Carboxyl, Not Bonded Directly To A Ring, In Acid Moiety Patents (Class 560/105)
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Patent number: 5235095Abstract: An improved process for the separation of enantiomers of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves: (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base; (ii) treating said salt solution with one-half molar equivalent of a chiral organic nitrogenous base having a base strength no stronger than said organic or inorganic base; and (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt, the improvement being adding to the salt solution of step (ii) an inert organic or inorganic base that is soluble in the salt solution.Type: GrantFiled: January 24, 1992Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventors: Abbas Kadkhodayan, Deepak R. Patil, Azfar A. Choudhury
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Patent number: 5235100Abstract: A process for the separation of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process comprises:i) separating a racemic mixture of an aliphatic carboxylic acid or ester thereof having the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; cycloalkyl; alkyl-substituted cycloalkyl; C.sub.6 to C.sub.14 aryl; C.sub.1 to C.sub.6 alkylthio; C.sub.2 to C.sub.8 cycloalkylthio; C.sub.6 to C.sub.10 arylthio; C.sub.6 to C.sub.10 arylcarbonyl; C.sub.4 to C.sub.8 cycloalkenyl; trifluoromethyl; halo; or C.sub.4 to C.sub.Type: GrantFiled: January 24, 1992Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventors: Azfar A. Choudhury, Abbas Kadkhodayan, Deepak R. Patil
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Patent number: 5221765Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.2 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 75.degree. C. to about 200.degree. C.Type: GrantFiled: January 24, 1992Date of Patent: June 22, 1993Assignee: Ethyl CorporationInventors: Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
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Patent number: 5220053Abstract: An improved process for the separation of enantiomers of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves adding a mixture of the aliphatic carboxylic acid to the material formed by: (i) forming a solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic solvent; (ii) treating said solution with a chiral organic nitrogenous base; (iii) precipitating from the reaction solution formed in step (ii) a crystalline material comprised of the less soluble diastereomeric salt. The solution is admixed with the crystalline material for a time sufficient to cause an increase in the amount of the less soluble diastereomeric salt in the crystalline material.Type: GrantFiled: January 24, 1992Date of Patent: June 15, 1993Assignee: Ethyl CorporationInventors: Azfar A. Choudhury, Abbas Kadkhodayan, Deepak R. Patil
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Patent number: 5214191Abstract: 2-Phenylalkanoate esters which are useful as inhibitors of human leukocyte elastase.Type: GrantFiled: May 22, 1990Date of Patent: May 25, 1993Assignee: Cortech, Inc.Inventors: Gary P. Kirschenheuter, Lyle W. Spruce, John C. Cheronis
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Patent number: 5210325Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalyst which comprises one or more compounds comprising a rare earth element and phosphorus supported on an inert porous support. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: August 10, 1992Date of Patent: May 11, 1993Assignee: Shell Oil CompanyInventors: Richard A. Kemp, Paul R. Weider
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Patent number: 5208224Abstract: Novel phosphorus containing compounds are described, as well as methods for the preparation and pharmaceutical composition of same, which are useful in preventing the intestinal absorption of cholesterol and thus are useful in the treatment of hypercholesterolemia and atherosclerosis.Type: GrantFiled: March 13, 1991Date of Patent: May 4, 1993Assignee: Warner-Lambert CompanyInventors: Gary L. Bolton, Janak K. Padia, Bharat K. Trivedi
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Patent number: 5198568Abstract: This invention relates to novel compositions of matter which are esters with enhanced water solubility, for use in aqueous enzymatic resolution reactions of racemic mixtures of these esters for producing the separate chiral isomers of the racemic mixture. The invention also relates to novel methods for preparing these esters. The importance of the production of the separate chiral isomers of the racemic mixtures resides in the isolation of the isomers which frequently have different biological activities. Of particular significance regarding the water soluble esters of this invention is that they are derivatized with groups which enhance their aqueous solubility and their reactivity with enzymatic resolving methods which are mediated in an aqueous environment.Type: GrantFiled: September 9, 1991Date of Patent: March 30, 1993Assignee: Sepracor, Inc.Inventors: Charles M. Zepp, Stephen A. Wald, David R. Dodds
