Alicyclic Acid Moiety Containing Oxy, Aldehyde Or Ketone Group Patents (Class 560/126)
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Patent number: 5750750Abstract: A complex alcohol ester which comprises the reaction product of an add mixture of the following: a polyhydroxyl compound represented by the general formula:R(OH).sub.nwherein R is any aliphatic or cyclo-aliphatic hydrocarbyl group and n is at least 2, provided that the hydrocarbyl group contains from about 2 to 20 carbon atoms; a polybasic acid or an anhydride of a polybasic acid, provided that the ratio of equivalents of the polybasic acid to equivalents of alcohol from the polyhydroxyl compound is in the range between about 1.6:1 to 2:1; and a monohydric alcohol, provided that the ratio of equivalents of the monohydric alcohol to equivalents of the polybasic acid is in the range between about 0.84:1 to 1.2:1; wherein the complex alcohol ester exhibits a pour point of less than or equal to -20.degree. C., a viscosity in the range between about 100-700 cSt at 40.degree. C. and having a polybasic acid ester concentration of less than or equal to 70 wt. %, based on the complex alcohol ester.Type: GrantFiled: February 7, 1997Date of Patent: May 12, 1998Assignee: Exxon Chemical Patents Inc.Inventors: Carolyn Boggus Duncan, Paul R. Geissler, David Wayne Turner, William Joseph Munley, Jr., Martin A. Krevalis
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Patent number: 5750765Abstract: Ethylenically unsaturated monomers are protected from premature polymerization during manufacture and storage by the incorporation therein of an effective stabilizing amount of a 7-substituted quinone methide compound.Type: GrantFiled: August 27, 1996Date of Patent: May 12, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Peter Nesvadba, Samuel Evans, Matthew E. Gande, Volker H. von Ahn, Roland A. E. Winter
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Patent number: 5698641Abstract: A coating composition applied to a substrate wherein the composition contains a solids content of at least about 65 percent by weight and includes a polyanhydride having more than one non-cyclic anhydride moiety, a glycidyl groups-containing oligomer, a catalyst and a surfactant or flow-control agent.Type: GrantFiled: January 29, 1997Date of Patent: December 16, 1997Assignee: The Dow Chemical CompanyInventors: Michael L. Gould, Marvin L. Dettloff, David A. Grilli, Richard A. Hickner, James A. Rabon
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Patent number: 5639902Abstract: The invention relates to a compound selected from these of formula (I): ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and B are as defined in the description, their enantiomers and diastereoisomers, their Z and E isomers, and their addition salts with a pharmaceutically-acceptable acid or base, and medicinal products containing the same which is useful for treating a disorder selected from an inflammatory disorder and a pathological inflammatory condition.Type: GrantFiled: February 15, 1994Date of Patent: June 17, 1997Assignee: Adir et CompagnieInventors: Jean-Pierre Girard, Pierre Hullot, Claude Bonne, Jean-Claude Rossi, Roger Escale, Agnes Muller
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Patent number: 5633330Abstract: A coating composition with a solids content of at least about 65% by weight comprises a polyanhydride having more than one non-cyclic anhydride moiety, a glycidyl groups-containing oligomer, a catalyst and a surfactant or flow-control agent.Type: GrantFiled: October 4, 1995Date of Patent: May 27, 1997Assignee: The Dow Chemical CompanyInventors: Michael L. Gould, David A. Grilli, Marvin L. Dettloff, Richard A. Hickner, James A. Rabon
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Patent number: 5633020Abstract: A coating composition with a solids content of at least about 65% by weight comprises a polyanhydride having more than one non-cyclic anhydride moiety, a co-reactant resin such as a glycidyl (meth)acrylate-containing polymer and a latent catalyst wherein the equivalent ratio of epoxy to anhydride is from about 0.8:1 to 1.3:1.Type: GrantFiled: October 4, 1995Date of Patent: May 27, 1997Assignee: The Dow Chemical CompanyInventors: Michael L. Gould, David A. Grilli, Marvin L. Dettloff, Richard A. Hickner, James A. Rabon
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Patent number: 5614486Abstract: The compounds of formula ##STR1## wherein the Z group can be located in positions ortho-, meta- or para-relative to the carboxylic group, symbol R.sup.1 stands for a saturated or unsaturated, linear or branched C.sub.1 to C.sub.4 alkyl radical anda. the dotted lines represent a cyclohexanic moiety and Z represents a ##STR2## group, R.sup.2 being a saturated or unsaturated, linear or branched C.sub.1 to C.sub.4 alkyl radical; orb. the dotted lines represent a cyclohexanic or benzenic moiety and Z represents a group of formula ##STR3## in which R.sup.2 is a saturated or unsaturated, linear or branched C.sub.1 to C.sub.4 alkyl radical, are useful as perfuming ingredients for the preparation of perfuming compositions and a variety of perfumed consumer articles. They impart to the latter odor notes of the fruity and floral type.Type: GrantFiled: May 23, 1995Date of Patent: March 25, 1997Assignee: Firmenich SAInventors: Wolfgang K. Giersch, Peter Fankhauser
