Plural Alicyclic Rings Containing Patents (Class 568/816)
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Publication number: 20030186939Abstract: A &ohgr;-cycloalkyl-prostaglandin E2 derivatives of the formula (I) 1Type: ApplicationFiled: September 11, 2002Publication date: October 2, 2003Inventors: Kousuke Tani, Shuichi Ohuchida
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Publication number: 20030119666Abstract: A catalyst which contains at least one element selected from the group consisting of Group V elements, Group VI elements, Group VII elements, Group VIII elements, Group IX elements, Group X elements, and Group XI elements in the periodic table, and is to be used for subjecting an epoxy alcohol represented by a general formula (1) to a hydrogenolysis reaction in the presence of at least one solvent selected from the group consisting of ethers, esters, aromatic hydrocarbon compounds, alicyclic hydrocarbon compounds and aliphatic hydrocarbon compounds. By use of such a catalyst, a both end-hydroxyl group-terminated diol having a high purity can be produced efficiently.Type: ApplicationFiled: March 26, 2002Publication date: June 26, 2003Inventors: Yasushi Kadowaki, Masato Kaneda, Hiroshi Uchida
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Patent number: 6576787Abstract: Hydroxymethyl-group-containing alicyclic compounds that are useful for making photosensitive resins and other functional polymers. Processes for producing the hydroxymethyl-group-containing alicyclic compounds. Polymerizable alicyclic compounds. The alicyclic moieties in all of these compounds may be a polycyclic ring such as a perhydroindene ring, a decalin ring, a perhydrofluorene ring, a perhydroanthracene ring, a perhydrophenanthrene ring, a tricyclo[5.2.1.02.6]decane ring, a perhydroacenaphthene ring, or a perhydrophenalene ring.Type: GrantFiled: October 6, 2000Date of Patent: June 10, 2003Assignee: Daicel Chemical Industries, Ltd.Inventors: Tatsuya Nakano, Hiroshi Shimojitosyo
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Patent number: 6562782Abstract: The present invention related to an oligocycloalkanoid compound comprising formula (I) wherein m, n, and o are independently an integer from 0 to 2; A1 through A10 are independently a direct link, alkylene, alkylene-O—, carbonyl, oxygen, or sulfur; X and Y are independently hydrogen, hydroxy, alkyl, or in combination an electrophilic group; and R1 through R10 are independently hydrogen, hydroxy, alkyl, alkenyl, alkynyl, substituted or unsubstituted aryl, N-, S-, or O-heterocycles, fused or multi-ring aryl with or without hetero ring members, arylalkyl, arylalkenyl, arylalkynyl, alkylphenyl, alkenylphenyl, alkynylphenyl, alkoxy, alkenyloxy, alkynyloxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylalkoxy, alkylacyl, alkenylacyl, alkynylacyl, arylacyl, aroyl, alkylaroyl, aminoaroyl, aminoalkylacyl, aminoalkyl, aminoalkenyl, aminoalkynyl, amino, alkylamino, alkenylamino, alkynylamino, arylamino, dialkylamino, dialkenylamino, dialkynylamino, arylalkylamino, arylalkType: GrantFiled: May 10, 2000Date of Patent: May 13, 2003Assignee: University of RochesterInventors: Benjamin L. Miller, Robert D. Hubbard
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Patent number: 6548715Abstract: A compound of the formula I: in which P is hydrogen or alkyl; Y and Y′ are each hydrogen or, when taken together, represent a group ═CH2; W and W′ are each hydrogen; X is selected from the group consisting of a hydroxyalkyl, a hydroxyalkoxy, an alkoxy optionally comprising an epoxide function, a hydroxyalkene, a hydroxyalkadiene, a hydroxyalkyne and isomeric forms thereof; and a) either R1 and R3 or R′3 form a saturated 5- or 6-membered carbocyclic ring and R2, R′2, R3 or R′3, R4, R′4, R5 and R′5 are each independently hydrogen or alkyl; or b) R2 or R′2 and R4 or R′4 form a saturated 5- or 6-membered carbocyclic ring, and R1, R2 or R′2, R3, R′3, R4 or R′4, R5 and R′5 are each independently hydrogen or alkyl; or c) R3 or R′3 and R5 or R′5 form a saturated or unsaturated 5- or 6-membered carbocyclic ring, and R1, R2, R′2, R3 or R′3, R4, R′4, and R5 or R′5 are each indepType: GrantFiled: October 28, 1999Date of Patent: April 15, 2003Assignee: Laboratoire Theramex S.A.Inventors: Roger Bouillon, Maurits Vandewalle, Pierre Jean De Clercq
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Publication number: 20030018221Abstract: The present invention provides a process for producing an acetylenediol continuously by reacting a ketone with acetylene in the presence of an alkali catalyst, which process comprises continuously feeding, into a first-stage reactor, a reaction solvent, an alkali catalyst, a ketone and acetylene to give rise to a reaction, continuously introducing the reaction mixture into a second-stage reactor, and continuously feeding a fresh portion of the same ketone into the second-stage reactor to give rise to a reaction.Type: ApplicationFiled: June 12, 2002Publication date: January 23, 2003Inventors: Hideki Omori, Goro Sawada, Hideo Fukuda, Kazuhiro Imanishi, Tomohiko Sato
