Polycyclo-alicyclic Ring System Patents (Class 568/445)
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Patent number: 4421935Abstract: Process for the preparation of Diels-Alder type adducts by reacting a compound with formula ##STR1## or the corresponding hydrated derivative, wherein R.sup.1, R.sup.2, and R.sup.4 are H or lower alkyl, R.sup.3 is lower alkyl, X is O,S, (O--CR.sup.5 R.sup.6 R.sup.7).sub.2 or ##STR2## wherein R.sup.5, R.sup.6 and R.sup.7 an H or lower alkyl, n is 2-5 and Y is H, alkyl or alkenyl or Y and R.sup.2 together form an alkylene group which may contain one or more substituents, with a cyclopentadiene and/or an oligomer thereof in the presence of an aqueous solution of a strong proton donor having a conjugate with a low nucleophilicity.Type: GrantFiled: May 3, 1982Date of Patent: December 20, 1983Assignee: Shell Oil CompanyInventor: Pieter A. Verbrugge
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Patent number: 4408077Abstract: A process and intermediates for preparing 6-(lower alkoxy)-5-(trifluoromethyl)-1-naphthalenecarboxylic acid derivatives are disclosed. The derivatives are useful for preparing aldose reductase inhibitors. With reference to the process, 1,1,1-trifluoro-5-(2-methylphenyl)-2,3-pentadione 3-oxime is cyclized to give a key intermediate 3,4-dihydro-1-hydroxy-5-methyl-1-(trifluoromethyl)-2(1H)-naphthalenone oxime; and 3,4-dihydro-1-hydroxy-5-methyl-1-(trifluoromethyl)-2(1H)-naphthalenone is aromatized to 5-methyl-1-(trifluoromethyl)-2-naphthalenol with a dehydrating agent.Type: GrantFiled: November 13, 1981Date of Patent: October 4, 1983Assignee: Ayerst, McKeena & Harrison, Inc.Inventors: Kazimir Sestanj, Steven Fung, Nedumparambil A. Abraham, Francesco Bellini
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Patent number: 4354043Abstract: Described is a compound having the structure: ##STR1## a norbornyl oxyacetaldehyde, prepared by oxidizing the norbornyl oxyethanol compound having the structure: ##STR2## using air or oxygen and a silver or copper chromite catalyst; and organoleptic uses of such oxidation product in the field of perfumery, colognes and perfumed articles (e.g. perfumed plastics, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions or drier-added fabric softener articles).Type: GrantFiled: September 17, 1981Date of Patent: October 12, 1982Assignee: International Flavors & Fragrances Inc.Inventors: Robert P. Belko, Richard M. Boden, Marie R. Hanna
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Patent number: 4334100Abstract: This invention is directed to a process for preparing aldehydes by hydroformylation of monoterpene compounds, which comprises reacting a monocyclic or bicyclic monoterpene compound with at least one double bond at from about 70.degree. to 160.degree. C. under a pressure of from about 100 to 400 bar and in the presence of a catalyst mixture of tertiary phosphines and rhodium carbonyl complexes containing tertiary phosphines. The aldehydes prepared are useful as perfuming agents.Type: GrantFiled: November 14, 1979Date of Patent: June 8, 1982Assignee: Henkel Kommanditgesellschaft auf Aktien (Henkel KGaA)Inventors: Jens Hagen, Klaus Bruns
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Patent number: 4319049Abstract: The present invention discloses tricyclic compounds having a gem-bis(hydroxymethyl) functional group. Compounds within the formulae of the present invention include those components having unsaturation in the ring structure and those in which the unsaturation has been converted a halogen or phosphite functionality.Type: GrantFiled: October 6, 1980Date of Patent: March 9, 1982Assignee: Henkel CorporationInventor: Edgar R. Rogier
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Patent number: 4317935Abstract: Stable biologically active thromboxane A.sub.2 analogues having the formula: ##STR1## wherein R.sup.1 is OR.sup.3, where R.sup.3 represents hydrogen or a pharmaceutically acceptable cation or lower alkyl group; orR.sup.1 is NR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 are the same or different substituents selected from the group consisting of hydrogen and lower alkyl group; andR.sup.2 is hydrogen or an -OH group.The thromboxane analogues are potent thrombotic agents, useful in cardiovascular treatment.Type: GrantFiled: October 6, 1980Date of Patent: March 2, 1982Assignee: Research CorporationInventors: Kyriacos C. Nicolaou, Ronald L. Magolda, David A. Claremon
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Patent number: 4298762Abstract: Improved conversions of primary allylic and benzylic alcohols are obtained in an Oppenauer oxidation process, under Oppenauer oxidation conditions, by carrying out the oxidation employing furfural as the hydrogen acceptor. Primary alcohols to which the present invention relates are allylic alcohols substituted in at least the 2-position with a hydrocarbon radical and benzylic alcohols.Type: GrantFiled: December 5, 1979Date of Patent: November 3, 1981Assignee: SCM CorporationInventors: William J. Ehmann, Walter E. Johnson, Jr.
