Alkylation Or Dealkylation Process Patents (Class 546/349)
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Patent number: 9012632Abstract: Provided is a method whereby a heteroaromatic ring aryl can be very rapidly methylated at a high yield. In an N-alkyl-2-pyrrolidinone, a heteroaromatic ring aryltrialkylstannan is cross-coupled with methyl iodide in the presence of a palladium complex, a phosphine ligand, a cuprous halide, a carbonic acid salt and/or an alkali metal fluoride to thereby rapidly methylate the heteroaromatic ring aryl. (Formula shows a case wherein the heteroaromatic ring aryl is a pyridyl group.Type: GrantFiled: December 25, 2009Date of Patent: April 21, 2015Assignee: RikenInventors: Masaaki Suzuki, Hisashi Doi, Hiroko Koyama
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Publication number: 20110263849Abstract: Provided is a method whereby a heteroaromatic ring aryl can be very rapidly methylated at a high yield. In an N-alkyl-2-pyrrolidinone, a heteroaromatic ring aryltrialkylstannan is cross-coupled with methyl iodide in the presence of a palladium complex, a phosphine ligand, a cuprous halide, a carbonic acid salt and/or an alkali metal fluoride to thereby rapidly methylate the heteroaromatic ring aryl. (Formula shows a case wherein the heteroaromatic ring aryl is a pyridyl group.Type: ApplicationFiled: December 25, 2009Publication date: October 27, 2011Applicants: GIFU UNIVERSITY, RIKENInventors: Masaaki Suzuki, Hisashi Doi, Hiroko Koyama
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Patent number: 7432268Abstract: There are disclosed compounds of the formula (I): prodrugs thereof, or pharmaceutically acceptable salts of the compounds or of said prodrugs which are useful as inhibitors of Type 3 17?-Hydroxysteroid Dehydrogenase. Also disclosed are pharmaceutical compositions containing said compounds and their use for the treatment or prevention of androgen dependent diseases.Type: GrantFiled: November 14, 2005Date of Patent: October 7, 2008Assignee: Schering CorporationInventors: Timothy Guzi, Kamil Paruch, Alan Mallams, Jocelyn D. Rivera, Ronald J. Doll, Viyyoor M. Girijavallabhan, Jonathan A. Pachter, Yi-Tsung Liu, Anil K. Saksena
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Patent number: 7041856Abstract: There are disclosed a process for producing a coupling compound of formula (1): (Y—)(n?1)R1—R2—(R1)(n??1),??(1) wherein R1 and R2 independently represent a substituted or unsubstituted aryl group, which process is characterized by reacting an unsaturated organic compound of formula (2): n?(R1X1n)??(2) wherein n, n?, and R1 are the same as defined above, and X1 is the same or different and independently represents a leaving group and bonded with a sp2 carbon atom of R1 group, with a boron compound of formula (3): m{R2(BX22)n?}??(3) wherein R2 and n? are the same as defined above, X2 represents a hydroxy group, an alkoxy group, in the presence of a catalyst containing (A) a nickel compound, and (B) a nitrogen-containing cyclic compound, and the catalyst.Type: GrantFiled: October 22, 2002Date of Patent: May 9, 2006Assignee: Sumitomo Chemical Company, LimitedInventors: Tamon Itahashi, Takashi Kamikawa
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Patent number: 7026478Abstract: A process for the production of compounds Ar—R1 by means of a cross-coupling reaction of an organometallic reagent R1-M with an aromatic or heteroaromatic substrate Ar—X catalyzed by one or several iron salts or iron complexes as catalysts or pre-catalysts, present homogeneously or heterogeneously in the reaction mixture. This new invention exhibits substantial advantages over established cross coupling methodology using palladium- or nickel complexes as the catalysts. Most notable aspects are the fact that (i) expensive and/or toxic nobel metal catalysts are replaced by cheap, stable, commercially available and toxicologically benign iron salts or iron complexes as the catalysts or pre-catalysts, (ii) commercially attractive aryl chlorides as well as various aryl sulfonates can be used as starting materials, (iii) the reaction can be performed under “ligand-free” conditons, and (iv) the reaction times are usually very short.Type: GrantFiled: May 10, 2002Date of Patent: April 11, 2006Assignee: Studiengesellschaft Kohle mbHInventors: Alois Fürstner, Andreas Leitner, María Méndez
