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: 5264448
    Abstract: The present invention relates to certain novel amide compound represented by the formula of ##STR1## wherein A is an oxazole and, X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, Y, the ring B, R.sup.5, R.sup.6, l and m are the same as defined in the present specification, its production and an insecticidal and/or acaricidal composition containing it as an active ingredient.
    Type: Grant
    Filed: October 17, 1991
    Date of Patent: November 23, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Akira Shuto, Hirosi Kisida, Naoto Meki, Tomotoshi Imahase, Hiroaki Fujimoto, Kimitoshi Umeda
  • Patent number: 5262540
    Abstract: Oxazole derivatives having Formula I or II are disclosed which are useful as inhibitors of mammalian blood platelet aggregation. ##STR1## Formula I and Formula XIX compounds are those wherein n is 7-9 and R is hydrogen or lower alkyl. Formula II compounds are those wherein R is hydrogen, lower alkyl or together with CO.sub.2 is tetrazol-1-yl; R.sub.1 is phenyl or thienyl; X is a divalent connecting group selected from the group consisting of CH.sub.2 CH.sub.2, CH.dbd.CH, and CH.sub.2 O; Y is a divalent connecting group attached to the 3 or 4 phenyl position selected from the group consisting of OCH.sub.2, CH.sub.2 CH.sub.2 and CH.dbd.CH. Formula XX compounds are those wherein the OCH.sub.2 CO.sub.2 R moiety is attached to the 3 or 4 phenyl position and R is hydrogen or lower alkyl.
    Type: Grant
    Filed: May 10, 1993
    Date of Patent: November 16, 1993
    Assignee: Bristol-Myers Squibb Company
    Inventor: Nicholas A. Meanwell
  • Patent number: 5260449
    Abstract: A method is provided for preparing bromooxazole intermediates of the structure ##STR1## wherein a vinyl compound of the structure ##STR2## wherein X.sup.1 and X.sup.2 are independently H and Br, is treated with a metal halide such as cupric bromide, and a base such as 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU). The resulting bromooxazole may be hydrolyzed and hydrogenolyzed to the final anti-thrombotic-anti-vasospastic compounds.
    Type: Grant
    Filed: August 12, 1992
    Date of Patent: November 9, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Janak Singh, Richard H. Mueller, Jagabandhu Das, Philip M. Sher
  • Patent number: 5260448
    Abstract: A method is provided for preparing 7-oxabicycloheptyl substituted heterocyclic amide prostaglandin analogs which are thromboxane A.sub.2 (TXA.sub.2) receptor antagonists or combined thromboxane A.sub.2 receptor antagonists/thromboxane synthetase inhibitors useful, for example, in the treatment of thrombotic and/or vasospastic disease, wherein a vinyl bromide of the formula, for example, ##STR1## wherein m, n, R.sup.1 and R.sup.2 are as defined herein is treated with a cyclizing agent to form the corresponding oxazole.
    Type: Grant
    Filed: June 18, 1992
    Date of Patent: November 9, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jagabandhu Das, David Kronenthal
  • Patent number: 5258401
    Abstract: Disclosed herein are compounds of structural formula (I) ##STR1## which are useful as cholesterol lowering agents. These compounds are also useful as inhibitors of squalene synthase, inhibitors of fungal growth, inhibitors of farnesyl-protein transferase and farnesylation of the oncogene protein Ras. These compounds are also useful in the treatment of cancer.
    Type: Grant
    Filed: September 10, 1992
    Date of Patent: November 2, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Gregory D. Berger, Robert W. Marquis, Jr., Albert J. Robichaud, Edward M. Scolnick
  • Patent number: 5258357
    Abstract: Carboxamides of the formulae Ia to Ic ##STR1## where X is oxygen or sulfur;R.sup.1 is hydrogen or substituted or unsubstituted cycloalkyl or alkyl;R.sup.2 is hydroxy, alkoxy, cyanoalkyl, substituted or unsubstituted alkenyl, alkynyl, phenyl or naphthyl, a substituted or unsubstituted 5- to 6-membered heterocyclic structure or one of the groups stated for R.sup.1, orR.sup.1 and R.sup.2 together are a 4- to 7-membered chain which contains, in addition to methylene groups, one of the following groups as ring member: oxygen, sulfur, N-methyl or carbonyl;R.sup.3 and R.sup.4 are each nitro, cyano, halogen, substituted or unsubstituted amino, alkoxy, alkylthio, a substituted or unsubstituted 5- to 6 -membered heterocyclic structure, substituted or unsubstituted alkenyl, alkynyl, phenyl, phenoxy or phenylthio, or one of the groups stated for R.sup.1 ;R.sup.5 is formyl, 4,5-dihydrooxazol-2-yl or COYR.sup.6 (Y=O,S);R.sup.