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Patent number: 5198559Abstract: The present invention relates to N acyl and O acyl derivatives of N,N-bis(2,2-dimethyl-3-hydroxypropyl)amine which are produced as follows: ammonium halide, sulphate or aldehyde, and isobutyl aldehyde are subjected to condensation reaction and the obtained product is reduced to the corresponding amino alcohol. The hydrogen atoms linked to the nitrogen atom and the oxygen atom are thereafter substituted by acyl groups. The N-acylation and esterification of hydroxyl groups can be performed simultaneously using a carboxyl acid, carboxyl acid halide, or carboxyl acid anhydride. The N,N-bis(2,2-dimethyl-3-hydroxypropyl)amine derivatives can be used as polymer stabilizers, PCV plasticizers, emulsifiers, corrosion resistance agents, and metal complexing agents.Type: GrantFiled: July 19, 1990Date of Patent: March 30, 1993Assignee: Neste OyInventors: Leila Lahtinen, Salme Koskimies, Simo Tuominen, Eija Valtonen
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Patent number: 5179224Abstract: Disclosed herein is a process for preparing a corresponding cinnamate ester by reacting a styrene compound, carbon monoxide, an alcohol and oxygen by the use of (1) metallic palladium or a compound thereof, (2) a copper compound, (3) a compound of at least one metal selected from Groups 4A, 5A, 7A, 8A (the iron group only) and 2B in the Periodic Table and (4) a halogen compound as a catalyst which comprises treating the catalyst components recovered from the reaction liquid after completion of the reaction with an oxidizing agent in the presence of an organic acid to regenerate their catalytic activity, using the resulting catalyst components again in the reaction as a catalyst and repeating the foregoing procedure.The regenerated catalyst is recovered in catalytic activity to the extent of that of a fresh catalyst and thus gives a high reaction performance in the subsequent reaction. Thus, the catalyst containing expensive metal can be used circulatively.Type: GrantFiled: October 1, 1991Date of Patent: January 12, 1993Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Usaji Takaki, Yoshihiro Yamamoto, Toshio Matsuhisa, Isamu Sudo, Shinobu Aoki
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Patent number: 5179229Abstract: A process for the preparation of 2,2-diorgano-3-arylpropionic acids is disclosed by the carbonylation of corresponding 2,2-diorgano-1-aryl ethanol in the presence of a Lewis acid catalyst. Furthermore, a process for the production of 2,2-diorgano-3-arylpropionic esters is disclosed by reacting a corresponding 2,2-diorgano-1-aryl ethanol with carbon monoxide and an alcohol in the presence of a Lewis acid catalyst.Type: GrantFiled: April 24, 1992Date of Patent: January 12, 1993Assignee: Hoechst Celanese CorporationInventor: Varadaraj Elango
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Patent number: 5177109Abstract: Compounds, compositions and methods are described for treating a CNS disorder such as a cognitive disorder, epilepsy, depression, Parkinson's disease, Alzheimer's disease, a neurodegenerative disease or neurotoxic injury. Compound of interest are 2-amino-4,5-methyleneadipic acid compounds and derivatives defined by the formula I: ##STR1## wherein R.sup.1 is selected from hydrido, alkyl, cycloalkyl, aralkyl, aryloxyalkyl, arylthioalkyl, ##STR2## with each of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 being independently selected from hydrido, alkyl, cycloalkyl, aryl and aralkyl; wherein each of X and Y is independently selected from hydroxyl, alkoxy, alkylthio, amino and ##STR3## with each of R.sup.6 and R.sup.7 being independently selected from hydrido, alkyl, cycloalkyl, aryl and aralkyl; wherein any of R.sup.1 through R.sup.Type: GrantFiled: July 19, 1991Date of Patent: January 5, 1993Assignee: G. D. Searle & Co.Inventors: Roberto Pellicciari, Benedetto Natalini, Maura Marinozzi, Alexis A. Cordi, Joseph B. Monahan, Thomas H. Lanthorn
