Preparing Directly From Cyano Containing Compound Patents (Class 564/124)
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Patent number: 9187409Abstract: The present invention provides novel process for the preparation of renin inhibitor Aliskiren or its derivatives, and its pharmaceutically acceptable salts. The present invention also provides novel intermediates used in the preparation of Aliskiren.Type: GrantFiled: October 19, 2011Date of Patent: November 17, 2015Assignee: Mylan Laboratories LimitedInventors: Rama Shankar, Vadali Lakshmana Rao, Palla Vijay Kumar, Saidugari Swamy, Dasari Srinivasa Rao, Srinivasa Rao Potla, Mittapelly Nagaraju, Jaldu Ravikanth, Vijaya Krishna Ravi, Seshadri Rao Manukonda, Dandala Ramesh
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Patent number: 8853449Abstract: Process for the industrial synthesis of the compound of formula (I)Type: GrantFiled: January 4, 2012Date of Patent: October 7, 2014Assignee: Les Laboratoires ServierInventors: Samir Zard, Béatrice Sire, Mehdi Boumediene
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Publication number: 20140296354Abstract: Described herein are the one-pot synthesis and characterization of a library of low molecular weight peptoid compounds that are able to form gels at room temperature. The compounds are synthesized from biologically-based starting materials, are biocompatible, and are resistant to degradation by proteases and peptidases.Type: ApplicationFiled: April 1, 2014Publication date: October 2, 2014Applicant: OLD DOMINION UNIVERSITY RESEARCH FOUNDATIONInventors: Guijun WANG, Hari P. R. MANGUNURU
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Patent number: 8802896Abstract: Disclosed is a polyether compound which is useful as a curing agent or the like, a curing agent using the compound and a producing method of the compound. The polyether compound of the present invention is represented by the following general formula (1). (In the formula, R1 represents a hydrogen atom or a methyl group and R2 represents a hydrogen atom or —C(?O)—C(R3)?CH2. R3 represents a hydrogen atom or a methyl group. R1, R2 and R3 may be the same as or different from each other.Type: GrantFiled: September 30, 2013Date of Patent: August 12, 2014Assignee: FUJIFILM CorporationInventors: Akihito Amao, Hirotaka Kitagawa
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Patent number: 8779199Abstract: The present invention relates to the intermediate compounds for preparation of agomelatine, as well as the preparation methods thereof The intermediate of the present invention for preparation of agomelatine is compound A as shown in the following formula. Also provided are two novel intermediate compounds. When we use these new intermediate compounds to prepare agomelatine, it is simple to manipulate, well-controlled and with high purity, without complicated operations such as rectification and column chromatography separation, and suitable for industrial production. Meanwhile, the preparation methods of the two new intermediates themselves is simple and high yield, only using the most commonly-used 7-methoxy-tetralone as original starting material and undergoing one step of reaction to obtain the intermediates, followed by one more step of converting the intermediate compounds to desired product agomelatine.Type: GrantFiled: June 8, 2011Date of Patent: July 15, 2014Assignee: Les Laboratoires ServierInventors: Peng Zhang, Yu Huang, Zhedong Yuan, Hanbin Shan, Xiong Yu
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Publication number: 20140186272Abstract: The present invention provides synthetic routes for preparing various isomers of cyclohexane-based coolants, such as menthyl esters and menthanecarboxamide derivatives, in particular those substituted at the amide nitrogen, for example with an aromatic ring or aryl moiety. Such structures have high cooling potency and long lasting sensory effect, which make them useful in a wide variety of consumer products. One synthetic route involves a copper catalyzed coupling of a primary menthanecarboxamide with an aryl halide, such reaction working best in the presence of potassium phosphate and water. Using this synthetic route, specific isomers can be prepared including the menthanecarboxamide isomer having the same configuration as l-menthol and new isomers such as a neoisomer having opposite stereochemistry at the carboxamide (C-1) position. The neoisomer unexpectedly has potent and long lasting cooling effect.Type: ApplicationFiled: March 5, 2014Publication date: July 3, 2014Applicant: The Procter & Gamble CompanyInventors: Kenneth Edward YELM, Gregory Mark BUNKE, John Christian HAUGHT
