Cyclopentyl-coor, -c-coor Or -c-c-coor Patents (Class 560/122)
-
Patent number: 4291057Abstract: Novel esters of halo-4-alkenoic acid compounds having pesticidal activity and methods of their preparation.Type: GrantFiled: July 2, 1979Date of Patent: September 22, 1981Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
-
Patent number: 4291061Abstract: 2,3-Dichloro-7-hydroxy-1H-inden-1-one derivatives of the formula I ##STR1## wherein R.sub.1 is hydrogen or one of the groups ##STR2## R.sub.2 and R.sub.3 independently of one another are each hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl or nitro,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.4 -alkenyl, each of which is unsubstituted or substituted by halogen, or R.sub.4 is phenyl which is unsubstituted or is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, trifluoromethyl, cyano or nitro, or it is a C.sub.3 -C.sub.6 -cycloalkyl group, andR.sub.5 is C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.2 -C.sub.4 -alkenyl.These compounds exhibit a microbicidal action against in particular phytopathogenic fungi and bacteria.Type: GrantFiled: October 31, 1979Date of Patent: September 22, 1981Assignee: Ciba-Geigy CorporationInventors: Elmar Sturm, Robert Nyfeler
-
Patent number: 4289896Abstract: Phosphonic acids are suitable catalysts for the transesterification of alkyl esters of carboxylic acids with aliphatic or cycloaliphatic diols containing more than 3 carbon atoms.Type: GrantFiled: September 17, 1979Date of Patent: September 15, 1981Assignee: Ciba-Geigy CorporationInventor: Lothar Buxbaum
-
Patent number: 4287100Abstract: Esters of 1,2,3,6-tetrahydrobenzyl alcohol have been found to exhibit powerful odorous notes such as floral, woody and fruity notes, rendering such compounds valuable as fragrance materials either alone or in compositions. These 1,2,3,6-tetrahydrobenzyl alcohol esters are prepared by reacting 1,2,3,6-tetrahydrobenzyl alcohol with an appropriate organic acid.Type: GrantFiled: March 14, 1978Date of Patent: September 1, 1981Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Kurt Kulka, Teodosij Zazula, John M. Yurecko, Jr.
-
Patent number: 4283414Abstract: The invention concerns novel pesticidal esters of the pyrethrin or pyrethroid type in which the methylene group bonded to the ester carbonyl and/or ester oxygen bears a fluorine substituent. The compounds of the invention are active against insect pests including flies, moths, aphids and beetles and acarina pests including ticks.Type: GrantFiled: June 8, 1979Date of Patent: August 11, 1981Assignee: ICI Australia LimitedInventors: Donald W. G. Harney, Peter G. Lehman, Joseph C. Rundle
-
Patent number: 4283553Abstract: Disclosed are novel hydroperoxide derivatives of hydroxyethylated compounds of the general formula: ##STR1## a-whole number 10 to 30, b, c are absent, R=n-alkyl from C.sub.8 to C.sub.20, secondary alkyl of C.sub.14, C.sub.15 and ##STR2## where R.sub.2 =n-alkyl from C.sub.8 to C.sub.12 ##STR3## where R.sub.3 and R.sub.4 =R.sub.8 --C.dbd.O, where R.sub.8 =--CH.sub.3 or H, if R.sub.6,7,9 =H R.sub.5 is absent or ##STR4## where R.sub.9 =--CH.sub.3 or H, if R.sub.6,7,8 =H, R.sub.5 is absent; R.sub.10 =n-alkyl of C.sub.1 to C.sub.9 of R.sub.3 .noteq.R.sub.4 R.sub.5 =--CH.sub.2 if R.sub.6,7,8,9 =H; if R.sub.5 is absent, R.sub.1 is acyclic and is ##STR5## R.sub.6 =--CH.sub.3 or H, if R.sub.7,8,9 =H, R.sub.5 is absent, R.sub.7 =--CH.sub.3 or H, if R.sub.6,8,9 =H, R.sub.5 is absent, with x=--O--, b-whole number of 8 to 24, (a+c)-whole number of 6 to 30R=R.sub.Type: GrantFiled: September 24, 1979Date of Patent: August 11, 1981Inventors: Sergei S. Ivanchev, Anatoly A. Syrov, Valery N. Pavljuchenko, Ninel N. Lesnikova, Diana A. Rozhkova
-
Patent number: 4280934Abstract: Cyclopentane derivatives useful as odor-modifying ingredients for manufacturing perfumes and perfumed products and perfume compositions containing same.Type: GrantFiled: February 17, 1979Date of Patent: July 28, 1981Assignee: Firmenich SAInventor: Karl-Heinrich Schulte-Elte
-
