Process Of Forming Pyridine Ring Patents (Class 546/250)
  • Patent number: 10618039
    Abstract: A process for increasing the overall yield of pyridine or its alkyl pyridine derivatives during a base synthesis reaction is disclosed. The process comprises reacting a C2 to C5 aldehyde, a C3 to C5 ketone or a combination thereof, with ammonia and, optionally, formaldehyde, in the gas phase and in the presence of an effective amount of a particulate catalyst comprising a zeolite, zinc, a binder, and clay and optionally a matrix, wherein the catalyst has a L/B ratio of about 1.5 to about 4.0. Preferably, the zeolite is ZSM-5. A process for enhancing the catalytic activity of a zinc and zeolite containing catalyst to increase the overall yield of pyridine and/or its derivatives during a base synthesis reaction is also disclosed.
    Type: Grant
    Filed: November 27, 2018
    Date of Patent: April 14, 2020
    Assignee: W.R. GRACE & CO.-CONN.
    Inventor: Dorai Ramprasad
  • Patent number: 9981911
    Abstract: 4-Amino-5-fluoro-3-chloro-6-(substituted)picolinates are prepared from trifluoroacetic acid, p-methoxyaniline, a 3,3-dialkoxyprop-1-yne and a substituted methylene amine by a series of steps.
    Type: Grant
    Filed: August 23, 2017
    Date of Patent: May 29, 2018
    Assignee: Dow AgroSciences LLC
    Inventors: James M. Renga, Gregory T. Whiteker, Peter Lee Johnson, Christopher Galliford
  • Patent number: 9822077
    Abstract: 4-Amino-5-fluoro-3-chloro-6-(substituted)picolinates are prepared from trifluoroacetic acid, p-methoxyaniline, a 3,3-dialkoxyprop-1-yne and a substituted methylene amine by a series of steps.
    Type: Grant
    Filed: June 13, 2014
    Date of Patent: November 21, 2017
    Assignee: Dow AgroSciences LLC
    Inventors: James M. Renga, Gregory T. Whiteker, Peter L. Johnson, Christopher Galliford
  • Patent number: 9212141
    Abstract: 4-Amino-5-fluoro-3-chloro-6-(substituted)picolinates are prepared from trifluoroacetic acid, p-methoxyaniline, a 3,3-dialkoxyprop-1-yne and a substituted methylene amine by a series of steps.
    Type: Grant
    Filed: December 12, 2013
    Date of Patent: December 15, 2015
    Assignee: Dow AgroSciences, LLC.
    Inventors: James M. Renga, Gregory T. Whiteker, Peter L. Johnson, Christopher Galliford
  • Patent number: 9123898
    Abstract: The present invention provides a phosphorescent compound of following formula: wherein each of X and Y is independently selected from an aromatic group and a heterocyclic group.
    Type: Grant
    Filed: July 18, 2013
    Date of Patent: September 1, 2015
    Assignee: LG Display Co., Ltd.
    Inventors: In-Bum Song, Jung-Keun Kim, Joong-Hwan Yang
  • Publication number: 20150133669
    Abstract: The present invention relates to new processes for the preparation of 2-cyclopentyl-6-methoxy-isonicotinic acid, which is a useful intermediate for the synthesis of pyridine-4-yl derivatives as immunomodulating agent. Moreover, the present invention also relates to new intermediates used in those processes.
    Type: Application
    Filed: May 21, 2013
    Publication date: May 14, 2015
    Applicant: ACTELION PHARMACEUTICALS LTD.
    Inventor: Gunther Schmidt
  • Patent number: 9012650
    Abstract: The compounds are therapeutic agents useful in the treatment of viral infections, particularly HIV infection. The compounds are substituted (3S, 11aR)-N-[(2,4 -difluorophenyl)methyl]-6-oxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamides of formula (I).
    Type: Grant
    Filed: May 21, 2014
    Date of Patent: April 21, 2015
    Assignees: Shionogi & Co., Ltd., ViiV Healthcare Company
    Inventors: Brian Alvin Johns, Jason Gordon Weatherhead, Toshikazu Hakogi, Yasunori Aoyama
  • Publication number: 20140296533
    Abstract: 4-Amino-5-fluoro-3-chloro-6-(substituted)picolinates are prepared from trifluoroacetic acid, p-methoxyaniline, a 3,3-dialkoxyprop-1-yne and a substituted methylene amine by a series of steps.
