14,17.beta.-ethano-14.beta.-estratrienes and estratetraenes, process for their production, and pharmaceutical preparations containing them
AssigneeSchering Corporation
InventorsJames R. Bull, Russell I. Thomson, Henry Laurent, Helmut Schroeder, Rudolf Wiechert
Life of this patent
Estimating the term…
Abstract
14,17.beta.-ethano-14.beta.-estratriene and estratetraene of Formula I ##STR1## wherein R.sup.1 is a hydrogen atom, a methyl or an acyl group of a monocarboxyclic acid of 1-12 carbon atoms, R.sup.2 is a hydrogen atom or an acyl group of a monocarboxylic acid of 1-12 carbon atoms, R.sup.3 is a hydrogen atom or a methyl group, and ##STR2## is a single or double C--C-bond show strong estrogenic activity.
Claims27
A 14,17.beta.-ethano-14.beta.-estratriene and estratetraene of Formula I ##STR6## wherein R.sup.1 is a hydrogen atom, a methyl or an acyl group of a monocarboxylic acid of 1-12 carbon atoms,
- R.sup.2 is a hydrogen atom or an acyl group of a monocarboxylic acid of 1-12 carbon atoms,
- R.sup.3 is a hydrogen atom or a methyl group, and ##STR7## is a single or double C--C-bond, with the proviso that
- (a) when R.sup.1 is methyl, ##STR8## is a double bond and R.sup.3 is H, then R.sup.2 is not acetyl or H;
- (b) when R is acyl, ##STR9## is a double bond and R.sup.3 is H, then R.sup.2 is not acetyl;
- and (c) when R.sup.1 is H, ##STR10## is a double bond and R.sup.3 is H, then R.sup.2 is not H.
A 14,17.beta.-ethano-14.beta.-estratriene or estratetraene of Formula I ##STR11## wherein (a) R.sup.2 is methyl, - - - is a double bond, R.sup.3 is H, and R.sup.2 is acetyl or H;
- (b) R.sup.1 is acetyl, - - - is a double bond, R.sup.3 is H, and R.sup.2 is acetyl;
- and
- (c) R.sup.1 is H, - - - is a double bond, R.sup.3 is H, and R.sup.2 is H.
A compound of claim 27 which is 14,17.beta.-Ethano-3-methoxy-14.beta.-estra-1,3,5(10),15-tetraene-17.alpha .-ol.
A pharmaceutical composition comprising an estrogenically effective amount of a compound of general Formula I, in unit dosage form and in admixture with a pharmaceutically acceptable carrier, wherein Formula I is ##STR12## wherein R.sup.1 is a hydrogen atom, a methyl or an acyl group of a monocarboxylic acid of 1-12 carbon atoms,
- R.sup.2 is a hydrogen atom or an acyl group of a monocarboxylic acid of 1-12 carbon atoms,
- R.sup.3 is a hydrogen atom or a methyl group, and ##STR13## is a single or double C--C-bond.
A method of treating symptoms of estrogen deficiency or for the control of fertility in women which comprises administering an effective amount of a compound of general Formula I, ##STR14## wherein R.sup.1 is a hydrogen atom, a methyl or an acyl group of a monocarboxylic acid of 1-12 carbon atoms,
- R.sup.2 is a hydrogen atom or an acyl group of a monocarboxylic acid of 1-12 carbon atoms,
- R.sup.3 is a hydrogen atom or a methyl group, and ##STR15## is a single or double C--C-bond.
A process for the preparation of a compound of general Formula I ##STR16## wherein R.sup.1 is a hydrogen atom, a methyl or an acyl group of a monocarboxylic acid of 1-12 carbon atoms,
- R.sup.2 is a hydrogen atom or an acyl group of a monocarboxylic acid of 1-12 carbon atoms,
- R.sup.3 is a hydrogen atom or a methyl group, and - - - is a single or double C--C-bond, comprising reductively removing, with amalgam or Raney nickel, the phenylsulphonyl group from a compound of general Formula II ##STR17## wherein R.sup.1 is a methyl or an acetyl group;
- R.sup.3 is a hydrogen atom or a methyl group;
- R.sup.4 is hydrogen and R.sup.5 is phenylsulfphonyl, when R.sup.3 is hydrogen;
- and one of R.sup.4 or R.sup.5 is phenylsulphonyl and the other is hydrogen, when R.sup.3 is methyl:
- and, optionally, subsequently hydrogenating the .DELTA..sup.15 double bond and, optionally, subsequently cleaving the 3 methyl ether or saponifying an acetoxy group and subsequently optionally esterifying a phenolic or tertiary hydroxy group and subsequently optionally partially saponifying a phenolic ester.
Dependencies are inferred from the claim text.