Of Benzene Ring Containing Compounds Patents (Class 564/304)
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Patent number: 9493418Abstract: A method for producing a purified amine compound represented by the formula (1), including: step (A) of reacting a crude form of the amine compound represented by the formula (1) with a hydrogen halide in the presence of water and an organic solvent insoluble in water; step (B) of separating a phase in which a hydrogen halide salt of the amine compound represented by the formula (1) produced in step (A) is dissolved from the other phase(es); step (C) of precipitating the hydrogen halide salt of the amine compound represented by the formula (1) from the phase obtained in step (B) in which the hydrogen halide salt of the amine compound represented by the formula (1) is dissolved; and step (D) of isolating the hydrogen halide salt of the amine compound represented by the formula (1) precipitated in step (C), and reacting the salt with a base.Type: GrantFiled: December 11, 2013Date of Patent: November 15, 2016Assignee: SUMITOMO CHEMICAL COMPANY, LIMITEDInventor: Tadafumi Matsunaga
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Patent number: 9358532Abstract: A chiral hydrogenated H8-BINOL bisphosphine compound is provided, with the structure shown as the following formula (I), wherein both R1 and R2 are halogen, H or C1-C10 aliphatic group; R3 is H or C1-C10 aliphatic group; R4 is halogen, amino, nitro, H, C1-C10 aliphatic group or C1-C10 aromatic group; and X is phenyl, substituted phenyl, cyclohexyl, substituted cyclohexyl, C6-C30 aromatic group, or C6-C30 heterocyclic aromatic group containing one or more heteroatoms selected from N, S, O. The present invention further provides a catalyst for an asymmetric catalytic hydrogenation reaction which contains the compound, wherein the catalyst can produce more than 90% of enantiomers and efficiency with the turnover number of greater than 100,000 in the asymmetric hydrogenation reaction of imines.Type: GrantFiled: March 2, 2011Date of Patent: June 7, 2016Assignees: Dalian Heterogeneous Catalyst Co. Ltd., Jiangsu Yangnong Chemical Co., Ltd., Youth Chemical Co., Ltd.Inventor: Jin Li
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Composition, method for manufacturing thin film, and method for manufacturing light-emitting element
Patent number: 8845926Abstract: It is an object to provide a composition in which an anthracene derivative is dissolved and a technique in which a thin film that has a favorable film quality is formed by a wet process using the composition. In addition, it is another object to manufacture a highly reliable light-emitting element using the composition at low cost with high productivity. A composition having a solvent and an anthracene derivative having one anthracene structure and one carbazolyl group which is bonded to the anthracene structure directly or through a phenyl group is formed. A thin film with a favorable film quality can be formed by a wet process using the composition. Accordingly, a highly reliable light-emitting element can be manufactured using such a thin film.Type: GrantFiled: August 26, 2013Date of Patent: September 30, 2014Assignee: Semiconductor Energy Laboratory Co., Ltd.Inventors: Satoko Shitagaki, Satoshi Seo, Tsunenori Suzuki, Sachiko Kawakami -
Patent number: 8604242Abstract: The present invention describes a novel process for the preparation of optically active (S)-(?)-2-(N-propylamino)-5-methoxytetraline and (S)-(?)-2-(N-propylamino)-5-hydroxytetraline compounds based on the optical resolution of mixtures of the enantiomers of 2-(N-propylamino)-5-methoxytetraline and 2-(N-propylamino)-5-hydroxytetraline respectively. This process comprises (a) reacting a mixture of the enantiomers of said compounds with an optically active organic acid to form diastereoisomeric salts and separating the salts by crystallization. Said compounds are useful in the preparation of (6S)-(?)-5,6,7,8-tetrahydro-6-[propyl-(2-thienyl)ethyl]amino-1-naphthol (Rotigotine). Rotigotine is a dopamine agonist and is indicated for the treatment of Parkinson's disease.Type: GrantFiled: October 9, 2009Date of Patent: December 10, 2013Assignee: Interquim, S.A.Inventors: Francisco Marquillas Olondriz, Marta Pomares Marco
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Composition, method for manufacturing thin film, and method for manufacturing light-emitting element
