Bicyclo Ring System Patents (Class 568/819)
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Patent number: 4582945Abstract: C-8-substituted 1,5-dimethyl-bicyclo[3.2.1]octane-8-ols having the general formula I ##STR1## wherein R is a lower open chained or cyclic alkyl- alkenyl- or alkinyl group having up to 6 carbon atoms and the wavy line at the C-8 atom means epimeric forms, the process for producing these compounds and their use as odorants and constituents of parfume composition for cosmetic and industrial parfuming or essential oils and flavoring agents.Type: GrantFiled: July 21, 1982Date of Patent: April 15, 1986Assignee: Dragoco Gerberding & Co. GmbHInventors: Ernst-Joachim Brunke, Hartmut Struwe
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Patent number: 4535192Abstract: Described are tertiary pentamethylindanol derivatives defined according to the structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond and uses thereof in augmenting or enhancing the aroma or taste of consumable materials selected from the group consisting of perfume compositions, colognes, perfumed articles, foodstuffs, smoking tobaccos and smoking tobacco compositions.Type: GrantFiled: November 14, 1984Date of Patent: August 13, 1985Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, Takao Yoshida
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Patent number: 4533749Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: February 16, 1982Date of Patent: August 6, 1985Assignee: The Upjohn CompanyInventors: Paul A. Aristoff, John C. Sih
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Patent number: 4525586Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), methano (C-6a,9), and an additional (olefinic) valence bond (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2', 9-methano (or 2', 9-methano)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.Type: GrantFiled: September 19, 1983Date of Patent: June 25, 1985Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4520032Abstract: Described are tertiary pentamethylindanol derivatives defined according to the structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond and uses thereof in augmenting or enhancing the aroma or taste of consumable materials selected from the group consisting of perfume compositions, colognes, perfumed articles, foodstuffs, smoking tobaccos and smoking tobacco compositions.Type: GrantFiled: March 14, 1984Date of Patent: May 28, 1985Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, Takao Yoshida
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Patent number: 4503240Abstract: Process for the preparation of 8,12-epoxy-13,14,15,16-tetranorlabdane by way of converting farnesyl bromide to farnesyl cyanide, followed by the saponification of the farnesyl cyanide to homofarnesic acid which is then cyclized to norambreinolide in the presence of titanium tetrachloride, converting the norambreinolide with LiAlH.sub.4 to 8-hydroxy-13,14,15,16-tetranorlabdane-12-ol, and cyclization of the diol in the presence of POCl.sub.3 to 8,12-epoxy-13,14,15,16-tetranorlabdane. The resulting product exhibits an amber scent, used in perfumery.Type: GrantFiled: July 28, 1983Date of Patent: March 5, 1985Assignee: Consortium F/u/ r Elektrochemische Industrie GmbHInventors: Gerhard Staiger, Antonio Macri
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Patent number: 4497830Abstract: Compounds of Formula I ##STR1## wherein X is oxygen or CH.sub.2 ;A is CH.sub.2 --CH.sub.2, trans-CH.dbd.CH or C.tbd.C;W is free or functionally modified hydroxymethylene or free or functionally modified ##STR2## and the OH groups may be in the .alpha.- or the .beta.-position; D is straight chain or branched, saturated or unsaturated hydrocarbon aliphatic of from 1 to 10 carbon atoms, which may be substituted by fluorine;E is C.tbd.C or CR.sub.3 .dbd.CR.sub.4, R.sub.3 and R.sub.4 being different and being hydrogen or alkyl of 1 to 5 carbon atoms;R.sub.1 is free or functionally modified hydroxy; andR.sub.2 is alkyl, cycloalkyl, optionally substituted aryl or heterocyclic,have valuable pharmacological properties, e.g., hypotensive and bronchodilatory characteristics. They can furthermore be used for prophylaxis and therapy of coronary infarct and as a treatment for stroke. They are produced by means of reduction of the corresponding 1-carbonic acid derivatives.Type: GrantFiled: May 24, 1982Date of Patent: February 5, 1985Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Jorge Casals-Stenzel, Ekkehard Schillinger, Gerda Mannesmann, Bob Nieuweboer
