Group Viii Noble Metal Containing Catalyst Utilized Patents (Class 564/358)
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Patent number: 9029421Abstract: The present invention provides a process for preparing a compound of formula (VI) or a salt thereof, the process comprising: (i) reacting 4-methoxyphenyl acetone with an amine of formula (VIII) under conditions of reductive amination to produce a compound of formula (II) or a salt thereof, wherein there is no isolation of an imine intermediate formed during the reductive amination; (ii) condensing the compound (II) or the acid addition salt thereof with an ?-haloketone of formula (III) to produce the compound of formula (IV); (iii) reducing the compound (IV) to a compound of formula (V); and (iv) reducing the compound (V) to the compound of formula (VI), wherein the reduction is carried out in the presence of either (1) a hydrogen donating compound in the presence of a hydrogen transfer catalyst; or (2) ammonium formate using a hydrogenation catalyst, wherein R1 and R2 are independently optionally substituted arylalkyl, and Hal is selected from chloro or bromo.Type: GrantFiled: June 2, 2009Date of Patent: May 12, 2015Assignee: Cipla LimitedInventors: Vaishali Vaman Haldavanekar, Mangesh Prabhu, Dharmaraj Ramachandra Rao, Rajendra Narayanrao Kankan
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Patent number: 8618326Abstract: Disclosed is a method of making a 2-substituted-1,4-benzenediamine by nucleophilic aromatic substitution.Type: GrantFiled: January 28, 2011Date of Patent: December 31, 2013Assignee: The Procter & Gamble CompanyInventors: John Michael Gardlik, Garry Steven Garrett, Bryan Patrick Murphy, Guiru Zhang, Robert Edward Shumate, James S. Anderson
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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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Patent number: 8207379Abstract: A novel ruthenium compound that is useful as an asymmetric reduction catalyst for carbonyl compounds. The ruthenium compound of the present invention is represented by a formula (I): (Ru(X)2(Pxx)[R1R2C(NH2)—R3R4C(NH2)] (I)), and when this compound is used as an asymmetric reduction catalyst, an optically active aminoalcohol compound can be produced from an ?-aminoketone, and particularly a compound represented by formula (IV), with high stereoselectivity and high yield.Type: GrantFiled: April 3, 2009Date of Patent: June 26, 2012Assignee: Nippon Soda Co., Ltd.Inventors: Masaya Akashi, Tsutomu Inoue
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Publication number: 20110166237Abstract: The present invention provides a process for preparing a compound of formula (VI) or a salt thereof, the process comprising: (i) reacting 4-methoxyphenyl acetone with an amine of formula (VIII) under conditions of reductive amination to produce a compound of formula (II) or a salt thereof, wherein there is no isolation of an imine intermediate formed during the reductive amination; (ii) condensing the compound (II) or the acid addition salt thereof with an ?-haloketone of formula (III) to produce the compound of formula (IV); (iii) reducing the compound (IV) to a compound of formula (V); and (iv) reducing the compound (V) to the compound of formula (VI), wherein the reduction is carried out in the presence of either (1) a hydrogen donating compound in the presence of a hydrogen transfer catalyst; or (2) ammonium formate using a hydrogenation catalyst, wherein R1 and R2 are independently optionally substituted arylalkyl, and Hal is selected from chloro or bromo.Type: ApplicationFiled: June 2, 2009Publication date: July 7, 2011Applicant: CIPLA LIMITEDInventors: Vaman Vaishali Haldavanekar, Mangesh Prabhu, Dharmaraj Ramachandra Rao, Rajendra Narayanrao Kankan
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Publication number: 20110028749Abstract: A novel ruthenium compound that is useful as an asymmetric reduction catalyst for carbonyl compounds. The ruthenium compound of the present invention is represented by a formula (I): (Ru(X)2(Pxx)[R1R2C(NH2)—R3R4C(NH2)] (I)), and when this compound is used as an asymmetric reduction catalyst, an optically active aminoalcohol compound can be produced from an ?-aminoketone, and particularly a compound represented by formula (IV), with high stereoselectivity and high yield.Type: ApplicationFiled: April 3, 2009Publication date: February 3, 2011Applicant: Nippon Soda Co., Ltd.Inventors: Masaya Akashi, Tsutomu Inoue
