Cyclopentyl Bonded To -coor, -ccoor, Or -cccoor Patents (Class 562/504)
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Patent number: 5099067Abstract: The present invention relates to a method of converting .beta.-nitro compounds, specifically alcohols, into the corresponding hydroxy amines with retention of configuration by the use of ammonium formate.Type: GrantFiled: August 15, 1991Date of Patent: March 24, 1992Assignee: Northwestern UniversityInventors: Anthony G. M. Barrett, Christopher D. Spilling
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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: 5091567Abstract: The instant invention concerns a novel process for the preparation of 1-aminomethyl-1-cyclohexaneacetic acid (gabapentin), a known compound useful for treating certain cerebral diseases such as epilepsy and dizziness.Type: GrantFiled: August 21, 1990Date of Patent: February 25, 1992Assignee: Godecke AktiengesellschaftInventors: Wolfram Geibel, Johannes Hartenstein, Wolfgang Herrmann, Joachim Witzke
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Patent number: 5091113Abstract: R is a straight or branched chain C.sub.4 -C.sub.30 alkyl group, a straight or branched chain C.sub.4 -C.sub.30 alkyl group interrupted by one, two or three oxygen atoms or substituted by one, two or three hydroxy groups, a C.sub.5 -C.sub.12 cycloalkyl group, a C.sub.6 -C.sub.10 aryl group, C.sub.6 -C.sub.10 aryl group substituted by one, two or three C.sub.1 -C.sub.12 alkyl groups, a C.sub.7 -C.sub.13 aralkyl group or a C.sub.7 -C.sub.13 aralkyl group which is substituted by a hydroxyl group;R.sub.1 is H or a straight- or branched chain C.sub.1 -C.sub.4 alkyl group;R.sub.2 is H, a straight or branched chain C.sub.1 -C.sub.4 alkyl group or CO.sub.2 H;R.sub.3 is H, a straight or branched chain C.sub.1 -C.sub.4 alkyl group, --CH.sub.2 CO.sub.2 H or --CH.sub.2 CH.sub.2 CO.sub.2 H;R.sub.4 is H, a straight or branched chain C.sub.1 -C.sub.4 alkyl or CO.sub.2 H;R.sub.5 is H, a straight or branched chain C.sub.1 -C.sub.4 alkyl group, CH.sub.2 CO.sub.2 H or CH.sub.2 CH.sub.2 CO.sub.Type: GrantFiled: July 27, 1990Date of Patent: February 25, 1992Assignee: Ciba-Geigy CorporationInventor: Brian G. Clubley
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Patent number: 5068413Abstract: Processes for the preparation of cyclic amino acid derivatives useful in the treatment of cerebral diseases such as epilepsy are disclosed. Novel intermediates useful in processes are also disclosed.Type: GrantFiled: August 21, 1990Date of Patent: November 26, 1991Assignee: Godecke AktiengesellschaftInventors: Klaus Steiner, Wolfgang Herrmann, Gunter Crone, Charles S. Combs
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Patent number: 5055604Abstract: A process for preparing a prostaglandin derivative by reacting an alkyne with zirconocene chloride hydride to produce a zirconium intermediate which is reacted with an alkyllithium and a first copper reagent selected from R.sup.2 Cu(CN)Li or the mixture CuCN and R.sup.2 Li to produce a higher order cuprate complex intermediate and reacting the higher order cuprate complex intermediate with a cyclopentenone to produce the prostaglandin derivative.Type: GrantFiled: April 17, 1990Date of Patent: October 8, 1991Assignee: G. D. Searle & Co.Inventors: Kevin A. Babiak, James R. Behling, John H. Dygos, John S. Ng
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Patent number: 5037809Abstract: (1R, 2S)-2-Aminocyclopentanecarboxylic acid and its salts useful as antimicrobial agents.Type: GrantFiled: January 26, 1990Date of Patent: August 6, 1991Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Michiyo Miyauchi, Eisaku Tsujii, Masami Ezaki, Seiji Hashimoto, Masakuni Okuhara
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Patent number: 5030654Abstract: A series of novel spiro-substituted glutaramide derivatives have been prepared, including the pharmaceutically acceptable salts thereof and bioprecursors therefor, wherein the spiro-substituent completes a 5- or 6-membered carbocycyclic ring and is located at the carbon atom adjacent to the carbamoyl group. These particular compounds are inhibitors of the neutral endopeptidase E.C.3.4.24.11 enzyme and are therefore useful in therapy as diuretic agents for the treatment of hypertension, heart failure, renal insufficiency and other disorders. Methods for preparing these compounds from known starting materials are provided.Type: GrantFiled: May 19, 1989Date of Patent: July 9, 1991Assignee: Pfizer Inc.Inventors: Ian T. Barnish, John C. Danilewicz, Keith James, Gillian M. R. Samuels, Nicholas K. Terrett, Michael T. Williams, Martin J. Wythes
