UNITED STTES PATENT AND TRADEMARK OFFICE
`
`____________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`____________
`
`STEADYMED LTD.,
`
`Petitioner,
`
`v.
`
`UNITED THERAPEUTICS CORPORATION
`
`Patent Owner.
`
`
`
`Case IPR2016-00006
`
`Patent No. 8,497,393
`
`____________
`
`PETITIONER’S NOTICE OF SUPPLEMENTAL AUTHORITY
`
`
`
`
`
`Mail Stop "Patent Board"
`Patent Trial and Appeal Board
`U.S. Patent and Trademark Office
`P.O. Box 1450
`Alexandria, VA 22313-1450
`
`
`
`
`
`
`
`
`
`

`
`Pursuant to the Board’s February 11, 2016, email in the above-captioned
`
`case, Petitioner SteadyMed hereby submits the Federal Circuit’s February 1, 2016
`
`Opinion in notice of supplemental authority pertaining to the decision in Purdue
`
`Pharma L.P. v. Epic Pharma, LLC, No. 2014-1294, 2016 WL 380174 (Fed. Cir.
`
`Feb. 1, 2016), as Attachment A.
`
`
`
`Date: February 11, 2016
`
`
`/s Stuart E. Pollack /
`Stuart E. Pollack, J.D., Ph.D.
`Reg. No. 43,862
`DLA Piper LLP (US)
`
`
`
`
`
`
`
`Respectfully submitted,
`
`
`/s Lisa A. Haile /
`Lisa A. Haile, J.D., Ph.D.
`Reg. No. 38,347
`DLA Piper LLP (US)
`
`1
`
`

`
`
`
`CERTIFICATE OF SERVICE
`
`The undersigned certifies that a copy of the attached Petitioner’s Notice of
`
`Supplemental Authority was served via electronic mail to the following:
`
`Stephen B. Maebius
`George Quillin
`FOLEY & LARDNER LLP
`UT393-IPR@foley.com
`
`Shaun R. Snader
`UNITED THERAPEUTICS CORP.
`ssnader@unither.com
`
`Douglas Carsten
`Richard Torczon
`Robert Delafield
`WILSON, SONSINI, GOODRICH & ROSATI
`dcarsten@wsgr.com
`rtorczon@wsgr.com
`bdelafield@wsgr.com
`
`
`
`Respectfully submitted,
`
`
`/s Lisa A. Haile /
`Lisa A. Haile, J.D., Ph.D.
`Reg. No. 38,347
`DLA Piper LLP (US)
`
`2
`
`
`
`Date: February 11, 2016
`
`
`/s Stuart E. Pollack /
`Stuart E. Pollack, J.D., Ph.D.
`Reg. No. 43,862
`DLA Piper LLP (US)
`
`
`
`
`
`
`
`WEST\268215459.1
`
`

`
`
`
`ATTACHMENT A
`
`ATTACHMENT A
`
`

`
`[1] claims reciting oxycodone active pharmaceutical
`ingredient (API) product with low alpha, beta unsaturated
`ketone (ABUK) levels were invalid for obviousness, and
`
`[2] patent covering abuse-resistant formulations was
`anticipated by prior art reference.
`
`
`
`Affirmed.
`
`
`
`
`West Headnotes (10)
`
`[1]
`
`
`
`
`[2]
`
`
`
`
`[3]
`
`
`
`
`Patents
`Single reference disclosing every element or
`limitation of claim
`
`A patent is invalid for anticipation if a single
`prior art reference discloses each and every
`limitation of the claimed invention. 35 U.S.C.A.
`§ 102.
`
`Cases that cite this headnote
`
`
`Patents
`Inherent anticipation
`
`
`A single prior art reference may anticipate
`without disclosing a feature of the claimed
`invention if such feature is necessarily present,
`or inherent, in that reference. 35 U.S.C.A. § 102.
`
`Cases that cite this headnote
`
`
`Patents
`Questions of law or fact
`
`
`Obviousness is a legal conclusion based on
`underlying facts. 35 U.S.C.A. § 103(a).
`
`
`
`
`
`
`
`Purdue Pharma L.P. v. Epic Pharma, LLC, --- F.3d ---- (2016)
`
`2016 WL 380174
`Only the Westlaw citation is currently available.
`United States Court of Appeals,
`Federal Circuit.
`
`PURDUE PHARMA L.P., the P.F. Laboratories,
`Inc., Purdue Pharmaceuticals L.P., Rhodes
`Technologies, Plaintiffs–Appellants
`v.
