Preparing Directly By Hydrolysis Patents (Class 564/377)
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Patent number: 8969623Abstract: A method for the preparation of Cinacalcet is disclosed comprising treating (R)-1-naphthyl ethylamine with an aromatic aldehyde to form (1R)-1-(2-naphthyl)-N-(aryl methylene)ethanamine derivative of Formula (IV), which is further treated with 1-(3-halopropyl)-3-(trifluoromethyl)benzene of Formula (V) to obtain an iminium salt of Formula (VI), followed by hydrolysis to obtain Cinacalcet free base.Type: GrantFiled: October 11, 2013Date of Patent: March 3, 2015Assignee: Amneal Pharmaceuticals, LLCInventors: Vijayavitthal Thippannachar Mathad, Navnath Chintaman Niphade, Gorakshanath Balasaheb Shinde, Sharad Subhash Ippar, Shrikant Prataprao Deshmukh, Raghavendra Kumar Panchangam
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Publication number: 20140288306Abstract: The present invention provides novel ruthenium based catalysts, and a process for preparing amines, by reacting a primary alcohol and ammonia in the presence of such catalysts, to generate the amine and water. According to the process of the invention, primary alcohols react directly with ammonia to produce primary amines and water in high yields and high turnover numbers. This reaction is catalyzed by novel ruthenium complexes, which are preferably composed of quinolinyl or acridinyl based pincer ligands.Type: ApplicationFiled: June 5, 2014Publication date: September 25, 2014Inventors: David Milstein, Chidambaram Gunanathan
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Publication number: 20140275569Abstract: The present application provides methods for decarboxylation of amino acids via imine formation with a catalyst under superheated conditions in either a microwave or oil bath.Type: ApplicationFiled: March 14, 2014Publication date: September 18, 2014Inventors: Richard W. Morrison, Douglas Michael Jackson
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Patent number: 8575395Abstract: A method for the preparation of Cinacalcet is disclosed comprising treating (R)-1-naphthyl ethylamine with an aromatic aldehyde to form (1R)-1-(2-naphthyl)-N-(aryl methylene)ethanamine derivative of Formula (IV), which is further treated with 1-(3-halopropyl)-3-(trifluoromethyl)benzene of Formula (V) to obtain an iminium salt of Formula (VI), followed by hydrolysis to obtain Cinacalcet free base.Type: GrantFiled: September 6, 2011Date of Patent: November 5, 2013Assignees: Amneal Pharmaceuticals, LLC, Megafine Pharma (P) Ltd.Inventors: Vijayavitthal Thippannachar Mathad, Navnath Chintaman Niphade, Gorakshanath Balasaheb Shinde, Sharad Subhash Ippar, Shrikant Prataprao Deshmukh, Raghavendra Kumar Panchangam
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Publication number: 20130197223Abstract: Among other things, the present invention encompasses methods of synthesizing salicylaldehyde derivatives comprising the steps of: a) providing salicylaldehyde or a derivative thereof, b) forming an anhydro dimer of the provided salicylaldehyde compound, c) performing one or more chemical transformations on the anhydro dimer and d) hydrolyzing the anhydro dimer to provide a salicylaldehyde derivative different from that provided in step (a).Type: ApplicationFiled: September 22, 2011Publication date: August 1, 2013Applicant: NOVOMER, INC.Inventors: Jay J. Farmer, Gabriel E. Job
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Publication number: 20110319663Abstract: A method for the preparation of Cinacalcet is disclosed comprising treating (R)-1-naphthyl ethylamine with an aromatic aldehyde to form (1R)-1-(2-naphthyl)-N-(aryl methylene)ethanamine derivative of Formula (IV), which is further treated with 1-(3-halopropyl)-3-(trifluoromethyl)benzene of Formula (V) to obtain an iminium salt of Formula (VI), followed by hydrolysis to obtain Cinacalcet free base.Type: ApplicationFiled: September 6, 2011Publication date: December 29, 2011Applicant: Amneal Pharmaceuticals, LLCInventors: Vijayvitthal Thippannachar Mathad, Navnath Chintaman Niphade, Gorakshanath Balasaheb Shinde, Sharad Subhash Ippar, Shrikant Prataprao Deshmukh, Ragavendra Kumar Panchangam
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Patent number: 6960691Abstract: The invention intends to provide means for producing halogenated aromatic methylamine useful as an intermediate in the production of agrochemical or medical preparations, by an industrially advantageous method. The process according to the present invention for producing halogenated aromatic methylamine is characterized by comprising hydrogen-reducing a halogenated aromatic nitrile represented by formula (1): (wherein X represents a chlorine atom or a fluorine atom, m represents an integer of 1 to 5, n represents an integer of 1 to 5, m+n?6, and when n is 2 or more, each X may be the same or different) using a hydrogenating catalyst in the presence of an organic acid in a solvent to produce a halogenated aromatic methylamine represented by formula (2): (wherein X, m and n have the same meanings as defined above, and a represents an integer of 1 to m).Type: GrantFiled: June 17, 2002Date of Patent: November 1, 2005Assignee: Showa Denko K.K.Inventors: Hideyuki Kondo, Yuseki Suyama, Kohei Morikawa
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Patent number: 6713652Abstract: The present invention relates to a process for hydrolyzing optically active amides to carboxylic acids and optically active amines with retention of the center of chirality, where the hydrolysis of the amides is carried out with an alkali metal or alkaline earth metal hydroxide in the presence of 5-30% by weight, based on the amide employed, of a polyol or an amino alcohol.Type: GrantFiled: September 11, 2001Date of Patent: March 30, 2004Assignee: BASF AktiengesellschaftInventors: Klaus Ditrich, Wolfgang Ladner, Johann-Peter Melder
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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: 4927969Abstract: Alkyl primary amines, e.g., tertiary alkyl primary amines, are prepared by reaction of the corresponding alkyl primary isocyanates with an alkanolamine to form an intermediate area reaction product, followed by heating to decompose the urea reaction product and form the amine product. The amine product can be recovered in high yield by vacuum distillation.Type: GrantFiled: May 2, 1988Date of Patent: May 22, 1990Assignee: PPG Industries, Inc.Inventors: Charles F. Kahle, II, Gregory J. McCollum, Craig A. Wilson
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Patent number: 4326067Abstract: The process of the invention for preparing a N-(2-substituted aminoethyl)amide of the formula: ##STR1## comprises contacting one or more compounds of the formula: ##STR2## with an amine of the formula: ##STR3## wherein A is nitrogen or a quaternary nitrogen of the formula: ##STR4## wherein B is ##STR5## when A is nitrogen and B is ##STR6## when A is IV; whereinX.sup..crclbar. is a counterion;b is zero or one; andR.sub.1 -R.sub.9 are as defined in the specification.In a preferred embodiment, the process is catalyzed by a Lewis acid or a protonic acid with a non-nucleophilic counterion.Type: GrantFiled: December 3, 1980Date of Patent: April 20, 1982Assignee: The Dow Chemical CompanyInventor: Michael J. Fazio
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Patent number: 4281197Abstract: Porous polyurethane solids such as open cell polyurethane foams are rapidly heated and hydrolytically decomposed into separate polyol component and diamine component by contacting the porous solids with saturated steam in a heated vacuum chamber. Separation of high quality liquid polyol and diamine is achieved.Type: GrantFiled: October 6, 1980Date of Patent: July 28, 1981Assignee: Ford Motor CompanyInventor: Fred G. Oblinger