Chalcogen Attached Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 549/78)
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Patent number: 5026759Abstract: 2-Substituted-1-naphthols are 5-lipoxygenase inhibitors which make them useful in the treatment of inflammation, obstructive lung diseases and/or psoriasis. Useful 2-substituent groups are alkyls, alkenyls, alkynyls, cycloalkyls, cycloalkenyls, the groups CH.sub.2 --C.tbd.C--(CH.sub.2).sub.m R.sup.5 and CH.dbd.CH--(CH.sub.2).sub.n R.sup.5 (where m is 1-4, n is 0-3 and R.sup.5 includes phenyl, COOR.sup.9, where R.sup.9 is H or alkyl of 1-4 carbons, AR.sup.6 (where A is a methylene chain and R.sup.6 is a variety of groups including Cl, Br, I, CHO, CN, COOR.sup.9, NH.sub.2, SC(NH)NH.sub.2, phenyl, P(O)(OR.sup.9).sub.2, etc.), and CHR.sup.7 R.sup.21 (where R.sup.7 is a variety of aromatic and heterocyclic groups and R.sup.21 is H, optionally substituted phenyl and a variety of heterocyclic groups).Type: GrantFiled: December 4, 1989Date of Patent: June 25, 1991Assignee: Du Pont Merck PharmaceuticalInventor: Douglas G. Batt
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Patent number: 5023382Abstract: 2,3-disubstituted-2-cyclopenenones (such as cisjasmone) are prepared by (a) reacting an alkl 2-chloro-2,3-disubstituted-3-butenoate with a lithiomercaptan compound, (b) subjecting that product to reductive dehydrosulfurization. Methods of preparing the reactants are also disclosed.Type: GrantFiled: January 24, 1990Date of Patent: June 11, 1991Assignee: Petrolite CorporationInventor: Jacob Mathew
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Patent number: 4992559Abstract: Thiophene derivatives of the formula ##STR1## wherein R.sup.1 and R.sup.2 are certain specified substituent groups can be homopolymerized or copolymerized to form polymers which are electroconductive. These polymers find many uses, for example, as EMI/RF shielding materials, in electrochromic display systems, as antistatics, as ion and pH sensors, as battery electrode materials etc.Type: GrantFiled: July 16, 1987Date of Patent: February 12, 1991Assignee: Cookson Group plcInventors: Poopathy Kathirgamanathan, Martin R. Bryce, David Parker, Nigel R. M. Smith, Andre D. Chissel
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Patent number: 4992577Abstract: A process for preparing a compound of the formula ##STR1## in which Y is halogen, alkyl or cycloalkyl optionally substituted by halogen or C.sub.1-4 -alkoxy, alkenyl optionally substituted by halogen, aryl, heteroaryl or alkoxycarbonyl,X is hydrogen, halogen or optionally halogen-substituted alkyl, orX and Y, together with the adjacent C atom, form a saturated cycloalkphatic ring having up to 6 C atoms, andR is hydrogen or C.sub.1 -C.sub.4 -alkyl, comprising reacting an aldehyde of the formula ##STR2## with 2-methylbutan-3-one of the formula ##STR3## in the presence of a hydrohalic acid thereby to form a 4,4-dimethyl-3-halogeno-1-hexen-5-one of the formula ##STR4## in which Hal is halogen, halogenating said compound to produce a compound of the formula ##STR5## and reacting said compound with a base of the formulaR--OM (VI)in whichM is one equivalent of an alkali or alkaline earth metal ion.Compounds IV and V are new. By suitable conditions the trans isomer is selectively produced.Type: GrantFiled: May 22, 1989Date of Patent: February 12, 1991Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
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Patent number: 4988727Abstract: A compound selected from the group consisting of all enantiomeric and diastereoisomeric forms possible of compounds of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, halogen, and alkyl and alkoxy of 1 to 5 carbon atoms, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, one of A and B being ##STR2## and the other being ##STR3## R is hydrogen or alkyl of 1 to 5 carbon atoms, Z is --(CH.sub.2).sub.n -- or branched alkylene of 2 to 8 carbon atoms, n is an integer from 0 to 5, Y is selected from the group consisting of naphthyl, indenyl, heterobicyclics and heteromonocyclic containing 5 to 6 ring members, all optionally substituted with at least one member of the group consisting of alkyl and alkoxy of 1 to 5 carbon atoms, halogen, --OH, --CF.sub.3, --NO.sub.2, --NH.sub.Type: GrantFiled: September 19, 1989Date of Patent: January 29, 1991Assignee: Roussel UclafInventors: Francois Clemence, Michel Fortin
