Plural Chalcogens Bonded Directly To Ring Carbons Of The Six-membered Hetero Ring Patents (Class 546/296)
  • Patent number: 5935977
    Abstract: The present invention relates to a substituted vinylpyridine derivative represented by the following formula (1): ##STR1## (wherein R.sup.1 represents a hydrogen atom, an alkyl group, etc., R.sup.2 represents an alkyl group; one of R.sup.3 and R.sup.4, which are different from each other, represents a hydrogen atom and the other represents a nitrile group, R.sup.5 represents an aryl group or a heteroaryl group, X represents an oxygen atom, etc., and one of Q.sup.1, Q.sup.2, and Q.sup.3 represents a nitrogen atom and the other two represent CH); a salt of the derivative; and a drug containing the derivative or salt as the active ingredient. Due to strong PDE inhibitory action and TNF-.alpha. production inhibitory action, the derivative, salt, and drug are useful for the prevention and treatment of a wide variety of inflammatory diseases and autoimmune diseases.
    Type: Grant
    Filed: May 26, 1998
    Date of Patent: August 10, 1999
    Assignee: SS Pharmaceutical Co., Ltd.
    Inventors: Kazuo Yamazaki, Yoichiro Ogawa, Hidehiko Kohya, Tadashi Mikami, Noriyuki Kawamoto, Noriaki Shioiri, Hiroshi Hasegawa, Susumu Sato
  • Patent number: 5922880
    Abstract: The dihalopropene compounds of the general formula ?I! have excellent insecticidal/acaricidal activity, so that they are satisfactorily effective for the control of noxious insects, mites and ticks.
    Type: Grant
    Filed: May 20, 1997
    Date of Patent: July 13, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noriyasu Sakamoto, Sanshiro Matsuo, Masaya Suzuki, Taro Hirose, Kazunori Tsushima, Kimitoshi Umeda
  • Patent number: 5919792
    Abstract: This invention relates to certain novel compounds and derivatives thereof, their synthesis, and their use as vitronectin receptor antagonists. The vitronectin receptor antagonist compounds of the present invention are .alpha.v.beta.3 antagonists, .alpha.v.beta.5 antagonists or dual .alpha.v.beta.3/.alpha.v.beta.5 antagonists useful for inhibiting bone resorption, treating and preventing osteoporosis, and inhibiting restenosis, diabetic retinopathy, macular degeneration, angiogenesis, atherosclerosis, inflammation and tumor growth.
    Type: Grant
    Filed: October 28, 1997
    Date of Patent: July 6, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Mark E. Duggan, George D. Hartman, William F. Hoffman, Nathan C. Ihle
  • Patent number: 5891895
    Abstract: Hydroxypyridine derivatives of the formula ##STR1## wherein R.sup.1 is a branched C.sub.3-8 alkyl group or a C.sub.3-8 cycloalkyl group, each of which may be substituted;R.sup.2 is a halogen atom, a C.sub.1-4 alkyl group or a C.sub.1-4 alkoxy group;X is an oxygen atom or NR.sup.3 in which R.sup.3 is a hydrogen atom or a C.sub.1-4 alkyl group;R.sup.4, R.sup.5 and R.sup.6 are independently (1) a hydrogen atom, (2) a halogen atom, (3) a cyano group, (4) a nitro group, (5) a C.sub.1-4 acyl group, (6) a C.sub.1-4 alkoxy group which may be substituted with halogen, (7) a C.sub.1-4 alkyl group which may be substituted with halogen or (8) a mercapto group which may be substituted with a C.sub.1-4 alkyl group;m is 0 to 3; andn is 0 or 1;provided that all of R.sup.4, R.sup.5 and R.sup.6 are not hydrogen atom, or a salt thereof, which have potassium channel opening activity and are useful as therapeutic agents of cardiovascular diseases such as angina pectoris, hypertension, etc.
    Type: Grant
    Filed: April 14, 1997
    Date of Patent: April 6, 1999
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Mitsuru Shiraishi, Tsuyoshi Maekawa, Toshifumi Watanabe
  • Patent number: 5892029
    Abstract: Disclosed is a series of improved chelating agents and the chelates formed from these agents, which are highly effective upon both injection and oral administration. Several of the most effective are of low toxicity. These chelating agents incorporate within their structure 3-hydroxy-2-pyridinone (3,2-HOPO) moieties with a substituted carbamoyl group ortho to the hydroxy group of the hydroxypyridinone ring. The electron-withdrawing carbamoyl group increases the acidity, as well as the chemical stability towards oxidation and reduction, of the hydroxypyridinones. In the metal complexes of the chelating agents, the amide protons form very strong hydrogen bonds with the adjacent HOPO oxygen donor, making these complexes very stable at physiological conditions. The terminal N-substituents provide a certain degree of lipophilicity to the 3,2-HOPO, increasing oral activity.
    Type: Grant
    Filed: April 22, 1997
    Date of Patent: April 6, 1999
    Assignee: The Regents of the University of California
    Inventors: Kenneth Raymond, Jide Xu
  • Patent number: 5877322
    Abstract: The invention relates to compounds of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are H, halogen, an aliphatic radical or an aromatic radical, X is O, S or optionally substituted imino, Y is a bond or a bivalent optionally substituted hydrocarbon radical and Z is optionally substituted cycloalkyl or cycloalkenyl. The invention furthermore relates to processes for their preparation and their use as pesticides, in particular as insecticides, acaricides and fungicides.
