Abstract: The present invention relates to a process for the synthesis of compounds of formula (I), wherein the meaning of R is dimethylamino or acetyl group, using the compound of formula (III) or (IV), wherein the meaning of R? is dimethylamino or 2-methyl-1,3-dioxan-2-yl group, as starting material and methoxymethyl lithium as reagent.
Type:
Grant
Filed:
February 16, 2015
Date of Patent:
June 20, 2017
Assignee:
Richter Gedeon Nyrt.
Inventors:
Sándor Mahó, Csaba Sánta, János Csörgei, Gábor Szabó, Tamás Schäfer, Zoltán Béni
Abstract: The present invention relates to a new process for the synthesis of compounds of formula (I) (wherein the meaning of R is dimethylamino or acetyl group) using the compound of formula (II) (wherein the meaning of R is dimethylamino or 2-methyl-1,3-dioxolan-2-yl group) as starting material, as well as to the intermediate of the process.
Type:
Grant
Filed:
October 1, 2014
Date of Patent:
June 13, 2017
Assignee:
RICHTER GEDEON NYRT.
Inventors:
Sándor Mahó, Csaba Sánta, János Csörgei, János Horváth, Antal Aranyi, Zoltán Béni
Abstract: Described herein are imidazolyl compounds which either act as pure antiprogestins and methods of using such pure antagonists for gynecological indications and breast cancer.
Type:
Application
Filed:
June 5, 2013
Publication date:
December 11, 2014
Inventors:
Klaus Nickisch, Walter Elger, Bindu Santhamma
Abstract: Provided are steroid analogues functionalized with polar substituents at the C3 and/or C20 positions of the steroid ring system that exhibit improved water solubility. Also provided are pharmaceutical compositions comprising the steroid analogues and methods using the novel steroid analogues for the treatment and prevention of neurodegeneration in a patient following injury to the central nervous system.
Type:
Application
Filed:
February 26, 2009
Publication date:
October 27, 2011
Inventors:
Christopher Macnevin, Donald G. Stein, Dennis C. Liotta, Iqbal Sayeed, David B. Guthrie, Mark A. Lockwood, Michael G. Natchus
Abstract: An efficient method for the synthesis of aminosterol compounds such as squalamine and compound 1436 is described. A method of the invention provides for regioselective oxidation and regioselective sulfonation of a fused ring system. The fused ring base can be, for example, a steroid ring base. The aminosterol compounds are effective as, for example, antibiotics, antiangiogenic agents and NHE3 inhibitors.
Type:
Application
Filed:
October 11, 2002
Publication date:
September 11, 2003
Inventors:
William A. Kinney, Xuehai Zhang, Ronald Michalak
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
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
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.
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
Abstract: A compound of the formula ##STR1## wherein R is=0 or ##STR2## and the rings A and B are selected from the group consisting of ##STR3## K is oxo or a protector group of oxo of the formula ##STR4## n is 2 or 3 and R.sub.1 is an ether or ester remainder, K' is oxo or a protector oxime, hydrazone or semicarbazone group and the wavy lines symbolize an isomer mixture, a process for their preparation and their use as intermediates.
Type:
Grant
Filed:
March 9, 1995
Date of Patent:
April 2, 1996
Assignee:
Roussel Uclaf
Inventors:
Jean Buendia, Remi Chauvin, Michel Vivat
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
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
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
Abstract: 13.alpha.-alkylgonanes of formula I ##STR1## where R is an acyl radical with as many as 10 C-atoms, andX is an oxygen atom or the grouping N--OH,have a strong antigestagenic effect and can be used for postcoital fertility control.
Type:
Grant
Filed:
December 18, 1985
Date of Patent:
October 25, 1988
Assignee:
Schering Aktiengesellschaft
Inventors:
Gunter Neef, Rudolf Wiechert, Sybille Beier, Walter Elger, David Henderson
Abstract: Novel 19-nor steroids and 19-nor-D-homo-steroids of the formula ##STR1## wherein R.sub.1 is an organic radical of 1 to 18 carbon atoms containing at least one atom selected from the group consisting of nitrogen, phosphorous and silicon with the atom immediately adjacent to the 11-carbon atom being carbon, R.sub.2 is a hydrocarbon of 1 to 8 carbon atoms, X is selected from the group consisting of a pentagonal ring and a hexagonal ring optionally substituted and optionally containing a double bond, B and C together form a double bond or an epoxy group, the C.dbd.A group at position 3 is selected from the group consisting of C.dbd.O, ketal, which may be open or closed ##STR2## are selected from the group consisting of alkyl of 1 to 8 carbon atoms and aralkyl of 7 to 15 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having anti-glucocorticoid activity and a process for their preparation.
Type:
Grant
Filed:
January 22, 1985
Date of Patent:
January 6, 1987
Assignee:
Roussel Uclaf
Inventors:
Vesperto Torelli, Jean G. Teutsch, Daniel Philibert