US 6,147,065 AGranted

14-.alpha., 17-.alpha.-C.sub.2 bridged norprogesterone derivatives

AssigneeSchering Corporation

InventorsKlaus Schollkopf, Wolfgang Halfbrodt, Joachim Kuhnke, Wolfgang Schwede, Karl-Heinrich Fritzemeier, Rolf Krattenmacher, Hans-Peter Muhn

Life of this patent

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Abstract

Described are 14,17-C.sub.2 -bridged steroids of the formula (I) defined in the specification. The compounds are available, even after peroral administration, with high gestagenic action and are suitable for the production of pharmaceutical agents.

Claims30

Dependent claims

A method for inducing a contraceptive effect in a patient desiring such an effect, comprising orally administering a contraceptively effective amount of a 14,17-C.sub.2 -bridged steroid of formula (I):

##STR15## wherein R.sup.3 is O, a hydroxyimino group or two H atoms,
R.sup.6 is H, fluorine, chlorine or bromine;
or a C.sub.1 -C.sub.4 alkyl radical in the .alpha.- or .beta.-position and R.sup.6' and R.sup.7 are H atoms, or
R.sup.6, is H, fluorine, chlorine or bromine;
or a C.sub.1 -C.sub.4 alkyl radical and R.sup.6' and R.sup.7 form an additional bond, or
R.sup.7 is a C.sub.1 -C.sub.4 alkyl radical in the .alpha.- or .beta.-position and R.sup.6 and R.sup.6' are H atoms, or
R.sup.6 and R.sup.7 together form a methylene group in the .alpha.- or .beta.-position and R.sup.6' is H, or
R.sup.6 and R.sup.6' together form an ethylene or methylene group and R.sup.7 is H,
R.sup.9 and R.sup.10 each are H or form an additional bond,
R.sup.11 and R.sup.12 each are H or form an additional bond,
R.sup.13 is a methyl or ethyl group,
R.sup.15 is H or a C.sub.1 -C.sub.3 -alkyl radical,
R.sup.16 and R.sup.16' each independently are H, a C.sub.1 -C.sub.3 alkyl radical or a C.sub.2 -C.sub.4 -alkenyl radical, or together form a C.sub.1 -C.sub.3 alkylidene group,
R.sup.15 and R.sup.16 form an additional bond and R.sup.16' is H or a C.sub.1 -C.sub.3 -alkyl radical, or
R.sup.15 and R.sup.16 together form a ring of partial formula ##STR16## wherein n is 1 or 2,
X is a methylene group or O, and
R.sup.16' is H,
R.sup.17.spsp.1 is H or a C.sub.1 -C.sub.3 -alkyl radical,
R.sup.17.spsp.2 is H, a C.sub.1 -C.sub.3 alkyl radical or a C.sub.2 -C.sub.4 -alkenyl radical,
R.sup.17.spsp.1' and R.sup.17.spsp.2' each are H or form an additional bond,
R.sup.21 is H or a C.sub.1 -C.sub.3 -alkyl radical,
R.sup.21' is H, a C.sub.1 -C.sub.3 -alkyl radical or a hydroxy group
with the proviso that the compound is not 14,17-ethano-19-norpregn-4-ene-3,20dione.

20 more elements

A method for treating gynecological disorders or for substitution therapy which comprises administering a 14,17-C.sub.2 -bridged steroid of formula (I):