    Type: Grant
    Filed: September 12, 1994
    Date of Patent: March 2, 1999
    Assignee: Hoechst Schering AgrEvo GmbH
    Inventors: Dieter Bernd Reuschling, Adolf Heinz Linkies, Volkmar Wehner, Rainer Preuss, Wolfgang Schaper, Harald Jakobi, Peter Braun, Werner Knauf, Burkhard Sachse, Anna Waltersdorfer, Manfred Kern, Peter Lummen, Werner Bonin
  • Patent number: 5874472
    Abstract: Compounds of formula (I) and salts, esters and amides thereof, wherein R.sup.1 is a C.sub.1-6 straight or branched chain alkyl group, a C.sub.3-6 cycloalkyl group, a thiol group optionally substituted by a C.sub.1-6 alkyl group, or an amino group optionally substituted by one or two alkyl or alkenyl groups; R.sup.2 is H, C.sub.1-7 straight or branched chain alkyl, C.sub.3-6 cycloalkyl, C.sub.2-7 alkenyl or benzyl; A is a 5 or 6 membered aromatic carbocyclic or heterocyclic ring which may optionally be substituted by one or more suitable substituents such as C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxy, halo, nitro, cyano, trifluoro C.sub.1-6 alkyl, amino, C.sub.1-6 alkylamino or di C.sub.1-6 alkylamino; r is 0, 1 or 2; their use in medicine and in particular for conditions requiring inhibition of the NO Synthase enzyme, pharmaceutical formulations and processes for the preparation thereof are disclosed.
    Type: Grant
    Filed: March 18, 1996
    Date of Patent: February 23, 1999
    Assignee: Glaxo Wellcome Inc.
    Inventors: Barry George Shearer, Karl Witold Franzmann, Harold Francis Hodson
  • Patent number: 5852042
    Abstract: The invention relates to novel substituted N-(4-pyridyl)carboxamides of the formula ##STR1## in which Q is substituted 4-pyridyl, A is hydrogen, alkyl, acyl or aralkyl and Y-Z is an optionally modified hydrocarbon radical or Y is a bond or a bivalent radical and Z is aryl, O-aryl, cycloalkyl, cycloalkenyl or heterocyclyl, all of which are optionally substituted, to processes for their preparation, to intermediates during their preparation, and to their use as pesticides, in particular as insecticides, acaricides and nematicides, and also as fungicides.
    Type: Grant
    Filed: September 26, 1995
    Date of Patent: December 22, 1998
    Assignee: Hoechst Schering AgrEvo GmbH
    Inventors: Harald Jakobi, Werner Knauf, Ulrich Sanft, Manfred Kern, Dieter Bernd Reuschling, Adolf Heinz Linkies, Werner Bonin
  • Patent number: 5837703
    Abstract: Therapeutic compounds have the formula:(X)j-(core moiety),j being an integer from one to three, the core moiety comprising a core moiety, the core moiety being a heterocycle having one ring or two-fused rings, each ring having five or six ring atoms, A being a carbon atom of the core moiety and attached to a terminal carbon atom of (CH.sub.2).sub.m, and X has a structure and X being a racemic mixture, R or S enantiomer, solvate, hydrate, or salt of: ##STR1## *C is a chiral carbon atom, n is an integer from one to four (preferably from one to three), one or more carbon atoms of (CH.sub.2).sub.n may be substituted by a keto or hydroxy group, and m is an integer from one to fourteen. Independently, R.sub.1 and R.sub.2 may be a hydrogen, a straight or branched chain alkyl or alkenyl of up to twelve carbon atoms in length, or --(CH.sub.2).sub.w R.sub.5, w being an integer from two to fourteen and R.sub.5 being a mono-, di- or tri-substituted or unsubstituted aryl group, substituents on R.sub.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: November 17, 1998
    Assignee: Cell Therapeutics, Inc.
    Inventors: Anil M. Kumar, John Michnick, Gail E. Underiner, J. Peter Klein, Glenn C. Rice
  • Patent number: 5811370
    Abstract: Azamethine dyes of the formula ##STR1## where W is oxygen, sulfur or a radical of the formula --NH--CO--, --NH--COO-- oder --NH--SO.sub.2 --,Z.sup.1 is C.sub.1 -C.sub.4 -alkyl with or without substitution, phenyl or C.sub.1 -C.sub.4 -alkoxy,Z.sup.2 and Z.sup.3 are each hydrogen or C.sub.1 -C.sub.4 -alkyl with or without substitution, provided --CZ.sup.1 Z.sup.2 Z.sup.3 is not linear and is not isopropyl,Z.sup.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,Z.sup.5 and Z.sup.6 are each C.sub.1 -C.sub.10 -alkyl with or without substitution, C.sub.3 -C.sub.4 -alkenyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl or tolyl, or together with the nitrogen atom joining them together a heterocyclic radical or Z.sup.4 and Z.sup.5 are together a bridge member, andT is a radical of a cyclic acidic--CH compound H.sub.2 T,are useful for thermal transfer.
    Type: Grant
    Filed: May 8, 1997
    Date of Patent: September 22, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Rudiger Sens, Andreas Johann Schmidt, Stefan Beckmann, Karl-Heinz Etzbach
  • Patent number: 5789426
    Abstract: The present invention relates to a method of treating a patient with a fibrotic or fibroproliferative disorder and a method of suppressing formation of collagen and collagen-like substances or biosynthesis of procollagen in living systems by administering to a patient or living system, respectively, an effective amount of a compound of Formulae (I) or (II) and derivatives thereof: ##STR1## R.sub.1, R.sub.2, R.sub.3, and R.sub.4 each individually represent a hydrogen, an alkyl, alkenyl, or alkoxy group containing 1 to about 8 carbon atoms, an aryl, aralkyl, or cycloalkyl group containing about 5 to 12 carbon atoms, or a carboalkoxy or carbamyl group containing up to 8 carbon atoms, or a peptide or peptidomimetic moiety containing 10 to about 30 carbon atoms.
