Reactant Having Halogen Bonded Directly To Sulfur By Nonionic Bonding Patents (Class 562/862)
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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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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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Publication number: 20120310010Abstract: A process for preparing sulfonamides I where the variables are each as defined in the description, by reacting m-nitrobenzoyl chlorides II with amino sulfones III, under the influence of B equivalents of base IV, wherein, in step a), the amino sulfone III is reacted with B1 equivalents of base IV, and, in step b), the reaction mixture resulting from step a) is reacted with m-nitrobenzoyl chlorides II and B2 equivalents of base IV; where B, B1 and B2 are each as defined in the description.Type: ApplicationFiled: August 13, 2012Publication date: December 6, 2012Applicant: BASF SEInventors: Thomas Schmidt, Joachim Gebhardt, Sandra Löhr, Michael Keil, Jan Hendrik Wevers, Michael Rack, Guido Mayer, Axel Pleschke
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Publication number: 20120130097Abstract: The invention relates to a novel process for the preparation of certain cyclopropyl carboxylic acid esters and other cyclopropyl carboxylic acid derivatives; a novel process for the preparation of dimethylsulfoxonium methylide and dimethylsulfonium methylide; to the use of certain cyclopropyl carboxylic acid esters in a process for the preparation of intermediates that can be used in the synthesis of pharmaceutically active entities; and to certain intermediates provided by these processes.Type: ApplicationFiled: January 30, 2012Publication date: May 24, 2012Applicant: AstraZeneca ABInventors: Adrian Clark, Elfyn Jones, Ulf Larsson, Anna Minidis
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Publication number: 20120053365Abstract: A method of producing an acid halide, including: reacting a compound represented by the following Formula (III) with a basic compound and a compound represented by the following Formula (IV) to obtain a compound represented by the following Formula (II); and reacting the compound represented by Formula (II) with an acid halogenating agent to obtain a compound represented by the following Formula (I):Type: ApplicationFiled: July 29, 2011Publication date: March 1, 2012Applicant: FUJIFILM CORPORATIONInventor: Akiyoshi GOTO
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Publication number: 20110190520Abstract: The invention relates to a novel process for the preparation of certain cyclopropyl carboxylic acid esters and other cyclopropyl carboxylic acid derivatives; a novel process for the preparation of dimethylsulfoxonium methylide and dimethylsulfonium methylide; to the use of certain cyclopropyl carboxylic acid esters in a process for the preparation of intermediates that can be used in the synthesis of pharmaceutically active entities; and to certain intermediates provided by these processes.Type: ApplicationFiled: February 8, 2011Publication date: August 4, 2011Applicant: AstraZeneca ABInventors: Adrian Clark, Elfyn Jones, Ulf Larsson, Anna Minidis
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Patent number: 7728171Abstract: A process for the preparation of acid halides of formula I which are useful as intermediates in the preparation of i.a. pharmaceutically active compounds.Type: GrantFiled: August 25, 2008Date of Patent: June 1, 2010Assignee: Hoffmann-La Roche Inc.Inventors: Ursula Hoffmann, Goesta Rimmler
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Publication number: 20090192333Abstract: A process for the preparation of acid halides of formula I which are useful as intermediates in the preparation of i.a. pharmaceutically active compounds.Type: ApplicationFiled: April 6, 2009Publication date: July 30, 2009Inventor: Ursula Hoffmann