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Patent number: 6911451Abstract: Phenylalanine derivatives of formula (1) are described: wherein L1 is a linker atom or group; X1 is a group selected from —N(R3)CO—, —N(R3)SO2—, —N(R3)C(O)O— or —N(R3)CON(R3a)—; and R is a carboxylic acid or a derivative thereof. The compounds are able to inhibit the binding of a 4 integrins to their ligands and are of use in the prophylaxis and treatment of diseases or disorders involving inflammation.Type: GrantFiled: June 4, 1999Date of Patent: June 28, 2005Assignee: Celltech R&D LimitedInventors: John Robert Porter, John Clifford Head, Graham John Warrellow, Sarah Catherine Archibald
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Patent number: 6642273Abstract: An unsaturated derivative at the 4-position of 6-tert-butyl-1,1-dimethylindane corresponding to the following formula: in which: X represents: a divalent radical of formula: and Y represents a divalent radical of following formula: R1 represents —CH3, —(CH2)p—OR4, —(CH2)p—COR5 or —S(O)t—R6, p being 0, 1, 2 or 3, t being 0, 1 or 2, R4 represents H, lower alkyl, —COR7, aryl, aralkyl, mono- or polyhydroxyalkyl, or a polyether radical, R5 represents H, lower alkyl, —OR8 or R6 represents H or lower alkyl, R7 represents lower alkyl, R8 represents H, alkyl, alkenyl, alkynyl, aryl, aralkyl, mono- or polyhydroxyalkyl, a sugar residue selected from the group consisting of residues deriving from glucose, galactose, mannose and glucuronic acid or an amino acid residue deriving from lysine, glycine and aspartic acid, r′ and r″, which are identical or different, represent H, lowType: GrantFiled: August 9, 2002Date of Patent: November 4, 2003Assignee: Galderma Research & DevelopmentInventors: Angel De Lera, Beatriz Dominguez
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Patent number: 6635645Abstract: The invention relates to 2,5-diazabicyclo[2.2.1]heptane derivatives, to pharmaceutical compositions containing them, and to methods for the treatment or prevention of disorders associated with a dysfunction of the nicotinic receptors utilizing them.Type: GrantFiled: August 16, 2001Date of Patent: October 21, 2003Assignee: Sanofi-SynthelaboInventors: Alistair Lochead, Samir Jegham, Alain Nedelec, Jean Jeunesse, Frédéric Galli, Luc Even
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Patent number: 6630510Abstract: This invention relates to novel substituted succinic acid metallo-&bgr;-lactamase inhibitors which are useful potentiators of &bgr;-lactam antibiotics. Accordingly, the present invention provides a method of treating bacterial infections in animals or humans which comprises administering, together with a b-lactam antibiotic, a therapeutically effective amount of a compound of formula I: including pharmaceutically acceptable salts, prodrugs, anhydrides, and solvates thereof.Type: GrantFiled: October 26, 2000Date of Patent: October 7, 2003Assignee: Merck & Co., Inc.Inventors: James M. Balkovec, Mark L. Greenlee, Steven H. Olson, Gregory P. Rouen
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Publication number: 20030162950Abstract: There are disclosed a process for producing a coupling compound of formula (1):Type: ApplicationFiled: October 22, 2002Publication date: August 28, 2003Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Tamon Itahashi, Takashi Kamikawa
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Publication number: 20030109713Abstract: A process for producing organic substituted aromatic or heteroaromatic compounds including biaryl and biheteroaryl compounds in a two-step reaction. In the first step, the aromatic or heteroaromatic compound is borylated in a reaction comprising a borane or diborane reagent (any boron reagent where the boron reagent contains a B—H, B—B or B—Si bond) and an iridium or rhodium catalytic complex. In the second step, a metal catalyst catalyzes the formation of the organic substituted aromatic or heteroaromatic compound from the borylated compound and an electrophile such as an aryl or organic halide, triflate (OSO2CF3), or nonaflate (OSO2C4F9). The steps in the process can be performed in a single reaction vessel or in separate reaction vessels. The present invention also provides a process for synthesis of complex polyphenylenes starting from halogenated aromatic compounds.Type: ApplicationFiled: July 12, 2002Publication date: June 12, 2003Applicant: Board of Trustees operating Michigan State UniversityInventors: Milton R. Smith, III, Robert E. Maleczka
