Cyclopropyl In Acid Moiety Patents (Class 560/124)
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Patent number: 6908945Abstract: A cyclopropanecarboxylic acid ester compound of formula (1): has an excellent pesticidal efficacy, and a pesticidal composition comprising it as an active ingredient is useful for controlling pests.Type: GrantFiled: April 10, 2003Date of Patent: June 21, 2005Assignee: Sumitomo Chemical Company, LimitedInventor: Tatsuya Mori
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Patent number: 6909014Abstract: The present invention relates to novel ether compounds, compositions comprising ether compounds, and methods useful for treating and preventing cardiovascular diseases, dyslipidemias, dysproteinemias, and glucose metabolism disorders comprising administering a composition comprising an ether compound. The compounds, compositions, and methods of the invention are also useful for treating and preventing Alzheimer's Disease, Syndrome X, peroxisome proliferator activated receptor-related disorders, septicemia, thrombotic disorders, obesity, pancreatitis, hypertension, renal disease, cancer, inflammation, and impotence. In certain embodiments, the compounds, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.Type: GrantFiled: September 5, 2003Date of Patent: June 21, 2005Assignee: Esperion Therapeutics, Inc.Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
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Patent number: 6894195Abstract: A process for the preparation of 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol comprising hydrogenating 4-methyl-2,3,5,6-tetrafluorobenzonitrile to 4-methyl-2,3,5,6-tetrafluorobenzylamine and converting 4-methyl-2,3,5,6-tetrafluorobenzylamine to 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol. The process optionally also comprises the further step of reacting 4-Methyl-2,3,5,6-tetrafluobenzyl alcohol with cis-Z-3-(2-chloro-1,1,1-trifluoro-2-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride to the form tefluthrin. 4-Methyl-2,3,5,6-tetrafluorobenzylamine and salts thereof are also claimed.Type: GrantFiled: October 18, 2001Date of Patent: May 17, 2005Assignee: Syngenta LimitedInventors: Raymond Vincent Heavon Jones, Stephen Martin Brown
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Patent number: 6878723Abstract: The invention concerns compounds inhibiting LTA4 hydrolase of formula (I). The invention also concerns their therapeutic, in particular anti-inflammatory, applications.Type: GrantFiled: April 6, 2000Date of Patent: April 12, 2005Assignees: Institut National de la Sante et de la rescherche Medicale (INSERM), BioprojetInventors: Denis Danvy, Thierry Monteil, Jean-Christophe Plaquevent, Pierre Duhamel, Lucette Duhamel, Nadine Noel, Claude Gros, Olivier Chamard, Jean-Charles Schwartz, Jeanne-Marie Lecomte, Serge Piettre
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Patent number: 6875885Abstract: A process for producing compounds of formula (VIIa) and (VIIb) wherein X is a leaving group; Y and Y1 are idependently Cl or Br; and Z is Cl, Br or a haloalkyl group which process comprises a) reacting a compound of formula (VII) wherein X, Y, Y1 and Z are as defined for compounds (VIIa) and (VIIb) with a substantially optically pure chiral amine in a solvent to form a diastereoisomeric salt; b) separating the diastereomeric salt of each enantiomer; c) converting the diastereomeric salt of each anantiomer separately to compounds of formulae (VIIa) and (VIIb) respectively by acid or base hydrolysis, the use of the compounds in making pyrethroid insecticides and novel intermediates.Type: GrantFiled: July 16, 2001Date of Patent: April 5, 2005Assignee: Syngenta LimitedInventors: Stephen Martin Brown, Brian David Gott
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Patent number: 6858650Abstract: The present invention concerns highly pure, crystalline, stable compounds of novel derivatives of 3,3-diphenylpropylamines in the form of their salts, a method for the manufacture and highly pure, stable intermediate products. The method is in particular characterized by regio- and chemoselectivity and high yield. Salts of phenolic monoesters of 3,3-diphenylpropylamines are provided, that are particularly well-suited for use in pharmaceutical formulations. Preferred compounds are R-(+)-2-(3-diisopropylamino-1-phenyl-propyl)-4-hydroxymethylphenylisobutyrate ester hydrogen fumarate and R-(+)-2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenylisobutyrate ester hydrochloride hydrate. Furthermore, stable, crystalline intermediate products that are essential for obtaining the abovementioned salts are provided. A preferred intermediate product is R-(?)-3-(3-diisopropylamino-phenyl-propyl)-4-hydroxy-benzoic acid methyl ester.Type: GrantFiled: November 15, 2000Date of Patent: February 22, 2005Assignee: Schwarz Pharma AGInventor: Claus Meese
