Five-membered Alicyclic Ring Containing Patents (Class 568/838)
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Patent number: 7425657Abstract: The invention provides palladium-catalyzed hydrogenations of bio-oils and certain organic compounds. Experimental results have shown unexpected and superior results for palladium-catalyzed hydrogenations of organic compounds typically found in bio-oils.Type: GrantFiled: June 6, 2007Date of Patent: September 16, 2008Assignee: Battelle Memorial InstituteInventors: Douglas C. Elliott, Jianli Hu, Todd R. Hart, Gary G. Neuenschwander
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Patent number: 7321057Abstract: The present invention provides a new method for manufacturing a prostaglandin analogue having one or more keto groups on the 5-membered ring and/or omega chain, which comprises the step of treating a corresponding hydroxyl group containing compound with a co-oxidizer under the presence of a tetramethylpyperidine-1-oxyl derivative to form the desired prostaglandin analogue. The method of the invention can be carried out easily under relatively mild conditions.Type: GrantFiled: August 1, 2005Date of Patent: January 22, 2008Assignee: R-Tech Ueno, Ltd.Inventors: Ryu Hirata, Tatsuya Matsukawa
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Patent number: 7161042Abstract: A process for the preparation of prostaglandin compounds having the formula (I): wherein A is selected from the group consisting of C1–C6 alkyl groups; C7–C16 aralkyl groups wherein an aryl portion thereof is unsubstituted or substituted with one to three substituents selected from the group consisting of C1–C6 alkyl groups, halo and CF3; and (CH2)nOR? wherein n is an integer from 1 to 3 and R? represents a C6–C10 aryl group which is unsubstituted or substituted with one to three substituents selected from the group consisting of C1–C6 alkyl groups, halo and CF3; B is selected from OR? and NHR? wherein R? is C1–C6 alkyl groups; and represents a double bond or a single bond, is disclosed. Novel intermediates are also disclosed.Type: GrantFiled: January 9, 2006Date of Patent: January 9, 2007Assignee: Johnson Matthey Public Limited CompanyInventors: Derek Wyndham Clissold, Stuart Wilbert Craig, Rajendrakumar Reddy Gadikota, Min He, Jurjus Fayez Jurayj, Shahrokh Kazerani, Erwin Rannala, Pradeep Kumar Sharma
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Patent number: 7141706Abstract: A process for the preparation of prostaglandin compounds having the formula (I): wherein A is selected from the group consisting of C1–C6 alkyl groups; C7–C16 aralkyl groups wherein an aryl portion thereof is unsubstituted or substituted with one to three substituents selected from the group consisting of C1–C6 alkyl groups, halo and CF3; and (CH2)nOR? wherein n is an integer from 1 to 3 and R? represents a C6–C10 aryl group which is unsubstituted or substituted with one to three substituents selected from the group consisting of C1–C6 alkyl groups, halo and CF3; B is selected from OR? and NHR? wherein R? is C1–C6 alkyl groups; and represents a double bond or a single bond, is disclosed. Novel intermediates are also disclosed.Type: GrantFiled: January 9, 2006Date of Patent: November 28, 2006Assignee: Johnson Matthey Public Limited CompanyInventors: Derek Wyndham Clissold, Stuart Wilbert Craig, Rajendrakumar Reddy Gadikota, Min He, Jurjus Fayez Jurayj, Shahrokh Kazerani, Erwin Rannala, Pradeep Kumar Sharma
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Patent number: 7132497Abstract: An aromatic dihydroxy compound conforming to formula 1 is disclosed. Also disclosed are (co)polycarbonates derived from the compound. The novel (co)polycarbonates are characterized by their reduced water uptake and improved flowability.Type: GrantFiled: August 19, 2004Date of Patent: November 7, 2006Assignee: Bayer Materialscience AktiengesellschaftInventors: Helmut-Werner Heuer, Rolf Wehrmann