Patent number: 8518492Abstract: It is an object to provide a composition in which an anthracene derivative is dissolved and a technique in which a thin film that has a favorable film quality is formed by a wet process using the composition. In addition, it is another object to manufacture a highly reliable light-emitting element using the composition at low cost with high productivity. A composition having a solvent and an anthracene derivative having one anthracene structure and one carbazolyl group which is bonded to the anthracene structure directly or through a phenyl group is formed. A thin film with a favorable film quality can be formed by a wet process using the composition. Accordingly, a highly reliable light-emitting element can be manufactured using such a thin film.Type: GrantFiled: July 25, 2012Date of Patent: August 27, 2013Assignee: Semiconductor Energy Laboratory Co., Ltd.Inventors: Satoko Shitagaki, Satoshi Seo, Tsunenori Suzuki, Sachiko Kawakami -
Patent number: 8461388Abstract: A process for preparing a compound of formula (V) or its enantiomer, which comprises: (a) reacting racemic aminoindan of formula (II) or its enantiomer with allylhalide in presence of a base and an organic solvent at a temperature ranging from 25 C to the reflux temperature of the solvent to give compound of formula (III); Where R is H or (b) reacting the compound (III) with halogenating agent in a suitable organic solvent to give a dihalo compound of formula (IV). (c) treating the dihalo compound (IV) with a suitable base to give compound (V).Type: GrantFiled: December 19, 2008Date of Patent: June 11, 2013Assignee: CIPLA LimitedInventors: Manjinder Singh Phull, Dharmaraj Ramachandra Rao, Rajendra Narayanrao Kankan
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Publication number: 20130096346Abstract: Provided herein is an improved and industrially advantageous optical resolution method for resolving (2R,3R)/(2S,3S)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol, and use thereof for the preparation of tapentadol or a pharmaceutically acceptable salt thereof. Provided further herein is an improved and industrially advantageous optical resolution method for resolving (2R,3R)/(2S,3S)-[3-(3-methoxyphenyl)-2-methylpentyl]-dimethylamine, and use thereof for the preparation of tapentadol or a pharmaceutically acceptable salt thereof. Disclosed also herein is an improved, commercially viable and industrially advantageous process for the preparation of tapentadol or a pharmaceutically acceptable salt thereof in high yield and purity.Type: ApplicationFiled: March 1, 2011Publication date: April 18, 2013Applicant: ACTAVIS GROUP PTC EHFInventors: Mayur Devjibhai Khunt, Sandipan Prabhurao Bondge, Nitin Sharadchandra Pradhan
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Publication number: 20130018194Abstract: This invention relates to octahydro-binaphthol derivatives, which can recognize amino acids and amino alcohols enantioselectively and transform L-amino acids into D-amino acids and optically resolve amino acids or amino alcohol with high efficiency.Type: ApplicationFiled: April 1, 2011Publication date: January 17, 2013Applicants: AMINOLUX, INC, EWHA UNIVERSITY-INDUSTRY COLLABORATION FOUNDATIONInventor: Kwan-Mook Kim
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Composition, method for manufacturing thin film, and method for manufacturing light-emitting element
Patent number: 8231942Abstract: It is an object to provide a composition in which an anthracene derivative is dissolved and a technique in which a thin film that has a favorable film quality is formed by a wet process using the composition. In addition, it is another object to manufacture a highly reliable light-emitting element using the composition at low cost with high productivity. A composition having a solvent and an anthracene derivative having one anthracene structure and one carbazolyl group which is bonded to the anthracene structure directly or through a phenyl group is formed. A thin film with a favorable film quality can be formed by a wet process using the composition. Accordingly, a highly reliable light-emitting element can be manufactured using such a thin film.Type: GrantFiled: May 15, 2009Date of Patent: July 31, 2012Assignee: Semiconductor Energy Laboratory Co., Ltd.Inventors: Satoko Shitagaki, Satoshi Seo, Tsunenori Suzuki, Sachiko Kawakami -
Patent number: 8198485Abstract: A method of resolving an important chemical intermediate, 4,5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane, comprises the following steps: reacting its two enantiomers of 4,5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane with di-p-toluoyl-L-tartaric acid (LDTTA) or di-p-toluoyl-D-tartaric acid (DDTTA) in an alcoholic solution or an alcohol in water solution to give the corresponding salts, and then resolving the salts. This method gives high enantiomer excess value, high yield which is more than 80% in total with normal resolution and reverse resolution.Type: GrantFiled: October 10, 2008Date of Patent: June 12, 2012Assignee: Jiangsu Hengrui Medicine Co., Ltd.Inventors: Piaoyang Sun, Yongjiang Chen, Guangliang Yu
