Carboxyl, Or Salt Thereof, Bonded Directly To A Ring Patents (Class 562/458)
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Patent number: 6710205Abstract: An agent comprising the benzoic acid of formula (I) wherein A, B, R6, R7 are carbocyclic ring, heterocyclic ring, etc.; R1 is hydroxy etc.; R2, R3, R4 are alkyl etc.; R5, D, E are alkylene, etc.; G is oxygen etc., as active ingredient. The compound of formula (I) is considered to be useful for the treatment and/or prophylaxis of bone diseases, cancer, systemic granuloma, immunological diseases, allergy, atopy, asthma, gumboil, gingivitis, periodontitis, neurocyte death, Alzheimer's diseases, lungs injury, pulmopathy, acute hepatitis, nephritis, myocardial ischemia, Kawasaki disease, ambustion, ulcerative colitis, Crohn's disease, multiple organ failure, sleeping disorder, platelet aggregation, etc.Type: GrantFiled: August 16, 2002Date of Patent: March 23, 2004Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Kousuke Tani, Kaoru Kobayashi, Takayuki Maruyama
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Patent number: 6699909Abstract: The present invention relates to therapeutically active novel aminoindanes of formula (I). Also provided is a method of preparing compounds of formula (I), and pharmaceutical compositions comprising the compounds. The novel compounds act as modulators of metabotropic glutamate receptors and, as such, are useful in treating diseases of the central nervous system related to the metabotropic glutamate receptor system.Type: GrantFiled: May 7, 2002Date of Patent: March 2, 2004Assignee: Prescient NeuroPharma Inc.Inventor: Kenneth Curry
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Patent number: 6603041Abstract: Enamide derivatives of formula (1) are described: wherein R1 is a group Ar1L2Ar2Alk- in which Ar1 is an optionally substituted aromatic or heteroaromatic group, L2 is a covalent bond or a linker atom or group, Ar2 is an optionally substituted arylene or heteroarylene group and Alk is a chain —CH2—CH(R)—, —CH═C(R)— or in which R is a carboxylic acid (—CO2H) or a derivative or biostere thereof; R2 is a hydrogen atom or a C1-6alkyl group; X is an O or S atom or the group NR30 group; j and k is each zero or the integer 1 or 2 provided that the sum of j and k is zero or the integer 1 or 2; Cy1 is an optionally substituted cycloaliphatic, heterocycloaliphatic, aromatic or heteroaromatic group; and the salts, solvates, hydrates and N-oxides thereof.Type: GrantFiled: September 5, 2001Date of Patent: August 5, 2003Assignee: Celltech R & D LimitedInventors: Timothy John Norman, John Robert Porter, John Clifford Head, Andrew James Ratcliffe
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Patent number: 6504052Abstract: Compounds of the formula (I) in which R1 is C1-10 allyl; C2-10 alkenyl; C2-10 alkynyl; phenyl-C2-10 alkyl or phenyl-C2-10 alkenyl; and salts and esters thereof, modulate metabotropic glutamate receptor function and are useful in treating disorders of the central nervous systemType: GrantFiled: November 16, 2001Date of Patent: January 7, 2003Assignee: Eli Lilly and CompanyInventors: Ivan Collado Cano, Concepcion Pedregal Tercero, Alicia Marcos Llorente
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Patent number: 6172239Abstract: The invention relates to compounds of the formula The compounds have agreat affinity for the neurotensin receptors.Type: GrantFiled: August 16, 1999Date of Patent: January 9, 2001Assignee: SanofiInventors: Bernard Labeeuw, Danielle Gully, Francis JeanJean, Jean-Charles Molimard, Robert Boigegrain
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Patent number: 6172058Abstract: A pharmaceutical compound of the formula in which R1 is C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C3-10 cycloalkyl, C3-10 cycloalkyl-C1-10 alkyl, C3-10 cycloalkyl-C2-10 alkenyl, C3-10 cycloalky-C2-10 alkynyl, optionally substituted phenyl-C1-10 alkyl, optionally substituted phenyl-C2-10 alkenyl, optionally substituted phenyl-C2-10 alkynyl, optionally substituted naphthyl, optionally substituted naphthyl-C1-10 alkyl, C1-10 alkoxy-C1-10 alkyl, C3-10 cycloalkoxy-C1-10 alkyl, optionally substituted heterocyclyl, optionally substituted heterocyclyl-C1-10 alkyl, optionally substituted phenyl fused to C5-10 cycloalkyl, optionally substituted tricyclic, optionally substituted tricyclic-C1-10 alkyl, or [optionally substituted phenyl(CH2)n]2-C1-10 alkyl, where n is 0 or 1 to 4, and R2 is hydrogen or one of the values for R1; or a salt or ester thereof.Type: GrantFiled: April 3, 1998Date of Patent: January 9, 2001Assignee: Lilly, SAInventors: Concepci{acute over (o)}n Pedregal Tercero, Ivan Collado Cano, Angel Maz{acute over (o)}n Ruiz