`EPIC PHARMA, LLC, Defendant
`Purdue Pharma L.P., the P.F. Laboratories, Inc.,
`Purdue Pharmaceuticals L.P., Rhodes
`Technologies, Plaintiffs–Appellants
`v.
`Mylan Pharmaceuticals Inc., Mylan Inc.,
`Defendants–Appellees
`Purdue Pharma L.P., the P.F. Laboratories, Inc.,
`Purdue Pharmaceuticals L.P., Rhodes
`Technologies, Grunenthal GMBH,
`Plaintiffs–Appellants
`v.
`Amneal Pharmaceuticals, LLC,
`Defendant–Appellee
`Grunenthal GMBH, Purdue Pharma L.P., the P.F.
`Laboratories, Inc., Purdue Pharmaceuticals L.P.,
`Rhodes Technologies, Plaintiffs–Appellants
`v.
`Teva Pharmaceuticals USA, Inc.,
`Defendant–Appellee.
`
`Nos. 2014–1294, 2014–1307, 2014–1313,
`2014–1296, 2014–1311, 2014–1314, 2014–1306,
`2014–1312.
`|
`Feb. 1, 2016.
`
`
`
`
`
`Synopsis
`Background: Patent owner brought action against
`manufacturer of generic pharmaceutical products, alleging
`infringement of patents reciting improved formulation of
`oxycodone and patents claiming technology making
`tablets resistant to abuse. Following bench trial, the
`United States District Court for the Southern District of
`New York, Sidney H. Stein, J., 994 F.Supp.2d 367, found
`patents infringed and invalid as anticipated by or obvious
`over the prior art. Patent owner appealed.
`
`
`
`Holdings: The Court of Appeals, Prost, Chief Judge, held
`that:
`
`
`Cases that cite this headnote
`
`
` © 2016 Thomson Reuters. No claim to original U.S. Government Works.
`
`1
`
`
`
`

`
`low-ABUK product of patents and commercial
`success of other products, or evidence of failure
`of others or long-felt but unaddressed need. 35
`U.S.C.A. § 103(a).
`
`Cases that cite this headnote
`
`
`Patents
`Drugs and medicines
`
`
`Patent covering abuse-resistant formulations
`was anticipated by prior art reference disclosing
`use of hot-melt extrusion of high molecular
`weight polyethylene oxide (PEO) to create a
`controlled-release
`dosage
`form
`for
`pharmaceuticals; reference was directed
`to
`sustained-release dosage
`forms and only
`analgesics on market in a sustained-release form
`at the time were opioids, and reference disclosed
`limitation
`that dosage forms had breaking
`strength of at least 500 N. 35 U.S.C.A. § 102.
`
`Cases that cite this headnote
`
`
`Federal Courts
`Conclusiveness;  res judicata and collateral
`estoppel
`
`On appeal from orders of dismissal due to
`collateral estoppel, the role of the Court of
`Appeals is limited to reviewing the district
`court’s application of collateral estoppel, not the
`correctness of the underlying verdict.
`
`Cases that cite this headnote
`
`
`Patents
`In general;  utility
`
`
`US Patent 6,177,567, US Patent 6,488,963, US
`Patent 7,153,966. Cited.
`
`Cases that cite this headnote
`
`[7]
`
`
`
`
`
`
`[8]
`
`
`
`
`
`
`[9]
`
`
`
`
`
`
`Purdue Pharma L.P. v. Epic Pharma, LLC, --- F.3d ---- (2016)
`
`
`
`
`
`[4]
`
`
`
`
`Patents
`Obviousness;  lack of invention
`
`
`the underlying
`Court of Appeals reviews
`findings of fact in an obviousness determination
`for clear error, and reviews de novo the court’s
`ultimate legal conclusion of whether the claimed
`invention would have been obvious. 35
`U.S.C.A. § 103(a).
`
`Cases that cite this headnote
`
`
`Patents
`In general;  multiple factors
`Patents
`In general;  multiple factors
`
`
`Underlying factual inquiries when determining
`obviousness include (1) the scope and content of
`the prior art, (2) the differences between the
`prior art and the claims at issue, (3) the level of
`ordinary skill in the field of the invention, and
`(4)
`relevant
`secondary considerations. 35
`U.S.C.A. § 103(a).