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Publication number: 20100152490Abstract: The invention relates to a process for preparing ?-aminoacetals substantially in racemic form, comprising a step of oxidizing optically enriched ?-aminoacetals to the corresponding oximes, in the presence of a catalyst, and a step of reducing the oximes thus obtained.Type: ApplicationFiled: May 21, 2007Publication date: June 17, 2010Applicant: CLARIANT SPECIALTY FINE CHEMICALS (FRANCE)Inventors: Muriel Albalat, Geraldine Primazot, Didier Wilhelm, Jean-Claude Vallejos
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Patent number: 7563931Abstract: A process for the preparation of a compound of formula I, wherein R1 and R2 are ortho or para substituents, independently selected from the group consisting of hydrogen, hydroxyl, C1-C6 alkyl, C1-C6 alkoxy, C7-C9 aralkoxy, C2-C7 alkanoyloxy, C1-C6 alkylmercapto, halo and trifluoromethyl; R3 is hydrogen or C1-C6 alkyl; R4 is hydrogen, C1-C6 alkyl, formyl or C2-C7 alkanoyl; n is one of the integers 0, 1, 2, 3 or 4; and the dotted line represents optional olefinic unsaturation; comprising hydrogenating a compound of formula III, in the presence of a nickel or cobalt catalyst at a temperature of about 5° C. to 25° C.Type: GrantFiled: February 20, 2007Date of Patent: July 21, 2009Assignee: WyethInventors: Keun-Sik Kim, Kwang-Il Kim, Ki-Byung Chai
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Patent number: 7488833Abstract: A process for the enantioselective preparation of amino alcohols of formula I by enantioselective hydrogenation of amino ketones of the formula II in the presence of a non-racemic catalyst. The catalyst is a transition-metal complex in which the transition metal is complexed to a chiral diphosphine ligand.Type: GrantFiled: August 1, 2003Date of Patent: February 10, 2009Assignee: Merck Patent GmbHInventors: Joachim Kralik, Kai Fabian, Christoph Mürmann, Norbert Schweickert
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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: 7294744Abstract: The present invention relates to an improved process for preparing enantiomerically pure 3-hydroxy-3-phenyl-propylamines on an industrial scale using asymmetrical hydrogenation as a key step and optionally a special sequence of subsequent steps, using a catalyst system consisting of rhodium and chiral 4-(dicyclohexylphosphino)-2-(diphenyl-phosphino-methyl)-N-methyl-aminocarbonyl-pyrrolidine.Type: GrantFiled: June 30, 2005Date of Patent: November 13, 2007Assignee: Boehringer Ingelheim Pharma GmbH & Co. KGInventors: Wolfgang Baumgarten, Robert Schiffers
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Patent number: 7247750Abstract: Disclosed are processes for preparing levosalbutamol or the pharmacologically acceptable salts thereof on an industrial scale, using asymmetric hydrogenation as the key step and optionally a special sequence of subsequent steps, using rhodium as catalyst and a chiral bidentate phosphine ligand such as (2R, 4R)-4-(dicyclohexylphosphino)-2-(diphenyl-phosphino-methyl)-N-methyl-aminocarbonyl-pyrrolidine as catalyst system.Type: GrantFiled: January 13, 2006Date of Patent: July 24, 2007Assignee: Boehringer Ingelheim Pharma GmbH & Co. KGInventors: Paul Kreye, Alfons Lenhart, Franz Dietrich Klingler
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Patent number: 7217847Abstract: The invention relates to a process for preparing optically active 2-amino-, 2-chloro-, 2-hydroxy- or 2-alkoxy-1-alcohols by catalytically hydrogenating appropriate optically active 2-amino-, 2-chloro-, 2-hydroxy- and 2-alkoxycarboxylic acids or their acid derivatives in the presence of catalysts comprising palladium and rhenium or platinum and rhenium.Type: GrantFiled: August 28, 2003Date of Patent: May 15, 2007Assignee: BASF AktiengesellschaftInventors: Rolf-Hartmuth Fischer, Nils Bottke
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Patent number: 7179944Abstract: A process for the preparation of a compound of formula I, wherein R1 and R2 are ortho or para substituents, independently selected from the group consisting of hydrogen, hydroxyl, C1–C6 alkyl, C1–C6 alkoxy, C7–C9 aralkoxy, C2–C7 alkanoyloxy, C1–C6 alkylmercapto, halo and trifuoromethyl; R3 is hydrogen or C1–C6 alkyl 1, 2, 3 or 4; and the dotted line represents optional olefinic unsaturation; comprising hydrogenating a compound of formula III, in the presence of a nickel or cobalt catalyst at a temperature of about 5° C. to 25° C.Type: GrantFiled: March 9, 2004Date of Patent: February 20, 2007Assignee: WyethInventors: Keun-sik Kim, Kwang-Il Kim, Ki-Byung Chai
