throbber
Paper No. ____
`Date Filed: May 26, 2015
`
`Filed On Behalf Of:
`
`Novartis AG and LTS Lohmann Therapie-Systeme AG
`
`By:
`
`Raymond R. Mandra
`ExelonPatchIPR@fchs.com
`(212) 218-2100
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`NOVEN PHARMACEUTICALS INC.
`AND MYLAN PHARMACEUTICALS INC.,
`Petitioners
`
`v.
`
`NOVARTIS AG AND LTS LOHMANN THERAPIE-SYSTEME AG,
`Patent Owners
`
`Inter Partes Review No. 2014-005501
`
`U.S. Patent 6,335,031
`
`PATENT OWNERS’ DEMONSTRATIVE
`EXHIBITS PURSUANT TO 37 C.F.R. § 42.70(b)
`
`1 Case IPR2015-00268 has been joined with this proceeding.
`
`

`

`UNITED STATES PATENT AND TRADEMARK OFFICE
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`NOVEN PHARMACEUTICALS INC.
`AND MYLAN PHARMACEUTICALS INC.,
`Petitioners
`
`v.
`
`NOVARTIS AG AND LTS LOHMANN THERAPIE-SYSTEME AG,
`Patent Owners
`
`Inter Partes Review Nos. 2014-00550, 2014-00268
`
`U.S. Patent 6,335,031
`
`PATENT OWNERS’ DEMONSTRATIVE
`EXHIBITS FOR ORAL HEARING
`
`June 2, 2015
`
`1
`
`

`

`Professor Alexander M. Klibanov
`
`• Professor of Chemistry and Bioengineering at M.I.T.
`
`• Elected to the U.S. National Academy of Sciences
`
`• Elected to the U.S. National Academy of Engineering
`
`• Over 45 years as a practicing chemist
`
`• Published over 300 scientific papers
`
`• Given 370 invited lectures
`
`Ex. 2012 at ¶¶ 1-8; Ex. 2013
`
`2
`
`

`

`Leo Recognizes That Discovery Of A
`Problem May Be A Patentable Invention
`Paper 25 at 5, 7-8
`
`Leo Pharm. Prods., Ltd. v. Rea, 726 F.3d 1346, 1354 (Fed. Cir. 2013)
`
`3
`
`

`

`Omeprazole Recognizes That Discovery
`Of A Problem May Be A Patentable Invention
`Paper 25 at 5
`
`In re Omeprazole Patent Litig., 536 F.3d 1361, 1380 (Fed. Cir. 2008)
`
`4
`
`

`

`Was Rivastigmine Known Or Reasonably Suggested
`To Have An Oxidative Degradation Problem?
`Paper 25 at 10-12, 13-44
`The Art Taught That Rivastigmine Was Chemically Stable
`• Enz (Ex. 1002)
`• Enz 1991 (Ex. 2026)
`• Rosin (Ex. 1008)
`• Weinstock 1994 (Ex. 2027)
`• Elmalem (Ex. 1009)
`A POSA Would Not Reasonably Have Predicted That
`Rivastigmine Would Oxidatively Degrade Based On Its Structure
`• Benzylic C-H bond and an adjacent tertiary amine (nicotine)
`• Amines (Sasaki) (Ex. 1005)
`A POSA Would Not Have Been Motivated To
`Combine Rivastigmine With An Antioxidant Unless Required
`• Ebert (Ex. 1006)
`• Handbook of Pharmaceutical Excipients (Ex. 1003)
`
`Ex. 2012 at ¶ 51
`
`5
`
`