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Patent number: 6150412Abstract: The invention relates to compounds of formula (I) ##STR1## wherein R.sub.1 is an electronegative substituent, preferably nitro, cyano, formyl or carboxy, R.sub.2 is --A--R.sub.4, wherein A is a branched or straight chain C.sub.1-9 alkylene and R.sub.4 is carboxy or 5-tetrazolyl; R.sub.3 is an electronegative substituent, preferably nitro, cyano, halogen, formyl, carboxy, C.sub.1-5 alkyl carbonyl, aryl carbonyl or SO.sub.2 R.sub.6, wherein R.sub.6 is a branched or straight chain C.sub.1-5 alkyl, aryl alkyl, aryl or NR.sub.7 R.sub.8, wherein R.sub.7 and R.sub.8 are independently hydrogen, a branched or straight chain C.sub.1-5 alkyl or together form a C.sub.3-6 ring; or a pharmaceutically acceptable ester or salt thereof. The compounds are peripheral, long acting COMT (catechol-O-methyl transferase) inhibitors and are useful, e.g., in the treatment of Parkinson's disease and hypertension.Type: GrantFiled: November 21, 1997Date of Patent: November 21, 2000Assignee: Orion-yhtyma OyInventors: Jarmo Pystynen, Anne Luiro, Timo Lotta, Martti Ovaska, Jukka Vidgren
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Patent number: 6127392Abstract: Compounds of the formula: wherein:R.sub.1, R.sub.2, R.sub.3, R.sub.4,R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are, independently, hydrogen, COOR.sub.15, halogen, nitro, cyano, C.sub.1-10 alkoxy, C.sub.1-10 haloalkoxy, sulfonic acid, C.sub.1-10 alkylsulfonyl, C.sub.6-12 arylsulfonyl, C.sub.6-12 aralkylsulfonyl, C.sub.1-10 alkylsulfinyl, C.sub.6-12 arylsufinyl, C.sub.6-12 aralkylsulfinyl, sulfamoyl, C.sub.1-10 alkylsulfamido, C.sub.6-12 arylsulfamido, C.sub.1-10 alkanoyl, C.sub.6-12 aryloyl, C.sub.6-12 aralkanoyl, amino, C.sub.1-10 alkylamino, C.sub.2-10 dialkylamino, C.sub.6-12 aralkylamino, C.sub.6-12 arylamino, carboxamido, C.sub.1-10 alkylcarboxamido, C.sub.6-12 arylcarboxamido, C.sub.1-10 haloalkyl, C.sub.1-10 alkyl, C.sub.2-12 alkenyl, C.sub.6-12 aryl, C.sub.6-12 aralkyl; with the proviso that at least one of R.sub.4 and R.sub.5 is COOR.sub.15 ;R.sub.9 is hydrogen, C.sub.1-10 alkyl and C.sub.1-10 haloalkyl;R.sub.10 is hydrogen, C.sub.1-10 alkyl, C.sub.1-10 haloalkyl, or C.sub.2-12 alkylidene;R.sub.Type: GrantFiled: August 3, 1998Date of Patent: October 3, 2000Assignee: American Home Products CorporationInventors: Joseph Richard Lennox, Schuyler Adam Antane, John Anthony Butera
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Patent number: 6114386Abstract: A sialidase inhibitor of the shown formula I: ##STR1## where dashed lines d.sub.1 and d.sub.2, X.sub.1, R.sub.1, R.sub.2, R.sub.6, R.sub.3, R.sub.4 and R.sub.5 are as described in the specification; or an analog, pharmaceutically acceptable salt, or derivative of the inhibitor, with the proviso that the inhibitor is not HANBA GBA or Neu5Ac2en. The inhibitor in a composition with a pharmaceutically acceptable carrier. Methods of making a pharmaceutical composition of an acceptable carrier and the inhibitor. Methods of inhibiting sialidase and methods of treating and preventing bacterial or trypanosomal infection using the inhibitor.Type: GrantFiled: October 14, 1997Date of Patent: September 5, 2000Assignee: University of AlabamaInventors: Ming Luo, Clinton L. White
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Patent number: 5965592Abstract: Compounds of the formula ##STR1## and their salts, in which R.sub.1, is a C.sub.1 -C.sub.7 aliphatic hydrocarbon radical; X.sub.1 is --CO; X.sub.2 is a divalent aliphatic hydrocarbon radical which comprises an ethyl group and an alkylene of 2 to 6 carbon atoms; R.sub.2 is hydroxy, carboxy or alkoxycarbonyl in which alkoxy is from 1 to 7 carbon atoms; X.sub.3 is a divalent aliphatic hydrocarbon; R.sub.3 is carboxyl or 5-tetrazolyl; and the rings A and B independently of one another are otherwise unsubstituted; can be prepared in a known manner and may be used as active ingredients for medicaments.Type: GrantFiled: July 29, 1998Date of Patent: October 12, 1999Assignee: Novartis CorporationInventors: Peter Buhlmayer, Franz Ostermayer, Tibur Schmidlin
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Patent number: 5935585Abstract: Novel pharmaceutically/cosmetically-active biaromatic amido compounds have the structural formula (I): ##STR1## in which Ar is a radical selected from among those of the following formulae (a)-(e): ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.Type: GrantFiled: February 23, 1996Date of Patent: August 10, 1999Assignee: Centre International de Recherches Dermatologiques GaldermaInventors: Jean-Michel Bernardon, Laurence Vigne
