The Chalcogen, X, Is Part Of A -c(=x)x- Group, Wherein The X's Are The Same Or Diverse Chalcogens Patents (Class 549/79)
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Patent number: 4577025Abstract: A method for the preparation of an ester of .alpha.-thio-.alpha.-aromatic propionic acid derivatives of the formula: ##STR1## wherein R.sup.1 is alkyl, phenyl or benzothiazolyl, R.sup.2 is alkyl and Ar is an aromatic substituent.The method comprises reacting an ester of .alpha.-chloro-.alpha.-thiopropionic acid of the formula: ##STR2## with an aromatic compound of the formula ARH, in the presence of a Lewis acid. The method provides good reactivity and positional selectivity in the Friedel-Crafts reaction. Many esters of the formula (2) are useful as pharmaceuticals, agricultural chemicals, perfumes or their intermediates.Type: GrantFiled: August 26, 1983Date of Patent: March 18, 1986Assignee: Nissan Chemical Industries, Ltd.Inventors: Kazutaka Arai, Yoshio Ohara, Yashio Takakuwa, Toyoko Iizumi
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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
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Patent number: 4562267Abstract: Variously substituted alkyl 2-(furyl or thienyl)-2-hydroxyacetates and 2-(furyl or thienyl)-2-hydroxyacetamides are useful as intermediates for hypoglycemic oxazolidine-2,4-diones.Type: GrantFiled: October 14, 1983Date of Patent: December 31, 1985Assignee: Pfizer Inc.Inventor: Rodney C. Schnur
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Patent number: 4560403Abstract: As new compound is provided a cyclohexane derivative of the formula ##STR1## wherein R represents a hydrogen atom or an alkyl group, an alkylthioalkyl group or an unsubstituted or substituted phenyl group; and R.sup.1 represents an alkyl group, an unsubstituted or substituted benzyl group, a phenethyl group, a phenoxymethyl group, a 2-thienylmethyl group, an alkoxymethyl group or an alkylthiomethyl group, or a salt of said cyclohexane compound.This cyclohexane compound exhibits useful plant-growth regulating effects on crop-plants and also non-crop plants such as lawn and may be prepared by cyclization of an acetonylsuccinic acid dialkyl ester, followed by reaction with an organic acid chloride and by intermolecular rearrangement.Type: GrantFiled: September 22, 1983Date of Patent: December 24, 1985Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Kenji Motojima, Takeshige Miyazawa, Yasufumi Toyokawa, Masafumi Matsuzawa, Hiroshi Hokari, Shoji Kusano
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Patent number: 4560763Abstract: A base precursor for heat-developable photosensitive material is disclosed. The precursor is comprised of a compound represented by general formula (I) or (II):(R--C.tbd.C--CO.sub.2 H).sub.x.B (I)R--C.tbd.C--CO.sub.2 H).sub.2.B.sub.y (II)The substituents within the general formulae are defined within the specification. The use of this novel base precursor makes it possible to obtain a material which is very stable at normal temperatures and which smoothly decomposes under heating at 80.degree. C. or higher in order to release a basic constituent.Type: GrantFiled: March 30, 1984Date of Patent: December 24, 1985Assignee: Fuji Photo Film Co., Ltd.Inventors: Kozo Sato, Hiroyuki Hirai
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Patent number: 4545993Abstract: Heterocyclic compounds comprising the formula (I): ##STR1## wherein: R.sub.1, R.sub.2, R.sub.4 and R.sub.5 each are hydrogen or a lower alkyl group;R.sub.3 is hydrogen, a halogen, an alkyl group, a haloalkyl group, an alkoxy group, an alkenyl group, an alkenyloxy group, an aryl group, an aryloxy group, an acyl group or a nitro group;and the broken line connotes a single or double bond at the C.sub.3 -C.sub.4 position, provided that when the broken line connotes a single bond, R.sub.3 is other than hydrogen; and pharmaceutically acceptable salts thereof,exhibiting antiinflammatory, antipyretic and analgesic action.Type: GrantFiled: July 20, 1982Date of Patent: October 8, 1985Assignee: Nippon Zoki Pharmaceutical Co. Ltd.Inventors: Kaoru Okamoto, Masaki Hamada, Teikichi Kurosaki