`

`Prior Art Reported Greater Chemical Stability Of
`Rivastigmine And RA7 And/Or Did No Add An Antioxidant
`Paper 25 at 13-15, 21-22, 25-26, 27-28, 36
`Enz (Ex. 1002) Did not add an antioxidant to rivastigmine
`Did not add an antioxidant to RA7
`Rosin
`(Ex. 1008)
`RA7’s greater in vivo activity over physostigmine “may
`be due to . . . greater chemical stability . . . .”
`RA7 has “a greater chemical stability and longer
`duration of action than that of physostigmine . . . .”
`Did not add an antioxidant to rivastigmine
`Rivastigmine “appears to have greater chemical
`stability . . . than does physostigmine.”
`Did not add an antioxidant to rivastigmine
`“In animals and human subjects [rivastigmine] showed
`superior chemical stability . . . than physostigmine.”
`
`Elmalem
`(Ex. 1009)
`
`Enz 1991
`(Ex. 2026)
`
`Weinstock 1994
`(Ex. 2027)
`
`Ex. 1002 at 19; Ex. 1008 at 3:37-39, 11:21-29; Ex. 1009 at 1; Ex. 2026 at 2; Ex. 2027 at 2-3; Ex. 2012 ¶¶ 47, 54, 68, 72, 74
`
`6
`
`

`

`Prior Art Reported Greater Chemical Stability Of
`Rivastigmine And RA7 And/Or Did No Add An Antioxidant
`Paper 25 at 13-15, 21-22, 25-26, 27-28, 36
`Reference
`Did Not Add An
`Antioxidant To
`Rivastigmine/RA7
`
`Reported
`Rivastigmine/RA7 Has
`Greater Chemical Stability
`Than Physostigmine
`
`Enz
`(Ex. 1002)
`Rosin
`(Ex. 1008)
`Elmalem
`(Ex. 1009)
`Enz 1991
`(Ex. 2026)
`Weinstock 1994
`(Ex. 2027)
`
`Ex. 1002 at 19; Ex. 1008 at 3:37-39, 11:21-29; Ex. 1009 at 1; Ex. 2026 at 2; Ex. 2027 at 2-3; Ex. 2012 ¶¶ 47, 54, 68, 72, 74
`
`7
`
`

`

`A POSA Would Not Add An
`Antioxidant Unless Required
`Paper 25 at 10-11
`Remington’s (Ex. 2017):
`
`Ansel (Ex. 2020):
`
`Ex. 2017 at 6; Ex. 2020 at 11; Ex. 2012 at ¶¶ 38-39, 41
`
`8
`
`

`

`A POSA Would Not Add An
`Antioxidant Unless Required
`Paper 25 at 10-11
`
`EMEA Guidelines (Ex. 2019):
`
`Ex. 2019 at 4; Ex. 2012 at ¶ 40
`
`9
`
`

`

`Petitioners Fail To Consider
`Elmalem And The Prior Art As A Whole
`Paper 25 at 29-31
`
`Elmalem (Ex. 1009):
`
`Ex. 1009 at 2; Ex. 2012 at ¶¶ 76, 97, 104
`
`10
`
`

`

`Physostigmine Was Known To Undergo Hydrolysis
`
`Paper 25 at 31
`
`Rosin (Ex. 1008):
`
`Ex. 1008 at 1:32-34, 2:45-47; Ex. 2012 at ¶¶ 78, 82
`
`11
`
`

`

`An Antioxidant Prevents The Oxidation
`Of Physostigmine’s Hydrolytic Degradant
`Paper 25 at 31
`
`Wilson & Gisvold (Ex. 2038):
`
`Ex. 2038 at 3; Ex. 2012 at ¶¶ 84-85
`
`12
`
`

`

`Elmalem States That RA7 Has Greater
`Chemical Stability Than Physostigmine
`Paper 25 at 28
`
`Elmalem (Ex. 1009):
`
`Ex. 1009 at 1; Ex. 2012 at ¶¶ 48, 96
`
`13
`
`

`

`Elmalem Quantitatively Compared The Effects Of Different
`Drugs On Morphine-Induced Respiratory Depression
`Paper 25 at 28
`
`Elmalem (Ex. 1009):
`
`Ex. 1009 at 1; Ex. 2012 at ¶¶ 77, 98
`
`14
`
`

