Abstract: 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:
Grant
Filed:
March 14, 2005
Date of Patent:
December 12, 2006
Assignee:
Board of Trustees of Michigan State University
Inventors:
Milton R. Smith, III, Robert E. Maleczka
Abstract: The invention is concerned with novel N-(4-carbamimidoyl-phenyl)-glycine derivatives of the formula: wherein R1, E, X1 to X4 and G1 and G2 are as defined in the description and the claims, as well as hydrates or solvates and physiologically usable salts thereof.
Type:
Grant
Filed:
August 12, 2003
Date of Patent:
July 4, 2006
Assignee:
Hoffmann-La Roche Inc.
Inventors:
Jean Ackermann, Leo Alig, Alexander Chucholowski, Katrin Groebke, Kurt Hilpert, Holger Kuehne, Ulrike Obst, Lutz Weber, Hans Peter Wessel
Abstract: The invention relates to a dye composition that is useful for dyeing keratin fibres, containing at least one oxidation base and at least one coupler of the 6-alkoxy-2,3-diaminopyridine type in which the amino radical in position 2 is a monosubstituted amino radical, to the use of this composition for dyeing keratin fibres and to the dyeing process using this composition. The invention also relates to novel 6-alkoxy-2,3-diaminopyridine compounds that are useful as couplers.
Abstract: A compound of Formula (1): ? wherein R1 represents an amidinophenyl group, etc.; R2 represents a hydrogen atom, etc.; R3 represents a carbamoylalkyl group, etc.; R4 represents a hydrogen atom, etc.; R5 represents a benzyl group, etc.; R6 represents a hydrogen atom, etc.; and R7 represents an alkylsulfonyl group, etc. A crystal of a complex between factor VIIa/human soluble tissue factor and a low-molecular weight reversible factor VIIa inhibitor. A medium carrying a part or all of structure coordinate data of a complex between human factor VIIa/human soluble tissue factor and a low-molecular weight reversible factor VIIa inhibitor, obtainable by X-ray crystal structure analysis of the crystal. A method for computationally designing a low-molecular weight reversible factor VIIa inhibitor using the coordinate data.
Abstract: Use of an extract of the plant Myrsine africana in oxidation dyeing for dyeing keratin fibres, a novel composition comprising this plant extract, a process for the oxidation dyeing of keratin fibres using this composition, as well as the coloured products obtained using the composition.
Type:
Grant
Filed:
November 14, 2002
Date of Patent:
December 13, 2005
Assignee:
L'Oreal S.A.
Inventors:
Béatrice Belcour-Castro, Hervé Burgaud, Georges Hussler, Michel Seite
Abstract: Process for the synthesis of 5-(3-pyridylmethyl)imidazolidine-2,4-dione, according to which 5-(3-pyridylmethylene)imidazolidine-2,4-dione is subjected to a hydrogenation reaction.
Abstract: 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:
Grant
Filed:
July 12, 2002
Date of Patent:
March 15, 2005
Assignee:
Board of Trustees of Michigan State University
Inventors:
Milton R. Smith, III, Robert E. Maleczka
Abstract: Dyeing compositions for the dyeing of keratin fibers comprising at least one oxidation base chosen from formula (I), as defined herein and addition salts thereof. The use of the compositions for the dyeing of keratin fibers. Dyeing processes employing the compositions. Novel 2,5-diaminopyridine compounds and addition salts thereof and their use as oxidation bases.
Abstract: The present invention provides processes for preparing terpyridine compounds. In particular, the present invention provides a process for the preparation of a C1-C4-alkyl pyridine-2-carboxylate compound, a 1,5-bis(2-pyridyl)pentane-1,3,5-trione compound, and a 2,6-bis(2-pyridyl)-4(1H)pyridinone compound.
