Naphthyl Group Patents (Class 562/490)
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Patent number: 4638079Abstract: Disclosed is a process for inhibiting polymerization of polymerizable ethylenically unsaturated monomers such as hydrocarbons, acids and esters, wherein a cobalt (III), nickel (II) or manganese (II) complex of N-nitrosophenylhydroxylamine is employed. A composition including a polymerizable ethylenically unsaturated monomer and the complex is also disclosed. In a preferred embodiment, polymerization of an acrylic acid or an acrylate ester is inhibited.Type: GrantFiled: January 17, 1985Date of Patent: January 20, 1987Assignee: Mallinckrodt, Inc.Inventors: Ervin B. Inskip, Joseph M. Patane
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Patent number: 4629808Abstract: A 6-alkoxy-5-trifluoromethyl-1-cyanonaphthalene is hydrolyzed to the corresponding acid in high yield by reacting it with an aqueous alcoholic base under moderate pressure at a temperature of about 115.degree.-130.degree. C. A preferred nitrile is 6-methoxy-5-trifluoromethyl-1-cyanonaphthalene, preferred bases are sodium and potassium hydroxides, utilizable alcohols are alkanols containing 1-3 carbons, and preferred pressures are in the range of about 90-110 psi.Type: GrantFiled: June 20, 1985Date of Patent: December 16, 1986Assignee: Ethyl CorporationInventor: K. Pushpananda A. Senaratne
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Patent number: 4613690Abstract: Optically active compounds having a chlorine atom attached to the chiral carbon atom such as 2-bromoaliphatic acids can be racemized without by-product formation by heating an acidified solution of the organic acid at a temperature sufficient to accomplish racemization, the solution being substantially devoid of ionized halogen other than bromine ions. The preferred acidifying agent is hydrobromic acid. The use of hydrochloric acid causes extensive by-product formation.Type: GrantFiled: August 30, 1985Date of Patent: September 23, 1986Assignee: Stauffer Chemical CompanyInventor: Samun K. Dahod
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Patent number: 4613689Abstract: Optically active compounds having a chlorine atom attached to the chiral carbon atom such as 2-chloroaliphatic acids can be racemized without by-product formation by heating an acidified solution of the compound in the presence of chloride ion at sufficient strength, and at a pH and temperature sufficient to accomplish racemization. The preferred acidifying agent and source of chloride ion is hydrochloric acid. The use of hydrochloric acid at room temperature as well as the use of either sulfuric acid or caustic soda failed to produce racemization.Type: GrantFiled: August 30, 1985Date of Patent: September 23, 1986Assignee: Stauffer Chemical CompanyInventors: Patricia Siuta-Mangano, Samun K. Dahod
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Patent number: 4607116Abstract: Provided is a process for preparing a diaryl or a mixture of diaryls represented by any or a combination of the following formulae (II), (III) and (V), characterized in that a diaryliodonium salt represented by the following formula (I) is reacted in a solvent in the presence of a transition metal catalyst and a reducing metal at a temperature in the range of room temperature to 100.degree. C.:[Ar.sub.1 -I.sup..sym. -Ar.sub.2 ]X.sup..crclbar. (I)Ar.sub.1 -Ar.sub.1 (II)Ar.sub.1 -Ar.sub.2 (III)Ar.sub.2 -Ar.sub.2 (IV)wherein Ar.sub.1 and Ar.sub.2, which may be alike or different, are each an aryl group which may have a substituent group or groups and X.sup..crclbar. is a counter ion which is inert to said reaction.Type: GrantFiled: March 8, 1984Date of Patent: August 19, 1986Assignee: Nippon Petrochemicals Company LimitedInventors: Yasuo Yamazaki, Takehiko Suzuki, Masaharu Uchiyama