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Patent number: 4542220Abstract: The invention relates to a process for the preparation of derivatives of dichloroacetic acid esters, by reaction of a glyoxylic acid ester having the general formula R.sub.1 --CO--COOR.sub.2, wherein R.sub.1 represents an optionally substituted aryl or heteroaryl group and R.sub.2 an alkyl, cycloalkyl or aryl group, with phosphoruspentachloride in the presence of a dispersant suitable for distributing the phosphoruspentachloride.Type: GrantFiled: September 15, 1982Date of Patent: September 17, 1985Assignee: Stamicarbon B.V., Licensing Subsidiary of DSMInventors: Antonius Corvers, Joannes M. C. A. Mulders
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Patent number: 4542151Abstract: Tetrahydrothienyl substituted ethers are provided having the structural formula ##STR1## wherein A is (CH.sub.2).sub.2, CH.dbd.CH or a single bond, m is 1 to 5, B is a single bond or CH.dbd.CH, n is 1 to 4, X is O or ##STR2## wherein n' is 0, 1 or 2, R is H, lower alkyl or alkali metal and R.sup.1 is lower alkyl, arylalkyl, aryl, cycloalkyl, cycloalkylalkyl or lower alkenyl and including all stereoisomers thereof.The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease and as antiinflammatory agents and analgesics.Type: GrantFiled: December 17, 1984Date of Patent: September 17, 1985Assignee: E. R. Squibb & Sons, Inc.Inventor: Jagabandhu Das
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Patent number: 4536595Abstract: Alpha-arylpropionic acids and alkaline salts thereof are prepared by catalytic reaction with carbon monoxide of the corresponding secondary halids in an anhydrous low alcohol solvent in the presence of a salt of cobalt hydrocarbonyl and in further presence of alkaline hydroxides under substantially ambient temperature and pressure conditions.The products obtained find useful applications in the field of pharmaceutics (analgesics, antipyretics, etc.) and as intermediates for chemical syntheses of fine chemicals, phytodrugs, etc.Type: GrantFiled: September 17, 1982Date of Patent: August 20, 1985Assignee: Montedison S.p.A.Inventors: Andrea Gardano, Franco Francalcanci, Marco Foa
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Patent number: 4535166Abstract: Rearrangement of alpha-halo-alkylarylketals in neutral or weakly alkaline conditions and in the presence of a polar-protic medium and subsequent hydrolysis of the thus obtained esters, in the same reaction medium, to afford the corresponding alpha-arylalkanoic acids or their salts which are particularly useful as anti-inflammatory, analgesic and antipyretic agents.Type: GrantFiled: August 3, 1983Date of Patent: August 13, 1985Assignee: Zambon S.p.A.Inventors: Graziano Castaldi, Claudio Giordano
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Patent number: 4533749Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: February 16, 1982Date of Patent: August 6, 1985Assignee: The Upjohn CompanyInventors: Paul A. Aristoff, John C. Sih
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Patent number: 4529721Abstract: A compound of the formula: ##STR1## wherein u represents hydrogen, carboxamido, N-hydroxycarboxamido, carboxy, azido, an aryl, an acylamino, a protected carboxy or an N-alkoxycarboxamido, or, together with v, can represent --S-- or --CH.sub.2 S--; v represents hydrogen, halogen, cyano or an alkylthio, or, together with u, can represent --S-- or --CH.sub.2 S--, or, together with w, can represent --(CH.sub.2).sub.3 CO--; w represents hydrogen, carboamoyl, cyano, carboxy, an N-alkylcarbamoyl, an alkyl, an aryl, a protected carboxy or a heterocycle, or, together with v, can represents --(CH.sub.2).sub.Type: GrantFiled: September 21, 1983Date of Patent: July 16, 1985Assignee: Shionogi & Co., Ltd.Inventors: Wataru Nagata, Mitsuru Yoshioka, Yasuhiro Nishitani, Tsutomu Aoki, Toshiro Konoike, Tadatoshi Kubota