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Patent number: 4490555Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: March 19, 1982Date of Patent: December 25, 1984Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4487961Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: February 16, 1982Date of Patent: December 11, 1984Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4487979Abstract: The purification of bis(4-hydroxycyclohexyl) alkane, particularly hydrogenated bisphenol A (HBPA) is carried out via recrystallization from at least one halogen-containing solvent solution.Type: GrantFiled: April 18, 1983Date of Patent: December 11, 1984Assignee: Phillips Petroleum CompanyInventor: Roger G. Gaughan
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Patent number: 4487960Abstract: Novel compounds of the following formula: ##STR1##Type: GrantFiled: April 19, 1982Date of Patent: December 11, 1984Assignee: The Upjohn CompanyInventor: Chiu-Hong Lin
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Patent number: 4473711Abstract: 1-Tetralone, an intermediate in the production of the insecticide, 1-naphthyl carbamate, is conveniently prepared by a liquid phase oxidation of tetralin in the presence of a novel chromium exchanged cation-exchange resin catalyst.Type: GrantFiled: August 6, 1981Date of Patent: September 25, 1984Assignee: Union Carbide CorporationInventor: Robert W. Coon
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Patent number: 4471135Abstract: Described is 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol as a mixture of isomers and in its isomeric forms having the structures: ##STR1## and the uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles, and colognes. Also described is a novel process for preparing 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol.Type: GrantFiled: September 26, 1983Date of Patent: September 11, 1984Assignee: International Flavors & Fragrances Inc.Inventors: William J. Evers, Braja D. Mookherjee, Anton Van Ouwerkerk, Augustinus G. Van Loveren
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Patent number: 4439614Abstract: 5,6-Methano-5,6-dihydroretinoids such as ethyl (E)-5,6-methano-5,6-dihydroretinoate and (E)-1-(4-carbethoxyphenyl)-2-methyl-4-(2,2,6-trimethylbicyclo[4.1.0]hept-1 -yl)-1,3-butadiene are disclosed. These componds are useful as chemopreventive agents for inhibiting tumor promotion in epithelial cells and for treating nonmalignant skin disorders.Type: GrantFiled: September 22, 1982Date of Patent: March 27, 1984Assignee: SRI InternationalInventors: Marcia I. Dawson, Rebecca Chan, Peter D. Hobbs
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Patent number: 4434306Abstract: A perfume composition is described, which contains at least one compound of bicyclo[2,2,2]octane and bicyclo[2,2,2]octene derivatives represented by the general formula (I) ##STR1## wherein the symbols are the same as defined hereinbefore.Type: GrantFiled: December 14, 1981Date of Patent: February 28, 1984Assignee: Takasago Perfumery Co., Ltd.Inventors: Toyohiko Kobayashi, Haruki Tsuruta
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Patent number: 4431843Abstract: Described are compounds having the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond; wherein X represents the moieties: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.8 and R.sub.9 represent hydrogen or methyl with the proviso that (i) at least three of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen and (ii) when the dashed line is a carbon-carbon single bond and X is: ##STR3## then one of R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is methyl and the other represents hydrogen; wherein R.sub.5 represents hydrogen, MgZ or Li; wherein Z represents chloro, bromo or iodo and wherein R.sub.Type: GrantFiled: April 26, 1982Date of Patent: February 14, 1984Assignee: International Flavors & Fragrances Inc.Inventor: Takao Yoshida