    Type: Application
    Filed: June 13, 2014
    Publication date: October 2, 2014
    Applicant: DOW AGROSCIENCES LLC
    Inventors: James M. Renga, Gregory T. Whiteker, Peter L. Johnson, Christopher Galliford
  • Patent number: 8785480
    Abstract: In one embodiment, processes for the preparation of certain functionalized pyridine N-oxides are provided. In one form, the functionalized pyridine N-oxides include 2-substituted-5-(1-alkylthio)alkyl-pyridine N-oxides. Further embodiments, forms, objects, features, advantages, aspects, and benefits shall become apparent from the description.
    Type: Grant
    Filed: June 13, 2013
    Date of Patent: July 22, 2014
    Assignee: Dow AgroSciences, LLC.
    Inventors: Douglas C. Bland, Ronald Ross, Jr., Peter L. Johnson, Timothy C. Johnson
  • Publication number: 20140171650
    Abstract: 4-Amino-5-fluoro-3-chloro-6-(substituted)picolinates are prepared from trifluoroacetic acid, p-methoxyaniline, a C1-C4 alkyl propiolate and a substituted methylene amine by a series of steps.
    Type: Application
    Filed: December 12, 2013
    Publication date: June 19, 2014
    Applicant: DOW AGROSCIENCES LLC
    Inventors: Natalie C. Giampietro, James M. Renga
  • Patent number: 8754111
    Abstract: A method for the synthesis of N-substituted 3-acylated pyridinium compounds by reacting a pentamethine precursor with a primary amine.
    Type: Grant
    Filed: July 18, 2013
    Date of Patent: June 17, 2014
    Assignee: Roche Diagnostics Operations, Inc.
    Inventors: Peter Gebauer, Dieter Heindl, Carina Horn
  • Publication number: 20140005403
    Abstract: In one embodiment, processes for the preparation of certain functionalized pyridine N-oxides are provided. In one form, the functionalized pyridine N-oxides include 2-substituted-5-(1-alkylthio)alkyl-pyridine N-oxides. Further embodiments, forms, objects, features, advantages, aspects, and benefits shall become apparent from the description.
    Type: Application
    Filed: June 13, 2013
    Publication date: January 2, 2014
    Inventors: Douglas C. Bland, Ronald Ross, JR., Peter L. Johnson, Timothy C. Johnson
  • Patent number: 8343893
    Abstract: The present application relates to substituted enaminocarbonyl compounds of the formula (I) in which A, B, D, R1 to R3 are each as defined in the description, to processes for preparation thereof and to the use thereof for controlling animal pests.
    Type: Grant
    Filed: June 17, 2010
    Date of Patent: January 1, 2013
    Assignee: Bayer Cropscience AG
    Inventors: Peter Jeschke, Thomas Schenke, Robert Velten, Peter Lümmen, Olga Malsam, Ulrich Görgens, Arnd Voerste
  • Publication number: 20120283446
    Abstract: The present invention relates to a method for synthesizing bio-based pyridine and picolines, said method including at least the following steps: a first step involving subjecting a glycerol filler, created from the methanolysis of vegetable oils or animal fats, to a dehydration reaction leading to acrolein; a second step involving partial condensation of the effluent from the first step so as to separate a water-rich flow as well as an acrolein-rich flow; and a third step involving reacting the acrolein from the preceding step with acetaldehyde in the presence of ammonia so as to obtain, by means of a condensation reaction, the biobased pyridine and picolines.
    Type: Application
    Filed: October 22, 2010
    Publication date: November 8, 2012
    Applicant: ARKEMA FRANCE
    Inventors: Jean-Luc Dubois, Jean-Francois Devaux
  • Publication number: 20120190855
    Abstract: Methods for the synthesis of N-substituted carboxylated pyridinium compounds by reaction of a pentamethine precursor with a primary amine are provided. In this reaction an N-substituted alkoxycarbonyl pyridinium heterocycle is formed.
    Type: Application
    Filed: January 27, 2012
    Publication date: July 26, 2012
    Applicant: ROCHE DIAGNOSTICS OPERATIONS, INC.