Patent number: 4276225Abstract: A carboxylic acid ester activated in .alpha.-position by a keto, ester or nitrile group, i.e. of the formula ##STR1## where X is COOR.sup.4, COR.sup.5 or CN, and the several R's can have various meanings but only R.sup.1 and R.sup.2 can be hydrogen, is decarbalkoxylated by heating in the presence of a salt, e.g. sodium chloride, and a phosphorus-containing solvent such as a phospholine oxide, phospholane oxide or phosphetane oxide of the formulas ##STR2## wherein a-k and R can have varied definitions. Water is present either at the outset or end of the reaction before product separation. The reaction proceeds smoothly and in good yields.Type: GrantFiled: August 8, 1977Date of Patent: June 30, 1981Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Hellmut Hoffmann
-
Patent number: 4275219Abstract: The invention relates to a novel process and novel intermediates useful in the preparation of sympathomimetic amines. The pharmacologically useful final products, which are acyl derivatives of mono- and dihydroxy aromatic amines (e.g., catechol amines) can be prepared in optically active or racemic form by reacting the corresponding mono- or dihydroxy aromatic amine with a reagent capable of forming the N-tert-butoxycarbonyl derivative thereof; reacting the novel intermediate thus obtained with an acyloxymethyl chloride to afford the corresponding novel mono- or diacylated N-protected aromatic amine; and removing the N-protecting group therefrom.Type: GrantFiled: September 24, 1979Date of Patent: June 23, 1981Assignee: INTERx Research CorporationInventor: Jacob A. Zupan
-
Patent number: 4270015Abstract: This invention concerns a two-step process for the preparation of ethylene from mixture of carbon monoxide and hydrogen (commonly known as synthesis gas) by reaction of said carbon monoxide/hydrogen mixtures with a carboxylic acid in the presence of one or more ruthenium catalyst complexes to form an ethyl ester of said carboxylic acid coreactant, followed by pyrolysis of said ethyl ester intermediate to ethylene.Type: GrantFiled: July 14, 1980Date of Patent: May 26, 1981Assignee: Texaco Inc.Inventor: John F. Knifton
-
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
-
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
-
Patent number: 4260830Abstract: A process described for the preparation of methyl dihydrojasmonate and lower alkyl homologues according to one of the reaction sequences: ##STR1## The first of the above reaction schemes also incorporates the novel process step: ##STR2## In the above reaction sequence, X is chloro or bromo and R is C.sub.1 -C.sub.4 alkyl.Type: GrantFiled: January 18, 1980Date of Patent: April 7, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Richard A. Wilson, Braja D. Mookherjee, John B. Hall, Gilbert Stork
-
Patent number: 4260512Abstract: Described is the use of Nor-Methyl Jasmonate having the structure: ##STR1## in augmenting or enhancing the aroma of a solid or liquid anionic, cationic, nonionic or zwitterionic detergent comprising the step of adding to a solid or liquid anionic, cationic, nonionic or zwitterionic detergent base from 0.01% up to 0.9% by weight of Nor-Methyl Jasmonate.Type: GrantFiled: June 5, 1980Date of Patent: April 7, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Braja D. Mookherjee, Richard A. Wilson, Frederick L. Schmitt, Manfred H. Vock
-
Patent number: 4259350Abstract: Iodopropargyl derivatives of formula:IC.tbd.CCH.sub.2 OR[wherein R represents an alkanoyl group (which may be unsubstituted or have one or more halogen, cyano, substituted or unsubstituted .alpha.Type: GrantFiled: March 13, 1979Date of Patent: March 31, 1981Assignee: Sankyo Company LimitedInventors: Yasuhiro Morisawa, Kiyoshi Konishi, Mitsuru Kataoka
-
Patent number: 4256745Abstract: Prostan-1-ol esters and intermediates for their preparation are described; the former compounds exhibit improved organ specificity and a longer duration of activity at lower dosages than the corresponding non-esterified prostaglandins and are useful, inter alia, in triggering abortion, inducing labor and regulating the menstrual cycle.Type: GrantFiled: March 2, 1978Date of Patent: March 17, 1981Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Eckehard Schillinger
