1,2,5-thiadiazoles (including Hydrogenated) Patents (Class 548/134)
  • 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: 5317103
    Abstract: A class of indole-substituted five-membered heteroaromatic compounds are specific agonists of 5-HT.sub.1 -like receptors and are therefore useful in the treatment of clinical conditions, in particular migraine and associated disorders, for which a selective agonist of these receptors is indicated.
    Type: Grant
    Filed: July 16, 1992
    Date of Patent: May 31, 1994
    Assignee: Merck Sharp & Dohme Limited
    Inventors: Raymond Baker, Austin J. Reeve, Leslie J. Street
  • 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: 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: 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: 5246952
    Abstract: Compounds of formula I ##STR1## wherein Z is thiazolyl or isothiazolyl, and 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.
    Type: Grant
    Filed: September 17, 1991
    Date of Patent: September 21, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Marc Lang
  • Patent number: 5245040
    Abstract: A process for the preparation of 1,3-disubstituted 2-nitroguanidines of the formula I ##STR1## in which R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl or a radical --CH.sub.2 B; A is an unsubstituted or mono- to tetrasubstituted aromatic or non-aromatic, monocyclic or bicyclic heterocyclic radical, which may contain one or two substituents from the group comprising C.sub.1 -C.sub.3 haloalkyl having 1 to 7 halogen atoms, cyclopropyl, halocyclopropyl having 1 to 3 halogen atoms, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 alkynyl, C.sub.2 -C.sub.3 haloalkenyl and C.sub.2 -C.sub.3 haloalkynyl having 1 to 4 halogen atoms, C.sub.1 -C.sub.3 haloalkoxy having 1 to 7 halogen atoms, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 haloalkylthio having 1 to 7 halogen atoms, allyloxy, propargyloxy, allylthio, propargylthio, haloallyloxy, haloallylthio, cyano and nitro and one to four substituents from the group comprising C.sub.1 -C.sub.3 alkyl, C.sub.
    Type: Grant
    Filed: October 16, 1991
    Date of Patent: September 14, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Maienfisch, Odd Kristiansen, Laurenz Gsell
  • Patent number: 5234946
    Abstract: The substituted alkylamine derivatives represented by formula (I) ##STR1## wherein R.sup.1 represents (a) substituted or unsubstituted C.sub.2-6 alkenyl group, (b) substituted or unsubstituted C.sub.3-6 cycloalkenyl group, (c) substituted or unsubstituted C.sub.2-6 alkynyl group, (d) substituted or unsubstituted aryl group, (e) substituted or unsubstituted heterocyclic group, (f) fused heterocyclic group which may be substituted, or (g) group represented by the formula Ru.sup.11 -Ar wherein R.sup.11 is a heterocyclic group and Ar is a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and which may be substituted; ##STR2## represents a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and may be substituted by R.sup.7,X and Y are linking groups,R.sup.2 is H or lower alkyl,R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl or lower cycloalkyl,R.sup.4 and R.sup.5 are independently hydrogen or halogen atoms,R.sup.
    Type: Grant
    Filed: August 30, 1991
    Date of Patent: August 10, 1993
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Hiroshi Takezawa, Masahiro Hayashi, Yoshikazu Iwasawa, Masaaki Hosoi, Yoshiaki Iida, Yoshimi Tsuchiya, Masahiro Horie, Toshio Kamei
  • Patent number: 5223616
    Abstract: A heterocyclic compound which is useful for dyeing or printing hydrophobic fiber materials and which has the following formula (I), ##STR1##wherein A.sub.1, A.sub.2, A.sub.3 and A.sub.4 are each hydrogen, halogen, alkyl, alkoxy or alkenyl, X.sub.1 is --O-- or the like, R.sub.1 is a methylene or the like, X.sub.2 is a direct linkage or a divalent group of --O--, --S--, --SO--, --SO.sub.2 --, ##STR2## in which R.sub.3 is a hydrogen atom or a C.sub.1-4 alkyl group, ##STR3## in which R.sub.3 is as defined above, T and u are each independently hydrogen or a C.sub.1-4 alkyl, l is O or an integer of 1 to 3, Q is an unsubstituted or substituted 5-, 6- or 7-membered saturated or unsaturated heterocyclic residue, Y is hydrogen, C.sub.1-4 alkyl, a C.sub.1-4 alkoxy group or the like.
