Carboxyl, Or Salt Thereof, Bonded Directly To A Ring Patents (Class 562/458)
  • Patent number: 6710205
    Abstract: 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: Grant
    Filed: August 16, 2002
    Date of Patent: March 23, 2004
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Kousuke Tani, Kaoru Kobayashi, Takayuki Maruyama
  • Patent number: 6699909
    Abstract: 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: Grant
    Filed: May 7, 2002
    Date of Patent: March 2, 2004
    Assignee: Prescient NeuroPharma Inc.
    Inventor: Kenneth Curry
  • Patent number: 6603041
    Abstract: 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: Grant
    Filed: September 5, 2001
    Date of Patent: August 5, 2003
    Assignee: Celltech R & D Limited
    Inventors: Timothy John Norman, John Robert Porter, John Clifford Head, Andrew James Ratcliffe
  • Patent number: 6504052
    Abstract: 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 system
    Type: Grant
    Filed: November 16, 2001
    Date of Patent: January 7, 2003
    Assignee: Eli Lilly and Company
    Inventors: Ivan Collado Cano, Concepcion Pedregal Tercero, Alicia Marcos Llorente
  • Patent number: 6172239
    Abstract: The invention relates to compounds of the formula The compounds have agreat affinity for the neurotensin receptors.
    Type: Grant
    Filed: August 16, 1999
    Date of Patent: January 9, 2001
    Assignee: Sanofi
    Inventors: Bernard Labeeuw, Danielle Gully, Francis JeanJean, Jean-Charles Molimard, Robert Boigegrain
  • Patent number: 6172058
    Abstract: 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: Grant
    Filed: April 3, 1998
    Date of Patent: January 9, 2001
    Assignee: Lilly, SA
    Inventors: Concepci{acute over (o)}n Pedregal Tercero, Ivan Collado Cano, Angel Maz{acute over (o)}n Ruiz
  • Patent number: 6150412
    Abstract: 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: Grant
    Filed: November 21, 1997
    Date of Patent: November 21, 2000
    Assignee: Orion-yhtyma Oy
    Inventors: Jarmo Pystynen, Anne Luiro, Timo Lotta, Martti Ovaska, Jukka Vidgren
  • Patent number: 6127392
    Abstract: 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: Grant
    Filed: August 3, 1998
    Date of Patent: October 3, 2000
    Assignee: American Home Products Corporation
    Inventors: Joseph Richard Lennox, Schuyler Adam Antane, John Anthony Butera
  • Patent number: 6114386
    Abstract: 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: Grant
    Filed: October 14, 1997
    Date of Patent: September 5, 2000
    Assignee: University of Alabama
    Inventors: Ming Luo, Clinton L. White
  • Patent number: 5965592
    Abstract: 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: Grant
    Filed: July 29, 1998
    Date of Patent: October 12, 1999
    Assignee: Novartis Corporation
    Inventors: Peter Buhlmayer, Franz Ostermayer, Tibur Schmidlin
  • Patent number: 5935585
    Abstract: 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: Grant
    Filed: February 23, 1996
    Date of Patent: August 10, 1999
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventors: Jean-Michel Bernardon, Laurence Vigne
  • Patent number: 5936119
    Abstract: 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: Grant
    Filed: January 27, 1998
    Date of Patent: August 10, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: John Barry Henshall, John Whitworth
  • Patent number: 5872282
    Abstract: 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: Grant
    Filed: March 13, 1998
    Date of Patent: February 16, 1999
    Assignee: Virginia Commonwealth University
    Inventors: Donald J. Abraham, Gajanan Joshi, Ramnarayan Randad
  • Patent number: 5744638
    Abstract: 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: Grant
    Filed: January 13, 1995
    Date of Patent: April 28, 1998
    Assignee: Riedel-de Haen Aktiengesellschaft
    Inventors: Horst Schmand, Bernd Kellermeier, Gunter Bartels, Hans-Jurgen Schmidt
  • Patent number: 5741926
    Abstract: 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: Grant
    Filed: February 12, 1997
    Date of Patent: April 21, 1998
    Assignee: Shaman Pharmaceuticals, Inc.