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Patent number: 7049469Abstract: The present invention relates to an improved process for preparing levosalbutamol or the pharmacologically acceptable salts thereof on an industrial scale, using asymmetric hydrogenation as the key step and optionally a special sequence of subsequent steps, using rhodium as catalyst and a chiral bidentate phosphine ligand such as (2R,4R)-4-(dicyclohexylphosphino)-2-(diphenyl-phosphino-methyl)-N-methyl-aminocarbonyl-pyrrolidine as catalyst system.Type: GrantFiled: October 23, 2003Date of Patent: May 23, 2006Assignee: Boehringer Ingelheim Pharma GmbH & Co. KGInventors: Paul Kreye, Alfons Lenhart, Franz Dietrich Klingler
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Patent number: 6984738Abstract: The present invention is to provide a process for producing an optically active amino alcohol which is useful for the synthesis of natural substances and as an intermediate for drugs and agricultural chemicals in a high yield, a high selectivity and an economical manner with a good working efficiency and the present invention relates to a process for producing an optically active amino alcohol represented by the following formula (2) (in the formula, R1 is a hydrocarbon group, a substituted hydrocarbon group, an aromatic heterocyclic group, a substituted aromatic heterocyclic group, an aliphatic heterocyclic group or a substituted aliphatic heterocyclic group; R2 and R3 each independently is hydrogen atom, a hydrocarbon group, a substituted hydrocarbon group, an acyl group, an acyloxy group, an alkyloxycarbonyl group, an aralkyloxycarbonyl group, an aryloxycarbonyl group, an aromatic heterocyclic group, a substituted aromatic heterocyclic group, an aliphatic heterocyclic group or a substituted aliphatic hType: GrantFiled: October 17, 2003Date of Patent: January 10, 2006Inventors: Tohru Yokozawa, Kenji Yagi, Takao Saito
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Patent number: 6756502Abstract: Processes for the preparation of Venlafaxine (IX) via the novel epoxy-nitrile intermediate (I), which when subjected to hydrogenation forms compound (X), and may subsequently be reduced to yield the desired product (IX). The epoxy-nitrile intermediate (I) itself may be synthesized via various alternative reaction strategies, from a range of starting materials. E.g. 4-methoxy-benzaldehyde (VI), upon treatment with cyclohexyl magnesium bromide yields compound (V). This in turn may be oxidized to yield compound (III), which forms compound (II) on treatment with an (x-keto-halogenation agent. Cyanation of compound (II), then yields the desired epoxy nitrile intermediate (I), from which Venlafaxine (IX) may be synthesized.Type: GrantFiled: April 10, 2002Date of Patent: June 29, 2004Assignee: Alembic LimitedInventors: Dhiraj Mohansinh Rathod, Srinivasan Rengaraju, Milind Moreshwar Gharpure, Nishant Mahendra Patel, Mandar Manohar Deoahar
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Patent number: 6686505Abstract: A process for producing an optically active amino alcohol is provided that includes a step in which a nitro ketone or a cyano ketone is reacted with a hydrogen-donating organic or inorganic compound in the presence of a transition metal compound catalyst having an optically active nitrogen-containing compound as an asymmetric ligand to give an optically active nitro alcohol or an optically active cyano alcohol, and a step in which the above optically active alcohol is further reduced to efficiently produce an optically active amino alcohol.Type: GrantFiled: October 31, 2002Date of Patent: February 3, 2004Assignee: Kanto Kaguku Kabushiki KaishaInventors: Masahito Watanabe, Kunihiko Murata, Takao Ikariya
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Patent number: 6605744Abstract: Disclosed is a process for the production of 2-amino-2-[2-(4-C2-20-alkyl-phenyl)ethyl]propane-1,3-diols.Type: GrantFiled: May 8, 2001Date of Patent: August 12, 2003Assignees: Novartis AG, Taito Co. Ltd., Mitsubishi Pharma Corp.Inventors: Stephan Abel, Tetsuro Fujita, Ryoji Hirose, Guido Jordine, Tadashi Mishina
