Oxygen Bonded Directly At The 12-position (e.g., Cholic Acids, Desoxycholic Acids, Dehydrocholic Acids, Etc.) Patents (Class 552/549)
  • Patent number: 10160782
    Abstract: The present invention discloses method for preparing deoxycholic acid (DCA) or an ester thereof or a pharmaceutically acceptable salt thereof. Said compounds may be applied to remove a fat deposition.
    Type: Grant
    Filed: February 26, 2016
    Date of Patent: December 25, 2018
    Assignee: NORATECH PHARMACEUTICALS, INC.
    Inventors: Cheng-Gang Lin, Li Gui, Pan Chen, Zhi-Xuan Wang, Tong-Wei Guan, Yuan-Yuan Yin, Yu-Ling Lu
  • Patent number: 10053486
    Abstract: Synthetic methods for preparing deoxycholic acid and intermediates thereof are provided.
    Type: Grant
    Filed: April 24, 2015
    Date of Patent: August 21, 2018
    Assignee: Kythera Biopharmaceuticals, Inc.
    Inventors: Achampeta Rathan Prasad, Roy A. Swaringen, Jr., John Gregory Reid, Robert M. Moriarty, Akhila Kumar Sahoo
  • Patent number: 9127036
    Abstract: Bile acids and related compositions and methods of synthesis and use. More specifically, deoxycholic acid and related compositions, said compositions being free of all moieties of animal origin and free of pyrogenic moieties.
    Type: Grant
    Filed: August 12, 2010
    Date of Patent: September 8, 2015
    Assignee: KYTHERA BIOPHARMACEUTICALS, INC.
    Inventors: Robert M. Moriarty, Nathaniel E. David, Nadir Ahmeduddin Mahmood
  • Publication number: 20150141679
    Abstract: Synthetic methods for preparing deoxycholic acid and intermediates thereof, high purity synthetic deoxycholic acid, compositions and methods of use are provided. Also, provided are processes for the synthesis of 12-keto or 12-?-hydroxysteroids from ?-9,11-ene, 11-keto or 11-hydroxy-?-steroids. This inversion is also directed to novel compounds prepared during the synthesis. This invention is also directed to the synthesis of deoxycholic acid starting from hydrocortisone.
    Type: Application
    Filed: November 4, 2014
    Publication date: May 21, 2015
    Applicant: Kythera Biopharmaceuticals, Inc.
    Inventors: Robert M. Moriarty, Achampeta Rathan Prasad, John Gregory Reid, Roy A. Swaringen, JR.
  • Patent number: 8883770
    Abstract: Bile acids and related compositions and methods of synthesis and use. More specifically, deoxycholic acid and related compositions, said compositions being free of all moieties of animal origin and free of pyrogenic moieties.
    Type: Grant
    Filed: January 14, 2013
    Date of Patent: November 11, 2014
    Assignee: Kythera Biopharmaceuticals, Inc.
    Inventors: Robert M. Moriarty, Nathaniel E. David, Nadir Ahmeduddin Mahmood
  • Publication number: 20140107328
    Abstract: Chemoselective isolation of aliphatic hydroxyl group-containing and aromatic hydroxyl group-containing compounds is accomplished via formation of polymeric siloxyl ethers. Chemoselective release of aliphatic hydroxyl group-containing and aromatic hydroxyl group-containing compounds from polymeric siloxyl reagents is described.
    Type: Application
    Filed: December 11, 2013
    Publication date: April 17, 2014
    Inventors: Erin E. CARLSON, Darci TRADER
  • Publication number: 20130267721
    Abstract: Synthetic methods for preparing deoxycholic acid and intermediates thereof are provided.
    Type: Application
    Filed: January 28, 2013
    Publication date: October 10, 2013
    Inventors: Achampeta Rathan Prasad, Roy A. Swaringen, JR., John Gregory Reid, Robert M. Moriarty, Akhila Kumar Sahoo
  • Publication number: 20130261317
    Abstract: This invention relates generally to methods for preparing certain bile acids from non-mammalian sourced starting materials as well as to synthetic bile acids and compositions comprising such acids wherein the acids are characterized by a different C14 population than naturally occurring bile acids as well as being free from any mammalian pathogens. This invention is also directed to the synthesis of intermediates useful in the synthesis of such bile acids. Accordingly, the C ring of the steroidal scaffold is oxidized to provide a synthetic route and intermediates to DCA. This invention also provides synthetic methods for preparing deoxycholic acid or a salt thereof starting from aromatic steroids such as estrogen, equilenin, and derivatives thereof. This invention is also directed to intermediates such as 12-oxo or delta-9,11-ene steroids as well as novel processes for their preparation.