Type:
Application
Filed:
April 14, 2004
Publication date:
December 30, 2004
Applicant:
BASF Aktiengesellschaft
Inventors:
Ralph Lunkwitz, Gunther Pabst, Gunter Scherr
Abstract: Couplers for hair coloring compositions for oxidative dyeing of hair are compounds of the formula (1):
wherein X is selected from halogen and R2SO4; R3 is selected from C1 to C2 alkyl or hydroxyethyl; R2 is selected from C1 to C22 alkyl and C1 to C22 mono and dihydroxyalkyl; and R is selected from of C1 to C16 alkyl, C1 to C10 hydroxyalkyl, C1 to C6 alkoxyalkyl and benzyl.
Abstract: 4-Aminopicolinic acids having aryl or heteroaryl substituents in the 6-position and their amine and acid derivatives are potent herbicides demonstrating a broad spectrum of weed control.
Type:
Grant
Filed:
July 30, 2002
Date of Patent:
August 31, 2004
Assignee:
Dow AgroSciences LLC
Inventors:
Terry William Balko, Ann Marie Buysse, Jeffrey Brian Epp, Stephen Craig Fields, Christian Thomas Lowe, Renee Joan Keese, John Sanders Richburg, III, James Melvin Ruiz, Monte Ray Weimer, Renard Antonio Green, Roger Eugene Gast, Kristy Bryan, Nicholas Martin Irvine, William Chi-Leung Lo, William Kirkland Brewster, Jeffery Dale Webster
Abstract: The present invention relates to a process for preparing 2-haloalkylnicotinic acids and haloalkylnicotinic acid derivatives starting from halomethyl-substituted enones and 3-dialkylaminoacrylic esters and also to intermediates of the process according to the invention.
Abstract: Process for the preparation of anti-ischemic and anti-hypertensive drug amlodipine besylate [2-{(2-aminoethoxy)-methyl-4-(2-chlorophenyl) 3-ethoxy carbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine} benzene sulphonate]. Phthalic anhydride is condensed with monoethanol amine at 150-190° C. The resulting N-(2-hydroxyethyl) phthalimide is coupled with 4-chloroethyl acetoacetate in the presence of sodium hydride in an organic solvent in an inert atmosphere at −11 to −15° C. Ethyl-4-[-2(phthalimido) ethoxy] acetoacetate formed is coupled with orthochloro benzaldehyde in the presence of pyridine salt at 70-90° C. Ethyl-2-(2-chloro benzylidine)4-[-2(phthalimido) ethoxy] acetoacetate fanned is condensed with methyl amino crotonate at 20-40° C.
Abstract: The present invention relates to a process for the preparation of halo-4-phenoxyquinolines.
Type:
Application
Filed:
June 30, 2003
Publication date:
March 4, 2004
Inventors:
Karl Leopold Krumel, Ruth Cezar Reed, Thomas A. Olmstead, Gary Alan Roth, Ian Robert King, Donald Neil Brattesani, Kent Douglas Campbell, John Davies
Abstract: A process is described for reacting a vinylogous amide with an &agr;,&bgr;-unsaturated ketone in the presence of a silicon compound to form an 1,5-diketone which is converted to a 1,4-dihydropyridine. Asymmetric substituted 1,4-dihydropyridines are synthesized by the process by preparing an asymmetric vinylogous amide by reacting a 1,3-cyclohexanedione with a substantially homo-chiral phenylethylamine. Reaction of the asymmetric vinylogous amide with an &agr;,&bgr;-unsaturated ketone in the presence of a silicon compound forms an asymmetric 1,5-diketone. The 1,5-diketone is converted to an asymmetric substituted 1,4-dihydropyridine.
Abstract: A process which comprises admixing in the absence of a solvent an amine of the formula R1—NH2 and a first ester of the formula
wherein R2 is an electron withdrawing group and R3 is an alkyl group; heating the mixture containing the amine and the first ester to form an intermediate compound of the formula
admixing the intermediate compound with a base and a second ester of the formula
said second ester being present in a molar excess relative to the intermediate compound, said base being present in a molar excess relative to the intermediate compound, and heating the mixture to form a pyridone compound of the formula
or a salt thereof. Also disclosed is a process for preparing diazopyridone colorants which comprises preparing a pyridone compound by the above process and reacting the pyridone compound with a diazonium salt to form a diazopyridone compound.
