Process Of Forming Pyridine Ring Patents (Class 546/250)
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Patent number: 12221457Abstract: A method for producing a boron-containing compound comprises a step of reacting a first raw material compound having a carbon-carbon double bond with a second raw material compound having a conjugated diene skeleton in the presence of a metal catalyst to obtain a boron-containing compound having a 1,4-diene skeleton, wherein at least one of the first raw material compound and the second raw material compound has a boron-containing group bonded to a carbon atom constituting the carbon-carbon double bond or the conjugated diene skeleton, and the boron-containing compound has the 1,4-diene skeleton and the boron-containing group.Type: GrantFiled: February 6, 2020Date of Patent: February 11, 2025Assignee: NATIONAL UNIVERSITY CORPORATION TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGYInventors: Masafumi Hirano, Nobuyuki Komine, Sayori Kiyota, Keita Shimada
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Patent number: 12077505Abstract: Improved methods for preparing chemical precursors to sulfonyl chloride III, which are important intermediates in the preparation of pyroxsulam herbicide, are provided. Also provided are compounds of Formula III, Formula VII, and IV, wherein R1 is a C1-C6 alkyl, X is Cl or OH, Y is halogen, OH, or OR2, and R2 is a C1-C6 alkyl.Type: GrantFiled: December 20, 2019Date of Patent: September 3, 2024Assignee: CORTEVA AGRISCIENCE LLCInventors: Jossian Oppenheimer, Matthias S. Ober, Mark E. Ondari
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Patent number: 11884644Abstract: Disclosed is a method for synthesizing (S)-nicotine and an intermediate thereof, which belongs to the field of synthesizing a heterocyclic compound. A chiral amino group is introduced into 4-hydroxy-1-(3-pyridyl)-1-butanone by transaminase chiral catalysis in the presence of an amino donor to obtain (S)-4-amino-4-(3-pyridyl)-1-butanol. An N-methylation reaction is performed on (S)-4-amino-4-(3-pyridyl)-1-butanol with a methylating agent to obtain (S)-4-(methylamino)-4-(3-pyridyl)-1-butanol. The intermediate is reacted with an acylating agent or a halogenating agent to convert an alcoholic hydroxyl group into a sulfonate group or a halogen. Finally, a ring closure reaction is performed to obtain (S)-nicotine in an alkaline condition. The raw materials are cheap and readily available, the reaction conditions are mild, the operation is simple, and the cost is low.Type: GrantFiled: September 1, 2023Date of Patent: January 30, 2024Assignee: Shandong Jincheng Pharmaceutical Chemical Co., Ltd.Inventors: Kai Fu, Jiaquan Li, Peng Wang, Qinyuan Ma, Xicheng Zhang, Gengxiu Zheng, Ruihua Hu
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Patent number: 11787806Abstract: This invention relates to pharmaceutically acceptable ergoline analogues and salts thereof. In particular, though not exclusively, the invention relates to formulations and uses of the same as a medicament.Type: GrantFiled: September 16, 2022Date of Patent: October 17, 2023Assignee: BECKLEY PSYTECH LIMITEDInventors: Massimo Muratore, Amir Lotfi Moghaddam, Christopher Wong
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Patent number: 11673896Abstract: The present disclosure is directed to inhibitors of SHP2 and their use in the treatment of disease. Also disclosed are pharmaceutical compositions comprising the same.Type: GrantFiled: July 22, 2019Date of Patent: June 13, 2023Assignee: REVOLUTION MEDICINES, INC.Inventors: Adrian Gill, Naing Aay, Kevin Mellem, Andreas Buckl, Elena S. Koltun, Christopher Semko, Gert Kiss
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Patent number: 10618039Abstract: 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: GrantFiled: November 27, 2018Date of Patent: April 14, 2020Assignee: W.R. GRACE & CO.-CONN.Inventor: Dorai Ramprasad
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Patent number: 9981911Abstract: 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: GrantFiled: August 23, 2017Date of Patent: May 29, 2018Assignee: Dow AgroSciences LLCInventors: James M. Renga, Gregory T. Whiteker, Peter Lee Johnson, Christopher Galliford
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Patent number: 9822077Abstract: 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: GrantFiled: June 13, 2014Date of Patent: November 21, 2017Assignee: Dow AgroSciences LLCInventors: James M. Renga, Gregory T. Whiteker, Peter L. Johnson, Christopher Galliford
