US2011112084A9PendingUtilityA9
Bicyclic androgen and progesterone receptor modulator compounds and methods
Est. expiryAug 27, 2019(expired)· nominal 20-yr term from priority
Inventors:Lin ZhiChristopher M. TegleyBarbara PioCorneils Arjan Van OeverenMehrnouch MotamediEsther MartinboroughRobert I. HiguchiLawrence G. Hamann
A61P 7/06A61P 5/26A61P 5/36A61P 7/04A61P 43/00A61P 5/24A61P 5/34A61P 35/00A61P 5/28A61P 15/00A61P 15/08A61P 15/18A61P 17/14A61P 17/10A61P 13/08A61P 15/10A61P 15/04A61P 15/16C07D 209/96C07D 413/04C07D 215/36C07D 311/14C07D 401/04C07D 215/38C07D 405/12C07D 417/04C07D 409/04C07D 209/34C07D 401/12C07D 277/68C07D 239/80C07D 311/20C07D 265/18C07D 215/227C07D 405/04C07D 409/12C07D 265/36
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Claims
Abstract
The present invention is directed to compounds, pharmaceutical compositions, and methods for modulating processes mediated by AR and PR. More particularly, the invention relates to nonsteroidal compounds and compositions that are high affinity, high specificity agonists, partial agonists (i.e., partial activators and/or tissue-specific activators) and antagonists for AR and PR. Also provided are methods of making such compounds and pharmaceutical compositions, as well as critical intermediates used in their synthesis.
Claims
exact text as granted — not AI-modified1 . A compound of the formula:
wherein:
R 1 and R 2 each independently is COR 3 , CSR 3 , SO 2 R 3 , NO, NR 3 R 4 , C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 haloalkyl, C 2 -C 8 haloalkenyl, C 2 -C 8 haloalkynyl, C 1 -C 8 heteroalkyl, C 2 -C 8 heteroalkenyl, C 2 -C 8 heteroalkynyl, (CH 2 ) n R 3A , aryl or heteroaryl, wherein the alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, heteroalkyl, heteroalkenyl, heteroalkynyl, aryl, and heteroaryl are optionally substituted with F, Cl, Br, I, OR 3 , NR 3 R 4 , CN, NO 2 , SR 3 , SOR 3 , SO 2 R 3 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl; or
R 1 and R 2 taken together form a three- to nine-membered alkyl, alkenyl, heteroalkyl, or heteroalkenyl ring, wherein the alkyl, alkenyl, heteroalkyl, or heteroalkenyl ring are optionally substituted with F, Cl, Br, I, OR 3 , NR 3 R 4 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl; or
R 1 and R 2 are taken together to form one of:
R 3 and R 4 each independently is hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 haloalkyl, C 1 -C 8 heteroalkyl, heteroaryl or aryl, wherein the alkyl, alkenyl, alkynyl, haloalkyl, heteroalkyl, heteroaryl, and aryl are optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl;
R 3A is aryl or heteroaryl, wherein the aryl and heteroaryl is optionally substituted with halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl;
R 5 is hydrogen, F, Cl, Br, I, OR 3 , SR 3 , NR 3 R 4 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl;
R 6 is F, Cl, Br, I, CH 3 , CF 3 , CHF 2 , CFH 2 , CN, CF 2 Cl, CF 2 OR 3 , OR 3 , SR 3 , SOR 3 , SO 2 R 3 , CO 2 R 3 , NR 3 R 4 , C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 1 -C 4 heteroalkyl, C 2 -C 4 heteroalkenyl or C 2 -C 4 heteroalkynyl, wherein the alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, heteroalkyl, heteroalkenyl, heteroalkynyl are optionally substituted with F, Cl, Br, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl;
R 7 and R 8 each independently is hydrogen, F, Cl, Br, I, CN, OR 3 , NR 3 R 4 , NR 3 CR 3 R 4 CONR 3 R 4 , C n (R 3 ) 2n OR 3 , SR 3 , SOR 3 , SO 2 R 3 , NR 3 COR 4 , C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, and C 1 -C 8 heteroalkyl;
R 9 is hydrogen, F, Br, Cl, I, OR 3 , NR 3 R 4 , SR 3 , SOR 3 , SO 2 R 3 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl;
R 10 is:
R 11 is F, Br, Cl, I, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 heteroalkyl, NO 2 , CN, CF 3 , OR 3 , NR 3 R 4 , SR 3 , SOR 3 or SO 2 R 3 ;
R 12 is F, Br, Cl, I, CN, OR 3 , SR 3 , SOR 3 , SO 2 R 3 , NR 3 R 4 or C 1 -C 4 haloalkyl;
R 13 is hydrogen, F, Cl, Br, I, CN, OR 3 , NR 3 R 4 , COR 3 , CO 2 R 3 , SR 3 , SOR 3 , SO 2 R 3 , C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 haloalkyl, C 2 -C 8 haloalkenyl, C 2 -C 8 haloalkynyl, C 1 -C 8 heteroalkyl, C 2 -C 8 heteroalkenyl, C 2 -C 8 heteroalkynyl or (CH 2 ) n R 3A , wherein the alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, heteroalkyl, heteroalkenyl and heteroalkynyl are optionally substituted with F, Cl, Br, I, CN, NO 2 , NR 3 R 4 , SR 3 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl;
R 13A is NHR 1 or heteroaryl, wherein the heteroaryl is optionally substituted with F, Cl, Br, I, CN, NO 2 , NR 3 R 4 , SR 3 , SOR 3 , SO 2 R 3 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl;