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Patent number: 4990662Abstract: Catalyst and process are disclosed for the improved preparation of alpha, beta-unsaturated acids. The catalyst comprises a porous silica gel component and a Group IA alkali metal component, which is present in an amount of from 200 to 20,000 parts per million and optionally another component such as tin (IV) oxide, and mixtures thereof. The process comprises reacting formaldehyde and an aliphatic carboxylic acid in the presence of said catalyst while maintaining catalyst activity and selectivity during the process by addition of a source of the alkali metal component.Type: GrantFiled: July 27, 1987Date of Patent: February 5, 1991Assignee: Amoco CorporationInventors: Gary P. Hagen, Ruth A. Montag
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Patent number: 4943659Abstract: Catalyst and process are disclosed for preparation of alpha, beta-unsaturated acids. Catalyst comprises a silica component and a Group IA alkali metal component which is present in an amount of from 200 to 15,000 parts per million, said silica component containing less than about 500 parts per million individually of aluminum, zirconium, titanium, iron and mixtures thereof. Process comprises reacting formaldehyde and a carboxylic acid of the formula RHC.sub.2 COOH wherein R is a member of the class consisting of --H, -alkyl, -aryl, -aralkyl, -cycloalkyl, and -alkylaryl radicals in the presence of said catalyst. Catalyst activity is maintained during process by addition of source of alkali metal component.Type: GrantFiled: December 29, 1986Date of Patent: July 24, 1990Assignee: Amoco CorporationInventor: Gary P. Hagen
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Patent number: 4918226Abstract: A process for converting formic acid esters or transesterification products thereof to carboxylic acids comprising contacting a formic acid ester of the formula (HCOO).sub.n --R where R is aliphatic, cycloaliphatic or aralkyl and n is 1 or 2 with a catalytically effective amount of a soluble iridium salt and an iodide promoter at a temperature of from about 100.degree. C. to about 300.degree. C. in the presence of an organic solvent containing at least one carboxylic acid.Type: GrantFiled: June 22, 1981Date of Patent: April 17, 1990Assignee: Exxon Research and Engineering CompanyInventor: Roy L. Pruett
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Patent number: 4894476Abstract: A novel crystalline form of gabapentin and a novel processes for the small and large scale preparations of the anticonvulsant compound in a highly pure state is disclosed. This novel hydrate is produced by a cost effective process which provides an additional purification stage.Type: GrantFiled: May 2, 1988Date of Patent: January 16, 1990Assignee: Warner-Lambert CompanyInventors: Donald E. Butler, Barbara J. Greenman
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Patent number: 4866205Abstract: New optically active intermediates and processes thereto are provided for use in synthesizing therapeutically active prostaglandins of the formula: ##STR1## wherein R.sup.1 is hydrogen or lower alkyl; from a compound of the formula: ##STR2## wherein R.sup.1 is as above and R.sup.2 is hydrogen or a carboxy blocking group convertible to an acid by hydrolysis.Type: GrantFiled: July 11, 1988Date of Patent: September 12, 1989Assignees: Hoffman-La Roche Inc., Hoffman-La Roche Inc.Inventors: David L. Coffen, George W. Holland, W. Harry Mandeville, Perry Rosen, Frederick Wong
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Patent number: 4822913Abstract: Esters of carboxylic acids of the formula RCH.sub.2 COOR"' and R'CH:C(R")COOR"' are reacted to form a carboxylic acid and an aliphatic alcohol R"'OH wherein R, R', and R" are individually selected from the group consisting of --H, alkyl moieties of from 1 to 18 carbon atoms and aralkyl moieties, cycloalkyl moieties and alkylaryl moieties of 3 to 18 carbon atoms and R"' is an alkyl moiety of 1 to 18 carbon atoms in the presence of an AMS-1B borosilicate crystalline molecular sieve catalyst under reaction conditions.Type: GrantFiled: October 28, 1983Date of Patent: April 18, 1989Assignee: Amoco CorporationInventor: Gary P. Hagen