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Patent number: 4605758Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.Type: GrantFiled: April 23, 1984Date of Patent: August 12, 1986Assignee: Syntex Pharmaceuticals International Ltd.Inventor: George C. Schloemer
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Patent number: 4582930Abstract: A process is disclosed for the preparation of optically active alpha-arylalkanoic acids, consisting in the rearrangement of optically active alpha-(haloalkyl)-aryl-ketals and in submitting to hydrolysis the so-obtained esters of alpha-arylalkanoic acids.The rearrangement reaction is carried out under neutral or slightly alkaline conditions in a polar protic medium.Type: GrantFiled: February 22, 1985Date of Patent: April 15, 1986Assignee: Zambon S.p.A.Inventors: Graziano Castaldi, Claudio Giordano, Fulvio Uggeri
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Patent number: 4579968Abstract: A process is disclosed for the preparation of optically active alpha-arylalkanoic acids, consisting in the rearrangement of optically active (alpha-haloalkyl)-aryl-ketals and in submitting to hydrolysis the thus obtained esters of alpha-arylalkanoic acids. The rearrangement reaction is carried out under neutral or alightly alkaline conditions, in an aprotic dipolar diluent and in the presence of a protic substance having a high dielectric constant.Type: GrantFiled: February 22, 1985Date of Patent: April 1, 1986Assignee: Zambon S.p.A.Inventors: Graziano Castaldi, Claudio Giordano, Fulvio Uggeri
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Patent number: 4578522Abstract: This invention relates to a method of synthesis of certain substituted carboxylic acids useful in lowering serum triglyceride and total cholesterol levels in mammals (including man) represented by the general formula I:Ar.sup.1 --Ar.sup.2 (I)whereinAr.sup.1 is selected from ##STR1## Ar.sup.2 is selected from ##STR2## and R is selected from C.sub.1-5 alkyl, halogen, perhalo-C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl, C.sub.1-4 acyl, C.sub.1-6 alkoxycarbonyl, amino or hydroxy.Type: GrantFiled: September 14, 1984Date of Patent: March 25, 1986Inventor: John F. Eaddy, III
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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: 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: 4546198Abstract: Stereoisomerically-enriched esters are prepared by treating a non-symmetrical ketene with a racemic or chiral tertiary-base-substituted alkylcarbinol. Optional hydrolysis of the esters gives the corresponding optically-active carboxylic acids corresponding to the non-symmetrical ketene.Type: GrantFiled: March 26, 1984Date of Patent: October 8, 1985Assignee: Shell Oil CompanyInventor: Donald W. Stoutamire
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Patent number: 4544766Abstract: This invention relates to a process for preparing an aryl acetic acid derivative represented by the formulaAr--CH.sub.2 COY).sub.ncomprising hydrolyzing in an alkaline substance a dichloroethenyl compound represented by the formulaAr--CH.dbd.CCl.sub.2).sub.n.Type: GrantFiled: February 26, 1982Date of Patent: October 1, 1985Assignee: Otsuka Kagaku Yakuhin Kabushiki KaishaInventor: Tatsuya Shono
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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: 4501913Abstract: Process for preparing esters of aryl alkanoic acids via oxidation of the corresponding ketones with bromine or iodine in the presence of a metal halide and an alcohol.The thus obtained esters are then easily hydrolized to give the corresponding aryl alkanoic acids which are particularly useful as anti-inflammatory, analgesic and anti-pyretic agents.Type: GrantFiled: November 1, 1983Date of Patent: February 26, 1985Assignee: Zambon S.p.A.Inventors: Claudio Giordano, Graziano Castaldi