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Publication number: 20120041235Abstract: The present invention relates to an improved process for the preparation of Tolterodine or salts thereof, which comprises the use of 3-(2-methoxy-5-methylphenyl)-3-phenylpropyl methane sulfonate.Type: ApplicationFiled: February 17, 2009Publication date: February 16, 2012Applicant: PHARMATHEN S.A.Inventors: Theoharis V. Koftis, Efstratios Neokosmidis, Rohit Ravikant Soni, Panagiota Mandalou, Aristotelis Menisiou
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Publication number: 20120041225Abstract: The present invention provides a means for the rapid selection of optimum resolving agents and solvents, combinations and conditions to separate optical isomers. The present invention combinedly describes and automates a full lifecycle of chiral separation method development and optimization through a series of kits and procedures providing screening, automation for screening, racemate recovery, enantiomer preparation, and method optimization.Type: ApplicationFiled: October 21, 2011Publication date: February 16, 2012Inventor: Niteen A. Vaidya
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Publication number: 20120004463Abstract: A method of resolving an important chemical intermediate, 4,5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane, comprises the following steps: reacting its two enantiomers of 4,5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane with di-p-toluoyl-L-tartaric acid (LDTTA) or di-p-toluoyl-D-tartaric acid (DDTTA) in an alcoholic solution or an alcohol in water solution to give the corresponding salts, and then resolving the salts. This method gives high enantiomer excess value, high yield which is more than 80% in total with normal resolution and reverse resolution.Type: ApplicationFiled: October 10, 2008Publication date: January 5, 2012Inventors: Piaoyang Sun, Yongjiang Chen, Guangling Yu
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Publication number: 20110313199Abstract: Provided herein are improved, convenient and industrially advantageous processes for the preparation of N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]formamide (Arformoterol) or a pharmaceutically acceptable salt thereof, in high yield and purity. Provided further herein is an improved and industrially advantageous process for the preparation of a substantially enantiomerically pure arformoterol intermediate, (R)-4-methoxy-?-methyl-N-(phenylmethyl)benzeneethanamine.Type: ApplicationFiled: December 28, 2009Publication date: December 22, 2011Applicant: ACTAVIS GROUP PTC EHFInventors: Girish Dixit, Nandkumar Gaikwad, Nitin Sharadchandra Pradhan
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Patent number: 8067640Abstract: The present invention relates to a novel method for the preparation of diol intermediates having the formula (II) and/or the opposite enantiomer of an acylated diol having the formula (IV) useful for the preparation of escitalopram involving selective enzymatic acylation or deacylation.Type: GrantFiled: May 17, 2010Date of Patent: November 29, 2011Assignee: H. Lundbeck A/SInventors: Naoki Taoka, Takahisa Kato, Shogo Yamamoto, Takashi Yoshida, Toshihiro Takeda, Yasuyoshi Ueda, Hans Petersen, Robert Dancer, Haleh Ahmadian, Lars O. Lyngso
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Patent number: 8063251Abstract: A process for the preparation of optically pure R (?) salbutamol of formula (6) and its pharmaceutically acceptable salts by using a (+) 4-nitro tartranilic acid as the resolving agent and a binary solvent system comprising alkyl acetate and C1 to C4 branched or normal chain alcohol for dissolution of the racemic mixture and resolving agent and purification of the 4-nitro tartranilic acid salt of R (?) salbutamol. 4-nitro tartranilic acid salt of R (?) salbutamol is converted into formic acid salt of R (?) 4-benzyl salbutamol followed by basification and debenzylation to form optically pure R (?) salbutamol. Optically pure (R)-salbutamol is obtained in good yield and high purity. The optically pure R (?) salbutamol is optionally converted into pharmaceutically acceptable salts.Type: GrantFiled: September 25, 2006Date of Patent: November 22, 2011Assignee: Aarti Healthcare LimitedInventors: Parimal Hasmukh Desai, Narendra Jagannath Salvi, Bharatkumar Surendra Patravale, Subramanian Seetharaman, Dilip Jibhau Patil, Khandu Shankar Ghogare