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Patent number: 8759580Abstract: The invention relates to a process for preparing aminoalkanamides by reacting cyanoalkanoic esters with a) ammonia or an amine and b) hydrogen in the presence of a catalyst, the reaction with component b) being started simultaneously or not later than a maximum of 100 minutes after commencement of the reaction of the cyanoalkanoic ester with component a).Type: GrantFiled: December 15, 2006Date of Patent: June 24, 2014Assignee: BASF SEInventors: Martin Ernst, Andreas Kusche, Gunnar Heydrich, Horst Grafmans, Holger Evers, Johann-Peter Melder, Harald Meiβner, Torsten Freund
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Publication number: 20140142337Abstract: The present invention relates to 1-amino-2-vinylcyclopropane carboxylic acid amide or a salt thereof. By obtaining optically active 1-amino-2-vinylcyclopropane carboxylic acid amide or a salt thereof by hydrolyzing optically active 1-amino-2-vinylcyclopropane carbonitrile or a salt thereof according to the production method of the present invention, 1-amino-2-vinylcyclopropane carboxylic acid amide or a salt thereof, which is useful as a pharmaceutical/agrochemical intermediate, can be easily obtained. The present invention is capable of providing a substrate to be subjected to optical resolution, which enables the production of optically active 1-amino-2-vinylcyclopropane carboxylic acid, which is widely used as a raw material for pharmaceutical and agrochemical products and is especially important as an intermediate for therapeutic agents for hepatitis C, inexpensively with high purity and high yield.Type: ApplicationFiled: June 18, 2012Publication date: May 22, 2014Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventor: Masahiro Matsumoto
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Patent number: 8604241Abstract: The present invention relates to a method for synthesizing a pharmaceutically acceptable acid addition salt of (1S, 2R)-milnacipran comprising the following successive steps: (a) reaction of phenylacetonitrile and of (R)-epichlorhydrin in the presence of a base containing an alkaline metal, followed by a basic treatment, and then by an acid treatment in order to obtain a lactone; (b) reaction of said lactone with MNEt2, wherein M represents an alkaline metal, or with NHEt2 in the presence of a Lewis acid-amine complex, in order to obtain an amide-alcohol; (c) reaction of said amide-alcohol with thionyl chloride in order to obtain a chlorinated amide; (d) reaction of said chlorinated amide with a phthalimide salt in order to obtain a phthalimide derivative; (e) hydrolysis of the phthalimide group of said phthalimide derivative in order to obtain (1S, 2R)-milnacipran, and (f) salification of (1S, 2R)-milnacipran in a suitable solvent system in the presence of a pharmaceutically acceptable acid.Type: GrantFiled: January 29, 2010Date of Patent: December 10, 2013Assignee: Pierre Fabre MedicamentInventors: Marc Nicolas, Paul Hellier, Catherine Diard, Laurent Subra
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Publication number: 20130289307Abstract: Process for the industrial synthesis of the compound of formula (I)Type: ApplicationFiled: January 4, 2012Publication date: October 31, 2013Applicant: Les Laboratoires ServierInventors: Samir Zard, Béatrice Sire, Mehdi Boumediene
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Publication number: 20130267738Abstract: The present invention relates to the intermediate compounds for preparation of agomelatine, as well as the preparation methods thereof. The intermediate of the present invention for preparation of agomelatine is compound A as shown in the following formula. Also provided are two novel intermediate compounds. When we use these new intermediate compounds to prepare agomelatine, it is simple to manipulate, well-controlled and with high purity, without complicated operations such as rectification and column chromatography separation, and suitable for industrial production. Meanwhile, the preparation methods of the two new intermediates themselves is simple and high yield, only using the most commonly-used 7-methoxy-tetralone as original starting material and undergoing one step of reaction to obtain the intermediates, followed by one more step of converting the intermediate compounds to desired product agomelatine.Type: ApplicationFiled: June 8, 2011Publication date: October 10, 2013Applicant: LES LABORATORIES SERVIERInventors: Peng Zhang, Yu Huang, Zhedong Yuan, Hanbin Shan, Xiong Yu
