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US 5,194,602 AGranted
9.alpha.-hydroxy-17-methylene steroids, process for their preparation and their use in the preparation of corticosteroids
AssigneeGist-Brocades N.V.
InventorsJacobus N. M. Batisi, Arthur F. Marx
Life of this patent
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Abstract
New 9.alpha.-hydroxy-17-methylene steroids are prepared by the introduction of a substituted 17-methylene group in 9.alpha.-hydroxyandrost-4-ene-3, 17-dione. The resulting compounds are useful starting compounds in the synthesis of corticosteroids.
Claims7
A 9.alpha.-Hydroxy-17-methylene steroid containing a D-ring according to formula I
- where
- R.sub.1 is hydrogen, halogen, cyano, isocyano, formamido, (1-6C) alkoxy,
- R.sub.2 is nitro, methyl, (1-6C) alkoxycarbonyl, hydroxymethyl, (1-6C) alkylcarbonyloxymethyl the 20-carbon atom being either in the Z- or in the E- configuration,
- R.sub.3 is hydrogen
- R.sub.4 is hydrogen, hydroxy, methyl or R.sub.3 and R.sub.4 together form methylene,
- R.sub.5 is hydrogen, alkyl or with R.sub.6 is a double bond, epoxy, methylene, 3,3-alkylenedioxy, 3,3-alkylenedithio or 3,3-alkyleneoxythio group, the alkylene group containing 2 or 3 carbon atoms,
- R.sub.6 is hydrogen, alkyl or with R.sub.5 is a double bond, epoxy, methylene, 3,3-alkylenedioxy, 3,3-alkylenedithio or 3,3-alkyleneoxythio group, the alkylene group containing 2 or 3 carbon atoms,
- R.sub.7 is hydrogen, hydroxy, oxo, (1-4C) alkoxy, (1-6C) alkylcarbonyloxy, alkoxyalkoxy, tetrahydropyranyloxy, amino, 3-alkylamino containing 1 through 4 carbon atoms, 3-dialkylamino wherein the alkyl groups are the same or different, each alkyl group containing 1 through 4 carbon atoms, or 3-dialkylamino groups in which the nitrogen atom together with the alkyl groups forms a heterocyclic ring having 3 through 6 ring atoms, or 3-morpholino imino, 3-hydroxyimino, 3-(1-6C) alkoxyimino, 3,3-alkylenedioxy, 3,3-alkylenedithio, 3,3-alkyleneoxythio, the alkylene group containing 2 or 3 carbon atoms, or with R.sub.8 is a double bond,
- R.sub.8 is hydrogen or with R.sub.7 or R.sub.9 is a double bond,
- R.sub.9 is hydrogen or with R.sub.8 or R.sub.10 is a double bond,
- R.sub.10 is hydrogen, halogen or alkyl or with R.sub.9 or R.sub.11 is a double bond,
- R.sub.11 is hydrogen, hydroxy or alkyl or with R.sub.9 or R.sub.11 is a double bond,
- R.sub.12 is hydrogen, hydroxy, halogen, alkoxy, alkoxyalkoxy, tetrahydropyranyloxy or with R.sub.13 is a double bond,
- R.sub.13 is hydrogen, hydroxy, oxo, (1-4C) alkoxy or with R.sub.12 is a double bond,
- R.sub.14 is hydrogen or hydroxy,
- with the exception of 9.alpha.,21-dihydroxypregna-4,17-(20)-diene-3,11-dione and the corresponding 21-acetate.
13 more elements
A 9.alpha.-Hydroxy-17-methylene steroid selected from the group consisting of (1-6C)alkyl 20-formamido-9.alpha.-hydroxy-3-oxopregna-4,17(20)-dien-21-oate;
- 20-formamido-9.alpha.,21-dihydroxypregna-4,17(20)-dien-3one;
- (1-6C)alkyl 20-chloro-9.alpha.-hydroxy-3-oxopregna-4,17(20)-dien-21-oate;
- (1-6C)alkyl 20-(1-6C)alkoxy-9.alpha.-hydroxy-3-oxopregna-4,17(20)-dien-21-oate;
- 20-(1-6C)alkoxy-9.alpha.,21-dihydroxypregna-4,17(20)-dien-3-one;
- 21-(1-6C)alkylcarbonyloxy-20-(1-6C)alkoxy-9.alpha.-hydroxypregna-4,17(20)- dien-3-one;
- 9.alpha.-hydroxy-17-nitromethyleneandrost-4-en-3-one;
- 9.alpha.-hydroxypregna-4,17-(20)-dien-3-one;
- 9.alpha.-hydroxy-20-isocyanopregna-4,17(20)-dien-3-one;
- 20-formamido-9.alpha.-hydroxypregna-4,17(20)-dien-3-one;
- (1-6C)alkyl-20-cyano-9.alpha.-hydroxy-3-oxopregna-4,17(20)-dien-21-oate, in which compounds the function on C3 may be properly protected and C16 may be substituted by a methyl, a methylene or a hydroxyl group.
7 more elements
Dependencies are inferred from the claim text.