    Type: Grant
    Filed: November 4, 1991
    Date of Patent: June 29, 1993
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Jun Yamamoto, Junichi Sekihachi, Yosuke Yamamoto, Kazuhiro Machiguchi, Yutaka Kayane
  • Patent number: 5205853
    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, imino (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: May 23, 1991
    Date of Patent: April 27, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hilmar Wolf, Rolf Kirsten, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
  • Patent number: 5194440
    Abstract: A class of substituted cyclic sulphamide derivatives are selective agonists of 5-HT.sub.1 -like receptors and are therefore useful in the treatment of clinical conditions, in particular migraine and associated disorders, for which a selective agonist of these receptors is indicated.
    Type: Grant
    Filed: February 20, 1992
    Date of Patent: March 16, 1993
    Assignee: Merck Sharp & Dohme Ltd.
    Inventor: Jose L. C. Pineiro
  • Patent number: 5194167
    Abstract: Quaternary ammonium salts of mercaptothiadiazoles and related heterocyclic derivatives have been found to be effective antioxidant and antiwear additives for lubricants and fuels.
    Type: Grant
    Filed: May 8, 1991
    Date of Patent: March 16, 1993
    Assignee: Mobil Oil Corporation
    Inventors: Shih-Ying Hsu, Andrew G. Horodysky
  • Patent number: 5158943
    Abstract: A sulfur-containing hetrocyclic compound of the formula (I) ##STR1## wherein the ring A is an optionally substituted benzene ring, R is a hydrogen atom or an optionally substituted hydrocarbon residue, B is a carboxyl group which may be esterified or amidated, X is --CH(OH)-- or --CO--, and n is an integer of 0, 1 or 2, or its salt, which is useful in the prevention or treatment of osteoporosis.
    Type: Grant
    Filed: May 23, 1991
    Date of Patent: October 27, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Takashi Sohda, Iwao Yamazaki
  • Patent number: 5138064
    Abstract: Novel 3-pyrrolidinylthio-1-azabiycyclo[3.2.0]hept-2-ene-2-carboxylic acid compounds and pharmaceutically acceptable salts thereof have antimicrobial activity and are useful as medicaments in the treatment of infectious diseases caused by pathogenic microorganisms.
    Type: Grant
    Filed: February 6, 1990
    Date of Patent: August 11, 1992
    Assignee: Fujisawa Pharmaceutical Company, Ltd.
    Inventors: Masayoshi Murata, Hideo Tsutsumi, Keiji Matsuda, Kohji Hattori, Takashi Nakajima
  • Patent number: 5086186
    Abstract: Preparation of 2-oxindole-1-carboxamides by reaction of 2-oxindoles with trichloracetyl isocyanate to produce novel N-trichloroacetyl-2-oxindole-1-carboxamides which are then hydrolyzed to 2-oxindole-1-carboxamides useful as analgesic and antiinflammatory agents and/or intermediates for such agents.
    Type: Grant
    Filed: May 31, 1990
    Date of Patent: February 4, 1992
    Assignee: Pfizer Inc.
    Inventor: Sarah E. Kelly
  • 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: 5007952
    Abstract: Herbicidally active pyrroles of the formula ##STR1## wherein R.sup.1 represents C.sub.1-4 alkyl, or one R.sup.1 together with the other R.sup.1 forms tetramethylene or butenylene,X represents hydrogen or halogen,Y represents O or S,n represents 0 or 1,R.sup.2 represents hydrogen or an organic radical.
    Type: Grant
    Filed: November 9, 1989
    Date of Patent: April 16, 1991
    Assignee: Nihon Tokushu Noyaku Seizo K.K.
    Inventors: Toyohiko Kume, Toshio Goto, Atsumi Kamochi, Akihiko Yanagi, Hiroshi Miyauchi, Tadao Asami
  • Patent number: 5001138
    Abstract: Novel insecticides of the formula ##STR1## in which n is 0 or 1,X is S, O, ##STR2## Y is N or ##STR3## Z is a 5- or 6-membered nitrogen-containing heterocyclic ring, and R to R.sup.9 variously represent hydrogen or specified organic radicals.
    Type: Grant
    Filed: May 4, 1989
    Date of Patent: March 19, 1991
    Assignee: Nihon Tokushu Noyaku Seizo, K.K.
    Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Koichi Moriya
  • Patent number: 4968691
    Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## in which X represents a group ##STR2## in which p represents an integer of 2 to 4; r represents an integer of 1 or 2; s represents 0 or 1; and A represents a 3-membered divalent residue completing a 5-membered aromatic ring and comprises one or two heteroatoms selected from oxygen, nitrogen and sulphur, any amino nitrogen optionally substituted by a C.sub.1-4 alkyl group, and when (p,r,s) is (2,2,0) or (2,2,1) any A comprising 2 heteroatoms is optionally C-substituted by a methyl group, and when (p,r,s) is (2,1,0), (2,1,1) or (3,1,0) any A comprising 2 heteroatoms is optionally C-substituted by C.sub.1-2 alkyl and any A comprising one heteroatom is optionally C-substituted by a methyl group, and wherein compounds of formula (I) having two asymetric centers have the stereo-chemical configuration in which the group X and the (CH.sub.2).sub.
    Type: Grant
    Filed: March 7, 1989
    Date of Patent: November 6, 1990
    Assignee: Beecham Group P.L.C.
    Inventors: Barry S. Orlek, Michael S. Hadley, Howard E. Rosenberg, Harry J. Wadsworth
  • Patent number: 4959379
    Abstract: Fungicidal 7-substituted 2-carboxamido-benzothiazole 3-oxides of the formula ##STR1## in which n stands for the numbers 0, 1, 2 or 3,R.sup.1 stands for hydrogen or optionally substituted alkyl,R.sup.2 stands for hydrogen, hydroxyl, ureido or for an optionally substituted radical from the group consisting of alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, aralkoxy, aralkyl, aryl, heterocyclyl and heterocyclylakyl, orR.sup.1 and R.sup.2 together stand for an alkylene chain which is optionally substituted and optionally interrupted by hetero atoms,R.sup.3 stands for halogen, alkyl or halogenoalkyl andR.sup.4 stands for halogen, alkyl or halogenoalykl.The intermediates of the formula ##STR2## are also new.
    Type: Grant
    Filed: March 21, 1989
    Date of Patent: September 25, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Wagner, Gerd Hanssler
  • Patent number: 4956356
    Abstract: Pesticidal 3-substituted 1-nitro-2-imino-1,3-diazacycloalkanes of the formula ##STR1## in which n stands for the numbers 0 or 1,R.sup.1 stands for a five- or six-membered heterocyclic group which contains 1, 2, 3 or 4 nitrogen atoms and/or one or two oxygen atoms or sulphur atoms as hetero atom ring members--the number of the hetero atoms being 1, 2, 3 or 4--and which is optionally substituted by halogen, cyano, nitro, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, alkinyl, alkoxy, halogenoalkoxy, alkenyloxy, halogenoalkenyloxy, alkinyloxy, alkylthio, halogenoalkylthio, alkenylthio, halogenoalkenylthio, alkinylthio, alkylsulphinyl, halogenoalkylsulphinyl, alkylsulphonyl, halogenoalkylsulphonyl, amino, alkylamino, dialkylamino, aryl, aryloxy, arylthio, arylamino, aralkyl, formylamino, alkylcarbonylamino, formyl, carbamoyl, alkylcarbonyl and/or alkoxycarbonyl,R.sup.2 stands for hydrogen or alkyl andR.sup.3 stands for hydrogen or nitro.
    Type: Grant
    Filed: May 19, 1989
    Date of Patent: September 11, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Diehr, Benedikt Becker
  • Patent number: 4952703
    Abstract: Preparation of 2-oxindole-1-carboxamides by reaction of 2-oxindoles with trichloracetyl isocyanate to produce novel N-trichloroacetyl-2-oxindole-1-carboxamides which are then hydrolyzed to 2-oxindole-1-carboxamides useful as analgesic and anti-inflammatory agents and/or intermediates for such agents.
    Type: Grant
    Filed: May 25, 1989
    Date of Patent: August 28, 1990
    Assignee: Pfizer Inc.
    Inventor: Sarah E. Kelly
  • Patent number: 4923889
    Abstract: Compounds are disclosed, including 2-diethylamino-3-isobutoxy-N-phenyl-N-2-furanyl-methyl-propylamine and compounds of the formula: ##STR1## wherein R.sub.1 is an iso-C.sub.4 -C.sub.6 -alkyl radical; A is a valency bond or a straight-chained or branched alkyl radical containing up to 6 carbon atoms; R.sub.4 is a phenyl radical which is unsubstituted or substituted one or more times by C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.2 -C.sub.6 -alkenyloxy, hydroxy-C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkylenedioxy, hydroxy-C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -alkoxy-C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.6 -alkylamino, di(C.sub.1 -C.sub.6 -alkyl)amino, C.sub.1 -C.sub.3 -alkoxycarbonyl-C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylsulphinyl, C.sub.1 -C.sub.6 -alkylsulphonyl, C.sub.1 -C.sub.6 -alkylsulphonyloxy, carboxyl, C.sub.1 -C.sub.3 -alkoxycarbonyl, aminocarbonyl, mono- or di(C.sub.1 -C.sub.6 -alkyl)aminocarbonyl, halo-C.
