NOTE: This disposit ion is nonprecedential.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from: United States Patent and Trademark Office Board of Patent Appeals and InterferencesNOTE: This disposition is nonprecedential.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 Kesk eny, and Jin Luo’s (“Casner’s”) U.S. Patent No. 7,153,966 (“the ’966 patent”) both claim methods of preparing oxycodone thatreduce 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 judgm ent that Chapman claims 96–118 were unpatentable under 35 U.S.C. § 103(a). Chapman appeals, a sking 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, ar guing that if we reverse the Board’s holdings as to the ’897 application, we s hould reverse its holdings on the ’966 patent and remand for a priority dete rmination. 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 onl y 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 condi tions suitable to promote reaction of 8,14-dihydroxy-7, 8-dihydrocodeinone to 14-hydroxycodeinone; and subsequently (c) exposing the mixture to hy drogenation 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 tr eated with acid during a final “salting”

2008-1427, -1428 2step to yield pharmaceutical grade oxycodone. Any 14-hydroxy remaining at the end of the reaction is problematic, as t he compound is potentially toxic. The 8,14-dihydroxys created dur ing the initial oxidati on step are stereoisomers— there are two forms, designated “8 α ” and an “8 β ,” that differ only by the relative orientation of a hydroxyl gr oup. Chapman claims that prio r to the ’897 application, persons of ordinary skill in t he art did not know that 8 α formed during the reaction. Instead, they believed that thebaine oxidized to form 14-hydroxy and 8 β , 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 8 α during the reaction’s salting step, and that the “new ” 14-hydroxy can therefore yield additional oxycodone. Chapm an purports to claim this method of eliminating the “new” 14-hydroxy in claim 96. The claim does not, however, differentiate between the 8 α and 8 β forms of 8,14-dihydroxy, nor does the claim language specifically disclose which conditions are “s uitable” for promoti ng 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 3determination 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 8 α was formed during thebaine oxidation. Nor, according to Chapman, was it known that 8 α could react with acid under certain “commercial conditions” to form additional 14-hydroxy. Chapman admits that th e prior art disclosed 8 β , but claims that “under commerc ial oxycodone production conditions,” 8 β converts into a benign salt, not into 14-hydroxy. In his view, the prior art would lead a person of ordinary skill in the ar t to believe that 8 β must be treated with “stronger than commercially used” amounts of hydrochloric acid before it converts to 14-hydroxy. Casner states that Chapman never claimed 8 α 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. Chapm an responds that both issues were raised, although the stereochemistry argument is emphasized on appeal because Ca sner did not produce the “Proksa” reference (upon which the B oard relied) until its response, leaving Chapman little opportunity to analyze and respond to the specific issues raised by that reference. Chapman also argues that sinc e the Board identified a “commercial need” for reduced levels of 14-hydrox y, and found that a person of sk ill in the art would work in the “highly competitive pharma ceutical 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 4Chapman clarified which conditions would qualify as “commercial conditions.” Similarly, although 8 α is identified in some of the ’897 application’s figures, and Chapman’s expert made references to stereoisomers in revie wing the prior art, Chapman has not identified any statement before the Boar d that explicitly different iated between the invention and the prior art based on stereochemistry. Regardless, we need not resolve the wa iver issue definit ively. Chapman maintains, and we agree, that “[t]he term ‘8,14-dihydroxy’ properly includes 8 α , but there is no reason for that term to be limited to t hat isomer in Chapman’s claims. The term ‘conditions’ properly includes commercial conditi ons, but there is no r eason 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-dihy drocodeinone includes either 8 α ,14-dihydroxy-7,8-di hydrocodeinone; or 8 β ,14-dihydroxy-7, 8-dihydrocodeinone or can include a mixture of both compounds.” ’897 application ¶ 0043. Thus, claim 96 merely requires one to in cubate the mixture “under conditions suitable to promote reaction” of 8,14-dihydroxy to 14-hydrox y. Therefore, prior art references that disclose either the 8 α or 8 β form of 8,14-dihydroxy converting to 14- hydroxy, or disclose any reaction condition (w hether “commercial” or not) that promotes the conversion of 8 α or 8 β to 14-hydroxy, may render the claim obvious. See In re May, 574 F.2d 1082, 1088–89 (C.C.P.A. 1978) (“[The refe rence] expressly discloses . . . a species within the genus of claim 1. Ther efore, [the reference] is a technical anticipation of claim 1. A ppellants’ assertions to the contrary notwithstanding, this finding does not constitute a new ground of reje ction; 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 52003) (concluding that first step of an interf erence-in-fact inquiry was satisfied where two method claims had a genus/species relations hip, 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, not ing that “[t]he only other difference between [the two method claims] is that the fo rmer 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 pr ior art discloses methods under which at least one 8,14-dihydroxy reacts to yi eld 14-hydroxy under certain conditions. Specifically, the Board noted that the FDA “recognized that t here was a need to eliminate impurities in oxycodone,” and then proceeded to walk through t he prior art, which disclosed: that both 14-hydroxy and 8,14-dihy droxy were known impurit ies during the thebaine oxidation reaction; that treatm ent of 8,14-dihydroxy with hydr ochloric acid converts 8,14- dihydroxy into 14-hydroxy under certain reac tion 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 8 β , at least, will