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Publication number: 20110218360Abstract: The present invention relates to processes for the preparation of rasagiline mesylate. Also provided is rasagiline mesylate having 90 volume percent of the particles (D90) with sizes less than about 6 ?m and processes for the preparation thereof.Type: ApplicationFiled: May 20, 2011Publication date: September 8, 2011Applicants: DR. REDDY'S LABORATORIES LTD., DR. REDDY'S LABORATORIES, INC.Inventors: Praveen Cherukupally, Venkata Reddy Vajrala, Vijaya Kumar Adla, Srinivasulu Rangineni, Sundaralakshmi Kanniah
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Publication number: 20110124899Abstract: The Invention relates to a method for preparing a combretastatin (A): formula (I) in the form of a base or of an addition salt with an acid, which comprises coupling, in the presence of a base and of T3P, the salt of the (Z)-amino compound of formula (II) with a doubly protected L-serine derivative of formula (III) in which PG denotes a group protecting the amine function, so as to obtain the compound of formula (Z)-(Ib): formula (IV), then deprotecting and opening the ring of (Z)-(Ib) in the presence of an acid, so as to obtain the combretastatin (A) in the form of a salt; and, optionally, adding a base, so as to obtain the combretastatin (A) in the form of a base, the salt of the (Z)-amino compound having been obtained by enrichment of the salt of the amino compound of formula (V) in (Z) isomer.Type: ApplicationFiled: August 27, 2010Publication date: May 26, 2011Applicant: SANOFI-AVENTISInventors: Marc FREDERIC, Sylviane LUTZ, Joel MALPART, Philippe MASSON, Stephane MUTTI
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Publication number: 20110092738Abstract: Described is a process of preparing a pure solid or crystalline racemic 3,3-diarylpropylamine compound and the compounds formed thereof. The solid and crystalline forms of racemic 3,3-diarylpropylamine compound are especially suitable for producing highly pure 3,3-diarylpropylamine salts such as tolterodine tartrate. Also described are the highly pure solid or crystalline forms of racemic tolterodine, racemic tolterodine salt and tolterodine tartrate.Type: ApplicationFiled: December 9, 2010Publication date: April 21, 2011Applicant: Medichem S.A.Inventors: Maria Angeles Conde Martinez, Ignasi Auquer i Pedemonte
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Publication number: 20110054218Abstract: A process for preparing a compound of formula (V) or its enantiomer, which comprises: (a) reacting racemic aminoindan of formula (II) or its enantiomer with allylhalide in presence of a base and an organic solvent at a temperature ranging from 25 C to the reflux temperature of the solvent to give compound of formula (III); Where R is H or (b) reacting the compound (III) with halogenating agent in a suitable organic solvent to give a dihalo compound of formula (IV). (c) treating the dihalo compound (IV) with a suitable base to give compound (V).Type: ApplicationFiled: December 19, 2008Publication date: March 3, 2011Applicant: CIPLA LIMITEDInventors: Manjinder Singh Phull, Dharmaraj Ramachandra Rao, Rajendra Narayanrao Kankan
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Publication number: 20110040101Abstract: Disclosed is an alanine racemase chiral binaphthol derivative having the ability to recognize amino alcohols selectively on the basis of chirality and transform amino acids from an L-form into a D-form. Methods for the optical resolution of amino acid or amino alcohol and for the optical transformation of D- and L-forms of amino acids using the binaphthol derivative are also provided.Type: ApplicationFiled: October 26, 2010Publication date: February 17, 2011Applicant: GREEN FORMULA CO. LTD.Inventors: Kim Kwan Mook, Tang Lijun
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Publication number: 20110034726Abstract: The invention relates to a process for preparing optically active ?-aminoacetals by resolution of a racemic mixture or of a mixture of enantiomers via the formation of diastereoisomeric salts, and also novel intermediates in the form of diastereoisomeric salts.Type: ApplicationFiled: January 21, 2009Publication date: February 10, 2011Applicant: CLARIANT SPECIALTY FINE CHEMICALS (FRANCE)Inventors: Muriel Albalat, Geraldine Primazot, Didier Wilhelm, Jean-Claude Vallejos
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Patent number: 7884247Abstract: Novel 3-[2-(dimethylamino)methyl-(cyclohex-1-yl)]-phenol maleate compounds corresponding to formula I and processes for preparing these compounds are provided. Pharmaceutical compositions including these compounds and methods of treating or alleviating pain with these compounds are also provided.Type: GrantFiled: July 24, 2006Date of Patent: February 8, 2011Assignee: Gruenenthal GmbHInventors: Michael Gruss, Wolfgang Hell, Martin Szelagiewicz, Joerg Berghausen, Susan Margaret De Paul, Markus Von Raumer