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Publication number: 20040234568Abstract: Odourant compounds selected from cycloalkanecarboxylic acid esters of 2-[1-(3,3-dimethylcyclohexyl)ethoxy]-2-methylpropan-1-ol, their preparation and their use as ingredients in fine-fragrances and functional perfumery compositions.Type: ApplicationFiled: June 14, 2004Publication date: November 25, 2004Inventors: Philip Kraft, Riccardo Cadalbert
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Patent number: 6770676Abstract: The present invention relates to 2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives represented by the formula: the pharmaceutically acceptable salts thereof, or the hydrates thereof. The compounds of the present invention are useful as a medicament, and in particular, are useful as modulators acting on group 2 metabotropic glutamate receptors, having effects for treating and/or preventing psychiatric disorders such as schizophrenia, anxiety and its associated diseases, depression, bipolar disorder, and epilepsy; and/or neurological diseases such as drug dependence, cognitive disorders, Alzheimer's disease, Huntington's chorea, Parkinson's disease, dyskinesia associated with muscular stiffness, cerebral ischemia, cerebral failure, myelopathy, and head trauma.Type: GrantFiled: December 6, 2002Date of Patent: August 3, 2004Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Atsuro Nakazato, Toshihito Kumagai, Kosuke Kanuma, Kazunari Sakagami
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Patent number: 6753443Abstract: The present invention relates to a process for preparing a chiral ester according to the formula (100): by reacting (i) a racemic alcohol, (ii) a selected ruthenium complex to activate racemization of the racemic alcohol, (iii) a lipase to selectively acylate one enantiomer of the racemic alcohol, and (iv) an acyl donor compound to supply an acyl group to the lipase.Type: GrantFiled: March 2, 2001Date of Patent: June 22, 2004Assignees: Samsung Fine Chemicals Co., Ltd., Pohang University of Science and TechnologyInventors: Jai Wook Park, Mahn-Joo Kim, Jeong Hwan Koh, Hyun Min Jung
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Patent number: 6750363Abstract: An efficient and selective process, capable of scale-up, to make itaconate derivatives of formula (IV), and/or succinate derivatives of formula (V) and/or (VI) by asymmetric hydrogenation of the itaconate derivatives. wherein R, R1 and R2 are as defined herein.Type: GrantFiled: July 18, 2002Date of Patent: June 15, 2004Assignee: Pfizer, Inc.Inventors: Andrew Michael Derrick, Nicholas Murray Thomson
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Patent number: 6740254Abstract: The present invention provides a phthalate-free plasticizer for polymer resins. The phthalate-free plasticizer according to the invention includes a mixture of different triesters of glycerin, at least one of which meets the formula: CH2(OOR1)CH(OOR2)CH2(OOR3) wherein at least two of R1, R2, and R3 are different alkyl or aryl groups. Phthalate-free plasticizers according to the invention can be made by esterifying glycerin with a mixture of acids in the presence of a catalyst. In the presently most preferred embodiment of the invention, the mixture of acids includes benzoic acid and butanoic acid. The plasticizer according to the invention can be used to modify the properties of a wide variety of polymers including vinyl polymers, rubbers, polyurethanes, and acrylics, and has superb thermostability and low volatility.Type: GrantFiled: December 9, 2002Date of Patent: May 25, 2004Assignee: Ferro CorporationInventors: Lei Zhou, George Schaefer
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Publication number: 20040092553Abstract: Compounds of the formula (I) in which R1, R2 and X1 have the meanings given in the specification, modulate metabotopic glotamate receptor function and are useful in treating disorders of the central nervous system.Type: ApplicationFiled: June 6, 2003Publication date: May 13, 2004Inventors: Ivan Collado Cano, Jesus Ezguera-Carrera, Alicia Marcos Liorente, Luisa Maria Martin-Cabrejas, James Allen Monn
