Rings Bonded Directly To Each Other Patents (Class 562/492)
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Patent number: 4251419Abstract: The products of the invention are vinyl end-capped oligomers which have the structure as shown in FIG. 3. The products are prepared from either of two (2) precursors. The first precursor is a compound which has the structure as shown in FIG. 2. The second precursor is a complex amine salt which has the structure shown in FIG. 5.Type: GrantFiled: April 5, 1979Date of Patent: February 17, 1981Assignee: Gulf Oil CorporationInventors: William J. Heilman, Daniel J. Hurley
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Patent number: 4251417Abstract: The products of the invention are acetylene end-capped polyimide oligomers prepared from a dianhydride of an aromatic tetracarboxylic acid such as 3,3',4,4' benzophenonetetracarboxylic acid, an aromatic triamine, and an acetylene-substituted aromatic monoamine. The structure of the polyimide oligomers is shown in FIG. 3.Type: GrantFiled: April 25, 1979Date of Patent: February 17, 1981Assignee: Gulf Oil CorporationInventors: Wai Y. Chow, William J. Heilman
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Patent number: 4229367Abstract: Trans-4-alkyl-cyanoarylcyclohexanes are prepared in a stereoselective manner from arylcarboxylic acids of the formula Ar-[Ar].sub.n -Ar-4-COOH, Ar being aryl and n being 0 to 2, by first converting such a carboxylic acid to a mixture of the cis and trans isomers of the corresponding cyclohexa-2,5-diene-4-carboxylic acid, esterifying the resulting isomer mixture with a lower alkanol and further hydrogenating the resulting esters/isomers to produce the cis and trans isomers of the corresponding cyclohexane-4-carboxylic acid esters, isomerizing the cis isomers in the mixture to the trans isomer thereby producing a mixture containing the trans isomer substantially free from cis isomer, stereospecifically saponifying the trans isomer, growing a carbon chain of desired length on the carboxyl group of the resulting carboxylic acid, reducing the carbonyl group thereof, and introducing a cyano group into the terminal aryl group. The resulting product is useful as a nematic liquid crystal.Type: GrantFiled: May 15, 1979Date of Patent: October 21, 1980Assignee: Siegfried AktiengesellschaftInventors: Bernhard Granwehr, Rene Gnehm
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Patent number: 4227016Abstract: Glyoxylic acid and hydrochloric acid are reacted with an aromatic compound having at least one substituent group selected from among the alkyl, aryl, hydroxy, alkoxy and aryloxy groups. The glyoxylic acid is used in a concentration comprised between 60 and 100% and the hydrochloric acid is used in as concentrated an aqueous solution as possible, e.g. in an organic solvent medium such as acetic acid. An acid catalyst such as zinc chloride may be used. The reaction may be carried out under pressure. The products are useful in various syntheses e.g. to produce amino acids or arylacetic acids with medicinal uses.Type: GrantFiled: December 28, 1977Date of Patent: October 7, 1980Assignee: Hoechst FranceInventors: Emmanuel Herman, Helmut Diery, Michel Soreau, Yani Christidis
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Patent number: 4220591Abstract: The (+), (-) and (.+-.) forms of the compounds of formula I ##STR1## wherein R.sup.1 is hydrogen or a methoxy, ethoxy, propoxy, methylthio, ethylthio, propylthio, fluoro, chloro, bromo, methyl, ethyl, nitro or amino group, andR.sup.2 is a hydrogen or methyl group or R.sup.1 and R.sup.2 together form a methylenedioxy group;R.sup.3 is hydrogen, or a lower alkyl group, or one of the following groups (a) to (d):(a) m-phenoxybenzyl(b) 2-benzyl-4-furylmethyl(c) .alpha.-cyano-m-phenoxybenzyl(d) 3,4-methylenedioxy-benzyl, andR.sup.4 and R.sup.5 are the same or different groups and each is a fluoro, bromo, chloro or methyl group.The compounds of formula I in which R.sup.3 is one of group (a) to (d) are extremely active as insecticides (except when R.sup.1 is an amino group). The compounds also possess the property of contact repellency to insects.Type: GrantFiled: November 17, 1976Date of Patent: September 2, 1980Assignee: Commonwealth Scientific and Industrial Research OrganizationInventors: George Holan, Reimund A. Walser