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Patent number: 4975451Abstract: Compounds of the formula ##STR1## in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; and Ar.sup.1 is 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, 2-methyl[1-1'-biphenyl]-3-yl, or 6-phenoxy-2-pyridyl, exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively nontoxic to fish.Type: GrantFiled: March 2, 1989Date of Patent: December 4, 1990Assignee: FMC CorporationInventors: Thomas G. Cullen, Scott McN. Sieburth, Gary A. Meier, John F. Engel, Leslie W. Stratton, Alan W. Fritz
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Patent number: 4962229Abstract: 3-R.sup.1 -3-oxoprop-1-ene-1,1-diphosphonic acids corresponding to the following general formula ##STR1## in which R.sup.1 is a tertiary substituted alkyl group, an optionally substituted cycloalkyl group, or an optionally substituted aryl or heteroaryl group, andM is hydrogen or the cation of a base;to a process for their production in which 3-R.sup.1 -3-oxo-1-aminopropane-1,1-diphosphonic acids corresponding to the following general formula ##STR2## in which R.sup.1 is as defined above, are reacted with an aqueous or alcoholic alkali metal hydroxide solution; then water followed by an alcohol infinitely miscible with water is added to the reaction mixture, and the pure olefinic diphosphonic acids are obtained by addition of an acid; to the use of the above compounds of formula III as complexing agents and as thresholders; and to compositions containing one or more compounds of formula (III).Type: GrantFiled: June 30, 1989Date of Patent: October 9, 1990Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Helmut Blum, Siglinde Hemmann
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Patent number: 4958033Abstract: A process for preparing an alcohol of the formula: ##STR1## by reacting a carbonyl compound of the formula: ##STR2## or an oxirane of the formula: ##STR3## magnesium and a propargyl halide of the formula: ##STR4## followed by hydrolysis, characterized in that the carbonyl compound (II) or the oxirane compound (III) and the propargyl halide (IV) are reacted simultaneously with magnesium in an inert solvent in the presence of zinc or a halide thereof.Type: GrantFiled: September 26, 1986Date of Patent: September 18, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Yukihisa Takisawa, Nobuharu Kono, Kenji Saito, Hiroshi Yamachika
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Patent number: 4943584Abstract: Novel (p-phenoxyphenoxy)-methyl-five-membered heeroaromatic radicals of the formula ##STR1## where the substituents have the following meanings: R.sup.1, R.sup.2, R.sup.3 hydrogen, halogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.3 -C.sub.10 -cycloalkyl, nitro or cyano,R.sup.4 hydrogen or C.sub.1 -C.sub.4 -alkyl, and a five-membered heteroaromatic ring, and their use for combating pests.Type: GrantFiled: April 20, 1988Date of Patent: July 24, 1990Assignee: BASF AktiengesellschaftInventors: Hans Theobald, Christoph Kuenast, Peter Hofmeister, Hans-Juergen Neubauer, Thomas Kuekenhoehner, Wolfgang Krieg, Joachim Leyendecker, Uwe Kardorff
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Patent number: 4939280Abstract: 4-Oxaaldehydes of the formula ##STR1## are prepared by catalytic isomerization of 1,3-dioxanes by a process in which a 1,3-dioxane of the formula ##STR2## where R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are identical or different and are each hydrogen, a straight-chain or branched alkyl, alkenyl or alkynyl radical of not more than 18 carbon atoms, a cycloalkyl or cycloalkenyl radical of 5 to 8 carbon atoms, an aryl, alkylaryl, aralkyl or alkenylaryl radical of 5 to 16 carbon atoms or a heterocyclic radical, and furthermore R.sup.1 and R.sup.2 and/or R.sup.4 and R.sup.5 together with the carbon atom to which they are bonded may form a cycloalkane, a cycloalkene or a heterocyclic structure, and the stated radicals may furthermore carry substituents which are inert under the reaction conditions, and R.sup.3 is hydrogen or straight-chain or branched alkyl, is isomerized using a phosphate as a catalyst.Type: GrantFiled: April 29, 1988Date of Patent: July 3, 1990Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Franz Merger, Helmut Lermer