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Patent number: 4816602Abstract: Process for the production of cycloalkanecarboxylic acids of general Formula I ##STR1## wherein n means the number 1 or 2,R.sub.1 and R.sub.3 are alkyl groups of 1-4 carbon atoms, andR.sub.2 and R.sub.4 symbolize hydrogen atoms or alkyl groups of 1-4 carbon atoms,characterized by reacting a compound of general Formula IIX--CR.sub.1 R.sub.2 --(CH.sub.2).sub.n --CH.sub.2 --CR.sub.3 R.sub.4 --X'(II),whereinn, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 have the meanings given above andX and X' mean a hydroxy group, a chlorine atom, a bromine atom, an alkylsulfonyloxy residue, or an arylsulfonyloxy residue,with 1,1-dichloroethylene;splitting off hydrogen chloride from the thus-obtained compounds of general Formula IIIX--CR.sub.1 R.sub.2 --(CH.sub.2).sub.n --CH.sub.2 --CR.sub.3 R.sub.4 --CH.sub.2 --CCl.sub.2 X (III),wherein n, X, X', R.sub.1, R.sub.2, R.sub.3 and R.sub.4 have the meanings given above; and cyclizing and hydrolyzing, by means of acids, the thus-prepared compounds of general Formula IVX--CR.sub.1 R.sub.Type: GrantFiled: May 26, 1987Date of Patent: March 28, 1989Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Herbert Mayr, Werner Heilmann, Helmut Vorbrueggen
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4-hydroxy-2-cyclopentenone, process for production thereof, pharmaceutical composition comprising it
Patent number: 4711895Abstract: A 4-hydroxy-2-cyclopentenone represented by the following formula (I) ##STR1## wherein X represents a hydrogen or halogen atom, A represents a hydrogen atom and B represents a hydroxyl group, or A and B are bonded to each other to represent a bond, R.sup.1 represents a substituted or unsubstituted alkyl, alkenyl or alkynyl group having 1 to 10 carbon atoms, R.sup.2 represents a substituted or unsubstituted alkyl, alkenyl or alkynyl group having 1 to 10 carbon atoms, and R.sup.3 represents a hydrogen atom or a protective group for a hydroxyl group, provided that R.sup.2 is not a 2-octenyl, 8-acetoxy-2-octenyl or 2,5-octadienyl group. The compounds of formula (I) in which A is hydrogen and B is hydroxyl group are prepared by subjecting a 5-unsubstituted cyclopentenone and an aldehyde to aldol condensation reaction. The compounds of formula (I) in which A and B form a bond is prepared by subjecting the compounds of the formula (I) in which A is hydrogen and B is hydroxyl group to dehydration.Type: GrantFiled: October 22, 1985Date of Patent: December 8, 1987Assignee: Teijin LimitedInventors: Atsuo Hazato, Satsohi Sugiura, Seizi Kurozumi, Ryoji Noyori -
Patent number: 4703127Abstract: Compounds of the general formula I are disclosed as useful intermediates in the preparation of prostanoids: ##STR1## wherein A represents O or H, OR.sup.z ;R.sup.z represents hydrogen or a protecting group;R.sup.x represents hydrogen or a protecting group; andR.sup.y represents halogen, a substituted thio group, di-substituted amino group, or a group of the formula R.sup.2, and R.sup.2 represents a straight- or branched-chain alkyl alkenyl or alkynyl group which may optionally be substituted by one or more carboxyl, carboxylic acid ester, or free or protected hydroxyl, thiol, aldehyde or keto groups;with the provisos that R.sup.x is not hydrogen when A is O and R.sup.y is R.sup.2 ; and that when A is H, OR.sup.z R.sup.y and R.sup.2 and R.sup.x and R.sup.z are not both hydrogen.Processes for the preparation of these compounds and of 2-substituted 4-hydroxy-cyclopent-2-en-1-one derivatives are also disclosed.Type: GrantFiled: September 2, 1983Date of Patent: October 27, 1987Assignee: The Australian National UniversityInventors: Rodney W. Rickards, Melvyn Gill, Robert M. Christie
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Patent number: 4701553Abstract: Unsaturated cyclic keto acid may be prepared by cyclizing alken-2-yl dicarboxylic acid anhydride with Lewis acid catalyst in anhydrous Friedel-Craft solvent. Amides of these unsaturated cyclic keto acids useful as friction improvers in lubricating oils, may be prepared by reaction of an amine such as ethanolamine with an unsaturated cyclic keto acid.Type: GrantFiled: January 28, 1983Date of Patent: October 20, 1987Assignee: Texaco Inc., WhiteInventor: Justin C. Powell
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Patent number: 4614816Abstract: A carboxylic acid or an ester thereof having at least two carbon atoms more than formic acid is prepared by reacting at elevated temperature e.g. 100.degree. to 250.degree. C. formic acid or a formate ester with an olefin e.g. ethylene in the presence of, as catalyst, a Group VIII noble metal e.g. iridium, preferably promoted by iodide, to cause addition of the formic acid or ester to the olefin and form the a higher acid e.g. propionic acid or ester thereof.A strong acid such as a sulphonic acid may be used as a copromoter. The catalyst is employed in solution.Type: GrantFiled: October 13, 1983Date of Patent: September 30, 1986Assignee: BP Chemicals LimitedInventors: David J. Drury, Peter S. Williams
