Polyoxy Patents (Class 568/648)
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Patent number: 5571803Abstract: Heteroarylpiperidines, pyrrolidines, and piperazines are useful as antipsychotic and analgesic agents, the compounds are especially useful for treating psychoses by administering to a mammal a psychoses-treating effective amount of one of the compounds. Depot derivatives of the compounds are useful for providing long acting effects of the compounds. The compounds are also useful as analgesics by administering a pain-relieving effective amount of one of the compounds to a mammal.Type: GrantFiled: December 22, 1995Date of Patent: November 5, 1996Assignee: Hoechst-Roussel Pharmaceuticals, Inc.Inventors: Joseph T. Strupczewski, Grover C. Helsley, Edward J. Glamkowski, Yulin Chiang, Kenneth J. Bordeau, Peter A. Nemoto, John J. Tegeler
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Patent number: 5563129Abstract: There are disclosed novel hydroquinone derivatives of the formula: ##STR1## The derivatives of the formula (I) have various pharmacological activities such as antioxidation in living bodies and are useful as medicaments.Type: GrantFiled: April 24, 1995Date of Patent: October 8, 1996Assignee: Takeda Chemical Industries, Ltd.Inventors: Hirotomo Masuya, Masayoshi Yamaoka
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Patent number: 5545763Abstract: Described are 1-oxo-substituted and unsubstituted isobutyl-4-ethoxy-benzenes and mixtures thereof with bicyclopentadiene derivatives, wherein the 1-oxo-substituted and unsubstituted isobutyl-4-ethoxy-benzenes are defined according to the structure: ##STR1## wherein Y.sub.1 represents one of the moieties: ##STR2## and wherein the bicyclopentadiene derivatives are defined according to the structure: ##STR3## wherein Z.sub.1 and Z.sub.2 represent hydrogen, C.sub.1 -C.sub.3 lower alkyl or C.sub.2 -C.sub.3 acyl and Z.sub.3 represents methyl or hydrogen with the proviso that Z.sub.1 and Z.sub.2 are not both hydrogen, and uses thereof in augmenting, enhancing or imparting aromas in and to perfume compositions, colognes, perfumed polymers and perfumed articles.Type: GrantFiled: April 25, 1995Date of Patent: August 13, 1996Assignee: International Flavors & Fragrances Inc.Inventors: Michael G. Monteleone, Richard A. Weiss, Mark D. Evans, Marie R. Hanna
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Patent number: 5495052Abstract: A tertiary amine is used to catalize the stereospecific ring-opening of chiral glycidol with o-methoxyphenol to afford high yields of enantiomerically enriched guaifenesin. The optical purity of the product may be even further enhanced by recrystallization.Type: GrantFiled: September 29, 1994Date of Patent: February 27, 1996Assignee: Arco Chemical Technology, L.P.Inventors: Wilfred P. Shum, Harry Mazurek, Jian Chen
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Patent number: 5463083Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i,e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase. Also disclosed is a method to treat disorders mediated by PAF and/or leukotrienes that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier, to a patient in need of such therapy.Type: GrantFiled: January 6, 1994Date of Patent: October 31, 1995Assignee: Cytomed, Inc.Inventors: Tesfaye Biftu, Xiong Cai, Sajjet Hussion, Gurmit Grewal, T. Y. Shen
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Patent number: 5462923Abstract: Described are 1-oxo-substituted and unsubstituted isobutyl-4-ethoxy-benzenes and mixtures thereof with bicyclopentadiene derivatives, wherein the 1-oxo-substituted and unsubstituted isobutyl-4-ethoxy-benzenes are defined according to the structure: ##STR1## wherein Y.sub.1 represents one of the moieties: ##STR2## and wherein the bicyclopentadiene derivatives are defined according to the structure: ##STR3## wherein Z.sub.1 and Z.sub.2 represent hydrogen, C.sub.1 -C.sub.3 lower alkyl or C.sub.2 -C.sub.3 acyl and Z.sub.3 represents methyl or hydrogen with the proviso that Z.sub.1 and Z.sub.2 are not both hydrogen, and uses thereof in augmenting, enhancing or imparting aromas in and to perfume compositions, colognes, perfumed polymers and perfumed articles.Type: GrantFiled: September 2, 1994Date of Patent: October 31, 1995Assignee: International Flavors & Fragrances Inc.Inventors: Michael G. Monteleone, Richard A. Weiss, Mark D. Evans, Marie R. Hanna