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Patent number: 4528384Abstract: Novel polymers having high activity as cationic surface-active agents are prepared by the addition polymerization of ethylenically unsaturated aromatic sulfonium salts, e.g., ##STR1## When such polymers are heated and/or dried, they are irreversibly converted to inert, nonionic residues without the elimination of odorous by-products.The novel sulfonium salt polymers having relatively low molecular weight and low charge density are particularly useful as surfactants or emulsifiers in the emulsion polymerization of ethylenically unsaturated monomers such as styrene, butadiene, alkyl acrylates and the like. The polymers having high molecular weight and high charge density are useful as thickeners and flocculants.Type: GrantFiled: June 30, 1980Date of Patent: July 9, 1985Assignee: The Dow Chemical CompanyInventors: Donald L. Schmidt, Thomas C. Klingler, Ritchie A. Wessling
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Patent number: 4525586Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), methano (C-6a,9), and an additional (olefinic) valence bond (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2', 9-methano (or 2', 9-methano)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.Type: GrantFiled: September 19, 1983Date of Patent: June 25, 1985Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4520207Abstract: 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: September 27, 1982Date of Patent: May 28, 1985Assignee: Iowa State University Research Foundation, Inc.Inventor: Richard C. Larock
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Patent number: 4518799Abstract: Novel processes for making arylpropionic acids are described. One process comprises carboxylating particular Grignard compounds which are the products of a catalyzed reaction between corresponding arylmagnesium bromides and ethylene. Furthermore, the reaction making the particular Grignard compounds is itself novel. Also, an improved method is disclosed for making coupled aryl compounds useful as intermediates for making compounds having a pharmaceutical use. For example, particular biaryls may be used to make some of the Grignard compounds herein from which the arylpropionic acids are made. Finally, an improved bromination is disclosed giving high yields of 4-bromo-2-fluoroaniline, which is thereafter coupled with benzene, then used to make the arylmagnesium bromide reacted with ethylene to obtain the particular Grignard compound and subsequent desired arylpropionic acid, i.e. 2-(2-fluoro-4-biphenylyl)propionic acid.Type: GrantFiled: June 8, 1982Date of Patent: May 21, 1985Assignee: The Upjohn CompanyInventor: Thomas A. Hylton
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Patent number: 4515970Abstract: A process for preparation of substituted acetic acids having the general formula I:Ar--CHR--COOH Iin which R is selected from the group consisting in one hydrogen atom and C.sub.1 -C.sub.4 -alkyl radicals, and Ar is selected from the group consisting in radicals of aromatic nature selected from the following radicals: 2-thienyl, 2-methoxy-1-naphthyl, 3,4-methylenedioxy-phenyl, and the substituted phenyls of the general formula II: ##STR1## where R.sub.1 is selected from the group consisting in hydrogen and C.sub.1 -C.sub.4 -alkyl groups, and R.sub.Type: GrantFiled: April 17, 1984Date of Patent: May 7, 1985Assignee: Societe Francaise HoechstInventors: Yani Christidis, Jean-Claude Vallejos
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Patent number: 4490555Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: March 19, 1982Date of Patent: December 25, 1984Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4487953Abstract: Compounds of Formula (I) ##STR1## wherein the 9-bromine atom can be in the .alpha.- or .beta.-position,R.sub.1 is CH.sub.2 OH or C(O)OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is C(O)NHR.sub.3 wherein R.sub.3 is an acid residue or R.sub.2 ; andA is --CH.sub.2 --CH.sub.2 -- or cis --CH.dbd.CH--;B is --CH.sub.2 --CH.sub.2 --, trans --CH.dbd.CH--, or --C.tbd.C--;W is a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position; D and E together are a direct bond; orD is straight-chain, branched, or cyclic alkylene of 1-10 carbon atoms, optionally substituted by fluorine atoms; andE is oxygen, sulfur, a direct bond --C.tbd.C--, or --CR.sub.6 .dbd.CR.sub.7 --, wherein R.sub.6 and R.sub.7 are different from each other and each is hydrogen, chlorine, or C.sub.1 -C.sub.4 -alkyl;R.sub.4 is a free or functionally modified hydroxy group;R.sub.Type: GrantFiled: December 6, 1982Date of Patent: December 11, 1984Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger
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Patent number: 4487961Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: February 16, 1982Date of Patent: December 11, 1984Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4487960Abstract: Novel compounds of the following formula: ##STR1##Type: GrantFiled: April 19, 1982Date of Patent: December 11, 1984Assignee: The Upjohn CompanyInventor: Chiu-Hong Lin
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Patent number: 4482502Abstract: Biaryl compounds are prepared by coupling an arylamine with an aromatic compound in the presence of an alkyl nitrite and about 0.04-0.6 mol of an acid having a dissociation constant of at least about 1.7.times.10.sup.-5 at 25.degree. C. and about 0.08-1.3 mols of a cuprous halide catalyst per mol of the arylamine. The invention has particular utility in the coupling with aromatic compounds of arylamines having acid-sensitive ar-substituents, e.g. flurbiprofen intermediates, such as 2-(4-amino-3-fluorobenzene)propionitrile and alkyl 2-(4-amino-3-fluorobenzene)propionates.Type: GrantFiled: April 25, 1983Date of Patent: November 13, 1984Assignee: Ethyl CorporationInventor: Venkataraman Ramachandran
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Patent number: 4468521Abstract: Novel .gamma.-lactone derivatives are provided. These lactone derivatives, when reacted with hydrogen halide in alcohol, yield .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters. This ring-opening process is useful for the purpose of increasing the yield of pyrethrin analogs which are of value as insecticides and agricultural chemicals. Thus, the .gamma.-lactone derivatives by-produced in the production process for dihalogenovinyl chrysanthemumates are caused to undergo ring-opening reaction to yield the corresponding .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters which are important intermediates for said pyrethrin analogs.Type: GrantFiled: February 22, 1982Date of Patent: August 28, 1984Assignee: Kuraray Co., Ltd.Inventors: Mori Fumio, Omura Toshiaki, Nishida Takashi, Itoi Kazuo
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Patent number: 4464536Abstract: Antiinflammatory compounds of the following formula are disclosed: ##STR1## wherein R is lower alkyl; R.sup.1 is selected from the group consisting of lower alkyl, benzyl, and N,N-dimethylaminoethyl; or R and R.sup.1 are fused to form an optionally-substituted five- or six-membered heterocyclic ring; and X is hydrogen, methyl or halogen; and pharmaceutically acceptable acid addition salts thereof. Pharmaceutical compositions containing the antiinflammatory compounds and methods of using the antiinflammatory compounds are also described as are a synthetic process and synthetic intermediates for preparing the antiinflammatory compounds.Type: GrantFiled: November 5, 1982Date of Patent: August 7, 1984Assignee: Riker Laboratories, Inc.Inventors: Robert A. Scherrer, George G. I. Moore
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Patent number: 4459305Abstract: The present invention relates to a cyclopropanecarboxylic acid ester derivative of the general formula I: ##STR1## in which R.sub.1 stands for a hydrogen atom, a methyl group, a halogen atom or a halomethyl group, R.sub.1 ' stands for a halomethyl or haloethyl group, R.sub.2 and R.sub.2 ' are the same or different, each standing for methyl group, a halogen atom or a halomethyl group, provided that if R.sub.1 is a hydrogen atom, R.sub.1 ' is a halomethyl group, and R.sub.2 and R.sub.2 ' are each a methyl group, and R stands for a group of the formula II, III, IV, V or VI: ##STR2## in which R.sub.3 stands for a hydrogen atom or a methyl group, R.sub.4 stands for an allyl, propargyl, benzyl or 2,4-pentadienyl group, X stands for an oxygen or sulfur atom, or a --CH.dbd.CH-- group, R.sub.5 stands for a hydrogen atom, or a cyano, ethynyl, propynyl or trifluoromethyl group, R.sub.6 stands for a hydrogen or halogen atom or a methyl or trifluoromethyl group, n is an integer of 1 to 4, R.sub.Type: GrantFiled: December 4, 1981Date of Patent: July 10, 1984Assignee: Dainippon Sochugiku Kabushiki KaishaInventors: Yoshio Katsuda, Yoshihiro Minamite