    Inventors: Donald E. Bierer, Larisa G. Dubenko
  • Patent number: 5717109
    Abstract: 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: Grant
    Filed: July 10, 1995
    Date of Patent: February 10, 1998
    Assignee: Eli Lilly and Company
    Inventors: M. Brian Arnold, Thomas J. Bleisch, David R. Helton, Mary Jeanne Kallman, Paul L. Ornstein, Darryle D. Schoepp, Joseph P. Tizzano
  • Patent number: 5705528
    Abstract: 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: Grant
    Filed: November 10, 1994
    Date of Patent: January 6, 1998
    Assignee: Ramot University Authority for Applied Research & Industrial Development
    Inventor: Yoel Kloog
  • Patent number: 5599814
    Abstract: 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: Grant
    Filed: April 24, 1995
    Date of Patent: February 4, 1997
    Assignee: Imperial Chemical Industries, PLC
    Inventors: Thomas M. Bare, Richard B. Sparks
  • Patent number: 5543550
    Abstract: 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: Grant
    Filed: October 6, 1994
    Date of Patent: August 6, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jochen Rapp, Siegfried Planker, Theodor Papenfuhs, G unter Bartels
  • Patent number: 5536878
    Abstract: 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: Grant
    Filed: December 2, 1994
    Date of Patent: July 16, 1996
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Teruyuki Nagata, Chiyuki Kusuda, Masaru Wada, Kenichi Satou, Masae Uchida
  • Patent number: 5523472
    Abstract: 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: Grant
    Filed: October 6, 1994
    Date of Patent: June 4, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Freimund Rohrscheid, Jochen Rapp, Theodor Papenfuhs
  • Patent number: 5482942
    Abstract: 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: Grant
    Filed: June 28, 1994
    Date of Patent: January 9, 1996
    Assignee: American Home Products Corporation
    Inventors: Richard M. Soll, Paul J. Dollings
  • Patent number: 5436368
    Abstract: 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: Grant
    Filed: November 14, 1994
    Date of Patent: July 25, 1995
    Assignee: Pfizer Inc.
    Inventor: Tamim F. Braish
  • Patent number: 5410082
    Abstract: 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: Grant
    Filed: May 9, 1994
    Date of Patent: April 25, 1995
    Inventor: Ralf Pfirmann
  • Patent number: 5403853
    Abstract: 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: Grant
    Filed: June 13, 1994
    Date of Patent: April 4, 1995
    Assignee: American Home Products Corporation
    Inventors: John A. Butera, Schuyler A. Antane
  • Patent number: 5393902
    Abstract: 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: Grant
    Filed: April 26, 1994
    Date of Patent: February 28, 1995
    Assignee: Lever Brothers Company, Division of Conopco, Inc.
    Inventors: Janet L. Coope, AnneMarie Brescia, Michael I. Hill, Martina Santoso, Stephen A. Madison
  • Patent number: 5387594
    Abstract: 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: Grant
    Filed: August 4, 1992
    Date of Patent: February 7, 1995
    Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)
    Inventors: Jean-Michel Bernardon, William R. Pilgrim
  • Patent number: 5359120
    Abstract: 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: Grant
    Filed: May 6, 1991
    Date of Patent: October 25, 1994
    Assignee: Cancer Research Campaign Technology Limited
    Inventor: Caroline J. Springer
  • Patent number: 5344959
    Abstract: 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: Grant
    Filed: May 18, 1993
    Date of Patent: September 6, 1994
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. Chandraratna
  • Patent number: 5310682
    Abstract: 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: Grant
    Filed: June 17, 1992
    Date of Patent: May 10, 1994
    Assignee: Indiana University Foundation
    Inventors: Milos V. Novotny, Osamu Shirota, Donald Wiesler
  • Patent number: 5306813
    Abstract: 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: Grant
    Filed: January 22, 1993
    Date of Patent: April 26, 1994
    Assignee: Imperial Chemical Industries PLC
    Inventors: Andrew H. M. Renfrew, John A. Taylor
  • Patent number: 5228899
    Abstract: 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: Grant
    Filed: August 24, 1990
    Date of Patent: July 20, 1993
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Yoshikazu Itoh, Akio Manabe, Masato Mizutani, Naonori Hirata, Sachiko Uwayokote, Kazuo Izumi, Kenji Arai
  • Patent number: 5189181
