Court Opinion

ID: 209138
Source: CourtListenerOpinion
Date Created: 2011-03-13 07:27:53+00
Date Added: 2024-06-11T09:48:50.252808
License: Public Domain

NOTE: This disposition is nonprecedential.

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,

                                         v.

                MICHAEL LAWRENCE CASNER, JEN-SEN DUNG,
                      ERNO M. KESKENY, and JIN LUO,

                                                    Cross Appellants.

       Joseph R. Robinson, Darby & Darby P.C., of New York, New York, argued for
appellants. With him on the brief were Samuel S. Woodley, and Martin S. Sulsky, of
Washington, DC.

      Douglas R. Nemec, Skadden, Arps, Slate, Meagher & Flom LLP, of New York,
New York, argued for cross-appellants. With him on the brief were Edward V. Filardi
and Stacey L. Cohen. Of counsel was Jeffrey A. Pade, of Washington, DC.

Appealed from: United States Patent and Trademark Office
               Board of Patent Appeals and Interferences
                      NOTE: This disposition is nonprecedential.

 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,

                                           v.

                  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 Circuit
Judge RADER.

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:
       (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
       (c) exposing the mixture to hydrogenation 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-7,8-

dihydrocodeinones (collectively, “8,14-dihydroxys”). The 14-hydroxy is converted via

hydrogenation into oxycodone, which is then treated with acid during a final “salting”

2008-1427, -1428                            2
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 “8α” and an “8β,” that differ only by the relative

orientation of a hydroxyl group. Chapman claims that prior to the ’897 application,

persons of ordinary skill in the art did not know that 8α formed during the reaction.

Instead, they believed that thebaine oxidized to form 14-hydroxy and 8β, 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 8α 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 8α and 8β 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).

                                     II. DISCUSSION

      Obviousness is a legal conclusion based on underlying findings of fact. In re

DBC, 545 F.3d 1373, 1377 (Fed. Cir. 2008).             We review the Board’s ultimate

2008-1427, -1428                            3
determination of obviousness de novo, while we review the Board’s underlying factual

findings for substantial evidence. Id.

       We first turn to Chapman’s arguments. Chapman claims that prior to the ’897

application, no one knew that 8α was formed during thebaine oxidation. Nor, according

to Chapman, was it known that 8α could react with acid under certain “commercial

conditions” to form additional 14-hydroxy. Chapman admits that the prior art disclosed

8β, but claims that “under commercial oxycodone production conditions,” 8β 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 8β must be treated with “stronger than

commercially used” amounts of hydrochloric acid before it converts to 14-hydroxy.

       Casner states that Chapman never claimed 8α 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.

       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

2008-1427, -1428                            4
Chapman clarified which conditions would qualify as “commercial conditions.” Similarly,

although 8α 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 8α, 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 8α,14-dihydroxy-7,8-dihydrocodeinone; or 8β,14-dihydroxy-7,8-dihydrocodeinone

or can include a mixture of both compounds.” ’897 application ¶ 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 8α or 8β form of 8,14-dihydroxy converting to 14-

hydroxy, or disclose any reaction condition (whether “commercial” or not) that promotes

the conversion of 8α or 8β to 14-hydroxy, may render the claim obvious. See In re May,

574 F.2d 1082, 1088–89 (C.C.P.A. 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.

2008-1427, -1428                            5
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., Inc., 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 “[o]ur 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 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 8β, at least, will

2008-1427, -1428                             6
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 8α or 8β 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.

                                  III. CONCLUSION

      For the reasons detailed above, we affirm the Board’s decision to reject claims

96–118 of the ’897 application under 35 U.S.C. § 103(a).

2008-1427, -1428                           7
                       NOTE: This disposition is nonprecedential.

 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,

                                             v.

                  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.

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 8α, 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 8α, 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 Eibel

Process Co. v. Minnesota & Ontario Paper Co., 261 U.S. 45 (1923). In Eibel, the

primary distinction of the invention over the prior art was discovery of the problem in that

discipline.   Id. at 67-68.   Eibel discovered that unequal speeds of stock and wire

produced a defective paper product under high machine speeds. Id. The variance in

paper speed created disturbances and ripples some ten feet from the discharge. Id.

With the problem defined, Eibel easily prescribed the solution by elevating one end of

the paper feed to equalize the speeds of the wire and the paper stock by gravity. Id. at

64.

       In this case, Chapman discovered that the salting of stereoisomer 8α, not the

oxidation of thebaine, created the additional 14-hydroxy impurity in oxycodone salt. He

solved this problem by isolating and hydrogenating the 14-hyrdroxy 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. Id. at 68.

       Similarly, in In re Conover, Conover discovered a solution to the problem of

connecting a rod to an outboard motor engine containing compact, anti-friction roller

bearings. 304 F.2d 680, 681 (C.C.P.A. 1962). A phenomenon known as “galling” could

destroy the bearings at unpredictable times by heating of the roller elements. Id. at 681-

82. To overcome this “galling,” Conover put a non-galling material, such as silver, on

2008-1427, -1428                              2
the end faces of the connecting rod bearings. Id. at 682. Citing the rationale of Eibel,

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,” i.e., (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 prior art at the time

the invention was made to a person having ordinary skill in this art.” Id. at 684.

       In In re Sponnoble, the pharmaceutical industry faced the problem of unwanted

moisture leakage between liquid and solid compartments in vials. 405 F.2d 578, 586

(C.C.P.A. 1969). Sponnoble discovered that the cause of this leakage was the passage

of moisture through, rather than around, the center plug of the vial. Id. 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.”            Id. 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.” Id. 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. Id.

       The CCPA in In 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

2008-1427, -1428                             3
nuclear reactors.” 612 F.2d 1287, 1290 (C.C.P.A 1980). Peehs discovered that “the

cause of this stressing was sticking between the metal surfaces of the claddings and the

contact elements of the spacer grids.” Id. He solved this problem by “roughening one

of the contact surfaces.” Id. Thus, as in Eibel, 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.” Id.

       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 claddings and the spacer grid contact elements caused the

stressing of the claddings.” Id. 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.’” Id. (citing In re Nomiya, 509 F.2d 566, 572 (C.C.P.A. 1975)).

       The Supreme Court in KSR International 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 not of innovation but of ordinary skill and

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

Sponnoble, and Peehs, is distinguished from KSR because there were no “finite number

2008-1427, -1428                              4
of identified, predictable solutions” that were used to discover the source of and solution

to the problems. Id. No persons of ordinary skill in the art knew of the existence of 8α

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.” Id.

      Following KSR, 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. Id.

at 1360.    This court attached particular importance to the objective criteria of

nonobviousness, including the powerful, unexpected results of topiramate (i.e.,

anticonvulsive activity), skepticism of experts, copying, and commercial success. Id. 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.” Id. (citing Catalina Lighting, Inc. v. Lamps Plus, Inc., 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 8α, 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

2008-1427, -1428                            5
in the art never discovered or appreciated the presence of 8α 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 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, I respectfully dissent.

2008-1427, -1428                             6