Oxy Containing Patents (Class 568/442)
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Patent number: 4542237Abstract: .alpha.-Arylalkanoic acids or esters, orthoesters or amides thereof are prepared by forming an .alpha.-hydroxy ketal or thioketal of an aryl alkyl ketone, activating the .alpha.-hydroxy substituent with an esterifying agent to form the corresponding ketal or thioketal ester substrate, wherein the ester group is sufficiently labile to non-catalytically disassociate from the substrate in a protic or dipolar, aprotic solvent, maintaining the ester substrate in contact with the protic or dipolar, aprotic solvent or mixtures thereof for a time sufficient to form the corresponding .alpha.-arylakanoic acid or ester, orthoester or amide thereof, and optionally concomitantly or sequentially hydrolyzing any ester, orthoester or amide formed to the corresponding .alpha.-arylalkanoic acid.Type: GrantFiled: June 7, 1983Date of Patent: September 17, 1985Assignee: Syntex Pharmaceuticals International LimitedInventor: George C. Schloemer
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Patent number: 4540827Abstract: Herbicidally active compounds of the formula ##STR1## in which .sup.1 represents a hydrogen or chlorine atom,R.sup.2 represents a hydrogen atom, a cyano group, an optionally substituted radical selected from alkyl, aryl, alkanoyl, benzoyl, alkoxycarbonyl, alkenoxycarbonyl, alkinoxycarbonyl, aralkoxycarbonyl and aryloxycarbonyl, or a radical of the general formula --COOM,in whichM represents a hydrogen atom, one equivalent of an alkali metal ion or alkaline earth metal ion or optionally substituted ammonium, andR.sup.3 represents a cyano group or a radical of the general formula ##STR2## wherein Y represent an oxygen or sulphur atom or an imino (NH) or alkylimino (Nalkyl) group,R.sup.4 and R.sup.5 independently of each other represent a hydrogen atom or a methyl group,n is 0 or 1 andZ represents an optionally substituted radical.Novel intermediates therefor are also shown.Type: GrantFiled: June 1, 1984Date of Patent: September 10, 1985Assignee: Bayer AktiengesellschaftInventors: Heinz Forster, Ludwig Eue, Robert Schmidt
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Patent number: 4537996Abstract: New hydroxybiphenyl compounds of the general formula: ##STR1## wherein R.sub.1 stands for a hydrogen atom or a hydroxyl group, R.sub.2 for a hydrogen atom or a hydroxyl group, R.sub.3 for a hydroxyl group, a group of the formula -CH.sub.2 -CH.dbd.CH.sub.2 or a group of the formula -CH.dbd.CH-CHO, R.sub.4 for a hydrogen atom or a group of the formula ##STR2## and R.sub.5 for a hydroxyl group or a group of the formula ##STR3## These compounds are obtained by extraction of "Tokoboku", i.e. dried cortex of Magnolia officinalis which belongs to the family Magnoliaceae. They are useful as pharmaceuticals or intermediates therefor, in particular as anti-allergics.Type: GrantFiled: September 22, 1983Date of Patent: August 27, 1985Assignee: Kabushiki Kaisha TsumurajuntendoInventors: Akihide Kooda, Itsuo Nishioka, Takeshi Nishiyori, Shoji Yahara
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Patent number: 4532364Abstract: Described are ether carboxaldehydes defined according to the generic structure: ##STR1## wherein X represents aryl, alkaryl, hydroxyalkyl, alkenyl, cycloalkenyl, lower alkyl or bicycloalkyl; wherein Y represents C.sub.1 -C.sub.3 lower alkylene; wherein Z completes an alkyl substituted C.sub.6 cycloalkyl ring or represents no moiety; wherein R represents hydrogen or methyl; wherein m represents 0 or 1; wherein n represents 0 or 1; wherein p represents 0 or 1 and wherein q represents 0 or 1 with the provisos that when m is 1, Z completes the alkyl substituted or unsubstituted C.sub.Type: GrantFiled: September 19, 1983Date of Patent: July 30, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4524032Abstract: A process for direct fluorination of etherified or unetherified hydroxy group-bearing aromatic compounds, which comprises reacting an etherified or unetherified hydroxy group-bearing aromatic compound with fluorine gas to give the corresponding etherified or unetherified hydroxy group and at least one fluorine atom-bearing aromatic compound.Type: GrantFiled: January 14, 1983Date of Patent: June 18, 1985Assignee: Daikin Kogyo Co., Ltd.Inventors: Susumu Misaki, Sadamu Ishii, Masahiro Suefuji
