Polycyclo-alicyclic Ring System Patents (Class 568/445)
  • Patent number: 4421935
    Abstract: 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: Grant
    Filed: May 3, 1982
    Date of Patent: December 20, 1983
    Assignee: Shell Oil Company
    Inventor: Pieter A. Verbrugge
  • Patent number: 4408077
    Abstract: 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: Grant
    Filed: November 13, 1981
    Date of Patent: October 4, 1983
    Assignee: Ayerst, McKeena & Harrison, Inc.
    Inventors: Kazimir Sestanj, Steven Fung, Nedumparambil A. Abraham, Francesco Bellini
  • Patent number: 4354043
    Abstract: 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: Grant
    Filed: September 17, 1981
    Date of Patent: October 12, 1982
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Robert P. Belko, Richard M. Boden, Marie R. Hanna
  • Patent number: 4334100
    Abstract: 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: Grant
    Filed: November 14, 1979
    Date of Patent: June 8, 1982
    Assignee: Henkel Kommanditgesellschaft auf Aktien (Henkel KGaA)
    Inventors: Jens Hagen, Klaus Bruns
  • Patent number: 4319049
    Abstract: 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: Grant
    Filed: October 6, 1980
    Date of Patent: March 9, 1982
    Assignee: Henkel Corporation
    Inventor: Edgar R. Rogier
  • Patent number: 4317935
    Abstract: 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: Grant
    Filed: October 6, 1980
    Date of Patent: March 2, 1982
    Assignee: Research Corporation
    Inventors: Kyriacos C. Nicolaou, Ronald L. Magolda, David A. Claremon
  • Patent number: 4298762
    Abstract: 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: Grant
    Filed: December 5, 1979
    Date of Patent: November 3, 1981
    Assignee: SCM Corporation
    Inventors: William J. Ehmann, Walter E. Johnson, Jr.
  • Patent number: 4292432
    Abstract: 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: Grant
    Filed: February 4, 1980
    Date of Patent: September 29, 1981
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keiichi Ono, Akihiko Sugie, Hajime Kawakami, Junki Katsube
  • Patent number: 4284824
    Abstract: 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: Grant
    Filed: May 22, 1980
    Date of Patent: August 18, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Philip T. Klemarczyk, James M. Sanders, Manfred H. Vock, Joaquin F. Vinals, Frederick L. Schmitt, Edward J. Granda
  • Patent number: 4284820
    Abstract: 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: Grant
    Filed: September 23, 1980
    Date of Patent: August 18, 1981
    Assignee: Shell Oil Company
    Inventor: Johannes L. M. Syrier
  • Patent number: 4277402
    Abstract: 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: Grant
    Filed: July 3, 1979
    Date of Patent: July 7, 1981
    Inventors: Robert A. Administrator of the National Aeronautics and Space Administration, with respect to an invention of Frosch, Algirdas C. Poshkus
  • Patent number: 4270007
    Abstract: 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: Grant
    Filed: November 14, 1979
    Date of Patent: May 26, 1981
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Jens Hagen, Klaus Bruns
  • Patent number: 4260806
    Abstract: 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: Grant
    Filed: October 24, 1979
    Date of Patent: April 7, 1981
    Assignee: Research Corporation
    Inventors: Kyriacos C. Nicolaou, Ronald L. Magolda, David A. Claremon
  • Patent number: 4250338
    Abstract: 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: Grant
    Filed: November 16, 1979
    Date of Patent: February 10, 1981
    Assignee: 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
  • Patent number: 4250120
    Abstract: 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: Grant
    Filed: June 20, 1979
    Date of Patent: February 10, 1981
    Assignee: Noda Institute for Scientific Research
    Inventors: Shingo Marumo, Masato Katayama
  • Patent number: 4229324
    Abstract: 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: Grant
    Filed: April 26, 1979
    Date of Patent: October 21, 1980
    Assignee: Kao Soap Company, Limited
    Inventors: Naotake Takaishi, Yoshiaki Inamoto, Masamoto Matsukane
  • Patent number: 4225515
    Abstract: 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: Grant
    Filed: October 25, 1978
    Date of Patent: September 30, 1980
    Assignee: Ruhrchemie Aktiengesellschaft
    Inventors: Jurgen Weber, Heinz Grau
  • Patent number: 4225508
    Abstract: 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: Grant
    Filed: July 5, 1979
    Date of Patent: September 30, 1980
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4224253
    Abstract: 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: Grant
    Filed: August 28, 1978
    Date of Patent: September 23, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Baumann, Werner Hoffmann