    Type: Grant
    Filed: August 11, 1988
    Date of Patent: May 8, 1990
    Assignee: Boehringer Mannheim GmbH
    Inventors: Herbert Leinert, Christos Tsaklakidis, Gisbert Sponer
  • Patent number: 4920231
    Abstract: A process for the preparation of trifluoromethylvinyl compounds in all their possible streoisomeric forms and mixtures thereof comprising reacting a salt of trifluoroacetic acid with a halovinyl compound in the presence of a cuprous salt to obtain the same stereo-specific compound and all possible stereo-isomeric forms and mixtures thereof of 1R, trans compounds of the formula ##STR1## wherein R is an alcohol residue used in pyrethrinoid series, or an alcohol residue capable of blocking the acid function, and Z is aryl or haloaryl and the double bond has Z geometry having pesticide activity.
    Type: Grant
    Filed: March 30, 1989
    Date of Patent: April 24, 1990
    Assignee: Roussel Uclaf
    Inventors: Werner Bonin, Jean-Pierre Demoute, Jean Tessier
  • Patent number: 4904660
    Abstract: Novel compounds of the following formula (I) and their salts: A compound of the formula (I) ##STR1## These compounds are expected to be useful for renin inhibitors. Thus, the compounds are useful medical agents, in particular, anti-hypertensive agents.
    Type: Grant
    Filed: February 25, 1988
    Date of Patent: February 27, 1990
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Kohji Nakano, Takashi Fujikura, Ryuichiro Hara, Masato Ichihara, Yukiko Fukunaga, Masayuki Shibasaki
  • Patent number: 4882342
    Abstract: The present invention concerns new 5-alkylbenzimidazoles of the formula: ##STR1## wherein R.sub.1 is a phenyl ring of the formula: ##STR2## or R.sub.1 is naphthyl, heterocycle or a bicyclic heterocycle and R.sub.1 -R.sub.7 are described in claim 1.These compounds are useful for prophylaxis or treatment of heart and circulatory disease especially to increase contractility of the heart, lower blood pressure and/or influence the thrombocyte function and improve the microcirculation.
    Type: Grant
    Filed: October 6, 1987
    Date of Patent: November 21, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Wolfgang von der Saal, Jens-Peter Holck, Alfred Mertens, Bernd Muller-Beckmann, Lothar Kling
  • Patent number: 4871719
    Abstract: Novel 13-spiro-2'-[tetrahydrofuran]-milbemycins of the formula I ##STR1## in which X represents one of the groups --CH(OR.sub.1)--, --C(.dbd.O)-- or --C(.dbd.N--OH)--;R.sub.1 represents hydrogen or a OH-protecting group;R.sub.2 represents methyl, ethyl, isopropyl or sec.-butyl or the group --C(CH.sub.3).dbd.CH--A in which A represents methyl, ethyl or isopropyl; andR.sub.3 represents hydrogen; C.sub.1 -C.sub.10 -alkyl; C.sub.1 -C.sub.10 -alkyl substituted by at least one substituent selected from the group consisting of halogen, C.sub.1 -C.sub.6 -alkoxy, C.sub.2 -C.sub.6 -alkoxyalkoxy C.sub.3 -C.sub.9 -alkoxyalkoxyalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.1 -C.sub.3 -alkyl-substituted C.sub.3 -C.sub.7 -cycloalkyl, hydroxy, benzyloxy, C.sub.1 -C.sub.6 -acyl and C.sub.1 -C.sub.6 -acyloxy, it being possible for each of the above-mentioned radicals representing or containing an alkoxy group to be terminally substituted at a terminal alkoxy group by hydroxy, halogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: March 16, 1988
    Date of Patent: October 3, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Maienfisch
  • Patent number: 4863945
    Abstract: Pyrrolobenzimidazoles of the formula: ##STR1## are useful for treatment of heart and circulatory diseases. R.sub.1 is substituted phenyl; or optionally substituted naphthyl or a five- or six-membered heterocyclic group which can be condensed with a phenyl ring to form a bicyclic radical. R.sub.2 is hydrogen, alkyl, alkenyl or cycloalkenyl; R.sub.3 is alkyl, alkenyl or hydroxyalkyl or with R.sub.2 together forms cycloakylene; or R.sub.2 and R.sub.3 together form alkylidene or cycloalkylidene. R.sub.4 is hydrogen or lower alkanoyl. X is a valency bond, alkylene, vinylene, imino or carbonylamino. T stands for two hydrogen atoms. When X is a valency bond, R.sub.1 can also be hydrogen, hydrocarbyl which may also contain oxygen, amino, sulfur, carbonyl and sulfonyl groups. When X is imino or carbonylamino or when R.sub.1 is a bicyclic radical, T can also be oxygen. The compounds also include the tautomers and physiologically acceptable salts with inorganic and organic acids.
