Cyano Or -c(=x)-, Wherein X Is Chalcogen, Attached Directly Or Indirectly To The Oxazole Ring By Nonionic Bonding Patents (Class 548/236)
  • Patent number: 5468761
    Abstract: Compound of formula (I): ##STR1## in which: R.sub.1 represents 1-adamantyl, dicyclopropylmethyl, substituted or unsubstituted (C.sub.3 -C.sub.6) cycloalkyl or substituted or unsubstituted bicyclo[2.2.2]oct-1-yl,R.sub.2 represents: ##STR2## in which: m represents 1, 2 or 3,X represents oxygen or sulfur or N--R,R.sub.3 or R.sub.4, which are identical or different, represent hydrogen, (C.sub.1 -C.sub.6) alkyl or trifluoromethyl, ##STR3## n represents 0, 1 or 2, R.sub.5 represents hydroxy, or (C.sub.1 -C.sub.6) alkoxy, and anti-inflammatory medicinal products containing the same.
    Type: Grant
    Filed: December 9, 1993
    Date of Patent: November 21, 1995
    Assignee: Adir et Compagnie
    Inventors: Guillaume de Nanteuil, Michel Vincent, Christine Lila, Jacqueline Bonnet, Armel Fradin
  • Patent number: 5464849
    Abstract: Compounds of formula I ##STR1## or salts thereof, where R is alkyl, phenyl, phenoxy or substituted phenyl and phenoxy; X is S or O; n is an integer of 1 or 2; A is --CH.sub.2 -- or --CH(CH.sub.3)--; and B is hydrogen or methyl, useful as antiallergy and antiinflammatory agents.
    Type: Grant
    Filed: October 5, 1994
    Date of Patent: November 7, 1995
    Assignee: Pfizer Inc.
    Inventors: Takashi Mano, Rodney W. Stevens, Masami Nakane
  • Patent number: 5463070
    Abstract: Certain 1-(benzyl or 5-benzofuranylmethyl)-1-hydroxyurea derivatives are useful as hypoglycemic and hypocholesterolemic agents.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: October 31, 1995
    Assignee: Pfizer Inc.
    Inventors: Steven W. Goldstein, Ruth E. McDermott
  • Patent number: 5461067
    Abstract: A retroviral protease inhibiting compound of the formula: ##STR1## is disclosed wherein R.sub.1, R.sub.2, R.sub.5, R.sub.6, Y.sub.m and Y'.sub.n are herein defined.
    Type: Grant
    Filed: February 1, 1994
    Date of Patent: October 24, 1995
    Assignee: Abbott Laboratories
    Inventors: Daniel W. Norbeck, Hing L. Sham, Dale J. Kempf, Chen Zhao
  • Patent number: 5459154
    Abstract: This invention relates to compounds having 5-lipoxygenase inhibiting properties and inhibition of oxidative modification of low density lipoprotein which have the formula: ##STR1## wherein: R.sup.1 and R.sup.3 are independently hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, trifluoromethyl, or C.sub.1 -C.sub.6 trifluoroalkoxy;R.sub.2 is hydrogen or methyl;R.sup.4 is hydrogen, methyl or hydroxy;R.sup.5 is hydrogen, --NH.sub.2, C.sub.1 -C.sub.6 alkyl, aryl, aralkyl, or --N.dbd.C(CH.sub.3).sub.2 ;X and Y are independently O or S;and n is 0 or 1; or a pharmaceutically acceptable salt thereof.Compounds which inhibit 5-lipoxygenase are useful in the treatment of diseases mediated by leukotrienes such as inflammation or bronchoconstriction. Compounds which inhibit oxidative metabolism of low density lipoprotein are useful in the inhibition of atherosclerotic plaque formation.
    Type: Grant
    Filed: November 8, 1993
    Date of Patent: October 17, 1995
    Assignee: American Home Products Corporation
    Inventors: Michael S. Malamas, James A. Nelson
  • Patent number: 5457122
    Abstract: The phenylalkan(en)oic acids of the formula: ##STR1## as defined herein, possess an antagonistic activity on leukotriene B.sub.4.
    Type: Grant
    Filed: July 13, 1993
    Date of Patent: October 10, 1995
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Mitoshi Konno, Takahiko Nakae, Nobuyuki Hamanaka
  • Patent number: 5446166
    Abstract: A process for preparation of new or previously known pyrrol derivatives is provided. The process involves reacting a nitroalkane or a nitroalkene with an isocyanoacetate in the presence of a proprophosphatrane "super base" to prepare the pyrrol compounds. Through production of new pyrrol compounds, new pyrrol derivatives such as dipyrromethane and porphyrin may be synthesized. In addition, the high yields of pyrrol compounds produced according to the method of the invention provide for more efficient production of previously known dipyrromethane and porphyrin compounds. The invention further provides a mild, high yield process for de-esterification of esterified pyrrol and dipyrromethane compounds. The invention also provides a synthetic method for the production of high yields of oxazoles through reaction of an aryl halide or acid anhydride with an isocyanoacetate in the presence of a prophosphatrane "super base".
    Type: Grant
    Filed: August 16, 1994
    Date of Patent: August 29, 1995
    Assignee: Iowa State University Research Foundation, Inc.