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Publication number: 20090076304Abstract: The present invention discloses methods for producing a carboxylic acid chloride compound which comprises the step of reacting an alkyl-substituted cyclohexyl carboxylic acid with a chlorinating agent in the presence of a specific urea compound. According to this invention, it is possible to produce a carboxylic acid chloride compound which has high reaction speed, and whose product has high purity or high yield. Thus produced carboxylic acid chloride compound is useful as an intermediate for producing D-phenylalanine derivatives which are used as agents for treating diabetes.Type: ApplicationFiled: September 30, 2008Publication date: March 19, 2009Applicant: AJINOMOTO CO., INC.Inventors: Tatsuya Ishikawa, Shouichi Kondou, Satoji Takahashi
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Publication number: 20090036703Abstract: A process for the preparation of acid halides of formula I which are useful as intermediates in the preparation of i.a. pharmaceutically active compounds.Type: ApplicationFiled: August 25, 2008Publication date: February 5, 2009Inventors: Ursula Hoffmann, Goesta Rimmler
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Patent number: 7435849Abstract: A process for the preparation of acid halides of formula I which are useful as intermediates in the preparation of i.a. pharmaceutically active compounds.Type: GrantFiled: October 17, 2006Date of Patent: October 14, 2008Assignee: Hoffmann-La Roche Inc.Inventors: Ursula Hoffmann, Goesta Rimmler
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Patent number: 7102046Abstract: The present invention relates to a process for the arylation of olefins by reaction of haloaromatics or arylsulfonates with olefins in the presence of a palladium catalyst, a bulky nitrogen base and a salt.Type: GrantFiled: November 27, 2002Date of Patent: September 5, 2006Assignee: Bayer AktiengesellschaftInventors: Florian Rampf, Markus Eckert
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Patent number: 7094926Abstract: A nitrous acid salt is added at a temperature of 10 to 80° C. to an aqueous solution which contains an optically active 2-aminocarboxylic acid (4) and a protonic acid, the amount of the latter acid being 1 to 3 equivalents to the former, and which has a proton concentration of 0.5 to 2 mol/kg to conduct a reaction to thereby produce an optically active 2-hydroxycarboxylic acid (1). Thionyl chloride and a basic compound are caused to act on the compound (1) to chlorinate it and simultaneously invert the configuration in the 2-position. Thus, an optically active 2-chlorocarboxylic acid chloride (5) is induced. The compound (5) is hydrolyzed to induce an optically active 2-chlorocarboxylic acid (2). The compound (2) is reacted with a thioacetic acid salt to incorporate an acetylthio group thereinto and simultaneously invert the configuration in the 2-position to thereby produce an optically active 2-acetylthiocarboxylic acid (3).Type: GrantFiled: January 25, 2001Date of Patent: August 22, 2006Assignee: Kaneka CorporationInventors: Susumu Amano, Masaru Mitsuda, Kenji Inoue, Koichi Kinoshita, Koki Yamashita, Yasuyoshi Ueda
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Patent number: 7034181Abstract: The invention relates to a method for producing o-chloromethyl benzoic acid chlorides of formula (I), in which R1 to R4 can be the same or different and represent hydrogen C1–C4 alkyl, halogen or trifluoromethyl, by reaction benzo condensed lactones of formula (II), in which R1 to R4 have the above-mentioned meaning, with thionyl chloride. The inventive method is characterized in that the reaction is carried out in the presence of catalytic quantities of a Lewis acid and in the presence of catalytic quantities of a phosphine derivative.Type: GrantFiled: November 27, 2000Date of Patent: April 25, 2006Assignee: BASF AktiengesellschaftInventors: Roland Götz, Norbert Götz, Michael Keil, Bernd Wolf, Adrian Steinmetz, Armin Stamm, Jochem Henkelmann
