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Details for Patent: 5,817,818

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Details for Patent: 5,817,818

Title: Androstenones
Abstract:The present invention relates to compounds of formula (I), wherein carbons 1 and 2 are joined by either a single or a double bond; R.sup.1 is hydrogen or methyl; R.sup.2 is hydrogen or methyl; R.sup.3 is (A) or (B) wherein X, W, Z, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are various groups, and pharmaceutically acceptable solvates thereof and their use in the treatment of androgen responsive and mediated diseases. ##STR1##
Inventor(s): Batchelor; Kenneth William (Durham, NC), Frye; Stephen Vernon (Durham, NC)
Assignee: Glaxo Wellcome Inc. (Research Triangle Park, NC)
Filing Date:Mar 14, 1996
Application Number:08/617,859
Claims:1. A compound of formula (I) ##STR17## wherein carbons 1 and 2 are joined by either a single or a double bond; R.sup.1 is hydrogen or methyl;

R.sup.2 is hydrogen or methyl;

R.sup.3 is (A) ##STR18## wherein R.sup.4 and R.sup.5 are independently hydrogen, lower alkyl, lower alkoxy, trifluoromethyl, cyano, halogen, phenyl (optionally substituted with one or more halogens), or when R.sup.4 and R.sup.5 are on adjacent carbons, taken together form a fused 5, 6 or 7 member ring optionally containing one or more oxygen or sulfur atoms;

W and Z are alkylene groups which taken together with the carbon to which they are attached form a saturated, 3 to 12 member ring system optionally:

1) substituted independently with one or more lower alkyl groups,

2) having an oxygen or sulfur atom,

3) two of said alkylene groups of said 3 to 12 member ring are joined with a (C.sub.1-6) alkylene group to form a bicyclic ring system; and

X is hydrogen or halogen;

or a pharmaceutically acceptable solvate thereof.

2. A compound as claimed in claim 1 wherein X is hydrogen.

3. A compound as claimed in claim 1 wherein R.sup.2 is hydrogen.

4. A compound as claimed in any one of claims 1 wherein carbons 1 and 2 are joined by a double bond.

5. A compound as claimed in claim 1 of formula (IA) ##STR19## wherein carbons 1 and 2 are joined by either a single or a double bond; R.sup.1 is hydrogen or methyl;

R.sup.4 and R.sup.5 are independently hydrogen, lower alkyl, lower alkoxy, trifluoromethyl, cyano, halogen, phenyl (optionally substituted with one or more halogens), or when R.sup.4 and R.sup.5 are on adjacent carbons, taken together form a fused 5, 6 or 7 member ring optionally containing one or more oxygen or sulfur atoms;

W and Z are alkylene groups which taken together with the carbon to which they are attached form a saturated, 3 to 12 member ring system optionally:

1) substituted with one or more lower alkyl groups,

2) containing an oxygen or sulfur atom,

3) two of said alkylene groups of said 3 to 12 member ring are joined with a (C.sub.1-6) alkylene group to form a bicyclic ring system; and

X is hydrogen or halogen.

6. A compound as claimed in claim 5 wherein R.sup.4 and R.sup.5 are independently hydrogen, lower alkyl, lower alkoxy, trifluoromethyl, cyano, halogen, or phenyl (optionally substituted with one or more halogens); and X is hydrogen.

7. A compound as claimed in claim 5 wherein at least one of X, R.sup.4 and R.sup.5 is other than hydrogen.

8. A compound as claimed in any one of claims 5 to 7 which carries a substituent in the para(4--) position of the phenyl ring.

9. A compound as claimed in claim 6 wherein at least one of R.sup.4 and R.sup.5 is lower alkyl, lower alkoxy, trifluoromethyl, halogen or phenyl.

10. A compound as claimed in claim 9 wherein at least one of R.sup.4 and R.sup.5 is branched alkyl, trifluoromethyl or halogen.

11. 17.beta.-N-1-(4-Chlorophenyl)cyclopentylcarbamoyl-4 -aza-5.alpha.-androst-1-en-3-one or a pharmaceutically acceptable solvate thereof.

