Alicyclic Acids Having An Oxy, Aldehyde, Or Ketone Group Patents (Class 562/508)
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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: 5077309Abstract: Novel compounds have the formula (I) ##STR1## where ##STR2## represents one of the divalent cyclic groups ##STR3## the letters a and b indicating in each case the points of attachment of the substituents R.sup.1 and CV(R.sup.2)-NV'R, respectively; R.sup.1 is a group --(CH.sub.2).sub.b --(A).sub.a --(CH.sub.2).sub.c --B--CH.sub.2 --CO.sub.2 R' in which A and B are each separately oxygen or sulphur, a is 0, b is 0 and c is an integer from 3 to 10, or a is 1, b is 0 or an integer from 1 to 7 and c is an integer from 2 to 9 with the sum of b and c being from 2 to 9, and CO.sub.2 R' is a carboxy group or an amide, ester or salt derivative thereof; V and V' either each separately is hydrogen or together are the second bond of a carbon-nitrogen double bond; R.sup.2 is hydrogen, an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted by an aromatic group directly or through an oxygen or sulphur atom; and R is a group --OR.sup.3, --OR.sup.4, --D--R.sup.3, --N.dbd. R.sup.5 or --NW.G.Type: GrantFiled: March 28, 1990Date of Patent: December 31, 1991Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 5068414Abstract: 1,2-Dihydroxycyclohexa-3,5-diene-1,4-dicarboxylic acid and its salts, which are novel intermediates yielding hydroxyterephthalic acid upon dehydration, can be prepared by culturing terephthalic acid and a carbon/energy source with a microorganism capable of oxidizing terephthalic acid but incapable of degradation of 1,2-dihydroxycyclohexa-3,5-diene-1,4-dicarboxylic acid thereby formed.Type: GrantFiled: January 26, 1990Date of Patent: November 26, 1991Assignee: Celgene CorporationInventors: Mark E. Ruppen, Scott Hagedorn
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Patent number: 5047582Abstract: A process for oxidation of a tetrahydro compound of the formula ##STR1## wherein R and R' independently are H, alkyl, aryl or halo, to a glycol of the formula ##STR2## comprises treating the tetrahydro compound with hydrogen peroxide at an elevated temperature in the absence of a catalyst.The thus-formed glycol can be further oxidized in a butanetetracarboxylic acid of the formula ##STR3## with hydrogen peroxide in the presence of a catalyst selected from the group consisting of a manganese salt, an iron salt, a chromium salt, a cerium salt, a persulfate, a perborate, a silicate, tungstic acid or an ammonium or alkali metal salt or heteropolyacid thereof, or molybdic acid or an ammonium or alkali metal salt or heteropolyacid thereof.Type: GrantFiled: October 2, 1989Date of Patent: September 10, 1991Assignee: Ortec, Inc.Inventors: David L. Brotherton, Kwok W. Fung
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Patent number: 5015645Abstract: Disclosed are the compounds of formula I ##STR1## wherein R and R.sub.1 -R.sub.3 independently represent hydrogen or lower alkyl, and m represents the integer 2 or 3; their methods of preparation; pharmaceutical compositions thereof, and their use for treating cognitive disorders in mammals.Type: GrantFiled: October 19, 1989Date of Patent: May 14, 1991Assignee: Ciba-Geigy CorporationInventor: Jan W. F. Wasley
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Patent number: 4990178Abstract: A novel compound names "cornexistin" has the formula (I): ##STR1## and it and the corresponding ring-opened diacid and salts thereof have herbicidal and growth regulating effects. Cornexistin can be prepared by cultivation of a microorganism of the genus Paecilomyces, e.g. Paecilomyces variotii Bainier SANK 21086.Type: GrantFiled: November 13, 1989Date of Patent: February 5, 1991Assignee: Sankyo Company, LimitedInventors: Tatsuo Haneishi, Mutsuo Nakajima, Kiyoshi Koi, Kohei Furuya, Seigo Iwado, Sadao Sata