    Inventors: John Verkade, Jiansheng Tang
  • Patent number: 5436347
    Abstract: A method is provided for preparing a chiral benzaldehyde of the structure ##STR1## by acylating an anhydride of the structure ##STR2## with a chiral oxazolidine of the structure ##STR3## where Q is MgHal or Li, and X, Y and Z are as described herein, to form a keto acid which is reduced and cyclized. The resulting benzaldehyde may be used in making the final anti-thrombotic--anti-vasospastic compounds. Novel intermediates are also provided.
    Type: Grant
    Filed: May 20, 1994
    Date of Patent: July 25, 1995
    Assignee: Bristol-Myers Squibb Company
    Inventors: Sharon D. Real, David R. Kronenthal
  • Patent number: 5434267
    Abstract: Process for the preparation of compounds of the formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, X and n have the meaning given in the description, by reacting acetates with carbon monoxide in the presence of a basic auxiliary, followed by alkylation. The products are intermediates for fungicidal acrylates.
    Type: Grant
    Filed: March 14, 1994
    Date of Patent: July 18, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Helmut Kraus, Alexander Klausener, Hans-Joachim Diehr
  • Patent number: 5430162
    Abstract: The invention provides compounds of formula ##STR1## wherein X, R and R.sup.1 are defined in the specification. These compounds are useful as antibiotic agents.
    Type: Grant
    Filed: March 21, 1994
    Date of Patent: July 4, 1995
    Assignee: American Cyanamid Company
    Inventors: Phaik-Eng Sum, Ving J. Lee, Joseph J. Hlavka, Raymond T. Testa
  • Patent number: 5424455
    Abstract: A heterocyclic compound of the formula, ##STR1## wherein A and B are each hydrogen, halogen, alkyl or alkoxy, R.sup.1 is alkylene having upto 6 carbon atoms, X is direct linkage or divalent group such as --O--, --S--and the like, T and U are each hydrogen or alkyl, l is 0 or 1 to 3, Q is 5-, 6- or 7- membered saturated or unsaturated heterocyclic residue, and Y is hydrogen, halogen, alkyl, alkoxy or ##STR2## and B are taken together with each other to form methylene-dioxy, which is useful for dyeing or printing hydrophobic fiber materials with superior dyeability to give a dyed or printed product of a red color excellent in fastness properties, particularly those such as washing fastness.
    Type: Grant
    Filed: July 28, 1993
    Date of Patent: June 13, 1995
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Jun Yamamoto, Yasuyoshi Ueda, Junichi Sekihachi, Yosuke Yamamoto, Takashi Omura
  • Patent number: 5422359
    Abstract: Alpha-aminoketone derivatives of the present invention strongly inhibit thiol protease such as papain, cathepsin B, cathepsin H, cathepsin L and calpain or the like and have excellent properties in absorbance on oral administration, tissue distribution and cell membrane permeability. The alpha-aminoketone derivatives can thus be used as therapeutic agents for treating muscular dystrophy, amyotrophy, cardiac infarction, stroke, Alzheimer's disease, disturbance of consciousness or dyskinesia caused upon brain trauma, multiple sclerosis, peripheral nervous neuropathy, cataract, inflammation, allergosis, fulminant hepatitis, osteoporosis, hypercalcemia, breast carcinoma, prostatic carcinoma or prostatomegaly. They may also be used as therapeutic agents for suppressing growth of cancer cells, preventing metastasis of cancer or suppressing aggregation of plaques.
    Type: Grant
    Filed: December 22, 1993
    Date of Patent: June 6, 1995
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Ryoichi Ando, Toshiro Sakaki, Yasuhiro Morinaka, Chizuko Takahashi, Yoshikuni Tamao
  • Patent number: 5418247
    Abstract: 3,4,N-Trisubstituted-4,5-dihydro-1H-pyrazole-1-carboxamide compounds wherein the substituent in the 4-position is a 5-membered heterocyclic ring moiety containing one ring oxygen or sulfur atom and one or two ring nitrogen atoms and the substituents in the 3-posit ion and the N-position are optionally substituted phenyl moieties, such as 4,5-dihydro-3-(4-fluorophenyl)-N-(4-trifluoromethylphenyl)-4-(2-trifluorom ethyl-5-thiazolyl)-1H-pyrazole-1-carboxamide were prepared from appropriate 3,4-disubstituted-4,5-dihydro-1H-pyrazole compounds, such as 4,5-dihydro-3-(4-fluorophenyl)-4-(2-trifluoromethyl-5-thiazolyl)-1H-pyrazo le and phenyl is ocyanates and isothiocyanates, such as 4-(trifluoromethyl)phenyl isocyanate. The compounds are insecticidal.
    Type: Grant
    Filed: October 14, 1993
    Date of Patent: May 23, 1995
    Assignee: DowElanco
    Inventors: Michael J. Ricks, Yulan C. Tong
  • Patent number: 5403852
    Abstract: Oxazole derivatives of the formula ##STR1## wherein R and R' are each hydrogen or alkyl containing 1 or 2 carbon atoms, R.sub.1 and R.sub.2 are the same or different and represent hydrogen, halogen or straight- or branched-chain (C.sub.1-4) alkyloxy radicals, and n is 3-6; their salts their isomers and mixtures and their preparation method, are method are described. These derivatives display anti-inflammatory activity.
    Type: Grant
    Filed: December 11, 1992
    Date of Patent: April 4, 1995
    Assignee: Laboratoire Roger Bellon
    Inventors: Michel Barreau, Michel Kryvenko, Marc-Pierre Lavergne, Auguste Techer
  • Patent number: 5401852
    Abstract: Intermediates for transforming (2S,3S)-2-amino-3-phenyl-1,3-propanediols into their (2R,3R)-enantiomers are described. The final compounds are useful intermediates for the synthesis of antibiotics like chloramphenicol, Thiamphenicol and Florfenicol.