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Publication number: 20130216486Abstract: The present invention provides synthetic routes for preparing various isomers of cyclohexane-based coolants, such as menthyl esters and menthanecarboxamide derivatives, in particular those substituted at the amide nitrogen, for example with an aromatic ring or aryl moiety. Such structures have high cooling potency and long lasting sensory effect, which make them useful in a wide variety of consumer products. One synthetic route involves a copper catalyzed coupling of a primary menthanecarboxamide with an aryl halide, such reaction working best in the presence of potassium phosphate and water. Using this synthetic route, specific isomers can be prepared including the menthanecarboxamide isomer having the same configuration as l-menthol and new isomers such as a neoisomer having opposite stereochemistry at the carboxamide (C-1) position. The neoisomer unexpectedly has potent and long lasting cooling effect.Type: ApplicationFiled: March 20, 2013Publication date: August 22, 2013Applicant: The Procter & Gamble CompanyInventor: The Procter & Gamble Company
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Patent number: 8426642Abstract: The invention relates to a method for isolating concentrated paraffin sulfonic acids from reaction mixtures that are produced during the sulfoxidation of n-paraffins, from which a major part of the sulfuric acid and the paraffin was removed by phase separation and which contain, in addition to the free paraffin sulfonic acids, n-paraffins, water and optionally minor amounts of sulfuric acids. The method according to the invention is characterized by removing paraffin and optionally residual water by vacuum distillation. The paraffin sulfonic acids obtained by distillation have a content of more than 85% by weight of the active substance. The material is pale, odorless and low in sulfuric acid and paraffin.Type: GrantFiled: April 29, 2008Date of Patent: April 23, 2013Assignee: Clariant Finance (BVI) LimitedInventors: Gerd Reinhardt, Peter Naumann, Lars Cuypers
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Publication number: 20130035322Abstract: Gold (I) hydroxide complexes of the form Z-Au-OH and digold complexes of the form Z—Au-(?OH)—Au—Z where groups Z are two electron donors are provided. The groups Z may be carbenes, for example nitrogen containing heterocyclic carbenes (NHCs), phosphines or phosphites. The complexes can be used as catalysts, for example in reactions such as hydration of nitriles, skeletal arrangement of enynes, alkoxycyclisation of enynes, alkyne hydration, the Meyer-Shuster reaction, 3,3? rearrangement of allylic acetates, cyclisation of propargylic acetates, Beckman rearrangements and hydroamination. The complexes can be used in medicine, for example in the treatment of cancer.Type: ApplicationFiled: March 2, 2011Publication date: February 7, 2013Applicant: University Court of The University of St. AndrewsInventor: Steven P. Nolan
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Patent number: 8329947Abstract: Process for the industrial synthesis of the compound of formula (I)Type: GrantFiled: August 3, 2009Date of Patent: December 11, 2012Assignee: Les Laboratoires ServierInventors: Pascal Bontempelli, Xavier Jalenques, Jerome-Benoit Starck, Jean-Pierre Sery
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Patent number: 8212075Abstract: Disclosed is a method for preparing a compound of Formula 1 comprising contacting a compound of Formula 2 with at least one alkali metal cyanide of Formula 3 and a compound of Formula 4. wherein R1 is NHR3 or OR4; R2 is CH3 or Cl; R3 is H, C1-C4 alkyl, cyclopropyl, cyclopropylcyclopropyl, cyclopropylmethyl or methylcyclopropyl; R4 is H or C1-C4 alkyl; X is Br, Cl or I; and R5, R6, R7, R8, R9 and R10 are as defined in the disclosure. Also disclosed is a method for preparing a compound of Formula 4 wherein R9 and R10 together are a cycloalkadiene bidentate ligand, comprising contacting a compound of Formula 5 wherein Y is Cl, Br or I, with a cycloalkadiene bidentate ligand, at least one metal reducing agent and a nitrile solvent.Type: GrantFiled: November 7, 2008Date of Patent: July 3, 2012Assignee: E.I. du Pont de Nemours and CompanyInventors: Vladimir Grushin, Albert Loren Casalnuovo