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Patent number: 4987151Abstract: The present invention provides a purified compound of the structure; ##STR1## wherein R may be palmitoyl or steroyl. The invention also provides compositions comprising an admixture of the foregoing palmitate and stearate esters.The invention also provides a compound of the structure: ##STR2## The invention further provides pharmaceutical compositions including the aforementioned compounds and compositions and methods of inhibiting the acyl CoA: cholesterol acyltransferase catalyzed conversion of cholesterol to cholesteryl esters.Type: GrantFiled: June 19, 1989Date of Patent: January 22, 1991Assignee: The Trustees of Columbia University in the City of New YorkInventor: Ira A. Tabas
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Patent number: 4976893Abstract: The invention relates to a process for preparing carboxylic acids by platinum-catalyzed oxidation of primary alcohols of limited water solubility with oxygen in a mixture of water and a solubilizer. The solubilizer used is an ether of the general formula R.sub.1 O(CH.sub.2 CH.sub.2 O).sub.n R.sub.2, where n is 1-4 and R.sub.1 and R.sub.2 are alkyl radicals having 1-4 carbon atoms.Type: GrantFiled: June 18, 1986Date of Patent: December 11, 1990Assignee: Hoechst AktiengesellschaftInventor: Ernst I. Leupold
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Patent number: 4950774Abstract: A 2,5-disubstituted-7,7,8,8-tetracyanoquinodimethane of the general formula ##STR1## wherein R.sup.1 is hydrogen or methyl, X is COOR.sup.2 (in which R.sup.2 is hydrogen or C.sub.1-10 alkyl), --CONR.sup.3 R.sup.4 (in which R.sup.3 and R.sup.4 each is hydrogen or C.sub.1-4 alkyl) or --CN, provided that when R.sup.1 is hydrogen, X is --CN or --CONR.sup.3 R.sup.4. The tetracyanoquinodimethane derivatives are starting materials for the production of polyamides, polyurethanes or organic semiconductor devices.Type: GrantFiled: October 23, 1987Date of Patent: August 21, 1990Assignee: Nippon Gohsei Kagaku Kogyo KabushikiInventor: Takeo Kawabata
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Patent number: 4936906Abstract: Agents for regulating plant growth containing an effective amount of at least one cyclohexanone derivative of the formula I ##STR1## where A, X, n, Y, Z and R have the meanings given in the disclosure, or salts of these compounds, and a process for regulating plant growth.Type: GrantFiled: July 2, 1986Date of Patent: June 26, 1990Assignee: BASF AktiengesellschaftInventors: Dieter Jahn, Michael Keil, Dieter Kolassa, Ulrich Schirmer, Rainer Becker, Johann Jung, Wilhelm Rademacher
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Patent number: 4898977Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonisation of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.Type: GrantFiled: August 13, 1987Date of Patent: February 6, 1990Assignee: Ciba-Geigy CorporationInventors: Peter Herold, Christof Angst
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Patent number: 4897420Abstract: Compounds of the formula: ##STR1## wherein l is an integer of 0 to 18, X is hydrogen, an alkyl having 1 to 4 carbon atoms or a carboxylic acyl having 2 to 4 carbon atoms and Y is a phenylene, a cycloalkylene having 3 to 7 carbon atoms or a group of the formula: ##STR2## in which m is an integer of 0 to 3, and R.sub.1 and R.sub.2 each is an alkyl having 1 to 4 carbon atoms, are novel compounds, possess circulatory disturbance-improving activity and inhibitory activity of the generation and release of SRS-A, and used for prophylactic or therapy of ischemic diseases such as cerebral apoplexy or allergic diseases.Type: GrantFiled: December 5, 1988Date of Patent: January 30, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Masazumi Watanabe, Isuke Imada
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Patent number: 4897104Abstract: A novel compound named "cornexistin" has the formula (I): ##STR1## and it and the corresponding ring-opened diacid and salts thereof have herbicidal and growth regulating effects. Cornexistin can be prepared by cultivation of a microorganism of the genus Paecilomyces, e.g. Paecilomyces variotii Bainier SANK 21086.Type: GrantFiled: April 21, 1988Date of Patent: January 30, 1990Assignee: Sankyo Company LimitedInventors: Tatsuo Haneishi, Mutsuo Nakajima, Kiyoshi Koi, Kohei Furuya, Seigo Iwado, Sadao Sato
