At Least Three Ring Hetero Atoms In The Polycyclo Ring System Patents (Class 548/218)
  • Patent number: 6242471
    Abstract: A compound represented by the formula: wherein X represents a sulfur atom or an oxygen atom; Y represents an optionally oxidized sulfur atom or an oxygen atom; Z represents a bond or a divalent hydrocarbon group; R1 represents an optionally substituted hydrocarbon group; R2 represents an optionally amidated or esterified carboxyl group; ring A represents an optionally substituted aromatic 5-membered heterocyclic ring; or a salt thereof. A compound of the above formula possesses cell differentiation inducing factor action-enhancing activity and anti-matrix metalloprotease activity and that is useful in the prevention and treatment of bone diseases such as osteoporosis, bone fractures, osteoarthritis and rheumatoid arthritis, arteriosclerosis, cancer metastasis, and diseases based on nerve degeneration.
    Type: Grant
    Filed: April 28, 2000
    Date of Patent: June 5, 2001
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Tsuneo Yasuma, Tsuneo Oda, Masatoshi Hazama, Shigehisa Taketomi
  • Patent number: 6211227
    Abstract: The present invention provides tricyclic compounds which are useful for the treatment of pollakiuria and urinary incontinence and which are represented by general formula (I): (wherein R1 represents hydrogen, substituted or unsubstituted lower alkyl, etc.; X1—X2—X3 represents CR5═CR6—CR7═CR8 (wherein R5, R6, R7 and R8, which may be the same or different, each represents hydrogen, substituted or unsubstituted lower alkyl, hydroxy, substituted or unsubstituted lower alkoxy, etc.), N(O)m═CR5—CR6═CR7 (wherein R5, R6 and R7 have the same significances as defined above, and m represents 0 or 1), S—CR7═CR8 (wherein R7 and R8 have the same significances as defined above), etc.
    Type: Grant
    Filed: October 14, 1999
    Date of Patent: April 3, 2001
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Makoto Yoshida, Takashi Seishi, Shigeru Aono, Tsuyoshi Yamagata, Kaoru Atsuki, Toshiaki Kumazawa, Haruki Takai, Koji Suzuki, Akira Karasawa
  • Patent number: 6197804
    Abstract: Disclosed are novel 4,5-azolo-oxindoles having the formula These compounds inhibit cyclin-dependent kinases (CDKs), in particular CDK2. Thus, these compounds and their pharmaceutically acceptable salts, and *prodrugs of said compounds, are anti-proliferative agents useful in the treatment or control of cell proliferative disorders, in particular cancer. Also disclosed are pharmaceutical compositions containing these compounds, and methods for the treatment and/or prevention of cancer, particularly in the treatment or control of solid tumors using these compounds, as well as intermediates useful in the preparation of compounds of formula I.
    Type: Grant
    Filed: May 16, 2000
    Date of Patent: March 6, 2001
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Kin-Chun Luk, Steven Gregory Mischke
  • Patent number: 6153634
    Abstract: Disclosed are novel 4,5-azolo-oxindoles having the formula ##STR1## These compounds inhibit cyclin-dependent kinases (CDKs), in particular CDK2. Thus, these compounds and their pharmaceutically acceptable salts, and prodrugs of said compounds, are anti-proliferative agents useful in the treatment or control of cell proliferative disorders, in particular cancer. Also disclosed are pharmaceutical compositions containing these compounds, and methods for the treatment and/or prevention of cancer, particularly in the treatment or control of solid tumors using these compounds, as well as intermediates useful in the preparation of compounds of formula I.
    Type: Grant
    Filed: December 15, 1999
    Date of Patent: November 28, 2000
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Kin-Chun Luk, Christophe Michoud, Steven Gregory Mischke
  • Patent number: 6124331
    Abstract: This invention is directed to tricyclic compounds which are selective antagonists for NPY (Y5) receptors. The invention provides a pharmaceutical composition comprising a therapeutically effective amount of the compound of the invention and a pharmaceutically acceptable carrier. This invention provides a pharmaceutical composition made by combining a therapeutically effective amount of the compound of this invention and a pharmaceutically acceptable carrier. This invention further provides a process for making a pharmaceutical composition comprising combining a therapeutically effective amount of the compound of the invention and a pharmaceutically acceptable carrier.
    Type: Grant
    Filed: June 30, 1999
    Date of Patent: September 26, 2000
    Assignee: Synaptic Pharmaceutical Corporation
    Inventors: Mohammad R. Marzabadi, Wai C. Wong, Stewart A. Noble
  • Patent number: 6096771
    Abstract: An isoxazole compound having the following formula: ##STR1## wherein R.sup.1 represents hydrogen, halogen, alkyl, alkoxy, hydroxyl, alkylthio, amino, alkanoyl, alkanoylamino, alkanoyloxy, alkoxycarbonyl, carboxy, (alkylthio)thiocarbonyl, carbamoyl, nitro or cyano; R.sup.2 represents an amino; m is 2 or 3; n is 1 to 6; ring A represents a phenyl ring, a naphthyl ring or an aromatic heterocycle; and X represents oxygen or sulfur. The isoxazole compound has an excellent monoamine oxidase inhibitory activity, and is useful for treating Parkinson's disease, depression and Alzheimer's disease.