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Patent number: 6504067Abstract: An industrial process to obtain xanthophyll concentrates of high purity from plant extracts, comprising: refining the plant extracts by treating them with a diluted alkali, followed by treating them with a diluted organic or inorganic acid in order to eliminate impurities and undesirable components and obtaining a refined extract; saponifying the refined extract by means of a strongly alkali aqueous solution; treating the diluted saponified mass with a dilute organic or inorganic acid to adjust the pH to a value from 4 to 7, in order to separate a xanthophylls concentrate; and removing any remaining impurities by extracting them by means of hexane.Type: GrantFiled: November 24, 1999Date of Patent: January 7, 2003Assignee: Industrial Organica S.A. DE C.V.Inventors: Ricardo Montoya-Olvera, Juan-Roberto Elizondo-Mireles, Carlos-Javier Torres-Gómez, José-Odon Torres-Quiroga
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Publication number: 20020147371Abstract: Novel proteins of Flavobacterium sp. R1534 and the DNA sequences which encode these proteins are disclosed which provide an improved biosynthetic pathway from famesyl pyrophosphate and isopentyl pyrophosphate to various carotenoid precursors and carotenoids, especially &bgr;-carotene, lycopene, zeaxanthin and cantaxanthin.Type: ApplicationFiled: April 11, 2000Publication date: October 10, 2002Inventors: Hans-Peter Hohmann, Luis Pasamontes, Michel Tessier, Adolphus van Loon
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Patent number: 6420614Abstract: A process for obtaining 3′-epilutein, by epimerization of a lutein-containing extract with an aqueous solution of a strong organic acid which is slowly added under agitation at room temperature, in the presence of an organic aprotic media, to obtain 3′-epilutein(crystals) in a solution which is neutralized with an alkali and extracting the 3′-epilutein from said solution by means of an organic media, then washing and drying the crystals and purifying them by chromatography by means of a chromatography column.Type: GrantFiled: October 10, 2000Date of Patent: July 16, 2002Assignee: Industrial Organica, S.A. DE C.V.Inventors: Conrad Hans Eugster, Ricardo Montoya-Olvera, José-Odon Torres-Quiroga
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Patent number: 6380442Abstract: A practical and effective process for isolating and purifying mixed carotenoids containing higher concentrations of specific compounds, such as all-trans lutein, without the use of harmful organic solvents, is disclosed. The process employs hydrolysis of carotenoid esters in a mixture of isopropanol, water, and alkali to separate the carotenoids from other impurities. The carotenoids are purified further using aqueous precipitation, followed by centrifugation and drying under vacuum. The product is a fine crystalline powder with very low residual solvents (hexane 0.22 ppm; isopropanol 0.53 ppm) suitable for human consumption, either in nutritional supplements or as a food additive.Type: GrantFiled: October 10, 2001Date of Patent: April 30, 2002Assignee: BioActives, LLCInventors: Doddabele L. Madhavi, Daniel I. Kagan
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Patent number: 6376722Abstract: A lutein to zeaxanthin isomerization process which includes a saponification or alkali treatment of a plant extract containing lutein followed by a heating period under controlled conditions, is carried out in the presence of a surface active agent having an HLB of from 1 to 40 as a catalyst for the lutein to zeaxanthin isomerization reaction, at a temperature between 70 to 140° C., in order to obtain a reaction product with high zeaxanthin concentrations of up to 80% of the total carotenoids.Type: GrantFiled: October 29, 1998Date of Patent: April 23, 2002Inventors: Vicente Ernesto Ridaura Sanz, Oscar Rubén García Correa, Armando Prado Naranjo
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Patent number: 6353141Abstract: Functionalized cyclopentene-derived oligomer mixtures are prepared by reacting oligomer mixtures which contain ethyleneic double bonds in one or more reaction steps starting from cyclopentene-derived oligomer mixtures of the formula I R1R2C═[═CH—(CH2)3—CH═]n═CR3R4 (I) where n is an integer from 1 to 15, and R1, R2, R3 and R4 are, independently of one another, hydrogen or alkyl, and are used as described.Type: GrantFiled: June 21, 1999Date of Patent: March 5, 2002Assignee: BASF AktiengesellschaftInventors: Edgar Zeller, Gerhard Schulz, Bernhard Geissler, Michael Röper, Guido Voit
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Publication number: 20020016516Abstract: An adamantanemethanol derivative of the invention is represented by the following formula (1), wherein Ra is a hydrogen atom or a hydrocarbon group; Rb is a hydrocarbon group having a carbon atom, to which carbon atom at least one hydrogen atom is bonded, at a bonding site with the adjacent carbon atom; Rc, Rd and Re are each a hydrogen atom, a hydroxyl group which may be protected by a protective group or the like; provided that a hydroxyl group protected by a protective group or the like is bonded to at least one carbon atom constituting the adamantane skeleton when Ra is a hydrogen atom or a methyl group and Rb is a methyl group; and at least one substituent, in addition to the HO—C(Ra) (Rb)— group indicated in the formula (1), is bonded to the adamantane ring when one of Ra and Rb is a methyl group and the other is an ethyl group.Type: ApplicationFiled: December 21, 1999Publication date: February 7, 2002Inventors: TATSUYA NAKANO, HIROSHI SHIMOJITOSYO