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Patent number: 7109371Abstract: A process for the preparation of prostaglandin compounds having the formula (I): wherein A is selected from the group consisting of C1–C6 alkyl groups; C7–C16 aralkyl groups wherein an aryl portion thereof is unsubstituted or substituted with one to three substituents selected from the group consisting of C1–C6 alkyl groups, halo and CF3; and (CH2)nOR? wherein n is an integer from 1 to 3 and R? represents a C6–C10 aryl group which is unsubstituted or substituted with one to three substituents selected from the group consisting of C1–C6 alkyl groups, halo and CF3; B is selected from OR? and NHR? wherein R? is C1–C6 alkyl groups; and represents a double bond or a single bond, is disclosed. Novel intermediates are also disclosed.Type: GrantFiled: January 5, 2004Date of Patent: September 19, 2006Assignee: Johnson Matthey Public Limited CompanyInventors: Derek Wyndham Clissold, Stuart Wilbert Craig, Rajendrakumar Reddy Gadikota, Min He, Jurjus Fayez Jurayj, Shahrokh Kazerani, Erwin Rannala, Pradeep Kumar Sharma
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Patent number: 7045643Abstract: The present invention describes a method of preparation of formulations of microcrystalline lutein, particularly in the form of esters, which are resistant to oxidation and are soluble in hydrophilic and/or lipophilic media. For these formulations, the esters of lutein are mixed with antioxidants, vegetable oils and/or organic solvents, and this initial mixture is submitted to various stages depending on the type of final formulation required. These formulations are suitable for direct application as colourants in the pharmaceutical, food and cosmetics fields. They can also be used as diet supplements.Type: GrantFiled: December 20, 2002Date of Patent: May 16, 2006Assignee: Vitatene, S.A.Inventors: Antonio Estrella De Castro, Nieves Fraile Yecora, Manuel Oliver Ruiz, Angel Muñoz, Juan Francisco Lopez Oritz, Walter Cabri
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Patent number: 6894198Abstract: An alkali metal alkoxide or alkaline earth metal alkoxide in granular form.Type: GrantFiled: October 15, 2002Date of Patent: May 17, 2005Assignee: Degussa AGInventors: Andreas Harthun, Christoph Theis, André Noppe, Josef Metz
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Patent number: 6720295Abstract: Compounds of the formula wherein the R groups represent, simultaneously or independently, a hydrogen atom or a methyl group, R′ represents a hydrogen atom or an acetyl group, G represents a cyclopentyl or a cyclopentenyl radical, and X represents a oxygen atom or a CH2 group are disclosed for use as perfuming ingredients and perfumed articles or in perfuming compositions that contain such compounds.Type: GrantFiled: August 19, 2002Date of Patent: April 13, 2004Assignee: Firmenich SAInventors: Koenraad Vanhessche, Jean-Marc Gaudin, George Lem, Györgyi Sneyers
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Publication number: 20040014633Abstract: An alkyl gycol ether having the following formula 1Type: ApplicationFiled: July 10, 2002Publication date: January 22, 2004Applicant: Takasago International CorporationInventors: Takashi Aida, Andrew T. Lupo, Hiroyuki Matsuda
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Patent number: 6667284Abstract: A magnetic recording medium and method for forming the magnetic recording medium are described. The magnetic recording medium includes a magnetic layer formed on a non-magnetic support, and a lubricant layer over the magnetic layer. The lubricant layer includes a compound selected from the group consisting of hydrocarbyl-substituted cyclopentanes, hydrocarbyl-substituted cyclopentenes, hydrocarbyl-substituted cyclopentadienes, and mixtures or derivatives thereof. The lubricant layer also may be used on a magnetic head for reading and writing information on a magnetic recording medium. The magnetic recording medium and the magnetic head may be used to manufacture computer disk drives, compact disk drives, audio equipment, and video equipment.Type: GrantFiled: March 22, 2001Date of Patent: December 23, 2003Assignee: Pennzoil-Quaker State CompanyInventors: Selda Gunsel, Clifford Venier, I-Ching Chiu
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Patent number: 6646170Abstract: The present invention relates to novel ether compounds, compositions comprising ether compounds, and methods useful for treating and preventing cardiovascular diseases, dyslipidemias, dysproteinemias, and glucose metabolism disorders comprising administering a composition comprising an ether compound. The compounds, compositions, and methods of the invention are also useful for treating and preventing Alzheimer's Disease, Syndrome X, peroxisome proliferator activated receptor-related disorders, septicemia, thrombotic disorders, obesity, pancreatitis, hypertension, renal disease, cancer, inflammation, and impotence. In certain embodiments, the compounds, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.Type: GrantFiled: April 26, 2002Date of Patent: November 11, 2003Assignee: Esperion Therapeutics, Inc.Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
