Forming Amine Group Directly By Reduction, Other Than By Reductive Amination Patents (Class 564/375)
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Patent number: 9090539Abstract: 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: GrantFiled: May 24, 2013Date of Patent: July 28, 2015Assignee: AMPAC Fine Chemicals LLCInventors: Brian Morgan, Olivier Dapremont, Patrick Berget, Ali Suleman, William Dubay, Jeffrey D. Butler
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Patent number: 8853393Abstract: 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: GrantFiled: July 29, 2011Date of Patent: October 7, 2014Assignee: Anhui New Star Pharmaceutical Development Co., Ltd.Inventors: Ziao Xu, Yuanhai Zhao, Degang Li, Xiaoxiang Li
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Patent number: 8669399Abstract: 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: GrantFiled: June 14, 2011Date of Patent: March 11, 2014Assignee: Grünenthal GmbHInventors: Helmut Heinrich Buschmann, Joerg Holenz
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Publication number: 20130338399Abstract: 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: ApplicationFiled: August 21, 2013Publication date: December 19, 2013Applicant: Gruenenthal GmbHInventors: Helmut Heinrich BUSCHMANN, Joerg Holenz
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Patent number: 8552219Abstract: 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: GrantFiled: September 20, 2011Date of Patent: October 8, 2013Assignee: Ind-Swift Laboratories LimitedInventors: Shekhar Bhaskar Bhirud, Perminder Singh Johar, Sushanta Mishra, Danish Jamshad
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Publication number: 20130231478Abstract: 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: ApplicationFiled: July 29, 2011Publication date: September 5, 2013Inventors: Ziao Xu, Yuanhai Zhao, Degang Li, Xiaoxiang Li
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Patent number: 8212080Abstract: 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: GrantFiled: December 8, 2009Date of Patent: July 3, 2012Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tatsuyuki Kumano, Kenji Nakaya, Shinichi Nagao
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Patent number: 8106242Abstract: 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: GrantFiled: May 23, 2007Date of Patent: January 31, 2012Assignee: DSM IP Assets B.V.Inventors: Rafael Wilhelmus Elisabeth Ghislain Reintjens, Quirinus Bernardus Broxterman, Martina Kotthaus, Peter Poechlauer
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Publication number: 20110306793Abstract: A process for the preparation of substituted 3-(1-amino-2-methylpentane-3-yl)phenyl compounds.Type: ApplicationFiled: June 14, 2011Publication date: December 15, 2011Applicant: Gruenenthal GmbHInventors: Helmut Heinrich BUSCHMANN, Joerg HOLENZ
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Publication number: 20110281954Abstract: 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: ApplicationFiled: May 17, 2011Publication date: November 17, 2011Inventors: Oliver Thiel, Charles Bernard, Robert Larsen, Michael John Martinelli, Masooma Tamim Raza
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Publication number: 20110034704Abstract: 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: ApplicationFiled: October 19, 2010Publication date: February 10, 2011Applicant: THALESNANO ZRT.Inventors: Ferenc Darvas, Lajos Gödörházy, Tamás Karancsi, Dániel Szalay, Ferenc Boncz, László Ürge
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Patent number: 7816533Abstract: 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: GrantFiled: December 15, 2004Date of Patent: October 19, 2010Inventor: Kamaluddin Abdur-Rashid
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Publication number: 20100094055Abstract: 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: ApplicationFiled: January 9, 2007Publication date: April 15, 2010Applicant: PHARMATHEN S.A.Inventors: Rohit Ravikant Soni, Theocharis Koftis, Theodoros Panagiotidis, Ioanna Georgopoulou
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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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Publication number: 20090208413Abstract: 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: ApplicationFiled: February 23, 2006Publication date: August 20, 2009Inventors: Alan J Reis, Christian Schafmeister
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Patent number: 7417170Abstract: 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: GrantFiled: December 6, 2005Date of Patent: August 26, 2008Assignee: Gruenenthal GmbHInventors: Wolfgang Hell, Markus Kegel, Bernhard Akteries, Helmut Buschmann, Jorg Holenz, Harmut Loebermann, Detlef Heller, Hans-Joachim Drexler, Stefan Gladow
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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: 6849767Abstract: 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: GrantFiled: July 24, 2003Date of Patent: February 1, 2005Assignee: The Board of Trustees of the University of IllinoisInventors: David C. Crich, Santhosh Neelamkavil
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Patent number: 6462242Abstract: 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: GrantFiled: June 5, 2000Date of Patent: October 8, 2002Assignee: Bayer AktiengesellschaftInventors: Torsten Neugebauer, Albrecht Marhold
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Patent number: 6441239Abstract: 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: GrantFiled: December 20, 2001Date of Patent: August 27, 2002Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Peter Müller
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Publication number: 20020082454Abstract: The invention relates to a process for preparing 2-(4-trifluoromethoxyphenyl)ethylamine in an advantageous manner byType: ApplicationFiled: December 20, 2001Publication date: June 27, 2002Inventors: Albrecht Marhold, Peter Muller
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Patent number: 6399828Abstract: 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 canType: GrantFiled: October 29, 2001Date of Patent: June 4, 2002Assignee: Boehringer Ingelheim Chemicals, Inc.Inventors: Robert Frederick Boswell, Young Sek Lo
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Publication number: 20020007086Abstract: The invention relates to a process for producing a trifluotomethylbenzylamine represented by the following general formula (1), 1Type: ApplicationFiled: April 12, 2001Publication date: January 17, 2002Inventors: Satoru Narizuka, Takashi Kume
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Patent number: 6252114Abstract: 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: GrantFiled: March 24, 2000Date of Patent: June 26, 2001Assignee: Council of Scientific and Industrial ResearchInventors: Sunil Kumar Chattopadhyay, Koneni Venkata Sashidhara, Vinayak Tripathi, Arun Kumar Tripathi, Veena Prajapati, Sushil Kumar