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Patent number: 5393776Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.Type: GrantFiled: May 13, 1994Date of Patent: February 28, 1995Assignee: Bristol-Myers Squibb CompanyInventor: Bradley C. Pearce
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Patent number: 5387718Abstract: Alkylphenyl alkyl ethers or alkylphenyl alkyl thioethers, of the formula ##STR1## where U represents O or S; and R.sub.1 -R.sub.6 each independently represent an alkyl or aryl group with 1-6 C atoms, but R.sub.1 -R.sub.5 may each independently represent a functional group other than these, particularly --COOR (R=C.sub.1-4 alkyl), --NO.sub.2, --NH.sub.2, --O--CH.sub.2 --CH.sub.2 --OH, --OH, --CHO, --H, or -halogen;R.sub.1 -R.sub.5 may be bridged by suitable bifunctional substituents, such as, e.g., --(CH.sub.2).sub.x --, or --(CH.sub.2).sub.x --Z--(CH.sub.2).sub.y -- (where Z represents a hetero atom; x=0-7 and y=0-7), or by unsaturated substituents or anellated ring systems; may be produced in high space-time yield by reacting the corresponding phenol or thiophenol with a arylalkyl carbonate at a temperature of 70.degree.-300.degree. C. under elevated or normal pressure, in the presence of a monocyclic, bicyclic, polycyclic, or acyclic amidine as a catalyst.Type: GrantFiled: July 14, 1992Date of Patent: February 7, 1995Assignee: Huels AktiengesellschaftInventors: Gunther Kohler, Peter Bickert
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Patent number: 5362835Abstract: A process for the production of a material having an increased molecular weight relative to the diepoxide starting material the material being either a hydroxy-terminated or an epoxy-terminated material comprisinga) reacting a diepoxide with a dihydroxy compound, in the presence, as catalyst, of a triflate salt of a metal of Group IIA, IIB, IIIA, IIIB, or VIIIA of the Periodic Table of Elements (according to the IUPAC 1970 convention);b) de-activating the triflate salt catalyst; andc) optionally advancing the material produced in step b), with an aromatic diol or phenol.Type: GrantFiled: December 9, 1991Date of Patent: November 8, 1994Assignee: Ciba-Geigy CorporationInventors: William M. Rolfe, Michael R. Thoseby, Bryan Dobinson
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Patent number: 5352845Abstract: A process for manufacturing an optically active saturated compound of the general formula (25): ##STR1## wherein R.sub.20 represents a group for protecting a hydroxy group, R.sub.21, R.sub.22, and R.sub.23 independently represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, is disclosed.Type: GrantFiled: March 25, 1993Date of Patent: October 4, 1994Assignee: Asahi Denka Kogyo K.K.Inventors: Seiichi Takano, Kunio Ogasawara
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Patent number: 5347050Abstract: The compounds of formula I, ##STR1## wherein the substituents have various significances, and physiologically acceptable hydrolyzable derivatives thereof having the hydroxy group in the 2 position of the 3-aminopropoxy side chain in esterified form, are useful as cardioselective .beta.-adrenoceptor blocking agents.Type: GrantFiled: April 13, 1993Date of Patent: September 13, 1994Inventors: Richard Berthold, William J. Louis
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Patent number: 5321167Abstract: An alkoxidation production low in alkylene oxide and 1,4-dioxane content is prepared by reacting an alkylphenol or fatty alcohol with an alkylene oxide in the presence of an alkali fatty alkoxide obtained by direct reaction of an alkali hydroxide with a fatty alcohol at elevated temperature.Type: GrantFiled: December 23, 1992Date of Patent: June 14, 1994Assignee: Huls AktiengesellschaftInventors: Egbert Schroer, Klaus Schulze, Ekkehard Wienhofer
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Patent number: 5221780Abstract: A 1-(2,6-dimethylphenyloxy)-2-alkanol of formula (1): ##STR1## wherein R is an alkyl group having 1 to 4 carbon atoms, and perfume compositions containing the alkanol having an intense woody note, and are useful as fragrance-imparting ingredients for various compositions, particularly in the cosmetic field.Type: GrantFiled: October 1, 1992Date of Patent: June 22, 1993Assignee: Kao CorporationInventors: Junji Koshino, Nao Toi, Katsuhiko Tajima, Yoshiaki Fujikura