    Type: Grant
    Filed: February 3, 1999
    Date of Patent: August 1, 2000
    Assignee: Sankyo Company, Limited
    Inventors: Koichi Kojima, Junichi Sakai, Yuichi Aizawa, Naozumi Samata, Masao Kozuka, Kenji Yoshimi, Isao Kaneko, Kazuo Koyama
  • Patent number: 5998408
    Abstract: The compounds of Formula I ##STR1## are useful as immunosuppressive agents.
    Type: Grant
    Filed: October 8, 1997
    Date of Patent: December 7, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Robert K. Baker, Frank Kayser, Jianming Bao, Andrew Kotliar, William H. Parsons, Kathleen M. Rupprecht
  • Patent number: 5998626
    Abstract: Disclosed are bisbenzazole compounds capable of emitting strong fluorescence, with the compounds having at particular positions specific substituent groups, such as alkoxy, aryloxy, dialkylamino, diarylamino or N-arylamino groups, to ensure high stability in organic photoluminescence elements. For example, bisbenzazole compounds show below are disclosed.
    Type: Grant
    Filed: January 27, 1999
    Date of Patent: December 7, 1999
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Tadahisa Sato
  • Patent number: 5990145
    Abstract: The present invention relates to compounds of the formula I,A--B--D--E--F--G (I)in which A, B, D, E, F and G have the meanings given in the patent claims, to their preparation and to their use as medicaments. The compounds of the invention are used as vitronectin receptor antagonists and as inhibitors of bone resorption.
    Type: Grant
    Filed: December 22, 1997
    Date of Patent: November 23, 1999
    Assignees: Hoechst Aktiengesellschaft, Genentech, Inc.
    Inventors: Volkmar Wehner, Hans Ulrich Stilz, Anuschirwan Peyman, Karlheinz Scheunemann, Jean-Marie Ruxer, Denis Carniato, Jean-Michel Lefrancois, Thomas Richard Gadek, Robert McDowell
  • Patent number: 5962683
    Abstract: A description is given of compounds of the formula I ##STR1## where r is 0 or 1 and y is a number from the range 1-3; X is a direct bond or --NR.sub.8 --, --CO--, --CONH-- or --COO-- or a divalent aliphatic or mixed aromatic-aliphatic C.sub.1 -C.sub.18 hydrocarbon radical;Z is an aromatic, aliphatic or mixed aromatic-aliphatic C.sub.3 -C.sub.18 hydrocarbon radical which is interrupted in the aliphatic moiety by one or more divalent functional groups, in each case in a carbon-carbon single bond, and/or in the aromatic or aliphatic moiety by one or more divalent functional groups, in each case in a carbon-hydrogen bond, possible functional groups being --O--, --NR.sub.8 --, --S--, --SO--, --SO.sub.
    Type: Grant
    Filed: June 17, 1997
    Date of Patent: October 5, 1999
    Assignee: Ciba Specialty Chemicals Corp.
    Inventors: Alfred Steinmann, Rolf Mulhaupt
  • Patent number: 5886046
    Abstract: This invention relates to chemical compounds that contain adjacent carbonyl groups, which effectively inhibit the biological, chemical, and/or physical properties of enzymes and other medicinally-significant proteins. In particular, the invention relates to dicarbonyl compounds that are capable of acting as enzyme inhibitors, including irreversible inhibitors of HIV-1 protease.
    Type: Grant
    Filed: January 19, 1996
    Date of Patent: March 23, 1999
    Assignee: The Trustees of the University of Pennsylvania
    Inventors: Ralph F. Hirschmann, Amos B. Smith, III, Paul Sprengeler, Wenqing Yao, Paul Anderson
  • Patent number: 5856478
    Abstract: The invention relates to new anellated (oxa) hydantoins, and herbicidal compositions containing same. The invention also relates to methods for controlling noxious plants using the anellated (oxa) hydantoins of the invention.