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Patent number: 4523037Abstract: By reacting, using as a catalyst a modified or unmodified cyclodextrin, a phenol compound with a haloform in the presence of an alkali metal hydroxide, while maintaining the molar ratio of the cyclodextrin to the haloform at 0.5 to 10, a substituent group derived from the haloform can be introduced to the para-position of the phenol compound with high selectivity, whereby useful para-substituted phenol derivatives can be advantageously obtained.Type: GrantFiled: September 7, 1983Date of Patent: June 11, 1985Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hidefumi Hirai, Makoto Komiyama
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Patent number: 4521634Abstract: Described are ether carbinols defined according to the generic structure: ##STR1## wherein X.sub.1 represents a moiety selected from the group consisting of: ##STR2## and wherein Y.sub.1 represents C.sub.4 or C.sub.5 alkylene or C.sub.4 or C.sub.5 alkenylene or C.sub.4 or C.sub.5 alkynylene; processes for preparing such ether carbinols by means of first reacting allyl ethers with a mixture of carbon monoxide and hydrogen by means of an oxoreaction to produce ether carboxaldehydes and then reducing the thus formed ether carboxaldehydes to ether carbinols; or reacting camphene with appropriate diols; as well as methods for augmenting or enhancing the aroma or taste of consumable materials including perfumes, colognes and perfumed articles; foodstuffs, chewing gums, chewing tobaccos, medicinal products and toothpastes; and smoking tobaccos and smoking tobacco articles by adding thereto an aroma or taste augmenting or enhancing quantity of the thus produced ether carbinols.Type: GrantFiled: January 26, 1984Date of Patent: June 4, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4518797Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO,--C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.Type: GrantFiled: March 15, 1979Date of Patent: May 21, 1985Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4515987Abstract: Described is a genus of compounds defined according to the structure: ##STR1## (Z) represents one of the moieties ##STR2## as well as the substantially pure compound defined according to the structure: ##STR3## and the use thereof for augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, medicinal products, toothpastes, chewing tobaccos, smoking tobaccos, smoking tobacco articles, perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, fabric softener articles, perfumed articles, hair preparations and the like.Type: GrantFiled: June 26, 1984Date of Patent: May 7, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Theodore J. Tyszkiewicz, Michael Licciardello, Manfred H. Vock, Joaquin F. Vinals, Patrick Whalen, Marie R. Hanna
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Patent number: 4508925Abstract: There is disclosed a novel process for preparing a number of cinnamaldehyde derivatives. These cinnamaldehyde derivatives can be reduced to dihydrocinnamaldehyde derivatives, a number of which are commercially important in the preparation of fragrances. The invention is also directed to a number of novel intermediates and their preparation.Type: GrantFiled: November 9, 1983Date of Patent: April 2, 1985Assignee: Givaudan CorporationInventors: Yvo Crameri, Paul A. Ochsner, Peter Schudel
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Patent number: 4491537Abstract: Described are tertiary hydroxyl carboxaldehydes defined according to the generic structure: ##STR1## wherein the lines* * * * *and-- -- -- -- -- --and/or+ + + + +represent covalent carbon-carbon bonds when m does not=0; and wherein the lines+ + + + +* * * * *and-- -- -- -- -- --do not represent any bonds when m=0; wherein R represents hydrogen or methyl; wherein p and q each represents 0 or 1 with the proviso that p=1 when q=0 and p=0 when q=1; wherein X and Z each represent one or more carbon atoms required to complete a bicyclo ring with the lines+ + + + +* * * * *and-- -- -- -- -- --representing