Sulfur In The Spiro Hetero Ring Patents (Class 540/30)
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Publication number: 20150031875Abstract: 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: ApplicationFiled: March 13, 2013Publication date: January 29, 2015Inventor: Martin Ostendorf
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Patent number: 6117994Abstract: A new process for the preparation of 16.beta.-methyl-steroids of the formula ##STR1## and novel intermediates.Type: GrantFiled: April 22, 1998Date of Patent: September 12, 2000Assignee: Hoechst Marion RousselInventors: Catherine Geurts, Michel Vivat
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Patent number: 5760256Abstract: 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: GrantFiled: February 21, 1995Date of Patent: June 2, 1998Assignee: Roussel UclafInventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
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Patent number: 5756722Abstract: 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: GrantFiled: September 6, 1996Date of Patent: May 26, 1998Assignee: Roussel UclafInventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
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Patent number: 5723638Abstract: 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: GrantFiled: June 26, 1995Date of Patent: March 3, 1998Assignee: Roussel UclafInventors: Robert Lett, Oleg Melnyk
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Patent number: 5594127Abstract: 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: GrantFiled: November 14, 1995Date of Patent: January 14, 1997Assignee: Roussel UclafInventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
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Patent number: 5585482Abstract: 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: GrantFiled: October 19, 1995Date of Patent: December 17, 1996Assignee: Roussel UclafInventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
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Patent number: 5556962Abstract: 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: GrantFiled: October 2, 1995Date of Patent: September 17, 1996Assignee: Roussel UclafInventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
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Patent number: 5502182Abstract: 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: GrantFiled: December 22, 1994Date of Patent: March 26, 1996Assignee: Roussel UclafInventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
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Patent number: 5401864Abstract: 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: GrantFiled: October 29, 1993Date of Patent: March 28, 1995Assignee: Roussel-UclafInventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
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Patent number: 5401840Abstract: 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: GrantFiled: August 12, 1993Date of Patent: March 28, 1995Assignee: Roussel-UclafInventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
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Patent number: 5399685Abstract: 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: GrantFiled: June 11, 1993Date of Patent: March 21, 1995Assignee: Roussel-UclafInventors: Jean Buendia, Veronique Crocq, Christian Masson, Denis Prat, Michel Vivat
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Patent number: 5294704Abstract: 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: GrantFiled: November 4, 1992Date of Patent: March 15, 1994Assignee: Roussel-UclafInventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
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Patent number: 5194602Abstract: 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: GrantFiled: December 12, 1990Date of Patent: March 16, 1993Assignee: Gist-Brocades N.V.Inventors: Jacobus N. M. Batisi, Arthur F. Marx
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Patent number: 5187273Abstract: 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: GrantFiled: May 18, 1992Date of Patent: February 16, 1993Assignee: Roussel UclafInventors: Francis Brion, Jean Buendia, Christian Diolez, Michel Vivat
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Patent number: 5182381Abstract: 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: GrantFiled: September 10, 1991Date of Patent: January 26, 1993Assignee: Roussel UlcafInventors: Daniel Philibert, Jean G. Teutsch, Germain Costerousse, Roger Deraedt
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Patent number: 4987128Abstract: 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: GrantFiled: February 24, 1987Date of Patent: January 22, 1991Assignee: Roussel UclafInventors: Lucien Nedelec, Francois Nique, Anne-Marie Moura
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Patent number: 4912097Abstract: 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: GrantFiled: April 30, 1987Date of Patent: March 27, 1990Assignee: Roussel UclafInventors: Jean-Georges Teutsch, Michel Klich, Daniel Philibert
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Patent number: 4808710Abstract: 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: GrantFiled: July 16, 1987Date of Patent: February 28, 1989Assignee: Akzo N.V.Inventors: Hendrik P. de Jongh, Martinus J. van den Heuvel
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Patent number: 4647410Abstract: 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: GrantFiled: April 27, 1984Date of Patent: March 3, 1987Assignee: Gist-Brocades N.V.Inventors: Albert M. van Leusen, Adriaan M. van Leusen