Novel 1,2-methylene-17.alpha.-acyloxy (or improved hydroxy)-9.beta., 10.alpha.-steroid compounds of the pregnane series, pharmaceutic preparations on the basis of the novel compounds and methods of producing said compounds and preparations
AssigneeU.S. Philips Corporation
InventorsHarmen Van Kamp, Pieter Westerhof, Lucas Morsink
Life of this patent
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Abstract
New 1,2-methylene-17.alpha. acyloxy-9.beta., 10.alpha. pregnane compounds having high progestational and anti-ovulatory activities.
Claims14
A compound of the formula ##SPC35##
- wherein X is hydrogen and Y is a member selected from the group consisting of hydroxy and esterified hydroxy of 1-20 carbon atoms derived from an acid containing only carbon, hydrogen and carboxylic moieties or X and Y together form a double bonded oxygen atom, R.sub.3 is a member selected from the group consisting of 3-keto-4-dehydro, 3-keto-4,6-bisdehydro-, 3-OR'-3,5-bisdehydro and 3-OR'-4,6-bisdehydro wherein OR' is a member selected from the group consisting of esterified hydroxy of 1-20 carbon atoms derived from an acid containing only carbon, hydrogen and carboxylic moieties, methoxy, ethoxy, butoxy, cyclohexyloxy, benzyloxy, tetrahydrofuranyloxy and tetrahydro-pyranyloxy, R.sub.6 is a member selected from the group consisting of hydrogen, chlorine, fluorine, 6,6-difluoro, 6,6-dichloro and methyl, R.sub.7 is a member selected from the group consisting of hydrogen and 6,7-methylene with the proviso that R.sub.7 is 6,7 methylene when R.sub.6 is hydrogen and R.sub.6 is a member of the group consisting of hydrogen, chlorine and fluorine and R.sub.3 is 3-keto-4-dehydro when R.sub.7 is 6,7-methylene, R.sub.17 is a member of the group consisting of esterified hydroxy of 1 to 5 carbon atoms and esterified hydroxy of 1 to 8 carbon atoms derived from an acid containing only carbon, hydrogen and carboxylic moieties, R.sub.21 is a member of the group consisting of hydrogen, fluorine, hydroxy and esterified hydroxy of 1 to 20 carbon atoms derived from an acid containing only carbon, hydrogen and carboxylic moieties, and R.sub.13 is a member of the group consisting of methyl and ethyl.
A compound of the formula:
- ##SPC36##
- wherein Hal is chlorine or fluorine and R.sub.17 is etherified hydroxy of 1-5 carbon atoms.
1,2-methylene-6-chloro-17.alpha.-hydroxy-9.beta.,10.alpha. -pregna-4,6-diene-3,20-dione 17-acetate.
1,2-methylene-6-fluoro-17.alpha.-hydroxy-9.beta.,10.alpha. -pregna-4,6-diene-3,20-dione 17-acetate.
1,2-methylene-6-fluoro-17.alpha.-hydroxy-9.beta.,10.alpha. -pregna-4,6-diene-3,20-dione 17-propionate.
1,2-methylene-6-chloro-17.alpha.-tetrahydropyranyloxy-9.beta.,10.alpha. -pregna-4,6-diene-3,20-dione.
1,2-methylene-6-fluoro-17.alpha.-tetrahydropyranyloxy-9.beta.,10.alpha. -pregna-4,6-diene-3,20-dione.
Dependencies are inferred from the claim text.