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Patent number: 5166218Abstract: Tertiary and secondary amines of the formulas ##STR1## and ##STR2## wherein n is the integer 1 or 2,R is hydrogen, lower-alkanoyl or phenyl-lower-alkanoyl,X.sup.1 is phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position,X.sup.2 is lower-alkyl, phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position or phenyl optionally monosubstituted by fluorine, chlorine, trifluoromethyl or lower-alkoxy,Y is hydrogen or methyl, andZ is a phenyl or thienyl residue substituted as hereinafter described,and the physiologically and pharmaceutically compatible salts are described. The compounds of formulas I and V-1 have catabolic activity and can be used for the treatment of obesity and diabetes mellitus or for the treatment of conditions which are associated with an increased protein breakdown, or as feed additives for fattening animals. The compounds of formulas I and V-1 can be prepared starting from corresponding primary amines.Type: GrantFiled: August 12, 1991Date of Patent: November 24, 1992Assignee: Hoffmann-La Roche Inc.Inventors: Leo Alig, Marcel Muller
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Patent number: 5166377Abstract: The invention concerns novel 4-phenyl-1,3-dioxan-5-ylalkenoic acid derivatives of the formula I having cis relative stereochemistry at positions 4 and 5 of the dioxane ring and wherein Ra and Rb are variously hydrogen, alkyl, halogenoalkyl, alkenyl, and optionally substituted aryl or arylalkyl, Rc is hydroxy, alkoxy or alkanesulphonamido, n is 1 or 2, A is ethylene or vinylene, Y is (2-5C)polymethylene optionally substituted by alkyl, and benzene ring B is optionally substituted phenyl, or, when Rc is hydroxy, a salt thereof. The acid derivatives antagonize one or more of the actions of thromboxane A.sub.2 (TXA.sub.2) and are expected to be of value in those disease conditions in which TXA.sub.2 is involved. The invention also provides pharmaceutical compositions containing an acid derivative of formula I, and processes for their chemical production.Type: GrantFiled: February 9, 1988Date of Patent: November 24, 1992Assignee: Imperial Chemical Industries PLCInventors: Andrew G. Brewster, Peter W. R. Caulkett
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Patent number: 5166419Abstract: A method for preparing .alpha.-(4-isobutylphenyl)propionic acid or its precursor is here disclosed which comprises the following steps (I), (II) and (III):step (I): subjecting isobutylbenzene and a polyalkylbenzene to disproportionation reaction in order to form p-isobutylethylbenzenestep (II): dehydrogenating p-isobutylethylbenzene obtained in the step (I) to form p-isobutylstyrene, andstep (III): the following step (IIIa) or (IIIb):step (IIIa): reacting p-isobutylstyrene obtained in the step (II) with carbon monoxide and hydrogen to prepare .alpha.-(4-isobutylphenyl)propionaldehyde, orstep (IIIb): reacting p-isobutylstyrene obtained in the preceding step (II) with carbon monoxide and water or a lower alcohol to prepare .alpha.-(4-isobutylphenyl)propionic acid or its alkyl ester.Type: GrantFiled: August 22, 1990Date of Patent: November 24, 1992Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Yuuichi Tokumoto, Isoo Shimizu, Satoru Inoue
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Patent number: 5162589Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of sodium barium phosphate or potassium barium phosphate. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvent, and chemical intermediates.Type: GrantFiled: June 8, 1992Date of Patent: November 10, 1992Assignee: Shell Oil CompanyInventors: Rudolf J. Wijngaarden, Kees Latjes
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Patent number: 5159090Abstract: A process and intermediates for the enantioselective synthesis of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid are disclosed.Type: GrantFiled: April 16, 1991Date of Patent: October 27, 1992Assignee: Eli Lilly and CompanyInventors: Charles J. Barnett, Thomas M. Wilson
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Patent number: 5155255Abstract: A process for the manufacture of certain cycloalkenylalkenes, e.g. vitamin A acetate, comprises dehydrating 1-(5-acetoxy-3-methyl-penta-1,3-dienyl)-2,6,6-trimethyl-cyclo hexanol or 4 aetoxy-1-(5-acetoxy-3-methyl-penta-1,3-dienyl)-2,6,6-trimethyl-cyclohexano l or 1-(9-acetoxy-3,7-dimethyl-4-hydroxy-nona-2,5,7-trienyl)-2,6,6-trimethyl- cyclohexene in the presence of an alkali metal bromide or of manganese bromide or of a hydrate of such a bromide as the catalyst and in an organic solvent.The products are especially suitable as intermediates in carotinoid syntheses.Type: GrantFiled: March 25, 1991Date of Patent: October 13, 1992Assignee: Hoffmann-La Roche Inc.Inventors: Mario Mazzuchelli, Milan Soukup, Paul Spurr, Claude Stritt
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Patent number: 5130462Abstract: Cyclobutane derivatives of the formulas ##STR1## wherein P is a hydroxy protecting group and X is a leaving group are useful intermediates in the preparation of antiviral compounds.Type: GrantFiled: February 19, 1991Date of Patent: July 14, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: William A. Slusarchyk, Robert Zahler