carbon-carbon bonds; wherein X and Z complete a phenyl moiety when the line-- -- -- -- -- --represents no bond; wherein X and Z complete a cycloalkyl ring moiety with the lines* * * * *and+ + + + +represent carbon-carbon bonds and with the line-- -- -- -- -- --representing no bond; and wherein when m is 0, X represents an alkylene moiety, processes for preparing same by means of reacting carbon monoxide and hydrogeType: GrantFiled: July 8, 1983Date of Patent: January 1, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4482736Abstract: Herbicidally active compounds of the formula ##STR1## in which R.sup.1 represents a hydrogen or chlorine atom,R.sup.2 represents a hydrogen atom, a cyano group, an optionally substituted radical selected from alkyl, aryl, alkanoyl, benzoyl, alkoxycarbonyl, alkenoxycarbonyl, alkinoxycarbonyl, aralkoxycarbonyl and aryloxycarbonyl, or a radical of the general formula--COOM,in whichM represents a hydrogen atom, one equivalent of an alkali metal ion or alkaline earth metal ion or optionally substituted ammonium, andR.sup.3 represents a cyano group or a radical of the general formula ##STR2## wherein Y represents an oxygen or sulphur atom or an imino (NH) or alkylimino (Nalkyl) group,R.sup.4 and R.sup.5 independently of each other represent a hydrogen atom or a methyl group,n is 0 or 1 andZ represents an optionally substituted radical,Novel intermediates therefor are also shown.Type: GrantFiled: July 14, 1983Date of Patent: November 13, 1984Assignee: Bayer AktiengesellschaftInventors: Heinz Forster, Ludwig Eue, Robert Schmidt
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Patent number: 4457939Abstract: A series of 5-(2-alkoxy-3-substituted phenyl)hydantoins and pharmaceutically acceptable salts thereof useful as aldose reductase inhibitors and as therapeutic agents for the treatment of chronic diabetic complications; intermediates therefore; and processes for preparation of said compounds.Type: GrantFiled: November 1, 1982Date of Patent: July 3, 1984Assignee: Pfizer Inc.Inventor: Rodney C. Schnur
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Patent number: 4454330Abstract: A process for the preparation of a two-functional-group-containing terpenoid having the general formula: ##STR1## in which n is an integer of from 1 to 5, R represents a hydroxymethyl, formyl or carboxyl group, and A represents the hydrogen atom, or a 2-tetrahydropyranyl, benzyl, methoxymethol or methoxyethoxymethyl group comprising the oxidation with a microorganism belonging to the genus Nocardia. Some of the terpenoids are of value as anti-ulcer agents, while others are useful as intermediates.Type: GrantFiled: March 22, 1982Date of Patent: June 12, 1984Assignees: Eisai Co., Ltd., General Director of the Agency of Industrial Science and TechnologyInventors: Akio Sato, Kenji Nakajima, Yoshimasa Takahara, Shizumasa Kijima, Noriaki Kuwana, Shinya Abe, Kouzi Yamada
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Patent number: 4452994Abstract: An improved process for isolating organic compounds from crude product or reaction mixtures by dissolving said crude product or reaction mixture in a suitable solvent, contacting the resulting solution with a lithium salt to form a solid metal salt complex, separating, and thereafter recovering a pure product by decomposing the lithium salt complex.Type: GrantFiled: March 2, 1981Date of Patent: June 5, 1984Assignee: G. D. Searle & Co.Inventors: John B. Hill, Robert A. Erickson
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Patent number: 4435585Abstract: There is disclosed a novel process for preparing a number of cinnamaldehyde derivatives. These cinnamaldehyde derivatives can be reduced to dihydrocinnamaldehyde derivatives, a number of which are commercially important in the preparation of fragrances. The invention is also directed to a number of novel intermediates and their preparation.Type: GrantFiled: November 17, 1981Date of Patent: March 6, 1984Assignee: Givaudan CorporationInventors: Yvo Crameri, Paul A. Ochsner, Peter Schudel