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Patent number: 4937253Abstract: This invention relates to ester prodrugs for alkanoic acid compounds useful as leukotriene antagonists, and pharmaceutical compositions containing such ester prodrug compounds. This invention also relates to methods of treating diseases in which leukotrienes are a factor by administration of an effective amount of the above compounds or compositions.Type: GrantFiled: September 23, 1988Date of Patent: June 26, 1990Assignee: SmithKline Beecham CorporationInventors: John G. Gleason, Ralph F. Hall, John F. Newton, Kathleen A. Phipps, Joanne Smallheer
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Patent number: 4927947Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## wherein A is pyridyl, furyl, thienyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH and its esters, amides and pharmaceutically acceptable salts, --CHO and its acetal derivatives, --COR.sub.1 and its ketal derivatives where R.sub.1 is --(CH.sub.2).sub.n CH.sub.3 where n is defined above, or --CH.sub.2 OH and its ether and acyl ester derivatives; or a pharmaceutically acceptable salt.Type: GrantFiled: January 30, 1989Date of Patent: May 22, 1990Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 4925479Abstract: Compounds of the formula ##STR1## wherein X is oxy, thio, sulfinyl or sulonyl;R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro;cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl with the proviso that R.sup.1 and R.sup.3 are not both phenyl or substituted phenyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; andR.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 aloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.Type: GrantFiled: November 21, 1988Date of Patent: May 15, 1990Assignee: Imperial Chemical Industries PLCInventor: David L. Lee
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Patent number: 4923884Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## wherein A is pyridyl, furyl, thienyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH and its esters, amides and pharmaceutically acceptable salts, --CHO and its acetal derivatives, --COR.sub.1 and its ketal derivatives where R.sub.1 is --(CH.sub.2).sub.n CH.sub.3 where n is defined above, or --CH.sub.2 OH and its ether and acyl ester derivatives; or a pharmaceutically acceptable salt.Type: GrantFiled: April 1, 1988Date of Patent: May 8, 1990Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 4920232Abstract: Known and novel substituted acroleins of the general formula I ##STR1## where R.sup.1 is alkoxy, phenoxy, halogen, haloalkyl, haloalkoxy, haloalkylthiyl or nitro, n is an integer from 1 to 5, in the case of n being greater than 1 the R.sup.1 s being identical or different and in the event of nitro substitution the aromatic ring carrying not more than 3 nitro groups, and where R.sup.2 is alkyl, cycloalkyl, unsubstituted or substituted aryl or hetaryl or a nonaromatic heterocyclic radical, are prepared by reacting a phenylacetaldehyde of the general formula II ##STR2## with an aldehyde of the general formula III[R.sup.2 -CHO] IIIin the presence of a base and a solvent. These acroleins are useful to prepare hydroxymethyloxiranes which are intermediates in the synthesis of antimycotic and fungicidal azoylmethyloxiranes.Type: GrantFiled: June 27, 1988Date of Patent: April 24, 1990Assignee: BASF AktiengesellschaftInventors: Norbert Goetz, Stefan Karbach, Hans-Gert Recker
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Patent number: 4913721Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein V is an oxygen or a sulphur atom; X and Y, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkynyl, haloalkyl, alkoxy, haloalkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, acylamino, nitro, nitrile, --CO.sub.2 R.sup.3, --CONR.sup.4 R.sup.5, or --COR.sup.6 groups; or the groups X and Y, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and Z is optionally substituted methylene, optionally substituted amino, oxygen or sulphur and when Z is a substituted methylene group, the substituent may join the 2-position of the phenyl ring to form a non-aromatic fused ring; R.sup.1 and R.Type: GrantFiled: October 31, 1988Date of Patent: April 3, 1990Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey
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Patent number: 4889865Abstract: Mono, di and tri-esters of 1,8-dihydroxy-10-phenyl-9-anthrone or -9-anthranol have the formula ##STR1## wherein p is 0 or 1,(a) when p=0, t=1 and R.sub.2 represents hydrogen or --COR.sub.3,(b) when p=1, t=0 and R.sub.1 and R.sub.2 each independently represent hydrogen or --COR.sub.3,R.sub.3 represents linear or branched alkyl having 1-17 carbon atoms, cycloalkyl, phenyl or phenyl substituted by lower alkyl, lower alkoxy, halogen, a nitro function, --CF.sub.3 or a hydroxyl function, and mixtures of said esters. These esters are prepared by reacting 1,8-dihydroxy-10-phenyl-9-anthrone with an activated form of an acid. The esters are useful in human or veterinary medicine and in cosmetic compositions.Type: GrantFiled: February 21, 1989Date of Patent: December 26, 1989Assignee: Centre International de Recherches Dermatologiques C.I.R.D.Inventors: Braham Shroot, Gerard Lang, Jean Maignan, Serge Restle, Christopher Hensby, Michel Colin