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Patent number: 6844468Abstract: The present invention relates to a process for preparing substituted benzoyl chlorides of the formula (1) where R, x and y have the meaning given below, which comprises reacting a benzaldehyde of the formula (2) where R, independently of each other, is identical or different and is an unsubstituted phenyl radical or a phenyl radical that is substituted by halogen, NO2, CN, (C1-C4)alkyl or (C1-C4)alkoxy, or is halogen, NO2, CN, NR?2, OR?, SO2R?, SO2OR?, COR? or CO2R?, where R? is an unbranched or branched C1-C10 alkyl radical, an unsubstituted phenyl radical or a phenyl radical which is substituted by halogen, NO2, CN, (C1-C4)alkyl or (C1-C4)alkoxy, x is 1 or 2 and y is 1, 2 or 3, with a chlorinating agent in the presence of a free-radical initiator and a solvent at from ?20 to +200° C.Type: GrantFiled: October 3, 2002Date of Patent: January 18, 2005Assignee: Clariant GmbHInventors: Lars Bierer, Joachim Ritzer, Berthold Schiemenz, Thomas Wessel
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Publication number: 20040152782Abstract: Provided is a process for preparation of an intermediate in the synthesis of nateglinide. Trans-4-isopropylcyclohexane acid chloride is formed by reacting 4-isopropylcyclohexanecarboxyl acid with thionyl chloride in the presence of an effective amount of an organic amide.Type: ApplicationFiled: July 3, 2003Publication date: August 5, 2004Inventors: Ronit Yahalomi, Evgeny Shapiro, Ben-Zion Dolitzky, Yigael Gozlan
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Patent number: 6465700Abstract: Novel 2-substituted 7-haloindenes and methods for synthesizing such indenes are described. The 2-substituted 7-haloindenes may be coupled with any aryl group to produce a metallocene catalyst intermediate.Type: GrantFiled: August 3, 1998Date of Patent: October 15, 2002Assignee: Boulder Scientific CompanyInventors: Jeffrey M. Sullivan, Hamlin H. Barnes
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Patent number: 6206819Abstract: N,N-disubstituted formamides, wherein the substituents are selected to provide formamides which have low volatility, are useful as halogenation catalysts. Such catalysts are generally less hazardous to use than typical formamide halogenation catalysts because toxic catalyst by-products are also less volatile. Methods for using such catalysts are provided.Type: GrantFiled: May 15, 2000Date of Patent: March 27, 2001Assignee: Rohm and Haas CompanyInventors: Deborah Diane Graves, Thomas Duncan Rose, David James Swank, Charles Chao Wu
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Patent number: 6166252Abstract: Process for preparing dichlorofluoroacetylfluoride (CFCl.sub.2 COF) comprising the following steps:a) fluorination with hydrofluoric acid (HF) of the trichloroacetyl halide in a fixed or fluidized tubular bed reactor, filled with fluorination catalysts and having a temperature profile between the inlet of the reactants and the outlet of the reaction products, in the range from 175.degree. C. to 275.degree. C.b) distillation of the reaction products with trichloroacetylfluoride recycle and recovery of a mixture formed by HF and CFCl.sub.2 COF;c) separation of the HF/CFCl.sub.2 COF mixture components by cooling at temperatures lower than -10.degree. C., and optionally the HF recycle.Type: GrantFiled: January 7, 1999Date of Patent: December 26, 2000Assignee: Ausimont S.p.A.Inventors: Piero Gavezotti, Julio A. Abusleme, Vito Tortelli
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Patent number: 6114467Abstract: Compounds having the formula F(CF.sub.2).sub.q --(CH.sub.2).sub.p-1 --COX' wherein q ranges from 6-15, p ranges from 3-15 and X' is halogen are useful as reactants for hydroxylated block copolymers or polyamines to produce fluorinated polymers.Type: GrantFiled: August 11, 1998Date of Patent: September 5, 2000Assignee: Cornell Research Foundation, Inc.Inventors: Christopher K. Ober, Jianguo Wang, Edward J. Kramer
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Patent number: 5939586Abstract: A process for the production of an intermediate for a liquid crystal compound, which comprises reacting an alkyloxybiphenylcarboxylic acid with purified thionyl chloride substantially free of sulfuryl chloride, the thionyl chloride being obtained by adding phenol, etc., to thionyl chloride, heating the mixture and distilling the resultant mixture; and a process for the production of a liquid crystal compound from the above intermediate. According to the present invention, thionyl chloride can be easily purified, and a liquid crystal compound having a very high purity can be obtained by the use of the purified thionyl chloride.Type: GrantFiled: October 31, 1997Date of Patent: August 17, 1999Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hiroshi Mineta, Tomoyuki Yui