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Patent number: 5840989Abstract: 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: GrantFiled: September 24, 1996Date of Patent: November 24, 1998Assignee: Rhone-Poulenc ChimieInventors: Georges Cordier, Pierre Fouilloux, Nathalie Laurain
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Patent number: 5756769Abstract: 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: GrantFiled: May 30, 1997Date of Patent: May 26, 1998Assignee: Sumitomo Chemical Company, Ltd.Inventors: Shinzo Seko, Akihiko Nakamura, Motoo Hazama
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Patent number: 5710274Abstract: 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: GrantFiled: February 28, 1996Date of Patent: January 20, 1998Assignee: Neurogen CorporationInventors: Jun Yuan, Xi Chen
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Patent number: 5679854Abstract: 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: GrantFiled: August 25, 1995Date of Patent: October 21, 1997Assignee: Hoechst Marion Roussel, Inc.Inventors: Jonathan C. Evans, Christian T. Goralski, Daniel R. Henton, Cynthia L. Rand, Paul C. Vosejpka
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Patent number: 5648540Abstract: 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: GrantFiled: May 22, 1995Date of Patent: July 15, 1997Assignee: NPS Pharmaceuticals, Inc.Inventors: Bradford C. VanWagenen, Steven R. Duff, William A. Nelson, Thomas E. D'Ambra
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Patent number: 5648541Abstract: 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: GrantFiled: September 28, 1995Date of Patent: July 15, 1997Assignee: NPS Pharmaceuticals, Inc.Inventors: Bradford C. VanWagenen, Robert M. Barmore
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Patent number: 5627293Abstract: 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: GrantFiled: February 23, 1996Date of Patent: May 6, 1997Assignee: Ciba-Geigy CorporationInventor: Benoit Pugin
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Patent number: 5530125Abstract: 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: GrantFiled: August 19, 1994Date of Patent: June 25, 1996Assignee: Schering CorportionInventors: Joel G. Berger, Wei K. Chang, Joseph A. Kozlowski, Guowei Zhou
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Patent number: 5504253Abstract: 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: GrantFiled: July 15, 1994Date of Patent: April 2, 1996Assignee: NPS Pharmaceuticals, Inc.Inventors: Bradford C. VanWagenen, Thomas E. D'Ambra
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Patent number: 5442120Abstract: 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: GrantFiled: April 8, 1994Date of Patent: August 15, 1995Assignee: Duphar International Research B.V.Inventors: Paulus F. C. van der Meij, Paulus P. G. de Jong
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Patent number: 5436371Abstract: 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: GrantFiled: August 29, 1994Date of Patent: July 25, 1995Assignee: Monsanto CompanyInventors: Michael K. Stern, Brian K. Cheng
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Patent number: 5360724Abstract: 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: GrantFiled: December 18, 1992Date of Patent: November 1, 1994Assignee: Celgene CorporationInventors: George W. Matcham, Seujo Lee
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Patent number: 5292893Abstract: 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: GrantFiled: November 14, 1991Date of Patent: March 8, 1994Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Christopher A. Willoughby
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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: 5220067Abstract: 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: GrantFiled: March 30, 1992Date of Patent: June 15, 1993Assignee: Hoechst Celanese CorporationInventors: Ahmed Tafesh, B. Frank Wood, Joseph A. McDonough, Graham N. Mott
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Patent number: 5220020Abstract: 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: GrantFiled: November 14, 1991Date of Patent: June 15, 1993Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
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Patent number: 5220066Abstract: 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: GrantFiled: March 30, 1992Date of Patent: June 15, 1993Assignee: Hoechst Celanese CorporationInventors: Ahmed Tafesh, B. Frank Wood, Joseph A. McDonough, Graham N. Mott
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Patent number: 5200561Abstract: 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: GrantFiled: October 7, 1991Date of Patent: April 6, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Naoto Konya, Yukio Yoneyoshi, Yoji Sakito, Shinji Nishii, Gohfu Suzukamo, Hiroko Sakane
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Patent number: 5175368Abstract: 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: GrantFiled: June 29, 1992Date of Patent: December 29, 1992Assignee: Hoechst Celanese CorporationInventors: Ahmed M. Tafesh, Joseph A. McDonough, Graham N. Mott
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Patent number: 5113025Abstract: 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: GrantFiled: March 5, 1991Date of Patent: May 12, 1992Assignee: Ethyl CorporationInventors: Won S. Park, Everett M. Marlett
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Patent number: 5057624Abstract: 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: GrantFiled: March 30, 1990Date of Patent: October 15, 1991Assignee: ALFA Wassermann S.p.A.Inventors: Vincenzo Cannata, Giancarlo Tamerlani, Graziano Zagnoni
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Patent number: 4960939Abstract: 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: GrantFiled: June 13, 1984Date of Patent: October 2, 1990Assignee: Farmos-Yhtyma OyInventor: Maire M. Eloranta
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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: 4937384Abstract: 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: GrantFiled: March 16, 1988Date of Patent: June 26, 1990Assignee: BP Chemicals LimitedInventor: Ian D. Dobson
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Patent number: 4836958Abstract: 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: GrantFiled: July 31, 1986Date of Patent: June 6, 1989Assignee: Ciba-Geigy CorporationInventor: Athanasios Karydas
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Patent number: 4564698Abstract: The present invention relates to new tricyclic compounds of the formula: ##STR1## having valuable CNS and cardiovascular properties.Type: GrantFiled: January 24, 1983Date of Patent: January 14, 1986Assignee: Akzo N.V.Inventors: Johannes H. Wieringa, Frans A. van der Vlugt