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Patent number: 4496736Abstract: Carboxylic acids and N-t.-alkylamines can be prepared simultaneously by the alkaline pressure hydrolysis of N-t.-alkyl carboxylic acid amides. A 5 to 50% strength by weight aqueous solution of an alkali metal hydroxide is employed for this purpose in an amount of 1.0 to 1.3 mols per mol of the amide. The process is carried out at 200.degree. to 350.degree. C.Type: GrantFiled: June 3, 1982Date of Patent: January 29, 1985Assignee: Bayer AktiengesellschaftInventors: Gerhard Bonse, Gerhard Marzolph, Heinz U. Blank
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Patent number: 4465855Abstract: Arylacetic acid derivatives of the formula ##STR1## with R.sup.1, R.sup.2 and R.sup.3 specifically defined and which are useful as antirheumatic and antiinflammatory pharmaceuticals are prepared by catalytic hydrogenation of new compounds of the formula ##STR2## in which R and R.sup.10 are also specifically defined. The method of making the latter compound is also set forth.Type: GrantFiled: April 15, 1982Date of Patent: August 14, 1984Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara RtInventors: Endre Palosi, Dezso Korbonits, Pal Kiss, Csaba Gonczy, Gergely Heja, Judit Cser nee Kun, Rudolf Szebeni, Maria Szomor nee Wundele, Ida Szvoboda nee Kanzel
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Patent number: 4456618Abstract: Naphthenic and heterocyclic retinoic acid analogues such as (E)-6-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]-2-naphthaldehyde, methyl 6-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]-2-naphthoate, 6-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]-2-naphthoic acid, (E)-1-(5-carbethoxy-2-furanyl)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1- yl)-1,3-butadiene, (E)-1-(5-carboxy-2-furanyl)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl) -1,3-butadiene, (E)-1-(5-carbethoxythien-2-yl)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1- yl)-1,3-butadiene, and (E)-1-(5-carboxythien-2-yl)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl) -1,3-butadiene. These retinoids are useful as chemopreventive agents for inhibiting tumor promotion in epithelial cells and for treating nonmalignant skin disorders.Type: GrantFiled: October 15, 1982Date of Patent: June 26, 1984Assignee: SRI InternationalInventors: Marcia I. Dawson, Rebecca L. S. Chan
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Patent number: 4454341Abstract: Compounds of the formulas: ##STR1## where X is methyl, methoxy, chlorine, or hydrogen, Y and Y.sub.1 are fluorine or hydrogen, R is hydroxy, alkoxy with 0 or 1 hydroxy substituent, aroxy, or NR.sup.1 R.sup.2 where R.sup.1 is hydrogen, alkyl with 0 or 1 hydroxy substituent or aryl and R.sup.2 is alkyl with 0 or 1 hydroxy substituent or aryl with the proviso that when Y or Y.sup.1 is fluorine, the other Y or Y.sup.1 is hydrogen. These compounds are useful as chemopreventive agents for inhibiting tumor promotion in epithelial cells and for treating nonmalignant skin disorders.Type: GrantFiled: March 3, 1983Date of Patent: June 12, 1984Assignee: SRI InternationalInventors: Marcia I. Dawson, Peter D. Hobbs, Krzysztof A. Derdzinski
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Patent number: 4440947Abstract: Substituted .alpha.-halogenopropionic acids and their derivatives of the general formula ##STR1## wherein R.sup.1 to R.sup.3, Y and X have the meanings given in the description, are prepared by a process which is characterized in that substituted vinylidene chlorides of the general formula ##STR2## are reacted with chlorine or bromine chloride in the presence of compounds of the formulaR.sup.5 --SO.sub.3 R.sup.6 (III)wherein R.sup.5 and R.sup.6 have the meaning given in the description, and the products obtained are treated, if appropriate, with water or alcohol. Certain of the substituted .alpha.-halogeno-propionic acids and the substituted vinylidene chloride of the formula ##STR3## are new. The end products are useful as herbicides and intermediates for insecticides.Type: GrantFiled: March 5, 1982Date of Patent: April 3, 1984Assignee: Bayer AktiengesellschaftInventor: Dieter Arlt
