Forming Directly By Amination Which Replaces Halogen Patents (Class 564/376)
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Patent number: 8952197Abstract: The present invention relates to processes and intermediates useful in the preparation of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (lorcaserin), a serotonin (5-HT) receptor modulator that is useful in the treatment of for example, central nervous system disorders, such as obesity.Type: GrantFiled: June 17, 2010Date of Patent: February 10, 2015Assignee: Arena Pharmaceuticals, Inc.Inventors: John A. DeMattei, Carlos Marlon, Ryan O. Castro, Tsung-Hsun Chuang, Mark Allen Hadd, Xiao-Xiong Lu, Mark Macias, Stephen M. Shaw
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Patent number: 8269044Abstract: Disclosed is a method for producing a primary amine compound represented by the formula (3): wherein, Ar is as defined below, which is characterized in that a halogen compound represented by the formula (1): wherein, Ar represents an unsubstituted aromatic group such as a phenyl group, a naphthyl group, a pyridyl group, a furyl group, a thienyl group, a pyrrolyl group, an oxazolyl group, an isoxazolyl group or a pyrimidinyl group, or an aromatic group obtained by substituting such an unsubstituted aromatic group with 1-3 substituents; and X represents a halogen atom, ammonia and formaldehyde are reacted with each other, thereby obtaining a hexahydrotriazine compound represented by the formula (2): wherein, Ar is as defined above, and then the thus-obtained hexahydrotriazine compound is decomposed. By this method, a primary amine compound can be commercially advantageously produced by using a low-cost ammonia while suppressing production of a secondary amine as a by-product.Type: GrantFiled: December 14, 2006Date of Patent: September 18, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Naoyuki Takano, Kazuyuki Tanaka, Shinzo Seko
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Publication number: 20120142967Abstract: The present invention relates to processes and intermediates useful in the preparation of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (lorcaserin), a serotonin (5-HT) receptor modulator that is useful in the treatment of, for example, central nervous system disorders, such as obesity.Type: ApplicationFiled: June 17, 2010Publication date: June 7, 2012Inventors: John A. DeMattei, Marlon Carlos, Ryan O. Castro, Tsung-Hsun Chuang, Mark Allen Hadd, Xiao-Xiong Lu, Mark Macias, Stephen M. Shaw
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Patent number: 7652170Abstract: Disclosed is a method for producing a primary amine compound represented by the formula (2) below, which is characterized in that a halogen compound represented by the formula (1) below, ammonia and formaldehyde are reacted with each other, and then the thus-obtained reaction product is [1] brought into contact with an aqueous solution of an acid or [2] reacted with a hydroxylamine under acidic conditions. By this method, a primary amine compound can be commercially advantageously produced by using a low-cost ammonia while suppressing production of a secondary amine as a by-product. (1) (In the formula, R1 and R2 independently represent a hydrogen atom, a C1-C5 alkyl group which may be substituted by a halogen atom or the like, a C1-C5 alkoxy group which may be substituted by a halogen atom, a cyano group, a C2-C11 alkenyl group or a phenyl group or the like; R3 represents a hydrogen atom, a linear or branched C1-C5 alkyl group or a cyano group; and X represents a halogen atom.Type: GrantFiled: December 25, 2006Date of Patent: January 26, 2010Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroshi Souda, Naoyuki Takano, Shinzo Seko
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Patent number: 7456318Abstract: This present invention relates to a process for preparing benzylated amines by the reaction of an amine selected from methamphetamine and propylhexedrine with benzyl halide. Numerous improvements are obtained by employing the amine in molar excess with respect to benzyl halide, preferably in a molar ratio of 2 to 1. The excess amine is employed to selectively neutralize by-product acid as the amine salt. The amine salt is then separated from the reaction mixture and basified to reclaim starting amine for recycle to the process.Type: GrantFiled: November 2, 2005Date of Patent: November 25, 2008Assignee: Mallinckrodt Inc.Inventor: Dennis J. Kalota