    Type: Application
    Filed: September 19, 2011
    Publication date: October 3, 2013
    Applicant: KYTHERA BIOPHARMACEUTICALS, INC.
    Inventors: Robert M. Moriarty, Photon Rao
  • Publication number: 20130252931
    Abstract: Bile acids and related compositions and methods of synthesis and use. More specifically, deoxycholic acid and related compositions, said compositions being free of all moieties of animal origin and free of pyrogenic moieties.
    Type: Application
    Filed: August 12, 2010
    Publication date: September 26, 2013
    Inventors: Robert M. Moriarty, Nathaniel E. David, Nadir Ahmeduddin Mahmood
  • Publication number: 20130085125
    Abstract: Synthesis and purification of deoxycholic acid and its salts are provided.
    Type: Application
    Filed: June 14, 2012
    Publication date: April 4, 2013
    Inventors: Daniel J. Ganley, Jeremy Wilt
  • Patent number: 8410083
    Abstract: The invention relates to compounds of Formula A: (A) or a pharmaceutically acceptable salt, solvate, hydrate, or prodrug thereof. The compounds of Formula A are TGR5 modulators useful for the treatment of various diseases, including obesity, insulin sensitivity, inflammation, cholestasis, and bile desaturation.
    Type: Grant
    Filed: January 18, 2008
    Date of Patent: April 2, 2013
    Assignee: Intercept Pharmaceuticals, Inc.
    Inventor: Roberto Pellicciari
  • Patent number: 8383858
    Abstract: This invention relates to processes and intermediates for the preparation of an alpha-amino beta-hydroxy acid of Formula 1 wherein the variables R1, R?1 and R2 are defined herein and the compound of Formula 1 has an enantiomeric excess (ee) of 55% or greater.
    Type: Grant
    Filed: August 4, 2010
    Date of Patent: February 26, 2013
    Assignee: Vertex Pharmaceuticals Incorporated
    Inventors: Gerald J. Tanoury, Minzhang Chen, Young Chun Jung, Raymond E. Forslund
  • Publication number: 20130041106
    Abstract: Chemoselective isolation of hydroxyl group-containing and carboxyl group-containing compounds is accomplished via formation of polymeric silyl ethers and polymeric siloxyl esters, respectively. Preparation of chemoselective polymeric reagents for capture of hydroxyl group containing compounds and carboxyl group containing compounds is described.
    Type: Application
    Filed: August 10, 2012
    Publication date: February 14, 2013
    Inventors: Erin E. Carlson, Darci Trader, Antoinette Odendaal
  • Patent number: 8367852
    Abstract: Synthetic methods for preparing deoxycholic acid and intermediates thereof are provided.
    Type: Grant
    Filed: May 25, 2011
    Date of Patent: February 5, 2013
    Assignee: Kythera Biopharmaceuticals, Inc.
    Inventors: Achampeta Rathan Prasad, Roy A. Swaringen, Jr., John Gregory Reid, Robert M. Moriarty, Akhila Kumar Sahoo
  • Patent number: 8362285
    Abstract: Synthetic methods for preparing deoxycholic acid and intermediates thereof are provided.
    Type: Grant
    Filed: January 20, 2011
    Date of Patent: January 29, 2013
    Assignee: Kythera Biopharmaceuticals, Inc.
    Inventors: Achampeta Rathan Prasad, Roy A. Swaringen, Jr., John Gregory Reid, Robert M. Moriarty, Akhila Kumar Sahoo
  • Publication number: 20120309728
    Abstract: The present invention relates to a compound of formula (I) for its use for reversing or inhibiting multidrug resistance.
    Type: Application
    Filed: December 17, 2010
    Publication date: December 6, 2012
    Inventors: Catherine Grenot, Claude Cuilleron
  • Publication number: 20120277198
    Abstract: The invention provides, in part, polyhydroxylated bile acids for treating biliary disorders, for example, biliary disorders arising out of cholestasis of portal hypertension. The invention also provides, in part, polyhydroxylated bile acids for stimulating bile flow. New compounds 2?,3?,7?,12?-tetrahydroxy-5?-cholanoic acid and 3?.4?,7?,12?-tetrahydroxy-5?-cholanoic acid are disclosed, uses thereof and synthesis thereof.