    Inventors: Dieter Heindl, Peter Gebauer
  • Patent number: 8084569
    Abstract: A liquid-phase process is provided for the synthesis from glutarimidines of diaminopyridines and related compounds, which are used industrially as compounds and as components in the synthesis of a variety of useful materials. The synthesis proceeds by means of a dehydrogenative aromatization process.
    Type: Grant
    Filed: December 18, 2007
    Date of Patent: December 27, 2011
    Assignee: E.I. DuPont de Nemours and Company
    Inventors: Aaron Minter, Berlin Stokes
  • Publication number: 20110301314
    Abstract: A liquid-phase, continuous process is provided for the manufacture of 2,6-diaminopyridine and related compounds from glutaronitriles, which are used industrially as compounds and as components in the synthesis of a variety of useful materials. The synthesis proceeds by means of a dehydrogenative aromatization process.
    Type: Application
    Filed: December 17, 2009
    Publication date: December 8, 2011
    Applicant: E.I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Keith W. Hutchenson, Aaron Minter
  • Patent number: 8022167
    Abstract: A liquid-phase process is provided for the manufacture from glutaronitriles and related compounds of 2,6-diaminopyridine and related compounds, which are used industrially as compounds and as components in the synthesis of a variety of useful materials. The synthesis proceeds by means of a dehydrogenative aromatization process.
    Type: Grant
    Filed: December 18, 2007
    Date of Patent: September 20, 2011
    Inventors: Aaron Minter, Berlin Stokes
  • Publication number: 20110077406
    Abstract: Embodiments of the invention provide methods and materials for chemical cross-coupling reactions that utilize unconventional phenol derivatives as cross-coupling partners. Embodiments of the invention can be used to synthesize a variety of useful organic compounds, for example the anti-inflammatory drug flurbiprofen.
    Type: Application
    Filed: September 24, 2010
    Publication date: March 31, 2011
    Applicant: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA
    Inventors: Neil K. Garg, Kyle W. Quasdorf, Xia Tian
  • Publication number: 20110015392
    Abstract: A route for preparing a compound of formula (I) where X, R1, R2, R7, R8 and R9 are as defined in the specification, is described. Process steps used in the route and novel intermediates prepared during the route are also described and claimed. Compounds of formula (I) are used in the preparation of pharmaceutical compounds, in particular inhibitors of MEK, useful in the treatment of hyperproliferative disease such as cancer and inflammatory conditions.
    Type: Application
    Filed: August 11, 2010
    Publication date: January 20, 2011
    Inventors: Mark Richard Fielding, John Leonard
  • Patent number: 7872021
    Abstract: Benzenesulfonamide derivative compounds corresponding to the general formula (I): and their pharmaceutically acceptable addition salts; a process for preparation of such compounds; pharmaceutical compositions containing such compounds, and the use of such compounds as a pharmacologically active substance, in particular in the treatment of neurodegenerative diseases, cardiovascular diseases, inflammatory diseases; hypercholesterolemia, and diabetes.
    Type: Grant
    Filed: November 7, 2006
    Date of Patent: January 18, 2011
    Assignee: Laboratories Fournier S.A.
    Inventors: Luc Lebreton, Christine Massardier, Christine Dumas, Pierre Dodey, Philippe Masson
  • Publication number: 20100292482
    Abstract: The present invention relates to a Compound of the formula (I), wherein X represents CN, COOR, wherein R represents hydrogen or a carboxyl protecting group, CONR?2, wherein R? represents hydrogen or a carboxyl protecting group, or nitro; R1, R2, R3, R4, R5 independently of each other represent hydrogen, C1-C6 alkyl, halogen, trifluoromethyl, cyano, nitro, substituted aryl or substituted heteroaryl group; Y represents hydrogen, C1-C6 alkyl, C3-C7 cycloalkyl, C7-C13 alkaryl, trifluoromethyl, cyano, nitro, substituted aryl or substituted heteroaryl group; and wherein the stereochemically unspecified double bonds in the above formula (I) represent either the E,E; E,Z; Z,E or Z,Z configuration.