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Patent number: 4219668Abstract: Compounds of metabolites of 3-(4-biphenylylcarbonyl)propionic acid useful as anti-inflammatory and anti-platelet aggregation agents.Type: GrantFiled: July 5, 1979Date of Patent: August 26, 1980Assignee: American Cyanamid CompanyInventor: Fortunato S. Chiccarelli
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Patent number: 4212992Abstract: Fire retardant adducts of 1,4-dihydronaphthalene and halocyclopentadienes and polymer compositions containing said adducts.Type: GrantFiled: December 16, 1976Date of Patent: July 15, 1980Assignee: Standard Oil Company (Indiana)Inventor: David J. Fenoglio
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Patent number: 4198510Abstract: A process for the preparation of carboxylic acids represented by a formula ##STR1## wherein R.sub.1 represents hydrogen atom or a lower alkyl radical, R.sub.2 represents hydrogen atom, lower alkyl or allyl radical and R.sub.3 represents phenyl, substituted phenyl, substituted naphthyl, dibenzofuranyl or substituted biphenyl. Following novel enamine and amidine compounds as intermediates for manufacturing the carboxylic acids and processes for the manufacture of said enamine and amidine compounds ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 represent the meanings as referred to and R.sub.4 represents dimethylamino, pyrrolidyl, piperidyl or morpholyl.Type: GrantFiled: July 7, 1978Date of Patent: April 15, 1980Assignees: Sanwa Kagaku Kenkyusho Co., Ltd., Takayuki ShioiriInventors: Takayuki Shioiri, Nobutaka Kawai, Masatoshi Ban
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Patent number: 4188491Abstract: A process is disclosed for preparing arylpropionic acids of formula Ar--CH(CH.sub.3)--COOH, by reacting an aryl Grignard reagent with a metal pyruvate or with a pyruvamide, to form a hydroxy acid of formula Ar--C(OH)(CH.sub.3)--COOH or its amide, and converting the acid or amide to the product.Type: GrantFiled: March 24, 1978Date of Patent: February 12, 1980Assignee: The Boots Company LimitedInventors: John S. Nicholson, John L. Turner
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Patent number: 4186270Abstract: Pure 2-(4-isobutylphenyl)propionic acid and related compounds are obtained in good yield by a multi-step process comprising chloromethylation of benzene or an alkylbenzene, conversion of the resulting benzyl chloride to the cyanide, alkylation of that product to the phenylpropionitrile or phenylbutyronitrile, reaction of unreacted benzyl cyanide with an aldehyde to inhibit its hydrolysis, and hydrolysis of the nitrile to the free acid. The products are antiinflammatory, antipyretic, and analgesic drugs.Type: GrantFiled: December 26, 1978Date of Patent: January 29, 1980Assignee: The Dow Chemical CompanyInventors: William Dowd, David H. Naffziger
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Patent number: 4179578Abstract: Stilbene derivatives having at least one further phenyl substituent in the para-position to a benzene ring in the stilbene are optical brighteners particularly suitable for incorporation on spinning masses.Type: GrantFiled: April 14, 1977Date of Patent: December 18, 1979Assignee: Sandoz Ltd.Inventors: Fritz Fleck, Hans Kittl, Salvatore Valenti
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Patent number: 4176196Abstract: Novel hypoglycemic agents comprising 3-hydroxy-3-arylcyclohexane-1-acetic acid, 3-arylcyclohexene-1-acetic acids and derivatives thereof are disclosed.Type: GrantFiled: November 4, 1977Date of Patent: November 27, 1979Assignee: Pfizer Inc.Inventor: Lawrence S. Melvin, Jr.