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Patent number: 4430354Abstract: Described is a genus of compounds defined according to the structure: ##STR1## (Z) represents one of the moieties ##STR2## as well as the substantially pure compound defined according to the structure: ##STR3## and the use thereof for augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, medicinal products, toothpastes, chewing tobaccos, smoking tobaccos, smoking tobacco articles, perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, fabric softener articles, perfumed articles, hair preparations and the like.Type: GrantFiled: May 20, 1983Date of Patent: February 7, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Theodore J. Tyszkiewicz, Michael Licciardello, Manfred H. Vock, Joaquin F. Vinals, Patrick Whalen, Marie R. Hanna
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9-Deoxy-9-methylene derivatives of (dl)-16-phenoxy and 16-phenoxy substituted prostatriene compounds
Patent number: 4418206Abstract: Novel compounds of the formula: ##STR1## wherein A is CHOH, CHO or COOR; R is hydrogen or a lower alkyl group of 1 to 4 carbon atoms; and the pharmaceutically acceptable, non-toxic salts of compounds in which R is hydrogen; and X is hydrogen, o-, m- or p-halo(fluoro, chloro or bromo), o-, m- or p-methyl or o-, m- or p-methoxy. These compounds possess prostaglandin-like activity and thus are useful in the treatment of mammals where prostaglandins are indicated. They are particularly useful as inhibitors of gastric acid secretions and as agents for the control of asthmatic attack, because of their bronchodilating activity.Type: GrantFiled: March 22, 1982Date of Patent: November 29, 1983Assignee: Syntex (U.S.A.) Inc.Inventor: Douglas L. Wren -
Patent number: 4408070Abstract: Pure crystalline racemic sodium parahydroxymandelate free from any ions of chloride, acetate, formate and sulfate group, is manufactured by condensing in water, in the presence of sodium hydroxide at a temperature between 30.degree. and 100.degree. C., glyoxylic acid or sodium glyoxylate with an excess of phenol, concentrating it hot, until the start of crystallization of the solution thus obtained after neutralization and removal of the unconverted phenol either by steam distillation, or by extraction with a water-immiscible organic solvent. The resulting suspension obtained is cooled, drained after some hours of standing at a temperature close to 5.degree. C., and the resulting precipitate recovered by washing it with iced water followed by drying to constant weight. The product is useful for the manufacture of crystalline sodium paraformylphenolate.Type: GrantFiled: July 20, 1981Date of Patent: October 4, 1983Inventors: Alain Schouteeten, Yani Christidis
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Patent number: 4395575Abstract: 9-Substituted, 4- or 6-fluorine substituted retinoic acid derivatives useful as antitumor agents and in the treatment of acne as well as a method for their manufacture are disclosed. Substituents at the 9-position include substituted phenyl, thienyl and furyl groups.Type: GrantFiled: March 3, 1982Date of Patent: July 26, 1983Assignee: Hoffmann-La Roche, Inc.Inventors: Ka-Kong Chan, Beverly A. Pawson
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Patent number: 4371547Abstract: 2-Benzylideneglutaraldehydes of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently are hydrogen or a substituent selected from the group consisting of halo, lower-alkyl, phenyl, carboxy, lower-alkoxycarbonyl, phenoxycarbonyl, aminocarbonyl, hydroxysulfonyl, nitro, cyano, hydroxy, lower-alkoxy and phenoxy, a method of use thereof as disinfectants, disinfectant compositions comprising them, and 2,6-dialkoxy-3-(.alpha.-alkoxybenzyl)tetrahydropyrans of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are as defined above and R.sup.4 and R.sup.5 independently are alkyl of one to four carbon atoms, which are intermediates for their preparation are disclosed.Type: GrantFiled: August 21, 1981Date of Patent: February 1, 1983Assignee: Sterling Drug Inc.Inventors: Wolfgang Munzenmaier, Heinz Eggensperger, Helmut H. Ehlers, Wolfgang Beilfuss, Lothar Bucklers, Hans-Peter Harke