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Patent number: 6630609Abstract: A process for the preparation of a composition having the formula: in which a compound having the formula: is treated with a base and a silylating agent.Type: GrantFiled: July 16, 2002Date of Patent: October 7, 2003Assignee: Florida State UniversityInventors: Robert A. Holton, Phong Vu, Tawfik Gharbaoui, Vincent Reboul
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Patent number: 6608235Abstract: In reduction of an epoxy group-containing organic compound, for example, a C5-C20 saturated or unsaturated epoxy cycloaliphatic compound, in the presence of a nickel catalyst, by bringing the compound into contact with hydrogen, the target compound can be produced at a high yield by adding a basic substance (for example, an alkali metal hydroxide, an alkali metal carbonate, an alkali metal alkoxide, and an amine compound having 1 to 3 C1-C12 alkyl groups), to the reduction reaction system, to thereby restrict production of by-products due to a side deoxidation reaction.Type: GrantFiled: August 6, 2001Date of Patent: August 19, 2003Assignee: Ube Industries, Ltd.Inventors: Nobuyuki Kuroda, Tokuo Matsuzaki, Mitsuo Yamanaka, Takato Nakamura, Osamu Yamazaki, Hirofumi Takemoto
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Patent number: 6495725Abstract: The present invention provides a simplified and convenient process for the preparation of an optically active enone such as 7,7-dimethyl-6,8-dioxabicyclo-[3,3,0]oct-3-en-2-one. The invention further provides novel optically active intermediate compounds.Type: GrantFiled: December 15, 2000Date of Patent: December 17, 2002Assignee: Chisso CorporationInventor: Kunio Ogasawara
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Patent number: 6489521Abstract: In the overall methods of hydrogenating esters and maleic anhydride, which methods comprise a hydration reaction, comprising conducting the hydration reaction in the presence of the shaped Raney metal fixed-bed catalysts of the invention.Type: GrantFiled: July 17, 2001Date of Patent: December 3, 2002Assignee: Degussa AGInventors: Daniel Ostgard, Konrad Moebus, Monika Berweiler, Barbara Bender, Gernot Stein
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Patent number: 6441253Abstract: A process for the preparation of a compound having the formula: the process comprising treating a compound having the formula: with an alkyl metal species or with a Lewis acid in the presence of a tertiary amine base, wherein P2 is hydrogen or a hydroxyl protecting group.Type: GrantFiled: July 17, 2000Date of Patent: August 27, 2002Assignee: Florida State UniversityInventors: Robert A. Holton, Phong Vu, Tawfik Gharbaoui, Vincent Reboul
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Patent number: 6365782Abstract: A method of producing tricyclodecane dicarbaldehyde and/or pentacyclopentadecane dicarbaldehyde by the hydroformylation of dicyclopentadiene and/or tricyclopentadiene. The tricyclodecane dicarbaldehyde and/or pentacyclopentadecane dicarbaldehyde in the hydroformylation product liquid are extracted with an extraction solvent comprising a polyhydric alcohol having 2 to 6 carbon atoms. With such extraction, the tricyclodecane dicarbaldehyde and/or pentacyclopentadecane dicarbaldehyde transfer into the extraction solvent while retaining the catalyst components in the hydroformylation solvent. The controlled extraction atmosphere with an oxygen concentration of 1000 ppm or lower prevents the rhodium compound from transferring into the extraction solvent, thereby avoiding the loss of expensive rhodium.Type: GrantFiled: July 3, 2000Date of Patent: April 2, 2002Assignee: Mitsbushi Gas Chemical Company, Inc.Inventors: Kenichi Nakamura, Kazuhiro Yamada, Takashi Fujii, Takashi Motoi