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Patent number: 4879403Abstract: Compounds of the formula I ##STR1## in which the carboxyl group on carbon atom 3 is orientated in the endo-position relative to the bicyclic ring system of cis-configuration, and in which R.sup.1 denotes hydrogen, allyl, vinyl or a side-chain of a naturally occurring .alpha.-aminoacid, which may be protected, R.sup.2 denotes hydrogen, alkyl, alkenyl or aralkyl, Y denotes hydrogen or hydroxyl and Z denotes hydrogen, or Y and Z together denote oxygen, and X denotes alkyl, alkenyl or cycloalkyl, or aryl which is optionally mono-, di- or tri-substituted by alkyl, alkoxy, hydroxyl, halogen, nitro, amino, alkylamino, dialkylamino or methylenedioxy, or denotes indol-3-yl, a process for their preparation, agents containing these compounds and their use.Type: GrantFiled: November 2, 1988Date of Patent: November 7, 1989Assignee: Hoechst AktiengesellschaftInventors: Volker Teetz, Rolf Geiger, Hansjorg Urbach, Reinhard Becker, Bernward Scholkens
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Patent number: 4803268Abstract: The present invention relates to a novel, optimized process for the preparation of cyclohexanedionecarboxylic acid derivatives of formula I which can be carried out in a single vessel affording a very good yield, which process comprises heating a reactive carboxylic acid derivative of formula III ##STR1## wherein X is a halide, an alkylsulfonic or arylsulfonic acid radical or the molecular radical ##STR2## which is necessary to form an anhydride and R.sub.1 is alkyl or cycloalkyl, with an alkali metal cyanide or copper cyanide, in an inert organic solvent, to give a mixture, then adding in succession to said mixture, at a temperature in the range from 0.degree. C.Type: GrantFiled: January 29, 1987Date of Patent: February 7, 1989Assignee: Ciba-Geigy CorporationInventors: Hans-Georg Brunner, Urs Muller
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Patent number: 4788315Abstract: A 2,5-substituted-cyclohexane-1,4-dione of the general formula ##STR1## wherein R.sup.1 and R.sup.2 each is hydrogen or methyl; X is --COOR.sup.3 (R.sup.3 .dbd.H or alkyl), --CONR.sup.4 R.sup.5 (R.sup.4 and R.sup.5 each is hydrogen or alkyl) or --CN and a process for production of the above compound.Type: GrantFiled: September 1, 1987Date of Patent: November 29, 1988Assignee: Nippon Gohsei Kagaku Kogyo Kabushiki KaishaInventor: Takeo Kawabata
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Patent number: 4785132Abstract: A process for preparing cyclohexanonecarboxylic acid compounds by catalytically hydrogenating the corresponding hydroxybenzoic acid compounds in a secondary alcohol or tertiary alcohol solvent.Type: GrantFiled: March 25, 1987Date of Patent: November 15, 1988Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Tohru Miura, Teruyuki Nagata, Hideki Mizuta
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Patent number: 4780129Abstract: Cyclohexenone derivatves of the formula ##STR1## where R.sup.1 is alkyl, R.sup.2 is alkyl, unsubstituted or substituted alkenyl or alkynyl, A is alkoxycarbonyl, carboxyl, cyano or trifluoromethyl, B is hydrogen or methyl, X is straight-chain, branched or cyclic alkylene, Z is hydrogen or alkoxycarbonyl and n is 0 or 1, and salts thereof, and their use for combatting unwanted plant growth.Type: GrantFiled: February 13, 1987Date of Patent: October 25, 1988Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Dieter Jahn, Ulrich Schirmer, Michael Keil, Bruno Wuerzer, Norbert Meyer
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Patent number: 4780564Abstract: Described is allyl 4-cyclooctenyl glycolate of our invention having the structure: ##STR1## and the perfumery use thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, hair preparations and cosmetic powders.Type: GrantFiled: June 29, 1987Date of Patent: October 25, 1988Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, William L. Schreiber, Robert P. Belko
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Patent number: 4772432Abstract: 7,7,8,8-Tetracyanoquinodimethane-2,5-ylene-(3-propionic acid) and derivatives thereof represented by the formula ##STR1## wherein R.sub.1 and R.sub.2 are each hydrogen or alkyl. The compounds are useful as materials for preparing polyesters, polyamides and polyurethanes or as intermediates for tetracyanoquinodimethanes for use as organic semiconductors.Type: GrantFiled: June 25, 1986Date of Patent: September 20, 1988Assignee: Nippon Gosei Kagaku Kogyo Kabushiki KaishaInventor: Masahiko Miyashita