    Type: Application
    Filed: February 27, 2012
    Publication date: November 1, 2012
    Inventors: VICTOR LING, RENXUE WANG, JONATHAN AHAB SHEPS
  • Patent number: 8242294
    Abstract: Bile acids and related compositions and methods of synthesis and use. More specifically, deoxycholic acid and related compositions, said compositions being free of all moieties of animal origin and free of pyrogenic moieties.
    Type: Grant
    Filed: August 13, 2009
    Date of Patent: August 14, 2012
    Assignee: Kythera Biopharmaceuticals, Inc.
    Inventors: Robert M. Moriarty, Nathaniel E. David, Nadir Ahmeduddin Mahmood
  • Patent number: 8114862
    Abstract: The invention relates to compounds of Formula A: or a salt, solvate, hydrate, or prodrug thereof. The compounds of Formula A are TGR5 modulators useful for the treatment of various diseases, including metabolic disease, inflammatory disease, liver disease, autoimmune disease, cardiac disease, kidney disease, cancer, and gastrointestinal disease.
    Type: Grant
    Filed: November 19, 2009
    Date of Patent: February 14, 2012
    Assignee: Intercept Pharmaceuticals, Inc.
    Inventor: Roberto Pellicciari
  • Patent number: 7994351
    Abstract: Synthetic methods for preparing deoxycholic acid and intermediates thereof are provided.
    Type: Grant
    Filed: November 6, 2009
    Date of Patent: August 9, 2011
    Assignee: Kythera Biopharmaceuticals, Inc.
    Inventors: Achampeta Rathan Prasad, Roy A. Swaringen, Jr., John Gregory Reid, Robert M. Moriarty, Akhila Kumar Sahoo
  • Patent number: 7982062
    Abstract: A process for the preparation of high purity cholanic acids, typically in purity equal to or higher than 99%.
    Type: Grant
    Filed: September 11, 2007
    Date of Patent: July 19, 2011
    Assignee: Dipharma Francis s.r.l.
    Inventors: Pietro Allegrini, Tiziano Scubla, Fausto Gorassini, Andrea Finco
  • Patent number: 7932243
    Abstract: The present disclosure relates to methods and compositions to offset, ameliorate and/or alleviate one or more unwanted and/or adverse gastrointestinal effects. For example, in some embodiments, the present disclosure relates to compositions that include a bile acid, a carbohydrate and/or a pharmaceutical compound, wherein the pharmaceutical is associated with an adverse gastrointestinal effect in a subject (e.g., mammal or human). Non-limiting examples of pharmaceutical compounds may include a nonsteroidal anti-inflammatory drug, a gastric irritating drug (e.g., an antibiotic, an adrenal cortocoid steroid and an anti-cancer drug) and combinations thereof. The disclosure further relates to methods of ameliorating or eliminating at least one adverse gastrointestinal effects of a composition, comprising administering to a subject an aqueous solution comprising a bile acid and a carbohydrate.
    Type: Grant
    Filed: March 10, 2006
    Date of Patent: April 26, 2011
    Inventor: Seo Hong Yoo
  • Patent number: 7902387
    Abstract: Synthetic methods for preparing deoxycholic acid and intermediates thereof are provided.
    Type: Grant
    Filed: May 16, 2008
    Date of Patent: March 8, 2011
    Assignee: Kythera Biopharmaceuticals, Inc.
    Inventors: Achampeta Rathan Prasad, Roy A. Swaringen, Jr., John Gregory Reid, Robert M. Moriarty, Akhila Kumar Sahoo
  • Publication number: 20100267684
    Abstract: The present invention relates to a use of a biological surfactant as an anti-inflammatory agent and a tissue preservative solution. More particularly, the present invention is directed to an anti-inflammatory agent and a tissue preservative solution comprising a biological surfactant which blocks a reaction of a proinflammatory factor with a receptor by emulsifying the proinflammatory factor.