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Patent number: 5124070Abstract: Disclosed are herein optically active ester derivatives represented by the formula (I): ##STR1## (wherein R.sub.1 represents an alkyl group having 3 to 20 carbon atoms; R.sub.2 represents an optically active alkyl or alkoxyalkyl group having 3 to 15 carbon atoms optionally substituted by halogen atoms; Y represents --O--, --COO-- or --OCO--; X represents --COO-- or --OCO--; l represents a number of 1 or 2; k and m each represents a number of 0 or 1; n represents a number of 1 to 6), preparation processes therefor, liquid crystal materials containing such ester derivatives as active ingredient, and a light switching element using said liquid crystal materials as liquid crystal element.Type: GrantFiled: August 28, 1989Date of Patent: June 23, 1992Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Takeshi Tani, Chizu Kawakami, Koichi Fujisawa, Kiyoshi Imamura
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Patent number: 5118870Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of a xerogel comprising one or more compounds comprising a rare earth element and phorphorus. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: April 23, 1990Date of Patent: June 2, 1992Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 5107053Abstract: A ruthenium phosphine complex having catalytic, hydrogenation activity is disclosed. The catalyst as the formula ##STR1## wherein R and R' are the same or different and are C.sub.1 to C.sub.6 linear or branched alkyl; R" is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.1 is C.sub.1 to C.sub.6 linear or branched alkyl; and n is an integer from 1 to 6.The phosphine complex is particularly useful in the asymmetric hydrogenation of unsaturated carboxylic acids or alkyl esters thereof.Type: GrantFiled: October 25, 1991Date of Patent: April 21, 1992Assignee: Ethyl CorporationInventor: Tse-Chong Wu
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Patent number: 5097061Abstract: A method for preparing .alpha.-(4-isobutylphenyl)propionic acid or its precursor is here disclosed which comprises a step A of forming p-isobutylstyrene from p-isobutylethylbenzene and a step B of forming .alpha.-(4-isobutylphenyl)propionaldehyde from p-isobutylstyrene or a step C of forming .alpha.-(4-isobutylphenyl)propionic acid or its alkyl ester from p-isobutylstyrene.Furthermore, a method for preparing said p-isobutylethylbenzene is also disclosed which comprises alkylating isobutylbenzene or 4-ethyltoluene with ethylene or propylene.Type: GrantFiled: June 19, 1989Date of Patent: March 17, 1992Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Isoo Shimizu, Yasuo Matsumura, Yuuichi Tokumoto, Kazumichi Uchida
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Patent number: 5095134Abstract: This application relates to monomers and homopolymers of diacetylenic ethers having the formula ##STR1## wherein X is alkyl, alkenyl, aryl, alkaryl, aralkyl, aralkenyl, monoalkylamino or dialkylamino and Y is alkyl, alkenyl or ##STR2## where X' is independently selected from the group of X. The invention also relates to the method of preparing and using said alkoxy diacetylenes.Type: GrantFiled: October 23, 1990Date of Patent: March 10, 1992Assignee: ISP Investments Inc.Inventor: Kou-Chang Liu
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Patent number: 5095137Abstract: The amides of cyclomethylen-1,2-bicarboxylic acids having the formula: ##STR1## wherein A represents ##STR2## R.sup.1 represents --H, --CH.sub.3, --CH.sub.2 --CH.sub.3, --CH(CH.sub.3).sub.2, ##STR3## R.sup.2 represents --H, CH.sub.3, --CH.sub.2 --CH.sub.3, --CH(CH.sub.3).sub.2, --CH.sub.2 --CH.sub.2 --CH.sub.3, --CH.sub.2 --CH(CH.sub.3).sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.3, --CH.sub.2 --C.sub.6 H.sub.5, --C.sub.6 --H.sub.5 ;R.sup.3 represents --H, --CH.sub.3, --C.sub.2 H.sub.5, ##STR4## R.sup.5 represents --H, --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 C.sub.6 H.sub.5, ##STR5## Y=--H, --CH.sub.3, --CH(CH.sub.3).sub.2 Z=--H,--CH.sub.3, --C(CH.sub.3).sub.3, --CH(C.sub.2 H.sub.5).sub.2, ##STR6## R.sup.4 =R.sup.5, ##STR7## m is 0 or 1 and n is an integer varying between 0 and 3, are endowed with ACE-inhibiting activity and are thus therapeutically useful as anti-hypertension agents.Type: GrantFiled: October 9, 1990Date of Patent: March 10, 1992Assignee: Laboratori Guidotti SpAInventors: Luigi Turbanti, Guido Cerbai, Marco Criscuoli