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Patent number: 5936119Abstract: The invention provides a process for the preparation of 3-(N,N-dimethylamino)benzoic acid which comprises subjecting an aqueous solution of an alkali metal salt or ammonium salt of 3-aminobenzoic acid to reductive methylation in the presence of a supported transition metal catalyst, by the controlled and continuous addition of a solution of formaldehyde over a period of 0.5 to 20 hours with a hydrogen pressure between 1 bar and 40 bar and with the temperature of the reaction mass gradually raised during the reduction, the reaction being carried out within the temperature range of 20.degree. C. to 120.degree. C., and wherein a buffering agent is added such that the pH of the reaction mass after reductive methylation is from 6.5 to 9.5.Type: GrantFiled: January 27, 1998Date of Patent: August 10, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: John Barry Henshall, John Whitworth
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Patent number: 5872282Abstract: A family of compounds has been found to be useful for right-shifting hemoglobin towards a low oxygen affinity state. The compounds are capable of acting on hemoglobin in whole blood. In addition, the compounds can maintain the oxygen affinity in blood during storage and can restore the oxygen affinity of outdated blood.Type: GrantFiled: March 13, 1998Date of Patent: February 16, 1999Assignee: Virginia Commonwealth UniversityInventors: Donald J. Abraham, Gajanan Joshi, Ramnarayan Randad
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Patent number: 5744638Abstract: The present invention relates to a process for the preparation of compounds of the general formula I ##STR1## in which X and Y, independently of each other, represent hydrogen, fluorine, chlorine or bromine, but cannot simultaneously represent hydrogen, characterised in that compounds of the general formula II ##STR2## in which X and Y are defined as above, are reacted with aqueous ammonia under copper catalysis, and to intermediates for the preparation of compounds of the general formula I.Type: GrantFiled: January 13, 1995Date of Patent: April 28, 1998Assignee: Riedel-de Haen AktiengesellschaftInventors: Horst Schmand, Bernd Kellermeier, Gunter Bartels, Hans-Jurgen Schmidt
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Patent number: 5741926Abstract: Aniline derivatives useful as antihyperglycemic agents, pharmaceutical compositions comprising the aniline derivatives and methods for their use are described. The aniline derivatives are useful for the treatment of insulin-dependent diabetes mellitus (IDDM or Type I) and non-insulin dependent diabetes mellitus (NIDDM or Type II).Type: GrantFiled: February 12, 1997Date of Patent: April 21, 1998Assignee: Shaman Pharmaceuticals, Inc.Inventors: Donald E. Bierer, Larisa G. Dubenko
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Patent number: 5717109Abstract: The present invention provides compounds of formula ##STR1## in which R represents an organic group, or a pharmaceutically acceptable metabolically labile ester or amide thereof, or a pharmaceutically acceptable salt thereof, which are useful as antagonists of one or more of the actions of L-glutamate at metabotropic excitatory amino acid receptors.Type: GrantFiled: July 10, 1995Date of Patent: February 10, 1998Assignee: Eli Lilly and CompanyInventors: M. Brian Arnold, Thomas J. Bleisch, David R. Helton, Mary Jeanne Kallman, Paul L. Ornstein, Darryle D. Schoepp, Joseph P. Tizzano
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Patent number: 5705528Abstract: Novel farnesyl derivatives which are inhibitors of the prenylated protein thyltransferase enzyme, and useful as anti-cancer drugs, have the following formula: ##STR1## wherein R.sup.1 represents farnesyl, geranyl or geranyl-geranyl;Z represents C--R.sup.6 or N;R.sup.2 represents H, CN, the groups COOR.sup.7, SO.sub.3 R.sup.7, CONR.sup.7 R.sup.8 and SO.sub.2 NR.sup.7 R.sup.7, wherein R.sup.7 and R.sup.8 are each independently hydrogen, alkyl, alkenyl, and the groups COOM and SO.sub.3 M, wherein M is a cation;R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently hydrogen, carboxyl, alkyl, alkenyl, aminoalkyl, nitroalkyl, nitro, halo, amino, mono- or di-alkylamino, mercapto, mercaptoalkyl, azido, or thiocyanato;X represents O, S, SO, SO.sub.2, NH or Se; and the quaternary ammonium salts and N-oxides of the compounds of formula I wherein Z is N.Type: GrantFiled: November 10, 1994Date of Patent: January 6, 1998Assignee: Ramot University Authority for Applied Research & Industrial DevelopmentInventor: Yoel Kloog
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Patent number: 5599814Abstract: The present invention relates to pyridazino[4,5-b]quinolines, and pharmaceutically useful salts thereof, which are excitatory amino acid antagonists and which are useful when such antagonism is desired such as in the treatment of neurological disorders. The invention further provides pharmaceutical compositions containing pyridazino[4,5-b]quinolines as active ingredient, and methods for the treatment of neurological disorders.Type: GrantFiled: April 24, 1995Date of Patent: February 4, 1997Assignee: Imperial Chemical Industries, PLCInventors: Thomas M. Bare, Richard B. Sparks