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Patent number: 5506358Abstract: There is disclosed a process for producing an alkoxyiminoacetamide compound which is useful as agricultural fungicides. Also dislclosed are novel intermediate compounds for the above process and their production.Type: GrantFiled: March 8, 1994Date of Patent: April 9, 1996Assignee: Shionogi & Co., Ltd.Inventors: Akira Takase, Hiroyuki Kai, Moriyasu Masui, Kazuo Ueda, Tsuneo Iwakawa
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Patent number: 5504249Abstract: A process for preparing o-chloromethylbenzoyl chlorides of the formula I ##STR1## where m is 0 or an integer from 1 to 4 andX is halogen or C-organic radicals,entails reacting a corresponding lactone of the formula II ##STR2## with thionyl chloride in the presence of a catalyst.Type: GrantFiled: March 31, 1995Date of Patent: April 2, 1996Assignee: BASF AktiengesellschaftInventors: Heinz Isak, Herbert Bayer, Michael Keil, Thomas Wettling
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Patent number: 5473095Abstract: The present invention relates to a process for the preparation of compounds of the formula ##STR1## in which R.sup.1 is --CN, --COOH, --COOR', R' being an organic radical having 1 to 6 carbon atoms, --CONH.sub.2, --COCl or --CHO and R.sup.2 is H or Cl, which comprises reacting a compound of the formula ##STR2## in which R.sup.1 is as defined above and R.sup.3 is H or Cl, with a chlorinating agent in the presence of a chlorination catalyst at -10.degree. to 200.degree. C.Type: GrantFiled: January 27, 1994Date of Patent: December 5, 1995Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Theodor Papenfuhs, Georg Weichselbaumer
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Patent number: 5380855Abstract: A process for preparing N,N-substituted carbamoyl halides comprising (a) contacting carbon dioxide and a secondary amine in the presence of an aprotic organic solvent and a base selected from the group consisting of a phosphazene compound, an organic, nitrogenous base, mixtures of pyridine and a phosphazene compound or an organic, nitrogenous base, and mixtures thereof, to produce the corresponding ammonium carbamate salt, and (b) reacting the ammonium carbamate salt with a halide-containing electrophilic compound to produce the corresponding N,N-substituted carbamoyl halides. A second embodiment comprises recovering the ammonium carbamate salt of step (a) prior to reacting the ammonium carbamate salt with an halide-containing electrophilic compound in the presence of an aprotic organic solvent and a base selected from the group consisting of a phosphazene compound, an organic, nitrogenous base, mixtures of pyridine and a phosphazene compound or an organic, nitrogenous base, and mixtures thereof.Type: GrantFiled: February 4, 1994Date of Patent: January 10, 1995Assignee: Monsanto CompanyInventors: William D. McGhee, John J. Talley
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Patent number: 5362909Abstract: 2,4,5-Trihalogenobenzene derivatives of the formula ##STR1## in which R is --COOH, --COCl, --COF, --CN, --CONH.sub.2, --CH.sub.2 OH, --CH.sub.2 Cl, --CHCl.sub.2, --CCl.sub.3 or --CHO,R.sup.1 is H, Cl or F, andR.sup.2 is Cl or F,it only being possible for R.sup.1 or R.sup.2 to be F, and processes for their preparation starting from benzonitriles reacted with potassium fluoride. The novel compounds are intermediates for antibacterials such as quinolone carboxylic acids.Type: GrantFiled: October 29, 1992Date of Patent: November 8, 1994Assignee: Bayer AktiengesellschaftInventors: Erich Klauke, Uwe Petersen, Klaus Grohe
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Patent number: 5344977Abstract: An improved process for the preparation of 2,3-dibromopropionyl chloride, which comprises brominating acrylic acid, adding iron powder or an iron salt to the resultant melt, chlorinating the dibromopropionic acid obtained, and removing the volatile components. The 2,3-dibromopropionyl chloride is obtained in high yield and purity and is an intermediate for synthesising in particular reactive dyes.Type: GrantFiled: January 22, 1993Date of Patent: September 6, 1994Assignee: Ciba-Geigy CorporationInventors: Alfons Arquint, Peter Leupin