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Patent number: 5093517Abstract: There is disclosed a method for making compounds such as 3,6,9-trioxaundecane-1,11-bis (3-n-dodecylthiopropionate) which comprises reacting an alkyl thiopropionate with a glycol at temperatures between 50.degree. C. and 180.degree. C. in the presence of a catalytic amount of a dialkyl tin oxide.Type: GrantFiled: March 9, 1987Date of Patent: March 3, 1992Assignee: The Goodyear Tire & Rubber CompanyInventors: Kirkwood S. Cottman, Joseph A. Kuczkowski
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Patent number: 5091558Abstract: Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: ##STR1## wherein: R.sup.1 is alkoxy, alkylthio, optionally substituted phenoxy or optionally substituted phenylthio;R.sup.2 is hydrogen, lower alkyl, optionally substituted phenyl or optionally substituted phenylalkyl;R.sup.3 is lower alkyl, lower alkoxy, or halo and m is 0, 1 or 2, or R.sup.3 is optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy, amino, lower alkylamino, lower dialkylamino, cyano, or S(0).sub.Type: GrantFiled: March 6, 1987Date of Patent: February 25, 1992Assignee: Syntex (U.S.A.) Inc.Inventors: Gordon H. Jones, Michael C. Venuti, John M. Young
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Patent number: 5089657Abstract: Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: ##STR1## wherein:R.sup.1 is lower alkoxy or optionally substituted phenoxy;R.sup.2 is hydrogen, lower alkyl, optionally substituted phenyl or optionally substituted phenyl-lower-alkyl;R.sup.3 is hydrogen, lower alkyl, lower alkoxy, halo, optionally substituted phenyl, optionally substituted phenyl-lower-alkyl or optionally substituted phenyl-lower-alkoxy, and m is 1 or 2;X and Y are different and are selected from the group consisting of hydrogen, R.sup.4 and -C(O)W, whereinW is alkyl of one to seven carbon atoms, optionally substituted phenyl or optionally substituted benzyl; andR.sup.4 is lower alkyl or optionally substituted phenyl-lower-alkyl.Type: GrantFiled: March 11, 1987Date of Patent: February 18, 1992Assignee: Syntex (U.S.A.) Inc.Inventor: Michael C. Venuti
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Patent number: 5079245Abstract: The compounds 2-trifluoromethyl-7-substituted-6,7,8,9-tetrahydro-[5H]-benzocycloheptenes are disclosed and disclosed to be useful in the treatment of metabolic illnesses such as diabetes, obesity, and their complications. A perferred compound is 2-trifluoromethyl-7-amino-6,7,8,9-tetrahydro-[5H-benzocycloheptane.Type: GrantFiled: July 5, 1989Date of Patent: January 7, 1992Assignee: Adir et CompagnieInventors: Michel Wierzbicki, Pierre Hugon, Jacques Duhault, Francoise Lacour
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Patent number: 5073641Abstract: Novel ester derivatives of carboxylic acid medicaments of formula (I), wherein R--COO--represents the acyloxy residue of a carboxylic acid drug or medicament, n is an integrer from 1 to 3, and R.sub.1 and R.sub.2 are the same or different and are selected from a group consisting of an alkyl, an alkenyl, an aryl, an aralkyl, a cycloalkyl and which group may be unsubstituted or substituted, or R.sub.1 and R.sub.2 together with the N forms a 4-, 5-, 6- or 7-membered heterocyclic ring, which in addition to the nitrogen atom may contain one or two further heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur and which heterocyclic group may be substituted. These compounds are highly biolabile prodrug forms of the corresponding carboxylic acid compounds and are highly susceptible to undergoing enzymatic hydrolysis in vivo whereas they are highly stable in aqueous solution.Type: GrantFiled: April 26, 1988Date of Patent: December 17, 1991Inventors: Hans Bundgaard, Niels M. Nielsen
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Patent number: 5066675Abstract: There are described new phenylacetic acid derivatives of general formula I ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 have the meanings given in the description, processes for their preparation and insecticidal and acaricidal compositions containing these compounds.Type: GrantFiled: August 31, 1990Date of Patent: November 19, 1991Assignee: Schering AktiengesellschaftInventors: Ulrich Buhmann, Hartmut Joppien, Dietrich Baumert