`
`Cases that cite this headnote
`
`
`Patents
`Drugs and medicines
`
`
`active
`reciting oxycodone
`claims
`Patent
`pharmaceutical ingredient (API) product with
`low alpha, beta unsaturated ketone (ABUK)
`levels were invalid for obviousness; prior art
`taught that oxidation of thebaine produced
`14–hydroxy and it was well known in the art
`that 14–hydroxy could be removed using
`hydrogenation, skilled artisan would have
`recognized that hydrogenation could be used to
`remove remaining 14–hydroxy, regardless of
`source of 14–hydroxy, and fact that 14–hydroxy
`was derived from 8α imparted no structural or
`functional
`differences
`in
`low-ABUK
`hydrocodone API as compared to prior art
`products, and there was no nexus between
`
`[5]
`
`
`
`
`
`
`[6]
`
`
`
`
`
`
`
`
` © 2016 Thomson Reuters. No claim to original U.S. Government Works.
`
`2
`
`

`
`represented by M. Jeffer Ali, Jennell Christine Bilek,
`Alexandra Jane Olson, Christopher A. Pinahs, Sarah
`Stensland, Todd S. Werner.
`
`Donald E. Knebel, Barnes & Thornburg LLP,
`Indianapolis, IN, for amici curiae Donald E. Knebel,
`Mark David Janis. Also represented by Mark David Janis,
`Indiana University Maurer School of Law, Bloomington,
`IN.
`
`Benjamin Conrad Block, Covington & Burling LLP,
`Washington, DC, for amicus curiae Center for Lawful
`Access and Abuse Deterrence.
`Before PROST, Chief Judge, REYNA, Circuit Judge, and
`STARK, Chief District Judge.*
`
`Opinion
`
`PROST, Chief Judge.
`
`
`*1 This appeal arises from consolidated Hatch–Waxman
`proceedings involving the reformulated version of the
`pain reliever OxyContin®. The Appellants, Purdue
`Pharma L.P., The P.F. Laboratories, Inc., Purdue
`Pharmaceuticals L.P.,
`and Rhodes Technologies
`(collectively,
`“Purdue”)
`and Grunenthal GmbH
`(“Grunenthal”) asserted a number of claims from multiple
`different patents against
`the Appellees, Amneal
`Pharmaceuticals, LLC (“Amneal”), Epic Pharma, LLC
`(“Epic”), Mylan Pharmaceuticals Inc. and Mylan Inc.
`(collectively, “Mylan”), and Teva Pharmaceuticals USA,
`Inc. (“Teva”), all of whom have filed Abbreviated New
`Drug Applications (“ANDAs”) seeking to sell generic
`versions of OxyContin®. The United States District Court
`for the Southern District of New York held a three-week
`bench trial in the case against Teva, following which it
`held all of the asserted patent claims invalid. In re
`OxyContin Antitrust Litig., 994 F.Supp.2d 367, 377
`(S.D.N.Y.2014) (“District Court Decision ”). The court
`then entered orders of dismissal in the three remaining
`cases against Amneal, Epic, and Mylan based on
`collateral estoppel. Purdue and Grunenthal appeal the
`final judgment in the Teva action, and Purdue also
`appeals the orders of dismissal in the three other cases.
`For the reasons stated below, we affirm the district court’s
`rulings.
`
`
`
`BACKGROUND
`
`Purdue Pharma L.P. v. Epic Pharma, LLC, --- F.3d ---- (2016)
`
`
`
`
`
`Patents
`In general;  utility
`
`
`US Patent 7,674,799, US Patent 7,674,800, US
`Patent 7,683,072, US Patent 8,114,383. Invalid.
`
`Cases that cite this headnote
`
`
`[10]
`
`
`
`
`
`
`
`
`Appeal from the United States District Court for the
`Southern District
`of New York
`in Nos.
`1:13–cv–00683–SHS,
`1:12–cv–02959–SHS,
`1:11–cv–08153–SHS,
`1:11–cv–02037–SHS,
`1:12–cv–05083–SHS, Senior Judge Sidney H. Stein.
`
`Attorneys and Law Firms
`
`Gregory A. Castanias, Jones Day, Washington, DC,
`argued for all plaintiffs-appellants. Plaintiffs-appellants
`Purdue Pharma L.P., The P.F. Laboratories, Inc., Purdue
`Pharmaceuticals L.P., Rhodes Technologies
`also
`represented by Jennifer Loraine Swize; John Joseph
`Normile, Jr., New York, NY; Robert J. Goldman, Ropes
`& Gray LLP, East Palo Alto, CA; Sona De, Christopher J.
`Harnett, New York, NY.
`
`Basil J. Lewris, Finnegan, Henderson, Farabow, Garrett &
`Dunner, LLP, Washington, DC, for plaintiff-appellant
`Grunenthal GmbH. Also represented by Jennifer Howe
`Roscetti, Erin McGeehan Sommers; Charles E. Lipsey,
`Reston, VA.
