Preparing Directly From An Amide (e.g., Preparing Directly From A Sulfenamide, Nitrosamine, Carboxamide, Thiourea, Etc.) Patents (Class 564/414)
  • Patent number: 9012690
    Abstract: Disclosed herein is a method for producing an alcohol and an amine from an amide under an atmosphere of hydrogen with the use of, as a catalyst, a ruthenium complex that is easily prepared, easy to handle, and relatively cheaply obtained. Specifically, the method is a method for producing an alcohol and/or an amine from an amide compound under an atmosphere of hydrogen with the use of as a catalyst, a ruthenium carbonyl complex represented by the following general formula (1): RuXY(CO)(L) (1) wherein X and Y may be the same or different from each other and each represents an anionic ligand and L represents a tridentate aminodiphosphine ligand containing two phosphino groups and a —NH— group.
    Type: Grant
    Filed: September 1, 2011
    Date of Patent: April 21, 2015
    Assignee: Takasago International Corporation
    Inventors: Osamu Ogata, Wataru Kuriyama, Takaji Matsumoto
  • Publication number: 20150105559
    Abstract: Disclosed is a method for producing a compound having an amino group and/or a hydroxyl group from a substrate compound having an atomic group containing CO or CS by eliminating such atomic group. The substrate compound, having an atomic group containing CO or CS (for example, an amide, a carbamate, or the like), is allowed to react with a compound expressed by formula (I) below, at a temperature of 120° C. or lower, preferably in the presence of an ammonium salt, to eliminate such atomic group containing CO or CS. In formula (I) A may not be present, and in a case where A is present, A represents an alkyl group having 1 to 6 carbon atoms. H2N-A—NH2 (I) - - -.
    Type: Application
    Filed: March 4, 2013
    Publication date: April 16, 2015
    Applicant: Kyushu University, National University Corporation
    Inventors: Takashi Ohshima, Hiroyuki Morimoto, Yuhei Shimizu
  • Patent number: 8968701
    Abstract: The invention relates to a process for the production of radiotracers. In particular, this invention relates the isolation of radiotracers with containers filled with a stationary phase.
    Type: Grant
    Filed: July 6, 2010
    Date of Patent: March 3, 2015
    Assignee: Piramal Imaging SA
    Inventors: Holger Siebeneicher, Keith Graham, Mathias Berndt
  • Patent number: 8901352
    Abstract: We have developed a new method for the synthesis of Rasagiline (Formula 1) based on the alkylation of trifluoroacetyl protected aminoindan. This protection enabled us to carry out an alkylation of aminoindan with a high yield and purity under very mild conditions with a wide range of reaction conditions and reagent selection. Considering the ease, purity and high yields of introducing and removal of the trifluoroacetyl group, this approach is a highly practical and economical way for the synthesis of rasagiline or its pharmaceutically acceptable salts.
    Type: Grant
    Filed: January 13, 2011
    Date of Patent: December 2, 2014
    Assignee: Nobel Ilaç Sanayii Ve Ticaret A.S.
    Inventors: Ömer Reis, Hasan Koyuncu, Ilker Esiringu, Yasemin Sahin, H. Ozan Gulcan
  • Patent number: 8835687
    Abstract: Provided is a method for preparing 4,4?-dinitrodiphenylamine (4,4?-DNDPA) in high yield via the NASH reaction using a mixture of a bis-quaternary ammonium base and a base catalyst for the reaction of urea with nitrobenzene, and a method of preparing 4,4?-bis(alkylamino)diphenylamine (4,4?BAADA) in high yield and purity by hydrogenating the resulting 4,4?-DNDPA with a ketone in the presence of hydrogen and hydrogenation catalyst. The catalyst complex used in the present invention allows easy recovery, provides superior alkaline stability and is capable of reducing production cost.
    Type: Grant
    Filed: June 17, 2011
    Date of Patent: September 16, 2014
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Jin-Eok Kim, Seoung-IL Kim, Han Jin Kwag, Sang hee Park
  • Patent number: 8759587
    Abstract: Provided is a method of preparing 4,4?-dinitrodiphenylamine (4,4?-DNDPA) in high yield by reacting 4-nitroaniline with excess nitrobenzene via the NASH reaction, and a method of preparing 4,4?-bis(alkylamino)diphenylamine (4,4?BAADA) in high yield and purity by hydrogenating the resulting 4,4?-DNDPA with a ketone compound in the presence of hydrogen and hydrogenation catalyst. The disclosed process is simple, allows selective preparation of 4,4?-DNDPA without byproducts, and thus allows preparation of 4,4?-BAADA in high yield without a complicated purification procedure.