    Type: Grant
    Filed: January 20, 1995
    Date of Patent: August 4, 1998
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Hartmut M. Hanauske-Abel, Timothy A. McCaffrey, Robert Walter Grady
  • Patent number: 5770614
    Abstract: A novel 2-(substituted phenyl)-2-alkoxyiino-N-alkylacetamide compounds having a wide fungicidal spectrum and especially an excellent activity of controlling Pseudocercosporella herpotrichoides; and a composition containing the compound for controlling Pseudocercosporella herpotrichoides.
    Type: Grant
    Filed: November 12, 1996
    Date of Patent: June 23, 1998
    Assignee: Shionogi & Co., Ltd.
    Inventors: Akira Murabayashi, Akira Takase, Hideyuki Takenaka, Michio Masuko
  • Patent number: 5766610
    Abstract: Novel pharmaceutically/cosmetically-active polycyclic aromatic compounds have the structural formula (I): ##STR1## wherein Ar is a radical having one of the 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: April 26, 1995
    Date of Patent: June 16, 1998
    Assignee: Centre International De Recherches Dermatologiques Galderma
    Inventor: Jean-Michel Bernardon
  • Patent number: 5760063
    Abstract: The subject invention, provides arylhydrazone compounds having the Formula 1: ##STR1## wherein A and B are independently aryl or heteroaryl and A and B independently are substituted with at least one group selected from alkyl, halogen, CN, COOR.sup.7, NR.sup.7 R.sup.8, CONR.sup.7 R.sup.8, NO.sub.2, SR.sup.7, SOR.sup.7, SO.sub.2 R.sup.7, NHCOR.sup.7, NHSO.sub.2 R.sup.7, OR.sup.7, hydroxyalkyl, and aminoalkyl. The compounds of this invention are useful for treating a wide variety of bacterial infections, including diseases of the skin, e.g., acne and skin ulcers, gastroenteritis, colitis, meningitis, keratinitis, conjunctivitis, diseases of the urinary and genital tracts, etc.
    Type: Grant
    Filed: September 13, 1996
    Date of Patent: June 2, 1998
    Assignee: Scriptgen Pharmaceuticals, Inc.
    Inventors: Kelvin T. Lam, David G. Powers
  • Patent number: 5750532
    Abstract: The disclosed invention is compounds represented by the formula ##STR1## and pharmacetically acceptable acid salts thereof, wherein each Z is independently tetiary butyl, phenyl, naphthyl or adamantyl; substituted phenyl, wherein the substituents are one or more of halogen, lower alkoxy, phenoxy, nitrile, nitro, phenylsulfonyl, loweralkyl-sulfonyl, oxazol-2-yl, lower alkanoyl, benzoyl, lower alkoxycarbonyl, lower alkyl, lower alkylthio, phenyl, phenylaminothiocarbonyl, or lower alkylaminothiocarbonyl, hydroxyiminoloweralkyl hydroxyloweralkyl or carbonyl; or 4 or 6 membered unsubstituted or substituted heterocyclic ring containing at least one nitrogen with the remaining member of the ring being at least one carbon, and optionally sulfur or oxygen,X and Y are each independently a bond, ##STR2## each Q is independently a divalent substituted or unsubstituted, straight or branched chain lower alkanediyl, lower alkanediyl-cycloalkanediyl-lower alkanediyl, lower alkenediyl, lower alkynediyl, phenylene, dihydrofura
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: May 12, 1998
    Assignee: Schering Corporation
    Inventors: Viyyoor M. Girijavallabhan, Ashit K. Ganguly, Patrick A. Pinto, Richard W. Versace
  • Patent number: 5726315
    Abstract: The compounds of the invention are tri-substituted pyridine intermediates, useful in the preparation of final products, wherein said final products are involved in the preparation of medicaments. Said medicaments are useful for the treatment of various diseases including psoriasis. A compound of the formula (II): ##STR1## wherein R.sup.1 is hydrogen, benzyl or a group of the formula (A): ##STR2## in which n is 1 to 20; and R.sup.5 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or trifluoromethyl; and R.sup.7 is a leaving group consisting of halogen, OTf or (Trifluorate, e.g. OSO.sub.2 CF.sub.3), OSO.sub.2 alkyl and OSO.sub.2 Ar wherein Ar represents optionally substituted aryl.
    Type: Grant
    Filed: May 23, 1996
    Date of Patent: March 10, 1998
    Assignee: SmithKline Beecham plc
    Inventors: Peter William Sheldrake, Laurence Charles Powling, Peter William Bickle
  • Patent number: 5723450
    Abstract: The invention relates to compounds of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are H, halogen, an aliphatic radical or an aromatic radical, X is O, S or optionally substituted imino, Y is a bond or an optionally substituted bivalent hydrocarbon radical and Z is optionally substituted cycloalkyl or cycloalkenyl. The invention furthermore relates to processes for their preparation and their use as pesticides, in particular as insecticides, acaricides and fungicides.