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Patent number: 4424376Abstract: A method is provided for preparing intermediates for use in prostacyclin syntheses which method includes the steps of aceylating ketopinic acid or its acid halide to form the corresponding ketopinoyl diene ester intermediate, subjecting the diene ester to a Diels-Alder reaction by reacting same with cyclopentendione, subjecting the resulting chiral ester intermediate to a fluorination and reduction to form the corresponding chiral ester diol intermediate, subjecting the diol to solvolysis to form the chiral triol intermediate, hydroxylating the chiral triol to form a pentol intermediate, subjecting the pentol to a ring cleavage to form the difluoro dihydroxy prostacyclin intermediate ##STR1## and subjecting same to a Witting reaction to form the difluoro dihydroxy prostacyclin intermediate ##STR2## All of the above-mentioned intermediates are novel compounds and thus are also provided.Type: GrantFiled: September 23, 1982Date of Patent: January 3, 1984Assignee: E. R. Squibb & Sons, Inc.Inventors: Jerome L. Moniot, Rita T. Fox, Peter W. Sprague, Martin F. Haslanger
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Patent number: 4420632Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet antiaggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.Type: GrantFiled: December 22, 1980Date of Patent: December 13, 1983Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4410515Abstract: A synthetic compound which is biologically active in maintaining calcium and phosphorous metabolism in animals, of the formula I ##STR1## wherein the double bond between positions C-22 and C-23 is single or double; R.sup.2 is hydrogen, CH.sub.3 or CH.sub.2 CH.sub.3 ; X is selected from the group consisting of hydrogen and --OR.sup.1, where R.sup.1 is hydrogen or a straight or branched chain glycosidic residue containing 1-20 glycosidic units per residue; with the proviso that at least one of the R.sup.1 is a glycosidic residue.Type: GrantFiled: April 1, 1981Date of Patent: October 18, 1983Assignee: Massachusetts General HospitalInventors: Sally A. Holick, Michael F. Holick
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Patent number: 4377714Abstract: Described are compounds having the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond; wherein X represents the moieties: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen or methyl with the proviso that (i) at least three of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen and (ii) when the dashed line is a carbon-carbon single bond and X is: ##STR3## then one of R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is methyl and the other represents hydrogen; wherein R.sub.5 represents hydrogen, MgX, MgR.sub.7, CdR.sub.7, ZnR.sub.7, Na, K or Li; wherein X represents Chloro, Bromo or Iodo; wherein R.sub.6 represents hydrogren or methyl; and wherein R.sub.Type: GrantFiled: October 22, 1981Date of Patent: March 22, 1983Assignee: International Flavors & Fragrances Inc.Inventor: Takao Yoshida
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Patent number: 4358406Abstract: This invention provides a new derivative of vitamin D, 26,26,26,27,27,27-hexafluoro-1.alpha.,25-dihydroxycholecalciferol, a process for preparing the same, and novel intermediate compounds.The compound is characterized by vitamin D-like activity substantially greater than that exhibited by 1.alpha.,25-dihydroxycholecalciferol which is considered to be the active hormonal form of vitamin D. The compound would find ready application as a substitute for vitamin D and in the treatment of or prophylaxis for disease states evincing metabolic calcium and phosphorous deficiences or imbalances.Type: GrantFiled: July 27, 1981Date of Patent: November 9, 1982Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Yoko Tanaka, Nobuo Ikekawa, Yoshiro Kobayashi
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Patent number: 4341908Abstract: Compounds useful as fragrance materials having the structure ##STR1## wherein each of R.sub.1, R.sub.2, and R.sub.3 are hydrogen or methyl can be prepared by reacting a halogen-containing cyclohexane, having the structure ##STR2## wherein each of R.sub.1, R.sub.2, and R.sub.3 are hydrogen or methyl and X is a halogen, with a reagent capable of effecting intramolecular cyclization.Type: GrantFiled: June 20, 1980Date of Patent: July 27, 1982Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Brian J. Willis, Philip A. Christenson, Robert A. Mack