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Patent number: 6734320Abstract: Novel non-symmetric, partially fluorinated compositions and method of manufacture which are useful as lubricants or as additives to lubricant formulations involving the molecular structure: R1f—F′—R2—F″—R3h where R1f represents a wholly or partially fluorinated organic residue end group, F′ and F″ represent functional linkages which may be alike or different, R2 represents the backbone and R3h represents a non-fluorinated organic residue end group. Such compositions are produced by reacting a mixture of alcohols, mercaptans or amines containing at least one partially fluorinated compound and at least one non-fluorinated compound in the mixture, thus producing the R1f and the R3h residues, with a difunctional organic compound (e.g., diacid, dinitrile, disulfonyl halide, diisocyanate, diisothiocyanate, diphosphoryl halide or dithiophosphoryl halide).Type: GrantFiled: April 30, 2002Date of Patent: May 11, 2004Assignee: E. I. du Pont de Nemours and CompanyInventor: Richard P. Beatty
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Patent number: 6730804Abstract: Cyclopropanecarboxylates of lower alcohols are prepared by esterification of the corresponding cyclopropanecarboxylic acids with the corresponding lower alcohols in the presence of an acid catalyst, while maintaining a considerable stoichiometric excess of the cyclopropanecarboxylic acid with respect to the lower alcohol, keeping the temperature at from 100 to 200° C. and distilling off the cyclopropanecarboxylate together with the water of reaction and small amounts of alcohol. Cyclopropanecarboxylates of lower alcohols are valuable intermediates in the pharmaceutical and agrochemical sectors.Type: GrantFiled: August 27, 1998Date of Patent: May 4, 2004Assignee: Degussa AGInventors: Manfred Kaufhold, Marcel Feld
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Publication number: 20040077502Abstract: A method to inhibit the ethylene response in plants with cyclopropene compounds by first generating stable cyclopropane precursor compounds and then converting these compounds to the gaseous cyclopropene antagonist compound by use of a reducing or nucleophilic agent.Type: ApplicationFiled: July 30, 2003Publication date: April 22, 2004Inventors: Richard Martin Jacobson, Martha Jean Kelly, William Nixon James
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Publication number: 20040063993Abstract: A process for the preparation of 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol comprising hydrogenating 4-methyl-2,3,5,6-tetrafluorobenzonitrile to 4-methyl-2,3,5,6-tetrafluorobenzylamine and converting 4-methyl-2,3,5,6-tetrafluorobenzylamine to 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol. The process optionally also comprises the further step of reacting 4-Methyl-2,3,5,6-tetrafluobenzyl alcohol with cis-Z-3-(2-chloro-1,1,1-trifluoro-2-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride to the form tefluthrin. 4-Methyl-2,3,5,6-tetrafluorobenzylamine and salts thereof are also claimed.Type: ApplicationFiled: April 25, 2003Publication date: April 1, 2004Inventors: Raymond Vincent Heavon Jones, Stephen Martin Brown
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Patent number: 6706910Abstract: There is provided a method for producing a cyclopropanecarboxylate of formula (1): which comprises contacting a cyclopropanecarboxylate of formula (2): with a monohydroxy compound of formula (3): R7OH (3) in the presence of a lithium compound of formula (4): R8OLi (4), wherein R1, R2, R3, R4 and R5 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted aryl group; R6 represents an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted phenyl group; R7 and R8 do not simultaneously represent the same and each independently represent a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.Type: GrantFiled: October 31, 2001Date of Patent: March 16, 2004Assignee: Sumitomo Chemical Company, LimitedInventors: Kazunori Iwakura, Hiroshi Souda, Tohei Takagaki, Yoshimi Yamada