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Patent number: 5614641Abstract: The present invention concerns a process for enantioselective catalytic hydrogenation of the ketone C.dbd.O double bond to a secondary alcohol function, said process using a neutral ruthenium complex as the catalyst and a compound containing a C.dbd.O group as the substrate to be hydrogenated, characterised in that it comprises hydrogenation of the substrate using a diallyl (diphosphino) ruthenium compound with formula ##STR1## where al preferably represents CH.sub.2 CH.dbd.CH.sub.2 or CH.sub.2 C(CH.sub.3).dbd.CH.sub.2,Q represents a hydrocarbon bridge containing at least two catenary carbon atoms and which can contain one to four catenary heteroatoms selected from O, S, N and Si,R.sup.1 to R.sup.4 may be identical or different and each represents a C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.7 cycloalkyl or C.sub.6 -C.sub.12 aryl group.Type: GrantFiled: March 9, 1995Date of Patent: March 25, 1997Assignee: Elf AquitaineInventors: Jean-Pierre Genet, Sylvain Juge, Jean-Alex Laffitte, Catherine Pinel, Serge Mallart
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Patent number: 5602196Abstract: Stabilisers of formula I ##STR1## wherein R.sub.1 and R.sub.2 may be C.sub.1 -C.sub.5 alkyl, the substituents R.sub.3 to R.sub.8 may be hydrogen, the variable n may be 1 or 2, and, when n is 1, A may be an alkoxy radical, and, when n is 2, A may be a diamine radical.Type: GrantFiled: November 27, 1995Date of Patent: February 11, 1997Assignee: Ciba-Geigy CorporationInventors: Bernard Gilg, Rita Pitteloud
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Patent number: 5599813Abstract: Thiazolopyrimidine derivatives represented by the formula ##STR1## and salts thereof are provided, which are characterized by a carboxamide residue substituted with R.sup.4 and R.sup.5. The derivatives and salts thereof exhibit antiangiogenic activity and are useful for treatment and cure of diseases, the development of which may be related to angiogenesis, including diabetic retinopathy, various chronic inflammation conditions, growth or metastasis of malignant solid tumors, rheumatism and psoriasis.Type: GrantFiled: April 1, 1994Date of Patent: February 4, 1997Assignee: Daiichi Pharmaceutical Co., Ltd.Inventors: Hiroo Matsumoto, Noriko Tanaka, Kiyoshi Nakayama, Haruko Chatani, Michio Iwahana
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Patent number: 5597932Abstract: The invention is drawn to a compound having the following formula ##STR1## in which X.sup.1 and X.sup.2, which may be the same or different, represent hydrogen or a hydroxy-protecting group, X.sup.4 is hydrogen, A is selected from --COOAlkyl and CH.sub.2 OH, and B is a hydroxy group, or A and B, when taken together, represent an oxo group. These compounds are useful as intermediates in the production of 19-nor vitamin D derivatives.Type: GrantFiled: May 16, 1995Date of Patent: January 28, 1997Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rolf E. Swenson
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Patent number: 5597938Abstract: A novel process for the production of a compound represented by the formula: ##STR1## wherein Z and Z' each represents a protective group for the hydroxyl group; R.sup.1 represents a hydrogen atom or an alkyl group; R.sup.2 represents an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a group represented by the formula --B--D (in which B is an alkylene group and D is a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenoxy group or a cycloalkyl group), a substituted or unsubstituted phenyl group or a substituted or unsubstituted phenoxy group; R.sup.3 and R.sup.4 each represents a hydrogen atom, an alkyl group or an alkoxy group; R.sup.5 represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a cyano group, an amino group, a hydroxyl group or a group represented by a formula --COOR.sup.8 ; R.sup.6 represents a group represented by a formula --COOR.sup.9, a cyano group, a hydroxyl group, a group represented by a formula --OCOR.sup.Type: GrantFiled: August 10, 1995Date of Patent: January 28, 1997Assignees: Taisho Pharmaceutical Co., Ltd., Fumie SatoInventor: Fumie Sato