R 14 is F, Br, Cl, I, CF 3 , CHF 2 , CH 2 F, CF 2 Cl or CF 2 OR 3 ;
R 15 is F, Br, Cl, I, CN, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 heteroalkyl, OR 16 , NR 16 R 4 , SR 16 , CH 2 R 16 , COR 3 , CO 2 R 3 , CONR 3 R 4 , SOR 3 or SO 2 R 3 ;
R 16 is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 heteroalkyl, CH 2 R 3A , aryl, heteroaryl, COR 17 , CO 2 R 17 or CONR 17 R 17 ;
R 17 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl;
R 18 and R 19 each independently is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 heteroalkyl; or
R 18 and R 19 taken together form a three- to seven-membered ring;
R 20 is aryl or heteroaryl, wherein the aryl or heteroaryl are optionally substituted with F, Cl, Br, CN, OR 3 , SR 3 , SOR 3 , SO 2 R 3 , NO 2 , NR 3 R 3 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl;
R 21 is CR 3 R 4 CONR 3 R 4 , C n (R 3 ) 2n OR 3 , SOR 3 , SO 2 R 3 , C 2 -C 8 alkyl, C 2 -C 8 haloalkyl or C 2 -C 8 heteroalkyl;
R 22 and R 23 each independently is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 heteroalkyl; or
R 22 and R 23 are taken together to form a three- to seven-membered ring;
R 24 is hydrogen or OR 3 ;
R 25 through R 30 each independently is hydrogen, F, Cl, Br, I, OR 3 , NR 3 R 4 , SR 3 , SOR 3 , SO 2 R 3 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 heteroalkyl, C 2 -C 6 alkynyl or C 2 -C 6 alkenyl, wherein the alkyl, haloalkyl, heteroalkyl, alkynyl and alkenyl are optionally substituted with F, Cl, Br, I, OR 3 , NR 3 R 4 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 heteroalkyl, aryl or heteroaryl, and wherein the aryl and heteroaryl are optionally substituted with F, Cl, Br, I, CN, NO 2 , OH, OCH 3 , CF 3 or C 1 -C 6 alkyl; or
any two of R 25 R 26 , R 27 , R 28 , R 29 and R 30 taken together form a three to seven-membered alkyl or alkenyl or heteroalkyl ring; or
any four of R 25 , R 26 , R 27 , R 28 , R 29 and R 30 taken together form a fused aromatic ring;
Q is O or S;
U is V, OCR 22 R 23 , SCR 22 R 23 , NR 3 CR 22 R 23 or CR 3 R 4 CR 22 R 23 ;
V is O, S, NR 3 , CR 22 R 23 , CR 3 R 4 O or CR 3 R 4 S, but V is not S when R 1 and R 2 are both methyl;
W is O, S, NR 3 or CR 25 R 26 ;
X is O or S;
Y is O, S, NR 3 , NOR 3 or CR 3 R 4 ;
Z is O, S, NR 3 , C═O, CR 25 R 26 or two hydrogens;
n is 1, 2 or 3; and
m is 1 to 5,
or a pharmaceutically acceptable salt thereof.
2 . A compound of formula I:
wherein:
R 3 and R 4 each independently is hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 haloalkyl, C 1 -C 8 heteroalkyl, heteroaryl or aryl, wherein the alkyl, alkenyl, alkynyl, haloalkyl, heteroalkyl, heteroaryl and aryl are optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl;
R 5 is hydrogen, F, Cl, Br, I, OR 3 , SR 3 , NR 3 R 4 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl;
R 6 is F, Cl, Br, I, CH 3 , CF 3 , CHF 2 , CFH 2 , CN, CF 2 Cl, CF 2 OR 3 , OR 3 , SR 3 , SOR 3 , SO 2 R 3 , CO 2 R 3 , NR 3 R 4 , C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 1 -C 4 heteroalkyl, C 2 -C 4 heteroalkenyl or C 2 -C 4 heteroalkynyl, wherein the alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, heteroalkyl, heteroalkenyl, heteroalkynyl are optionally substituted with F, Cl, Br, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl;
R 7 and R 8 each independently is hydrogen, F, Cl, Br, I, CN, OR 3 , NR 3 R 4 , NR 3 CR 3 R 4 CONR 3 R 4 , C n (R 3 ) 2n OR 3 , SR 3 , SOR 3 , SO 2 R 3 , NR 3 COR 4 , C 1 -C 8 alkyl, C 1 -C 8 haloalkyl and C 1 -C 8 heteroalkyl;
R 9 is hydrogen, F, Br, Cl, I, OR 3 , NR 3 R 4 , SR 3 , SOR 3 , SO 2 R 3 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl;
R 10 is:
R 24 is hydrogen or OR 3 ;
R 25 through R 30 each independently is hydrogen, F, Cl, Br, I, OR 3 , NR 3 R 4 , SR 3 , SOR 3 , SO 2 R 3 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 heteroalkyl, C 2 -C 6 alkynyl or C 2 -C 6 alkenyl, wherein the alkyl, haloalkyl, heteroalkyl, alkynyl and alkenyl are optionally substituted with F, Cl, Br, I, OR 3 , NR 3 R 4 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 heteroalkyl, aryl or heteroaryl, and wherein the aryl and heteroaryl are optionally substituted with F, Cl, Br, I, CN, NO 2 , OH, OCH 3 , CF 3 or C 1 -C 6 alkyl; or
any two of R 25 R 26 , R 27 , R 28 , R 29 and R 30 taken together form a three to seven-membered alkyl or alkenyl or heteroalkyl ring; or any four of R 25 , R 26 , R 27 , R 28 , R 29 and R 30 taken together form a fused aromatic ring;
X is O or S;
Y is O, S, NR 3 , NOR 3 or CR 3 R 4 ;
Z is O, S, NR 3 , C═O, CR 25 R 26 or two hydrogens;
n is 1, 2 or 3; and
m is 1 to 5,
or a pharmaceutically acceptable salt thereof.