    Type: Grant
    Filed: September 12, 1994
    Date of Patent: March 3, 1998
    Assignee: Hoechst Schering AgrEvo GmbH
    Inventors: Dieter Bernd Reuschling, Adolf Heinz Linkies, Volkmar Wehner, Rainer Preuss, Wolfgang Schaper, Harald Jakobi, Peter Braun, Werner Knauf, Burkhard Sachse, Anna Waltersdorfer, Manfred Kern, Peter Lummen, Werner Bonin
  • Patent number: 5712393
    Abstract: The present invention provides a compound of formula (1) ##STR1## in which: R.sub.4 represents a hydrogen atom, a halogen atom or a nitro group;R.sub.6 represents a hydrogen atom or a straight or branched (C.sub.1 -C.sub.6) alkyl group;R.sub.7 represents a chlorine atom or a hydroxyl group; andZ represents: a phenyl group optionally substituted with one or more halogen atoms, straight or branched (C.sub.1 -C.sub.4)alkyl groups, straight or branched (C.sub.1 -C.sub.4)alkoxy groups, or trifluoromethyl, formyl, --CH.sub.2 OR, --CH.sub.2 OCOR, --CH.sub.2 CONRR', --CH.sub.2 ONCOR, --COOR, nitro, --NHR, --NRR' or --NHCOR groups, wherein R and R' are each, independently, a hydrogen atom or a (C.sub.1 -C.sub.7) alkyl group; a heterocyclic group optionally substituted as defined above for phenyl; or a cyclo(C.sub.5 -C.sub.8)alkyl group; additionally, when R.sub.
    Type: Grant
    Filed: November 24, 1995
    Date of Patent: January 27, 1998
    Assignee: Synthelabo
    Inventors: Jean Michel Altenburger, Gilbert Lassalle
  • Patent number: 5705513
    Abstract: A compound, composition, and method for controlling Take-all disease of plants by applying to the seed prior to planting, a fungicide of the formula: ##STR1## wherein Z.sub.1 and Z.sub.2 are C and are part of an aromatic ring which is pyridine; R and n are defined herein; A is selected from the group consisting of --C(O)--SR.sub.3, --NH--C(X)R.sub.4, --C(.dbd.NR.sub.3)--XR.sub.7, and --C(X)-amine wherein the amine is substituted with with an alkylaminocarbonyl and a hydrogen or wherein the amine has a first and a second amine substituent defined herein; B is --W.sub.m --Q(R.sub.2).sub.3 or selected from 0-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R.sub.4 ; Q is C, Si, Ge, or Sn; W is --C(R.sub.3).sub.p H.sub.(2-p) --; or when Q is C, W may also be selected from --N(R.sub.3).sub.m H(.sub.1-m)--, --S(O)p--, and --O--; X is O or S; n is 0, 1, 2, or 3; m is 0 or 1; p is 0, 1, or 2; each R.sub.
    Type: Grant
    Filed: December 28, 1994
    Date of Patent: January 6, 1998
    Assignee: Monsanto Company
    Inventors: Dennis Paul Phillion, Diane Susan Braccolino, Matthew James Graneto, Wendell Gary Phillips, Karey Alan Van Sant, Daniel Mark Walker, Sai Chi Wong
  • Patent number: 5700943
    Abstract: This invention relates to a process of making a compound of formula I ##STR1## where R.sub.1 contains an .alpha.,.beta.-unsaturated carbonyl group & R.sub.n is hydrogen or nonhydrogen radicals which do not have a functional group which interferes with the coupling reaction, which process comprises coupling a thiolphenol or phenylalkylmercaptan with a chloromethylpyridine in the presence of DBU under an inert atmosphere. These compounds are leukotriene antagonists and as such can be used in treating various diseases associated with leukotrienes.
    Type: Grant
    Filed: December 20, 1994
    Date of Patent: December 23, 1997
    Assignee: SmithKline Beecham Corporation
    Inventor: Robert A. Daines
  • Patent number: 5698550
    Abstract: Compounds of the formula ##STR1## wherein R is an optionally substituted heteroaryl group such as 2-chromanyl, 2-pyridyl or 5-fluoro-2-benzothiazoyl;X is O, S or (CH.sub.2).sub.m ;R.sup.1 is phenyl or pyridyl, optionally substituted by one or more (C.sub.1 -C.sub.3)alkyl, (C.sub.1 -C.sub.3)alkoxy, carboxy or ?(C.sub.1 -C.sub.3)alkoxy!carbonyl groups;n is 0, 1 or 2;m is 1 or 2;Y and Y.sup.1 are taken together and are oxygen, or Y and Y.sup.1 are taken separately, Y is hydrogen and Y.sup.1 is hydroxy or an in vivo hydrolyzable acyloxy group;Z is CH.sub.2, NR.sup.2, O or S; andR.sup.2 is hydrogen or (C.sub.1 -C.sub.3)alkyl;are useful in the treatment of asthma, arthritis and related diseases mediated by leukotrienes.
    Type: Grant
    Filed: June 14, 1993
    Date of Patent: December 16, 1997
    Assignee: Pfizer Inc.
    Inventors: James F. Eggler, Anthony Marfat, Lawrence S. Melvin, Jr.
  • Patent number: 5696140
    Abstract: The present invention relates to hitherto unknown compounds of formula or their tautomeric forms, the attachment to the pyridine ring being in the 3- or 4-position, in which R', R" are the same or different and stand for hydrogen, halogen, or trifluoromethyl, hydroxy, C.sub.1 -C.sub.4 alkyl or alkoxy, nitro, or cyano groups. Alkylene stands for a straight or branched C.sub.1 -C.sub.8 carbon chain, which may be substituted by hydroxy or halogen, nitro or cyano groups. X stands for oxygen, for --S(O).sub.n -- where n stands for an integer from 0 to 2, or for ##STR1## where R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl. R stands for hydrogen or for one or more C.sub.1 -C.sub.4 alkyl or alkoxy, hydroxy, halogen, trifluoromethyl, cyano, carboxamido, sulfamoyl or nitro radicals. The present compounds are of value in the human and veterinary practice for treating asthma, allergy, CNS disorders, or cancer.