    Type: Grant
    Filed: June 17, 2011
    Date of Patent: June 24, 2014
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Jin-Eok Kim, Seoung-Il Kim, Han Jin Kwag, Sang hee Park
  • Publication number: 20140163225
    Abstract: There is provided a process for the reduction of one or more amide moieties in a compound comprising contacting the compound with hydrogen gas and a transition metal catalyst in the presence or absence of a base under conditions for the reduction an amide bond. The presently described processes can be performed at low catalyst loading using relatively mild temperature and pressures, and optionally, in the presence or absence of a base or high catalyst loadings using low temperatures and pressures and high loadings of base to effect dynamic kinetic resolution of achiral amides.
    Type: Application
    Filed: July 18, 2012
    Publication date: June 12, 2014
    Applicant: THE GOVERNORS OF THE UNIVERSITY OF ALBERTA
    Inventors: Steven Bergens, Jeremy M. John
  • Publication number: 20140057990
    Abstract: This invention provides a convenient method for converting oximes into enamides. The process does not require the use of metallic reagents. Accordingly, it produces the desired compounds without the concomitant production of a large volume of metallic waste. The enamides are useful precursors to amides and amines. The invention provides a process to convert a prochiral enamide into the corresponding chiral amide. In an exemplary process, a chiral amino center is introduced during hydrogenation through the use of a chiral hydrogenation catalyst. In selected embodiments, the invention provides methods of preparing amides and amines that include the 1,2,3,4-tetrahydro-N-alkyl-1-naphthalenamine or 1,2,3,4-tetrahydro-1-naphthalenamine substructure.
    Type: Application
    Filed: August 1, 2013
    Publication date: February 27, 2014
    Applicant: SUNOVION PHARMACEUTICALS INC.
    Inventors: Hang Zhao, Stefan G. Koenig, Charles P. Vandenbossche, Surendra Singh, Harold Scott Wilkinson, Roger P. Bakale
  • Publication number: 20140046074
    Abstract: The present invention relates to a (2R, 3R)-3-(3-substituted phenyl)-2-methyl n-pentanamide compounds as shown in the formula I and the preparation method thereof, wherein, the substituents are as defined in the specification, the present invention further relates to a use of the above compounds for the preparation of tapentadol II or its pharmaceutically acceptable salt, and the intermediates involved in the preparation process.
    Type: Application
    Filed: January 31, 2012
    Publication date: February 13, 2014
    Inventors: Qiang Zhang, Rongxia Zhang, Guanghui Tian, Jianfeng Li, Fuqiang Zhu, Xiangrui Jiang, Jingshan Shen
  • Publication number: 20140018578
    Abstract: We have developed a new method for the synthesis of Rasagiline (Formula 1) based on the alkylation of trifluoroacetyl protected aminoindan. This protection enabled us to carry out an alkylation of aminoindan with a high yield and purity under very mild conditions with a wide range of reaction conditions and reagent selection. Considering the ease, purity and high yields of introducing and removal of the trifluoroacetyl group, this approach is a highly practical and economical way for the synthesis of rasagiline or its pharmaceutically acceptable salts.
    Type: Application
    Filed: January 13, 2011
    Publication date: January 16, 2014
    Inventors: Ömer Reis, Hasan Koyuncu, Ilker Esiringu, Yasemin Sahin, H. Ozan Gulcan
  • Publication number: 20130281664
    Abstract: The present invention relates to novel Ruthenium catalysts and related borohydride complexes, and the use of such catalysts, inter alia, for (1) hydrogenation of amides (including polyamides) to alcohols and amines; (2) preparing amides from alcohols with amines (including the preparation of polyamides (e.g., polypeptides) by reacting dialcohols and diamines and/or by polymerization of amino alcohols); (3) hydrogenation of esters to alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di-lactones) or polyesters); (4) hydrogenation of organic carbonates (including polycarbonates) to alcohols and hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (5) dehydrogenative coupling of alcohols to esters; (6) hydrogenation of secondary alcohols to ketones; (7) amidation of esters (i.e.