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Patent number: 6803462Abstract: This invention discloses a rubbery polymer which is comprised of repeat units that are derived from (1) at least one conjugated diolefin monomer, and (2) at least one functionalized monomer having of the structural formula: wherein R represents an alkyl group containing from 1 to about 10 carbon atoms or a hydrogen atom, and wherein R1 and R2 can be the same or different and represent hydrogen atoms or a moiety selected from the group consisting of wherein R3 groups can be the same or different and represent alkyl groups containing from 1 to about 10 carbon atoms, aryl groups, allyl groups, and alkyloxy groups of the structural formula —(CH2)y—O—(CH2)z—CH3, wherein Z represents a nitrogen containing heterocyclic compound, wherein R4 represents a member selected from the group consisting of alkyl groups containing from 1 to about 10 carbon atoms, aryl groups, and allyl groups, and wherein n, x, y and z represents integers from 1 to about 10, with theType: GrantFiled: June 30, 2003Date of Patent: October 12, 2004Assignee: The Goodyear Tire & Rubber CompanyInventors: Stephan Rodewald, Steven Kristofer Henning, Brian Earl Burkhart
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Patent number: 6710210Abstract: Novel N-substituted-aminomethyl cyclopropyl ketone derivatives are represented by following Formula (1): wherein R1, R2 and R3 are each a hydrogen atom or an aliphatic hydrocarbon group; and R4 and R5 are each a hydrogen atom or an arylmethyl group which may have a substituent, where at least one hydrogen atom or aryl group as a substituent is combined with a carbon atom in the methyl moiety of the arylmethyl group, and at least one of R4 and R5 is an arylmethyl group which may have a substituent. These compounds are useful for the preparation of aminomethyl cyclopropyl ketone derivatives and 2-amino-1-cyclopropylethanol derivatives or salts thereof.Type: GrantFiled: April 8, 2002Date of Patent: March 23, 2004Assignee: Daicel Chemical Industries, Ltd.Inventors: Hiroki Tanaka, Li Rui Pan, Kiyoshi Ikura
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Patent number: 6670471Abstract: This invention discloses a rubbery polymer which is comprised of repeat units that are derived from (1) at least one conjugated diolefin monomer, and (2) at least one functionalized monomer having of the structural formula: wherein R represents an alkyl group containing from 1 to about 10 carbon atoms or a hydrogen atom, and wherein R1 and R2 can be the same or different and represent hydrogen atoms or a moiety selected from the group consisting of wherein R3 groups can be the same or different and represent alkyl groups containing from 1 to about 10 carbon atoms, aryl groups, allyl groups, and alkyloxy groups of the structural formula —(CH2)y—O—(CH2)z—CH3, wherein Z represents a nitrogen containing heterocyclic compound, wherein R4 represents a member selected from the group, consisting of alkyl groups containing from 1 to about 10 carbon atoms, aryl groups, and allyl groups, and wherein n, x, y and z represents integers from 1 to about 10, with theType: GrantFiled: February 4, 2003Date of Patent: December 30, 2003Assignee: The Goodyear Tire & Rubber CompanyInventors: Stephan Rodewald, Steven Kristofer Henning, Brian Earl Burkhart
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Patent number: 6235871Abstract: The transition metal-catalyzed amination of aryl halides, in conjunction with an orthogonal protective group scheme, forms the basis of two routes to oligoaniline precursors. The oligoaniline precursors are soluble in a variety of common organic solvents, and are easily converted to the deprotected oligoanilines. The method allows the preparation of oligoanilines of even or odd chain lengths, and the incorporation of a variety of functional groups into the oligomers. Polyanilines of low polydispersity can also be prepared by this method.Type: GrantFiled: December 2, 1998Date of Patent: May 22, 2001Assignee: Massachusetts Institute of TechnologyInventors: Robert A. Singer, Joseph P. Sadighi, Stephen L. Buchwald, Thomas Mackewitz