    Type: Grant
    Filed: October 3, 1996
    Date of Patent: December 9, 1997
    Assignee: Leo Pharmaceutical Products Ltd.
    Inventors: Erik Bramm, Hans J.o slashed.rgen Petersen
  • Patent number: 5691277
    Abstract: A 2-(unsubstituted or substituted) (benzyloxy or phenoxy)-4-substituted-6-(meta-substituted phenoxy)pyridine represented by the formula (I): ##STR1## wherein R represents C.sub.1 -C.sub.4 alkoxy or cyano; each X, which may be identical or different if n is greater than 1, represents a halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkythio, C.sub.3 -C.sub.5 alkenyloxy, or C.sub.3 -C.sub.5 alkynyloxy;Y represents trifluoromethyl, difluoromethoxy, trifluoromethoxy, or trifluoromethylthio;m represents an integer of 0 or 1; andn represents an integer of 0 to 5, which is useful as a herbicide.
    Type: Grant
    Filed: July 13, 1995
    Date of Patent: November 25, 1997
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hisashi Kanno, Youichi Kanda, Susumu Shimizu, Yoshikazu Kubota, Tsutomu Sato, Masato Arahira
  • Patent number: 5688815
    Abstract: Described are 3-hydroxypyridin-4-ones of formula I ##STR1## wherein R.sub.1 -R.sub.4, A and B are as defined in the description. The compounds have valuable pharmaceutical properties and are especially effective as chelators of iron. They can be used to treat excess iron in the bodies of warm-blooded animals.
    Type: Grant
    Filed: September 27, 1996
    Date of Patent: November 18, 1997
    Assignee: Ciba Geigy Corporation
    Inventor: Paul Zbinden
  • Patent number: 5686460
    Abstract: The present invention relates to the carbocyclic diarylmethylene derivatives of formula (I): ##STR1## and to their use in therapeutics, especially as drugs with anti-inflammatory and analgesic properties.
    Type: Grant
    Filed: October 7, 1996
    Date of Patent: November 11, 1997
    Assignee: Laboratoires UPSA
    Inventors: Eric Nicolai, Michele Launay, Dominique Potin, Jean-Marie Teulon
  • Patent number: 5675013
    Abstract: The present invention relates to novel 1-hydroxy-6-substituted pyridine-2-one and 1-hydroxy-6-substituted pyridine-2-thione compounds. Also disclosed is a process for producing the compound(s) and an antimicrobial composition comprising the compound(s) and at least one component selected from the group consisting of soaps, adhesives, coatings, elastomers, sealants, shampoos, skin care medicaments, cosmetics, paints and other polymer compositions.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: October 7, 1997
    Assignee: Olin Corporation
    Inventors: Rahim Hani, Phillip T. Berkowitz
  • Patent number: 5668156
    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: April 28, 1995
    Date of Patent: September 16, 1997
    Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)
    Inventors: Jean-Michel Bernardon, William Robert Pilgrim
  • Patent number: 5663355
    Abstract: Broad spectrum glycosidase inhibitors are produced from monosaccharide lactams by conversion to amidines, amidrazones or amidoximes. The inhibitors have the general formula: ##STR1## wherein the N and C are joined as part of a monosaccharide azaanalog ring and wherein --NRQ, together with the nitrogen and carbon atoms, form a chemical group selected from amidines, amidrazones, and amidoximes.
    Type: Grant
    Filed: January 19, 1995
    Date of Patent: September 2, 1997
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Bruce Ganem, Michael K. Tong, George Papandreou
  • Patent number: 5650417
    Abstract: Substituted pyridines, their preparation, and their use as pesticides and fungicides.The invention relates to compounds of the formula ##STR1## and to salts thereof in which 1, 2, 3 or 4 of the radicals R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are an aliphatic, alicyclic or araliphatic radical bonded by a --O--CH.sub.2 -- or --O--CO--, and the remaining ones of these radicals are H, halogen or an aliphatic or aromatic radical, X is O, S or optionally substituted imino, Y is a bond or a bivalent radical and Z is an aromatic radical or optionally substituted cycloalkyl or cycloalkenyl. The invention furthermore relates to processes for their preparation and to their use as pesticides, in particular as insecticides, acaricides and fungicides.
    Type: Grant
    Filed: September 12, 1994
    Date of Patent: July 22, 1997
    Assignee: Hoechst Schering AgrEvo GmbH
    Inventors: Dieter Bernd Reuschling, Adolf Heinz Linkies, Volkmar Wehner, Rainer Preuss, Wolfgang Schaper, Harald Jakobi, Peter Braun, Werner Knauf, Burkhard Sachse, Anna Waltersdorfer, Manfred Kern, Peter Lummen, Werner Bonin
  • Patent number: 5643914
    Abstract: This invention relates to a compound of formula 1 ##STR1## or an N-oxide, or a pharmaceutically acceptable salt, where A is CH.sub.2 and Z is S(O).sub.q where q is 0, 1 or 2, CH.sub.2, CHOH, CO, NR.sub.x, or O, orA is C.dbd.O and Z is NR.sub.x ;m is 0-5;R.sub.x is hydrogen or lower alkyl;R is C.sub.1 to C.sub.20 -aliphatic, unsubstituted or substituted five-membered heteroaryl-C.sub.1 to C.sub.10 -aliphatic-O--, unsubstituted or substituted phenyl-C.sub.1 to C.sub.10 -aliphatic where substituted p from the group consisting of lower alkoxy, lower alkyl, trihalomethyl, and halo, or R is C.sub.1 to C.sub.20 -aliphatic-O--, or R is unsubstituted or substituted phenyl-C.sub.1 to C.sub.10 -aliphatic-O-- where substituted phenyl has one or more radicals selected from the group consisting of lower alkoxy, lower alkyl, trihalomethyl, and halo;R.sub.1 is R.sub.4, --(C.sub.1 to C.sub.5 aliphatic)R.sub.4, --(C.sub.1 to C.sub.5 aliphatic)CHO, --(C.sub.1 to C.sub.5 aliphatic)CH.sub.2 OR.sub.5;R.sub.2 and R.sub.
