Petition for Writ of Certiorari — Chapman v. Casner (No. 09-320)

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Supreme Court, U.S.

(i) ee BOS

\? No. 09- 09-320 SEP 1 0 2009

Intyp OFFICE OF THE CLERK

Supreme Court of the United States

ROBERT CHAPMAN, LONN S. RIDER, Qi Honc, DONALD KYLE

AND ROBERT KUPPER,

Petitioners,

MICHAEL LAWRENCE CASNER, JEN-SEN DUNG,

ERRNO M. KESKENY AND JIN LUO,

Respondents.

ON PETITION FOR A Writ OF CERTIORARI TO THE

UNITED STATES COURT OF APPEALS

FOR THE FEDERAL CIRCUIT

PETITION FOR A WRIT OF CERTIORARI

PHILLIP C. STRASSBURGER JOSEPH R. ROBINSON*

PURDUE PHARMA L.P Counsel of Record

One Stamford Forum Darpy & Darsy PC.

Stamford, CT 06901 7 World Trade Center

250 Greenwich Street

New York, NY 10007

(212) 527-7700

+ Admission pending

Attorneys for Petitioners

24953 ce

(S00) 274 382] © (S00) 359 6859

QUESTIONS PRESENTED

Two questions are presented:

1. How is the principle in Eibel Process Co. v.

Minnesota & Ontario Paper Co., 261 U.S. 45, 68 (1923),

that a claim may be non-obvious when the inventor

discovers a “source [of trouble or a problem] not before

known” and then claims the resulting “application of the

remedy,” applied in light of ASR International Co. v.

Teleflex, 550 U.S. 398 (2007)?

2. Does #£ibel require recitation of the newly

discovered source of the problem as claim limitations?

mm)

LIST OF PARTIES

The parties below are listed in the caption of this

Petition:

Robert Chapman, Lonn S. Rider, Qi Hong,

Donald Kyle and Robert Kupper (collectively,

“Chapman”), Petitioners, Appellants and

Senior Party in the Interference; and

Michael Lawrence Casner, Jen-Sen Dung,

Erno M. Keskeny and Jin Luo (collectively,

“Casner”), Respondents, Cross-Appellants

and Junior Party in the Interference.

The real party-in-interest for Chapman is Purdue

Pharma L.P

The real party-in-interest for Casner is Johnson-

Matthey Public Limited Company.

CORPORATE DISCLOSURE

The parent corporations and publicly held

companies that own ten percent or more of the

partnership interests of Purdue L.P:

NONE.

Upon information and belief, the parent

corporations and publicly held companies that own ten

percent or more of the stock of Johnson-Matthey Public

Limited Company:

Johnson Matthey Inc.

iil

TABLE OF CONTENTS

Pave

QUESTIONS PRESENTED ................ j

eG We Pee Ee i eee ee eee ii

CORPORATE DISCLOSURE ............... ii

TAB iss OF CAI EIOPC ED és 0s 6 cee se ovens lii

TABLE OF APPENDICES .................. iv

TABLE OF CITED AUTHORITIES ......... Vv

OPINION AND JUDGMENT BELOW ....... l

STATEMENT OF JURISDICTION .......... 1

STATUTORY PROVISION INVOLVED ...... ]

STATEMENT OF THE CASE ............... 4

SUMMARY OF THE ARGUMENT .......... 10

A. The Discovery of the Previously Unknown

Source of a Known or Unknown Problem

Must Still Indicate that the Remedy to

that Problem Is Non-Obvious .......... 10

BK. FEibel Does not Require the Problem or

Its Cause to Be Claim Limitations ...... 17

CHIP EASORUIEN 6 os as kas Vea ease ee 19

TABLE OF APPENDICES

Appendix A — Opinion Of The United States

Court Of Appeals For The Federal Circuit

Decided’ Maren 11, ZOOS onc cess ccc ce sececes

Appendix B — Memorandum Opinion And Order

Of The United States Patent And Trademark

Office Board Of Patent Appeals And

Interferences Entered March 18, 2008......

Appendix C — Order Of The United States

Court Of Appeals For The Federal Circuit

Denying Petition For Rehearing Filed June

Se Pe rr ee er rr ery mere

Appendix D — Judgment Of The United States

Court Of Appeals For The Federal Circuit

EXOCOG DEBTOR 14, Bee cc ccs is cccccccevccsess

Appendix E — Chapman Clean Copy Of Involved

Claims Dated May 3, 2007 .................

80a

TABLE OF CITED AUTHORITIES

Page

Cases:

Chapman v. Casner,

Appeal Nos. 2008-1427

(Fed. Cir. March 11, 2009) ................. l

Fibel Process Co.

v. Minnesota & Ontario Paper Co.,

ee Si ED ok eee ks peered cee yee passim

Graham v. Deere,

ee ae a vk vee ee ae a eee 14, 16

In re Peehs,

GIS Fee 1667 (CRA TORO) nn ccc ccc ceciucs 7

In re Sponnoble,

405 F.2d 678 (C.C.PA. 1969) ......cccccscces t

KSR International Co. v. Teleflex,

Oe Sis ED ns bc bs te eneeteeeeses passim

U.S. Constitution:

PETIOLES F.C TION © ck. s 0 cao 400060 0kdensenves 16

Cited Authorities

Page

Statutes:

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OPINION AND JUDGMENT BELOW

The opinion of the United States Court of Appeals

for the Federal Circuit is unreported and is dated March

11, 2009. Appendix A. The Judgment of the United

States Court of Appeals for the Federal Circuit is dated

March 11, 2009 and issued as a mandate on June 22,

2009. Appendix D. A timely request for rehearing was

denied on June 15, 2009. Appendix C.

STATEMENT OF JURISDICTION

This Court’s jurisdiction is invoked under 28 U.S.C.

§ 1254(1). This is a petition for a writ of certiorari from

a judgment of the United States Court of Appeals for

the Federal Circuit entered on March 11, 2009, and

issued as a mandate on June 22, 2009, in Chapman v.

Casner, Appeal Nos. 2008-1427, -1428 (Fed. Cir. March

11, 2009). Appendix D. See also Appendix A. A timely

request for rehearing was denied on June 15, 2009.

Appendix C,

STATUTORY PROVISION INVOLVED

Title 35 United States Code, Section 103(a)

§ 103. Conditions for patentability; non-

obvious subject matter

(a) A patent may not be obtained though the

invention is not identically disclosed or

described as set forth in section 102 of this

title, if the differences between the subject

matter sought to be patented and the prior

art are such that the subject matter as a

whole would have been obvious at the time

the invention was made to a person having

ordinary skill in the art to which said subject

matter pertains.

Patentability shall not be negatived by the manner

in which the invention was made.!

' Reference is made to Title 35 United States Code, Section

102 which reads:

§ 102. Conditions for patentability; novelty and loss

of right to patent

A person shall be entitled to a patent unless—

(a) the invention was known or used by others in

this country, or patented or described in a printed

publication in this or a foreign country, before the

invention thereof by the applicant for patent, or

(b) the invention was patented or described in a

printed publication in this or a foreign country or in

public use or on sale in this country, more than one

year prior to the date of the application for patent

in the United States, or

(d) the invention was first patented or caused to be

patented, or was the subject of an inventor’s

certificate, by the applicant or his lega!

representatives or assigns in a foreign country prior

to the date of the application for patent in this

country on an application for patent or inventor's

certificate filed more than twelve months before the

filing of the application in the United States, or

(Cont'd)

(Cont’d)

(e) the invention was described in

(1) an application for patent, published under

section 122 (b), by another filed in the United States

before the invention by the applicant for patent or

(2) a patent granted on an application for patent by

another filed in the United States before the

invention by the applicant for patent, except that an

internationa! application filed under the treaty

defined in section 351 (a) shall have the effects for

the purposes of this subsection of an application

filed in the United States only if the international

application designated the United States and was

published under Article 21(2) of such treaty in the

English language; or

(f) he did not himself invent the subject matter

sought to be patented, or

(g) (1) during the course of an interference

conducted under section 135 or section 291, another

inventor involved therein establishes, to the extent

permitted in section 104, that before such person’s

invention thereof the invention was made by such

other inventor and not abandoned, suppressed, or

concealed, or

(2) before such person’s invention thereof, the

invention was made in this country by another

inventor who had not abandoned, suppressed, or

concealed it. In determining priority of invention

under this subsection, there shall be considered not

only the respective dates of conception and

reduction to practice of the invention, but also the

reasonable diligence of one who was first to conceive

and last to reduce to practice, from a time prior to

conception by the other.

STATEMENT OF THE CASE

The Court of Appeals for the Federal Circuit

affirmed the order of the United States Patent and

Trademark Office Board of Appeals and Interferences

(“Board”) that all of the claims of Chapman’s U.S.

patent application no. 11/391,897 (Supplemental

Appendix and Appendix E) are unpatentable under

35 U.S.C. § 103(a) as obvious, not-withstanding that

Chapman discovered the previously unknown source of

a problem and then claimed the remedy. The Board’s

basis for federal jurisdiction was under 35 U.S.C. §§ 6(b)

and 135(a). The Federal Circuit’s basis for federal

jurisdiction was under 28 U.S.C. § 1295(a)(4)(A) and

35 U.S.C. § 141. Ada.

The Court of Appeals addressed the question of

obviousness in a manner contrary to 35 U.S.C. § 103

and the precedents of this Court. The Federal Circuit’s

majority decision (A2a-8a) directly conflicts with this

Court’s holding in Fibel Process Co. v. Minnesota &

Ontario Paper Co., 261 U.S. 45 (1923) that a claim may

be non-obvious when the inventor discovers a previously

unknown source or cause of trouble or a problem and

then claims the resulting application of the remedy. The

Federal Circuit’s decision also highlights a conflict

between Hibel and this Court’s decision in ASR

International Co. v. Teleflex, 550 U.S. 398 (2007).

The wisdom of Libel is of utmost importance today.

The Court should note that extraordinary amounts of

human and financial resources are expended by the

pharmaceutical industry in discovering the causes and

sources of medical problems such as diseases.

Pharmaceutical inventions are not the result of simply

a need or the knowledge that a problem exists. If so,

cancer and heart disease would have been cured decades

ago. Real and inventive research is directed to the

causes or sources of these known problems and diseases,

and this research must be patentable if the industry is

to continue its large investments. This Court should

affirm the modern relevance of #ibel and direct that

the discovery of the source of a problem is an important,

non-obvious part of the inventive process.

Here, Chapman invented a method for preparing

pharmaceutical oxycodone salts that have low levels of

the potentially toxic impurity, 14-hydroxy. *:’ A22a-24a.

' The following abbreviated chemical terms are used:

Ra = &a,14-dihydroxy-7,8-dihydrocodeinone;

8 = 8$,14-dihydroxy-7,8-dihydrocodeinone;

14-hydroxy = 14-hydroxycodeinone; and

ABUK = oa,f-unsaturated ketone.

’ Chapman’s sole independent claim reads as follows

(A2l1a):

96. A process for preparing oxycodone or an

oxycodone salt, which process comprises steps

of:

(a) preparing a mixture of oxycodone, solvent and

an acid;

(b) ineubating the mixture under conditions

suitable to promote reaction of 8,14-dihydroxy

7,8-dihydrocodeinone to 14-hydroxycodeinone;

and subsequently

reayents under conditions sufficient for

conversion of 14-hydroxycodeinone to

oxycodone.

Chapman’s invention was based upon their discovery of

the previously unknown cause (the formation of 8a, a

compound that Chapman first discovered and that

converts to new 14-hydroxy) of a problem (the impurities

in oxycodone salts that Chapman discovered were from

the formation of new 14-hydroxy) that was

misunderstood by the prior art. A9¥a, 40a-41a.

Oxycodone salt is a potent pain reliever (A3a, 23a)

prepared by the following steps: (1) converting thebaine

to 14-hydroxy; (2) converting the 14-hydroxy to

oxycodone; and (3) adding dilute acid at room

temperature to convert the oxycodone to its salt. Ada-

4a. However, oxycodone salts prepared in this manner

contain relatively high amounts of 14-hydroxy

impurities. A3a, 22a-23a.

The prior art believed that the 14-hydroxy

impurities in oxycodone salts were old 14-hydroxy that

was created in step (1), was unreacted in step (2), and

was carried over through step (3). A9¥a, 25a-26a. The

prior art taught that step (1) only produced a single by-

product, 88, which was of no concern because, in step

(3), 88 was converted to its benign, inert, stable salt, 8

salt. A43a-47a.

Chapman proved that the prior art understanding

of how 14-hydroxy impurities appeared in oxycodone salt

was wrong. Chapman discovered that the actual problem

was not old, carry-over 14-hydroxy created in step (1);

rather, it was 14-hydroxy that was newly formed in step

(3) from a previously unknown source. A3a-4a, Ya.

Chapman discovered that step (1) also produced a

previously unknown compound, 8a, which, when salted

in step (3), was converted into new 14-hydroxy. A3a-4a,

9a-10a. This was why, no matter how thoroughly the

prior art tried to remove old, left-over, excess 14-hydroxy

that was formed in step (1), but which remained

unconverted in step (2), pharmaceutical oxycodone salts

still had unaccountable and unexpected higher levels of

14-hydroxy impurities.

Chapman remedied this problem by designing the

claimed process: first, mixing the ingredients for salting

oxycodone (Chapman step (a), which starts at the end

of typical oxycodone production); second, letting the

salting progress to convert all of the 8, 14-dihydroxy to

something else (8 becoming its benign, inert, stable

salt (A5a) and 8a becoming new 14-hydroxy (A3a-5a,

9a-10a)) (Chapman step (b)); and third, converting the

new 14-hydroxy derived from 8@ to oxycodone with little

or no 14-hydroxy impurities remaining (Chapman step

(c)). Ada.

The Federal Circuit majority erred by ignoring this

Court’s holding in £7bel.* The majority below looked to

the obviousness of only a single step out of the sequence

that Chapman claimed. A6a-7a. The Federal Circuit

reasoned that Chapman’s invention was obvious because

the prior art disclosed that “8B, at least, will under

certain reaction conditions form 14-hydroxy.” A8a;

see also A6a-7a.

‘ The Court of Customs and Patent Appeals had followed

this Court’s holding in Libel. See, e.g., 1n re Pechs, 612 F.2d 1287,

1290 (C.C.PA 1980); Jn re Sponnoble, 405 F.2d 578, 586 (C.C.PA.

1969); Alla-12a.

This reasoning begs the question: why would anyone

apply the foregoing reaction to a mixture of benign,

inert, stable 8B salt and oxycodone salt in the absence

of Chapman’s discoveries that 8a was also there and

formed new 14-hydroxy? The answer is that no one

would and no one did. That is why Eibel should be

followed even in light of this Court’s discussion of

obviousness in ASR.

The Federal Circuit majority relied upon the United

States Food and Drug Administration’s recognition that

there was a need to eliminate impurities in oxycodone,

as sufficient reason to combine elements of the prior

art. A7a-8a. However, despite ASR, a mere need,

regardless of the number of possible remedies, cannot

serve as the reason to combine prior art elements if the

application of the remedy is the result of a new discovery,

as here.

There is a sharp conflict between this Court’s

decision in Hibel and this Court’s decision in ASR. The

application of Hibel here clearly results in the non-

obviousness of Chapman’s claims; however, the

application of ASR can force obviousness. There was

an industry need here, and when the source of the

problem was discovered by Chapman, the remedy may

have been to use well-known reactions. The fact

remains, however, that, despite this need, the prior art

did not disclose or suggest 8a, that 8a was also formed

in step (1), or that step (3) converted 8a into new 14-

hydroxy. These discoveries were Chapman’s alone and

were what led Chapman to the starting point and the

subsequent steps in their claimed process.