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Patent number: 4885404Abstract: Disclosed is a process for the production of acids of the formula ##STR1## wherein R is 2-fluoro-4-(1,1'-biphenyl), 4-(2-methylpropyl)phenyl, 6-methoxy-2-napthyl, 3-benzophenyl, 4-(2-thienylcarbonyl)-phenyl or 7-chlorocarbazole-3-yl which comprises contacting an organometallic compound of the formula R--M--R.sub.Type: GrantFiled: March 6, 1987Date of Patent: December 5, 1989Assignee: The Upjohn CompanyInventor: Peter G. M. Wuts
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Patent number: 4880575Abstract: 3-R.sup.1 -3-oxoprop-1-ene-1,1-diphosphonic acids corresponding to the following general formula ##STR1## in which R.sup.1 is a tertiary substituted alkyl group, an optionally substituted cycloalkyl group, or an optionally substituted aryl or heteroaryl group, andM is hydrogen or the cation of a base;to a process for their production in which 3-R.sup.1 -3-oxo-1-aminopropane-1,1-diphosphonic acids corresponding to the following general formula ##STR2## in which R.sup.1 is as defined above, are reacted with an aqueous or alcoholic alkali metal hydroxide solution; then water followed by an alcohol infinitely miscible with water is added to the reaction mixture, and the pure olefinic diphosphonic acids are obtained by addition of an acid; to the use of the above compounds of formula III as complexing agents and as thresholders; and to compositions containing one or more compounds of formula (III).Type: GrantFiled: July 22, 1988Date of Patent: November 14, 1989Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Helmut Blum, Siglinde Hemmann
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Patent number: 4868337Abstract: A process for synthesizing an optically pure ketone comprising the steps of: treating an appropriate optically pure boronic ester with an organolithium compound at -78.degree. C. to obtain the "ate" complex, separating the optically pure borinic ester from the complex and converting said borinic ester into an optically pure ketone represented by the formulae:R*COR.sup.1 and R*COC.tbd.CR.sup.1wherein R* is a chiral organyl moiety and R.sup.1 is an achiral organyl moeity.Type: GrantFiled: December 17, 1987Date of Patent: September 19, 1989Assignee: Aldrich-Boranes, Inc.Inventor: Herbert C. Brown
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Patent number: 4845236Abstract: A compound having the structural formula ##STR1## where R is C.sub.1 -C.sub.6 alkyl or C.sub.5 -C.sub.6 cycloalkyl; X is hydrogen or methyl;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and are hydrogen, halogen, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.7 -C.sub.9 aralkyl, phenyl, nitro, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, C.sub.7 -C.sub.9 aralkoxy, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, tetrahydro-2-thienyl, dioxytetrahydro-2-thienyl, alkali metal carboxylate, C.sub.2 -C.sub.5 alkoxycarbonyl, phenoxycarbonyl or N(R.sup.5)R.sup.6 ;R.sup.5 and R.sup.6 are the same or different and are hydrogen or C.sub.1 -C.sub.2 alkyl; andn is 0, 1 or 2 is disclosed. A method for controlling insects using an insecticidally effective amount of this compound is also taught.Type: GrantFiled: August 10, 1988Date of Patent: July 4, 1989Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd./LteeInventors: Anupama Mishra, Richard C. Moore
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Patent number: 4826829Abstract: Thiophene derivatives of the following formula are effective as acaricdies: ##STR1## wherein A is selected from -phenylthienyl and -phenyl optionally carrying one or more substitutents selected from -lower alkyl, -lower alkoxy, -phenoxy, -hydroxy, -halogen, -lower haloalkyl, -phenylcarbonyl, -lower alkyl carbonyloxy, -lower alkyl sulfonyl, -lower alkyl sulfonyloxy, -amino, -lowr alkyl carboxamido, and -lower haloalkyl carboxamido;R.sub.4 is selected from -hydrogen and -lower alkyl; andR.sub.5 is selected from -thienyl optionally carrying one or more substituents selected from -lower alkyl, -phenylethynyl, -lower alkylthio, -lower haloalkyl carbonyl, and lower alkyl sulfoxy; or -phenyl optionally carrying one or more substituents selected from -lower alkyl and -lower alkoxy.Type: GrantFiled: March 9, 1988Date of Patent: May 2, 1989Assignee: FMC CorporationInventors: Susan E. Eurkart, Richard B. Phillips, David M. Roush