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Patent number: 4421929Abstract: Novel tetracarboxylic acids are described of the formula ##STR1## wherein Ar, R.sub.1 and R.sub.2 are named substituents, and both n's are zeros or ones.Type: GrantFiled: December 2, 1981Date of Patent: December 20, 1983Assignee: The Dow Chemical CompanyInventor: Edmund P. Woo
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Patent number: 4405810Abstract: 7-arylhept-5-ynoic acids and derivatives thereof are anti-allergy and anti-inflammatory agents. As such, they are useful in the treatment of allergy-caused diseases, particularly chronic obstructive lung diseases.Type: GrantFiled: June 14, 1982Date of Patent: September 20, 1983Assignee: Schering CorporationInventors: David Blythin, Michael J. Green
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Patent number: 4390476Abstract: Phosphonium compounds of the formula(R).sub.3 P.sup..sym. --CH.sub.2 --X--CH.dbd.CH--R.sub.1 --Y.sup..crclbar.in which R is preferably alkyl having 1 to 4 C atoms, cyclohexyl or phenyl, R.sub.1 is a substituted or unsubstituted aromatic radical, especially a phenyl radical, X is phenylene, 4,4'-biphenylene or 1,4- or 2,6-naphthylene and Y.sup..crclbar. is SO.sub.3.sup..crclbar., SO.sub.2.sup..crclbar. or COO.sup..crclbar., a process for their preparation and a process for the preparation of asymetrically substituted fluorescent brightening agents of the formulaZ--CH.dbd.CH--X--CH.dbd.CH--R.sub.1 --Y.sup..crclbar. M.sup..sym.in which R.sub.1, X and Y.sup..crclbar. are as defined above, M.sup..sym. is a cation and Z is preferably a substituted or unsubstituted phenyl or 2-phenyl-triazol-4-yl radical, by reacting a bis-phosphonium compound of the formula ##STR1## in which Q.sup..crclbar. is an anion, with an aldehyde of the formula M.sup..sym. Y.sup..crclbar. --R.sub.Type: GrantFiled: November 5, 1981Date of Patent: June 28, 1983Assignee: Ciba-Geigy CorporationInventor: Michael Marky
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Patent number: 4356188Abstract: This invention relates to 1-naphthyl-acetic acid derivatives having the general formula: ##STR1## in which: R.sub.1 is hydrogen atom or a straight- or branched-chain C.sub.1-6 alkyl group,R.sub.2 is a straight- or branched-chain alkyl group having 1-12 carbon atoms,R.sub.3 is a hydroxy group, a C.sub.1-6 straight- or branched-chain alkoxy group, and their pharmaceutically acceptable salts.Said compounds have anti-inflammatory, anti-pyretic and analgesic activities and are free from ulcerogenic activity under the administration conditions.Type: GrantFiled: July 28, 1980Date of Patent: October 26, 1982Assignee: Institut de Recherche Scientifique "I.R.S."Inventors: Henri Pacheco, Marie-Ange Descours-Saint-Martino, Demetre Yavordios, Jean Koeberle
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Patent number: 4345089Abstract: Disclosed is a process for the recovery of aromatic carboxylic acid or ester thereof from the residue fraction of the oxidation or esterification reaction mixture resulting from the oxidation or oxidation and esterification of an aromatic compound having at least one methyl or formyl group directly bonded to a ring carbon atom. The process comprises treating the residue fraction with hydrogen and a hydrogenation catalyst.Type: GrantFiled: April 28, 1980Date of Patent: August 17, 1982Assignee: HercofinaInventors: Kenji Nagura, Shinichi Takeda, Koshi Namie, Takao Fujii, Michio Yamamoto, Seiichi Yokoyama
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Patent number: 4326055Abstract: This invention is directed to 5,6,7,8-tetrahydro-naphthyl or indanyl stilbene derivatives which are useful as tumor inhibiting agents, in the treatment of neoplasms, dermatological conditions and rheumatic illnesses.Type: GrantFiled: December 15, 1978Date of Patent: April 20, 1982Assignee: Hoffmann-La Roche Inc.Inventor: Peter Loeliger