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Patent number: 4458090Abstract: Novel .gamma.-lactone derivatives are provided. These lactone derivatives, when reacted with hydrogen halide in alcohol, yield .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters. This ring-opening process is useful for the purpose of increasing the yield of pyrethrin analogs which are of value as insecticides and agricultural chemicals. Thus, the .gamma.-lactone derivatives by-produced in the production process for dihalogenovinyl chrysanthemumates are caused to undergo ring-opening reaction to yield the corresponding .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters which are important intermediates for said pyrethrin analogs.Type: GrantFiled: October 15, 1981Date of Patent: July 3, 1984Assignee: Kuraray Co., Ltd.Inventors: Mori Fumio, Omura Yoshiaki, Nishida Takashi, Itoi Kazuo
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Patent number: 4454339Abstract: 9-Fluoroprostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is the residue ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 and A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C,W is a free or functionally modified hydroxymethylene group wherein the OH-group can be in the .alpha.- or .beta.-position,D and E jointly are a direct bond orD is straight-chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen or sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine, or alkyl,R.sub.4 is a free or functionally modified hydroxy group, andR.sub.5 is hydrogen, an optionally substituted aliphatic group, e.g.Type: GrantFiled: July 6, 1982Date of Patent: June 12, 1984Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
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Patent number: 4452979Abstract: A process for preparing antiinflammatory enamines of the following formula ##STR1## wherein R is lower alkyl; R.sup.1 is selected from the group consisting of lower alkyl, benzyl, and N,N-dimethylaminoethyl; or R and R.sup.1 are fused to form an optionally-substituted five- or six-membered heterocyclic ring; and X is hydrogen, methyl or halogen, comprising (a) reacting a 3,5-bis(t-butyl)-4- hydroxybenzoyl-substituted thiophene with a chlorine source selected from thionyl chloride and phosphorus pentachloride; and (b) reacting the resulting intermediate with an amine to provide the enamine.Type: GrantFiled: November 5, 1982Date of Patent: June 5, 1984Assignee: Riker Laboratories, Inc.Inventor: Robert A. Scherrer
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Patent number: 4433160Abstract: A process for producing an .alpha.-arylalkanoic acid ester represented by the general formula ##STR1## wherein Ar represents an aryl group which may optionally be substituted, and R.sup.1 and R.sup.2, independently from each other, represent a lower alkyl group,which comprises reacting a Grignard reagent prepared from an aryl halide of the general formulaAr--X.sup.1 (II)wherein Ar is as defined above and X.sup.1 represents a halogen atom,and magnesium, with an .alpha.-haloalkanoic acid ester of the general formula ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, and X.sup.2 represents a halogen atom,said reaction of the Grignard reagent with the .alpha.-haloalkanoic acid ester of general formula (III) being carried out in the presence of a nickel compound.Type: GrantFiled: August 25, 1982Date of Patent: February 21, 1984Assignee: Taisho Pharmaceutical Company, Ltd.Inventors: Takehiro Amano, Kensei Yoshikawa, Tatsuhiko Sano, Yutaka Ohuchi, Michihiro Ishiguro, Manzo Shiono, Yoshiji Fujita, Takashi Nishida