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Patent number: 5216024Abstract: The present invention discloses new and useful compounds including methyl p-hydroxyphenyllactate, its analogues, chemical derivatives and chemically related compounds and their use as antitumor agents, as inhibitors of proliferative cell growth and as prophylactic agents to inhibit and prevent cancer and non-malignant cell growth.Type: GrantFiled: July 15, 1988Date of Patent: June 1, 1993Assignee: Baylor College of MedicineInventors: Barry M. Markaverich, James H. Clark, Rebecca Gregory, Mary Alejandro, Brian S. Middleditch, Gregory A. Johnson, Rajender S. Varma
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Patent number: 5191108Abstract: The invention relates to catechol carboxylic acid derivatives of the formula ##STR1## wherein, R.sub.1 is ##STR2## acetyl, hydrogen, hydroxy or alkanoyloxy, R.sub.2 is ##STR3## hydroxy, hydrogen or alkanoyloxy, wherein R is hydrogen, lower alkyl or --(CH.sub.2).sub.n --N--(lower alkyl).sub.2,R.sub.3 is hydrogen, lower alkyl or amino,R.sub.4 is hydrogen, lower alkyl, halogen or aminoA is ##STR4## wherein, R.sub.5 is hydrogen or acyl, R.sub.6 is hydrogen, halogen, lower alkyl, aryl or cycloalky, and R.sub.7 and R.sub.8, independently, are hydrogen, lower alkyl or halogen, orA is ##STR5## wherein, R.sub.5 is hydrogen or acyl, R.sub.9 is hydrogen, lower alkyl, R.sub.10 is hydrogen, lower alkyl or halogen, R.sub.11 is hydrogen, lower alkyl, cycloalkyl or halogen, m is 0 or 1, n is an integer of 2-10, provided, that no more than one of R.sub.1 or R.sub.2 can be hydroxy, alkanoyloxy or ##STR6## and when R is hydrogen, salts thereof with pharmaceutically acceptable bases or when R is --(CH.sub.2).sub.Type: GrantFiled: April 3, 1991Date of Patent: March 2, 1993Assignee: Hoffmann-La Roche Inc.Inventors: Matthew Carson, Ru-Jen L. Han, Ronald A. Lemahieu
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Patent number: 5117010Abstract: The present invention relates to the preparation of di-secondary alcohols comprising the reaction of an alcohol and a diglycidyl ether of a dihydric phenol in the presence of a catalyst of the formula (IV):MX (IV)wherein M is a metal from Groups IB to VIIIB or a metal or metalloid from Groups IIA to VA of the Periodic Chart of Elements or an ammonium ion and X is an anion selected from the group consisting of BF.sub.4.sup.-, PF.sub.6.sup.-, AsF.sub.6.sup.-, SbF.sub.6.sup.-, AlF.sub.4.sup.-, TiF.sub.6.sup.2-, SiF.sub.6.sup.2-, and ZrF.sub.6.sup.2- to produce the di-secondary alcohol, which can then be subjected to glycidylation to produce a glycidyl ether, orthe reaction of an alcohol, glycol or polyol and epichlorohydrin in the presence of the foregoing catalyst, followed by ring closure employing an alkali to produce a mono- or polyglycidyl ether. The monoglycidyl ether can be further reacted with a dihydric phenol to produce a di-secondary alcohol which is then glycidylized to produce a glycidyl ether.Type: GrantFiled: August 15, 1991Date of Patent: May 26, 1992Assignee: Ciba-Geigy CorporationInventor: Chi-Wen F. Cheng
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Patent number: 5110992Abstract: A process for the preparation of a glycol ether by reacting an olefin oxide with an excess of an alcohol over a catalyst; characterized in that the catalyst comprises a material which has been prepared by calcination of an anionic double hydroxide clay having a structure comprising magnesium and aluminum in combination, followed by rehydration and subsequent recalcination.Type: GrantFiled: September 24, 1990Date of Patent: May 5, 1992Assignee: The British Petroleum Co., p.l.c.Inventors: Martin P. Atkins, William Jones, Malama Chibwe
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Patent number: 5106885Abstract: What is provided herein are radiation curable compositions containing(a) multifunctional vinyl ether monomers having the formula:X--R.sub.1 --Y.sub.1 --R.sub.2 --Y.sub.2).sub.n CH.dbd.CH.sub.2 ].sub.mwhereX is a 5-8 membered ring, saturated or unsaturated;R.sub.1 is a direct bond or C.sub.1 -C.sub.10 straight or branched chain alkylene;Y.sub.1 and Y.sub.2 are independently oxygen or sulfur;R.sub.2 is C.sub.2 -C.sub.10 straight or branched chain alkylene;n is 0-10; andm is 3-5;(b) a cationic initiator, and, optionally,(c) a polymerizable vinyl ether, epoxide, or acrylate oligomer.Type: GrantFiled: November 3, 1989Date of Patent: April 21, 1992Assignee: ISP Investments Inc.Inventors: Kou-Chang Liu, Fulvio J. Vara, James A. Dougherty