    Type: Grant
    Filed: December 10, 1987
    Date of Patent: September 5, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Walter-Gunar Friebe, Alfred Mertens, Klaus Strein, Erwin Boehm
  • Patent number: 4851422
    Abstract: The compound represented by the formula: ##STR1## where R.sup.1 stands for amino or an organic residue bonded through nitrogen; R.sup.2 stands for carboxyl or a group derivable therefrom; R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently stand for hydrogen or an organic residue, including the case where R.sup.5 or R.sup.6 forms a chemical bond or a ring with R.sup.7 or R.sup.8 ; X stands for hydrogen, methoxy or formylamino; or a salt thereof, produceable by the present method, exhibits excellent antimicrobial activity, and is utilized as antimicrobial agents.
    Type: Grant
    Filed: April 30, 1986
    Date of Patent: July 25, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hideaki Natsugari, Yasuhiko Kawano, Akira Morimoto, Kouichi Yoshioka
  • Patent number: 4851406
    Abstract: The present invention provides indole derivatives of the general formula: ##STR1## wherein R.sub.1 is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, cycloalkenyl, carboxyl, cyano, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or aryl radical, R.sub.2 is a hydrogen atom or an alkyl, trihalogenomethyl, hydroxyl, cycloalkyl, cyano, carboxyl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl radical; R.sub.2 is a heterocyclic five-membered ring containing 1 to 4 heteroatoms or a heterocyclic six-membered ring containing 1 to 5 heteroatoms, the heteroatoms of the five- and six-membered rings being the same or different and being nitrogen, oxygen or sulphur and one or more of the nitrogen atoms optionally carrying an oxygen atom, the said five- and six-membered rings optionally being substituted by one or more alkyl, alkoxy, alkylthio, oxo, hydroxyl, nitro, amino, halogen or cyano groups; or R.sub.
    Type: Grant
    Filed: September 4, 1986
    Date of Patent: July 25, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Alfred Mertens, Wolfgang von der Saal, Walter-Gunar Friebe, Bernd Muller-Beckmann, Gisbert Sponer
  • Patent number: 4849432
    Abstract: Novel heterocyclic compounds of the formula ##STR1## wherein, R.sup.1 represents a hydrogen atom or an alkyl group, A represents an ethylene group which may be substituted by alkyl or a trimethylene group which may be substituted by alkyl, X represents an oxygen or sulfur atom or the group ##STR2## in which R.sup.2 represents a hydrogen atom of an optionally substituted alkyl, an alkenyl, an alkynyl or an acyl group, and R.sup.3 represents a hydrogen atom or an alkyl group, and Z represents an optionally sibstituted 5- or 6-membered heterocyclic group which contains at least two hetero atoms selected from oxygen, sulfur and nitrogen atoms, or an optionally substituted 3- or 4-pyridyl group.The above defined novel heterocyclic compounds of formula (I) exhibit powerful insecticidal properties.
    Type: Grant
    Filed: February 24, 1987
    Date of Patent: July 18, 1989
    Assignee: Nihon Tokushu Noyaku Seizo K.K.
    Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Shoko Sasaki, Koichi Moriya, Yumi Hattori
  • Patent number: 4835280
    Abstract: The present invention provides Indolines of the formula: ##STR1## ps useful to provide pharmaceutically active pyrrolobenzimidazoles or tautomers thereof, of the formula: These compounds are useful for treating heart or circulatory diseases, especially those which respond to a change of blood pressure, an increase in cardiac output and/or a change in micro-circulation.
