Roussel Uclaf

Aventis Pharma S.a.

Hoechst Marion Roussel

Other

Andre Claussner

Jean-Georges Teutsch

Lucien Nedelec

Daniel Philibert

Francois Goubet

Patrick Van De Velde

Jacques Leclaire

Francois Nique

Neerja Bhatnagar

Michele Resche Rigon

Christian Marchandeau

Jean G Teutsch

Martine Moguilewsky

Jean-George Teutsch

19-Nor steroids having a thiocarbonated chain in position 11beta, their preparation process and the intermediates of this process, their use as medicaments and compositions

Steroids, their use as medicaments, their preparation process, the intermediates of this process and the compositions containing them

Compounds of formula (I), wherein R,and R&prime;,are such that: either R,and R&prime;,together form ketone, hydrazono, oxime or methylene, or R,is hydroxyl, hydroxymethyl or acyloxy and R&prime;,is hydrogen, alkyl or optionally substitued alkenyl or alkynyl; R,is hydrogen or alkyl; R,is hydrogen, halogen or alkyl; m is 0, 1 or 2; X, Y and Z are such that: X is methylene, arylene or arylenoxy bonded to the steroid by a carbon atom; Y is a saturated or unsaturated straight or branched aliphatic chain which is optionally interrupted by oxygen; and Z is aryl, arylalkyl or straight or branched alkyl; addition salts thereof, a preparation method therefor, medicinal uses thereof, compositions containing said compounds, and resulting novel intermediates.

19-nor steroids having a thiocarbonated chain in position 11beta, their preparation process and the intermediates of this process, and the intermediates of this process, their use as medicaments and compositions

The subject of the invention is the products of formula (I):

Pregnane derivatives with no alpha-17 substitutent, their medicinal use, manufacturing method and its intermediaries and related compounds

A subject of the invention is the products of formula (I):

Phenylimidazolidines containing nitrooxy or carbonyloxy groups

1-Imidazolidinyl-phenyls

Novel imidazoles of the formula ##STR1## wherein the substituents are as defined in the disclosure and their non-toxic, pharmaceutically acceptable addition salts with acids and bases having antiandrogenic activity.

Imidazolidines substituted with a heterocycle

Optionally substituted phenylimidazolidines, their preparation process

A 19-nor-steroid having a formula selected from the group consisting of ##STR1## wherein the A and B rings have a structure selected from the group consisting of ##STR2##

19-nor-steroids

Described herein are novel imidazoles of the formula ##STR1## wherein the substituents are as defined in the disclosure and their non-toxic, pharmaceutically acceptable addition salts with acids and bases having antiandrogenic activity.

Method of inducing antiandrogenic activity using imidazolidines

A compound selected from the group consisting of compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of --CN, --NO.sub.2, halogen, --CF.sub.3, free carboxy, salified carboxy, and carboxy esterified with lower alkyl; -A-B- is selected from the group consisting of ##STR2## and X, R.sub.3, R.sub.4 and R.sub.5 are defined as in the specification and their non-toxic, pharmaceutically acceptable acid addition salts having anti-androgenic activity.

Phenylimidazolidines

A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.A, R.sub.A.sup.1, R.sub.B R.sub.B.sup.1 are individually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms or R.sub.A and R.sub.A.sup.1 or R.sub.B and R.sub.B.sup.1 together with the nitrogen atom to which they are attached form a 5- to 6-member heterocycle optionally substituted with alkyl of 1 to 3 carbon atoms and Y is hydrogen or ##STR2## wherein R.sub.6 is selected from the group consisting of hydrogen, --CH.sub.3, --F and --Cl, R.sub.9 and R.sub.11 form a second bond at 9(11) or R.sub.9 is hydrogen or --F and R.sub.11 is hydrogen, --OH or .dbd.0, R.sub.16 is --CH.sub.3 or hydrogen, R.sub.17 is hydrogen, --OH or acyloxy, the dotted lines indicate the possible presence of a second bond at 1(2) and 6(7)-positions and the wavy line indicates the .alpha.- and .beta.-position and their non-toxic, pharmaceutically acceptable acid addition salts having anti-inflammatory and antioxidant activity.

N,N,N',N'-6-(1-piperazinyl)-2,5-pyridinediamines

The novel compounds of the invention are 19 nor-steroids of the formula: ##STR1## Where A, B, C, D, X, Y, Z, R.sub.17, and R.sup.1 are as defined in the specification, having hormonal properties and their preparation and intermediates.

A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.A, R'.sub.A, R.sub.B and R'.sub.B are individually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms or R.sub.A and R'.sub.A or R.sub.B and R'.sub.B together with the nitrogen atom to which they are attached form a 5- to 6-member heterocycle optionally substituted with alkyl of 1 to 3 carbon atoms and Y is hydrogen or ##STR2## wherein R.sub.6 is selected from the group consisting of hydrogen, --CH.sub.3, --F and --Cl, R.sub.9 and R.sub.11 form a second bond at 9(11) or R.sub.9 is hydrogen or --F is hydrogen, --OH or .dbd.O, R.sub.16 is --CH.sub.3 or hydrogen, R.sub.17 is hydrogen, --OH or acyloxy, the dotted lines indicate the possible presence of a second bond at 1(2) and 6(7)-positions and the wavy line indicates the .alpha.- and .beta.-position and their non-toxic, pharmaceutically acceptable acid addition salts having anti-inflammatory and antioxidant activity.

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Villemomble, France

Andre Claussner