Polycyclo Ring System Patents (Class 568/817)
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Patent number: 5107037Abstract: The invention concerns a novel process for the manufacture of 2-hydroxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene, I, commonly known as .alpha.-ambrinol. ##STR1## The process comprises reducing either an 8-halo-2-hydroxy-2,5,5-trimethyl-2,3,4,4a,5,6,7,8-octahydronaphthalene (IIa), alone or in a mixture with a 1-halo-2-hydroxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (IIb), or reduced the 1,2-epoxide which can be formed therefrom, namely, 1,2-epoxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octanhydronaphthalene (III). The halohydrins II are prepared from 1,1,6-trimethyl-1,2,3,7,8,8a-hexahydronaphthalene, IV.The compounds of formulas II and III are novel and form part of the present invention. The formula III epoxide possesses valuable odorant properties and its use as an odorant also forms part of the invention.Type: GrantFiled: June 6, 1990Date of Patent: April 21, 1992Assignee: Givaudan CorporationInventor: Peter Naegeli
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Patent number: 5039710Abstract: Aphidicolane derivatives of the formula: ##STR1## wherein R.sup.1 stands for hydrogen or a hydroxy radical, R.sup.2 stands for a hydroxy or methyl radical, or the group CR.sup.1 R.sup.2 stands for a keto group; R.sup.3 stands for a formyl or hydroxymethyl radical, or for the group --CH.sub.2 O.CO.OR.sup.6, wherein R.sup.6 stands for a defined radical or R.sup.2 and R.sup.3 are joined together to form the group --O.CO.OCH.sub.2 --; R.sup.4 stands for a hydroxy radical; R.sup.5 stands for a formyl radical, a hydroxyalkyl radical --(CH.sub.2).sub.1-3 OH, a radical --CHR.sup.7 OH, wherein R.sup.7 stands for a defined radical, or R.sup.5 stands for an azidomethyl or pyrrolidinylcarbonyloxymethyl radical, or for the group --CH.sub.2 O.CO.OR.sup.8, wherein R.sup.8 stands for a defined radical, or R.sup.5 stands for the group --CH.sub.2 O.CO.(CH.sub.2).sub.m.CR.sup.11 R.sup.12.(CH.sub.2).sub.n.NR.sup.9 R.sup.10, wherein m, n, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 have defined values, or R.sup.Type: GrantFiled: September 17, 1990Date of Patent: August 13, 1991Assignee: Imperial Chemical Industries PLCInventor: Arnold H. Ratcliffe
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Patent number: 5030772Abstract: This invention relates to hydroxylated derivatives of vitamin D.sub.2 and a process for preparing such compounds. In particular, a process for preparing the 24-epimer of vitamin D.sub.2 and the corresponding 1.alpha.-hydroxylated derivative thereof is disclosed. The vitamin D.sub.2 derivatives would find application in the treatment of or prophylaxsis for various disease states characterized by calcium and phosphorous imbalances.Type: GrantFiled: February 14, 1990Date of Patent: July 9, 1991Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Shigeya Okada
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Patent number: 5028631Abstract: Compounds of the formula: ##STR1## useful as anti-cancer agents, anti-obesity agents, anti-hyperglycemic agents, anti-aging agents, anti-hyperglycemic agents and anti-autoimmune agents.Type: GrantFiled: November 25, 1987Date of Patent: July 2, 1991Inventors: Arthur G. Schwartz, Marvin L. Lewbart
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Patent number: 5015761Abstract: Novel tricycloundecanones are disclosed having the general formula ##STR1## wherein R.sub.1, R.sub.2, and R.sub.3 are hydrogen or 1 to 3 carbon alkyl groups having a total carbon number of six or less. These compounds are useful perfumery ingredients characterized by odors of the woody type.Useful derivatives of the compounds are also disclosed as well as a novel procedure for preparation thereof.Type: GrantFiled: December 5, 1988Date of Patent: May 14, 1991Assignee: PFW(Nederland)B.V.Inventors: Willem Lenselink, Gerben Sipma