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Patent number: 4339467Abstract: Described are compounds having the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond; wherein X represents the moieties: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.8 and R.sub.9 represent hydrogen or methyl with the proviso that (i) at least three of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen and (ii) when the dashed line is a carbon-carbon single bond and X is: ##STR3## then one of R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is methyl and the other represents hydrogen; wherein R.sub.5 represents hydrogen, MgZ or Li; wherein Z represents chloro, bromo or iodo and wherein R.sub.Type: GrantFiled: June 25, 1981Date of Patent: July 13, 1982Assignee: International Flavors & Fragrances Inc.Inventor: Takao Yoshida
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Patent number: 4338457Abstract: The present invention relates to novel compositions of matter and novel processes for preparing these compositions of matter. Moreover, there are provided novel methods by which certain of these novel compositions of matter are employed for pharmacologically useful purposes.Type: GrantFiled: February 28, 1980Date of Patent: July 6, 1982Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4331602Abstract: Compounds having the formula ##STR1## wherein ##STR2## R.sub.1 is hydrogen, benzyl or alkanoyl, X is C.sub.2-4 alkylene; andZ-W is alkyl, phenylalkyl or pyridylalkyl which can have an oxygen atom as part of the alkyl chain and their use as CNS agents, antidiarrheals and antiemetics. Processes for their preparation and intermediates therefor are described.Type: GrantFiled: March 16, 1981Date of Patent: May 25, 1982Assignee: Pfizer Inc.Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4322567Abstract: In a process for producing an aromatic alcohol by catalytic hydrogenation of at least one tertiary peroxide selected from the group consisting of tertiary aromatic hydroperoxides and tertiary aromatic peroxides in the presence of a palladium catalyst in a lower aliphatic alcohol solvent to form the corresponding alcohol; the improvement wherein said catalyst has a palladium metal surface area, determined by the CO chemisorption method, of up to about 200 m.sup.2 /g.multidot.Pd.Type: GrantFiled: May 22, 1980Date of Patent: March 30, 1982Assignee: Mitsui Petrochemical Industries Ltd.Inventors: Fujihisa Matsunaga, Norio Ohno, Hirohiko Nambu
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Patent number: 4311644Abstract: A method is provided for preparing intermediates for use in 10,10-difluoro prostacyclin syntheses which method includes the steps of aceylating ketopinic acid or its acid halide to form the corresponding ketopinoyl diene ester intermediate, subjecting the diene ester to a Diels-Alder reaction by reacting same with cyclopentendione, subjecting the resulting chiral ester intermediate to a fluorination and reduction to form the corresponding chiral ester diol intermediate, subjecting the diol to solvolysis to form the chiral triol intermediate, hydroxylating the chiral triol to form a pentol intermediate, subjecting the pentol to a ring cleavage to form the difluoro dihydroxy prostacyclin intermediate ##STR1## and subjecting same to a Wittig reaction to form the difluoro dihydroxy prostacyclin intermediate ##STR2## All of the above-mentioned intermediates are novel compounds and thus are also provided.Type: GrantFiled: January 30, 1981Date of Patent: January 19, 1982Assignee: E. R. Squibb & Sons, Inc.Inventors: Jerome L. Moniot, Rita T. Fox, Peter W. Sprague, Martin F. Haslanger
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Patent number: 4296038Abstract: A four-step process for producing (-)-dihydrochrysanthemolactone from 2-caren-4-one is disclosed. The four steps in order are methylating 2-caren-4-one, oxidizing, methylating the tautomeric mixture resulting from the oxidation, and finally lactonizing the single hydroxy acid resulting from the second methylation. Additionally, three novel intermediate compounds that are produced by the steps in the process are disclosed.Type: GrantFiled: April 24, 1980Date of Patent: October 20, 1981Assignee: SCM CorporationInventors: T. L. Ho, Zia U. Din