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Patent number: 6329557Abstract: The present invention provides an industrial scale process for obtaining lutein and zeaxanthin concentrates of high purity from saponified marigold extracts that may have high levels of chlorophyll.Type: GrantFiled: June 9, 2000Date of Patent: December 11, 2001Assignee: Prodemex, S.A. de C.V.Inventors: Gustavo Rodriguez, Mario-David Torres-Cardona, Alejandro Diaz
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Patent number: 6262316Abstract: An oral preparation for the prophylactic and/or therapeutic treatment of inflammation in the mucous membrane of mammalian gastrointestinal tract (especially the human stomach) caused by Hicobacter sp. (especially H. pylori) infection is described. The preparation comprises a prophylactically and/or therapeutically effective amount of at least one type of xanthophylles. The most preferred xanthophyll is astaxanthin which is soluble in oil, preferably naturally produced astaxanthin which is esterified with fatty acids. The oral preparation may further comprise carbohydrate structures, such as those which derive from the cell wall of the production alga Haematococcus sp. The preparation may also comprise a prophylactically and/or therapeutically effective amount of a water soluble antioxidant, such as ascorbic acid (vitamin C). The oral preparation is presented in a separate unit dose or in mixture with food.Type: GrantFiled: January 21, 2000Date of Patent: July 17, 2001Assignee: Astacarotene ABInventors: Torkel Wadström, Pär Alejung
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Patent number: 6255439Abstract: 1,1 -Bis(4-hydroxyphenyl)-3-alkylcyclohexanes, as illustrated by 1,1-bis (4-hydroxyphenyl)-3-pentadecylcyclohexane, are prepared by hydrogenating a composition comprising 3-alkylphenols to the corresponding cyclohexanol, oxidizing the cyclohexanol to a cyclohexanone and contacting the cyclohexanone with phenol in the presence of an acidic catalyst. The preferred 3-alkylphenols are those derived from cashew nut shell liquid. The products can be used to prepare polycarbonates.Type: GrantFiled: August 31, 2000Date of Patent: July 3, 2001Assignee: General Electric CompanyInventors: Chilukuri Ver Avadhani, Prakash Purushottam Wadgaonkar, Swaminathan Sivaram
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Patent number: 6191293Abstract: Trans-xanthophyll ester concentrates having a trans-xanthophyll ester content of at least four times greater and preferably at least nine times greater than the cis-xanthophyll ester content are obtained. Xanthophyll ester concentrates having a total xanthophyll ester content of at least 40 wt. % and preferably greater than about 55 wt. % are also obtained.Type: GrantFiled: January 12, 1999Date of Patent: February 20, 2001Assignee: Inexa, Industria Extractora C.A.Inventor: Luis W. Levy
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Patent number: 6169217Abstract: The method of the invention uses raw corn, or a corn by-product as a source. The source is mixed with an alcohol to produce an alcohol-corn slurry. Centrifugation or filtration produces a clear filtrate from the alcohol-corn slurry. A membrane filtration step is then used to separate purified xanthophylls. Other steps may be combined with the basic process to produce additional corn products, such as oil and zein.Type: GrantFiled: October 20, 1999Date of Patent: January 2, 2001Assignee: Board of Trustees of the University of IllinoisInventor: Munir Cheryan
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Patent number: 6162954Abstract: The invention relates to compounds of the general formula ##STR1## in which R.sup.1 to R.sup.7 are, independently, H, methyl or ethyl, R.sup.8 +R.sup.9 together form methylene (--CH.sub.2 --) or a single bond, or R.sup.1 +R.sup.2 together form --(CH.sub.2).sub.n --, with n being 3 or 4, or R.sup.3 +R.sup.5 or R.sup.5 +R.sup.7 represent methylene or a single bond; and the presence of at least one cyclopropane ring in the molecule is compulsory and the side chain can be saturated or contains one double bond in position .alpha.,.beta. or .beta.,.gamma., a process for the manufacture of these compounds, compounds used to perform the process and the use of these compounds as an odorant or as an ingredient of an odorant composition.Type: GrantFiled: April 21, 1999Date of Patent: December 19, 2000Assignee: Givaudan Roure (International) SAInventors: Jerzy A. Bajgrowicz, Georg Frater