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Patent number: 4371712Abstract: An alkyl-substituted salicylaldehyde whose alkyl-substituent contains at least 6 and up to 2000 or more carbon atoms are novel composition of matter. Said novel alkylsalicylaldehyde can be prepared by the novel reaction of an alkylphenol containing at least six carbon atoms and up to 2000 or more carbon atoms in the phenol's alkyl-substituent, a dialkyloxy methane and a peroxide in the presence of a free radical forming catalyst.Type: GrantFiled: October 22, 1981Date of Patent: February 1, 1983Assignee: Standard Oil Company (Indiana)Inventors: Richard J. Lee, Leonard J. Baranowski
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Patent number: 4351950Abstract: Novel substituted arylene compounds and methods for their preparation and use are disclosed. These new compounds are useful as anti-arteriosclerotic agents.Type: GrantFiled: January 2, 1980Date of Patent: September 28, 1982Assignee: Warner-Lambert CompanyInventor: Ila Sircar
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Patent number: 4351962Abstract: A process is provided for the preparation of hydroxy benzene carboxaldehydes having the formula: ##STR1## wherein: R is selected from the group consisting of alkyl, alkoxy, cycloalkyl, aryl, alkoxyalkyl, fluoroalkyl, and hydroxyalkyl oxyalkylene having from one to about twenty carbon atoms; hydroxyalkyl having at least two to about twenty carbon atoms; hydroxy; aldehyde CHO; and halogen;n.sub.1, n.sub.2 and n.sub.3 are zero or 1; and at least one of n.sub.1, n.sub.2 and n.sub.3 is 1; andx is zero, 1, 2, 3 or 4, which comprises:(1) condensing with a formaldehyde compound a phenol having the formula: ##STR2## wherein R is selected from the group consisting of alkyl, alkoxy, hydroxyalkyl, cycloalkyl, aryl, alkoxyalkyl, fluoroalkyl, and hydroxyalkyl oxyalkylene having from one to about twenty carbon atoms; hydroxy; and halogen; andx is zero, 1, 2, 3 or 4,and unsubstituted in at least one ortho or para position in an aqueous reaction medium comprising phenol:HCHO in a molar ratio within the range from about 1:0.Type: GrantFiled: July 11, 1980Date of Patent: September 28, 1982Assignee: Rhone Poulenc Inc.Inventors: Peter S. Gradeff, Stanley T. Murayama
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Patent number: 4350833Abstract: Terephthaldialdehyde monoacetals represented by the general formula: ##STR1## (wherein, R.sub.1 and R.sub.2 are lower alkyl groups) are novel compounds, and they are produced by the reaction of terephthaldialdehyde with alcohols in the presence of a strongly acidic substance as a catalyst.Type: GrantFiled: January 28, 1981Date of Patent: September 21, 1982Inventor: Kunihiro Ichimura
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Patent number: 4346238Abstract: Sodium paraformylphenolate crystallized with two molecules of water is manufactured by:(a) condensing glyoxylic acid with an excess of phenol in water in the presence of sodium hydroxide at a temperature comprised between 30.degree. C. and 100.degree. C.;(b) neutralizing the solution thus obtained and then freeing it from the unconverted phenol by steam distillation or extraction with a water-immiscible organic solvent and then subjecting it hot under a pressure of oxygen, to a catalytic decarboxylating oxidizing degradation in the presence of sodium hydroxide;(c) allowing the aqueous solution so-obtained, after removal of the catalyst by filtration, and then concentration hot under vacuum to 60% plus or minus 10% of its initial volume, to crystallize; and(d) draining the precipitated crystals, washing them and then drying them to constant weight under vacuum of 1 mm of mercury at 20.degree. C.Type: GrantFiled: May 7, 1980Date of Patent: August 24, 1982Assignee: Societe Francaise HoechstInventors: Alain Schouteeten, Yani Christidis
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Patent number: 4340765Abstract: 4-Phenoxy-2-butene derivatives are disclosed as inhibitors of cytokinin plant growth regulatory activity and as possessing seed germination regulatory properties and senescence delaying activity when applied to plants. 4-Phenoxy-2-butene derivatives can also be useful as plant dwarfing agents, agents to retard seedling development or as herbicides.Type: GrantFiled: August 14, 1980Date of Patent: July 20, 1982Inventors: Gary M. Gray, George Schwartzkopf, Jr., J. T. Baker Chemical Co.