Since one of ordinary skill at the time of Chapman’s

invention did not know that 8,14-dihydroxy was actually

two compounds (the prior art 88 and Chapman’s newly

discovered 8a, each of which reacted differently under

similar conditions), the skilled person would not have

applied any prior knowledge about oxycodone

production or about 8B to 8a. Furthermore, it would not

have been even remotely obvious to try the foregoing

reaction in the absence of Chapman’s discovery that 8a

existed. If one did not know that 8a existed, one could

not have known to react it or how it reacted in

comparison to 8B under oxycodone salting conditions.

In fact, once one skilled in the art was told by Chapman

of 8a’s existence, it would have been a total surprise

that it reacted entirely differently than 88 under the

pertinent conditions.

Therefore, it was error for the Federal Circuit

majority to have ignored this Court’s holding in Ebel

and to have concluded that Chapman’s remedy to a

problem with a previously unknown cause was obvious

at the time of its invention. A8a. It is illogical for an

industry need, with or without a finite number of

remedies, to serve as a reason to combine references or

to find obviousness when the source of the problem

confronting the industry had previously been completely

misunderstood. The discovery of the source of the

problem is an innovation. Necessity can be the mother

of a patentable invention, not its antithesis. ASR and

Eibel must be reconciled.

As Judge Rader correctly stated in his dissent:

Chapman, thus, was the first person to identify

the true nature of the “leftover” 14-hydroxy

problem and the first to solve it. ... this

important and innovative solution deserves a

patent over the prior art.

AQa.

SUMMARY OF THE ARGUMENT

A. The Discovery of the Previously Unknown Source

of a Known or Unknown Problem Must Still

Indicate that the Remedy to that Problem Is Non-

Obvious

Chapman’s discovery of the previously unknown

compound, 8a, as the source of problematic 14-hydroxy

impurities in oxycodone salts is precisely the type of

discovery that gave rise to a patent in Libel Process Co.

v. Minnesota & Ontario Paper Co., 261 U.S. 45, 67-68

(1923). Eibel discovered the previously unknown source

of a problem and then was granted a patent to the

problem’s remedy.

Eibel concerned a newsprint paper-making

machine. Before Eibel entered the field, a standard

paper-making machine could only run at about 500 feet/

minute. Faster speeds resulted in defective paper.

Inventor Eibel discovered that the defects were due to

disturbances and ripples in the stock used to make the

paper as the stock was forming (through the removal of

water) on a traveling wire screen. He observed that the

wire screen was traveling much faster than the stock.

This led him to conclude that, if the speed of the stock

could be increased to approximately the speed of the

wire, the disturbance and rippling in the stock would

cease and the paper defects would disappear. Hibel

proposed to increase the speed of the stock through the

use of gravity, by inclining the wire. The use of an incline

and gravity was known in the prior art to increase speed.

However, no one had previously used an incline and

gravity to increase stock speed to match the speed of

the wire in paper production, because no one had

previously understood the cause or source of the paper

defects. Eibel made that discovery. The accused

infringer alleged, inter alia, that the obvious application

of the well-known principles of an incline and gravity

made Eibel’s invention unpatentable.

This Court confirmed the validity of Eibel’s patent

and held that although Libel did not invent the paper-

making machine, he did discover what caused the paper

defects and used well known principles to fix it. Chief

Justice Taft wrote:

[OJne essential part of Eibel’s discovery was

that the trouble causing the defective paper

product under high machine speed was in the

disturbance and ripples some ten feet from

the discharge and that they were due to the

unequal speeds of stock and wire at that point

and could be removed by equalizing the

speeds. The invention was not the mere use

of a high or substantial pitch to remedy a

known source of trouble. It was the discovery

of the source not before known and the

application of the remedy for which Eibel was

entitled to be rewarded in his patent.

FKibel, 261 U.S. at 67-68 (emphasis added).

Chapman’s invention, like Eibel’s, is patentable.

Chapman addressed a market need, as did Eibel,

discovered the cause or source of a problem, as did Eibel,

and applied a remedy, as did Eibel; and Chapman, as

Eibel, is entitled to a patent covering that remedy.

It is irrelevant whether Chapman used known

reaction schemes. They were never before applied to

Chapman’s reactants; nor were they ever before applied

to remedy the previously unknown source (which

Chapman first discovered) of the problem Chapman

addressed. Chapman’s discoveries and invention have

allowed the industry to move forward and to make low

ABUK oxycodone.

As Judge Rader aptly summarized the matter in his

dissent:

Chapman unexpectedly discovered that the

stereoisomer 8a, when salted, creates

additional 14-hydroxy. This additional

14-hydroxy can be isolated and hydrogenated

to create additional oxycodone, containing

much less of the 14-hydroxy that the FDA

desired removed from oxycodone salt.

Persons of ordinary skill] in the art never

discovered or appreciated the presence of 8a

as the source of the additional 14-hydroxy. The

prior art disclosed that 14-hydroxy was a

carry-over from the oxidation of thebaine,

resulting in leftover, unreacted 14-hydroxy in

the oxycodone salt. “[T]he challenges of this

inventive process would have prevented one

of ordinary skill in this art from traversing the

multiple obstacles to easily produce the

invention in light of the evidence available at

the time of the invention.” Ortho-McNeil,

52 F.3d at 1365. Chapman, therefore,

unexpectedly discovered the true source of

the additional 14-hydroxy and solved the

problem by removing the impurity from

oxycodone salt. Because the prior art could

not have intended or appreciated Chapman’s

discovery or solution, the invention deserves

patent protection.

Alda.

The application of KSR International Co. v. Teleflex,

550 U.S. 398 (2007) gives a contrary result. This Court

stated in ASR that:

any need or problem known in the field of

endeavor at the time of invention and

addressed by the patent can provide a reason

for combining the elements in the manner

claimed.

KSR, 550 U.S. at 420 (emphasis added).

However, this is in conflict with the facts and

reasoning of this Court in Hibel. See Fibel, 261 U.S. at

68 (“It was the discovery of the source not before known

and the application of the remedy for which Eibel was

entitled to be rewarded in his patent.” (emphasis

added)). There was a need in the newspaper industry,

and the problem was known to be defects in the paper.

Eibel discovered the unknown source of the known

problem and, then, claimed a remedy using known

principles of physics to satisfy an industry need.

The Federal Circuit majority, in the case now before

this Court, pointed out that “the Board noted that the

FDA ‘recognized that there was a need to eliminate

impurities in oxycodone,’ and then proceeded to walk

through the prior art... .” A7a-8a. The alleged “need”

was the Federal Circuit majority’s invitation to combine

elements of the prior art and directly resulted in the

holding of obviousness of Chapman’s claims. See KSR,

550 U.S. at 420 (any known need or problem can provide

a reason to combine elements as claimed).°

However, in this case, as in Libel, there was no

reason to combine any prior art elements before the

® It is also incongruous that in KSR, a need is a reason to

combine prior art elements and make an invention obvious, but

in Graham, 383 U.S. at 17, this Court found long-felt need to be

objective evidence of non-obviousness. The speed at which an

inventor makes his or her invention should not be a determining

factor in the obviousness analysis. Speed of invention can be

inventor-specific and dependent upon many different factors,

including the skill of the inventor, the depth of his or her

understanding of the problem or its source, the financial

resources at his or her disposal, or even luck. None of these

negates an inventor’s innovation.

inventors’ new discovery of the source of the problem.

KSR is in conflict with /ibel on this point. The reasoning

of ASR would make Ejibel’s invention unpatentable

because the problem in £2bel was previously known and

because there was an industry need. [t was the

previously unknown source of the problem that was

Eibel’s discovery and was the key to Eibel’s claimed

invention.

This conflict cannot be what this Court intended its

reasoning in KSR to create. An examination of the facts

of KSR is useful here. The patent-at-issue in KSR

claimed a combination of a sensor and an adjustable

pedal, where the pedal’s position could be transmitted

to a computer controlling the vchicle’s throttle. The

prior art, Asano, disclosed pedals that could be adjusted

to change their position where one of the pedal’s pivot

points stayed fixed even when the pedal was adjusted.

Appropriate electronic sensors and preferred sensor

positions were also in the prior art, as were the facts

that it was better to detect the position of the pedal

position from within the pedal assembly rather than from

within the engine and that it was better to place the

sensor on a fixed part of the pedal assembly rather than

on the pedal’s footpad because of wire chaffing caused

by the movement of a moveable sensor. The legal

question was “whether a pedal designer of ordinary skill

starting with Asano would have found it obvious to put

the sensor on a fixed pivot point.” ASR, 550 U.S. at

424-25.

This Court concluded that the ASF invention was

obvious because a designer would have known to place

the sensor on a non-moving point of the structure and

the most obvious suitable non-moving point was the

pivot point. ASR, 550 U.S. at 425. The starting point,

the problem, and the source of the problem were known

at the time of the ASR invention; and the analysis could

be performed without hindsight.

However, neither the starting point nor the source

of the problem was known at the times of Ejibel’s or

Chapman’s inventions. Regarding the former, no one

knew where to start. The prior art believed that

14-hydroxy was only created in step (1). No one knew

that new 14-hydroxy was created in step (3), that 8a

was its source, or that 8a reacted differently than 86

under the pertinent conditions. The source of the

impurities, 8a, was Chapman’s discovery alone, and

absent the license of KSR to combine references based

upon a “need” or a “known problem”, only hindsight of

Eibel’s or Chapman’s discovery could lead to a

conclusion that their respective inventions were obvious.

See KSR, 550 U.S. at 421 citing Graham v. Deere, 383

U.S. 1, 36 (1966) “(See Graham, 336 U.S. at 36 (warning

against “temptation to read into the prior at the

teachings of the invention in issue” and instructing

courts to “‘guard against slipping into the use of

hindsight’” (quoting Monroe Auto Equipment Co. v.

Keckethorn Mfg. & Supply Co., 332 F.2d 406, 412 (CA6

1964)))).”

It is important for the promotion of the progress of

science and useful arts, that this Court clarify that ASR

does not abrogate its earlier holding in Aibel. See Fibel,

261 U.S. 45 at 68; see also U.S. ConsTITUTION, ARTICLE

1, Section 8. A claimed remedy may be non-obvious

when any one of the starting point for the remedy, the

problem, or the source of the problem was unknown

before it was discovered by the applicant for a patent

claiming the remedy.

Accordingly, since Chapman discovered the

previously unknown source of a problem, Chapman’s

claims are non-obvious.

B. Eibel Does not Require the Problem or Its Cause

to Be Claim Limitations

Nothing in £ibel requires the problem or its cause

to be limitations of the claimed remedy. However, the

Federal Circuit majority required just that. The majority

stated:

Chapman argues that he was the first to

recognize that additional 14-hydroxy is

created from 8a during the reaction’s salting

step, and that the “new” 14-hydroxy can

therefore yield additional oxycodone.

Chapman purports to claim this method of

eliminating the “new” 14-hydroxy in claim 96.

The claim does not, however, differentiate

between the 8a and 8f forms of 8,14

dihydroxy, nor does the claim language

specifically disclose which conditions are

“suitable” for promoting the desired reaction

from 8, 14-dihydroxy to 14-hydroxy.

Ada.

Differentiation between the 8a and 8f forms of 8,14-

dihydroxy and the conditions “suitable” for promoting

the desired reaction from 8, 14-dihydroxy to 14-hydroxy

are pertinent to Chapman’s discovery of a new problem

and its source. They are not necessary to claim a remedy

to these problems and are not required claim limitations.

Eibel discovered that defects in paper were due to

the fact that the wire screen on which stock formed

paper traveled faster than the stock. This lead him to

conclude that if the speed of the stock were increased

to about the speed of the wire, disturbances and rippling

in the stock would cease and the paper defects would

disappear. The problem was disturbances and rippling

in the stock, and this was caused by mismatched stock

and wire speeds. The solution was to decline the wire

and to move the suction boxes of the paper-making

machine, neither of which was much of an invention

absent the fact that these moves solved the problem.

However, Eibcl’s claims 7 and 8 read:

7. A Fourdrinier machine having the paper-

making wire declined from the breast-roll to

the guide-roll, and the suction-boxes

supported at corresponding declination,

substantially as described.

8. A Fourdrinier machine having the paper

making wire declined from the breast-roll to

the guide-roll, and the several suction-boxes

arranged at different elevations, substantially

as described.

Eibel, 261 U.S. at Prior History. Neither claim stated

the problem or its source. However, this Court found

that these claims were patentable.

Similarly, Chapman’s claims as drafted (7.e., absent

the term 8a and species of suitable conditions) are

patentable. Chapman’s claims, even in their broadest

interpretation, do not read on any single reference, and

there was no reason to combine any references in the

absence of Chapman’s discovery. Therefore, Chapman’s

claims as written are non-obvious.

CONCLUSION

Wor all of the foregoing reasons, petitioners request

that the Supreme Court grant this petition for a writ of

certiorari and review this matter.

Respectfully submitted,

JOSEPH R. ROBINSON *

Counsel of Record

Darey & Darry PC.

7 World Trade Center

250 Greenwich Street

New York, NY 10007

(212) 527-7700

PHILLIP C. STRASSBURGER

PURDUE PHARMA L.P

One Stamford Forum

Stamford, CT 06901

Attorneys for Petitioners

Ys,

+ Admission pending

APPENDIX

APPENDIX A — OPINION OF THE UNITED

STATES COURT OF APPEALS FOR THE FEDERAL

CIRCUIT DECIDED MARCH 11, 2909

UNITED STATES COURT OF APPEALS

FOR THE FEDERAL CIRCUIT

2008-1427, -1428

(Interference No. 105,553)

ROBERT CHAPMAN, LONN S. RIDER, QI HONG,

DONALD KYLE, and ROBERT KUPPER,

Appellants,

MICHAEL LAWRENCE CASNER, JEN-SEN

DUNG, ERNO M. KESKENY, and JIN LUO,

Cross Appellants.

Appeals from the United States Patent and Trademark

Office, Board of Patent Appeals and Interferences.

DECIDED: March 11, 2009

Before LOURIE, RADER, and PROST, Circuit Judges.

Opinion for the court filed by Circuit Judge PROST.

Dissenting opinion filed by C?rcuit Judge RADER.

Appendix A

PROST, Circuit Judge.

Robert Chapman, Lonn Rider, Qi Hong, Donald

Kyle, and Robert Kupper’s (“Chapman’s”) U.S. Patent

Application No. 11/391,897 (“the ’897 application”) and

Michael Casner, Jen-Sen Dung, Erno Keskeny, and Jin

Luo’s (“Casner’s”) U.S. Patent No. 7,153,966 (“the 966

patent”) both claim methods of preparing oxycodone

that reduce the levels of a potentially toxic intermediate,

14-hydroxycodeinone. In Interference No. 105,553, the

Board of Patent Appeals and Interferences (“the

Board”) granted Casner’s motion seeking judgment that

Chapman claims 96-118 were unpatentable under

35 U.S.C. § 103(a). Chapman appeals, asking us to hold

claims 96-118 of the ’897 application nonobvious. Casner

maintains that those claims were obvious, but has also

lodged a cross-appeal, arguing that if we reverse the

Board’s holdings as to the ’897 application, we should

reverse its holdings on the ’966 patent and remand for

a priority determination. For the reasons set forth below,

we affirm the Board’s obviousness determination.