    Type: Grant
    Filed: September 28, 1993
    Date of Patent: March 28, 1995
    Assignee: Zambon Group S.p.A.
    Inventors: Marco Villa, Claudio Giordano, Silvia Cavicchioli, Silvio Levi
  • Patent number: 5401868
    Abstract: The present invention relates to hitherto unknown intermediate of formula, in which R.sub.1 stands for hydrogen or a straight or branched aliphatic C.sub.1 -C.sub.20 carbon chain or an aryl or aralkyl group, aryl and "ar" meaning an aromatic or heterocyclic, 5- or 6-membered ring substituent containing 1 or 2 hetero atoms selected among O, S and N, R.sup.1 optionally being further substituted, and its chain being interrupted by hetero atoms like oxygen, or by carbonyl group(s); and R.sup.3 stands for hydrogen or C.sub.1 -C.sub.3 alkyl. The present intermediates can be used in a one step method for producing prodrugs of formula, where D-H =drug itself.
    Type: Grant
    Filed: February 26, 1992
    Date of Patent: March 28, 1995
    Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Productionsaktieselskab)
    Inventor: Frantz J. Lund
  • Patent number: 5399561
    Abstract: Compounds of the formula ##STR1## where R.sub.1 and R.sub.2 are hydrogen, lower alkyl of 1-6 carbons, or halogen; R.sub.3 is hydrogen, lower alkyl of 1-6 carbons, halogen, OR.sub.11, SR.sub.11, OCOR.sub.11, SCOR.sub.11, NH.sub.2, NHR.sub.11, N(R.sub.11).sub.2, NHCOR.sub.11 or NR.sub.11 COR.sub.11 ; X is O, S or NR' where R' is hydrogen or lower alkyl of 1-6 carbons; Y is phenyl or a heteroaryl group selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl and oxazolyl; 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: January 7, 1994
    Date of Patent: March 21, 1995
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. Chandraratna
  • Patent number: 5391564
    Abstract: Rhizoxin and rhizoxin-2-ene derivatives of formula (I): ##STR1## in which: n is 1 to 25: A is an extra bond or oxygen, X is oxygen, sulfur, nitrogen or carbonyl; and R is hydrogen, carboxylic acyl having from 1 to 25 carbon atoms, alkoxycarbonyl group having from 2 to 26 carbon atoms, phosphono, alkylphosphono group in which the alkyl part has from 1 to 25 carbon atoms, dialkylphosphono group in which each alkyl part has from 1 to 25 carbon atoms, alkyl group having from 1 to 25 carbon atoms, aralkyl, cycloalkyl, heterocyclic, alkylthio group in which the alkyl part has from 1 to 25 carbon atoms, aralkylthio, or heterocyclylthio, or when X represents a nitrogen atom, R is R.sup.1 and R.sup.2, where R.sup.1 and R.sup.2 are hydrogen, alkyl, acyl, alkoxycarbonyl, phosphono, alkylphosphono or dialkylphosphono have valuable anti-tumor activity. They may be prepared by acylation of rhizoxin or rhizoxin-2-ene.
    Type: Grant
    Filed: February 14, 1994
    Date of Patent: February 21, 1995
    Assignee: Sankyo Company, Limited
    Inventors: Masakatsu Kaneko, Makoto Kamokari, Tomowo Kobayashi, Kazuhiko Sasagawa
  • Patent number: 5380738
    Abstract: 2-Substituted-4-(4-fluorophenyl)-5-(4-(methylsulfonyl)phenyl)oxazoles or 2-substituted-5-(4-fluorophenyl)-4-(4-(methylsulfonyl)phenyl)oxazoles and derivatives thereof are found to posses significant antiinflammatory activity, especially useful for the treatment of arthritis without deleterious side effects.
    Type: Grant
    Filed: May 21, 1993
    Date of Patent: January 10, 1995
    Assignee: Monsanto Company
    Inventors: Bryan H. Norman, Len F. Lee, Jaime L. Masferrer, John J. Talley
  • Patent number: 5380854
    Abstract: A novel series of oxazole derivatives having enhanced water solubility bioavailability and metabolic stability is disclosed in the Formula I ##STR1## or pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: July 14, 1993
    Date of Patent: January 10, 1995
    Assignee: Bristol-Myers Squibb Company
    Inventors: Jeffrey L. Romine, Nicholas A. Meanwell, Scott W. Martin
  • Patent number: 5378721
    Abstract: Compounds of formula I ##STR1## wherein Z, X, R, R.sub.0, R.sub.1, R.sub.2 and R.sub.3 are as defined in the description, have valuable pharmaceutical properties and are effective especially against tumors. They are prepared in a manner known per se.
    Type: Grant
    Filed: June 24, 1993
    Date of Patent: January 3, 1995
    Assignee: Ciba-Geigy Corporation
    Inventor: Marc Lang
  • Patent number: 5374643
    Abstract: Novel compounds useful, for example, in the treatment of ischemic conditions and arrhythmia having the formula I ##STR1## wherein X is oxygen, sulfur or --NCN and the R groups are as defined herein.