`
`William A. Rakoczy, Rakoczy Molino Mazzochi Siwik
`LLP, Chicago, IL, argued for defendants-appellees Mylan
`Pharmaceuticals Inc., Mylan Inc. Also represented by
`Amy D. Brody, Eric R. Hunt, Natasha L. White.
`
`Barbara Mullin, Akin, Gump, Strauss, Hauer & Feld,
`LLP, Philadelphia, PA, argued for defendant-appellee
`Amneal Pharmaceuticals, LLC. Also represented by
`Steven D. Maslowski, Matthew A. Pearson, Angela
`Verrecchio,
`Jason Weil; Emily Curtis
`Johnson,
`Washington, DC; Kenneth E. Crowell, Stuart D. Sender,
`Budd Larner, P.C., Short Hills, NJ.
`
`Mark David Schuman, Carlson, Caspers, Vandenburgh,
`Lindquist & Schuman, P.A., Minneapolis, MN, argued for
`defendant-appellee Teva Pharmaceuticals USA, Inc. Also
`
`Oxycodone hydrochloride—the active pharmaceutical
`ingredient
`(“API”)
`in OxyContin®—is an opioid
`analgesic used to treat moderate to severe pain. This
` © 2016 Thomson Reuters. No claim to original U.S. Government Works.
`3
`
`
`
`

`
`Purdue Pharma L.P. v. Epic Pharma, LLC, --- F.3d ---- (2016)
`
`
`
`consolidated appeal concerns four patents associated with
`the reformulated version of OxyContin®: U.S. Patent No.
`7,674,799 (“′799 patent”), U.S. Patent No. 7,674,800
`(“′800 patent”), U.S. Patent No. 7,683,072 (“′072 patent”)
`(collectively, “the low-ABUK patents”), and U.S. Patent
`No. 8,114,383 patent (“′383 patent”).
`
`
`
`I. The Low–ABUK Patents
`
`The low-ABUK patents recite an improved formulation of
`oxycodone hydrochloride. Those patents describe an
`oxycodone salt with extremely low levels of a particular
`impurity, 14–hydroxycodeinone (“14–hydroxy”), which
`belongs to a class of potentially dangerous compounds
`known as alpha, beta unsaturated ketones (“ABUKs”).
`The prior art method of synthesizing oxycodone
`hydrochloride involved three steps: first, thebaine, a
`derivative of the opium poppy, was oxidized to form
`14–hydroxy; second, the 14–hydroxy was converted to
`oxycodone free base through hydrogenation; and third,
`the oxycodone free base was reacted with hydrochloric
`acid to form oxycodone hydrochloride. The end product
`created by that process, however, contained high levels of
`14–hydroxy, on the order of 1500 parts per million
`(“ppm”).
`
`In January 2004, the U.S. Food and Drug Administration
`(“FDA”) became concerned
`that 14–hydroxy was
`potentially toxic and thus mandated that oxycodone
`hydrochloride manufacturers either provide evidence that
`the 14–hydroxy levels in their formulations were safe or
`reduce the amount of 14–hydroxy to less than 10 ppm.
`Even before the FDA’s mandate, however, Rhodes
`Technologies—a subsidiary of Purdue—had begun
`researching methods to reduce 14–hydroxy levels in its
`oxycodone API. The scientists initially hypothesized that
`the 14–hydroxy present in the final salt was leftover
`14–hydroxy that had not been hydrogenated in the second
`step. Thus, they extended the hydrogenation reaction to
`completion,
`confirming
`that
`every molecule of
`14–hydroxy converted to oxycodone free base at step two.
`But
`the
`scientists
`found
`that
`after
`step
`three—transforming
`the oxycodone
`free base
`into
`oxycodone hydrochloride—the 14–hydroxy had returned.
`
`
`*2 The scientists thus shifted their focus to step three. It
`was well known
`in
`the art
`that an
`impurity,
`8,14—dihydroxy–7,
`8—dihydrocodeinone
`(“8,14–dihydroxy”) was produced as a byproduct of the
`oxidation of thebaine (step one). More specifically, it was
`known that a particular isomer of 8,14–dihydroxy was
`formed: 8β, 14—dihydroxy—7, 8—dihydrocodeinone
` © 2016 Thomson Reuters. No claim to original U.S. Government Works.
`
`
`
`(“8β”). Scientists did not know with certainty, however,
`whether
`8α,14–dihydroxy–7,
`8—dihydrocodeinone
`(“8α”)—a diastereomer of 8α—was also produced during
`the oxidation step. Purdue scientists had previously noted
`the potential existence of 8α, but no scientific literature
`discussed
`that
`particular
`isomer.