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Patent number: 4283575Abstract: The present invention provides novel 2-decarboxy-2-hydroxymethyl-19-hydroxy-6a-carba-PGI.sub.1 compounds which are useful for pharmacological purposes, e.g., anti-asthmatic indications.Type: GrantFiled: March 3, 1980Date of Patent: August 11, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4271091Abstract: Cyclohexanone and/or cyclohexanol can be oxidized in the vapor phase to phenol by contacting the cyclohexanone and/or cyclohexanol with a suitable oxidation catalyst in the presence of molecular oxygen. Suitable catalysts are solids comprising Mo, W, Sb and/or V oxides or complexes thereof. The catalysts may be promoted with additional elements.Type: GrantFiled: June 17, 1978Date of Patent: June 2, 1981Assignee: Standard Oil CompanyInventors: Robert K. Grasselli, Dev D. Suresh
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Patent number: 4267395Abstract: The present invention provides novel 2-decarboxy-2-hydroxymethyl-19-hydroxy-19-methyl-6a-carba-PGI.sub.1 compounds which are useful for pharmacological purposes, e.g., anti-asthmatic indications.Type: GrantFiled: March 3, 1980Date of Patent: May 12, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4247409Abstract: Described is a process for augmenting or enhancing the aroma of a solid or liquid anionic, cationic or nonionic detergent comprising the step of intimately admixing with a solid or liquid anionic, cationic or nonionic detergent base, a product prepared by a process comprising the steps of (i) intimately admixing aluminum isopropylate, toluene and a caryophyllene derivative selected from the group consisting of caryophyllene oxide and dihydro caryophyllene oxide to form a mixture; (ii) heating the resulting mixture at a temperature of from 100.degree. C. up to 150.degree. C. for a period of time from about one up to about five hours; and (iii) the rearranged caryophyllene oxide or dihydro caryophyllene oxide, a mixture of alcohols, from the reaction mass; the concentration of aluminum isopropylate catalyst in the reaction mass varying from about 0.025 molar up to about 0.75 molar; and the concentration of caryophyllene oxide or dihydro caryophyllene oxide in the reaction mass varying from about 0.Type: GrantFiled: December 21, 1979Date of Patent: January 27, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Cynthia J. Mussinan, Braja D. Mookherjee, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala, Frederick L. Schmitt
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Patent number: 4229599Abstract: A process for preparing a mixture of isomers of caryophyllene alcohol and dihydrocaryophyllene alcohol including 10,10-dimethyl-2,6-dimethylene bicyclo[7.2.0]undecan-5-ol by isomerizing caryophyllene oxide or dihydrocaryophyllene oxide using an aluminum isopropylate catalyst in a toluene solvent at temperatures in the range of from about 100.degree. C. up to about 150.degree. C. is described.Type: GrantFiled: September 29, 1978Date of Patent: October 21, 1980Assignee: International Flavors & Fragrances Inc.Inventors: Cynthia J. Mussinan, Braja D. Mookherjee, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala, Frederick L. Schmitt
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Patent number: 4201881Abstract: The invention provides new derivatives of vitamin D, 24,24-difluoro-1.alpha.,25-dihydroxycholecalciferol and 24,24-difluoro-1.alpha.,25-dihydroxy-5,6-trans-cholecalciferol and processes for preparing the same.The compounds are characterized by vitamin D-like activity essentially equivalent to the vitamin D-like activity of 1.alpha.,25-dihydrocholecalciferol which is considered to be the hormonal form and most active derivative of vitamin D. The compounds of this invention are characterized by their ability to increase intestinal calcium transport, increase serum calcium and to prevent the development of rickets. These compounds would find ready application as a substitute for vitamin D and in the treatment of disease states evincing metabolic calcium and phosphorus deficiencies.Type: GrantFiled: March 28, 1979Date of Patent: May 6, 1980Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Heinrich K. Schnoes, Nobuo Ikekawa, Yoko Tanaka, Yoshiro Kobayashi
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Patent number: 4163866Abstract: .alpha.-Ambrinol, a bicyclic alcohol of formula ##STR1## is prepared by a novel process starting from .beta.-ionone via cyclization followed by catalytic reduction.Type: GrantFiled: July 12, 1977Date of Patent: August 7, 1979Assignee: Firmenich SAInventor: Hugo Strickler