    Type: Application
    Filed: November 16, 2009
    Publication date: October 21, 2010
    Applicant: SEOUL NATIONAL UNIVERSITY INDUSTRY FOUNDATION
    Inventors: Seung-yong Seong, Chang Gu Kang, Youn Hee Kim
  • Patent number: 7772220
    Abstract: The present disclosure is related to clear aqueous solutions of one or more bile acids and either an aqueous soluble starch conversion product or a non-starch polysaccharide. Solutions of the disclosure may be administered to a subject in conjunction with a pharmaceutical compound having one or more toxic effects. In some embodiments, solutions of the disclosure are administered to a mammal in conjunction with a pharmaceutical compound associated with a peripherial neurotoxicity (e.g., cisplatin and/or suramin) to reduce or eliminate the neuropathic effect(s).
    Type: Grant
    Filed: October 14, 2005
    Date of Patent: August 10, 2010
    Inventor: Seo Hong Yoo
  • Patent number: 7601708
    Abstract: This invention is directed to methods for providing sustained systemic concentrations of therapeutic or prophylactic agents such as GABA analogs following oral administration to animals. This invention is also directed to compounds and pharmaceutical compositions that are used in such methods.
    Type: Grant
    Filed: July 19, 2005
    Date of Patent: October 13, 2009
    Assignee: XenoPort, Inc.
    Inventors: Kenneth C. Cundy, Mark A. Gallop, Cindy X. Zhou
  • Patent number: 7598235
    Abstract: This invention is directed to compounds that provide for sustained systemic concentrations of therapeutic or prophylactic agents following administration to animals. This invention is also directed to pharmaceutical compositions including and methods using such compounds.
    Type: Grant
    Filed: September 6, 2005
    Date of Patent: October 6, 2009
    Assignee: XenoPort, Inc.
    Inventors: Kenneth C. Cundy, Mark A. Gallop
  • Patent number: 7501403
    Abstract: The present invention relates to the use of a bile acid or bile salt fatty acid conjugate of general formula II W-X-G in which G is a bile acid or bile salt radical, which, if desired, is conjugated in position 24 with a suitable amino acid, W stands for one or two fatty acid radicals having 14-22 carbon atoms and X stands for a suitable bonding member or for a direct C?C bond between said bile acid or bile salt radical and the fatty acid(s) or of a pharmaceutical composition comprising same for the reduction of Cholesterol in blood, for the treatment of Fatty Liver, Hyperglycemia and Diabetes.
    Type: Grant
    Filed: April 15, 2002
    Date of Patent: March 10, 2009
    Assignee: Galmed International Limited
    Inventor: Tuvia Gilat
  • Patent number: 7141559
    Abstract: This invention relates to novel compounds that are liver selective glucocorticoid receptor antagonists, to methods of preparing such compounds, and to methods for using such compounds in the regulation of metabolism, especially lowering serum glucose levels, insulin levels, or lipid levels, and/or decreasing body weight.
    Type: Grant
    Filed: June 12, 2003
    Date of Patent: November 28, 2006
    Assignee: Karo Bio AB
    Inventors: Richard D. Bishop, Russell Drew Cink, Bradley D. Gates, Lars T. Hagberg, Peer B. Jacobsen, Philip R. Kym, Chunqiu Lai, Marvin Robert Leanna, James T. Link, Steven J. Richards, Noah Tu, Tom W. von Geldern
  • Patent number: 7002027
    Abstract: The present invention is directed to compositions and methods of treating cancer by gene therapy using a therapeutic gene formulated in a buffer comprising a delivery-enhancing agent. The delivery-enhancing agents of the invention can be used to formulate therapeutic or diagnostic agents, such as proteins, nucleic acids, antisense RNA, small molecules, etc., for administration to any tissue or organ having an epithelial membrane. The delivery-enhancing agents include detergents, alcohols, surfactants and other molecules.
    Type: Grant
    Filed: July 8, 1997
    Date of Patent: February 21, 2006
    Assignees: Canji, Inc., Schering Corporation
    Inventors: Heidrun Engler, Tattanahalli L. Nagabhushan, Stephen Kenneth Youngster
  • Patent number: 6984634
    Abstract: This invention is directed to compounds that provide for sustained systemic concentrations of therapeutic or prophylactic agents following administration to animals. This invention is also directed to pharmaceutical compositions including and methods using such compounds.
    Type: Grant
    Filed: October 9, 2001
    Date of Patent: January 10, 2006
    Assignee: XenoPort, Inc.