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Patent number: 4820858Abstract: The invention relates to a process for the preparation of 2-(hydroxyalkyl)acrylic compounds having the formula ##STR1## wherein X represents a --CN group, a --COOR.sub.3 group, a --COR.sub.4 group or a --CONR.sub.4 R.sub.5 group wherein R.sub.3 is an alkyl group containing 1-4 C atoms and R.sub.4 and R.sub.5 independently represent an H atom or R.sub.3, andwherein R.sub.1 and R.sub.2 independently represent an H atom or an alkyl group with 1-4 C atoms or an (hetero) aryl group, or R.sub.1 and R.sub.2 together represent a cyclic compound with 5-12 C atomsby contacting an acrylic compound H.sub.2 C.dbd.CH--X with a carbonyl compound of the formula ##STR2## wherein X, R.sub.1 and R.sub.2 denote the same as in the above, this being effected in the liquid phase in the presence of a tertiary amine, characterized in that the reaction is carried out at a pressure in excess of 500 bar in excess of 500 bar, advantageously 1,500-18,000 bar.Type: GrantFiled: March 18, 1988Date of Patent: April 11, 1989Assignee: Stamicarbon B.V.Inventors: Neil S. Isaacs, Jonathan Hill
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Patent number: 4820827Abstract: A small group of 2,3-diaryl-5-bromothiophene compounds such as 5-bromo-2-(4-methylthiophenyl)-3-(4-fluorophenyl)thiophene have been found to possess significant and unexpected antiinflammatory activity, and inhibition of prostaglandin synthetase useful for the treatment of arthritis and dysmenorrhea.Type: GrantFiled: February 10, 1984Date of Patent: April 11, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventor: Stephen B. Haber
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Patent number: 4810716Abstract: The present invention is novel diarylalkanoids having activity as lipoxygenase inhibitors, novel pharmaceutical compositions therefor, and novel methods of use in treating asthma, allergies, cardiovascular diseases, migraines, psoriasis and immunoinflammatory diseases for diarylalkanoids. The compounds of this invention are also useful as cytoprotective agents.Type: GrantFiled: March 3, 1987Date of Patent: March 7, 1989Assignee: Warner-Lambert CompanyInventors: David T. Connor, Daniel L. Flynn
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Patent number: 4808762Abstract: Compounds of the formula ##STR1## in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; Z is oxygen, sulfur, or methylene; and Ar' is 2-methyl[1,1'-biphenyl]-3-yl, 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, or 6-phenoxy-2-pyridyl exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively harmless to aquatic fauna.Type: GrantFiled: September 9, 1987Date of Patent: February 28, 1989Assignee: FMC CorporationInventors: Gary A. Meier, Scott M. Sieburth, Thomas G. Cullen, John F. Engel
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Patent number: 4797456Abstract: Water-soluble sulfonium salts are converted, without the elimination of odorous volatile by-products, to water-insoluble products useful as binders in coating formulations by heating a water-soluble cyclic sulfonium salt in which the sulfonium sulfur is bonded only to aliphatic carbons.Type: GrantFiled: December 9, 1982Date of Patent: January 10, 1989Assignee: The Dow Chemical CompanyInventors: Ritchie A. Wessling, Donald L. Schmidt, Kiyoshi I. Aikawa
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Patent number: 4792567Abstract: Acaricidal aryl arylthien-2-yl ethenes of the formula ##STR1## in which R.sup.2 and R.sup.3 are each an optionally substituted phenyl or thienyl group are disclosed and claimed.Type: GrantFiled: June 9, 1987Date of Patent: December 20, 1988Assignee: FMC CorporationInventors: Susan E. Burkart, Cesar Rodriguez, David M. Roush, Richard B. Phillips
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Patent number: 4781750Abstract: Enols, their geometric isomers, tautomers and halogen addition products having the formula ##STR1## as defined herein and compositions containing these compounds exhibit herbicidal activity.Type: GrantFiled: August 27, 1985Date of Patent: November 1, 1988Assignee: Rohm and Haas CompanyInventor: John W. Ashmore