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Patent number: 4292432Abstract: A process for producing novel aldol derivatives of the formula, ##STR1## wherein C=W is a carbonyl group or a protected carbonyl group which comprises reacting a compound of the formula: ##STR2## wherein C=W is as defined above in the presence of an acid or a base at a temperature ranging from -70.degree. C. to room temperature. The novel aldol derivatives of the above formula are useful as intermediate for producing methanoprostacyclin derivatives which are useful medicines for prevention of thrombosis.Type: GrantFiled: February 4, 1980Date of Patent: September 29, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Keiichi Ono, Akihiko Sugie, Hajime Kawakami, Junki Katsube
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Patent number: 4284824Abstract: Described are methyl-substituted norbornane carboxaldehyde having the generic structure: ##STR1## wherein the dashed line is a carbon-carbon single bond, or a carbon-carbon double bond, and R.sub.1 R.sub.2 and R.sub.3 each represent methyl or hydrogen with the proviso that (i) R.sub.1 is hydrogen when R.sub.3 is methyl and (ii) R.sub.1 is methyl when R.sub.3 is hydrogen.Also described are processes and compositions for augmenting or enhancing the flavor and/or aroma of consumable materials including foodstuffs, chewing gums, medicinal products, toothpastes, chewing tobaccos, perfumes, colognes and perfumed articles such as solid or liquid anionic, cationic, nonionic or zwitterionic detergents or fabric softeners or fabric softener articles using as the essential ingredient at least one of the methyl substituted norbornane carboxaldehydes of our invention.Type: GrantFiled: May 22, 1980Date of Patent: August 18, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Philip T. Klemarczyk, James M. Sanders, Manfred H. Vock, Joaquin F. Vinals, Frederick L. Schmitt, Edward J. Granda
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Patent number: 4284820Abstract: 4-Formyl-3,6,6-trimethylbicyclo[3.1.0]hex-3-ene is oxidized in one vessel by a peroxy acid via 3,4-epoxy-4-formyl-3,6,6-trimethylbicyclo[3.1.0]hexane and 3,4-epoxy-4-formyloxy-3,6,6-trimethylbicyclo[3.1.0]hexane to 3,6,6-trimethyl-3-hydroxybicyclo[3.1.0]hexan-4-one. The four compounds are novel and are intermediates to pyrethroid insecticides.Type: GrantFiled: September 23, 1980Date of Patent: August 18, 1981Assignee: Shell Oil CompanyInventor: Johannes L. M. Syrier
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Patent number: 4277402Abstract: Formals of CH.sub.2 OH(CHOH).sub.n CH.sub.2 OH polyols (n=2 to 4) are prepared in less than 15 minutes by heating to about 125.degree. C., a mixture of e.g. sorbitol and paraformaldehyde in slight excess (5 to 10%), in the presence of e.g. sulfuric acid in catalytic quantities. Elution with methanol and filtration yield the pure solid cyclic triformal. The process can be carried in stages, using almost stoichiometric quantities of paraformaldehyde, but without any change in overall heating time.Type: GrantFiled: July 3, 1979Date of Patent: July 7, 1981Inventors: Robert A. Administrator of the National Aeronautics and Space Administration, with respect to an invention of Frosch, Algirdas C. Poshkus
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Patent number: 4270007Abstract: This invention is directed to mixtures of aldehydes of formulas ##STR1## This invention is also directed to the preparation of the mixture and the use of said mixture as a perfuming agent.Type: GrantFiled: November 14, 1979Date of Patent: May 26, 1981Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Jens Hagen, Klaus Bruns
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Patent number: 4260806Abstract: Stable biologically active thromboxane A.sub.2 analogues having the formula: ##STR1## wherein R.sup.1 is OR.sup.3, where R.sup.3 represents hydrogen or a pharmaceutically acceptable cation or lower alkyl group; orR.sup.1 is NR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 are the same or different substituents selected from the group consisting of hydrogen and lower alkyl group; andR.sup.2 is hydrogen or an --OH group.The thromboxane analogues are potent thrombotic agents, useful in cardiovascular treatment.Type: GrantFiled: October 24, 1979Date of Patent: April 7, 1981Assignee: Research CorporationInventors: Kyriacos C. Nicolaou, Ronald L. Magolda, David A. Claremon