    Type: Application
    Filed: October 11, 2011
    Publication date: October 24, 2013
    Inventors: David Milstein, Ekambaram Balaraman, Chidambaram Gunanathan, Boopathy Gnanaprakasam, Jing Zhang
  • Publication number: 20130172619
    Abstract: Disclosed herein is a method for producing an alcohol and an amine from an amide under an atmosphere of hydrogen with the use of, as a catalyst, a ruthenium complex that is easily prepared, easy to handle, and relatively cheaply obtained. Specifically, the method is a method for producing an alcohol and/or an amine from an amide compound under an atmosphere of hydrogen with the use of as a catalyst, a ruthenium carbonyl complex represented by the following general formula (1): RuXY(CO)(L) (1) wherein X and Y may be the same or different from each other and each represents an anionic ligand and L represents a tridentate aminodiphosphine ligand containing two phosphino groups and a —NH— group.
    Type: Application
    Filed: September 1, 2011
    Publication date: July 4, 2013
    Applicant: TAKASAGO INTERNATIONAL CORPORATION
    Inventors: Osamu Ogata, Wataru Kuriyama, Takaji Matsumoto
  • Patent number: 8299241
    Abstract: The present invention provides processes and intermediates for the preparation of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine and salts thereof which are useful as serotonin-2C (5-HT2C) receptor agonists for the treatment of, for example, obesity.
    Type: Grant
    Filed: December 4, 2007
    Date of Patent: October 30, 2012
    Assignee: Arena Pharmaceuticals, Inc.
    Inventors: Tawfik Gharbaoui, Sagun K. Tandel, You-An Ma, Marlon Carlos, John Robert Fritch
  • Patent number: 8263808
    Abstract: The invention relates to a method for removing an alkyl sulfonyl or aryl sulfonyl protecting group from a primary or secondary amine by contacting an alkyl sulfonamide or an aryl sulfonamide with a Stage 0 or Stage I alkali metal-silica gel material in the presence of a solid proton source under conditions sufficient to form the corresponding amine. The invention also relates to a method for removing an alkyl sulfonyl or aryl sulfonyl protecting group from a primary or secondary amine by a) reacting an alkyl sulfonamide or an aryl sulfonamide with a Stage 0 or Stage I alkali metal-silica gel material, and b) subsequently reacting the reaction product from step a) with an electrophile or a proton source. Preferred Stage 0 or Stage I alkali metal-silica gel materials include Na, K2Na, and Na2K.
    Type: Grant
    Filed: February 13, 2007
    Date of Patent: September 11, 2012
    Assignee: SiGNa Chemistry, Inc.
    Inventors: Michael Lefenfeld, James L. Dye, Partha Nandi, James Jackson
  • Publication number: 20120184749
    Abstract: The invention relates to a process for the production of radiotracers. In particular, this invention relates the isolation of radiotracers with containers filled with a stationary phase.
    Type: Application
    Filed: July 6, 2010
    Publication date: July 19, 2012
    Applicant: BAYER PHARMA AKTIENGESELLSCHAFT
    Inventors: Holger Siebeneicher, Keith Graham, Mathias Berndt
  • Publication number: 20120157713
    Abstract: Provided is a method for preparing 4,4?-dinitrodiphenylamine (4,4?-DNDPA) in high yield via the NASH reaction using a mixture of a bis-quaternary ammonium base and a base catalyst for the reaction of urea with nitrobenzene, and a method of preparing 4,4?-bis(alkylamino)diphenylamine (4,4?BAADA) in high yield and purity by hydrogenating the resulting 4,4?-DNDPA with a ketone in the presence of hydrogen and hydrogenation catalyst. The catalyst complex used in the present invention allows easy recovery, provides superior alkaline stability and is capable of reducing production cost.
    Type: Application
    Filed: June 17, 2011
    Publication date: June 21, 2012
    Applicant: KOREA KUMHO PETROCHEMICAL CO., LTD.
    Inventors: Jin-Eok Kim, Seoung-IL Kim, Han Jin Kwag, Sang hee Park
  • Publication number: 20120157714
    Abstract: Provided is a method of preparing 4,4?-dinitrodiphenylamine (4,4?-DNDPA) in high yield by reacting 4-nitroaniline with excess nitrobenzene via the NASH reaction, and a method of preparing 4,4?-bis(alkylamino)diphenylamine (4,4?BAADA) in high yield and purity by hydrogenating the resulting 4,4?-DNDPA with a ketone compound in the presence of hydrogen and hydrogenation catalyst. The disclosed process is simple, allows selective preparation of 4,4?-DNDPA without byproducts, and thus allows preparation of 4,4?-BAADA in high yield without a complicated purification procedure.
    Type: Application
    Filed: June 17, 2011
    Publication date: June 21, 2012
    Applicant: KOREA KUMHO PETROCHEMICAL CO., LTD.