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Patent number: 5095153Abstract: Diethers of general formula: ##STR1## where R, R.sup.I, R.sup.II, R.sup.III, R.sup.IV and R.sup.V are the same or different and are H, C.sub.1-18 linear or branched alkyl, C.sub.5-18 cycloalkyl, C.sub.6.about. aryl, C.sub.7-18 alkylaryl or C.sub.7-18 arylalkyl radicals, provided that when R is alkyl, R.sup.I is other than H or alkyl and when R.sup.I is alkyl, R is other than H or alkyl; R.sup.VI and R.sup.VIII are the same or different and are C.sub.1-18 linear or branched alkyl, C.sub.5-18 cycloalkyl, C.sub.6-18 aryl, or C.sub.7-18 arylalkyl radicals; and two or more of R to R.sup.V may be bonded to form a cyclic structure having 5 to 18 carbon atoms.The diethers are particularly useful in the preparation of Ziegler-Natta catalysts.Type: GrantFiled: October 11, 1990Date of Patent: March 10, 1992Assignee: HIMONT IncorporatedInventors: Giovanni Agnes, Giampietro Borsotti, Giuliana Schimperna, Elisabetta Barbassa
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Patent number: 5091531Abstract: Compounds of general formula (I) ##STR1## wherein R.sup.1 represents an optinally substituted carbocyclic or heterocyclic aryl group, or an optionally substituted alkyl, alkenyl, cycloalkyl or cycloalkenyl group; R.sup.2 represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl group or an optionally substituted carbocyclic or heterocyclic aryl or aralkyl group; R.sup.3 represents a hydrogen atom or an alkyl group; and either X represents an oxygen or sulphur atom, a group --CH.sub.2 -- or a group NR.sup.4 where R.sup.4 represents a hydrogen atom or a C.sub.1-4 alkyl group; and Y represents a group --CH.sub.2 -- or --CH.sub.2 CH.sub.2 -- X-Y together represent the group --CH.dbd.CH--; and salts and physiologically functional derivatives thereof are useful in the treatment of tumours. Processes for preparing the compounds, intermediates useful in their preparation, pharmaceutical compositions containing them and their use in the treatment of tumours are also described.Type: GrantFiled: August 12, 1988Date of Patent: February 25, 1992Assignee: Burroughs Wellcome Co.Inventor: Simon T. Hodgson
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Patent number: 5082978Abstract: Mono-, di- and triphenols are selectively monomethylated by reaction with para-dimethoxybenzene in the presence of a catalytically effective amount of an acid catalyst.Type: GrantFiled: May 9, 1991Date of Patent: January 21, 1992Assignee: Rhone-Poulenc ChimieInventors: Michel Gubelmann, Christian Allandrieu
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Patent number: 5068460Abstract: A process for preparation of resorcinol bis(hydroxyethyl)ether by first contacting resorcinol with ethylene carbonate and an alkali metal carbonate and then adding a solution of water and an alkali metal hydroxide and then recovering the resorcinol bis(hydroxyethyl)ether by crystallization.Type: GrantFiled: December 6, 1990Date of Patent: November 26, 1991Assignee: Eastman Kodak CompanyInventors: Charles E. Sumner, Jr., Brenda J. Hitch, Bobby L. Bernard
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Patent number: 5068451Abstract: A method of producing 3-phenoxy propanal derivatives of 3-phenoxy propanal derivatives of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are --H, --CH.sub.3 or a halogen radical, which comprises oxidizing allyl phenoxy ether derivatives of the formula ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above, in an alcohol as a solvent in the presence of a palladium salt, an oxidant, optionally an alkali metal salt of an onganic acid, and/or an acid at a temperature of 5.degree. C. -100.degree. C.Type: GrantFiled: May 4, 1990Date of Patent: November 26, 1991Assignee: National Science CouncilInventors: Ivan J. B. Lin, S. J. Jong
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Patent number: 5059723Abstract: This invention relates to the use of triorganophosphine compounds as catalyst for the reaction of phenols or thiophenols with cyclic organic carbonates.Type: GrantFiled: July 13, 1990Date of Patent: October 22, 1991Assignee: Indspec Chemical CorporationInventor: Hans Dressler