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Patent number: 4250120Abstract: 5-Isopropyl-8-methyl bicyclo[5.3.0]deca-2,8-diene-2-carboxylic acid having a chemical structure represented by the following formula: ##STR1## and 5-isopropyl-8-methyl bicyclo[5.3.0]deca-2,8-diene-2-carboaldehyde having a chemical structure represented by the following formula: ##STR2## can be obtained by cultivating a microbial strain belonging to Genus Sclerotinia and having an ability to produce them, and collecting them from the cultivated mixture.Type: GrantFiled: June 20, 1979Date of Patent: February 10, 1981Assignee: Noda Institute for Scientific ResearchInventors: Shingo Marumo, Masato Katayama
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Patent number: 4250338Abstract: Described are compounds covered by the generic structure; ##STR1## where one, two or all of R.sub.1, R.sub.2 and R.sub.3 are the same or different and each represents hydrogen or lower alkyl of from 1 up to 3 carbon atoms; a process for preparing same using compounds having the generic structure; ##STR2## where one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines represents carbon-carbon single bonds and organoleptic uses thereof in perfumes, colognes, perfumed articles such as anionic, cationic and non-ionic detergents, cosmetic powders and dryer-added fabric softener articles, as well as in smoking tobaccos and smoking tobacco articles, e.g., the body of smoking tobacco, the wrapper or the filter therefor.Type: GrantFiled: November 16, 1979Date of Patent: February 10, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, James M. Sanders, William L. Schreiber, Hugh Watkins, Joaquin F. Vinals, Edward J. Shuster, Thomas J. O'Rourke, Myrna L. Hagedorn, Philip Klemarczyk
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Patent number: 4229324Abstract: A tricyclo-.alpha.,.beta.-unsaturated aldehyde represented by the formula (I), ##STR1## wherein the group ##STR2## is attached to the exo side of the norbornane ring at the 8- or 9-position, R represents an alkyl group having 1 to 6 carbon atoms, and the dotted line between carbon 3 and carbon 4 represents a saturated or ethylenically unsaturated bond possesses odorous characteristics and is useful for perfume compositions.Type: GrantFiled: April 26, 1979Date of Patent: October 21, 1980Assignee: Kao Soap Company, LimitedInventors: Naotake Takaishi, Yoshiaki Inamoto, Masamoto Matsukane
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Patent number: 4225515Abstract: A perfume composition comprising an isomeric hydroxymethyl tricyclo(5,2,1,0.sup.2,6)-decane of the formula ##STR1## wherein R.sub.1 and R.sub.2 are the hydroxymethyl CH.sub.2 OH or the formyl CHO group andR.sub.1 represents CH.sub.2 OH, when R.sub.2 is CHO and vice versaor a mixture thereof.Type: GrantFiled: October 25, 1978Date of Patent: September 30, 1980Assignee: Ruhrchemie AktiengesellschaftInventors: Jurgen Weber, Heinz Grau
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Patent number: 4225508Abstract: Prostacyclin and prostacyclin-type derivatives having a 19-hydroxy feature are disclosed, including processes for preparing them and the appropriate intermediates. The compounds are useful for pharmacological purposes such as inhibition of blood platelate aggregation.Type: GrantFiled: July 5, 1979Date of Patent: September 30, 1980Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4224253Abstract: Novel 2-methylene-3-methyl-3-(1',3'-pentadien-1'-yl)-bicyclo-[2,2,1]-heptanes substituted in the 4'-position by methyl, alkoxycarbonyl, formyl, hydroxymethyl or cyano are obtained by reacting the novel aldehyde 2-methylene-3-methyl-3-formyl-bicyclo-[2,2,1]-heptane with 3-methyl-, 3-alkoxycarbonyl- or acetalized 3-formyl-2-butene-1-triarylphosphorylidene under the conditions of a Wittig reaction, with or without hydrolytic cleavage of the acetal group, or hydrolytic cleavage of the acetal group followed by reduction of the formyl group to the hydroxymethyl group, or hydrolytic cleavage of the acetal group, reaction of the aldehyde with a hydroxylammonium salt, and dehydration of the resulting oxime.The novel compounds are distinguished by interesting scent characteristics.Type: GrantFiled: August 28, 1978Date of Patent: September 23, 1980Assignee: BASF AktiengesellschaftInventors: Manfred Baumann, Werner Hoffmann