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Patent number: 6359181Abstract: The present invention provides a novel compound represented by the general formula I; wherein R is H or COR3; R1 is H, R2, phenyl, or COR3, wherein R2 is C1-C5 lower alkyl and R3 is R2 or phenyl; Z is CH2 or O; Y is OH, OCOR3 or ═O; x is 0 or 1; and X is C1-C5 n-alkyl, C3-C7 cycloalkyl, phenyl, furanyl, thienyl or substituted derivatives thereof, wherein the substituents maybe selected from the group consisting of C1-C5 alkyl, halogen, CF3, CN, NO2, NR42, CO2R4 and OR4 wherein R4 is hydrogen or C1-C5 alkyl and dotted lines represent the presence or absence of a double bond and wavy lines represent a cis or trans bond. These novel compounds are especially useful for treating elevated intraocular pressure (ocular hypertension) and glaucoma.Type: GrantFiled: July 26, 2001Date of Patent: March 19, 2002Assignee: Allergan Sales, Inc.Inventors: Robert M. Burk, Mark Holoboski, Mari F. Posner
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Patent number: 6313087Abstract: Perfumes and perfumed products comprising 3-alkylcycloalkan-1-ols of formula (I), wherein R1 represents hydrogen or a methyl, ethyl or propyl group; R2, R4 and R5 independently represent hydrogen or a methyl group; R3 represents a saturated hydrocarbon group with 4-8 carbon atoms, provided that the first carbon atom of this hydrocarbon group is not a tertiary carbon atom, and n represents the numbers 1, 2 and 3. The invention also concerns compounds of formula (I) wherein R1 represents a methyl, ethyl or propyl group and R2-R5 are as outlined above.Type: GrantFiled: October 25, 1999Date of Patent: November 6, 2001Assignee: Quest International BVInventor: Karen Jane Rossiter
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Patent number: 6284703Abstract: A shaped, activated, fixed-bed Raney metal catalyst prepared by a method comprising preparing a mixture of powders comprising at least one catalyst alloy of (1) at least one catalytically active Raney process metal, a leachable alloy component and optionally a promoter, (2) at least one binder containing at least one pure Raney metal and (3) a moistening agent. Shaping, calcining and activating said catalyst and doping said catalyst with rhenium.Type: GrantFiled: August 5, 1999Date of Patent: September 4, 2001Assignee: Degussa-Huels AktiengesellschaftInventors: Daniel Ostgard, Konrad Moebus, Monika Berweiler, Barbara Bender, Gernot Stein
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Patent number: 6278031Abstract: The fixed-bed catalyst comprises palladium and selenium or tellurium or a mixture of selenium and tellurium on a silicon dioxide support and has a BET surface area of from 80 to 380 m2/g and a pore volume of from 0.6 to 0.95 cm3/g in the pore diameter range from 3 nm to 300 &mgr;m, with from 80 to 95% of the pore volume being in the pore diameter range from 10 to 100 nm. It is prepared by impregnating a silicon dioxide support with a solution of a palladium compound and a selenium compound or tellurium compound or a mixture of a selenium compound and a tellurium compound, drying it and reducing it in the presence of hydrogen. The catalyst is used, in particular, for isomerizing 3-buten-1-ol compounds.Type: GrantFiled: January 16, 2001Date of Patent: August 21, 2001Assignee: BASF AktiengesellschaftInventors: Franz Josef Bröcker, Werner Aquila, Klemens Flick, Gerd Kaibel, Ernst Langguth
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Publication number: 20010012907Abstract: A halogenated substituted cyclopentene derivative of formula (I): 1Type: ApplicationFiled: February 1, 2001Publication date: August 9, 2001Applicant: Nissan Chemical Industries, Ltd.Inventor: Fumie Sato
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Patent number: 6271425Abstract: A novel process for producing alcohols, characterized by reacting an organic halide represented by the formula R—X (wherein R means an organic residue and X means a halogen atom) with oxygen molecules in the presence of an organotin compound and a reducing agent and optionally in the presence of a free-radical inhibitor in an amount up to 0.3 equivalent based on the organic halide to obtain an alcohol represented by the general formula R—OH (wherein R has the same meaning as the above).Type: GrantFiled: September 7, 1999Date of Patent: August 7, 2001Assignees: Fujisawa Pharmaceutical Co., Ltd.Inventors: Eiichi Nakamura, Masaya Sawamura