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Publication number: 20100204516Abstract: A process for the preparation of optically pure R (?) salbutamol of formula (6) and its pharmaceutically acceptable salts by using a (+) 4-nitro tartranilic acid as the resolving agent and a binary solvent system comprising alkyl acetate and C1 to C4 branched or normal chain alcohol for dissolution of the racemic mixture and resolving agent and purification of the 4-nitro tartranilic acid salt of R (?) salbutamol. 4-nitro tartranilic acid salt of R (?) salbutamol is converted into formic acid salt of R(?) 4-benzyl salbutamol followed by basification and debenzylation to form optically pure R(?) salbutamol. Optically pure (R)-salbutamol is obtained in good yield and high purity. The optically pure R(?)salbutamol is optionally converted into pharmaceutically acceptable salts.Type: ApplicationFiled: September 25, 2006Publication date: August 12, 2010Applicant: AARTI HEALTHCARE LIMITEDInventors: Parimal Desai, Narendra Salvi, Bharatkumar Patravale, Subramanian Seetharaman, Dilip Patil, Khandu Ghogare
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Patent number: 7649114Abstract: The invention concerns a method for the isolation of a stereoisomer from a mixture comprising the two stereoisomers of the general formulae (I-A) and (I-A?) and/or the two stereoisomers of the general formulae (I-B) and (I-B?) in which R1, R2 and R3, identical or different, are selected from the group consisting of —H, —F, —Cl, —C1-C6-alkyl, —S—C1-C6-alkyl, —OH, —O—C1-C6-alkyl, —O—C1-C6-alkylenephenyl, —OCO—C1-C6-alkyl, —OCON(C1-C6-alkyl)2 and —O—SiR8R9R10 (in which R8, R9 and R10, identical or different, are —C1-C6-alkyl or -phenyl); R4 is —H or —C1-C6-alkyl; R5 is —C1-C6-alkyl; and R6 and R7, identical or different, are —H or —C1-C6-alkyl; or their salts with organic or inorganic acids; comprising the step (a) manipulating the mixture ratio of the stereoisomers in the mixture so that at least one of the stereoisomers is present in an enantiomeric excess.Type: GrantFiled: May 29, 2006Date of Patent: January 19, 2010Assignee: Gruenenthal GmbHInventors: Helmut Heinrich Buschmann, Wolfgang Hell
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Patent number: 7544840Abstract: The compound of formula (III), optionally its alkaline salt, is reacted with a compound of formula VII, wherein X is a leaving group, resulting in (S)-rivastigmine of formula II, which is then optionally converted into (S)-rivastigmine hydrogentartrade of formula I.Type: GrantFiled: October 21, 2003Date of Patent: June 9, 2009Assignee: Zentiva, a.s.Inventors: Hana Stepankova, Josef Hajicek, Stanislav Simek
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Patent number: 7470816Abstract: A process for the resolution of isomeric tramadol mixtures comprising: providing a purification stock comprising both cis and trans tramadol; contacting the purification stock with an acid under conditions effective to form an acid salt of the cis and trans tramadol in the purification stock; and separating the cis tramadol acid salt from the trans tramadol to obtain a purified cis tramadol acid salt; and optionally converting the cis tramadol acid salt to cis tramadol or to a pharmaceutically active salt thereof.Type: GrantFiled: November 13, 2006Date of Patent: December 30, 2008Assignee: IPAC Laboratories LimitedInventors: Ashok Kumar, Suneel Yeshwant Dike, Satish Rajanikant Soudagar, Chirag Hasmukh Shah, Sandeep Madhavrao Burudkar, Prashant Gautam, Byju Nellithanath Thankachen, Ashvini Saxena, Manavalan Saravanan, Gunjan Pramod Pathak, Virendra Pal, Rahul Karde, Jaysingh Gehlot
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Patent number: 7414153Abstract: An efficient cost-effective process for preparation of 1-erythro-2-amino-1-phenyl-1-propanol from 1-1-phenyl-1-hydroxy-2-propanone, which comprises converting 1-1-phenyl-1-hydroxy-2-propanone to 1-1-phenyl-1-hydroxy-2-propanone oxime and reducing the oxime with a catalyst consisting of finely divided nickel and aluminium metals giving good diastereomeric purity and yield.Type: GrantFiled: March 9, 2005Date of Patent: August 19, 2008Assignee: Emmellen Biotech Pharmaceuticals LimitedInventors: Subrahmanyam Gollapudy, Sunil Vaman Joshi