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Patent number: 4172093Abstract: The present invention relates to new pharmacodynamically active compounds of the general structure ##STR1## as well as the corresponding amine oxides, quarternary ammonium compounds and salts with physiologically acceptable acids. In formula I R.sup.1 signifies hydrogen, halogen or alkoxy radicals having 1-3 carbon atoms, R.sup.2 and R.sup.3 signify alkyl radicals having 1-3 carbon atoms, which togetner with the carbon atom, to which they are connected, may form a ring, A either signifies a possibly lower alkyl substituted ethylene, trimethylene or tetramethylene group, in which case D is a group ##STR2## wherein R.sup.4 and R.sup.Type: GrantFiled: March 20, 1973Date of Patent: October 23, 1979Assignee: AB KabiInventors: Barbro K. Goransson-Dahlander, Nils A. Jonsson, Ferenc Merenyi
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Patent number: 4160842Abstract: New insecticidal (.beta.-phenylvinyl)cyclopropanecarboxylates having on the phenyl ring one or more substituents such as halogen, cyano, nitro, lower alkyl, aryl, aralkyl, lower alkoxy, lower alkylthio, aryloxy, arylthio, lower haloalkyl, di(lower alkyl)amino, or methylenedioxy are described, and their preparation and insecticidal utility are exemplified.Type: GrantFiled: August 27, 1976Date of Patent: July 10, 1979Assignee: FMC CorporationInventor: John F. Engel
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Patent number: 4157447Abstract: Intermediates for insecticidal (.beta.-phenyl-.beta.-substituted-vinyl)cyclopropanecarboxylates in which the .beta.-substituent may be halogen, lower alkyl, lower haloalkyl, cyano, carbomethoxy, or carbethoxy are described and exemplified.Type: GrantFiled: February 21, 1978Date of Patent: June 5, 1979Assignee: FMC CorporationInventor: John F. Engel
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Patent number: 4154697Abstract: Novel liquid crystals have the formula ##STR1## wherein two of the rings A, B and C are aromatic and the third is a trans-1,4-disubstituted cyclohexane ring and R is alkyl or alkoxy each of 1 - 12 C-atoms. These compounds are particularly useful as additional components in liquid crystal dielectrics whereby the clear point of the dielectric is raised and the viscosity thereof is not deleteriously affected.Type: GrantFiled: January 11, 1978Date of Patent: May 15, 1979Assignee: Merck Patent Gesellschaft mit beschraenkter HaftungInventors: Rudolf Eidenschink, Joachim Krause, Ludwig Pohl
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Patent number: 4154922Abstract: Methyl-substituted polyphenylacyl compounds are prepared by selective oxidation of oligomers of mesitylene. These methyl-substituted polyphenylacyl compounds are useful as intermediates for polyamides and polyesters. The esters are useful as plasticizers for polyvinylchloride.Type: GrantFiled: October 15, 1975Date of Patent: May 15, 1979Assignee: Standard Oil Company (Indiana)Inventor: John A. Donohue
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Patent number: 4153629Abstract: 9,10-Dihydro-9,10-methanoanthracene N-oxide derivatives represented by the formula: ##STR1## wherein A represents a straight or branched C.sub.1 -C.sub.6 alkylene; R.sup.1 and R.sup.2 each represents C.sub.1 -C.sub.4 alkyl or phenyl-C.sub.1 -C.sub.4 alkyl, or ##STR2## represents the group ##STR3## and X represents methylene, hydroxymethylene, C.sub.1 -C.sub.4 ##STR4## or hydroxy-C.sub.1 -C.sub.4 ##STR5## and their pharmaceutically acceptable acid addition salts which are useful as anti-depressants, tranquilizers, or anti-epileptics.Type: GrantFiled: December 15, 1976Date of Patent: May 8, 1979Assignee: Shionogi & Co., Ltd.Inventors: Hiroshi Tanida, Tadashi Irie
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Patent number: 4151302Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and are F, Cl or Br;Q is --CH(CH.sub.3)--CH.sub.2 --, --C(OH)(CH.sub.3)--CH.sub.2 -- or --C(CH.sub.3).dbd.CH--;Y is COOH, COOR.sup.3, CH.sub.2 OH or CH.sub.2 OAc;N is 0 or 1;R.sup.3 is alkyl or aryl of up to 8 carbon atoms or C.sub.6 H.sub.4 NHCOCH.sub.3 ; andAc is acyl of 1-8 carbon atoms;And physiologically acceptable salts thereof, are anti-inflammatory agents, which can be made from compounds of the formula Z--X, wherein Z is ##STR2## X can be converted to --Q--Y.Type: GrantFiled: August 19, 1977Date of Patent: April 24, 1979Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Joachim Gante, Hans-Adolf Kurmeier, Dieter Orth, Erich Schacht, Albrecht Wild