    Inventors: Jin-Eok Kim, Seoung-IL Kim, Han Jin Kwag, Sang hee Park
  • Publication number: 20120071651
    Abstract: The present invention relates to processes for preparing enantiomerically pure cyclopropyl amine derivatives and salts thereof; the chiral intermediates such as the chiral salts are useful for the preparation of such chiral compounds and salts; pharmaceutical compositions comprising the compounds and salts; and method of using such compositions. The chiral cyclopropyl amine derivatives are useful for binding to histamine H3 receptor sites and for providing therapeutic agents for histamine H3 mediated disease.
    Type: Application
    Filed: September 14, 2011
    Publication date: March 22, 2012
    Applicant: ABBOTT LABORATORIES
    Inventors: Yi-Yin Ku, Timothy A. Grieme, Jeffrey M. Kallemeyn, Mathew M. Mulhern
  • Publication number: 20110295038
    Abstract: A process for the preparation of substituted 1-aminomethyl-2-phenyl-cyclohexane compounds.
    Type: Application
    Filed: May 27, 2011
    Publication date: December 1, 2011
    Applicant: Gruenenthal GmbH
    Inventors: Joerg HOLENZ, Helmut Heinrich Buschmann
  • Publication number: 20110105698
    Abstract: This invention provides alignment materials for liquid crystal display device of vertical alignment mode and methods for the preparation of the same, and more particularly, it provides diaminobenzene derivatives represented by the following formula 1 (shown in description), capable of aligning liquid crystal in uniform and vertical way and remarkably improving clarity and solubility against organic solvents, methods for the preparation of the same and liquid crystal alignment films using the same.
    Type: Application
    Filed: February 9, 2007
    Publication date: May 5, 2011
    Applicant: DONGJIN SEMICHEM Co., Ltd.
    Inventors: Jin wook Choi, Dal bong Seo, Jae cheol Park, Yong bae Kim
  • Publication number: 20110034461
    Abstract: The invention relates to novel compounds of formula I where R1, R2, R3, R4, R5, R9, Ar, Q1, Q2 and Q3 are each as defined below. The compounds of the formula I have antithrombotic activity and inhibit especially protease-activated receptor 1 (PAR1). The invention further relates to a process for preparing the compound of the formula I and to the use thereof as a medicament.
    Type: Application
    Filed: August 5, 2010
    Publication date: February 10, 2011
    Applicant: sanofi-aventis
    Inventors: Uwe HEINELT, Volkmar WEHNER, Matthias HERRMANN, Karl SCHOENAFINGER, Henning STEINHAGEN
  • Publication number: 20100331578
    Abstract: There are provided a 4-(trichloromethylthio)aniline represented by the general formula (II): wherein R1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R2 each independently represents a halogen atom, an alkyl group having 1 to 3 carbon atoms, or a perfluoroalkyl group having 1 to 3 carbon atoms, R3 represents a formyl group, an acetyl group, or a trifluoroacetyl group, and m represents an integer of 0 to 4, a method for producing the same, and a method for producing a 4-(trifluoromethylthio)aniline derivative using the 4-(trichloromethylthio)aniline. It becomes possible to produce a 4-(trifluoromethylthio)aniline with a high yield by using raw materials that can easily be obtained industrially and using general purpose production facilities.
    Type: Application
    Filed: July 1, 2008
    Publication date: December 30, 2010
    Inventors: Yoshitomo Tohyama, Kengo Kanematsu
  • Publication number: 20100305316
    Abstract: The present invention provides processes and intermediates for the preparation of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine and salts thereof which are useful as serotonin-2C (5-HT2C) receptor agonists for the treatment of, for example, obesity.
    Type: Application
    Filed: December 4, 2007
    Publication date: December 2, 2010
    Inventors: Tawfik Gharbaoui, Sagun K. Tandel, You-An Ma, Marlon Carlos, John Robert Fritch
  • Patent number: 7838582
    Abstract: A hyperdispersant for use in a fluorocarbon coating composition is disclosed. The fluorocarbon coating composition generally comprises a fluorocarbon resin, a binder resin, a cross-linking agent, and the hyperdispersant. The hyperdispersant comprises the reaction product of a polyglycidyl oligomer and at least one amino compound. The polyglycidyl oligomer comprises a carbon chain having from 1 to 25 carbon atoms with at least one of an internal ether linkage and an internal ester linkage and comprises a plurality of epoxy groups. The at least one amino compound has a cyclic, heterocyclic, alkyl, or heteroalkyl structure substituted with at least one primary or secondary amine group for reacting with and opening at least one of the epoxy groups.