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Patent number: 9212141Abstract: 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: GrantFiled: December 12, 2013Date of Patent: December 15, 2015Assignee: Dow AgroSciences, LLC.Inventors: James M. Renga, Gregory T. Whiteker, Peter L. Johnson, Christopher Galliford
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Patent number: 9123898Abstract: 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: GrantFiled: July 18, 2013Date of Patent: September 1, 2015Assignee: LG Display Co., Ltd.Inventors: In-Bum Song, Jung-Keun Kim, Joong-Hwan Yang
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Publication number: 20150133669Abstract: 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: ApplicationFiled: May 21, 2013Publication date: May 14, 2015Applicant: ACTELION PHARMACEUTICALS LTD.Inventor: Gunther Schmidt
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Patent number: 9012650Abstract: 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: GrantFiled: May 21, 2014Date of Patent: April 21, 2015Assignees: Shionogi & Co., Ltd., ViiV Healthcare CompanyInventors: Brian Alvin Johns, Jason Gordon Weatherhead, Toshikazu Hakogi, Yasunori Aoyama
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Publication number: 20140296533Abstract: 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: ApplicationFiled: June 13, 2014Publication date: October 2, 2014Applicant: DOW AGROSCIENCES LLCInventors: James M. Renga, Gregory T. Whiteker, Peter L. Johnson, Christopher Galliford
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Patent number: 8785480Abstract: 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: GrantFiled: June 13, 2013Date of Patent: July 22, 2014Assignee: Dow AgroSciences, LLC.Inventors: Douglas C. Bland, Ronald Ross, Jr., Peter L. Johnson, Timothy C. Johnson
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Publication number: 20140171650Abstract: 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: ApplicationFiled: December 12, 2013Publication date: June 19, 2014Applicant: DOW AGROSCIENCES LLCInventors: Natalie C. Giampietro, James M. Renga
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Patent number: 8754111Abstract: A method for the synthesis of N-substituted 3-acylated pyridinium compounds by reacting a pentamethine precursor with a primary amine.Type: GrantFiled: July 18, 2013Date of Patent: June 17, 2014Assignee: Roche Diagnostics Operations, Inc.Inventors: Peter Gebauer, Dieter Heindl, Carina Horn
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Publication number: 20140005403Abstract: 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: ApplicationFiled: June 13, 2013Publication date: January 2, 2014Inventors: Douglas C. Bland, Ronald Ross, JR., Peter L. Johnson, Timothy C. Johnson
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Patent number: 8343893Abstract: 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: GrantFiled: June 17, 2010Date of Patent: January 1, 2013Assignee: Bayer Cropscience AGInventors: Peter Jeschke, Thomas Schenke, Robert Velten, Peter Lümmen, Olga Malsam, Ulrich Görgens, Arnd Voerste
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Publication number: 20120283446Abstract: 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: ApplicationFiled: October 22, 2010Publication date: November 8, 2012Applicant: ARKEMA FRANCEInventors: Jean-Luc Dubois, Jean-Francois Devaux
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Publication number: 20120190855Abstract: 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: ApplicationFiled: January 27, 2012Publication date: July 26, 2012Applicant: ROCHE DIAGNOSTICS OPERATIONS, INC.Inventors: Dieter Heindl, Peter Gebauer
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Patent number: 8084569Abstract: 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: GrantFiled: December 18, 2007Date of Patent: December 27, 2011Assignee: E.I. DuPont de Nemours and CompanyInventors: Aaron Minter, Berlin Stokes
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Publication number: 20110301314Abstract: 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: ApplicationFiled: December 17, 2009Publication date: December 8, 2011Applicant: E.I. DU PONT DE NEMOURS AND COMPANYInventors: Keith W. Hutchenson, Aaron Minter