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Patent number: 6700012Abstract: This invention relates to compounds of the formula: wherein R1 is H or C1-C6alkyl and the C1-C6alkyl moiety is straight or branched; R2 and R3 are each independently C1-C6alkyl and the C1-C6alkyl moiety is straight or branched; or stereoisomers thereof.Type: GrantFiled: March 22, 2002Date of Patent: March 2, 2004Assignee: Aventis Pharmaceuticals Inc.Inventor: Timothy A. Ayers
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Patent number: 6670500Abstract: There is disclosed an optically active salicylideneaminoalcohol compound of formula (1): wherein R1 represents an alkyl group or the like, R2 represents an aryl group and the like, and when X1 represents a nitro, X2 is a hydrogen atom, when X1 represents a chlorine atom, X2 is a chlorine atom, and when X1 is a hydrogen atom, X2 is a fluorine atom; and the carbon atom denoted by “*” is an asymmetric carbon atom having either an S or R configuration, and a chiral copper complex produced from the optically active salicylidenaminoalcohol compound and a copper compound.Type: GrantFiled: January 23, 2001Date of Patent: December 30, 2003Assignee: Sumitomo Chemical Company, LimitedInventors: Masashi Kamitamari, Gohfu Suzukamo, Michio Yamamoto, Koji Hagiya, Makoto Itagaki
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Publication number: 20030212294Abstract: Poly(3-cyclopropyl-3-hydroxypropionates) (I) which are useful for the preparation of vinylcyclopropane and cyclopropylacetylene are disclosed. Methods for the preparation of a variety of intermediates obtained from (I) such as 3-cyclopropyl-3-hydroxypropionic acid and esters and salts thereof, 3-cyclopropylacrylic acid, and vinylcyclopropane also are disclosed.Type: ApplicationFiled: April 16, 2003Publication date: November 13, 2003Inventors: John Clark Hubbs, Theresa Sims Barnette, Neil Warren Boaz
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Publication number: 20030208092Abstract: Poly(3-cyclopropyl-3-hydroxypropionates) (I) which are useful for the preparation of vinylcyclopropane and cyclopropylacetylene are disclosed. Methods for the preparation of a variety of intermediates obtained from (I) such as 3-cyclopropyl-3-hydroxypropionic acid and esters and salts thereof, 3-cyclopropylacrylic acids and vinylcyclopropane also are disclosed.Type: ApplicationFiled: April 16, 2003Publication date: November 6, 2003Inventors: John Clark Hubbs, Theresa Sims Barnette, Neil Warren Boaz
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Patent number: 6642418Abstract: The invention relates to processes for the preparation of compounds of formula (I), wherein R1 and R2 are as defined in the description.Type: GrantFiled: December 4, 2000Date of Patent: November 4, 2003Assignee: Aventis Cropscience SAInventors: Susan Mary Cramp, Neil Jonathan Geach
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Patent number: 6635784Abstract: Disclosed are processes for the preparation of enantiomerically-enriched cyclopropylalanine derivatives by the hydrogenation of certain enamides in the presence of a catalyst comprising a transition metal and a substantially enantiomerically-pure bis-phosphine catalyst and certain novel enamide ester compounds which are intermediates in the processes. The processes include novel 2-step and 3-step processes for the preparation of enantiomerically-enriched cyclopropylalanine derivatives. The two-step process comprises the steps of reacting cyclopropanecarboxaldehyde with a substituted phosphorylglycine to afford an enamide ester which then is hydrogenated in the presence of a catalyst comprising a transition metal and a substantially enantiomerically-pure bis-phosphine catalyst.Type: GrantFiled: September 20, 2001Date of Patent: October 21, 2003Assignee: Eastman Chemical CompanyInventors: Sheryl Davis Debenham, Neil Warren Boaz
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Patent number: 6613935Abstract: A process includes allowing a &bgr;-ketoester derivative represented by following Formula (1): wherein R1 is a hydrogen atom or a hydrocarbon group; and R2 is a hydrocarbon group, to react with 1,2-dichloroethane and there by produces a 1-acyl-1-cyclopropanecarboxylate derivative represented by following Formula (2): wherein R1 and R2 have the same meanings as defined above.Type: GrantFiled: September 12, 2002Date of Patent: September 2, 2003Assignee: Daicel Chemical Industries, Ltd.Inventors: Hiroki Tanaka, Li Rui Pan, Kiyoshi Ikura