I. BACKGROUND

The ’897 application is entitled “Process for

Preparing Oxycodone Hydrochloride Having Less Than

25 ppm 14-Hydroxycodeinone.” The only independent

claim at issue is claim 96, which recites:

A process for preparing oxycodone or an

oxycodone salt, which process comprises steps

of:

Appendix A

(a) preparing a mixture of oxycodone, solvent

and an acid;

(b) incubating the mixture under conditions

suitable to promote reaction of 8, 14-

dihydroxy-7, 8-dihydrocodeinone to 14-

hydroxycodeinone; and subsequently

reagents under conditions sufficient for

conversion of 14-hydroxycodeinone to

oxycodone.

J.A. 77 (emphases added).

Oxycodone is a synthetic analgesic opioid used to

relieve pain. Typically, one prepares oxycodone by

first oxidizing thebaine. This step converts thebaine into

two types of compounds: 14-hydroxycodeinone

(“14-hydroxy”) and the 8, 14-dihydroxy-7, &-

dihydrocodeinones (collectively, “8, 14-dihydroxys”). The

14-hydroxy is converted via hydrogenation into

oxycodone, which is then treated with acid during a final

“salting” step to yield pharmaceutical grade oxycodone.

Any 14-hydroxy remaining at the end of the reaction is

problematic, as the compound is potentially toxic.

The 8, 14-dihydroxys created during the initial

oxidation step are stereoisomers—there are two forms,

designated “8a” and an “8,” that differ only by the

relative orientation of a hydroxyl group. Chapman

claims that prior to the ’897 application, persons of

Appendix A

ordinary skill in the art did not know that 8a formed

during the reaction. Instead, they believed that thebaine

oxidized to form 14-hydroxy and 88, and that any 14-

hydroxy remaining at the end of the reaction was

leftover, unreacted 14-hydroxy. In fact, during the

salting step at least one of the 8, 14-dihydroxys reacts

with acid to form “new” 14-hydroxy; this 14-hydroxy can

then, of course, undergo hydrogenation to become

additional oxycodone.

Chapman argues that he was the first to recognize

that additional 14-hydroxy is created from 8a during

the reaction’s salting step, and that the “new” 14-

hydroxy can therefore yield additional oxycodone.

Chapman purports to claim this method of eliminating

the “new” 14-hydroxy in claim 96. The claim does not,

however, differentiate between the 8a and 8B forms of

8, 14-dihydroxy, nor does the claim language specifically

disclose which conditions are “suitable” for promoting

the desired reaction from 8, 14-dihydroxy to 14-hydroxy.

We have jurisdiction under 28 U.S.C. § 1295(a)(4)(A).

Il. DISCUSSION

Obviousness is a legal conclusion based on

underlying findings of fact. Jn re DBC, 545 F.3d 1373,

1377 (Fed.Cir.2008). We review the Board’s ultimate

determination of obviousness de novo, while we review

the Board’s underlying factual findings for substantial

evidence. /d.

Appendix A

We first turn to Chapman’s arguments. Chapman

claims that prior to the ’897 application, no one knew

that 8a was formed during thebaine oxidation. Nor,

according to Chapman, was it known that 8a could react

with acid under certain “commercial conditions” to form

additional 14-hydroxy. Chapman admits that the prior

art disclosed 88, but claims that “under commercial

oxycodone production conditions,” 8f converts into a

benign salt, not into 14-hydroxy. In his view, the prior

art would lead a person of ordinary skill in the art to

believe that 8 must be treated with “stronger than

commercially used” amounts of hydrochloric acid before

it converts to 14-hydroxy.

Casner states that Chapman never claimed 8a@ as

crucial to the invention before the Board; in other words,

Chapman never tried to distinguish the prior art based

on stereochemistry. Casner likewise argues that

Chapman waived any “commercial conditions” limitation.

Chapman responds that both issues were raised,

although the stereochemistry argument is emphasized

on appeal because Casner did not produce the “Proksa”’

reference (upon which the Board relied) until its

response, leaving Chapman little opportunity to analyze

and respond to the specific issues raised by that

reference. Chapman also argues that since the Board

identified a “commercial need” for reduced levels of

14-hydroxy, and found that a person of skill in the art

would work in the “highly competitive pharmaceutical

industry,” the Board understood that commercial

conditions were at issue.

Appendix A

Chapman does not direct us to specific arguments

in submissions to the Board where counsel pursued the

claim that commercial conditions were necessary; nor

has Chapman clarified which conditions would qualify

as “commercial conditions.” Similarly, although 8a is

identified in some of the ’897 application’s figures, and

Chapman’s expert made references to stereoisomers in

reviewing the prior art, Chapman has not identified any

statement before the Board that explicitly differentiated

between the invention and the prior art based on

stereochemistry.

Regardless, we need not resolve the waiver issue

definitively. Chapman maintains, and we agree, that

“{t]he term ‘8, 14-dihydroxy’ properly includes 8a, but

there is no reason for that term to be limited to that

isomer in Chapman’s claims. The term ‘conditions’

properly includes commercial conditions, but there is

no reason to limit that term to commercial conditions in

Chapman’s claims.” Appellant’s Reply Br. 27. Further,

the ’897 application states: “The term 8, 14-dihydroxy-

7, 8-dihydrocodeinone includes either 8a, 14-dihydroxy-

7, 8-dihydrocodeinone; or 8B, 14-dihydroxy-7, 8-

dihydrocodeinone or can include a mixture of both

compounds.” ’897 application 11 0043.

Thus, claim 96 merely requires one to incubate the

mixture “under conditions suitable to promote reaction”

of 8, 14-dihydroxy to 14-hydroxy. Therefore, prior art

references that disclose either the 8a or 8B form of &,

14-dihydroxy converting to 14-hydroxy, or disclose any

reaction condition (whether “commercial” or not) that

Appendix A

promotes the conversion of 8a or 8B to 14-hydroxy, may

render the claim obvious. See In re May, 574 F.2d 1082,

1088-89 (C.C.PA.1978) (“{The reference] expressly

discloses .. . a species within the genus of claim 1.

Therefore, [the reference] is a technical anticipation of

claim 1. Appellants’ assertions to the contrary

notwithstanding, this finding does not constitute a new

ground of rejection; lack of novelty is the epitome of

obviousness.”); cf Medichem, S.A. v. Rolabo, S.L., 353

F.3d 928, 934-35 (Fed. Cir. 2003) (concluding that first

step of an interference-in-fact inquiry was satisfied

where two method claims had a genus/species

relationship, since “ ‘[i]t is .. . an elementary principle

of patent law that when, as by a recitation of ranges or

otherwise, a claim covers several compositions, the claim

is “anticipated” if one of them is in the prior art.’ ”)

(quoting Titanium Metals Corp. v. Banner, 778 F.2d 775,

782 (Fed.Cir.1985)); Eli Lilly & Co. v. Barr Labs., Ine.,

251 F.3d 955, 971 (Fed. Cir. 2001) (in context of an

obviousness-type double patenting analysis, noting that

“(t]he only other difference between [the two method

claims] is that the former is directed to humans while

the latter is directed to animals,” and “[ojur case law

firmly establishes that a later genus claim limitation is

anticipated by, and therefore not patentably distinct

from, an earlier species claim.”).

The Board found that the prior art discloses

methods under which at least one 8, 14-dihydroxy reacts

to yield 14-hydroxy under certain conditions. Specifically,

the Board noted that the FDA “recognized that there

was a need to eliminate impurities in oxycodone,” and

Appendix A

then proceeded to walk through the prior art, which

disclosed: that both 14-hydroxy and 8, 14-dihydroxy were

known impurities during the thebaine oxidation

reaction; that treatment of 8, 14-dihydroxy with

hydrochloric acid converts 8, 14-dihydroxy into

14-hydroxy under certain reaction conditions; that one

of skill in the art would be able to identify those

conditions; and that 14-hydroxy may be removed from

oxycodone via hydrogenation.

As mentioned, claim 96 would have been obvious if

properly-combinable references disclosed conditions

suitable to promote reaction of 8, 14-dihydroxy to

14-hydroxy. The prior art references here do just that:

they indicate that 8B, at least, will under certain reaction

conditions form 14-hydroxy. Given that claims directed

to the genus (methods for eliminating 8, 14-dihydroxys)

can be anticipated or rendered obvious by references

disclosing the species (methods for eliminating either

the 8a or 8B form of 8, 14-dihydroxy), we agree with the

Board that the method described in claim 96 would have

been obvious. As a result, we need not address Casner’s

cross appeal.

Ill. CONCLUSION

For the reasons detailed above, we affirm the

Board’s decision to reject claims 96-118 of the ’897

application under 385 U.S.C. § 103(a).

Appendix A

RADER, Circuit Judge, dissenting.

The Food and Drug Administration seeks the

removal of impurities such as 14-hydroxy from the pain

medicine oxycodone salt. During research on oxycodone,

Chapman discovered that oxidation of thebaine creates

the stereoisomer 8a, which in turn creates additional

14-hydroxy during formulation of this important

pharmaceutical. Until this discovery, this field of art

believed that the original oxidation step created the

additional 14-hydroxy impurity. After discovering 8a,

Chapman learned to isolate and hydrogenate the

additional 14-hydroxy to eliminate most of these

impurities. Chapman, thus, was the first person to

identify the true nature of the “leftover” 14-hydroxy

problem and the first to solve it. Because this important

and innovative solution deserves a patent over the prior

art, I would reverse the Board.

Chapman’s invention calls to mind the Supreme

Court’s resolution of Hibel Process Co. v. Minnesota &

Ontario Paper Co., 261 U.S. 45, 43 S.Ct. 322, 67 L.Ed.

523 (1923). In Hibel, the primary distinction of the

invention over the prior art was discovery of the problem

in that discipline. /d. at 67-68, 43 S.Ct. 322. Eibel

discovered that unequal speeds of stock and wire

produced a defective paper product under high machine

speeds. /d. The variance in paper speed created

disturbances and ripples some ten feet from the

discharge. /d. With the problem defined, Ejibel easily

prescribed the solution by elevating one end of the paper

10a

Appendix A

feed to equalize the speeds of the wire and the paper

stock by gravity. /d. at 64, 43 S.Ct. 322.

In this case, Chapman discovered that the salting

of stereoisomer 8a, not the oxidation of thebaine,

created the additional 14-hydroxy impurity in oxycodone

salt. He solved this problem by isolating and

hydrogenating the 14-hydroxy to form additional

oxycodone. Chapman’s invention was not the mere use

of a known technique to remedy a known source of

trouble, but was, as Chief Justice Taft stated, “the

discovery of the source not before known and the

application of the remedy” for which he seeks reward of

the grant of a patent. /d. at 68, 43 S.Ct. 322.

Similarly, in /n re Conover, Conover discovered a

solution to the problem of connecting a rod to an

outboard motor engine containing compact, anti-friction

roller bearings. 49 C.C.PA. 1205, 304 F.2d 680, 681 (1962).

A phenomenon known as “galling” could destroy the

bearings at unpredictable times by heating of the roller

elements. /d. at 681-82. To overcome this “galling,”

Conover put a non-galling material, such as silver, on

the end faces of the connecting rod bearings. /d. at 682.

Citing the rationale of Erbel, the Court of Customs and

Patent Appeals (“CCPA”) found that the differences

between Conover’s patent application and the prior art

were such that “the subject matter as a whole,” 7.¢., (a)

“the discovery of the cause of the bearing failures” and

(b) “its elimination by the claimed plating of... the

contacting areas of the face portions of the connecting

rods and the crank cheeks, were not obvious from the

lla

Appendix A

prior art at the time the invention was made to a person

having ordinary skill in this art.” /d. at 684.

In In re Sponnoble, the pharmaceutical industry

faced the problem of unwanted moisture leakage

between liquid and solid compartments in vials.

56 C.C.PA. 823, 405 F.2d 578, 586 (1969). Sponnoble

discovered that the cause of this leakage was the passage

of moisture through, rather than around, the center

plug of the vial. 7d. He solved the problem by fabricating

a center seal plug of butyl rubber with a silicone coating.

Id, The CCPA found, “a patentable invention may lie in

the discovery of the source of a problem even though

the remedy may be obvious once the source of the

problem is identified. This is part of the ‘subject matter

as a whole’ which should always be considered in

determining the obviousness of an invention under

35 USC 103.” Jd. at 585. In resolving the issue of

obviousness, the court stated, “The crux of the matter

.. is the discovery by appellant that passage through

the center plug was a major cause of moisture

transmission.” Jd. at 586. The court reasoned that “[t]he

question here is whether the prior art recognized the

cause of the problem,” which it did not. /d.

The CCPA in Jn re Peehs found that Peehs had

represented to the Patent and Trademark Office that

up until the time of the claimed invention, “the nuclear

[power] industry faced the problem of undesirable

stressing of fuel rod claddings in gas-cooled nuclear

reactors.” 612 F.2d 1287, 1290 (C.C.PA.1980). Peehs

discovered that “the cause of this stressing was sticking

|2a

Appendix A

between the metal surfaces of the claddings and the

contact elements of the spacer grids.” /d. He solved this

problem by “roughening one of the contact surfaces.”

Id. Thus, as in Libel, Conover, and Sponnoble, “the crux

of the matter is the discovery by appellants of the cause

of a problem, and the determinative question is whether

that cause would have been recognized by one of

ordinary skill in the art at the time the invention was

made.” Jd.

In reversing the Board’s holding of obviousness, the

CCPA found “no support for the conclusion that those

of ordinary skill in the art would have recognized that

sticking between the fuel rod cladding and the spacer

grid contact elements caused the stressing of the

claddings.” /d. The court also found that “ [where] there

is no evidence of record that a person of ordinary skill

in the art at the time of [an applicant’s] invention would

have expected [a problem]’, e.g., sticking, ‘to exist at

all, it is not proper to conclude that [an invention]’, e.g.,

roughening one of the contact surfaces, ‘which solves

this problem, ... would have been obvious to that

hypothetical person of ordinary skill in the art.’” /d.

(citing Jr re Nomiya, 509 F.2d 566, 572 (C.C.PA.1975)).

The Supreme Court in ASR /nternational Co. v.

Teleflex Inc. recently held that “[w]hen there is a design

need or market pressure to solve a problem and there

are a finite number of identified, predictable solutions,

a person of ordinary skill has good reason to pursue the

known options within his or her technical grasp. If this

leads to the anticipated success, it is likely the product

l3a

Appendix A

not of innovation but of ordinary skill and common

sense.” 127 S.Ct. 1727, 1742 (2007). This case, as are

Kibel, Conover, Sponnoble, and Peehs, is distinguished

from ASR because there were no “finite number of

identified, predictable solutions” that were used to

discover the source of and solution to the problems. /d.

No persons of ordinary skill in the art knew of the

existence of 8a before Chapman and, in fact, were trying

to solve the problem of removing excess 14-hydroxy

impurities from oxycodone salt by other means. Because

no other persons had discovered and solved this

problem as Chapman did, his invention is the product

of innovation and not of “ordinary skill and common

sense.” /d.

Following ASR, this court in 2008 in Ortho-McNeil

Pharmaceutical, Inc. v. Mylan Laboratories, Inc.,

found an invention worthy of a patent when a researcher

in his search for a new antidiabetic drug, accidentally

discovered topiramate. 520 F.3d 1358 (Fed. Cir. 2008).

Topiramate is a reaction intermediate that has powerful

anticonvulsant properties marketed by Ortho-McNeil

as TOPOMAX® for the treatment of epilepsy. /d. at

1360. This court attached particular importance to the

objective criteria of nonobviousness, including the

powerful, unexpected results of topiramate (7.e.,

anticonvulsive activity), skepticism of experts, copying,

and commercial success. /d. at 1365. “As this court has

repeatedly explained, this evidence is not just a

cumulative or confirmatory part of the obviousness

calculus but constitutes independent evidence of

nonobviousness.” /d. (citing Catalina Lighting, Ine. v.

l4a

Appendix A

Lamps Plus, /nc., 295 F.3d 1277, 1288 (Fed.Cir.2002)

(“Objective indicia may often be the most probative and

cogent evidence of nonobviousness in the record.”)).