    Type: Grant
    Filed: November 19, 1996
    Date of Patent: January 5, 1999
    Assignee: Degussa Aktiengesellschaft
    Inventors: Matthias Schafer, Helmut Baier, Karlheinz Drauz, Hans-Peter Krimmer, Sabine Landmann
  • Patent number: 5754271
    Abstract: The invention relates to photochromic compounds of general formula: ##STR1## wherein R.sup.a, R.sup.b and R.sup.c is denote hydrogen; alkyl; aryl; OR, SR, COR or COOR, in which R denotes hydrogen, alkyl or aryl, amino of formula NR.sub.1 R.sub.2 in which R.sub.1 and R.sub.2 denote hydrogen, alkyl, cycloalkyl or an aryl; a halogen atom; a mono- or polyhaloalkyl group; or an NO.sub.2, CN or SCN group; n and m denote integers from 1 to 5; p is equal to 1 or 2; and H is a 5-members aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen and sulfur, these heterocyclic nuclei being eventually substituted by one or more alkyl, alkoxy, amino, aryl or aralkyl groups or condensed with a phenyl nucleus, a substituted phenyl nucleus or a 6-members cycloaliphatic nucleus and to their use in ophtalmic optics.
    Type: Grant
    Filed: June 3, 1996
    Date of Patent: May 19, 1998
    Assignee: Essilor International (Compagnie General d'Optique)
    Inventors: Robert Guglielmetti, Jean Luc Pozzo, Andre Samat
  • Patent number: 5733648
    Abstract: Organic compounds having at least one ethylenically-unsaturated group are described, the organic compounds being suitable for use in coatable compositions as reactive diluents; compounds of the invention preferably have a divalent organic linking moiety devoid of reactive groups other than optional ethylenically-unsaturated groups, and a polar organic moiety and are particularly adept in solubilizing aminoplast resins having radiation-curable pendant groups.
    Type: Grant
    Filed: February 23, 1996
    Date of Patent: March 31, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Ernest L. Thurber, Eric G. Larson, Alan R. Kirk, Gregg D. Dahlke
  • Patent number: 5718845
    Abstract: Nonlinear optical compounds which contain a heteroaromatic ring and may further comprise a tricyanovinyl group attached to the heteroaromatic ring.
    Type: Grant
    Filed: January 18, 1995
    Date of Patent: February 17, 1998
    Assignee: Enichem S.p.A.
    Inventors: Kevin J. Drost, Pushkara Rao Varanasi, Kwan-Yue Alex Jen, Michael Anthony Drzewinski
  • Patent number: 5705509
    Abstract: Compounds of formula (I) or a pharmaceutically acceptable salt thereof, wherein X.sub.1 --(CH.sub.2).sub.x --X.sub.2 and the aromatic carbon atoms to which they are attached form 5-7 membered ring wherein X.sub.1 is O or S; X.sub.2 is O, S, NR.sub.5 or NR.sub.6 CO wherein R.sub.5 is hydrogen or C.sub.1-6 alkyl; or one of X.sub.1 and X.sub.2 is O, S or CH.sub.2 and the other is CH.sub.2 ; x is 1, 2 or 3; R.sub.1 and R.sub.2 together are Q--CH.sub.2 --CH.sub.2, Q--CH.dbd.CH, or Q--CH.dbd.N where Q is linked either to the R.sub.1 or the R.sub.2 substitution position and Q is O, S or NR.sub.t wherein R.sub.t is hydrogen or C.sub.1-6 alkyl; R.sub.3 is hydrogen halo, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or amino; R.sub.4.sup.1 and R.sub.4.sup.2 are independently hydrogen or C.sub.1-6 alkyl; Y is O or NH; Z is of sub-formula (a), (b) or (c) and their use as pharmaceuticals in the treatment of gastrointestinal disorders, cardiovascular disorders and CNS disorders.
    Type: Grant
    Filed: July 28, 1995
    Date of Patent: January 6, 1998
    Assignee: SmithKline Beecham plc
    Inventors: Laramie Mary Gaster, Paul Adrian Wyman
  • Patent number: 5693460
    Abstract: This invention provides a silver halide photographic element comprising a silver halide emulsion in reactive association with a dioxide compound represented by the following formula: ##STR1## wherein b is C(O), C(S), C(Se), CH2 or (CH2)2; and R.sup.1 and R.sup.2 are independently H, or aliphatic, aromatic or heterocyclic groups, or R.sup.1 and R.sup.2 together represent the atoms necessary to form a five or six-membered ring or a multiple ring system. This invention further provides a method of making silver halide emulsions containing the dioxide compounds.
    Type: Grant
    Filed: June 24, 1996
    Date of Patent: December 2, 1997
    Assignee: Eastman Kodak Company
    Inventor: Roger Lok
  • Patent number: 5668278
    Type: Grant
    Filed: July 31, 1996
    Date of Patent: September 16, 1997
    Assignee: Hoeschst Schering AgrEvo GmbH
    Inventors: Uwe Hartfiel, Gabriele Dorfmeister, Helga Franke, Jens Geisler, Gerhard Johann, Richard Rees
  • Patent number: 5661109
    Abstract: The invention relates to new anellated (oxa) hydantoins, and herbicidal compositions containing same. The invention also relates to methods for controlling noxious plants using the anellated (oxa) hydantoins of the invention.