12. A coumpound of formula (IVa) ##STR20## wherein R.sup.1 and R.sup.2 are independently hydrogen or methyl and R.sup.3 is as defined in claim 1, or a solvate thereof.

13. 17-N-1-(4-Chlorophenyl)cyclopentylcarbamoyl-4-aza-androst-5-en-3-one or a solvate thereof.

14. The compound of claim 1 wherein said compound is selected from the group consisting of: 17.beta.-N-1-(4-Chlorophenyl)cyclopentylcarbamoyl-4-aza-5.alpha.-androstan -3-one, 17.beta.-N-1-(4-Chlorophenyl)cyclopentylcarbamoyl-4-methyl-4-aza-5.alpha.- androstan-3-one, 17.beta.-N-1-(4-Chlorophenyl)cyclopentylcarbamoyl-4-aza-5.alpha.-androst-1 -en-3-one, 17.beta.-N-1-(4-t-Butylphenyl)cyclopentylcarbamoyl-4-aza-5.alpha.-androst- 1-en-3-one, 17.beta.-N-1-(4-t-Butylphenyl)cyclohexylcarbamoyl-4-aza-5.alpha.-androst-1 -en-3-one, 17.beta.-N-1-(4-Chlorophenyl)cyclohexylcarbamoyl-4-aza-5.alpha.-androst-1- en-3-one, 17.beta.-N-1-(4-Trifluoromethylphenyl)cyclopentylcarbamoyl-4-aza-5.alpha.- androst-1-en-3-one, 17.beta.-3-N-1-(4-Methoxyphenyl)cyclopentylcarbamoyl-4-aza-5.alpha.-andros t-1-en-3-one, 17.beta.-N-1-(4-Fluorophenyl)cyclopentylcarbamoyl-4-aza-5.alpha.-androst-1 -en-3-one, 17.beta.-N-1-(4-Fluorophenyl)cyclohexylcarbamoyl-4-aza-5.alpha.-androst-1- en-3-one, 17.beta.-N-1-(4-Methoxyphenyl)cyclohexylcarbamoyl-4-aza-5.alpha.-androst-1 -en-3-one, 17.beta.-N-1-(3,4-Methylenedioxyphenyl)cyclohexylcarbamoyl-4-aza-5.alpha.- androst-1-en-3-one, 17.beta.-N-1-(4-t-Butylphenyl)cycloheptylcarbamoyl-4-aza-5.alpha.-androst- 1-en-3-one, 17.beta.-N-4-(4-t-Butylphenyl)tetrahydropyranylcarbamoyl-4-aza-5.alpha.-an drost-1-en-3-one, 17.beta.-N-1-(2,4-Dichlorophenyl)cyclopropylcarbamoyl-4-aza-5.alpha.-andro st-1-en-3-one, 17.beta.-N-1-(4-Trifluoromethylphenyl)-2,2-diethylcyclopropylcarbamoyl-4-a za-5.alpha.-androst-1-en-3-one, 17.beta.-N-1-(4-t-Butylphenyl)-4,4-dimethylcyclohexylcarbamoyl-4-aza-5.alp ha.-androst-1-en-3-one, 17.beta.-N-1-(4-t-Butylphenyl)-4-t-Butylcyclohexylcarbamoyl-4-aza-5.alpha. -androst-1-en-3-one, 17.beta.-N-1-(3-Trifluoromethylphenyl)cyclopentylcarbamoyl-4-aza-5.alpha.- androst-1-en-3-one, 17.beta.-N-4-(4-t-Butylphenyl)tetrahydrothiopyranylcarbamoyl-4-aza-5.alpha .-androst-1-en-3-one, 17.beta.-N-1-(4-Biphenyl)-2,2-diethylcyclopropylcarbamoyl-4-aza-5.alpha.-a ndrost-1-en-3-one, 17.beta.-N-1-(4-Chlorophenyl)cyclopentylcarbamoyl-4-aza-7.beta.-methyl-5.a lpha.-androst-1-en-3-one, and 17.beta.-N-9-(4-t-Butylphenyl)bicyclo[3.3.1]nonylcarbamoyl-4-aza-5.alpha.- androst-1-en-3-one.
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