    Type: Application
    Filed: October 24, 2008
    Publication date: November 18, 2010
    Inventors: David Alexander Learmonth, Laszlo Erno Kiss
  • Publication number: 20100261764
    Abstract: The present invention relates to novel therapeutic compounds of formula (I) wherein R1 is selected from the group consisting of C2-8alkyl, R2 is a methyl group, R3 is independently selected from the group consisting of H and C1-8alkyl, R4 is independently selected from the group consisting of C1-8alkyl or pharmaceutically acceptable salts thereof, pharmaceutical compositions containing the same, the compounds for use as medicaments, and use of the compounds for the manufacture of specific medicaments. The present invention also concerns a method of treatment involving administration of the compounds. The novel compounds are useful for the treatment of age-related disorders accompanied with dysfunctional insulin receptor signaling.
    Type: Application
    Filed: December 18, 2007
    Publication date: October 14, 2010
    Inventors: Dmitri Valerievich Biryukov, Igor Antatolievich Pomytkin
  • Patent number: 7723522
    Abstract: A method in which a pyridinium derivative such as 1,3-dimethyl-2,3-dihydro-2-oxopyrimidinium chloride is reacted with an acetyl compound such as 4-acetylpyridine, and then the reaction product is reacted with ammonia or an ammonium salt.
    Type: Grant
    Filed: February 1, 2005
    Date of Patent: May 25, 2010
    Assignee: Fujifilm Finechemicals Co., Ltd
    Inventors: Hirokazu Kuwabara, Chang Shan Zhang, Hiromitsu Saitoh, Takayuki Sonoda
  • Patent number: 7709650
    Abstract: 2-Substituted-5-(1-alkylthio)alkylpyridines are produced efficiently and in high yield from a non-pyridine source by cyclization.
    Type: Grant
    Filed: February 25, 2009
    Date of Patent: May 4, 2010
    Assignee: Dow AgroSciences LLC
    Inventors: James M. Renga, Ronald Ross, Jr., Timothy P. Martin, Kim E. Arndt, Nicholas M. Irvine
  • Patent number: 7709648
    Abstract: 2-Substituted-5-(1-alkylthio)alkylpyridines are produced efficiently and in high yield.
    Type: Grant
    Filed: February 9, 2007
    Date of Patent: May 4, 2010
    Assignee: Dow AgroSciences LLC
    Inventors: Kevin G. Meyer, Kim E. Arndt
  • Patent number: 7705154
    Abstract: 2-Substituted-5-(1-alkylthio)alkylpyridines are produced efficiently and in high yield by cyclization and thioalkylation.
    Type: Grant
    Filed: February 9, 2007
    Date of Patent: April 27, 2010
    Assignee: Dow AgroSciences LLC
    Inventors: Stephen T. Heller, Ronald Ross, Nicholas M. Irvine, James M. Renga, Mark W. Zettler, Kim E. Arndt
  • Publication number: 20100087646
    Abstract: [Problem] To provide an organoboron compound-containing reagent for organic synthesis reactions which undergoes no trimerization with dehydration, does not necessitate activation with a base, and is stable and highly active. [Means for Solving Problems] The reagent for organic synthesis reactions contains an organic triol borate salt represented by any of the general formulae (I) to (III) and general formula (XVI): (wherein R1 represents alkyl, alkenyl, etc.; R2 represents optionally substituted alkyl, alkenyl, alkynyl, etc. or represents hydrogen; m+ represents an alkaline metal ion, phosphonium ion, or given ammonium ion; M2+ represents an alkaline earth metal; X represents halogen or alkoxide; Y represents an alkali metal ion, etc.; A represents optionally substituted methylene; and n represents an integer).
    Type: Application
    Filed: January 28, 2008
    Publication date: April 8, 2010
    Applicant: WAKO PURE CHEMICAL INDUSTRIES, LTD.
    Inventors: Norio Miyaura, Yasunori Yamamoto
  • Publication number: 20100029948
    Abstract: A liquid-phase process is provided for the manufacture from glutaronitriles and related compounds of 2,6-diaminopyridine and related compounds, which are used industrially as compounds and as components in the synthesis of a variety of useful materials. The synthesis proceeds by means of a dehydrogenative aromatization process.