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Patent number: 5543550Abstract: The present invention relates to a process for the preparation of 5-fluoroanthranilic alkyl esters and/or 5-fluoroanthranilic acid, which comprises dissolving a 3-fluorobenzoic alkyl ester in sulfuric acid and reacting the solution with a nitrating acid at from -10.degree. to 30.degree. C., then adding water, separating off the nitrated reaction product and reacting it with hydrogen at from 50.degree. to 120.degree. C. under elevated pressure in the presence of a catalyst comprising a metal of the platinum group and sulfur, and, if desired, removing 5-fluoroanthranilic alkyl esters by distillation and hydrolyzing them to give 5-fluoroanthranilic acid.Type: GrantFiled: October 6, 1994Date of Patent: August 6, 1996Assignee: Hoechst AktiengesellschaftInventors: Jochen Rapp, Siegfried Planker, Theodor Papenfuhs, G unter Bartels
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Patent number: 5536878Abstract: Disclosed are (1) a method for preparing an aromatic secondary amino compound which comprises reacting an N-cyclohexylideneamino compound in the presence of a hydrogen moving catalyst and a hydrogen acceptor by the use of a sulfur-free polar solvent and/or a cocatalyst, and (2) a method for preparing an aromatic secondary amino compound which comprises reacting cyclohexanone or a nucleus-substituted cyclohexanone, an amine and a nitro compound corresponding to the amine in a sulfur-free polar solvent in the presence of a hydrogen moving catalyst, a cocatalyst being added or not added. In a further aspect, a method is provided for the preparation of aminodiphenylamine by reacting phenylenediamine and cyclohexanone in the presence of a hydrogen transfer catalyst in a sulfur-free polar solvent while using nitroaniline as a hydrogen acceptor.Type: GrantFiled: December 2, 1994Date of Patent: July 16, 1996Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Teruyuki Nagata, Chiyuki Kusuda, Masaru Wada, Kenichi Satou, Masae Uchida
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Patent number: 5523472Abstract: The present invention relates to a process for the preparation of 5-fluoroanthranilic acid, which comprises reacting 5-fluoro-2-bromotoluene in the presence of a catalyst and of an acidic solvent, with oxygen or an oxygen-containing gas at from 80.degree. to 220.degree. C., separating off the 5-fluoro-2-bromobenzoic acid formed and reacting it with ammonia at from 70.degree. to 180.degree. C.Type: GrantFiled: October 6, 1994Date of Patent: June 4, 1996Assignee: Hoechst AktiengesellschaftInventors: Freimund Rohrscheid, Jochen Rapp, Theodor Papenfuhs
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Patent number: 5482942Abstract: This invention relates to novel 4-(3,4-dioxocyclobuten-1-yl)chromenes and dihydronaphthalenones and 3-(3,4-dioxocyclobuten-1-yl)indenes and salts thereof having smooth muscle relaxing activity, to their use in the treatment of hypertension as well as for treatment of peripheral vascular disease, congestive heart failure, disorders involving excessive smooth muscle contraction of the urinary tract such as incontinence or of the gastrointestinal tract such as irritable bowel syndrome, asthma, and hair loss and to pharmaceutical compositions containing an invention compound. The present invention discloses compounds represented by the formula (I): ##STR1## wherein: R.sub.1 and R.sub.2, independent from each other, are selected from the following: C.sub.1-6 perfluoroalkoxy, C.sub.1-6 perfluoroalkyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxyl, C.sub.1-6 alkoxycarbonyl, nitro, cyano, halogen, C.sub.1-6 alkylsulfonamido, C.sub.1-6 perfluoroalkylsulfonamido, amino, C.sub.1-6 acylamino, C.sub.Type: GrantFiled: June 28, 1994Date of Patent: January 9, 1996Assignee: American Home Products CorporationInventors: Richard M. Soll, Paul J. Dollings
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Patent number: 5436368Abstract: Compounds of the formula ##STR1## which are intermediates in the preparation of 4,5-difluoroanthranilic acid, an intermediate itself in the synthesis of quinolone antibacterials, and methods of preparing these intermediates.Type: GrantFiled: November 14, 1994Date of Patent: July 25, 1995Assignee: Pfizer Inc.Inventor: Tamim F. Braish
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Patent number: 5410082Abstract: Process for preparing amines by reacting amides in aqueous-alkaline solutions and/or suspensions with halogens or hypohalites in the presence of alcohols, and converting the reaction products into the amines by hydrolysis, hydrogenation or reductive methods.Type: GrantFiled: May 9, 1994Date of Patent: April 25, 1995Inventor: Ralf Pfirmann
