Roussel Uclaf

Other

Aventis Pharma S.a.

Lucien Nedelec

Claude Dumont

Daniel Philibert

Jacques Guillaume

Daniel Frechet

Vesperto Torelli

Francois Nique

Andre Claussner

Patrick Fauveau

Martine Moguilewsky

Andre Pierdet

Robert Fournex

Gilles Hamon

Patrick Van De Velde

Jean-Claude Gasc

Jacques Leclaire

Claude Oberlander

Claude Rettien

Marie-Helene Kannengiesser

Jean-Georges Teutsch

Roger Deraedt

Anne-Marie Moura

Marie-Madeleine Bouton

Neil L Brown

Guy Plassard

Dinah W Nanopoulos

Francois Clemence

Francoise Delevallee

Constantin Agouridas

Daniel Humbert

Andre Allais

Hans H Sedlacek

Jorg Czech

Peter F Hunt

Michel Hardy

Colette Tournemine

Martine Gaillard-Kelly

Christian Marchandeau

Fran&ccedil;ois Nique

Francois Nioue

Martine Moguilewski

Claude Gueniau

Ana Maria Boaventura

Andr&egrave; Claussner

19-Nor-steroids

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

A compound selected from the group consisting of a compound of the formula ##STR1## wherein the substituents are defined as in the application having antiglucocorticoid and antiprogestomimetic properties and a process and intermediates for their preparation.

17 Methylene lactones of steroids

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 of the formula ##STR1## wherein R.sub.1 is an aliphatic hydrocarbon of 1 to 8 carbon atoms, R.sub.2 and R.sub.3 are individually hydrogen or alkyl of 1 to 4 carbon atoms, G is a hydrocarbon of 1 to 18 carbon atoms optionally containing at least one heteroatom and linked to the steroid nucleus by a carbon atom, X is X.sub.A or X.sub.B, X.sub.A is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, aralkyl of 7 to 15 carbon atoms, acyl of an organic carboxylic acid of 1 to 8 carbon atoms and Y is -B-O--CO--A-Z, B is a saturated or unsaturated, linear or branched alkylene of 1 to 8 carbon atoms, A is a saturated or unsaturated, linear or branched alkylene of 1 to 6 carbon atoms and optionally interrupted or ended by a bivalent aromatic or is a bivalent aromatic and Z is --COOH or --SO.sub.3 H which may be salified with an alkali metal, alkaline earth metal, an organic amine or --NH.sub.4 or X.sub.B is --COAZ, A and Z are defined as above and Y is selected from the group consisting of --C.tbd.C--R.sub.4, --CH.dbd.CH--R.sub.4 and --CH.sub.2 --CH.sub.2 --R.sub.4, R.sub.4 is selected from the group consisting of hydrogen, halogen, alkyl of 1 to 6 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms and phenyl, the alkyl and phenyl being optionally substituted and the 13-wavy line indicates that R.sub.1 can be in the .alpha.- or .beta.-position having antiprogestomimetic and antiglucocorticoid properties among others.

19-nor-steroid esters

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.

Use of derivatives of 9,10-dihydrophenanthrene for the preparation of an

A compound of the formula ##STR1## wherein R.sub.1 is an aliphatic hydrocarbon of 1 to 8 carbon atoms, R.sub.a and R.sub.b are individually hydrogen or alkyl of 1 to 4 carbon atoms, R.sub.2 is hydrogen or optionally substituted alkyl of 1 to 12 carbon atoms, n is an integer from 1 to 6, Z is free carboxy or salified with an alkali metal, alkaline earth metal or NH.sub.4 and X is the remainder of an optionally substituted and optionally unsaturated 5 or 6-member ring and the wavy line indicates the .alpha.- or .beta.-position for R.sub.1 having anti-glucocorticoid activity.

Amino acid cyclopentanophenonthrene compounds

Novel 19-nor-steroids of the formula ##STR1## wherein the A and B rings have a structure selected from the group consisting of ##STR2## having hormonal properties and their preparation and intermediates.

19.fwdarw.nor.fwdarw.steroids

A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.2 and R'.sub.2 are individually hydrogen or methyl, R.sub.11 is an organo of 1 to 18 carbon atoms optionally containing at least one heteroatom with the atom adjacent to the 11-carbon atom being a carbon, the wavy lines at the 13 and 17-positions indicate that when the 13-methyl is .alpha., R'.sub.17 group is .beta. and R.sub.17 is .alpha. and when the 13-methyl is .sub..beta., R.sub.17 is .sub..beta. and R'.sub.17 is .alpha., R.sub.17 is --OH or acyloxy of 1 to 18 carbon atoms and R'.sub.17 is ##STR2## is hydrogen or --OH or acyloxy of 1 to 18 carbon atoms, Z is selected from the group consisting of a single bond, alkylene of 1 to 5 carbon atoms and alkenylene and alkynylene of 2 to 5 carbon atoms and P is selected from the group consisting of pyrimidinyl and pyridyl optionally substituted with 1 or 2 individual members of the group consisting of amino, alkylamino and dialkylamino of 1 to 4 alkyl carbon atoms and (B aminated 5- or 6-membered heterocycle optionally substituted with alkyl of 1 to 3 carbon atoms) and its non-toxic, pharmaceutically acceptable acid addition salts having anti-inflammatory and anti-oxidant activity.

