Forming Amine Group Directly By Reduction, Other Than By Reductive Amination Patents (Class 564/375)
  • Patent number: 9090539
    Abstract: Compounds and methods for preparing substituted 3-(1-amino-2-methylpentane-3-yl)phenyl compounds from an isomerically pure starting material are described. In particular, methods of preparing a 3-(1-(dimethylamino)-2-methylpentane-3-yl)phenol as a substantially optically pure (R,R) stereoisomer are described. Using a method of the present invention, only the (R,R) and (S,S) stereoisomers of the target compound are produced, increasing the yield and stereoselectivity of the desired (R,R) stereoisomer.
    Type: Grant
    Filed: May 24, 2013
    Date of Patent: July 28, 2015
    Assignee: AMPAC Fine Chemicals LLC
    Inventors: Brian Morgan, Olivier Dapremont, Patrick Berget, Ali Suleman, William Dubay, Jeffrey D. Butler
  • Patent number: 8853393
    Abstract: The invention discloses a novel intermediate for preparing tapentadol and analogues thereof, wherein the structural formula is shown as formula I or II, and the groups are defined as the specification. The invention further discloses a method for preparing the novel intermediate and use of the intermediate for preparing tapentadol and analogues thereof. The invention can remarkably improve the product yield and quality of tapentadol, reduce the production cost, and simplify the production procedure. The preparation process is environment friendly, thus more suitable for the requirements of industrial production.
    Type: Grant
    Filed: July 29, 2011
    Date of Patent: October 7, 2014
    Assignee: Anhui New Star Pharmaceutical Development Co., Ltd.
    Inventors: Ziao Xu, Yuanhai Zhao, Degang Li, Xiaoxiang Li
  • Patent number: 8669399
    Abstract: A process for the preparation of substituted 3-(1-amino-2-methylpentane-3-yl)phenyl compounds which has advantages over conventional processes with respect to higher conversions and yields, flexibility, a shorter overall route, environmentally acceptable conditions, influence of stereoselectivity such as diastereoselectivity in a targeted manner and at least partial suppression of the formation of undesired side-products and/or undesired stereoisomers, in particular undesired diastereomers.
    Type: Grant
    Filed: June 14, 2011
    Date of Patent: March 11, 2014
    Assignee: Grünenthal GmbH
    Inventors: Helmut Heinrich Buschmann, Joerg Holenz
  • Publication number: 20130338399
    Abstract: A process for the preparation of substituted 3-(1-amino-2-methylpentane-3-yl)phenyl compounds which has advantages over conventional processes with respect to higher conversions and yields, flexibility, a shorter overall route, environmentally acceptable conditions, influence of stereoselectivity such as diastereoselectivity in a targeted manner and at least partial suppression of the formation of undesired side-products and/or undesired stereoisomers, in particular undesired diastereomers.
    Type: Application
    Filed: August 21, 2013
    Publication date: December 19, 2013
    Applicant: Gruenenthal GmbH
    Inventors: Helmut Heinrich BUSCHMANN, Joerg Holenz
  • Patent number: 8552219
    Abstract: Provided is a process for the preparing 1-phenyl-3-dimethylaminopropane derivatives of formula I, (The formula should be inserted here) and its pharmaceutically acceptable salts thereof via novel intermediates.
    Type: Grant
    Filed: September 20, 2011
    Date of Patent: October 8, 2013
    Assignee: Ind-Swift Laboratories Limited
    Inventors: Shekhar Bhaskar Bhirud, Perminder Singh Johar, Sushanta Mishra, Danish Jamshad
  • Publication number: 20130231478
    Abstract: The invention discloses a novel intermediate for preparing tapentadol and analogues thereof, wherein the structural formula is shown as formula I or II, and the groups are defined as the specification. The invention further discloses a method for preparing the novel intermediate and use of the intermediate for preparing tapentadol and analogues thereof. The invention can remarkably improve the product yield and quality of tapentadol, reduce the production cost, and simplify the production procedure. The preparation process is environment friendly, thus more suitable for the requirements of industrial production.
    Type: Application
    Filed: July 29, 2011
    Publication date: September 5, 2013
    Inventors: Ziao Xu, Yuanhai Zhao, Degang Li, Xiaoxiang Li
  • Patent number: 8212080
    Abstract: A method of producing xylylenediamine by the hydrogenation of dicyanobenzene obtained by the ammoxidation of xylene in a high yield while prolonging the catalyst life. In the method, a molten dicyanobenzene from which compounds having a boiling point lower than that of dicyanobenzene have been removed but compounds having a boiling point higher than that of dicyanobenzene are not removed is dissolved in a solvent containing liquid ammonia. By this dissolution, at least part of dicyanobenzene polymers precipitates as insolubles. The precipitates are removed by a solid-liquid separation. By subjecting the resulting solution containing the dicyanobenzene polymers in a reduced amount to hydrogenation, xylylenediamine is produced in a high yield and the life time of hydrogenation catalyst is prolonged.