##STR17## wherein R.sup.3 is O, a hydroxyimino group or two H atoms,
R.sup.6 is H, fluorine, chlorine or bromine;
or a C.sub.1 -C.sub.4 alkyl radical in the .alpha.- or .beta.-position and R.sup.6' and R.sup.7 are H atoms, or
R.sup.6 is H, fluorine, chlorine or bromine;
or a C.sub.1 -C.sub.4 alkyl radical and R.sup.6' and R.sup.7 form an additional bond, or
R.sup.7 is a C.sub.1 -C.sub.4 alkyl radical in the (.alpha.- or .beta.-position and R.sup.6 and R.sup.6' are H atoms, or
R.sup.6 and R.sup.7 together form a methylene group in the .alpha.- or .beta.-position and R.sup.6' is H, or
R.sup.6 and R.sup.6' together form an ethylene or methylene group and R.sup.7 is H,
R.sup.9 and R.sup.10 each are H or form an additional bond,
R.sup.11 and R.sup.12 each are H or form an additional bond,
R.sup.13 is a methyl or ethyl group,
R.sup.15 is H or a C.sub.1 -C.sub.3 -alkyl radical,
R.sup.16 and R.sup.16' each independently are H, a C.sub.1 -C.sub.3 alkyl radical or a C.sub.2 -C.sub.4 -alkenyl radical, or together form a C.sub.1 -C.sub.3 alkylidene group,
R.sup.15 and R.sup.16 form an additional bond and R.sup.16' is H or a C.sub.1 -C.sub.3 -alkyl radical, or
R.sup.15 and R.sup.16 together form a ring of partial formula ##STR18## wherein n is 1 or 2,
X is a methylene group or O, and
R.sup.16' is H,
R.sup.17.spsp.1 is H or a C.sub.1 -C.sub.3 -alkyl radical,
R.sup.17.spsp.2 is H, a C.sub.1 -C.sub.3 alkyl radical or a C.sub.2 -C.sub.4 -alkenyl radical,
R.sup.17.spsp.1' and R.sup.17.spsp.2' each are H or form an additional bond,
R.sup.21 is H or a C.sub.1 -C.sub.3 -alkyl radical,
R.sup.21' is H, a C.sub.1 -C.sub.3 -alkyl radical or a hydroxy group
with the proviso that the compound is not 14,17-ethano-19-norpregn-4-ene-3,20-dione.

20 more elements

A method for female birth control in a patient which comprises administering a birth control effective amount of a competitive progesterone antagonist and a 14,17-C.sub.2 -bridged steroid of formula (I):

##STR19## R.sup.3 is O, a hydroxyimino group or two H atoms, R.sup.6 is H, fluorine, chlorine or bromine;
or a C.sub.1 -C.sub.4 alkyl radical in the .alpha.- or .beta.-position and R.sup.6' and R.sup.7 are H atoms, or
R.sup.6 is H, fluorine, chlorine or bromine;
or a C.sub.1 -C.sub.4 alkyl radical and R.sup.6' and R.sup.7 form an additional bond, or
R.sup.7 is a C.sub.1 -C.sub.4 alkyl radical in the .beta.- or .beta.-position and R.sup.6 and R.sup.6' are H atoms, or
R.sup.6 and R.sup.7 together form a methylene group in the .alpha.- or .beta.-position and R.sup.6' is H, or
R.sup.6 and R.sup.6' together form an ethylene or methylene group and R.sup.7 is H,
R.sup.9 and R.sup.10 each are H or form an additional bond,
R.sup.11 and R.sup.12 each are H or form an additional bond,
R.sup.13 is a methyl or ethyl group,
R.sup.15 is H or a C.sub.1 -C.sub.3 -alkyl radical,
R.sup.16 and R.sup.16' each independently are H, a C.sub.1 -C.sub.3 alkyl radical or a C.sub.2 -C.sub.4 -alkenyl radical, or together form a C.sub.1 -C.sub.3 alkylidene group,
R.sup.15 and R.sup.16 form an additional bond and R.sup.16' is H or a C.sub.1 -C.sub.3 -alkyl radical, or
R.sup.15 and R.sup.16 together form a ring of partial formula ##STR20## wherein n is 1 or 2,
X is a methylene group or O, and
R.sup.16' is H,
R.sup.17.spsp.1 is H or a C.sub.1 -C.sub.3 -alkyl radical,
R.sup.17.spsp.2 is H, a C.sub.1 -C.sub.3 alkyl radical or a C.sub.2 -C.sub.4 -alkenyl radical,
R.sup.17.spsp.1' and R.sup.17.spsp.2' each are H or form an additional bond,
R.sup.21 is H or a C.sub.1 -C.sub.3 -alkyl radical,
R.sup.21' is H, a C.sub.1 -C.sub.3 -alkyl radical or a hydroxy group
with the proviso that the compound is not 14,17-ethano-19-norpregn-4-ene-3,20-dione.