    Type: Application
    Filed: December 18, 2007
    Publication date: February 4, 2010
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Aaron Minter, Berlin Stokes
  • Publication number: 20100016603
    Abstract: A production process where 2,3?-bipyridyl-6?-one can be produced in high purity at low cost on an industrial scale without using an expensive catalyst or special equipment is provided. A process for producing 2,3?-bipyridyl-6?-one comprises reacting an acetylpyridine derivative with at least one of compounds represented by formulae (II) to (V) to synthesize a bipyridine derivative and hydrolyzing the bipyridine derivative by one-pot preparation. In formulae (II) to (V), each of R2 to R8, X and Y represents a given group.
    Type: Application
    Filed: January 29, 2007
    Publication date: January 21, 2010
    Applicants: FUJIFILM FINECHEMICALS CO., LTD., EISAI R&D MANAGEMENT CO., LTD.
    Inventors: Takayuki Sonoda, Taichi Shintou, Kenichi Onoue, Takashi Nagayama
  • Publication number: 20100010189
    Abstract: A gas-phase, continuous process is provided for the manufacture of 2,6-diaminopyridine and related compounds from glutaronitriles, which are used industrially as compounds and as components in the synthesis of a variety of useful materials. The synthesis proceeds by means of a dehydrogenative aromatization process.
    Type: Application
    Filed: July 8, 2008
    Publication date: January 14, 2010
    Inventors: KEITH W. HUTCHENSON, AARON MINTER, GREGG SUNSHINE
  • Publication number: 20100004457
    Abstract: 2-Trifluoromethyl-5-(1-substituted)alkylpyridines are produced efficiently and in high yield from an alkyl vinyl ether and trifluoroacetyl chloride by cyclization.
    Type: Application
    Filed: June 15, 2009
    Publication date: January 7, 2010
    Applicant: DOW AGROSCIENCES LLC
    Inventors: Douglas C. Bland, Gary A. Roth
  • Patent number: 7569725
    Abstract: Disclosed are anthranilic acid derivatives having Formula (I): and pharmaceutically acceptable salts thereof; and pharmaceutical compositions comprising such compounds. Also disclosed are methods of using such compounds in the treatment of conditions or diseases such as prostate cancer, and methods of using such compounds in the inhibition of 17?-hydroxysteroid dehydrogenase type 3 enzyme.
    Type: Grant
    Filed: October 21, 2005
    Date of Patent: August 4, 2009
    Assignee: Britsol-Myers Squibb Company
    Inventors: Ellen K. Kick, R. Michael Lawrence, Brian E. Fink, Raj N. Misra, Gregory D. Vite
  • Patent number: 7557216
    Abstract: To provide an industrially advantageous process for producing 5-chloro-2,4-dihydroxypyridine, which is an inhibitor acting on a biodegradation enzyme that biodegrades an anti-malignant-tumor agent 5-fluorouracil. The process is carried out under mild conditions with a small number of steps and produces less industrial waste. The process employs a 5-chloro-1,3-dioxin-4-one derivative (2) as a starting substance to thereby form a pyrone derivative (4) represented by formula (4): (wherein R3 and R4, which are identical to or different from each other, each represent a C1 to C6 linear-chain or branched-chain alkyl group, or a silyl group having a C1 to C6 linear-chain or branched-chain alkyl group), and subsequently, 5-chloro-2,4-dihydroxypyridine (1) is produced from the pyron derivative.
    Type: Grant
    Filed: January 25, 2006
    Date of Patent: July 7, 2009
    Assignee: Taiho Pharmaceutical Co., Ltd.
    Inventors: Hiroshi Nagasawa, Katsuyuki Higurashi, Etsuji Yamanaka
  • Patent number: 7541469
    Abstract: 2-Substituted-5-(1-alkylthio)alkylpyridines are produced efficiently and in high yield from a non-pyridine source by cyclization.
    Type: Grant
    Filed: February 9, 2007
    Date of Patent: June 2, 2009
    Assignee: Dow AgroScience LLC
    Inventors: James M. Renga, Ronald Ross, Timothy P. Martin, Kim E. Arndt, Nicholas M. Irvine
  • Patent number: 7528260
    Abstract: A method is disclosed for preparing compounds of Formula 1 by combining compounds of Formulae 2 and 3 and a sulfonyl chloride. Also disclosed are compounds of Formula 3, which are useful as starting materials for this method.