    Type: Grant
    Filed: December 8, 2009
    Date of Patent: July 3, 2012
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tatsuyuki Kumano, Kenji Nakaya, Shinichi Nagao
  • Patent number: 8106242
    Abstract: Multi-step process for the preparation of compounds via hazardous intermediates comprising the steps of a) preparing in a microreactor a hazardous intermediate and b) optionally performing one or more reaction steps on the hazardous intermediate in one or more additional microreactors and c) further converting the hazardous intermediate with a suitable reaction agent in a subsequent microreactor until a stable end product is formed.
    Type: Grant
    Filed: May 23, 2007
    Date of Patent: January 31, 2012
    Assignee: DSM IP Assets B.V.
    Inventors: Rafael Wilhelmus Elisabeth Ghislain Reintjens, Quirinus Bernardus Broxterman, Martina Kotthaus, Peter Poechlauer
  • Publication number: 20110306793
    Abstract: A process for the preparation of substituted 3-(1-amino-2-methylpentane-3-yl)phenyl compounds.
    Type: Application
    Filed: June 14, 2011
    Publication date: December 15, 2011
    Applicant: Gruenenthal GmbH
    Inventors: Helmut Heinrich BUSCHMANN, Joerg HOLENZ
  • Publication number: 20110281954
    Abstract: Methods of preparing cinacalcet, cinacalcet derivatives, and salts thereof is disclosed herein. Also disclosed herein are polymorphs of cinacalcet, compositions of cinacalcet, and methods of treating a subject by administering cinacalcet, wherein cinacalcet is prepared by the disclosed methods.
    Type: Application
    Filed: May 17, 2011
    Publication date: November 17, 2011
    Inventors: Oliver Thiel, Charles Bernard, Robert Larsen, Michael John Martinelli, Masooma Tamim Raza
  • Publication number: 20110034704
    Abstract: A process for hydrogenating a sample in a pressure range below supercritical pressure values includes supplying at least a solvent of the sample to be hydrogenated by a feed pump with a constant volume rate into a flow path to create a base solution; adding the sample being dissolved into the flow path; feeding hydrogen into the flow path through a valve configured to transmit hydrogen only into a single direction; leading the dissolved sample in the presence of a catalyst through a hydrogenation reactor, where the reactor is inserted into a section of the flow path located after the hydrogen feeding position; maintaining the pressure of the reaction in a given pressure range by element of a pressure-adjusting unit, and collecting a hydrogenate formed within the hydrogenation reactor in a product receptacle connected to the end of the flow path.
    Type: Application
    Filed: October 19, 2010
    Publication date: February 10, 2011
    Applicant: THALESNANO ZRT.
    Inventors: Ferenc Darvas, Lajos Gödörházy, Tamás Karancsi, Dániel Szalay, Ferenc Boncz, László Ürge
  • Patent number: 7816533
    Abstract: A process for the catalytic hydrogenation or asymmetric hydrogenation of imines of Formula (I) to the corresponding amines of Formula (II) is provided in which R1 is aryl; R2 is aryl, cyclic, alkyl, alkenyl or alkynyl; and R3 is alkyl. The catalytic system includes a ruthenium complex containing (1) a diamine and (2) a diphosphine or two monodentate phosphines ligands. Such process also relates to the asymmetric hydrogenation of prochiral imines to the chiral amines using chiral ruthenium complexes bearing chiral diphosphines or chiral monodentate phosphines and chiral diamines.
    Type: Grant
    Filed: December 15, 2004
    Date of Patent: October 19, 2010
    Inventor: Kamaluddin Abdur-Rashid
  • Publication number: 20100094055
    Abstract: The present invention relates to an improved process for the preparation of essentially pure Venlafaxine Hydrochloride. Particularly, the process for the preparation of Venlafaxine Hydrochloride comprises the following steps: i) Preparation of 1-[Cyano-1-(4-methoxyphenyl)methyl]cyclohexanol, ii) Preparation of crude Venlafaxine Hydrochloride by reduction of 1-[Cyano-1-(4-methoxyphenyl)methyl]cyclohexanol with Alkali metal borohydride and Lewis acid and subsequent conversion to Venalfaxine hydrochloride with formic acid and paraformaldehyde and finally iii) Purification of crude Venlafaxine Hydrochloride.