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Patent number: 4162258Abstract: Novel compounds trans- and/or cis-spiro[5-isopropylbicyclo[3.1.0]hexane-2,2'-oxiranes], process for the production of the novel compounds comprising reacting 3-isopropyl-2-cyclopenten-1-one with sulfoxonium methylide to form the novel compounds, process for the production of novel compounds comprising reacting 5-isopropylbicyclo[3.1.0]hexan-2-one with sulfonium methylide or sulfoxonium methylide to form the novel compounds, and process for the production of novel compounds comprising the steps of reacting 3-isopropyl-2-cyclopenten-1-one with sulfoxonium methylide to form 5-isopropylbicyclo[3.1.0]hexan-2-one and then reacting the 5-isopropylbicyclo[3.1.0]hexan-2-one with sulfonium methylide or sulfoxonium methylide to form the novel compounds. Trans- and/or cis-sabinene hydrates can readily be prepared from the novel compounds trans- and/or cis-spiro[5-isopropylbicyclo[3.1.0]hexane-2,2'-oxiranes].Type: GrantFiled: March 27, 1978Date of Patent: July 24, 1979Assignee: The Lion Dentifrice Co., Ltd.Inventors: Moriaki Higo, Haruhiko Toda, Kunitomo Suzuki, Yasukuni Nishida
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Patent number: 4149017Abstract: Useful intermediates in the preparation of bicycloalkyl analogues or derivatives of prostaglandins are represented by the formula ##STR1## wherein: X is an iodo or bromo radical;A is an acid-labile hydroxyl-protecting group;G is an integer having a value of from 0 to 10; andB is selected for the class of bicycloalkyl radicals of the formula: ##STR2## WHERE M AND P ARE INTEGERS HAVING A VALUE OF FROM 1 TO 4; N IS AN INTEGER HAVING A VALUE OF FROM 0 TO 4 SUCH THAT THE SUM OF M, N AND P IS GREATER THAN OR EQUAL TO 3 AND THE POINT OF ATTACHMENT OF THE ALKYL CHAIN (CH.sub.2).sub.g to the bicycloalkyl radical is in the (CH.sub.2).sub.m bridge or in the bridgehead position.Type: GrantFiled: July 25, 1977Date of Patent: April 10, 1979Assignee: Miles Laboratories, Inc.Inventors: Warren D. Woessner, Charles J. Sih, Harold C. Kluender, Henry C. Arndt, William G. Biddlecom
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Patent number: 4144191Abstract: Olefins are converted to alcohols by a one-step, hydroformylation process comprising contacting an olefin, such as 1-hexene, with a gaseous mixture of carbon monoxide and hydrogen in the presence of a catalyst prepared by loading a bimetallic cluster of the formula: Rh.sub.x Co.sub.y CO.sub.12 wherein both x and y are independently integers 1-3 with the proviso that .SIGMA. (x+y)=4, onto an amine resin, such as Dowex.RTM. MWA-1.Type: GrantFiled: June 6, 1977Date of Patent: March 13, 1979Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, Philip E. Garrou
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Patent number: 4119575Abstract: Compounds represented by the structural formulae ##STR1## wherein n is an integer 0 or 1; A, B and C each independently represent hydrogen or alkyl having from 1 to 3 carbon atoms, provided that when n is 0 at least one of A, B or C cannot be hydrogen; R represents hydrogen or an alkyl having from 1 to 6 carbon atoms; D and E each independently represent hydrogen or alkyl having from 1 to 6 carbon atoms, provided that the sum of the carbon atoms in D and E does not exceed 6, provided that, in the bicyclo compounds, at least one of A, B, C, D or E must be an alkyl; m is an integer 1 through 8; F and G represent hydrogen or alkyl having from 1 to 3 carbon atoms; X represents ##STR2## WHEREIN P IS AN INTEGER 0 THROUGH 2 AND I and J each independently represent hydrogen or methyl, provided that if p is 0 then m must be greater than 2; provided that the sum of the carbon and oxygen atoms in the compound is no greater than 23, are useful as fragrances or as components in fragrance compositions.Type: GrantFiled: February 28, 1977Date of Patent: October 10, 1978Assignee: Monsanto CompanyInventors: Jordan J. Bloomfield, Dennis C. Owsley
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Patent number: 4100110Abstract: Novel compounds of use in perfumery are obtained by performing a Prins reaction on isolongifolene. They include novel primary and secondary alcohols, their esters and the corresponding aldehydes and ketones.Type: GrantFiled: August 11, 1975Date of Patent: July 11, 1978Assignee: Bush Boake Allen LimitedInventors: Hifzur Rahman Ansari, Neville Unwin, Horst Richard Wagner