Chapman unexpectedly discovered that the

stereoisomer 8a, when salted, creates additional 14-

hydroxy. This additional 14-hydroxy can be isolated and

hydrogenated to create additional oxycodone,

containing much less of the 14-hydroxy impurities that

the FDA desired removed from oxycodone salt. Persons

of ordinary skill in the art never discovered or

appreciated the presence of 8a as the source of the

additiona! 14-hydroxy. The prior art disclosed that

14-hydroxy was a carry-over from the oxidation of

thebaine, resulting in leftover, unreacted 14-hydroxy in

the oxycodone salt. “{Tlhe challenges of this inventive

process would have prevented one of ordinary skill in

this art from traversing the multiple obstacles to easily

produce the invention in light of the evidence available

at the time of invention.” Ortho-McNeil, 520 F.3d at 1365.

Chapman, therefore, unexpectedly discovered the true

source of the additional 14-hydroxy and solved the

problem by removing the impurity from oxycodone salt.

Because the prior art could not have intended or

appreciated Chapman’s discovery or solution, this

invention deserves patent protection.

For the foregoing reasons, | respectfully dissent.

lSa

APPENDIX B — MEMORANDUM OPINION AND

ORDER OF THE UNITED STATES PATENT AND

TRADEMARK OFFICE BOARD OF PATENT

APPEALS AND INTERFERENCES

ENTERED MARCH 13, 2008

UNITED STATES PATENT AND TRADEMARK

OFFICE BOARD OF PATENT APPEALS AND

INTERFERENCES

Patent Interference 105,553 McK

Technology Center 1600

MICHAEL LAWRENCE CASNER, JEN-SEN

DUNG, ERNO M. KESKENY and JIN LUO,

Patent 7,153,966 B2,

Junior Party,

ROBERT CHAPMAN, LONN S. RIDER, QI HONG,

DONALD KYLE and ROBERT KUPPER,

Application 11/391,897,

Senior Party,

Before: FRED E. McKELVEY, Senior Administrative

Patent Judge, and RICHARD TORCZON and

MICHAEL P. TIERNEY, Administrative Patent

Judges.

l6a

Appendix B

McKELVEY, Senior Administrative Patent Judge.

MEMORANDUM OPINION and ORDER

Decisions on Motions

A. Statement of the case

The interference is before a motions panel for

consideration of non-priority motions filed by the parties.

Chapman Motion 1

Chapman Motions 1-2 seeks an earlier constructive

reduction to practice. Paper 24.

Casner timely filed Casner Oppositions 1-2. Paper 42.

Chapman timely filed Chapman Replies 1-2. Paper 59.

Chapman Motion 1 is dismissed as moot.

Casner Motion 1

Casner Motion 1 seeks judgment based on no

interference-in-fact. Paper 28.

Chapman timely filed Chapman Opposition 1. Paper

44.

Casner timely filed Casner Reply 1. Paper 58.

Chapman Motion 1] is denied.

17a

Appendix B

Casner Motion 2

Casner Motions 2-5 seeks to deny earlier

constructive reductions to practice accorded to

Chapman when the interference was declared. Paper

“ao.

Chapman timely filed Chapman Oppositions 2-5.

Paper 45.

Casner timely filed Casner Replies 2-5. Paper 54.

Casner Motions 2-5 is dismissed as moot.

Casner Motions 6-7

Casner Motions 6-7 seeks judgment based on an

alleged lack of written description on the part of

Chapman. Paper 30.

Chapman timely filed Chapman Oppositions 6-7.

Paper 46.

Casner timely filed Casner Replies 6-7. Paper 55.

Casner Motions 6-7 is denied.

18a

Appendix B

Casner Motions 9-10

Casner Motions 9-10 seeks judgment based on

alleged unpatentability of the Chapman claims. Paper

32.

Chapman timely filed Chapman Oppositions 9-10.

Paper 48.

Casner timely filed Casner Replies 9-10. Paper 57.

Casner Motions 9-10 is granted. We also hold that

involved Casner claims 1-12 are unpatentable under

35 U.S.C. § 103.

Order of deciding motions

The rules authorize the Board to take up motions

for decisions in any order. 37 C.ER. § 41.125(a) (2007).

First, we elect to consider first Casner Motions 9-

10 which urges unpatentability under 35 U.S.C. § 103.

We do so because we believe the case is more easily

understood by discussing the evidence relevant to that

motion.

Second, we then take up Casner Motion 1 urging

no interference-in-fact.

Third, we take up Casner Motions 6-7 urging

unpatentability for lack of written description and lack

of enablement.

19a

Appendix B

In view of the disposition of Casner Motions 9-10,

Casner Motion 1 and Casner Motions 6-7, we do not

believe it necessary to consider the remaining motions.

The interference—parties

The interference involves junior party patentee

Casner versus senior party applicant Chapman.

Junior party patentee Casner is involved on the

basis of Casner patent 7,153,966 B2 issued 26 December

2006, which is based on application 11/234,627 filed 23

September 2005.

The Casner real party in interest is Johnson

Matthey Public Limited Company. Paper 6.

Casner has been accorded earlier constructive

reductions to practice (7.e., benefit for the purpose of

priority) based on the following applications:

British patent application 04-21149.6 filed 23

September 2004

Senior party applicant Chapman is involved on the

basis of Chapman application 11/391,897, filed 29 March

2006.

The Chapman real party in interest is Purdue

Pharma L.P. Paper 9.

20a

Appendix B

Chapman has been accorded earlier constructive

reductions to practice based on the following

applications:

Application 11/093,626,

filed 30 March 2005,

now U.S. Patent 7,129,248,

issued 3] October 2006

Provisional application 60/620,072,

filed 18 October 2004

Provisional application 60/601,534,

filed 13 August 2004

Provisional application 60/557,492,

filed 30 March 2004

The interference—subject matter (2.e., count)

A process according to claim 1 of Casner Patent

7,153,966 B2 or a process according to claim 96 of

Chapman application 11/391,897.

Claim 1 of Casner reads:

A process for preparing oxycodone or an

oxycodone salt, comprising the steps of:

a) preparing a mixture comprising

oxycodone and a solvent, adjusting

the pH of the mixture to less than 6

2la

Appendix B

and heating the mixture at the

temperature of at least 55°C fora

period of at least 1 hour; and

subsequently

b) exposing the mixture to

hydrogenation reagents for a period

of at least 1 hour.

Claim 96 of Chapman reads:

A process for preparing oxycodone or an

oxycodone salt, which process comprises [the]

steps of:

(a) preparing a mixture of

oxycodone, solvent and an acid;

(b) incubating the mixture under

conditions suitable to promote

reaction of 8,14-dihydroxy-7,8-

dihydrocodeinone to 14-hydrox-

ycodeinone; and subsequently

hydrogenation reagents under

conditions sufficient for conversion of

14-hydroxycodeinone to oxycodone.

22a

Appendix B

The claims of the parties are:

Casner: 1-12

Chapman: 96-118

The claims that correspond to Count 1 are:

Casner: 1-12

Chapman: 96-118

The claims that do not correspond to Count 1 are:

Casner: None

Chapman: None

B. Findings of fact

The following findings of fact are believed to be

supported by a preponderance of the evidence. To the

extent that a finding of fact is a conclusion of law, it may

be treated as such. Additional findings as necessary may

appear in the Discussion portions of the opinion.

The rnvention

The invention relates to a method for making

oxycodone using a hydrogenation step. An object of the

method is the formation of oxycodone having low levels

(i.e., a few parts per million (ppm)) of o,B-unsaturated

23a

Appendix B

ketone impurities. Ex 2001, col. 1:65 to col. 2:9; Ex 2002,

page 1, 11 0002 & 0014. See also Ex 1028, 4 4.

Oxycodone is known to be useful in pharmaceutical

products as an analgesic. Ex 2001, col. 3:42-45; Ex 2002,

page 1, 1 0003.

Oxycodone has a ring structure.

The ring-numbering system used by the parties

appears to be the Chemical Abstracts numbering

system, an example of which appears in Chin, U.S.

Patent 6,177,567 B1, col. 2:15-20.

Specifically, oxycodone has the chemical structure

shown in Figure 1. Ex 1008, page 4, { 15 (ring positions

7,8 and 14 are hand-labeled).

24a

Appendix B

Figure 1—Structural formula of oxycodone

Important features of the structure are (1) a

hydroxyl group [—OH] attached at the 14-position and

(2) the absence of unsaturation |2z.e., a double bond

(—-CH=CH—)] between the 7- and 8-positions.

The principal a,f-unsaturated ketone impurity,

which the invention seeks to minimize, if not remove, is

14-hydroxycodeinone.

14-hydroxycodeinone has the chemical structure

shown in Figure 2. Ex 2001, col. 1:40 (formula on the

right); Ex 2002, page 070, Fig. 2 (ring positions 7, 8 and

14 hand-labeled).

eae

25a

Appendix B

Figure 2—Structural formula of 14-hydroxycodeinone

An important feature of the structure is the double

bond between the 7- and 8-positions.

The double bond results in an o,f-unsaturated

compound with o being the 7-position and {3 being the

8-position.

Oxycodone can be manufactured from a compound

known as “thebaine” by a known process disclosed in

U.S. Patent 6,090,943. Ex 2001, col. 1:31-38.

The involved Chapman application explains the

overall process in the following words. Ex 2002, page

006, {1 0013.

26a

Appendix B

During the oxidation of thebaine to give 14

hydroxycodeinone, several overoxidized products are

formed including 8,14-dihydroxy-7,8-dihydrocodeinone.

In the production of oxycodone free base from 14-

hydroxycodeinone, the 8,14-dihydroxy-7,8-dihydro-

codeinone is carried through the process. During

conversion of the oxycodone free base to oxycodone

hydrochloride, the impurity [i.e., 8,14-dihydroxy-7,8-

dihydrocodeinone| undergoes’ acid-catalyzed

dehydration and is converted into 14-hydroxycodeinone.

Thus, 14-hydroxycodeinone can be present in the final

oxycodone hydrochloride composition.

Thebaine has the structural formula shown in

‘

Figure 3.

CH,O

] 14 NCH,

CH,O

Figure 3—Structural formula of thebaine

27a

Appendix B

The structural formula of thebaine was copied from

U.S. Patent 6,090,943, col. 1:20, the patent mentioned

in the involved Casner patent. Ex 2001, col. 1:31-33.

By oxidation, Chapman means a reaction which

results in 14-hydroxycodeinone by (1) addition of a

hydroxy group (—OH) at the 14-position, (2) conversion

of the methoxy group [—OCII,] at the 6-position to a

keto group | =O], and (3) replacing the two double bonds

between the 6- and 7- and 8- and 14-positions with a

single double bond between the 7- and 8-positions.

Compare Figure 3 (thebaine) with Figure 2

(14-hydroxycodeinone) and see Ex 1028, page 5, 9 13.

By overoxidized, Chapman means a reaction which

results in (1) addition of a hydroxyl group (—OH) at both

the 8- and 14-positions along with (2) elimination of a

double bond between the 8-position and the 14-position

resulting in formation of 8,14-dihydroxy-7,8-

dihydrocodeinone.

8a,14-dihydroxy-7,8-dihydrocodeinone has the

structural formula shown in Figure 4 (ring positions 7,

8 and 14 and two methyl groups (—CH,) are hand-

labeled).

28a

Appendix B

ck,—O Oo

8a, 14-dih ydroxy-7,8-dihydrocodcinone

Figure 4-Structure of 8a,14-dihydroxy-7,8-

dihydrocodeinone

As shown in Figure 4, there is a hydroxyl group at

both the 8- and 14-positions and there is no double bond

between the 7- and 8-positions. The chemical structure

was reproduced from Ex 2002, page 070, Fig. 2.

Casner process

The Casner invention provides a process for

preparing oxycodone or an oxycodone salt having low

levels of impurities, comprising the steps of:

(a) preparing a mixture comprising oxycodone

and a solvent and adjusting the pH of the

mixture to less than 6; and subsequently

29a

Appendix B

(b) exposing the mixture to hydrogenation

reagents for a period of at least 1 hour. Ex

2001, col. 2:7-15.

According to Casner, the process is said to

surprisingly provide oxycodone with low levels of a,(-

unsaturated ketone impurities, 7.e., 14-hydro-

xycodeinone at Jess than 15 ppm. Ex 2001, col. 2:16-19.

Further according to Casner, in order to achieve low

levels of 14-hydroxycodeinone, the pH must be adjusted

by adding an acid before the hydrogenation step.

Ex 2001, col. 2:16-21.

More specifically, Casner discloses that suitably the

mixture is heated after the pH of the mixture is

adjusted, so that the process comprises the steps of:

(a) preparing a mixture comprising oxycodone

and a solvent, adjusting the pH of the mixture

to less than 6 and heating the mixture at the

temperature of at least 55° C. for a period of

at least 1 hour; and subsequently

(b) exposing the mixture to hydrogenation

reagents for a period of at least 1 hour. Ex

2001, col. 2:21-29.

The process is said to provide oxycodone with very

low levels of a,B-unsaturated ketone impurities, 7.e., 14-

hydroxycodeinone at less than 5 ppm.

30a

Appendix B

Chapman process

One object of Chapman is a process for reducing

the 14-hydroxycodeinone in an oxycodone hydrochloride

composition to an amount of less than about 5 ppm.

Ex 2002, pages 0006-0007, 1 0016.

In one embodiment, Chapman describes

hydrogenating a mixture of oxycodone and 14-

hydroxycodeinone to prepare a mixture having less than

5 ppm of 14-hydroxycodeinone. Ex 2002, page 008,

1 0023.

Example 3 describes one method of implementing

the Chapman invention. Ex 2002, pages 043-044,

11 0180-0187 |]

EXAMPLE 3

[0180] In Example 3, 27.83 g of oxycodone

free-base, water wet (24.57 g dry basis, 0.0779

mol, ca. 3000 ppm 14-hydroxycodeinonc), 39.8

g of deionized water, 81.9 g of isopropanol, 0.49

g 5% Pd/C [palladium on carbon] catalyst, 50%

water wet Johnson Matthey type 87L), and

conc. HC] [hydrochloric acid] (11.3 g, 0.117 mol,

1.50 equivalents based on 37.7% HCl assay)

were combined in a 500 ml Parr shaker bottle.

[0181] The mixture was placed under an

inert atmosphere and heated to 75° C. with

3la

Appendix B

shaking. The pressure in the bottle was

relieved, and the system was pressurized with

hydrogen (45 PSIG). The solution was held

under these conditions for 21.7 hours.

Analysis by HPLC [high performance liquid

chromatography] showed that the ratio of the

area of the 8,14-dihydroxy-7,8-dihydro-

codeinone peak to that of oxycodone was

reduced from 0.29% to 0.04% during this time.

[0182] The hydrogen pressure was vented

and the system was placed under an inert

atmosphere. In order to prevent further

dehydration of any residual &,14-dihydroxy-

7,8-dihydrocodeinone, the pH of the solution

was adjusted from 0.5 to 1.8 with 20.7 g NaOH

[sodium hydroxide] saturated isopropanol

(some solid sodium hydroxide was also

present).