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Patent number: 4338251Abstract: A process for the preparation of a two-functional-group-containing terpenoid having the general formula: ##STR1## in which n is an integer of from 1 to 5, R represents a hydroxymethyl, formyl or carboxyl group, and A represents the hydrogen atom, or a 2-tetrahydropyranyl, benzyl, methoxymethol or methoxyethoxymethyl group comprising the oxidation with a microorganism belonging to the genus Nocardia. Some of the terpenoids are of value as anti-ulcer agents, while others are useful as intermediates.Type: GrantFiled: December 29, 1980Date of Patent: July 6, 1982Assignees: Eisai Co., Ltd., Agency of Industrial Science and TechnologyInventors: Akio Sato, Kenji Nakajima, Yoshimasa Takahara, Shizumasa Kijima, Noriaki Kuwana, Shinya Abe, Kouzi Yamada
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Patent number: 4337346Abstract: An optically active or racemic .alpha.-hydroxyaldehyde represented by the general formula (2), ##STR1## wherein R.sub.1 represents a C.sub.6 -C.sub.14 aryl group, C.sub.1 -C.sub.10 alkyl group, C.sub.3 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7 -C.sub.14 aralkyl group, or a group containing a functional group in the organic portion of said groups and R.sub.2 represents a C.sub.1 -C.sub.10 alkyl group, C.sub.2 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7-C.sub.14 aralkyl group, C.sub.6 -C.sub.14 aryl group, or a group containing a functional group in the organic portion of these groups, which is an important intermediate for preparation of pharmaceuticals and agricultural chemicals, and prepared by allowing an optically active or racemic compound represented by the general formula (1), ##STR2## (wherein A represents a C.sub.6 -C.sub.14 aryl group or a C.sub.1 -C.sub.4 alkyl or alkoxy group- or halogen-substituted C.sub.6 -C.sub.14 aryl group and R.sub.Type: GrantFiled: October 30, 1979Date of Patent: June 29, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Teruaki Mukaiyama, Yoji Sakito, Masatoshi Asami
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Patent number: 4336268Abstract: Cyclohexenes of the formula ##STR1## wherein R.sup.1 is hydroxy or lower alkoxy; n is 1 or 2; R.sup.2 is lower alkyl; and R.sup.3 is hydrogen, lower alkyl, lower alkenyl or lower cycloalkylmethyl, and their pharmaceutically acceptable acid addition salts are disclosed. The compounds of formula I have analgesic activity and are useful for the control of pains.Type: GrantFiled: January 27, 1981Date of Patent: June 22, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Hans Bruderer, Albert E. Fischli, Rudolf Pfister
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Patent number: 4333952Abstract: Compounds of formula (I): ##STR1## wherein: R.sup.1 is hydrogen, halogen or C.sub.1-4 alkoxy;X is oxygen; NR.sup.3 in which R.sup.3 is hydrogen, C.sub.1-4 alkyl, or -Y-R.sup.2 ; --C.dbd.O; or --CHOH;Y is --CH.sub.2 --CHOH, and when X is --C.dbd.O it may also be --CH.dbd.CH--; andR.sup.2 is C.sub.1-4 alkyl, one carbon atom of which is di- or tri-halogenated;or salts thereof, are useful in promoting growth of ruminants. Processes for their production, veterinary formulations and treatments are described.Type: GrantFiled: June 30, 1980Date of Patent: June 8, 1982Assignee: Beecham Group LimitedInventor: Brian G. McDonald
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Patent number: 4327025Abstract: A process for the preparation of a styrylcyclopropane-1-carboxylic acid ester of the formula ##STR1## in which R is C.sub.1-4 -alkyl or an alcohol radical customary in pyrethroids,R.sup.1 is alkoxy or alkylthio, either of which may be optionally substituted by halogen,R.sup.2 is hydrogen or alkoxy, orR.sup.1 and R.sup.2 together are optionally halogen-substituted alkylenedioxy, andR.sup.3 is hydrogen or chlorine,comprising reacting an ester of the formula ##STR2## in which Hal is chlorine or bromine,with a base.The compounds are insecticidally active. Numerous syntheses of the starting materials, some involving new intermediates, are also shown.Type: GrantFiled: April 7, 1980Date of Patent: April 27, 1982Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Dieter Arlt, Reinhard Lantzsch, Rainer Fuchs, Hans-Jochem Riebel, Rolf Schroder, Horst Harnisch
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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: 4322563Abstract: Substituted biphenyl-2-carboxaldehydes are prepared in good yield by reacting palladium complexes of substituted benzaldehyde aniline Schiff bases with substituted phenylmagnesium bromides in the presence of at least six, preferably eight, molar equivalents of triphenylphosphine.Type: GrantFiled: February 11, 1981Date of Patent: March 30, 1982Assignee: Merck & Co., Inc.Inventor: William F. Hoffman