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Patent number: 4316860Abstract: Phosphonium compounds of the formula(R).sub.3 P.sup..sym. --CH.sub.2 --X--CH.dbd.CH--R.sub.1 --Y.sup..crclbar.in which R is preferably alkyl having 1 to 4 C atoms, cyclohexyl or phenyl, R.sub.1 is a substituted or unsubstituted aromatic radical, especially a phenyl radical, X is phenylene, 4,4'-biphenylene or 1,4- or 2,6-naphthylene and Y.sup..crclbar. is SO.sub.3.sup..crclbar., SO.sub.2.sup..crclbar. or COO.sup..crclbar., a process for their preparation and a process for the preparation of asymetrically substituted fluorescent brightening agents of the formulaZ--CH.dbd.CH--X--CH.dbd.CH--R.sub.1 Y.sup..crclbar. M.sup..sym.in which R.sub.1, X and Y.sup..crclbar. are as defined above, M.sup.61 is a cation and Z is preferably a substituted or unsubstituted phenyl or 2-phenyl-triazol-4-yl radical, by reacting a bis-phosphonium compound of the formula ##STR1## in which Q.sup..crclbar. is an anion, with an aldehyde of the formula M.sup..sym. Y.sup..crclbar. --R.sub.Type: GrantFiled: May 15, 1980Date of Patent: February 23, 1982Assignee: Ciba-Geigy CorporationInventor: Michael Marky
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Patent number: 4277490Abstract: New compounds are described that fall within the general formula I ##STR1## wherein R is hydrogen, or a lower alkyl group, or one of the following groups:(a) 3-phenoxybenzyl(b) 2-benzyl-4-furylmethyl(c) .alpha.-cyano-3-phenoxybenzyl(d) 3,4-methylenedioxybenzyl(e) .alpha.-ethynyl-3-phenoxybenzyl(f) .alpha.-cyano-3-(4-chlorophenoxy)-benzyland A is one of the groups X or Y ##STR2## wherein X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are the same or different groups and each is hydrogen or fluoro, chloro, bromo or methyl group, with the proviso that if X.sup.1 or X.sup.3 is a fluoro group then X.sup.2 or X.sup.4 should not be a bromo group; and wherein Y.sup.1, Y.sup.2, Y.sup.3, Y.sup.4, Y.sup.5 and Y.sup.6 are the same or different groups and each is hydrogen or a fluoro, bromo, chloro or methyl group.Processes of making the compounds are described. The compounds in which R.sup.3 is one of groups (a) to (f) are insecticides and insecticidal methods and compositions containing them are described.Type: GrantFiled: November 30, 1979Date of Patent: July 7, 1981Assignee: Commonwealth Scientific and Industrial Research OrganizationInventors: George Holan, Reimund A. Walser
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Patent number: 4268442Abstract: There are disclosed processes for preparing an aromatic acetic acid by the reaction of an aromatic aldehyde with a combination of a trihalomethane and an alkanethiol, and by the reaction of an alcohol derivative (2,2,2-trihalo-1-arylethanol) with an alkanethiol, in the presence of a base in a mixed medium of water and an aprotic polar solvent.Type: GrantFiled: November 13, 1979Date of Patent: May 19, 1981Assignee: Sagami Chemical Research CenterInventors: Kiyosi Kondo, Tamotsu Fujimoto, Minoru Suda, Daiei Tunemoto
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Patent number: 4255313Abstract: The products of the invention are end-capped polyimide oligomers prepared from a dianhydride of an aromatic tetracarboxylic acid such as 3,3'4',4'-benzophenonetetracarboxylic acid, an aromatic diamine, and a 1-(aminoaryl)-3-hydroxy-3-methyl-1-butyne. The structure of the polyimide oligomers is shown in FIG. 3.Type: GrantFiled: April 20, 1979Date of Patent: March 10, 1981Assignee: Gulf Oil CorporationInventors: Patricia A. Antonoplos, William J. Heilman
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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: 4251420Abstract: The products of the invention are 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 a 1-(aminoaryl)-3-hydroxy-3-methyl-1-butyne. The structure of the polyimide oligomers is shown in FIG. 3.Type: GrantFiled: April 23, 1979Date of Patent: February 17, 1981Assignee: Gulf Oil CorporationInventors: Patricia A. Antonoplos, William J. Heilman