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Patent number: 8129560Abstract: A process for the preparation of a compound of formula (I), the process comprising: (i) the reaction of a compound of formula (III), with a compound of formula (IV) to give a compound of formula (II), and (ii) the reaction of the compound of formula (II) with a leaving group, to give the compound of formula (I).Type: GrantFiled: August 8, 2006Date of Patent: March 6, 2012Assignee: Syngenta Crop Protection, Inc.Inventors: Martin Charles Bowden, Thomas Aitcheson Clark, Fanny Giordano, Beat Jau, Hans-Dieter Schneider, Gottfried Seifert, Martin Zeller, Dominik Faber, Juerg Wiss
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Publication number: 20110295035Abstract: A method for producing a phenylacetamide compound represented by formula (1): wherein Q represents a hydrogen atom or a halogen atom, R2 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R4 represents an alkyl group having 1 to 4 carbon atoms, Ar represents an unsubstituted or substituted phenyl group, R5 represents R4 when R2 is a hydrogen atom, and R5 represents a hydrogen atom when R2 is an alkyl group having 1 to 4 carbon atoms; including reacting a phenylacetamide compound represented by formula (2): wherein Q, R2 and Ar have the same meanings as defined above; with a dialkyl sulfate represented by formula (3): wherein R4 has the same meaning as defined above; in the presence of a base.Type: ApplicationFiled: February 12, 2010Publication date: December 1, 2011Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Hajime Ishida, Masaji Hirota, Yoko Miyanaga, Yuya Mizushima
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Publication number: 20110104765Abstract: Provided herein are compositions including diastereomers in substantially diastereomerically pure form and enantiomers in substantially enantiomerically pure form, and processes for preparing them and converting them to metyrosine.Type: ApplicationFiled: October 29, 2010Publication date: May 5, 2011Inventors: Kevin John HALLORAN, Alex COMELY, Zhengming CHEN, Shyam KRISHNAN
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Publication number: 20110034695Abstract: Disclosed is a method for preparing a compound of Formula 1 comprising contacting a compound of Formula 2 with at least one alkali metal cyanide of Formula 3 and a compound of Formula 4. wherein R1 is NHR3 or OR4; R2 is CH3 or Cl; R3 is H, C1-C4 alkyl, cyclopropyl, cyclopropylcyclopropyl, cyclopropylmethyl or methylcyclopropyl; R4 is H or C1-C4 alkyl; X is Br, Cl or I; and R5, R6, R7, R8, R9 and R10 are as defined in the disclosure. Also disclosed is a method for preparing a compound of Formula 4 wherein R9 and R10 together are a cycloalkadiene bidentate ligand, comprising contacting a compound of Formula 5 wherein Y is Cl, Br or I, with a cycloalkadiene bidentate ligand, at least one metal reducing agent and a nitrile solvent.Type: ApplicationFiled: November 7, 2008Publication date: February 10, 2011Applicant: E.I. Du pont de Nemours and CompanyInventors: Vladimir Grushin, Albert Loren Casalnuovo
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Publication number: 20100249449Abstract: The present invention relates to a process for preparing carboxamides by amidating nitriles in the presence of sulphuric acid, wherein the reaction is performed in a Taylor reactor. The process enables a simple and inexpensive preparation of these compounds. The present invention further provides processes for preparing (meth)acrylamides and alkyl(meth)acrylates, which comprise an inventive amidation reaction.Type: ApplicationFiled: August 15, 2008Publication date: September 30, 2010Applicant: Evonik Roehm GmbHInventors: Lorenza Sartorelli, Andreas Perl, Udo Gropp, Arndt Selbach
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Publication number: 20100216837Abstract: The present invention relates to compounds of formula (I), or salts or solvates thereof, their use in the manufacture of medicaments for treating neurological and neuropsychiatric disorders, in particular psychoses, dementia or attention deficit disorder. The invention further comprises processes to make these compounds and pharmaceutical formulations thereof.Type: ApplicationFiled: December 21, 2005Publication date: August 26, 2010Applicant: GLAXO GROUP LIMITEDInventors: Andrea Bozzoli, Daniel Marcus Bradley, Steven Coulton, Martin Leonard Gilpin, Jacqueline Anne MacRitchie, Roderick Alan Porter, Kevin Michael Thewlis
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Patent number: 7737284Abstract: This invention relates to a novel process for the synthesis of Temozolomide, an antitumor compound, and analogs, and to intermediates useful in this novel process.Type: GrantFiled: September 26, 2008Date of Patent: June 15, 2010Assignee: Schering Plough Corp.Inventors: Shen-Chun Kuo, Janet L. Mas, Donald Chen-tung Hou