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Patent number: 5583247Abstract: Ethylenically unsaturated monomers are protected from premature polymerization during manufacture and storage by the incorporation therein of an effective stabilizing amount of a 7-substituted quinone methide compound.Type: GrantFiled: April 14, 1995Date of Patent: December 10, 1996Assignee: Ciba-Geigy CorporationInventors: Peter Nesvadba, Samuel Evans, Matthew E. Gande, Volker H. von Ahn, Roland A. E. Winter
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Patent number: 5565490Abstract: p-Hydroxyaniline derivatives of the formula I ##STR1## where the substituents have the following meanings: R.sup.1 is hydrogen, or unsubstituted or substituted alkyl;R.sup.2 and R.sup.3 independently of one another are halogen, alkyl, haloalkyl, alkoxy or haloalkoxy;R.sup.4 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl,OR.sup.5 or NR.sup.6 R.sup.7, whereR.sup.5, R.sup.6 are unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl, andR.sup.7 is hydrogen or alkyl,and their salts, processes for their preparation, compositions containing them and their use for controlling harmful fungi or pests, and also compounds of the formula VI ##STR2## and their salts, processes for their preparation, compositions containing them and their use as intermediates and for controlling pests are described.Type: GrantFiled: November 10, 1994Date of Patent: October 15, 1996Assignee: BASF AktiengesellschaftInventors: Oliver Wagner, Karl Eicken, Norbert G otz, Harald Rang, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5563286Abstract: A process is disclosed for the removal of the 4-protected hydroxy group from compounds of the following formula: ##STR1## where A is --COOAlkyl and B is hydroxy, or A and B together represent either oxo or .dbd.CHCOOAlkyl, where X.sup.1 and X.sup.2 are the same or different and represent hydrogen or a hydroxy-protecting group, and where X.sup.3 is ##STR2## with a hydrogen radical source, such as tributyltin hydride or tris(trimethylsilyl)silane, and a radical initiator, such as AIBN or irradiation.Type: GrantFiled: May 16, 1995Date of Patent: October 8, 1996Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rolf E. Swenson
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Patent number: 5523462Abstract: Cyclohexenone derivatives I ##STR1## The cyclohexenone derivatives I are suitable as herbicides and for regulating plant growth.Type: GrantFiled: April 19, 1994Date of Patent: June 4, 1996Assignee: BASF AktiengesellschaftInventors: Juergen Kast, Thomas Zierke, Matthias Bratz, Ulf Misslitz, Norbert Meyer, Andreas Landes, Wilhelm Rademacher, Karl-Otto Westphalen, Helmut Walter
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Patent number: 5491255Abstract: A process for the transesterification of dimethyl succinylsuccinate with one or more aliphatic alcohols which in each case have at least 2 C atoms, in the presence of an acidic catalyst and in the presence or absence of a diluent which is inert under the reaction conditions, with exclusion of oxygen and under pressure, at least one of the two methoxy groups being replaced by the oxy group corresponding to the alcohol used.Type: GrantFiled: October 18, 1994Date of Patent: February 13, 1996Assignee: Chemie Linz GmbHInventors: Franz T. Schwarz, Johann Altreiter, Franz Mostl
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Patent number: 5488136Abstract: Racemates are obtained from non-racemic 3-oxocyclopentane or 3-oxocyclohexane carboxylic acids or their esters by esterification and ketalization of the non-racemic acid with orthoformic acid ester in an alocohol, racemization and hydrolysis of the product obtained with an alcoholate and isolation of the racemate.Type: GrantFiled: April 16, 1993Date of Patent: January 30, 1996Assignee: Boehringer Ingelheim KGInventor: Rainer Sobotta
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Patent number: 5468880Abstract: Improvement in the technique of synthesizing prostaglandins, particularly those having at least one halogen atom at the 16- or 17-position, which comprises introducing a .omega. chain into the aldehyde thereby to enable considerable yield improvement in the production of .alpha.,.beta.-unsaturated ketones, and which does not involve hydrogen generation and can insure safe operation.A method of producing .alpha.,.beta.-unsaturated ketones by reacting aldehyde with 2-oxoalkyl phosphonate, wherein the reaction was carried out under the presence of a base and a zinc compound.Type: GrantFiled: May 31, 1994Date of Patent: November 21, 1995Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkyujoInventors: Ryuji Ueno, Tomio Oda
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Patent number: 5453464Abstract: This invention provides the use and preparation of certain 2,2'-diacetyl-bisacetoacetates and bis(beta-ketoesters). These compounds are useful in coating formulations as crosslinkers in conjunction with polyester, acrylic and/or other hydroxylated resins to provide coatings that cure at about 100.degree. and 175.degree. C. Certain combinations of these crosslinkers and resins cure at unusually low temperatures and provide films with good combinations of flexibility, hardness and adhesion.Type: GrantFiled: April 28, 1994Date of Patent: September 26, 1995Assignee: Eastman Chemical CompanyInventors: J. Stewart Witzeman, Allen L. Crain