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Patent number: 5064863Abstract: Tertiary and secondary amines of the formulas ##STR1## wherein n is the integer 1 or 2, p0 R is hydrogen, lower-alkanoyl or phenyl-lower-alkanoyl,X.sup.1 is phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position,X.sup.2 is lower-alkyl, phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position or phenyl optionally monosubstituted by fluorine, chlorine, trifluoromethyl or lower-alkoxy,Y is hydrogen or methyl, andZ is a phenyl or thienyl residue substituted as hereinafter described,and the physiologically and pharmaceutically compatible salts are described. The compounds of formulas I and V-1 have catabolic activity and can be used for the treatment of obesity and diabetes mellitus or for the treatment of conditions which are associated with an increased protein breakdown, or as feed additives for fattening animals. The compounds of formulas I and V-1 can be prepared starting from corresponding primary amines.Type: GrantFiled: December 10, 1987Date of Patent: November 12, 1991Assignee: Hoffmann-La Roche Inc.Inventors: Leo Alig, Marcel Muller
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Patent number: 5059719Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more C.sub.2 to C.sub.4 vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more soluble basic compounds of one or more elements of the lanthanum series (atomic numbers 57-71, inclusive). The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates. When the process is applied to the preparation of alkylene oxide, particularly ethylene oxide, adducts of alkanols, particularly primary alkanols in the C.sub.6 to C.sub.24 range, the product is a valuable narrow range nonionic surfactant, characterized by relatively narrow distribution of alkylene oxide adducts.Type: GrantFiled: March 23, 1990Date of Patent: October 22, 1991Assignee: Shell Oil CompanyInventor: Charles L. Edwards
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Patent number: 5057627Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more of the phosphate salts of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: February 20, 1990Date of Patent: October 15, 1991Assignee: Shell Oil CompanyInventor: Charles L. Edwards
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Patent number: 5057628Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more compounds of one or more of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: February 20, 1990Date of Patent: October 15, 1991Assignee: Shell Oil CompanyInventors: Charles L. Edwards, Richard A. Kemp
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Patent number: 5051527Abstract: The invention lies in novel ferroelectric liquid crystal compounds particularly represented by the general formulae, having a good responsibility in relation to the applied electric field and a wide range of phase transition points inclusive of the room temperature so as to be useful alone as the liquid crystal material but also to be mixed with other liquid crystal compounds for expanding the phase transition points to a desired range and making the response speed of the liquid crystal composition faster. ##STR1## In the formulae, m and n are same or different with each other and represent an integral of 1-20.Type: GrantFiled: February 28, 1989Date of Patent: September 24, 1991Assignee: Showa Shell Sekiyu K.K.Inventors: Yoshiichi Suzuki, Takashi Hagiwara, Hiroyuki Mogamiya
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Patent number: 5026923Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more of the borate salts of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: May 29, 1990Date of Patent: June 25, 1991Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 5026899Abstract: The invention relates to novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof with herbicidal and plant growth regulating properties.The novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof are of the formula I ##STR1## wherein A is a 2- or 7-membered alkylene bridge, or a 3- to 7-membered alkenylene bridge which may be mono- or polyunsaturated,n is 0, 1 or 2,R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl,R.sub.2 is C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; or is C.sub.3 -C.sub.6 cycloalkyl; or phenyl, benzyl or phenylethyl, the phenyl ring of each of which may be substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, cyano or nitro,X is oxygen or a radical --NOR.sub.3, andR.sub.3 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.Type: GrantFiled: December 13, 1989Date of Patent: June 25, 1991Assignee: Ciba-Geigy CorporationInventor: Hans Tobler
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Patent number: 5025017Abstract: Seco-mevinic acid derivatives are provided which has the structure ##STR1## including all stereoisomers thereof, wherein Z is ##STR2## R is H, alkali metal or lower alkyl, R.sup.1 is H, lower alkyl, aryl, lower alkoxy, cycloalkyl, heteroaryl, aralkyl, heteroaralkyl or heterocyclic; R.sup.2 is lower alkyl, cycloalkyl or aralkyl, and X is O or NR.sup.5 wherein R.sup.5 is H or lower alkyl, and are HMG CoA reductase inhibitors and thus are useful as antihypercholesterolemic agents and in treating atherosclerosis. New intermediates for preparing the above seco-mevinic acid derivatives are also provided.Type: GrantFiled: September 28, 1989Date of Patent: June 18, 1991Assignee: E. R. Squibb & Sons, Inc.Inventor: Donald S. Karanewsky