    Type: Grant
    Filed: December 19, 1994
    Date of Patent: July 1, 1997
    Assignee: SmithKline Beecham Corporation
    Inventor: Robert A. Daines
  • Patent number: 5644063
    Abstract: Imidazo[4,5-c]pyridin-4-amines that induce interferon (.alpha.) biosynthesis in human cells. Also disclosed are pharmaceutical compositions containing such compounds and methods of inducing interferon (.alpha.) biosynthesis involving the use of such compounds.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: July 1, 1997
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Kyle J. Lindstrom, Nick Nikolaides
  • Patent number: 5631377
    Abstract: This invention relates to a novel polyimide or polyimide copolymer having excellent heat resistance and greatly improved processability, and has a novel aromatic diamino compound used for the polyimide, a preparation process thereof, a polyimide-based resin composition comprising the polyimide or polyimide copolymer and a fibrous reinforcement, a process for preparing the resin composition, an injection molded article of the resin composition.The polyimide comprise a requisite structural unit having one or more recurring structural units of the formula: ##STR1## wherein L is an oxygen atom, carbonyl, isopropylidene or hexafluoroisopropylidene, and X is ##STR2## , and Ar is a tetravalent radical having 6 to 27 carbon atoms and being selected from the group consisting of a monoaromatic radical, condensed polyaromatic radical and noncondensed polyaromatic radical having aromatic radicals connected to each other with a direct bond or a bridge member.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: May 20, 1997
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Mitsunori Matsuo, Tsutomu Ishida, Akio Karasawa, Keizaburo Yamaguchi, Akihiro Yamaguchi
  • Patent number: 5624901
    Abstract: Disclosed is a series of improved metal chelating agents, which are highly effective upon both injection and oral administration; several of the most effective are of low toxicity. These chelating agents incorporate within their structure 1-hydroxy-2-pyridinone (1,2-HOPO) and 3-hydroxy-2-pyridinone (3,2-HOPO) moieties with a substituted carbamoyl group ortho to the hydroxy or oxo groups of the hydroxypyridinone ring. The electron-withdrawing carbamoyl group increases the acidity of the hydroxypyridinones. In the metal complexes of said chelating agents, the amide protons form very strong hydrogen bonds with its adjacent HOPO oxygen donor, making these complexes very stable at physiological conditions. The terminal N-substituents provides a certain degree of lipophilicity to said 3,2-HOPO, increasing oral activity.
    Type: Grant
    Filed: August 2, 1994
    Date of Patent: April 29, 1997
    Assignee: The Regents of the University of California
    Inventors: Kenneth N. Raymond, Jide Xu
  • Patent number: 5620995
    Abstract: The invention relates to compounds of the formula I, to a process for their preparation and to their use as pharmaceuticals. ##STR1## In particular, the compounds are used as inhibitors of prolyl-4-hydroxylase and as inhibitors of collagen biosynthesis, as pharmaceuticals against fibrotic diseases of the liver, the lung and the skin.
    Type: Grant
    Filed: December 28, 1994
    Date of Patent: April 15, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Klaus Weidmann, Karl-Heinz Baringhaus, Georg Tschank, Martin Bickel
  • Patent number: 5597836
    Abstract: N-(4-Pyridyl) arylacetamides, for example N-((3-chloro-2-ethyl)-4-pyridyl)(4-(4-chlorophenoxy)phenyl)-acetamide, and 4-(aralkyoxy or aralkylamino)pyridines, for example 4-[2-[4-(2,2,2-trifluoroethoxy)phenyl]ethoxy]pyridine, are active against nematodes, insects, mites, and plant pathogens.
    Type: Grant
    Filed: February 7, 1995
    Date of Patent: January 28, 1997
    Assignee: DowElanco
    Inventors: Ronald E. Hackler, Peter L. Johnson
  • Patent number: 5591857
    Abstract: An improved process for the preparation of 2,3,5,6-tetrachloropyridine of the formula ##STR1## consists in that 3,3,5-trichloroglutarimide of the formule ##STR2## is reacted either a. with phosphorus trichloride or phosphorus oxytrichloride or mixtures thereof in the presence from the start of catalytic amounts of hydrogen chloride, followed by a conversion of polyphosphorous compounds formed into phosphorus oxytrichloride by supplying chlorine, optionally only after supplying further phosphorus trichloride, orb. with phosphorus trichloride and chlorine, optionally in the presence of phosphorus oxytrichloride as a solvent, followed by a dehydrochlorination of the reaction mixture and finally conversion of polyphosphorus compounds formed into phosphorus oxytrichloride by supplying chlorine, optionally only after supplying further phosphorus trichloride.Improved yields of a purer product are obtained.
    Type: Grant
    Filed: August 22, 1994
    Date of Patent: January 7, 1997
    Assignee: Cheminova Agro A/S
    Inventors: Niels Friis, Per Fr.o slashed.lich
  • Patent number: 5589485
    Abstract: Novel antifungal and antitumor agents having the formula ##STR1## as well as pharmaceutically acceptable salts, esters, amides and pro-drugs thereof, wherein R is selected from the group consisting of ##STR2## Also disclosed are pharmaceutical compositions comprising such compounds, and methods of treatment and processes of manufacture relating thereto.
