Nitrogen Attached Directly Or Indirectly To The Bicyclo Ring System By Nonionic Bonding Patents (Class 549/55)
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Patent number: 4663344Abstract: 3-Hydroxybenzo[b]thiophene derivatives, such as 2-aralkyl, 2-alkyl and 2-alkenyl-3-hydroxybenzo[b]-thiophenes, were prepared by, among other methods, ring closure of 2-(2-carboxy-phenylthio)-.alpha.-substituted acetic acids. These compounds are found to be useful in the treatment of pain, fever, inflammation, arthritic conditions, asthma, allergic disorders, skin diseases, cardiovascular disorders, psoriasis, inflammatory diseases and other prostaglandin and/or leukotriene mediated diseases.Type: GrantFiled: March 11, 1985Date of Patent: May 5, 1987Assignee: Merck & Co., Inc.Inventors: Philippe L. Durette, Bruce E. Witzel, Kathleen M. Rupprecht, Allan N. Tischler, Timothy F. Gallagher
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Patent number: 4652660Abstract: Process for preparing thioindigo compounds of the formula ##STR1## in which A and B denote identical or different, optionally substituted benzene rings or benzene rings to which may be joined further carbocyclic and heterocyclic rings,characterized in that compounds of the formulae ##STR2## in which A and B have the abovementioned meaning andX denotes halogen, such as bromine and preferably chlorine,are reacted in a liquid mixture of an aluminium halide, an alkali metal halide and a carboxamide or sulphonamide, and the resulting intermediate product is subsequently, if desired after prior isolation, oxidized in a manner known per se, and the batch is worked up for the compounds of the formula (I).Type: GrantFiled: July 15, 1985Date of Patent: March 24, 1987Assignee: Bayer AktiengesellschaftInventors: Detlef-Ingo Schutze, Klaus Wunderlich
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Patent number: 4636505Abstract: Acylanilides of the formula ##STR1## wherein R.sup.1 and R.sup.2, the same or different, each is cyano, carbamoyl, nitro, halogeno, perfluoroalkyl or other defined substituents;R.sup.3 is hydrogen or halogen;R.sup.4 is hydrogen or alkyl, or is joined to R.sup.5 ;R.sup.5 is hydrogen, hydroxy, alkoxy or acyloxy or is joined to R.sup.4 ;R.sup.6 is alkyl or halogenoalkyl, or has the formula --A.sup.3 --R.sup.8 or --A.sup.4 --X.sup.2 --A.sup.5 --R.sup.9 ;A.sup.1 and A.sup.4, the same or different, each is alkylene;A.sup.2, A.sup.3 and A.sup.5, the same or different, each is a direct link or alkylene;X.sup.1 and X.sup.2, the same or different, each is oxygen, sulphur, sulphinyl, sulphonyl, imino or alkylimino;R.sup.7 and R.sup.9, the same or different, each is alkyl, alkenyl, hydroxyalkyl, cycloalkyl, phenyl optionally substituted, naphthyl or heterocyclic optionally substituted;and R.sup.8 is phenyl, naphthyl or heterocyclic as defined above for R.sup.7 or R.sup.Type: GrantFiled: July 15, 1983Date of Patent: January 13, 1987Assignee: Imperial Chemical Industries PLCInventor: Howard Tucker
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Patent number: 4581457Abstract: There are disclosed compounds of the formula ##STR1## wherein X is ##STR2## W is ##STR3## Y is ##STR4## n is 0-8; R.sup.1 is hydrogen, loweralkyl, loweralkoxy, lower alkanoyl, halo, trifluoromethyl, cyano or nitro;R.sup.2 is hydrogen or loweralkyl;and the pharmaceutically acceptable salts thereof, and their use in the treatment of leukotriene-mediated naso-bronchial obstructive airpassageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like, and in antithrombotic therapy.Type: GrantFiled: September 21, 1984Date of Patent: April 8, 1986Assignee: American Home Products CorporationInventors: John H. Musser, Dennis M. Kubrak