    Type: Grant
    Filed: September 21, 1992
    Date of Patent: November 2, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Muenster, Gerd Steiner, Wolfgang Freund, Bruno Wuerzer, Karl-Otto Westphalen
  • Patent number: 5256632
    Abstract: Herbicidal sulphonylated carboxamides of the formulaR.sup.1 --CO--NH--SO.sub.2 --(A).sub.n --R.sup.2 (I)in whichn represents the numbers 0 or 1,A represents oxygen, iminio (NH) or methylene (CH.sub.2),R.sup.1 represents a five-membered heteroaryl radical which contains 1 or 2 nitrogen atoms and additionally one oxygen or sulphur atom in the ring and which is optionally substituted by halogen or by alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or phenyl which are in each case optionally substituted, andR.sup.2 represents aryl or heteroaryl which are in each case optionally substituted,or salts thereof, with the exclusion of the compound 2-dimethylamino-N-(4-methyl-phenylsulphonyl)-5-thiazole carboxamide.
    Type: Grant
    Filed: June 18, 1992
    Date of Patent: October 26, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hilmar Wolf, Rolf Kirsten, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
  • Patent number: 5254576
    Abstract: A novel series of oxazole derivatives having enhanced water solubility bioavailability and metabolic stability is disclosed in the Formula I ##STR1## X is ##STR2## R is CH.sub.2 R.sup.2, H; R.sup.1 is Ph or Th;R.sup.2 is ##STR3## H, CN, CO.sub.2 R.sup.3, or OR.sup.3 ; and R.sup.3 is H, or C.sub.1 -C.sub.4 lower alkyl;or pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: April 3, 1992
    Date of Patent: October 19, 1993
    Assignee: Bristol-Myers Squibb Company
    Inventors: Jeffrey L. Romine, Nicholas A. Meanwell, Scott W. Martin
  • Patent number: 5250501
    Abstract: A compound of formula (I): ##STR1## or a salt, enamine or the like, acylate, sulphonate, carbamate or ether derivative thereof; wherein X, X.sup.1 and X.sup.2 are independently oxygen or sulphur, R.sup.1 is an optionally substituted heterocyclic or cycloalkyl group, and Y is an optionally substituted C.sub.2 -C.sub.4 alkylene group which is optionally interposed by an oxygen atom, a group ##STR2## or an optionally mono-substituted nitrogen atom, wherein p is 0, 1 or 2, s is 0 or 1 and R.sup.b is alkyl or alkoxy; provided that when X, X.sup.1 and X.sup.2 are oxygen R.sup.1 is not pyridyl or pyrimidinyl. Processes for the preparation of these compounds and herbicidal compositions containing them are also described and claimed.
    Type: Grant
    Filed: January 10, 1992
    Date of Patent: October 5, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Americas, Inc.
    Inventors: John E. D. Barton, David Cartwright, John M. Cox, Glynn Mitchell, Charles G. Carter, David L. Lee, Francis H. Walker, Frank X. Woolard
  • Patent number: 5248784
    Abstract: A novel 4-carbonyl-substituted coumarin compound which is substituted with a carbonyl group in the position-4 of a 7-alkylaminocoumarin derivative and has photosensitivity in the visible region.
    Type: Grant
    Filed: April 16, 1992
    Date of Patent: September 28, 1993
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Tsukasa Ohyama, Kazuhiko Murayama, Yoriaki Matsuzaki, Susumu Kasamatsu, Keisuke Takuma, Kimitoshi Kato
  • Patent number: 5248682
    Abstract: The present invention is novel compounds which are 2-substituted-4,6-di-tertiarybutyl-5-hydroxy-1,3-pyrimidines and pharmaceutically acceptable acid addition or base salts thereof, pharmaceutical compositions and methods of use therefor. The invention compounds are now found to have activity as inhibitors of 5-lipoxygenase and/or cyclooxygenase providing treatment of conditions advantageously affected by such inhibition including inflammation, arthritis, pain, fever and the like. Thus, the present invention is also a pharmaceutical composition or method of manufacturing a pharmaceutical composition for the use of treating the noted conditions.
    Type: Grant
    Filed: August 3, 1992
    Date of Patent: September 28, 1993
    Assignee: Warner-Lambert Company
    Inventors: David T. Connor, Catherine R. Kostlan
  • Patent number: 5244867
    Abstract: Oxazole- and thiazolecarboxamides of the formulae Ia and Ib ##STR1## where the substituents have the following meanings: X oxygen or sulfur;R.sup.2 formyl, 4,5-dihydrooxazol-2-yl or --COYR.sup.5 ;Y oxygen or sulfur; andR.sup.4 is methyl and herbicidal agents containing compounds of the formulae Ia or Ib as active ingredients.
    Type: Grant
    Filed: December 26, 1991
    Date of Patent: September 14, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Ditrich, Volker Maywald, Gerhard Hamprecht, Albrecht Harreus, Bruno Wuerzer, Karl-Otto Westphalen
  • Patent number: 5240925
    Abstract: This invention relates to 2-aryl-2-cyano-2-(heterocyclylalkyl)ethyl-1,2,4-triazoles of the formula ##STR1## wherein Ar is an optionally substituted aryl group, Het is an optionally substituted five or six membered saturated or unsaturated heterocyclic ring containing one, two or three heteroatoms selected from oxygen, nitrogen and sulfur, or is a bicyclic unsaturated ring system containing up to ten atoms including one heteroatom selected from oxygen, nitrogen and sulfur, R is hydrogen or alkyl, n is zero or an integer of at least one, and the agronomically acceptable enantiomorphs, geometric isomers, acid addition salts and metal salt complexes thereof.