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Patent number: 5403853Abstract: The compounds of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are, independently, hydrogen, straight or branched chain alkyl or mono- or bi-cyclic alkyl;A is a substituted phenyl group containing one or two substituents selected from cyano, nitro, alkyl, perfluoroalkyl, alkoxy, perfluoroalkoxy, amino, alkylamino, dialkylamino, sulfamyl, alkylsulfonamido, arylsulfonamido, alkylcarboxamido, arylcarboxamido, alkylsulfone, perfluoroalkylsulfone, arylsulfone, chloro, bromo, fluoro, iodo, 1-imidazolyl or carboxyl; or a pharmaceutically acceptable salt thereof, are smooth muscle relaxants.Type: GrantFiled: June 13, 1994Date of Patent: April 4, 1995Assignee: American Home Products CorporationInventors: John A. Butera, Schuyler A. Antane
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Patent number: 5393902Abstract: A process is reported for the preparation of bis(amidocarboxylic acid) involving reacting an ester with an aminocarboxylate compound, the latter being formed from lactams or aminocarboxylic acids and salts thereof. The ester and aminocarboxylate compound are present in a weight ratio of about 1:1 to about 1:4, and reaction is conducted in a mono- or polyhydric alcohol solvent.Type: GrantFiled: April 26, 1994Date of Patent: February 28, 1995Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Janet L. Coope, AnneMarie Brescia, Michael I. Hill, Martina Santoso, Stephen A. Madison
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Patent number: 5387594Abstract: Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## n=1 or 2 or: ##STR3## X represents a divalent radical, Z represents O, S or a divalent radical,and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent a hydrogen atom or various organic radicals, and the salts of the compounds of formula (I) when R.sub.1 is a carboxylic acid function.Use in human and veterinary medicine and in cosmetics.Type: GrantFiled: August 4, 1992Date of Patent: February 7, 1995Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)Inventors: Jean-Michel Bernardon, William R. Pilgrim
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Patent number: 5359120Abstract: The invention provides compounds of the formula XX: M-Ar-CONH-R, where Ar represents an aromatic ring system, R-NH is the residue of an .alpha.-amino acid R-NH.sub.2 or oligopeptide R-NH.sub.2 and contains at least one carboxylic acid group in the form of a tertiary butyl ester and M represents a nitrogen mustard group of formula (a), where Y and L, which may be the same or different in a molecule, are leaving groups. The compounds are useful intermediates for the production of nitrogen mustard prodrugs.Type: GrantFiled: May 6, 1991Date of Patent: October 25, 1994Assignee: Cancer Research Campaign Technology LimitedInventor: Caroline J. Springer
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Patent number: 5344959Abstract: Compounds of the formula ##STR1## wherein m is 1-4; R.sub.1 -R.sub.4 independently are hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, or I; R.sub.5 is hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1-6 carbons; R.sub.6 is hydrogen, lower alkyl, Cl, Br, I, OR.sub.11, SR.sub.11, OCOR.sub.11, SCOR.sub.11, NH2, NHR.sub.11, N(R.sub.11).sub.2, NHCOR.sub.11 OR NR.sub.11 --COR.sub.11 ; R.sub.20 is independently hydrogen or lower alkyl; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.7 OR.sub.13 O, where R.sub.Type: GrantFiled: May 18, 1993Date of Patent: September 6, 1994Assignee: Allergan, Inc.Inventor: Roshantha A. Chandraratna
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Patent number: 5310682Abstract: Compounds containing .alpha.-discarbonyl groups are rendered capable of fluorescent emission by conjugation with carboxylic acid-terminated ortho-diaminoaryl reagents. The carboxylic acid groups serve as ionizable moieties which facilitate the conjugation reaction, and are retained in the conjugation product to enable, or enhance the ability of, the conjugated compounds to be separated in chromatographic and electromigration separation processes, notably electrophoresis. Ortho-dinitro derivatives of the reagents are also disclosed, these derivatives offering the advantage of stability as well as the ability to be used directly in the reaction in the presence of a reducing agent.Type: GrantFiled: June 17, 1992Date of Patent: May 10, 1994Assignee: Indiana University FoundationInventors: Milos V. Novotny, Osamu Shirota, Donald Wiesler