    Type: Grant
    Filed: July 14, 1987
    Date of Patent: May 30, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Alfred Martens, Jens-Peter Holck, Herbert Berger, Bernd Muller-Beckman, Klaus Strein, Egon Roesch
  • 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: 4820867
    Abstract: Compounds of the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic and anti-inflammatory agents.
    Type: Grant
    Filed: April 22, 1986
    Date of Patent: April 11, 1989
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Patrice Belanger, Rejean Fortin, Yvan Guindon, Christiane Yoakim, Joshua Rokach
  • Patent number: 4810282
    Abstract: This invention relates to ortho-(isoxazolyl, isothiazolyl, pyrazolyl, thiadiazolyl, oxadiazolyl, and triazolyl)benzenesulfonamides and their use as herbicides.
    Type: Grant
    Filed: June 10, 1987
    Date of Patent: March 7, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Morris P. Rorer
  • Patent number: 4803277
    Abstract: Novel insecticidally active heterocyclic compounds of the formula ##STR1## wherein W represents a substituted pyridyl group, or a 5- or 6-membered optionally substituted heterocyclic group containing at least two hetero atoms selected from oxygen, sulfur and nitrogen atoms,R represents a hydrogen atom or an alkyl group,Y represents .dbd.N--or ##STR2## R' represents a hydrogen atom, an alkyl group, an aryl group, an acyl group, an alkoxycarbonyl group or a cyano group,Z represents a nitro group or a cyano group, andT represents 3 or 4 optionally substituted ring members of a 5- or 6-membered unsaturated heterocyclic ring which it forms together with the adjoining carbon atom and nitrogen atom, said 5- or 6-membered unsaturated heterocyclic ring containing 1 to 3 hetero atoms which are selected from oxygen, sulfur and nitrogen atoms and at least one of which is a nitrogen atom.
    Type: Grant
    Filed: August 24, 1987
    Date of Patent: February 7, 1989
    Assignee: Nihon Tokushu Noyaku Seizo K.K.
    Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shoko Sasaki, Koichi Moriya, Yumi Hattori, Katsuhiko Shibuya
  • Patent number: 4782169
    Abstract: Compounds of the Formula I, II, III, VI and VII ##STR1## wherein the symbols have defined meanings are herbicides, plant growth regulators or intermediates thereof.
    Type: Grant
    Filed: October 6, 1986
    Date of Patent: November 1, 1988
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Samuel B. Soloway, Pierre Vogel, Claude H. Aubin Le Drian, James E. Powell
  • Patent number: 4782083
    Abstract: Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein: one of R.sub.1 and R.sub.2 is hydrogen or C.sub.1-4 alkyl and the other is C.sub.1-4 alkyl or R.sub.1 and R.sub.2 together are C.sub.2-5 -polymethylene;either R.sub.3 is hydrogen, hydroxy, C.sub.1-6 alkoxy or C.sub.1-7 acyloxy and R.sub.4 is hydrogen or R.sub.3 and R.sub.4 together are a bond;R.sub.5 is hydrogen C.sub.1-6 alkyl optionally substituted by halogen hydroxy, C.sub.1-6 alkoxy, C.sub.1-6 alkoxycarbonyl, carboxy or amino optionally substituted by one or two independent C.sub.1-6 alkyl groups, or C.sub.2-6 alkenyl, amino optionally substituted by a C.sub.1-6 alkyl or C.sub.1-6 alkenyl group or by a C.sub.1-6 alkanoyl group optionally substituted by up to three halo atoms, by a phenyl group optionally substituted by C.sub.1-6 alkyl, C.sub.1-6 alkoxy or halogen, or aryl or hetroaryl, either being optionally substituted by one or more groups or atoms selected from the class of C.sub.1-6 alkyl, C.sub.
    Type: Grant
    Filed: August 29, 1986
    Date of Patent: November 1, 1988
    Assignee: Beecham Group P.L.C.