    Type: Grant
    Filed: April 26, 1995
    Date of Patent: December 31, 1996
    Assignee: Abbott Laboratories
    Inventors: Jill E. Hochlowski, Marianna Jackson, Sunil K. Kadam, James P. Karwowski, James B. McAlpine
  • Patent number: 5587387
    Abstract: The present invention is concerned with antiretroviral (e.g. anti-HIV-1)compounds having the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently are halo or methyl; R.sup.3 is hydrogen, halo, nitro or trifiuoromethyl; R.sup.4 is trifiuoromethyl or methylcarbonyl; or a radical --C(.dbd.X)--NR.sup.5 R.sup.6 wherein X is O or S, and R.sup.5 and R.sup.6 each independently are hydrogen or C.sub.1-4 alkyl; or a radical -Alk-R.sup.7, wherein Alk is C.sub.1-4 alkanediyl; and R.sup.7 is hydrogen or hydroxy; Het is a heterocyclic radical of formula: ##STR2## Pharmaceutical compositions containing said compounds of formula (I) and processes of preparing said compounds and compositions.
    Type: Grant
    Filed: May 2, 1995
    Date of Patent: December 24, 1996
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Marcel A. C. Janssen, Georges H. P. Van Daele, Jean-Paul R. M. A. Bosmans, Marc G. C. Verdonck, Paul A. J. Janssen
  • Patent number: 5585327
    Abstract: 4-substituted pyridyl-3-carbinols of the formula ##STR1## wherein R is hydrogen, or an acyl, alkyl or carbamyl group exhibit desirable preemergent and postemergent herbicidal activity. Also disclosed are herbicidal compositions comprising such compounds and methods of controlling undesirable vegetation employing such compounds. The compounds wherein AR is hydroxyl serve as useful intermediates for the production of the alpha-benzyl substituted compounds as well as exhibiting herbicidal activity.
    Type: Grant
    Filed: May 2, 1994
    Date of Patent: December 17, 1996
    Assignee: Zeneca Limited
    Inventors: Hsiao-Ling Chin, Yi-Qiu Wei, Nhan H. Nguyen, Michael P. Ensminger, Linda Willitts, Derek P. Dagarin
  • Patent number: 5583147
    Abstract: This invention provides amide compounds as inhibitors of acyl-Coenzyme A: cholesterol O-acyltransferase (ACAT), pharmaceutical compositions containing such compounds, processes for the preparation of such compounds, and the use of such compounds as antihypercholesterolemic and/or antiatherosclerotic agents.
    Type: Grant
    Filed: March 23, 1994
    Date of Patent: December 10, 1996
    Assignee: The Dupont Merck Pharmaceutical Company
    Inventors: Soo S. Ko, Richard G. Wilde, Indawati DeLucca, Hui-Yin Li, Hollis S. Kezar, III, George A. Boswell, Anurag S. Srivastava
  • Patent number: 5565413
    Abstract: Herbicidal compounds have the formula ##STR1## in which: R.sub.1 is hydrogen, halogen; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 haloalkyl; C.sub.1 -C.sub.4 alkoxy; C.sub.1 -C.sub.4 haloalkoxy; C.sub.2 -C.sub.8 alkoxyalkyl; nitro; cyano; thiocyano; or R.sub.7 S(O).sub.m - where m is 0, 1 or 2 and R.sub.7 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl;R.sub.2 and R.sub.3 are independently hydrogen; halogen; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkoxy; C.sub.1 -C.sub.4 haloalkyl; C.sub.1 -C.sub.4 haloalkoxy; C.sub.2 -C.sub.8 alkoxyalkyl; nitro; R.sub.8 S(O).sub.2 O- or R.sub.8 S(O).sub.n - where n is 0, 1 or 2 and R.sub.8 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 cyanoalkyl, phenyl or benzyl; NR.sub.9 R.sub.10 where R.sub.9 and R.sub.10 are independently hydrogen or C.sub.1 -C.sub.4 alkyl; R.sub.11 CO- where R.sub.11 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, SO.sub.2 NR.sub.12 R.sub.13 where R.sub.12 and R.sub.13 are independently hydrogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: December 6, 1994
    Date of Patent: October 15, 1996
    Assignee: Zeneca Limited
    Inventor: David B. Kanne
  • Patent number: 5563160
    Abstract: The present invention relates to hitherto unknown compounds of formula or their tautomeric forms, the attachment to the pyridine ring being in the 3- or 4-position, in which R', R" are the same or different and stand for hydrogen, halogen, or trifluoromethyl, hydroxy, C.sub.1 -C.sub.4 alkyl or alkoxy, nitro, or cyano groups. Alkylene stands for a straight or branched C.sub.1 -C.sub.8 carbon chain, which may be substituted by hydroxy or halogen, nitro or cyano groups. X stands for oxygen, for --S(O).sub.n -- where n stands for an integer from 0 to 2, or for .dbd.N--R.sub.1 where R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl. R stands for hydrogen or for one or more C.sub.1 -C.sub.4 alkyl or alkoxy, hydroxy, halogen, trifluoromethyl, cyano, carboxamido, sulfamoyl or nitro radicals. The present compounds are of value in the human and veterinary practice as selective serotonin receptor antagonists.