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Patent number: 5453534Abstract: A process for the preparation of alkoxycarboxylic acid esters of the general formula I ##STR1## in which Y denotes CR.sup.4 R.sup.5 or CR.sup.4 R.sup.5 -CR.sup.6 R.sup.7,R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 denote C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.8 cycloalkyl, aryl, C.sub.7 -C.sub.20 aralkyl, and C.sub.7 -C.sub.20 alkylaryl andR.sup.2, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 can additionally denote hydrogen, and n is 0 or 1,by the reaction of hydroxycarboxylic acid esters of the general formula II ##STR2## in which R.sup.2, R.sup.3, R.sup.8, Y, and n have the aforementioned meanings, with alcohols of the general formula IIIR.sub.1 --OH (III),in which R.sup.1 has the aforementioned meanings, in the presence of heterogeneous catalysts at temperatures ranging from 100.degree. to 400.degree. C. and pressures ranging from 0.01 to 150 bar, wherein the heterogeneous catalysts used are zeolites and/or hydrothermally prepared phosphates.Type: GrantFiled: June 27, 1994Date of Patent: September 26, 1995Assignee: BASF AktiengesellschaftInventor: Karsten Eller
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Patent number: 5449684Abstract: Compounds isolated from a marine sponge, and derivatives thereof, have the formulae: ##STR1## in which R.sup.1 is H or lower alkyl; R.sup.2 is OH or CH.sub.3 ; R.sup.3 is OH or CH.sup.3, and R.sup.4 H or MPTA. The compounds have antitumor and antiviral activity. The invention also provides pharmaceutical compositions containing the compounds and methods of treatment employing them.Type: GrantFiled: February 3, 1994Date of Patent: September 12, 1995Assignee: PharmaMar, S.A.Inventors: Jun-Ichi Tanaka, Tatsuo Higa, Khanit Suwanoborirux, C. W. Jefford, G. Bernardinelli, Dolores G. Gravalos
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Patent number: 5446191Abstract: A 1-cyclohexyl-1-methylethylperoxy carbonate represented by the formula: ##STR1## (wherein n.sub.1 stands for 1 or 2 and, when n.sub.1 is 1, R.sub.1 stands for an alkyl group of up to 14 carbon atoms, an aralkyl group of up to 14 carbon atoms, an alkoxyalkyl group of up to 14 carbon atoms, a cycloalkyl group of up to 14 carbon atoms, or an aryl group of up to 14 carbon atoms, and when n.sub.1 is 2, R.sub.1 stands for an alkylene group of up to 16 carbon atoms, an aralkylene group of up to 16 carbon atoms, an oxaalkylene group of up to 16 carbon atoms, a cycloalkylene group of up to 16 carbon atoms, or a phenylene group of up to 16 carbon atoms) is a novel compound. It is produced by causing a chloroformate represented by the formula: ##STR2## (wherein n.sub.2 has the same meaning as n.sub.1 in the preceding formula) to react with 1-cyclohexyl-1-methylethylhydroperoxide.Type: GrantFiled: February 2, 1994Date of Patent: August 29, 1995Assignee: NOF CorporationInventors: Shuji Suyama, Tooru Nishikawa, Masaru Matsushima, Hiroshi Okada
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Patent number: 5426186Abstract: This invention encompasses compounds of the formula: ##STR1## and pharmaceutically acceptable non-toxic salts thereof wherein: n is 0, 1, or 2, X is ##STR2## and R.sub.1, R.sub.2, R.sub.3, W and Y are variables These compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs thereof and are useful in the diagnosis and treatment of anxiety, sleep, and seizure disorders, overdose with benzodiazepine type drugs, and enhancement of alertness.Type: GrantFiled: March 3, 1993Date of Patent: June 20, 1995Assignee: Neurogen CorporationInventors: Kenneth Shaw, Alan Hutchison
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Patent number: 5391755Abstract: A convergent synthesis of 19-nor-vitamin D compounds, specifically 19-nor-1.alpha.,25-dihydroxyvitamin D.sub.3, is disclosed. The synthesis can also readily be utilized for preparing other 1.alpha.-hydroxylated 19-nor-vitamin D compounds. The key step in the synthesis is a suitable application of Lythgoe's procedure i.e. a Horner-Wittig reaction of the lithium anion of a phosphine oxide with a Windaus Grundmann ketone to give, after any necessary deprotection, the desired 19-nor-vitamin D compound.Type: GrantFiled: January 13, 1994Date of Patent: February 21, 1995Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rolf E. Swenson