    Type: Grant
    Filed: August 26, 1991
    Date of Patent: August 31, 1993
    Assignee: Rohm and Haas Company
    Inventors: Steven H. Shaber, Ted T. Fujimoto, Katherine E. Flynn
  • Patent number: 5239080
    Abstract: Oxazole compounds having the formula: ##STR1## in which A is a group of the formula --CH.sub.2 OR.sup.3 (R.sup.3 is a hydrogen atom, an optionally substituted hydrocarbon residue, an optionally substituted heterocyclic group or an acyl group), or an aldehyde group and B is an optionally substituted phenyl group, or their salts, which are useful as antidiabetic agents.
    Type: Grant
    Filed: June 27, 1991
    Date of Patent: August 24, 1993
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Takashi Sohda, Hitoshi Ikeda, Yu Momose
  • Patent number: 5234937
    Abstract: The novel 3,5-di-tertiary-butyl-4-hydroxyphenyloxazolyl methanones and methanone oximes of the present invention are antiinflammatory agents having activity as inhibitors of 5-lipoxygenase, cyclooxygenase or both.
    Type: Grant
    Filed: October 17, 1991
    Date of Patent: August 10, 1993
    Assignee: Warner-Lambert Company
    Inventors: Thomas Capiris, David T. Connor, Jagadish C. Sircar
  • Patent number: 5234917
    Abstract: Angiotensin II receptor antagonists having the formula: ##STR1## which are useful in regulating hypertension and in the treatment of congestive heart failure, renal failure, and glaucoma pharmaceutical compositions including these antagonists, and methods of using these compounds to produce angiotensin II receptor antagonism in mammals.
    Type: Grant
    Filed: November 30, 1990
    Date of Patent: August 10, 1993
    Inventors: Joseph A. Finkelstein, Judith Hempel, Richard M. Keenan, James Samanen, Joseph Weinstock
  • Patent number: 5225589
    Abstract: Processes, intermediates, and products involved in preparing 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 at a temperature below about 110.degree. C. to give a polymer having the repeating unit ##STR2## wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed with alcoholic or aqueous base 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 mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3.
    Type: Grant
    Filed: February 3, 1992
    Date of Patent: July 6, 1993
    Assignee: Eastman Kodak Company
    Inventor: Charles A. McCombs
  • Patent number: 5223517
    Abstract: Heterocyclically substituted cycloalkano[b]-indolesulphonamides can be prepared by reaction of appropriate N-unsubstituted indoles with acrylonitrile, followed by hydrolysis, esterification or amidation, or by reaction of heterocyclically substituted hydrazines with cycloalkanones or by subsequent introduction of the heterocyclic group into appropriate indole derivatives. The heterocyclically substituted cycloalkano[b]-indolesulphonamides can be employed for the treatment of thromboembolic disorders, ischaemias, arteriosclerosis, asthma, allergies and for the prophylaxis of myocardial infarcts.
    Type: Grant
    Filed: August 23, 1991
    Date of Patent: June 29, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ulrich E. Muller, Ulrich Niewohner, Elisabeth Perzborn, Erwin Bischoff, Hans-Georg Dellweg
  • Patent number: 5223489
    Abstract: A compound of the formula: ##STR1## wherein R.sup.1 is lower alkyl optionally substituted aryl; or amino optionally substituted; andR.sup.2 is hydrogen or lower alkyl; orR.sup.1 and R.sup.2 are taken together with the attached nitrogen atom to form a heterocyclic group optionally substituted;R.sup.3 is hydrogen or lower alkyl; andR.sup.
    Type: Grant
    Filed: January 30, 1992
    Date of Patent: June 29, 1993
    Assignee: Ujisawa Pharmaceutical Co., Ltd.
    Inventors: Keiji Hemmi, Masahiro Neya, Hiroshi Marusawa, Keisuke Imai, Natsuko Kayakiri, Masashi Hashimoto
  • Patent number: 5218124
    Abstract: There are disclosed compounds of the formulaA(CH.sub.2).sub.n O--BwhereinA is a group having the formula ##STR1## wherein X is --N-- or ##STR2## Z is ##STR3## R.sup.1 is hydrogen, lower alkyl or phenyl; R.sup.2 is hydrogen or lower alkyl; orR.sup.1 and R.sup.2 taken together form a benzene ring, with the proviso that when X is --N--, Z is other than ##STR4## R.sup.3 is hydrogen or lower alkyl; n is 1-2;B is ##STR5## wherein Y is OR.sup.5 or N(OH)R.sup.8 ;R.sup.4 and R.sup.5 are each, independently, hydrogen or lower alkyl;R.sup.6 is hydrogen, halo or nitro;R.sup.7 is ##STR6## R.sup.