    Type: Application
    Filed: January 9, 2007
    Publication date: April 15, 2010
    Applicant: PHARMATHEN S.A.
    Inventors: Rohit Ravikant Soni, Theocharis Koftis, Theodoros Panagiotidis, Ioanna Georgopoulou
  • Patent number: 7652170
    Abstract: 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: Grant
    Filed: December 25, 2006
    Date of Patent: January 26, 2010
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Souda, Naoyuki Takano, Shinzo Seko
  • Publication number: 20090208413
    Abstract: The present invention provides compositions and methods for synthesizing labeled drugs. The present invention further provides methods for preventing or stopping prescription drug abuse for all agents registered as a Drug Enforcement Agency (DEA) schedule II through schedule V medications. According to the present invention, methods are provided for monitoring patient compliance with prescribed drug treatment. The present invention also provides methods for facilitating a replacement prescription when a patient is left without access to their prescribed drug. Furthermore, the present invention provides a method to improve employee compliance with an employer's drug policies via either a voluntary or compulsory system for enhanced drug testing.
    Type: Application
    Filed: February 23, 2006
    Publication date: August 20, 2009
    Inventors: Alan J Reis, Christian Schafmeister
  • Patent number: 7417170
    Abstract: Methods for the dehydration of substituted 1-amino-3-aryl-butan-3-ol compounds for the preparation of substituted 3-aryl-butyl-amine compounds.
    Type: Grant
    Filed: December 6, 2005
    Date of Patent: August 26, 2008
    Assignee: Gruenenthal GmbH
    Inventors: Wolfgang Hell, Markus Kegel, Bernhard Akteries, Helmut Buschmann, Jorg Holenz, Harmut Loebermann, Detlef Heller, Hans-Joachim Drexler, Stefan Gladow
  • 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: 6849767
    Abstract: A method of hydroborating an alkene or alkyne, or reducing an organic functionality, oxidizing primary and secondary alcohols using a fluorous borane-sulfide is disclosed. The method includes regeneration and recycling the fluorous borane-sulfide.
    Type: Grant
    Filed: July 24, 2003
    Date of Patent: February 1, 2005
    Assignee: The Board of Trustees of the University of Illinois
    Inventors: David C. Crich, Santhosh Neelamkavil
  • Patent number: 6462242
    Abstract: Benzyl alcohols, particularly those which bear fluorine substituents or fluoroalkyl substituents on the benzyl ring, can be obtained by formylation of corresponding aryl bromides to form benzaldehydes and reduction of the latter using further formate, wherein the benzaldehydes formed do not have to be isolated.
    Type: Grant
    Filed: June 5, 2000
    Date of Patent: October 8, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Torsten Neugebauer, Albrecht Marhold
  • Patent number: 6441239
    Abstract: The invention relates to a process for preparing 2-(4-trifluoromethoxyphenyl)ethylamine in an advantageous manner by (a) converting trifluoromethoxybenzene by halomethylation into halogenomethyl-1-trifluoromethoxybenzene, (b) converting the halogenomethyl-1-trifluoromethoxybenzene by halogen-cyano exchange into 4-(trifluoromethoxyphenyl)acetonitrile, and (c) reducing the 4-(trifluoromethoxyphenyl)acetonitrile using hydrogen in the presence of a nickel catalyst to form 2-(4-trifluoromethoxyphenyl)ethylamine. The first step of this process also represents an advantageous process for preparing 4-bromomethyl- and 4-chloromethyl-1-trifluoromethoxybenzene.
    Type: Grant
    Filed: December 20, 2001
    Date of Patent: August 27, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Peter Müller
  • Publication number: 20020082454
    Abstract: The invention relates to a process for preparing 2-(4-trifluoromethoxyphenyl)ethylamine in an advantageous manner by
    Type: Application
    Filed: December 20, 2001
    Publication date: June 27, 2002
    Inventors: Albrecht Marhold, Peter Muller
  • Patent number: 6399828
    Abstract: A process for making compound of formula I from a phenylpropanolamine salt of formula II wherein: R1 is hydrogen or a lower alkyl group; each R2 is independently a hydrogen, halogen, lower alkyl group, lower alkoxy groups, lower alkyl group substituted with 1 to 5 halogens, lower alkoxy groups substituted with 1 to 5 halogens, or both R2 together when on adjacent carbons constitute a —O(CH2)xO— where x is 1 to 4, thereby forming a ring structure fused with the phenyl group; R3 is a C1-C8-alkyl group, a C1-C12-aralkyl group, C1-C12-alkaryl group, or a phenyl group, each optionally substituted by 1 to 5 substituents selected from halogen, hydroxy, or C1-C6-alkyl; and HX is an equivalent of an organic or inorganic acid, the process comprising: (a) acylating the phenylpropanolamine salt of formula II with an acylating agent in a solvent at elevated temperature to make a reaction mixture containing an O-acylated phenylpropanolamine salt of formula III which can
    Type: Grant
    Filed: October 29, 2001
    Date of Patent: June 4, 2002
    Assignee: Boehringer Ingelheim Chemicals, Inc.