`

`Elmalem Was A Well-Controlled Study
`Paper 25 at 28-29, 32
`
`Formulation Controls:
`• All drugs formulated with an antioxidant
`Route Of Administration Controls:
`• All drugs administered by injection
`Test Subject Controls:
`• At least 4 rabbits/treatment
`• All rabbits similar size (2.5 to 3 kg)
`• Dosages calculated per kg body weight
`• Blood samples analyzed before treatment
`• Changes in body temperature monitored
`• Differences in respiration rates normalized
`
`Ex. 1009 at 1-2; Ex. 2012 at ¶¶ 99-103
`
`15
`
`

`

`Weinstock 1994 Did Not Suggest That Rivastigmine
`Requires An Antioxidant In Any Formulation
`Paper 25 at 36
`
`Weinstock 1994 (Ex. 2027):
`
`Ex. 2027 at 2; Ex. 2012 at ¶¶ 47, 74
`
`16
`
`

`

`Petitioners’ Reading Of Elmalem Adds
`A Variable To The Well-Controlled Study
`Paper 25 at 33-34
`
`Elmalem (Ex. 1009):
`
`Ex. 1009 at 2; Ex. 2012 at ¶ 110
`
`17
`
`

`

`Antioxidant Amount Is Not
`Calculated Based On The Amount Of Drug
`Paper 42 at 9-10; see also Paper 25 at 33-34
`
`Dr. Kydonieus (Ex. 1049):
`
`Ex. 1049 at 59:9-20; see also Ex. 2012 at ¶ 110
`
`18
`
`

`

`Elmalem And Weinstock 1981 Studies
`Were Conducted For Different Purposes
`Paper 25 at 34-35 n.7
`
`Elmalem (Ex. 1009):
`
`Weinstock 1981 (Ex. 2046):
`
`Ex. 1009 at 1; Ex. 2046 at 1; Ex. 2012 at ¶¶ 112-16
`
`19
`
`

`

`Elmalem And Weinstock 1981
`Used Different Experimental Designs
`Paper 25 at 34-35 n.7; Paper 42 at 10-11
`
`Elmalem (Ex. 1009):
`
`Weinstock 1981 (Ex. 2046):
`
`Ex. 1009 at 2; Ex. 2046 at 2; Ex. 2012 at ¶¶ 117-18
`
`20
`
`

`

`Rosin Discloses Millions Of
`“Compounds Of The Invention”
`Paper 25 at 24-25
`
`Rosin (Ex. 1008):
`
`Ex. 1008 at 4:21-53; Ex. 2012 at ¶ 63
`
`21
`
`

`

`Rosin Discloses Compositions
`For Oral And Parenteral Administration
`Paper 25 at 25
`
`Rosin (Ex. 1008):
`
`Ex. 1008 at 7:15-19; Ex. 2012 at ¶ 69
`
`22
`
`

`

`Rosin Discloses Use Of Antioxidants In Sterile
`Compositions For Injection Only As Required
`Paper 25 at 25
`
`Rosin (Ex. 1008):
`
`Ex. 1008 at 7:45-53; Ex. 2012 at ¶¶ 64-67
`
`23
`
`

`

`Enz Confirms That Rosin Does Not Suggest
`An Oxidative Degradation Problem For RA7
`Paper 25 at 26-27
`
`Enz (Ex. 1002):
`
`Ex. 1002 at 3; Ex. 2012 at ¶ 57
`
`24
`
`

`

`Rosin Discloses Millions Of
`“Compounds Of The Invention”
`Paper 25 at 24-25
`
`Rosin (Ex. 1008):
`
`Ex. 1008 at 4:21-53; Ex. 2012 at ¶ 63
`
`25
`
`

`

`The “Compounds Of The Present Invention” Are
`The Large Class Of Eight Million-Plus Compounds
`Paper 42 at 7-8; see also Paper 25 at 24-25 & n.4
`
`Rosin Priority Application (Ex. 2058):
`
`Ex. 2058 at 18, 31; Ex. 1049 at 35:23-36:19, 37:16-39:5
`
`26
`
`