    Type: Grant
    Filed: March 12, 2007
    Date of Patent: November 23, 2010
    Assignee: PPG Industries Ohio, Inc.
    Inventors: James L. Anderson, David Lindow, Donald J. Algrim
  • Patent number: 7705185
    Abstract: Alkylated antioxidant macromolecules are represented by Structural Formula 1: wherein the variables are described herein. Also included are methods of making the molecules and methods of using the molecules as antioxidants.
    Type: Grant
    Filed: March 24, 2006
    Date of Patent: April 27, 2010
    Assignee: Polnox Corporation
    Inventors: Rajesh Kumar, Ashok L. Cholli
  • Patent number: 7638652
    Abstract: Provided is a one-step efficient production method for an ?,?-difluoroamine of a general formula (1) below from an amide compound. The method is an economical method capable of producing the intended ?,?-difluoroamine at high yield by reacting a starting amide compound with carbonyl fluoride and/or oxalyl fluoride under a specific condition.
    Type: Grant
    Filed: July 11, 2007
    Date of Patent: December 29, 2009
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takafumi Yoshimura, Toshio Hidaka, Norio Fushimi
  • Publication number: 20090312571
    Abstract: The present invention relates to a process for the preparation of (2S,3S)-3-amino-N-cyclopropyl-2-hydroxyalkanamides as well as novel compounds prepared or used in the process.
    Type: Application
    Filed: June 12, 2009
    Publication date: December 17, 2009
    Applicant: ViroBay, Inc.
    Inventor: Jeffrey Dener
  • Publication number: 20090286968
    Abstract: Disclosed are 2-quinoxalinol salen compounds and in particular 2-quinoxalinol salen Schiff-base ligands. The disclosed 2-quinoxalinol salen compounds may be utilized as ligands for forming complexes with cations, and further, the formed complexes may be utilized as catalysts for oxidation reactions. The disclosed 2-quinoxalinol salen compounds also may be conjugated to solid supports and utilized in methods for selective solid-phase extraction or detection of cations.
    Type: Application
    Filed: April 24, 2009
    Publication date: November 19, 2009
    Applicant: Auburn University
    Inventors: Anne E. V. Gorden, Xianghong Wu
  • Patent number: 7592488
    Abstract: The present invention relates to a method of preparing optically active amines and chiral amines prepared thereby. The method includes reacting an amine compound, a metal catalyst, a biocatalyst including a lipase, and an acyl donor compound in an organic solvent to obtain a chiral amide compound, and then hydrolyzing the chiral amide compound to obtain a chiral amine.
    Type: Grant
    Filed: August 18, 2007
    Date of Patent: September 22, 2009
    Assignee: Postech Academy-Industry Foundation
    Inventors: Mahn-Joo Kim, Jaiwook Park, Won-Hee Kim, Kiwon Han, Yoon Kyung Choi
  • Patent number: 7585930
    Abstract: A method of decomposing a polycarbonate with water in a supercritical or subcritical state. A high-purity dihydroxy compound which is a constituent component of the polycarbonate can be recovered at a high yield by this decomposition method. This decomposition method is environment-friendly because it does not use an organic solvent, easy to be carried out, has a high decomposition rate and rarely causes a side reaction.
    Type: Grant
    Filed: February 8, 2005
    Date of Patent: September 8, 2009
    Assignee: Teijin Limited
    Inventors: Mai Kitahara, Masumi Hirata, Tetsuo Ban, Toru Sawaki
  • Publication number: 20090203910
    Abstract: Organic compounds having nitrogen atoms protected with t-butoxycarbonyl are effectively deprotected by heating in a fluorinated alcohol solution.
    Type: Application
    Filed: December 11, 2008
    Publication date: August 13, 2009
    Inventors: Jason Chi-Chung Choy, Saul Jaime-Figueroa, Joseph M. Muchowski, Paul J. Wagner
  • Publication number: 20090149549
    Abstract: This invention provides a convenient method for converting oximes into enamides. The process does not require the use of metallic reagents. Accordingly, it produces the desired compounds without the concomitant production of a large volume of metallic waste. The enamides are useful precursors to amides and amines. The invention provides a process to convert a prochiral enamide into the corresponding chiral amide. In an exemplary process, a chiral amino center is introduced during hydrogenation through the use of a chiral hydrogenation catalyst. In selected embodiments, the invention provides methods of preparing amides and amines that include the 1,2,3,4-tetrahydro-N-alkyl-1-naphthalenamine or 1,2,3,4-tetrahydro-1-naphthalenamine substructure.