    Type: Grant
    Filed: June 1, 1992
    Date of Patent: June 8, 1993
    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: 5214162
    Abstract: The invention is concerned with a process for the manufacture of 5-cyano-4-lower alkyl-oxazoles by dehydrating a 5-carbamoyl-4-lower alkyl-oxazole in the gas phase in the presence of a heterogeneous catalyst based on silicon dioxide and in the presence of an inert solvent. The heterogeneous catalyst used is formed SiO.sub.2 or SiO.sub.2 doped with an oxide of V, Mo, Fe, Co and/or Zn. An N-lower alkyl-pyrrolidone is preferably used as the inert solvent.
    Type: Grant
    Filed: December 5, 1991
    Date of Patent: May 25, 1993
    Assignee: Hoffman-La Roche Inc.
    Inventor: Paul Nosberger
  • Patent number: 5204359
    Abstract: Insecticidally active nitro compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, cyano or alkyl,R.sup.2 is hydrogen or an organic radical,R.sup.3 is ##STR2## R.sup.4 is an organic radical, R.sup.5 and R.sup.6 are hydrogen or organic radicals,Y is CH or N, andZ is an optionally substituted 5- or 6-membered heterocyclic group,with certain conditions and exceptions.
    Type: Grant
    Filed: September 11, 1991
    Date of Patent: April 20, 1993
    Assignee: Nihon Bayer Agrochem K.K.
    Inventors: Kozo Shiokawa, Shinichi Tsuboi, Koichi Moriya, Yumi Hattori, Ikuro Honda, Katsuhiko Shibuya
  • Patent number: 5201934
    Abstract: Carboxamides of the formulae Ia to Ic ##STR1## where X is oxygen or sulfur;R.sup.1 is hydrogen or substituted or unsubstituted cycloalkyl or alkyl;R.sup.2 is hydroxy, alkoxy, cyanoalkyl, substituted or unsubstituted alkenyl, alkynyl, phenyl or naphthyl, or one of the groups stated for R.sup.1 ;R.sup.3 and R.sup.4 are nitro, cyano, halogen, substituted or unsubstituted amino, alkoxy, alkylthio, substituted or unsubstituted alkenyl, alkynyl, phenyl, phenoxy or phenylthio, or one of the groups stated for R.sup.1 ;R.sup.5 is formyl, 4,5-dihydrooxazol-2-yl or COYR.sup.6 (Y.dbd.O,S);R.sup.6 is hydrogen, cycloalkyl, substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkenyl or phenyl,phthalimido, tetrahydrophthalimido, succinimido, maleimido, benzotriazolyl ora group --N.dbd.CR.sup.7 R.sup.8, whereR.sup.7 and R.sup.8 are hydrogen or alkyl, and R.sup.8 may also be cycloalkyl, phenyl, or R.sup.7 and R.sup.8 together form a 4- to 7-membered alkylene chain;and if R.sup.
    Type: Grant
    Filed: October 3, 1990
    Date of Patent: April 13, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Muenster, Gerd Steiner, Wolfgang Freund, Bruno Wuerzer, Karl-Otto Westphalen
  • Patent number: 5198547
    Abstract: Intermediates and a process for the synthesis of 6-monosubstituted tetrahydropteridine C6-stereoisomers, including (6S)-tetrahydrofolic acid. The intermediates are shown in their two enantiomeric forms as follows: ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and represent hydrogen, methyl, hydroxy, amino, alkyl or dialkylamino, alkoxy, benzyloxy, or benzylthio; R.sub.3 represents an alkene, alkyne, cycloalkyl, benzyl, alkyl (substituted with hydroxy, acetoxy, benzyloxy, alkoxy, alkylthio, amino, carboxy, oxo, or phosphate), a protected aldehyde, or ##STR2## wherein n=1 or 2, R.sub.4 is hydrogen, formyl, methyl, or propargyl, and ZZ represents an amino acid or amino acid polymer. Also, a process for tetrahydropteridine N5-formylation for the preparation of, for example, N5-formyl-(6S)-tetrahydrofolic acid.
    Type: Grant
    Filed: March 16, 1992
    Date of Patent: March 30, 1993
    Assignee: South Alabama Medical Science Foundation, USA
    Inventors: Steven W. Bailey, June E. Ayling
  • Patent number: 5196532
    Abstract: Compounds of formula I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen or methyl, A is an ethylene or methylene radical which is unsubstituted or substituted by methyl, hydroxyl or oxo,L is a saturated or unsaturated five-membered or six-membered heterocyclic structure which is unsubstituted or substituted by hydroxyl, mercapto, C.sub.1 -C.sub.6 -alkyl, or C.sub.1 -C.sub.4 -alkanoyl and has from 1 to 3 heteroatoms from the group consisting of N, O and S, the second and third heteroatoms being a nitrogen atom,R.sup.3 is hydrogen, a hydroxy or C.sub.1 -C.sub.6 -alkoxy group,R.sup.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl, halogen or methoxy,R.sup.5 is hydrogen or methoxy or tert-butyl,R.sup.6 is hydrogen methyl, nitrile or a C.sub.2 -C.sub.10 -ketal group or the radical --CHR.sup.7 OR.sup.8 --CHR.sup.7 --NR.sup.9 R.sup.10, --COR.sup.11, --SR.sup.12, ##STR2## in which R.sup.7 is hydrogen or C.sub.1 -C.sub.4 -alkyl,R.sup.8 is hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.