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Patent number: 4782079Abstract: Thiophene derivatives of the following formula are effective as acaricides: ##STR1## wherein R.sub.A is selected from -hydrogen, -halogen, -lower alkyl, hydroxy, -lower alkoxy, -lower alkylthio, -lower alkoxyalkoxy, -lower alkoxycarbonyl, -aryloxycarbonyl, -lower alkoxycarbonyloxy, -lower alkylsulfonyl, -lower alkylsulfonyloxy, -arylsulfonyloxy, and -lower alkyl phosphonyloxy;R.sub.B is -hydrogen, or R.sub.A and R.sub.B together are --C.sub.4 H.sub.4 --bridging 2'-3' or 3'-4';R.sub.3 and R.sub.4 are selected from -hydrogen, -lower alkyl, and -aryl;X is -halogen; andY is selected from -hydrogen and -halogen.Type: GrantFiled: January 26, 1988Date of Patent: November 1, 1988Assignee: FMC CorporationInventors: Susan E. Burkart, Richard B. Phillips, David M. Roush
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Patent number: 4778818Abstract: Substituted cinnamyl-2,3-dihydrobenzofurans and analogs were prepared from the nucleophlic substitution of a cinnamylhalide with a 2,3-dihydrobenzofuran anion or an analog thereof. These compounds were found to be potent topical anti-inflammatory agents.Type: GrantFiled: April 17, 1987Date of Patent: October 18, 1988Assignee: Merck & Co., Inc.Inventors: Michael N. Chang, Norman P. Jensen, Milton L. Hammond, Robert A. Zambias, John McDonald, Kathleen M. Rupprecht
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Patent number: 4772714Abstract: Disclosed is a process for the preparation of alpha-aryl and alpha-heteroaryl ketones useful as intermediates in the synthesis of various pharmaceutical and agricultural chemicals, which process operates according to the following reaction scheme: ##STR1##Type: GrantFiled: July 7, 1986Date of Patent: September 20, 1988Assignee: Agency of Industrial Science & TechnologyInventors: Masato Tanaka, Toshiyasu Sakakura
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Patent number: 4769470Abstract: 5-(Phenyl or phenoxymethyl)-3-(2-thienyl)-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolid ines and related derivatives in which one or more hydrogens on the 5-phenyl or phenoxy rings are replaced by halogen, lower alkyl, lower alkoxy, nitro and combinations thereof are useful as antifungal agents.Type: GrantFiled: October 2, 1987Date of Patent: September 6, 1988Assignee: Pennwalt CorporationInventors: Vassil S. Georgiev, George B. Mullen
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Patent number: 4766198Abstract: This invention relates to novel conductive thienylene- and furanylene-vinylene polymers and to a process for their preparation. The polymer can be formed into coherent films in which no voids are visible up to magnifications of up to 5000 times. These polymers have band gaps below 2 eV which makes them more suitable than conventional polyphenylene and poly(phenylene vinylene) polymers for use e.g. in batteries.Type: GrantFiled: May 19, 1987Date of Patent: August 23, 1988Assignee: The British Petroleum Company p.l.c.Inventors: Kevin Harper, William J. W. Watson
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Patent number: 4757084Abstract: Analogs of 2,5-Diaryl tetrahydrothiophenes which were substituted or unsubstituted on 3,4-positions were prepared.These compounds are found to be leukotriene inhibitors and potent and specific PAF (Platelet Activating Factor) antagonists. They are therefore useful in the treatment of various diseases or disorders mediated by the leukotriene and/or PAF, for example, inflammation, cardiovascular disorder, asthma, lung edema, adult respiratory distress syndrome, pain, and aggregation of platelets.Type: GrantFiled: September 13, 1985Date of Patent: July 12, 1988Assignee: Merck & Co., Inc.Inventor: Tesfaye Biftu
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Patent number: 4749712Abstract: 5-Alkyl-2,3-diarylthiophenes, such as 5-(1,1-dimethylethyl)-2,3-bis(4-methoxyphenyl)thiophene, 5-(1-methylpropyl)-2,3-bis(4-methoxyphenyl)thiophene and 5-cyclohexyl-2,3-bis(4-methoxyphenyl)thiophene, are useful in the treatment of inflammation and/or pain.Type: GrantFiled: December 5, 1984Date of Patent: June 7, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventor: Stephen B. Haber
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Patent number: 4743694Abstract: The addition of organolithium to dimethylhydrazones of certain ethers of a-hydroxyaldehydes results in the synthesis of threo- or erythro- intermediates readily convertible to threo- or erythro-2-amino alcohols.Type: GrantFiled: April 11, 1986Date of Patent: May 10, 1988Assignee: Mercek & Co., Inc.Inventor: David A. Claremon