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Patent number: 4755617Abstract: A process for the preparation of 4'-hydroxybiphenyl-4-carboxylic acid by reacting a cyclohexanone-4-carboxylic acid compound with phenol in the presence of an acid catalyst, and then subjecting the resulting 4,4-bis(4-hydroxyphenyl)cyclohexanecarboxylic acid compound to decomposition and dehydrogenation reactions in the presence of a base and a dehydrogenation catalyst. The aforesaid cyclohexanone-4-carboxylic acid compound is obtained by catalytically hydrogenating a 4-hydroxybenzoic acid compound in a secondary alcohol or tertiary alcohol solvent, and the reaction mixture thus obtained is directly used for the reaction with phenol.Type: GrantFiled: March 30, 1987Date of Patent: July 5, 1988Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Tohru Miura, Teruyuki Nagata, Hideki Mizuta
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Patent number: 4755616Abstract: Novel 4,4-bis(4-hydroxyphenyl)cyclohexanecarboxylic acid derivatives. These compounds can be prepared by reacting a cyclohexanone-4-carboxylic acid with a phenol.Type: GrantFiled: March 12, 1987Date of Patent: July 5, 1988Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Tohru Miura, Teruyuki Nagata
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Patent number: 4755502Abstract: Described is allyl-4-cyclooctenyl glycolate of our invention having the structure: ##STR1## and the perfumery use thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, hair preparations and cosmetic powders. The genus defined according to the structure: ##STR2## wherein R represents hydrogen, allyl or alkali metal and: represents a covalent bond wherein R represents hydrogen or allyl and an ionic bond where R represents alkali metal defines all of the products of our invention including intermediates useful in the process for preparing the compound having the structure: ##STR3## .Type: GrantFiled: October 29, 1987Date of Patent: July 5, 1988Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, William L. Schreiber, Robert P. Belko
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Patent number: 4733003Abstract: Compounds of formula (I): ##STR1## [wherein X represents a hydrogen atom or a 2-methylbutyryl group, Y represents a hydrogen atom or a methyl group and R.sup.1 and R.sup.2 are the same or different and each represents an oxygen atom or a group of formula .dbd.N--OR.sup.3 (wherein R.sup.3 represents a hydrogen atom or an alkyl group)], the free hydroxy-carboxylic acids corresponding thereto and salts and esters of said acids may be prepared by oxidizing and, if necessary, oximating a corresponding ML-236A, ML-236B, MB-530A or MB-530B compound, and these compounds have valuable antihypercholesteraemic activity.Type: GrantFiled: May 6, 1986Date of Patent: March 22, 1988Assignee: Sankyo Company LimitedInventors: Junya Ide, Shigeki Muramatsu, Yoshio Tsujita, Msao Kuroda
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Patent number: 4713485Abstract: The invention relates to a process for preparing .alpha.-hydroxy-alkanoic acids of general formula: ##STR1## in which R represents hydrogen or a lower alkyl radical and Cy represents phenyl or a heterocyclic radical, both radicals optionally comprising one or more substituents selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl radicals and halogen atoms, process which comprises the treatment of an .alpha.,.alpha.-dihalogenated ketone of general formula: ##STR2## in which R and Cy have the same meaning as above and X represents chlorine, bromine or iodine, in the presence of an aqueous solution of an alkali metal hydroxide and a non polar organic solvent selected from an aromatic or alicyclic hydrocarbon, the treatment being carried out at a temperature between the boiling temperature of the reaction medium at atmospheric pressure and 240.degree. C. under pressure and the alkali metal so formed is then acidified to obtain the desired acid.Type: GrantFiled: November 21, 1985Date of Patent: December 15, 1987Assignee: SANOFI and Industria Chimica Prodotti FRANCIS S.p.A.Inventors: Jean-Daniel Andre, Pierre-Jean Grossi, Alain Heymes, Giovanni V. Manzaroli