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Patent number: 5306813Abstract: A compound which, in the free acid form, is of Formula (1): ##STR1## wherein: D is optionally substituted phenyl or optionally substituted naphthyl;K is optionally substituted phenylene or optionally substituted naphthylene;R.sup.1 and R.sup.4 are each independently H or optionally substituted alkyl;R.sup.2 and R.sup.3 are each independently H or optionally substituted alkyl, provided at least one of R.sup.2 and R.sup.3 is optionally substituted alkyl;B is H, optionally substituted alkyl or optionally substituted each A is H or a substituent; andeachA is H or a substituent; andL is an optionally substituted divalent organic radical. The compound is useful as a reactive dye for textiles.Type: GrantFiled: January 22, 1993Date of Patent: April 26, 1994Assignee: Imperial Chemical Industries PLCInventors: Andrew H. M. Renfrew, John A. Taylor
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Patent number: 5228899Abstract: Plant growth regulators comprising, as an active ingredient, a substituted dicarboxylic acid derivative having the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, D and G are the same as defined in the present specification, the substituted dicarboxylic acid derivatives, and processes for preparing the same, are disclosed. The plant growth regulators provided according to the present invention have a regulating activity on plant growth; more specifically, an action thereof of lowering the content of endogenous ethylene in a plant is utilized.Type: GrantFiled: August 24, 1990Date of Patent: July 20, 1993Assignee: Sumitomo Chemical Company LimitedInventors: Yoshikazu Itoh, Akio Manabe, Masato Mizutani, Naonori Hirata, Sachiko Uwayokote, Kazuo Izumi, Kenji Arai
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Patent number: 5189181Abstract: A process for the preparation of a polycyclic dye of the Formula (1): ##STR1## by reacting a substituted acetic acid of the Formula (2): ##STR2## with a compound of the Formula (3): ##STR3## and oxidation of the intermediate leuco compound to dehydrogenate the peripheral heterocyclic rings whereinY is an optionally substituted aromatic or heteroaromatic radical;Ring A is unsubstituted or is substituted by from one to five groups;Z is --NR.sup.1 R.sup.2 ;R.sup.1 and R.sup.2 are each independently H or are independently selected from optionally substituted alkyl, alkenyl, cycloalkyl, aralkyl, aryl and heteroaryl; orR.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached form a heterocyclic ring; orR.sup.1 and R.sup.2 each independently together with the nitrogen to which they are attached and the adjacent carbon atom of Ring B form a heterocyclic ring; andX.sup.1 and X.sup.Type: GrantFiled: January 7, 1992Date of Patent: February 23, 1993Assignee: Imperial Chemical Industries PLCInventors: Nigel Hall, Nigel Hughes, Prakash Patel
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Patent number: 5157151Abstract: Novel salts of 1-adamantamine are formed by reacting non-steroidal anti-inflammatory carboxylic acids with 1-adamantamine. Formulations of 1-adamantamine hydrochloride and non-steroidal anti-inflammatory carboxylic acids are also described.Type: GrantFiled: December 18, 1990Date of Patent: October 20, 1992Inventor: Isaac Angres
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Patent number: 5155229Abstract: Derivatives of pravastatin are provided which are useful in inhibiting cholesterol biosynthesis and in preparing radiolabeled compounds useful in the radioimmunoassay (RIA) of pravastatin and derivatives thereof. The pravastatin derivatives have the structure ##STR1## wherein R is hydroxy, lower alkylamine, arylamine, arylalkylamine or heterocyclic alkylamine such as histamine, tyramine, O-benzyltyramine, methyl tyrosinate as well as iodinated derivatives thereof.Type: GrantFiled: July 1, 1991Date of Patent: October 13, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: Richard A. DiPietro, Jan-I Tu, Noor Z. Turabi
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Patent number: 5084592Abstract: Azulenesquaric acid dyes of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each have specified meanings are prepared from azulene derivatives of the formula ##STR2## where R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each have specified meanings as intermediates, and used in an optical recording medium.Type: GrantFiled: September 30, 1988Date of Patent: January 28, 1992Assignee: BASF AktiengesellschaftInventors: Wolfgang Schrott, Peter Neumann, Sibylle Brosius, Helmut Barzynski, Klaus D. Schomann, Harald Kuppelmaier
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Patent number: 5041672Abstract: A process for producing p-phenylenediamine or a derivative thereof which comprises reducing p-nitroaniline or a derivative thereof by hydrazine in the presence of an aromatic quinone compound or an aromatic dihydroxy compound.Type: GrantFiled: October 16, 1990Date of Patent: August 20, 1991Assignee: Nippon Kayaku Kabushiki KaishaInventor: Tsukasa Ishikura