    Type: Grant
    Filed: June 18, 1991
    Date of Patent: March 23, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Heiner Wuest, Bernd Janssen, William V. Murray, Michael P. Wachter, Stanley Bell
  • Patent number: 5194622
    Abstract: A process for the preparation of a compound of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, halogen, --CF.sub.3, alkyl, alkoxy and alkylthio of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, --SO.sub.2 alk and alk is alkyl of 1 to 8 carbon atoms, optionally substituted aryl, aryloxy and arylthio of 6 to 18 carbon atoms and optionally substituted heteroaryl, heteroaryloxy and heterocyclic of 5 to 6 ring members, R.sub.3 is selected from the group consisting of alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, aryl of 6 to 18 carbon atoms and alkoxyalkoxyalkyl of 3 to 14 carbon atoms, X is selected from the group consisting of --O--, --S-- and --NR.sub.4 --, R.sub.4 is selected from the group consisting of hydrogen, alkyl, alkenyl and alkynyl of up to 8 carbon atoms, --SO.sub.2 alkyl, --SO.sub.2 alkenyl and --SO.sub.2 alkynyl of up to 8 carbon atoms and optionally substituted aryl and --SO.sub.
    Type: Grant
    Filed: November 18, 1991
    Date of Patent: March 16, 1993
    Assignee: Roussel Uclaf
    Inventors: Jean-Louis Brayer, Jean-Pierre Demoute
  • Patent number: 5192782
    Abstract: This invention relates to compounds of Formula I and the stereoisomers and pharmaceutically acceptable salts thereof ##STR1## wherein R is alkyl, alkenyl, alkynyl, or (CH.sub.2).sub.m R.sup.3 whereR.sup.3 is cycloalkyl and m is 1 or 2;R.sup.1 is alkyl;R.sup.2 is hydrogen or alkyl;R.sup.4 is alkyl;n is an integer from 1 to 5;p is an integer from 0 to 6;Y is oxygen; andZ is hydrogen, alkyl, alkoxy, NR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently hydrogen or alkyl, or SR.sup.6 wherein R.sup.6 is hydrogen, benzyl or alkyl.The compounds of Formula I are leukotriene B.sub.4 antagonists and are useful as anti-inflammatory agents and in the treatment of leukotriene B.sub.4 mediated conditions.
    Type: Grant
    Filed: September 13, 1991
    Date of Patent: March 9, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Thomas D. Penning, James P. Snyder
  • Patent number: 5189165
    Abstract: A process for preparing a compound I ##STR1## with A=t-butyl, aryl andR=alkyl, alkenyl, alkynyl, alkenynyl, cycloalkyl(alkyl), aryl, arylalkyl, alkyl-S-(-O)-arylby reacting a compound III ##STR2## with a compound IV ##STR3## under the conditions of a phase-transfer reaction, is described. The process gives excellent yields and is not associated with the unpleasant odor of mercaptans.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: February 23, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Burdinski, Reinhard Kirsch, Hariolf Kottmann
  • Patent number: 5187188
    Abstract: A novel series of oxazole derivatives is disclosed in the Formula I ##STR1## wherein Y and Z are independently hydrogen or together form a bond;X is CN, CO.sub.2 R.sup.1 or CO.NR.sup.2 R.sup.3 ;R and R.sup.1 are independently or together H, Na, or C.sub.1 -C.sub.5 lower alkyl;R.sup.2 and R.sup.3 are independently or together H, or C.sub.1 -C.sub.5 lower alkyl;or alkali metal 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: February 16, 1993
    Assignee: Bristol-Myers Squibb Company
    Inventor: Nicholas A. Meanwell
  • Patent number: 5185351
    Abstract: Angiotensin II receptor antagonists having the formula: ##STR1## which are useful in regulating hypertension and in the treatment of congestive heart failure, renal failure, and glaucoma, pharmaceutical compositions including these antagonists, and methods of using these compounds to produce angiotensin II receptor antagonism in mammals.
    Type: Grant
    Filed: August 14, 1991
    Date of Patent: February 9, 1993
    Assignee: SmithKline Beecham Corporation
    Inventors: Joseph A. Finkelstein, Richard M. Keenan, Joseph Weinstock
  • Patent number: 5185353
    Abstract: A method for killing or controlling nematode pests which comprises applying to the locus of the pests or to a plant susceptible to attack by the pest an effective amount of a compound of formula (I): ##STR1## wherein R.sup.1 is an optionally substituted aryl or optionally substituted heterocyclic group and novel compounds of formula (I) where R.sup.1 is not phenyl.