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Patent number: 4570014Abstract: Novel plant growth regulant composition comprising as an active ingredient at least one cycloalkanecarboxylic acid compound of the formula ##STR1## in which R is hydroxyl, alkoxy, aralkoxy, amino, alkylamino, dialkylamino or the radicalO.sup..crclbar. M.sup..sym.whereinM.sup..sym. is one alkali metal ion equivalent or alkaline earth metal ion equivalent, or an ammonium, alkylammonium, dialkylammonium, trialkylammonium or tetraalkylammonium ion,R.sup.1 is amino or the radical ##STR2## wherein R.sup.2 is hydrogen, alkyl or aryl, orR.sup.1 is the radical --N.sup..sym. H.sub.3 X.sup..crclbar.,wherein X.sup.63 is chloride, bromide or iodide, and n is 1, 2, 3, 4 or 5,in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.Type: GrantFiled: December 15, 1981Date of Patent: February 11, 1986Assignee: Bayer AktiengesellschaftInventors: Rolf Schroder, Klaus Lurssen
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Patent number: 4568762Abstract: New optically active intermediates and processes for producing optically active prostaglandins which are useful for various therapeutic purposes such as antisecretory agents, cardiovascular agents, antiulcerogenic agents and as agents for inducing labor or terminating pregnancy in pregnant females.Type: GrantFiled: October 9, 1984Date of Patent: February 4, 1986Assignee: Hoffmann-La Roche Inc.Inventor: Percy Manchand
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Patent number: 4536594Abstract: A process for the preparation of beta-disubstituted monocarboxylic acids derived from tertiary acyclic, monocyclic or bicyclic hydrocarbons. The process consists in reacting said hydrocarbons with vinylidene chloride and either a functional compound where the molecule includes a tertiary carbon atom bonded to the heteroatom of a functional group such as a tertiary alcohol, an ether, or a tertiary halide or an alkene, in the presence of a concentrated protonic acid. The reaction can be carried out in the presence of a catalyst of the Lewis acid type and particularly BF.sub.3. These acids are useful as synthesis intermediates and as additives for oils and lubricants.Type: GrantFiled: October 7, 1983Date of Patent: August 20, 1985Assignee: Elf FranceInventors: Patrice P. M. Deschamps, Roger Gallo, Henri Grangette
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Patent number: 4510321Abstract: Processes for the autoxidative cleavage of selected ketones such as C.sub.4 -C.sub.10 cycloalkanones having at least one hydrogen or at least one R group on a carbon alpha to the carbonyl carbon or aryl alkyl ketones having the formula III ##STR1## comprising contacting a liquid phase comprising said ketone with elemental oxygen gas, preferably air, in the presence of a pulverized alkali metal hydroxide at a temperature of no more than 50.degree. C. for a time sufficient to produce an oxidized product are disclosed. Preferred cycloalkanones, 2-alkyl- and 2-arylcyclohexanone are autoxidized in pulverized sodium hydroxide/dimethoxyethane to produce 6-alkyl- or 6-aryl-6-oxohexanoic acids, respectively.Type: GrantFiled: January 31, 1983Date of Patent: April 9, 1985Assignee: Allied CorporationInventors: Divakaran Masilamani, Edward H. Manahan
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Patent number: 4501687Abstract: Novel cyclopentanols of the formula ##STR1## wherein R.sub.1 and R.sub.2 are identical and are selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R.sub.3 is selected from the group consisting of --OH, alkoxy of 1 to 8 carbon atoms and acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms, R.sub.4 is selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms, R.sub.5 and R.sub.8 are individually selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and alkenyl and alkynyl of 2 to 8 carbon atoms and R.sub.6 and R.sub.7 are individually selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, --CN, --COCH.sub.3 and --COOAlK.sub.2 and AlK.sub.2 is alkyl of 1 to 8 carbon atoms useful as perfumery agents and their preparation and novel intermediates.Type: GrantFiled: November 30, 1981Date of Patent: February 26, 1985Assignee: Roussel UclafInventors: Jacques Martel, Jean Buendia, Francois Nezot