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Patent number: 6610878Abstract: Poly(3-cyclopropyl-3-hydroxypropionates) (I) which are useful for the preparation of vinylcyclopropane and cyclopropylacetylene are disclosed. Methods for the preparation of a variety of intermediates obtained from (I) such as 3-cyclopropyl-3-hydroxypropionic acid and esters and salts thereof, 3-cyclopropylacrylic acid, and vinylcyclopropane also are disclosed.Type: GrantFiled: April 11, 2000Date of Patent: August 26, 2003Assignee: Eastman Chemical CompanyInventors: John Clark Hubbs, Theresa Sims Barnette, Neil Warren Boaz
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Patent number: 6552217Abstract: Disclosed is a 4-step process for the preparation of alkyl esters of 1-methylcyclopropanecarboxylic acid which comprises the steps of (1) converting &ggr;-butyrolactone to &agr;-methyl-&ggr;-butyrolactone; (2) converting the &agr;-methyl-&ggr;-butyrolactone from step (1) to an alkyl 4-halo-2-methylbutyrate; (3) producing a xylene solution of the alkyl 4-halo-2-methylbutyrate; and (4) contacting the xylene solution of an alkyl 4-halo-2-methylbutyrate from step (3) with an alkali metal alkoxide under conditions of temperature and pressure which causes vaporization of (i) an alkanol as it is formed and (ii) an alkyl 1-methylcyclopropanecarboxylate as it is formed from the alkyl 4-halo-2-methylbutyrate. Also disclosed are processes whereby the alkyl 1-methylcyclopropanecarboxylate, prepared as described above, is converted to 1-methylcyclopropylamine.Type: GrantFiled: July 2, 2001Date of Patent: April 22, 2003Assignee: Eastman Chemical CompanyInventors: John Clark Hubbs, David Carl Attride, Neil Warren Boaz, James Charles Ciula, John Thorton Maddox, Thomas Nabih, William Dell Nottingham, David Chris Spencer
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Publication number: 20030065212Abstract: A process includes allowing a &bgr;-ketoester derivative represented by following Formula (1): 1Type: ApplicationFiled: September 12, 2002Publication date: April 3, 2003Inventors: Hiroki Tanaka, Li Rui Pan, Kiyoshi Ikura
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Patent number: 6531626Abstract: There is disclosed a method for producing cyclopropanecarboxylates of the formula (3): by transesterification in the presence of a lanthanoid metal alkoxideType: GrantFiled: October 7, 1999Date of Patent: March 11, 2003Assignee: Sumitomo Chemical Company, LimitedInventors: Yoshiaki Oda, Makoto Yako
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Publication number: 20030032839Abstract: There is disclosed a process for the racemization of a vinyl-substituted cyclopropanecarboxylic acid or a derivative thereof, which is characterized by reacting an optically active vinyl-substituted cyclopropanecarboxylic acid compound of formula (1): 1Type: ApplicationFiled: July 16, 2002Publication date: February 13, 2003Inventors: Hiroshi Souda, Kazunori Iwakura, Fumisato Goto
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Publication number: 20030008913Abstract: Compounds of formula (I) in which R represents the remainder of an alcohol used in the pyrethroid series, in all their possible stereoisomer forms as well as their mixtures, and compositions comprising them. The compounds of formula (I) are useful as pesticides.Type: ApplicationFiled: May 7, 2002Publication date: January 9, 2003Inventors: Andrew Adams, Jean Pierre Demoute, Jacques Demassey, Didier Babin
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Patent number: 6498180Abstract: Compounds of formula (I) in which R1 is halo-C1-10 alkyl; halo-C2-10 alkenyl; or (CH2)nY in which n is 1 or 2 and Y is OH, CN, N3, OR3, SH, S(O)pR4, S(O)3H, NH2, NHR5, NR6R7, NHCOR8, NO2, CO2H, CONHR9, 1H-tetrazol-5-yl, 5-phenyltetrazol-2-yl or PO3H2; R3, R5, R6, R7, R8 and R9 are each selected independently from C1-4 alkyl, aryl and aryl-C1-4 alkyl; R4 is selected from C1-4 alkyl, aryl, aryl-C1-4 alkyl, and 1H-tetrazol-5-yl, carboxy-(1-4C)alkyl and 1H-tetrazol-5-yl-C1-4 alkyl; and p is 0, 1, 2 or 3; or a salt or ester thereof, provided that R1 is not methoxymethyl, modulate metabotropic glutamate receptor function and are useful in treating disorders of the central nervous system.Type: GrantFiled: November 16, 2001Date of Patent: December 24, 2002Assignee: Eli Lilly and CompanyInventors: Ivan Collado Cano, Concepcion Pedregal Tercero, Alicia Marcos Llorente, Beatriz Lopez de Uralde Garmendia, Maria Rosario Gonzalez Garcia, Ana Belen Bueno Melendo