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Publication number: 20030050500Abstract: The present invention encompasses a process for preparing arylolefins by reacting one or more arylamines with one or more organic nitrites, in the presence of one or more olefins which bear at least one hydrogen atom on the double bond and in the presence of acid and in the presence of palladium or one or more palladium compounds.Type: ApplicationFiled: August 12, 2002Publication date: March 13, 2003Inventors: Markus Eckert, Albert Schnatterer, Walter Lange
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Publication number: 20020183516Abstract: Improved methods for generating a —C—C— bond by cross-coupling of a transferable group with an acceptor group. The transferable group is a substituent of an organosilicon nucleophile and the acceptor group is provided as an organic electrophile. The reaction is catalyzed by a Group 10 transition metal complex (e.g., Ni, Pt or Pd), particularly by a palladium complex. Certain methods of this invention use improved organosilicon nucleophiles which are readily prepared, can give high product yields and exhibit high stereo selectivity. Methods of this invention employ activating ions such as halides, hydroxide, hydride and silyloxides. In specific embodiments, organosilicon nucleophilic reagents of this invention include siloxanes, particularly cyclic siloxanes. The combination of the cross-coupling reactions of this invention with ring-closing metathesis, hydrosilylation and intramolecular hydrosilylation reactions provide useful synthetic strategies that have wide application.Type: ApplicationFiled: June 6, 2001Publication date: December 5, 2002Inventors: Scott E. Denmark, Jun Young Choi, Daniel Wehrli, Zhicai Wu, Luc Neuville, Weitao Pan, Ramzi F. Sweis, Zhigang Wang, Shyh-Ming Yang
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Patent number: 6245918Abstract: Process for the preparation of an ionic compound, Q+A− liquid at less than 150° C., wherein a trialkyloxonium of the anion is reacted with an amine in a hydrocarbon solvent. The aforesaid ionic compound can be used as a solvent in numerous catalytic reactions.Type: GrantFiled: June 1, 1999Date of Patent: June 12, 2001Assignee: Institut Francais du PetroleInventors: Hélène Olivier, Frédéric Favre
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Patent number: 6096894Abstract: A method of producing a 2-(p-alkylphenyl)pyridine compound economically, easily and industrially, which comprises adding manganese dioxide and trimethylchlorosilane, or adding manganese chloride to an organic ether solvent, and reacting p-alkylphenylmagnesium halide and 2-halopyridine in the obtained organic ether solvent.Type: GrantFiled: July 27, 1999Date of Patent: August 1, 2000Assignee: Sumika Fine Chemicals Co., Ltd.Inventors: Kozo Matsui, Yoshihide Umemoto, Kiyoshi Sugi, Tetsuya Shintaku, Nobushige Itaya
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Patent number: 5763668Abstract: Amines are prepared by reacting a mixture obtained in the cracking of mineral oil fractions with ammonia or a primary or secondary amine of the general formula I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.2 -C.sub.20 -alkynyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.20 -alkylcycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl, aryl, C.sub.7 --C.sub.20 -alkylaryl or C.sub.7 --C.sub.20 -aralkyl or together are a saturated or unsaturated C.sub.2 -C.sub.12 -alkylene ene chain,at from 200.degree. to 350.degree. C.Type: GrantFiled: July 3, 1996Date of Patent: June 9, 1998Assignee: BASF AktiengesellschaftInventors: Uwe Dingerdissen, Jurgen Herrmann, Karsten Eller