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Patent number: 5004843Abstract: Process for preparing predominantly Z-substituted allylic alcohols of the formula: ##STR1## wherein R.sup.1 is a straight or branched C.sub.1 -C.sub.25 alkyl group optionally bearing at least one substituent and/or at least one unsaturated linkage and R.sup.2 is a hydrogen atom or a methyl group, which comprises reacting a vinyl epoxide of the formula: ##STR2## wherein R.sup.2 is as defined above with an organolithium compound of the formula above. More particularly, there is disclosed a process for R.sup.1 --Li wherein R.sup.1 is as defined above; particularly, process for preparing .alpha.-santalol of the formula: ##STR3## which comprises reacting 3-methyl-3,4-epoxybutene-1 with lithiomethyl-2,3-dimethyltricyclo[2.2.1.0.sup.2,6 ]heptane.Type: GrantFiled: May 29, 1990Date of Patent: April 2, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Mitsuhisa Tamura, Gohu Suzukamo, Ken-ichi Hirose
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Patent number: 5001120Abstract: A-Nor-5.alpha.-androstane compounds, such as the dipropionate and disuccinate esters of 2.alpha.,17.alpha.-diethynyl-A-Nor-5.alpha.-androstane-2.beta.,17.beta.-di ol and the corresponding 2.alpha.,17.alpha.-diol stereoisomers have an inhibitory effect on malignant cell growth and can be used to treat various carcinomas in mammals.Type: GrantFiled: May 10, 1989Date of Patent: March 19, 1991Assignee: Natural Pharmacia International, Inc.Inventors: Rui-Lin Li, David Y. Lee, Qi-Lu Cheng
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Patent number: 4952737Abstract: An improved polymerization catalyst, its preparation, and use are disclosed. The catalyst is one prepared by reacting a benzoic acid ester, an alkoxy titanium compound, and a magnesium halide having alkanol associated therewith to form a first catalyst component then reacting said first catlyst component with an organoaluminum halide and then reacting the resulting solid with a halogenating agent comprising a titanium halide. Also novel crystalline MgCl.sub.2 electron donor complexes are disclosed, one of which, MgCl.sub.2.CH.sub.3 OH, can be used in the preparation of the improved polymerization catalyst herein.Type: GrantFiled: October 11, 1988Date of Patent: August 28, 1990Assignee: Phillips Petroleum CompanyInventor: Kenneth E. Inkrott
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Patent number: 4876399Abstract: The present invention is directed to novel taxols useful as a chemotherapeutic agent. Moreover, the present invention is directed to the process of preparing taxols and various intermediates in said process. A key intermediate is this process is 2,5-dihydroxy-2-patchoulenes. Therefore the present invention is also related to said intermediate and the process for its preparation.Type: GrantFiled: November 2, 1987Date of Patent: October 24, 1989Assignee: Research Corporation Technologies, Inc.Inventors: Robert A. Holton, Rouh-Rong Juo, Richard Lowenthal
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Patent number: 4866181Abstract: A process for preparing optically active alcohols by reducing ketones using mono- or diisopinocampheylhaloboranes as reducing agents.Type: GrantFiled: December 17, 1987Date of Patent: September 12, 1989Assignee: Aldrich-Boranes, Inc.Inventor: Herbert C. Brown
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Patent number: 4863932Abstract: Azadecalins and C-7 substituted decalins with squalene oxide cyclase inhibitory activity are useful as inhibitors of cholesterol synthesis and hence may be used in pharmaceuticals for regulating cholesterol levels in a mammal.Type: GrantFiled: March 11, 1988Date of Patent: September 5, 1989Assignees: Somatogenetics International, Inc., Dartmouth CollegeInventors: Michael Sinensky, Thomas A. Spencer
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Patent number: 4841005Abstract: A tricyclodecane derivative represented by formula (I): ##STR1## wherein R.sup.1 represents a group X.sup.1 O-- or a hydrogen atom;R.sup.2 represents a hydrogen atom when R.sup.1 represents a group X.sup.1 O--, or R.sup.2 represents a group X.sup.1 O-- when R.sup.1 represents a hydrogen atom;wherein X.sup.1 represents a group ##STR2## or a hydrogen atom, wherein X.sup.2 represents a hydrogen atom, a methyl group, or a trifluoromethyl group;R.sup.3 represents a fluoroalkyl group containing from 1 to 21 carbon atoms, an iodine atom, or a hydrogen atom; andR.sup.4 represents an iodine atom or a hydrogen atom when R.sup.3 represents a fluoroalkyl group containing from 1 to 21 carbon atoms, or R.sup.4 represents a fluoroalkyl group containing from 1 to 21 carbon atoms when R.sup.3 represents an iodine atom or a hydrogen atom.Type: GrantFiled: February 12, 1988Date of Patent: June 20, 1989Assignee: Daikin Industries, Ltd.Inventors: Sinji Tamaru, Motonobu Kubo