    Inventors: Robert Frederick Boswell, Young Sek Lo
  • Publication number: 20020007086
    Abstract: The invention relates to a process for producing a trifluotomethylbenzylamine represented by the following general formula (1), 1
    Type: Application
    Filed: April 12, 2001
    Publication date: January 17, 2002
    Inventors: Satoru Narizuka, Takashi Kume
  • Patent number: 6252114
    Abstract: The invention provides a process for the preparation of 4-(p-methoxyphenyl)-2-aminobutane represented by structural formula (1) as shown herein below: [C11H17ON=4-(p-methoxy phenyl)-2-amino butane] said process comprising the steps of, (a) isolating a phenolic compound 4-hydroxyphenyl)-butan-2-ol from the leaves of Taxus wallichiana by known methods, (b) treating the phenolic compound in aqueous mineral acid to obtain a phenolic halide derivative, (c) converting the phenolic halide derivative into its methyl ether by treating it with a methating agent, (d) reacting the methyl ether halide with azide to obtain an azido derivative, and (e) hydrogenating the azido compound to obtain 4-(p-methoxyphenyl)-2-aminobutane.
    Type: Grant
    Filed: March 24, 2000
    Date of Patent: June 26, 2001
    Assignee: Council of Scientific and Industrial Research
    Inventors: Sunil Kumar Chattopadhyay, Koneni Venkata Sashidhara, Vinayak Tripathi, Arun Kumar Tripathi, Veena Prajapati, Sushil Kumar
  • Patent number: 5840989
    Abstract: The invention relates to a method of doping a Raney nickel catalyst doped with metals by the incorporation of the doping metals in the form of a complex into the alkaline attack medium. Also disclosed is a process for the hydrogenation of nitriles to amines using said catalyst.
    Type: Grant
    Filed: September 24, 1996
    Date of Patent: November 24, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Georges Cordier, Pierre Fouilloux, Nathalie Laurain
  • Patent number: 5756769
    Abstract: A method for producing a propargylamine compound represented by the general formula (I): ##STR1## which comprises reacting a propargyl compound represented by the general formula (II): ##STR2## with an aromatic aldehyde represented by the general formula (III):ArCHO (III)and ammonia to obtain an imine compound represented by the general formula (IV): ##STR3## and hydrolyzing the resultant imine compound. It is to provide a method for producing a propargylamine compound from a propargyl compound by a simple operation without using a special facility, using ammonia as a reaction reagent, without producing a dipropatygylamine compound and a tripropargylamine compound as by-products.
    Type: Grant
    Filed: May 30, 1997
    Date of Patent: May 26, 1998
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Shinzo Seko, Akihiko Nakamura, Motoo Hazama
  • Patent number: 5710274
    Abstract: Disclosed are compounds of the formula: ##STR1## or the pharmaceutically acceptable acid addition salts thereof, wherein: R.sub.1, R.sub.2, R.sub.3, R.sub.4 are the same or different and represent hydrogen, C.sub.1 -C.sub.6 alkyl, halogen, hydroxy, amino, cyano, nitro, trifluoromethyl, trifluoromethoxy, C.sub.1 -C.sub.6 alkoxy, --O.sub.2 CR', --NHCOR', --COR', --SO.sub.m R', where R' is C.sub.1 -C.sub.6 alkyl and wherein m is 0, 1, or 2; orR.sub.1, R.sub.2, R.sub.3, R.sub.4 independently represent --CONR'.sub.m, or --NR'.sub.m where m is 0, 1 or 2 and R' is hydrogen or C.sub.1 -C.sub.6 alkyl;R.sub.5 is hydrogen or C.sub.1 -C.sub.6 alkyl; andR represents an aminoalkyl group,which compounds are useful in the treatment of affective disorders such as schizophrenia, depression, Alzheimer's disease, movement disorders such as Parkinsonism and dystonia, and other disorders which respond to dopaminergic blockage such as substance abuse and obsessive compulsive disorders.