    Inventors: Kenneth C. Cundy, Mark A. Gallop
  • Patent number: 6803030
    Abstract: Compounds able to chelate paramagnetic metal ions and the use thereof as contrast agents in the technique known as “Magnetic Resonance Imaging” (M.R.I.).
    Type: Grant
    Filed: August 27, 2002
    Date of Patent: October 12, 2004
    Assignee: Bracco Imaging S.p.A.
    Inventors: Christoph De Haen, Andrea Beltrami, Enrico Cappelletti, Luciano Lattuada, Mario Virtuani
  • Patent number: 6793943
    Abstract: An object of the present invention is to provide a very effective health food exhibiting the effect near that which has been already achieved by the traditional Chinese medical science. The present invention relates to a health food product comprising cholic acid, especially to a health food product comprising cholic acid and isoflavone and/or isoflavone glycoside.
    Type: Grant
    Filed: April 10, 2001
    Date of Patent: September 21, 2004
    Assignee: Daicho Kikaku Incorporated Company
    Inventor: Takao Daicho
  • Patent number: 6624156
    Abstract: The present invention provides hybrid molecules and methods of synthesizing such hybrid molecules from a cholinergic agent and a bile acid. The hybrid molecules function as cholinergic agents and may be either cholinergic agonists or cholinergic antagonists. Further disclosed herein are compositions comprising hybrid cholinergic agents and methods of making such compositions. Methods of treating a patient having a cholinergic disorder are also disclosed.
    Type: Grant
    Filed: June 25, 2002
    Date of Patent: September 23, 2003
    Assignee: Board of Trustees of the University of Arkansas
    Inventors: Jean-Pierre Raufman, Piotr Zimniak, Kunrong Cheng
  • Patent number: 6589946
    Abstract: The present invention relates to bile acid or bile salt fatty acid conjugates (hereinafter called “BAFAC), to their use in dissolving cholesterol gallstones in bile, preventing their occurrence or recurrence, to their use in reducing or preventing arteriosclerosis and to methods for the treatment of said diseases. The conjugates are of the formula W—X—G in which G is a bile acid or bile salt radical, W stands for one or two saturated fatty acid radicals and X is either a direct bond or a bonding member between bile acid or bile salt and the fatty acid(s). The conjugation is advantageously performed at a position selected among the 3, 6, 7, 12 and 24 positions of the bile acid or bile salt nucleus. The fatty acids are preferably saturated fatty acids having 6-26 carbon atoms.
    Type: Grant
    Filed: February 21, 2002
    Date of Patent: July 8, 2003
    Assignee: Galmed International Limited
    Inventor: Tuvia Gilat
  • Patent number: 6468975
    Abstract: Novel glucocorticoid receptor ligands and methods of treating diseases such as diabetes, wherein the ligands have general formula (I) wherein the variables are as defined by the present specification.
    Type: Grant
    Filed: February 11, 2002
    Date of Patent: October 22, 2002
    Assignee: Karo Bio AB
    Inventors: Theresa Apelqvist, Jinchang Wu, Konrad Koehler
  • Patent number: 6448420
    Abstract: A novel ester compound having an exo-form 2-alkylbicyclo[2.2.1]heptan-2-yl ester as the acid-decomposable site is used as a dissolution regulator to formulate a resist composition having a high sensitivity, resolution, etching resistance and storage stability.
    Type: Grant
    Filed: May 18, 2000
    Date of Patent: September 10, 2002
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeshi Kinsho, Tsunehiro Nishi, Takeru Watanabe, Koji Hasegawa, Mutsuo Nakashima, Jun Hatakeyama
  • Publication number: 20020115874
    Abstract: A novel ester compound having an exo-form 2-alkylbicyclo[2.2.1]heptan-2-yl ester as the acid-decomposable site is used as a dissolution regulator to formulate a resist composition having a high sensitivity, resolution, etching resistance and storage stability.
    Type: Application
    Filed: May 18, 2000
    Publication date: August 22, 2002
    Inventors: Takeshi Kinsho, Tsunehiro Nishi, Takeru Watanabe, Koji Hasegawa, Mutsuo Nakashima, Jun Hatakeyama
  • Publication number: 20020111338
    Abstract: This invention is directed to compounds that provide for sustained systemic concentrations of therapeutic or prophylactic agents following administration to animals. This invention is also directed to pharmaceutical compositions including and methods using such compounds.
