Sulfur In The Spiro Hetero Ring Patents (Class 540/30)
  • Publication number: 20150031875
    Abstract: The present invention relates to a synthesis route and to steroid derivatives of general formula VI and VII useful in the synthesis of desogestrel and etonogestrel.
    Type: Application
    Filed: March 13, 2013
    Publication date: January 29, 2015
    Inventor: Martin Ostendorf
  • Patent number: 6117994
    Abstract: A new process for the preparation of 16.beta.-methyl-steroids of the formula ##STR1## and novel intermediates.
    Type: Grant
    Filed: April 22, 1998
    Date of Patent: September 12, 2000
    Assignee: Hoechst Marion Roussel
    Inventors: Catherine Geurts, Michel Vivat
  • Patent number: 5760256
    Abstract: A process for the production of a compound of the formula ##STR1## wherein R.sub.1 is acyl of 1 to 8 carbon atoms,. The compound is formed by the reduction of an intermediary to form an alcohol, epoxidation and hydrolyzation of the alcohol to form a compound of formula ##STR2## followed by the acylation of the hydroxy functions and the elimination of the 17.alpha.-substituent.
    Type: Grant
    Filed: February 21, 1995
    Date of Patent: June 2, 1998
    Assignee: Roussel Uclaf
    Inventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
  • Patent number: 5756722
    Abstract: The novel intermediates of the formula ##STR1## wherein L, K and M are as defined in the specification which are useful intermediates for the preparation of .DELTA..sup.4,9(11),16 -pregnatriene-3-ones.
    Type: Grant
    Filed: September 6, 1996
    Date of Patent: May 26, 1998
    Assignee: Roussel Uclaf
    Inventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
  • Patent number: 5723638
    Abstract: The invention is drawn to a process for the preparation of a steroid of the formula ##STR1## wherein R.sub.1 is hydrogen or alkyl of 1 to 4 carbon atoms, R.sub.2 is alkyl of 1 to 4 carbon atoms and theo A, B, C, and D ring system has at least one double bond and is optionally substituted by at least one optionally protected hydroxy, optionally protected keto, halogen, alkyl and alkoxy of 1 to 4 carbon atoms, and alkenyl and alkynyl of 2 to 4 carbon atoms by reacting the corresponding 17-ketosteroid with a compound of the formula ##STR2## and then by reacting the resulting compound with an aryl sulfenyl halide. The intermediate produced then undergoes rearrangement followed by epimerization with a strong base to obtain a mixture of the corresponding sulfoxide diastereoisomers which is reacted with a thiophilic compound. The intermediate produced undergoes acid hydrolysis to provide the compound of formula I.
    Type: Grant
    Filed: June 26, 1995
    Date of Patent: March 3, 1998
    Assignee: Roussel Uclaf
    Inventors: Robert Lett, Oleg Melnyk
  • Patent number: 5594127
    Abstract: A compound having a formula ##STR1## in which K is defined as above, C--P being CH.sub.2 or --C.dbd.CH.sub.2 or ##STR2## and J is --SO.sub.2 R.sub.2, or C--P is C.dbd.O and J is --CH.sub.2 Hal.sub.2, or C--P is --CH SO.sub.2 R.sub.2 and J is CO.sub.2 R or Hal.sub.1, R.sub.2 is methyl, phenyl, tolyl or xylyl, R is alkyl of 1 to 6 carbon atoms, aralkyl of 7 to 15 is carbon atoms or a silylated remainder selected from the group consisting of trimethylsilyl, tert.-butyldimethylsilyl, triphenylsilyl and diphenyltert.-butylsilyl, Hal.sub.1 is halogen, Hal.sub.2 is chlorine, bromine or iodine and the wavy lines symbolize any one of the isomer forms or their mixtures which are intermediates.
    Type: Grant
    Filed: November 14, 1995
    Date of Patent: January 14, 1997
    Assignee: Roussel Uclaf
    Inventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
  • Patent number: 5585482
    Abstract: A process for the preparation of a compound of the formula ##STR1## wherein R and R' and the A and B are as defined in the specification. ##STR2## K is selected from the group consisting of ##STR3## n is 2 or 3 and the dotted lined is an optional bond.