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Patent number: 5380900Abstract: Disclosed herein is an .alpha.-methylene-cyclopentanone derivative represented by the formula [I] below which is useful as an intermediate for pharmaceuticals and insecticides, especially prostaglandins. Also disclosed herein is a process for producing the derivative advantageously on an industrial scale. ##STR1## where X denotes (.alpha.-OZ, .beta.-H) or (.alpha.-H, .beta.-OZ), with Z representing a protecting group for the hydroxyl group; U denotes (.alpha.-H, .beta.-R.sup.1) or (.beta.-R.sup.1, .alpha.-H); R.sup.1 denotes ##STR2## where R.sup.2 denotes a protected hydroxyl group, a substituted or unsubstituted C.sub.1-15 alkyl group, a substituted or unsubstituted C.sub.2-15 alkenyl group, a substituted or unsubstituted C.sub.2-15 alkynyl group, or a substituted or unsubstituted C.sub.6-15 aryl group; Z' denotes a protecting group for the hydroxyl group; and k is 0 or 1).Type: GrantFiled: February 12, 1992Date of Patent: January 10, 1995Assignee: Nissan Chemical Industries, LimitedInventors: Fumie Sato, Kazutaka Arai, Katsuaki Miyaji
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Patent number: 5359126Abstract: Preparing cyclohexanediones of the formula ##STR1## an aldehyde is reacted with a ketene to give a polymer having the repeating unit ##STR2## wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3. The unsaturated ester is contacted with a basic catalyst to cyclize it to the cyclic dione ester of the formula ##STR3## and this ester is then hydrolyzed and decarboxylated to give the cyclohexanedione give the productwherein:R is selected, e.g.Type: GrantFiled: February 7, 1994Date of Patent: October 25, 1994Assignee: Eastman Chemical CompanyInventor: Charles A. McCombs
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Patent number: 5349112Abstract: Novel cyclic anti-tumor promoter compounds and therapeutic compositions are disclosed, along with method for their production and use as anti-cancer and cancer-prevention agents.Type: GrantFiled: November 26, 1993Date of Patent: September 20, 1994Assignee: University of HawaiiInventor: Marcus A. Tius
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Patent number: 5346919Abstract: The present invention relates to the compound A of the formula (A), the related compound B, carboxylic acid derived from acid anhydride group of these compounds and esters and salts thereof, microorganisms for producing the compounds, methods for producing the compounds A and/or B by using the microorganisms, and a treated or untreated fermentation broth obtained by culturing strains belonging to genus Zopfiella or Zopfiella curvata No. 37-3 strain. ##STR1## The present invention provides the compounds A and B, derivatives thereof, and treated or untreated fermentation broth obtained by culturing the strains belonging to genus Zopfiella or Zopfiella curvata No. 37-3 strain, which show an excellent activities as antifungal agent and anti-thrombotic agent.Type: GrantFiled: August 2, 1993Date of Patent: September 13, 1994Assignee: Nissan Chemical Industries, Ltd.Inventors: Tsuneo Watanabe, Takeshi Yasumoto, Michio Murata, Michito Tagawa, Hiroyuki Narushima, Takashi Furusato, Masao Kuwahara, Masami Hanaue, Tatsuya Seki
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Patent number: 5347039Abstract: This invention is directed to a method for stereoselectively preparing a syn-dihydroxylated compound comprising reacting a 3-hydroxyket-1-one with a borohydride in the presence of titanium derivative.Type: GrantFiled: August 11, 1993Date of Patent: September 13, 1994Assignee: Rhone-Poulenc Rorer S.A.Inventors: Patrick Leon, Xavier Radisson, Viviane Massonneau
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Patent number: 5344939Abstract: The preparation of magnesium benzyl fluoromalonate and other equivalent materials, the synthetic equivalents of the --CH.sub.2 F moiety, is described. Reaction between these reagents and the in situ-formed imidazolides of various carboxylic acids gives beta-keto-alpha-fluoroesters, which upon hydrogenation and spontaneous decarboxylation yields fluoromethyl ketones in excellent yields. The overall transformation from RCOOH to RCOCH.sub.2 F is thus illustrated.Type: GrantFiled: March 11, 1993Date of Patent: September 6, 1994Assignee: Prototek, Inc.Inventor: James T. Palmer
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Patent number: 5336484Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising a polymeric material capable of forming a coating on the gastrointestinal tract and an x-ray producing agent of the formula ##STR1## and methods for their use in diagnostic radiology of the gastrointestinal tract wherein ##STR2## Z=H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R=C.sub.1 -C.sub.25 alkyl, cycloalkyl, aryl or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl, lower-alkenyl, lower-alkynyl, lower-alkylene or lower-alkoxy-carbonyloxy,n is 1-5;y is 0-4; andw is 1-4.Type: GrantFiled: March 31, 1993Date of Patent: August 9, 1994Assignee: Sterling Winthrop Inc.Inventors: Edward R. Bacon, Sol J. Daum, Kimberly G. Estep, Kurt A. Josef, Brent D. Douty, Carl R. Illig