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Patent number: 5932767Abstract: Protriptyline can be prepared from 5-dihydrodibenzocycloheptatriene, by deprotonation, followed by reaction at low temperatures with 1,3-bromochloropropane to give the 5-(chloropropyl)-dibenzocycloheptatriene, which is reacted with methylamine in a displacement reaction to give the protriptyline product.Type: GrantFiled: December 22, 1997Date of Patent: August 3, 1999Assignee: Merck & Co., Inc.Inventors: Robert S. Hoerrner, Joseph Auerbach, John Carolan
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Patent number: 5929281Abstract: A heterocyclic aromatic halide or an aryl halide is reacted with an amine compound in the presence of a base to give a heterocyclic aromatic amine or an arylamine, respectively. In this reaction, a catalyst comprising a palladium compound and a tertiary phosphine is used for the preparation of a heterocyclic aromatic amine, and a catalyst comprising a palladium compound and a trialkylphosphine is used for the preparation of an arylamine.Type: GrantFiled: April 15, 1997Date of Patent: July 27, 1999Assignee: Tosoh CorporationInventors: Masakazu Nishiyama, Yasuyuki Koie
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Patent number: 5663440Abstract: An object of the invention is to propose diamino compounds expressed by the following general formula (1) which are suitable to obtain a raw material, a polyimide resin, for a liquid crystal aligning film without any image sticking and with a high voltage holding ratio at from a low temperature to a high temperature as well as the preparation thereof: ##STR1##Type: GrantFiled: October 2, 1995Date of Patent: September 2, 1997Assignee: Chisso CorporationInventors: Toshiya Sawai, Seiji Oikawa, Masaaki Yazawa, Shizuo Murata, Masaharu Hayakawa, Etsuo Nakagawa, Shinichi Sawada
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Patent number: 5576460Abstract: A method of preparing an arylamine compound includes reacting a metal amide comprising a metal selected from the group consisting of tin, boron, zinc, magnesium, indium and silicon, with an aromatic compound comprising an activated substituent in the presence of a transition metal catalyst to form an arylamine. The method is useful in preparing mixtures of arylamines for use in screening for pharmaceutical and biological activity and in preparing poly(anilines).Type: GrantFiled: July 27, 1994Date of Patent: November 19, 1996Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Anil Guram
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Patent number: 5449828Abstract: The present invention relates to a process for the preparation of L-isomer of propargyl-ammonium-chloride derivatives of the formula (I) ##STR1## by decomposing D-tartarte of L-isomer of the amine of the general ##STR2## wherein y is hydrogen or fluoro and by reacting the obtained L-issomer amine of the formula (II) in the presence of a base with a halide of the formula (V), X--CH.sub.2 --C.ident.CCH wherein X is halogen and by reacting the so obtained L-isomer of the Formula (III) ##STR3## with hydrogen-chloride in an organic solvent, wherein x is a halogen atom,y is a hydrogen or fluorine atom.Type: GrantFiled: December 9, 1994Date of Patent: September 12, 1995Assignee: Chinoin Gyogyszer- Es Vegyeszeti Termekek Gyara Rt.Inventors: Zsuzsanna Nad, Tamas Kallay, Maria Sziladi, Tibor Montay