    Type: Grant
    Filed: November 8, 1990
    Date of Patent: February 9, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael D. Turnbull, Robert W. Parsons, Andrew D. S. Watkins
  • Patent number: 5166357
    Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## in which one of X and Y represents hydrogen and the other represents Z, where Z is a group ##STR2## in which Q represents a 3-membered divalent residue completing a 5-membered aromatic ring and comprises one heteroatom selected from oxygen, nitrogen and sulphur or two heteroatoms selected from sulphur and nitrogen, any amino nitrogen being optionally substituted by a C.sub.1-2 alkyl, and at least one ring carbon atom being substituted by a group R.sub.1 ; or a group ##STR3## in which A.sub.1, A.sub.2 and A.sub.3 complete a 5-membered aromatic ring and A.sub.1 is oxygen or sulphur, A.sub.2 is CR.sub.2 and A.sub.3 is nitrogen or CH, or A.sub.2 is oxygen or sulphur, A.sub.1 is CH and A.sub.3 is CR.sub.2 ; and R.sub.1 and R.sub.2 are selected from, halogen, CN, OR.sub.4, SR.sub.4, N(R.sub.4).sub.2, NHCOR.sub.4, NHCOOCH.sub.3, NHCOOC.sub.2 H.sub.5, NHOR.sub.4 NHNH.sub.2, NO.sub.2, COR.sub.4, COR.sub.5, C.sub.2-4 alkenyl, C.sub.
    Type: Grant
    Filed: October 10, 1989
    Date of Patent: November 24, 1992
    Assignee: Beecham Group p.l.c.
    Inventors: Barry S. Orlek, Richard E. Faulkner
  • Patent number: 5166153
    Abstract: Novel N-acylated 2-[4-(halophenoxy)-phenoxy]-ethylcarbamic acid esters of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.8 alkyl or C.sub.3 -C.sub.5 alkenyl,R.sub.2 is C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, --CO--R.sub.7 or --NR.sub.8 R.sub.9,R.sub.3 and R.sub.4 independently of one another are hydrogen or methyl,R.sub.5 is chlorine or fluorine,R.sub.6 is either the same substituent as R.sub.5 or is hydrogen,R.sub.7 is C.sub.1 -C.sub.8 alkoxy or --NR.sub.10 R.sub.11,R.sub.8 is C.sub.1 -C.sub.4 alkyl,R.sub.9 is C.sub.1 -C.sub.4 alkyl orR.sub.8 and R.sub.9 together form a C.sub.4 -C.sub.6 alkylene chain which may be interrupted by oxygen, sulfur or --NCH.sub.3 --,R.sub.10 is hydrogen or C.sub.1 -C.sub.4 alkyl andR.sub.11 is hydrogen or C.sub.1 -C.sub.4 alkyl, benzyl, phenyl, or phenyl substituted by halogen or by methyl, orR.sub.10 and R.sub.11 together form a C.sub.4 -C.sub.6 alkylene chain which may be interrupted by oxygen, sulfur or --NCH.sub.
    Type: Grant
    Filed: April 24, 1990
    Date of Patent: November 24, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Friedrich Karrer
  • Patent number: 5166216
    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: May 13, 1991
    Date of Patent: November 24, 1992
    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: 5162352
    Abstract: 7-Oxabicycloheptyl substituted heterocyclic amide prostaglandin analogs are provided which are thromboxane A.sub.2 (TXA.sub.2) receptor antagonists and have the structural formula ##STR1## wherein m is 1, 2 or 3, n is 1, 2, 3 or 4 and p is 2 to 18. These compounds are also useful in identifying thromboxane receptors in various tissue.
    Type: Grant
    Filed: August 22, 1991
    Date of Patent: November 10, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Steven E. Hall, Martin L. Ogletree
  • Patent number: 5158967
    Abstract: 7-Oxabicycloheptyl substituted heterocyclic amide prostaglandin analogs are provided which are thromboxane A.sub.2 (TXA.sub.2) receptor antagonists or combined thromboxane A.sub.2 receptor antagonist/thromboxane synthetase inhibitors and have the structural formula ##STR1## wherein R is SO.sub.3 H, P(O)OR.sup.3 OH or P(O)R.sup.4 OH, X is O or NH, and Z, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined herein.
    Type: Grant
    Filed: June 12, 1991
    Date of Patent: October 27, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Steven E. Hall
  • Patent number: 5126370
    Abstract: Prostaglandin analogs useful in treating thrombotic and vasospastic disease having the structural formula ##STR1## wherein: m is 1, 2 or 3:n is 1, 2 or 3, except that n is O when Y is vinylene;p is 1, 2 or 3;R is CO.sub.2 R', CH.sub.2 OH, CONHSO.sub.2 R.sup.3, CONHR.sup.4, or --CH.sub.2 -5-tetrazolyl;R' is hydrogen, alkyl, or alkali metal;Y is --O--, a single bond or vinylene, except that Y cannot be --O-- when n is 0;and the remaining symbols are as defined in the specification.