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Patent number: 4492799Abstract: Novel halo-4-alkenoic acid compounds which are useful intermediates for the synthesis of insecticides and miticides.Type: GrantFiled: July 2, 1979Date of Patent: January 8, 1985Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4487953Abstract: Compounds of Formula (I) ##STR1## wherein the 9-bromine atom can be in the .alpha.- or .beta.-position,R.sub.1 is CH.sub.2 OH or C(O)OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is C(O)NHR.sub.3 wherein R.sub.3 is an acid residue or R.sub.2 ; andA is --CH.sub.2 --CH.sub.2 -- or cis --CH.dbd.CH--;B is --CH.sub.2 --CH.sub.2 --, trans --CH.dbd.CH--, or --C.tbd.C--;W is a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position; D and E together are a direct bond; orD is straight-chain, branched, or cyclic alkylene of 1-10 carbon atoms, optionally substituted by fluorine atoms; andE is oxygen, sulfur, a direct bond --C.tbd.C--, or --CR.sub.6 .dbd.CR.sub.7 --, wherein R.sub.6 and R.sub.7 are different from each other and each is hydrogen, chlorine, or C.sub.1 -C.sub.4 -alkyl;R.sub.4 is a free or functionally modified hydroxy group;R.sub.Type: GrantFiled: December 6, 1982Date of Patent: December 11, 1984Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger
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Patent number: 4482572Abstract: 1-Acylamino-1-cyclopentanecarboxylic acids have been prepared by acylation of certain 1-amino-1-cyclopentanecarboxylic acids and found to have renal vasodilating and diuretic properties.Type: GrantFiled: May 5, 1983Date of Patent: November 13, 1984Assignee: SmithKline Beckman CorporationInventors: David L. Ladd, Joseph Weinstock
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Patent number: 4454339Abstract: 9-Fluoroprostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is the residue ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 and A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C,W is a free or functionally modified hydroxymethylene group wherein the OH-group can be in the .alpha.- or .beta.-position,D and E jointly are a direct bond orD is straight-chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen or sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine, or alkyl,R.sub.4 is a free or functionally modified hydroxy group, andR.sub.5 is hydrogen, an optionally substituted aliphatic group, e.g.Type: GrantFiled: July 6, 1982Date of Patent: June 12, 1984Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
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Patent number: 4431835Abstract: Alkyl carboxylates are hydrocarbonylated and/or carbonylated with carbon monoxide and hydrogen, in an aqueous medium, and in the presence of a catalytically effective amount of a catalyst system comprising (i) ruthenium, (ii) cobalt, (iii) at least one iodine-containing promoter, and (iv) chromium. The subject hydrocarbonylation/carbonylation is admirably well suited, e.g., for the preparation of acetaldehyde, ethanol, ethyl acetate and acetic acid, especially from a methyl carboxylate.Type: GrantFiled: July 6, 1981Date of Patent: February 14, 1984Assignee: Rhone-Poulenc IndustriesInventors: Jean Gauthier-Lafaye, Robert Perron
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Patent number: 4430507Abstract: New optically active intermediates and processes for producing optically active prostaglandins which are useful for various therapeutic purposes such as antisecretory agents, cardiovascular agents, antiulcerogenic agents and as agents for inducing labor or terminating pregnancy in pregnant females.Type: GrantFiled: March 11, 1983Date of Patent: February 7, 1984Assignee: Hoffmann-La Roche Inc.Inventor: Percy Manchand
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Patent number: 4430506Abstract: Alkyl carboxylates are hydrocarbonylated and/or carbonylated with carbon monoxide and hydrogen, in an aqueous medium, and in the presence of a catalytically effective amount of a catalyst system comprising (i) ruthenium, (ii) cobalt, (iii) at least one iodine-containing promoter, and (iv) vanadium. The subject hydrocarbonylation/carbonylation is admirably well suited, e.g., for the preparation of acetaldehyde, ethanol, ethyl acetate and acetic acid, especially from a methyl carboxylate.Type: GrantFiled: July 6, 1981Date of Patent: February 7, 1984Assignee: Rhone-Poulenc IndustriesInventors: Jean Gauthier-Lafaye, Robert Perron