Type:
Grant
Filed:
June 27, 2002
Date of Patent:
February 24, 2004
Assignee:
Xerox Corporation
Inventors:
James D. Mayo, James M. Duff, Rina Carlini, Roger E. Gaynor, George Liebermann
Abstract: Photoresists and associated processes for microlithography in the extreme, far, and near UV are disclosed. The photoresists in some embodiments comprise (a) a fluorine-containing copolymer comprising a repeat unit derived from at least one ethylenically unsaturated compound characterized in that at least one ethylenically unsaturated compound is polycyclic and at least one ethylenically unsaturated compound contains at least one fluorine atom covalently attached to an ethylenically unsaturated carbon atom; and (b) at least one photoactive component.
Abstract: Disclosed is a process for preparing substituted pyridone compounds which comprises (a) admixing in the absence of a solvent (1) an amine of the formula R1—NH2 wherein R1 is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and (2) a first ester of the formula 1
Type:
Application
Filed:
June 27, 2002
Publication date:
January 8, 2004
Applicant:
Xerox Corporation
Inventors:
James D. Mayo, James M. Duff, Rina Carlini, Roger E. Gaynor, George Liebermann
Abstract: The invention relates to compounds of the general formula
wherein R1, R2, R3, R4, R5, X1, X2, X3, m and n have the significances given in claim 1, and optionally the enantiomers thereof. The active ingredients have advantageous pesticidal properties. They are especially suitable for the control of pests on domestic and farm animals.
Type:
Grant
Filed:
May 16, 2002
Date of Patent:
December 23, 2003
Assignee:
Novartis Animal Health US, Inc.
Inventors:
Pierre Ducray, Jacques Bouvier, Urs Müller
Abstract: Commercially viable process for producing 2,6-dihydroxy-3,4-dimethlpridine. The process includes reacting 2-cyanoacetamide with sodium methoxide followed by condensation with ethyl 2-methylacetoacetate in methanol to give the sodium salt of 2,6-dihydroxy-4,5-dimethyl-3-pyridinecarbonitrile. The sodium salt of 2,6-dihydroxy-4,5-dimethyl-3-pyridinecarbonitrile is hydrolyzed with hydrobromic acid and decarboxylated to the hydrobromide salt of 2,6-dihydroxy-3,4-dimethylpyridine. The desired 2,6-dihydroxy-3,4-dimethylpyridine is produced from the hydrobromide salt by neutralizing the same with sodium hydroxide.
Abstract: The present invention relates to a process for preparing 2-haloalkylnicotinic acids and haloalkylnicotinic acid derivatives starting from halomethyl-substituted enones and 3-dialkylaminoacrylic esters and also to intermediates of the process according to the invention.
Abstract: The present invention relates to an improved process for the preparation of 2-chloro-5-methyl pyridine-3-carbaldehyde which is a useful intermediate in the preparation of a variety of pharmaceutical and pesticide products.
Abstract: An intermediate for the synthesis of amlodipine, a process for the preparation thereof and the corresponding use are disclosed. The intermediate is ethyl 3-amino-4-(2-(phthalimido)ethoxy)crotonate and is of formula III:
The process for the preparation thereof comprises reacting the acetoacetate of formula:
with ammonium acetate; and the use thereof is for the preparation of the compound of formula:
the process being conducted by reacting ethyl 3-amino-4-[2-(phthalimido)ethoxy]crotonate with a benzylidene derivative.
Type:
Grant
Filed:
January 10, 2002
Date of Patent:
August 5, 2003
Assignee:
Esteve Química, S.A.