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Patent number: 5334740Abstract: Cyclohexanetriol derivatives represented by the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are the same or different, and each denotes a hydrogen atom or a protecting group of a hydroxyl group,X denotes an oxygen atom, .dbd.CHCH.sub.2 OR.sup.4, .dbd.CHCHO or .dbd.CHCO.sub.2 R.sup.5, Y denotes a hydrogen atom and Z denotes --OR.sup.6, or Y and Z together form a single bond; or X and Z together form .dbd.NO--, .dbd.CHCH(OR.sup.7)O-- or .dbd.CHCO.sub.2 -- and Y is a hydrogen atom, R.sup.4 and R.sup.6 denote a hydrogen atom or a protecting group of a hydroxyl group respectively, R.sup.5 denotes a lower alkyl group, and R.sup.7 denotes a hydrogen atom or a lower alkyl group.Said derivatives are useful as synthetic intermediates of 1-hydroxyvitamin D derivatives.Type: GrantFiled: March 13, 1992Date of Patent: August 2, 1994Assignee: Kurary Co., Ltd.Inventors: Takashi Takahashi, Manzo Shiono
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Patent number: 5318769Abstract: Disclosed are contrast agents of the formula ##STR1## contained in aqueous compositions and methods for their use in diagnostic radiology of the gastrointestinal tract whereinX= ##STR2## Z=H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R=C.sub.1 -C.sub.25 alkyl, cycloalkyl, aryl, or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl, lower-alkenyl, lower-alkynyl, lower-alkylene, lower-alkoxy-carbonyloxy;n=1-5;y=0-4; andw=1-4in an aqueous pharmaceutically acceptable carrier.Type: GrantFiled: March 31, 1993Date of Patent: June 7, 1994Assignee: Sterling Winthrop Inc.Inventors: Edward R. Bacon, Sol J. Daum, Kimberly G. Estep, Kurt A. Josef, Brent D. Douty, Carl R. Illig
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Patent number: 5302745Abstract: Process for the preparation of alkyl 3-oxo-2-pentyl-1-cyclopentene acetates starting from an epoxy-ester of formula ##STR1## wherein R designates a lower linear or branched alkyl radical of C.sub.1 -C.sub.6 and wherein the wavy line stands for a C--C bond of cis or trans configuration via an isomerization process.Type: GrantFiled: June 16, 1993Date of Patent: April 12, 1994Assignee: Firmenich S.A.Inventor: Beat Winter
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Patent number: 5294731Abstract: A process for the preparation of .beta.-hydroxycarboxylates of the general formula I ##STR1## in which R.sup.1 and R.sup.2 individually denoteC.sub.1 -C.sub.20 alkyl optionally substituted by C.sub.1 -C.sub.8 alkoxy and/or halogen, C.sub.3 -C.sub.20 alkoxycarbonylalkyl, C.sub.2 -C.sub.20 alkenyl, C.sub.5 -C.sub.30 acetalalkenyl, aryl optionally mono- to penta-substituted by C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, and/or halogen, C.sub.7 -C.sub.20 aralkyl, C.sub.7 -C.sub.20 aralkenyl, hetaryl, C.sub.3 -C.sub.20 cycloalkyl, or C.sub.4 -C.sub.20 cycloalkylalkyl,or together denote a C.sub.2 -C.sub.8 alkylene chainand one or other of R.sup.1 and R.sup.2 denotes hydrogen, andR.sup.3 denotes hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.20 alkenyl, aryl optionally mono- to penta-substituted by C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, and/or halogen, C.sub.7 -C.sub.20 aralkyl, C.sub.3 -C.sub.20 cycloalkyl, or C.sub.4 -C.sub.20 cycloalkylalkyl, andR.sup.4 denotes C.sub.1 -C.sub.20 alkyl, C.sub.Type: GrantFiled: March 23, 1993Date of Patent: March 15, 1994Assignee: BASF AktiengesellschaftInventors: Joachim Paust, Wolfgang Siegel
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Patent number: 5286746Abstract: Antihypercholesterolemic activity is exhibited by compounds of the formula ##STR1## wherein: X is hydrogen, alkali metal or ammonium;Y is hydrogen, alkyl, cycloalkyl, aryl, or aralkyl; ##STR2## R is hydrogen, alkyl, ammonium, alkylammonium, or alkali metal (such as Na, Li, or K); andn is 1 or 2.Type: GrantFiled: December 20, 1991Date of Patent: February 15, 1994Assignee: E. R. Squibb & Sons, Inc.Inventor: Kathleen M. Poss
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Patent number: 5254708Abstract: The present invention relates to substituted cyclopentanone and cyclohexanone derivatives and substituted cyclopentenone and cyclohexenone derivatives, which are useful as intermediates for pharmaceutical products and agricultural chemicals and especially useful for the synthesis of prostaglandins, and also to a process for producing the same.Type: GrantFiled: December 14, 1990Date of Patent: October 19, 1993Assignee: Nissan Chemical Industries, Ltd.Inventors: Fumie Sato, Kazutaka Arai, Katsuaki Miyaji