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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: 4246281Abstract: Acenaphthenes of formula (I) ##STR1## where Ph represents an optionally substituted phenyl group and wherein R.sup.1 represents hydrogen or C.sub.1-4 alkyl are useful anti-inflammatory agents.Type: GrantFiled: September 10, 1979Date of Patent: January 20, 1981Assignee: Lilly Industries LimitedInventor: William R. N. Williamson
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Patent number: 4218473Abstract: The present invention relates to derivatives of 4-cyclohexyl-1-naphthalene-acetic acid of formula ##STR1## wherein R is a lower alkyl group and pharmaceutically acceptable salts and derivatives thereof the invention also relates to pharmaceutic compositions containing such derivatives.These derivatives are useful as drugs, notably for the treatment of inflammatory syndromes.Type: GrantFiled: September 26, 1978Date of Patent: August 19, 1980Assignee: Centre Europeen de Recherches MauvernayInventors: Jean-Jacques Godfroid, Efroim Steiner
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Patent number: 4214087Abstract: A nitrile, such as terephthalonitrile or nicotinonitrile is hydrolyzed, in the vapor phase, in the presence of a solid acid catalyst, with ammonia which is evolved in the reaction and absorbed by the catalyst being stripped from the catalyst to reduce the production of intermediate amide products.Type: GrantFiled: December 13, 1978Date of Patent: July 22, 1980Assignee: The Lummus CompanyInventors: Anthony J. Fanelli, Abraham P. Gelbein
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Patent number: 4204071Abstract: Benzyl esters and thiolesters of 4-aryl-3-butenoic acids, intermediates therefor, synthesis thereof, and the use of said esters and thiolesters for the control of pests.Type: GrantFiled: May 4, 1978Date of Patent: May 20, 1980Assignee: Zoecon CorporationInventors: Richard J. Anderson, Clive A. Henrick
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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: 4174452Abstract: A nitrile, such as terephthalonitrile or nicotinonitrile is reacted with water, in the vapor phase, in the presence of a catalyst, such as supported phosphoric acid, to produce the corresponding carboxylic acid.Type: GrantFiled: February 13, 1978Date of Patent: November 13, 1979Inventors: Abraham P. Gelbein, John E. Paustian, Anthony J. Fanelli
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Patent number: 4164415Abstract: This invention relates to .alpha.-(branched C.sub.3 -C.sub.4 alkyl)naphthaleneacetic acids and a method for the control of undesirable plant species therewith. The invention also relates to a method for the preparation of the compounds.CROSS REFERENCE TO RELATED APPLICATIONOur copending application Ser. No. 673,244 filed of even date, now U.S. Pat. No. 4,046,799, discloses the use of the compounds of this invention as intermediates for the manufacture of substituted-benzyl .alpha.-C.sub.1 -C.sub.4 alkyl-2-naphthaleneacetate insecticides.Type: GrantFiled: April 2, 1976Date of Patent: August 14, 1979Assignee: American Cyanamid Co.Inventors: Venkataraman Kamesaran, Roger W. Addor
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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: 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: 4116967Abstract: A nitrile, such as terephthalonitrile is catalytically reacted with water, in the vapor phase, to produce a gaseous effluent containing the corresponding carboxylic acid, as well as unreacted nitrile, ammonia and water. The acid product is separated from the gas by sublimation, preferably at a temperature above the dew point of the other components of the mixture.Type: GrantFiled: October 7, 1976Date of Patent: September 26, 1978Assignee: The Lummus CompanyInventors: Abraham P. Gelbein, Morgan C. Sze