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Patent number: 4783558Abstract: Flavoring and perfume compositions, flavored foodstuffs and luxury consumables and perfumed products which contain (+)-spathulenol and/or (+)-4a-allospathulenol, having respective structural formula ##STR1## as the base material, (+)-4a-allospathulenol per se and a process for the preparation of these spathulenols.Type: GrantFiled: April 10, 1987Date of Patent: November 8, 1988Assignee: Naarden International N.V.Inventors: Leendert M. van der Linde, Franciscus P. van Lier, Antonius J. A. van der Weerdt
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Patent number: 4762819Abstract: The invention relates to 2,6-exo-configured tricyclo-5.2.1.0.sup.2,6 decane derivatives that correspond to general formula A wherein ##STR1## R.sup.a, R.sup.b, R.sup.c, R.sup.d are hydrogen or R.sup.d is a methyl group and R.sup.a, R.sup.b, R.sup.c are hydrogen or methyl groups, one of the substituents being a methyl group and both the others being hydrogen,the broken line represents a C-C double bond optionally at (-3) or (-4),the wavy line represents geometric isomers,R.sup.1 and R.sup.2 are hydrogen, or lower alkyl groups with a total of 1-6 carbon atoms, andX represents a carbonyl or hydroxyl function, as well as a process for their synthesis and their use as scents.Type: GrantFiled: May 5, 1987Date of Patent: August 9, 1988Assignee: Dragoco Gerberding & Co. GmbHInventor: Ernst-Joachim Brunke
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Patent number: 4704232Abstract: Flavouring and perfume compositions, flavoured foodstuffs and luxury consumables and perfumed products which contain (+)-spathulenol and/or (+)-4a-allospathulenol, having respective structural formulae ##STR1## as the base material (+)-4a-allospathulenol per se and a process for the preparation of these spathulenols.Type: GrantFiled: November 27, 1984Date of Patent: November 3, 1987Assignee: Naarden International N.V.Inventors: Leendert M. van der Linde, Franciscus P. van Lier, Antonius J. A. van der Weerdt
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Patent number: 4683083Abstract: The invention concerns1. Mixtures of tricyclo[5.2.1.0.sup.2,6 ]decane derivatives, having principal isomers corresponding to the general formula A, whereinR.sup.1 and R.sup.2 are hydrogen atoms or are a methyl group or a hydrogen atom, one of the substituents being a methyl group and the other a hydrogen atom,R.sup.3 and R.sup.4 are hydrogen atoms or are a methyl group or a hydrogen atom, one of the substituents being a methyl group and the other a hydrogen atom,Y is a tetrahydrofurane system at C-4/C-5 or a substituted oxymethyl group at C-5 and a hydrogen atom at C-4,R.sup.5 is a hydrogen atom or a C.sub.1 -C.sub.6 -acyl-, C.sub.1 -C.sub.6 -alkyl-, C.sub.1 -C.sub.6 -alkenyl-, C.sub.1 -C.sub.4 -alkoxymethyl-, C.sub.1 -C.sub.2 alkoxycarbonyl-, formylmethyl-, or di-C.sub.1 -C.sub.4 -alkoxyethyl-group, andthe broken lines indicate a C--C-single bond and a C--C-double bond or alternatively two C--C-single bonds. ##STR1## 2.Type: GrantFiled: January 10, 1985Date of Patent: July 28, 1987Assignee: Dragoco Gerberding and Co. GmbHInventors: Ernst-Joachim Brunke, Hartmut Struwe
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Patent number: 4683330Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.Type: GrantFiled: January 11, 1985Date of Patent: July 28, 1987Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4671798Abstract: Bicyclic carbinol of formula ##STR1## or 1,2,3,4,4a,5,8,8a-octahydro-2,2,6,8-tetramethyl-1-naphthalenol possesses useful odorous properties and it can be used advantageously as perfuming ingredient. A two-step process for its synthesis is disclosed starting from 2-methylpenta-1,3-diene and 6,6-dimethyl-cyclohex-2-en-1-one.Type: GrantFiled: March 26, 1985Date of Patent: June 9, 1987Assignee: Firmenich SAInventor: Claudio Tarchini