`Through
`experimentation, the scientists determined that 8α was
`indeed being produced at step one and, in fact, was
`transforming into 14–hydroxy during the acid-catalyzed
`dehydration at step three. To remove the 14–hydroxy
`from the oxycodone API, the scientists added another
`hydrogenation step at the end of step three to convert the
`remaining 14–hydroxy into oxycodone free base. By June
`2003, Rhodes’s
`laboratory could routinely produce
`oxycodone API with 14–hydroxy levels less than 10 ppm
`using the double-hydrogenation process. Purdue and
`Rhodes thus sought approval from the FDA and patent
`protection for their low-ABUK oxycodone product.
`
`
`The low-ABUK patents continue from application No.
`11/391,897, known as the “Chapman Application.” The
`claims of the Chapman Application have previously been
`before us; we authored a non-precedential decision
`affirming the Board of Patent Appeals and Interferences’
`determination that the Chapman claims were obvious.
`Chapman v. Casner, 315 F. App’x 294, 295
`(Fed.Cir.2009) (Rader, CJ., dissenting). In that case, the
`Board declared an interference between the Chapman
`Application and U.S. Patent No. 7,153,966 (“Casner”).
`The relevant claims in the Chapman Application related
`to a method for making oxycodone API using a
`hydrogenation step to remove 14–hydroxy, but they did
`not require that some of the remaining 14–hydroxy be
`derived from the 8α isomer. Id. The Board compared
`Chapman’s claims to the prior art and concluded that they
`were obvious. Chapman appealed directly to us, and we
`agreed with the Board. We reasoned that, because the
`claims did not specify the source of the 14–hydroxy, any
`prior art reference that disclosed conditions under which
`either 8α or 8β converted to 14–hydroxy would render the
`claim obvious. Id. at 297. We further noted that the prior
`art references did just that—they disclosed the conversion
`of 8β to 14–hydroxy under certain conditions. Id. Thus we
`affirmed the Board’s decision to reject the Chapman
`claims as obvious. Id. at 297–98.
`
`
`Purdue eventually amended the Chapman claims to
`include the claims now on appeal. Unlike the claims in
`the Chapman Application, the claims at issue here are
`product claims instead of process claims, and they
`explicitly recite 8α as the source of at least a portion of
`the minimal amounts of 14–hydroxy remaining in the
`oxyco-done API. In 2010, the U.S. Patent and Trademark
`Office allowed the claims and issued the low-ABUK
`
`4
`
`

`
`exerted 500 N of force.
`
`
`After a series of negotiations, Purdue obtained a license
`from Grunenthal to use the abuse deterrent technology of
`the ′383 patent in its Reformulated OxyContin® product.
`Purdue submitted a New Drug Application to the FDA in
`November 2007, proposing a Reformulated OxyContin®,
`which the FDA approved in April 2010. By July 2012,
`Purdue noted reductions in the abuse of Oxy–Contin®
`and provided that information to the FDA. On April 16,
`2013, the FDA withdrew its approval for Original
`OxyContin® and stopped accepting ANDAs
`that
`proposed generic versions of
`it,
`reasoning
`that
`Reformulated OxyContin® was available to provide the
`same benefits with lower risks of abuse and misuse. On
`the same day, the FDA approved a new label that allowed
`Purdue to market Reformulated OxyContin® on the basis
`of its abuse deterrent properties.
`
`
`
`III. Procedural History
`
`Purdue Pharma L.P. v. Epic Pharma, LLC, --- F.3d ---- (2016)
`
`II. The ′383 Patent
`
`
`
`patents.
`
`
`
`*3 The ′383 patent covers abuse-resistant formulations.
`Original OxyContin® was a popular opioid analgesic
`which delivered a large dose of oxycodone over a
`twelve-hour period. In the early 2000s, however, reports
`of widespread abuse of Original OxyContin® emerged,
`and the problem began to garner significant public
`attention. Original OxyContin® was susceptible
`to
`tampering because abusers could crush the tablets easily
`into powder, which could then be swallowed, snorted, or
`injected for an instant opioid “high.” In 2001, Purdue and
`the FDA changed the label of Original OxyContin® to
`warn doctors about the potential for abusers to tamper
`with the dosage form.
`
`
`reformulate
`to
`investigated ways
`thus
`Purdue
`OxyContin® to deter abuse. Purdue initially considered,
`among other ideas, creating a tablet that would be difficult
`*4 In March 2011, Purdue sued Teva for infringement of
`to crush and difficult to inject, but those efforts were
`ANDA seeking FDA approval to market generic versions
`unsuccessful.
