17 Alpha-position Substituted (e.g., 17 Alpha-ethynyl-19 Nortestosterones, Etc.) Patents (Class 552/648)
  • Patent number: 5407928
    Abstract: This invention relates to 11.beta.-aryl-gona-4,9-dienes of the general formula I ##STR1## wherein the variables are defined in the specification. The compounds are progesterone antagonists and are suitable for inducing labor or an abortion.
    Type: Grant
    Filed: November 17, 1993
    Date of Patent: April 18, 1995
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Kasch, Gudrun Bertram, Kurt Ponsold, Gerd Schubert, Heidemarie Rohrig, Anatoli Kurischko, Bernd Menzenbach
  • Patent number: 5276023
    Abstract: 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.
    Type: Grant
    Filed: April 30, 1992
    Date of Patent: January 4, 1994
    Assignee: Roussel Uclaf
    Inventors: Martine Moguilewsky, Lucien Nedelec, Francois Nique, Daniel Philibert
  • Patent number: 5273971
    Abstract: There are provided 13-alkyl-11beta-phenyl-gonanes of formula I ##STR1## wherein Z is an oxygen atom or N--OH;R.sup.2 is alpha- or beta-position methyl or ethyl;R.sup.1 is selected from heteroaryl radicals, cycloalkyl radicals, cycloalkenyl radicals, aryl radicals, alkenyl radicals, and alkyl radicals where R.sup.2 is in the alpha-position and an ethyl radical where R.sup.2 is in the beta-position; andR.sup.3 and R.sup.4 are selected from one of two different groups of substituent pairs, the group from which the selection is made being determined by the position of R.sup.2.
    Type: Grant
    Filed: July 3, 1989
    Date of Patent: December 28, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Stefan Scholz, Eckhard Ottow, Guenter Neef, Walter Elger, Sybille Beier, Krzysztof Chwalisz
  • Patent number: 5166146
    Abstract: 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.
    Type: Grant
    Filed: August 16, 1990
    Date of Patent: November 24, 1992
    Assignee: Roussel Uclaf
    Inventors: Martine Moguilewsky, Lucien Nedelec, Francois Nique, Daniel Philibert
  • Patent number: 5064822
    Abstract: Novel 3-keto-19-nor-.DELTA..sup.4,9 -steroids of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of naphthyl, phenylphenyl, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms optionally containing additional unsaturations, phenoxy, furyl, cycloalkyl of 3 to 6 carbon atoms, thienyl optionally substituted with at least one member of the group consisting of halogen and alkyl and haloalkyl of 1 to 6 carbon atoms and phenyl optionally substituted with at least one member of the group consisting of --OH, halogen, --CF.sub.3, alkyl and alkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, phenoxy and alkylthio of 1 to 6 carbon atoms optionally oxidized to the sulfoxide or sulfone, R.sub.2 is selected from the group consisting of methyl and ethyl, R.sub.
    Type: Grant
    Filed: November 16, 1989
    Date of Patent: November 12, 1991
    Assignee: Roussel Uclaf
    Inventors: Daniel Philibert, Jean G. Teutsch, Germain Costerousse, Roger Deraedt
  • Patent number: 4945064
    Abstract: Estrane and androstane derivatives of formula I ##STR1## wherein X is bromine, iodine, triphenyltin or trialkyltin of 1 to 6 carbon atoms per alkyl radical,Y represents two hydrogen atoms or methylene,Z represents two hydrogen atoms, oxo or alkylenedioxy of 2 to 6 carbon atoms andV is ethylene, vinylene, 1,3-propylene or cyclopropylene,R.sub.1 is hydrogen or a hydrocarbon radical of up to 8 hydrocarbon atoms, optionally interrupted by an oxa group or substituted by an oxo group,R.sub.2 is methyl or ethyl,R.sub.3 and R.sub.4 represent a carbon-carbon bond or R.sub.3 is hydrogen and R.sub.4 is hydrogen or methyl,.DELTA.symbolizes a 4(5)-double bond if Z signifies two hydrogen atoms or an oxo group; or a 5(6)-double bond or, for the estrane derivatives of formula I, also a 5(10)-double bond, if Z is alkylenedioxy,are pharmacologically effective substances or intermediates for preparation thereof.
    Type: Grant
    Filed: January 19, 1988
    Date of Patent: July 31, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Hofmeister, Henry Laurent, Paul E. Schulze, Klaus Annen, Rudolf Wiechert, Kunhard Pollow, Bernhard Manz, Hans-Joerg Grill
  • Patent number: 4943566
    Abstract: A compound selected from the group consisting of compounds of the formula ##STR1## wherein R.sub.1 is an organo of 1 to 18 carbon atoms optionally containing at least one heteroatom connected to the C ring by a carbon atom, R.sub.2 is methyl or ethyl, the A and B rings being selected from the group consisting of ##STR2## Re is selected from the group consisting of hydrogen, optionally substituted alkyl of 1 to 6 carbon atoms and acyl and the D ring is selected from the group consisting of ##STR3## one of R.sub.3 and R.sub.4 is selected from the group consisting of hydroxy, protected hydroxy, acyl and alkoxy and the other is an optionally substituted aryl, R.sub.5 is an optionally substituted aryl and their non-toxic, pharmaceutically acceptable salts with acids and bases with the proviso that when the A and B rings are ##STR4## R.sub.1 is ##STR5## R.sub.2 is methyl, R.sub.3 is --OH, R.sub.4 is phenyl having anti proliferative properties.
    Type: Grant
    Filed: July 28, 1988
    Date of Patent: July 24, 1990
    Assignee: Roussel Uclafi
    Inventors: Lucien Nedelec, Francois Nique, Daniel Philibert, Martine Moguilewsky, Marie-Madeleine Bouton
  • Patent number: 4923640
    Abstract: A process for the production of 17.alpha.-ethinyl-17.beta.-hydroxy-18-methyl-4,15-estradien-3-one is described comprising reacting a 17-enolester of formula II ##STR1## wherein R.sub.1 represents an alkyl radical with 1-3 carbon atoms andR.sub.2 represents an acyl or a trialkylsilyl group with 1-10 carbon atomsunder palladium catalysis, with compounds of formula II ##STR2## wherein R.sub.1 represents an alkyl radical with 1-3 carbon atoms, reducing the 17-keto group to the 17-hydroxy group in a manner known in the art, reducing the aromatic A-ring according to Birch, with liquid ammonia, to 3-methoxy-2,5(10),15-estratrien-17.beta.-ol, reoxidizing the 17-hydroxy group to the 17-keto group, ethinylating the 17-keto group and splitting off the 3-enolether to form 17.alpha.-ethinyl-17.beta.-hydroxy-18-methyl-4,15-estradiene-3-one.
    Type: Grant
    Filed: March 31, 1988
    Date of Patent: May 8, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Rolf Bohlmann, Henry Laurent, Helmut Hofmeister, Rudolf Wiechert