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Patent number: 4390724Abstract: Novel 3-formyl-4-methyl-pentanoic acid derivatives of the formula ##STR1## wherein Y is an aromatic group, R.sub.2 and R.sub.3 are individually alkyl of 1 to 4 carbon atoms or taken together with the carbon atom to which they are attached form a carbon homocycle of 3 to 6 carbon atoms, the Rs are alkyl of 1 to 6 carbon atoms or together form a polymethylene of 2 to 3 carbon atoms and Z' is selected from the group consisting of --COOH and Z and Z is selected from the group consisting of cyano and --COOR.sub.1 wherein R.sub.1 is alkyl of 1 to 6 carbon atoms and their preparation which are useful for the preparation of 3-formyl-4-R.sub.2 R.sub.3 -but-3-ene-1-oic acid which is an intermediate for the preparation of a compound of the formula ##STR2## wherein R.sub.4 is hydrogen or the remainder of an alcohol of the formula R.sub.1 OH by the process of copending, commonly assigned U.S. patent application Ser. No. 153,338 filed May 27, 1980.Type: GrantFiled: April 16, 1982Date of Patent: June 28, 1983Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
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Patent number: 4390718Abstract: New optically active intermediates and processes for producing optically active prostaglandins which are useful for various therapeutic purposes such as antisecretory agents, cardiovascular agents, antiulcerogenic agents and as agents for inducing labor or terminating pregnancy in pregnant females.Type: GrantFiled: July 1, 1981Date of Patent: June 28, 1983Assignee: Hoffmann-La Roche Inc.Inventor: Percy Manchand
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Patent number: 4386103Abstract: Dichloroamino acid derivatives other than .alpha.-dichloroamino acids are prepared from chlorination of corresponding amino acids, and are found to be potent germicidal and fungicidal agents.Type: GrantFiled: January 30, 1981Date of Patent: May 31, 1983Assignee: Merck & Co., Inc.Inventors: Stefano A. Pogany, Takeru Higuchi
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Patent number: 4371706Abstract: Alkali metal aminoalkanoate is prepared by contacting in the presence of an alkali metal carboxylate a reaction mixture in which there is at least one alkali metal hydroxide, at least one lactam, and water. Arylene sulfide polymer is prepared by contacting at polymerization conditions a reaction mixture that contains at least one alkali metal aminoalkanoate prepared as described above; at least one polyhalo-substituted aromatic compound; at least one organic amide as solvent and H.sub.2 S. In an embodiment of the polymerization the organic amide used as solvent can be the same as the lactam from which the alkali metal aminoalkanoate was produced.Type: GrantFiled: October 22, 1981Date of Patent: February 1, 1983Assignee: Phillips Petroleum CompanyInventors: James T. Edmonds, Jr., Lacey E. Scoggins
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Patent number: 4367340Abstract: Compounds of the general formula I are disclosed as useful intermediates in the preparation of prostanoids: ##STR1## wherein A represents O or H, OR.sub.z ;R.sup.z represents hydrogen or a protecting group;R.sup.x represents hydrogen or a protecting group; andR.sup.y represents halogen, a substituted thio group, di-substituted amino group, or a group of the formula R.sup.2, and R.sup.2 represents a straight-or branched-chain alkyl alkenyl or alkynyl group which may optionally be substituted by one or more carboxyl, carboxylic acid ester, or free or protected hydroxyl, thiol, aldehyde or keto groups;with the provisos that R.sup.x is not hydrogen when A is O and R.sup.y is R.sup.2 ; and that when A is H, OR.sup.z R.sup.y is R.sup.2 and R.sup.x and R.sup.z are not both hydrogen.Processes for the preparation of these compounds and of 2-substituted 4-hydroxy-cyclopent-2-en-1-one derivatives are also disclosed.Type: GrantFiled: March 4, 1981Date of Patent: January 4, 1983Assignee: The Australian National UniversityInventors: Rodney W. Rickards, Melvyn Gill, Robert M. Christie