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Patent number: 5030733Abstract: Novel hydroxy-, alkoxy- and benzyloxy-substituted phospholipids, a process for the preparation thereof, and methods for treating pain, phospholipase, A.sub.2 mediated inflammation and similar conditions utilizing compounds or compositions thereof are disclosed.Type: GrantFiled: June 15, 1989Date of Patent: July 9, 1991Assignee: Hoechst-Roussel Pharmaceticals IncorporatedInventors: John J. Tegeler, Kirk D. Shoger
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Patent number: 4971995Abstract: Pharmaceutical or veterinary preparations containing (a) at least one compound with the formula: ##STR1## where:R.sub.o represents a C.sub.3 -C.sub.6 alkyl group or a benzyl group with the formula: ##STR2##in which R.sub.3 =H, a halogen, a C.sub.1 -C.sub.4 alkyl, a C.sub.1 -C.sub.4 alkoxy, CF.sub.3, NO.sub.2 or a CN group; andR.sub.2 represents:a C.sub.1 -C.sub.4 alkoxy group, in which case the pair (X, R.sub.1)=(O, OH), (O, C.sub.1 -C.sub.4 alkoxy), (CHOH, H), (O, H), (CH.sub.2, H) or (CO, H);and OH group, in which case the pair (X, R.sub.1)=(O, OH), (O, C.sub.1 -C.sub.4 alkoxy), (O, H) or (CH.sub.2, H), with the reservation that when (X, R.sub.1)=(O, OH), R.sub.o is different from a C.sub.3 -C.sub.6 alkyl or a benzyl group; ora CN or C.sub.1 -C.sub.4 alkyl-NH group, in which case the pair (X, R.sub.1)=(O, H) or (CH.sub.2, H), together with (b) a carrier or vehicle which is physiologically acceptable and appropriate for the compound used.Type: GrantFiled: January 26, 1989Date of Patent: November 20, 1990Assignee: Delande S.A.Inventors: Alain R. Schoofs, Michel Langlois, Christian R. Jeanpetit, Maryse F. Masson
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Patent number: 4954659Abstract: A grignard synthesis of pharmacologically active 1,4-bis(dihydroxyphenyl)butane and analogs, as well as novel intermediates, is provided, comprising preparing a grignard reagent preferably, a 3,4-dialkoxyphenyl propyl magnesium bromide, which may be reacted with carbonyl compounds to form intermediates of desired end products, said carbonyl compounds preferably being 3,4-dialkoxybenzaldehydes. The resulting alcohol is converted to a corresponding ether or siloxy compound, at the carbonyl site. The oxy-substituent is cleaved off; and the benzene ring or rings dealkylated to leave hydroxy substituents on the rings.Type: GrantFiled: August 19, 1988Date of Patent: September 4, 1990Assignee: Chemex Pharmaceuticals, Inc.Inventors: Robert M. Parkhurst, Ronald S. Pardini
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Patent number: 4929784Abstract: Optionally substituted benzyl-benzenes can be prepared by reaction of a benzyl alcohol of the formula ##STR1## with a benzene of the formula ##STR2## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 independently of one another denote hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine or chlorine, where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently of one another may also represent hydroxyl and R.sup.5 may additionally be C.sub.5 -C.sub.8 -alkyl,R.sup.6 represents hydrogen or one of the groups ##STR3## R.sup.8 denotes hydrogen or hydroxymethyl, in a ratio of 1 mole of benzene to 0.8-5 moles of benzyl alcohol in the presence of an amount of activated bleaching earth of 0.05-5% by weight, relative to the amount of benzyl alcohol, at a temperature between 90.degree. C. and 140.degree. C. in the presence of a diluent.Type: GrantFiled: October 11, 1989Date of Patent: May 29, 1990Assignee: Bayer AktiengesellschaftInventors: Kurt Klinkmann, Michael Herzhoff, Gerhard Burmeister
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Patent number: 4918241Abstract: A method of preparing an ether corresponding to the structure ##STR1## comprising reacting an aromatic iodine compound corresponding to the structure ##STR2## with methanol in the presence of a basic compound a copper catalyst and an amount of hydrogen which is effective to lower the oxidation state of the copper catalyst.Type: GrantFiled: August 7, 1989Date of Patent: April 17, 1990Assignee: Eastman Kodak CompanyInventor: Thomas H. Larkins, Jr.