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Patent number: 5705648Abstract: Mepiquat chloride is formed from the reaction between N-methylpiperidine and chloromethane in an anhydrous liquid solvent selected from the group consisting of acetone, methyl ethyl ketone, toluene, tetrahydrofuran, isopropanol, acetonitrile, N,N-dimethylformamide and methylene chloride in the absence of sodium hydroxide. Mepiquat chloride precipitates as a solid of high purity and is recovered under a substantially moisture-free atmosphere.The solid mepiquat chloride can be sealed into a water soluble pouch or into a water soluble encapsulated solid form (e.g., granule, pellet, or briquette) for convenient handling. The pouch contains powdered mepiquat chloride or the encapsulated solid is merely introduced directly into a spray tank or reservoir for application with low human exposure and no containers in contact with the mepiquat chloride that require disposal.Mepiquat chloride is used as a component of a system for growing a number of commodity plants including cotton.Type: GrantFiled: October 17, 1994Date of Patent: January 6, 1998Assignee: Micro Flo Co.Inventors: Richard U. Clark, James S. Lovell, James C. Thigpen, David William Bristol, John Raymond Tyndall, Albert Roger Frisbee
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Patent number: 5360911Abstract: A novel process is disclosed for producing stilbazolium salts. Said novel process employs a heterocyclic amine catalyst, such as pyrrolidine, an alkylated pyridine salt and a substituted benzaldehyde which unexpectedly results in increased reaction rates and product yields.Type: GrantFiled: June 17, 1993Date of Patent: November 1, 1994Assignee: General Electric CompanyInventors: Eugene P. Boden, Peter D. Phelps, Kevin R. Stewart
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Patent number: 5290932Abstract: Amines of the general formula I ##STR1## where R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.20 -alkylcycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl, aryl, C.sub.7 -C.sub.20 -alkylaryl, C.sub.7 -C.sub.20 -aralkyl or a heterocyclic radical and n is an integer of from 3 to 7, are prepared by a process in which a ketone of the general formula II ##STR2## where R.sup.1 and R.sup.2 have the abovementioned meanings, is reacted with a cyclic amine of the general formula III ##STR3## where n has the abovementioned meanings, in the presence of a zeolite and/or SiO.sub.2 having a zeolite structure and/or a phosphate and/or a phosphate having a zeolite structure as catalysts at from 50.degree. to 500.degree. C. and from 0.01 to 50 bar.Type: GrantFiled: October 30, 1992Date of Patent: March 1, 1994Assignee: BASF AktiengesellschaftInventors: Uwe Dingerdissen, Wolfgang Hoelderich
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Patent number: 5080719Abstract: This invention privdes novel heteroaromatic compounds, and smoking compositions which contain an invention heteroaromatic compound as a flavorant-release additive as illustrated by the following additive structure: ##STR1## Under typical cigarette smoking conditions, 2-isopropylpyrazine and acetophenone are released as pyrolysis products, and enhance the flavor and aroma of the mainstream and sidestream smoke.Type: GrantFiled: September 24, 1987Date of Patent: January 14, 1992Assignee: Philip Morris IncorporatedInventors: Yoram Houminer, Henry V. Secor, Jeffrey I. Seeman
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Patent number: 5061805Abstract: A process for dealkylating the 2-position on a trisubstituted pyridine derivative having the formula ##STR1## where R.sub.1 is a straight chain alkyl group from about C.sub.2 -C.sub.5 and where R.sub.2 and R.sub.3 are alkyl, aryl or aralkyl groups up to about C.sub.10, comprising the step of reacting said pyridine derivative at reflux with excess sulfur. Of particular note is the preparation of 2,3,5-trimethylpyridine including the initial preparation of its 2-ethyl precursor by the Chichibabin reaction of propionaldehyde and ammonia.Type: GrantFiled: August 10, 1990Date of Patent: October 29, 1991Assignee: Reilly Industries, Inc.Inventor: Gerald L. Goe
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Patent number: 4701530Abstract: Process for the production of 2,4,6-trimethyl pyridine wherein a carbonyl compound such as acetone is reacted with ammonia in the presence of a condensation catalyst at a temperature in the range from 100.degree. to 200.degree. C. to produce a mixture of products containing 2,2,4,6-tetramethyl-1,2-dihydropyridine which is then purified. The substantially pure dihydropyridine is then contacted with a cracking catalyst at a temperature in the range from 250.degree. to 450.degree. C. to produce 2,4,6-trimethyl pyridine in high yield.Type: GrantFiled: October 1, 1986Date of Patent: October 20, 1987Assignee: The Dow Chemical CompanyInventors: Loren L. Swearingen, Randy J. LaTulip