`In 2003, Purdue became aware of
`of Reformulated OxyContin®. Between November 2011
`technology developed by Grunenthal that made tablets
`and January 2013, Purdue filed similar lawsuits against
`extremely hard (in order to prevent crushing) and formed
`Epic, Mylan, and Amneal. In addition, in June 2012,
`a gel upon dissolution in water (in order to prevent
`Grunenthal and Purdue jointly sued Teva for infringement
`injecting).
`of the ′383 patent. The two Teva cases were consolidated
`
`
`and joined with the Epic, Mylan, and Amneal cases, along
`to research abuse resistant
`Grunenthal first began
`with
`six actions
`involving other defendants,
`in
`properties for its opioid product, tapentadol. In October
`multi-district litigation for pretrial purposes.
`2002, Johnson & Johnson proposed a joint venture with
`
`Grunenthal, using Johnson & Johnson’s osmotically
`controlled-release oral delivery system (“OROS”) to deter
`In September 2013, the district court held a three-week
`abuse. The OROS technology consists of a tablet with an
`bench trial in the Teva cases.1 The district court found that
`outer shell that limits the flow of the API from an inner
`the asserted claims were infringed by Teva’s proposed
`core through the use of a “push compartment” in the
`generic product, but it also held that all of the claims were
`tablet. The hard outer shell is composed of high molecular
`invalid as anticipated by or obvious over the prior art.
`District Court Decision, 994 F.Supp.2d at 377. Based on
`weight polyethylene oxide (“PEO”), and the “push
`compartment” expands to force the API through a hole in
`that decision, the district court issued an order for Purdue
`the outer shell. But the tablet could still be easily crushed
`to show cause as to why the actions against Epic, Mylan,
`with a mortar and pestle, so it was not a workable
`and Amneal should not be dismissed under the doctrine of
`solution. Dr. Johannes Bartholomaeus, who was the head
`collateral estoppel. Purdue stated that it intended to appeal
`of pharmaceutical development for Grunenthal at the
`the Teva decision but it agreed that the district court’s
`time, tried to strengthen tapentadol’s dosage form by
`decision regarding the invalidity of the low-ABUK
`making the entire tablet, instead of just the outer shell,
`patents precluded Purdue’s claims for relief against the
`resistant to crushing. Dr. Bartholomaeus thus designed a
`other defendants. Accordingly, the district court dismissed
`formulation that contained a matrix of API and PEO
`the three remaining actions based on collateral estoppel.
`throughout the tablet. Moreover, Dr. Bartholomaeus’s
`
`
`experimentation with PEO demonstrated that using both
`Purdue and Grunenthal appeal the final judgment in the
`heat and pressure to form the tablet resulted in a stronger
`Teva actions and Purdue also appeals the orders of
`solid that resisted breaking by a hammer or by a mortar
`dismissal in the three other cases. We have jurisdiction
`and pestle, and withstood a breaking strength test that
`under 28 U.S.C. § 1295(a)(1).
` © 2016 Thomson Reuters. No claim to original U.S. Government Works.
`
`
`
`5
`
`

`
`of the source of the 14–hydroxy. Id. at 405–06. Moreover,
`the court concluded that the claim limitation requiring that
`the remaining 14–hydroxy is at least in part “derived from
`8α[ ]” is a product-by-process limitation and thus
`immaterial in the obviousness determination. Id. at 405.
`Finally, the district court found that the secondary
`considerations did not demonstrate nonobviousness. Id. at
`407. Purdue alleges clear error in a number of the court’s
`findings, but none of its arguments are meritorious.
`
`
`
`A. Discovery of 8α
`
`Purdue Pharma L.P. v. Epic Pharma, LLC, --- F.3d ---- (2016)
`
`DISCUSSION
`
`
`
`
`
`
`[1] [2] A patent is invalid for anticipation under 35 U.S.C. §
`102 if a single prior art reference discloses each and every
`limitation of the claimed invention. Schering Corp. v.
`Geneva Pharm., 339 F.3d 1373, 1377 (Fed.Cir.2003). A
`single prior art
`reference may anticipate without
`disclosing a feature of the claimed invention if such
`feature
`is necessarily present, or
`inherent,
`in
`that
`reference. Id. Anticipation is a question of fact, which we
`review for clear error. Atlas Powder Co. v. Ireco, Inc.,
`190 F.3d 1342, 1346 (Fed.Cir.1999).