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Patent number: 4579865Abstract: Compounds of the structure; ##STR1## and pharmaceutically acceptable salts thereof, wherein:R.sub.1 is H, alkyl, alkoxy, carboxyl, alkylcarboxy, trifluoromethyl, halogen, nitro or hydroxy;X is O, N, S or C;Y is O, N or S; andR.sub.2 is H, alkyl, cycloalkyl, aryl or heteroaryl useful in the treatment of ischemic heart disease and hypertriglyceridemia.Type: GrantFiled: March 28, 1984Date of Patent: April 1, 1986Assignee: USV Pharmaceutical Corp.Inventors: John H. Musser, Charles A. Sutherland
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Patent number: 4571406Abstract: Compounds of formula (I): ##STR1## wherein: either one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from the class of C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkoxysulphinyl, C.sub.1-6 alkoxysulphonyl, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkoxycarbonylamino, C.sub.1-6 alkyl-thiocarbonyl, C.sub.1-6 alkoxy-thiocarbonyl, C.sub.1-6 alkyl-thiocarbonyloxy, 1-mercapto C.sub.2-7 alkyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C.sub.1-6 alkyl groups, or C.sub.1-6 alkylsulphinylamino, C.sub.1-6 alkylsulphonylamino C.sub.1-6 alkoxysulphinylamino or C.sub.1-6 alkoxysulphonylamino, or ethylenyl terminally substituted by C.sub.1-6 alkylcarbonyl, nitro or cyano, or --C(C.sub.1-6 alkyl)NOH or --C(C.sub.1-6 alkyl)NNH.sub.2, or one of R.sub.1 and R.sub.Type: GrantFiled: May 16, 1984Date of Patent: February 18, 1986Assignee: Beecham Group p.l.c.Inventors: John M. Evans, Frederick Cassidy
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Patent number: 4479002Abstract: Carbamate-carbamoyl fluoride compounds are useful intermediates for the production of insecticidal bis-carbamate compounds.Type: GrantFiled: December 1, 1975Date of Patent: October 23, 1984Assignee: Union Carbide CorporationInventor: Wei C. Liang
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Patent number: 4458085Abstract: 3-Benzothienylglycines are prepared by reaction of a benzothiophene with an .alpha.-hydroxyglycine derivative in the presence of trifluoroacetic acid.Type: GrantFiled: April 12, 1983Date of Patent: July 3, 1984Assignee: Eli Lilly and CompanyInventor: George W. Huffman
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Patent number: 4454158Abstract: Compounds of the formula ##STR1## wherein: R is phenyl, phenyl monosubstituted, disubstituted, or trisubstituted by (C.sub.1 -C.sub.8) alkyl, (C.sub.1 -C.sub.8)alkoxy, hydroxy, chlorine, bromine, iodine, fluorine, trifluoromethyl, nitro, (C.sub.1 -C.sub.6)alkylcarbonyl, benzoyl, or phenyl; 1-, or 2-naphthyl; 1-, 2-, or 3-indenyl; 1-, 2-, or 9-fluorenyl; 1-, 2-, or 3-piperidinyl; 2- or 3-pyrrolyl; 2- or 3-thienyl; 2- or 3-furanyl; 2- or 3- indolyl; 2- or 3-thianaphthenyl; or 2- or 3-benzofuranyl;R.sub.1 is hydrogen, (C.sub.1 -C.sub.8)alkyl, benzyl, or phenethyl;X and Y independently, are hydrogen, fluorine, chlorine, or bromine; andA is a divalent radical of the formula: ##STR2## wherein R.sub.2 is hydrogen, methyl, or ethyl, and m and n, independently, are an integer from 0 to 4, provided that m+n cannot be greater than 4; --(CH.sub.2).sub.p --D--(CH.sub.2).sub.Type: GrantFiled: June 1, 1981Date of Patent: June 12, 1984Assignee: Merrell Toraude et CompagnieInventor: Philippe Bey
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Patent number: 4435421Abstract: Sulfur-containing bis-amino carbamate compounds exhibit outstanding acaricidal, nematocidal and insecticidal activity.Type: GrantFiled: November 3, 1978Date of Patent: March 6, 1984Assignee: Union Carbide CorporationInventor: Themistocles D. J. D'Silva
