| US 7,482,359 B2 | ||
| Androgen receptor modulators | ||
| Jiabing Wang, Chalfont, Pa. (US); and Joshua Close, Abington, Mass. (US) | ||
| Assigned to Merck & Co., Inc., Rahway, N.J. (US) | ||
| Appl. No. 11/660,289 PCT Filed Aug. 19, 2005, PCT No. PCT/US2005/029592 § 371(c)(1), (2), (4) Date Feb. 15, 2007, PCT Pub. No. WO2006/026196, PCT Pub. Date Mar. 09, 2006. |
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| Claims priority of provisional application 60/604368, filed on Aug. 25, 2004. | ||
| Prior Publication US 2007/0269405 A1, Nov. 22, 2007 | ||
| Int. Cl. A61K 31/4738 (2006.01); C07D 471/06 (2006.01) | ||
| U.S. Cl. 514—283 [546/52; 544/322; 514/256] | 8 Claims |
1. A compound of structural formula I:
 a-b represents CH═CH or CH2CH2;
d is 0 or 1;
R1 is selected from hydrogen, C1-4 alkyl, wherein said C1-4 alkyl is optionally substituted with one or more substituents independently selected from halogen, hydroxy, C1-4 alkoxy, and C1-4 alkylamino, and
R2 is chosen from
hydrogen,
hydroxy C0-10alkyl,
perfluoroC1-6alkyl,
perfluoroC1-6alkoxy,
C1-10 alkyl,
C2-10 alkenyl,
C2-10 alkynyl,
aryl C0-10 alkyl,
C3-8 cycloalkyl C0-10 alkyl,
C3-8 heterocyclyl C0-10 alkyl,
(C0-10 alkyl)1-2aminocarbonyloxy C0-10 alkyl,
(aryl C0-10 alkyl)1-2aminocarbonyloxy C0-10 alkyl,
(C3-8 cycloalkyl C0-10 alkyl)1-2aminocarbonyloxy C0-10 alkyl,
(C3-8 heterocyclyl C0-10 alkyl)1-2aminocarbonyloxy C0-10 alkyl,
(C0-10 alkyl)1-2aminocarbonylaminoC1-10 alkyl,
(aryl C0-10 alkyl)1-2aminocarbonylamino C1-10 alkyl,
(C3-8 cycloalkyl C0-10 alkyl)1-2aminocarbonylamino C1-10 alkyl,
(C3-8 heterocyclyl C0-10 alkyl)1-2aminocarbonylamino C1-10 alkyl,
(C0-10 alkyl)1-2aminocarbonyl C0-10 alkyl,
(aryl C0-10 alkyl)1-2aminocarbonyl C0-10 alkyl,
C3-8 cycloalkyl C0-10 alkyl aminocarbonyl C0-10 alkyl,
C3-8 heterocyclyl C0-10 alkyl aminocarbonyl C0-10 alkyl,
C0-10 alkyl carbonylamino C1-10 alkyl,
C3-8 cycloalkyl C0-10 alkyl carbonylamino C1-10 alkyl,
C3-8 heterocyclyl C0-10 alkyl carbonylamino C1-10 alkyl,
aryl C0-10 alkyl carbonylamino C1-10 alkyl,
C0-10 alkyloxy carbonylamino C1-10 alkyl,
C3-8 cycloalkyl C0-10 alkyloxy carbonylamino C1-10 alkyl,
C3-8 heterocyclyl C0-10 alkyloxy carbonylamino C1-10 alkyl,
aryl C0-10 alkyloxy carbonylamino C1-10 alkyl,
C0-10 alkyloxy carbonyloxy C0-10 alkyl,
C3-8 cycloalkyl C0-10 alkyloxy carbonyloxy C0-10 alkyl,
C3-8 heterocyclyl C0-10 alkyloxy carbonyloxy C0-10 alkyl,
aryl C0-10 alkyloxy carbonyloxy C0-10 alkyl,
C1-10 alkoxy (carbonyl)0-1C0-10 alkyl,
C1-10alkyloxy C0-10alkyl,
aryloxy C0-10 alkyl,
C3-8 cycloalkyloxy C0-10 alkyl,
C3-8 heterocyclyloxy C0-10 alkyl,
C3-8 heterocyclylC0-10alkyloxy C0-10 alkyl, and
C1-10 alkylcarbonyloxy C0-10 alkyl;
wherein in R2, said aryl is selected from phenyl, naphthyl, indanyl, and tetrahydronapthyl, and said heterocyclyl is selected from azabenzimidazolyl,
benzimidazolyl, benzofuranyl, benzothiophenyl, benzoxazolyl, benzothiazolyl, benzodihydrofuranyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl,
imidazolyl, indanyl, indolyl, indazoyl, isoquinolyl, isothiazolyl, isoxazolyl, quinolyl, furanyl, thienyl, oxazolyl, thiazolyl,
pyrazolyl, pyrrolyl, pyridyl, pyrimidyl, pyrazinyl, thiadiazolyl, oxadiazolyl, triazolyl, imidizopyridinyl, and tetrazolyl;
and
further wherein in R2 is optionally substituted with one or more groups, R3, chosen from halogen, aryl, C1-8 alkyl, C3-8 cycloalkyl, C3-8 cycloheteroalkyl, aryl-C1-6 alkyl, amino-C0-6 alkyl, C1-6 alkylamino-C0-6 alkyl, (C1-6 alkyl)2amino-C0-6 alkyl, aryl-C0-6 alkylamino-C0-6 alkyl, (aryl-C0-6 alkyl)2amino-C0-6 alkyl, C1-6 alkylthio, aryl-C0-6 alkylthio, C1-6 alkylsulfinyl, aryl-C0-6 alkylsulfinyl, C1-6 alkylsulfonyl, aryl-C0-6 alkylsulfonyl, C1-6 alkoxy-C0-6 alkyl, aryl-C0-6 alkoxy-C0-6 alkyl, hydroxycarbonyl-C0-6 alkyl, C1-6 alkoxycarbonyl-C0-6 alkyl, aryl-C0-6 alkoxycarbonyl-C0-6 alkyl, hydroxycarbonyl-C1-6 alkyloxy, hydroxy-C0-6 alkyl, cyano, nitro, perfluoro-C1-4 alkyl, perfluoro-C1-4 alkoxy, C1-6 alkylcarbonyloxy, aryl-C0-6 alkylcarbonyloxy, C1-6alkylcarbonylamino, aryl-C0-6 alkylcarbonylamino, C1-6 alkylsulfonylamino, aryl-C0-6 alkylsulfonylamino, C1-6 alkoxycarbonylamino, aryl-C0-6 alkoxycarbonylamino, C1-6 alkylaminocarbonylamino, aryl-C0-6 alkylamino-carbonylamino, (C1-6 alkyl)2 aminocarbonylamino, (aryl-C0-6 alkyl)2 aminocarbonylamino, (C1-6 alkyl)2 aminocarbonyloxy, and (aryl-C0-6 alkyl)2 aminocarbonyloxy; and
wherein R3 is optionally substituted with one or more groups chosen from: OH, C1-6 alkoxy, halogen, CO2H, CN, O(C═O) C1-6 alkyl, NO2, trifluoromethoxy, trifluoroethoxy, —O(d)(C1-10)perfluoroalkyl, and NH2.
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