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Patent number: 6218575Abstract: An improved process for preparing adrenaline, or an addition salt thereof, on an industrial scale, with asymmetric hydrogenation as a key step and a special sequence of successive steps, using [Rh(COD)Cl]2 as catalyst and a chiral, bidentate phosphine ligand such as (2R,4R)-4-(dicyclohexylphosphino)-2-(diphenylphosphinomethyl)-N-methylaminocarbonylpyrrolidine as the catalyst system.Type: GrantFiled: July 26, 2000Date of Patent: April 17, 2001Assignee: Boehringer Ingelheim Pharma KGInventors: Franz Dietrich Klingler, Lienhard Wolter
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Patent number: 6187956Abstract: The present invention relates to an improved process for preparing L-phenylephrine hydrochloride 3 on an industrial scale by asymmetric hydrogenation as the key step and a special sequence of subsequent steps, using [Rh(COD)Cl]2 as catalyst and a chiral, two-pronged phosphine ligand such as (2R,4R)-4-(dicyclohexylphosphino)-2-(diphenylphosphino-methyl)-N-methyl-aminocarbonyl-pyrrolidine as the catalyst system.Type: GrantFiled: January 19, 2000Date of Patent: February 13, 2001Assignee: Boehringer Ingelheim Pharma KGInventors: Franz Dietrich Klinger, Lienhard Wolter, Wolfgang Dietrich
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Patent number: 6031134Abstract: The invention relates to a novel process for the preparation of 2-amino-2-arylehanols of the formula (I) ##STR1## in which Ar represents aryl or hetaryl each unsubstituted or identically or differently monosubstituted to pentasubstituted, where as substituents there may be mentioned:halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, unsubstituted or substituted cycloalkyloxy or unsubstituted or substituted phenyl,which comprises catalytically hydrogenating .alpha.-hydroxyketoximes of the formula (II) ##STR2## in which Ar has the meaning given above,using Raney nickel or Raney cobalt in the presence of a diluent and in the presence of a base andnovel 2-amino-2-arylethanols and novel .alpha.-hydroxyketoximes.Type: GrantFiled: November 4, 1998Date of Patent: February 29, 2000Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Ernst Kysela, Albrecht Marhold
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Patent number: 5672706Abstract: A process is disclosed for the preparation of the substantially pure compound of the formula: ##STR1## comprising catalytic hydrogenation of a compound of the formula: ##STR2## wherein R.sub.6 and R.sub.7 are independently selected from ##STR3## wherein R.sub.a and R.sub.b are independently selected from hydrogen, loweralkyl and phenyl and R.sub.c, R.sub.d and R.sub.e are independently selected from hydrogen, loweralkyl, trifluoromethyl, alkoxy, halo and phenyl; and ##STR4## wherein the naphthyl ring is unsubstituted or substituted with one, two or three substitutents independently selected from loweralkyl, trifluoromethyl, alkoxy and halo; or R.sub.6 and R.sub.7 taken together with the nitrogen atom to which they are bonded are ##STR5## wherein R.sub.f, R.sub.g, R.sub.h and R.sub.i are independently selected from hydrogen, loweralkyl, alkoxy, halogen and trifluoromethyl; or an acid addition salt thereof.Type: GrantFiled: April 17, 1996Date of Patent: September 30, 1997Assignee: Abbott LaboratoriesInventors: Anthony R. Haight, Owen J. Goodmonson, Shyamal I. Parekh, Timothy A. Robbins, Lou S. Seif
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Patent number: 5631405Abstract: The present invention relates to a method of forming a 1,3-diamino-3-substituted-2-propanol chemical intermediate from which various chemicals, such as selected protease-inhibitors and other drugs, as well as polymers, can be synthesized.This method includes contacting a nitromethyl amino acid compound with at least one reducing agent to form the 1,3-diamino-3-substituted-2-propanol chemical intermediate.Type: GrantFiled: June 7, 1995Date of Patent: May 20, 1997Assignee: Pharm-Eco Laboratories, IncorporatedInventors: Biman Pal, Siya Ram, Bing Cai, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard L. Gabriel
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Patent number: 5618966Abstract: The present invention relates to a method of forming a 1,3-diamino-3-substituted-2-propanol chemical intermediate from which various chemicals, such as selected protease-inhibitors and other drugs, as well as polymers, can be synthesized.This method includes contacting a nitromethyl amino acid compound with at least one reducing agent to form the 1,3-diamino-3-substituted-2-propanol chemical intermediate.Type: GrantFiled: May 16, 1995Date of Patent: April 8, 1997Assignee: Pharm-Eco Laboratories, IncorporatedInventors: Biman Pal, Siya Ram, Bing Cai, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard Gabriel