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Patent number: 8022167Abstract: 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: GrantFiled: December 18, 2007Date of Patent: September 20, 2011Inventors: Aaron Minter, Berlin Stokes
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Publication number: 20110077406Abstract: 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: ApplicationFiled: September 24, 2010Publication date: March 31, 2011Applicant: THE REGENTS OF THE UNIVERSITY OF CALIFORNIAInventors: Neil K. Garg, Kyle W. Quasdorf, Xia Tian
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Publication number: 20110015392Abstract: 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: ApplicationFiled: August 11, 2010Publication date: January 20, 2011Inventors: Mark Richard Fielding, John Leonard
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Patent number: 7872021Abstract: 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: GrantFiled: November 7, 2006Date of Patent: January 18, 2011Assignee: Laboratories Fournier S.A.Inventors: Luc Lebreton, Christine Massardier, Christine Dumas, Pierre Dodey, Philippe Masson
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Publication number: 20100292482Abstract: 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: ApplicationFiled: October 24, 2008Publication date: November 18, 2010Inventors: David Alexander Learmonth, Laszlo Erno Kiss
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Publication number: 20100261764Abstract: 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: ApplicationFiled: December 18, 2007Publication date: October 14, 2010Inventors: Dmitri Valerievich Biryukov, Igor Antatolievich Pomytkin
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Patent number: 7723522Abstract: 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: GrantFiled: February 1, 2005Date of Patent: May 25, 2010Assignee: Fujifilm Finechemicals Co., LtdInventors: Hirokazu Kuwabara, Chang Shan Zhang, Hiromitsu Saitoh, Takayuki Sonoda
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Patent number: 7709648Abstract: 2-Substituted-5-(1-alkylthio)alkylpyridines are produced efficiently and in high yield.Type: GrantFiled: February 9, 2007Date of Patent: May 4, 2010Assignee: Dow AgroSciences LLCInventors: Kevin G. Meyer, Kim E. Arndt
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Patent number: 7709650Abstract: 2-Substituted-5-(1-alkylthio)alkylpyridines are produced efficiently and in high yield from a non-pyridine source by cyclization.Type: GrantFiled: February 25, 2009Date of Patent: May 4, 2010Assignee: Dow AgroSciences LLCInventors: James M. Renga, Ronald Ross, Jr., Timothy P. Martin, Kim E. Arndt, Nicholas M. Irvine
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Patent number: 7705154Abstract: 2-Substituted-5-(1-alkylthio)alkylpyridines are produced efficiently and in high yield by cyclization and thioalkylation.Type: GrantFiled: February 9, 2007Date of Patent: April 27, 2010Assignee: Dow AgroSciences LLCInventors: Stephen T. Heller, Ronald Ross, Nicholas M. Irvine, James M. Renga, Mark W. Zettler, Kim E. Arndt
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Publication number: 20100087646Abstract: [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: ApplicationFiled: January 28, 2008Publication date: April 8, 2010Applicant: WAKO PURE CHEMICAL INDUSTRIES, LTD.Inventors: Norio Miyaura, Yasunori Yamamoto
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Publication number: 20100029948Abstract: 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: ApplicationFiled: December 18, 2007Publication date: February 4, 2010Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: Aaron Minter, Berlin Stokes
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Publication number: 20100016603Abstract: 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: ApplicationFiled: January 29, 2007Publication date: January 21, 2010Applicants: FUJIFILM FINECHEMICALS CO., LTD., EISAI R&D MANAGEMENT CO., LTD.Inventors: Takayuki Sonoda, Taichi Shintou, Kenichi Onoue, Takashi Nagayama
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Publication number: 20100010189Abstract: 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: ApplicationFiled: July 8, 2008Publication date: January 14, 2010Inventors: KEITH W. HUTCHENSON, AARON MINTER, GREGG SUNSHINE