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Patent number: 6271408Abstract: This invention relates to trimethylsilyloxy-cyclopentane derivatives: 3-(1-Acetoxy-1-methylethyl)- 2-formyl-1-methyl-1-trimethylsilyloxy-cyclopentane; 4-[5-(1-Hydroxy-1-methylethyl)-2-methyl-2-trimethylsilyloxy-cyclopentyl]-3-buten-2-one; 5-[5-(1-Hydroxy-1-methylethyl)-2-methyl-2-trimethylsilyloxy-cyclopentyl]-3-methyl-penta-1,4-dien-3-ol and alkyl 5-[5-(1-Hydroxy-1-methylethyl)-2-methyl-2-trimethylsilyloxy-cyclopentyl]-3-methyl-penta-2,4-dienoates.Type: GrantFiled: September 13, 2000Date of Patent: August 7, 2001Assignee: Roche Vitamins Inc.Inventors: Hanspeter Pfander, Bruno Traber
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Patent number: 6245952Abstract: The present invention relates to a process for the preparation of alcohols by reduction of the carbonyl function in substrates belonging to the class of aldehydes, ketones, esters or lactones, which substrates may contain unsaturated functions other than carbonyl. This process includes the steps of reacting the carbonyl substrate with stoichiometric amounts of a silane in the presence of catalytic amounts of an active zinc compound which is monomeric and not a hydride, hydrolyzing the thus-obtained siloxane with a basic agent, and separating and purifying, if necessary, the thus-obtained alcohol. The catalytically active compound is generally obtained by the reaction of an oligomeric or polymeric precursor compound of zinc with a complexing agent.Type: GrantFiled: March 1, 1999Date of Patent: June 12, 2001Assignee: Firmenich SAInventor: Hubert Mimoun
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Patent number: 6166267Abstract: A method of converting Compound A (1,3-dehydro-cyclopenta[1]phenanthren-2-one) to Compound C (1H-cyclopenta[1]penanthren) in situ in a single reactor is disclosed.Type: GrantFiled: September 2, 1999Date of Patent: December 26, 2000Assignee: Boulder Scientific CompanyInventor: Fredric Askham
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Patent number: 6166091Abstract: 2,3,4-trihydroxycyclopentanone represented by the following formula [I], its optically active substance or salt thereof.Type: GrantFiled: September 29, 1999Date of Patent: December 26, 2000Assignee: Takara Shuzo Co., Ltd.Inventors: Kaoru Kojima, Katsushige Ikai, Tatsuji Enoki, Nobuto Koyama, Ikunoshin Kato
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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: 6093857Abstract: A process for preparing cyclopentyl formates of the formula (II) ##STR1## by reacting cyclopentenes of the formula (I) ##STR2## where R.sup.1, R.sup.2 and R.sup.3, independently of one another, are hydrogen atoms or C.sub.1-8 -alkyl,with formic acid in the presence of an acid catalyst.Type: GrantFiled: September 12, 1997Date of Patent: July 25, 2000Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Rolf Pinkos, Norbert Rieber, Michael Schulz, Joaquim Henrique Teles
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Patent number: 6084138Abstract: An (E)-(R)-2-alkyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-2-buten-1-ol represented by formula (I): ##STR1## wherein R represents an alkyl group having 1 to 3 carbon atoms, and a process for preparing the same comprising hydrogenating a corresponding (E)-(R)-2-alkyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-2-buten-1-al in the presence of a ruthenium-phosphine complex as a catalyst, a base comprising an alkali metal or an alkaline earth metal, and an amine. The compound (I) has an excellent sandalwood oil odor.Type: GrantFiled: July 1, 1998Date of Patent: July 4, 2000Assignee: Takasago International CorporationInventors: Takashi Aida, Makoto Harada, Takeshi Yamamoto, Hisao Iwai, Akira Amano, Tetsuro Yamasaki
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Patent number: 6040475Abstract: This invention is concerned with the synthesis of 3-(1-acetoxy-1-methylethyl)-6-oxo-heptanal; 3-(1-acetoxy-1-methylethyl)-2-formyl-1-methyl-cyclopentanol; 5-[2-hydroxy-5-(1-hydroxy-1-methylethyl)-2-methyl-2-cyclopentyl]-3-methyl- penta-2,4-dien-1-ol and 2,7,11-trimethyl-13-[2-hydroxy-5-(1-hydroxy-1-methylethyl)-2-methyl-cyclop entyl]-trideca-2,4,6,8,10,12-hexaenal which are useful as intermediates for the synthesis of lycopene metabolites.Type: GrantFiled: May 12, 1999Date of Patent: March 21, 2000Assignee: Roche Vitamins Inc.Inventors: Hanspeter Pfander, Bruno Traber