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Patent number: 7737300Abstract: The present invention is directed to a process for preparing certain cysteine protease inhibitors.Type: GrantFiled: September 16, 2005Date of Patent: June 15, 2010Assignee: ViroBay, Inc.Inventor: Jiayao Li
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Publication number: 20100087414Abstract: The invention relates to a novel method for the synthesis of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-N-(3,5 -difluorophenyl)methylsulfonamide.Type: ApplicationFiled: December 11, 2009Publication date: April 8, 2010Applicant: SANOFI-AVENTISInventors: Philippe BOFFELLI, Michel DELTHIL, Luc GRONDARD, Maxime LAMPILAS, Joel MALPART, Stephane MUTTI, Lahlou NAIT-BOUDA, Joerg RIEKE-ZAPP
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Patent number: 7670986Abstract: A manganese dioxide catalyst for hydrolysing organic nitrites which bear readily oxidizable groups such as thiol or thioether groups to the corresponding carboxamides, and to a process for preparing the catalyst and to its use for hydrolysing organic nitrites.Type: GrantFiled: October 5, 2006Date of Patent: March 2, 2010Assignee: Degussa AGInventors: Horst Weigel, Axel Ronneburg, Christoph Weckbecker
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Publication number: 20100036161Abstract: Process for the industrial synthesis of the compound of formula (I)Type: ApplicationFiled: August 3, 2009Publication date: February 11, 2010Applicant: LES LABORATOIRES SERVIERInventors: Pascal Bontempelli, Xavier Jalenques, Jerome-Benoit Starck, Jean-Pierre Sery
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Publication number: 20090253928Abstract: A process for the preparation of a compound of formula (Ia): which are useful as intermediates in the preparation of i.a. pharmaceutically active compounds.Type: ApplicationFiled: March 31, 2009Publication date: October 8, 2009Inventors: Gerard John Harnett, Ursula Hoffmann, Michael Jansen, Reinhard Reents, Tim Sattelkau, Dennis A. Smith, Helmut Stahr
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Publication number: 20090118532Abstract: A process for the preparation of a compound of formula (I) wherein: R is an alkynyl group; R1 is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, phenyl and phenylalkyl, it being possible in turn for all of the receding groups to carry one or more identical or different halogen atoms; alkoxy; alkenyloxy; alkynyloxy; alkoxyalkyl; haloalkoxy; alkylthio; haloalkylthio; alkysulfonyl; formyl; alkanoyl; hydroxy; halogen; cyano; nitro; amino; alkylamino; dialkylamino; carboxyl; alkoxycarbonyl; alkenyloxycarbonyl; or alkynyloxycarbonyl; and n is an integer from 0 to 3, said process comprising: (i) the reaction of a compound of formula (III) wherein R, R1 and n are as hereinbefore defined; m and m? are independently 0 or 1; when m and m? are both 0, A is an alkyl, alkenyl or alkynyl group (suitably having up to eight carbon atoms), optionally substituted by one or more groups independently selected from halogen, hydroxy, alkoxy, C1-4 dialkylamino or cyano; when one of m and m? is 0 and the other is 1, A is an alType: ApplicationFiled: August 8, 2006Publication date: May 7, 2009Applicant: SYNGENTA CROP PROTECTION, INC.Inventors: Martin Charles Bowden, Thomas Aitcheson Clark, Fanny Giordano, Beat Jau, Hans-Dieter Schneider, Gottfried Seifert, Martin Zeller, Dominik Faber, Juerg Wiss
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Publication number: 20090118544Abstract: A process for the industrial synthesis of the compound of formula (I) Application in the synthesis of agomelatine.Type: ApplicationFiled: November 26, 2008Publication date: May 7, 2009Applicant: LES LABORATOIRS SERVIERInventors: Jean-Claude Souvie, Isaac Gonzalez Blanco
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Patent number: 7485751Abstract: The invention is directed at a new process for the preparation of pure enantiomers from the racemate of amidoacetonitrile compounds of formula wherein R1, R2 and R3, independently of each other, signify hydrogen, halogen, nitro, cyano, C1-C6-alkyl, halogen-C1-C6-alkyl, C1-C6-alkoxy, halogen-C1-C6-alkoxy, C2-C6-alkenyl, halogen-C2-C6-alkenyl, C2-C6-alkinyl, halogen-C2-C6-alkinyl, C2-C6-alkenyloxy, halogen-C2-C6-alkenyloxy, C1-C6-alkylthio, halogen-C1-C6-alkylthio, C1-C6-alkylsulfonyloxy, halogen-C1-C6-alkylsulfonyloxy, C1-C6-alkylsulfinyl, halogen-C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, halogen-C1-C6-alkylsulfonyl, C1-C6-alkenylthio, halogen-C1-C6-alkenylthio, C1-C6-alkenylsulfinyl, halogen-C1-C6-alkenylsulfinyl, C1-C6-alkenylsulfonyl, halogen-C1-C6-alkenylsulfonyl, C1-C6-alkylamino, di-(C1-C6-alkyl)amino, C1-C6-alkylaminocarbonyl, di-(C1-C6-alkyl)aminocarbonyl, C1-C6-alkylsulfonylamino, halogen-C1-C6-alkylsulfonylamino, C1-C6-alkylcarbonyl, halogen-C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, unsubstitutType: GrantFiled: November 7, 2005Date of Patent: February 3, 2009Assignee: Novartis Animal Health US, Inc.Inventors: Pierre Ducray, Noelle Gauvry, Thomas Goebel, Francois Pautrat