    Type: Grant
    Filed: December 6, 2005
    Date of Patent: May 5, 2009
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Rafael Shapiro, Eric de Guyon Taylor, William T. Zimmerman
  • Publication number: 20090099368
    Abstract: Processes comprising: providing a dehydrogenatable compound; and subjecting the dehydrogenatable compound to a dehydrogenation reaction at a temperature of from 150 to 400° C., in the presence of oxygen, and at a temperature profile of the dehydrogenation reaction which does not differ substantially from the temperature profile of the dehydrogenation reaction in the absence of oxygen under otherwise identical conditions.
    Type: Application
    Filed: February 7, 2007
    Publication date: April 16, 2009
    Inventors: Stefan Kotrel, Martin Ernst
  • Patent number: 7491828
    Abstract: The present invention relates to a process for producing annulated pyridines by reacting cyclic ketone, aldehyde and ammonia in presence of molecular sieve type catalysts in an environmentally friendly, economical and highly selective heterogeneous method.
    Type: Grant
    Filed: December 30, 2004
    Date of Patent: February 17, 2009
    Assignee: Council of Scientific and Industrial Research
    Inventors: Shivanand J. Kulkarni, Veera V. Krishna Kandepi, Narender Nama, Kondapuram V. Raghavan
  • Publication number: 20090043101
    Abstract: To provide an industrially advantageous process for producing 5-chloro-2,4-dihydroxypyridine, which is an inhibitor acting on a biodegradation enzyme that biodegrades an anti-malignant-tumor agent 5-fluorouracil. The process is carried out under mild conditions with a small number of steps and produces less industrial waste. The process employs a 5-chloro-1,3-dioxin-4-one derivative (2) as a starting substance to thereby form a pyrone derivative (4) represented by formula (4): (wherein R3 and R4, which are identical to or different from each other, each represent a C1 to C6 linear-chain or branched-chain alkyl group, or a silyl group having a C1 to C6 linear-chain or branched-chain alkyl group), and subsequently, 5-chloro-2,4-dihydroxypyridine (1) is produced from the pyron derivative.
    Type: Application
    Filed: January 25, 2006
    Publication date: February 12, 2009
    Applicant: TAIHO PHARMACEUTICAL CO., LTD.
    Inventors: Hiroshi Nagasawa, Katsuyuki Higurashi, Etsuji Yamanaka
  • Patent number: 7468437
    Abstract: The present invention is directed to certain phenyl pyrrolidine ether compounds which are useful as neurokinin-1 (NK-1) receptor antagonists, and inhibitors of tachykinin and in particular substance P. The invention is also concerned with pharmaceutical formulations comprising these compounds as active ingredients and the use of the compounds and their formulations in the treatment of certain disorders, including emesis, depression, and anxiety.
    Type: Grant
    Filed: September 24, 2004
    Date of Patent: December 23, 2008
    Assignee: Merck & Co., Inc.
    Inventors: Robert J. DeVita, Peter Lin, Sander G. Mills, Jonathan R. Young
  • Patent number: 7439366
    Abstract: The present invention relates to a phenacylamine derivative of the formula (I) or a salt thereof: wherein A is alkyl, cycloalkyl, phenyl which may be substituted by Y, pyridyl which may be substituted by Y, or pyrazolyl which may be substituted by Y, R1 and R2 are each alkyl, or R1 and R2 may together form a 3- to 6-membered saturated carbocycle, R3 is hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl or COR4, X is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, alkenylthio, haloalkenylthio, alkynylthio, haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano, phenyl which may be substituted by Y, phenoxy which may be substituted by Y, benzyloxy which may be substituted by Y, or pyridyloxy which may be substituted by Y, and n is an integer of from 0 to 5.
    Type: Grant
    Filed: February 9, 2001
    Date of Patent: October 21, 2008
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Yuji Nakamura, Masayuki Morita, Kenji Izakura
  • Publication number: 20080214825
    Abstract: Methods for producing substituted halopyridines (II) by reacting a ?-hydroxy-y-acyl butyronitrile (I) or a suitable acyl-protected derivative with hydrogen halides, or substances or mixtures that can release hydrogen halides. In the formulae (I) and (II): R, R4 represent H, a linear or branched alkyl group, optionally a substituted aryl group, an aralkyl group, or optionally a substituted heteroaryl group; R1, R2, R3 represent H, a linear or branched alkyl group, optionally a substituted aryl, aralkyl, optionally a substituted heteroaryl group or one of the following groups CnH(2n+1?m)Xm, COOR, or CN; R5 represents H, a linear or branched alkyl group, optionally a substituted aryl group, an aralkyl, optionally a substituted heteroaryl or one of the following groups CnH(2n+1?m)Xm, COOR, CN, SO2R, SOR, PO(OR)2; n represents a positive whole number; m represents a positive whole number ?2n+1; and X represents F, Cl, Br, or I.