Inventors:
Laura Coppi, Yolanda Gasanz Guillén, Julio Campón Pardo
Abstract: A five-step process for preparing 1-(6-methylpyridin-3-yl)-2-[4-methylsulfonyl)phenyl]ethanone of formula (I):
The process involves the following steps: (a) 4-(methylthio)benzyl alcohol is converted into 4-(methylthio)benzyl chloride; (b) 4-(methylthio)benzyl chloride is converted with an alkali metal cyanide into 4-(methylthio)phenylacetonitrile; (c) 4-(methylthio)phenylacetonitrile is condensed with a 6-methyinicotinic ester to give 3-[2-(2-(methylthio)phenyl)-2-cyanoacetyl](6-methyl)pyridine; (d) 3-[2-(4-(methylthio)phenyl-2-cyanoacetyl](6-methyl)pyridine is hydrolyzed and decarboxylated under acidic conditions to give 3-[2-(4-(methylthio)-phenyl)acetyl](6-methyl)pyridine is hydrolyzed and decarboxylated under acidic conditions to give 3-[2-(4-(methylthio)phenyl)acetyl(6-methyl)pyridine; and (e) 3-[2(4-(methylthio)phenyl)acetyl](6-methyl)pyridine is oxidized to give the end product.
Abstract: The present invention provides of method of preparing phenyl-substituted azoles. This method uses an efficient ligand-accelerated Ullmann coupling reaction of anilines with azoles. The coupling products are useful for preparing factor Xa inhibitors.
Type:
Grant
Filed:
July 25, 2001
Date of Patent:
April 1, 2003
Assignee:
Bristol-Myers Squibb Pharma Company
Inventors:
Jiacheng Zhou, Pasquale N. Confalone, Hui-Yin Li, Philip Ma, Lynette M. Oh, Lucius T. Rossano, Charles G. Clark, Chris Teleha
Abstract: 4-Haloalkylnicotinonitriles having the formula (I)
which are suitable as intermediates in the preparation of pesticides, are obtained by:
(a) reacting a 3-amino-1-haloalkyl-2-propen-1-one
RF—C(O)—CH═CH—NH2 (II)
in a condensation reaction with a compound of the formula (III) to (VII),
(R1Z)CH═CH—CN (III)
(R1Z)2CH—CH2—CN (IV)
Hal-CH═CH—CN (V)
Hal2CH—CH2CN (VI)
HC≡C—CN (VII),
to give a compound of the formula (VIII), (IX) and/or (X),
RF—C(O)—CH═CH—NH—CH═CH—CN (VIII)
RF—C(O)—CH═CH—NH—CH(ZR1)—CH2—CN (IX)
RF—C(O)—CH═CH—NH—CH(Hal)—CH2—CN (X)
wherein RF is (C1-C4)-haloalkyl, R1 is alkyl, Hal is Cl or Br and each Z, independently, is O, S, NR or OCO; and
(b) subjecting the react
Type:
Grant
Filed:
December 13, 2001
Date of Patent:
April 1, 2003
Assignee:
Aventis Cropscience GmbH
Inventors:
Sergiy Pazenok, Henricus Maria Martinus Bastiaans
Abstract: A process for producing a 2-pyridylpyridine derivative usable as an intermediate for medicines or agricultural chemicals is provided, which does not require expensive metal catalysts, which does not cause environmental problems, and which can be conducted on an industiral scale. The process comprises the step (A) of producing an amidrazone compound from a cyano group-containing heterocyclic compound in water, the step (B) of producing a 1,2,4-triazine compound from the amidrazone compound in water, and the step (C) of producing a 2-pyridylpyridine derivative from the 1,2,4-triazine compound.
Type:
Grant
Filed:
December 12, 2001
Date of Patent:
January 7, 2003
Assignee:
Sankio Chemical Co., Ltd.