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Patent number: 5220068Abstract: The present invention relates to a pharmaceutical composition comprising as active ingredient a compound of the Formula I ##STR1## wherein R.sup.1 stands for straight or branched chain alkyl comprising 1 to 8 carbon atoms; phenyl alkyl having 7 to 10 carbon atoms; phenyl; or cycloalkyl comprising 3 to 8 carbon atoms;R.sup.2 stands for straight or branched chain alkyl comprising 1 to 8 carbon atoms; alkyl comprising 1 to 8 carbon atoms substituted by halogen, hydroxy, alkoxy having 1 to 4 carbon atoms or by one or two phenyl groups; phenyl; or cycloalkyl having 3 to 8 carbon atoms,with the proviso that groups R.sup.1 and R.sup.2 together contain at least three carbon atoms. The invention also relates to a process for the preparation of compounds of the Formula I by methods known per se.Type: GrantFiled: January 29, 1991Date of Patent: June 15, 1993Assignee: Chinoin Gyogyszer - es Vegyeszeti Termekek Gyara Rt.Inventors: Jozsef Knoll, Antal Simay, Eva Szinnyei, Eva Somfai, Zoltan Torok, Karoly Mozsolits, Janos Bergmann
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Patent number: 4960797Abstract: The invention relates to the new N-[2-/4-fluorophenyl/-1-methyl]-ethyl-N-methyl-N-propynyl amine of the Formula I ##STR1## and isomers and salts thereof. The compound of the formula I is useful as a selective MAO inhibitor.Type: GrantFiled: February 15, 1989Date of Patent: October 2, 1990Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.Inventors: Zoltan Ecsery, deceased, Jozsef Knoll, Eva Somfai, Zoltan Torok, Eva Szinnyei, Karoly Mozsolics
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Patent number: 4777294Abstract: A compound of the formula: ##STR1## wherein A is a chain hydrocarbon group having 1 to 10 carbon atoms optionally substituted by hydroxyl, phenoxy, thienyl, furyl, pyridyl, cyclohexyl or an optionally substituted phenyl group, or a cyclic hydrocarbon group having 3 to 7 carbon atoms optionally substituted by hydroxyl, B is hydrogen or hydroxyl, and their production and use.These compounds exhibit excellent inhibitory activity against .alpha.-glucoside hydrolase, thus are useful for hyperglycemic symptoms and various disorders caused by hyperglycemia.Type: GrantFiled: April 17, 1987Date of Patent: October 11, 1988Assignee: Takeda Chemical Industries, Ltd.Inventors: Satoshi Horii, Yukihiko Kameda, Hiroshi Fukase
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Patent number: 4701559Abstract: A compound of the formula: ##STR1## wherein A is a chain hydrocarbon group having 1 to 10 carbon atoms optionally substituted by hydroxyl, phenoxy, thienyl, furyl, pyridyl, cyclohexyl or an optionally substituted phenyl group, or a cyclic hydrocarbon group having 3 to 7 carbon atoms optionally substituted by hydroxyl, B is hydrogen or hydroxyl, and their production and use.These compounds exhibit excellent inhibitory activity against .alpha.-glucoside hydrolase, thus are useful for hyperglycemic symptoms and various disorders caused by hyperglycemia.Type: GrantFiled: December 28, 1981Date of Patent: October 20, 1987Assignee: Takeda Chemical Industries, Inc.Inventors: Satoshi Horii, Yukihiko Kameda, Hiroshi Fukase
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Patent number: 4564706Abstract: The invention relates to a new process for the preparation of propargyl ammonium chlorides of the Formula I ##STR1## by alkaline decomposition of the d-tartarate of the 1-isomer of an amine of the Formula II ##STR2## and subsequent reaction of the amine of the Formula II with a halide of the Formula IIIX--CH.sub.2 --C.tbd.Type: GrantFiled: July 14, 1983Date of Patent: January 14, 1986Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara R.T.Inventors: Zoltan Ecsery, Eva Somfai, Judit Hermann nee Voros, Lajos Nagy, Gabor Szabo, Otto Orban, Laslzo Arvai
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Patent number: 4486602Abstract: A compound of the formula: ##STR1## wherein A is a chain hydrocarbon group having 1 to 10 carbon atoms optionally substituted by hydroxyl, phenoxy, thienyl, furyl, pyridyl, cyclohexyl or an optionally substituted phenyl group; or a cyclic hydrocarbon group having 3 to 7 carbon atoms optionally substituted by hydroxyl, and their production and use.These compounds exhibit excellent inhibitory activity against glucoside hydrolase, thus are useful for hyperglycemic symptoms and various disorders caused by hyperglycemia.Type: GrantFiled: September 29, 1981Date of Patent: December 4, 1984Assignee: Takeda Chemical Industries, Ltd.Inventors: Satoshi Horii, Yukihiko Kameda, Hiroshi Fukase