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Patent number: 6028231Abstract: A process to obtain 2-methyl-4-(2, 2, 3-trimethyl-cyclopent-3-en-1-yl)-but-2-en-1-ol by reacting campholene aldehyde and propionaldehyde via aldol condensation and further subjecting the resulting reaction mixture to Meerwein-Ponndorf reduction with aluminum alcoholates in the presence of a basic amine compound.Type: GrantFiled: April 20, 1999Date of Patent: February 22, 2000Assignee: Henkel Kommanditgesellschaft auf AktienInventor: Thomas Markert
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Patent number: 6025518Abstract: A substituted cyclopentene derivative of formula (V): whereinX.sup.1 is (.alpha.-OZ.sup.a, .beta.-H) or (.alpha.-H, .beta.-OZ.sup.a), X.sup.3 is (.alpha.-OZ.sup.d, .beta.-H), (.alpha.-H, .beta.-OZ.sup.d), or oxygen atom, each of Z.sup.a and Z.sup.d, which may be the same or different, is a hydrogen atom or a protective radical for a hydroxyl radical;U is a radical selected from the group consisting of CR.sup.1 HCH.sub.2, CR.sup.1 .dbd.CH and C.tbd.C,whereinR.sup.1 is a hydrogen atom, halogen atom, substituted silyl radical represented by SiR.sup.9 R.sup.10 R.sup.11 or substituted stannyl radical represented by SnR.sup.14 R.sup.15 R .sup.16,m is an integer of 0 to 6;X.sup.2 is CH.dbd.CH or C.tbd.C,p is an integer of 0 or 1, each of n and q is an integer of 0 to 5; andZ.sup.1 is a hydrogen atom, COOR.sup.y, CN, OH, OCOR.sup.2, CONR.sup.b R.sup.c or NR.sup.d R.sup.e.Type: GrantFiled: September 8, 1998Date of Patent: February 15, 2000Assignees: Nissan Chemical Industries, Ltd., Fumie SATOInventor: Fumie Sato
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Patent number: 6008417Abstract: The invention is concerned with a multi-stage process for making an oxidative metabolite of the carotenoid lycopene, 2,6-cyclolycopene-1,5-diol having the formula ##STR1## In this process .alpha.-terpinyl acetate is oxidatively dihydroxylated to a cyclohexanediol (IV), the cyclohexanediol (IV) is oxidatively cleaved to a ketoaldehyde (V), the ketoaldehyde (V) is subjected to an intramolecular aldol condensation to give a cyclopentanol (VI), the cyclopentanol (VI) is silylated to its silylated derivative formylcylopentane (VII), the formylcyclopentane (VII) is subjected to a C.sub.Type: GrantFiled: October 7, 1998Date of Patent: December 28, 1999Assignee: Roche Vitamins Inc.Inventors: Hanspeter Pfander, Bruno Traber
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Patent number: 5994291Abstract: An (E)-(R)-2-alkyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-2-buten-1-ol represented by formula (I): wherein R represents an alkyl group having 1 to 3 carbon atoms,and a process for preparing the same comprising hydrogenating a corresponding (E)-(R)-2-alkyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-2-buten-1-al in the presence of a ruthenium-phosphine complex as a catalyst, a base comprising an alkali metal or an alkaline earth metal, and an amine. The compound (I) has an excellent sandalwood oil odor.Type: GrantFiled: September 11, 1997Date of Patent: November 30, 1999Assignee: Takasago International CoporationInventors: Takashi Aida, Makoto Harada, Takeshi Yamamoto, Hisao Iwai, Akira Amano, Tetsuro Yamasaki
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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: 5874649Abstract: The object of the present invention resides in efficiently providing unsaturated alcohol from an .alpha.,.beta.-unsaturated aldehyde.The present invention provides a process for preparing unsaturated alcohol by selectively reducing the aldehyde group of an .alpha.,.beta.-unsaturated aldehyde in the presence of a primary or a secondary alcohol having 2 to 8 carbon atoms using an aluminum alcoholate to produce an unsaturated alcohol such as compounds represented by the formula (III). ##STR1## (wherein R represents an alkyl group having 1 to 3 carbon atoms) wherein the reaction is carried out with addition of a protonic acid.Type: GrantFiled: November 5, 1997Date of Patent: February 23, 1999Assignee: Kao CorporationInventors: Shigeyoshi Tanaka, Shinji Kotachi, Junji Koshino, Junko Yamamoto