    Type: Grant
    Filed: December 24, 1990
    Date of Patent: June 30, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Raj N. Misra
  • Patent number: 5118683
    Abstract: Compounds of the formula I ##STR1## wherein R.sup.5 represents C.sub.1 to C.sub.6 -alkyl or the group --(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --Ar;Z represents O, S or --CH.sub.2 --;n represents an integer of 1 to 8;m represents zero or an integer of 1 to 8;one of R.sup.1 and R.sup.2 represents the group ##STR2## and the other represents hydrogen or R.sup.7 CO--; R.sup.7 is C.sub.1 to C.sub.10 alkyl, C.sub.3 to C.sub.8 cycloalkyl, aryl, heteroaryl, --N(R.sup.9 R.sup.10), or R.sup.11 O--; R.sup.3, R.sup.4, R.sup.9, and R.sup.10 are each independently selected from hydrogen, C.sub.1 to C.sub.6 alkyl and Ar.sup.1 ; R.sup.6 and R.sup.11 are each independently C.sub.1 -C.sub.8 alkyl; Ar and Ar.sup.1 are each independently selected from the group consisting of phenyl or phenyl substituted by one or two substituents selected from the group consisting of R.sup.12, R.sup.13 O--; R.sup.14 S(O).sub.x --, R.sup.15 CO--, (R.sup.16 R.sup.17)NCO--, F, Cl, Br, I, NO.sub.2, CF.sub.3, CN, or phenyl; R.sup.12, R.sup.13, R.sup.
    Type: Grant
    Filed: June 13, 1990
    Date of Patent: June 2, 1992
    Assignee: Schering Corporation
    Inventors: David J. Blythin, Ho-Jane Shue
  • Patent number: 5116850
    Abstract: Heterocyclic pyrazoline carboxanilide insecticides including all geometric and stereoisomers thereof, as well as agricultural compositions containing them.
    Type: Grant
    Filed: May 21, 1990
    Date of Patent: May 26, 1992
    Assignee: E. I. Du Pont de Nemours and Co.
    Inventor: Thomas M. Stevenson
  • Patent number: 5110956
    Abstract: A new benzodioxole derivative has a substituent in the phenyl ring which is a carboxyalkylthioalkyl or the like and is effective to treat a liver disease.
    Type: Grant
    Filed: April 23, 1990
    Date of Patent: May 5, 1992
    Assignee: Eisai Co., Ltd.
    Inventors: Yoshitake Ogata, Makoto Ikeda, Seiichiro Nomoto, Makoto Okita, Naoyuki Shimomura, Toshihiko Kaneko, Takashi Yamanaka, Ieharu Hishinuma, Junichi Nagakawa, Kazuo Hirota, Kaname Miyamoto, Toru Horie, Tsuneo Wakabayashi
  • Patent number: 5110986
    Abstract: This application relates to a process for preparing a N-t-alkyl-1,2-diacylhydrazine by reacting a 1,3,4-oxadiazole with a tertiary alkyl cation precursor in the presence of a strong acid catalyst. Preferably, the 1,3,4-oxadiazole is a 2,5-disubstituted-1,3,4-oxadiazole and more preferably a 2,5-diaryl-1,3,4-oxadiazole. The strong acid catalyst is preferably a sulfur containing acid and more preferably sulfuric acid.
    Type: Grant
    Filed: April 26, 1988
    Date of Patent: May 5, 1992
    Assignee: Rohm and Haas Company
    Inventor: Martha J. Kelly
  • Patent number: 5104869
    Abstract: Renin inhibiting compounds containing a single .alpha.-amino acid of the formula: ##STR1## and analogs thereof which inhibit the substrate-cleaving acting or renin, pharmaceutical compositions containing these compounds, processes for producing the compounds and methods of treating hypertension which employ the novel renin inhibitors.
    Type: Grant
    Filed: October 25, 1990
    Date of Patent: April 14, 1992
    Assignee: American Cyanamid Company
    Inventors: Jay D. Albright, Charles Frederick, Jeremy I. Levin, Fuk-Wah Sum, Marvin F. Reich
  • Patent number: 5103014
    Abstract: There are disclosed compounds of the formula ##STR1## wherein X is ##STR2## Y is ##STR3## Z is --(CH.sub.2).sub.n O--, --(CH.sub.2).sub.n S--, ##STR4## R.sup.1 is ##STR5## n is 0-5; R.sup.2 is hydrogen, loweralkyl, loweralkoxy, lower alkoxycarbonyl, trifluoromethyl, nitro, cyano or halo;R.sup.3 is ##STR6## W represents a bond or --O--, --S-- or ##STR7## m is 1-15; R.sup.4 is hydrogen or loweralkyl;R.sup.5 is lower alkyl, monofluoroloweralkyl, difluroloweralkyl, polyfluroloweralkyl, perfluoroloweralkyl or ##STR8## R.sup.6 is hydrogen lower alkyl, --COOR.sup.4 or ##STR9## R.sup.7 is OR.sup.4 or N(R.sup.4).sub.2 ; R.sup.8 is OR.sup.4 or N(R.sup.4).sub.2 ;and the pharmaceutically acceptable salts thereof, and their use in the treatment of leukotriene-mediated naso-bronchial obstruction airpassageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like, as antiinflammatory agents.