3 . A compound of the formula:
wherein:
R 1 and R 2 each independently is COR 3 , CSR 3 , SO 2 R 3 , NO, NR 3 R 4 , C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 haloalkyl, C 2 -C 8 haloalkenyl, C 2 -C 8 haloalkynyl, C 1 -C 8 heteroalkyl, C 2 -C 8 heteroalkenyl, C 2 -C 8 heteroalkynyl, (CH 2 ) n R 3A , aryl or heteroaryl, wherein the alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, heteroalkyl, heteroalkenyl, heteroalkynyl, aryl and heteroaryl are optionally substituted with F, Cl, Br, I, OR 3 , NR 3 R 4 , CN, NO 2 , SR 3 , SOR 3 , SO 2 R 3 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl; or
R 1 and R 2 taken together form a three- to nine-membered alkyl, alkenyl, heteroalkyl, or heteroalkenyl ring, wherein the alkyl, alkenyl, heteroalkyl, or heteroalkenyl ring are optionally substituted with F, Cl, Br, I, OR 3 , NR 3 R 4 , C 1 -C 4 alkyl, C 1 -C a haloalkyl or C 1 -C 4 heteroalkyl; or
R 1 and R 2 are taken together to form one of:
R 3 and R 4 each independently is hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 haloalkyl, C 1 -C 8 heteroalkyl, heteroaryl or aryl, wherein the alkyl, alkenyl, alkynyl, haloalkyl, heteroalkyl, heteroaryl and aryl are optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl;
R 7 and R 8 each independently is hydrogen, F, Cl, Br, I, CN, OR 3 , NR 3 R 4 , NR 3 CR 3 R 4 CONR 3 R 4 , C n (R 3 ) 2n OR 3 , SR 3 , SOR 3 , SO 2 R 3 , NR 3 COR 4 , C 1 -C 8 alkyl, C 1 -C 8 haloalkyl and C 1 -C 8 heteroalkyl;
R 9 is hydrogen, F, Br, Cl, I, OR 3 , NR 3 R 4 , SR 3 , SOR 3 , SO 2 R 3 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl;
R 10 is:
R 24 is hydrogen or OR 3 ;
R 25 through R 30 each independently is hydrogen, F, Cl, Br, I, OR 3 , NR 3 R 4 , SR 3 , SOR 3 , SO 2 R 3 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 heteroalkyl, C 2 -C 6 alkynyl or C 2 -C 6 alkenyl, wherein the alkyl, haloalkyl, heteroalkyl, alkynyl and alkenyl are optionally substituted with F, Cl, Br, I, OR 3 , NR 3 R 4 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 heteroalkyl, aryl or heteroaryl, and wherein the aryl and heteroaryl are optionally substituted with F, Cl, Br, I, CN, NO 2 , OH, OCH 3 , CF 3 or C 1 -C 6 alkyl; or
any two of R 25 R 26 , R 27 , R 28 , R 29 and R 30 taken together form a three to seven-membered alkyl or alkenyl or heteroalkyl ring; or
any four of R 25 , R 26 , R 27 , R 28 , R 29 and R 30 taken together form a fused aromatic ring;
Q is O or S;
U is V, OCR 22 R 23 , SCR 22 R 23 , NR 3 CR 22 R 23 or CR 3 R 4 CR 22 R 23 ;
V is O, S, NR 3 , CR 22 R 23 , CR 3 R 4 O or CR 3 R 4 S, but V is not S when R 1 and R 2 are both methyl;
W is O, S, NR 3 or CR 25 R 26 ;
X is NR 16 ;
Y is O, S, NR 3 , NOR 3 or CR 3 R 4 ;
Z is O, S, NR 3 , C═O, CR 25 R 26 or two hydrogens; and
n is 1, 2 or 3;
or a pharmaceutically acceptable salt thereof.
4 . A compound of claim 1 , wherein:
R 3 and R 4 each independently is hydrogen or optionally substituted C 1 -C 6 alkyl; R 3A is optionally substituted aryl or heteroaryl; R 5 is hydrogen, halogen or optionally substituted C 1 -C 6 alkyl; R 7 and R 8 each independently is hydrogen or halogen; and R 9 is hydrogen or halogen.
5 . A compound of claim 2 , wherein:
R 11 is halogen, CN, NO 2 or optionally substituted C 1 -C 6 haloalkyl; R 12 is halogen or optionally substituted haloalkyl; R 13 is hydrogen, halogen, C 1 -C 6 alkyl or C 1 -C 6 heteroalkyl, wherein the C 1 -C 6 alkyl and C 1 -C 6 heteroalkyl are optionally substituted; R 15 is halogen or OR 16 ; and R 18 and R 19 each independently is optionally substituted C 1 -C 6 alkyl; or R 18 and R 19 taken together form a five- to six-membered ring.
6 . A compound of claim 3 , wherein:
R 22 and R 23 each independently is hydrogen or optionally substituted C 1 -C 6 alkyl; or R 22 and R 23 taken together form a three- to seven-membered ring; R 25 through R 30 each independently is hydrogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl, wherein the C 1 -C 6 alkyl and C 1 -C 6 haloalkyl are optionally substituted; Y is O, S or NOR 3 ; and m is 1 to 3.
7 . A compound of claim 1 , wherein:
R 1 and R 2 each independently is COR 3 , CSR 3 , SO 2 R 3 , NO, NR 3 R 4 , C 1 -C 8 alkyl, C 2 C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 haloalkyl, C 2 -C 8 haloalkenyl, C 2 -C 8 haloalkynyl, C 1 -C 8 heteroalkyl, C 2 -C 8 heteroalkenyl, C 2 -C 8 heteroalkynyl, (CH 2 ) n R 3A , aryl or heteroaryl, wherein the alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, heteroalkyl, heteroalkenyl, heteroalkynyl, aryl and heteroaryl are optionally substituted with F, Cl, Br, I, OR 3 , NR 3 R 4 , CN, NO 2 , SR 3 , SOR 3 , SO 2 R 3 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl; R 3 and R 4 each independently is hydrogen or optionally substituted C 1 -C 6 alkyl; R 3A is optionally substituted aryl or heteroaryl; R 5 is hydrogen, halogen or optionally substituted C 1 -C 6 alkyl; R 7 and R 8 each independently is hydrogen or halogen; R 9 is hydrogen or halogen. R 11 is halogen, CN, NO 2 or optionally substituted C 1 -C 6 haloalkyl; R 12 is halogen or optionally substituted haloalkyl; R 13 is hydrogen, halogen, C 1 -C 6 alkyl or C 1 -C 6 heteroalkyl, wherein the C 1 -C 6 alkyl and C 1 -C 6 heteroalkyl are optionally substituted; R 15 is halogen or OR 16 ; R 18 and R 19 each independently is optionally substituted C 1 -C 6 alkyl; or R 18 and R 19 taken together form a five- to six-membered ring; R 22 and R 23 each independently is hydrogen or optionally substituted C 1 -C 6 alkyl; or R 22 and R 23 together form a three- to seven-membered ring; R 25 through R 30 each independently is hydrogen, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl, wherein the C 1 -C 6 alkyl and C 1 -C 6 haloalkyl are optionally substituted; Y is O, S and NOR 3 ; and m is 1 to 3.