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Patent number: 4705867Abstract: 1,2-Dithiolane-3-pentanoic acid (D,L-thioctic acid) of the formula ##STR1## is prepared by a process comprising (a) reacting a 2-(3-alkylthiopropionyl)-cyclopentanone-1 of the formula ##STR2## where R is a C.sub.1 -C.sub.4 alkyl, phenyl or benzyl in aqueous alkaline solution at a temperature of about 20.degree. C. to about 90.degree. C. to form the corresponding carboxylic acid of formula VI ##STR3## (b) reacting the compound of formula VI with an alkyl mercaptan at a temperature between -20.degree. C. and 0.degree. C. to form the corresponding thioketal of formula VII ##STR4## (c) reacting the compound of formula VII with sodium in liquid ammonia at a temperature between -60.degree. C. and -10.degree. C.Type: GrantFiled: April 4, 1986Date of Patent: November 10, 1987Assignee: Degussa AktiengesellschaftInventors: Guenes Giray, Klaus Huthmacher, Axel Kleemann, Thomas Lied
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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: 4693745Abstract: Novel cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties. The cyclohexanedionecarboxylic acid derivatives have the formula I ##STR1## wherein A is an --OR.sub.2 or --NR.sub.3 R.sub.4 radical,R is C.sub.3 -C.sub.6 cycloalkyl,R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkylthioalkyl; C.sub.3 -C.sub.6 alkenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; C.sub.3 -C.sub.6 alkynyl; phenyl or C.sub.1 -C.sub.6 aralkyl, wherein the phenyl nucleus is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, nitro or cyano; one of R.sub.3 and R.sub.4 is methoxy; orR.sub.3 and R.sub.Type: GrantFiled: October 9, 1985Date of Patent: September 15, 1987Assignee: Ciba-Geigy CorporationInventor: Hans-Georg Brunner
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Patent number: 4678496Abstract: As new compound is provided a cyclohexane derivative of the formula ##STR1## wherein R represents a hydrogen atom or an alkyl group, an alkylthioalkyl group or an unsubstituted or substituted phenyl group; and R.sup.1 represents an alkyl group, an unsubstituted or substituted benzyl group, a phenethyl group, a phenoxymethyl group, a 2-thienylmethyl group, an alkoxymethyl group or an alkylthiomethyl group, or a salt of said cyclohexane compound.This cyclohexane compound exhibits useful plant-growth regulating effects on crop-plants and also non-crop plants such as lawn and may be prepared by cyclization of an acetonylsuccinic acid dialkyl ester, followed by reaction with an organic acid chloride and by intermolecular rearrangement.Type: GrantFiled: August 1, 1985Date of Patent: July 7, 1987Assignee: Kumiai Chemical Industry Co., Ltd.Inventors: Kenji Motojima, Takeshige Miyazawa, Yasufumi Toyokawa, Masafumi Matsuzawa, Hiroshi Hokari, Shoji Kusano
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Patent number: 4663478Abstract: By reacting a phenol compound with an organic halide selected from the group consisting of a haloform, a carbon tetrahalide and a substituted or unsubstituted allyl halide in the presence of an alkali metal hydroxide, using as a catalyst a fixed cyclodextrin having hydroxyl groups crosslinked with a bivalent hydrocarbon group having free valences at its both ends, said hydrocarbon group having at least one hydrogen atom substituted or unsubstituted with a member selected from the group consisting of an alkyl group, a halogen atom and a hydroxyl group and containing or not containing at least one combination of two neighboring carbon atoms having therebetween at least one member selected from the group consisting of an oxygen atom, a sulfur atom and a phenylene, various useful para-substituted phenol derivatives can be advantageously obtained.Type: GrantFiled: April 18, 1985Date of Patent: May 5, 1987Assignee: Hidefuni HiraiInventors: Hidefuni Hirai, Makoto Komiyama, Izuru Sugiura
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Patent number: 4645858Abstract: Compounds of formula I are described which are useful to inhibit the formation of serum cholesterol by virtue of their ability to inhibit .beta.-hydroxy-.beta.-methylglutaryl-CoA(HMG CoA), the rate-controlling substance in the synthesis of serum cholesterol.Type: GrantFiled: October 10, 1985Date of Patent: February 24, 1987Assignee: G. D. Searle & Co.Inventors: Harman S. Lowrie, John S. Baran