    Type: Grant
    Filed: February 28, 1996
    Date of Patent: January 20, 1998
    Assignee: Neurogen Corporation
    Inventors: Jun Yuan, Xi Chen
  • Patent number: 5679854
    Abstract: The present invention relates to a novel process for preparing (E)-1-amino-2-(fluoromethylene)-4-(p-fluorophenyl)butane, also known in the art as (E)-(p-fluorophenethyl)-3-fluoroallylamine, novel intermediates thereof, a novel process for the preparing (E)-2-(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol, and a novel process for preparing alkali metal salts of diformylamide.
    Type: Grant
    Filed: August 25, 1995
    Date of Patent: October 21, 1997
    Assignee: Hoechst Marion Roussel, Inc.
    Inventors: Jonathan C. Evans, Christian T. Goralski, Daniel R. Henton, Cynthia L. Rand, Paul C. Vosejpka
  • Patent number: 5648540
    Abstract: A method of making (R)-N-[1-(3-methoxyphenyl)ethyl]-3-(2-chlorobenzene)propanamine which involves reducing the appropriate amidyl or iminyl precursor with an appropriate reducing agent. The appropriate amidyl or iminyl precursor is made from a synthesis involving the use of (R)-3-methoxy-.alpha.-methylbenzylamine. A method of condensing a nitrile with a primary or secondary amine to form an imine involves the reaction of a nitrile with diisobutylaluminum hydride; and then reacting the resultant compound with a primary or secondary amine to form the imine. The process is especially useful for producing enantiomerically pure chiral imines, and, ultimately, amines. Typical such imines have the formula: ##STR1## wherein R, R.sub.1, R.sub.2 and R.sub.3 are independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, aryl and aralkyl.
    Type: Grant
    Filed: May 22, 1995
    Date of Patent: July 15, 1997
    Assignee: NPS Pharmaceuticals, Inc.
    Inventors: Bradford C. VanWagenen, Steven R. Duff, William A. Nelson, Thomas E. D'Ambra
  • Patent number: 5648541
    Abstract: A process for preparing an R enantiomer of a compound of the formula (I): ##STR1## wherein Ar is 3-methoxyphenyl, 3-chlorophenyl, or 1-naphthyl, and X is independently selected from the group consisting of H, F, Cl, Br, I, phenyl, CF.sub.3, CF.sub.2 H, CFH.sub.2, lower alkyl (e.g., Me), O-lower alkyl (e.g., OMe), OCH.sub.2 CF.sub.3, OH, CN, NO.sub.2, C(O)-lower alkyl (e.g., C(O)Me), C(O)O-lower alkyl (e.g., C(O)OMe), C(O)NH-lower alkyl (e.g., C(O)NH--Me), C(O)N-lower alkyl.sub.2 (e.g., C(O)NMe.sub.2), OC(O)-lower alkyl (e.g., OC(O)Me), and NH--C(O)-lower alkyl (e.g., NH--C(O)Me), where "lower alkyl" is selected from a group consisting of 1 to 6 carbon atoms, and m is an integer between 1 and 5, by asymmetrically and enantioselectively reducing an imine with a reducing agent/chiral auxiliary agent complex so as to produce an enantiomeric excess of R enantiomer of the compound of formula (I) over the S enantiomer of the compound of formula (I).
    Type: Grant
    Filed: September 28, 1995
    Date of Patent: July 15, 1997
    Assignee: NPS Pharmaceuticals, Inc.
    Inventors: Bradford C. VanWagenen, Robert M. Barmore
  • Patent number: 5627293
    Abstract: The invention relates to ferrocenyldiphosphine ligands containing a silylene group, ferrocenyldiphosphines bound to inorganic or polymeric organic supports by this silylene group, their preparation and also their metal complexes with transition metals such as rhodium or iridium. The invention also relates to the use of these complexes for hydrogenating organic double or triple bonds, in particular olefinic double bonds and carbon-heteroatom double bonds. The complexes are particularly suitable for enantioselective hydrogenation using chiral diphosphines and prochiral unsaturated compounds.The preparation of these immobilized ferrocenyldiphosphines has only been made possible by the provision of correspondingly functionalized ferrocenyldiphosphines. These compounds and their preparation are likewise novel.Accordingly, the invention also provides compounds of the formula I ##STR1## in which R.sub.1 is C.sub.1 -C.sub.8 alkyl, phenyl or phenyl substituted by from 1 to 3 C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.