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Patent number: 4347379Abstract: Numerous alpha-carboxylic acids are prepared in a liquid medium by the reaction of an organic compound having at least one reactive hydroxyl or thiol group, with a monoketone, and a haloform, in the presence of a phase transfer catalyst and an alkali metal hydroxide. The term "alpha-alkoxycarboxylic acids" includes alpha-phenoxycarboxylic acids, alpha-thioalkoxycarboxylic acids and alpha-thiophenoxycarboxylic acids. Specific substituents on the beta carbon atom of an alpha-alkoxycarboxylic (or "2-alkoxycarboxylic") acid reaction product formed in this novel synthesis, are introduced by appropriate choice of the ketone reactant; alkoxy and phenoxy substituents on the alpha carbon atom of a 2-alkoxycarboxylic acid are introduced by appropriate choice of the organic compound having a hydroxyl or thiol group. De-alkoxylation of the 2-alkoxycarboxylic acid yields alpha-beta monoolefinically unsaturated carboxylic acids which are necessarily alpha substituted, and may also be beta-substituted.Type: GrantFiled: March 10, 1980Date of Patent: August 31, 1982Assignee: The B. F. Goodrich CompanyInventor: John T. Lai
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Patent number: 4331608Abstract: Unsaturated compounds having at least 4 carbon atoms, including unsaturated alicyclic compounds having at least 4 carbon atoms, unsaturated aliphatic compounds having at least one carbon-carbon unsaturated bond and having at least 4 carbon atoms and unsaturated aromatic compounds having at least one carbon-carbon unsaturated bond in the branched chain thereof and (ii) aldehydes or ketones having at least 4 carbon atoms are catalytically co-oxidized with an oxygen-containing gas in a liquid phase to form a cleaveged product or products of unsaturated bond of the unsaturated compounds at a high yield. This co-oxidation reaction is carried out in the presence of a heavy metal containing iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, copper, silver, chromium, molybdenum, tungsten, manganese and rhenium and the compounds thereof.Type: GrantFiled: June 2, 1980Date of Patent: May 25, 1982Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Keiji Kawamoto, Toshihiro Yoshioka
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Patent number: 4324730Abstract: Prostaglandin and prostacyclin compounds which are fluorine substituted in any one or more of the following positions, 4,4; 7,7; 10,10; and 5.Type: GrantFiled: October 8, 1980Date of Patent: April 13, 1982Assignee: The University of ChicagoInventor: Josef Fried
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Patent number: 4322550Abstract: Various mercaptoalkanoic acids are recovered from an aqueous medium or water in which they are contained by a liquid-liquid solvent extraction operation employing at least one of an alkanoic acid ester and an alkylene glycol ether. In one embodiment, thioglycolic acid has been extracted with ethyl acetate. In another embodiment, it has been recovered with ethylene glycol monoethyl ether acetate. In a further embodiment, it has been recovered with diethylene glycol diethyl ether.Type: GrantFiled: October 3, 1980Date of Patent: March 30, 1982Assignee: Phillips Petroleum CompanyInventor: James B. Kimble
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Patent number: 4318855Abstract: The instant invention provides a new and improved method of preparing .alpha.-hydroxycarbonyl compounds, particulary substituted cyclopent-2-en-2-ol-1-ones and substituted 3-hydroxy-2(5H)-furanones. The novel sequence involves a number of novel intermediates including substituted 2-cyanocyclopentanones, substituted 2-cyano-2-hydroxycyclopentanones, and 2-cyano-2-hydroxyvalero-.gamma.-lactones.Type: GrantFiled: January 24, 1980Date of Patent: March 9, 1982Assignee: Givaudan CorporationInventors: Ulrich Huber, Hans-Jakob Wild
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Patent number: 4315031Abstract: This invention relates to thiosubstituted cyclic amino acids, to a process for their preparation and to pharmaceutical compositions containing them together with an inert non toxic pharmaceutical carrier.Type: GrantFiled: August 28, 1978Date of Patent: February 9, 1982Assignee: Science Union et CieInventors: Michel Vincent, Georges Remond, Jacques Bure
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Patent number: 4265819Abstract: A process for the preparation of a dihalogenovinylcyclopropanecarboxylic acid or an ester thereof, of the formula ##STR1## in which Hal each independently is fluorine, chlorine or bromine,R.sup.1 and R.sup.2 each independently is hydrogen or C.sub.1-4 -alkyl, or R.sup.1 and R.sup.2 together with the adjacent carbon atom form a cycloaliphatic ring with up to 7 carbon atoms, andR.sup.3 is hydrogen, C.sub.1-4 -alkyl or optionally substituted arylmethyl or hetero-arylmethyl,which comprises reacting a 3-chloro-2-(2',2'-dihalovinyl)propanecarboxylic acid ester of the formula ##STR2## in which R.sup.4 is C.sub.1-4 -alkyl or optionally substituted arylmethyl or hetero-arylmethyl,with a base. The propane carboxylic acid esters are new and may be formed in situ by reacting a 3-(2',2'-dihalovinyl)-.gamma.-butyrolactone of the formula ##STR3## with a chlorinating agent and then with an alcohol of the formula R.sup.4 --OH.Type: GrantFiled: September 13, 1979Date of Patent: May 5, 1981Assignee: Bayer AktiengesellschaftInventor: Reinhard Lantzsch