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Patent number: 5202469Abstract: Partially fluorinated dicarboxylic acid and the acid chloride thereof, a process for its preparation and its use.The compound of the formula (I) ##STR1## and the acid chloride thereof are prepared by air oxidation in the presence of a catalyst mixture composed of the ions of cobalt, manganese and bromine in an acid organic medium. The compounds can be used for the preparation of linear polycarboxamides and polycarboxylic acid esters.Type: GrantFiled: June 20, 1991Date of Patent: April 13, 1993Assignee: Hoechst AktiengesellschaftInventors: Freimund Rohrscheid, Wolfgang Appel, Gunter Siegemund
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Patent number: 5072038Abstract: 2,3,4,5-trihalogenobenzene derivatives of the formula ##STR1## in which R is --COOH, --COCl, --COF, --CN, --CONH.sub.2, --CH.sub.2 OH, --CH.sub.2 Cl, --CHCl.sub.2, --CCl.sub.3 or --CHO,R.sup.1 is H, Cl or F, andR.sup.2 is Cl or F,it only being possible for R.sup.1 or R.sup.2 to be F, and processes for their preparation starting from benzonitriles reacted with potassium fluoride. The novel compounds are intermediates for antibacterials such as quinolone carboxylic acids.Type: GrantFiled: January 2, 1990Date of Patent: December 10, 1991Assignee: Bayer AktiengesellschaftInventors: Erich Klauke, Uwe Petersen, Klaus Grohe
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Patent number: 4880576Abstract: An N-alkylated formamide of the formula ##STR1## wherein R.sup.1 denotes alkylR.sup.2 denotes alkyl with at least 9 carbon atoms or the group ##STR2## wherein A denotes straight-chain or branched alkanediyl,R.sup.1 denotes lower alkyl andn denotes an integer from 2 to 6,a process for the preparation of the same and its use in the replacement of a hydroxyl group in an organic compound by chlorine or bromine the improvement wherein the replacement is carried out in the presence of an N-alkylated formamide.Type: GrantFiled: September 17, 1986Date of Patent: November 14, 1989Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Norbert Langenfeld, Wolfgang Heydkamp
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Patent number: 4851160Abstract: A process for the preparation of a compound of the formula ##STR1## in which X.sup.1 and X.sup.2 each independently is chlorine or fluorine, andY is chlorine, bromine, fluorine or iodine, comprising subjecting a compound of the formula ##STR2## to a Sandmeyer or Balz-Schiemann reaction thereby to produce a carboxylic acid of the formula ##STR3## and converting the carboxylic acid (Ia) into an acyl chloride of the formula ##STR4## The compound (II) is new. The products are known intermediates for anti-bacterials.Type: GrantFiled: August 28, 1987Date of Patent: July 25, 1989Assignee: Bayer AktiengesellschaftInventors: Uwe Petersen, Michael Schriewer, Ernst Kysela, Klaus Grohe
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Patent number: 4107099Abstract: Anion exchange resins containing borohydride counter ions display essentially the same chemical activity as solutions of sodium borohydride but have the added advantage that products treated therewith are not contaminated with sodium ions or borate ions. Thus, alcohols can now be freed of carbonyl components without thereby being contaminated with borate; metal ions, such as silver, can be reduced to the free element; metal ions of groups IV-A to VI-A can be converted to volatile metal hydrides; and transition metal ions can be converted to the boride. The anion exchange resin is prepared by treating a strong base anion exchanger with aqueous sodium borohydride or sodium cyanoborohydride. Regeneration of the borohydride form from the borate proceeds directly with aqueous sodium borohydride.Type: GrantFiled: February 10, 1977Date of Patent: August 15, 1978Assignee: Ventron CorporationInventor: Ramesh Subayya Hedge