    Type: Grant
    Filed: August 12, 1993
    Date of Patent: December 20, 1994
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Karnail S. Atwal, George C. Rovnyak
  • Patent number: 5371098
    Abstract: An oxazole compound having the formula (I): ##STR1## in which A is a group of the formula --CH.sub.2 OR.sup.2 (wherein R.sup.2 is a hydrogen atom, an optionally substituted hydrocarbon residue, an optionally substituted heterocyclic group or an acyl group) or an aldehyde group, B is an optionally substituted phenyl group, R.sup.1 is a hydrogen atom or an optionally substituted alkyl group, and n is an integer of 0 to 6, provided that when n is 2, R.sup.1 is an optionally substituted alkyl group, or its salt, which is useful as a therapeutic agent for metabolic bone diseases including osteoporosis.
    Type: Grant
    Filed: August 13, 1992
    Date of Patent: December 6, 1994
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Takashi Sohda, Iwao Yamazaki, Yu Momose
  • Patent number: 5366984
    Abstract: Methyl .alpha.-arylacrylates substituted by a heterocyclic radical and having the general formula ##STR1## where R is alkyl, alkenyl, haloalkyl, cycloalkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, halogen or aryl, the aromatic ring being unsubstituted or substituted, Het is a five-membered heteroaromatic ring which is unsubstituted or substituted and has from one to three heteroatoms, and A is ethenylene, ethylene, methyleneoxy or methylenethio, and fungicides and pesticides containing these compounds.
    Type: Grant
    Filed: December 3, 1993
    Date of Patent: November 22, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Schuetz, Hans-Juergen Neubauer, Thomas Kuekenhoehner, Ulrich Schirmer, Peter Hofmeister, Christoph Kuenast, Eberhard Ammermann, Gisela Lorenz, Uwe Kardorff
  • Patent number: 5364944
    Abstract: There are disclosed substituted benzoylbenzene-, biphenyl- and 2-oxazole- alkanoic acid derivatives and the pharmacologically acceptable salts thereof as inhibitors of PLA.sub.2 and lipoxygenase, and their use in the treatment of inflammatory conditions, such as rheumatoid arthritis, ulcerative colitis, psoriasis and other immediate hypersensitivity reactions; in the treatment of leukotriene-mediated naso-bronchial obstructive air-passageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like; and as gastric cytoprotective agents.
    Type: Grant
    Filed: January 6, 1993
    Date of Patent: November 15, 1994
    Assignee: American Home Products Corporation
    Inventors: Amedeo A. Failli, Anthony F. Kreft, III, John H. Musser, Annette L. Banker, James A. Nelson, Uresh S. Shah, Dennis M. Kubrak
  • Patent number: 5364844
    Abstract: Compounds of formula (I): ##STR1## A is a carbon-carbon bond or C.sub.1 -C.sub.3 alkylene; B is imino group or C.sub.1 -C.sub.2 alkylene; R.sup.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, heterocyclic or optionally substituted amino; R.sup.2 is optionally substituted phenyl or optionally substituted naphthyl; R.sup.3 is thiazolyl, isoxazolyl or imidazolyl; R.sup.4 is isopropyl or cyclohexyl; R.sup.5 and R.sup.6 are C.sub.1 -C.sub.4 alkyl, or, together with the carbon atom to which they are attached, C.sub.3 -C.sub.7 cycloalkyl; R.sup.7 is hydrogen, optionally substituted C.sub.1 -C.sub.6 alkyl group; and R.sup.8 is hydrogen or C.sub.1 -C.sub.4 alkyl. These compounds have renin-inhibitory and, hence, hypotensive activities. The invention also provides a method for the treatment or prophylaxis of hypertension induced by failures in the renin-angiotensin system.
    Type: Grant
    Filed: August 27, 1992
    Date of Patent: November 15, 1994
    Assignee: Sankyo Company, Limited
    Inventors: Yasuhiro Morisawa, Mitsuru Kataoka, Yuichiro Yabe, Hiroyuki Koike, Yasuteru Iijima, Hidekuni Takahagi, Tatsuo Kokubu, Kunio Hiwada
  • Patent number: 5362879
    Abstract: A novel series of oxazole derivatives having the Formulae I and II ##STR1## wherein R is H or C.sub.1 -C.sub.5 lower alkyl,X is N or CH,Y is H or CO.sub.2 R.sup.1, or CO.R.sup.2, provided that when X isCH, Y is not H,R.sup.1 is C.sub.1 -C.sub.5 lower alkyl, or phenylmethyl, andR.sup.2 is C.sub.1 -C.sub.5 alkyl; ##STR2## wherein R is H or C.sub.1 -C.sub.5 lower alkyl,X is (CH.sub.2).sub.n or para or meta substituted phenylwherein the substituent is OR.sup.2,R.sup.2 is C.sub.1 -C.sub.5 alkyl, andn is an integer of 4 to 8,or a pharmaceutically acceptable salt thereof.The compounds are useful as inhibitors of ADP-induced blood platelet aggregation in human platelet-rich plasma.