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Patent number: 5239108Abstract: A process for producing an aliphatic or alicyclic aldehyde is disclosed, which process comprises the step of hydrogenating an aliphatic or alicyclic carboxylic acid or a derivative thereof with molecular hydrogen in the presence of a catalyst, wherein the catalyst is a zirconium oxide catalyst which contains chromium as an essential component, has a weakly basic site amount of more than 0.03 mmol/g as determined by a temperature programmed desorption method using carbon dioxide as an adsorbate in which the amount of carbon dioxide desorbed in the temperature range of from 100.degree. to 250.degree. C. is measured, and has pores having a radius of from 20 to 500 .ANG. in an amount of not less than 0.1 cc/g and pores having a radius of from 1,000 to 50,000 .ANG. in an amount of not less than 0.05 cc/g as measured with a mercury porosimeter. Aldehydes can be obtained directly from aliphatic or alicyclic carboxylic acids or derivatives thereof in high yield.Type: GrantFiled: October 20, 1992Date of Patent: August 24, 1993Assignee: Mitsubishi Kasei CorporationInventors: Toshiharu Yokoyama, Naoko Matsuyama, Takao Maki
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Patent number: 5238602Abstract: Compounds of the formula ##STR1## wherein n stands for the number 0 or 1; the rings A.sup.1, A.sup.2 and A.sup.3 represent 1,4-phenylene, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also represents a 2,5-disubstituted pyrimidine ring or a trans-2,5-disubstituted m-dioxane ring; X.sup.1 represents a single covalent bond, --COO--, --OOC--, --CH.sub.2 CH.sub.2 --, p--C.sub.6 H.sub.4 --, --CH.sub.2 CH.sub.2 --p-- C.sub.6 H.sub.4 --, --CH.sub.2 CH.sub.2 --p--C.sub.6 H.sub.4 --CH.sub.2 CH.sub.2 -- or, insofar as the rings A.sup.1 and A.sup.2 represent 1,4-phenylene, also --NON--; R.sup.2 represents 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or alkenyloxy, with the proviso that the oxygen atom in alkenyloxy is linked with a saturated carbon atom; and R.sup.1 signifies 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or, insofar as R.sup.2 represents alkenyloxy, also alkyl, their manufacture, as well as liquid crystalline mixtures and the use for electro-optical purposes.Type: GrantFiled: May 26, 1987Date of Patent: August 24, 1993Assignee: Hoffmann La Roche Inc.Inventors: Martin Petrzilka, Martin Schadt
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Patent number: 5235101Abstract: An improved process for the separation of enantiomers of a mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves adding an inert liquid to the reaction solution formed by: (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base; (ii) treating said salt solution with less that equimolar equivalents of a chiral organic nitrogenous base; (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt; (iv) addition of a countersolvent to the slurry formed in step (iii); (v) extracting the more soluble diastereomeric salt or the salt of carboxylic acid and the base added in step (i) into the countersolvent. The inert liquid and the countersolvent must be of sufficiently different density.Type: GrantFiled: January 24, 1992Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventors: Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
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Patent number: 5235100Abstract: A process for the separation of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process comprises:i) separating a racemic mixture of an aliphatic carboxylic acid or ester thereof having the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; cycloalkyl; alkyl-substituted cycloalkyl; C.sub.6 to C.sub.14 aryl; C.sub.1 to C.sub.6 alkylthio; C.sub.2 to C.sub.8 cycloalkylthio; C.sub.6 to C.sub.10 arylthio; C.sub.6 to C.sub.10 arylcarbonyl; C.sub.4 to C.sub.8 cycloalkenyl; trifluoromethyl; halo; or C.sub.4 to C.sub.Type: GrantFiled: January 24, 1992Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventors: Azfar A. Choudhury, Abbas Kadkhodayan, Deepak R. Patil
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Patent number: 5235095Abstract: An improved process for the separation of enantiomers of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves: (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base; (ii) treating said salt solution with one-half molar equivalent of a chiral organic nitrogenous base having a base strength no stronger than said organic or inorganic base; and (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt, the improvement being adding to the salt solution of step (ii) an inert organic or inorganic base that is soluble in the salt solution.Type: GrantFiled: January 24, 1992Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventors: Abbas Kadkhodayan, Deepak R. Patil, Azfar A. Choudhury