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Patent number: 4618360Abstract: Novel cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties. The cyclohexanedionecarboxylic acid derivatives have the formula I ##STR1## wherein A is an --OR.sub.2 or --NR.sub.3 R.sub.4 radical,B is hydroxyl, an --NHOR.sub.1 radical or a metal or ammonium salt thereofR is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each unsubstituted or substituted by halogen, C.sub.1 -C.sub.6 alkoxy or C.sub.2 -C.sub.4 alkythio,R.sub.1 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.sub.6 alkynyl,R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkylthioalkyl; C.sub.3 -C.sub.6 alkenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; C.sub.3 -C.sub.6 alkynyl; phenyl or C.sub.1 -C.sub.Type: GrantFiled: November 19, 1984Date of Patent: October 21, 1986Assignee: Ciba-Geigy CorporationInventor: Hans-Georg Brunner
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Patent number: 4605749Abstract: There is provided a process for the production of aldehydes wherein an oric halide is reacted with carbon monoxide at a superatmospheric pressure in the presence of a hydrogen donor and in the presence of a base and of a catalyst in a solvent system.Catalysts of choice are transition metal catalysts. A preferred temperature range is from about 50.degree. to 150.degree. C.Type: GrantFiled: June 20, 1985Date of Patent: August 12, 1986Assignee: State of Israel, Prime Minister's Office, Atomic Energy CommissionInventors: Ouri Buchman, Ilan Pri-Bar
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Patent number: 4584013Abstract: Novel cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties.The cyclohexanedionecarboxylic acid derivatives have the formula I ##STR1## wherein A is an --OR.sub.2 or --NR.sub.3 R.sub.4 radical,B is hydroxyl, an --NHOR.sub.1 radical or a metal or ammonium salt thereofR is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each unsubstituted or substituted by halogen, C.sub.1 -C.sub.6 alkoxy or C.sub.2 -C.sub.4 alkylthio,R.sub.1 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.sub.6 alkynyl,R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkylthioalkyl; C.sub.3 -C.sub.6 alkenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; C.sub.3 -C.sub.6 alkynyl; phenyl or C.sub.1 -C.sub.Type: GrantFiled: May 14, 1984Date of Patent: April 22, 1986Assignee: Ciba-Geigy CorporationInventor: Hans-Georg Brunner
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Patent number: 4560403Abstract: As new compound is provided a cyclohexane derivative of the formula ##STR1## wherein R represents a hydrogen atom or an alkyl group, an alkylthioalkyl group or an unsubstituted or substituted phenyl group; and R.sup.1 represents an alkyl group, an unsubstituted or substituted benzyl group, a phenethyl group, a phenoxymethyl group, a 2-thienylmethyl group, an alkoxymethyl group or an alkylthiomethyl group, or a salt of said cyclohexane compound.This cyclohexane compound exhibits useful plant-growth regulating effects on crop-plants and also non-crop plants such as lawn and may be prepared by cyclization of an acetonylsuccinic acid dialkyl ester, followed by reaction with an organic acid chloride and by intermolecular rearrangement.Type: GrantFiled: September 22, 1983Date of Patent: December 24, 1985Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Kenji Motojima, Takeshige Miyazawa, Yasufumi Toyokawa, Masafumi Matsuzawa, Hiroshi Hokari, Shoji Kusano
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Patent number: 4554359Abstract: This invention relates to methods of preventing or reducing the degradation of elastin and other proteins and thereby preventing or retarding the disease states caused by said degradation by administering compounds of the formula: ##STR1## or their pharmacologically acceptable salts.Type: GrantFiled: January 9, 1984Date of Patent: November 19, 1985Assignee: G. D. Searle & Co.Inventors: Harman S. Lowrie, John S. Baran