    Type: Grant
    Filed: April 21, 1995
    Date of Patent: August 26, 1997
    Assignee: DEGUSSA Aktiengesellschaft
    Inventors: Matthias Schafer, Helmut Baier, Karlheinz Drauz, Hans-Peter Krimmer, Sabine Landmann
  • Patent number: 5659015
    Abstract: This invention relates to a method of producing peracetyloxazolines from peracetyl saccharides. The method involves reacting the starting material, a peracetyl saccharide, with a reagent combination, to directly produce the peracetyl oxazoline. This method may be used for the activation of oligosaccharides, wherein an oligosaccharide containing a reducing GlcNAc terminus is activated by the formation of an oxazolide at the terminal GlcNAc, and then coupled with a bifunctional spacer to provide an oligosaccharide-spacer conjugate. The activated oligosaccharide-spacer conjugate is then coupled to a protein, such as granulocyte colony stimulating factor or .gamma.-interferon, providing a neoglycoprotein conjugate. The invention provides a method for forming neoglycoprotein conjugates which may improve biological and physiochemical properties of the protein. For example, serum lifetime or efficiency of drug delivery of the peptide to a target organ or cell may be improved.
    Type: Grant
    Filed: October 13, 1992
    Date of Patent: August 19, 1997
    Inventors: Marcelo Colon, Jeffrey T. Davis, James R. Rasmussen, Marianne Borowski, Barbara Y. Wan, Shirish Hirani
  • Patent number: 5637725
    Abstract: Disclosed are compounds of the formula: ##STR1## wherein: T is NH, O, or S;X is hydrogen, hydroxyl, lower alkyl, or an optionally substituted amide;the W ring is an optionally substituted aryl or heteroaryl group; and ##STR2## represents an optionally substituted benzo group or an optionally substituted 5, 6, 7, or 8 membered ring.These compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs of agonists, antagonists or inverse agonists for GABAa brain receptors. These compounds are useful in the diagnosis and treatment of anxiety, sleep and seizure disorders, overdose with benzodiazepine drugs and for enhancement of memory.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: June 10, 1997
    Assignee: Neurogen Corporation
    Inventors: Robert W. DeSimone, Charles A. Blum
  • Patent number: 5637724
    Abstract: Disclosed are compounds of the formula: ##STR1## wherein: T is NH, O, or S;X is hydrogen, hydroxyl, lower alkyl, or an optionally substituted amide;the W ring is an optionally substituted aryl or heteroaryl group; and ##STR2## represents an optionally substituted benzo group or an optionally substituted 5, 6, 7, or 8 membered ring.These compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs of agonists, antagonists or inverse agonists for GABAa brain receptors. These compounds are useful in the diagnosis and treatment of anxiety, sleep and seizure disorders, overdose with benzodiazepine drugs and for enhancement of memory.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: June 10, 1997
    Assignee: Neurogen Corporation
    Inventors: Robert W. DeSimone, Charles A. Blum
  • Patent number: 5612479
    Abstract: Novel polycyanate compositions containing one or more mesogenic moieties as lateral substituents are disclosed which provide improved processability relative to polycyanates containing one or more mesogenic moieties in the main chain of the molecule. Molecular level ordering of the resulting thermosets is maintained much similar to that found thermosets of polycyanates which have one or more mesogenic moieties in the main chain.
    Type: Grant
    Filed: August 17, 1994
    Date of Patent: March 18, 1997
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5569655
    Abstract: Substitutued heterocyclylisoquinolinium salts, pharmaceutical compositions containing them and methods for the treatment or prevention of neurodegenerative disorders or neurotoxic injuries utilizing them.
    Type: Grant
    Filed: July 29, 1994
    Date of Patent: October 29, 1996
    Assignee: Sterling Winthrop Inc.
    Inventors: John A. Dority, Jr., William G. Earley, Virendra Kumar, John P. Mallamo, Matthew S. Miller, Chakrapani Subramanyam
  • Patent number: 5565482
    Abstract: A class of benzopyranopyrazolyl derivatives is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula I ##STR1## wherein A is --(CH.sub.2).sub.m --X--(CH.sub.2).sub.n --; wherein X is S(O).sub.p or O; wherein m is 0 or 1; wherein n is 0 or 1; wherein p is 0 or 1; wherein B is selected from phenyl and five and six membered heteroaryl; wherein R.sup.1 is selected from lower haloalkyl, cyano, formyl, lower alkoxycarbonyl, lower alkoxy, lower N-alkylaminocarbonyl, N-phenylaminocarbonyl, lower N,N-dialkylaminocarbonyl and lower N-alkyl-N-phenylaminocarbonyl; wherein R.sup.2 is phenyl substituted at a substitutable position with a radical selected from lower alkylsulfonyl and sulfamyl; and wherein R.sup.