-
Patent number: 4237308Abstract: A process for preparing 2-cyclopentenone derivative represented by the formula ##STR1## wherein A is ##STR2## and R.sub.2 is lower straight-chain or branched-chain alkyl, alkenyl or aralkyl, and perfume composition containing the derivative.Type: GrantFiled: June 8, 1978Date of Patent: December 2, 1980Assignee: Otsuka Kagaku Yakuhin Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Yuichi Kobayashi
-
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
-
Patent number: 4232169Abstract: An operationally simple and economical process for preparing alpha-oxoesters is provided by reacting an acetylenic compound of formulaR--C.tbd.C--OR'with an oxidizing mixture composed of osmium tetroxide and an alkaline or alkaline earth chlorate and recovering the osmium tetroxide at the end of the reaction.Type: GrantFiled: April 24, 1979Date of Patent: November 4, 1980Assignee: Snamprogetti S.p.A.Inventors: Luciano Re, Alberto Brandt, Luciano Bassignani
-
Patent number: 4227015Abstract: Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester. The intermediate iodides are prepared by condensing a methyl cyclopropyl ketone with an aromatic aldehyde to give an arylvinyl cyclopropyl ketone, reducing the latter to an arylethyl cyclopropyl carbinol or arylvinyl cyclopropyl carbinol, treating the carbinol with phosphorus tribromide and then with zinc bromide to give an arylalkyl or arylalkenyl bromide, and then replacing the bromine atom by iodine.Type: GrantFiled: February 14, 1979Date of Patent: October 7, 1980Assignee: Sterling Drug Inc.Inventor: Joseph C. Collins
-
Patent number: 4225726Abstract: This invention relates to an improved method for the catalyzed condensation of aldehydes in the liquid phase to form 1,3-glycol monoesters utilizing tin metal or a tin oxide catalyst. Condensation can be visualized as an aldol condensation followed by a Tischenko reaction between the aldol and a third molecule of aldehyde. In its simplest form the condensation can be illustrated by the following general formula ##STR1## R or R.sup.1 =Hydrogen or alkyl group of 1 to 20 carbon atoms or aromatic groups. R and R.sup.1 can also be part of a cyclic system.Type: GrantFiled: May 23, 1979Date of Patent: September 30, 1980Assignee: Eastman Kodak CompanyInventors: Don L. Morris, Anthony W. McCollum
-
Patent number: 4223160Abstract: Niobium and ruthenium salts are employed as catalyst in the reaction of oxirane compounds with carboxylic acids. The acrylate esters produced can be used in photocurable compositions.Type: GrantFiled: March 26, 1979Date of Patent: September 16, 1980Assignee: Union Carbide CorporationInventor: Lawrence G. Hess
-
Patent number: 4221918Abstract: Carboxylic acid anhydrides are contacted with hydrogen in the presence of an insoluble metal hydrogenation catalyst and strong protonic acid to produce 1,1-diesters.Type: GrantFiled: October 30, 1978Date of Patent: September 9, 1980Assignee: Chevron Research CompanyInventor: Shigeto Suzuki
-
Patent number: 4221916Abstract: Saturated vicinal esters produced by reacting olefins with carboxylic acid and anhydrides thereof in the presence of oxygen and a vanadium- or ruthenium-containing catalyst.Type: GrantFiled: August 25, 1978Date of Patent: September 9, 1980Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
-
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
-
Patent number: 4221917Abstract: Monoolefins and diolefins are converted to corresponding esters in a process by contacting together at least one monoolefin, diolefin or mixture thereof, oxygen, at least one iodosoaryl dicarboxylate and at least one carboxylic acid, carboxylic acid anhydride or mixture thereof.Type: GrantFiled: March 3, 1978Date of Patent: September 9, 1980Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
-