`
`[3] [4] [5] A patent is invalid for obviousness “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.” 35 U.S.C. §
`103(a). Obviousness is a legal conclusion based on
`underlying facts. Graham v. John Deere Co., 383 U.S. 1,
`17, 86 S.Ct. 684, 15 L.Ed.2d 545 (1966). We review the
`underlying findings of fact for clear error, and we review
`de novo the court’s ultimate legal conclusion of whether
`the claimed invention would have been obvious. Novo
`Nordisk A/S v. Caraco Pharm. Labs., Ltd., 719 F.3d 1346,
`1354 (Fed.Cir.2013). Underlying factual inquiries include
`(i) the scope and content of the prior art; (ii) the
`differences between the prior art and the claims at issue;
`(iii) the level of ordinary skill in the field of the invention;
`and (iv) relevant secondary considerations. KSR Int’l Co.
`v. Teleflex, Inc., 550 U.S. 398, 406, 127 S.Ct. 1727, 167
`L.Ed.2d 705 (2007); Graham, 383 U.S. at 17–18.
`
`
`
`First, Purdue contends that the court failed to properly
`credit the discovery of 8α as the core of the claimed
`inventions. It relies heavily on Eibel Process Co. v.
`Minnesota & Ontario Paper Co., 261 U.S. 45, 68, 43
`S.Ct. 322, 67 L.Ed. 523 (1923), for the proposition that
`“where an inventor discovers a non-obvious source of a
`problem and then applies a remedy in response, the
`invention is nonobvious and worthy of a patent—even if
`the remedy, standing alone, would generally appear to be
`known in the art.” Purdue Br. 40. In Eibel Process, the
`invention was a machine that could make quality paper at
`high speeds. 261 U.S. at 54. At the time, paper-making
`machines could not operate at high speeds without
`producing wrinkled paper. Id. Eibel discovered that the
`unequal speeds of paper stock and a wire in the machine
`produced the wrinkled paper. Thus, he made a minor
`modification in the existing paper-making machines: he
`increased the pitch (angle) of the wire so that, through
`gravity, the paper stock would travel at substantially the
`same speed as the wire, and the paper would not wrinkle.
`Id. at 57–58, 64–65. The Supreme Court upheld the
`validity of Eibel’s patent, reasoning that the discovery of
`the problem—unequal speeds of paper stock and the
`wire-was nonobvious, and thus the solution was as well.
`Id. at 68. Purdue contends that, similarly here, the
`discovery of the source of 14–hydroxy was not obvious,
`so the solution of hydrogenating the oxycodone salt must
`also be nonobvious.
`
`
`Purdue’s reliance on Eibel Process is misplaced. Even if
`determining the source of 14–hydroxy in the end product
`was not obvious, that problem did not need to be solved to
`arrive at the claimed invention; thus, Eibel Process does
`not apply. As discussed above, the claimed invention in
`Eibel Process was a machine that remedied the problem
`of wrinkled paper at high-speed printing. But, here,
`Purdue did not claim the remedy of the problem of
`remaining
`14–hydroxy
`in
`the
`oxycodone
`API—performing a second hydrogenation step. Instead, it
`claimed the end product—an oxycodone API with low
` © 2016 Thomson Reuters. No claim to original U.S. Government Works.
`6
`
`I. Invalidity of the Low–ABUK Patents
`
`*5 [6] Purdue challenges the district court’s conclusion
`that the asserted claims of the low-ABUK patents are
`invalid as obvious. Those claims recite an oxycodone API
`product with low ABUK levels.2 The district court found
`that the prior art taught that oxidation of thebaine
`produced 14–hydroxy and that it was well known in the
`art
`that 14–hydroxy
`could be
`removed using
`hydrogenation. District Court Decision, 994 F.Supp.2d at
`395–96. The court further determined that the discovery
`of 8α was not necessary to the claimed invention: a
`skilled artisan would recognize that hydrogenation could
`be used to remove the remaining 14–hydroxy, regardless
`
`
`
`

`
`was because of our decision in Chapman where we said
`the claims were obvious because the claims did not
`differentiate between the 8α and 8β. 315 F. App’x at 297.
`The district court rejected that argument because it found
`that the “derived from 8α[ ]” limitation was a process
`limitation and
`thus
`immaterial
`to
`the obviousness
`analysis.
`
`
`Purdue says, first, the limitation is not a process
`limitation, and, second, even if it is, it should not be
`wholly disregarded. Again, Purdue’s arguments fail.
`
`
`The relevant claim language provides:
`
`An oral dosage form comprising ...