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Publication number: 20080319226Abstract: A process for the preparation of highly pure (E)-N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide (Entacapone). It comprises condensing 3,4-dihydroxy-5-nitro benzaldehyde with N,N-diethyl cyano acetamide in an organic solvent in the presence of an organic base and an acid under reflux conditions followed by distilling off the solvent under vacuum and treating the residue with a lower aliphatic carboxylic acid at 40-8O0 C. The resulting residue is extracted with a chlorinated solvent and the solvent is distilled off under vacuum. The resulting residue is extracted with an organic solvent to obtain crude N,N-diethyl-2-cyano-3-3,4-dihydroxy-5-nitrophenyl)acrylamide. The crude product N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl) acrylamide formed is treated with a mixture of organic alcohol and organic acid in the molar ratio of the crude product to organic alcohol 1:5 to 15 and crude product to organic acid 1:1 to 3 under reflux conditions.Type: ApplicationFiled: November 9, 2005Publication date: December 25, 2008Applicant: USV LIMITEDInventors: Venkatasubramanian Radhakrishnan Tarur, Dhananjay Govind Sathe, Nandu Baban Bhise, Avinash Venkatraman Naidu, Umesh Parashram Aher, Sachin Shivaji Patil
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Publication number: 20080312205Abstract: The invention relates to a novel method for the synthesis of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-N-(3,5-difluorophenyl)methylsulfonamide.Type: ApplicationFiled: August 20, 2008Publication date: December 18, 2008Applicant: SANOFI-AVENTISInventors: Philippe BOFFELLI, Michel DELTHIL, Luc GRONDARD, Maxime LAMPILAS, Joel MALPART, Stephane MUTTI, Lahlou NAIT-BOUDA, Joerg RIEKE-ZAPP
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Publication number: 20080306299Abstract: The invention relates to a process for preparing aminoalkanamides by reacting cyanoalkanoic esters with a) ammonia or an amine and b) hydrogen in the presence of a catalyst, the reaction with component b) being started simultaneously or not later than a maximum of 100 minutes after commencement of the reaction of the cyanoalkanoic ester with component a).Type: ApplicationFiled: December 15, 2006Publication date: December 11, 2008Applicant: BASF SEInventors: Martin Ernst, Andreas Kusche, Gunnar Heydrich, Horst Grafmans, Holger Evers, Johann-Peter Melder, Harald Meissner, Torsten Freund
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Publication number: 20080214774Abstract: Thiourethane prepolymer compositions, thiourethane polymer compositions, methods of making the compositions, and methods of using the thiourethane polymer compositions are provided. The thiourethane polymer composition can be produced by contacting a thiol ester composition and an isocyanate composition to produce a prepolymer composition and then curing the prepolymer composition to produce the thiourethane polymer composition. The prepolymer composition can also include a property modifying agent. In some embodiments, the thiol ester compositions include thiol esters, hydroxy thiol esters, and cross-linked thiol esters.Type: ApplicationFiled: March 1, 2007Publication date: September 4, 2008Inventors: Chad W. Brown, Jim D. Byers, Mitchell D. Refvik
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Patent number: 7227036Abstract: There is provided a process for producing an aminomethyl group-containing benzamide compound represented by the general formula (II): wherein —CONH2 and —X represent a substituent on the benzene ring and —CONH2 exists at the meta- or para-position of —CH2NH2, and X and n are as defined below, which comprises hydrating an aminomethyl group-containing benzonitrile compound represented by the general formula (I): wherein —CN and —X represent a substituent on the benzene ring and —CN exists at the meta- or para-position of —CH2NH2, X represents a chlorine atom or a fluorine atom, and n represents an integer of 0 to 4, provided that, when n is 2 or more, X may be the same or differentType: GrantFiled: May 2, 2003Date of Patent: June 5, 2007Assignee: Showa Denko K.K.Inventors: Yutaka Ohnishi, Hideo Miyata, Kimitaka Ohshiro