    Type: Grant
    Filed: September 29, 1995
    Date of Patent: October 15, 1996
    Assignee: G.D. Searle & Co.
    Inventors: John J. Talley, Stephen R. Bertenshaw, Matthew J. Graneto, Donald J. Rogier
  • Patent number: 5552422
    Abstract: The invention encompasses the novel compound of Formula I as well as a method of treating cyclooxygenase-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.
    Type: Grant
    Filed: January 11, 1995
    Date of Patent: September 3, 1996
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Jacques Y. Gauthier, Cheuk K. Lau, Yves LeBlanc, Chun-Sing Li, Patrick Roy, Michel Therien, Zhaoyin Wang
  • Patent number: 5541323
    Abstract: Anhydride compounds which contain at least one rodlike mesogenic moiety and at least two anhydride groups per molecule, wherein each of said aromatic anhydride groups is linked to the mesogen via an ester linkage are prepared. These anhydride compounds are useful in curing epoxy resins to provide the cured products with one or more improved properties.
    Type: Grant
    Filed: January 18, 1995
    Date of Patent: July 30, 1996
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5527914
    Abstract: Methine compounds are described, which can be represented by general formula [Ic]: ##STR1##
    Type: Grant
    Filed: May 3, 1994
    Date of Patent: June 18, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Takanori Hioki, Tadashi Ikeda
  • Patent number: 5462694
    Abstract: A mesomorphic compound of the formula (I) according to claim 1 characterized by having at least one cyclic group selected from .beta. class including, e.g., thiazole-2,5-diyl, benzoxazole-2,5-diyl, indan-2,5-diyl, and quinoxaline-2,6-diyl and also having a linkage of Y.sup.1 (CH.sub.2).sub.m Y.sup.2, where Y.sup.1 and Y.sup.2 are --CH.sub.2 --, --O--, --COO-- or --OCO-- and m is 1-16, is suitable as a component for a liquid crystal composition providing improved response characteristics. A liquid crystal device is constituted by disposing the liquid crystal composition between a pair of substrates. The liquid crystal device is used as a display panel constituting a liquid crystal apparatus providing good display characteristics.
    Type: Grant
    Filed: August 30, 1994
    Date of Patent: October 31, 1995
    Assignee: Canon Kabushiki Kaisha
    Inventors: Yoko Kosaka, Takao Takiguchi, Takashi Iwaki, Takeshi Togano, Shinichi Nakamura, Ikuo Nakazawa
  • Patent number: 5405829
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: April 11, 1995
    Assignee: Schering Aktiengesellschaft
    Inventors: Uwe Hartfiel, Gabriele Dorfmeister, Helga Franke, Jens Geisler, Gerhard Johann, Richard Rees
  • Patent number: 5399673
    Abstract: Compounds containing at least one alkenyl group, at least one maleimide group and at least one rodlike mesogenic moiety are prepared by reacting one or more aminophenols containing one or more rodlike mesogenic moieties with a stoichiometric quantity of a maleic anhydride per amine group of said aminophenol and then alkenylating the resulting phenolic functional maleimide.
    Type: Grant
    Filed: February 9, 1993
    Date of Patent: March 21, 1995
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 5378680
    Abstract: Dicarboximides of the formulae Ia, Ib and Ic ##STR1## where X is oxygen or sulfur,R.sup.1 is hydrogen, halogen, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, haloalkoxy, haloalkylthio, alkylsulfonyl, haloalkylsulfonyl, phenyl, phenylalkyl, phenoxy or phenylthio, a 5-membered or 6-membered saturated or aromatic heterocyclic radical containing one or two hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, where the stated organic radicals may be further substituted, andR.sup.2 is hydrogen, hydroxyl, alkoxy, alkyl, cycloalkyl, alkenyl, alkynyl, di-C.sub.1 -C.sub.
    Type: Grant
    Filed: August 19, 1992
    Date of Patent: January 3, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Volker Maywald, Klaus Ditrich, Thomas Kuekenhoehner, Gerhard Hamprecht, Wolfgang Freund, Karl-Otto Westphalen, Matthias Gerber, Helmut Walter
  • Patent number: 5350760
    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: August 4, 1993
    Date of Patent: September 27, 1994
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Mark LaBelle, Yibin Xiang, Claude Dufresne, Michel Belley
  • Patent number: 5252769
    Abstract: Anthraquinonic colorant represented by the formula (I): ##STR1## wherein Q.sup.1 and Q.sup.2 are each independently substituted or unsubstituted anthraquinonyl groups, Z.sup.1 and Z.sup.2 are bridge groups, A is an aromatic divalent group, and n is 0 or 1. The polarizing film which contains at least one colorant of the present invention in a hydrophobic resin, has excellent durability and moisture resistance.