    Type: Grant
    Filed: February 23, 1996
    Date of Patent: May 6, 1997
    Assignee: Ciba-Geigy Corporation
    Inventor: Benoit Pugin
  • Patent number: 5530125
    Abstract: A novel process for the preparation of .alpha.-substituted arylacetamides wherein the substituent is an aromatic group or a 1-alkenyl or 1-cycloalkenyl group and wherein the nitrogen atom carries no hydrogen atoms comprises the reaction of an arylacetamide having one or two hydrogen atoms on the .alpha.-carbon atom, wherein the nitrogen atom carries no hydrogen atoms, with a strong base in an inert aprotic organic solvent, followed by reaction with a zerovalent transition metal catalyst and then with a compound of the formula R.sup.4 --X, wherein R.sup.4 is selected from aromatic groups, 1-alkenyl groups and 1-cycloalkenyl groups and X is a particular leaving group, especially a triflate group. The .alpha.-substituted arylacetamides are useful as intermediates in the preparation (by reduction) of .alpha.-substituted arylethylamines, e.g., 1-substituted-2,3,4,5-tetrahydro-1H-3-benzazepines, having pharmacological activity. Certain benzazepines wherein the 1-substituent R.sup.4 is 1-(1-cycloalkenyl) are novel.
    Type: Grant
    Filed: August 19, 1994
    Date of Patent: June 25, 1996
    Assignee: Schering Corportion
    Inventors: Joel G. Berger, Wei K. Chang, Joseph A. Kozlowski, Guowei Zhou
  • Patent number: 5504253
    Abstract: A method of making (R)-N- 1-(3-methoxyphenyl)ethyl!-3-(2-chlorobenzene)propanamine which involves reducing the appropriate amidyl or iminyl precursor with an appropriate reducing agent. The appropriate amidyl or iminyl precursor is made from a synthesis involving the use of (R)-3-methoxy-.alpha.-methylbenzylamine. A method of condensing a nitrile with a primary or secondary amine to form an imine involves the reaction of a nitrile with diisobutylaluminum hydride; and then reacting the resultant compound with a primary or secondary amine to form the imine. The process is especially useful for producing enantiomerically pure chiral imines, and, ultimately, amines. Typical such imines have the formula: ##STR1## wherein R, R.sub.1, R.sub.2 and R.sub.3 are independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, aryl and aralkyl.
    Type: Grant
    Filed: July 15, 1994
    Date of Patent: April 2, 1996
    Assignee: NPS Pharmaceuticals, Inc.
    Inventors: Bradford C. VanWagenen, Thomas E. D'Ambra
  • Patent number: 5442120
    Abstract: The invention relates to a process for the production of an acid addition salt of a dobutamine compound of the general formula ##STR1## wherein R is a hydrogen atom or a methyl group, and n is 1 or 2,by reacting a mineral acid--addition salt of a dopamine compound of the general formula ##STR2## with a ketone of the general formula ##STR3## under the influence of a catalytic amount of a base, and in the presence of hydrogen and a hydrogenation catalyst, after which the pH of the reaction mixture is adjusted to approx. 6 at most and the product is isolated.
    Type: Grant
    Filed: April 8, 1994
    Date of Patent: August 15, 1995
    Assignee: Duphar International Research B.V.
    Inventors: Paulus F. C. van der Meij, Paulus P. G. de Jong
  • Patent number: 5436371
    Abstract: A process for preparing p-nitroaromatic amides is provided which comprises contacting a nitrile, nitrobenzene, a suitable base and water in the presence of a suitable solvent system to form a mixture, and reacting the mixture at a suitable temperature in a confined reaction zone in the presence of a controlled amount of protic material. The p-nitroaromatic amides of the invention can be reduced to p-aminoaromatic amides. In one embodiment, the p-aminoaromatic amide is further reacted with ammonia under conditions which produce the corresponding p-aminoaromatic amine and the amide corresponding to the nitrile starting material or with water in the presence of a suitable basic or acidic catalyst under conditions which produce the corresponding p-aminoaromatic amine and the acid or salt thereof corresponding to the nitrile starting material. In another embodiment, the p-aminoaromatic amine is reductively alkylated to produce alkylated p-aminoaromatic amine.
    Type: Grant
    Filed: August 29, 1994
    Date of Patent: July 25, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K. Cheng
  • Patent number: 5360724
    Abstract: One chiral form of a 1-aryl-2-aminopropane is produced in preference to its enantiomer by allowing a 1-arylpropan-2-one to react with a 1-amino-1-phenylethane of predominantly one chiral form and reducing the resultant 1-(1-arylprop-2-ylideneimino)-1-phenylethane to yield phenylethane and a mixture of 1-aryl-2-aminopropanes in which one chiral form thereof is present in preference to its enantiomer. The mixture of 1-aryl-2-aminopropanes then is subjected to the action of an omega-amino acid transaminase which converts one of the two chiral forms of 1-aryl-2-aminopropane into the corresponding arylpropanone which can be separated from the remaining chiral form of the 1-aryl-2-aminopropane.