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Patent number: 6025531Abstract: A process for preparing an optically active alcohol by reacting a prochiral ketone corresponding to the optically active alcohol and an acid with a mixture of (1) a boron-containing compound selected from the group consisting of i) a borane compound which is obtained from an optically active .beta.-aminoalcohol and a boron hydride; or obtained from the optically active .beta.-aminoalcohol, a metal borohydride and an acid and ii) an optically active oxazaborolidine and (2) a metal borohydride; and a process for preparing an optically active amine by reacting an oxime derivative and an acid with a mixture of (1) a boron-containing compound selected from the group consisting of i) a borane compound which is obtained from an optically active .beta.-aminoalcohol and a boron hydride, or obtained from said optically active .beta.-aminoalcohol, a metal borohydride and an acid and ii) an optically active oxazaborolidine, and (2) a metal borohydride.Type: GrantFiled: June 3, 1998Date of Patent: February 15, 2000Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Naoto Konya, Gohfu Suzukamo
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Patent number: 5998678Abstract: A process for the preparation of the carotenoid Zeaxanthin by isomerization and optional hydrolysis of a carotenoid precursor with an alkaline reagent in a polar organic solvent selected from the group consisting of an ether, polyhydroxyl alcohol, an ether-alcohol or a combination thereof. Also disclosed is a method of improving the pigment power of an oleoresin or vegetable extract by isomerizing and optionally simutanously saponifying the optically active carotenoids found therein by the action of an alkaline reagent in an organic medium; oxidizing the resulting optically active dihydroxycarotene and; reducing the resulting optically active keto product to generate the 3,3' dihydroxycarotenoid as a racemic mixture.Type: GrantFiled: December 22, 1997Date of Patent: December 7, 1999Assignee: Investigaciones Quimicas y Farmaceutics, S.A.Inventors: Nuria Sanroma Virgili, Joan Carles Ferrater Martorell, Mildred De Bloos De Clercq, Juan A. Fernandez Martin
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Patent number: 5973211Abstract: A method of isomerizing lutein to yield a mixture of epimers of zeaxanthin includes the following steps: mixing a lutein-containing extract in a glycol solution to obtain a mixture, treating the mixture with alkali to obtain an alkali-containing mixture, reacting the alkali-containing mixture in the presence of heat for a duration consistent with achieving a desired level of isomerization of lutein to zeaxanthin.Type: GrantFiled: July 18, 1997Date of Patent: October 26, 1999Assignee: Prodemex, S.A. DE C.V.Inventor: Gustavo Rodriguez
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Patent number: 5936126Abstract: A process for the hydrogenation of an aromatic compound, in which at least one hydroxyl group is attached to an aromatic core, or an aromatic compound, in which at least one amino group is attached to an aromatic core, in the presence of a catalyst containing, as active metal, ruthenium and optionally one or more other Group IB, VIIB, or VIIIB metals, applied to a macroporous support.Type: GrantFiled: June 18, 1997Date of Patent: August 10, 1999Assignee: BASF AktiengesellschaftInventors: Thomas Ruhl, Boris Breitscheidel, Jochem Henkelmann, Wolfgang Reif, Helmuth Menig, Sabine Weiguny
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Patent number: 5929291Abstract: The invention relates to compounds of the general formula ##STR1## in which R.sup.1 to R.sup.7 are, independently, H, methyl or ethyl, R.sup.8 +R.sup.9 together form methylene (--CH.sub.2 --) or a single bond, or R.sup.1 +R.sup.2 together form --(CH.sub.2).sub.n --, with n being 3 or 4, or R.sup.3 +R.sup.5 or R.sup.5 +R.sup.7 represent methylene or a single bond; and the presence of at least one cyclopropane ring in the molecule is compulsory and the side chain can be saturated or contains one double bond in position .alpha.,.beta. or .beta., .gamma. a process for the manufacture of these compounds, compounds used to perform the process and the use of these compounds as an odorant or as an ingredient of an odorant composition.Type: GrantFiled: April 9, 1997Date of Patent: July 27, 1999Assignee: Givaudan Roure (International) SAInventors: Jerzy A. Bajgrowicz, Georg Frater
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Patent number: 5876782Abstract: This invention relates to the in sito process for converting non-free form xanthophylls to free xanthophylls in the biological material of the plant. The method, more particularly, relates to a method that would liberate xanthophylls by transesterification of acyl-xanthophylls in plant materials.Type: GrantFiled: May 14, 1997Date of Patent: March 2, 1999Assignee: Kemin Industries, Inc.Inventors: Benedikt J. Sas, Clifford Adams
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Patent number: 5847238Abstract: Improved methods for the recovery of xanthophylls from corn gluten meal are provided. More specifically, methods for the recovery of xanthophylls from corn gluten whereby relatively dry corn gluten is extracted with an organic alcohol followed by a saponification reaction to convert xanthophyll esters to xanthophylls is described. Also described are methods for the recovery of xanthophylls from corn gluten meal whereby relatively dry corn gluten meal is extracted with a first solvent containing and antioxidant and the resulting extract is, optionally, purified. Using these is methods, xanthophylls can be recovered from corn gluten meal in higher yields, at greater efficiencies, and in higher purity as to compared to prior art methods. Moreover, the xanthophyll products recovered in these methods are ideally suited for use in food products and in pharmaceuticals. These materials are especially suited for use in poultry feeds to provide the desired, healthy yellow color or hue in broiler and egg yolks.Type: GrantFiled: November 29, 1996Date of Patent: December 8, 1998Assignee: Cargill, IncorporatedInventors: Harapanahalli S. Muralidhara, Tracy Lee Cornuelle