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Patent number: 4319048Abstract: Novel 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraenoic acid, tetraenal or tetraenol derivatives useful as anti-tumor agents.Type: GrantFiled: July 30, 1980Date of Patent: March 9, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
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Patent number: 4317933Abstract: This invention comprises an alkylation, reduction and transesterification process for the preparation of ester substituted phenols. The products are useful as antioxidants and may be prepared in high yields and with a high degree of purity.Type: GrantFiled: November 9, 1977Date of Patent: March 2, 1982Assignee: The Goodyear Tire & Rubber CompanyInventor: Dane K. Parker
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Patent number: 4309349Abstract: The process depicted, for example, by the formulae ##STR1## yields valuable intermediates in the manufacture of drugs.Type: GrantFiled: October 1, 1980Date of Patent: January 5, 1982Assignee: Ciba-Geigy CorporationInventors: Heinz W. Gschwend, Charles F. Huebner
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Patent number: 4306097Abstract: Cycloalkanones, cycloalkanols and unsaturated analogs thereof, each of which has at the 3-position a 2-hydroxy-4-substituted phenyl group wherein the 4-position substituent is alkyl which can have an oxygen atom as part of the chain, or aralkyl which can have an oxygen atom as part of the alkyl chain, their use for pharmacological and medicinal purposes, intermediates therefor and processes for their preparation.Type: GrantFiled: September 8, 1980Date of Patent: December 15, 1981Assignee: Pfizer Inc.Inventors: Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4301081Abstract: The invention includes novel alkali metal complex compounds (and processes for their preparation) which are useful, inter alia for the hydrogenation of alkali metals at room temperature or below room temperature to form hydrides or nitrides.Type: GrantFiled: January 28, 1980Date of Patent: November 17, 1981Assignee: Studiengesellschaft Kohle mbHInventor: Borislav Bogdanovic
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Patent number: 4297520Abstract: p-Methoxytoluene is oxidized with a dichromate ion forming substance and sulfuric acid to give anisaldehyde in good yields. The oxidation proceeds with improved efficiency in the presence of a manganese compound.Type: GrantFiled: March 4, 1980Date of Patent: October 27, 1981Assignee: Daiwa Chemical Company Ltd.Inventor: Kozo Nakaoji
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Patent number: 4296042Abstract: This process relates to the synthesis of unsaturated aliphatic esters useful as insect sex attractants, including gossyplure, the insect sex pheromone of the pink bollworm moth, Pectinophora gossypiella, and intermediates therefor. The process utilizes a cyclic phosphonium (Wittig) reagent.Type: GrantFiled: June 18, 1980Date of Patent: October 20, 1981Assignee: Syntex (U.S.A.) Inc.Inventors: Joseph M. Muchowski, Michael C. Venuti
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Patent number: 4290974Abstract: The invention relates to oxybenzylidenebornanones which correspond to the general formula: ##STR1## in which Z and Z' denote hydrogen or a radical SO.sub.3 H, at least one of the two radicals Z and Z' denoting hydrogen, R.sub.1 denotes hydrogen, an alkyl radical having 2 to 18 carbon atoms, an alkenyl radical having 3 to 18 carbon atoms, a radical --(CH.sub.2 CH.sub.2 O).sub.n H, ##STR2## --(CH.sub.2).sub.m CO.sub.2 R, in which R denotes H or an alkyl radical, --(CH.sub.2).sub.3 SO.sub.3 H or a divalent radical --(CH.sub.2).sub.m or --CH.sub.2 --CHOH--CH.sub.2, m having the values 1 to 10, n having the values 1 to 20 and p having the values 1 to 6, and R.sub.3 and R.sub.4 representing hydrogen or an optionally branched or hydroxylic alkyl radical, or forming an aminoaliphatic heterocyclic ring with the nitrogen atom, R.sub.2 denotes a hydrogen atom, an alkoxy radical or a divalent radical --O-- bonded to the radical R.sub.1 if the latter is also divalent, and q denotes 1 or 2; if q has the value 2, R.sub.Type: GrantFiled: July 10, 1979Date of Patent: September 22, 1981Assignee: L'OrealInventors: Claude Bouillon, Charles Vayssie