    Type: Grant
    Filed: May 18, 1990
    Date of Patent: April 7, 1992
    Assignee: American Home Products Corporation
    Inventors: John H. Musser, Reinhold H. W. Bender, Anthony F. Kreft, III, James A. Nelson
  • Patent number: 5103007
    Abstract: Lipid derivatives represented by the formula: ##STR1## wherein R.sup.1 stands for an optionally substituted higher alkyl group, R.sup.2 stands for an optionally substituted lower alkyl group or an optionally substituted nitrogen-containing heterocyclic group, R.sup.3 stands for a tertiary amino group or a quaternary ammonium group, J stands for oxygen atom or S(O)t (where t deontes 0, 1 or 2), m and n respectively denotes 1 or 2, p denotes 0, 1 or 2, q and r respectively denote an integer of 2 to 5.and salts thereof have antitumor activities including differentiation-inducing activity and are useful as antitumor agents.
    Type: Grant
    Filed: October 27, 1989
    Date of Patent: April 7, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Keizo Inoue
  • Patent number: 5100889
    Abstract: 7-Oxabicycloheptane substituted prostaglandin analogs useful in treating thrombotic and vasopastic 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 0, if Z is ##STR3## then Y cannot be O, and 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: June 18, 1990
    Date of Patent: March 31, 1992
    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: 5089514
    Abstract: Certain 3-(phenyl, chroman-2-yl, benzofuran-5-yl, or benzoxazol-5-yl)-2-(hydroxy or mercapto)propionic acid derivatives and analogs are useful as hypoglycemic and hypocholesterolemic agents.
    Type: Grant
    Filed: June 14, 1990
    Date of Patent: February 18, 1992
    Assignee: Pfizer Inc.
    Inventor: Bernard Hulin
  • Patent number: 5087288
    Abstract: A method of controlling plant growth is provided comprising applying to the plants or to a habitat thereof a herbicidally effective amount of a compound having the structure: ##STR1## wherein R.sup.1 is selected from the group consisting of carboxy, cyano, ester ##STR2## or amido ##STR3## wherein R.sup.2 is selected from the group consisting of a straight-chained alkyl group or a branched-chain alkyl group, of about 1 to 8 carbon atoms,R.sup.3 and R.sup.4 are selected from the group consisting of hydrogen, alkyl of about 1 to 8 carbon atoms, cycloalkyl of about 5 to 6 carbon atoms, and heterocyclyl of about 5 to 6 carbon and hetero atoms, or,R.sup.3 and R.sup.4 taken together with the nitrogen atoms to which they are attached form a heterocyclyl group having 5 to 6 carbon and hetero atoms. Also, novel compounds having the above structure are provided.
    Type: Grant
    Filed: September 17, 1990
    Date of Patent: February 11, 1992
    Assignee: Eastman Kodak Company
    Inventor: Thomas R. Welter
  • Patent number: 5081245
    Abstract: A compound represented by the formula: ##STR1## wherein R represents a hydrogen atom or a lower alkyl group;R.sup.1 represents a higher alkyl group which may be substituted;R.sup.2 represents a hydrogen atom or a lower alkyl group, a lower alkanoyl group or a nitrogen-containing 5- to 7-membered heterocyclic group each of which may be substituted; X represents a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --wherein p represents an integer of 1 to 5, a divalent group represented by the formula:--O(CH.sub.2).sub.q --wherein q represents an integer of 3 to 8, or a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --J--(CH.sub.2).sub.q --wherein J represents an oxygen atom or a group represented by the formula: --S(O).sub.
    Type: Grant
    Filed: August 18, 1989
    Date of Patent: January 14, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Eiko Imamiya, Keizo Inoue
  • Patent number: 5051421
    Abstract: Benzo[b]thiophene derivatives of formula ##STR1## their tautomers and salts, in which the index n is 0, 1 or 2, alk is lower alkylene, Ar is phenyl, naphthyl or a monocyclic, five- or six-membered heteroaryl radical, wherein the aromatic radical is unsubstituted or is mono- or poly-substituted by lower alkyl, halo-lower alkyl, halogen and/or by nitro, and the ring A is unsubstituted or is mono- or poly-substituted by lower alkyl, lower alkoxy, lower alkylthio, lower alkanesulfinyl, lower alkanesulfonyl, halo-lower alkyl, halogen and/or by nitro, can be used, for example, as active ingredients in medicaments.
    Type: Grant
    Filed: January 18, 1990
    Date of Patent: September 24, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Pier G. Ferrini
  • Patent number: 5047549
    Abstract: Derivatives of pravastatin are provided which are useful in inhibiting cholesterol biosynthesis and in preparing radiolabeled compounds useful in the radioimmunoassay (RIA) of pravastatin and derivatives thereof. The pravastatin derivatives have the structure ##STR1## wherein R is hydroxy, lower alkylamine, arylamine, arylalkylamine or heterocyclic alkylamine such as histamine, tyramine, O-benzyltyramine, methyl tyrosinate as well as iodinated derivatives thereof.
    Type: Grant
    Filed: April 17, 1989
    Date of Patent: September 10, 1991
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Richard A. DiPietro, Jan-I Tu, Noor Z. Turabi