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Patent number: 5792876Abstract: A process is described for producing acetals comprising reacting an aldehyde or a ketone with an alcohol in the presence of a titanium compound having an acetylacetone as a ligand, or in the presence of a compound selected from the group consisting of stannous chloride dihydrate, cerium chloride hexahydrate and bismuth chloride. The process can be used in the synthesis of unstable acetals or when water exists in the reaction mixture, and therefore the process can be used for a wide variety of applications.Type: GrantFiled: November 6, 1996Date of Patent: August 11, 1998Assignee: Kuraray Co., Ltd.Inventors: Hideharu Iwasaki, Masahiko Kitayama, Takashi Onishi
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Patent number: 5780693Abstract: A process for the conversion of lutein or of its esters into zeaxanthin by base-catalyzed isomerization is disclosed. The process is carried out by heating an optionally pre-treated lutein-containing material in a mixture of an aqueous solution of an alkali hydroxide and either dimethyl sulphoxide or an organic solvent based on saturated aliphatic and/or aromatic hydrocarbons at temperatures in the range from about 50.degree. C. to about 120.degree. C. The process is carried out in the presence of a phase transfer catalyst when an organic solvent based on hydrocarbons is used. Being carotenoids, lutein and zeaxanthin are used correspondingly, especially as pigments for egg yolk, the integuments and the subcutaneous fat of poultry, the flesh and the integuments of fish and crustaceans, as well as foodstuffs. Zeaxanthin is preferably used in many applications, since in comparable dosages it produces a more intensive golden yellow pigmentation than lutein.Type: GrantFiled: September 22, 1997Date of Patent: July 14, 1998Assignee: Roche Vitamins Inc.Inventors: Kurt Bernhard, Alfred Giger
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Patent number: 5780692Abstract: A process for producing a benzhydrol compound (II) which comprises hydrogenating a benzophenone compound (I) in the presence of a hydrogenation catalyst consisting of a transition metal complex, a base and an optically active diamine compound: ##STR1## wherein R.sup.1 to R.sup.10 each represents H, OH, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkanoyl, etc., R.sup.2 and R.sup.3, and R.sup.8 and R.sup.9 may form --CH.dbd.CH--CH.dbd.CH--, or any two of R.sup.1 to R.sup.9 adjacent to each other may be bonded to thereby form --OCH.sub.2 O-- or --(CH.sub.2).sub.3 --. By using this process, optically active benzhydrol compounds which have a high purity and are useful as, for example, intermediates in the synthesis of drugs can be produced by simple procedures.Type: GrantFiled: December 24, 1996Date of Patent: July 14, 1998Assignee: Takasago International CorporationInventors: Minzo Sakaguchi, Takashi Imai, Takashi Miura, Tetsuro Yamazaki
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Patent number: 5776884Abstract: The invention relates to the use of 2-cyclopentylidene-cyclopentanol as fragrance and flavour material. The compound has an indolic odour and is therefore very useful for replacing indole in perfumes and flavourings. Unlike indole it is stable to light and in alkaline media and gives no discolouration.Type: GrantFiled: November 1, 1996Date of Patent: July 7, 1998Assignee: Quest International B.V.Inventor: Angela Martin
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Patent number: 5741880Abstract: A hydroxy-functional polymer having a number average molecular weight, as determined by gel permeation chromatography, of from about 1800 to about 2700 and which consists essentially of polymerized monomers of 10-40% by weight, based on the total weight of the polymer, styrene; 20-55% by weight isobornyl methacrylate; and 20-55% by weight hydroxypropyl methacrylate; where the total of the monomers equals 100% are disclosed. The polymers are especially useful in combination with polyisocyanates as clearcoats in clearcoat/basecoat coating applications.Type: GrantFiled: April 28, 1997Date of Patent: April 21, 1998Assignee: The Sherwin-Williams CompanyInventors: Richard S. Valpey, III, Eugene I. Bzowej