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Patent number: 4423243Abstract: A process for the production of 2,2-dimethyl-3-vinyl-cyclopropanecarboxylic acid derivative of the formula ##STR1## in which R.sup.1 is a hydrogen atom, an alkyl group or a radical of an alcohol which can be used in pyrethroids, andX.sup.1 and X.sup.2 each independently is a halogen atomor a fluorine-substituted alkyl radical, comprising adding (a) a polyhalogenoalkene of the formula ##STR2## in which X.sup.3 and X.sup.4 each independently is a halogen atom, to 1-chloro-3,3-dimethyl-pent-4-en-2-one of the formula ##STR3## in the presence of a catalyst which yields free radicals, or in the presence of a metal salt of the VIII main group or of the sub-group IVa, VIIa or Ib of the periodic system, thereby to obtain a mixture of compounds of the formula ##STR4## and (b) reacting either or both of such compounds with a base of a formula(R.sup.1 --O.sup..crclbar.).sub.n M.sup.n+in whichM is an alkali metal or alkaline earth metal, andn is 1 or 2.Type: GrantFiled: December 16, 1981Date of Patent: December 27, 1983Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Dieter Arlt
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Patent number: 4423064Abstract: This invention relates to novel ester compounds derived from alkynoic acids and to their preparation. This invention is also directed to insecticidal and miticidal compositions comprising an acceptable carrier and an insecticidally or miticidally effective amount of a novel ester compound of this invention as well as a method of controlling pests by subjecting them to an insecticidally or miticidally effective amount of a novel ester compound of this invention.Type: GrantFiled: June 29, 1981Date of Patent: December 27, 1983Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4423067Abstract: Carbacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, a heterocyclic residue, or NHR.sub.3, wherein R.sub.3 is an acid residue or hydrogen;X is oxygen;A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--;W is free or functionally modified hydroxymethylene or free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position; D is a straight-chain or branched, saturated or unsaturated aliphatic group of 1-10 carbon atoms, which can optionally be substituted by fluorine atoms, 1,2-methylene, 1,1-trimethylene;E is --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 are hydrogen or alkyl of 1-5 carbon atoms;R.sub.4 is an aliphatic group, cycloalkyl, optionally substituted aryl, or a heterocyclic group;R.sub.5 is free or functionally modified hydroxy and,when R.sub.Type: GrantFiled: December 21, 1981Date of Patent: December 27, 1983Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Norbert Schwarz, Helmut Vorbruggen, Jorge Casals-Stenzel, Ekkehard Schillinger, Michael H. Town
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Patent number: 4420632Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet antiaggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.Type: GrantFiled: December 22, 1980Date of Patent: December 13, 1983Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4418202Abstract: Novel 2-vinyl(or ethyl)-1-cyanocyclopropane-1-carboxylates and 2-vinyl(or ethyl)-1-arylcyclopropane-1-carboxylates useful as herbicides, pesticides and chemical intermediates are provided. The invention also relates to a method of modifying plant growth by the application of vinyl(or ethyl)cyclopropane derivatives wherein the carboxylate group contains an amine or quaternized amine moiety.Type: GrantFiled: December 21, 1981Date of Patent: November 29, 1983Assignee: Emery Industries, Inc.Inventors: Richard G. Fayter, Jr., Allen L. Hall
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Patent number: 4409227Abstract: 4-(((Heterocyclo)thio)methyl)benzoic acids, esters, amides and pharmaceutically-acceptable salts thereof having hypoglycemic activity in mammals, including a method of use and pharmaceutically-acceptable compositions.Type: GrantFiled: March 9, 1982Date of Patent: October 11, 1983Assignee: The Dow Chemical Co.Inventor: Donald P. Matthews
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Patent number: 4403100Abstract: The present invention provides novel (11R)-11-deoxy-11-alkyl-6-oxo-prostaglandins which are useful for curing and preventing duodenal ulcers and for preventing or treating gastrointestinal cell damage caused by the use of other pharmacological agents.Type: GrantFiled: October 30, 1981Date of Patent: September 6, 1983Assignee: The Upjohn CompanyInventor: Douglas R. Morton, Jr.