    Type: Grant
    Filed: June 26, 1992
    Date of Patent: October 12, 1993
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Tsutami Misawa, Hisato Itoh, Tsutomu Nishizawa, Masami Nakano, Hiroyuki Katayama
  • Patent number: 5250517
    Abstract: Compounds which are amino acid derivatives and have the formula ##STR1## in which R.sup.1 is hydrogen or methyl, R.sup.2 is ethyl, propyl or imidazol-4-yl, R.sup.3 is isobutyl, cyclohexylmethyl or benzyl, and A is defined as herein are useful as renin inhibitors.
    Type: Grant
    Filed: May 4, 1992
    Date of Patent: October 5, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Quirico Branca, Albrecht Edenhofer, Eva-Maria Gutknecht, Werner Neidhart, Henri Ramuz, Wolfgang Wostl
  • Patent number: 5241072
    Abstract: This invention relates to a method of producing peracetyloxazolines from peracetyl saccharides. The method involves reacting the starting material, a peracetyl saccharide, with a reagent combination, to directly produce the peracetyl oxazoline. This method may be used for the activation of oligosaccharides, wherein an oligosaccharide containing a reducing GlcNAc terminus is activated by the formation of an orazoline at the terminal GlcNAc, and then coupled with a bifunctional spacer to provide an oligosaccharide-spacer conjugate. The activated oligosaccharide-spacer conjugate is then coupled to a protein, such as granulocyte colony stimulating factor or .gamma.-interferon, providing a neoglycoprotein conjugate. The invention provides a method for forming neoglycoprotein conjugates which may improve biological and physiochemical properties of the protein. For example, serum lifetime or efficiency of drug delivery of the peptide to a target organ or cell may be improved.
    Type: Grant
    Filed: May 25, 1990
    Date of Patent: August 31, 1993
    Assignee: Genzyne Corporation
    Inventors: Marcelo Colon, Jeffrey T. Davis, James R. Rasmussen, Marianne Borowski, Barbara Y. Wan, Shirish Hirani
  • Patent number: 5231186
    Abstract: Quaternary ammonium salts having a 2, 3, 5, 6-tetrahydroxazolo [2, 3-b] oxazole nucleus, such as 4-aralkyl or alkyl-2, 3, 5, 6-tetrahydroxazolo [2, 3-b] oxazolium salts are disclosed. These quarternary ammonium salts are useful a cationic polymerization initiator or proton-donating catalyst of the heat latent type to be incorporated heat-curable coating and other resinous compositions.
    Type: Grant
    Filed: March 20, 1992
    Date of Patent: July 27, 1993
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Shinji Nakano, Satoshi Urano
  • Patent number: 5204467
    Abstract: Photopolymerizable compositions containing photoinitiator systems that absorb in the visible are disclosed.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: April 20, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William K. Smothers
  • Patent number: 5180419
    Abstract: There are provided o-carboxy-(5-oxo-2-imidazolin-2-yl)benzo-(5-membered)-heterocyclic compounds and derivatives thereof and a method for the use therewith to control monocotyledenous and dicotyledenous plant species.
    Type: Grant
    Filed: November 22, 1991
    Date of Patent: January 19, 1993
    Assignee: American Cyanamid Company
    Inventors: David M. Gange, Michael A. Guaciaro, Robert F. Doehner, Jr.
  • Patent number: 5179093
    Abstract: Compounds of the formula ##STR1## or a pharmaceutically acceptable salt thereof wherein, R is H, halogen, (C.sub.1 -C.sub.6) alkyl, N(C.sub.1 -C.sub.6 alkyl/aryl).sub.2, OH, O--(C.sub.1 -C.sub.6) alkyl/aryl, CH.sub.2 OH, COOH, COO-alkyl/aryl, SO.sub.2 NH.sub.2, or SO.sub.2 NH (C.sub.1 -C.sub.6 alkyl/aryl);R.sub.1 is C.sub.1 -C.sub.6 alkyl, cycloalkyl, C.sub.2 -C.sub.6 alkenyl, heteroaryl, substituted heteroaryl, heterocycloalkyl, --CH.sub.2 -aryl, --CH.sub.2 -substituted aryl, --CH.sub.2 -heteroaryl, or --CH.sub.2 -substituted heteroaryl;R.sub.2 is H, C.sub.1 -C.sub.6 alkyl or aryl; ##STR2## is an aromatic ring or a heteroaromatic ring; and X is O or N-(alkyl/aryl/alkyl-aryl/alkoxylalkoxyaryl)are described. These compounds are useful as agents for treating viruses.
