# US 5,705,495 A · Sulfamate derivatives of 1,3,5(10)-estratriene derivatives, methods for their production and pharmaceuticals containing these compounds

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- Number: US 5,705,495 A
- Document ID: US5705495A
- Status: Granted
- Kind: A
- Application number: 08/732,742
- Filed: 1996-10-18
- Granted: 1998-01-06
- Earliest claimed: 1995-10-19
- Assignees: Jenapharm GmbH & Co. KG
- Inventors: Sigfrid Schwarz; Walter Elger; Gudrun Reddersen; Birgitt Schneider; Ina Thieme; Margit Richter
- Web page: https://patentgrep.com/patent/US5705495A

## CPC

- C07J 41/0072: {the A ring of the steroid being aromatic}
- C07J: STEROIDS (seco-steroids C07C)

## Abstract

The invention relates to new sulfamate derivatives of 1,3,5(10)-estratriene derivatives of the general formula I ##STR1## wherein the 3-sulfamate moiety is acylated, sulfonated or amidosulfonated. Furthermore, methods for the production of the compound and pharmaceutical preparations containing this compound are described. The compounds according to the invention have an estrogenic effect.

## Claims

### Claim 1

Sulfamate derivatives of the general formula I ##STR5## wherein R.sup.1 is a --CO--R.sup.3, --CO--OR.sup.4, --CO--NR.sup.5 R.sup.6, --SO.sub.2 --R.sup.4 or --SO.sub.2 --NU.sup.5 R.sup.6 group,
in which
R.sup.3 is a hydrogen atom or is as defined in R.sup.4,
R.sup.4 represents a C.sub.1 -C.sub.5 alkyl residue, a C.sub.2 -C.sub.5 alkenyl residue, a C.sub.3 -C.sub.6 cycloalkyl residue or an aryl residue containing up to 9 carbon atoms,
R.sup.5 and R.sup.6 are independent of each other and represent a hydrogen atom, a C.sub.1 -C.sub.5 alkyl residue, an aryl residue containing up to 9 carbon atoms, or, together with the N atom, represent a polymethylene imino residue containing 3 to 6 carbon atoms, or a morpholino residue,
R.sup.2 is a hydrogen atom or a physiologically tolerable metal, or is as defined in R.sup.4,
R.sup.7 and R.sup.8 are independent of each other and represent a hydrogen atom, a hydroxy group or a C.sub.1 -C.sub.5 alkoxy residue,
R.sup.9 and R.sup.10 each represent a hydrogen atom, or together represent a methylene group,
R.sup.11, R.sup.12 and R.sup.13 are independent of each other and represent a hydrogen atom or a hydroxy group that may optionally be esterified with physiologically tolerable inorganic or organic acids,
or R.sup.12 or R.sup.13 is an alkinyl residue containing up to 5 carbon atoms,
rings B and C may optionally contain one or two double bonds,
and R.sup.8, R.sup.11 and R.sup.12 are independently placed either at the .alpha.- or .beta.-position.

### Claim 2 (depends on 1)

A method for the production of the sulfamate derivatives according to claim 1, comprising
a) estra-1,3,5(10)-triene-3-yl sulfamate derivatives that carry at least one hydrogen atom at the nitrogen atom of their sulfamate residue, are reacted with an activated carboxylic acid, carbamic acid, sulfonic acid or amidosulfonic acid or
b) 3-hydroxy-estra-1,3,5(10)-triene derivatives are reacted with an activated N-acyl amidosulfonic acid, N-sulfonyl amidosulfonic acid or N-amidosulfonyl amidosulfonic acid,
optionally in the presence of a base.

### Claim 3 (depends on 1)

A pharmaceutical preparation at least one sulfamate derivative according to claim 1 and a pharmaceutically acceptable adjuvants or substrates.