    Type: Grant
    Filed: December 18, 1992
    Date of Patent: November 1, 1994
    Assignee: Celgene Corporation
    Inventors: George W. Matcham, Seujo Lee
  • Patent number: 5292893
    Abstract: A process is provided for catalytically reducing imines, oximes, hydrazones and related compounds. Moreover, there is provided a process for the catalytic asymmetric reduction of imines, oximes, hydrazones, and the like, using enantiomerically enriched catalysts, to provide chiral amine reaction products which are enriched in one enantiomer. Catalytic asymmetric reduction can also be carried out using an achiral precatalyst in combination with aThe U.S. Government has rights in this invention pursuant to NIH Grant Number GM 34917.
    Type: Grant
    Filed: November 14, 1991
    Date of Patent: March 8, 1994
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen L. Buchwald, Christopher A. Willoughby
  • Patent number: 5220067
    Abstract: This invention provides a process for directly preparing hydrohalide salts of arylethylamines from (.alpha.-chloro-.alpha.-oximino)acetophenones. The process involves hydrogenation in presence of a transition metal catalyst in an organic acid in substantial absence of moisture. The process is illustrated by conversion of 4-hydroxy (.alpha.-chloro-.alpha.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: June 15, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Ahmed Tafesh, B. Frank Wood, Joseph A. McDonough, Graham N. Mott
  • Patent number: 5220066
    Abstract: This invention provides a process for directly preparing arylethylamines and their salts from (.alpha.-halo-.alpha.-oximino)acetophenones. The process involves hydrogenation in presence of a transition metal catalyst. The process is illustrated by conversion of 4-hydroxy-(.alpha.-chloro-.alpha.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: June 15, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Ahmed Tafesh, B. Frank Wood, Joseph A. McDonough, Graham N. Mott
  • Patent number: 5220020
    Abstract: A process is provided whereby organic carbonyl substrates, including esters, lactones, ketones, amides and imides are reduced in a reaction with a silane reducing reagent and a catalyst. Exemplary catalysts include metal alkoxides and metal aryloxides.
    Type: Grant
    Filed: November 14, 1991
    Date of Patent: June 15, 1993
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
  • Patent number: 5220068
    Abstract: 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: Grant
    Filed: January 29, 1991
    Date of Patent: June 15, 1993
    Assignee: Chinoin Gyogyszer - es Vegyeszeti Termekek Gyara Rt.
    Inventors: Jozsef Knoll, Antal Simay, Eva Szinnyei, Eva Somfai, Zoltan Torok, Karoly Mozsolits, Janos Bergmann
  • Patent number: 5200561
    Abstract: Disclosed is a process for producing an optically active amine represented by the formula (IV) ##STR1## wherein R.sub.7 and R.sub.8 each denote an alkyl group, aryl group or aralkyl group, providing that they do not denote the same group at the same time, and * indicates an asymmetric carbon atom, which comprises reacting an asymmetric reducing agent obtained from (1) an optically active amine derivative represented by the formula (I) ##STR2## wherein R.sub.1 denotes an alkyl group, aryl group or aralkyl group; R.sub.2 denotes a hydrogen atom, alkyl group or aralkyl group; R.sub.3 denotes an aryl group or a substituent represented by the formula (II) ##STR3## wherein R.sub.4 and R.sub.5 each denote a hydrogen atom, aryl group or aralkyl group, and * is as defined above, (2) a metal borohydride and (3) sulfuric acid, with either the syn-isomer or the anti-isomer of an oxime derivative represented by the formula (III) or with a mixture rich in either one of the two isomers ##STR4## wherein R.sub.
    Type: Grant
    Filed: October 7, 1991
    Date of Patent: April 6, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Naoto Konya, Yukio Yoneyoshi, Yoji Sakito, Shinji Nishii, Gohfu Suzukamo, Hiroko Sakane
  • Patent number: 5175368
    Abstract: Arylalkylamines (as the hydrochloride salt), e.g. tyramine hydrochloride, are prepared by hydrogenating substituted or unsubstituted aryl-.alpha.-oximinoalkyl ketones, e.g. p-hydroxyisonitroacetophenone, in either in an aqueous reaction medium comprising hydrochloric acid, essentially without the presence of a lower alkyl alcohol in said reaction medium, or in an aqueous reaction medium comprising water, hydrochloric acid, and a lower alkyl alcohol, wherein the alcohol comprises less than about 90% by volume of the reaction medium. A substituent on the aryl portion of the aryl-.alpha.-oximinoalkyl ketone must be on a position which activates the aromatic ring.