Patent number: 4220800Abstract: Saturated vicinal esters are produced by reacting olefins with carboxylic acids and oxygen in the presence of a boron-containing catalyst component.Type: GrantFiled: September 5, 1978Date of Patent: September 2, 1980Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
-
Patent number: 4219665Abstract: Polycarboxylic acid-2-hydroxyalkyl esters of the formula ##STR1## wherein A is an aliphatic, cycloaliphatic, or aromatic radical which is optionally substituted or interrupted by heteroatoms, and/or optionally substituted by hydroxyl groups, R.sub.1 is hydrogen or an alkyl radical having 1 to 12 carbon atoms, and R.sub.2 is an alkyl radical having 10 to 22 carbon atoms, n.gtoreq.0 and m.gtoreq.2, with the proviso that m.gtoreq.n and the total of n+m.gtoreq.3, and their use as emulsifying agents and cosmetic emulsions containing them.Type: GrantFiled: June 30, 1978Date of Patent: August 26, 1980Assignee: Henkel Kommanditgesellschaft auf Aktien (Henkel KGaA)Inventors: Ulrich Zeidler, Fanny Scheuermann
-
Patent number: 4212984Abstract: 4-Oxy-6-alkenyl-bicyclo[3.1.0]hexan-2-one compounds represented by the formula (I) ##STR1## wherein R represents a hydrogen atom or a protective group for a hydroxy group, R.sup.1 represents an alkyl group having 1 to 4 carbon atoms or an aryl group, R.sup.2 represents a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms and R.sup.3 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;4-oxycyclopentanone compounds represented by the formula (II) ##STR2## wherein R, R.sup.2 and R.sup.3 are as defined above, R.sup.4 represents a hydroxymethyl group, a methylene group (.dbd.CH.sub.2) or a --COOR.sup.1 group wherein R.sup.1 is as defined above, and R.sup.5 represents an alkyl group having 1 to 4 carbon atoms or an aryl group, useful as prostaglandin precursors; and processes for preparing the same.Type: GrantFiled: December 20, 1977Date of Patent: July 15, 1980Assignee: Sagami Chemical Research CenterInventors: Kiyosi Kondo, Daiei Tunemoto, Teruo Umemoto
-
Patent number: 4208533Abstract: Process for synthesizing the lactone, (dl) 3,3a beta-4,5-6,6a betahexahydro-4beta(3-hydroxyl-1-trans-octenyl)-5alpha-hydroxy-2-oxo-2H-cy clopenta [b] furan, a known intermediate for producing prostaglandin E.sub.2 and F.sub.2.alpha. and a process for preparing 11-desoxy and 11-alkyl prostaglandins from dihydroresorcyclic acid.Type: GrantFiled: February 23, 1978Date of Patent: June 17, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Frank Kienzle, Perry Rosen
-
Patent number: 4206089Abstract: Novel bicyclic ketones having the structure: ##STR1## wherein R is a C.sub.1 -C.sub.5 alkyl group, either straight-chain or branched, and saturated analogs have been prepared. These compounds exhibit floral and woody odors and/or desirable flavor properties, and are useful as fragrance and/or flavor materials. The compounds are conveniently prepared from alkylidene cyclopentanones by Michael addition with alkyl metalloacetoacetates and subsequent decarboxylative cyclization of the adducts. The saturated analogs may then be prepared by hydrogenation.Type: GrantFiled: March 21, 1978Date of Patent: June 3, 1980Assignee: Fritzsche Dodge & Oloctt Inc.Inventors: Brian J. Willis, Robert G. Eilerman
-
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
-
Patent number: 4182761Abstract: Acyloxy-substituted aryloxyalkyl diketones, useful as anti-viral agents, are prepared either by esterification of the corresponding hydroxy-substituted compounds or by reacting a haloalkyl diketone with an alkali metal salt of an acyloxy-substituted phenol.Type: GrantFiled: June 7, 1978Date of Patent: January 8, 1980Assignee: Sterling Drug Inc.Inventors: Joseph C. Collins, Guy D. Diana
-
Patent number: 4180676Abstract: A catalyst comprising a uranium compound, an alkali metal ion, and a halide, is effective to convert conjugated dienes in carboxylic acid media to diacyloxy olefins.Type: GrantFiled: August 25, 1977Date of Patent: December 25, 1979Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
-