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Patent number: 7368609Abstract: An optically active 1-(fluoro-, trifluoromethyl- or trifluoromethoxy-substituted phenyl)alkylamine N-monoalkyl derivative represented by the formula 4 is produced by a process including (a) reacting an optically active secondary amine, represented by the formula 1, with an alkylation agent R2—X, in the presence of a base, thereby converting the secondary amine into an optically active tertiary amine represented by the formula 3; and (b) subjecting the tertiary amine to a hydrogenolysis, thereby producing the N-monoalkyl derivative, wherein R represents a fluorine atom, trifluoromethyl group or trifluoromethoxy group, n represents an integer of from 1 to 5, each of R1 and R2 independently represents an alkyl group having a carbon atom number of from 1 to 6, Me represents a methyl group, Ar represents a phenyl group or 1- or 2-naphthyl group, * represents a chiral carbon, and X represents a leaving group.Type: GrantFiled: February 12, 2007Date of Patent: May 6, 2008Assignee: Central Glass Company, LimitedInventors: Akihiro Ishii, Masatomi Kanai, Yokusu Kuriyama, Manabu Yasumoto, Kenjin Inomiya, Takashi Ootsuka, Koji Ueda
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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: 7186865Abstract: An optically active 1-(fluoro-, trifluoromethyl- or trifluoromethoxy-substituted phenyl)alkylamine N-monoalkyl derivative represented by the formula 4 is produced by a process including (a) reacting an optically active secondary amine, represented by the formula 1, with an alkylation agent R2—X, in the presence of a base, thereby converting the secondary amine into an optically active tertiary amine represented by the formula 3; and (b) subjecting the tertiary amine to a hydrogenolysis, thereby producing the N-monoalkyl derivative, wherein R represents a fluorine atom, trifluoromethyl group or trifluoromethoxy group, n represents an integer of from 1 to 5, each of R1 and R2 independently represents an alkyl group having a carbon atom number of from 1 to 6, Me represents a methyl group, Ar represents a phenyl group or 1- or 2-naphthyl group, * represents a chiral carbon, and X represents a leaving group.Type: GrantFiled: September 5, 2003Date of Patent: March 6, 2007Assignee: Central Glass Company, LimitedInventors: Akihiro Ishii, Masatomi Kanai, Yokusu Kuriyama, Manabu Yasumoto, Kenjin Inomiya, Takashi Ootsuka, Koji Ueda
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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: 7030276Abstract: A process for preparing 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol with high stereoselectivity and high yield by reacting 2-[(dimethylamino)methyl]-cyclohexanone in a Grignard reaction with a Grignard compound of 3-bromoanisole in a suitable solvent and in the presence of an inorganic lithium salt and an ?,?-dialkoxyalkane.Type: GrantFiled: February 9, 2005Date of Patent: April 18, 2006Assignee: Gruenenthal GmbHInventors: Michael Finkam, Bernhard Akteries
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Patent number: 6995286Abstract: A process for making optically pure (R) and (S) salbutamol comprises obtaining the (R) or (S) isomer of either salbutamol or a salbutamol precursor in substantially optically pure form by resolving a racemic or optically impure mixture of enantiomers of salbutamol or of said precursor with either (L) or (D) tartaric acid, and where necessary converting said isomer of said precursor into either (R or (S) salbutamol respectively; then optionally converting said optically pure (R) and/or (S) salbutamol into a pharmaceutically acceptable salt.Type: GrantFiled: December 10, 2001Date of Patent: February 7, 2006Assignee: Cipla LimitedInventors: Yusuf Khwaja Hamied, Rajendra Narayanrao Kankan, Dharmaraj Ramachandra Rao
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Patent number: 6989465Abstract: The present invention relates to a novel compound S-(?)-1-{4-[2-(allyloxy)-ethyl] phenoxy}-3-isopropylamino propan-2-ol of formula 1 and to a process for the preparation thereof. More particularly the present invention relates to a process for preparing S-(?)-1-{4-[2-(allyloxy)-ethyl]phenoxy}-3-isopropylamino propan-2-ol of formula 1 by selective allylation of p-hydroxy phenyl ethanol.Type: GrantFiled: November 1, 2004Date of Patent: January 24, 2006Assignee: Council of Scientific and Industrial ResearchInventors: Ramesh Anna Joshi, Muthukrishnan Murugan, Dinesh Rämesh Garud, Sanjay Pandurang Borikar, Mukund Keshav Gurjar
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Patent number: 6982350Abstract: Process for the synthesis of the compound of formula (I): Application in the synthesis of ivabradine, addition salts thereof with a pharmaceutically acceptable acid, and hydrates thereof.Type: GrantFiled: February 17, 2005Date of Patent: January 3, 2006Assignee: Les Laboratoires ServierInventors: Jean-Michel Lerestif, Isaac Gonzalez Blanco, Jean-Pierre Lecouve, Daniel Brigot