    Type: Grant
    Filed: June 29, 1992
    Date of Patent: December 29, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Ahmed M. Tafesh, Joseph A. McDonough, Graham N. Mott
  • Patent number: 5113025
    Abstract: A process for selective reduction is provided wherein an organic compound containing a reducible group such as acid, acid chloride, ester, aldehyde, ketone, epoxide, amide, oxime, imine, nitrile, or the like, is reacted with a tertiary amine alane such that an alcohol or an amine is produced, substantially without reduction of another group in the molecule such as a halogen-containing functionality, nitro group, or double bond.
    Type: Grant
    Filed: March 5, 1991
    Date of Patent: May 12, 1992
    Assignee: Ethyl Corporation
    Inventors: Won S. Park, Everett M. Marlett
  • Patent number: 5057624
    Abstract: New process for the synthesis of the N-methyl-3,4-dimetoxyphenylethylamine of formula ##STR1## intermediate in the synthesis of the drug internationally known as verapamil. The process starts from the 3,4-dimethoxybenzaldehyde which, by means of a Darzens condensation, gives an epoxyester that, by alkaline hydrolysis and subsequent decarboxylation, gives the 3,4-dimethoxyphenylacetaldehyde. This aldehyde gives the amine of formula I by reaction with monomethylamine followed by reduction with sodium borohydride.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: October 15, 1991
    Assignee: ALFA Wassermann S.p.A.
    Inventors: Vincenzo Cannata, Giancarlo Tamerlani, Graziano Zagnoni
  • 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: 4960939
    Abstract: N-benzyl-N-methyl-3,4-dimethoxyphenethylamine is prepared by reacting 3,4-dimethoxyphenethylamine with a mixture of benzaldehyde and formaldehyde in the presence of hydrogen and a catalyst such as palladium on carbon.
    Type: Grant
    Filed: June 13, 1984
    Date of Patent: October 2, 1990
    Assignee: Farmos-Yhtyma Oy
    Inventor: Maire M. Eloranta
  • Patent number: 4937384
    Abstract: An amine is produced by reacting an amide with hydrogen at elevated temperature in the presence as catalyst of a composition comprising as a first component (i) a noble metal of Group VIII of the Periodic Table of the Elements, particularly palladium or ruthenium, and (ii) rhenium, which component may be supported, and as a second component either an alumina or a zeolite, preferably a low silica aluminosilicate zeolite, for example type A or type Y zeolite.
    Type: Grant
    Filed: March 16, 1988
    Date of Patent: June 26, 1990
    Assignee: BP Chemicals Limited
    Inventor: Ian D. Dobson
  • Patent number: 4836958
    Abstract: The instant invention relates to fluorinated cationic compounds of the formula ##STR1## wherein R.sub.f is a perfluoroalkyl or perfluoroalkoxy-perfluoroalkyl group;R.sub.1 is alkylene optionally interrupted by --O--, --S--, --SO.sub.2 --, --SO.sub.2 NR'--, --CO.sub.2 --, --NR'--, or --CONR'-- where R' is hydrogen or lower alkyl;m is 0, 1 or 2;R.sub.2 is linear or branched alkylene;R.sub.3, R.sub.4, and R.sub.5 independently of one another represent alkyl or arylalkyl groups which are unsubstituted or substituted by hydroxyl, lower alkoxy, halogen, cyano or by polyalkyleneoxy, or R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached represent a 5- or 6-membered heterocyclic radical or R.sub.3, R.sub.4 and R.sub.5 together with nitrogen atom that links them represent a substituted or unsubstituted pyridine ring; andA.sup..crclbar. represents the anion of an organic or inorganic acid; and their particular use as surfactants.
    Type: Grant
    Filed: July 31, 1986
    Date of Patent: June 6, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanasios Karydas
  • Patent number: 4564705
    Abstract: Aromatic-aliphatic diamines of the formula ##STR1## in which Ar is an arylene or substituted arylene are useful in preparing thermally stable, rigid, polyamides, polyureas and polyurethanes having a repeating unit of the formula ##STR2## in which Ar is arylene or substituted arylene, X is --NH-- or --O--, n is 0 or 1, and R is a divalent organic radical.
    Type: Grant
    Filed: May 21, 1981
    Date of Patent: January 14, 1986
    Assignee: E. I. Du Pont De Nemours and Company
    Inventors: August H. Frazer, John F. Harris, Jr.