UNITED STATES PATENT AND TRADEMARK OFFICE
`__________________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`__________________
`
`FLATWING PHARMACEUTICALS, LLC,
`Petitioner,
`
`v.
`
`ANACOR PHAMACEUTICALS, INC.,
`Patent Owner
`__________________
`
`Case No. IPR2018-00168
`Patent No. 9,549,938
`__________________
`
`PATENT OWNER’S EXHIBIT LIST
`
`
`
`
`
`
`
`__________________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`__________________
`
`FLATWING PHARMACEUTICALS, LLC,
`Petitioner,
`
`v.
`
`ANACOR PHAMACEUTICALS, INC.,
`Patent Owner
`__________________
`
`Case No. IPR2018-00168
`Patent No. 9,549,938
`__________________
`
`PATENT OWNER’S EXHIBIT LIST
`
`
`
`
`
`
`
`
`Exhibit
`2002
`
`2003
`
`2004
`
`2005
`
`2006
`
`2007
`
`2008
`
`2009
`
`2010
`
`2011
`
`2012
`
`2013
`2014
`2015
`
`Case No. IPR2018-00168
`U.S. Patent No. 9,549,938
`
`
`LIST OF EXHIBITS
`
`Description
`Transcript of May 2016 Deposition of S. Narasimha Murthy,
`Ph.D.
`Transcript of September 2016 Deposition of S. Narasimha
`Murthy, Ph.D.
`Nair et al., Alteration of the diffusional barrier property of
`the nail leads to greater terbinafine drug loading and perme-
`ation, Int’l J. Pharm., vol. 375, pp. 22–27 (2009)
`Nair et al., A study on the effect of inorganic salts in transun-
`gual drug delivery of terbinafine, J. Pharm. Pharmacol., vol.
`61, pp. 431–37 (2009)
`Shivakumar et al., Bilayered Nail Lacquer of Terbinafine Hy-
`drochloride for Treatment of Onychomycosis, J. Pharm. Sci.,
`vol. 99, pp. 4267–76 (2010)
`Shivakumar et al., Transungual drug delivery: an update, J.
`Drug Del. Sci. Tech., vol. 24, pp. 301–10 (2014)
`Murthy et al., Iontophoretic Drug Delivery across Human
`Nail, J. Pharm. Sci., vol. 96, pp. 305–11 (2007)
`Gupta et al., The use of topical therapies to treat onychomy-
`cosis, Dermatol. Clin., vol. 21, pp. 481–89 (2003)
`Transcript of April 2016 Deposition of Stephen B. Kahl,
`Ph.D.
`Transcript of September 2016 Deposition of Stephen B. Kahl,
`Ph.D.
`Structural Diagrams from August 2018 Deposition of Stephen
`B. Kahl, Ph.D.
`Declaration of Paul J. Reider, Ph.D.
`Declaration of Majella E. Lane, Ph.D.
`Baker et al., Therapeutic potential of boron-containing com-
`pounds, Future Med. Chem., vol. 1, pp. 1275–88 (2009)
`
`1
`
`
`
`Exhibit
`2016
`
`2017
`
`2018
`
`2019
`
`2020
`
`2021
`
`2022
`
`2023
`
`2024
`
`2025
`
`2026
`
`Case No. IPR2018-00168
`U.S. Patent No. 9,549,938
`
`
`Description
`Dennis G. Hall, Structure, Properties, and Preparation of
`Boronic Acid Derivatives: Overview of Their Reactions and
`Applications, in Boronic Acids: Preparation and Applications
`in Organic Synthesis, Medicine and Materials, Second Edi-
`tion (Dennis G. Hall ed. 2011)
`Transcript of August 23, 2018 Deposition of Stephen B.
`Kahl, Ph.D.
`Transcript of August 20, 2018 Deposition of S. Narasimha
`Murthy, Ph.D.
`McNamara et al., Synthesis of Unsymmetrical Dithioacetals:
`An Efficient Synthesis of a Novel LTD4 Antagonist, L-
`660,711, J. Org. Chem., vol. 54, pp. 3718–21 (1989)
`Ryan et al., Enhanced Reactivity of Iminium Ions as Hetero-
`dienophiles in Lewis Acid Mediated 4+2 Cycloaddition Reac-
`tions, Tetrahedron Letters, vol. 28, pp. 2103–06 (1987)
`Brown et al., Boron in Plant Biology, Plant Biol. vol. 4, pp.
`205–23 (2002)
`J.D. Lloyd, Borates and their biological applications, 29th
`Annual meeting of the International Research Group on
`Wood Preservation (June 1998)
`William G. Woods, Review of Possible Boron Speciation Re-
`lating to its Essentiality, J. Trace Elements in Exp. Med., vol.
`9, pp. 153–63 (1996)
`Steiner et al., Diphenylborinic Acid Is a Strong Inhibitor of
`Serine Proteases, Bioorg. & Med. Chem. Lett., vol. 4, pp.
`2417–20 (1994)
`Zhdankin et al, Synthesis and structure of benzoboroxoles:
`novel organoboron heterocycles, Tetrahedron Letters, vol.
`40, pp. 6705–08 (1999)
`Dowlut & Hall, An Improved Class of Sugar-Binding Boronic
`Acids, Soluble and Capable of Complexing Glycosides in
`Neutral Water, J. Am. Chem. Soc., vol. 128, pp. 4226–27
`(2006)
`
`2
`
`
`
`Exhibit
`2027
`
`2028
`
`2029
`
`2030
`
`2031
`
`2032
`
`2033
`
`2034
`
`2035
`
`Case No. IPR2018-00168
`U.S. Patent No. 9,549,938
`
`
`Description
`Boni E. Elewski, Onychomycosis: Pathogenesis, Diagnosis,
`and Management, Clin. Microbiology Revs., vol. 11, pp.