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Patent number: 4529704Abstract: A device for preparing a control solution for ketone analysis is disclosed, as well as a method for preparing it. The device comprises a carrier vehicle incorporated with an ester of a .beta.-ketoalkanoic acid, and a hydrolyzing substance capable of converting the ester to the corresponding .beta.-ketoalkanoic acid. The ester has the structure ##STR1## in which R is a lower alkyl group and R' is an aliphatic or cyclic group having 1 to about 7 carbon atoms. The method comprises contacting a predetermined volume of solvent with the device.Type: GrantFiled: November 25, 1981Date of Patent: July 16, 1985Assignee: Miles Laboratories, Inc.Inventors: Robert W. Trimmer, William I. White
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Patent number: 4523031Abstract: By reacting, using as a catalyst a modified or unmodified cyclodextrin, a phenol compound with an organic halide selected from the group consisting of a carbon tetrahalide and a substituted or unsubstituted allyl halide in the presence of an alkali metal hydroxide, a substituent group derived from said organic halide can be introduced to the para-position of the phenol compound with high selectivity, whereby various useful para-substituted phenol derivatives can be advantageously obtained.Type: GrantFiled: September 7, 1983Date of Patent: June 11, 1985Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hidefumi Hirai, Makoto Komiyama
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Patent number: 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: 4487972Abstract: This specification discloses a process for the production of oxygenated compounds, more specifically aldehydes and alcohols, by reacting an olefin with hydrogen and carbon monoxide in the presence of, as a ctalyst, an insoluble polymer containing a functional group, which may be an amine, thiol, phosphine, or arsine group, having chemically bonded thereto a metal of Group VIII of the Periodic Table. The metal can be, for example, rhodium, cobalt, or ruthenium. The olefin can contain more than one carbon-to-carbon double bond, may be an open chain or a cyclic olefin, and may be substituted. Further, the olefin may be contained in a refinery stream such as a cracked gasoline. The reaction may be carried out in the presence of a polar solvent.Type: GrantFiled: April 22, 1980Date of Patent: December 11, 1984Assignee: Mobil Oil CorporationInventors: Werner O. Haag, Darrell D. Whitehurst
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Patent number: 4425321Abstract: Deodorant compositions containing at least one zinc or magnesium salt of a polyacid of the general formula: ##STR1## in which X is--CH.dbd.CH--or--CHOH--CHOH--, Y is H, a saturated or unsaturated aliphatic radical of 1 to 10 carbon atoms, which is unsubstituted or substituted by one or more hydroxyls, a saturated or unsaturated alicyclic radical of up to 30 carbon atoms, which is unsubstituted or substituted by one or more hydroxyls and/or a carboxylic acid group, or Y denotes a carboxylic acid radical when p=O, Z denotes a saturated or unsaturated hydrocarbon radical of up to 6 carbon atoms, n is an integer less than 10, p is O or an integer less than or equal to n, and R is H or a lower alkyl group, and of a positional isomer of such a polyacid, exhibit the advantage that they prevent the development of odors without thereby destroying the biological equilibrium of the skin.Type: GrantFiled: July 28, 1978Date of Patent: January 10, 1984Assignee: L'OrealInventors: Bernard Jacquet, Gerard Lang, Alain Malaval
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Patent number: 4413139Abstract: Described is a process for preparing the compound having the structure: ##STR1## comprising the steps of reacting 1-acetyl-3,3-dimethylcyclohexane with a dialkyl carbonate; thereby forming a ketoester having the structure: ##STR2## wherein R represents C.sub.1 -C.sub.3 lower alkyl; reacting the said ketoester with an allyl halide to form a substituted ketoester having the structure: ##STR3## saponifying the substituted ketoester with base forming a substituted keto carboxylic ester salt; and hydrolyzing the said keto carboxylic acid salt with acid to form the corresponding acid; and then heating and decarboxylating the resulting keto carboxylic acid to form the desired compound.Type: GrantFiled: May 6, 1982Date of Patent: November 1, 1983Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, Mark A. Sprecker