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Patent number: 4668814Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.Type: GrantFiled: January 11, 1985Date of Patent: May 26, 1987Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4622430Abstract: Pentacyclo[6.3.0.0..sup.2,6.0.sup.3,10.0.sup.5,9 ]undecane and its derivatives are prepared. The compounds find use as antiviral agents.Type: GrantFiled: December 21, 1982Date of Patent: November 11, 1986Assignee: Noristan LimitedInventors: Theodor G. Dekker, Douglas W. Oliver, Friedrich O. Snyckers, Cornelis J. van der Schyf
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Patent number: 4533770Abstract: Disclosed is 2-exo-hydroxy-endo-tricyclo[6.2.1.0.sup.2,7 ]undecane represented by the following formula (I): ##STR1## The tricycloundecanol of the formula (I) has green, camphor-like and woody odor and is useful as an aroma chemical. Furthermore, owing to the aliphatic polycyclic structure like adamantyl alcohol, it is expected to have antiviral, antimicroviral and plant hormone activities.The tricycloundecanol (I) of the invention is prepared by subjecting endo-tricyclo[6.2.1.0.sup.2,7 ]undecane to hydroxylation at the bridgehead position with a substituted perbenzoic acid.Type: GrantFiled: July 3, 1984Date of Patent: August 6, 1985Assignee: Kao CorporationInventors: Naotake Takaishi, Hitoshi Takahashi, Yoshiaki Inamoto
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Patent number: 4460795Abstract: Described are mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives having the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond; wherein R.sub.1, R.sub.1 ', R.sub.1 ", R.sub.1 "', R.sub.1 "", R.sub.3, R.sub.5, R.sub.5 ', R.sub.5 ", R.sub.5 "', R.sub.5 "" and R.sub.6 represent hydrogen or methyl with the provisos:(i) at least four of R.sub.1, R.sub.1 ', R.sub.1 ", R.sub.1 "' and R.sub.1 "" are hydrogen; and (ii) at least four of R.sub.5, R.sub.5 ', R.sub.5 ", R.sub.5 "' and R.sub.5 "" represent hydrogen;and wherein Z represents one of the moieties:(i) carboxaldehyde having the structure: ##STR2## (ii) alkylene dioxy or dialkoxy methyl having the structure: ##STR3## (iii) hydroxy methyl having the structure: ##STR4## (iv) acetoxymethyl having the structure: ##STR5## and wherein R.sub.7 and R.sub.8 taken separately represent C.sub.1 -C.sub.4 lower alkyl or R.sub.7 and R.sub.8 taken together represent C.sub.2 -C.sub.Type: GrantFiled: March 24, 1983Date of Patent: July 17, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Marie R. Hanna, Richard J. Tokarzewski, Robert P. Belko, Hugh Watkins, Manfred H. Vock
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Patent number: 4453000Abstract: New tricyclic compounds and use thereof as perfume ingredients. Perfume compositions and perfumed articles containing same.Type: GrantFiled: May 19, 1983Date of Patent: June 5, 1984Assignee: Firmenich, S.A.Inventors: Karl-Heinrich Schulte-Elte, Herve Pamingle
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Patent number: 4444982Abstract: (+)- or (-)-7-hydroxymethyl-2,6,6-trimethyltricyclo[6,2,1,0.sup.Type: GrantFiled: September 29, 1982Date of Patent: April 24, 1984Assignee: Takasago Perfumery Co., Ltd.Inventors: Tsukasa Nagashima, Toshio Yoshida
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Patent number: 4439354Abstract: Described are compounds having the generic structure: ##STR1## wherein R.sub.1 represents hydrogen, methyl or acetyl and wherein R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent the same or different hydrogen, methyl or ethyl; a process for preparing same using compounds designed according to the generic structure: ##STR2## and organoleptic uses thereof in perfumes, colognes and perfumed articles.Type: GrantFiled: October 13, 1981Date of Patent: March 27, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, Joseph A. McGhie, Futoshi Fujioka, Takao Yoshida
