16-Methylene-17.alpha.-hydroxy-progesterones
AssigneeThe Upjohn Company
InventorVerlan H. VanRheenen
Life of this patent
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Abstract
16-Methylene-17-keto steroids (III) are transformed to the corresponding 16-methylene-17.alpha.-hydroxyprogesterones (VII) which are intermediates useful in the production of betamethasone, diflorasone diacetate and melengesterol acetate.
Claims79
A 17.beta.-hydroxy steroid selected from the group consisting of
- and C.sub.3 protected forms thereof where
- R.sub.6 is a hydrogen or fluorine atom, methyl or methylene group, when R.sub.6 is methylene, there are no 6-7 double bonds in formula (A) or 5-6 double bonds in formula (C);
- R.sub.9 is nothing or a hydrogen or fluorine atom, which includes the .DELTA.9(11) and 9.beta.,11.beta.-epoxide functionality;
- R.sub.11 is nothing or a hydrogen or oxygen atom, an .alpha.-hydroxy group, or a .beta.-hydroxy group, which includes the .DELTA.9(11) and 9.beta.,11.beta.-epoxide functionality;
- .about. indicates that the attached atom or group can be in either the .alpha. or .beta. configuration;
- and
- .sub.---- is a single or double bond.
A 17.beta.-hydroxy steroid according to claim 16 which is 17.alpha.-acetyl-17.beta.-hydroxy-6-methyl-16-methyleneandrosta-4,6-dien-3 -one.
A sulfoxide according to claim 16 of the formula ##STR10## where R.sub.22 is defined in claim 32, R.sub.6, R.sub.11, .about. and .sub.---- are defined in claim 1.
A sulfoxide according to claim 16 of the formula ##STR11## and C.sub.3 protected forms thereof where R.sub.22 is defined in claim 32, R.sub.6, R.sub.9, R.sub.11, .about. and .sub.---- are defined in claim 1.
17.alpha.-hydroxy-6,16-dimethylenepregna-4-ene-3,20-dione 17-acetate.
17.alpha.-hydroxy-16-methylenepregna-1,4,9(11)-triene-3,20-dione.
A process for the preparation of a 17.beta.-hydroxy steroid of the formula ##STR15## which comprises contacting a 17.alpha.-ethynyl steroid of the formula ##STR16## with a mercuric agent.
17.alpha.,21-Dihydroxy-16-methylenepregna-1,4,9(11)-triene-3,20-dione 21-acetate.
A 17-ethynyl steroid which is 17.alpha.-ethynyl-17.beta.-hydroxy-16-methyleneandrost-4-en-3-one.
17.alpha.-Hydroxy-3.beta.-methoxy-16-methylenepregna-3,5-diene-20-one.
Dependencies are inferred from the claim text.