Inventors:
Fumiaki Ikeuchi, Taichi Shintou, Hirokazu Suda
Abstract: The invention relates to a method for producing hydroxymethylpyridines from the corresponding vinylpyridines by means of ozonisation in an alcohol as solvent and by means of hydrogenation of the peroxide-containing solution produced thereby, in the presence of a hydrogenation catalyst The hydrogenation solution is adjusted to a pH value of 10 to 14 by adding a base and the alcohol is distilled off and the desired hydroxymethylpyridine is isolated in high purity by extracting with an organic solvent and by means of subsequent distillative purification.
Type:
Grant
Filed:
May 2, 2002
Date of Patent:
November 26, 2002
Assignee:
DSM Fine Chemicals Austria NFG GmbH & Co KG
Inventors:
Karlheinz Giselbrecht, Rudolf Hermanseder
Abstract: The present invention provides a process for synthesis of tri- and tetra-alkylated pyridines (i.e. collidines) in high yields by reacting methyl ethyl ketone with formaldehyde in presence of ammonia in gas phase in the presence of a zeolite catalyst which comprises of silica-alumina with atleast one metal ion and/or metal selected from the group consisting of lanthanum, lead, manganese, iron, copper and cobalt. This process provides eco-friendly, more economical and shape-selective heterogeneous method.
Type:
Application
Filed:
March 27, 2001
Publication date:
November 21, 2002
Applicant:
COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH
Abstract: The invention is concerned with novel N-(4-carbamimidoyl-phenyl)-glycine derivatives of the formula:
wherein R1, E, X1 to X4 and G1 and G2 are as defined in the description and the claims, as well as hydrates or solvates and physiologically usable salts thereof.
Type:
Grant
Filed:
January 12, 2001
Date of Patent:
November 5, 2002
Assignee:
Hoffmann-La Roche Inc.
Inventors:
Jean Ackermann, Leo Alig, Alexander Chucholowski, Katrin Groebke, Kurt Hilpert, Holger Kuehne, Ulrike Obst, Lutz Weber, Hans Peter Wessel
Abstract: The present invention relates to the use of 2-aminothiazoline derivatives of formula:
in which either R1 is a hydrogen atom or an alkyl radical and R2 is an alkyl, -alk—NH2, —CH2—R3, —CH2—S—R4 or phenyl radical substituted with a nitro or —NH— C (═NH) CH3 radical, or R1 is an alkyl radical and R2 is a hydrogen atom, R3 is a (3-6C) cycloalkyl, pyridyl, pyridyl N-oxide, thienyl, thiazolyl, imidazolyl, pyrazinyl, triazolyl or phenyl radical or a phenyl radical substituted with a nitro, hydroxy or carboxyl radical, R4 represents a pyridyl or pyridyl N-oxide radical, alk represents an alkylene radical, or pharmaceutically acceptable salts thereof, as inhibitors of inducible NO-synthase.
Type:
Grant
Filed:
June 8, 2001
Date of Patent:
September 17, 2002
Assignee:
Aventis Pharma S.A.
Inventors:
Jean-Christophe Carry, Dominique Damour, Claude Guyon, Serge Mignani, Antony Bigot, Eric Bacque, Michel Tabart
Abstract: A process for the catalytic coupling of cyclic hydrocarbons with a functionalizing reagent under thermal conditions to functionalize the cyclic hydrocarbon at its secondary or aromatic C—H site.
Type:
Application
Filed:
March 1, 2001
Publication date:
November 8, 2001
Inventors:
John Frederick Hartwig, Thomas Carl Semple, Huiyuan Chen
Abstract: The present invention provides an intermediate for producing a thienopyridine derivative useful as a GnRH antagonist as well as an efficient and safe method for producing the same in an industrial scale at a high yield.
Abstract: Acylsulfamoylbenzamides of the formula I and crop protection compositions comprising them are described. In this formula I, R1, R2, R3, R4 and R5 are various organic radicals and X is CH or N.