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Patent number: 5227505Abstract: The present invention relates to substituted cyclopentanone and cyclohexanone derivatives and substituted cyclopentenone and cyclohexenone derivatives, which are useful as intermediates for pharmaceutical products and agricultural chemicals and especially useful for the synthesis of prostaglandins, and also to a process for producing the same.Type: GrantFiled: December 14, 1990Date of Patent: July 13, 1993Assignee: Nissan Chemical Industries, Ltd.Inventors: Fumie Sato, Kazutaka Arai, Katsuaki Miyaji
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Patent number: 5221765Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.2 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 75.degree. C. to about 200.degree. C.Type: GrantFiled: January 24, 1992Date of Patent: June 22, 1993Assignee: Ethyl CorporationInventors: Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
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Patent number: 5214160Abstract: The invention concerns novel odorants of formula I wherein R is hydrogen or methyl. ##STR1## The invention also concerns fragrance compositions containing I. Formula I is intended to particularly embrace as the racemates, (.+-.)-3.alpha.-acetyl-3.beta.,4.beta.,5,5-tetramethyl-2,3,4,4a.beta.,5,6, 7,8-octahydronapthalene and (.+-.)-3.alpha.-acetyl-4.beta.,5,5,-trimethyl-2,3.beta.,4,4a.beta.,5,6,7,8 -octahydronapthalene.Type: GrantFiled: September 25, 1992Date of Patent: May 25, 1993Assignee: Givaudan CorporationInventors: Franz Etzweiler, Daniel Helmlinger, Cornelius Nussbaumer, Mario Pesaro
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Patent number: 5214056Abstract: A 1,3,2-dioxathiolane oxide derivative is represented by the following formula: ##STR1## wherein X represents --S(O)-- or --S(O).sub.2 --;R.sup.1 represents a hydrogen atom, an alkali metal atom, a benzyl group, or a lower alkyl group;R.sup.2 represents a lower alkyl group which may be substituted with a methylthio group, or a benzyl group, andR.sup.3 and R.sup.4 may be the same or different and independently represent a hydrogen atom, an alkyl group having one to ten carbon atoms, a lower alkyl group substituted with a guanidyl group, a cycloalkyl group having 3 to 6 carbon atoms, a phenyl group, a benzyl group, or a phenethyl group, or together form an alkylene group.Type: GrantFiled: August 20, 1991Date of Patent: May 25, 1993Assignee: Japan Tobacco Inc.Inventors: Jun-ichi Haruta, Masahiro Tanaka, Itsuo Uchida, Akira Ohta, Shin Hara
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Patent number: 5206389Abstract: These acrylates are those of formulae: ##STR1## where R=C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, aryl, arylalkyl or alkylaryl; Y=C.sub.1 -C.sub.12 alkyl, C.sub.6 -C.sub.12 aryl, heterocyclic radical whose ring contains from 5 to 10 members and whose heteroatom is chosen from N, O and S, an alkylaryl in which the alkyl part contains from 1 to 4 carbon atoms, Y not being able to denote 1,4-phenylene when R denotes methyl; and Z=hydrocarbon radical containing at least 2 C forming with O and the 2 adjacent Cs a ring containing from 4 to 8 members.To prepare them, an acrylate of formula CH.sub.2 .dbd.CH--COOR is reacted with a dialdehyde OHC--Y--CHO in the presence of an effective quantity of at least one functionalisation catalyst.The invention also relates to the preparation of new polymers and copolymers from the said acrylates.Type: GrantFiled: June 27, 1991Date of Patent: April 27, 1993Assignee: AtochemInventors: Marie-Christine Berthe, Paul Caubere, Yves Fort
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Patent number: 5202460Abstract: Terpene derivatives of formula I, their preparation and their use. In formula I, R represents a hydrogen atom or an alkanoyl radical and R' represents a hydrogen atom or an aliphatic hydrocarbon radical.Type: GrantFiled: December 12, 1991Date of Patent: April 13, 1993Assignee: Rhone Poulenc SanteInventor: Claude Mercier
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Patent number: 5194671Abstract: The invention relates to a process for the preparation of .beta.-ketocarboxylic acid esters of the general formula ##STR1## in which R.sup.1 is an alkyl radical having 1 to 4 C atoms, R.sup.2 is an alkyl radical or alkenyl radical having 2 to 15 C atoms or a phenyl radical and R.sup.3 is hydrogen or an alkyl or alkenyl radical having 1 to 6 C atoms, characterized in that acetocarboxylic acid esters of the general formula ##STR2## in which R.sup.1 and R.sup.3 are as defined, are reacted with calcium hydroxide or calcium oxide in the presence of an organic solvent and in the absence of water, the calcium chelate complexes formed are acylated with carboxylic acid chloride and the products are then cleaved with aqueous ammonium salt solution to form the .beta.-ketocarboxylic acid esters of formula (I).The .beta.Type: GrantFiled: March 11, 1992Date of Patent: March 16, 1993Assignee: Wacker-Chemie GmbHInventor: Josef Meier