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Patent number: 5017606Abstract: Fluorobenzyl esters of the formula: ##STR1## wherein X represents the residue of any carboxylic acid of formula X-COOH which forms an insecticidally active ester with a 3-phenoxybenzyl alcohol, and R, R.sup.6 and R.sup.7 are each selected from hydrogen, halogen and alkyl of up to four carbon atoms, provided that at least one of R, R.sup.6 and R.sup.7 represents halogen, and further provided that R and R.sup.6 are not both bromine when R.sup.7 is hydrogen. The compounds are useful for combatting insect and acarine pests.Type: GrantFiled: June 11, 1990Date of Patent: May 21, 1991Assignee: Imperial Chemical Industries PLCInventor: Michael J. Robson
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Patent number: 5015764Abstract: A process for the separation of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process comprises (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base (ii) treating said salt solution with one-half molar equivalent of a chiral organic nitrogenous base having a base strength no stronger than said organic or inorganic base (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt and (iv) separating said precipitated diastereomeric salt.Type: GrantFiled: June 18, 1990Date of Patent: May 14, 1991Assignee: Ethyl CorporationInventors: Thanikavelu Manimaran, Fred J. Impastato
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Patent number: 5004569Abstract: The invention relates to a process for the production of carboxylic acid esters from carboxylic acids and alcohols which is characterized in that neutral phosphites containing oxetane groups are used as esterification catalysts.Type: GrantFiled: December 6, 1988Date of Patent: April 2, 1991Assignee: Bayer AktiengesellschaftInventors: Helmut-Martin Meier, Klaus Kircher, Klaus Berg
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Patent number: 5001148Abstract: Antihypercholesterolemic activity, due to competitive inhibition of HMG CoA reductase, has been found in compounds of the formula ##STR1## wherein: R.sup.1, R.sup.2 and R.sup.3 are independently selected from:(1) alkyl,(2) substituted alkyl in which one or more substituents are selected from(a) halogen,(b) hydroxyl,(c) alkoxy,(d) alkoxycarbonyl,(e) acyloxy,(f) cycloalkyl,(g) phenyl,(h) substituted phenyl in which one or more substituents are X or Y,(i) alkyl-S(O).sub.n,(j) cycloalkyl-S(O).sub.n,(k) phenyl-S(O).sub.n,(l) substituted phenyl-S(O).sub.n in which one or more substituents are X or Y, and(m) oxo,(3) alkoxy,(4) alkenyl,(5) cycloalkyl,(6) substituted cycloalkyl in which one or more substituents are selected from(a) alkyl,(b) substituted alkyl in which one or more substituents are selected from(i) halogen,(ii) hydroxy,(iii) alkoxy,(iv) alkoxycarbonyl(v) acyloxy(vi) phenyl(vii) substituted phenyl in which one or more substituents are X and Y,(viii) alkyl-S(O).sub.n,(ix) cycloalkyl-S(O).sub.Type: GrantFiled: June 7, 1989Date of Patent: March 19, 1991Assignee: E. R. Squibb & Sons, Inc.Inventors: Jeffrey O. Saunders, Eric M. Gordon
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Patent number: 4997978Abstract: Alkyl carboxylates of the formula:R--CO--O--CH.sub.2 R'are prepared by hydrocarbonylating a compound of the formula:R--CO--O--R'in the simultaneous presence, in the reaction medium, of cobalt, ruthenium, an alkyl iodide and an ionic iodide, the atomic ratio Co/Ru being less than or equal to 1, and the total amount of iodine-containing promoters present in the medium being such that I/Ru is greater than or equal to 5.Type: GrantFiled: October 24, 1988Date of Patent: March 5, 1991Assignee: Rhone-Poulenc IndustriesInventors: Jean Gauthier-Lafaye, Robert Perron
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Patent number: 4990658Abstract: A new process for preparing ibuprofen or its alkyl esters is provided. A 1-halo-1-(4-isobutylphenyl)ethane is reacted with carbon monoxide in the presence of water or an alcohol at a temperature between about 10.degree. C. and about 200.degree. C. An excess of several moles of water or alcohol is preferred. An acid such as hydrochloric acid may also be added. As catalyst, a palladium compound and at least one acid-stable ligand are present; however an excess of ligand over palladium is advantageous.Type: GrantFiled: December 18, 1989Date of Patent: February 5, 1991Assignee: Ethyl CorporationInventors: Barbara C. Stahly, Ronny W. Lin, E. E. Atkinson, Jr.