    Type: Application
    Filed: October 5, 2001
    Publication date: August 15, 2002
    Inventors: Kenneth C. Cundy, Mark A. Gallop, Cindy X. Zhou
  • Publication number: 20020091111
    Abstract: The present invention relates to bile acid or bile salt fatty acid conjugates (hereinafter called “BAFAC), to their use in dissolving cholesterol gallstones in bile, preventing their occurrence or recurrence, to their use in reducing or preventing arteriosclerosis and to methods for the treatment of said diseases. The conjugates are of the formula W—X—G in which G is a bile acid or bile salt radical, W stands for one or two saturated fatty acid radicals and X is either a direct bond or a bonding member between bile acid or bile salt and the fatty acid(s). The conjugation is advantageously performed at a position selected among the 3, 6, 7, 12 and 24 positions of the bile acid or bile salt nucleus. The fatty acids are preferably saturated fatty acids having 6-26 carbon atoms.
    Type: Application
    Filed: February 21, 2002
    Publication date: July 11, 2002
    Applicant: Galmed International Limited
    Inventor: Tuvia Gilat
  • Patent number: 6342489
    Abstract: Bile acid metal salts of therapeutic interest and pharmaceutical and veterinary composition containing same for the treatment of anemias and other conditions are described.
    Type: Grant
    Filed: April 4, 2000
    Date of Patent: January 29, 2002
    Assignees: ICE s.r.l.
    Inventors: Beniamino Palmieri, Alessandro Medici, Enzo Bartoli
  • Patent number: 6255502
    Abstract: A pharmaceutical composition contains an acid addition salt of a basic drug and a fatty acid or bile acid. The acid addition salts thus formed exhibit enhanced transmucosal and transdermal penetration of the basic drug. The acid addition salts, an inclusion complex containing said salts and a use of said salts are also disclosed.
    Type: Grant
    Filed: April 19, 1999
    Date of Patent: July 3, 2001
    Assignee: Farmarc Nederland B.V.
    Inventors: Lawrence John Penkler, Lu├ęta-Ann De Kock, Darryl Vanstone Whittaker
  • Patent number: 5610151
    Abstract: Monomeric bile acid derivatives, processes for their preparation and the use of these compounds as medicamentsMonomeric bile acid derivatives of the formula IZ--X--GS I,in which GS, X and Z have the meanings given, and processes for their preparation are described. The compounds have useful pharmacological properties and can therefore be used as medicaments.
    Type: Grant
    Filed: May 5, 1994
    Date of Patent: March 11, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heiner Glombik, Alfons Enhsen, Werner Kramer, G unther Wess
  • Patent number: 5559258
    Abstract: Ethylenically unsaturated bile acid derivatives of the formula IG--X--A Iin which G, X and A have the meanings indicated, are described. They are suitable for the preparation of polymeric bile acid derivatives. Bile acid derivatives of the formula IVaG--X' IVain which G and X' have the meanings indicated, are also described. They are useful synthesis components for the preparation of pharmaceuticals.
    Type: Grant
    Filed: November 22, 1994
    Date of Patent: September 24, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Alfons Enhsen, Heiner Glombik, Stefan M ullner, G unther Wess
  • Patent number: 5541348
    Abstract: Novel bile acids according to the general formula ##STR1## wherein R.sub.1 represents a hydroxyl group, R.sub.2 and R.sub.3 both represent a hydrogen or a hydroxyl group, or R.sub.2 represents a hydroxyl group or a .beta. hydroxyl group and R.sub.3 represents a hydrogen or R.sub.3 represents a hydroxyl group and R.sub.2 represents a hydrogen, and R.sub.4 represents a (CH.sub.2).sub.n R.sub.5 wherein n is from 1 to 6, and R.sub.5 represents --0--PO(OH).sub.2, --CH(OH)COOH, a nitrogen containing saturated heterocyclic ring group, NR.sub.6 R.sub.7, wherein R.sub.6 and R.sub.7 are the same or different and each represent hydrogen or a C.sub.1 -C.sub.10 alkyl group or CO--R.sub.8 wherein R.sub.8 represents an amino acid moiety, R-phenylglycine, 12-aminododecanoic acid or 4-aminohippuric acid are synthesized from cholic, deoxycholic, chenodeoxycholic, ursodeoxycholic and lithocholic acids and iodo-derivatives thereof by known processes and/or by novel processes according to the present invention.