Patent number: 4173707Abstract: A cyclopentanol derivative represented by the formula ##STR1## wherein R.sub.1 and R.sub.2 are lower straight-chain or branched-chain alkyl, alkenyl or aralkyl, and R.sub.4 is 2-pentenyl or 2-pentynyl, and process for preparing the same.Type: GrantFiled: June 8, 1978Date of Patent: November 6, 1979Assignee: Otsuka Kagaku Yakuhin Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Yuichi Kobayashi
-
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
-
Patent number: 4166188Abstract: A 2-(2-pentynyl) cyclopentanol derivative represented by the formula ##STR1## wherein R.sub.2 is lower straight-chain or branched-chain alkyl, alkenyl or aralkyl, and process for preparing the same.Type: GrantFiled: June 8, 1978Date of Patent: August 28, 1979Assignee: Otsuka Kagaku Yakuhin Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Yuichi Kobayashi
-
Patent number: 4165331Abstract: This disclosure describes certain 11-(2-hydroxyethylthio)-9-keto-prostenoic acid E series derivatives, and their intermediates, useful as bronchodilators and inflammatory medeator release inhibitors.Type: GrantFiled: October 17, 1977Date of Patent: August 21, 1979Assignee: American Cyanamid CompanyInventors: Martin J. Weiss, Gerald J. Siuta
-
Patent number: 4164615Abstract: A catalyst comprising a titanium compound, an alkali metal ion, and a halide, is effective for the conversion of conjugated diolefins to diacyloxy olefins.Type: GrantFiled: August 25, 1977Date of Patent: August 14, 1979Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
-
Patent number: 4163111Abstract: A 2-cyclopentenone derivative represented by the formula ##STR1## wherein R.sub.1 and R.sub.2 are lower straight-chain or branched-chain alkyl, alkenyl or aralkyl, and R.sub.4 is 2-pentenyl or 2-pentynyl, and process for preparing the same.Type: GrantFiled: June 8, 1978Date of Patent: July 31, 1979Assignee: Otsuka Kagaku Yakuhim Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Yuichi Kobayashi
-
Patent number: 4163109Abstract: A process for the preparation of compounds of the formula I ##STR1## by reacting of a compound of the formula II ##STR2## with up to 1.5 molar equivalent of water at elevated temperature. R represents an alkyl group containing 1 to 3 carbon atoms, R.sup.1 represents an alkyl or alkenyl group containing 3 to 6 carbon atoms and n represents 1 or 2.Type: GrantFiled: July 13, 1977Date of Patent: July 31, 1979Assignee: Societe Anonyme Roure Bertrand DupontInventors: Paul J. Teisseire, Marcel Plattier, Edouard Giraudi
-
Patent number: 4163106Abstract: 6-Alkenyl-bicyclo[3.1.0]hexanone compounds represented by the formula (I) ##STR1## wherein R.sup.1 represents an alkyl group having 1 to 4 carbon atoms or an aryl group, and R.sup.2 represents a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms;Cyclopentanone compounds represented by the formula (II) ##STR2## wherein R.sup.2 is as defined above, R.sup.3 represents a hydrogen atom or a --COOR.sup.1 group wherein R.sup.1 is as defined above, R.sup.4 represents a hydrogen atom or a --CH.sub.2 --Y--(CH.sub.2).sub.n --COOR.sup.6 wherein Y represents a --CH.sub.2 CH.sub.2 -- group or a --CH.dbd.CH-- group, R.sup.6 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and n is an integer of 0 to 6, R.sup.5 represents a --S--R.sup.7 group or a --SO--R.sup.7 group wherein R.sup.7 represents an alkyl group having 1 to 4 carbon atoms or an aryl group, with the proviso that R.sup.3 and R.sup.Type: GrantFiled: February 25, 1977Date of Patent: July 31, 1979Assignee: Sagami Chemical Research CenterInventors: Kiyosi Kondo, Daiei Tunemoto
-
Patent number: 4162363Abstract: Conjugated dienes or monoolefins are converted to diesters in a process utilizing a catalyst system comprising an alkali metal compound and a sulfur source comprising elemental sulfur or a sulfur halide, optionally with a halide source, in carboxylic acid media.Type: GrantFiled: August 25, 1977Date of Patent: July 24, 1979Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
-