8 . A compound of claim 1 , wherein:
R 1 and R 2 taken together form a three- to nine-membered alkyl, alkenyl, heteroalkyl, or heteroalkenyl ring, wherein the alkyl, alkenyl, heteroalkyl, or heteroalkenyl ring are optionally substituted with F, Cl, Br, I, OR 3 , NR 3 R 4 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl; R 3 and R 4 each independently is hydrogen or optionally substituted C 1 -C 6 alkyl; R 3A is optionally substituted aryl or heteroaryl; R 5 is hydrogen, halogen or optionally substituted C 1 -C 6 alkyl; R 7 and R 8 each independently is hydrogen or halogen; R 9 is hydrogen or halogen; R 11 is halogen, CN, NO 2 or optionally substituted C 1 -C 6 haloalkyl; R 12 is halogen or optionally substituted haloalkyl; R 13 is hydrogen, halogen, C 1 -C 6 alkyl or C 1 -C 6 heteroalkyl, wherein the C 1 -C 6 alkyl and C 1 -C 6 heteroalkyl are optionally substituted; R 15 is halogen or OR 16 ; R 18 and R 19 each independently is optionally substituted C 1 -C 6 alkyl; or R 18 and R 19 taken together form a five- to six-membered ring; R 22 and R 23 each independently is hydrogen or optionally substituted C 1 -C 6 alkyl; or R 22 and R 23 together form a three- to seven-membered ring; R 25 through R 30 each independently is hydrogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl, wherein the C 1 -C 6 alkyl and C 1 -C 6 haloalkyl are optionally substituted; Y is O, S and NOR 3 ; and m is 1 to 3.
9 . A compound of claim 1 , wherein:
R 1 and R 2 taken together form one of:
R 3 and R 4 each independently is hydrogen or optionally substituted C 1 -C 6 alkyl;
R 3A is optionally substituted aryl or heteroaryl;
R 5 is hydrogen, halogen or optionally substituted C 1 -C 6 alkyl;
R 7 and R 8 each independently is hydrogen or halogen;
R 9 is hydrogen or halogen;
R 11 is halogen, CN, NO 2 or optionally substituted C 1 -C 6 haloalkyl;
R 12 is halogen or optionally substituted haloalkyl;
R 13 is hydrogen, halogen, C 1 -C 6 alkyl or C 1 -C 6 heteroalkyl, wherein the C 1 -C 6 alkyl and C 1 -C 6 heteroalkyl are optionally substituted;
R 15 is halogen or OR 16 ;
R 18 and R 19 each independently is optionally substituted C 1 -C 6 alkyl; or
R 18 and R 19 taken together form a five- to six-membered ring;
R 22 and R 23 each independently is hydrogen or optionally substituted C 1 -C 6 alkyl; or
R 22 and R 23 together form a three- to seven-membered ring;
R 25 through R 30 each independently is hydrogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl, wherein the C 1 -C 6 alkyl and C 1 -C 6 haloalkyl are optionally substituted;
Y is O, S or NOR 3 ; and
m is 1 to 3.
10 . A compound of claim 1 , wherein:
R 1 and R 2 are each independently selected from the group of COR 3 , CSR 3 , SO 2 R 3 , C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 1 -C 8 haloalkyl, C 2 -C 8 haloalkenyl, C 1 -C 8 heteroalkyl, C 2 -C 8 heteroalkenyl, CH 2 R 3A , aryl or heteroaryl, wherein the aryl or heteroaryl are optionally substituted with F, Cl, Br, CN, NO 2 , OR 3 , NR 3 R 4 , SR 3 , COMe, COCF 3 , C 1 -C 4 alkyl, or C 1 -C 4 haloalkyl; or R 1 and R 2 are taken together to form one of:
R 3 and R 4 each independently is hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 1 -C 8 haloalkyl or C 1 -C 8 heteroalkyl;
R 3A is heteroaryl or aryl, wherein the heteroaryl and aryl are optionally substituted with F, Cl, Br, CN, OMe, SMe, C 1 -C 4 alkyl, or C 1 -C 4 haloalkyl;
R 5 is hydrogen, F, Cl, Br, OH, OMe, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
R 6 is F, Cl, Br, CH 3 , CF 3 , CHF 2 , CFH 2 , CN, CF 2 Cl, CF 2 OR 3 , OR 3 , SR 3 , NR 3 R 4 , C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 1 -C 4 heteroalkyl or C 2 -C 4 heteroalkenyl;
R 7 and R 8 each independently is hydrogen, F, Cl, Br, OR 3 , NR 3 R 4 , SR 3 , C 1 -C 8 alkyl, C 1 -C 8 haloalkyl or C 1 -C 8 heteroalkyl;
R 9 is hydrogen, F, Br, Cl, OR 3 , NR 3 R 4 , SR 3 , C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
R 10 is:
R 11 is F, Br, Cl, I, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, NO 2 , CN, CF 3 , OH, OMe, NR 3 R 4 or SR 3 ;
R 12 is F, Br, Cl or C 1 -C 4 haloalkyl;
R 13 is hydrogen, F, Cl, Br, I, CN, OR 3 , NR 3 R 4 , SR 3 , C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 haloalkyl, C 2 -C 8 haloalkenyl, C 2 -C 8 haloalkynyl, C 1 -C 8 heteroalkyl or CH 2 R 3A ;
R 14 is F, Br, Cl, CF 3 , CHF 2 , CH 2 F, CF 2 Cl or CF 2 OMe;
R 15 is F, Br, Cl, CN, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 heteroalkyl, OR 16 , NR 16 R 4 or SR 16 ;
R 16 is hydrogen, C 1 -C alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 heteroalkyl, COR 17 , CO 2 R 17 or CONR 17 R 17 ;
R 17 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl;
R 18 and R 19 each independently is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 heteroalkyl; or
R 18 and R 19 are taken together to form a four- to seven-membered ring;
R 20 is aryl or heteroaryl, wherein the aryl or heteroaryl is optionally substituted with F, Cl, Br, CN, NO 2 , CF 3 or C 1 -C 4 alkyl;
R 21 is C 2 -C 8 alkyl, C 2 -C 8 haloalkyl or C 2 -C 8 heteroalkyl;
R 22 and R 23 each independently is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 heteroalkyl; or
R 22 and R 23 are taken together to form a three- to seven-membered ring;
R 24 is hydrogen or OR 3 ;
R 25 through R 30 each independently is hydrogen, F, Cl, Br, OR 3 , NR 3 R 4 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 heteroalkyl or C 2 -C 6 alkenyl, wherein the alkyl, haloalkyl, heteroalkyl and alkenyl are optionally substituted with F, Cl, Br, OR 3 , NR 3 R 4 , aryl or heteroaryl, and wherein the aryl and heteroaryl are optionally substituted with F, Cl, Br, CN, NO 2 , OH, OCH 3 , CF 3 or C 1 -C 6 alkyl;
any two of R 25 , R 26 , R 27 , R 28 , R 29 and R 30 taken together form a three to seven-membered alkyl or alkenyl or heteroalkyl ring; or
any four of R 25 , R 26 , R 27 , R 28 , R 29 and R 30 taken together form a fused aromatic ring;
X is S;
Y is O, S, NR 3 or NOR 3 ;
Z is O, S, NR 3 , CR 25 R 26 or two hydrogens;
n is 1 or 2; and
m is 1 to 4.