    Type: Grant
    Filed: March 10, 1994
    Date of Patent: July 30, 1996
    Assignee: National Research Council of Canada
    Inventors: Prabhat Ayra, Graham W. Burton
  • Patent number: 5252729
    Abstract: The present invention is directed toward a process for extracting compounds from plant material, comprisinga) contacting hydrolyzed plant material with a supercritical fluid and optionally with a co-solvent and p1 b) recovering the compound from the supercritical fluid.In another embodiment, the present invention is directed toward a process for removing a compound from plant material, comprising contacting the plant material with an acid, a supercritical fluid and a co-solvent, and recovering the compound from the supercritical fluid. The sterols, diosgenin and sarsapogenin, are efficiently extracted from barbasco root and Yucca seed, respectively.
    Type: Grant
    Filed: October 23, 1991
    Date of Patent: October 12, 1993
    Assignee: Schering Corporation
    Inventors: Michelle A. De Crosta, Peter Kabasakalian, Frederick J. F. Honold, Sr.
  • Patent number: 4981983
    Abstract: New derivatives of chenodeoxycholic, ursodeoxy cholic, cholic and ursocholic acids, bearing a methyl group in the side chain in an alfa position to the carboxylic group, the corresponding nor- and di-nor- derivatives, and the corresponding conjugates with taurine and glycine, are described.The compounds of the invention are prepared by methylation of the esters with methyl iodide in the presence of lithium-dialkylamides.
    Type: Grant
    Filed: October 2, 1989
    Date of Patent: January 1, 1991
    Assignee: Gipharmex S.p.A.
    Inventors: Virginio Castagnola, E. Giuliano Frigerio, Roberto Pellicciari, Aldo Roda
  • Patent number: 4927921
    Abstract: A compound of the formula ##STR1## wherein R.sub.1 is hydrogen or methyl, R.sub.2 is methyl or ethyl, and A,B,C and D rings optionally containing at least one double bond and optionally substituted with at least one member of the group consisting of optionally protected --OH, .dbd.O, alkyl and alkoxy of 1 to 4 carbon atoms, halogen and alkenyl and alkynyl of 2 to 4 carbon atoms, R is selected from the group consisting of halogen, --OH, alkylthio and alkoxy of 1 to 6 carbon atoms, aralkoxy, arylthio and aralkylthio of 7 to 15 carbon atoms and ##STR2## R.sub.3 and R.sub.4 are individually hydrogen, or alkyl of 1 to 6 carbon atoms or aralkyl of 7 to 15 carbon atoms or taken together with the nitrogen form a heterocycle optionally containing another nitrogen or oxygen atom, excepting the product in which R is methoxy, R.sub.1 and R.sub.2 each represent methyl, A ring carries a 3.beta.-acetoxy function and B ring contains a double bond in 5(6) useful as intermediates for the preparation of 20-keto-pregnanes.
    Type: Grant
    Filed: December 4, 1987
    Date of Patent: May 22, 1990
    Assignee: Roussel Uclaf
    Inventors: Michel Vivat, Jean Buendia
  • Patent number: 4921848
    Abstract: Compounds of formula I ##STR1## wherein: R.sub.1 is hydrogen or hydroxy, and the methyl and hydroxy groups at 6- and 7-positions respectively can be either in .alpha. or .beta. configuration, are useful in human therapy. Compounds I are prepared by methylation of the corresponding appropriately protected 7-keto-derivatives.
    Type: Grant
    Filed: October 19, 1988
    Date of Patent: May 1, 1990
    Assignee: Gipharmex S.P.A.
    Inventors: Giuliano Frigerio, Roberto Pellicciari, Aldo Roda
  • Patent number: 4921999
    Abstract: A method is provided for making tertiary butyl esters by effecting reaction between an organic carboxylic acid and isobutylene in the presence of an effective amount of trifluoromethane sulfonic acid at temperatures below about -7.degree. C. Tertiary butyl esters are useful as dissolution inhibitors for novolak resins.
    Type: Grant
    Filed: August 23, 1988
    Date of Patent: May 1, 1990
    Assignee: General Electric Company
    Inventor: Michael J. O'Brien