[0183] The solution was re-heated to 75°

C. and then pressure filtered through a 0.2

um PTFE membrane filter housed in

heat-traced 47 mm SS filter holder into a

500 ml jacketed cylindrical reactor (condenser,

N2, mechanical stirrer, programmable

refrigerated recirculator). The Parr bottle

was rinsed with 8.6 g of deionized water, which

was added to the flask through the filter.

32a

Appendix B

[0184} Isopropanol (222.5 g) was added to

the solution in the flask and the resulting

slurry was heated to approximately 75° C. to

re-dissolve the solids. After reaching the

desired temperature, the solution was held for

two hours (to simulate typical processing

times). No 14-hydroxycodeinone was detected

inasample of the crystallization mixture after

this hold.

{0185] The circulator was set to cool from

80° C. to 0° C. over 8 hours. Approximately 24

hours after starting the cooling program, the

solids were collected by suction filtration and

washed three times with 95:5 isopropanol/

water (232.8 g total). The material was dried

as described in Example 1.

[0186] Analysis of the dried material

using the low 14-hydroxycodeinone method of

Example 4 below gave a result of 5 ppm of 14-

hydroxycodeinone.

[0187] Analysis of the dried material

using the method of Example 6 below gave a

result of < 5ppm of codeinone and 10 ppm of

14-hydroxycodeinone.

33a

Appendix B

Chapman original claim 33 describes the following

(Ex 2002, page 061):

A process for preparing an oxycodone

hydrochloride composition having a 14-

hydroxycodeinone level in an amount of less

than 25 ppm comprising reacting in a suitable

solvent an oxycodone base composition

having an amount of 8,14-dihydroxy-7,8-

dihydrocodeinone; with hydrochloric acid in an

amount greater than 1.0 molar equivalent as

compared to the oxycodone base composition

to promote the dehydration of the 8,14-

dihydroxy-7,8-dihydrocodeinone to 14-

hydroxycodeinone to form an oxycodone

hydrochloride composition having a

14-hydroxycodeinone level in an amount of

less than 25 ppm; the reacting step

being performed under reducing conditions

to promote the conversion of 14-

hydroxycodeinone to oxycodone.

Chapman original claim 38 describes the process of

claim 33 comprising hydrogenating the resultant

oxycodone hydrochloride composition having 14-

hydrocodeinone level in an amount of less than 25 ppm.

Ex 2002, page 062.

34a

Appendix B

Marketplace demands

What marketplace demands were distributors of

oxycodone facing in early 2004?

It appears that in the January 2004 time-frame, the

FDA [Food and Drug Administration] may have been

concerned about high levels of 14-hydroxycodeinone in

oxycodone approved for use in the United States.

The first hint we have of the DA's concern is

testimony by Dr. Steven W. Baldwin, a witness for

Chapman.

During cross-examination, Dr. Baldwin was asked

whether he had an understanding of why there was a

continuing need in the art to provide an oxycodone

hydrochloride composition with reduced amounts of 14-

hydroxycodeinone. Ex 1027, page 85:14-18.

According to Dr. Baldwin, the FDA wanted a

commercial product that had lower amounts of the 14-

hydroxycodeinone. Ex 1027, page 85:21-23.

Further cross-examination revealed that Dr. Baldwin

gained his knowledge about FDA concerns from a

conversation with Dr. Samuel 8S. Woodley, Esq., backup

counsel for Chapman. Ex 1027, page &86:4-6.

Dr. Baldwin testified that Dr. Woodley had told

Dr. Baldwin that the FDA told Purdue that it needed to

decreased the amount of 14-hydroxycodeinone from its

35a

Appendix B

product and that was the driving force behind finding a

way to do that. Ex 1027, page 86:14-22.

The record also contains a Citizen Petition filed by

Purdue Pharma L.P with the FDA. Ex 2034.

The Purdue Citizen Petition requests that the FDA

adopt, announce and implement a standard for the

acceptable level of 14-hydroxycodeinone impurity in

oxycodone HC! active ingredient approved by the FDA

in use for drug products. Ex 2034, page 1 (Action

Requested).

At some point, Purdue sought approval from the

FDA to use oxycodone HCl active ingredient. Fx 2034,

page 1 (Statement of Grounds).

According to Purdue, the FDA approval was

contingent on successfully addressing the presence of

14-hydrocodeinone (an a,f-unsaturated ketone)

impurity common to all commercial supplies of oxycodone

HCl active ingredient. Id.

Specifically, in January of 2004, the FDA instructed

Purdue to (1) provide extensive safety qualification data

or (2) reduce the 14-hydrocodeinone level to not more

than 10 parts per million (ppm). Ex 2034, page 002, first

paragraph.

The representations in the Citizen Petition are

consistent with statements in the Casner patent and the

(Chapman application.

36a

Appendix B

Casner says that “[rjecently there has been a

concern about the presence of «,f-unsaturated ketone

impurities in pharmaceuticals and the Casner invention

seeks to offer oxycodone having preferably below 10 ppm

14-hydroxcodeinone. Ex 2001, page 002, col. 1:65 through

col. 2:6.

Likewise Chapman reveals that there is a need in

the art to provide an oxycodone hydrochloride

composition that contains reduced amounts of

14-hydroxycodeinone as compared to compositions

known in the art.

To the extent that the need was a result of FDA

directive in January of 2004 (Ex 2034, paragraph

bridging pages 001-002), we note that on 30 March 2004,

Purdue filed a provisional application containing

Example 3 (reproduced above) describing a

14-hydrocodeinone content of 5 ppm. Ex 2008, page 035-

36 (see last sentence of Example 3 on page 036).

On 23 September 2004, Casner filed a British patent

application describing a method for making oxycodone

with less than 5 ppm of 14-hydrocodeinone.

Of course it is possible that both Casner and

Chapman were working on the known problem before

the FDA directive in January of 2004.

However, based on the evidence—including the

testimony, documents and statements in the

specifications—we find that there was a commercial

37a

Appendix B

need to reduce the amount of 14-hydrocodeine in

oxycodone around the time Casner and Chapman made

their inventions.

Both Casner and Chapman represent that they

solved the commercial need. Ex 2002, pages 006-007,

{1 0016; Ex 2001, page 002, col. 2:7-32.

Level of skill in the art

Dr. Gilbert Stork, a professor emeritus at Columbia

University, testified on behalf of Casner. Ex 2004, page

4,115.

Dr. Steven W. Baldwin, a professor at Duke

University, testified on behalf of Chapman. Ex 1008,

page 1,1 2.

Both Dr. Stork and Dr. Baldwin have been awarded

a Ph.D. in Chemistry and have worked extensively in

the field of synthetic organic chemistry.

The invention involved in this interference falls

within the scientific field of synthetic organic chemistry.

Both Dr. Stork and Dr. Baldwin are qualified as

experts in the field of synthetic organic chernistry.

Accordingly, we find that both Dr. Stork and

Dr. Baldwin are competent to give opinions in the field

synthetic organic chemistry, the subject matter involved

in this interference.

38a

Appendix B

Both Dr. Stork and Dr. Baldwin testified on level of

skill of a hypothetical person skilled in the art involved

in this interference.

As will become apparent, Dr. Stork's and

Dr. Baldwin's views on the level of skill in the art went

through a metamorphosis from (1) an early view for a

need for a B.S. degree or equivalent training to (2) to

an ultimate view for a need for a Ph.D. degree.

Since the testimony regarding the level of skill in

the art was based on an evolving understanding of a

hypothetical legal personality, we do not fault the

metamorphosis in any respect.

Instead we commend the flexible manner in which

both Dr. Stork and Dr. Baldwin adjusted their views in

reaching their ultimate positions for the need for a Ph.D.

According to his direct declaration testimony,

Dr. Stork expressed an opinion that a "skilled person"

would have at least the equivalent of a Bachelor of

Science degree in chemistry and will have had a least

one year of laboratory experience either in academia or

in industry. Ex 2004, page 008, 11 26.

On cross-examination when asked the basis for his

opinion, Dr. Stork candidly acknowledged that that is

what counsel for Casner had told him. Ex 2025,

transcript page 18:22 through page 19:19.

39a

Appendix B

Dr. Stork later clarified that the skilled person would

be capable of following directions of a person working

in the same laboratory, preferably in a pharmaceutical

house. Ex 2025, transcript page 20:4-8; Ex 2025,

transcript page 58:9-15.

Dr. Stork further clarified that the skilled person

probably would have a Ph.D. Ex 2025, transcript page

24:20-24.

In his direct declaration testimony, Dr. Baldwin did

not testify extensively as to the qualifications, as such,

of a person having ordinary skill in the art.

However, Dr. Baldwin initially expressed an opinion

that the steps involved in the “count” “involve only

routine techniques that students with an undergraduate

degree in chemistry or an equivalent level of education

and training are able to perform. Ex 1008, page 27-28,

1 95. See also Ex 1008, page 22, 1 75.

On cross-examination (agreeing gencrally with

Dr. Stork), Dr. Baldwin felt that a person with an

undergraduate degree and some experience, working

in a pharmaceutical company, would be able to perform

the manipulations involved with direction from their

supervisor, who of course, would have more training.

See generally Ex 1027, page 72:25 through page 76:25.

Dr. Baldwin noted that (1) a supervisor typically

would have at least a Ph.D. in synthetic organic

chemistry and (2) it is the level of the supervisor—not a

40a

Appendix B

technician —who is skilled in the synthetic chemistry art.

Ix 1028, page 3, 11 9-10.

In general, we have no trouble agreeing with Dr.

Stork and Dr. Baldwin that a person of ordinary skill in

this art would have been awarded a Ph.D. degree and

would have experience in synthetic organic chemistry.

The person would know how to research the

scientific literature to gain knowledge concerning any

particular synthetic chemical reaction.

The person would know that experimental work may

be necessary to optimize result oriented variables.

Scope and content of the prior art

Oxycodone (Figure 1) can be made from thebaine

(Figure 38).

When oxycodone is made from thebaine, a 14-

hydroxycodeinone (Figure 2) by-product is produced.

As earlier noted, the presence of 14-

hydroxycodeinone in commercially marketed oxycodone

is not desirable.

Chapman, but not Casner, states in its specification

that in addition to 14-hydroxycodeinone, another

compound known as 8a,14-dihydroxy-7,8-dihydro-

codeinone (Figure 4) is also produced when making

oxycodone from thebaine. Ex 2002, page 006, 1) 0013.

4la

Appendix B

Specifically, Chapman revealed in the Background

of the Invention in its 2004 specification the following

(Ex 2008, page 002, third paragraph—bracketed matter

added):

During the oxidation of thebaine to give 14-

hydroxycodeinone [Figure 2], several

overoxidized products are formed including

[the impurity] 8,14-dihydroxy-7,8-

dihydrocodeinone [Figure 4]. In the

production of oxycodone free base from the

14 hydroxycodeinone, the 8,14-dihydroxy-7,8-

dihydrocodeinone is carried through the

process. During conversion of the

oxycodone free base to oxycodone

hydrochloride, the impurity undergoes acid-

catalyzed dehydration and is converted into

14-hydro|xy]-codeinone. Thus, 14-

hydroxycodeinone is present in the final

oxycodone composition.

The parties are in disagreement whether the

Chapman Background of the Invention is prior art.

Casner says yes and Chapman says no.

Here is what Chapman has to say (Chapman

Opposition 9-10, Paper 48, page 1—citations to the

record omitted and bracketed matter added):

Chapman's invention was his |there are

co-inventors] discovery of the’source of that

42a

Appendix B

14-hydroxycodeinone and * * * how to remove

it. Chapman discovered that when the * * *

thebaine is converted by H,O, (hydrogen

peroxide] oxidation to the originally desired

intermediate, 14-hydroxycodeinone, a

contaminating by-product, 8,14-dihydroxy-7,8-

dihydrocodeinone, is also formed. This

contaminating 8,14-by-product” is unreacted

when the original 14-hydroxycodeinone is

hydrogenated to oxycodone. Rather, the 8,14-

by-product is converted to new 14-

hydroxycodeinone, when the oxycodone is

reacted with hydrochloric acid to form a salt.

The new 14-hydroxycodeinone is

contaminating 14-hydroxycodeinone that

Chapman's invention eliminates. No one

before Chapman knew that contaminating

8,14-by-product was being formed and

converted to new 14-hydroxycodeinone in the

production of oxycodone HCL. Chapman's

discovery lead to his method to convert the

new 14-hydroxycodeinone to oxycodone using

two well-known chemical reactions: [1] the acid

catalyzed dehydration of (}-hydroxyl carbony!

fi.e., the 8,14-by-product (see Ex 2028, 1] 28)|

and |2| hydrogenation.

Casner's reply is that the prior art reveals that the

information contained in the Background of the

Invention was known-—-whether or not Chapman

“independently” discovered that information. Casner

Reply 9-10, Paper 57, page 1.

43a

Appendix B

Dr. Stork did a search on “SciFinder” and found

Proksa, 10-Hydroxythebaine, Arch. Pharm. Med.

Chem. 369-70 (1999). Ex 2039, pages 12-13, 91 28.

As Dr. Stork explains, in 1999 Proksa described that

the oxidation of thebaine with H,0, {hydrogen peroxide |

in the presence of a strong acid resulted in the formation

of 14-hydroxycodeinone [Proksa Structure 2] as well

other compounds including a compound identified as

Proksa Structure 5. /d.

A person having ordinary skill in the art would have

understood in 1999, and would understand today, that

the Proksa compound having Structure 5 is &,14-

dihydroxy-7,8-dihydrocodeinone. /d.

It may be true that Chapman discovered

independently from Proksa that when thebaine is

converted by H,O, [hydrogen peroxide] oxidation to the

desired intermediate, 14-hydroxycodeinone, a

contaminating by-product, 8,14-dihydroxy-7,8-

dihydrocodeinone, is also formed.

However, Chapman's discovery that 8,14-dihydroxy-

7,8-dihydrocodeinone is also formed was known in the

prior art.

Whatis the significance of this prior art knowledge?

One skilled in the art would have understood—based

on Proksa—that when step (a) of Chapman claim 96 calls

for preparing a mixture of (i) oxycodone, (11) solvent and

44a

Appendix B

(iii) an acid what is being prepared is a mixture which

comprises (1) oxycodone, (2) 14-hydroxycodeinone, (3)

8,14-dihydroxy-7,8-dihydrocodeinone, (4) a solvent and

(5) an acid.

One skilled in the art also would have known that

the 14-hydroxycodeinone is “removed” (via conversion

to oxycodone) through a hydrogenation process. See (1)

Ex 2016, Chiu, col. 11:51-60, Example 5 (col. 15) and col.

16:33-34; (2) Ex 2002, page 006, {1 0012 referring to a

scientific article by Krabnig; and (3) Ex 1028, page 21,

1 60 [testimony of Dr. Baldwin]

Would one skilled in the art also have known how to

“remove” the 8,14-dihydroxy-7,8-dihydrocodeinone?

Referring to Weiss, Derivatives of Morphine. IT.

Demethylation of 14-hydroxycodeinone, 14-Hydroxy-

morphincve and 8,14-dihydroxydihydro-morphinone,

22 J. Org. Chem. 1505-08 (1957) (Ex 2027), Dr. Stork

testified that Weiss reveals that treatment with dilute

HCl (1:1) in a boiling water bath for 20 minutes converted

8,14-dihydroxy-7,8-dihydrocodeinone into a compound

having structure III. Ex 2081, page 010,

1 30; Ex 2027, page 1508 (sentence bridging cols. 1

and 2).

Dr. Stork further testified that one skilled in the

art (v.e., a synthetic organic chemist) would have

understood that the compound having structure I{]

(see page 1507 structure III which results when R =

CH.) is 14-hydroxycodcinone. Ex 2031, page 010, 1 30.