Type:
Grant
Filed:
September 25, 1998
Date of Patent:
June 26, 2001
Assignee:
Hoechst Schering AgrEvo GmbH
Inventors:
Frank Ziemer, Lothar Willms, Thomas Auler, Hermann Bieringer, Christopher Rosinger
Abstract: The invention relates to a process for producing pyridinoline and deoxypyridinoline crosslinks and derivatives thereof and their use in determining connective tissue disorders in humans and animals.
Abstract: 2,3,5-Collidine and 2-ethyl-5-methylpyridine are prepared in high yields at the same time by reacting methacrolein and methyl ethyl ketone with ammonia in a gas phase in the presence of a catalyst which comprises silica-alumina containing at least one element selected from the group consisting of cobalt, zinc, cadmium, thallium and lead.
Abstract: The present invention concerns a process for the preparation of a 2,5 disubstituted pyridine of the formula (I) ##STR1## which comprises the steps of a) reacting a compound of the formula (II)R.sup.1 --CH.dbd.CH--R.sup.2 (II)with an acrylic compound of the formula (III) ##STR2## to form a compound of the formula (IV) ##STR3## and b) reacting the compound of formula (IV) under water free conditions with a hydrogen halide in which formula R.sup.1 signifies lower alkyl, R.sup.2 signifies di-(lower alkyl)amino or a 5- or 6-membered --N-heterocyclyl group having the free valence bond at the nitrogen atom, and X signifies halogen.
Abstract: There is provided a high efficiency base synthesis process for shape selective production of pyridine and picoline products from ammonia and C.sub.1-5 carbonyl compounds. The process includes reacting ammonia and at least one C.sub.1-5 carbonyl reactant under suitable reaction conditions of temperature, pressure, and space velocity in the presence of a catalyst comprising a molecular sieve to produce a primary product comprising pyridine or picoline products and polyalkylpyridines or other higher molecular weight aromatic species, separating and collecting the pyridine or picoline products from the polyalkylpyridines or other higher molecular weight aromatic species, and circulating the polyalkylpyridines or other higher molecular weight aromatic species to the same or another catalyst under conversion conditions to yield additional pyridine or picoline products with substantially reduced amounts of polyalkylpyridines or other higher molecular weight aromatic species.
Type:
Grant
Filed:
December 31, 1997
Date of Patent:
October 19, 1999
Assignee:
Mobil Oil Corporation
Inventors:
Arthur Chester, Scott Han, Dominick N. Mazzone, Chaya R. Venkat
Abstract: Disclosed is a process for the preparation of pyridine bases by a reaction of an aliphatic aldehyde and/or ketone with ammonia under gaseous phase using a specified catalyst in which a specified metal or combined metals are carried in or onto specified zeolites, for example, such as zeolites having a specified specific density range.
Abstract: A process has been found for preparing pyridine-2,6-diamines, i.e., 2,6-diaminopyridine (DAP) and derivative compounds in which one of the amino groups is a substituted amine (secondary or tertiary). According to this process, 3-hydroxy pentane 1,5-dinitrile (3-hydroxyglutaronitrile) is reacted with an ammonium donor in the form of ammonia, a primary amine such as n-butylamine, or a secondary amine such as piperidine.
Type:
Grant
Filed:
November 13, 1997
Date of Patent:
August 17, 1999
Assignee:
Akzo Nobel N.V.
Inventors:
Adrianus Maria Reichwein, Doetze Jakob Sikkema
Abstract: Described are preferred processes for preparing heterocycles having one or more nitrogen and/or oxygen heteroatoms, utilizing a 1,3-dihalopropene as an effective 3-carbon fragment. Preferred processes yield pyridines, quinolines, oxazoles, pyrimidines and pyrazoles, depending upon the other reactant or reactants utilized with the 1,3-dihalopropene.
Abstract: The present invention relates to new N-substituted cis-N-propenyl-acetamides of the general formula (I) ##STR1## in which R.sup.1 represents in each case optionally substituted alkyl, -C(alkyl).sub.2 -alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aralkyl or hetarylalkyl;a process for their preparation, and their use for the preparation of 2-chloro-5-methyl-pyridine.