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Patent number: 4733011Abstract: Compounds of the formula ##STR1## wherein A is C--C single bond, --CH.sub.2 --, --CH(CH.sub.3)--, --C(CH.sub.3).sub.2 --, --CH.sub.2 --CH.sub.2 --, CH(CH.sub.3)CH.sub.2 --, --C(CH.sub.3).sub.2 CH.sub.2 --, --CH.sub.2 --CH.sub.2 --CH.sub.2 -- or --CH.sub.2 O--; R.sup.1a and R.sup.1 each independently is hydrogen or a protective group which can be cleaved by solvolysis or by hydrogenolysis; R.sup.2 is H or alkyl of 1 to 3 C atoms; R.sup.3 is alkyl of 3 to 5 C atoms, phenyl or phenyl which is monosubstituted to trisubstituted by F, Cl, OH, OCH.sub.3, OC.sub.2 H.sub.5, CF.sub.3 or alkyl of 1 to 3 C atoms, or, when A is not --CH.sub.2 O--, can also be pyridyl, thienyl, naphthyl or alkoxy of 1 to 4 C atoms; indicates a bond in the .beta.-position and wavy line ( ) means that the bond can be in the .alpha.- or .beta.-position, are valuable intermediates for the stereospecific preparation of 13-thiaprostaglandin derivatives. The latter are prepared by U.V.Type: GrantFiled: August 19, 1985Date of Patent: March 22, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Bernhard Riefling, Hans-Eckart Radunz
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Patent number: 4709097Abstract: 4-oxa-aldehydes are prepared by catalytic isomerization of a 1,3-dioxane using an acidic zeolite catalyst.Type: GrantFiled: April 14, 1986Date of Patent: November 24, 1987Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Franz Merger, Rolf Fischer
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Patent number: 4696941Abstract: Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and represent a straight-chain or branched alkyl group of 1 to 15 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, a 2-furyl, 3-furyl, 3-pyridyl, 4-pyridyl or 2-thienyl group or an aromatic group of the formula ##STR2## wherein X, Y and Z are the same or different and represent hydrogen, alkyl of 1 to 3 carbon atoms, trifluoromethyl, alkoxy with 1 to 4 carbon atoms, halogen, nitro or hydroxy groups are useful as pharmaceutical, veterinary and cosmetic agents.Type: GrantFiled: June 28, 1985Date of Patent: September 29, 1987Assignee: Groupement d'Interet Economique dit: Centre International 'de Recherches Dermatologiques C.I.R.D.Inventors: Braham Shroot, Gerard Lang, Jean Maignan
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Patent number: 4686291Abstract: A process for the preparation of a methyl ketone of the formula ##STR1## in which R.sup.1 is alkyl, alkenyl, alkinyl, optionally substituted aryl or optionally substituted heteroaryl,R.sup.2 is alkyl,R.sup.3 is alkyl orR.sup.2 and R.sup.3, together with the carbon atom to which they are bonded, from a cycloalkyl ring,comprising reacting a methyl sec.-alkyl ketone of the formula ##STR2## with a halide of the formulaR.sup.1 --CH.sub.2 --Xin whichX is halogen,in the presence of a base, a diluent, and a phase-transfer catalyst.Type: GrantFiled: November 26, 1985Date of Patent: August 11, 1987Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Hans-Ludwig Elbe
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Patent number: 4684743Abstract: .beta.-Dicarbonyl, .beta.-cyanocarbonyl and .beta.-dicyano compounds I ##STR1## where R.sup.1 is an organic radical, X and Y are COOR.sup.2, --CO--R.sup.2 or --CN and R.sup.2 is an organic radical, are prepared from R.sup.1 --CHO (II) and X--CH.sub.2 --Y (III) by reaction in the presence of a condensation catalyst, hydrogen and a hydrogenation catalyst, using an oxide or phosphate of Mg, Al, Ti, Zn or a rare earth metal as the condensation catalyst.Type: GrantFiled: October 1, 1985Date of Patent: August 4, 1987Assignee: BASF AktiengesellschaftInventors: Walter Gramlich, Klaus Halbritter, Gerd Heilen