Patent number: 4154963Abstract: Process for synthesizing the lactone, (dl) 3,3a beta-4,5-6,6a beta-hexahydro-4beta(3-hydroxyl-1-trans-octenyl)-5alpha-hydroxy-2-oxo-2H-c yclopenta[b]furan, a known intermediate for producing prostaglandin E.sub.2 and F.sub.2.alpha. and a process for preparing 11-desoxy and 11-alkyl prostaglandins from dihydroresorcyclic acid.Type: GrantFiled: February 23, 1978Date of Patent: May 15, 1979Assignee: Hoffmann-La Roche Inc.Inventors: Frank Kienzle, Perry Rosen
-
Patent number: 4151199Abstract: Propanoic acid derivatives of the formula: ##STR1## where R.sup.1 is a C.sub.1-8 alkyl group optionally substituted by hydroxyl or --COOH and R.sup.2 is hydrogen or a protecting group, are useful as anti-thrombotic agents.Type: GrantFiled: December 4, 1975Date of Patent: April 24, 1979Assignee: Lilly Industries LimitedInventors: William Dawson, Michael J. Foulis, Norman J. A. Gutteridge, Colin W. Smith
-
Patent number: 4146553Abstract: Improved procedures and intermediates for synthesizing 11-deoxyprostaglandins wherein trans-2,3-dicarbomethoxycyclopentanone is prepared by the novel kinetically-controlled cyclization of 1,2,4-tricarbomethoxybutane using a dispersion of sodium hydride in dry p-xylene. Selective alcoholysis of the 2-position carbomethoxy group with benzyl alcohol, followed by alkylation allows for a wide range of upper side chains to be introduced at the 2-position of the cyclopentanone ring. The unwanted carbobenzyloxy group at the 2-position can then be removed easily by controlled hydrogenolysis followed by decarboxylation. This procedure allows for simultaneous epimerization of the 2-position side chain to the desired trans-configuration, relative to the carbomethoxy group in the 3-position, as well as for reduction of the 2-hexynyl moiety of the side chain to the desired cis-olefinic group of the E.sub.2 -type 11-deoxyprostaglandins, or through total reduction to the alkane upper side chain of E.sub.Type: GrantFiled: June 19, 1978Date of Patent: March 27, 1979Assignee: The Dow Chemical CompanyInventors: William L. White, Francis Johnson
-
Patent number: 4143230Abstract: The copper enolate of 3-allylcyclopentanone is alkylated with an alkyne so as to form the 2-alkynyl, 3-allylcyclopentanone which is then subjected to ozonolysis and oxidative cleavage to form 2-alkynylcyclopentan-3-one-1-yl alkylcarboxlic acid. The acid can be esterified to form a 2-alkynyl-3-carbalkoxyalkyl ketone which, in turn, can be hydrogenated to convert the alkynyl moiety to alkenyl or alkyl moieties. The procedure is particularly useful in the synthesis of methyl dl-jasmonate, dehydrojasminate and dihydrojasmonate.Type: GrantFiled: October 28, 1976Date of Patent: March 6, 1979Assignee: CHON CorporationInventors: Andrew E. Greene, Pierre Crabbe
-
Patent number: 4140708Abstract: An asymmetric synthesis of optically active prostaglandin F.sub.2.alpha. from cyclopentadiene including intermediates in this synthesis.Type: GrantFiled: September 19, 1977Date of Patent: February 20, 1979Assignee: Hoffmann-La Roche Inc.Inventors: Naresh K. Chadha, John J. Partridge, Jr., Milan R. Uskokovic
-
Patent number: 4139716Abstract: The present disclosure relates to D-homosteroids. More particularly, the disclosure is concerned with 19-nor-D-homopregnanes, a process for the manufacture thereof and pharmaceutical preparations containing same.Type: GrantFiled: March 25, 1976Date of Patent: February 13, 1979Assignee: Hoffmann-La Roche Inc.Inventors: Andor Furst, Jurg A. W. Gutzwiller, Marcel Muller, Ulrich Kerb, Rudolf Wiechert
-
Patent number: 4137269Abstract: The present disclosure relates to steroids. More particularly, the disclosure is concerned with D-homosteroids, a process for the manufacture thereof and pharmaceutical preparations containing same. The subject D-homosteroids have high endocrinal activity and are particularly active as anti-inflammatory agents.Type: GrantFiled: October 12, 1976Date of Patent: January 30, 1979Assignee: Hoffmann-La Roche Inc.Inventors: Leo Alig, Andor Furst, Marcel Muller, Ulrich Kerb, Klaus Kieslich, Rudolf Wiechert