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Patent number: 4430508Abstract: Described are substituted tricyclodecane derivatives having the generic structure: ##STR1## wherein Y is a moiety having a structure selected from the group consisting of: ##STR2## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; wherein R.sub.1 and R.sub.2 represent hydrogen or methyl with the proviso that one of R.sub.1 and R.sub.2 is hydrogen and the other of R.sub.1 and R.sub.2 is methyl; wherein R.sub.3 is hydrogen, C.sub.1 -C.sub.3 acyl, C.sub.3 or C.sub.4 alkyl or C.sub.3 or C.sub.4 alkenyl; wherein R.sub.4, R.sub.5 and R.sub.6 represent hydrogen or methyl with the additional proviso that one of R.sub.4, R.sub.5 and R.sub.6 is methyl and the other two of R.sub.4, R.sub.5 and R.sub.6 is hydrogen.Type: GrantFiled: December 29, 1981Date of Patent: February 7, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, John B. Hall
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Patent number: 4426505Abstract: New polymers are disclosed comprising recurring units of the formula ##STR1## wherein R is hydrogen or lower alkyl containing from 1 to 5 carbon atoms, L is a divalent linking group, and each X is independently chloro or bromo. The polymers are capable of providing a relatively high index of refraction in combination with a relatively high Abbe number and can be utilized as raw materials in the manufacture of plastic optical articles or elements such as lenses or prisms and in the manufacture of optical films and coatings.Type: GrantFiled: February 25, 1982Date of Patent: January 17, 1984Assignee: Polaroid CorporationInventor: Richard A. Minns
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Patent number: 4410740Abstract: Described are substituted tricyclodecane derivatives having the generic structure: ##STR1## wherein Y is a moiety having a structure selected from the group consisting of: ##STR2## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; wherein R.sub.1 and R.sub.2 represent hydrogen or methyl with the proviso that one of R.sub.1 and R.sub.2 is hydrogen and the other of R.sub.1 and R.sub.2 is methyl; wherein R.sub.3 is hydrogen, C.sub.1 -C.sub.3 acyl, C.sub.3 or C.sub.4 alkyl or C.sub.3 or C.sub.4 alkenyl; wherein R.sub.4, R.sub.5 and R.sub.6 represent hydrogen or methyl with the additional proviso that one of R.sub.4, R.sub.5 and R.sub.6 is methyl and the other two of R.sub.4, R.sub.5 and R.sub.6 is hydrogen.Type: GrantFiled: September 23, 1982Date of Patent: October 18, 1983Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, John B. Hall
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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: 4374284Abstract: This invention relates to an antiulcer, antiinflammatory, and antiallergic agent comprising as the main ingredient olean-12-ene-3.beta., 30-diol which is devoid of side effects of glycyrrhetinic acid and a process for preparation of olean-12-ene-3.beta., 30-diol.Type: GrantFiled: March 27, 1981Date of Patent: February 15, 1983Assignee: Minophagen Pharmaceutical CompanyInventors: Shoji Shibata, Akira Kumagai, Masatoshi Harada, Singo Yano, Hiroshi Saito, Kunio Takahashi
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Patent number: 4373108Abstract: Described are the compounds covered by the generic structure: ##STR1## wherein "R" represents hydrogen or lithium. The compound having the structure: ##STR2## is useful in augmenting or enhancing the patchouli aroma of a perfume, cologne or perfumed article, such as a solid or liquid anionic, cationic, nonionic or zwitterionic detergent.Type: GrantFiled: July 29, 1981Date of Patent: February 8, 1983Assignee: International Flavors & Fragrances, Inc.Inventors: Kenneth K. Light, Joseph A. McGhie, Futoshi Fujioka, Takao Yoshida
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Patent number: 4357360Abstract: Described in the use for augmenting or enhancing the aroma or taste of foodstuffs of compounds defined according to the generic structure: ##STR1## wherein R.sub.1 represents hydrogen, methyl or acetyl and wherein R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are the same or different and each represents hydrogen, methyl or ethyl.Type: GrantFiled: October 13, 1981Date of Patent: November 2, 1982Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, Joseph A. McGhie, Futoshi Fujioka, Takao Yoshida