19-nor-3-keto steroids

Compounds of the formula ##STR1## wherein .dbd.X is .dbd.O or ##STR2## R is hydrogen or acyl of an organic carboxylic acid of 1 to 12 carbon atoms, the wavy lines indicate the .alpha.- or .beta.-position, the dotted line in the 17-position indicates the bond is in the .alpha.-position and the dotted lines in the 9'(10') and 11'(12') positions indicate an optional double bond in the 9'(10') position or two optional double bonds in the 9'(10') and 11'(12') positions having progestomimetic and antiestrogenic activity.

Novel steroids

A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.6 is selected from the group consisting of halogen, --CH.sub.3, fluorine and chlorine, R.sub.9 and R.sub.11 together form a second bond at 9(11) or R.sub.9 is hydrogen or fluorine and R.sub.11 is selected from the group consisnting of hydrogen, --OH and .dbd.O, the dotted lines in rings A and B indicate a possible additonal bond at 1(2) and 6(7), R.sub.17 is hydrogen or acyl or an organic carboxylic acid of 1 to 18 carbon atoms, R'.sub.17 is ##STR2## Z is selected from the group consisting of a single bond, alkylene of 1 to 5 carbon atoms and alkenylene and alkynylene of 2 to 5 carbon atoms, P is pyrimidinyl or pyridyl optionally substituted with one or two individual members of the group consisting of --NH.sub.2, alkylamino, dialkylamino and aminated 5- or 6- membered heterocycles optionally substituted with alkyl of 1 to 3 carbon atoms and its non-toxic, pharmaceutically acceptable acid addition salts having anti-inflammatory and anti-oxidation activity.

Novel 3-keto-steroids

Novel 19-nor steroids of the formula ##STR1## wherein R' is selected from the group consisting of propyl, propenyl, iodoethenyl, iodoethynyl or --C.tbd.C--CH.sub.2 --Hal.sub.1, Hal.sub.1 is selected from the group consisting of fluorine, chlorine and bromine and their non-toxic, pharmaceutically acceptable acid addition salts having a remarkable antiglucocorticoid and antiprogestomimetic activity.

Novel 17.beta.-hydroxy-19-nor-steroids

Novel 10.beta.-alkynyl-steroids of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, optionally substituted alkyl and alkoxy of 1 to 8 carbon atoms, optionally substituted alkenyl and alkynyl of 2 to 8 carbon atoms, optionally substituted aryl and aralkyl, optionally esterified carboxy, dialkylamino with alkyl of 1 to 6 carbon atoms, halogen and trialkylsilyl of 1 to 7 alkyl carbon atoms, R.sub.6 and R.sub.7 taken together with the carbon atoms to which they are attached form cyclopropyl or R.sub.6 is hydrogen and R.sub.7 is R.sub.1, R.sub.1 is selected from the group consisting of hydrogen, optionally substituted alkyl of 1 to 6 carbon atoms, optionally substituted alkenyl and alkynyl of 2 to 6 carbon atoms and acetylthio, R.sub.2 is methyl or ethyl, X and Y taken together form a member selected from the group consisting of ##STR2## Alk is alkyl of 1 to 8 carbon atoms or X is hydroxy and Y is ##STR3## or X is optionally acylated or etherified hydroxy and Y is selected from the group consisting of --CH.sub.2 --CH.sub.2 --CH.sub.2 --OH, hydrogen, R.sub.4, and --CH.sub.2 --CH.sub.2 --COOM, M is selected from the group consisting of hydrogen, --NH.sub.4 and alkali metal and R.sub.4 is selected from the group consisting of alkyl of 1 to 6 carbon atoms and alkenyl and alkynyl of 2 to 6 carbon atoms, the dotted lines indicate the optional presence of a second carbon-carbon bond when R.sub.6 and R.sub.7 and the carbon to which they are attached do not form cyclopropyl and the wavy lines indicate that R.sub.6 and R.sub.7 may be in the .alpha. or .beta. position with the proviso that R is not hydrogen when R.sub.6 and R.sub.7 are hydrogen, R.sub.2 is methyl, X is optionally acylated or etherified hydroxy, Y is hydrogen or R.sub.4 and the dotted lines are not a second carbon-carbon bond having aldosterone antagonistic activity and increased hydrosodic diuresis with organic potassium conservation with little secondary hormone effects.

Novel 10.beta.-alkynyl-steroids

Growing community of inventors

Le Raincy, France

Lucien Nedelec