`

`Neither Rosin Nor Elmalem Discloses Transdermals
`Paper 42 at 13; Paper 44 at 12-13; see also Paper 25 at 3-4, 27, 36
`
`Dr. Kydonieus (Ex. 1025):
`
`Ex. 1025 at 249:16-18, 257:17-19; see also Ex. 1025 at 186:6-10; Ex. 1049 at 39:15-25
`
`27
`
`

`

`Whether Rivastigmine Undergoes
`Oxidative Degradation Is Formulation-Specific
`Paper 25 at 4, 13, 27, 35-36
`
`Dr. Schöneich (Ex. 1025):
`
`Ex. 1025 at 95:24-96:6; see also Ex. 2012 at ¶ 49
`
`28
`
`

`

`Whether Rivastigmine Undergoes
`Oxidative Degradation Is Formulation-Specific
`Paper 25 at 4, 13, 27, 35-36
`
`Dr. Kydonieus (Ex. 1025):
`
`Ex. 1025 at 258:8-13; see also Ex. 2012 at ¶ 49
`
`29
`
`

`

`Dosage Form Can Determine
`Whether An Antioxidant Is Required
`Paper 44 at 12-13; see also Paper 25 at 13
`
`Dr. Schöneich
`(Ex. 1048):
`
`Ex. 1048 at 70:3-6, 70:21-71:12; see also Ex. 2012 at ¶ 49
`
`30
`
`

`

`Hydrolysis Of Carbamates Had Been
`Studied Experimentally Since The 1930s
`Paper 25 at 31-32; Paper 44 at 13
`
`Dr. Schöneich (Ex. 1048):
`
`Ex. 1048 at 25:17-26:2; Ex. 2012 at ¶¶ 78, 81-82, 84-96
`
`31
`
`

`

`Mechanisms Of Hydrolysis Of Carbamates
`Had Been Experimentally Determined As Of 1998
`Paper 25 at 31-32; Paper 44 at 13
`
`Dr. Schöneich (Ex. 1048):
`
`Ex. 1048 at 26:11-20; Ex. 2012 at ¶¶ 78, 81-82, 84-96
`
`32
`
`

`

`Oxidative Mechanisms Were
`Poorly Understood As Of 1998
`Paper 25 at 18
`
`Modern Pharmaceutics (Ex. 2014):
`
`Connors (Ex. 1015):
`
`Ex. 2014 at 7; Ex. 1015 at 3; Ex. 2012 at ¶ 121
`
`33
`
`

`

`Testing Was Required To Determine Intrinsic Stability
`Paper 25 at 19
`
`Dr. Kydonieus (Ex. 1010):
`
`Ex. 1010 at ¶ 25; Ex. 1014 at 2; Ex. 2012 at ¶ 35
`
`34
`
`

`

`Bond Strengths Do Not Indicate The
`Conditions Under Which A Radical Will Form
`Paper 44 at 1; see also Paper 25 at 16
`Dr. Schöneich (Ex. 1048):
`
`Ex. 1048 at 22:6-23:22
`
`35
`
`

`

`Testing Is Required To Determine Whether Rivastigmine
`Oxidative Degrades Under Pharmaceutically Relevant Conditions
`Paper 25 at 2, 13-14, 16, 19-20, 22, 23, 27, 35-36, 42
`
`Dr. Schöneich (Ex. 1025):
`
`Ex. 1025 at 96:10-18
`
`36
`
`

`

`Testing Is Required To Determine Whether Rivastigmine
`Oxidative Degrades Under Pharmaceutically Relevant Conditions
`Paper 25 at 2, 13-14, 16, 22, 23, 27, 35-36, 42
`
`Dr. Kydonieus (Ex. 1025):
`
`Ex. 1025 at 232:6-13
`
`37
`
`