45a

Appendix B

Dr. Stork's testimony is consistent with his cross-

examination where he stated that the “reaction,

changing 8,14-dihydroxy[-7,8-dihydrocodeinone] into 14-

hydro-codeinone, did exist in the literature before 2003

** *” Ex 2025, transcript page 30:7-21.

On cross-examination, Dr. Stork also testified about

other aspects of Weiss, but not about treatment of 8, 14-

dibydroxy-7,8-dihydrocodeinone being converted to 14-

hydroxy-codeinone. Ex 2025, transcript page 202:4

through transcript page 204:23.

Referring to Iijima, The Oxidation of Thebaine with

m-Chloroperbenzoic Acid Studies in the (+)-

Morphinan Series. IIT, 60 Helvetica Chimica Acta, 2135-

37 (1977) (Ex 2028), Dr. Stork observes that lijima

reports obtaining a compound having structure 5. Ex

2031, page 010, 1 33.

Dr. Stork testified that the compound having

structure 5 (Ex 2028, page 2) would have been

understood to correspond to 8,14-dihydroxy-7,8-

dihydrocodeinone. Ex 2081, page 010, 11 33, last

sentence.

Dr. Stork is of the opinion that if 8,14-

dihydroxydihydrothebaine |not 8,14-dihydroxy, 7,8-

dihydrocodeinone] is heated to 80° C. for 15 minutes in

the presence of 5% hydrochloric acid [HCl], a stable

(because it has a melting point) hydrochloride salt of

8,14-dihydroxy-7,8-dihydrocodeinone may exist.

Ex 2031, pages 010-011, 111 34-35.

46a

Appendix B

Referring to Tada, Ketalisation of «,B-Unsaturated

Ketones, Part I 3-Methoxy-N-methylmorphinan

Derivatives and 14-Hydroxycodeinone, 22 Tetrahedron

Letter, 1805-09 (1969) (Ex 2029), Dr. Stork notes that

Compound 11 was obtained when Compound 7 was

treated with 6N HCl [hydrochloric acid] at 100° C. for 3

hours. Ex 2031, page 011, 11 38.

Compound 7 would be understood by one skilled in

the art to be 14-hydroxycodeinone. Ex 2031, page 011,

1 39.

Compound 11 would have been understood by one

skilled in the art to be 8,14-dihydroxy-7,8-

dihydrocodeinone. /d.

Dr. Stork's point seems to be that while some

conditions result in 8,14-dihydroxy-7,8-dihydro-

codeinone being converted to 14-dihydroxycodeinone

(e.g., Weiss), other conditions result in just the opposite

(e.g., Tada). Ex 2031, page 012, If 41.

Dr. Stork expressed the opinion that a person having

ordinary skill in the art would understand that the

pH, the temperature, and reaction time can each affect

the compound or compounds produced from the

combination of 8,14-dihydroxy-7,8-dihydrocodeinone and

hydrochlorie acid [HCl] in a solvent. Ex 2031, page 011,

1 37.

Weiss and lijima support Dr. Stork's opinion.

47a

Appendix B

Based on Tada, Dr. Stork expressed the view that

greater specificity as to the particular reaction

conditions, including the pH, time and temperature, is

necessary to practice the 8,14-dihydroxy-7,8-

dihydrocodeinone to 14-hydroxycodeinone reaction

recited in what Dr. Stork refers to as Element IV of

Chapman's claim 96. Ex 2031, page 012, 141.

Element IV is “incubating the mixture under

conditions suitable to promote reaction of 8,1 4-dihydroxy-

7,8-dihydrocodeinone to 14-hydro-xycodeinone.” See Paper

48, Appendix 3.

Dr. Baldwin agrees with Dr. Stork that a person

having ordinary skill in the art (e.g., a person with a

Ph.D. and specializing in synthetic organic chemistry)

would understand that the pH, the temperature, and

reaction time can each affect the compound or

compounds produced from the combination of 8,14-

dihydroxy-7,8-dihydrocodeinone and hydrochloric acid

{HCl} in a solvent.

Dr. Baldwin expressed the view that a person of

ordinary skill would have no trouble identifying

conditions suitable to promote reaction of

8,14-dihydroxy-7,8-dihydrocodeinone to 14-hydro-

xycodeinone. Ex 1028, page 20, 11 55.

Referring to a standard text book (Ex 1029) and

testimony by Dr. Stork, Dr. Baldwin explained that it

was known that decreasing the pH of a reaction mixture

promotes and accelerates dehydration. Ex 1028, page

20, 156.

48a

Appendix B

Referring to the same standard text book (Ex 1029)

and testimony of Dr. Stork, Dr. Baldwin further

explained that it was known that heat also promotes

acid catalyzed dehydration reactions, of which

conversion of 8,14-dihydroxy-7,8-dihydrocodeinone to

)4-hydrocodeine is one example. Ex 1028, page 20, 1 57.

Dr. Baldwin still further explained that

hydrogenation of 14-hydroxycodeinone to oxycodone was

a traditional step in the synthesis of oxycodone before

March 2004. Ex 1028, page 20, 1 59.

Differences

The principal differences between the "prior art" and

the subject matter claims by Casner and Chapman is

that no one reference describes all of the claimed process

steps.

On the other hand each process step is generally

known.

Furthermore, both Casner and Chapman use each

step for its known purpose to achieve what one skilled

in the art would have expected.

Level of skill in the art

As our findings make clear, both Dr. Stork initially

expressed an opinion that a person skilled in the art

had a relatively low skill level, e.g., a B.S. degree and

some lab experience (a technician in the lab).

49a

Appendix B

Dr. Stork's initial opinion was based on what he was

told by counsel.

Dr. Baldwin had a similar initial opinion.

However, as they gained insight during cross-

examination, both came to the view that the skilled

person would have had a Ph.D. and would have had

knowledge in synthetic organic chemistry.

What happened in this case is that while an initial

“low” level was suggested by Dr. Stork and Dr. Baldwin,

both came to an ultimate view that the skill level was

quite “high.”

In DyStar Textilfarben GmbH. v. C.H. Patrick Co.,

464 F.3d 1356, 1862-63 (Fed. Cir. 2006), the level of skill

in the art was disputed.

The Federal Circuit held that the person of ordinary

skill was not a “dyer” (as urged by one party) but a

“person designing an optimal dyeing process” (as urged

by the other party). 464 F.3d at 1363.

The person skilled in the art in the case before is

not the “technician” in the lab taking direction from a

supervisor; rather it is a synthetic organic chemist

with considerable and sophisticated knowledge of

(1) chemical reactions relevant to the field, (2) how to

search the relevant literature and (3) how to accomplish

complicated organic chemistry reactions in the relevant

field.

50a

Appendix B

To the extent that there is any lingering view by

either party that the person is a “technician” with a B.S.

degree in chemistry, we would point out that such a view

is inconsistent with prior art called to our attention by

Dr. Stork and Dr. Baldwin.

We do not think that prior art can be ignored in the

case before us anymore than the Brochet, Wimmer, and

Chaumat prior art was implicitly ignored by the jury in

DyStar. 464 F.3d at 1363.

Resolution of credibility

Dr. Stork and Dr. Baldwin, while agreeing on many

points, disagree on significant points relevant to

resolution of the factual and legal issues before us.

Based on a consideration of their direct testimony

and cross-examination, as a whole, and because we fee]

that Dr. Baldwin's explanations are more persuasive and

faithful to the content of the patent and application

before us, as well as the prior art, we credit the testimony

of Dr. Baldwin over that of Dr. Stork to the extent that

their testimony is conflicting.

It is manifest that Dr. Baldwin has high respect for

Dr. Stork (“professionally he's first rate, he's terrific and

personally he's a great guy, very nice, very nice fellow”)

and that Dr. Stork is qualified to offer opinions in the

field of synthetic organic chemistry. Ex 1027, page 15:5

through page 17:11.

Sla

Appendix B

It is also manifest that Dr. Stork has a high regard

for Dr. Baldwin. Ex 2025, transcript page 208:8-12.

We wish to make clear that in making our credibility

findings that we are confident that both Dr. Stork and

Dr. Kaldwin have candidly stated their respective

opinions.

In our experience it is not unusual for highly

qualified scientists to disagree on a point, particularly

when the point involves application of what Dr. Stork

legitimately characterized “legalese” (e.g., the definition

of a person having ordinary skill in the art). Ex 2025,

transcript page 98:10-13 (“my knowledge of legalese was

[understandably] not up to some of them”).

Interference-in-fact

Casner moves for entry of a judgment of no

interference-in-fact. Paper 28.

Casner does not deny that the subject matter of

Casner claim 1 anticipates (35 U.S.C. § 102) the subject

matter of Chapman claim 96.

Casner maintains, however, that the subject matter

of Chapman claim 96 does not anticipate or render

obvious (35 U.S.C. § 103) the subject matter of Casner

claim 1.

The differences between the subject matter of

Casner claim | and the subject matter of Chapman claim

96 are manifest from Appendix 3 of Casner Motion 1.

52a

Appendix B

APPENDIX 3

COMPARISON OF CASNER CLAIM | AND CHAPMAN CLAIM 9%

ChartA

Element

Casner Claim 1

Chapman Claim 96

A process for preparing oxycodone or

an oxycodone salt, comprising the

A process for preparing oxycodone or an

oxycodone sah, which process comprises

steps of. Steps of.

i (a) preparing a mixture comprising | (a) preparing a mixture of oxycodune,

oxycodone and a solvent, solvent,

Til =| adjusting the pH of the mixture to and an acid

less than 6,

IV and heating the mixture (b) incubsting the mixture under condi iuns

suitable (o promote reaction of 8, 14-

dihydroxy-7, 8-dihydrocodcinone to |4-

hydroxycodeinone;

Vv at the temperature of at least $5°C (Element not present}

vi for a period of at least | hour; [Element not present]

VU | and subsequent ly (b) exposing the and subsequently (c) exposing the mixture

mixture (o hydrogenation reagents to hydrogenation reagents under conditions

sufficrent for converswn of |4-

hydroxycodeinone to oxycodone.

VILE | for a period of at least | hour [Element not present]

Elements I and Il in Casner Appendix 3 are present

in both Casner claim 1 and Chapman claim 96.

53a

Appendix B

Element III differs in that Casner adjusts the pH

to less than 6 while Chapman adds an “acid” to the

mixture of oxycodone and solvent.

Casner discloses that the pH is suitably adjusted

by addition of a strong acid, such as concentrated

hydrochloric acid, preferably at least one equivalent.

The pH is to be adjusted to below 6 and can be adjusted

to as low as l.

Nothing critical is set out in Casner revealing that

use of a pH higher than 6, but lower than 7, will not

achieve (albeit perhaps inefficiently) the result sought

be Casner. Ex 2001, page 002, col. 2:52-57,

The Casner patent does not explain why the pH has

to be lower than 6.

Chapman Example 3 describes mixing inter alia

oxycodone free-base and 1.50 equivalents of HC]

(hydrochloric acid).

Dr. Baldwin agrees one cannot rigorously calculate

the precise pH of the mixture described in Chapman

Example 3.

Nevertheless we find convincing, Dr. Baldwin

explanation why the pH in Chapman Example 3 would

probably be in the 1-2 range.

54a

Appendix B

As Dr. Baldwin notes, there are 1.5 equivalents of

HCl with no apparent base present to neutralize the

acid effect of adding HCI. Ex 1027, page 98:10 through

page 100:11.

Based on Dr. Baldwin's testimony, one skilled in the

art would recognize that the pH in the first step of

Example 3 is probably in the 1-2 range.

In any event, it is manifest that sufficient HC] has

to be added to achieve a pH of less than 7 if one skilled

in the art seeks to achieve Chapman’s objective of

obtaining an HC] salt of oxycodone.

Dr. Stork's testimony is that the pH would almost

certainly be below 7 and depending on concentration of

the acid, could be below 6. Ex 2004, page 010, 4] 35;

Kix 2025, transcript page 120:21 through page 121:13.

Dr. Stork apparently was not asked to explicitly

comment on the presence of 1.5 equivalents of acid.

Incubation v. heating

Casner maintains that ‘incubating” (used in

Chapman claim 96) and “heating” (used in Casner claim

1) are not the same thing.

Dr. Stork says “incubating” is not a term commonly

used in the field of synthetic organic chemistry. Ex 2004,

page 010, 11 39.

55a

Appendix B

Dr. Stork goes on to say that “incubating” means

maintaining a temperature and does not necessarily

include heating the material to be incubated to that

temperature. Ex 2004, page 011, 9% 42.

Dr. Stork says that Chapman’s use of the term

“incubating” does not permit one skilled in the art to

know the meets and bounds of Chapman claim 96.

Ex 2004, page 011, 9 44.

Dr. Stork undertook no convincing analysis of the

Chapman specification to see if it might shed some light

on his understanding of “incubating.”

Dr. Baldwin acknowledged that he typically does not

use the terms “incubation” or “incubating” in his

writings. Ex 1027, page 44:16 through page 45:2.

Nevertheless, Dr. Baldwin, referring to the

Chapman specification, had no difficulty understanding

that “incubating” was to be conducted to achieve a

result set out in the Chapman specification. Ex 1008,

1 31-35.

As earlier mentioned, we have credited the

testimony of Dr. Baldwin over that of Dr. Stork.

Dr. Baldwin's reference to and analysis of the

Chapman specification and Dr. Stork’s absence of a

similar analysis is an example of why generally we credit

Dr. Baldwin's testimony over that of Dr. Stork.

Sha

Appendix B

Example 3 describes mixing ingredients and heating

to 75° C. with shaking. Ex 2002, page 043, 110181.

Dr. Baldwin's analysis is consistent with Chapman

Example 3.

In the context of the invention described by

Chapman, we have no difficulty finding that “incubating”

means maintaining a temperature to achieve the result

set out in Chapman claim 96: promoting a stated

reaction.

It seems rather apparent to us that, given the

testimony and the nature of the Chapman invention, an

incubating temperature is above room temperature that

one has to “heat” before one can “incubate.”

Temperature of 55° C for at least 1 hour

As Appendix 3, supra, reveals, Elements V and VI

are not recited in involved Chapman claim 96.

Casner claim | requires that the mixture of Element

II be heated to at least 55°C for a period of at least |

hour.

Chapman claim 96 has no temperature or time period

requirement.

Casner, of course, maintains that since Chapman

claim 96 does not have the temperature and time

limitation, the subject matter of Chapman claim 96

S7a

Appendix B

cannot render obvious the subject matter of Casner

claim 1.

Step (b) of Chapman claim 96 says, however, that

the “incubating” must occur “under conditions suitable”

to promote a stated reaction.

Dr. Stork testified that “promote” has a variety of

meanings. Ex 2004, page 011, {1 47.

On cross-examination, however, Dr. Stork

acknowledged that an individual with a Ph.D. would

know where to search the prior art literature to find

the conditions necessary to accomplish the stated

objective of Chapman's “incubating.” Ex 2025,

transcript page 30:6-21.

Dr. Baldwin recognized that the conditions had to

be suitable to accomplish a stated objective. Ex 1008,

1 33-35.

On cross-examination, Dr. Baldwin was asked to

elaborate on his views. Ex 1027, pages 101-110.

In particular, Dr. Baldwin discussed why the data in

Chapman Example 8 describes a reported reduction of

8,14 dihydroxy-7,8-dihydrocodeinone from 0.29% to

0.04%. Ex 2002, page 043, 1 0181 and Ex 1027, page

103:25 through page 104:24.