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Patent number: 4144397Abstract: Valuable 2-aryl-propionic acids are prepared by the direct coupling of aryl magnesium bromides with a mixed magnesium halide complex of alpha-bromopropionic acid.Type: GrantFiled: December 19, 1977Date of Patent: March 13, 1979Assignee: Syntex CorporationInventors: Gary J. Matthews, Robert A. Arnold
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Patent number: 4142054Abstract: 2-Aryl-C.sub.3 to C.sub.6 -alkanoate esters are prepared economically by reacting an enol ether of an aryl alkyl ketone with a trivalent thallium salt in an organic solvent. The trivalent thallium ions can be regenerated by adding a peracid and a reactive form of manganese, ruthenium, cobalt, iridium, hafnium, osmium or neobium to oxidize monovalent thallium ions to the trivalent state, in a sequential, continuous or stoichiometric procedure. A continuous process using a Scheibel column is disclosed. The ester intermediate product is then converted to the corresponding 2-aryl-C.sub.3 - to C.sub.6 -alkanoic acid or salt thereof. The aryl group is selected so the resulting acid product will be a useful compound such as an anti-inflammatory, analgesic and anti-pyretic drug or agriculturally useful product. Examples of drug acids which can be made by this process include ibuprofen, flurbiprofen, fenoprofen and naproxen and the like.Type: GrantFiled: June 16, 1977Date of Patent: February 27, 1979Assignee: The Upjohn CompanyInventors: Sanjay I. Amin, Jerry A. Walker
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Patent number: 4138419Abstract: A novel cyclopentadiene derivative of the general formula: ##STR1## wherein R.sup.1 is hydrogen, a mono- to tetra-hydric alcohol moiety having 1 to 12 carbon atoms, a metal of Groups Ia, IIa and IIb of the Periodic Table, an ammonium group or an organic amine residue; R.sup.2, R.sup.3, and R.sup.4 are independently hydrogen or alkyl groups having 1 to 6 carbon atoms; R.sup.a, R.sup.b, and R.sup.c are independently hydrogen or alkyl groups having 1 to 3 carbon atoms; m is 0 or 1; and n is an integer of 1 to 4. This cyclopentadiene derivative is comparable or even superior to natural rosin in effectiveness as an emulsifier for use in the production of SBR and ABS resins or as a sizing agent in paper making.Type: GrantFiled: April 29, 1977Date of Patent: February 6, 1979Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Masatoshi Arakawa, Ryotaro Ohno, Katuhiro Ishikawa, Noboru Yamahara, Hisashi Matsui
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Patent number: 4135051Abstract: 2-Aryl-C.sub.3 to C.sub.6 -alkanoate esters are prepared economically by reacting an enol ether of an aryl alkyl ketone with a trivalent thallium salt in an organic solvent. The trivalent thallium ions can be regenerated by adding a peracid and a reactive form of manganese, ruthenium, cobalt, iridium, hafnium, osmium or neobium to oxidize monovalent thallium ions to the trivalent state, in a sequential, continuous or stoichiometric procedure. The ester intermediate product is then converted to the corresponding 2-aryl-C.sub.3 - to C.sub.6 -alkanoic acid or salt thereof. The aryl group is selected so the resulting acid product will be a useful compound such as anti-inflammatory, analgesic and anti-pyretic drug or agriculturally useful product. Examples of drug acids which can be made by this process include ibuprofen, flurbiprofen, fenoprofen and naproxen and the like.Type: GrantFiled: June 16, 1977Date of Patent: January 16, 1979Assignee: The Upjohn CompanyInventor: Jerry A. Walker
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Patent number: 4131747Abstract: A process for preparing an .alpha.-substituted phenylalkanecarboxylic acid, having useful pharmaceutical properties such as analgesic, anti-inflammatory and anti-pyretic properties, from the corresponding ethylidenecyanoacetate by oxidation, hydrolysis, decarboxylation and oxidation.Type: GrantFiled: November 19, 1976Date of Patent: December 26, 1978Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Masayasu Kurono, Masaaki Toda, Haruki Niwa, Syunji Kosuge, Takahumi Iida, Kenichi Narita