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Patent number: 5817880Abstract: There is provided an intermediate alcohol ester compound represented by the formula VII: ##STR1## wherein R.sub.1 is a methyl group or a hydrogen atom; R.sub.2 is a C.sub.2-4 alkyl group; substituted with two or more fluorine atoms.Type: GrantFiled: March 14, 1997Date of Patent: October 6, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Tomonori Iwasaki, Kazunori Tsushima, Takashi Furukawa, Takao Ishiwatari, Toru Tsuchiya, Mikako Nakamachi
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Patent number: 5808112Abstract: The present invention relates to a novel process for preparing cis-4-O-protected-substituted-2-cyclopentenol derivatives comprising, a) dissolving a 4-O-protected-2-cyclopentenone in a suitable organic solvent; and b) treating the solution with a suitable Lewis acid and a suitable reducing agent at a temperature of from about -100.degree. C. to about 20.degree. C. The cis-4-O-protected-substituted-2-cyclopentenol derivatives are useful intermediates in the preparation of various cyclopentanyl and cyclopentenyl purine analogs which are useful as immunosuppressants and in the preparation of various prostaglandins.Type: GrantFiled: June 17, 1997Date of Patent: September 15, 1998Assignee: Hoechst Marion Roussel Inc.Inventors: Timothy T. Curran, David A. Hay, Jonathan C. Evans
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Patent number: 5750805Abstract: Epoxides containing hydroxy groups are rearranged enantioselectively using a chiral base to give allyl alcohols in high enantiomeric excess, e.g. ##STR1## If R.sup.3 .noteq.H, the reaction also has the effect of generating a chiral tetrasubstituted carbon atom.Type: GrantFiled: September 12, 1996Date of Patent: May 12, 1998Assignee: The University of ReadingInventors: David Michael Hodgson, Jason Witherington
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Patent number: 5728890Abstract: A cycloalkylhydroperoxide, preferably having a C.sub.5-20 cycloalkyl group, is decomposed by bringing it into contact with a ruthenium complex of the formula:?RuCl.sub.2 L.sub.n !.sub.m (I)wherein L=a neutral ligand, n=1-4 and m.gtoreq.1, for example, ?RuCl.sub.2 (PPh.sub.3).sub.3 !, to produce a cycloalkanol and cycloalkanone.Type: GrantFiled: January 30, 1996Date of Patent: March 17, 1998Assignee: Ube Industries, Ltd.Inventors: Toshikazu Hamamoto, Mitsuo Yamanaka, Takato Nakamura, Tetsuro Shimano
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Patent number: 5728899Abstract: The present invention relates to a novel process for preparing cis-4-O-protected-substituted-2-cyclopentenol derivatives comprising, a) dissolving a 4-O-protected-2-cyclopentenone in a suitable organic solvent; and b) treating the solution with a suitable Lewis acid and a suitable reducing agent at a temperature of from about -100.degree. C. to about 20.degree. C. The cis-4-O-protected-substituted-2-cyclopentenol derivatives are useful intermediates in the preparation of various cyclopentanyl and cyclopentenyl purine analogs which are useful as immunosuppressants and in the preparation of various prostaglandins.Type: GrantFiled: February 1, 1996Date of Patent: March 17, 1998Assignee: Hoechst Marion Roussel Inc.Inventors: Timothy T. Curran, David A. Hay, Jonathan C. Evans
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Patent number: 5714351Abstract: The individual enantiomers of the compounds (Ia), (Ib), (IIa) or (IIb), optionally substituted by non-interfering substituent(s). The novel enantiomers can be obtained by biotransformation. The (Ia) or (IIa) compounds can be used for the synthesis of chiral carbocyclic nucleosides.Type: GrantFiled: February 13, 1995Date of Patent: February 3, 1998Assignee: Chiroscience LimitedInventors: Christopher Thomas Evans, Stanley Michael Roberts, Karoline Shoberu, Rosemary Mackeith
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Patent number: 5696075Abstract: Described herein are compounds of the formula ##STR1## wherein R represents a hydrogen atom or a methyl radical and X stands for a --CHO, or a --CN group, are useful as perfuming ingredients for preparing perfuming compositions and a variety of perfumed articles, to which they impart sandalwood-type odor notes, together with marine, ozone type odor characters, such that said compositions and articles thus acquire a "transparent" connotation. The aldehydes of formula (I) are also useful as starting products for the preparation of the corresponding fragrant alcohols and nitriles.Type: GrantFiled: July 27, 1995Date of Patent: December 9, 1997Assignee: Firmenich SAInventors: Christian Chapuis, Pierre-Alain Blanc