Based on Dr. Baldwin's testimony, we find that the

temperature and time conditions are result oriented

58a

Appendix B

variables which one skilled in the art (someone with a

Ph.D. with experience in synthetic organic chemistry)

would be able to determine through routine

experimentation.

Nothing in the Casner specification reveals why the

claimed temperature and time period are critical,

provided of course that the desired reaction takes place.

Hydrogenation for at least 1 hour

Casner Appendix reveals that Casner claim 1

requires hydrogenation for at least 1 hour while

Chapman claim 96 is silent about the time needed for

hydrogenation. See Element VIII.

Casner also notes that in Element VII Chapman

uses the “under conditions sufficient” language.

Dr. Stork testified that “conditions sufficient” has

to take into account various reaction parameters,

including temperature and pH, as well as time. Ex 2004,

page 015, 9155.

Casner claim 1 does not mention a hydrogenation

temperature or the pII under which hydrogenation

takes place.

Dr. Baldwin testified that hydrogenation is a term

used by chemists and that a typical hydrogenation

reaction is used to convert a double bond into a single

bond consistent with the following general reaction

scheme. Fx 1008, 11 37-38.

59a

Appendix B

H oH

: Catalyst fh Mn, | | nll

4 \

Hydrogenation reactions are fundamental to

chemistry and are routinely taught in university

curricula. Ex 1028, page 6, 197 15-16.

Dr. Baldwin testified about the conditions needed

to accomplish hydrogenation.

As the reaction scheme reveals, hydrogen (e.g., H,)

is needed. Ex 1008, 1 39.

A catalyst is also needed. Ex 1008, {1 40.

Dr. Baldwin testified that the Chapman application

teaches the use of hydrogen and a catalyst. Ex 1008,

1 44.

On cross-examinaticn, Dr. Baldwin elaborated.

Ex 1027, page 66:21 through page 68:6.

Chapman Example 8 confirms the need for

hydrogen (“pressurized with hydrogen”) and a catalyst

(“0.49 g 5% Pd/C catalyst”). Ex 2002, page 043, 11 0180-

0181.

60a

Appendix B

The “subsequently” limitation

Casner notes that Casner claim 1 requires

“hydrogenation” to take place “subsequently” to Casner

step (b), whereas Chapman claim 96 does not mention

“subsequently.”

Dr. Baldwin testified that he understood

“subsequently” to mean that hydrogenation step (c) has

to occur after step (b) is performed. Ex 1008, {| 47.

On cross-examination, Dr. Baldwin further testified

that: “Until the dehydration [step (b)] has occurred

hydrogenation will have no impact, and so for this whole

process to work, we have to generate this double bond

* * *” 1.e., the double bond between the 7- and 8-

position of 14-dihydrocodeinone.

Once the “double bond is generated, then we can

hydrogenate it.” Ex 1027, page 58:18 through page 59:2.

Dr. Stork said essentially the same thing. Ex 2025,

transcript page 86:22 through page 87:21.

In the context of this invention, the broadest

reasonable construction of “subsequently” includes, but

is not limited to, [1] completing step (b) by making all

the 14-hydrocodeinone you are going to make, [2]

stopping the making of 14-hydrocodeinone, and then [3]

starting hydrogenating all of it to remove the double

bond in 14-hydrocodeinone.

6la

Appendix B

Rather, it means that hydrogenation must take place

after dehydration of 8,14-dihydroxy-7,8-dihydro-

codeinone to 14-hydroxycodeinone otherwise their

would be no "dehydration" 14-hydroxycodeinone product

to hydrogenate.

Ilowever, even if step (b) has to be completed before

starting step (c), and assuming Chapman does not

explicitly describe a stop/start process, one skilled in

the art would find the difference insignificant because

as Dr. Baldwin points out until you have 14-

hydrocodeinone to hydrogenate, there is no reason to

hydrogenate.

C. Casner Motions 9-10-obviousness

Legal principles

The legal principles application to the cbviousness

issues before us are straightforward.

A claimed invention is not patentable if the subject

matter of the claimed invention would have been obvious

to a person having ordinary skill in the art. 35 U.S.C.

§ 103(a); ASR Int'l Co. v. Teleflivx Inc., 1278S. Ct. 1727

(2007); Graham v. John Deere Co., 383 U.S. 1 (1966).

Facts relevant to a determination of obviousness

include (1) the scope and content of the prior art, (2)

any differences between the claimed invention and the

prior art, (3) the level of skill in the art and (4) any

62a

Appendix B

relevant objective evidence of obviousness or non-

obviousness. KSR, 127 S. Ct. at 1734; 1389, Graham,

383 U.S. at 17-18.

A person having ordinary skill in the art uses known

elements and process steps for their intended purpose.

Anderson's-Black Rock, Inc. v. Pavement Salvage Co..,

396 U.S. 57 (1969) (radiant-heat burner used for its

intended purpose in combination with a spreader and a

tamper and screed); Sukraida v. AG Pro, Inc., 425 U.S.

273, 282 (1976) (the involved patent simply arranges old

elements with each performing the same function it had

been known to perform); Dunbar v. Myers, 4 Otto (94

U.S.) 187, 195 (1876) (ordinary mechanics know how to

use bolts, rivets and screws and it is obvious that any

one knowing how to use such devices would know how

to arrange a deflecting plate at one side of a circular

saw which had such a device properly arranged on the

other side); DyStar Textilfarben GmbH. v. C.H. Patrick

Co., 464 F.3d 1356, 1862-63 (Fed. Cir. 2006).

Chapman claim 96

Oxycodone has been made from thebaine. Ex 2002,

page 005, 1 0006; Ex 2001, page 002, col. 1:65 through

col. 2:6.

The FDA and the oxycodone industry recognized

that there was a need to eliminate impurities in

oxycodone.

63a

Appendix B

Those skilled in the art recognized that one known

impurity in oxycodone made from thebaine was

14-hydroxycodeinone.

The Chapman background of the invention states,

and Proksa confirms, that another known impurity was

8,14-dihydroxy-7,8-dihydrocodeinone. In view of Proksa,

we need not resolve whether or not the Chapman

background of the invention is prior art.

The 14-hydroxycodeinone impurity can be removed

from oxycodone made from thebaine by a well-known

hydrogenation process. Ex 2016, page 007, col. 11:46-

60.

The hydrogenation process removes the double

bond between the 7- and 8-positions.

However, since 8,14-dihydroxy-7,8-dihydrocodeinone

impurity does not have a double bond between the

7- and 8-positions, one skilled in the art would have

recognized that hydrogenation would not eliminate or

reduce the amount of that impurity in oxycodone.

One skilled in the art, a synthetic organic chemist

having at least a Ph.D. degree, would have known based

on Weiss that appropriate treatment of &,14-dihydroxy-

7,8-dihydrocodeinone with hydrochloric acid would

convert the 8,14-dihydroxy-7,8-dihydrocodeinone to

14-hydroxycodeinone.

64a

Appendix B

We will divert from a straightforward analysis at this

point to address a concern raised by Dr. Stork, namely,

that of making 14-hydroxycodeinone from 8,14-

dihydroxy-7,8-dihydrocodeinone.

Based on lijima and Tada, Dr. Stork expressed an

opinion that the art is not predictable, that 8,14-

dihydroxy-7,8-dihydrocodeinone may be a stable

compound (Lijima), and that there are conditions under

which treatment 14-hydroxycodeinone results in 8,14-

dihydroxy-7,8-dihydrocodeinone (Tada).

We do not share Dr. Stork’s concern, because one

skilled in this art seeking to convert 8,14-dihydroxy-7,8-

dihydrocodeinone to 14-hydrocodeinone would not use

process conditions which do not accomplish the desired

result.

Accordingly, one skilled in the art—while perhaps

advised to be careful by lijima and Tada—is going to

use process conditions which achieve the desired result,

those being shown by Weiss.

We agree instead with Dr. Baldwin's testimony that

one skilled in the art would be able to identify the

conditions suitable to promote reaction of 8,14-

dihydroxy-7,8-dihydrocodeinone to 14-hydrocodeinone.

Ix 1028, page 20, {I 55.

The facts in this case confirm the observation in

KASH that “la] person of ordinary skill is a person of

ordinary creativity, not automaton.” 127 S. Ct. at 1742.

65a

Appendix B

The person of ordinary skill in the art in this case is a

highly sophisticated synthetic organic chemist who

known how to search the literature and implement

processes to achieve particular reactions. To that we

would add that the person skilled in the art works in a

highly competitive pharmaceutical industry. One skilled

in the art in this case would have had a very high

incentive to solve the problem identified by the FDA.

The literature tells one skilled in the art how to do so.

Back to the analysis, one skilled in the art would

have known that once the 8,14-dihydroxy-7,8-

dihydrocodeinone is converted to 14-hydrocodeinone

then hydrogenation would have converted most of the

converted 14-hydrocodeinone to oxycodone.

Casner claim 1

Casner maintains that its involved claims are not

unpatentable over the art it relies on to attack Chapman.

We disagree.

The differences between Casner claim 1 and

Chapman claim 96 are set out in Appendix 3 reproduced

above.

What these differences amount to (1) use of a pH

below 6, (2) a step (a) reaction temperature of at least

55°C for a period of at least 1 hour, and (3) hydrogenation

for at least | hour.

66a

Appendix B

In our view these differences do not make the

subject matter of Casner claim 1 non-obvious over the

prior art.

While Casner does not mention in its specification

any problem associated with the presence of 8,14-

dihydroxy-7,8-dihydrocodeinone impurity, the relevant

literature, of which one skilled in the art would have

been aware, reveals what needs to be done. To be sure,

Casner does not have to actually know why its invention

works—only that it does work. However, one skilled in

the art aware of the literature called to our attention

would immediately know why the Casner invention

works—it works for the same reason that Chapman's

invention works.

Back to the differences related to pH and reaction

times and temperatures.

We will start with the proposition that one skilled in

the art would have known that a pH would be necessary

and that reactions times and temperatures would be

necessary. The question is: “Would one skilled in the

art know, or be able to figure out, what pH, reaction

time and reaction temperatures to use?” In our view

the answer, based on Dr. Baldwin's testimony—and in

part on Dr. Stork's testimony--is “yes.”

First, one skilled in the art would have known that

reaction conditions affect the compound or compounds

produced from the combination of 8,14-dihydroxy-7,8-

dihydrocodeinone and hydrochloric acid. Dr. Stork seems

to agree.

67a

Appendix B

Second, dehydration is a well-known process.

Dr. Baldwin convincing|y told us that dehydration, along

with hydrogenation, is a well known chemical process—

processes which are taught in college chemical curricula

and that hydrogenation is a traditional step in making

oxycodone.

Third, when, as here, “there is a... market pressure

to solve a problem and there are a finite number of

identified, predictable solutions [determining pII and

reaction times and temperatures], a person of ordinary

skill has good reason to pursue the known options

[dehydration and hydrogenation] within his or her

technical grasp. If this leads to the anticipated success,

[as did here,] it is likely the product not of innovation

but of ordinary skill and common sense.” ASR, 127

S. Ct. at 1742.

Fourth, there is no credible evidence before us which

would make ovt a case that any unexpected result is

achieved by use of the particular parameters ultimately

described to be useful by Casner.

Based on the record before us, we hold that the

subject matter of Chapman claim 96 and the subject

matter of Casner claim 1 would have been obvious within

the meaning of 35 U.S.C. § 103.

68a

Appendix B

Chapman and Casner dependent claims

What about the dependent claims of the parties?

In presenting Casner Motions 9-10, Casner was

under a burden to establish unpatentability of all of the

Chapman claims, including the dependent claims.

37 C.E.R. § 41.121(b) (2007) and 37 C.FE.R. § 41.207(b),

last sentence (2007).

In its motion, Casner addresses all of Chapman's

claims. Paper 32, pages 14-18.

In Chapman Oppositions 9-10, Chapman does not

Single out any of its dependent claims for separate

consideration, Instead, Chapman bottoms its argument

on Chapman claim 96,

In Casner Motions 9-10, Casner makes an attempt

to establish that its claims are not unpatentable even if

the Chapman claims are unpatentable. See 37 C.F.R.

§ 4).207(c) (2007). Paper 32, pages 18-20.

In Chapman Oppositions 9-10, Chapman expressed

disagreement concerning the Casner dependent claims.

Paper 48, pages 14-20.

In Casner Replies 9-10, Casner does not single out

any dependent claim for separate consideration. Paper

57, pages 8-10.

69a

Appendix B

In this inter partes case, the parties have elected

to argue the patentability of their respective dependent

claims along with the patentability of Chapman claim 96

and Casner claim 1.

In view of the manner in which the case has been

presented, in our view the dependent claims stand or

fall together with Chapman claim 96 and Casner claim

1. We prefer to decide the contested issues rather than

issues which might have been, but apparently for

litigation reasons, were not contested. Cf Brand ».

Miller, 487 F.3d 862 (Fed. Cir. 2007).

The Fibel Process argument

Chapman attempts to convince us that the case is

controlled by Libel Process Co. v. Minnesota & Ontario

Paper Co., 261 U.S. 45 (1923). The inventor in Fibel

solved an industrial problem of long-standing using a

technique which a person skilled in the art would not

have appreciated. It took many years for the inventor

to solve a long-standing problem of trying to reach

printing speeds of 500-600 feet per minute. The same is

true of the invention found patentable in Webster Loom

Co. v. Higgins, 15 Otto (105 U.S.) 580 (1881), where a

loom was invented which would produce 50 yards of

product per day when no one had been able to produce

more than 40 yards per day. Here, on the other hand,

the IDA and the pharmaceutical industry were faced

with a problem which seems to have been solved in

rather short order by those skilled in the art using their

sophisticated skilled through application of known

70a

Appendix B

techniques reported in the literature or which were

otherwise known.

Conclusion of law

All the involved claims of both parties are

unpatentable under 35 U.S.C. § 103 and a judgment

against both parties is entered concurrently with this

MEMORANDUM OPINION and ORDER.

D. Casner Motion 1-interference-in-fact

The underlying legal principles governing the

motion are relatively simple.

An interference exists if the subject matter of a

claim of one party (e.g., Casner claim 1) would, if prior

art, have anticipated (35 U.S.C. § 102) or rendered

obvious (35 U.S.C. § 103) the subject matter of a claim

of the opposing party (e.g., Chapman claim 96) and vice

versa. 37 C.FR. § 41.208(a) (2007).

Casner, as movant, has the burden of proof on the

issue of no interference-in-fact. 837 C.FR. § 41.121(b)

(2007).

Casner does not contest the fact that the subject

matter of its claim 1 anticipates (35 U.S.C. § 102) the

subject matter of Chapman claim 96,

Tla

Appendix B

Rather, Casner maintains that given differences

between the subject matter of Chapman claim 96 and

Casner claim 1 that the subject matter of Chapman claim

96 does not render obvious (35 U.S.C. § 108) the subject

matter of Casner claim 1.

We disagree with Casner and deny Casner Motion 1.

Casner claim 1 is unpatentable over the prior art

under 35 U.S.C. § 103.

When patentability under § 103 is considered in

light of that art, and the additional presumed prior art

embodied in the subject matter of Chapman

claim 96, it is not difficult to see that Chapman and

Casner are claiming the same “patentable” (perhaps

“unpatentable” would be a better word) invention.

The scope and content of Chapman claim 96, when

interpreted in light of the Chapman specification

(including Example 3) appears in the findings.

Like the differences between Chapman claim 96 and

Casner claim 1 appear in the findings.

There is not much we need to add to findings already

made for the reader to understand why we believe

Casner has failed to establish that the subject matter

of Chapman claim 96 does not render obvious the subject

matter of Casner claim 1.