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Patent number: 4393075Abstract: New quinone compounds of the formula: ##STR1## wherein R.sup.1 is methyl or methoxy, or the two R.sup.1 groups jointly represent --CH.dbd.CH--CH.dbd.CH--; X is --CH.dbd.CH-- or --C.dbd.C--; Y.sup.1 is hydrogen, hydroxyl, carboxyl, cyano, acyloxy or --COZ in which Z is amino which may be substituted; m is zero or an integer of 1 to 3; n is zero or an integer of 1 to 10; n' is an integer of 1 to 5; k is an integer of 1 to 3; and when k is 2 or 3, n' is optionally variable within the range of 1 to 5 in each occurrence of the --X--(CH.sub.2).sub.n' group; and their hydroquinone forms and salts, have useful physiological activities such as antiasthmatic, antiallergic and bloodpressure decreasing activities.Type: GrantFiled: March 26, 1981Date of Patent: July 12, 1983Assignee: Takeda Chemical Industries, Ltd.Inventors: Shinji Terao, Mitsuru Shiraishi, Yoshitaka Maki
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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: 4377709Abstract: 5-Oxoalkanoic acids are prepared by addition of a ketone containing at least one hydrogen atom in the .alpha.-position with regard to the keto group, to an .alpha.,.beta.-unsaturated acid. As catalysts secondary amines are present.Type: GrantFiled: December 19, 1980Date of Patent: March 22, 1983Assignee: Hoechst AktiengesellschaftInventor: Werner H. Muller
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Patent number: 4370488Abstract: The invention includes novel alkali metal complex compounds (and processes for their preparation) which are useful, inter alia for the hydrogenation of alkali metals at room temperature or below room temperature to form hydrides or nitrides.Type: GrantFiled: June 18, 1981Date of Patent: January 25, 1983Assignee: Studiengesellschaft Kohle mbHInventor: Borislav Bogdanovic
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Patent number: 4366076Abstract: Corrosion-inhibited compositions are described comprising a functional fluid in contact with a ferrous metal and, as corrosion inhibitor, a compound having the formula: ##STR1## wherein X is H, an alkali- or alkaline earth metal, NH.sub.4, the residue of a protonated amine, or the group --OX is the residue of an alkanol having from 1 to 20 carbon atoms or of di-, tri- or tetra-ol having from 2 to 12 carbon atoms; R.sup.1, R.sup.2 and R.sup.4 are the same or different and each is H or --CH.sub.2 CH.sub.2 COOX wherein X has its previous meaning; R.sup.3 and R.sup.5 are the same or different and each is H, --CH.sub.2 CH.sub.2 COOX wherein X has its previous meaning, or R.sup.3 or R.sup.5 is a straight- or branched chain alkyl group having from 3 to 16 carbon atoms; or R.sup.3 and R.sup.5, together with the carbon atom to which they are each attached, may form a cycloalkanone ring containing from 5 to 15 carbon atoms.Type: GrantFiled: May 28, 1981Date of Patent: December 28, 1982Assignee: Ciba-Geigy CorporationInventor: David R. Clark
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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: 4340753Abstract: A method is provided for oxidatively cleaving .alpha.,.beta.-unsaturated cyclic ketones, such as isophorone, with an oxidizing agent, for example, ozone, and thereafter recovering the resulting keto acid. In instances where ozone is used, an aqueous hydroperoxide and phase transfer catalyst can be used to recover the keto acid. Dione cyclics, for example, dimedone, can be obtained by direct dehydration of the keto acid.Type: GrantFiled: September 2, 1980Date of Patent: July 20, 1982Assignee: General Electric CompanyInventor: James A. Cella
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Patent number: 4334087Abstract: A novel process for the manufacture of .alpha.-ketocarboxylic acids which comprises the reaction of oximinohalide with cyanide ion to form oximinonitrile which is reacted with hydroxide ion to form oximinoacid and hydrolysis thereof to the .alpha.-ketoacid.Type: GrantFiled: September 11, 1980Date of Patent: June 8, 1982Assignee: Zoecon CorporationInventors: Ted A. Baer, Jeffrey N. Labovitz