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Patent number: 6861557Abstract: The present invention relates to a new process for the synthesis of racemic and optically active bicalutamide starting from ethyl pyruvate and methyl methacrylate. The present invention discloses processes of preparing bicalutamide intermediates including ethyl-[2-{4-fluorophenyl sulfone}]-2-hydroxy propionate, 1,2-epoxy-2-methyl propionate and 2-hydrox-2-methyl-3-(4-fluorophenylthio) propionic acid. The present invention further discloses micronized rac-bicalutamide and the preparation thereof.Type: GrantFiled: March 8, 2004Date of Patent: March 1, 2005Assignee: Biogal Gyógyszergyár Rt.Inventors: Ben-Zion Dolitzky, Ofer Reany, Jenny Shammai
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Publication number: 20040220410Abstract: The invention relates to &bgr;-alanine amides of general formula (I), wherein: R1 represents hydrogen or C1-6 alkyl that is optionally substituted by hydroxy, amino, carboxy, carbamoyl, methylmercapto, guanidino, optionally substituted aryl or heteroaryl, and; R2 represents hydrogen or R1 and R2, together, form a group of formula —(CH2)n—, wherein n is 3 or 4. Said &bgr;-alanine amides are produced without using an amino protective group by reacting the corresponding amine with a cyanoacetic ester in order to form an acetamide and by effecting a subsequent catalytic hydrogenation. The method is suited, in particular, for producing Carcinine (&bgr;-alanyl-histamine, R?1 =imidazol-4-ylmethyl, R2=H), a naturally occurring pseudo dipeptide, which is used as an active ingredient having an antioxidative effect in medicaments and cosmetics.Type: ApplicationFiled: March 5, 2004Publication date: November 4, 2004Inventors: Paul Hanselmann, Stefan Hildbrand
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Patent number: 6750368Abstract: The present invention relates to a process for preparing sulphuric methacrylamide. The process can include adding sulphur trioxide and a second part of acetone cyanohydrin without sulfuric add to a reaction medium, after a first part of acetone cyanohydrin with sulphuric acid free of sulfur trioxide is mixed and dehydrated by heating.Type: GrantFiled: July 12, 2002Date of Patent: June 15, 2004Assignee: AtofinaInventors: Jean-François Croisy, Michel Tosi
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Patent number: 6696605Abstract: The present invention relates to a process for preparing a &agr;-hydroxyamide or &agr;-ketoamide, said process comprising the steps of: a) reacting a resin which comprises a polymer-supported isocyanide with an aldehyde in the presence of a catalyst, to form a resin-bound &agr;-hydroxyamide; b) optionally reacting said resin-bound &agr;-hydroxyamide with a reagent which is capable of oxidizing said resin-bound &agr;-hydroxyamide to a resin-bound &agr;-ketoamide; and c) reacting said resin-bound &agr;-hydroxyamide or resin-bound &agr;-ketoamide with a reagent which cleaves the nitrogen-resin bond to form a &agr;-hydroxyamide &agr;-ketoamide.Type: GrantFiled: January 1, 2003Date of Patent: February 24, 2004Assignee: The Procter & Gamble CompanyInventor: Jian Chen
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Patent number: 6673967Abstract: A method for processing of hydrogen for the reductive acylation of nitro, azido and cyano arenes is disclosed. More particularly, improved process for the preparation of amides and anilides using C3-C7 carboxylic acids as proton source/acylating agents employing Fe3+-montmorillonite as a catalyst is disclosed.Type: GrantFiled: November 29, 2002Date of Patent: January 6, 2004Assignee: Council of Scientific and Industrial ResearchInventors: Boyapati Manoranjan Choudary, Venkati Sri Ranganath Kalluri, Lakshmi Kantam Mannepalli
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Patent number: 6649796Abstract: The invention provides a process for the preparation of diphenylmethylthioacetamide (I) as described in Scheme 4 comprising reacting of the isothiouronium salt or its corresponding base of the formula IV with an acetamide of the formula XCH2CONH2, wherein X represents a halogen, M represents an alkali metal and A represents an anion, in a protic medium at a temperature of less than 100° C.Type: GrantFiled: April 2, 2002Date of Patent: November 18, 2003Assignee: Chemagis, Ltd.Inventors: Vladimir Naddaka, Naim Menashe, Jael Lexner, Shadi Saeed, Joseph Kaspi, Ori Lerman