`

`Dextromethorphan Is “Especially Susceptible”
`To Oxidative Degradation But “Very Stable”
`Paper 25 at 17; Paper 44 at 2-4
`
`Carey & Sundberg
`(Ex. 1007):
`• Benzylic positions are
`“especially susceptible” to
`oxidation
`Dr. Schöneich’s opinion
`(Exs. 1011, 1032):
`•
`“Dextromethorphan Was
`Known To Be Susceptible
`To Oxidation”
`• Dextromethorphan was
`“prone to oxidation”
`
`The prior art teaches
`(Exs. 2050, 2051):
`• Dextromethorphan is “very
`stable”
`• Dextromethorphan is
`“stable under all normal
`conditions of storage”
`• Dextromethorphan has
`“excellent stability” under
`pharmaceutically relevant
`conditions
`
`Ex. 1007 at 45; Ex. 1011 at ¶ 47; Ex. 1032 at ¶¶ 11, 60; Ex. 2050 at 6; Ex. 2051 at 4-5; Ex. 2012 at ¶¶ 140-41
`
`38
`
`

`

`Drugs With Structural Features Of Rivastigmine
`Were Not Reported To Undergo Oxidation
`Paper 25 at 18
`
`Ampicillin
`
`Mirtazapine
`
`Hydroxyzine
`
`Benzquinamide
`
`Meclizine
`
`Ex. 2022 at 68, 73, 75, 77, 78, 82, 92; Ex. 2012 at ¶¶ 132-34
`
`39
`
`

`

`Dr. Schöneich Provided No Evidence To Show
`Dr. Klibanov’s Real-World Pharmaceuticals Were Unstable
`Paper 44 at 5-6; Paper 25 at 18
`
`Dr. Schöneich (Ex. 1048):
`
`Ex. 1048 at 49:13-22
`
`40
`
`

`

`Dr. Schöneich Provided No Evidence To Show
`Dr. Klibanov’s Real-World Pharmaceuticals Were Unstable
`Paper 44 at 5-6; see also Paper 25 at 18
`
`Dr. Schöneich (Ex. 1048):
`
`Ex. 1048 at 50:5-16; see also Ex. 2012 at ¶¶ 132-34
`
`41
`
`

`

`PDR Reports Chemical Instability Of Nicotine
`Paper 44 at 8; see also Paper 25 at 17-18
`
`Physicians’ Desk Reference (Ex. 2022):
`
`Dr. Schöneich (Ex. 1048):
`
`Ex. 2022 at 27, 46; Ex. 1048 at 54:12-58:18
`
`42
`
`

`

`There Are Reasons Other Than
`Oxidative Instability To Select A Dry Dosage Form
`Paper 44 at 11; see also Paper 25 at 18
`
`Dr. Schöneich (Ex. 1048):
`
`Ex. 1048 at 71:21-73:7; see also Ex. 2012 at ¶ 134
`
`43
`
`

`

`The Salt Form Of A Drug May
`Undergo Oxidative Degradation
`Paper 42 at 4-5; see also Paper 25 at 18
`
`Dr. Kydonieus (Ex. 1049):
`
`Ex. 1049 at 93:6-94:5; see also Ex. 2012 at ¶ 134
`
`44
`
`

`

`Formulation In A Dry Dosage Form Does Not Indicate
`The Real-World Pharmaceuticals Are Susceptible To Oxidation
`Paper 44 at 11; see also Paper 25 at 18
`
`Petitioners’ Response (Paper 52):
`
`Paper 52 at 10-11; see also Ex. 2012 at ¶ 134
`
`45
`
`

`

`Whether Rivastigmine Would Degrade In An Acrylic Adhesive
`Could Not Be Reasonably Predicted From Its Structure
`Paper 25 at 42
`
`Dr. Kydonieus (Ex. 1025):
`
`Ex. 1025 at 283:12-24; see also Ex. 2012 at ¶ 156 & n.17
`
`46
`
`

`

`Enz Discloses Rivastigmine In An Acrylic
`Adhesive Without Requiring An Antioxidant
`Paper 25 at 43
`
`Enz (1002):
`
`Ex. 1002 at 19; Ex. 2012 at ¶ 158
`
`47
`
`