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Patent number: 4264623Abstract: Novel .beta.-lactones of 2-hydroxy-cyclopentane-carboxylic acids of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen and methyl and R.sub.2 is selected from the group consisting of --CH.sub.2 --O--CH.sub.2 --CH.sub.3 and --X--Ar, X is selected from the group consisting of --O-- and --CH.sub.2 --, Ar is an optionally substituted member selected from the group consisting of thienyl, thiazolyl, phenyl and thiadiazolyl, the optional substituents being at least one member selected from the group consisting of halogen and --CF.sub.3 and thw wavy lines indicate that the groups may be in the .alpha., .beta. or .beta., .alpha.-positions or mixtures thereof having hypotensive activity and their preparation.Type: GrantFiled: November 16, 1979Date of Patent: April 28, 1981Assignee: Roussel UclafInventors: Jean Buendia, Michel Vivat, Laurent Taliani
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Patent number: 4233454Abstract: The disclosure relates to a novel sequence of reactions for manufacturing known prostaglandin intermediates, and to novel chemical intermediates obtained in the course of the novel reaction sequence, for example methyl 5.beta.-chloro-2.beta.-dimethoxymethyl-3.alpha.-hydroxycyclopent-1.alpha.- ylacetate.Type: GrantFiled: September 10, 1979Date of Patent: November 11, 1980Assignee: Imperial Chemical Industries LimitedInventor: Keith B. Mallion
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Patent number: 4221809Abstract: Novel lactones of the formula ##STR1## wherein the dotted line indicates the optional presence of a second bond, A is a single bond or --CH.sub.2 --CH.sub.2 --, R is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and alkenyl and alkynyl of 2 to 4 carbon atoms, R.sub.6 is --OR'.sub.A, R'.sub.A is selected from the group consisting of hydrogen, tetrahydropyranyl, alkyl of 1 to 3 carbon atoms and ##STR2## R".sub.A is selected from the group consisting of alkyl of 1 to 3 carbon atoms optionally substituted with carboxyl and phenyl optionally substituted with a member of the group consisting of carboxyl, free hydroxyl, hydroxyl protected with an acyl of 2 to 4 carbon atoms and hydroxyl protected with an easily hydrolyzable group and R and R.sub.6 together form a keto group, R.sub.7 is --(CH.sub.2)m.sub.A --CH.sub.3, m.sub.A is 3,4,5 or 6 and R.sub.6 and R.sub.7 taken together form .dbd. CH--(CH.sub.2)n.sub. A --CH.sub.3 n.sub.Type: GrantFiled: May 8, 1979Date of Patent: September 9, 1980Assignee: Roussel UclafInventors: Jean Buendia, Michel Vivat
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Patent number: 4206137Abstract: Thioalkanoylalkanoic acid compounds and salts thereof having the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each is hydrogen or lower alkyl;R.sub.5 is hydrogen, lower alkanoyl, benzoyl or ##STR2## A and B each is hydrogen or join together as a polymethylene chain --(CH.sub.2).sub.n -- to complete a 4-, 5- or 6- membered cycloalkyl group, and m is 0 or 1,are angiotensin converting enzyme inhibitors and are useful as hypotensive agents.Type: GrantFiled: November 20, 1978Date of Patent: June 3, 1980Assignee: E. R. Squibb & Sons, Inc.Inventors: Michael E. Condon, Miguel A. Ondetti
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Patent number: 4202822Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.Type: GrantFiled: December 8, 1977Date of Patent: May 13, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4172954Abstract: Organic compounds having a substituent represented by the formula ##STR1## wherein M is alkali metal or ammonium are useful complexing agents for metal and/or alkaline earth metal ions.Type: GrantFiled: September 2, 1977Date of Patent: October 30, 1979Assignee: Monsanto CompanyInventor: Kent P. Lannert
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Patent number: 4172839Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.2 series.Type: GrantFiled: December 8, 1977Date of Patent: October 30, 1979Assignee: American Cyanamid CompanyInventor: Allan Wissner