    Type: Application
    Filed: March 30, 2007
    Publication date: June 11, 2009
    Inventors: Hang Zhao, Stefan G. Koenig, Charles P. Vandenbossche, Surendra Singh, H. Scott Wilkinson, Roger P. Bakale
  • Publication number: 20080293971
    Abstract: A process for synthesis of R-(?)-N,?-Dimethylphenethylamine (Levmetamfetamine, formula I), or S-(+)-N,?-Dimethyl phenethylamine (Methamphetamine, formula II), from d-ephedrine of formula III or l-ephedrine formula IV, the process comprising the steps of (a) acylating the d- or l-ephedrine base of formula III or formula IV with an acylating agent to make a reaction mixture containing a N-acylated ephedrines of formula V or formula VI; (b) deoxygenation of N-acylated ephedrines to make the compound of the formula VII or Formula VIII by using Raney Nickel catalyst; and (c) acid hydrolysis of the above deoxygenated products to get the levmetamfetamine or methamphetamine.
    Type: Application
    Filed: December 22, 2004
    Publication date: November 27, 2008
    Applicant: EMMELLEN BIOTECH PHARMACEUTICALS LIMITED
    Inventors: Subrahmanyam Gollapudy, Ramana Nittala Venkata
  • Patent number: 7456320
    Abstract: A process for the preparation of optically active substituted alpha-amino-indane derivatives of formula (I), which include: an asymmetric hydrogenation reaction of an en-amide derivative of formula (III) in presence of hydrogen and an optically active catalyst, in order to obtain an amide derivative of formula (II), a hydrolysis reaction of the amide derivative of formula (II) obtained in the previous step, in order to obtain optically active substituted alpha-amino-indane derivatives of formula (I).
    Type: Grant
    Filed: February 21, 2005
    Date of Patent: November 25, 2008
    Assignee: ZaCh System
    Inventors: Blandine Bertrand, Sylvie Blanchet, Alain Burgos, Juliette Martin, Florence Perrin, Sonia Roussiasse, Yvon Derrien
  • Publication number: 20080139846
    Abstract: A process for preparing a compound of formula I wherein R1 is H, C1-6alkyl, C2-6alkenyl, C1-6alkoxy, —OH, or amino; and n, m, and p are independently selected from 0, 1 and 2; which process comprises reacting a compound of formula II, by combining it with a reducing agent in a suitable solvent into a reaction mixture.
    Type: Application
    Filed: August 28, 2007
    Publication date: June 12, 2008
    Applicant: ASTRAZENECA AB
    Inventors: Lars Hansson, Martin Hedberg
  • Publication number: 20080039633
    Abstract: The invention relates to a process for preparing arylamines or heteroarylamines or arylamides or heteroarylamides by cross-coupling of primary or secondary amines or amides with substituted aryl or heteroaryl compounds in the presence of a Brønsted base and a catalyst or precatalyst, wherein the catalyst comprises a) a transition metal, a complex, a salt or a compound of this transition metal selected from the group consisting of Ni, Pd and b) at least one ligand selected from the group consisting of bidentate bis(phosphino)alkanediyls having the following formula in a solvent or solvent mixture, where the radicals Ar1-4 are each, independently of one another, an aryl or heteroaryl substituent selected from the group consisting of phenyl, naphthyl, pyridyl and biphenyl or Ar1-4 is hydrogen, C1-, C2-alkyl, straight-chain, branched or cyclic C3-C8-alkyl, and L is an alkanediyl bridge which has from 1 to 20 carbon atoms.
    Type: Application
    Filed: August 9, 2007
    Publication date: February 14, 2008
    Inventors: Joerg JUNG, Andreas Meudt, Bernd Wilheilm Lehnemann
  • Patent number: 7329780
    Abstract: Provided is a method of preparing an optically pure compound having formula 1 or its salts. The method includes: reacting (R)-2-(4-methoxy-3-aminosulfonyl-phenyl)-1 -methylethylamine or its salts with a compound selected from the group consisting of chloroacetic acid, bromoacetic acid, fluoroacetic acid, iodoacetic acid, ?-halogenoacetic acid anhydride, and ?-halogenoacetyl halide in the presence of a base or an acylating agent.