    Abstract: 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: Grant
    Filed: January 7, 1992
    Date of Patent: February 23, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Nigel Hall, Nigel Hughes, Prakash Patel
  • Patent number: 5157151
    Abstract: 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: Grant
    Filed: December 18, 1990
    Date of Patent: October 20, 1992
    Inventor: Isaac Angres
  • Patent number: 5155229
    Abstract: 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: Grant
    Filed: July 1, 1991
    Date of Patent: October 13, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Richard A. DiPietro, Jan-I Tu, Noor Z. Turabi
  • Patent number: 5084592
    Abstract: 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: Grant
    Filed: September 30, 1988
    Date of Patent: January 28, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Schrott, Peter Neumann, Sibylle Brosius, Helmut Barzynski, Klaus D. Schomann, Harald Kuppelmaier
  • Patent number: 5041672
    Abstract: 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: Grant
    Filed: October 16, 1990
    Date of Patent: August 20, 1991
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventor: Tsukasa Ishikura
  • Patent number: 4994606
    Abstract: 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: Grant
    Filed: June 4, 1990
    Date of Patent: February 19, 1991
    Assignee: Occidental Chemical Corporation
    Inventors: Lawrence B. Fertel, Henry C. Lin
  • Patent number: 4990661
    Abstract: 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: Grant
    Filed: March 29, 1989
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Michael Schriewer, Ernst Kysela, Klaus Grohe
  • Patent number: 4954639
    Abstract: 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: Grant
    Filed: August 28, 1989
    Date of Patent: September 4, 1990
    Assignee: Occidental Chemical Corporation
    Inventors: Lawrence B. Fertel, Neil J. O'Reilly
  • Patent number: 4910282
    Abstract: 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: Grant
    Filed: August 15, 1988
    Date of Patent: March 20, 1990
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Tonson Abraham, Robert C. Evers, Edward J. Soloski
  • Patent number: 4868347
    Abstract: 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: Grant
    Filed: December 9, 1987
    Date of Patent: September 19, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz U. Blank, Edwin Ritzer
  • Patent number: 4857660
    Abstract: 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: Grant
    Filed: April 22, 1988
    Date of Patent: August 15, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Alex Alder, Jaroslav Stanek, Daniel Bellus
  • Patent number: 4833270
    Abstract: 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: Grant
    Filed: December 21, 1987
    Date of Patent: May 23, 1989
    Assignee: American Cyanamid Company
    Inventors: Panayota Bitha, Yang-I Lin
  • Patent number: 4804765
    Abstract: 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: Grant
    Filed: December 18, 1985
    Date of Patent: February 14, 1989
    Assignee: Societe D'Etudes Scientifiques et Industrielles de L'Ile-d-France
    Inventors: Jacques Acher, Jean-Claude Monier
  • Patent number: 4709096
    Abstract: 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: Grant
    Filed: February 22, 1985
    Date of Patent: November 24, 1987
    Assignee: Ricoh Company, Ltd.
    Inventor: Masaomi Sasaki
  • Patent number: 4639518
    Abstract: The synthesis of 5,6-dioxy substituted quinazolinediones is described. The novel quinazolinediones are useful as cardiotonic agents.
    Type: Grant
    Filed: September 24, 1984
    Date of Patent: January 27, 1987
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: Victor T. Bandurco, Stanley C. Bell, Donald W. Combs, Robert Falotico, Alfonso J. Tobia
  • Patent number: 4620032
    Abstract: 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: Grant
    Filed: December 11, 1984
    Date of Patent: October 28, 1986
    Assignee: Celanese Corporation
    Inventor: Marvin L. Doerr
  • Patent number: 4551549
    Abstract: 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: Grant
    Filed: April 18, 1983
    Date of Patent: November 5, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: George N. Milford, Jr.
  • Patent number: RE32944
    Abstract: 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: Grant
    Filed: June 1, 1977
    Date of Patent: June 6, 1989
    Assignee: Kissei Yakuhin Kogyo Kabushiki
    Inventors: Kozaburo Harita, Yukiyoshi Ajisawa, Kinji Iizuka, Yukihiko Kinoshita, Tetsuhide Kamijo, Michihiro Kobayashi