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Patent number: 4424231Abstract: There are described compounds of formula I, ##STR1## in which Ra, Rb, Rc, Rd, Re, Rf and Rg, which may be the same or different, each represent hydrogen, amino, hydroxy, alkoxy, alkenyloxy, halogen, acyl, alkenyl, alkyl, or alkoxy substituted by phenyl,Rh is hydrogen, alkyl or --COOH.X is a hydrocarbon chain containing from 2 to 10 carbon atoms and optionally substituted by a hydroxy group,A has no significance or represents Y, OY, or SY and Y represents a C 1 to 4 hydrocarbon chain which is optionally substituted by alkyl C 1 to 4,E and G, which may be the same or different, each represent --O--, --S-- or --CH.sub.2 --, provided that at least one of E and G is --O-- or --S--,L, together with the carbon atoms to which it is attached, forms a benzene, furan, thiophene, pyrrole, or pyran-2-one ring,and pharmaceutically acceptable derivatives thereof.Type: GrantFiled: March 19, 1982Date of Patent: January 3, 1984Assignee: Fisons LimitedInventors: John R. Bantick, John Fuher, David N. Hardern, Thomas B. Lee
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Patent number: 4396621Abstract: Oxothia compounds, especially 2-oxo-2,3-dihydro-benzo[b]-thiophene compounds of the formula ##STR1## in which Ph represents an optionally substituted 1,2-phenylene radical, X represents oxygen or sulphur, R.sub.1 represents an organic radical bonded via a carbon atom and R.sub.2 denotes hydrogen or an optionally substituted hydrocarbon radical of aliphatic character, and their salts are useful as peripheral analgetics and/or as antiphlogistic uricosuric and/or thrombolytic agents.Type: GrantFiled: November 7, 1980Date of Patent: August 2, 1983Assignee: Ciba-Geigy CorporationInventors: Raymond Bernasconi, Pier G. Ferrini, Richard Goschke, Jacques Gosteli
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Patent number: 4391627Abstract: Novel N-(heterocyclicaminocarbonyl)carbonyl-substituted benzothiophene- and benzofuransulfonamides are useful as herbicides. The invention also includes novel sulfonamides and sulfonyl isocyanates useful in preparing such compounds.Type: GrantFiled: June 22, 1981Date of Patent: July 5, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventor: George Levitt
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Patent number: 4362740Abstract: New spiro compounds of the formula: ##STR1## wherein n is an integer of 1 to 4, and X is halogen, lower alkyl, nitro, amino which may be substituted, hydroxyl which may be substituted, acyl, carboxyl, lower alkoxycarbonyl, carbamoyl which may be substituted, sulfamoyl which may be substituted, lower alkylthio or lower alkylsulfonyl, or two of X at the 5- and 6-positions together form --CH.dbd.CH--CH.dbd.CH--, exhibit inhibitory activity to thrombocyte aggregation and are useful for the prophylaxis or treatment of cardiovascular disturbance such as thrombosis.Type: GrantFiled: September 19, 1980Date of Patent: December 7, 1982Assignee: Takeda Chemical Industries, Ltd.Inventors: Isuke Imada, Hirosada Sugihara, Mitsuru Kawada
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Patent number: 4304919Abstract: The invention relates to asymmetrical thioindigo compounds of the formula I ##STR1## wherein at least one substituent R is different from a substituent R' and preferably at most three Rs or R's are different from hydrogen, e.g. the compound (I), wherein theRs and R's in the positions 4, 6, 7, 4', 6' and 7' are hydrogen, the R in position 5 is methyl and the R' in position 5' is --(CH.sub.2) OCOCH.sub.3. These compounds can be obtained by a novel process in simple and economic manner and in high purity by reacting a compound of the formula II ##STR2## (wherein X is halogen) with corresponding thiophenols, and cyclising the unsubstituted or substituted 2-thiophenyl-carboxymethylene-benzothiophen-3-ones thereby obtained. Some of the compounds of the formula I are known per se and they are used, inter alia, as disperse, melt spinning and pigment dyes.Type: GrantFiled: July 14, 1980Date of Patent: December 8, 1981Assignee: Ciba-Geigy CorporationInventors: Niklaus Buhler, Hans Bosshard
