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US 4,732,897 AGranted
Steroidic 5.alpha.-reductase inhibitors
AssigneesFarmitalia Carlo Erba S.p.A., Consiglio Nazionale Delle Ricerche
InventorsGianfranco Cainelli, Giorgio Martelli, Mauro Panunzio, Giuseppe Spunta, Giuliano Nannini, Enrico di Salle
Life of this patent
Estimating the term…
Abstract
The present invention relates to new 4-aza-17.beta.-substituted 5.alpha.-androstan-3-ones, to a process for their preparation, to pharmacological compostions containing them, and to the use of said compounds as inhibitors of androgen action by means of testosterone 5-reductase inhibition.
Claims9
A compound of the following formula (I) ##STR63## wherein R.sub.1 is
- (a) hydrogen;
- (b) C.sub.1 -C.sub.6 alkyl unsubstituted or substituted by a substituent chosen from carboxy, halogen and amino;
- (c) a phenyl, .alpha.-naphthyl, .beta.-naphthyl or benzyl group, either unsubstituted or ring substituted by a substituent chosen from C.sub.1 -C.sub.6 alkyl, halogen, nitro, amino and hydroxy, or
- (d) --OR.sub.2 wherein R.sub.2 either has one of the meanings (a), (b) and (c) reported above for R.sub.1 ;
- or is a C.sub.2 -C.sub.12 -aliphatic or aromatic carboxylic acyl or a hydroxy protecting group chosen from the group consisting of dimethyltert butyl silyl, trimethylsilyl, and 2-tetrahydropyranyl;
- X is direct bond or a straight or branched C.sub.1 -C.sub.6 -aliphatic hydrocarbon chain;
- the symbol .dbd.Y represents ##STR64## or .dbd.O;
- Z is
- (a') hydroxy;
- (b') C.sub.1 -C.sub.6 alkoxy;
- or
- (c') ##STR65## wherein each of R.sub.3 and R.sub.4 is, independently, hydrogen or C.sub.1 -C.sub.6 alkyl;
- or R.sub.3 and R.sub.4 taken together with the nitrogen atom to which they are linked, from a hexatomic heteromonocyclic ring chosen from piperidino, piperazino, morpholino and thiomorpholino;
- the symbol ------ represents a single or double bond, and the pharmaceutically acceptable salts thereof.
11 more elements
A compound selected from the group consisting of:
- 24-N,N-diethylcarbamoyl-4-methyl-4-azachol-5-en-3,12-dione;
- 24-N,N-diethylcarbamoyl-4-ethyl-4-azachol-5-en-3,12-dione;
- 24-N,N-dimethylcarbamoyl-4-dimethyl-4-azachol-5-en-3,12-dione;
- 24-N,N-dimethylcarbamoyl-4-ethyl-4-azachol-5-en-3,12-dione;
- 24-N,N-diethylcarbamoyl-4-methyl-4-azachol-5-en-12.alpha.-hydroxy-3-one;
- 24-N,N-diethylcarbamoyl-4-methyl-4-aza-5.alpha.-cholan-3,12-dione;
- 24-methoxycarbonyl-4-methyl-4-aza-chol-5-en-3,12-dione;
- and
- 24-methoxycarbonyl-4-methyl-4-aza-5.alpha.-cholan-3,12-dione.
6 more elements
Dependencies are inferred from the claim text.