11 . A compound of claim 1 , wherein:
R 1 and R 2 each independently is COR 3 , C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 1 -C 8 haloalkyl, C 2 -C 8 haloalkenyl, C 1 -C 8 heteroalkyl, CH 2 R 3A , aryl or heteroaryl, wherein the aryl and heteroaryl are optionally substituted with F, Cl, Br, OH, OMe, SH, OMe, SMe, CN, NO 2 , CF 3 , Me, COMe, or COCF 3 ; or R 1 and R 2 are taken together to form:
R 3 and R 4 each independently is hydrogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;
R 3A is heteroaryl or aryl, wherein the heteroaryl and aryl are optionally substituted with F, Cl, Br, CN, OMe, C 1 -C 4 alkyl, or C 1 -C 4 haloalkyl;
R 5 is hydrogen, F, Cl, OH, OMe, C 1 -C 4 alkyl or CF 3 ;
R 6 is F, Cl, Br, C 1 -C 4 alkyl, CF 3 , CHF 2 , CFH 2 , CN, CF 2 Cl, CF 2 OMe or OMe;
R 7 is hydrogen, F, Cl, Me, OMe or CF 3 ;
R 8 is hydrogen, F, Cl, Br, OR 3 , NR 3 R 4 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 heteroalkyl;
R 9 is hydrogen, F, Cl, OH, Me, OMe or CF 3 ;
R 10 is:
R 11 is selected from the group of F, Br, Cl, C 1 -C 6 alkyl, NO 2 , CN, CF 3 , OH and OMe;
R 12 is selected from the group of F, Cl, CF 3 , CF 2 H and CFH 2 ;
R 13 is hydrogen, F, Cl, Br, OR 3 , SR 3 , C 1 -C 8 alkyl, C 2 -C 8 alkenyl or C 1 -C 8 haloalkyl;
R 14 is F, Cl, CF 3 , CHF 2 , CH 2 F or CF 2 Cl;
R 15 is F, Cl, CN, CF 3 , OR 16 or SR 16 ;
R 16 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, COR 17 , CO 2 R 17 or CONR 17 R 17 ;
R 17 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl;
R 18 and R 19 each independently is C 1 -C 6 alkyl or C 1 -C 6 haloalkyl; or
R 18 and R 19 taken together form a five- to six-membered ring;
R 21 is C 2 -C 8 alkyl or C 2 -C 8 haloalkyl;
R 22 and R 23 each independently is hydrogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl; or
R 22 and R 23 taken together form a four- to six-membered ring;
R 24 is hydrogen or OH;
R 25 through R 30 each independently is hydrogen, F, Cl, OH, OMe, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 heteroalkyl or C 2 -C 6 alkenyl; or
any two of R 25 , R 26 , R 27 , R 28 , R 29 and R 30 taken together form a four to six-membered alkyl or alkenyl ring; or
any four of R 25 , R 26 , R 27 , R 28 , R 29 and R 30 taken together form a fused aromatic ring;
V is CR 22 R 23 , CR 3 R 4 O and CR 3 R 4 S;
W is O or CR 3 R 4 ;
X is O;
Y is O, S or NOR 3 ;
Z is O, CR 25 R 26 or two hydrogens;
n is 1 or 2; and
m is 1 to 3.
12 . A compound of claim 1 , wherein:
the compound is represented by any one of formula III, IV and VI-VIII; R 1 and R 2 each independently is C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 1 -C 8 haloalkyl, C 1 -C 8 heteroalkyl and CH 2 R 3A ; or R 1 and R 2 are taken together to form:
R 3 and R 4 each independently is hydrogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;
R 3A is heteroaryl or aryl, wherein the heteroaryl and aryl are optionally substituted with F, Cl, Br, CN, CF 3 , OMe, or C 1 -C 4 alkyl;
R 5 is hydrogen, F, Cl, OMe or Me;
R 6 is F, Cl, C 1 -C 4 alkyl, CF 3 , CHF 2 , CFH 2 , CF 2 Cl, CF 2 OMe or OMe;
R 7 is hydrogen, F, Cl, Me or OMe;
R 8 is hydrogen, F, Cl, Br, OR 3 , NR 3 R 4 , C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;
R 9 is hydrogen, F, Cl, Me, OMe or CF 3 ;
R 10 is:
R 13 is hydrogen, F, Cl, Br, C 1 -C 4 alkyl, C 2 -C 4 alkenyl or C 1 -C 8 haloalkyl;
R 14 is Cl, CF 3 , CHF 2 , CH 2 F or CF 2 Cl;
R 15 is Cl, OR 16 or SR 16 ;
R 16 is hydrogen, C 1 -C 6 alkyl, COR 17 , CO 2 R 17 or CONR 17 R 17 ;
R 17 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl;
R 18 and R 19 each independently is C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; or
R 18 and R 19 are taken together to form a five- to six-membered ring;
R 21 is C 2 -C 8 alkyl, C 2 -C 8 haloalkyl or C 2 -C 8 heteroalkyl;
R 24 is hydrogen or OH;
R 25 through R 30 each independently is hydrogen, F, Cl, OH, OMe, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
W is O;
Y is O or S;
Z is two hydrogens; and
n is 1 or 2.
13 . A compound of claim 1 , wherein R 10 is represented by the formula:
wherein:
R 25 , R 26 , R 29 , R 30 each independently is hydrogen, F, Cl, Br, I, OR 3 , NR 3 R 4 , SR 3 , SOR 3 , SO 2 R 3 , COR 3 , CO 2 R 3 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 heteroalkyl, C 2 -C 6 alkynyl or C 2 -C 6 alkenyl, wherein the alkyl, haloalkyl, heteroalkyl, alkynyl and alkenyl are optionally substituted with F, Cl, Br, I, OR 3 , NR 3 R 4 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, aryl or heteroaryl, and wherein the aryl and heteroaryl are optionally substituted with F, Cl, Br, I, CN, NO 2 , OH, OCH 3 , CF 3 or C 1 -C 6 alkyl;
R 3 and R 4 each independently is hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 haloalkyl, C 1 -C 8 heteroalkyl, heteroaryl or aryl, wherein the alkyl, alkenyl, alkynyl, haloalkyl, heteroalkyl, heteroaryl and aryl are optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl; and
n is 1, 2, 3 or 4.