    Type: Grant
    Filed: May 10, 1991
    Date of Patent: January 12, 1993
    Assignee: Schering Corporation
    Inventors: Adriano Afonso, Stuart W. McCombie, Jay Weinstein
  • Patent number: 5140033
    Abstract: Antibacterial 5-alkylquinolonecarboxylic acids of the formula ##STR1## in which R.sup.3 is C.sub.1 -C.sub.4 -alkyl,R.sup.1 is optionally substituted alkyl or cycloalkyl, alkenyl, alkoxy, amino or alkylamino or optionally substituted phenyl,R.sup.2 is hydrogen or optionally substituted alkyl,R.sup.4 is a nitrogen-containing heterocyclic radical, andA is hydrogen, halogen, methyl, cyano or nitro, or forms a bridge with R.sup.1.and hydrates and salts thereof.
    Type: Grant
    Filed: October 1, 1990
    Date of Patent: August 18, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Schriewer, Klaus Grohe, Andreas Krebs, Uwe Petersen, Thomas Schenke, Ingo Haller, Karl G. Metzger, Rainer Endermann, Hans-Joachim Zeiler
  • Patent number: 5140011
    Abstract: The compounds of the formula ##STR1## wherein A, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the significance given in claim 1, in the form of optically pure diastereomers, mixtures of diastereomers, diastereomeric racemates or mixtures of diastereomeric racemates as well as pharmaceutically usable salts thereof inhibit the activity of the natural enzyme renin and can accordingly be used in the form of pharmaceutical preparations in the control or prevention of high blood pressure and cardiac insufficiency.
    Type: Grant
    Filed: March 29, 1990
    Date of Patent: August 18, 1992
    Assignee: Hoffmann-La Roche, Inc.
    Inventors: Quirico Branca, Hans P. Marki, Werner Neidhart, Henri Ramuz, Wolfgang Wostl
  • Patent number: 5116968
    Abstract: Compounds of formula (1) ##STR1## wherein R represents a sugar residue or an acylated derivative thereof;R.sup.1 represents a methyl, ethyl or isopropyl group;Y.sup.1 is --CH.sub.2, Y.sup.2 is --CH-- and X represents ##STR2## [wherein R.sup.2 represents a hydrogen atom or a group OR.sup.6 (where OR.sup.6 is a hydroxyl group or a substituted hydroxyl group having up to 25 carbon atoms) and R.sup.3 represents a hydrogen atom, or R.sup.2 and R.sup.3 together with the carbon atom to which they are attached represent >C.dbd.0, >C.dbd.CH.sub.2 or >C.dbd.NOR.sup.7 (where R.sup.7 represents a hydrogen atom, a C.sub.1-8 alkyl group or a C.sub.3-8 alkenyl group) and the group >C.dbd.NOR.sup.7 is in the E configuration] or --Y.sup.1 --X--Y.sup.2 -- represents --CH.dbd.CH--CH-- or --CH.sub.2 --CH.dbd.C--; andR.sup.4 represents a group OR.sup.6 as defined above and R.sup.5 represents a hydrogen atom, or R.sup.4 and R.sup.5 together with the carbon atom to which the are attached represent >C.dbd.0 or >C.
    Type: Grant
    Filed: December 20, 1990
    Date of Patent: May 26, 1992
    Assignee: American Cyanamid Company
    Inventors: Gordon C. Lawrence, Michael J. Dawson, David Noble, Michael V. J. Ramsay, Richard Bell, Derek R. Sutherland, Edward P. Tiley
  • Patent number: 5095118
    Abstract: D-(+)-biotin can be prepared from optically active hydantoins of the formula I ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, X and Y have the meaning given in Patent claim 1, in a simple, stereospecific manner. Furthermore bicyclic nitriles of the formula XI ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, X and Y have the meaning given represent precious intermediate products and educts of a multitude of possibilities to synthesize optically active D-(+)-biotin.
    Type: Grant
    Filed: April 13, 1990
    Date of Patent: March 10, 1992
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Eike Poetsch, Michael Casutt
  • Patent number: 5068341
    Abstract: Optically active hydantoins of the formula I ##STR1## wherein X, Y, R.sup.1, R.sup.2 and R.sup.3 have the meaning given in Patent claim 1, are useful intermediate products for the preparation of D-(+)-biotin.
    Type: Grant
    Filed: September 5, 1989
    Date of Patent: November 26, 1991
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Eike Poetsch, Michael Casutt
  • Patent number: 5057526
    Abstract: Compounds of the formula I ##STR1## wherein R is a hydrogen atom or an alkyl radical, R.sub.1 is a hydrogen atom or an alkyl, alkenyl or a cycloalkyl radical, R.sub.2 is a hydrogen atom or an alkyl, alkenyl, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl or hydrazinocarbonyl radical or R.sub.1 and R.sub.2, together with the carbon atom to which they are attached, form a cycloalkyl ring, X is a valency bond or an alkylene or vinylene radical, R.sub.3 is an aromatic heterocyclic five-membered ring containing 1 to 4 heteroatoms or pyridinyl which the five- and six-membered rings are optionaly substituted one or more times by alkyl, alkoxy, alkoxycarbonyl, carboxyl, alkylthio, hydroxyl, nitro, amino, halogen or cyano and the tautomers, optically-active forms and physiologically acceptable salts thereof with inorganic and organic acids.