    Type: Grant
    Filed: April 15, 1993
    Date of Patent: November 8, 1994
    Assignee: Bristol-Myers Squibb Company
    Inventor: Nicholas A. Meanwell
  • Patent number: 5352689
    Abstract: Rhizoxin and rhizoxin-2-ene derivatives of formula ##STR1## in which: n is 1 to 25; A is an extra bond or oxygen, X is oxygen, sulfur, nitrogen or carbonyl; and R is hydrogen, carboxylic acyl having from 1 to 25 carbon atoms, alkoxycarbonyl group having from 2 to 26 carbon atoms, phosphono, alkylphosphono group in which the alkyl part has from 1 to 25 carbon atoms, dialkylphosphono group in which each alkyl part has from 1 to 25 carbon atoms, alkyl group having from 1 to 25 carbon atoms, aralkyl, cycloalkyl, heterocyclic, alkylthio group in which the alkyl part has from 1 to 25 carbon atoms, aralkylthio, or heterocyclylthio, or when X represents a nitrogen atom, R is R.sup.1 and R.sup.2, where R.sup.1 and R.sup.2 are hydrogen, alkyl, acyl, alkoxycarbonyl, phosphono, alkylphosphono or dialkylphosphono, have valuable anti-tumor activity. They may be prepared by acylation of rhizoxin or rhizoxin-2-ene.
    Type: Grant
    Filed: September 27, 1993
    Date of Patent: October 4, 1994
    Assignee: Sankyo Company, Limited
    Inventors: Masakatsu Kaneko, Makoto Kamokari, Tomowo Kobayashi, Kazuhiko Sasagawa
  • Patent number: 5348969
    Abstract: A novel series of oxazole derivatives having enhanced water solubility bioavailability and metabolic stability is disclosed in the Formula I ##STR1## Y is CH.sub.3, Ph, or OH, provided that when Y is OH, the compound exists in the keto-enol tautaumerism form ##STR2## R.sup.1 is Ph or Th; R.sup.2 is H or CH.sub.2 R.sup.3 ;R.sup.3 is H, OCH.sub.3, C.sub.1 -C.sub.5 lower alkyl, or CO.sub.2 R.sup.4 ;R.sup.4 is H or C.sub.1 -C.sub.5 lower alkyl;R.sup.5 is H or CH.sub.3 ;R.sup.6 is OHCHN or H.sub.2 N; andR.sup.7 is H or OH;or pharmaceutically acceptable salt thereof.The compounds are useful as inhibitors of ADP-induced blood platelet aggregation in human platelet-rich plasma.
    Type: Grant
    Filed: April 3, 1992
    Date of Patent: September 20, 1994
    Assignee: Bristol-Myers Squibb Company
    Inventors: Jeffrey L. Romine, Nicholas A. Meanwell
  • Patent number: 5346895
    Abstract: Novel compounds of the formula ##STR1## where X is S, O; R.sub.1 -R.sub.5 are hydrogen or lower alkyl; R.sub.6 is lower alkyl, lower alkenyl, lower cycloalkyl having 1 to 6 carbons, or halogen; A is lower branched chain alkyl having 2 to 6 carbons, cycloalkyl having 3 to 6 carbons, alkenyl having 2 to 6 carbons and 1 or 2 double bonds, alkynyl having 2 to 6 carbons and 1 or 2 triple bonds, (CH.sub.2).sub.n where n is 0-5; and B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, COONR.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", CR"(OR.sub.12).sub.2, or CR"OR.sub.13 O, where R" is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R.sub.8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.
    Type: Grant
    Filed: January 6, 1993
    Date of Patent: September 13, 1994
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5340832
    Abstract: A novel prolinal derivative of the general formula: ##STR1## [wherein A represents alkylene or alkenylene group of from 1 to 8 carbon atom(s) or a saturated hydrocarbon ring of from 3 to 7 carbon atoms, R represents hydrogen atom, phenyl group, benzyl group, alkyl group of from 1 to 8 carbon atom(s) or cycloalkyl group of from 3 to 7 carbon atoms,B represents alkylene group of from 1 to 8 atom(s) unsubstituted or substituted by phenyl group or benzyl group, or a single bond,D represents carbocyclic or heterocyclic ring unsubstituted or substituted by from one to three of halogen atom, alkyl or alkoxy group of from 1 to 4 carbon atom(s), nitro group or trifluoromethyl group.]possess inhibitory activity on prolyl endopeptidase, and therefore are useful for treating and/or preventing agent as a amnesia.
    Type: Grant
    Filed: August 17, 1993
    Date of Patent: August 23, 1994
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Masaaki Toda, Shuichi Ohuchida, Hiroyuki Ohno
  • Patent number: 5338856
    Abstract: 3,4,N-Trisubstituted-4,5-dihydro-1H-pyrazole-1-carboxamide compounds wherein the substituent in the 4-position is a 5-membered heterocyclic ring moiety containing one ring oxygen or sulfur atom and one or two ring nitrogen atoms and the substituents in the 3-position and the N-position are optionally substituted phenyl moieties, such as 4,5-dihydro-3-(4-fluorophenyl)-N-(4-trifluoromethylphenyl)-4-(2-trifluorom ethyl-5-thiazolyl)-1H-pyrazole-1-carboxamide were prepared from appropriate 3,4-disubstituted-4,5-dihydro-1H-pyrazole compounds, such as 4,5-dihydro-3-(4-fluorophenyl)-4-(2-trifluoromethyl-5-thiazolyl)-1H-pyrazo le and phenyl isocyanates and isothiocyanates, such as 4-(trifluoromethyl)phenyl isocyanate. The compounds are insecticidal.