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Patent number: 4895987Abstract: Ruthenium-cobalt- or cobalt-containing catalysts which have been promoted with phosphonites or phosphinites effectively catalyze the dealkoxyhydroxymethylation of aldehyde acetals to form glycol monoethers. Methylal, for example, may be reacted with syngas, i.e., CO and H.sub.2, in the presence of these phosphonite- or phosphinite-promoted cobalt or ruthenium- cobalt catalysts to form the monomethyl ether of ethylene glycol. In a like manner acetaldehyde may be converted to the corresponding propylene glycol monoether. The process may advantageously be carried out with high yields and selectivities in the presence of a polar or non-polar organic solvent in combination with the catalyst system of this invention.The invention is also directed to the phosphonite- or phosphonite-promoted cobalt and ruthenium-cobalt catalyst system per se.Type: GrantFiled: June 6, 1986Date of Patent: January 23, 1990Assignee: Sun Refining and Marketing CompanyInventors: D. Michael Duggan, James E. Lyons, Harry K. Myers, Robert E. Ledley
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Patent number: 4886891Abstract: The present invention provides a process for preparing a 1,1-disubstituted ethylene derivative of the formula ##STR1## which comprises reacting lead with a carbinol derivative of the formula ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, X, Y, m and n are defined in the specification. The reaction is conducted more advantageously in the presence of a metal having higher ionization tendency than lead.Type: GrantFiled: December 18, 1987Date of Patent: December 12, 1989Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Shigeru Torii, Masatoshi Taniguchi, Michio Sasaoka, Yoshihisa Tomotaki, Mitsuo Akada, Hideo Tanaka, Akira Suzuki, Shiro Yamashita
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Patent number: 4842775Abstract: A method for producing a compound of the formula: ##STR1## [wherein R.sup.1 and R.sup.2 each stand for a lower alkyl group; n denotes an integer of 0 to 21; X stands for hydrogen atom or an optionally protected hydroxyl group; and Y stands for an optionally protected hydroxyl group], which comprises reducing an ester compound of the formula: ##STR2## [wherein R.sup.1, R.sup.2, n, X and Y are of the same meaning as defined above, and R.sup.3 stands for a lower alkyl group ] with a mixture of sodium borohydride and aluminum chloride. This method give the desired compound in a high yield, and is advantageous from the industrial point of view.Type: GrantFiled: April 26, 1988Date of Patent: June 27, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Taiiti Okada, Yasuaki Abe
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Patent number: 4816491Abstract: p-Allyl or cycloalkyl phenoxy alkanols and esters are provided having the structure: ##STR1## in which: R.sub.1 is an alkyl group having from one to six carbon atoms, preferably tertiary, and still more preferably tertiary-butyl; or a bivalent cycloalkylene group condensed with the phenyl group at adjacent ring carbons thereof, such as in indane;R.sub.2 is lower alkyl having from one to three carbon atoms or hydrogen;R.sub.3 is hydroxyl or an ester group selected from the group consisting of COOR.sub.4 and OOCR.sub.4 derived from unsubstituted and hydroxy-substituted monocarboxylic acids and COOR.sub.5 OOC and OOCR.sub.Type: GrantFiled: May 7, 1987Date of Patent: March 28, 1989Assignee: Frank M. BergerInventors: Frank M. Berger, Joseph I. Degraw, Howard L. Johnson
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Patent number: 4808736Abstract: In this process of the invention a compound of the formula ##STR1## wherein R is a leaving group, is reacted with a compound of the formula ##STR2## wherein R.sup.1 is an ether protecting group, and, if desired a thus-obtained compound of the formula ##STR3## is converted in a known manner into d-.alpha.-tocopherol.Type: GrantFiled: August 10, 1987Date of Patent: February 28, 1989Assignee: Hoffmann-LaRoche Inc.Inventors: Richard Barner, Josef Hubscher
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Patent number: 4731488Abstract: A catalyst for vapor-phase hydrogen transfer reaction between a carbonyl compound having an alkenyl or aryl group and a primary or secondary alcohol, said catalyst having a composition represented by the following general formulaMg.sub.a X.sub.b Y.sub.c O.sub.dwherein X represents at least one element selected from the group consisting of boron, aluminum, silicon, phosphorus, titanium, vanadium, iron, yttrium, zirconium, niobium, tin, antimony, lead, bismuth, lanthanum and cerium, Y represents at least one element selected from the group consisting of alkali metals and alkaline earth metals excepting magnesium, O represents oxygen, and a, b, c and d represent the atomic ratios of the individual elements, and when a is 1, b represents a number of 0.01 to 0.5, c represents a number of 0 to 0.5, and d is a number determined by the atomic valences and atomic ratios of the individual elements.Type: GrantFiled: June 6, 1986Date of Patent: March 15, 1988Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Yuuji Shimasaki, Youichi Hino, Michio Ueshima
