US 9,034,856 B2 · 17-(1′propenyl)-17-3′-oxidoestra-4-en-3-one derivative, use thereof, and medicament containing said derivative

Abstract

The invention relates to 17-(1′-propenyl)-17-3′-oxidoestra-4-en-3-one derivatives with the general chemical formula I, where the residues Z, R4, R6a, R6b, R7, R15, R16a, R16b and R18 have the meanings stated in Claim 1, and their solvates, hydrates and salts, including all stereoisomers of these compounds. The invention further relates to the use of these derivatives for the production of a medicinal product for oral contraception and for the treatment of pre-, peri- and postmenopausal complaints and medicinal products that contain said derivatives, and in particular application in the aforementioned indications. The derivatives according to the invention have a progestational and in preferred cases additionally an antimineralocorticoid and neutral to slightly androgenic action.

The 17-(1′-Propenyl)-17-3′-oxidoestra-4-en-3-one derivative selected from the group comprising of:

7α-Methyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
7β-Methyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
7α-Ethyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
7β-Ethyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
7α-Vinyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
7β-Vinyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
7α-Cyclopropyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
7β-Cyclopropyl-17α-(1-propenyl)-17β-3′-oxidoestra-4-en-3-one;
6-Methylene-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
6α-Hydroxymethylene-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
6β-Hydroxymethylene-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
6,6-(1,2-Ethanediyl)-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
6α,7α-Methylene-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
6β,7β-Methylene-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
17α-(1′-Propenyl)-17β-3′-oxidoestra-4,6-dien-3-one;
16,16-(1,2-Ethanediyl)-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
(E/Z)-3-(Hydroxyimino)-7α-methyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-7β-methyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-7α-ethyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-7β-ethyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-7α-vinyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-7β-vinyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-7α-cyclopropyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-7β-cyclopropyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-6-methylene-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-6α-hydroxymethylene-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-6β-hydroxymethylene-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-6,6-(1,2-ethanediyl)-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-6α,7α-methylene-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-6β,7β-methylene-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-17α-(1′-propenyl)-17β-3′-oxidoestra-4,6-diene;
(E/Z)-3-(Hydroxyimino)-16,16-(1,2-ethanediyl)-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
7 α,18-Dimethyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
7 β,18-Dimethyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
7β-Ethyl-18-methyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
7α-Vinyl-18-methyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
7β-Vinyl-18-methyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
7α-Cyclopropyl-18-methyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
7β-Cyclopropyl-18-methyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-en-3-one;
6-Methylene-17α-(1′-propenyl)-18-methyl-17β-3′-oxidoestra-4-en-3-one;
6α-Hydroxymethylene-17α-(1′-propenyl)-18-methyl-17β-3′-oxidoestra-4-en-3-one;
6,6-(1,2-Ethanediyl)-17α-(1′-propenyl)-18-methyl-17β-3′-oxidoestra-4-en-3-one;
6α,7α-Methylene-17α-(1′-propenyl)-18-methyl-17β-3′-oxidoestra-4-en-3-one;
6β,7β-Methylene-17α-(1′-propenyl)-18-methyl-17β-3′-oxidoestra-4-en-3-one;
17α-(1′-Propenyl)-18-methyl-17β-3′-oxidoestra-4,6-dien-3-one;
16,16-(1,2-Ethanediyl)-17α-(1′-propenyl)-18-methyl-17β-3′-oxidoestra-4-en-3-one;
(E/Z)-3-(Hydroxyimino)-18-methyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-7α,18-dimethyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-7β,18-dimethyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-7α-ethyl-18-methyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-7β-ethyl-18-methyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-7α-vinyl-18-methyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-7β-vinyl-18-methyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-7α-cyclopropyl-18-methyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-7β-cyclopropyl-18-methyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-6-methylene-17α-(1′-propenyl)-18-methyl-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-6α-hydroxymethylene-17α-(1′-propenyl)-18-methyl-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-6β-hydroxymethylene-17α-(1-propenyl)-18-methyl-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-6,6-(1,2-ethanediyl)-17α-(1′-propenyl)-18-methyl-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-6α,7α-methylene-17α-(1′-propenyl)-18-methyl-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-6β,7β-methylene-17α-(1′-propenyl)-18-methyl-17β-3′-oxidoestra-4-ene;
(E/Z)-3-(Hydroxyimino)-18-methyl-17α-(1′-propenyl)-17β-3′-oxidoestra-4,6-diene;
and
(E/Z)-3-(Hydroxyimino)-16,16-(1,2-ethanediyl)-17α-(1′-propenyl)-18-methyl-17β-3′-oxidoestra-4-ene.

61 more elements

17-(1′propenyl)-17-3′-oxidoestra-4-en-3-one derivative, use thereof, and medicament containing said derivative

Life of this patent

17-(1′propenyl)-17-3′-oxidoestra-4-en-3-one derivative, use thereof, and medicament containing said derivative

Life of this patent

Abstract

Claims9