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Patent number: 6878848Abstract: A process for interconverting a mixture of cis-trans isomers of a compound of formula I into the substantially pure cis isomer. Cis isomers of formula I are useful intermediates in the synthesis of cis isomers of benzamide piperidine compounds which exhibit activity as NK-1 receptor antagonists.Type: GrantFiled: November 10, 2003Date of Patent: April 12, 2005Assignee: Pfizer IncInventors: John Michael Humphrey, Norma Jacqueline Tom
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Patent number: 6821998Abstract: Methods for treating CMV and CMV-related diseases are provided that use compounds having the formula: wherein the subscripts m and n are each independently integers from 1 to 2; and the R groups are as defined in the specification.Type: GrantFiled: August 29, 2002Date of Patent: November 23, 2004Assignee: ChemoCentryx, Inc.Inventors: Brian E. McMaster, Thomas J. Schall, Mark Penfold, J. J. Wright, Daniel J. Dairaghi
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Patent number: 6809221Abstract: The present invention is directed to (+)-cis-sertraline hydrochloride and methods of preparation. The present invention also includes processes for making sertraline having a cis/trans ratio greater than 3:1, greater than or equal to 8:1, or between about 8:1 and about 12:1, from the Schiff base of sertralone, sertraline-1-imine.Type: GrantFiled: February 12, 2003Date of Patent: October 26, 2004Assignee: Teva Pharmaceutical Industries Ltd.Inventors: Marioara Mendelovici, Tamar Nidam, Gideon Pilarsky, Neomi Gershon
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Patent number: 6806386Abstract: The present invention relates to a process for the preparation of compounds of formula (1), in which R1, R2 and R3 independently of one another are hydrogen, halogen , trifluoromethyl of or C1-C4alkoxy, wherein a compound of formula (2), in which R1, R2 and R3 are as defined in formula (1), is reacted with methlyamine in the presence of a non-alcoholic solvent and, if desired, in the presence of a sulfonic acid catalyst to give the compound of formula (2) and, if desired, is subject to purification by recrystallization.Type: GrantFiled: May 14, 2002Date of Patent: October 19, 2004Assignee: Ciba Specialty Chemicals CorporationInventors: Marc Thommen, Andreas Hafner, Frédëric Brunner, Hans-Jörg Kirner, Roman Kolly
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Patent number: 6570036Abstract: A process for isolating one or more enantiomer components from a mixture of enantiomers through co-crystallization is disclosed.Type: GrantFiled: August 31, 2001Date of Patent: May 27, 2003Assignee: Reuter Chemische Apparatebau KG [DE/DE]Inventor: Karl Reuter
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Patent number: 6552227Abstract: The present invention is directed to (+)-cis-sertraline hydrochloride and methods of preparation. The present invention also includes processes for making sertraline having a cis/trans ratio greater than 3:1, greater than or equal to 8:1, or between about 8:1 and about 12:1, from the Schiff base of sertralone, sertraline-1-imine.Type: GrantFiled: March 14, 2001Date of Patent: April 22, 2003Assignee: Teva Pharmaceutical Industries Ltd.Inventors: Marioara Mendelovici, Tamar Nidam, Gideon Pilarsky, Neomi Gershon
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Patent number: 6506940Abstract: A process for converting the cis (1R, 4R), trans (1S, 4R), and trans (1R, 4S) stereoisomers of sertraline into sertraline comprises, starting with an initial reaction mixture which contains at least one of these stereoisomers, converting the sertraline stereoisomers into an imine form of sertraline. The imine form of sertraline is then reduced so that sertraline and at least one sertraline stereoisomer byproduct is produced in the reaction mixture. The sertraline is then recovered from the reaction mixture, e.g., by fractional crystallization (followed by resolution of sertraline from the cis (1R, 4R) stereoisomer, if necessary). The reaction mixture is then recycled through the same steps so that sertraline is produced from its stereoisomers in an asymptotic yield.Type: GrantFiled: November 10, 2000Date of Patent: January 14, 2003Assignee: Sun Pharmaceuticals Industries Ltd.Inventors: Kanaksinh J. Jadav, Trinadha Rao Chitturi, Rajamannar Thennati
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Patent number: 6469213Abstract: Cis-Tramadol hydrochloride is prepared by forming a Mannich hydrochloride, liberating the Mannich base, reacting the Mannich base with a Grignard reagent to form a base hydrate of cis-Tramadol which is used to form pure cis-Tramadol hydrochloride. Also claimed is the base hydrate of cis-Tramadol per se and its use as a medicament.Type: GrantFiled: January 14, 2000Date of Patent: October 22, 2002Assignee: Russinsky LimitedInventors: Helmut Schickaneder, Aggelos Nikolopoulos