    Type: Grant
    Filed: December 9, 2004
    Date of Patent: February 12, 2008
    Assignee: CJ Corporation
    Inventors: Seong Hwan Cho, Dong Kwon Lim, Kwang Hyeg Lee, Yong Sik Youn, Choong Sil Park
  • Publication number: 20070249868
    Abstract: A process for the preparation of 4-hydroxyalkylamino-2-nitro-anisoles of the general formula (I) wherein m is 2 or 3; by reaction of a 4-halogeno-3-nitro-aniline of formula (II) with a chloroalkyl-chloroformate of formula (III), alkaline ring closure of the resulting carbamate and nucleophilic replacement of the halogeno atom by a methoxy group to form a derivative of formula (IV), and finally ring opening of the resulting cyclic carbamate by treatment with methanolic alkali metal hydroxide, followed by neutralization with inorganic or organic acids, wherein the complete reaction is executed in a non-aqueous medium; as well as process for the preparation of 2-amino-4-hydroxyalkylamino-anisoles of formula (V).
    Type: Application
    Filed: April 19, 2007
    Publication date: October 25, 2007
    Inventors: Otto Gottel, Emmanuel Morand, Hans-Jurgen Braun
  • Patent number: 7205440
    Abstract: The invention relates to a special two-step method for producing amines on the basis of amides by reacting them with halides or hypohalites in an aqueous solution in a Hofmann degradation reaction. The amide is reacted in an alkaline solution and/or suspension with halides or hypohalites and the reaction mixture obtained in step 1 is added to an aqueous alkaline solution having a temperature of at least 40° C.
    Type: Grant
    Filed: December 17, 2002
    Date of Patent: April 17, 2007
    Assignee: Lanxess Deutschland GmbH
    Inventors: Peter Wenzl, Friedrich Dürrholz, Herbert V. Diehl
  • Patent number: 7154005
    Abstract: This invention describes the reaction of an alpha fluoroalkyl ketone with a bis(trialkylsilyl)amide to give a stable N-trialkylsilyl imine. Treatment of the N-trialkylsilyl imine with an alcohol leads to solvolysis of the trialkylsilyl group and yields a stable mixture of an aminal and an imine in high yield. Catalytic reduction of this mixture, or of the individual components, in the presence of a chiral catalyst leads to a fluoroalkyl amine with high enantioselectivity and high yield.
    Type: Grant
    Filed: September 7, 2005
    Date of Patent: December 26, 2006
    Assignee: Merck Frosst Canada, Ltd.
    Inventors: Paul O'Shea, Francis Gosselin
  • Patent number: 6933410
    Abstract: A process for preparing 5,6-diethyl-2,3-dihydro-1H-inden-2-amine and acid addition salts thereof from 2-aminoindan. The process comprises protecting the amino group of 2-aminoindan, acetylating the ring in the protected compound, reducing the acetyl group to ethyl to form a monoethyl derivative, acetylating the monoethyl derivative, reducing the acetyl group to form a diethyl derivative, deprotecting the latter by hydrolysis and recovering the product in free or salt form. The process does not use deleterious Grignard reagents or nitrites such as isoamyl nitrite, and provides high regioselectivity and high yield of 5,6-diethyl-2,3-dihydro-1H-inden-2-amine. In addition, the process uses acetyl halide as both a reactant and a solvent.
    Type: Grant
    Filed: February 14, 2003
    Date of Patent: August 23, 2005
    Assignee: Novartis AG
    Inventors: Mahavir Prashad, Bin Hu, Olivier Lohse
  • Patent number: 6835831
    Abstract: Disclosed is a method of preparing a composition comprising a compound represented Structural Formula (I): The method comprises the step of reacting an aldehyde compound R10CHO with an isonitrile compound represented by Structural Formula (II):
    Type: Grant
    Filed: November 26, 2002
    Date of Patent: December 28, 2004
    Assignee: Genzyme Corporation
    Inventor: Bradford H. Hirth
  • Publication number: 20040126720
    Abstract: The present invention relates to a silver halide color photographic light-sensitive material wherein at least one of light-sensitive silver halide emulsion layers includes a silver halide emulsion having a silver chloride content of at least 95 mol % and a silver iodide content of 0.05 mol % to 0.75 mol % and/or a silver bromide content of 0.05 mol % to 4.
    Type: Application
    Filed: December 18, 2003
    Publication date: July 1, 2004
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventors: Atsushi Matsunaga, Tadashi Inaba, Shinichi Ichikawa
  • Patent number: 6710209
    Abstract: The present invention relates to a method of preparation for compounds of Formula 23: wherein R3, R4, R5, R6, R7, and W are as defined herein.