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Patent number: 4303669Abstract: Novel hybrid 1,3-dione-carbamate compounds which exhibit utility as insecticides and acaricides. Also included are insecticidal and acaricidal compositions containing these compounds and a method of controlling insects and acarids.Type: GrantFiled: March 25, 1980Date of Patent: December 1, 1981Assignee: Union Carbide CorporationInventor: Themistocles D. J. D'Silva
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Patent number: 4298613Abstract: Heterocyclic sulfenamides, such as N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-trifluoromethyl)ph enyl]-3-nitro-2-pyridinesulfenamide, are useful as miticides, insecticides, fungicides and ovicides.Type: GrantFiled: May 5, 1980Date of Patent: November 3, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Gerald E. Lepone
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Patent number: 4288437Abstract: Compounds of the formula ##STR1## wherein Ar is phenyl; mono- or di-substituted phenyl, where the substituents are one to two halogens, one to two alkyls of 1 to 3 carbon atoms, or one amino, nitro, cyano or trifluoromethyl; or pyridinyl;R is hydrogen, chlorine, methyl or methoxy;R.sub.1 is hydrogen or methyl;R.sub.2 is hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, methyl-(cycloalkyl of 3 to 8 carbon atoms) or --A--R.sub.4,where A is alkylene of 2 to 3 carbon atoms, and R.sub.4 is hydroxyl, methylamino, dimethylamino, N-methyl-ethylamino, diethylamino, pyrrolidino, piperidino, hexamethyleneimino, morpholino or 4-methyl-1-piperazinyl; orR.sub.1 and R.sub.Type: GrantFiled: July 28, 1980Date of Patent: September 8, 1981Assignee: Boehringer Ingelheim GmbHInventors: Wolfhard Engel, Gunter Trummlitz, Ernst Seeger, Joachim Kahling
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Patent number: 4260779Abstract: Oxothia compounds, especially 2-oxo-2,3-dihydro-benzo[b]thiophene compounds of the formula ##STR1## in which Ph represents an optionally substituted 1,2-phenylene radical, X represents oxygen or sulphur, R.sub.1 represents an organic radical bonded via a carbon atom and R.sub.2 denotes hydrogen or an optionally substituted hydrocarbon radical of aliphatic character, and their salts are useful as peripheral analgetics and/or as antiphlogistic uricosuric and/or thrombolytic agents.Type: GrantFiled: November 9, 1979Date of Patent: April 7, 1981Assignee: Ciba-Geigy CorporationInventors: Raymond Bernasconi, Pier G. Ferrini, Richard Goschke, Jacques Gosteli
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Patent number: 4252739Abstract: This invention provides a convenient and commercially adaptable process for the preparation of vinylcyclopropane derivatives in high yields. The process involves reacting an alkylating agent and an activated methylene compound in the presence of an onium compound, an alkali metal compound and water, which while only necessary in trace amounts can be present in substantial quantities.Type: GrantFiled: August 20, 1979Date of Patent: February 24, 1981Assignee: Emery Industries, Inc.Inventors: Richard G. Fayter, Jr., John F. White, Eugene G. Harris