    Type: Grant
    Filed: October 19, 1995
    Date of Patent: December 17, 1996
    Assignee: Roussel Uclaf
    Inventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
  • Patent number: 5556962
    Abstract: A compound of the formula ##STR1## wherein K is a protective group of the oxo of the formula ##STR2## wherein n is 2 or 3 and L is a 11.beta.-hydroxy, the dotted line in the 11-position is not a bond and X is chlorine, bromine or iodine which avoids an 11-hydroxylation step in the preparation of hydrocortisone.
    Type: Grant
    Filed: October 2, 1995
    Date of Patent: September 17, 1996
    Assignee: Roussel Uclaf
    Inventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
  • Patent number: 5502182
    Abstract: A compound of the formula ##STR1## wherein K represents a protective group of the oxo of the formula ##STR2## wherein n is 2 or 3, and M is chlorine, bromine, or ##STR3## wherein R.sub.a and R.sub.b are individually selected from the group consisting of hydrogen, --OH, and alkyl and alkoxy of 1 to 4 carbon atoms and R is selected from the group consisting of alkyl of 1 to 6 carbon atoms, aralkyl of 7 to 15 carbon atoms, trialkyl silyl triphenyl silyl and diphenyl alkyl silyl.
    Type: Grant
    Filed: December 22, 1994
    Date of Patent: March 26, 1996
    Assignee: Roussel Uclaf
    Inventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
  • Patent number: 5401864
    Abstract: A process for the preparation of a compound of the formula ##STR1## wherein R.sub.1 is acyl of 1 to 8 carbon atoms, by reducing an intermediary to form an alcohol, oxidizing the alcohol to form an aidehyde, which is subjected to the action of an acyloxylation agent.
    Type: Grant
    Filed: October 29, 1993
    Date of Patent: March 28, 1995
    Assignee: Roussel-Uclaf
    Inventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
  • Patent number: 5401840
    Abstract: Novel compounds of the formula ##STR1## wherein either K' is oxygen or a K, a protective group of the oxo of the formula ##STR2## wherein n is 2 or 3, the 17-position dotted line is a bond, R.sub.a and R.sub.b are individually selected from the group consisting of hydrogen, hydroxy, alkyl and alkoxy of 1 to 4 carbon atoms or K' is an oxygen, the 17-position dotted line is an epoxy and R.sub.a and R.sub.b have the meaning indicated above which are useful intermediates for the preparation of hydrocortisone.
    Type: Grant
    Filed: August 12, 1993
    Date of Patent: March 28, 1995
    Assignee: Roussel-Uclaf
    Inventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
  • Patent number: 5399685
    Abstract: A process for the preparation of a compound of the formula ##STR1## wherein R.sub.1 is alkyl of 1 to 3 carbon atoms, R.sub.2 is alkyl of 1 to 12 carbon atoms, R.sub.3 is alkyl of 1 to 4 carbon atoms comprising reacting a compound of the formula ##STR2## wherein R.sub.4 is a remainder of an easily cleavable ether, K is a protected ketone function in the form of ketal, thioketal or mixed ketal and R.sub.1 has the above definition with a magnesium organic compound reagent of the formulaHalMg--CH.sub.2 --R.sub.2 Awherein Hal is a halogen and R.sub.2 is defined as above to obtain a compound of the formula ##STR3## wherein R.sub.1, R.sub.2 and K are defined as above, reacting the latter with an acylation agent to obtain a compound of the formula ##STR4## wherein R.sub.5 is alkyl of 1 to 6 carbon atoms or aryl of 6 to 10 carbon atoms and R.sub.1, R.sub.2 and K are defined as above, reacting the latter with an appropriate alkylation agent to obtain a compound of the formula ##STR5## wherein R.sub.1, R.sub.2, R.sub.
    Type: Grant
    Filed: June 11, 1993
    Date of Patent: March 21, 1995
    Assignee: Roussel-Uclaf
    Inventors: Jean Buendia, Veronique Crocq, Christian Masson, Denis Prat, Michel Vivat
  • Patent number: 5294704
    Abstract: A process for the production of a compound of the formula ##STR1## wherein R is an acyl group of 1 to 8 carbon atoms. The compound is formed through an intermediate compound of the formula ##STR2## wherein R.sub.1 is selected from the group consisting of methyl, phenyl, tolyl, and xylyl and wherein K is a protective group selected from the group consisting of ##STR3## in which n is 2 or 3 and the wavy line means that the group SO.sub.2 --R.sub.1 may have either isomeric form or are mixtures thereof.