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Patent number: 5716945Abstract: The present invention relates to compounds of formula in which formula X is hydrogen or hydroxy; R.sup.1 and R.sup.2, which may be the same or different, stand for hydrogen or C.sub.1 -C.sub.4 hydrocarbyl; or R.sup.1 and R.sup.2, taken together with the carbon atom bearing the group X, can form a C.sub.3 -C.sub.8 carbocyclic ring; Q is a single bond or a C.sub.1 -C.sub.4 hydrocarbylene diradical; R.sup.1, R.sup.2 and/or Q may be optionally substituted with one or more fluorine atoms; and prodrugs of formula in which one or more of the hydroxy groups are masked as groups which can be reconverted to hydroxy groups in vivo. The compounds show antiinflammatory and immunomodulating effects as well as stong activity in inducing differentiation and inhibiting undesirable proliferation of certain cells.Type: GrantFiled: November 7, 1995Date of Patent: February 10, 1998Assignee: Leo Pharmaceutical Products Ltd. A/S (L.o slashed.vens Kemiske Fabrik Produktionsaktieselskab)Inventor: Gunnar Grue-S.o slashed.rensen
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Patent number: 5602286Abstract: An improved method for the recovery of xanthophylls from corn gluten is provided. More specifically, a method for the recovery of xanthophylls from corn gluten whereby relatively dry corn gluten is extracted with an organic alcohol followed by a saponification reaction to convert xanthophyll esters to xanthophylls is described. Using this method, xanthophylls can be recovered from corn gluten in higher yields, greater efficiencies, and higher purity as to compared to prior art methods. Moreover, the xanthophyll product recovered in this method is a crystalline, powdery solid ideally suited for use in food products and pharmaceuticals. This material is especially suited for use in poultry feeds to provide the desired, healthy yellow color or hue in broiler and egg yolks.Type: GrantFiled: June 7, 1995Date of Patent: February 11, 1997Assignee: Cargill, IncorporatedInventor: Harapanahalli S. Muralidhara
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Patent number: 5498734Abstract: The magnesium complexes of cyclic hydrocarbons containing conjugated dienes, such as 1,2-dimethylenecycloalkanes, and 1,3-butadienes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4 diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, alkylditriflates, bromoalkylnitriles, esters, or amides serve as a convenient method for synthesizing carbocyclic systems. Significantly, carbocycles prepared by this method contain functional groups such as the exocyclic double bond or a keto group in one of the rings which could be used for further elaboration of these molecules. Furthermore, fused bicyclic systems containing a substituted five-membered ring can be conveniently prepared at high temperatures by the reactions of (2-butene-1,4-diyl)magnesium complexes with carboxylic esters or acid halides whereas low temperatures lead to regioselective synthesis of .beta.,.gamma.-unsaturated ketones. Additionally, .gamma.Type: GrantFiled: July 30, 1993Date of Patent: March 12, 1996Assignee: University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5399587Abstract: The present invention relates to novel potassium channel agonists which are useful in activating the calcium activated Maxi-K potassium channel in mammalian neuronal and smooth muscle tissue. The claimed compounds are of the general formula: ##STR1## In addition, a novel microbiological process for producing the claimed compounds is described.Type: GrantFiled: December 13, 1993Date of Patent: March 21, 1995Assignee: Merck & Co., Inc.Inventors: Maria L. Garcia, Robert A. Giacobbe, Otto D. Hensens, Gregory J. Kaczorowski, Seok H. Lee, Owen B. McManus, Deborah L. Zink
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Patent number: 5382714Abstract: A method of isolating, purifying and recrystallizing substantially pure lutein, preferably from saponified marigold oleoresin in its pure free form, apart from chemical impurities and other carotenoids. Lutein may be used as an analytical standard or in cancer prevention trials and as a safe and effective color additive for human food.Type: GrantFiled: March 17, 1994Date of Patent: January 17, 1995Assignee: The Catholic University of AmericaInventor: Frederick Khachik
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Patent number: 5264606Abstract: A process for the preparation of monomeric polyvinyl compounds and/or oligomers thereof comprising:(i) preactivating a supported rhenium oxide catalyst with a hydrocarbyl metal compound; and(ii) reacting, under metathesis reaction conditions, norbornene or one or more substituted norbornenes, or mixtures thereof, with ethylene in the presence of the activated supported catalyst of step (i).Type: GrantFiled: November 9, 1992Date of Patent: November 23, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Kenneth G. Moloy, Bernard D. Dombek
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Patent number: 5264638Abstract: A process for the extraction and purification of the diterpene alcohol Plaunotol from the leaves of the medicinal plant, Croton sublyratus Kurz. The process involves extracting firstly with a lower aliphatic alcohol followed by extracting from the alcohol solution with a chlorinated hydrocarbon. Then impurities are hydrolysed and the required Plaunotol separated by extraction with a hydrocarbon. This process is simple and gave much better yields than prior processes.Type: GrantFiled: January 28, 1992Date of Patent: November 23, 1993Assignee: Chulalongkorn UniversityInventor: Naline Nilubol