14 . A compound of claim 1 , wherein R 1 and R 2 are taken together to form:
wherein:
R 25 and R 30 each independently is hydrogen, F, Cl, Br, I, OR 3 , NR 3 R 4 , SR 3 , SOR 3 , SO 2 R 3 , COR 3 , CO 2 R 3 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 heteroalkyl, C 2 -C 6 alkynyl or C 2 -C 6 alkenyl, wherein the alkyl, haloalkyl, heteroalkyl, alkynyl and alkenyl are optionally substituted with F, Cl, Br, I, OR 3 , NR 3 R 4 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 heteroalkyl, aryl or heteroaryl, and wherein the aryl and heteroaryl are optionally substituted with F, Cl, Br, I, CN, NO 2 , OH, OCH 3 , CF 3 or C 1 -C 6 alkyl;
R 3 and R 4 each independently is hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 haloalkyl, C 1 -C 8 heteroalkyl, heteroaryl or aryl, wherein the alkyl, alkenyl, alkynyl, haloalkyl, heteroalkyl, heteroaryl and aryl are optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 heteroalkyl; and
n is 1, 2, 3 or 4.
15 . A compound of claim 1 , wherein R 10 is represented by the formula:
wherein:
R A is hydrogen, OR C , O 2 CR C , (CH 2 ) n OR C , NHR C , NHCOR C , F, Cl, Br, I, CN, SCN or SCH 3 ;
R B is hydrogen, F, Cl, Br, I, CHF 2 , CF 3 , C 1 -C 6 alkyl, aryl or heteroaryl, wherein the alkyl, aryl and heteroaryl are optionally substituted with F, Cl, Br, I, CN, NO 2 , OH, OCH 3 , CF 3 , or C 1 -C 6 alkyl;
R C is hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 haloalkyl, C 1 -C 8 heteroalkyl or (CH 2 ) n R D ;
R D is aryl or heteroaryl, wherein the aryl or heteroaryl is optionally substituted with F, Cl, Br, I, CN, NO 2 , OH, OCH 3 , CF 3 or C 1 -C 6 alkyl; and
n is 1, 2 or 3.
16 . The compound of claim 1 , wherein the compound is an androgen receptor modulator.
17 . The compound of claim 16 , wherein the compound is an androgen receptor antagonist.
18 . The compound of claim 16 , wherein the compound is an androgen receptor agonist.
19 . The compound of claim 16 , wherein the compound is an androgen receptor partial agonist.
20 . The compound of claim 1 , wherein the compound is a progesterone receptor modulator.
21 . The compound of claim 20 , wherein the compound is a progesterone receptor antagonist
22 . The compound of claim 20 , wherein the compound is a progesterone receptor agonist.
23 . The compound of claim 20 , wherein the compound is a progesterone receptor partial agonist.
24 . A compound that is selected from among:
(±)-3,4-Dihydro-6-(bis-2,2,2-trifluoroethyl)amino-4-trifluoromethylcoumarin (Compound 476); 6-(2,2,2-trifluoroethyl)amino-4-trifluoromethylcoumarin (Compound 477); 6-(N-Isopropyl-N-2,2,2-trifluoroethyl)amino-4-trifluoromethylcoumarin (Compound 478); 6-N-Isobutylamino-4-trifluoromethylcoumarin (Compound 479); 6-N-Propylamino-4-trifluoromethylcoumarin (Compound 482); 1,4-Dihydro-4,4-dimethyl-6-methylamino-1,3-benzo[d]oxazin-2-one (Compound 485); 1,4-Dihydro-4,4-dimethyl-6-dipropylamino-1,3-benzo[d]oxazin-2-one (Compound 489); 1,4-Dihydro-4,4-dimethyl-6-(bis-N,N-2,2,2-trifluoroethyl)amino-1,3-benzo[d]oxazin-2-one (Compound 490); 1,4-Dihydro-4,4-dimethyl-6-(N-2,2,2-trifluoroethyl)amino-1,3-benzo[d]oxazin-2-one (Compound 491); (±)-1,4-Dihydro-4-methyl-6-diallylamino-1,3-benzo[d]oxazin-2-one (Compound 492); 6-Diallylamino-3,4-dihydro-4,4-dimethyl-2(1H)-quinolinone (Compound 497); 3,4-Dihydro-4,4-dimethyl-6-dipropylamino-2(1H)-quinolinone (Compound 498); 3,4-Dihydro-4,4-dimethyl-6-propylamino-2(1H)-quinolinone (Compound 499); 3,4-Dihydro-4,4-dimethyl-6-(N-2,2,2-trifluoroethyl)amino-2(1H)-quinolinone (Compound 500); 3,4-Dihydro-4,4-dimethyl-6-(bis-N,N-2,2,2-trifluoroethyl)amino-2(1H)-quinolinone (Compound 501); 3,4-Dihydro-6-(N-2,2,2-trifluoroethyl)amino-2(1H)-quinolinone (Compound 502); 3,4-Dihydro-6-(bis-N,N-2,2,2-trifluoroethyl)amino-2(1H)-quinolinone (Compound 505); 5-(bis-N,N-2,2,2-Trifluoroethyl)amino-3,3-spirocyclohexyl-2-indolone (Compound 506); 7-(bis-N,N-2,2,2-Trifluoroethyl)amino-1,4-benzoxazin-3(4H)-one (Compound 508); 6-(bis-N,N-2,2,2-Trifluoroethyl)amino-2,4-dichloroquinoline (Compound 510); 7-Benzylamino-4-trifluoromethyl-2(1H)-quinolinone (Compound 519); 7-Cyclohexylamino-4-trifluoromethyl-2(1H)-quinolinone (Compound 524); 7-Cyclopentylamino-4-trifluoromethyl-2(1H)-quinolinone (Compound 525); 7-Cyclobutylamino-4-trifluoromethyl-2(1H)-quinolinone (Compound 526); 7-(2-Hydroxy-2-methylpropionyl)amino-4-trifluoromethyl-2(1H)-quinolinone (Compound 527); 7-(Trifluoroacetamido)-4-trifluoromethyl-2(1H)-quinolinone (Compound 528); 1-Methyl-7-methylamino-4-trifluoromethyl-2(1H)-quinolinone (Compound 529); 3-Fluoro-7-cyclopentylamino-4-trifluoromethyl-2(1H)-quinolinone (Compound 536); 3-Fluoro-7-cyclohexylamino-4-trifluoromethyl-2(1H)-quinolinone (Compound 537); 3-Fluoro-7-cyclobutylamino-4-trifluoromethyl-2(1H)-quinolinone (Compound 538); 7-(1,1-Dimethyl-3-oxobutyl)amino-4-trifluoromethyl-2(1H)-quinolinone (Compound 550); 7-(1,1,3-Trimethyl-3-hydroxybutyl)amino-4-trifluoromethyl-2(1H)-quinolinone (Compound 551); 7-(1,1,3-Trimethyl-3-butenylamino)-4-trifluoromethyl-2(1H)-quinolinone (Compound 552); 7-(1-Phenylaminocarbonylisopropyl)amino-4-trifluoromethyl-2(1H)-quinolinone (Compound 553); 7-(2-Hydroxy-1,1-dimethylethyl)amino-4-trifluoromethyl-2(1H)-quinolinone (Compound 556); 7-(N-1-Formylisopropyl)amino-4-trifluoromethyl-2(1H)-quinolinone (Compound 558); 7-(1,1-Dimethylallyl)amino-4-trifluoromethyl-2(1H)-quinolinone (Compound 559); 7-(1,1-Dimethylpropyl)amino-4-trifluoromethyl-2(1H)-quinolinone (Compound 560); 