    Inventors: Frederick Cassidy, Geoffrey Stemp, John M. Evans
  • Patent number: 4775406
    Abstract: The salts of 1-phenylimidazole-5-carboxylic acids substituted in the phenyl ring, of the general formula (I) ##STR1## exhibit a good plant growth-regulating activity. In the general formula the symbols have the following meaning:Y is an ammonium ion substituted up to fourfold by (substituted) alkyl, (substituted) alkenyl, alkynyl, (substituted) cycloalkyl, cycloalkenyl, and (substituted) phenyl, wherein the charged N may be part of a heterocyclic radial (NH.sub.4.sup.+ is excepted); phosphonium ion substituted fourfold by alkyl, (substituted) phenyl or (substituted) benzyl; sulfonium- or sulfoxonium ion substituted threefold by alkyl, (substituted) phenyl or (substituted) benzyl; the guanidinium ion or an O-alkylisourea cation;R.sup.1, R.sup.2 independently of each other are alkyl;R.sup.3 is alkyl, alkoxy or halogen; andn is 0, 1, 2 or 3.
    Type: Grant
    Filed: November 21, 1985
    Date of Patent: October 4, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Roland Schmierer, Ernst-Friedrich Schulze, Helmut Bustell, Erwin Hacker
  • Patent number: 4772309
    Abstract: A 5-Acylamino-pyrazole derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, halogen or nitro,R.sup.2 represents hydrogen, alkyl, alkenyl, alkinyl or optionally substituted cycloalkyl,R.sup.3 represents hydrogen or alkyl,R.sup.4 represents hydrogen or alkyl,X represents oxygen or sulphur,n represents the integer 0, 1 or 2,Ar represents in each case optionally substituted phenyl or pyridyl andHet represents an optionally substituted 5- or 6- membered heterocyclic radical linked via a carbon atom,which exhibit herbicidal and plant growth regulating activity.
    Type: Grant
    Filed: March 19, 1987
    Date of Patent: September 20, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jorg Stetter, Reinhold Gehring, Otto Schallner, Hans-Joachim Santel, Robert R. Schmidt, Klaus Lurssen
  • Patent number: 4748165
    Abstract: This invention relates to amidine derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 is hydrogen or a 1-10C alkyl, 3-8C cycloalkyl, 4-14C cycloalkylalkyl, 3-6C alkenyl, 3-6C alkynyl, 1-6C alkanoyl, 6-10C aryl, 7-11C aralkyl or 7-11C aroyl radical, the latter three being optionally substituted; ring X is a heterocyclic ring as defined in the specification; A is phenylene or 5-7C cycloalkylene or a 1-8C alkylene chain into which is optionally inserted one or two groups; and R.sup.2 and R.sup.3 are a variety of radicals described in the specification: and the pharmaceutically-acceptable acid-addition salts thereof. Manufacturing processes and pharmaceutical compositions are also described.
    Type: Grant
    Filed: May 11, 1982
    Date of Patent: May 31, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Derrick F. Jones, Keith Oldham
  • Patent number: 4746669
    Abstract: Thiazole derivatives have been made, for example, by reacting a 2-aryl-2,2-dialkoxyethylamine with an appropriately substituted aryl acetyl halide followed by treating the resulting amide with diphosphoryl pentasulfide. The thiazole derivatives are found to be effective immunoregulants.
    Type: Grant
    Filed: March 26, 1987
    Date of Patent: May 24, 1988
    Assignee: Merck & Co., Inc.
    Inventors: Charles G. Caldwell, Ihor Kopka, Milton L. Hammond, Robert A. Zambias
  • Patent number: 4742060
    Abstract: Novel insecticides of the formula ##STR1## in which n is 0 or 1,X is S, O, ##STR2## Y is N or ##STR3## Z is a 5- or 6-membered nitrogen-containing heterocyclic ring, and R to R.sup.9 variously represent hydrogen or specified organic radicals.
    Type: Grant
    Filed: January 21, 1986
    Date of Patent: May 3, 1988
    Assignee: Nihon Tokushu Noyaku Seizo K. K.
    Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Koichi Moriya
  • Patent number: 4740231
    Abstract: 1-Aryl-5-alkoximinoalkylamino-pyrazoles of the formula ##STR1## in which R represents cyano or nitro, or represents an optionally substituted heterocyclic radical,R.sup.1 represents hydrogen or alkyl,R.sup.2 represents hydrogen or alkyl, or represents optionally substituted aryl,R.sup.3 represents hydrogen, alkyl or alkenyl, or represents in each case optionally substituted aralkyl or aryl andAr represents optionally substituted phenyl or pyridyl,are active as herbicides and plant growth regulants. Compounds of the formula ##STR2## in which R" has the same definition as R other than cyano, are also active and useful as intermediates as well.
