Preparing Directly By Hydrolysis Patents (Class 564/377)
  • Patent number: 8969623
    Abstract: 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: Grant
    Filed: October 11, 2013
    Date of Patent: March 3, 2015
    Assignee: Amneal Pharmaceuticals, LLC
    Inventors: Vijayavitthal Thippannachar Mathad, Navnath Chintaman Niphade, Gorakshanath Balasaheb Shinde, Sharad Subhash Ippar, Shrikant Prataprao Deshmukh, Raghavendra Kumar Panchangam
  • Publication number: 20140288306
    Abstract: 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: Application
    Filed: June 5, 2014
    Publication date: September 25, 2014
    Inventors: David Milstein, Chidambaram Gunanathan
  • Publication number: 20140275569
    Abstract: 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: Application
    Filed: March 14, 2014
    Publication date: September 18, 2014
    Inventors: Richard W. Morrison, Douglas Michael Jackson
  • Patent number: 8575395
    Abstract: 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: Grant
    Filed: September 6, 2011
    Date of Patent: November 5, 2013
    Assignees: 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
  • Publication number: 20130197223
    Abstract: 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: Application
    Filed: September 22, 2011
    Publication date: August 1, 2013
    Applicant: NOVOMER, INC.
    Inventors: Jay J. Farmer, Gabriel E. Job
  • Publication number: 20110319663
    Abstract: 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: Application
    Filed: September 6, 2011
    Publication date: December 29, 2011
    Applicant: Amneal Pharmaceuticals, LLC
    Inventors: Vijayvitthal Thippannachar Mathad, Navnath Chintaman Niphade, Gorakshanath Balasaheb Shinde, Sharad Subhash Ippar, Shrikant Prataprao Deshmukh, Ragavendra Kumar Panchangam
  • Patent number: 6960691
    Abstract: 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: Grant
    Filed: June 17, 2002
    Date of Patent: November 1, 2005
    Assignee: Showa Denko K.K.
    Inventors: Hideyuki Kondo, Yuseki Suyama, Kohei Morikawa
  • Patent number: 6713652
    Abstract: 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: Grant
    Filed: September 11, 2001
    Date of Patent: March 30, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Ditrich, Wolfgang Ladner, Johann-Peter Melder
  • Patent number: 4960797
    Abstract: 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: Grant
    Filed: February 15, 1989
    Date of Patent: October 2, 1990
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.
    Inventors: Zoltan Ecsery, deceased, Jozsef Knoll, Eva Somfai, Zoltan Torok, Eva Szinnyei, Karoly Mozsolics
  • Patent number: 4927969
    Abstract: 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: Grant
    Filed: May 2, 1988
    Date of Patent: May 22, 1990
    Assignee: PPG Industries, Inc.
    Inventors: Charles F. Kahle, II, Gregory J. McCollum, Craig A. Wilson
  • Patent number: 4326067
    Abstract: 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: Grant
    Filed: December 3, 1980
    Date of Patent: April 20, 1982
    Assignee: The Dow Chemical Company
    Inventor: Michael J. Fazio
  • Patent number: 4281197
    Abstract: 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: Grant
    Filed: October 6, 1980
    Date of Patent: July 28, 1981
    Assignee: Ford Motor Company
    Inventor: Fred G. Oblinger