7-(1-Methyl-1-acetylenylpropyl)amino)-4-(trifluoromethyl)-2(1H)-quinolinone (Compound 561); 7-(1-Ethyl-1-methylpropyl)amino-4-(trifluoromethyl)-2(1H)-quinolinone (Compound 562); 8-Methyl-7-(3-methyl-2-butenyl)amino-4-trifluoromethyl-2(1H)-quinolinone (Compound 563); 8-Methyl-7-(3-methylbutyl)amino-4-(trifluoromethyl)-2(1H)-quinolinone (Compound 566); 8-Methyl-7-propylamino-4-(trifluoromethyl)-2(1H)-quinolinone (Compound 567); 8-Methyl-7-isobutylamino-4-(trifluoromethyl)-2(1H)-quinolinone (Compound 569); 7-Amino-6-(2,2,2-trifluoroethoxy)-4-trifluoromethyl-2(1H)-quinolinone (Compound 571); 7-(2-Picolylamino)-6-(2,2,2-trifluoroethoxy)-4-trifluoromethyl-2(1H)-quinolinone (Compound 575); 7-Amino-6-cyclohexyl-4-trifluoromethyl-2(1H)-quinolinone (Compound 582); 6-Isobutyl-7-methylamino-4-trifluoromethyl-2(1H)-quinolinone (Compound 588); 7-(1-Morpholino)-4-trifluoromethyl-2(1H)-quinolinone (Compound 589); 6-(bis-N,N-2,2,2-trifluoroethyl)amino-5-methoxy-4-trifluoromethyl-2(1H)-quinolinone (Compound 600); (±)-6-(3-Hydroxy-1-)cyclohexenyl-4-trifluoromethyl-2(1H)-quinolinone (Compound 658); 6-(1-Hydroxy-1,1-diphenyl)methyl-4-trifluoromethyl-2(1H)-quinolinone (Compound 659); 6-(3-hydroxy-3-methyl-1-)butynyl-4-trifluoromethyl-2(1H)-quinolinone (Compound 661); 6-(1-Hydroxy)cyclopentyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 662); 6-(1-Cyclopentenyl)-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 664); 6-Cyclopentyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 665); 6-(1-Hydroxy)cyclohexyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 666); 6-(1-Cyclohexenyl)-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 667); 6-Cyclohexyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 668); 6-(1-Hydroxy)cycloheptyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 669); 6-(1-Cycloheptenyl)-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 670); 6-(1-Cycloheptyl)-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 671); 6-(2,6,6-Trimethyl-1-)cyclohexenyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 672); (±)-6-(3,3,5-Trimethyl-1-)cyclohexenyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 673); (±)-6-(3,5,5-Trimethyl-1-)cyclohexenyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 674); (±)-6-(5-Methyl-1-)cyclohexenyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 675); (±)-6-(3-Methyl-1-)cyclohexenyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 676); (±)-6-(2,6-Dimethyl-1-)cyclohexenyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 677); (±)-6-(2-Bicyclo[2.2.1]heptenyl)-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 678); (±)-6-(4,5-trans-Dimethyl-1-)cyclohexenyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 679); (±)-6-(3,4-trans-Dimethyl-1-)cyclohexenyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 680); 6-(6,6-Dimethyl-1-)cyclohexenyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 681); 6-(5,5-Dimethyl-1-)cyclopentenyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 682); (±)-6-(3,3,5-cis-Trimethyl)cyclohexyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 683); (±)-6-(3,3,5-trans-Trimethyl)cyclohexyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2, one (Compound 684); (±)-6-(3-cis-Methyl)cyclohexyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 685); (±)-6-(3-trans-Methyl)cyclohexyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 686); (±)-6-(2,6-cis,cis-Dimethyl)cyclohexyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 687); (E)-6-(1,4-Dimethyl-1-)pentenyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 688); 6-(1-Cyclohexenyl)-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-thione (Compound 689); 6-(3-Oxo-1-)cyclopentenyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 690); 6-(3-Oxo-1-)cyclohexenyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 691); (±)-6-(3-Hydroxy-1-)cyclohexenyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 692); (±)-6-(3-cis-Hydroxy)cyclohexyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-one (Compound 693); (±)-6-(3-Butyl-3-hydroxy-1-)cyclohexenyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]-oxazin-2-one (Compound 694); 6-(3-Oxo-1-)cyclohexenyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-thione (Compound 695); (±)-6-(3-Hydroxy-1-)cyclohexenyl-1,4-dihydro-4,4-dimethyl-1,3-benzo[d]oxazin-2-thione (Compound 697); (±)-6-(1-Cyclohexenyl)-1,4-dihydro-4-methyl-1,3-benzo[d]oxazin-2-one (Compound 698); 6-(1-Cyclohexenyl)-1,4-dihydro-4,4,5-trimethyl-1,3-benzo[d]oxazin-2-one (Compound 701); 6-(1-Cyclohexenyl)-3,4-dihydro-4,4-dimethyl-2(1H)-quinolinone (Compound 705); 6-Cyclohexyl-3,4-dihydro-4,4-dimethyl-2(1H)-quinolinone (Compound 707); (±)-8-Bromo-6-(1-cyclohexenyl)-1,4-dihydro-4-trifluoromethyl-1,3-benzo[d]oxazin-2-one (Compound 708); 5-(3-Oxo-1-)cyclohexenyl-3,3-dimethyl-2-indolone (Compound 712); (±)-5-(3-Hydroxy-1-)cyclohexenyl-3,3-dimethyl-2-indolone (Compound 714); (±)-5-(3-Oxocyclohexyl)-3,3-dimethyl-2-indolone (Compound 715); 5-Cyclohexyl-3,3-spirocyclohexyl-2-indolone (Compound 716); 5-Cyclopentyl-3,3-spirocyclohexyl-2-indolone (Compound 718); 6-(1-Hydroxycyclohexyl)-2(3H)-benzothiazolone (Compound 719); 6-Cyclohexenyl-2(3H)-benzothiazolone (Compound 720); 1-Benzyl-6-cyclohexyl-3,4-dihydro-3-methyl-2(1H)-quinazolinone (Compound 724); 4-Trifluoromethyl-6-(4,4,4-trifluoro-1(E)-butenyl)-2(1H)-quinolinone (Compound 771); 4-Trifluoromethyl-6-(4,4,4-trifluorobutyro)-2-isopropyloxyquinoline (Compound 772); 4-Trifluoromethyl-6-(1-hydroxy-4,4,4-trifluorobutyl)-2-isopropyloxyquinoline (Compound 773); 4-Trifluoromethyl-6-(1-(3,3,3-trifluoropropyl)-1(E)-propenyl)-2(1H)-quinolinone (Compound 774); 2-Chloro-4-trifluoromethyl-6-(bis-N,N-2,2,2-trifluoroethyl)aminoquinoline (Compound 778); 2-Methoxy-4-trifluoromethyl-6-(bis-2,2,2-trifluoroethyl)aminoquinoline (Compound 779); 2-Isopropyloxy-4-trifluoromethyl-6-(bis-2,2,2-trifluoroethyl)aminoquinoline (Compound 780); 2-Ethoxy-4-trifluoromethyl-6-(bis-2,2,2-trifluoroethyl)aminoquinoline (Compound 781); 2-Acetyloxy-4-trifluoromethyl-6-(bis-2,2,2-trifluoroethyl)aminoquinoline (Compound 782); 2-(2-Dimethylamino)ethoxy-4-trifluoromethyl-6-(bis-2,2,2-trifluoroethyl)amino-quinoline (Compound 783); 2-Isobutyryloxy-4-trifluoromethyl-6-(bis-2,2,2-trifluoroethyl)aminoquinoline (Compound 784); 2-(2,2-Dimethyl)propyryloxy-4-trifluoromethyl-6-(bis-2,2,2-trifluoroethyl)-aminoquinoline (Compound 785); 2-N,N-Dimethylcarbamyloxy-4-trifluoromethyl-6-(bis-2,2,2-trifluoroethyl)-aminoquinoline (Compound 786); 2-Cyano-4-trifluoromethyl-6-(bis-2,2,2-trifluoroethyl)aminoquinoline (Compound 787); and 4-Trifluoromethyl-6-(bis-2,2,2-trifluoroethyl)amino-2(1H)-quinolinone oxime (Compound 788).
25 . A pharmaceutical composition, comprising:
a pharmaceutically acceptable carrier; and a compound of claim 1 .
26 . A pharmaceutical composition, comprising:
a pharmaceutically acceptable carrier; and a compound of claim 2 .
27 . A pharmaceutical composition, comprising:
a pharmaceutically acceptable carrier; and a compound of claim 3 .
28 . The pharmaceutical composition of claim 25 , wherein the compound is an androgen receptor modulator.
29 . A pharmaceutical composition according to claim 28 , wherein the compound is an androgen receptor antagonist.
30 . A pharmaceutical composition according to claim 28 , wherein the compound is an androgen receptor agonist.
31 . A pharmaceutical composition according to claim 28 , wherein the compound is an androgen receptor partial agonist.
32 . A pharmaceutical composition according to claim 25 , wherein the compound is a progesterone receptor modulator.
33 . A pharmaceutical composition according to claim 32 , wherein the compound is a progesterone receptor antagonist.
34 . A pharmaceutical composition according to claim 32 , wherein the compound is a progesterone receptor agonist.
35 . A pharmaceutical composition according to claim 32 , wherein the compound is a progesterone receptor partial agonist.
36 . A pharmaceutical composition, comprising:
a pharmaceutically acceptable carrier; and a compound of claim 24 .
37 . The pharmaceutical composition of claim 25 , wherein the composition is formulated for oral, topical, intravenous, suppository or parenteral administration.
38 . A method of treating an individual having a condition responsive to treatment with an androgen receptor agonist, comprising administering to the individual a pharmaceutically effective amount of a compound of claim 1 that is an androgen receptor agonist and thereby treating the condition.
39 . The method of claim 38 , wherein the condition is impotence, a sexual dysfunction, a wasting disease, hypogonadism, osteoporosis, cancer cachexia or breast cancer.
40 . A method of treating an individual having a condition responsive to treatment with an androgen receptor antagonist, comprising administering to the individual a pharmaceutically effective amount of a compound of claim 1 that is an androgen receptor antagonist and thereby treating the condition.
41 . The method of claim 40 , wherein the condition is acne, male-pattern baldness, a sexual dysfunction, hirsutism, prostatic hyperplasia or prostate cancer.
42 . A method of treating prostate cancer, comprising administering to a patient in need thereof an effective amount of a compound of claim 1 that is an androgen receptor antagonist and thereby treating the prostate cancer.
43 . A method for affecting androgen receptor activity in a mammal, comprising administering to the mammal a compound of claim 1 that is an androgen receptor modulating compound.
44 . A method for affecting progesterone receptor activity in a mammal, comprising administering to the mammal a compound of claim 1 that is a progesterone receptor modulating compound.
45 . A method for affecting androgen receptor activity in a mammal, comprising administering to the mammal a compound of claim 24 that is an androgen receptor modulating compound.
46 . A method for affecting progesterone receptor activity in a mammal, comprising administering to the mammal a compound of claim 24 that is a progesterone receptor modulating compound.
47 . A method for modulating a process in a mammal mediated through androgen receptors, comprising administering to the mammal a pharmaceutically effective amount of a compound of claim 1 that is an androgen receptor modulating compound.
48 . A method for modulating a process in a mammal mediated through progesterone receptors, comprising administering to the mammal a pharmaceutically effective amount of a compound of claim 1 that is a progesterone receptor modulating compound.
49 . A method of modulating a process in a mammal mediated through androgen receptors, comprising administering to the mammal a pharmaceutically effective amount of a compound of claim 24 .
50 . A method of modulating a process in a mammal mediated by progesterone receptors, comprising administering to a mammal a pharmaceutically effective amount of a compound of claim 24 .Cited by (0)
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