Reactant Having Halogen Bonded Directly To Sulfur By Nonionic Bonding Patents (Class 562/862)
  • Patent number: 8853393
    Abstract: The invention discloses a novel intermediate for preparing tapentadol and analogues thereof, wherein the structural formula is shown as formula I or II, and the groups are defined as the specification. The invention further discloses a method for preparing the novel intermediate and use of the intermediate for preparing tapentadol and analogues thereof. The invention can remarkably improve the product yield and quality of tapentadol, reduce the production cost, and simplify the production procedure. The preparation process is environment friendly, thus more suitable for the requirements of industrial production.
    Type: Grant
    Filed: July 29, 2011
    Date of Patent: October 7, 2014
    Assignee: Anhui New Star Pharmaceutical Development Co., Ltd.
    Inventors: Ziao Xu, Yuanhai Zhao, Degang Li, Xiaoxiang Li
  • Publication number: 20130231478
    Abstract: The invention discloses a novel intermediate for preparing tapentadol and analogues thereof, wherein the structural formula is shown as formula I or II, and the groups are defined as the specification. The invention further discloses a method for preparing the novel intermediate and use of the intermediate for preparing tapentadol and analogues thereof. The invention can remarkably improve the product yield and quality of tapentadol, reduce the production cost, and simplify the production procedure. The preparation process is environment friendly, thus more suitable for the requirements of industrial production.
    Type: Application
    Filed: July 29, 2011
    Publication date: September 5, 2013
    Inventors: Ziao Xu, Yuanhai Zhao, Degang Li, Xiaoxiang Li
  • Publication number: 20120310010
    Abstract: 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: Application
    Filed: August 13, 2012
    Publication date: December 6, 2012
    Applicant: BASF SE
    Inventors: Thomas Schmidt, Joachim Gebhardt, Sandra Löhr, Michael Keil, Jan Hendrik Wevers, Michael Rack, Guido Mayer, Axel Pleschke
  • Publication number: 20120130097
    Abstract: 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: Application
    Filed: January 30, 2012
    Publication date: May 24, 2012
    Applicant: AstraZeneca AB
    Inventors: Adrian Clark, Elfyn Jones, Ulf Larsson, Anna Minidis
  • Publication number: 20120053365
    Abstract: 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: Application
    Filed: July 29, 2011
    Publication date: March 1, 2012
    Applicant: FUJIFILM CORPORATION
    Inventor: Akiyoshi GOTO
  • Publication number: 20110190520
    Abstract: 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: Application
    Filed: February 8, 2011
    Publication date: August 4, 2011
    Applicant: AstraZeneca AB
    Inventors: Adrian Clark, Elfyn Jones, Ulf Larsson, Anna Minidis
  • Patent number: 7728171
    Abstract: 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: Grant
    Filed: August 25, 2008
    Date of Patent: June 1, 2010
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Ursula Hoffmann, Goesta Rimmler
  • Publication number: 20090192333
    Abstract: 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: Application
    Filed: April 6, 2009
    Publication date: July 30, 2009
    Inventor: Ursula Hoffmann
  • Publication number: 20090076304
    Abstract: 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: Application
    Filed: September 30, 2008
    Publication date: March 19, 2009
    Applicant: AJINOMOTO CO., INC.