    Type: Grant
    Filed: August 17, 1992
    Date of Patent: August 16, 1994
    Assignee: DowElanco
    Inventors: Michael J. Ricks, Yulan C. Tong
  • Patent number: 5334604
    Abstract: There are disclosed preparative processes and hypoglycemic compounds of the formula ##STR1## wherein R is hydrogen or C1 to C3 alkyl;R.sup.1 and R.sup.2 are taken together and are carbonyl; or R.sup.1 and R.sup.2 are taken separately, wherein R.sup.1 is hydrogen or R.sup.4 and R.sup.2 is--COR.sup.5 and COOR.sup.5 ;R.sup.3, R.sup.4 and R.sup.5 are each independently C1 to C9 alkyl, C3 to C7 cycloalkyl, phenyl, naphthyl, furyl, benzofuryl or thienyl or one of said groups mono- or disubstituted with C1 to C3 alkyl, C1 to C3 alkoxy, C1 to C3 alkoxy-carbonyl, trifluoromethyl, fluoro or chloro; and n is 0 or 1; or pharmaceutically acceptable cationic salts thereof.
    Type: Grant
    Filed: February 22, 1993
    Date of Patent: August 2, 1994
    Assignee: Pfizer Inc.
    Inventors: Steven W. Goldstein, Ruth E. McDermott
  • Patent number: 5324723
    Abstract: 1,3-Oxazole and 1,3-thiazole compounds of formula I, and their pharmaceutically acceptable salts and prodrugs: ##STR1## wherein X represents oxygen or sulphur;R.sup.1 represents a non-aromatic azacyclic or azabicyclic ring system.
    Type: Grant
    Filed: July 1, 1993
    Date of Patent: June 28, 1994
    Assignee: Merck Sharpe & Dohme Ltd.
    Inventors: Raymond Baker, John Saunders, Roger J. Snow, Graham A. Showell
  • Patent number: 5324837
    Abstract: 3,4-Diaryl-4,5-dihydro-1H-pyrazole compounds having a selected 5- or 6-membered aromatic heterocyclic moiety in the 4-position and an optionally substituted phenyl moiety in the 3-position, such as 4,5-dihydro-3-(4-fluorophenyl)-4-(5-trifluoromethyl-2-pyridinyl)-1H-pyrazo le were prepared as intermediates in the preparation of insecticidal 3,4,N-triaryl-4,5-dihydro-1H-pyrazole-1-carboxamide compounds. The 3,4-diaryl-4,5-dihydro-1H-pyrazole compounds can be prepared from appropriate 1,2-diarylethanone compounds by successive treatments with N,N,N',N'-tetramethyldiaminomethane in dichloromethane in the presence of acetic anhydride (to form a Mannich adduct) and hydrazine in the presence of a catalytic amount of trifluoroacetic acid.
    Type: Grant
    Filed: August 17, 1992
    Date of Patent: June 28, 1994
    Assignee: DowElanco
    Inventors: James M. Renga, Kevin L. McLaren, James T. Pechacek, Michael J. Ricks, Yulan C. Tong
  • Patent number: 5321036
    Abstract: Compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof where A is ##STR2## R.sub.3 is --(CH.sub.2).sub.n -- or in the case where R.sub.2 is ##STR3## R.sub.3 in addition to the above may be ##STR4## R.sub.4 is hydroxy, alkoxy, amino, alkylamino or dialkylamino; R.sub.5 is hydrogen, fluorine, chlorine, bromine, iodine, --CN, CF.sub.3, lower alkyl, lower alkoxy, cycloalkyl or aryl;R.sub.6 is lower alkyl, cycloalkyl or aryl;R.sub.7, R.sub.7 ', R.sub.8 and R.sub.8 ' are independently hydrogen or a lower alkyl or R.sub.7 and R.sub.8 may together be CH.sub.2 CH.sub.2 ;Z is hydrogen or ##STR5## m is an integer of 1 or 2; n is zero or an integer of 1 to 6; andp is an integer of 1 to 5. These compounds are beta 3 adrenergic receptor agonists and are useful, therefore for example, in the treatment of diabetes, obesity and gastrointestinal diseases.
    Type: Grant
    Filed: February 10, 1993
    Date of Patent: June 14, 1994
    Assignee: Bristol-Myers Squibb Company
    Inventor: Philip M. Sher
  • Patent number: 5312826
    Abstract: Disclosed are a dicarboxylic acid compound represented by the formula (I): ##STR1## wherein R represents hydrogen atom, a lower alkyl group, phenyl group or hydroxyl group; R.sup.1 represents a straight or branched alkyl group having 1 to 10 carbon atoms or a lower alkyl group substituted by a group selected from aryl group, a sulfur- or nitrogen-containing heterocyclic monocyclic group and a cycloalkyl group having 4 to 8 carbon atoms; R.sup.2 represents a substituted or unsubstituted aryl group, a cycloalkyl group having 4 to 8 carbon atoms or a sulfur-containing or nitrogen-containing heterocylcic group; X represents sulfur atom, oxygen atom or a substituted or unsubstituted imino group; Y.sup.1 represents imino group, oxygen atom or sulfur atom and Y.sup.2 represents nitrogen atom, or Y.sup.1 represents a vinylene group and Y.sup.2 represents a group: --CH.dbd.
    Type: Grant
    Filed: June 19, 1992
    Date of Patent: May 17, 1994
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Ken-ichi Nunami, Tameo Iwasaki, Kazuo Matsumoto, Koji Yano, Isao Yamaguchi
  • Patent number: 5312831
    Abstract: The invention relates to novel ureas and urethanes of Formula I: ##STR1## which stimulate cytokine production and may be used to accelerate recovery from neutropenia accompanying radio- or chemotherapy, bone marrow transplantation, or infections. Compounds in the invention or pharmaceutical compositions employing these compounds may be useful in the treatment of cancer, AIDS, aplastic anemia, myelodysplastic syndrome, and infectious diseases, and in the enhancement of immune response.