`415–29 (1998)
`Wang et al., Keratin: Structure, mechanical properties, oc-
`currence in biological organisms, and efforts at bioinspira-
`tion, Prog. Mater. Sci., vol. 76, pp. 229–318 (2016)
`Runne & Orfanos, The Human Nail: Structure, Growth and
`Pathological Changes, Curr. Prob. Derm. vol. 9, pp. 102–49
`(1981)
`Topical Nail Products and Ungual Drug Delivery (Murthy &
`Maibach eds. 2013)
`Walters et al., Physicochemical characterization of the hu-
`man nail: permeation pattern for water and the homologous
`alcohols and differences with respect to the stratum corneum,
`J. Pharm. Pharmacol. vol. 35, pp. 28–33 (1983)
`Kobayashi et al., In vitro permeation of several drugs through
`the human nail plate: relationship between physicochemical
`properties and nail permeability of drugs, Eur. J. Pharm. Sci.,
`vol. 21 pp. 471–77 (2004)
`Mertin & Lippold, In-vitro Permeability of the Human Nail of
`a Keratin Membrane from Bovine Hooves: Influence of the
`Partition Coefficient Octanol/Water and the Water Solubility
`of Drugs on their Permeability and Maximum Flux, J. Pharm.
`Pharmacol., vol. 49, pp. 30–34 (1997)
`Mertin & Lippold, In-vitro Permeability of the Human Nail
`and of a Keratin Membrane from Bovine Hooves: Penetra-
`tion of Chloramphenicol from Lipophilic Vehicles and a Nail
`Lacquer, J. Pharm. Pharmacol., vol. 49, pp. 241–45 (1997)
`Pollak et al., Efinaconazole Topical Solution, 10%: Factors
`Contributing to Onychomycosis Success, J. Fungi, vol. 1, pp.
`107–14 (2015)
`
`3
`
`
`
`Case No. IPR2018-00168
`U.S. Patent No. 9,549,938
`
`
`Description
`Sugiura et al., The Low Keratin Affinity of Efinaconazole
`Contributes to Its Nail Penetration and Fungicidal Activity in
`Topical Onychomycosis Treatment, Antimicrobial Agents &
`Chemotherapy, vol. 58, pp. 3837–42 (2014)
`Tatsumi et al., Therapeutic Efficacy of Topically Applied KP-
`103 against Experimental Tinea Unguium in Guinea Pigs in
`Comparison with Amorolfine and Terbinafine, Antimicrobial
`Agents & Chemotherapy, vol. 46, pp. 3797–801 (2002)
`Biobor JF Service Bulletin No. 982
`Yao et al., Borate Esters Used as Lubricant Additives, Lubri-
`cation Science, vol. 14, pp. 415–23 (2002)
`Lee & Wong, Toxic Effects of Some Alcohol and Ethylene
`Glycol Derivatives on Cladosporium resinae, Applied & En-
`vtl. Microbiol., vol. 38, pp. 24–28 (1979)
`Marova et al., Non-enzymatic glycation of epidermal proteins
`of the stratum corneum in diabetic patients, Acta Diabetolog-
`ica, vol. 32, pp. 38–43 (1995)
`Bakan & Bakan, Glycosylation of nail in diabetics: possible
`marker of long-term hyperglycaemia, Clin. Chim. Acta, vol.
`147, pp 1–5 (1985)
`Bo Forslind, Biophysical Studies of the Normal Nail, Acta
`Derm Venerol, vol. 5, pp. 161–68, (1970)
`Curriculum Vitae of Paul J. Reider, Ph.D.
`Curriculum Vitae of Majella E. Lane, Ph.D.
`
`Exhibit
`2036
`
`2037
`
`2038
`2039
`
`2040
`
`2041
`
`2042
`
`2043
`
`2044
`2045
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`
`
`Date: September 7, 2018
`
`
`
`
`
` Respectfully submitted,
`
`/s/ Aaron P. Maurer
`Aaron P. Maurer (Reg. No. 44,911)
`David I. Berl (Reg. No. 72,751)
`Anthony. H. Sheh (Reg. No. 70,576)
`Williams & Connolly LLP
`725 Twelfth Street, N.W.
`
`
`
`4
`
`
`
`Case No. IPR2018-00168
`U.S. Patent No. 9,549,938
`
`
`Washington, DC 20005
`T: (202) 434-5000
`F: (202) 434-5029
`amaurer@wc.com
`dberl@wc.com
`asheh@wc.com
`
`Counsel for Patent Owner
`
`
`
`
`
`
`
`5
`
`
`
`CERTIFICATE OF SERVICE (37 C.F.R. § 42.6(e))
`
`Case No. IPR2018-00168
`U.S. Patent No. 9,549,938
`
`
`Pursuant to 37 C.F.R. § 42.6, I hereby certify that this 7th day of September
`
`2018, a true and correct copy of the foregoing was served via electronic mail on
`
`the following counsel of record.
`
`Philip D. Segrest, Jr.
`Eric J. Rakestraw
`Edward D. Manzo
`Husch Blackwell LLP
`120 South Riverside Plaza, Suite 2200
`Chicago, Illinois 60606
`Philip.Segrest@HuschBlackwell.com
`Eric.Rakestraw@HuschBlackwell.com
`PTAB-ERakestraw@HuschBlackwell.com
`Edward.Manzo@HuschBlackwell.com
`
`
`
`
`
`
`
`
`
`/Anthony H. Sheh/
`Anthony H. Sheh (Reg. No. 70,576)
`
`
`
`
`6
`
`
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