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Publication number: 20030176739Abstract: The present invention relates to a process for preparing a &agr;-hydroxyamide or &agr;-ketoamide, said process comprising the steps of:Type: ApplicationFiled: January 1, 2003Publication date: September 18, 2003Applicant: The Procter & Gamble CompanyInventor: Jian Chen
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Publication number: 20030120113Abstract: A process for obtaining an amide of the general formula R-(CO)—NH—CH2—X involves contacting a nitrile of the general formula R-CN with:Type: ApplicationFiled: November 5, 2002Publication date: June 26, 2003Applicant: Millennium Specialty Chemicals, Inc.Inventors: Mikhail Yu Lebedev, Mark B. Erman
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Publication number: 20030083503Abstract: Acylated ketoamides are prepared from sulfonyl amides and aldehydes or their related derivatives by a step of 1Type: ApplicationFiled: June 20, 2002Publication date: May 1, 2003Inventors: Doug E. Frantz, Lisa F. Frey, Karen Marcantonio, Jerry Anthony Murry, Richard Tillyer
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Patent number: 6521794Abstract: For the production of an aromatic compound by hydrolyzing and decarboxylating a corresponding aromatic cyano compound in the presence of an acidic substance, this invention provides a method for the production of the aromaic compound, characterized by carrying out the reactions of hydrolysis and decarboxylaion in multiple steps. Particularly when the aromatic cyano compound contains a halogen, this method effectively prevents the reaction vessels from being corroded by the by-produced hydrogen halogenide and enables the target compound to be produced in a high yield.Type: GrantFiled: February 1, 2002Date of Patent: February 18, 2003Assignee: Nippon Shokubai Co., Ltd.Inventor: Kouichi Hirota
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Patent number: 6482983Abstract: A process for obtaining an amide of the general formula R—(CO)—NH—CH2—X involves contacting a nitrile of the general formula R—CN with: a) an acid; and c) an alkoxy-containing compound comprising at least one alkoxy functionality of the general formula —OCH2—X; wherein R is hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, or heterocyclic substituent, which substituents can be substituted or unsubstituted; wherein X is hydrogen or a radical having the general formula —CHR1R2; and wherein R1 and R2 independently or collectively represent hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, or heterocyclic substituent, or any combination thereof, which substituents can be substituted or unsubstituted.Type: GrantFiled: July 31, 2001Date of Patent: November 19, 2002Assignee: Millennium Specialty ChemicalsInventors: Mikhail Yu. Lebedev, Mark B. Erman
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Patent number: 6441232Abstract: There is provided a method of selectively replacing a carbon-hydrogen bond at an unactivated saturated sp3 hybridised carbon atom in an organic compound by a carbon-nitrogen bond, the method comprising reacting the compound with a fluorinating agent in a solvent reaction medium comprising a nitrile compound and providing a Lewis acid whereby the carbon-hydrogen bond is replaced by a carbon-nitrogen bond. Advantageously, the reaction may be performed in one stage and/or in one vessel. Advantageously, the method may be carried out at or just below ambient or room temperature.Type: GrantFiled: January 1, 2002Date of Patent: August 27, 2002Assignee: F2 Chemicals Ltd.Inventors: Richard Dickinson Chambers, Mandy Parsons, Graham Sandford
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Patent number: 6437183Abstract: The invention relates to the manufacture of amide compounds provided through the reaction of nitrile compounds and a sulfate compound to form the related amide compound. In a preferred embodiment a diol or a triol is employed as a solvent, thereby increasing the yield of the product.Type: GrantFiled: August 8, 2001Date of Patent: August 20, 2002Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Carlos Ramirez
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Patent number: RE46218Abstract: Process for the industrial synthesis of the compound of formula (I)Type: GrantFiled: February 11, 2015Date of Patent: November 29, 2016Assignee: LES LABORATOIRES SERVIERInventors: Samir Zard, Béatrice Sire, Mehdi Boumediene