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Patent number: 5602282Abstract: The invention relates to a novel process for the preparation of 2-amino-2-arylethanols of the formula (I) ##STR1## in which Ar represents aryl or hetaryl each unsubstituted or identically or differently monosubstituted to pentasubstituted, where as substituents there may be mentioned:halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, unsubstituted substituted cycloalkyloxy or unsubstituted or substituted phenyl,which comprises catalytically hydrogenating .alpha.-hydroxyketoximes of the formula (II) ##STR2## in which Ar has the meaning given above,using Raney nickel or Raney cobalt in the presence of a diluent and in the presence of a base andnovel 2-amino-2-arylethanols and novel .alpha.-hydroxyketoximes.Type: GrantFiled: August 4, 1995Date of Patent: February 11, 1997Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Ernst Kysela, Albrecht Marhold
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Patent number: 5599994Abstract: The present invention relates to a method of forming a 1,3-diamino-3-substituted-2-propanol chemical intermediate from which various chemicals, such as selected protease-inhibitors and other drugs, as well as polymers, can be synthesized.The method includes contacting a nitromethyl amino acid compound with at least one reducing agent to form the 1,3-diamino-3-substituted-2-propanol chemical intermediate.Type: GrantFiled: June 7, 1995Date of Patent: February 4, 1997Assignee: Pharm-Eco Laboratories, Inc.Inventors: Biman Pal, Siya Ram, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard L. Gabriel
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Patent number: 5554794Abstract: The invention includes a compound of formula I ##STR1## where R' is hydrogen, an alkyl, or aryl group; R"O is derived from R"OH which is a polyether mono-ol or hydrocarbyl mono-ol; and R"' independently is a hydrogen, an alkyl group or a substituted alkyl group. The invention also includes an unleaded fuel composition containing a compound of formula I and a process for making the compound of formula I.Type: GrantFiled: August 18, 1994Date of Patent: September 10, 1996Assignee: Shell Oil CompanyInventor: Thomas H. Johnson
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Patent number: 5536879Abstract: Optically active amino alcohols are prepared by reducing optically active amino acids with hydrogen in the presence of ruthenium catalysts.Type: GrantFiled: August 2, 1995Date of Patent: July 16, 1996Assignee: Bayer AktiengesellschaftInventors: Stefan Antons, Bernhard Beitzke
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Patent number: 5491233Abstract: A catalytic asymmetric reduction process, which, by hydrogenating trisubstituted olefins, yields a corresponding organic compound having a high level of enantiomeric purity is disclosed. The process is also effective for the catalytic asymmetric reduction of certain enamines and related compounds to yield a corresponding amine or related compound, respectively, having a high level of enantiomeric purity. The reduction process utilizes a chiral metal catalyst that includes a metal or metal complex that is selected from groups 3, 4, 5, or 6, lanthanides and actinides. Moreover, the process uses hydrogen as the stoichiometric reducing agent and may be carried out at pressures ranging from about 0.5 to 200 atmospheres. The reaction can also be carried out using an acidic compound as a rate enhancing additive.Type: GrantFiled: July 12, 1994Date of Patent: February 13, 1996Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Richard D. Broene, Nancy E. Lee
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Patent number: 5489682Abstract: A catalytic asymmetric reduction process, which, by hydrogenating enamines, yields a corresponding amine having a high level of enantiomeric purity is disclosed. The reduction process utilizes a chiral metal catalyst that includes a metal or metal complex that is selected from groups 3, 4, 5, or 6, lanthanides and actinides. Moreover, the process uses hydrogen as the stoichiometric reducing agent and may be carried out at pressures ranging from about 0.5 to 200 atmospheres.Type: GrantFiled: February 10, 1994Date of Patent: February 6, 1996Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Nancy E. Lee