    Type: Grant
    Filed: May 12, 1993
    Date of Patent: May 17, 1994
    Assignee: American Cyanamid Company
    Inventors: Semiramis Ayral-Kaloustian, Steven R. Schow, Mila T. Du, James J. Gibbons, Jr.
  • Patent number: 5296607
    Abstract: In chemical structure of a fulgide type photochromic compound having the following general formula; ##STR1## introduction of electron donative groups into its heteroaromatic structure is effective in improving the long wave length sensitivity without any lowering in its thermal stability. Thanks to such combined functional properties, the products are advantageously used for optical recording media, copying media, printing media, optical filters and display materials.
    Type: Grant
    Filed: June 23, 1992
    Date of Patent: March 22, 1994
    Assignee: Yamaha Corporation
    Inventors: Akihiko Tomoda, Hisao Suzuki, Akira Kaneko, Hideki Tsuboi
  • Patent number: 5294733
    Abstract: Preparation of cyclohexanediones of the formula ##STR1## are disclosed. An aldehyde of the formula R--CHO is reacted with a ketene type compound of the formula (R.sub.1) (R.sub.2) C.dbd.C.dbd.O to give a polymer: ##STR2## wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1) (R.sub.2)--COOR.sub.3, the acids in the mixture are converted for esters. The hydroxy ester of the ester mixture is converted to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3. The unsaturated ester is contacted with a basic catalyst to cyclize it to the cyclic dione ester of the formula ##STR3## and this ester is then hydrolyzed and decarboxylated to give the product ##STR4## wherein: R is selected, e.g.
    Type: Grant
    Filed: May 20, 1993
    Date of Patent: March 15, 1994
    Assignee: Eastman Kodak Company
    Inventor: Charles A. McCombs
  • Patent number: 5290798
    Abstract: Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion, dysmenorrhea, and migraine.
    Type: Grant
    Filed: September 25, 1992
    Date of Patent: March 1, 1994
    Assignee: Merck Frosst Canada, Inc.
    Inventors: John W. Gillard, John H. Hutchinson, Michel Therien
  • Patent number: 5290799
    Abstract: 7-Oxabicycloheptane substituted prostaglandin analogs useful in treating thrombotic and vasospastic disease have the structural formula ##STR1## wherein m is 1, 2 or 3; n is 1, 2, 3 or 4; Z is --(CH.sub.2).sub.2 --, --CH.dbd.CH-- or ##STR2## wherein Y is O, a single bond or vinyl, with the proviso that when n is O, if Z is ##STR3## then Y cannot be O, and when Z is --CH.dbd.CH--, n is 1, 2, 3 or 4; and when Y=vinyl, n=0; R is CO.sub.2 H, CO.sub.2 lower alkyl, CH.sub.2 OH, CO.sub.2 alkali metal, CONHSOR.sup.3, CONHR.sup.3a or --CH.sub.2 -5-tetrazolyl, X is O, S or NH; and where R.sup.1, R.sup.2, R.sup.3 and R.sup.3a are as defined herein.
    Type: Grant
    Filed: September 19, 1990
    Date of Patent: March 1, 1994
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Raj N. Misra, Philip M. Sher, Philip D. Stein, Steven E. Hall, David Floyd, Joel C. Barrish
  • Patent number: 5288732
    Abstract: Novel fungicides of the formula ##STR1## in which R.sup.1 represents optionally substituted hydroxyalkyl, optionally substituted hydroxyalkoxyalkyl, optionally substituted heteroarylalkyl or optionally substituted heteroaryl, andR.sup.2 represents optionally substituted alkyl, optionally substituted alkenyl, or alkinyl.Intermediates therefor, wherein R.sup.2 is hydrogen or an alkali metal cation, are also new.
    Type: Grant
    Filed: March 31, 1993
    Date of Patent: February 22, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Herbert Gayer, Klaus Jelich, Winfried Lunkenheimer, Wilhelm Brandes, Gerd Hanssler
  • Patent number: 5286741
    Abstract: There are provided N-oxy- and thioalkylcarbonyloxyalkylpyrrole compounds of formula I and their use for the control of insects, acarina and mollusks. Further provided are compositions and methods comprising those compounds for the protection of plants from attack by insects, acarina and mollusks.
    Type: Grant
    Filed: October 27, 1992
    Date of Patent: February 15, 1994
    Assignee: American Cyanamid Company
    Inventors: David G. Kuhn, Stephen F. Donovan, Joseph A. Furch
  • Patent number: 5284821
    Abstract: Oxazole- and thiazolecarboxamides of the formulae Ia and Ib ##STR1## where the substituents have the following meanings: X oxygen or sulfur;R.sup.1 hydrogen; halogen; substituted or unsubstituted C.sub.1 -C.sub.6 -alkyl, benzyl, cycloalkyl, alkenyl, alkynyl, phenyl, phenoxy or phenylthio; alkoxy; alkylthio; haloalkoxy; haloalkylthio; or a substituted or unsubstituted 5- or 6-membered heterocyclic radical;R.sup.2 formyl, 4,5-dihydrooxazol-2-yl or --COYR.sup.5 ;Y oxygen or sulfur;R.sup.5 hydrogen; cycloalkyl; substituted or unsubstituted alkyl, phenyl, benzyl, alkenyl, cycloalkenyl or alkynyl; a substituted or unsubstituted 5- or 6-membered heterocyclic radical; phthalimido; tetrahydrophthalimido; succinimido; maleiimido; one equivalent of a cation; or--N.dbd.CR.sup.6 R.sup.7 ;R.sup.6, R.sup.7 hydrogen; alkyl; cycloalkyl; phenyl; furyl or together a methylene chain of 4 to 7 members;R.sup.3 hydrogen or substituted or unsubstituted alkyl or cycloalkyl;R.sup.