    Inventors: Tatsuya Ishikawa, Shouichi Kondou, Satoji Takahashi
  • Publication number: 20090036703
    Abstract: 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: Application
    Filed: August 25, 2008
    Publication date: February 5, 2009
    Inventors: Ursula Hoffmann, Goesta Rimmler
  • Patent number: 7435849
    Abstract: 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: Grant
    Filed: October 17, 2006
    Date of Patent: October 14, 2008
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Ursula Hoffmann, Goesta Rimmler
  • Patent number: 7102046
    Abstract: 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: Grant
    Filed: November 27, 2002
    Date of Patent: September 5, 2006
    Assignee: Bayer Aktiengesellschaft
    Inventors: Florian Rampf, Markus Eckert
  • Patent number: 7094926
    Abstract: 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: Grant
    Filed: January 25, 2001
    Date of Patent: August 22, 2006
    Assignee: Kaneka Corporation
    Inventors: Susumu Amano, Masaru Mitsuda, Kenji Inoue, Koichi Kinoshita, Koki Yamashita, Yasuyoshi Ueda
  • Patent number: 7034181
    Abstract: 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: Grant
    Filed: November 27, 2000
    Date of Patent: April 25, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Roland Götz, Norbert Götz, Michael Keil, Bernd Wolf, Adrian Steinmetz, Armin Stamm, Jochem Henkelmann
  • Patent number: 6844468
    Abstract: 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: Grant
    Filed: October 3, 2002
    Date of Patent: January 18, 2005
    Assignee: Clariant GmbH
    Inventors: Lars Bierer, Joachim Ritzer, Berthold Schiemenz, Thomas Wessel
  • Publication number: 20040152782
    Abstract: 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: Application
    Filed: July 3, 2003
    Publication date: August 5, 2004
    Inventors: Ronit Yahalomi, Evgeny Shapiro, Ben-Zion Dolitzky, Yigael Gozlan
  • Patent number: 6465700
    Abstract: 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: Grant
    Filed: August 3, 1998
    Date of Patent: October 15, 2002
    Assignee: Boulder Scientific Company
    Inventors: Jeffrey M. Sullivan, Hamlin H. Barnes
  • Patent number: 6206819
    Abstract: 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: Grant
    Filed: May 15, 2000
    Date of Patent: March 27, 2001
    Assignee: Rohm and Haas Company
    Inventors: Deborah Diane Graves, Thomas Duncan Rose, David James Swank, Charles Chao Wu
  • Patent number: 6166252
    Abstract: 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: Grant
    Filed: January 7, 1999
    Date of Patent: December 26, 2000
    Assignee: Ausimont S.p.A.
    Inventors: Piero Gavezotti, Julio A. Abusleme, Vito Tortelli
  • Patent number: 6114467
    Abstract: 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: Grant
    Filed: August 11, 1998
    Date of Patent: September 5, 2000
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Christopher K. Ober, Jianguo Wang, Edward J. Kramer
  • Patent number: 5939586
    Abstract: 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: Grant
    Filed: October 31, 1997
    Date of Patent: August 17, 1999
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hiroshi Mineta, Tomoyuki Yui
  • Patent number: 5506358
    Abstract: 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: Grant
    Filed: March 8, 1994
    Date of Patent: April 9, 1996
    Assignee: Shionogi & Co., Ltd.
    Inventors: Akira Takase, Hiroyuki Kai, Moriyasu Masui, Kazuo Ueda, Tsuneo Iwakawa
  • Patent number: 5504249
    Abstract: 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: Grant
    Filed: March 31, 1995
    Date of Patent: April 2, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Isak, Herbert Bayer, Michael Keil, Thomas Wettling
  • Patent number: 5473095
    Abstract: 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: Grant
    Filed: January 27, 1994
    Date of Patent: December 5, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralf Pfirmann, Theodor Papenfuhs, Georg Weichselbaumer
  • Patent number: 5380855
    Abstract: 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: Grant
    Filed: February 4, 1994
    Date of Patent: January 10, 1995
    Assignee: Monsanto Company
    Inventors: William D. McGhee, John J. Talley
  • Patent number: 5362909
    Abstract: 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: Grant
    Filed: October 29, 1992
    Date of Patent: November 8, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Erich Klauke, Uwe Petersen, Klaus Grohe
  • Patent number: 5344977
    Abstract: 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: Grant
    Filed: January 22, 1993
    Date of Patent: September 6, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Alfons Arquint, Peter Leupin
  • Patent number: 5202469
    Abstract: 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: Grant
    Filed: June 20, 1991
    Date of Patent: April 13, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Freimund Rohrscheid, Wolfgang Appel, Gunter Siegemund
  • Patent number: 5072038
    Abstract: 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: Grant
    Filed: January 2, 1990
    Date of Patent: December 10, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Erich Klauke, Uwe Petersen, Klaus Grohe
  • Patent number: 4880576
    Abstract: 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: Grant
    Filed: September 17, 1986
    Date of Patent: November 14, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz U. Blank, Norbert Langenfeld, Wolfgang Heydkamp
  • Patent number: 4851160
    Abstract: 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: Grant
    Filed: August 28, 1987
    Date of Patent: July 25, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Michael Schriewer, Ernst Kysela, Klaus Grohe
  • Patent number: 4107099
    Abstract: 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: Grant
    Filed: February 10, 1977
    Date of Patent: August 15, 1978
    Assignee: Ventron Corporation
    Inventor: Ramesh Subayya Hedge