2008-1427, -1428 62008-1427, -1428 7 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 8 α or 8 β 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).NOTE: This disposit ion 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 Stat es 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 ox idation of thebaine creat es the stereoisomer 8 α , which in turn creates additional 14-hydroxy during formu lation of this important pharmaceutical. Until this discovery, this field of art believe d that the original ox idation step created the additional 14-hydroxy impurit y. After discovering 8 α , 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 tr ue nature of the “lefto ver” 14-hydroxy problemand the first to solve it. Because this im portant 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 t he 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, Ei bel easily prescribed the solu tion 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 t hat the salting of stereoisomer 8 α , not the oxidation of thebaine, created the additional 14- hydroxy impurity in ox ycodone salt. He solved this problem by isolating and hydr ogenating the 14-hyrdroxy to form additional oxycodone. Chapman’s invention was not t he 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 k nown and the application of t he 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 outboar d 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 pu t a non-galling material, such as silver, on

2008-1427, -1428 2the end faces of the connecting rod bearings. Id. at 682. Citing the rationale of Eibel , the Court of Customs and Pat ent 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 failu res” and (b) “its elimination by the claim ed plating of . . . the contacting areas of the face portions of the connecting rods and the crank cheeks, were not obvious from the pr ior art at the time the invention was made to a person havi ng 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 vi als. 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 discover y of the source of a problem even though the remedy may be obvious once t he source of the prob lem is identified. This is part of the ‘subject matter as a whole’ which should a lways be considered in determining the obviousness of an invention under 35 USC 103.” Id. at 585. In resolving the issue of obviousne ss, 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 reaso ned 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 repr esented to the Patent and Trademark Office that up until th e time of the claimed inve ntion, “the nuclear [power] industry faced the problem of undesirable stressing of fuel rod claddings in gas-cooled

2008-1427, -1428 3nuclear 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 pr oblem 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 ca use would have been recognized by one of ordinary skill in the art at the time the inv ention was made.” Id. In reversing the Board’s holding of obv iousness, the CCPA f ound “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 spac er 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 th e art at the time of [an applicant’s] invention would have expected [a problem]’, e.g. , sticking, ‘to exist at a ll, 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 pers on 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 Inter national Co. v. Teleflex Inc. recently held that “[w]hen there is a design need or market pre ssure to solve a problem and there are a finite number of identified, predictable so lutions, a person of ordinary skill has good reason to pursue the known options within his or her technical gr asp. 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 4of identified, predictable solutions” that were used to discove r the source of and solution to the problems. Id. No persons of ordinary skill in th e art knew of the existence of 8 α before Chapman and, in fact, were trying to solve the problem of removing excess 14- hydroxy impurities from oxycodo ne salt by other means. Be cause no other persons had discovered and solved this problem as Chapm an did, his invention is the product of innovation and not of “ordinar y 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, accide ntally discovered topiramate. 520 F.3d 1358 (Fed. Cir. 2008). Topiramate is a reaction inte rmediate that has powe rful 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, unex pected results of topiramate (i.e. , anticonvulsive activity), skepticism of experts, copying, and commercial success. Id. at 1365. “As this court has repeatedl y 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 discover ed that the stereoisomer 8 α , when salted, creates additional 14-hydroxy. This ad ditional 14-hydroxy can be isolated and hydrogenated to create additiona l oxycodone, containing mu ch less of the 14-hydroxy impurities that the FD A desired removed from oxycodone salt. Persons of ordinary skill

2008-1427, -1428 52008-1427, -1428 6 in the art never discovered or appreciated the presence of 8 α as the source of the additional 14-hydroxy. The prior art disclosed that 14-hy droxy was a carry-over from the oxidation of thebaine, re sulting 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 traver sing the multiple obstacles to easily produce t he invention in light of the evidence available at t he time of invention.” Ortho-McNeil , 520 F.3d at 1365. Chapman, therefore, unexpect edly discovered the true sour ce of the additional 14- hydroxy and solved the problem by remo ving the impurity from oxycodone salt. Because the prior art could not have int ended or appreciated Ch apman’s discovery or solution, this invention deser ves patent protection. For the foregoing reasons, I respectfully dissent.