    Type: Grant
    Filed: July 27, 1992
    Date of Patent: February 8, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Ditrich, Volker Maywald, Gerhard Hamprecht, Albrecht Harreus, Bruno Wuerzer, Karl-Otto Westphalen
  • Patent number: 5281716
    Abstract: A method is provided for preparing oxazole intermediates of the structure ##STR1## (wherein R is alkyl) wherein an oxazoline of the structure ##STR2## is oxidized employing an oxidizing agent such as cupric bromide, a base such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and a non-hydride donor amine base such as hexamethylenetetraamine (HMTA). The resulting oxazole may be hydrolyzed to the final anti-thrombotic - anti-vasospastic compounds.
    Type: Grant
    Filed: February 22, 1993
    Date of Patent: January 25, 1994
    Assignee: Bristol-Myers Squibb Company
    Inventors: Richard H. Mueller, Janak Singh
  • Patent number: 5280034
    Abstract: Thromboxane receptor antagonist activity is exhibited by compounds of the formula ##STR1## wherein: W is --(CH.sub.2).sub.m -- or ##STR2## but if R.sup.3 and R.sup.4 complete an aromatic ring, then W cannot be ##STR3## X is --(CH.sub.2).sub.2 --, --CH.dbd.CH-- or phenylene; Y is --O--, a single bond or vinylene, except that Y cannot be --O-- when n is 0, and if Y is vinylene, then n must be 0;Z is O or NH;R.sup.3 and R.sup.4 are each independently hydrogen, alkyl, alkenyl, or alkynyl, or R.sup.3 and R.sup.4 together complete a ring as defined in the specification, optionally substituted through a ring carbon with an oxo or hydroxyl group; and the remaining symbols are as defined in the specification.
    Type: Grant
    Filed: August 23, 1991
    Date of Patent: January 18, 1994
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Steven E. Hall, Philip M. Sher
  • Patent number: 5278184
    Abstract: Antirhinoviral compounds having the formula ##STR1## wherein R is hetrocyclic, particularly pyrrole or pyrrolidine, X is H.sub.2 or O, n IS 3 to 7, and R.sub.1 is substituted phenyl are disclosed.
    Type: Grant
    Filed: April 17, 1992
    Date of Patent: January 11, 1994
    Assignee: Repla Chemical Ltd.
    Inventors: Marino Artico, Federico Corelli, Silvio Massa, Antonello Mai, Enzo Tramontano
  • Patent number: 5276037
    Abstract: The invention concerns an aryl derivative of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl, naphthyl or a heterocyclic moiety, and X.sup.1 is oxy, thio, sulphinyl, sulphonyl, difluoromethylene, imino, (1-4C)alkylimino or optionally substituted (1-4C)alkylene, or X.sup.1 is a group of the formula--X.sup.4 --CR.sub.2 -- or --CR.sub.2 --X.sup.4 --whereinX.sup.4 is oxy, thio, sulphinyl, sulphonyl or carbonyl and each R is hydrogen, methyl or ethyl;each of Ar.sup.2 and Ar.sup.3 is optionally substituted phenylene;X.sup.2 is oxy, thio, sulphinyl or sulphonyl;R.sup.1 is (1-4C)alkyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.1 --X.sup.3 --A.sup.2 -- which together with the carbon atom to which A.sup.1 and A.sup.2 are attached define a ring having 5 to 7 ring atoms, wherein each of A.sup.1 and A.sup.2 is (1-3C)alkylene and X.sup.
    Type: Grant
    Filed: April 14, 1993
    Date of Patent: January 4, 1994
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Robert I. Dowell, Philip N. Edwards, Keith Oldham
  • Patent number: 5272167
    Abstract: Compounds of the formulaZ--X--Q--Y--Wpharmaceutically acceptable acid addition, basic addition salts or quaternary amine salts thereof, whereinZ is phenyl, substituted phenyl, wherein the substituents are independently one or more of halogen, lower alkylthio, loweralkylsulfonyl, lower alkoxy, oxazol-2-yl; imidazo-1-yl; lower alkyl substituted imidazo-1-yl; or tert-butyl;X is a bond, ##STR1## Q is lower alkane-diyl or 5, 6, or 7 carbon atoms optionally substituted by --OH; loweralkylnediyl of 6-8 carbon atoms; methylcyclohexylmethyl; tetrahydrofurandiyl; or (C.sub.1 -C.sub.2) lower alkane-diyl tetrahydrofurandiyl-C.sub.1 -C.sub.2 loweralkanediyl; wherein the tetrahydrofuran ring is substituted by 0-2 hydroxy groups;Y is a bond; andW is benzimidazol-1-yl or benzimidazol-2-yl are described. These compounds have antiviral activity, antiinflammatory activity and are PAF inhibitors.
    Type: Grant
    Filed: December 18, 1991
    Date of Patent: December 21, 1993
    Assignee: Schering Corporation
    Inventors: Viyyoor M. Girijavallabhan, Ashit K. Ganguly, Patrick A. Pinto, Richard W. Versace