Alicyclic Acids Having An Oxy, Aldehyde, Or Ketone Group Patents (Class 562/508)
  • Patent number: 5091113
    Abstract: 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: Grant
    Filed: July 27, 1990
    Date of Patent: February 25, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Brian G. Clubley
  • Patent number: 5077309
    Abstract: 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: Grant
    Filed: March 28, 1990
    Date of Patent: December 31, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 5068414
    Abstract: 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: Grant
    Filed: January 26, 1990
    Date of Patent: November 26, 1991
    Assignee: Celgene Corporation
    Inventors: Mark E. Ruppen, Scott Hagedorn
  • Patent number: 5047582
    Abstract: 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: Grant
    Filed: October 2, 1989
    Date of Patent: September 10, 1991
    Assignee: Ortec, Inc.
    Inventors: David L. Brotherton, Kwok W. Fung
  • Patent number: 5015645
    Abstract: 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: Grant
    Filed: October 19, 1989
    Date of Patent: May 14, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Jan W. F. Wasley
  • Patent number: 4990178
    Abstract: 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: Grant
    Filed: November 13, 1989
    Date of Patent: February 5, 1991
    Assignee: Sankyo Company, Limited
    Inventors: Tatsuo Haneishi, Mutsuo Nakajima, Kiyoshi Koi, Kohei Furuya, Seigo Iwado, Sadao Sata
  • Patent number: 4987151
    Abstract: 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: Grant
    Filed: June 19, 1989
    Date of Patent: January 22, 1991
    Assignee: The Trustees of Columbia University in the City of New York
    Inventor: Ira A. Tabas
  • Patent number: 4976893
    Abstract: 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: Grant
    Filed: June 18, 1986
    Date of Patent: December 11, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Ernst I. Leupold
  • Patent number: 4950774
    Abstract: 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: Grant
    Filed: October 23, 1987
    Date of Patent: August 21, 1990
    Assignee: Nippon Gohsei Kagaku Kogyo Kabushiki
    Inventor: Takeo Kawabata
  • Patent number: 4936906
    Abstract: 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: Grant
    Filed: July 2, 1986
    Date of Patent: June 26, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Jahn, Michael Keil, Dieter Kolassa, Ulrich Schirmer, Rainer Becker, Johann Jung, Wilhelm Rademacher
  • Patent number: 4898977
    Abstract: 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: Grant
    Filed: August 13, 1987
    Date of Patent: February 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Herold, Christof Angst
  • Patent number: 4897420
    Abstract: 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: Grant
    Filed: December 5, 1988
    Date of Patent: January 30, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Masazumi Watanabe, Isuke Imada
  • Patent number: 4897104
    Abstract: 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: Grant
    Filed: April 21, 1988
    Date of Patent: January 30, 1990
    Assignee: Sankyo Company Limited
    Inventors: Tatsuo Haneishi, Mutsuo Nakajima, Kiyoshi Koi, Kohei Furuya, Seigo Iwado, Sadao Sato
  • Patent number: 4879403
    Abstract: 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: Grant
    Filed: November 2, 1988
    Date of Patent: November 7, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Volker Teetz, Rolf Geiger, Hansjorg Urbach, Reinhard Becker, Bernward Scholkens
  • Patent number: 4803268
    Abstract: 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: Grant
    Filed: January 29, 1987
    Date of Patent: February 7, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Georg Brunner, Urs Muller
  • Patent number: 4788315
    Abstract: 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: Grant
    Filed: September 1, 1987
    Date of Patent: November 29, 1988
    Assignee: Nippon Gohsei Kagaku Kogyo Kabushiki Kaisha
    Inventor: Takeo Kawabata
  • Patent number: 4785132
    Abstract: A process for preparing cyclohexanonecarboxylic acid compounds by catalytically hydrogenating the corresponding hydroxybenzoic acid compounds in a secondary alcohol or tertiary alcohol solvent.
    Type: Grant
    Filed: March 25, 1987
    Date of Patent: November 15, 1988
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Tohru Miura, Teruyuki Nagata, Hideki Mizuta
  • Patent number: 4780129
    Abstract: 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: Grant
    Filed: February 13, 1987
    Date of Patent: October 25, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Dieter Jahn, Ulrich Schirmer, Michael Keil, Bruno Wuerzer, Norbert Meyer
  • Patent number: 4780564
    Abstract: 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: Grant
    Filed: June 29, 1987
    Date of Patent: October 25, 1988
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, William L. Schreiber, Robert P. Belko
  • Patent number: 4772432
    Abstract: 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: Grant
    Filed: June 25, 1986
    Date of Patent: September 20, 1988
    Assignee: Nippon Gosei Kagaku Kogyo Kabushiki Kaisha
    Inventor: Masahiko Miyashita
  • Patent number: 4755617
    Abstract: 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: Grant
    Filed: March 30, 1987
    Date of Patent: July 5, 1988
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Tohru Miura, Teruyuki Nagata, Hideki Mizuta
  • Patent number: 4755616
    Abstract: 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: Grant
    Filed: March 12, 1987
    Date of Patent: July 5, 1988
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Tohru Miura, Teruyuki Nagata
  • Patent number: 4755502
    Abstract: 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: Grant
    Filed: October 29, 1987
    Date of Patent: July 5, 1988
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, William L. Schreiber, Robert P. Belko
  • Patent number: 4733003
    Abstract: 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: Grant
    Filed: May 6, 1986
    Date of Patent: March 22, 1988
    Assignee: Sankyo Company Limited
    Inventors: Junya Ide, Shigeki Muramatsu, Yoshio Tsujita, Msao Kuroda
  • Patent number: 4713485
    Abstract: 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: Grant
    Filed: November 21, 1985
    Date of Patent: December 15, 1987
    Assignee: SANOFI and Industria Chimica Prodotti FRANCIS S.p.A.