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Publication number: 20100004457Abstract: 2-Trifluoromethyl-5-(1-substituted)alkylpyridines are produced efficiently and in high yield from an alkyl vinyl ether and trifluoroacetyl chloride by cyclization.Type: ApplicationFiled: June 15, 2009Publication date: January 7, 2010Applicant: DOW AGROSCIENCES LLCInventors: Douglas C. Bland, Gary A. Roth
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Patent number: 7569725Abstract: 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: GrantFiled: October 21, 2005Date of Patent: August 4, 2009Assignee: Britsol-Myers Squibb CompanyInventors: Ellen K. Kick, R. Michael Lawrence, Brian E. Fink, Raj N. Misra, Gregory D. Vite
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Patent number: 7557216Abstract: 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: GrantFiled: January 25, 2006Date of Patent: July 7, 2009Assignee: Taiho Pharmaceutical Co., Ltd.Inventors: Hiroshi Nagasawa, Katsuyuki Higurashi, Etsuji Yamanaka
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Patent number: 7541469Abstract: 2-Substituted-5-(1-alkylthio)alkylpyridines are produced efficiently and in high yield from a non-pyridine source by cyclization.Type: GrantFiled: February 9, 2007Date of Patent: June 2, 2009Assignee: Dow AgroScience LLCInventors: James M. Renga, Ronald Ross, Timothy P. Martin, Kim E. Arndt, Nicholas M. Irvine
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Patent number: 7528260Abstract: 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: GrantFiled: December 6, 2005Date of Patent: May 5, 2009Assignee: E. I. du Pont de Nemours and CompanyInventors: Rafael Shapiro, Eric de Guyon Taylor, William T. Zimmerman
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Publication number: 20090099368Abstract: 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: ApplicationFiled: February 7, 2007Publication date: April 16, 2009Inventors: Stefan Kotrel, Martin Ernst
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Patent number: 7491828Abstract: 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: GrantFiled: December 30, 2004Date of Patent: February 17, 2009Assignee: Council of Scientific and Industrial ResearchInventors: Shivanand J. Kulkarni, Veera V. Krishna Kandepi, Narender Nama, Kondapuram V. Raghavan
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Publication number: 20090043101Abstract: 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: ApplicationFiled: January 25, 2006Publication date: February 12, 2009Applicant: TAIHO PHARMACEUTICAL CO., LTD.Inventors: Hiroshi Nagasawa, Katsuyuki Higurashi, Etsuji Yamanaka
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Patent number: 7468437Abstract: 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: GrantFiled: September 24, 2004Date of Patent: December 23, 2008Assignee: Merck & Co., Inc.Inventors: Robert J. DeVita, Peter Lin, Sander G. Mills, Jonathan R. Young
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Patent number: 7439366Abstract: 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: GrantFiled: February 9, 2001Date of Patent: October 21, 2008Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Yuji Nakamura, Masayuki Morita, Kenji Izakura
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Publication number: 20080214825Abstract: 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: ApplicationFiled: June 14, 2006Publication date: September 4, 2008Inventors: Bernd Wilhelm Lehnemann, Joerg Jung, Andreas Meudt
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Patent number: 7417041Abstract: 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: GrantFiled: February 20, 2004Date of Patent: August 26, 2008Assignees: Pfizer Inc., Pfizer Products Inc.Inventors: Laura C. Blumberg, Michael J. Munchhof, Andrei Shavnya
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Patent number: 7238211Abstract: 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: GrantFiled: October 6, 2003Date of Patent: July 3, 2007Assignee: L'Oreal S.A.Inventors: Laurent Vidal, Aziz Fadli
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Patent number: 7232909Abstract: 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: GrantFiled: September 30, 2005Date of Patent: June 19, 2007Assignee: Bayer AktiengesellschaftInventors: 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