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Patent number: 4683330Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.Type: GrantFiled: January 11, 1985Date of Patent: July 28, 1987Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4681952Abstract: A process for the preparation of 2,2-dimethyl-3-arylcyclopropanecarboxylic acid or ester of the formula ##STR1## in which Ar is naphthyl or the radical ##STR2## R.sup.1 is H or C.sub.1 -C.sub.4 -alkyl, Z is oxygen, sulphur, or 1,2-ethenediyl, andR.sup.2 represents hydrogen, halogen, cyano, nitro or trialkylsilyl or a radical, which is optionally substituted by halogen, from the series comprising alkyl, cycloalkyl, alkenyl, alkoxy, alkylenedioxy, alkylthio, alkylsulphinyl, alkylsulphonyl, dialkylamino, phenyl and phenoxy,comprising reacting a 1-aryl-1-halogeno-2,2-dimethyl-3-butanone of the formula ##STR3## in which X.sup.1 is chlorine or bromine, with a base in the presence of a diluent at a temperature between about -20.degree. and +150.degree. C., thereby to form a 2,2-dimethyl-3-arylcyclobutanone of the formula ##STR4## and reacting such 2,2-dimethyl-3-arylcyclobutanone with chlorine or bromine in the presence of an inert diluent at a temperature between about -30.degree. and +50.degree. C.Type: GrantFiled: November 7, 1984Date of Patent: July 21, 1987Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
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Patent number: 4668814Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.Type: GrantFiled: January 11, 1985Date of Patent: May 26, 1987Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4665196Abstract: There are provided compounds which are alkyl sulfonates substituted on a 5-membered heterocyclic or cyclic ring. The hetero-substituents of the ring may be O, S, R.sub.2 N, R.sub.3 R.sub.4.sup.+ N<, ##STR1## where R.sub.2, R.sub.3 and R.sub.4 are the same or different substituted or unsubstituted, and are hydrogen, alkyl or aryl. Optionally, the hetero-substituent may be replaced by R.sub.3 R.sub.4 C. The alkyl sulfonate substituent is in the 3 position of the ring and a substituted or unsubstituted alkyl substituent is in the 4 position of the ring. The compounds may be prepared by reacting X(CH.sub.2 CH.dbd.CHR).sub.2, where X is the above mentioned hetero-substituents or R.sub.3 R.sub.4 C<, with a bisulfate salt.Type: GrantFiled: April 18, 1985Date of Patent: May 12, 1987Assignee: Mobil Oil CorporationInventor: Kirk D. Schmitt
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Patent number: 4644009Abstract: Provided are new compounds having valuable therapeutic activity. These compounds are of the formula: ##STR1## and salts thereof, whereinX=O, S or NR.sub.2 ;Z=(CHR.sub.3).sub.n C(R.sub.3))OH)--, ##STR2## --CH.sub.3 .dbd.CH.sub.3 CR.sub.3 (OH)--, or --(CHR.sub.3).sub.n', M=--O--, --S--, or ##STR3## Z.sub.1 is an alkylene chain of 0-5 carbon atoms in the principal chain and a total of 7 carbon atoms;R.sub.1 is H, phenyl, naphthyl or a sulfur, nitrogen or oxygen-heterocyclic ring;R.sub.2 is H, alkyl, aryl or aralkyl;R.sub.3 is H or CH.sub.3 ;n=0-5; andn'=1-5.Type: GrantFiled: October 29, 1984Date of Patent: February 17, 1987Assignee: USV Pharmaceutical CorporationInventors: Fu-chih Huang, Joseph Auerbach
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Patent number: 4618725Abstract: .alpha.-Methyl-substituted ketones are prepared by reacting the corresponding unsubstituted ketones, which must possess two or more geminal hydrogen atoms in the .alpha.-position, with methanol in the gas phase at from 350.degree. to 500.degree. C. and under from 1 to 20 bar in the presence of a metal oxide.Type: GrantFiled: June 13, 1985Date of Patent: October 21, 1986Assignee: BASF AktiengesellschaftInventor: Hans-Heinrich Lenz
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Patent number: 4607035Abstract: There are described 1-phenoxy(phenylthio)-4-aryl-alkynyloxy-benzene derivatives endowed with a juvenile hormonic activity towards insects and with an acaricide activity. The use of these compounds for controlling insects infestations in both the agrarian and civil field and the processes for preparing said compounds are described too.Type: GrantFiled: July 22, 1983Date of Patent: August 19, 1986Assignee: Montedison S.p.A.Inventors: Franco Bettarini, Pietro Massardo, Paolo Piccardi, Franca Reggiori, Angelo Longoni
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Patent number: 4563537Abstract: New organopalladium reactions involving the addition of thienylpalladium compounds to strained bicyclic alkenes, and subsequent chain extension reactions employing the chemistry of organopalladium compounds are disclosed. By these techniques a large number of bicyclic prostaglandin analogs are prepared, which are useful as inhibitors of arachidonic acid induced blood platelet aggregation, and are specific inhibitors of thromboxane synthetase.Type: GrantFiled: June 4, 1984Date of Patent: January 7, 1986Assignee: Iowa State University Research Foundation, Inc.Inventor: Richard C. Larock