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Patent number: 4658032Abstract: Process for producing 2,3,5-collidine and/or 2,3,5,6-tetramethylpyridine which is characterized by reacting 3,5-lutidine as the starting material with an aliphatic alcohol having 1 to 4 carbon atoms, in the presence of a catalyst for hydrogenation at a temperature of 200.degree. C. or higher.The above-mentioned 2,3,5-collidine and/or 2,3,5,6-tetramethylpyridine are important compounds as intermediates for synthesizing various pharmaceutical chemicals.Type: GrantFiled: July 10, 1985Date of Patent: April 14, 1987Assignee: Koei Chemical Co., Ltd.Inventor: Mitsuharu Yamaji
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Patent number: 4656299Abstract: A complex of an electron-attracting group-substituted .eta..sup.5 -cyclopentadienylcobalt with a polyene or an acetylene for use as a catalyst, for example, for the synthesis of a substituted pyridine from an alkyne and a nitrile.Type: GrantFiled: January 13, 1986Date of Patent: April 7, 1987Assignees: Denki Kagaku Kogyo Kabushiki Kaisha, Rikagaku KenkyusyoInventors: Chiyuki Fujii, Seiichi Watanabe
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Patent number: 4294968Abstract: The catalytic method of preparing .alpha.-picoline from 5-oxohexanenitrile is improved by using as the catalyst carbon-supported palladium.Type: GrantFiled: July 7, 1980Date of Patent: October 13, 1981Assignee: The Dow Chemical CompanyInventors: Frederick C. Stone, Gary G. Schupska
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Patent number: 4220785Abstract: This invention relates to substituted pyridines prepared by reacting aldehydes, amines, lower carboxylic acids such as acetic acid in the presence of oxygen. The N-substituted pyridinium salts formed can be converted to pyridines by thermal dealkylation.Type: GrantFiled: August 25, 1978Date of Patent: September 2, 1980Assignee: Petrolite CorporationInventors: Bernardus A. Oude Alink, Neil E. S. Thompson
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Patent number: 4189585Abstract: A process for preparing pyridine with 2,6 lutidine as by-product, by catalytic demethylation of .alpha.-picoline in the gaseous phase with steam is disclosed wherein the demethylation step is conducted at a temperature of 250.degree.-360.degree. C. using a metallic hydrogenation catalyst at a contact time of about 0.5 to 15 seconds. Pyridine is a known important organic base with many uses, such as denaturant for alcohols and solvent in the rubber and paint industries.Type: GrantFiled: April 21, 1978Date of Patent: February 19, 1980Assignee: Stamicarbon, B.V.Inventors: Egidius J. M. Verheijen, Nicolaas L. G. Duys
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Patent number: 4186148Abstract: 3,7-Dimethyl-2,6-octadienylamine derivatives are produced by reacting isoprene with a secondary amine in the presence of a catalyst prepared by reacting a secondary amine, a conjugated diene and/or a polycyclic aromatic compound, a lithium salt and sodium and/or potassium metal.Type: GrantFiled: May 3, 1978Date of Patent: January 29, 1980Assignee: Nissan Chemical Industries LimitedInventors: Atsuo Murata, Shuji Tsuchiya, Akihiro Konno, Jun Uchida
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Patent number: 4179580Abstract: A process for increasing the reaction rate of condensation reactions which occur between non-conjugated non-aromatic olefinically unsaturated hydrocarbons and active hydrogen-containing organic compounds in the presence of alkali metal comprising carrying out the reaction in the presence of titanium metal.Type: GrantFiled: May 11, 1978Date of Patent: December 18, 1979Assignee: Phillips Petroleum CompanyInventor: Raymond L. Cobb
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Patent number: 4138488Abstract: Disclosed herein are substituted diphenylmethyl picolinic acids, pharmaceutically acceptable salts, amides and esters thereof. The compounds disclosed are useful as topical anti-acne agents.Type: GrantFiled: January 10, 1977Date of Patent: February 6, 1979Assignee: Schering CorporationInventors: Margaret H. Sherlock, Heide Roebke