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Patent number: 6498267Abstract: 5-Halo-4-fluoro-4,7,7-trimethyl-3-oxabicyclo[4.1.0]heptan-2-ones, process for their preparation and their use for preparing cyclopropanecarboxylic acids Compounds of the formula (I), in which Hal is Cl, Br or I, are suitable for use as intermediates in the preparation of pyrethroids.Type: GrantFiled: October 17, 2001Date of Patent: December 24, 2002Assignee: Aventis CropScience GmbHInventors: Jean Pierre Demoute, Günter Hömberger, Sergej Pazenok, Didier Babin
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Patent number: 6469198Abstract: There is disclosed chiral copper complex catalyst composition, which is obtained by contacting an optically active N-salicylideneaminoalcohol compound of formula (1): with a mono-valent or di-valent copper compound in an inert solvent, wherein R1 and R2 represent an alkyl group and the like, X1 and X2 represent a hydrogen atom, a halogen atom, a nitro group, an alkyl group, an alkoxy group, a cyano group or the like, and the amount of the mono-valent or di-valent copper compound is less than 1 mole per 1 mole of the optically active N-salicylideneaminoalcohol compound of formula (1), and a process for producing an optically active cylopropane-carboxylic acid ester using the same.Type: GrantFiled: January 23, 2001Date of Patent: October 22, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Gohfu Suzukamo, Makoto Itagaki, Michio Yamamoto
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Publication number: 20020151741Abstract: There is disclosed a process process for producing a cyclopropanecarboxylate of formula (1): 1Type: ApplicationFiled: January 24, 2002Publication date: October 17, 2002Inventors: Hiroshi Souda, Kazunori Iwakura
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Patent number: 6462224Abstract: 1,1-cyclopropanedicarboxylic diesters are prepared from malonic diesters, 1,2-dihaloethane and alkali metal carbonate in the presence of a mixture of available or in situ-produced phase transfer catalyst and polyalkylene glycol or derivatives thereof which are capped at one or both ends, in particular those with ether end groups, where the molar ratio of malonic diester: 1,2-dihaloethane: alkali metal carbonate is 1:(1 to 7):(1 to 1.4).Type: GrantFiled: December 19, 2000Date of Patent: October 8, 2002Assignee: Degussa AGInventors: Andreas Harthun, Manfred Neumann, Christoph Theis
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Patent number: 6462225Abstract: An ester compound, which is a production intermediate of a pyrethroid compound, given by formula wherein R1 represents C1-6 alkyl group, etc., can be produced by allowing to react an aldehyde compound given by formula wherein R1 has the same meaning above, with a phosphorane compound given by formula wherein R2 represents a hydrogen atom, halogen atom or C1-4 alkyl group, in an organic solvent, and obtaining a liquid distillate by heating the above reaction mixture with water in high yield.Type: GrantFiled: December 22, 2000Date of Patent: October 8, 2002Assignee: Sumitomo Chemical Company, LimitedInventor: Tomonori Yoshiyama
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Patent number: 6448412Abstract: The invention is directed to multiply-substituted fullerene derivatives of novel configurations, and methods for their preparation and use. The methods involve the combinatorial synthesis of a library of fullerene derivatives and comprises the steps of forming a mixture of fullerene derivatives by reacting the Cn fullerene with two or more reactive precursor compounds, and removing the unreacted compounds to yield the fullerene derivatives having the desired activity. Methods for the identification and screening of a combinatorial library of fullerenes by 3He-nuclear magnetic resonance and electrospray mass spectrometry to define members with the optimal desired activity are also provided.Type: GrantFiled: October 30, 2000Date of Patent: September 10, 2002Assignee: Sphere Biosystems, Inc.Inventors: Randall B. Murphy, Stephen R. Wilson, Quing Lu
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Patent number: 6441176Abstract: Methods of preparing NHE-1 disclosed. The NHE-1 inhibitors are useful for the reduction of tissue damage resulting from tissue ischemia.Type: GrantFiled: August 10, 2000Date of Patent: August 27, 2002Assignee: Pfizer Inc.Inventor: Norma J. Tom
