Case 1:18-cv-00202-IMK Document 1-4 Filed 10/30/18 Page 1 of 238 PageID #: 739
`Case 1:18-cv-00202-IMK Document 1-4 Filed 10/30/18 Page 1 of 238 PageID #: 739
`
`EXHIBIT D
`EXHIBIT D
`
`

`

`Case 1:18-cv-00202-IMK Document 1-4 Filed 10/30/18 Page 2 of 238 PageID #: 740
`
`11111111111111111111111111111101!1111181I11111111111111111110111111
`
`(12) United States Patent
`Baker et al.
`
`(10) Patent No.: (cid:9)
`(45) Date of Patent: (cid:9)
`
`US 9,572,823 B2
`*Feb. 21, 2017
`
`(54)
`
`BORON-CONTAINING SMALL MOLECULES
`
`
`
`
`
`
`
`Applicant: Anacor Pharmaceuticals, Inc., Palo
`Alto, CA (US)
`
`Inventors: Stephen J. Baker, Collegeville, PA
`(US); Tsutomu Akama, Sunnyvale, CA
`(US); Vincent S. Hernandez,
`Watsonville, CA (US); Karin M. Hold,
`Belmont, CA (US); Kirk Maples, San
`Jose. CA (US): Jacob J. Plattner,
`Berkeley, CA (US); Virginia Sanders,
`San Francisco, CA (US); Yong-Kang
`Zhang, San Jose, CA (US); Gregory T.
`Fieldson, Morgantown, WV (US);
`James J. Leyden, Malvern, CA (US)
`
`Assignee: (cid:9) Anacor Pharmaceuticals, Inc., Palo
`Alto, CA (US)
`
`(52)
`
`(58)
`
`( * )
`
`Notice: (cid:9)
`
`Subject to any disclaimer, the term of this
`patent is extended or adjusted under 35
`U.S.C. 154(b) by 0 days.
`
`This patent is subject to a terminal dis-
`claimer.
`
`(56)
`
`Appl. No.: 15/091,394
`
`Filed: (cid:9)
`
`Apr. 5, 2016
`
`(65) (cid:9)
`
`Prior Publication Data
`
`US 2016/0206638 Al (cid:9)
`
`Jul. 21, 2016
`
`Related U.S. Application Data
`(60) Continuation of application No. 15/068,352, filed on
`Mar. 11,2016, which is a continuation of application
`No. 15/046,322, filed on Feb. 17, 2016, which is a
`continuation of application No. 14/537,771, filed on
`Nov. 10, 2014, now abandoned, which is a
`continuation of application No. 14/201,459, filed on
`Mar. 7, 2014, now Pat. No. 9,353,133, which is a
`continuation of application No. 13/356,488, filed on
`Jan. 23, 2012, now Pat. No. 8,722,917, which is a
`continuation of application No. 12/629,753, filed on
`Dec. 2, 2009, now Pat. No. 8,115,026, which is a
`division of application No. 11/505,591, filed on Aug.
`16, 2006, now Pat. No. 7,767,657, which is a
`continuation-in-part of application No. 11/357,687,
`filed on Feb. 16, 2006, now Pat. No. 7,582,621,
`application No. 14/537,771, which is a
`continuation-in-part of application No. 13/874,329,
`filed on Apr. 30,2013, now Pat. No. 8,889,656, which
`is a continuation of application No. 13/224,252, filed
`on Sep. 1, 2011, now Pat. No. 8,440,642, which is a
`continuation of application No. 12/507,010, filed on
`Jul. 21, 2009, now Pat. No. 8,039,451, which is a
`(Continued)
`
`(51) hit. Cl.
`461K 31/69
`CO7F 5/02
`CO7F 5/04
`
`(2006.01)
`(2006.01)
`(2006.01)
`
`C0711 19/06 (cid:9)
`CO7H 19/16 (cid:9)
`CO7H 21/00 (cid:9)
`CO7H 23/00 (cid:9)
`461K 31/70 (cid:9)
`461K 31/7076 (cid:9)
`461K 9/00 (cid:9)
`461K 47/10 (cid:9)
`461K 9/08 (cid:9)
`U.S. Cl.
`CPC (cid:9)
`
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`
` A61K 31/69 (2013.01); 461K 9/0012
`(2013.01); 461K 9/08 (2013.01); A61K 31/70
`(2013.01); 461K 31/7076 (2013.01); 461K
`47/10 (2013.01); CO7F 5/025 (2013.01); CO7F
`5/04 (2013.01); C0711 19/06 (2013.01); CO7H
`19/16 (2013.01); C0711 21/00 (2013.01);
`CO7H 23/00 (2013.01)
`Field of Classification Search
` 514/64
`USPC (cid:9)
`See application file for complete search history.
`
`References Cited
`
`U.S. PATENT DOCUMENTS
`
`2.260,336 A
`2,741,548 A
`
`10/1941 Prescott et al.
`4/1956 Darling ct al.
`(Continued)
`
`FOREIGN PATENT DOCUMENTS
`
`EP
`EP
`
`1/2000
`0969531 (cid:9)
`8/2000
`0765331 B1 (cid:9)
`(Continued)
`
`OTHER PUBLICATIONS
`
`Baudoin, Olivier, et al. "A Novel 1,3-Central-to-Axial Chirality
`Induction Approach to Cyclooctadiene Lignans", Synlett, Oct. 16,
`2003, No. 13, pp. 2009-2012.
`(Continued)
`
`Primary Examiner — Rei-Tsang Shiao
`(74) Attorney, Agent, or Firm — Morgan, Lewis &
`Bockius LLP
`
`(57) (cid:9)
`
`ABSTRACT
`
`This invention relates to compounds useful for treating
`fungal infections, more specifically topical treatment of
`onychomycosis and/or cutaneous fungal infections. This
`invention is directed to compounds that are active against
`fungi and have properties that allow the compound, when
`placed in contact with a patient, to reach the particular part
`of the skin, nail, hair, claw or hoof infected by the fungus.
`In particular the present compounds have physiochemical
`properties that facilitate penetration of the nail plate.
`
`6 Claims, 63 Drawing Sheets
`
`(cid:9)
`(cid:9)
`(cid:9)
`(cid:9)
`(cid:9)
`(cid:9)
`(cid:9)
`(cid:9)
`(cid:9)
`

`

`Case 1:18-cv-00202-IMK Document 1-4 Filed 10/30/18 Page 3 of 238 PageID #: 741
`
`US 9,572,823 B2
`Page 2
`
`Related U.S. Application Data (cid:9)
`continuation of application No. 11/357,687, filed on (cid:9)
`Feb. 16, 2006, now Pat. No. 7,582,621. (cid:9)
`
`(60) Provisional application No. 60/755.227, filed on Dec. (cid:9)
`30, 2005, provisional application No. 60/746,361, (cid:9)
`
`filed on May 3, 2006, provisional application No. (cid:9)
`60/654,060, filed on Feb. 16, 2005. (cid:9)
`
`(56) (cid:9)
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`

`Case 1:18-cv-00202-IMK Document 1-4 Filed 10/30/18 Page 4 of 238 PageID #: 742
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`
`

`

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`
`US 9,572,823 B2
`Page 4
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`
`

`

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`US 9,572,823 B2
`Page 5
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