`

`A POSA Would Not Believe That All Amines Break Down
`In Acrylic Adhesives Based On Two Amines In Sasaki
`Paper 25 at 41-42
`
`Sasaki (Ex. 1005):
`
`Dr. Klibanov (Ex. 2012):
`
`Ex. 1005 at 1; Ex. 2012 at ¶ 156
`
`48
`
`

`

`Rivastigmine
`Rivastigmine
`Paper 25 at 17
`Paper 25 at 17
`
`CH3
`
`o
`
`Hep/\ITIJLO
`
`Ex. 1001 at 1:8-15; Ex. 2012 at ¶¶ 80, 96 n.8, 145
`Ex. 1001 at 1:8-15; Ex. 2012 at1l1l 80, 96 n.8, 145
`
`49
`
`

`

`Amine-Containing Drugs Were Not Reported To
`Contain Antioxidants In Commercial Formulations
`Paper 25 at 42
`
`Fentanyl
`
`Meclizine
`
`Scopolamine
`
`Mirtazapine
`
`Hydroxyzine
`
`Benzquinamide
`
`Ex. 2022 at 32, 36, 68, 73, 75, 77, 82; Ex. 2012 at ¶¶ 132-35, 157
`
`50
`
`

`

`Amine Or Phenolic Hydroxyl Compounds In An Acrylic
`Adhesive Were Not Reported To Contain An Antioxidant
`Paper 25 at 42-43 & n.11
`
`Physicians’ Desk Reference (Ex. 2022):
`
`Estradiol
`
`Nicotine
`
`Ex. 2022 at 6, 23, 27; Ex. 2012 at ¶¶ 157 & n.18
`
`51
`
`

`

`“Susceptibility” Does Not Indicate Whether
`Rivastigmine Will Undergo Any Oxidative Degradation
`Paper 42 at 4; see also Paper 25 at 13, 16
`
`Dr. Kydonieus (Ex. 1031):
`
`Ex. 1031 at ¶ 10; Ex. 1025 at 96:10-18
`
`52
`
`

`

`Ebert Discloses An Unconventional Method
`Paper 25 at 37-38
`
`Dr. Klibanov (Ex. 2012):
`
`Ex. 2012 at ¶¶ 169, 171; Ex. 1006 at 1:13-20, 5:16-21, 19:34-20:12
`
`53
`
`

`

`Rivastigmine Transdermal Can Be
`Prepared Using Conventional Methods
`Paper 25 at 37-38
`
`Enz (Ex. 1002):
`
`Ex. 1002 at 11, 17, 20; Ex. 2012 at ¶ 169
`
`54
`
`

`

`Dated: May 26, 2015
`
`Respectfully submitted,
`
`/s/ Raymond R. Mandra
`Raymond R. Mandra
`Registration No. 34,382
`FITZPATRICK, CELLA, HARPER
`& SCINTO
`1290 Avenue of the Americas
`New York, NY 10104-3800
`
`

`

`CERTIFICATE OF SERVICE
`
`I certify that a copy of the foregoing PATENT OWNERS’
`
`DEMONSTRATIVE EXHIBITS PURSUANT TO 37 C.F.R. § 42.70(b) were
`
`served on May 26, 2015 by causing them to be sent by email to counsel for
`
`Petitioners at the following email addresses:
`
`Steven J. Lee (slee@kenyon.com)
`
`Michael K. Levy (mlevy@kenyon.com)
`
`Chris Coulson (ccoulson@kenyon.com)
`
`Joseph M. Reisman (BoxMylan2@knobbe.com)
`
`Jay R. Deshmukh (BoxMylan2@knobbe.com)
`
`William R. Zimmerman (BoxMylan@knobbe.com)
`
`Dated: May 26, 2015
`
`/s/ Raymond R. Mandra
`Raymond R. Mandra
`Registration No. 34,382
`FITZPATRICK, CELLA, HARPER
`& SCINTO
`1290 Avenue of the Americas
`New York, NY 10104-3800
`Tel. 212-218-2100
`
`

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