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Patent number: 5672779Abstract: The present invention provides a compound represented by the formula: ##STR1## wherein R.sub.1 denotes a hydrogen atom or a methyl group; R.sub.2 represents a 1-methyl-2-propenyl group, a 1-methyl-2-propynyl group, a 3,3-dihalogeno-1-methyl-2-propenyl group or a C.sub.1 -C.sub.6 alkyl group which may be substituted with at least one halogen atom; and A' represents a hydrogen atom or a protecting group for a hydroxyl group. The compound is useful in the preparation of esters which can be used to control insect pests.Type: GrantFiled: May 1, 1996Date of Patent: September 30, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Tomonori Iwasaki, Masaya Suzuki, Takashi Furukawa, Kazunori Tsushima, Takao Ishiwatari, Toru Tsuchiya
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Patent number: 5656635Abstract: The invention relates to the use of alcohol derivatives of F-type prostaglandins as ocular hypotensives. The PGF derivatives used in accordance with the invention are encompassed by the following structure formula I: ##STR1## wherein wavy line attachments indicate either the alpha (.alpha.) or beta (.beta.) configuration; hatched lined indicate .alpha. configuration, solid triangles are used to indicate .beta. configuration, dashed bonds represent a double bond, or a single bond; n is 0, or an integer of from 1 to 3; R is hydrogen or a --(CO)R.sub.4 group; R.sub.1, R.sub.2, and R.sub.3 independently are hydroxyl, or --O(CO)R.sub.5 groups, wherein R.sub.4 and R.sub.5 independently stand for saturated or unsaturated acyclic hydrocarbon having from 1 to 20 carbon atoms, or --(CH.sub.2).sub.m R.sub.6 where m is 0-10 and R.sub.6 is an aliphatic, aromatic or heteroaromatic ring, R.sub.7 and R.sub.8 independently are hydrogen or alkyl of 1 to 6 carbon atoms or pharmaceutically acceptable salts thereof.Type: GrantFiled: June 8, 1993Date of Patent: August 12, 1997Assignee: AllerganInventor: Ming Fai Chan
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Patent number: 5574196Abstract: A process for preparing tertiary alkanols which comprises the step of oxidizing with ozone a saturated hydrocarbon having a tertiary carbon center in the presence of a carboxylic acid and for a sufficient period of time and at suitable temperature and pressure to form said alkanols.Type: GrantFiled: February 28, 1995Date of Patent: November 12, 1996Assignee: Hoechst Celanese CorporationInventors: Charles E. Tucker, Diane E. Allen, Charles C. Hobbs
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Patent number: 5552434Abstract: Compounds of the formula ##STR1## where the dotted line represents a bond or the absence of a bond, the wavy lines represent bonds which are either in cis or trans configuration; R.sub.1 represents H, or CO--R.sub.2 where R.sub.2 is lower alkyl of 1 to 6 carbons, carbocyclic aryl or heterocyclic aryl; or carbocyclic aryl or heteroaryl substituted lower alkyl group; X represents CO--NR.sub.3 R.sub.4, CH.sub.2 OH, CH.sub.2 OR.sub.5, CH.sub.2 O--COR.sub.6, and CH.sub.2 --NR.sub.3 R.sub.4, where R.sub.3 and R.sub.4 independently are H or lower alkyl, R.sub.5 is lower alkyl of 1 to 6 carbons, and R.sub.6 is lower alkyl of 1 to 6 carbons, carbocyclic aryl or heterocyclic aryl; or carbocyclic aryl or heteroaryl substituted lower alkyl group, and n is an integer between 0 and 8 are capable of lowering intraocular pressure in the eye of a mammal.Type: GrantFiled: December 14, 1994Date of Patent: September 3, 1996Assignee: AllerganInventors: Michael E. Garst, Robert M. Burk
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Patent number: 5550260Abstract: A process for the production of a cyclopentenol compound represented by the formula I: ##STR1## wherein R.sub.1 represents a 2-propenyl group or a 2-propynyl group from a cyclopentenolone compound represented by the formula II: ##STR2## by protecting the hydroxyl group of the compound II, reacting the protected compound II with a reagent system obtained from TiCl.sub.4, Zn and CH.sub.2 Br.sub.2 or CH.sub.2 I.sub.2 and removing the protecting group from the resulting reaction product.Type: GrantFiled: June 2, 1994Date of Patent: August 27, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Kazunori Tsushima, Tomonori Iwasaki, Masaya Suzuki, Noritada Matsuo