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Patent number: 6441220Abstract: There is provided a method for producing a cyclopropanecarboxylate of formula (3): wherein R1, R2, R3, R4 and R5 each independently represent: a hydrogen atom, halogen atom, an optionally substituted alkyl group and the like; and R7 represents: an optionally substituted alkyl group, and the like, which is characterized by reacting a cyclopropanecarboxylate of the formula (1) wherein R1, R2, R3, R4 and R5 are as defined above, and R6 represents an alkyl group having 1 to 10 carbon atoms or an optionally substituted phenyl group, with a monohydroxy compound of the formula (2): R7OH (2) wherein R7 is the same as defined above, in the presence of an alkali metal hydroxide.Type: GrantFiled: June 16, 2000Date of Patent: August 27, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroshi Souda, Kazunori Iwakura
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Patent number: 6423865Abstract: The invention relates to compounds with the general formula Y1—A1—M1—A2—Y2 wherein Y1 and Y2 are different from each other and Y1 is an acrylate or methacrylate residue and Y2 is a vinyl ether, epoxy, or azide residue, A1 and A2 are identical or different residues with the general formula CnH2n in which n is a whole number from 0 to 20 and one or more methylene groups can be replaced by oxygen atoms, and M1 has the general formula —R1—X1—R2—X2—R3—X3—R4— wherein R1, R2, R3, and R4 are identical or different doubly bonded residues from the group —O—, —COO—, —CONH—, —CO—, —S—, —C≡C—, —CH═CH—, —CH═N—, —CH2—, —N═N—, and —N═N(O)—, and R2—X2—R3 can also be a C—C bond, and X1, X2, and X3 are identical or different residues from the group 1,4-phenylene, 1,4-cyclohexylenType: GrantFiled: March 1, 2000Date of Patent: July 23, 2002Assignee: DaimlerChrysler AGInventors: Peter Strohriegl, Katja Strelzyk, Andreas Stohr, Petra Grundig, Michael Gailberger, Fritz Dannenhauer, Anne Barth
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Patent number: 6417389Abstract: This invention relates to a novel advantageous process for the stereoselective preparation of 2-hydroxy-4-phenylbutyrates (HPB esters) and of their precursors. This is done by starting from readily accessible &agr;-unsaturated &agr;-hydroxy-&ggr;-keto esters which can be prepared by Claisen condensation.Type: GrantFiled: September 25, 2000Date of Patent: July 9, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Martin Studer, Peter Herold, Adriano Indolese, Stefan Burckhardt
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Patent number: 6414181Abstract: Provided are processes of producing a cyclopropanecarboxylate compound of Formula (I): The processes comprise reacting a cyclopropanecarbaldehyde compound of Formula (II): with a dicarboxylate compound of Formula (III): in the presence of at least one secondary amine from among piperidine, morpholine, pyrrolidine, diethylamine or N-methylethanolamine.Type: GrantFiled: January 5, 2000Date of Patent: July 2, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Takashi Furukawa, Noritada Matsuo
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Patent number: 6403638Abstract: Compounds having the formulas below, where R is H, lower alkyl, or a pharmaceutically acceptable salt, and where R1 represents i-propyl, t-butyl or n-butyl groups, have selective RXR retionoid agonist activity.Type: GrantFiled: March 21, 2000Date of Patent: June 11, 2002Assignee: Allergan Sales, Inc.Inventors: Vidyasagar Vuligonda, Kwok Yin Tsang, Jayasree Vasudevan, Roshantha A. Chandraratna
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Patent number: 6399785Abstract: The invention is directed to multiply-substituted fullerene derivatives of novel configurations, and methods for their preparation and use. The methods involve the combinatorial synthesis of a library of fullerene derivatives and comprises the steps of forming a mixture of fullerene derivatives by reacting the Cn fullerene with two or more reactive precursor compounds, and removing the unreacted compounds to yield the fullerene derivatives having the desired activity. Methods for the identification and screening of a combinatorial library of fullerenes by 3He-nuclear magnetic resonance and electrospray mass spectrometry to define members with the optimal desired activity are also provided.Type: GrantFiled: October 30, 2000Date of Patent: June 4, 2002Assignee: C-Sixty, Inc.Inventors: Randall B. Murphy, Stephen R. Wilson, Quing Lu