    Inventors: Jean-Daniel Andre, Pierre-Jean Grossi, Alain Heymes, Giovanni V. Manzaroli
  • Patent number: 4705867
    Abstract: 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: Grant
    Filed: April 4, 1986
    Date of Patent: November 10, 1987
    Assignee: Degussa Aktiengesellschaft
    Inventors: Guenes Giray, Klaus Huthmacher, Axel Kleemann, Thomas Lied
  • Patent number: 4701553
    Abstract: 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: Grant
    Filed: January 28, 1983
    Date of Patent: October 20, 1987
    Assignee: Texaco Inc., White
    Inventor: Justin C. Powell
  • Patent number: 4693745
    Abstract: 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: Grant
    Filed: October 9, 1985
    Date of Patent: September 15, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans-Georg Brunner
  • Patent number: 4678496
    Abstract: 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: Grant
    Filed: August 1, 1985
    Date of Patent: July 7, 1987
    Assignee: Kumiai Chemical Industry Co., Ltd.
    Inventors: Kenji Motojima, Takeshige Miyazawa, Yasufumi Toyokawa, Masafumi Matsuzawa, Hiroshi Hokari, Shoji Kusano
  • Patent number: 4663478
    Abstract: 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: Grant
    Filed: April 18, 1985
    Date of Patent: May 5, 1987
    Assignee: Hidefuni Hirai
    Inventors: Hidefuni Hirai, Makoto Komiyama, Izuru Sugiura
  • Patent number: 4645858
    Abstract: 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: Grant
    Filed: October 10, 1985
    Date of Patent: February 24, 1987
    Assignee: G. D. Searle & Co.
    Inventors: Harman S. Lowrie, John S. Baran
  • Patent number: 4618360
    Abstract: 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: Grant
    Filed: November 19, 1984
    Date of Patent: October 21, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans-Georg Brunner
  • Patent number: 4605749
    Abstract: 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: Grant
    Filed: June 20, 1985
    Date of Patent: August 12, 1986
    Assignee: State of Israel, Prime Minister's Office, Atomic Energy Commission
    Inventors: Ouri Buchman, Ilan Pri-Bar
  • Patent number: 4584013
    Abstract: 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: Grant
    Filed: May 14, 1984
    Date of Patent: April 22, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans-Georg Brunner
  • Patent number: 4560403
    Abstract: 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: Grant
    Filed: September 22, 1983
    Date of Patent: December 24, 1985
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Kenji Motojima, Takeshige Miyazawa, Yasufumi Toyokawa, Masafumi Matsuzawa, Hiroshi Hokari, Shoji Kusano
  • Patent number: 4554359
    Abstract: 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: Grant
    Filed: January 9, 1984
    Date of Patent: November 19, 1985
    Assignee: G. D. Searle & Co.
    Inventors: Harman S. Lowrie, John S. Baran
  • Patent number: 4529704
    Abstract: 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: Grant
    Filed: November 25, 1981
    Date of Patent: July 16, 1985
    Assignee: Miles Laboratories, Inc.
    Inventors: Robert W. Trimmer, William I. White
  • Patent number: 4523031
    Abstract: 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: Grant
    Filed: September 7, 1983
    Date of Patent: June 11, 1985
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Hidefumi Hirai, Makoto Komiyama
  • Patent number: 4510321
    Abstract: 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: Grant
    Filed: January 31, 1983
    Date of Patent: April 9, 1985
    Assignee: Allied Corporation
    Inventors: Divakaran Masilamani, Edward H. Manahan
  • Patent number: 4487972
    Abstract: 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: Grant
    Filed: April 22, 1980
    Date of Patent: December 11, 1984
    Assignee: Mobil Oil Corporation
    Inventors: Werner O. Haag, Darrell D. Whitehurst
  • Patent number: 4425321
    Abstract: 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: Grant
    Filed: July 28, 1978
    Date of Patent: January 10, 1984
    Assignee: L'Oreal
    Inventors: Bernard Jacquet, Gerard Lang, Alain Malaval
  • Patent number: 4413139
    Abstract: 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: Grant
    Filed: May 6, 1982
    Date of Patent: November 1, 1983
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Mark A. Sprecker
  • Patent number: 4393075
    Abstract: 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: Grant
    Filed: March 26, 1981
    Date of Patent: July 12, 1983
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shinji Terao, Mitsuru Shiraishi, Yoshitaka Maki
  • Patent number: 4390724
    Abstract: 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: Grant
    Filed: April 16, 1982
    Date of Patent: June 28, 1983
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4377709
    Abstract: 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: Grant
    Filed: December 19, 1980
    Date of Patent: March 22, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Werner H. Muller
  • Patent number: 4370488
    Abstract: 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: Grant
    Filed: June 18, 1981
    Date of Patent: January 25, 1983
    Assignee: Studiengesellschaft Kohle mbH
    Inventor: Borislav Bogdanovic
  • Patent number: 4366076
    Abstract: 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: Grant
    Filed: May 28, 1981
    Date of Patent: December 28, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: David R. Clark
  • Patent number: 4347379
    Abstract: 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: Grant
    Filed: March 10, 1980
    Date of Patent: August 31, 1982
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 4340753
    Abstract: 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: Grant
    Filed: September 2, 1980
    Date of Patent: July 20, 1982
    Assignee: General Electric Company
    Inventor: James A. Cella
  • Patent number: 4334087
    Abstract: 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: Grant
    Filed: September 11, 1980
    Date of Patent: June 8, 1982
    Assignee: Zoecon Corporation
    Inventors: Ted A. Baer, Jeffrey N. Labovitz