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Patent number: 5475138Abstract: The present invention relates to a method of forming a 1,3-diamino-3-substituted-2-propanol chemical intermediate from which various chemicals, such as selected protease-inhibitors and other drugs, as well as polymers, can be synthesized.This method includes contacting a nitromethyl amino acid compound with at least one reducing agent to form the 1,3-diamino-3-substituted-2-propanol chemical intermediate.Type: GrantFiled: July 7, 1994Date of Patent: December 12, 1995Assignee: Pharm-Eco Laboratories IncorporatedInventors: Biman Pal, Siya Ram, Bing Cai, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard Gabriel
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Patent number: 5338884Abstract: Acylamides or amine acylate salts of arylalkanolamines are prepared by reacting an arylisonitrosoalkanone with hydrogen and a carboxylic acid, carboxylic acid anhydride or carboxylic acid ester or mixture thereof in the presence of a transition metal catalyst; optionally the product is converted to the corresponding arylalkanolamine hydrochloride salt by reaction of the acylamide or amine acylate salt of the arylalkanolamine with hydrogen chloride in a C.sub.1 -C.sub.3 alkyl alcohol.Type: GrantFiled: October 2, 1992Date of Patent: August 16, 1994Assignee: Hoechst CelaneseInventors: Ahmed M. Tafesh, Olan S. Fruchey, Charles B. Hilton
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Patent number: 5099067Abstract: The present invention relates to a method of converting .beta.-nitro compounds, specifically alcohols, into the corresponding hydroxy amines with retention of configuration by the use of ammonium formate.Type: GrantFiled: August 15, 1991Date of Patent: March 24, 1992Assignee: Northwestern UniversityInventors: Anthony G. M. Barrett, Christopher D. Spilling
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Patent number: 4952729Abstract: There is disclosed an improved process for preparing albuterol which comprises reacting a 5-(haloacetyl)-2-hydroxybenzaldehyde with 1,1-dimethylethanamine in an organic solvent and in an inert atmosphere to form 5-[[(1,1-dimethylethyl)amino]acetyl]-2-hydroxybenzaldehyde and reducing the carbonyl functions to the corresponding hydroxy groups to form albuterol.Type: GrantFiled: November 3, 1989Date of Patent: August 28, 1990Assignee: Schering-Plough Corp.Inventors: Esther Babad, Nicholas Carruthers, Martin Steinman
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Patent number: 4916252Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a 1,3-diketone in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.Type: GrantFiled: June 16, 1988Date of Patent: April 10, 1990Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
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Patent number: 4788010Abstract: Hypotensive activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof wherein R.sub.1 is hydrogen or alkyl;R.sub.2 and R.sub.3 are each independently phenyl, substituted phenyl, cycloalkyl, or R.sub.2 is hydrogen and R.sub.3 is heteroaryl;R.sub.4 and R.sub.5 are the same or different and each is hydrogen, hydroxy, alkoxy, alkanoyl or alkyl;R.sub.6 is hydrogen or alkyl; andn is 1, 2, 3 or 4; with the proviso that if R.sub.2 and R.sub.3 are each phenyl, at least one of R.sub.1, R.sub.4, R.sub.5 and R.sub.6 is other than hydrogen.Type: GrantFiled: April 24, 1985Date of Patent: November 29, 1988Assignee: E. R. Squibb & Sons, Inc.Inventors: David M. Floyd, Spencer D. Kimball, Steven Brandt
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Patent number: 4490392Abstract: A benzylalcohol derivative of the formula: ##STR1## wherein R is hydroxy, benzyloxy, halogen or alkoxy having one to four carbon atoms, and Ring A is monomethoxyphenyl, dimethoxyphenyl, trimethoxyphenyl or 3,4-methylenedioxyphenyl, or a pharmaceutically acceptable acid addition salt thereof is prepared by reducing a compound of the formula: ##STR2## wherein R' is benzyloxy, halogen or alkoxy having one to four carbon atoms, and Ring A is the same as defined above, to give a compound of the formula: ##STR3## wherein R' and Ring A are the same as defined above, and when R' is benzyloxy, if required, further subjecting the compound [I'] to catalytic hydrogenation to give a compound of the formula: ##STR4## wherein Ring A is the same as defined above. The benzylalcohol derivative [I] is useful as an anti-diabetic agent.Type: GrantFiled: July 27, 1978Date of Patent: December 25, 1984Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Muneyoshi Ikezaki, Takeshi Kanno, Hajime Iwai, Masanori Inamasu