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Patent number: 4349689Abstract: 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), 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: September 14, 1982Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4318863Abstract: Described are substituted tricyclodecane derivatives having the generic structure: ##STR1## wherein Y is a moiety having a structure selected from the group consisting of: ##STR2## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; wherein R.sub.1 and R.sub.2 represent hydrogen or methyl with the proviso that one of R.sub.1 and R.sub.2 is hydrogen and the other of R.sub.1 and R.sub.2 is methyl; wherein R.sub.3 is hydrogen, C.sub.1 -C.sub.3 acyl, C.sub.3 or C.sub.4 alkyl or C.sub.3 or C.sub.4 alkenyl; wherein R.sub.4, R.sub.5 and R.sub.6 represent hydrogen or methyl with the additional proviso that one of R.sub.4, R.sub.5 and R.sub.6 is methyl and the other two of R.sub.4, R.sub.5 and R.sub.6 is hydrogen.Type: GrantFiled: December 29, 1980Date of Patent: March 9, 1982Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, John B. Hall
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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: 4311852Abstract: New oxygen containing derivatives of tricyclo[6.2.1.0.sup.2,7 ]undecane useful as perfuming or flavor-modifying ingredients in the manufacture of perfumes, perfumed articles, artificial flavors, foodstuffs, feedstuffs, beverages, pharmaceutical preparations or tobacco products.Perfume or flavoring compositions containing same as organoleptically active ingredients.Type: GrantFiled: July 2, 1979Date of Patent: January 19, 1982Assignee: Firmenich SAInventors: Werner Skorianetz, Gunther Ohloff
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Patent number: 4301302Abstract: Described is the compound having the structure: ##STR1## which is used as an intermediate in preparing compounds having organoleptic properties for augmenting or enhancing the aroma or taste of consumable materials, which compounds have the structures: ##STR2##Type: GrantFiled: November 13, 1980Date of Patent: November 17, 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: 4300002Abstract: A polycyclic diol is produced by a hydroformylation of a polycyclic bridged ring olefinic compound having another double bond, formyl or methylol group, in the presence of a cobalt compound and a phosphine as a catalyst in the presence of a saturated hydrocarbon or aromatic hydrocarbon.Polycyclic diols such as tricyclodecanedimethylol are useful for hardeners for non-solvent type lacquers polyurethanes having heat resistant and chemical resistance or epoxy resins.Type: GrantFiled: February 29, 1980Date of Patent: November 10, 1981Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Haruo Shibatani, Yuji Ogomori, Takashi Kameda, Yoshio Yanagi
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Patent number: 4277631Abstract: A novel norpatchoulenol synthesis is disclosed. The key step in the synthesis is an intramolecular Diels-Alder condensation of a trisubstituted silyloxy derivative of cyclohexadienone. Novel intermediates, namely trisubstituted silyloxy methanonaphthalenes (Formula V, infra) and trisubstituted silyloxy cyclohexadienes (Formula IV, infra) are also disclosed.Type: GrantFiled: August 6, 1979Date of Patent: July 7, 1981Assignee: Givaudan CorporationInventor: Wolfgang Oppolzer
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Patent number: 4275251Abstract: Described are substituted tricyclodecane derivatives having the generic structure: ##STR1## wherein Y is a moiety having a structure selected from the group consisting of: ##STR2## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; wherein R.sub.1 and R.sub.2 represent hydrogen or methyl with the proviso that one of R.sub.1 and R.sub.2 is hydrogen and the other of R.sub.1 and R.sub.2 is methyl; wherein R.sub.3 is hydrogen, C.sub.1 -C.sub.3 acyl, C.sub.3 or C.sub.4 alkyl or C.sub.3 or C.sub.4 alkenyl; wherein R.sub.4, R.sub.5 and R.sub.6 represent hydrogen or methyl with the additional proviso that one of R.sub.4, R.sub.5 and R.sub.6 is methyl and the other two of R.sub.4, R.sub.5 and R.sub.6 is hydrogen.Type: GrantFiled: April 29, 1980Date of Patent: June 23, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, John B. Hall