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Patent number: 4716146Abstract: This invention relates to compounds of the general structure ##STR1## wherein R and R.sup.1 are lower alkyl having from 1 to 2 carbon atoms useful as fragrance additives and to the fragrance compositions containing the same.Type: GrantFiled: December 19, 1986Date of Patent: December 29, 1987Assignee: National Distillers and Chemical CorporationInventor: Eugene G. Harris
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Patent number: 4713458Abstract: Ketones and aldehydes are converted to ethenylidene-containing compounds by reaction thereof with dimethyl carbonate and a phosphine compound.Type: GrantFiled: August 21, 1984Date of Patent: December 15, 1987Assignee: The Dow Chemical CompanyInventors: Kevin A. Frazier, James M. Renga
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Patent number: 4700005Abstract: Phenolic ethers are produced by reacting a phenol with a compound selected from an alkyl halide, an aryl halide, a dialkyl sulphate and a diaryl sulphate in the presence as catalyst of an amidine.Type: GrantFiled: June 6, 1986Date of Patent: October 13, 1987Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4654446Abstract: Alkylarylethers are produced according to the invention using phenols and ethers of aliphatic alcohols as the starting materials, in the presence of BPO.sub.4.Type: GrantFiled: February 27, 1986Date of Patent: March 31, 1987Assignee: Eniricerche S.p.A.Inventors: Maurizio Brunelli, Pierferdinando Ferrari, Fabrizio Stroppa, Giuseppe Bellussi
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Patent number: 4652563Abstract: This invention relates to dihydropyridazinone compounds having a cyclopropylmethoxyethyl group in the 6-substituent. These compounds are vasodilators and .beta.-adrenoceptor antagonists. A particular compound of the invention is 6-[4-[3-[2-hydroxy-3-[4-(2-(cyclopropylmethoxy) ethyl)phenoxy]propylamino]propionamido]phenyl]-5-methyl-4,5-dihydro-3 (2H)-pyridazinone.Type: GrantFiled: May 16, 1985Date of Patent: March 24, 1987Assignee: Smith Kline & French Laboratories Ltd.Inventor: Robert A. Slater
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Patent number: 4650910Abstract: Substituted styrenes are prepared by treatment on N-acyl-B-phenethylamines with bases and removal by distillation of the styrene which is formed during the reaction.Type: GrantFiled: March 4, 1986Date of Patent: March 17, 1987Assignee: Bayer AktiengesellschaftInventors: Karl-Wilhelm Henneke, Karlfried Wedemeyer
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Patent number: 4644085Abstract: The invention relates to a new anti-cancer chemical compound which has been called rooperol and certain derivatives thereof of the general formula ##STR1## in which A is chosen from the group including a phenyl group, a substituted phenyl group and --CH.sub.2 --O--R.sup.5 where R.sup.5 =H, an alkyl (C.sub.1 -C.sub.5), aralkyl or acyl substituent; R.sup.1 and R.sup.2 are chosen from substituents including H for both or singly if one of them is --OH, --NH.sub.2, --SH, ##STR2## or taken together R.sup.1 and R.sup.2 are =0; R.sup.3 is H or ##STR3## where R.sup.6 is an alkyl group (C.sub.1 -C.sub.7); either of R.sup.4 or B are chosen from substituents including H, ##STR4## a phenyl group, substituted phenyl group or a furyl group.Type: GrantFiled: June 4, 1985Date of Patent: February 17, 1987Assignee: Rooperol (NA) NVInventors: Siegfried Drewes, Roelof W. Liebenberg
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Patent number: 4619780Abstract: 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; 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 oxo reaction 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: August 24, 1984Date of Patent: October 28, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4618729Abstract: The ruthenium-cobalt carbonyl metal cluster catalyst Co.sub.2 Ru(CO).sub.11 effectively catalyzes the dealkoxyhydroxymethylation of aldehyde acetals to form glycol monoethers. Methylal, for example, may be reacted with syngas, i.e., CO and H.sub.2, in the presence of this ruthenium-cobalt cluster catalyst to form the monomethyl ether of ethylene glycol.Type: GrantFiled: October 2, 1985Date of Patent: October 21, 1986Assignee: Sun Refining and Marketing CompanyInventors: D. Michael Duggan, James E. Lyons, Harry K. Myers, Jr.