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Patent number: 4985572Abstract: An alcohol and/or a carboxylic acid ester is produced from a carboxylic acid or anhydride thereof by reacting the acid or anhyride with hydrogen at elevated temperature in the presence as catalyst of a composition comprising an alloy of (i) at least one noble metal of Group VIII of the Periodic Table and (ii) at least one metal capable of alloying with the Group VIII noble metal, optionally including a support and at least one of the metals rhenium, tungsten or molybdenum. The process is particularly applicable to the hydrogenation of monobasic acids, for example acetic acid, and the hydrogenation of maleic acid or maleic anhydride to gamma-butyrolactone.Type: GrantFiled: November 21, 1988Date of Patent: January 15, 1991Assignees: The British Petroleum Company, p.l.c., BP Chemicals LimitedInventors: Melanie Kitson, Peter S. Williams
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Patent number: 4983758Abstract: A process for producing an optically active .alpha.-isopropyl-p-chlorophenylacetic acid (ICPA) of the formula: ##STR1## wherein the symbol * stands for an asymmetric carbon atom.Type: GrantFiled: December 2, 1988Date of Patent: January 8, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Yoshiaki Oda, Takaharu Ikeda, Hiroshi Yamachika
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Patent number: 4966915Abstract: An L-dopa derivative represented by formula (I) ##STR1## wherein one of R.sup.1 and R.sup.2 denotes a hydrogen atom and the other denotes a group of formula R--CO-- in which R denotes an alkyl, alkenyl, optionally substituted cycloalkyl, optionally substituted phenyl, optionally substituted aralkyl, lower alkoxy or optionally substituted aralkyloxy group,and its acid addition salt. The compounds are useful in the medical field, especially in the treatment of a series of diseases called Parkinson's disease or Parkinsonism.Type: GrantFiled: September 16, 1988Date of Patent: October 30, 1990Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Yoshimi Tsuchiya, Masahiro Hayashi, Hiroshi Takehana, Akihiro Hisaka, Yoshio Sawasaki, Masaki Ihara
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Patent number: 4965361Abstract: Process is disclosed for the preparation of 4-substituted aryl olefins from 4-substituted aryl iodides. 4-Substituted aryl iodides are contacted with an olefin in an ester solvent in the presence of a catalyst system comprising a palladium compound and a Bronsted base.Type: GrantFiled: February 27, 1989Date of Patent: October 23, 1990Assignee: Eastman Kodak CompanyInventor: Kevin J. Edgar
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Patent number: 4960926Abstract: Process for the carbonylation of olefinically unsaturated compounds with carbon monoxide in the presence of a hydroxyl-group-containing compound, a palladium catalyst, an organic phosphine, an acid with a pKa value <2, with the exception of halogen acids and carboxylic acids as promoter, and a catlayst stabilizer selected from the group consisting of compounds of the general formula; ##STR1## wherein X represents an element of group Va with a valency greater than 3, selected from P. As or Sb, where Y represents an element of group VIa, selected from O, S or Se, and where either a, b and c are 0 or 1, where R.sub.4, R.sub.5 and R.sub.6 are the same or different and represent hydrocarbon groups, or a and b=0 and c=0 or 1 and R.sub.4 and R.sub.5 together with X form a heterocyclic group, or a, b and c=0 and R.sub.4, R.sub.5 R.sub.6 together with X form a heterocyclic group, compounds of the general formula: ##STR2## wherein R.sub.7 is a hydrocarbon group and where R.sub.8 and R.sub.Type: GrantFiled: July 27, 1989Date of Patent: October 2, 1990Assignee: Shell Oil CompanyInventor: Eit Drent