(12) United States Patent
`US 9,549,938 B2
`(10) Patent N0.:
`
` Baker et al. (45) Date of Patent: *Jan. 24, 2017
`
`
`US009549938B2
`
`(72)
`
`(54) BORON-CONTAINING SMALL MOLECULES
`.
`(71) Applicant: Anacor Pharmaceuticals, Inc., Palo
`A110, 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)
`
`(73) Assignee: Anacor Pharmaceuticals, Inc., Palo
`Alto, CA (US)
`
`( * ) Notice:
`
`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.
`
`(21) Appl. N0.: 15/068,352
`
`(22)
`
`Filed:
`
`Mar. 11, 2016
`
`(65)
`
`Prior Publication Data
`
`US 2016/0184334 A1
`
`Jun. 30, 2016
`
`Related U.S. Application Data
`
`(60) 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, 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. 15/068,352, filed on Mar. 11, 2016,
`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 continuation of application No.
`11/357,687.
`(60) Provisional application No. 60/654,060, filed on Feb.
`16, 2005, provisional application No. 60/755,227,
`(Continued)
`
`(5 1 )
`
`Int. Cl.
`A61K 31/69
`C07F 5/02
`
`(2006.01)
`(2006.01)
`
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(200601)
`(200601)
`(200601)
`(200901)
`(200901)
`(200901)
`
`C07F 5/04
`C07H 19/06
`C07H 19/16
`C07H 21/00
`C07H 23/00
`A61K 31/70
`A61K 31/7076
`A61K 9/00
`A61K 47/10
`A61K 9/08
`(52) U.S. Cl.
`CPC ............. A61K 31/69 (2013.01); A61K 9/0012
`(2013.01); A61K 9/08 (2013.01); A61K 31/70
`(2013.01); A61K 31/7076 (2013.01); A61K
`47/10 (2013.01); C07F 5/025 (2013.01); C07F
`5/04 (2013.01); C07H 19/06 (2013.01); C07H
`19/16 (2013.01); C07H 21/00 (2013.01);
`C07H 23/00 (2013.01)
`(58) Field of Classification Search
`USPC ............................................................ 514/64
`
`See application file for complete search history.
`
`(56)
`
`References Cited
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`(Continued)
`
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`U.S. Appl. No. 13/673,860, filed Nov. 9, 2012, Anacor Pharmaceu-
`ticals, Inc.
`
`(Continued)
`
`Primary Examiner 7 Rei-Tsang Shiao
`(74) Attorney, Agent, or Firm 7 Morgan, Lewis &
`Bockius LLP
`
`(57)
`
`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
`
`MYLAN - EX. 1001, p. 1
`
`MYLAN - Ex. 1001, p. 1
`
`

`

`US 9,549,938 B2
`
`Page 2
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`Related US. Application Data
`
`filed on Dec. 30, 2005, provisional application No.
`60/746,361, filed on May 3, 2006.
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`(56)
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`>>>>>>>>>>>>>>>>>>>>>>>>>>>>>
`
`3,093,659
`3,104,255
`3,297,525
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`3,686,398
`3,816,472
`3,873,279
`4,202,894
`4,602,011
`4,716,035
`4,766,113
`4,822,822
`4,894,220
`4,919,934
`4,977,268
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