    Type: Grant
    Filed: March 15, 1995
    Date of Patent: October 8, 1996
    Assignee: Leo Pharmaceutical Products Ltd. A/S (L.o slashed.vens Kemiske Fabrik Produktionsaktieselskab)
    Inventors: Erik Bramm, Hans J.o slashed.rgen Petersen
  • Patent number: 5554578
    Abstract: Oxime ether derivatives of the formula I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen or alkyl, Het is pyridyl, quinolyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, quinoxalinyl, isoxazolyl, benzoxazolyl or benzothiazolyl bedeutet, the heterocyclic ring system being unsubstituted or substituted, and X is oxygen or sulfur, their plant-tolerated acid addition salts, metal complexes and N-oxides, and fungicides containing these compounds.
    Type: Grant
    Filed: August 8, 1995
    Date of Patent: September 10, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Wenderoth, Siegbert Brand, Franz Schuetz, Thomas Kuekenhoehner, Franz Roehl, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5554737
    Abstract: Azo dyes of the formula ##STR1## where D is the radical of a diazo component, andX is substituted or unsubstituted C.sub.2 -C.sub.8 -alkylene, in the form of the free acid or its salts, the use thereof for dyeing or printing natural or synthetic substrates, sulfopyridones as coupling components for these dyes, and a process for preparing them.
    Type: Grant
    Filed: May 2, 1995
    Date of Patent: September 10, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Gunther Lamm, Helmut Reichelt, Matthias Wiesenfeldt
  • Patent number: 5552418
    Abstract: The invention relates to a compound selected from those of formula (I): ##STR1## in which R, R.sub.1, R.sub.2 and R.sub.3 are as defined in the specification,and a medicinal product containing said compound for treating a disorder of the melatoninergic system.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: September 3, 1996
    Assignee: Adir et Compagnie
    Inventors: Patrick Depreux, Hamid Ait Mansour, Daniel Lesieur, Fran.cedilla.ois Lefoulon, Pierre Renard, G erard Adam, Philippe Delagrange
  • Patent number: 5548078
    Abstract: A fungicidal composition for agricultural use, which comprises a compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each hydrogen, lower alkyl or cyclo(lower)alkyl; R.sup.3 is lower alkyl or cyclo(lower)alkyl; R.sup.4 and R.sup.5 are each hydrogen, lower alkyl, lower alkoxy, halogen-substituted lower alkyl, lower alkyl-substituted silyl, halogen or nitro; A represents an unsaturated hydrocarbon group, a halogen-substituted unsaturated hydrocarbon group, a phenyl group or a heterocyclic group, among which the phenyl group and the heterocyclic group may be optionally substituted with not more than three substituents; and Z is --CH.sub.2 --, --CH(OH)--, --CO--, --O--, --S--, --NR-- (R being hydrogen or lower alkyl), --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, ##STR2## --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 SO--, --OCH.sub.2 --, --SCH.sub.2 -- or --SOCH.sub.2 --.
    Type: Grant
    Filed: December 20, 1994
    Date of Patent: August 20, 1996
    Assignee: Shionogi Seiyaku Kabushiki Kaisha
    Inventors: Yoshio Hayase, Takahiro Kataoka, Hideyuki Takenaka, Mitsuhiro Ichinari, Michio Masuko, Toshio Takahashi, Norihiko Tanimoto
  • Patent number: 5530014
    Abstract: The cyclohexadiene derivatives are prepared by reaction of cyclohexanones with amines and subsequent dehydration. The compounds are suitable as active compounds in medicaments on account of their property of being selective modulators of calcium channel-dependent potassium channels.
    Type: Grant
    Filed: August 18, 1995
    Date of Patent: June 25, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Urbahns, Hans-Georg Heine, Bodo Junge, Rudolf Schohe-Loop, Hartmund Wollweber, Henning Sommermeyer, Thomas Glaser, Reilinde Wittka, Jean-Marie-Viktor De Vry
  • Patent number: 5506227
    Abstract: Compounds having the formula I: ##STR1## are antagonists of the actions of leukotrienes. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection.
    Type: Grant
    Filed: April 13, 1992
    Date of Patent: April 9, 1996
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Robert Zamboni, Daniel Guay, Jacques-Yves Gauthier
  • Patent number: 5500429
    Abstract: This invention relates to 1-aryl-3-pyridinyl-2-propene-1-ones, the use of these compounds as calcium uptake inhibitors in leukocytes and thrombocytes, and pharmaceutical compositions containing these compounds as active ingredients, and the process of their preparation.
    Type: Grant
    Filed: November 17, 1993
    Date of Patent: March 19, 1996
    Assignee: Merrell Pharmaceuticals Inc.
    Inventors: Robert J. Dinerstein, Michael L. Edwards, David M. Stemerick, Keith A. Diekema
  • Patent number: RE35948
    Abstract: Pharmaceutical compositions containing a 3-hydroxypyrid-2-one or 3-hydroxypyrid one in which the hydrogen atom attached to the nitrogen atom is replaced by an aliphatic acyl group, by an aliphatic hydrocarbon group, or by an aliphatic hydrocarbon group substituted by one or, except in the case of ionizable groups, more than one substituent selected from aliphatic acyl, alkoxy, aliphatic amine, aliphatic amide, carboxy, aliphatic ester, halogen, hydroxy and sulpho groups and, optionally, in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by one of said substituents, by an aliphatic hydrocarbon group, or by an aliphatic hydrocarbon group substituted by an alkoxy, aliphatic ester, halogen or hydroxy group, but excluding compounds in which said replacement of hydrogen atoms in the compound is effected only by aliphatic hydrocarbon groups, or a salt thereof containing a physiologically acceptable ion or ions, are of value for removing toxic amounts of metals, particularly iron, f
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: November 3, 1998
    Assignee: British Technology Group Ltd.
    Inventors: Robert C. Hider, George Kontoghiorghes, Jack Silver