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Patent number: 4284587Abstract: A new radioenzymatic assay for catecholamines utilizing the catechol-O-methyl transferase transfer of a methyl group from a labeled methyl donor to the catecholamines followed by isolation of the O-methylated(.sup.3 H)catecholamine and the subsequent measurement of radioactivity.Type: GrantFiled: October 12, 1978Date of Patent: August 18, 1981Assignee: The Upjohn CompanyInventors: Garland A. Johnson, Jacob D. Peuler
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Patent number: 4281207Abstract: Disclosed herein are monomeric compounds having the formula (I): ##STR1## wherein: R, R.sup.1, R.sup.2 and R.sup.3 are independently hydrogen or alkyl having from 1 to 4 carbon atoms;R.sup.4 is arylene having 6 to 18 carbon atoms;m is an integer from 1 to 4; andn is an integer from 0 to 4.These monomers can be homopolymerized or copolymerized with one or more other polymerizable monomers, and can particularly be copolymerized with those monomers having substituents which are susceptible to attack or degradation by a base. The resulting crosslinkable polymers are useful in relief image materials, such as photoresists and lithographic plates.Type: GrantFiled: October 26, 1979Date of Patent: July 28, 1981Assignee: Eastman Kodak CompanyInventor: John C. Wilson
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Patent number: 4275241Abstract: A process for the preparation of a-phenoxy-benzaldehyde which comprises contacting the 3-phenoxy-benzyl alcohol of the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and represent hydrogen or halogen with an aqueous solution of a dichromate in the presence of aqueous sulphuric acid at a temperature in the range of 50.degree. to 125.degree. C. The 3-phenoxy-benzaldehyde can be in a mixture of other organic compounds such as obtained by hydrolyzing a 3-phenoxy toluene chlorinated in the side chain at a temperature of 140.degree.-210.degree. C. under pressure.Type: GrantFiled: October 29, 1979Date of Patent: June 23, 1981Assignee: Bayer AktiengesellschaftInventors: Siegfried Bohm, Alfons Klein, Karlfried Wedemeyer
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Patent number: 4267344Abstract: N-Substituted N-carboxyanhydrides of .alpha.-amino acids, useful in peptide syntheses, and peptide synthesis process using such compounds, are disclosed. The N-substituent is penta(lower alkoxy)benzyl, or optionally substituted 9-xanthyl, 9-thioxanthyl or 9-selenoxanthyl.Type: GrantFiled: November 20, 1978Date of Patent: May 12, 1981Assignee: Proteinkemisk Institut. tilknyttet Akademiet for de tekniske VidenskaberInventors: John B. Halstrom, Karoly G. Kovacs
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Patent number: 4267382Abstract: Novel 9-(halo-substituted phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraene derivatives useful as anti-tumor agents are disclosed.Type: GrantFiled: February 4, 1980Date of Patent: May 12, 1981Assignee: Hoffmann-La Roche Inc.Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
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Patent number: 4266073Abstract: Compounds representd by the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are lower alkyl, R.sub.4 is lower alkoxy, R.sub.6 and R.sub.8 are methyl or trifluoro methyl, R.sub.9 is formyl, hydroxymethyl, alkoxymethyl, alkanoyloxymethyl, carboxyl, alkoxycarbonyl, lower alkenoxycarbonyl, lower alkynoxycarbonyl, carbamoyl, mono(lower alkyl)-carbamoyl, di(lower alkyl)carbamoyl or N-heterocyclylcarbonyl, R.sub.5, R.sub.7, R.sub.10, R.sub.11, R.sub.12 and R.sub.13 are hydrogen or fluorine with the proviso that at least one of R.sub.5, R.sub.7, R.sub.10, R.sub.11, R.sub.12 or R.sub.13 is fluorine or at least one of R.sub.6 or R.sub.8 is trifluoro methyl, or pharmaceutically acceptable salts thereof useful as antitumor agents are disclosed.Type: GrantFiled: November 21, 1979Date of Patent: May 5, 1981Assignee: Hoffmann-La Roche Inc.Inventors: Ka-Kong Chan, Beverly A. Pawson
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Patent number: 4263223Abstract: A chemical compound of the formula: ##STR1## wherein X is a halogen selected from bromine, chlorine, iodine and fluorine, and preferably bromine; Z is selected from the group constituted by --CHO, --CH.dbd.NOH, --C.tbd.N; n is an integer from 1 to 11; m.sub.1 and m.sub.2, identical or different, are integers from 1 to 4.Type: GrantFiled: April 20, 1977Date of Patent: April 21, 1981Assignee: Laboratoires Serobiologiques S.A.Inventor: Marc Pauly
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Patent number: 4258207Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO, --C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.Type: GrantFiled: March 15, 1979Date of Patent: March 24, 1981Assignee: Shell Oil CompanyInventor: Steven A. Roman