72a

Appendix B

While Chapman did not have the burden of proof, it

has not gone unnoticed by that Dr. Baldwin's testimony

more than establishes the obviousness of the subject

matter of Casner claim 1] vis-a-vis Chapman claim 96 to

a person having ordinary skill in the art.

Much of the Casner argument is about differences.

However, the mere existence of differences is not

enough to render subject matter non-obvious under

§ 103. Dann v. Johnston, 425 U.S. 219, 230 (1976) [the

mere existence of difference between the prior art

(Chapman claim 96) and an invention (Casner claim 1)

does not establish the invention's non-obviousness }.

Dr. Baldwin has convincingly established why those

differences do not overcome the § 103 hurdle in the

context of a no interference-in-fact analysis.

Conclusion of law

Casner has failed to establish that there is no

interference-in-fact.

E. Casner Motions 6-7—lack of written

description/enablement

The legal principles applicable to a written

description issue are set out in /n re Alton, 76 F:3d 1168

(Fed. Cir. 1996), and need not be repeated here.

73a

Appendix B

The legal principles applicable to an enablement

issue are straightforward.

A specification must teach a person of ordinary skill

in the art how to make and use the invention without

resort to undue experimentation. A’nzo biochem Ine. v.

Calgene, Inc., 188 F.3d 13862, 1371-72 (Fed. Cir. 1999).

Factors which can be taken into account to

determine whether undue experimentation is involved

are set out in /n re Wands, 858 F.2d 731, 737 (Fed. Cir.

1988), adopting factors previously set out in Ax parte

Forman, 230 USPQ 546, 547 (Bd. Pat. App. & Int. 1986).

The following observations by the Supreme Court

are also applicable: the specification of the patent is not

addressed to lawyers, or even to the public generally,

but to those skilled in the art; and any description which

is sufficient to apprise them in the language of the art

of the definite feature of the invention, and to serve as

a warning to others of what the patent claims as a

monopoly, is sufficiently definite to sustain the patent

and an inventor may assume that what was already

known in the relevant art was known to those skilled in

the art. Carnegie Steel Co. v. Cambria Iron Co., 185 U.S.

403, _ (1902) (specification involving manufacturing of

steel addressed to manufacturers of steel). See also

Webster Loom Co. v. Higgins, 15 Otto (105 U.S.) 580,

586 (1881) (an inventor may begin a description of an

invention at the point where his invention begins, and

describe what he has made that is new, and what it

replaces of the old; that which is common and known is

74a

Appendix B

as if it were written out in the patent and delineated in

the drawings).

Casner starts with the assertion that "Incubation"

is undefined. Dr. Baldwin explained otherwise and we

are comfortable with Dr. Baldwin's explanation.

Arguing that conversion of 8,14-dihydroxy-7,8-

dihydrocodeinone to 14-hydroxycodeinone would be

dependent on a number of variable (including

temperature, pH, and reaction times), Casner says the

Chapman claims are unacceptable because those

variables are not set out in the claims.

Dr. Baldwin and Dr. Stork acknowledged that one

skilled in the art would know that those variables would

need to be considered and Dr. Baldwin testified that one

skilled in the art would be able to determine appropriate

reaction temperatures, pH, and times.

We credit Dr. Baldwin's testimony.

Casner next attacks the language “under conditions

suitable to promote dehydration.”

However, the claim states the objective to be

achieved and Dr. Baldwin testified that one skilled in

the art would have been able to determine appropriate

conditions.

Nor have we overlooked Chapman Example 3 which

seems to provide a roadmap for carrying out the

Chapman process.

75a

Appendix B

The complaint Casner has with Example 3 is that

while Chapman had possession of a temperature,

Chapman did not have possession of a time of reaction.

Dr. Baldwin disagrees maintaining that one skilled

in the art would have been able to determine an

appropriate time.

Casner maintains that Chapman flunks /n7 re

Wands.

Dr. Baldwin disagrees.

We agree with Dr. Baldwin.

The fact that some search of the literature and some

experimentation may be necessary is not per se

sufficient to say any experimentation is “undue.”

Casner has failed to establish that the

experimentation which Dr. Baldwin found to be routine

is “undue.”

In addition to the points made by Dr. Baldwin,

Example 3 and original claim 33 provide additional

evidence that Chapman has a written description of the

invention it now claims.

76a

Appendix B

Conclusions of law

Casner has failed to establish that Chapman lacks a

written description.

Casner has filed to establish that Chapman has

failed to provide an enabling disclosure.

EK Other motions

The other motions before us seek earlier

constructive reductions to practice or attack earlier

constructive reductions to practice accorded in the

declaration of the interference.

Since all the claims of the parties are unpatentable

under 35 U.S.C. § 103, we see no occasion to reach the

other motions.

They are dismissed as moot.

G. Observation on “objections” during cross-

examination

During cross-examination, both parties often made

an “Objection” without any brief reason in support of

the objection.

The objections were technical violations of the

Guidelines for Cross-examination.

77a

Appendix B

We note that neither Dr. Stork nor Dr. Baldwin

(much to their credit) seem to have been affected—

hence we find there was no unwarranted witness

coaching.

For further discussion and education, we call

attention to Pevarello v. Lan, 85 USPQ2d 1771 (Bd. Pat.

App. & Int. 2007).

H. Order

Upon consideration of the motions, and for the

reasons given, it is

ORDERED that Chapman Motion 1 seeking an

earlier constructive reduction to practice is dismissed

as moot.

FURTHER ORDERED that Casner Motion 1

seeking judgment based on no interference-in-fact is

denied.

FURTHER ORDERED that Casner Motion 2

attacking earlier constructive reductions to practice

accorded to Chapman is dismissed as moot.

FURTHER ORDERED that Casner Motions 6-7

seeking judgment based on lack of written description

and enablement is denied.

FURTHER ORDERED that Casner Motions 9-10

seeking judgment that the involved Chapman claims are

unpatentable under 35 U.S.C. § 103 is granted.

78a

Appendix B

FURTHER ORDERED that the involved Casner

claims are also unpatentable under 35 U.S.C. § 103.

FURTHER ORDERED a judgment against both

parties is entered concurrently herewith.

/ss/ Fred E. McKelvey

FRED E. McKELVEY

Senior Administrative

Patent Judge

/ss/ Richard Torezon BOARD OF

RICHARD TORCZON PATENT

Administrative Patent Judge APPEALS

AND

/ss/ Michael P Tierney INTERFERENCES

MICHAEL P TIERNEY

Administrative Patent Judge

ec (via electronic mail):

Attorney for Casner

(real party in interest

Johnson Matthey Public Limited Company):

F.dward V. Filardi, Fisq.

Douglas R. Nemec, Esq.

SKADDEN, ARPS, SLATE, MEAGHER & FLOM LLP

Four Times Square

New York, NY 10036

79a

Appendix B

Tel: 212-735-3060 (Filardi)

Tel: ele- 735-2419 (Nemec)

Fax: 212-777-3060 (Filardi)

TT-%

)

Fax: 212-777-2419 (Nemec)

Email: efilardi@skadden.com

Email: dnemec@skadden.com

Attorney for Chapman

(real party in interest

Purdue Pharma L.P):

Joseph R. Robinson, Esq.

Samuel S. Woodley, Esq.

DARBY & DARBY PC

PO. Box 5257, New York, NY 10150

7 World ‘lrade Center

250 Greenwich Street

New York, NY 10007-0042

Tel: 212-527-7700

Fax: 212-527-7001

Email: 7robinson@darbylaw.corm

Kmail: swoodley@darbylaw.com

SOa

APPENDIX C — ORDER OF THE UNITED STATES

COURT OF APPEALS FOR THE FEDERAL

CIRCUIT DENYING PETITION FOR REHEARING

FILED JUNE 15, 2009

2008-1427, -1428

(Interference No. 105,553)

ROBERT CHAPMAN, LONNS. RIDER, QI HONG,

DONALD KYLE, and ROBERT KUPPER,

Appellants,

MICHAEL LAWRENCE CASNER,

JEN-SEN DUNG, ERNO M. KESKENY,

and JIN LUO,

Cross Appellants.

Appeals from the United States Patent and Trademark

Office, Board of Patent Appeals and Interferences.

ORDER

A combined petition for panel rehearing and for

rehearing en banc having been filed by the Appellants,

and a response thereto having been invited by the court

and filed by the Cross-Appellants, and the petition for

rehearing and response, having been referred to the

panel that heard the appeal, and thereafter tne petition

for rehearing en bane and response having been referred

to the circuit judges who are in regular active service,

Sila

Appendix ©

UPON CONSIDERATION THEREOR it i:

ORDERED that the petition for panel rehearing be,

and the same hereby is, DENIED and it is further

ORDERED that the petition for rehearing en banc

be, and the same hereby is, DENIED.

The mandate of the court will issue on June 22, 2009

FOR THE COURT

s/ Jan Horbaly

Jan Horbaly

Clerk

Dated: 06/15/2009

APPENDIX D — JUDGMENT OF THE UNITED

STATES COURT OF APPEALS FOR THE FEDERAL

CIRCUIT DATED MARCH I11, 2009

UNITED STATES COURT OF APPEALS

FOR THE FEDERAL CIRCUIT

2008-1427, -1428

(Interference No. 105,553)

ROBERT CHAPMAN, LONN 8S. RIDER, QI HONG,

DONALD KYLE, and ROBERT KUPPER,

Appellants,

MICHAEL LAWRENCE CASNER, JEN-SEN DUNG,

KERNO M. KESKENY, and JIN LUO,

(ross Appellants.

ON APPEAL from the lInited States Patent and

lrademark Office, Board of

Patent Appeals and Interfer

ence:

his CAUSE having been heard and considered, it j

ORDERED and ADJUDGED:

LhEIRMED

ip; Child

LNTERED BY ORDER OF THE COURT

Jan Horbaly/kw

Jan Horbaly, Clerk

DATED MAR 11 2009

ISSUED AS A MANDATI JUN 22 2009

APPENDIX E — CHAPMAN CLEAN COPY OF

INVOLVED CLAIMS DATED MAY 3, 2007

Paper No

Dated filed: 03 Vay 2OO7

l’iled on behalf of Chapman et a/

By: Joseph R. Robinson

Samuel 8S. Woodley

DARBY & DARBY RC

S05 Third Avenue

New York, New York 10022-7513

Tel: (212) 527-7700

Fax: (212) 753-770]

Email: jrobinson@darbylaw.com

swoodley@darbylaw.com

(Attorney Docket No. 02755/7001437-000

UNITED STATES PATENT AND

TRADEMARK OFFICE

BOARD OF PATENT APPEALS

AND INTERFERENCES

Interference 105.553 (McK)

Technology Center 1625

MICHAEL LAWRENCE CASNER, JEN-SEN DUNG

MRNOM. KENSKENY and JIN LUO

Patent No. 7.153.966 B2.

Junior Party

85a

Appendix E

ROBERT CHAPMAN, LONN S. RIDER, QI HONG,

DONALD KYLE and ROBERT KUPPER,

Application No. 11/391,897

Senior Party

CHAPMAN CLEAN COPY OF INVOLVED CLAIMS

Pursuant to the requirements of Bd. R. 110(a), the

senior party Chapman et al. submits herewith, at

Appendix 1 of this paper, a clean copy of its involved

claims in this interference; ?7.e., claims 96-118 of

Application No. 11/391,897.

Dated, 03 May 2007

Respectfully submitted,

/Samuel 8. Woodley/

Joseph R. Robinson (Reg. No. 33,448)

Samuel S. Woodley (Reg. No. 43,287)

DARBY & DARBY PC.

805 Third Avenue

New York, New York 10022-7513

Tel: (212) 527-7700

Fax: (212) 753-7701

Kmail: jrobinson@darbylaw.com

swoodley@ darbylaw.com

Attachment: Appendix 1 - Clean Copy of Claims 96-118

of Chapman’s Application No. 11/391,897

cc (by Federal Express overnight delivery):

RATNER & PRESTIA

(Attorney for Casner et al.)

1235 Westlak Drive, Suite 301

Berwyn, PA 19312

%6a

Appendix F

APPENDIX 1: CLEAN COPY OF CLAIMS 96-118

(Of Chapman’s Application No. 11/391,897)

Claim 96: A process for preparing oxycodone or an

oxycodone salt, which process comprises steps of:

(a) preparing a mixture of oxycodone,

solvent and an acid;

(b) ineubating the mixture under conditions

suitable to promote reaction of 8,14-

dihydroxy-7,8-dihydrocodeinone to 14-

hydroxycodeinone; and subsequently

reagents under conditions sufficient for

conversion of 14-hydroxycodeinone to

oxycodone.

Claim 97: The process according to claim 96,

vherein in step (b) the mixture is heated to a

temperature of about 75 °C.

Claim 98: The process according to claim 96,

wherein the mixture has a pH of about 2.5 or less.

Claim 99: The process according to claim 98,

wherein the mixture has a pH of about 1.8 or less.

Claim 100: The process according to claim 99,

wherein the mixture has a pH of about 1.5 or less.

87a

Appendix E

Claim 101: The process according to claim 100,

wherein the mixture has a pH of about 1 or less.

Claim 102: The process according to claim 96,

wherein the hydrogenation reagents are a

hydrogenation catalyst and either hydrogen or a

hydrogen transfer reagent.

Claim 103: The process according to claim 96,

wherein step (b) is carried out at a temperature between

about 20 °C to about 100 °C.

Claim 104: The process according to claim 103,

wherein step (b) is carried out at a temperature between

about 40 °C to about 85 °C.

Claim 105: The process according to claim 96,

wherein in step (c) the mixture is exposed to the

hydrogenation reagents for between about 10 minutes

to about 36 hours.

Claim 106: The process according to claim 108,

wherein in step (c) the mixture is exposed to the

hydrogenation reagents for at least about 4 hours.

Claim 107: The process according to claim 106,

wherein in step (c) the mixture is exposed to the

hydrogenation reagents for at least about 5 hours.

Claim 108: The process according to claim 107,

wherein in step (c) the mixture is exposed to the

hydrogenation reagents for about 21 hours.

88a

Appendix E

Claim 109: The process according to claim 96,

wherein the acid in said mixture is present in an amount

greater than 1 molar equivalent compared to the

amount of oxycodone.

Claim 110: The process according to claim 96,

wherein the acid is hydrochloric acid.

Claim 111: The process according to claim 119,

wherein the hydrochloric acid is present in an amount

greater than 1 molar equivalent compared to the

amount of oxycodone.

Claim 112: The process according to claim 111,

wherein the hydrochloric acid is present in an amount

greater than about 1.2 molar equivalents compared to

the amount of oxycodone.

Claim 1138: The process according to claim 112,

wherein the hydrochloric acid is present in an amount

greater than about 1.4 molar equivalents compared to

the amount of oxycodone.

Claim 114: The process according to claim 113,

wherein the hydrochloric acid is present in an amount

greater than about 1.5 molar equivalents compared to

the amount of oxycodone.

Claim 115: The process according to claim 96,

wherein the resultant oxycodone contains 14-

hydroxycodeinone in an amount less than about 25 parts

per million (“ppm’’).

89a

Appendix FE

Claim 116: The process according to claim 115,

wherein the resultant oxycodone contains 14-

hydroxycodeinone in an amount less than about 15 ppm.

Claim 117: The process according to claim 116,

wherein the resultant oxycodone contains 14-

hydroxycodeinone in an amount less than about 10 ppm.

Claim 118: The process according to claim 117,

wherein the resultant oxycodone contains 14-

hydroxycodeinone in an amount less than about 5 ppm.

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