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Patent number: 4397851Abstract: Antimicrobial compounds of the formula: ##STR1## wherein Hal is bromine or chlorine; R is C.sub.1-4 alkyl, straight or branched chain; and one of R.sup.1 and R.sup.2 is hydrogen and the other is selected from the group consisting of C.sub.3-8 cycloalkyl; C.sub.3-8 cycloalkyl C.sub.1-3 alkyl; phenyl; phenyl C.sub.1-3 alkyl; mono- or disubstituted phenyl or phenyl C.sub.1-3 alkyl wherein the substituents are halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, hydroxy, nitro, cyano, or trifluoromethyl; a heterocyclic radical selected from the group consisting of thienyl, furanyl, pyrrolyl, isoxazolyl, oxazolyl, isothiazolyl, thiazolyl, pyrazolyl, imidazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, and pyridinyl, and N-oxides thereof; and a saturated heterocyclic radical selected from the group consisting of pyrrolidinyl, tetrahydrofuranyl, tetrahydrothienyl, isoxazolidinyl, oxazolidinyl, isothiazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperazinyl, and piperidinyl.Type: GrantFiled: December 22, 1981Date of Patent: August 9, 1983Assignee: Merck & Co., Inc.Inventors: John E. Engelhart, Marshall R. Angeles, Michael J. D'Errico
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Patent number: 4381311Abstract: 4,5-Diaryl-.alpha.-(polyhalomethyl)-2-thiophenemethanols such as 4-(4-methoxyphenyl)-5-(4-methylthiophenyl)-.alpha.,.alpha.-bis(trifluorome thyl)-2-thiophenemethanol useful for treating arthritis and/or alleviating pain.Type: GrantFiled: August 27, 1981Date of Patent: April 26, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventor: Stephen B. Haber
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Patent number: 4380656Abstract: Novel 2-vinyl- and 2-ethylcyclopropane carboxylates useful as pesticides, herbicides and chemical intermediates are provided. The products of this invention contain two gem carboxylate ##STR1## groups, which can be the same or different. The carboxylate groups will contain an aliphatic, cycloaliphatic, aromatic, heteroalkyl or heterocyclic moiety.Type: GrantFiled: July 27, 1981Date of Patent: April 19, 1983Assignee: Emery Industries, Inc.Inventor: Richard G. Fayter, Jr.
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Patent number: 4368205Abstract: Disclosed are novel compounds of the formula ##STR1## wherein R.sup.1 is a heterocyclic radical selected from furanyl, thienyl, pyridyl, pyrimidyl, oxazolyl, pyrrolyl, isoxazolyl, thiazolyl, and isothiazolyl, and R.sup.2 is hydrogen, a tetramethylcylopropanecarbonyl group, a 1-(substituted-phenyl)-2-methylpropyl-1-carbonyl group, a 1-(4-ethoxyphenyl)-2-dichlorocyclopropanecarbonyl group, or a substituted-vinyl-cyclopropanecarbonyl group. The compounds wherein R.sup.2 is other than hydrogen are insecticides.Type: GrantFiled: September 17, 1981Date of Patent: January 11, 1983Assignee: FMC CorporationInventor: John F. Engel
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Patent number: 4362880Abstract: An improved process for the preparation of 3-substituted thiophenes. The thiophenes are useful for the preparation of penicillins and cephalosporins.The process is for the preparation of a thiophene of formula (I): ##STR1## where R.sup.1 represents a carboxylic acid group, or an ester or amide thereof or a nitrile group; R.sup.2 represents a group suitable for use as an .alpha.-substituent in the side-chain of a penicillin or cephalosporin; which comprises treating under basic conditions a compound of formula (II): ##STR2## wherein X represents halogen or optionally functionalized hydroxyl, Y represents halogen, hydroxyl, or alkoxy; with a source of nucleophilic sulphur ionically bound to a polymeric support.Type: GrantFiled: March 30, 1981Date of Patent: December 7, 1982Assignee: Beecham Group LimitedInventors: Kenneth T. Veal, Trevor J. Grinter
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Patent number: 4359580Abstract: The invention is an improved process for the preparation of lower alkyl esters of tetrahydrothiophenium carboxymethylide intermediates of insecticidal pyrethroids, and to insecticidal prethroids derived from said ylides.Type: GrantFiled: February 12, 1981Date of Patent: November 16, 1982Assignee: American Cyanamid CompanyInventor: Charles P. Grasso