    Type: Grant
    Filed: March 23, 1989
    Date of Patent: October 15, 1991
    Assignee: Boehringer Mannheim GmbH
    Inventors: Wolfgang von der Saal, Rainer Haag
  • Patent number: 4835167
    Abstract: The present invention provides new tricyclic benzotriazoles of the general formula: ##STR1## wherein Z is a hydrogen atom or an acyl radical, Y is an oxygen or sulphur atom or two hydrogen atoms and X is an oxygen or sulphur atom or a >CR.sub.1 R.sub.2 or >NR.sub.3 group, R.sub.1 is a hydrogen atom or an alkyl, alkenyl or cycloalkyl radical, R.sub.2 is a hydrogen atom or an alkyl, alkenyl or cyano group or a carbonyl group substituted by a hydroxyl, alkyl, alkoxy, amino, alkylamino, dialkylamino or hydrazino group or R.sub.2, together with R.sub.1, represents a cycloalkylene radical or R.sub.1 and R.sub.2 together form an alkylidene or cycloalkylidene radical and R.sub.3 is a hydrogen atom or an alkyl radical; the tautomers thereof and the physiologically acceptable acid-addition salts thereof with inorganic and organic acids.
    Type: Grant
    Filed: August 3, 1987
    Date of Patent: May 30, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Wolfgang Von Der Saal, Walter-Gunar Friebe, Alfred Mertens, Bernd Muller-Beckmann, Gisbert Sponer
  • Patent number: 4833243
    Abstract: Novel substituted carboxylic acid amide herbicides of the formula ##STR1## wherein n is an integer from 1 to 4each R is independently selected from hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, dialkylamino, nitro cyano and alkoxycarbonyl; and two R radicals taken together can represent methylenedioxy, dichloromethylenedioxy or difluoromethylenedioxy,R.sup.1 is hydrogen or alkyl,R.sup.2 and R.sup.3 are individually selected from hydrogen or a radical selected from alkyl, alkenyl, alkynyl, aralkyl, cycloalkyl, aryl and nitrogen-containing heterocycles, each of which radicals may be substituted and each of which radicals may, together with the nitrogen atom to which they are attached, form an optionally substituted, optionally partially unsaturated and optionally benzo-fused monocyclic or bicyclic radical, which may contain one or more further hetero-atoms, andX is oxygen or sulfur.
    Type: Grant
    Filed: December 4, 1984
    Date of Patent: May 23, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Forster, Wolfgang Hofer, Volker Mues, Ludwig Eue, Robert R. Schmidt
  • Patent number: 4831032
    Abstract: The present invention provides benzimidazoles of the general formula: ##STR1## wherein R.sub.1, X, A, and R.sub.2 are as defined in the specification. The present invention also provides processes for the preparation of these new benzimidazoles and pharmaceutical compositions containing them, as well as intermediates for the preparation thereof.The new benzimidazoles are useful to treat heart or circulatory diseases which respond to a lowering of blood pressure, a positive inotropic action and/or an improvement in microcirculation.
    Type: Grant
    Filed: July 3, 1986
    Date of Patent: May 16, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Wolfgang von der Saal, Alfred Mertens, Herbert Berger, Bernd Muller-Beckmann, Klaus Strein
  • Patent number: 4764622
    Abstract: A light-collecting system, which contains a coumarin derivative of the formula ##STR1## in which T denotes O or NR.sub.4,R.sub.4 represents hydrogen, optionally substituted aryl, cycloalkyl or aralkyl,R.sub.1 denotes a carbocyclic or heterocyclic 5 or 6 membered ring bonded via a C.atom, or a 5 or 6 membered heterocyclic ring which is bonded via a N atom and is rotationally asymmetrical to an axis placed through the coumarin/N-heterocyclic bond, the 5 or 6 membered rings may carry non-ionic substituents and for an optionally substituted benzene ring or naphthalene ring to be fused to the said rings;X signifies ##STR2## or --OR.sub.2 ', R.sub.2 represents hydrogen, alkyl, cycloalkyl, aralkyl or aryl, hydrocarbon radicals may be substituted, andR.sub.3, in addition to having the definitions given for R.sub.2, also signifies a radical of the formulaeR.sub.6 --(X).sub.n --CO-- or R.sub.7 --(X).sub.n --SO.sub.2 --R.sub.6 and R.sub.
    Type: Grant
    Filed: October 17, 1986
    Date of Patent: August 16, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Claussen, Horst Harnisch