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Patent number: 6458955Abstract: Improved processes for preparation of high enantiomeric purity compounds center on resolution using simulated moving bed chromatography of a racemic precursor early in the synthesis. Resolution is effected with high enantiomeric purity, and subsequent reactions of the desired enantiomer performed with high optical specificity to maintain enantiomeric purity. The undesired enantiomer is racemized and recycled to the resolution phase to avoid loss.Type: GrantFiled: November 3, 2000Date of Patent: October 1, 2002Assignee: UOP LLCInventor: Mark J. Gattuso
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Patent number: 6455736Abstract: Improved processes for preparation of sertraline or sertraline analogs in high enantiomeric purity centers on resolution using simulated moving bed chromatography of isomeric racemic sertraline or sertraline analogs. Resolution is effected with high enantiomeric purity, and the undesired enantiomer may be racemized and recycled to the resolution phase to avoid loss.Type: GrantFiled: November 3, 2000Date of Patent: September 24, 2002Assignee: UOP LLCInventors: Herman A. Zinnen, Mark J. Gattuso
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Patent number: 6399826Abstract: Methods of making and using racemic and optically pure metabolites of sibutramine, and pharmaceutically acceptable salts, solvates, and clathrates thereof, are disclosed. Pharmaceutical compositions and dosage forms are also disclosed which comprise a dopamine reuptake inhibitor, such as a racemic or optically pure sibutramine metabolite, and optionally an additional pharmacologically active compound.Type: GrantFiled: January 11, 2000Date of Patent: June 4, 2002Assignee: Sepracor Inc.Inventors: Chrisantha Hugh Senanayake, Qun Kevin Fang, Zhengxu Han, Dhileepkumar Krishnamurthy
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Patent number: 6399829Abstract: (R*,R*)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol (Tramadol) is synthesized in a Grignard reaction in the presence of an additive resulting in a higher trans:cis ratio of product than is obtained in the absence of the additive. The Grignard reaction between 3 bromoanisole and the appropriate Mannich base in the presence of an amine or ether additive gives the amine product in an improved trans/cis ratio. The base is converted to its hydrochloride and recrystallized from a low molecular weight nitrile such as acetonitrile until a greater than 98% trans/cis ratio is obtained. Recrystallization from isopropanol gives (R*,R*)2-[(dimethylamino)methyl]-1-(3-metboxyphenyl)cyclohexanol hydrochloride free of the nitrile solvent. A hydrochloride of Tramadol can be synthesized without increasing a ratio of trans:cis by including a step in which HCl is added to Tramadol base in the presence of toluene.Type: GrantFiled: November 20, 2000Date of Patent: June 4, 2002Assignee: Mallinckrodt Inc.Inventors: Esa T. Jarvi, Neile A. Grayson, Robert E. Halvachs
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Patent number: RE43844Abstract: A process for making optically pure (R) and (S) salbutamol comprises obtaining the (R) or (S) isomer of either salbutamol or a salbutamol precursor in substantially optically pure form by resolving a racemic or optically impure mixture of enantiomers of salbutamol or of said precursor with either (L) or (D) tartaric acid, and where necessary converting said isomer of said precursor into either (R or (S) salbutamol respectively; then optionally converting said optically pure (R) and/or (S) salbutamol into a pharmaceutically acceptable salt.Type: GrantFiled: December 10, 2001Date of Patent: December 4, 2012Assignee: Cipla LimitedInventors: Yusuf Khwaja Hamied, Rajendra Narayanrao Kankan, Dharmaraj Ramachandra Rao
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Patent number: RE43984Abstract: A process for making optically Optically pure (R) and (S) salbutamol comprises obtaining the (R) or (S) isomer of either salbutamol or a salbutamol precursor in substantially optically pure form is obtained by resolving a racemic or optically impure mixture of enantiomers of salbutamol or of said a salbutamol precursor with either (L) or (D) tartaric acid, and where necessary converting said isomer of said precursor into either (R) or (S) salbutamol respectively; then optionally converting said optically pure (R) and/or (S) salbutamol into a pharmaceutically acceptable salt.Type: GrantFiled: December 10, 2001Date of Patent: February 5, 2013Assignee: Cipla LimitedInventors: Yusuf Khwaja Hamied, Rajendra Narayanrao Kankan, Dharmaraj Ramachandra Rao