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Patent number: 4994606Abstract: 4,5-Difluoroanthranilic acid may be prepared by decarboxylating 4,5-difluorophthalic anhydride or 4,5-difluorophthalic acid by heating in dimethyl acetamide, N-methyl-2-pyrrolidone or quinoline, optionally by reaction with copper, copper oxide, copper salts, or halides and salts of Zn, Cd, Ag and Ni as a catalyst, whereby 3,4-difluorobenzoic acid is formed; nitrating said 3,4-difluorobenzoic acid in a mixture of nitric and sulfuric acids to form 2-nitro-4,5-difluorobenzoic acid, and reducing said 2-nitro-4,5-difluorobenzoic acid to form 4,5-difluoroanthranilic acid.Type: GrantFiled: June 4, 1990Date of Patent: February 19, 1991Assignee: Occidental Chemical CorporationInventors: Lawrence B. Fertel, Henry C. Lin
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Patent number: 4990661Abstract: A process for the preparation of a compound of the formula ##STR1## in which X.sup.1 and X.sup.2 each independently is chlorine or fluorine, andY is chlorine, bromine, fluorine or iodine, comprising subjecting a compound of the formula ##STR2## to a Sandmeyer or Balz-Schiemann reaction thereby to produce a carboxylic acid of the formula ##STR3## and converting the carboxylic acid (Ia) into an acyl chloride of the formula ##STR4## The compound (II) is new. The products are known intermediates for anti-bacterials.Type: GrantFiled: March 29, 1989Date of Patent: February 5, 1991Assignee: Bayer AktiengesellschaftInventors: Uwe Petersen, Michael Schriewer, Ernst Kysela, Klaus Grohe
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Patent number: 4954639Abstract: Disclosed is a method of making ionized fluoroanthranilic acid from a fluorophthalic compound in a single pot process without isolating any intermediate product. A composition is prepared which comprises an aqueous solution of water, a fluorophthalic compound selected from the group consisting of ##STR1## and mixtures thereof, where "n" is 1 to 4, at a concentration of about 5 to about 30 percent by weight based on the water weight, and about 1 to about 1.5 equivalents of hydroxylamine or a mineral acid salt thereof. The pH of the composition is maintained at at least about 11 and the temperature of the composition is maintained at at least about 90.degree. C. The unionized form of the acid is made by cooling below 50.degree. C. and lowering the pH to between about 4 and about 5. Also disclosed are the intermediate compounds, fluoro-N-hydroxyphthalimides, and a method of making them.Type: GrantFiled: August 28, 1989Date of Patent: September 4, 1990Assignee: Occidental Chemical CorporationInventors: Lawrence B. Fertel, Neil J. O'Reilly
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Patent number: 4910282Abstract: There is provided an aromatic polyamide having repeating units of the formula: ##STR1## wherein X is -O-, -S-, -CO- or -SO.sub.2 - and y has a value of 1 or 2. Also provided is an aromatic polyamide having repeating units of the formula: ##STR2## and a new composition of matter 3-[4-(3-aminophenoxy benzoyl)phenoxy] benzoic acid.Type: GrantFiled: August 15, 1988Date of Patent: March 20, 1990Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Tonson Abraham, Robert C. Evers, Edward J. Soloski
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Patent number: 4868347Abstract: Substituted fluorobenzenes which are produced in aprotic, polar solvents or in mixtures which contain such solvents can be obtained by extracting the substituted fluorobenzenes from the solvents or solvent mixtures with aliphatic extracting agents and then seaprating the extracting agents from the substituted fluorobenzenes.Type: GrantFiled: December 9, 1987Date of Patent: September 19, 1989Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Edwin Ritzer
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Patent number: 4857660Abstract: 1-Phenyl-3-azabicyclo[3.1.1]-heptane-2,4-diones of the formula ##STR1## in which R.sub.1 represents hydrogen or a saturated or unsaturated, aliphatic, cycloaliphatic, cycloaliphatic-aliphatic, aromatic or aromatic-aliphatic hydrocarbon radical having up to and including 18, preferably up to and including 12, carbon atoms, R.sub.2 represents hydrogen, lower alkyl, sulpho or acyl, R.sub.3 represents hydrogen or lower alkyl and R.sub.4 represents hydrogen, lower alkyl, phenyl or phenyl substituted by --N(R.sub.2)(R.sub.3), and salts of these compounds, have valuable pharmacological properties, are effective as aromatase inhibitors and can therefore be used for the treatment of hormone-dependent diseases, especially mammary carcinoma.Type: GrantFiled: April 22, 1988Date of Patent: August 15, 1989Assignee: Ciba-Geigy CorporationInventors: Alex Alder, Jaroslav Stanek, Daniel Bellus