19 more elements

Dependencies are inferred from the claim text.

Facts

Application: 09/362,214Filed 28 Jul 1999 · continuation
Priority: DE 44 47 40123 Dec 1994
Granted: 14 Nov 2000
Term ends: Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07J 71/0005
Steroids in which the cyclopentahydrophenanthrene skeleton is condensed with a heterocyclic ring: oxygen-containing hetero ring
A61P 5/34
Of the sex hormones: gestagens
A61P 15/00
Drugs for genital or sexual disorders
A61P 15/18
Drugs for genital or sexual disorders ; Contraceptives: feminine contraceptives

Family

Serial578,847Parent of this division · filed 26 Dec 1995
Serial135,483Parent of this continuation · filed 18 Aug 1998
US 5,973,172 AParent of this continuation
US 5,827,842 AParent of this division
US 6,147,065 AThis patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

##STR15## wherein R.sup.3 is O, a hydroxyimino group or two H atoms,
R.sup.6 is H, fluorine, chlorine or bromine;
or a C.sub.1 -C.sub.4 alkyl radical in the .alpha.- or .beta.-position and R.sup.6' and R.sup.7 are H atoms, or
R.sup.6, is H, fluorine, chlorine or bromine;
or a C.sub.1 -C.sub.4 alkyl radical and R.sup.6' and R.sup.7 form an additional bond, or
R.sup.7 is a C.sub.1 -C.sub.4 alkyl radical in the .alpha.- or .beta.-position and R.sup.6 and R.sup.6' are H atoms, or
R.sup.6 and R.sup.7 together form a methylene group in the .alpha.- or .beta.-position and R.sup.6' is H, or
R.sup.6 and R.sup.6' together form an ethylene or methylene group and R.sup.7 is H,
R.sup.9 and R.sup.10 each are H or form an additional bond,
R.sup.11 and R.sup.12 each are H or form an additional bond,
R.sup.13 is a methyl or ethyl group,
R.sup.15 is H or a C.sub.1 -C.sub.3 -alkyl radical,
R.sup.16 and R.sup.16' each independently are H, a C.sub.1 -C.sub.3 alkyl radical or a C.sub.2 -C.sub.4 -alkenyl radical, or together form a C.sub.1 -C.sub.3 alkylidene group,
R.sup.15 and R.sup.16 form an additional bond and R.sup.16' is H or a C.sub.1 -C.sub.3 -alkyl radical, or
R.sup.15 and R.sup.16 together form a ring of partial formula ##STR16## wherein n is 1 or 2,
X is a methylene group or O, and
R.sup.16' is H,
R.sup.17.spsp.1 is H or a C.sub.1 -C.sub.3 -alkyl radical,
R.sup.17.spsp.2 is H, a C.sub.1 -C.sub.3 alkyl radical or a C.sub.2 -C.sub.4 -alkenyl radical,
R.sup.17.spsp.1' and R.sup.17.spsp.2' each are H or form an additional bond,
R.sup.21 is H or a C.sub.1 -C.sub.3 -alkyl radical,
R.sup.21' is H, a C.sub.1 -C.sub.3 -alkyl radical or a hydroxy group
with the proviso that the compound is not 14,17-ethano-19-norpregn-4-ene-3,20dione.

20 more elements

Facts

Application

09/362,214Filed 28 Jul 1999 · continuation

Priority

DE 44 47 40123 Dec 1994

Granted

14 Nov 2000

Term ends

Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07J 71/0005
Steroids in which the cyclopentahydrophenanthrene skeleton is condensed with a heterocyclic ring: oxygen-containing hetero ring
A61P 5/34
Of the sex hormones: gestagens
A61P 15/00
Drugs for genital or sexual disorders
A61P 15/18
Drugs for genital or sexual disorders ; Contraceptives: feminine contraceptives