`US009566290B2
`
`c12) United States Patent
`Baker et al.
`
`(10) Patent No.:
`(45) Date of Patent:
`
`US 9,566,290 B2
`*Feb.14,2017
`
`(54) BORON-CONTAINING SMALL MOLECULES
`
`(71) Applicant: Anacor Pharmaceuticals, Inc., Palo
`Alto, CA (US)
`
`(72)
`
`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 ofthis
`patent is extended or adjusted under 35
`U.S.C. 154(b) by 0 days.
`
`This patent is subject to a terminal dis(cid:173)
`claimer.
`
`(21) Appl. No.: 15/134,286
`
`(22) Filed:
`
`Apr. 20, 2016
`
`(65)
`
`Prior Publication Data
`
`US 2016/0228463 Al
`
`Aug. 11, 2016
`
`Related U.S. Application Data
`
`(60) Continuation of application No. 15/091,394, filed on
`Apr. 5, 2016, which is a 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, and a continuation-in-part of application
`No. 11/357,687, filed on Feb. 16, 2006, now Pat. No.
`7,582,621, said application No. 14/537,771 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
`
`(60) Provisional application No. 60/755,227, filed on Dec.
`30, 2005, provisional application No. 60/746,361,
`filed on May 3, 2006, provisional application No.
`(Continued)
`
`(51)
`
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`
`Int. Cl.
`A61K 31169
`C07F 5102
`C07F 5104
`C07H 19106
`C07H 19116
`C07H 21100
`C07H 23100
`A61K 31170
`A61K 3117076
`A61K 9100
`A61K 47110
`A61K 9108
`(52) U.S. Cl.
`CPC ............. A61K 31169 (2013.01); A61K 910012
`(2013.01); A61K 9108 (2013.01); A61K 31170
`(2013.01); A61K 3117076 (2013.01); A61K
`47110 (2013.01); C07F 51025 (2013.01); C07F
`5104 (2013.01); C07H 19106 (2013.01); C07H
`19116 (2013.01); C07H 21100 (2013.01);
`C07H 23100 (2013.01)
`(58) Field of Classification Search
`USPC ............................................................ 514/64
`See application file for complete search history.
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`OTHER PUBLICATIONS
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`U.S. Appl. No. 14/537,771, filed Nov. 10, 2014.
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`(Continued)
`Primary Examiner - Rei-Tsang Shiao
`(74) Attorney, Agent, or Firm - Morgan, Lewis &
`Bockius LLP
`ABSTRACT
`(57)
`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.
`12 Claims, 63 Drawing Sheets
`
`MYLAN - Ex. 1001, p. 1
`
`
`
`US 9,566,290 B2
`Page 2
`
`Related U.S. Application Data
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`continuation of application No. 11/357,687, filed on
`Feb. 16, 2006, now Pat. No. 7,582,621.60/654,060,
`filed on Feb. 16, 2005, provisional application No.
`60/654,060, filed on Feb. 16, 2005.
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`
`MYLAN - Ex. 1001, p. 4
`
`
`
`US 9,566,290 B2
`Page 5
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`(56)
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