    Type: Grant
    Filed: March 7, 2002
    Date of Patent: March 23, 2004
    Assignee: Pfizer Inc
    Inventor: Bingwei V. Yang
  • Patent number: 6683216
    Abstract: Disclosed is a process for the preparation of amines by continuously feeding a carboxamide, aqueous alkaline hypohalite, and aqueous alkaline hydroxide to a first reaction zone to form a N-halocarboxamide, measuring the concentration of at least one reaction component in the effluent from the first reaction zone, and using the result of that measurement to control the feed rate of at least one of the feed components of to achieve at least 90% conversion of the carboxamide in the first reaction zone. The effluent from the first reaction zone is fed continuously to a second reaction zone where it further reacts to form an aqueous solution of an amine. The effluent from the second reaction zone may be fed continuously to a distillation column. The process is particularly useful for the preparation of cyclopropylamine.
    Type: Grant
    Filed: November 6, 2002
    Date of Patent: January 27, 2004
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Norma Lindsey Buchanan, Elizabeth Celia Sharkey, Daniel Latham Terrill, Steven Paul Bellner
  • Patent number: 6673960
    Abstract: A process for working up distillation residues from the synthesis of tolylene diisocyanate by reaction of the distillation residues with water comprises reacting the TDI distillation residues with water in a continuous or semicontinuous process in a backmixed reactor in the presence of hydrolysate.
    Type: Grant
    Filed: December 14, 2000
    Date of Patent: January 6, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Volkmar Schwarz, Markus Maurer, Michael Sander, Eckhard Ströfer, Rene Leuthold, Burghard Hantel, Siegfried Richter, Jörg Therre
  • Publication number: 20040002614
    Abstract: In the process of the present invention, xylylenediamine and/or cyanobenzylamine is produced by a catalytic liquid-phase hydrogenation of a phthalonitrile compound. The liquid-phase hydrogenation is performed by controlling the concentration of a benzamide compound to a specific level or lower. In a preferred embodiment, the concentration of a benzoic acid compound is further controlled to a specific level or lower. By the process, xylylenediamine and/or cyanobenzylamine is produced at high yields and the catalyst life is prolonged.
    Type: Application
    Filed: June 30, 2003
    Publication date: January 1, 2004
    Inventors: Kazuhiko Amakawa, Takuji Shitara
  • Patent number: 6660773
    Abstract: A process for preparing 6-hydroxy-3,4-dihydroquinolinone by intramolecular Friedel-Crafts alkylation of N-(4-methoxyphenyl)-3-chloropropionamide in which an equivalent of N-(4-methoxyphenyl)-3-chloropropionamide is contacted with a Lewis acid in DMSO or a high boiling amide or amine at an elevated temperature of from about 150° C. to about 220° C. is provided. The process produces 6-HQ in high yield and a high state of purity such that it may be used in subsequent reactions toward the preparation of cilostazol without intermediate purification. A process for preparing cilostazol from 6-hydroxy-3,4-dihydroquinolinone prepared by the process and improved processes for preparing N-(4-methoxyphenyl)-3-chloropropionamide are also provided.
    Type: Grant
    Filed: March 8, 2002
    Date of Patent: December 9, 2003
    Assignee: Teva Pharmaceutical Industries, Ltd.
    Inventors: Marioara Mendelovici, Gideon Pilarsky, Tamar Nidam, Ben-Zion Dolitzky
  • Patent number: 6635783
    Abstract: Bicyclic amino alcohols, whose amino group and hydroxy group are bonded in positions 1,3 adjacent to the bridge, for example are valuable ligands for metal complexes of the d-8 metals of the periodic table of elements. The metal complexes in question are catalysts or catalyst precursors for the asymmetric hydrogenation or asymmetric transfer hydrogenation with hydrogen donors of prochiral organic compounds with carbon double bonds or carbon/hetero atom double bonds, for example ketones and imines.
    Type: Grant
    Filed: March 6, 2001
    Date of Patent: October 21, 2003
    Assignee: Solvias AG
    Inventor: Peter Herold
  • Patent number: 6552222
    Abstract: A process for the preparation of racemic amino acids, characterized in that an acylamino acid of the formula R1—CH(NH—CO—R2)COOH wherein R1 is hydrogen, a linear, branched or cyclic alkyl that has from 1 to 7 carbon atoms and that may contain substituents such as a hydroxyl, alkyloxy or alkylthio group; and R2 is a hydrogen atom or an alkyl having from 1 to 3 carbon atoms; is heated in the presence of water, in a pressure-resistant vessel, to a temperature in the range from 110° C. to 220° C. and is hydrolyzed.
    Type: Grant
    Filed: August 13, 2001
    Date of Patent: April 22, 2003
    Assignee: Degussa AG
    Inventors: Klaus Huthmacher, Christoph Weckbecker, Horst Weigel