    Type: Application
    Filed: June 14, 2006
    Publication date: September 4, 2008
    Inventors: Bernd Wilhelm Lehnemann, Joerg Jung, Andreas Meudt
  • Patent number: 7417041
    Abstract: Novel fused heteroaromatic compounds, including derivatives thereof, to intermediates for their preparation, to pharmaceutical compositions containing them and to their medicinal use are described. The compounds of the present invention are potent inhibitors of transforming growth factor (“TGF”)-? signaling pathway. They are useful in the treatment of various TGF-related disease states including, for example, cancer and fibrotic diseases.
    Type: Grant
    Filed: February 20, 2004
    Date of Patent: August 26, 2008
    Assignees: Pfizer Inc., Pfizer Products Inc.
    Inventors: Laura C. Blumberg, Michael J. Munchhof, Andrei Shavnya
  • Patent number: 7238211
    Abstract: The invention relates to a dye composition that is useful for dyeing keratin fibers, 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 disubstituted amino radical, to the use of this composition for dyeing keratin fibers 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.
    Type: Grant
    Filed: October 6, 2003
    Date of Patent: July 3, 2007
    Assignee: L'Oreal S.A.
    Inventors: Laurent Vidal, Aziz Fadli
  • Patent number: 7232909
    Abstract: This invention is to provide a process for producing 2-amino-4,6-disubstituted nicotinic acid ester analogs and salts thereof, comprising the reaction shown by the following scheme. The ester analogs can be prepared in one pot, and in good yield by using tertiary alkyl cyanoacetate. Furthermore, the method is useful for preparing derivatives of various analogs of the ester, e.g. alkyl substituted and aryl substituted analogs.
    Type: Grant
    Filed: September 30, 2005
    Date of Patent: June 19, 2007
    Assignee: Bayer Aktiengesellschaft
    Inventors: Toshiki Murata, Masaomi Umeda, Sachiko Sakakibara, Takashi Yoshiro, Hiroki Sato, Tsutomu Masuda, Yuji Koriyama, Mitsuiyuki Shimada, Takuya Shintani, Hiroshi Kadono, Timothy B. Lowinger, Karl B. Ziegelbauer, Kinji Fuchikami, Hiroshi Komura
  • Patent number: 7179307
    Abstract: Use of an extract of the plant Myrsine africana in oxidation dyeing for dyeing keratin fibers, a novel composition comprising this plant extract, a process for the oxidation dyeing of keratin fibers using this composition, as well as the colored products obtained using the composition.
    Type: Grant
    Filed: September 23, 2005
    Date of Patent: February 20, 2007
    Assignee: L'Oreal, S.A.
    Inventors: Béatrice Belcour-Castro, Hervé Burgaud, Georges Hussler, Michel Seite
  • Patent number: 7175670
    Abstract: The present invention relates to a dye composition comprising at least one oxidation base and at least one coupler of the 2,3,5-triaminopyridine type. This composition may be useful for dyeing keratin fibers, such as the hair. Also disclosed are a process for dyeing keratin fibers and a multi-compartment dyeing kit using the claimed dye composition. Such a composition can make it possible to obtain strong, uniform dyeing results between the end and the root, which are resistant to external agents, while at the same time being capable of giving varied shades, for example, in fundamental shades such as chestnut, grey or black shades.
    Type: Grant
    Filed: March 12, 2004
    Date of Patent: February 13, 2007
    Assignee: L'Oreal S.A.
    Inventors: Aziz Fadli, Laurent Vidal
  • Patent number: 7148356
    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
  • Patent number: 7071212
    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
  • Patent number: 7044987
    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.
    Type: Grant
    Filed: October 6, 2003
    Date of Patent: May 16, 2006
    Assignee: L'Oreal S.A.
    Inventors: Laurent Vidal, Aziz Fadli