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Patent number: 5240907Abstract: Described are substituted cyclopentyl oxabicyclooctanes, cyclopentyl vinyl pyrans, cyclopentylformylcyclohexenes and cyclopentylhydroxymethyl cyclohexenes having the generic structures: ##STR1## wherein R.sub.1, R.sub.2, R', R", R.sub.1 ', R.sub.2 ', R.sub.1 " and R.sub.2 " represent hydrogen or methyl with the provisos that:(i) R.sub.1 and R.sub.2 are not both methyl;(ii) R' and R" are not both methyl;(iii) when R.sub.1 ' is methyl, R.sub.2 ' is hydrogen; and(iv) when R.sub.2 " is methyl, then R.sub.1 " is hydrogen,processes for preparing same and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles, e.g., solid or liquid, anionic, cationic, nonionic or zwitterionic detergents, cosmetic preparations, fabric softener compositions, fabric softener articles, hair preparations and perfumed polymers.Type: GrantFiled: October 23, 1992Date of Patent: August 31, 1993Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, John J. De Virgilio, Franc T. Schiet, Charles E. J. Beck, Charles J. Vinals, Marie R. Hanna
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Patent number: 5240908Abstract: Described are cyclohexenylmethylooxabicyclooctanes defined according to the generic structures: ##STR1## as well as intermediates for producing same defined according to the generic structures: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 ', and R.sub.3 " are each hydrogen or methyl with the provisos:(i) one or both of R.sub.1 and R.sub.2 is methyl;(ii) when R.sub.1 and R.sub.2 are both methyl then R.sub.3 ' and R.sub.3 " each represents hydrogen;(iii) one of R.sub.3 ' and R.sub.3 " is methyl and the other is hydrogen or R.sub.3 ' and R.sub.3 " both represent hydrogen; and(iv) when R.sub.3 ' and R.sub.3 " are both methyl then R.sub.1 is methyl and R.sub.2 is hydrogen;and R.sub.4 ' is hydrogen or C.sub.1 -C.sub.5 alkyl. Also described are the organoleptic uses of said cyclohexenylmethyloxabicyclooctanes wherein implementing or enhancing the aroma of perfume compositions, colognes and perfumed articles.Type: GrantFiled: April 11, 1991Date of Patent: August 31, 1993Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, John J. De Virgilio
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Patent number: 5206229Type: GrantFiled: October 10, 1990Date of Patent: April 27, 1993Assignee: Leo Pharmaceutical Products LTDInventors: Martin J. Calverley, Lise Binderup, Ernst T. Binderup
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Patent number: 5196601Abstract: Disclosed herein is a process for producing an alcohol or an amine by reducing a compound having a formyl, keto, nitro, oxirane, ester, nitrile, amide or halogenated carboxyl group with an alkali metal boro-hydride in the presence of a compound having a hydroxyl group and ether linkage. According to the present invention, a functional group having a great steric hindrance can be reduced, and a corresponding alcohol or amine can efficiently be produced under very mild conditions on an industrial scale.Type: GrantFiled: June 17, 1992Date of Patent: March 23, 1993Assignee: Kao CorporationInventors: Tomohito Kitsuki, Yoshiaki Fujikura
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Patent number: 5189013Abstract: 1,2-Dimethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-2-cyclohexen-1-ol is useful as a perfuming ingredient, for the preparation of perfuming compositions and perfumed articles to which it imparts woody-sandalwood type odor notes.Type: GrantFiled: February 21, 1992Date of Patent: February 23, 1993Assignee: Firmenich S.A.Inventor: Christian Chapuis
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Patent number: 5136112Abstract: A process for preparing 2-hydroxy-2, 5, 5, 9-tetramethyldecalyl ethanol of formula (II): ##STR1## which comprises reducing 3a, 6, 6, 9a-tetramethyldecahydro-naphto[2, 1-b]furan-2(1H)-one of formula (I): ##STR2## with an alkali metal boron hydride in the presence of a hydroxyl ether compound.Type: GrantFiled: July 29, 1991Date of Patent: August 4, 1992Assignee: Kao CorporationInventors: Tomohito Kitsuki, Yoshiaki Fujikura
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Patent number: 5128317Abstract: Described are camphonyl spirocyclooxaoctane-containing compositions having the generic structures: ##STR1## and mixtures of same with substituted cyclopentenyl-oxabicyclooctanes defined according to the generic structures: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 ' and R.sub.3 " each represents hydrogen or methyl and R.sub.4 ' represents hydrogen or C.sub.1 -C.sub.5 alkyl, processes for preparing same and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles, e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, cosmetic preparations, fabric softener compositions, fabric softener articles, hair preparations and perfumed polymers.Type: GrantFiled: July 25, 1991Date of Patent: July 7, 1992Assignee: International Flavors and Fragrances Inc.Inventors: Anubhav P. S. Narula, John J. De Virgilio, Carlos Benaim, Anton Van Ouwerkerk, Olivier Gillotin