    Type: Grant
    Filed: November 4, 1992
    Date of Patent: March 15, 1994
    Assignee: Roussel-Uclaf
    Inventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
  • Patent number: 5194602
    Abstract: New 9.alpha.-hydroxy-17-methylene steroids are prepared by the introduction of a substituted 17-methylene group in 9.alpha.-hydroxyandrost-4-ene-3, 17-dione.The resulting compounds are useful starting compounds in the synthesis of corticosteroids.
    Type: Grant
    Filed: December 12, 1990
    Date of Patent: March 16, 1993
    Assignee: Gist-Brocades N.V.
    Inventors: Jacobus N. M. Batisi, Arthur F. Marx
  • Patent number: 5187273
    Abstract: A compound of the formula ##STR1## wherein Hal is chlorine or bromine, R is selected from the group consisting of alkyl of 1 to 6 carbon atoms, aralkyl of 7 to 15 carbon atoms and a silylated group, K is a protective group selected from the group consisting of ##STR2## n is 2 or 3 and the wavy lines mean the groups may have either isomer form or are mixtures thereof which are intermediates for .DELTA..sup.4,9(11),16 -pregnatriene-3-ones.
    Type: Grant
    Filed: May 18, 1992
    Date of Patent: February 16, 1993
    Assignee: Roussel Uclaf
    Inventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
  • Patent number: 5182381
    Abstract: Novel 3-keto-19-nor-.DELTA..sup.4,9 -steroids of the formula ##STR1## and their non-toxic, pharmaceutically acceptable acid addition salts possessing a remarkable antiglucocorticoidal activity.
    Type: Grant
    Filed: September 10, 1991
    Date of Patent: January 26, 1993
    Assignee: Roussel Ulcaf
    Inventors: Daniel Philibert, Jean G. Teutsch, Germain Costerousse, Roger Deraedt
  • Patent number: 4987128
    Abstract: 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.
    Type: Grant
    Filed: February 24, 1987
    Date of Patent: January 22, 1991
    Assignee: Roussel Uclaf
    Inventors: Lucien Nedelec, Francois Nique, Anne-Marie Moura
  • Patent number: 4912097
    Abstract: Novel 11.beta.-alkynylphenyl-19-nor-steroids of the formula ##STR1## wherein R.sub.1 is alkynyl of 2 to 8 carbon atoms optionally substituted with at least one member of the group consisting of --OH halogen, trialkylsilyl of 1 to 6 alkyl carbon atoms, alkoxy and alkylthio of 1 to 6 carbon atoms and dialkylamino of 1 to 6 alkyl carbon atoms having remarkably antiprogestomimetic and antiglucocorticoidal activity.
    Type: Grant
    Filed: April 30, 1987
    Date of Patent: March 27, 1990
    Assignee: Roussel Uclaf
    Inventors: Jean-Georges Teutsch, Michel Klich, Daniel Philibert
  • Patent number: 4808710
    Abstract: A novel class of steroids having pregnancy-terminating and/or pregnancy-preventing activity and a very low antiglucocorticoid activity have been found. The compounds have the general formula: ##STR1## wherein R.sub.1 and R.sub.2 each separately represent H or a (1-4 C) hydrocarbon radical or together represent a (2-6 C) hydrocarbon radical, R.sub.3 represents H or a (1-4 C) hydrocarbon radical, optionally having an OH substituent, R.sub.4 represents OH or an ester or ether group, or together with R.sub.3 represents O or a heterocyclic ring system containing O, and wherein the broken line indicates an optionally present double bond between the carbon atoms at positions 9 and 10 of the steroid skeleton.
    Type: Grant
    Filed: July 16, 1987
    Date of Patent: February 28, 1989
    Assignee: Akzo N.V.
    Inventors: Hendrik P. de Jongh, Martinus J. van den Heuvel
  • Patent number: 4647410
    Abstract: Novel 17-(formamidosulfonylmethylene)-steroids of the formula ##STR1## useful as intermediates for the novel 17-(isocyanosulfonylmethylene)-steroids of the formula ##STR2## which are useful intermediates for 21-hydroxy-20-keto-.DELTA..sup.16 -steroids and 20-keto-.DELTA..sup.16 -steroids.
    Type: Grant
    Filed: April 27, 1984
    Date of Patent: March 3, 1987
    Assignee: Gist-Brocades N.V.
    Inventors: Albert M. van Leusen, Adriaan M. van Leusen