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Patent number: 4355168Abstract: There is disclosed and claimed a process for preparing aryl- and heteroarylhexadienoic acids which is characterized in that an aryl- or heteroarylacetylene having the formula: R--C.tbd.CH, wherein R is an aryl or heteroaryl group, optionally substituted and having in the aggregate up to 20 carbon atoms, is reacted with 3-butenoic acid CH.sub.2 .dbd.CH--CH.sub.2 --COOH, in an alcoholic medium, at temperatures maintained between 50.degree. C. and 120.degree. C., approximately, in the presence of a catalyst selected from among the phosphinic complexes of rhodium having the formulas: III, Rh(PR'.sub.3).sub.n L.sub.m X associated with alkaline salts of carboxylic acids having up to 4 carbon atoms, and IV, Rh(PR'.sub.3).sub.n L.sub.p.sup.+ Y.sup.Type: GrantFiled: December 2, 1980Date of Patent: October 19, 1982Assignee: Montedison S.p.A.Inventors: Gian P. Chiusoli, William Giroldini, Luciano Pallini, Giuseppe Salerno
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Patent number: 4349690Abstract: The present invention provides novel 9-deoxy-9-methylene-6-keto-PGE derivatives which are useful for platelet aggregation inhibition and gastric cyctoprotection.Type: GrantFiled: April 23, 1981Date of Patent: September 14, 1982Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4349689Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.Type: GrantFiled: December 22, 1980Date of Patent: September 14, 1982Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4332815Abstract: Perhaloalkylvinylcyclopropanecarboxylates having the general formula ##STR1## are disclosed wherein one of Y and Z is a perhaloalkyl group. Compounds in which R is hydroxy, halogen or lower alkoxy are novel intermediates for preparation of insecticidal esters in which R is --OR.sup.1 where R.sup.1 is a wide variety of alcohol residues. The insecticidal efficacy and preparation of the compounds and intermediates therefor are described and exemplified.Type: GrantFiled: July 1, 1980Date of Patent: June 1, 1982Assignee: FMC CorporationInventor: John F. Engel
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Patent number: 4328237Abstract: Pyrethroid type insecticides are described having the formula: ##STR1## Compounds of general formula I are endowed with a high insecticide and acaricide activity.Type: GrantFiled: February 26, 1979Date of Patent: May 4, 1982Assignee: Montedison S.p.A.Inventors: Paolo Piccardi, Francesco Corda, Franco Gozzo, Augusto Menconi, Angelo Longoni
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Patent number: 4327109Abstract: A compound of the formula, ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are respectively hydrogen atom or methyl, R.sub.5 is a member of ##STR2## wherein R.sub.6 is hydrogen atom or methyl, R.sub.7 is alkenyl, alkadienyl, alkynyl or benzyl, R.sub.8 is hydrogen atom, ethynyl or cyano, R.sub.9 is hydrogen atom, a halogen atom or alkyl, R.sub.10 is a halogen atom, alkyl, alkenyl, alkynyl, benzyl, thenyl, furylmethyl, phenoxy, substituted phenoxy of phenylthio, or R.sub.9 and R.sub.10 are bonded at the ends to form polymethylene chain containing or not containing oxygen or sulfur atom, Y is oxygen atom, sulfur atom or --CH.dbd.CH--, n is 1 or 2, Z is phthalimido, thiophthalimido, di- or tetra-hydrophthalimido or dialkylmaleimido, R.sub.11 is phenyl, thienyl or furyl and X is a halogen atom, which is useful as an active ingredient of insecticides.Type: GrantFiled: April 22, 1980Date of Patent: April 27, 1982Assignee: Sumitomo Chemical Company LimitedInventors: Toshio Mizutani, Nobushige Itaya, Nobuo Ohno, Takashi Matsuo, Shigeyoshi Kitamura, Yositosi Okuno
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Patent number: 4325959Abstract: 4-(((Heterocyclo)thio)methyl)benzoic acids, esters, amides and pharmaceutically-acceptable salts thereof having hypoglycemic activity in mammals, including a method of use and pharmaceutically-acceptable compositions.Type: GrantFiled: August 9, 1979Date of Patent: April 20, 1982Assignee: The Dow Chemical CompanyInventor: Donald P. Matthews
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Patent number: 4324903Abstract: A process for the preparation of new malonic esters of the formula: ##STR1## wherein R is a substituted or unsubstituted C.sub.1 to C.sub.6 alkyl, a substituted or unsubstituted aromatic ring, a heterocyclic ring, a cycloalkyl group, or a fused ring system; R.sup.1 is hydrogen, lower alkyl, aralkyl, aralkyl substituted by halogen or alkyl or a substituted aromatic, cycloaliphatic or heterocyclic ring; and X is halogen.Type: GrantFiled: June 21, 1976Date of Patent: April 13, 1982Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara RT.Inventors: Magda Huhn, Eva Somfai, Gabor Szabo, Gabor Resovszki, Livia Gneth nee Zalantai