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Patent number: 4833270Abstract: This disclosure describes a novel process for preparing 2-chloro-4,5-difluorobenzoic acid which is useful in the preparation of 7-(substituted)piperazinyl-1-substituted-6-fluoro-1,4-dihydro-4-oxo-3-quin oli necarboxylic acid antibacterial agents.Type: GrantFiled: December 21, 1987Date of Patent: May 23, 1989Assignee: American Cyanamid CompanyInventors: Panayota Bitha, Yang-I Lin
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Patent number: 4804765Abstract: The invention concerns a novel process for the synthesis of N-[(1'-allyl-2'-pyrrolidinyl) methyl]-2-methoxy-4,5-azimidobenzamide, which successively comprises the preparation of 2-methoxy-4,5-diaminobenzoic acid, 2-methoxy-4,5-diacetylaminobenzoic acid, N-(2',5'-dihalopentyl)-2-methoxy-4,5-diacetylaminobenzamide, N-[(1'-allyl-2'-pyrrolidinyl) methyl]-2-methoxy-4,5-diacetylaminobenzamide and then N-[(1'-allyl-2'-pyrrolidinyl) methyl]-2-methoxy-4,5-azimido benzamide.Type: GrantFiled: December 18, 1985Date of Patent: February 14, 1989Assignee: Societe D'Etudes Scientifiques et Industrielles de L'Ile-d-FranceInventors: Jacques Acher, Jean-Claude Monier
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Patent number: 4709096Abstract: Stilbene derivatives of the formula (I) ##STR1## and distyryl derivatives of the formula (II), ##STR2## as defined in the specification, and an electrophotographic photoconductor comprising an electroconductive support material and a photosensitive layer overlayed thereon comprising at least one of the above derivatives, are disclosed.Type: GrantFiled: February 22, 1985Date of Patent: November 24, 1987Assignee: Ricoh Company, Ltd.Inventor: Masaomi Sasaki
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Patent number: 4639518Abstract: The synthesis of 5,6-dioxy substituted quinazolinediones is described. The novel quinazolinediones are useful as cardiotonic agents.Type: GrantFiled: September 24, 1984Date of Patent: January 27, 1987Assignee: Ortho Pharmaceutical CorporationInventors: Victor T. Bandurco, Stanley C. Bell, Donald W. Combs, Robert Falotico, Alfonso J. Tobia
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Patent number: 4620032Abstract: There is disclosed a process for reducing the reaction time in the hydrolysis of a condensation polymer wherein molten condensation polymer is intimately admixed with a depolymerizing agent which is either (i) one of the products resulting from the complete hydrolytic depolymerization of the condensation polymer; or (ii) water. The depolymerization agent is present in the mixture in an amount which is less than the weight of the condensation polymer and the materials are intimately admixed for a time sufficient that the molecular of the condensation polymer is reduced by at least 50%. The treated condensation polymer of lower molecular weight is thereafter subjected to neutral hydrolysis. In addition to decreasing the overall time required to effect complete hydrolytic depolymerization, this process additionally permits the use of a smaller hydrolysis vessel, thereby reducing the fabrication cost of the hydrolysis unit.Type: GrantFiled: December 11, 1984Date of Patent: October 28, 1986Assignee: Celanese CorporationInventor: Marvin L. Doerr
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Patent number: 4551549Abstract: 2- and 3-Nitroterephthalamic acids are prepared by ammonolysis of dialkyl nitroterephthalates. The terephthalamic acids are useful as intermediates in the preparation of difunctional compounds useful in the preparation of aromatic polyamides and polybenzimidazoles.Type: GrantFiled: April 18, 1983Date of Patent: November 5, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: George N. Milford, Jr.
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Patent number: RE32944Abstract: Novel aromatic carboxylic amides of the general formula: ##STR1## wherein each of R.sub.1 and R.sub.2 is a hydrogen atom or an alkyl group having 1-4 carbon atoms, R.sub.3 and R.sub.4 are hydrogen atoms or together form another chemical bond, each X is a hydroxyl group, a halogen atom, an alkyl group having 1-4 carbon atoms and an alkoxy group containing 1-4 carbon atoms, and n is an integer of 1-3 with the proviso that when .[.Xs.]. .Iadd.X's .Iaddend.are alkyl or alkoxy groups, they may be connected together to form a ring, as well as pharmaceutically acceptable salts thereof.These compounds possess a strong antiallergenic action and are thus useful for treatment of asthma, hay fever, .[.anticaria.]. .Iadd.urticaria .Iaddend.and atopic dermatitis.The above aromatic carboxylic amides can be prepared by reacting a reactive functional derivative of the general formula: ##STR2## where R.sub.1, R.sub.2, R.sub.3, R.sub.Type: GrantFiled: June 1, 1977Date of Patent: June 6, 1989Assignee: Kissei Yakuhin Kogyo KabushikiInventors: Kozaburo Harita, Yukiyoshi Ajisawa, Kinji Iizuka, Yukihiko Kinoshita, Tetsuhide Kamijo, Michihiro Kobayashi