Carboxylic acids and carboxylic acid isosteres of N-heterocyclic compounds

62 Pages·2013·6.41 MB·English

US006331537B1
(12) United States Patent (10) Patent N0.: US 6,331,537 B1
Hamilton et al. (45) Date of Patent: Dec. 18, 2001
(54) CARBOXYLIC ACIDS AND CARBOXYLIC 5,192,773 3/1993 Armistead et a1. .
ACID ISOSTERES OF N-HETEROCYCLIC 5,204,338 4/1993 Baader et a1. .
COMPOUNDS 5,214,034 5/1993 Nakayama et a1. .
5,215,969 6/1993 Springer et a1. .
(75) Inventors: Gregory S. Hamilton, Catonsville, MD 5,232,923 8/1993 FukaZaWa et a1. .
(US); Mark H. Norman, Thousand 5,294,603 3/1994 Rinehart .
Oaks, CA (US); Yong-Qian Wu, 5,321,009 6/1994 Baeder et a1. .
5,330,993 7/1994 Armistead et a1. .
Columbia, MD (US)
5,342,942 8/1994 Jaen et a1. .
5,348,944 9/1994 Gold et al. .
(73) Assignee: GPI Nil Holdings, Inc., Wilmington,
5,359,138 10/1994 Takeuchi et a1. .
DE (US) 5,447,915 9/1995 Schreiber et a1. .
( * ) Notice: Subject to any disclaimer, the term of this (List continued on neXt page.)
patent is extended or adjusted under 35
FOREIGN PATENT DOCUMENTS
U.S.C. 154(b) by 0 days.
3508251 11/1986 (DE).
(21) Appl. N0.: 09/453,571 4015255 11/1991 (DE).
4425950 1/1996 (DE).
(22) Filed: Dec. 2, 1999 012401 6/1980 (EP).
048159 3/1982 (EP).
Related US. Application Data 050800 5/1982 (EP).
073143 3/1983 (EP).
088350 9/1983 (EP).
(63) Continuation-in-part of application No. 09/204,237, ?led on
Dec. 3, 1998, now abandoned 180 544 5/1986 (EP).
(60) Provisional application No. 60/087,788, ?led on Jun. 3, 196841 10/1986 (EP).
1998. 3636278 10/1986 (EP).
333174 9/1989 (EP).
(51) Int. C1.7 ........................ .. A01N 43/46; A61K 31/55; 35200 1/1990 (EP).
C07D 403/12 378318 7/1990 (EP).
(52) us. Cl. ........................ .. 514/215; 548/200; 548/201; 405994 1/1991 (EP).
548/123; 548/124; 548/127; 548/128; 548/131; 443983 8/1991 (EP).
548/132; 548/134; 548/135; 548/136; 548/143;
(List continued on neXt page.)
548/182; 548/206; 548/215; 548/240; 548/255;
548/262.2; 548/300.1; 548/311.1; 548/356.1;
OTHER PUBLICATIONS
548/364.1; 548/366.4; 548/540; 548/212;
548/326; 548/360; 548/361; 548/362; 548/363; Likhosherstov et al. “Azacycloalkanes. XX. Derivatives of
548/364; 548/365; 548/369; 548/371; 548/572; heXahydroaZepine—2—carboXylic acid” Ca 89:24120, 1978.*
548/374; 548/376; 548/378; 548/380; 548/383;
Narasaka et al. “OXidative generation of . . . ” CA
548/396; 548/401; 548/402; 548/406; 540/596; 120:191500, 1993.*
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Wermuth “Molecular variations based on isosteric replace
546/209; 546/210
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(58) Field of Search ................................... .. 548/200, 201,
King “Bioisosters, conformational restriction and
548/540, 123, 124, 127, 128, 131, 132,
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387, 1985.*
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(56) References Cited
Primary Examiner—Ceila Chang
(74) Attorney, Agent, or Firm—Gary M. Nath; Todd L.
U.S. PATENT DOCUMENTS
Juneau; Joshua B. Goldber
4,374,829 2/1983 Harris et a1. .
(57) ABSTRACT
4,431,644 2/1984 Smith et a1. .
4,472,380 9/1984 Harris et a1. .
This invention relates to novel N-heteorocyclic carboXylic
4,692,458 9/1987 Ryan et a1. .
acids and carboXylic acid isosteres, their preparation and use
4,734,420 3/1988 Ryan et a1. .
for treating neurological disorders including physically
4,745,124 5/1988 Ryan et a1. .
4,766,110 * 8/1988 Ryan et a1. .......................... .. 514/19 damaged nerves and neurodengenerative diseases, for treat
4,808,573 2/1989 Gold et a1. . ing alopecia and promoting hair groWth, for treating vision
4,818,749 4/1989 Gold et a1. . disorders and/or improving vision, and for treating memory
5,002,962 3/1991 LoscalZo. impairment and/or enhancing memory performance by
5,002,963 3/1991 De Luca et a1. . administering such compounds.
5,128,483 7/1992 Trybulski et a1. .
5,147,877 9/1992 Goulet.
5,166,317 11/1992 Wallace et a1. . 18 Claims, 12 Drawing Sheets
US 6,331,537 B1
Page 2
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WO 93/18736 9/1993 (W0).
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5,843,960 12/1998 Steiner et al. . WO 98/20892 5/1998 (W0) _
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FOREIGN PATENT DOCUMENTS WO 9855090 12/1998 (WO) .
W0 9855091 12/1998 (W0).
468339 1/1992 (EP) - W0 99/10340 3/1999 (W0) .
471135 2/1992 (EP) - W0 9962881 12/1999 (W0) .
476933 3/1992 (EP) . PCT/US99/
488 258 6/1992 (EP) - 28663 11/2000 (W0) .
494005 7/1992 (EP) . PCT/US99/
519819 12/1992 (EP) - 28663 12/2000 (W0) .
610744 10/1993 (EP) - 9207782 9/1992 (ZA) .
652229 5/1995 (EP) .
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