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Publication number: 20020052525Abstract: There is provided a method for producing a cyclopropanecarboxylate of formula (1): 1Type: ApplicationFiled: October 31, 2001Publication date: May 2, 2002Inventors: Kazunori Iwakura, Hiroshi Souda, Tohei Takagaki, Yoshimi Yamada
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Publication number: 20020049331Abstract: Disclosed are processes for the preparation of enantiomerically-enriched cyclopropylalanine derivatives by the hydrogenation of certain enamides in the presence of a catalyst comprising a transition metal and a substantially enantiomerically-pure bis-phosphine catalyst and certain novel enamide ester compounds which are intermediates in the processes. The processes include novel 2-step and 3-step processes for the preparation of enantiomerically-enriched cyclopropylalanine derivatives. The two-step process comprises the steps of reacting cyclopropanecarboxaldehyde with a substituted phosphorylglycine to afford an enamide ester which then is hydrogenated in the presence of a catalyst comprising a transition metal and a substantially enantiomerically-pure bis-phosphine catalyst.Type: ApplicationFiled: September 20, 2001Publication date: April 25, 2002Inventors: Sheryl Davis Debenham, Neil Warren Boaz
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Patent number: 6376699Abstract: Hydroazinecarboxylic acid ester of the formula In which R1 is an optionally substituted alkyl group, an aryl group, an arylalkyl group or a cycloalkyl group, and R3 is an optionally substituted alkyl group.Type: GrantFiled: January 26, 2001Date of Patent: April 23, 2002Assignee: Lonza AGInventor: Ulrich Veith
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Patent number: 6369194Abstract: The invention relates to compounds of formula where R is a structural diversity element selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, peptidyl, heteroatom-substituted alkyl, cycloalkyl, and amines; and Nu is a structural diversity element derived from a nucleophile, NuH, selected from the group consisting of amines, amino acids, peptide, water, hydrogen sulfide, alcohols, and thiols. The invention also relates to arrays and combinatorial libraries of such compounds, and to a method of preparing such compounds.Type: GrantFiled: November 9, 1998Date of Patent: April 9, 2002Assignee: Yale UniversityInventor: Harry H. Wasserman
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Patent number: 6359164Abstract: The present invention relates generally to novel methods for the preparation of cyclopropylacetylene which is an essential reagent in the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one; a useful human immunodeficiency virus (HIV) reverse transcriptase inhibitor with superior anti-retroviral activity. In the process, for example, cyclopropane carboxaldehyde is alkylated to form 1,1,1-trichloro-2-cyclopropyl-ethanol; which in turn undergoes elimination to form 1,1-dichloro-2-cyclopropyl-ethene; which in turn undergoes elimination to form cyclopropyl acetylene.Type: GrantFiled: September 30, 1999Date of Patent: March 19, 2002Inventors: Zhe Wang, Joseph M. Fortunak
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Publication number: 20020016493Abstract: Disclosed is a 4-step process for the preparation of alkyl esters of 1-methylcyclopropanecarboxylic acid which comprises the steps of (1) converting &ggr;-butyrolactone to &agr;-methyl-&ggr;-butyrolactone; (2) converting the &agr;-methyl-&ggr;-butyrolactone from step (1) to an alkyl 4-halo-2-methylbutyrate; (3) producing a xylene solution of the alkyl 4-halo-2-methylbutyrate; and (4) contacting the xylene solution of an alkyl 4-halo-2-methylbutyrate from step (3) with an alkali metal alkoxide under conditions of temperature and pressure which causes vaporization of (i) an alkanol as it is formed and (ii) an alkyl 1-methylcyclopropanecarboxylate as it is formed from the alkyl 4-halo-2-methylbutyrate. Also disclosed are processes whereby the alkyl 1-methylcyclopropanecarboxylate, prepared as described above, is converted to 1-methylcyclopropylamine.Type: ApplicationFiled: July 2, 2001Publication date: February 7, 2002Inventors: John Clark Hubbs, David Carl Attride, Neil Warren Boaz, James Charles Ciula, John Thorton Maddox, Thomas Nabih, William Dell Nottingham, David Chris Spencer