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Patent number: 4461914Abstract: A method for the preparation of 1-(4'-amino-3',5'-dichlorophenyl)-2-alkyl)or dialkyl)aminoethanols. The method involves preparation of the above compounds from the corresponding aminoketones by reduction with hydrogen in the presence of platinum oxide catalyst and a promoter, such as stannous chloride.Type: GrantFiled: February 1, 1983Date of Patent: July 24, 1984Assignee: American Cyanamid CompanyInventor: Terence J. Bentley
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Patent number: 4317930Abstract: Novel phenethylamine derivatives represented by the general formula: ##STR1## wherein R is a lower alkyl group, C.sub.n H.sub.2n is a branched or straight alkylene group, A is a phenyl group unsubstituted or substituted with hydroxy, a lower alkoxy or a lower alkylene dioxy group, and n is an integer from 1 to 4, and pharmacologically acceptable acid addition salts thereof, and bronchdilator containing the same. These bronchdilator has an intense and durable bronchdilating effect and a weak heart stimulating action.Type: GrantFiled: March 16, 1977Date of Patent: March 2, 1982Assignee: Eisai Co., Ltd.Inventors: Noriyasu Hirose, Shigeru Souda
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Patent number: 4313005Abstract: This invention relates to a process for reducing amidine formation during reduction of organonitriles. The process comprises including a boron compound in the reaction medium in sufficient amount to complex the amidine compound as it is formed.Type: GrantFiled: April 3, 1980Date of Patent: January 26, 1982Assignee: Air Products and Chemicals, Inc.Inventors: Michael E. Ford, Randall J. Daughenbaugh
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Patent number: 4307248Abstract: Supported coprecipitated catalysts comprised of one or more metals of Group VIII, one or more metals of Group IIA, and aluminum are used for hydrogenating hydrogenatable organic compounds. The catalysts are produced by preparing, under agitation; an aqueous mixture containing ions of Group VIII, Group IIA, and aluminum, as well as solid porous particles to form a coprecipitate of the metal ions and aluminum ions with the solid porous support particles; heating the aqueous reaction mixture; and adding precipitating agent to precipitate the metal ions and aluminum ions onto the solid support.Type: GrantFiled: November 28, 1980Date of Patent: December 22, 1981Assignee: Exxon Research & Engineering Co.Inventors: Allan E. Barnett, Albert P. Halluin
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Patent number: 4273939Abstract: Supported coprecipitated non-ferrous Group VIII metal aluminum catalysts are used for hydrogenating hydrogenatable organic compounds. The catalysts are produced by preparing an aqueous mixture containing the metal ions, aluminum ions and solid porous support particles under agitation to form a coprecipitate of the metal ions and aluminum ions with the solid porous support particles; heating the aqueous reaction mixture; and adding precipitating agent to further precipitate the metal ions and aluminum ions onto the solid support.Type: GrantFiled: November 6, 1979Date of Patent: June 16, 1981Assignee: Exxon Research & Engineering Co.Inventors: Allan E. Barnett, Albert P. Halluin
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Patent number: 4252824Abstract: New compounds of the formula ##STR1## are disclosed wherein R.sub.1 =H, linear or branched alkyl-radical with from 1 to 6 carbon atoms, cycloalkyl radical with from 3 to 6 carbon atoms, alkylphenyl radical where the phenyl group may be in turn substituted with a hydroxy or methoxy group;R.sub.2 =hydroxy, hydromethylR.sub.3 =H, alkyl with 1-4 carbon atoms, formyl, carboalkyl where the alkyl groups have 1-3 carbon atoms, carbomido group simple or mono- or di-substituted on the nitrogen atom with alkyl radicals containing 1-3 carbon atoms.The new compounds are useful in the treatment of bronchial affections. They are endowed with unique properties in that they provide the desired bronchial dilation effect without any concomitant cardiac stimulation.Type: GrantFiled: November 10, 1976Date of Patent: February 24, 1981Assignee: Valeas S.R.L., Industria Chimica e FarmaceuticaInventors: Virgilio Bernareggi, Giuseppe Crespi, Giuseppe Bugada