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Patent number: 4617287Abstract: Ruthenium carbonyl-cobalt carbonyl catalyst mixtures effectively catalyze the dealkoxyhydroxymethylation of aldehyde acetals, wherein said acetal may be prepared separately or in situ from an aldehyde and an alcohol. Methylal, for example, may be reacted with syngas, i.e., CO and H.sub.2, in the presence of this ruthenium carbonyl-cobalt carbonyl catalyst to form the monomethyl ether of ethylene glycol.The invention also is directed to the ruthenium carbonyl-promoted cobalt carbonyl catalysts per se, including novel precipitated forms of these ruthenium-cobalt carbonyl catalyst mixtures.Type: GrantFiled: October 2, 1985Date of Patent: October 14, 1986Assignee: Sun Refining and Marketing CompanyInventor: James E. Lyons
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Patent number: 4616082Abstract: New hydroquinone ether compounds of formula I are described: ##STR1## wherein p is 1 or 2 and Q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification,The new compounds are useful e.g. as stabilizers in photographic material.Type: GrantFiled: June 7, 1985Date of Patent: October 7, 1986Assignee: Ciba-Geigy AGInventor: Frederick H. Howell
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Patent number: 4613682Abstract: The vapor phase reaction of phenolic compounds with organic halides to form aromatic ethers is catalyzed by metal oxides. The halide value of the organic halide is retained as hydrogen halide which can be reacted with a halide acceptor such as methanol to form methyl halide and water.Type: GrantFiled: August 19, 1985Date of Patent: September 23, 1986Assignee: The Dow Chemical CompanyInventor: Kathryn A. Eickholt
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Patent number: 4582905Abstract: Convenient intermediates for preparing 3-substituted-2-hydroxypropyl aryl ether .beta.-blockers, a reaction to the intermediates of the following formula and a conversion to obtain the said .beta.-blockers are disclosed. ##STR1## (wherein X is hydrogen or halogen; Y is halogen, hydroxy, lower acyloxy, amino, lower alkylamino, lower aralkylamino, lower acylamino, di-lower alkylamino, lower alkyleneamino, N-lower alkyl-N-lower aralkylamino, di-lower acylamino, N-lower alkyl-N-lower acylamino or N-tri-lower alkylsilylamino;one of P and R combined together with Q represents lower alkylene or alkenylene optionally interrupted by O, N or S and optionally substituted by lower alkyl, lower aralkyl, lower carboxylic acyl, carboxy, protected carboxy; hydroxy, lower alkoxy, lower acyloxy, oxo; amino, lower alkylamino, lower acylamino, nitro, nitroso, lower alkylthio, lower sulfonic acyl or halogen;and the remaining R or P is hydrogen or halogen;and dotted line represents the presence of one or two double bonds).Type: GrantFiled: December 20, 1984Date of Patent: April 15, 1986Assignee: Shionogi & Co., Ltd.Inventor: Makiko Sakai
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Patent number: 4578210Abstract: Six-membered ring compounds of the formula I ##STR1## wherein A is a benzene or cyclohexane ring,X.sup.1 to X.sup.6 independently of one another in each case are H, --OR, --COOR, --SR, --SOR, --SO.sub.2 R or, if A is a cyclohexane ring, also --O--COR, andR is in each case an alkyl group which has up to 15 C atoms and in which one or two CH.sub.2 groups can be replaced by O atoms, at least three of the substituents X.sup.1 to X.sup.6 being other than H,can be used as constituents of discotic liquid-crystal phases for liquid-crystal display elements.Type: GrantFiled: September 13, 1984Date of Patent: March 25, 1986Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Klaus Praefcke, Bernd Kohne, Wadi Poules, Rudolf Eidenschink, Bernhard Scheuble
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Patent number: 4568497Abstract: Preparation of monoethers of dihydroxybenzenes from an alkenylphenol and an alkylating agent and thereafter oxidizing in the presence of an acid catalyst.Type: GrantFiled: May 29, 1984Date of Patent: February 4, 1986Assignee: The Dow Chemical CompanyInventors: Abel Mendoza, Eric W. Otterbacher