`oxycodone hydrochloride active
`pharmaceutical ingredient having
`less than 25 ppm 14–hydroxy[ ],
`wherein at least a portion of the
`14–hydroxy [ ] is derived from 8 α[
`] during conversion of oxycodone
`free
`base
`to
`oxycodone
`hydrochloride[.]
`
`*7 See, e.g., ′799 patent col. 34 l. 65 to col. 35 l. 4
`(emphasis added). We agree with the district court that
`“derived from 8α[ ]” does not describe the structure of
`14–hydroxy and thus is a process limitation. The patent
`specification describes methods
`for detecting and
`removing 14–hydroxy without regard to the source. For
`example, the written description defines 8,14–dihydroxy
`as 8α, 8β, or a mixture of the two and does not indicate
`any difference in the resulting 14–hydrodxy depending on
`the particular isomer from which it is derived. More
`specifically, there is no suggestion in the patents that the
`hydrogenation process changes depending on whether the
`14–hydroxy is created by 8α or 8β. Indeed, even Purdue’s
`expert testified that “[t]he structure of the 14–hydroxy
`that is generated from 8α is the same structure that is
`generated from 8β .” J.A. 4428. Because the source of the
`14–hydroxy has no effect on its structure or its removal
`through hydrogenation, the limitation that it be “derived
`from 8α[ ]” cannot be a structural limitation.
`
`
`We also conclude that, because “derived from 8α[ ]” is a
`process limitation, the district court did not err in
`disregarding the limitation in its obviousness analysis. We
`have clearly stated that “ ‘[i]n determining validity of a
`product-by-process claim, the focus is on the product and
`not the process of making it.’ “ Greenliant Sys., Inc. v.
`Xicor LLC, 692 F.3d 1261, 1268 (Fed.Cir.2012) (quoting
`Amgen Inc. v. F. Hoffman–La Roche Ltd., 580 F.3d 1340,
`1369 (Fed.Cir.2009)). “That
`is because of
`the
`...
`longstanding rule that an old product is not patentable
`
`Purdue Pharma L.P. v. Epic Pharma, LLC, --- F.3d ---- (2016)
`
`
`
`found,
`the district court
`levels. And, as
`ABUK
`identification of the source of the remaining 14–hydroxy
`as being 8α had no effect on the structure or nature of the
`low-ABUK oxycodone product. Because “[o]ne molecule
`of 14–hydroxy is the same as the next, whether derived
`from 8α or 8β,” knowledge of 8α “did not make
`hydrogenation more or less effective as a technique for
`converting 14–hydroxy to oxycodone.” District Court
`Decision, 994 F.Supp.2d at 405.
`
`
`*6 Purdue also argues that, without knowing that the
`14–hydroxy was derived from 8α, a person of ordinary
`skill in the art would not know when to conduct the
`hydrogenation step or under what conditions to run the
`hydrogenation to create low-ABUK oxycodone. Purdue
`notes that the prior art references were directed to
`lowering 14–hydroxy levels in the oxycodone free base,
`not the API or salt. For example, U.S. Patent No.
`6,177,567 (“Chiu reference”) disclosed a method for
`preparing low-ABUK free base, but it did not teach how
`to convert the low-ABUK free base into low-ABUK salt.
`In fact, as Purdue and the district court noted, Chiu
`completed his method by adding acetic acid to the free
`base. In so doing, Chiu likely converted the latent 8α into
`14–hydroxy in the final product because 8α reacts with
`the acid to form 14–hydroxy. But, again, Purdue claimed
`the end product; it did not claim a particular method for
`creating that product, such as the use of hydrogenation
`after the salting step. In fact, Teva’s generic product
`would not infringe if that were the case because the Teva
`product is not made by hydrogenating the salt—instead
`the free base is purified through two hydrogenation cycles
`and then is treated with acid to create the oxycodone salt.
`Similarly, nothing in the asserted patents indicates that the
`hydrogenation process to remove 14–hydroxy derived
`from 8α must be conducted under different conditions
`from the process used to remove 14–hydroxy that is
`derived from 8β. The issue again comes down to whether
`it would be obvious to a person having ordinary skill in
`the art to use hydrogenation to remove the excess
`14–hydroxy in the oxyco-done API. One need not know
`that the 14–hydroxy was derived from 8α as opposed to
`8β to answer that question.
`
`
`
`B. “Derived from 8α[ ]” Limitation
`
`Purdue next argues that, because the asserted claims
`require that the remaining 14–hydroxy in the oxycodone
`API is derived from 8α and because 8α was not
`previously known in the art as being the source of
`14–hydroxy, th