    Type: Grant
    Filed: May 22, 1986
    Date of Patent: April 26, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhold Gehring, Otto Schallner, Jorg Stetter, Hans-Joachim Santel, Robert R. Schmidt, Klaus Lurssen
  • Patent number: 4721712
    Abstract: Certain 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position, and also on the carboxamide nitrogen atom, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic agents and anti-inflammatory agents in mammalian subjects. These 2-oxindole-1-carboxamide compounds are of particular value for acute administration for ameliorating pain in human patients recovering from surgery or trauma, and also for chronic administration to human subjects for alleviating the symptoms of chronic diseases, such as rheumatoid arthritis and osteoarthritis. Certain 2-oxindole-1-carboxamide compounds unsubstituted at C-3, but having an acyl substituent on the carboxamide nitrogen atom, are useful as intermediates to the aforementioned analgesic and anti-inflammatory agents.
    Type: Grant
    Filed: November 13, 1984
    Date of Patent: January 26, 1988
    Assignee: Pfizer Inc.
    Inventor: Saul B. Kadin
  • Patent number: 4695567
    Abstract: The present invention provided pyrrolobenzimidazoles or tautomer thereof, of the general formula: ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.3 -C.sub.7 cycloalkyl;R.sub.2 is hydrogen, cyano, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, or a carbonyl group substituted by hydroxyl, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkyoxy, amino, C.sub.1 -C.sub.6 alkylamino, C.sub.2 -C.sub.12 dialkylamino or hydrazino, orR.sub.2 and R.sub.1 together with the carbon to which they are attached form a C.sub.3 -C.sub.8 spirocycloalkyl ring, or R.sub.1 and R.sub.2 together form C.sub.3 -C.sub.7 alkylidene or C.sub.3 -C.sub.7 cycloalkylkidene,X is a valency bond, C.sub.1 -C.sub.
    Type: Grant
    Filed: January 17, 1986
    Date of Patent: September 22, 1987
    Assignee: Boehringer Mannheim GmbH
    Inventors: Alfred Mertens, Jens-Peter Holck, Herbert Berger, Bernd Muller-Beckmann, Klaus Strein, Egon Roesch
  • Patent number: 4692513
    Abstract: Alpha-L-Aspartyl-D-heteroaromatic-substituted glycine esters and amides are disclosed to be useful as high intensity sweeteners. These compounds can be used to sweeten a variety of foods, beverages and other oral products.
    Type: Grant
    Filed: December 20, 1985
    Date of Patent: September 8, 1987
    Assignee: The Procter & Gamble Company
    Inventors: Robert B. Blum, John M. Gardlik, John M. Janusz, George P. Rizzi
  • Patent number: 4692531
    Abstract: Histamine H.sub.2 -receptor antagonists of the formula ##STR1## wherein A, m, Z, n and R.sup.
    Type: Grant
    Filed: September 25, 1986
    Date of Patent: September 8, 1987
    Assignee: Bristol-Myers Company
    Inventors: Aldo A. Algieri, Ronnie R. Crenshaw
  • Patent number: 4690943
    Abstract: Certain novel 2-oxindole compounds, having an acyl substituent at both the 1-position and the 3-position, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic agents and antiinflammatory agents in mammalian subjects. These 1,3-diacyl-2-oxindole compounds are of particular value for acute administration for ameliorating pain in human patients recovering from surgery or trauma, and also for chronic administration to human subjects for alleviating the symptoms of chronic diseases such as rheumatoid arthritis and osteoarthritis.
    Type: Grant
    Filed: June 20, 1985
    Date of Patent: September 1, 1987
    Assignee: Pfizer Inc.
    Inventor: Saul B. Kadin
  • Patent number: 4666502
    Abstract: The invention provides 5-membered heteroaromatic compounds of formula IArN(Y)COCH.sub.2 Cl Iwherein Ar is a 5-membered heteroaromatic group comprising 1 or 2 heteroatoms selected from O, S and N and linked by a ring C-atom to the N-atom of the N(Y)COCH.sub.2 Cl group to which it is bound, whereby where Ar is pyrazolyl, said N(Y)COCH.sub.2 Cl group is in the 4-position,and Y is as specified in the description,the use of these compounds as herbicides, compositions for facilitating such use and the preparation of the chloroacetamides.
    Type: Grant
    Filed: February 3, 1983
    Date of Patent: May 19, 1987
    Assignee: Sandoz Ltd.
    Inventors: Karl Seckinger, Fred Kuhnen, Karlheinz Milzner