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Details for Patent: 4,578,221

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Details for Patent: 4,578,221

Title: Androstane carbothioic acids
Abstract:Androstane carbothioic acids of the formula: ##STR1## wherein R.sup.1 represents a hydrogen atom, a hydroxy group in the .alpha.-configuration, a methyl group which may be in either the .alpha.- or .beta.-configuration, or a methylene group; R.sup.2 represents a hydroxy or protected hydroxy group in either the .alpha.- or .beta.-configuration or an oxo group; R.sup.3 represents a hydrogen, bromine, chlorine or fluorine atom; or R.sup.2 and R.sup.3 together represent a carbon-carbon bond or an epoxy group in the .beta.-configuration; R.sup.4 represents a hydrogen or fluorine atom; and the symbol represents a single or double bond and the salts thereof are useful as intermediates in the preparation of anti-inflammatory androstane 17.beta.-carbothioate esters. The compounds of formula I are prepared by reaction of a reactive derivative of a 17.beta.-carboxylic acid corresponding to the compound of formula I with hydrogen sulphide or a sulphide or hydrosulphide salt.
Inventor(s): Phillipps; Gordon H. (Wembley, GB2), Bain; Brian M. (Chalfont St. Peter, GB2), Laing; Stuart B. (Harrow, GB2)
Assignee: Glaxo Group Limited (GB2)
Filing Date:Jul 14, 1983
Application Number:06/513,396
Claims:1. A process for the preparation of a compound of the formula: ##STR10## wherein R.sup.1 represents a hydrogen atom, a hydroxy group in the .alpha.-configuration, a methyl group which may be in either the .alpha.- or .beta.-configuration or a methylene group;

R.sup.2 represents a hydroxy or protected hydroxy group in either the .alpha.-or .beta.-configuration or an oxo group;

R.sup.3 represents a hydrogen, bromine, chlorine or fluorine atom; or R.sup.2 and R.sup.3 together represent a carbon-carbon bond or an epoxy group in the .beta.-configuration;

R.sup.4 represents a hydrogen or fluorine atom; and the symbol represents a single or double bond; and the salts thereof, in which a compound of the formula: ##STR11## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined above and R.sup.5 represents a group of the formula: ##STR12## in which X, Y and Z, which may be the same or different, each represents CH or N, one or two of X, Y and Z being N, the heterocyclic ring optionally being substituted on at least one carbon atom by a lower alkyl group and/or where the heterocyclic ring contains two adjacent carbon atoms, the said ring optionally carrying a benzene ring fused to the said adjacent carbon atoms;

is reacted with hydrogen sulphide or a sulphide or hydrosulphide salt.

2. A process according to claim 1 wherein the compound of formula III is first prepared by reaction of a corresponding compound of formula III carrying a carboxylic acid group at the 17.beta.-position with a symmetric or asymmetric compound of the formula:

wherein W represents the group CO, CS, SO or SO.sub.2 and the groups R.sup.5, which may be the same or different, are as defined in claim 1.

3. A process according to claim 2 wherein a compound of formula IV is used in which W represents the group CO, CS or SO.

4. A process according to claim 3 wherein the compound of formula IV used is N,N'-carbonyldi(1,2,4-triazole), N,N'-carbonyldibenzotriazole, N,N'-carbonyldibenzimidazole, N,N'-carbonyldi(3,5-dimethylpyrazole) or N,N-thionyldiimidazole.

5. A process according to claim 3 wherein the compound of formula IV used is N,N'-carbonyldiimidazole or N,N'-thiocarbonyldiimidazole.

6. A process according to claim 2 wherein reaction of a compound corresponding to a compound of formula III, but carrying a 17.beta.-carboxylic acid group with a compound of formula IV is followed in situ by reaction of the compound of formula III thus obtained, with hydrogen sulphide or a sulphide or hydrosulphide salt without isolation of the compound of formula III.

7. A process for the preparation of a compound of the formula: ##STR13## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined in claim 1 and R.sup.a represents a C.sub.1-6 alkyl group or a C.sub.1-2 alkyl group carrying a terminal halogen atom or a benzyl group which may be substituted by a C.sub.1-4 alkyl or C.sub.1-4 alkoxy group or a halogen atom,

which process comprises esterifying the 17.beta.-carbothioic acid group of a compound of formula I or a salt thereof.

8. A process according to claim 7, wherein R.sup.a represents a C.sub.1-2 alkyl group carrying a terminal halogen atom.
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