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Patent number: 5107037Abstract: The invention concerns a novel process for the manufacture of 2-hydroxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene, I, commonly known as .alpha.-ambrinol. ##STR1## The process comprises reducing either an 8-halo-2-hydroxy-2,5,5-trimethyl-2,3,4,4a,5,6,7,8-octahydronaphthalene (IIa), alone or in a mixture with a 1-halo-2-hydroxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (IIb), or reduced the 1,2-epoxide which can be formed therefrom, namely, 1,2-epoxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octanhydronaphthalene (III). The halohydrins II are prepared from 1,1,6-trimethyl-1,2,3,7,8,8a-hexahydronaphthalene, IV.The compounds of formulas II and III are novel and form part of the present invention. The formula III epoxide possesses valuable odorant properties and its use as an odorant also forms part of the invention.Type: GrantFiled: June 6, 1990Date of Patent: April 21, 1992Assignee: Givaudan CorporationInventor: Peter Naegeli
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Patent number: 5104851Abstract: A 2-(alkyl-cyclohexyl)-1-propanol is disclosed. The compound is represented by formula (I): ##STR1## wherein R.sub.1 and R.sub.2 individually represent a group selected from the members consisting of methyl-, ethyl-, n-propyl-, i-propyl-, t-butyl-, and sec-butyl groups, provided that the total carbon atoms of the R.sub.1 and R.sub.2 groups are 4 to 7; either R.sub.1 and R.sub.2 is a hydrogen atom, the other being a cyclohexyl group; or R.sub.1 and R.sub.2 together form a hexamethylene ring together with 2 carbon atoms in the cyclohexane ring. The compound possesses a long-lasting, woody, floral odor, and can be widely used as perfumery materials such as perfumes, soaps, shampoos, aromatic goods, and detergents.Type: GrantFiled: January 25, 1991Date of Patent: April 14, 1992Assignee: Kao CorporationInventors: Yoshiaki Fujikura, Hiroaki Ohnuma, Manabu Fujita, Nao Toi
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Patent number: 5087707Abstract: Described are cyclopentenyl-oxabicyclooctanes, cyclopentenyl-formylcyclohexenes and cyclopentylhydroxymethyl cyclohexenes having the generic structures: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 ', and R.sub.3 " each represents hydrogen or methyl with the provisos:(i) one or two or R.sub.1, R.sub.2, R.sub.3 ' and R.sub.3 " represents methyl;(ii) R.sub.1 and/or R.sub.2 are methyl;(iii) at least one of R.sub.3 ' and R.sub.3 " is hydrogen; and(iv) when R.sub.1 and R.sub.2 is methyl then each of R.sub.3 ' and R.sub.3 " is hydrogenwherein R.sub.4 ' is hydrogen or C.sub.1 -C.sub.5 alkyl, processes for preparing same and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles, e.g., solid or liquid, anionic, cationic, nonionic or zwitterionic detergents, cosmetic preparations, fabric softener compositions, fabric softener articles, hair preparations and perfumed polymers.Type: GrantFiled: April 11, 1991Date of Patent: February 11, 1992Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, John J. De Virgilio, Carlos Benaim, Anton V. Ouwerkerk, Olivier Gillotin
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Patent number: 5081262Abstract: Described are cyclopentenyl-oxabicyclooctanes, cyclopentenyl-formylcyclohexenes and cyclopentyl-hydroxymethyl cyclohexenes having the generic structures: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 ', and R.sub.3 " each represents hydrogen or methyl with the provisos:(i) one or two of R.sub.1, R.sub.2, R.sub.3 ' and R.sub.3 " represents methyl;(ii) R.sub.1 and/or R.sub.2 are methyl;(iii) at least one of R.sub.3 ' and R.sub.3 " is hydrogen; and(iv) when R.sub.1 and R.sub.2 is methyl then each of R.sub.3 ' and R.sub.3 " is hydrogenwherein R.sub.4 ' is hydrogen or C.sub.1 -C.sub.5 alkyl, processes for preparing same and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles, e.g., solid or liquid, anionic, cationic, nonionic or zwitterionic detergents, cosmetic preparations, fabric softener compositions, fabric softener articles, hair preparations and perfumed polymers.Type: GrantFiled: September 27, 1990Date of Patent: January 14, 1992Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, John J. De Virgilio, Carlos Benaim, Anton Van Ouwerkerk, Olivier Gillotin
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Patent number: 5068363Abstract: Described are cyclohexenylmethyloxabicyclooctanes defined according to the generic structures: ##STR1## as well as intermediates for producing same defined according to the generic structures: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 ', and R.sub.3 " are each hydrogen or methyl with the provisos:(i) one or both of R.sub.1 and R.sub.2 is methyl;(ii) when R.sub.1 and R.sub.2 are both methyl then R.sub.3 ' and R.sub.3 " each represents hydrogen;(iii) one of R.sub.3 ' and R.sub.3 " is methyl and the other is hydrogen or R.sub.3 ' and R.sub.3 " both represent hydrogen; and(iv) when R.sub.3 ' and R.sub.3 " are both methyl then R.sub.1 is methyl and R.sub.2 is hydrogen;and R.sub.4 ' is hydrogen or C.sub.1 -C.sub.5 alkyl. Also described are the organoleptic uses of said cyclohexenylmethyl-oxabicyclooctanes wherein implementing or enhancing the aroma of perfume compositions, colognes and perfumed articles.Type: GrantFiled: September 27, 1990Date of Patent: November 26, 1991Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, John J. De Virgilio