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Patent number: 4262147Abstract: Dicyclopentadiene is selectively and substantially hydroformylated to its dimethanolic derivatives by a process comprising contacting dicyclopentadiene with a gaseous mixture of carbon monoxide and hydrogen at a temperature of at least about 100.degree. C. and a pressure of at least about 1,000 psig in the presence of a catalytic amount of a catalyst consisting essentially of a rhodium-cobalt bimetallic cluster, such as Rh.sub.2 Co.sub.2 CO.sub.12, supported on an amine resin, such as DOWEX.RTM. MWA-1.Type: GrantFiled: March 16, 1979Date of Patent: April 14, 1981Assignee: The Dow Chemical CompanyInventors: Philip E. Garrou, George E. Hartwell
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Patent number: 4229323Abstract: Nor-dehydropatchoulol having the formula I is disclosed. ##STR1## This previously unknown compound has been extracted from natural Patchouli Oil. It can be used in odorant compositions such as perfumes, detergents, aerosols, cosmetic products, etc.Type: GrantFiled: August 23, 1972Date of Patent: October 21, 1980Assignee: Societe Anonyme Roure Bertrand DupontInventors: Paul J. Teisseire, Pierre Maupetit
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Patent number: 4163737Abstract: The use of unsaturated bicyclooctenemethanols to augment or enhance the organoleptic properties of perfumes, particularly the aroma of perfumes together with compositions containing such bicyclooctenemethanols and processes for preparing them, said bicyclooctenemethanols having the generic structures: ##STR1## wherein the wavy line represents exo or endo configurations of the ethanol moiety.Type: GrantFiled: June 8, 1978Date of Patent: August 7, 1979Assignee: International Flavors & Fragrances Inc.Inventors: James M. Sanders, Joaquin F. Vinals, Frederick L. Schmitt
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Patent number: 4151194Abstract: A mixture of 3,8- and 4,8-dicyanotricyclo[5.2.1.0]decane is prepared by the hydrocyanation of 8-cyanotricyclo[5.2.1.0]dec-3-ene in the presence of a catalyst system comprising a zero valent nickel complex, free of carbon monoxide, a promoting amount of a metal compound such as zinc chloride and a hydroxy-containing aryl compound such as p-cresol as a solvent.Type: GrantFiled: December 12, 1977Date of Patent: April 24, 1979Assignee: Gulf Research & Development CompanyInventors: Ching-Yong Wu, Harold E. Swift
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Patent number: 4146740Abstract: Intermediates useful for the synthesis of the valuable perfume material norpatchoulenol, said intermediates having the formula, for instance ##STR1## This intermediate, which is a novel compound, is useful as an intermediate for the production of ethers, esters and other intermediates, which are also novel compounds, such as, for instance, methyl, ethyl, isopropyl and benzyl ethers which can be represented by the formulae ##STR2## wherein R is hydrogen or lower carboxylic acyl. ##STR3## WHERE R is lower alkyl, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, benzyl, etc., and ##STR4## where ##STR5## is a lower acyl radical such as acetyl, propionyl, butyryl, benzoyl, etc. Such intermediates are readily prepared by etherification and esterification reaction procedures and said intermediates are useful as intermediates for the preparation of other odorants.Type: GrantFiled: February 10, 1977Date of Patent: March 27, 1979Assignee: Societe Anonyme Roure Bertrand DupontInventor: Paul J. Teisseire
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Patent number: 4124648Abstract: A process for the preparation of norpatchoulenol is described according to the reaction scheme: ##STR1## Novel intermediates of formulae ##STR2## wherein R.sup.1 is methyl or benzyl and ##STR3## wherein R.sup.1 is methyl or benzyl and X is hydroxy, trityloxy, tosyloxy or halogen, are also described.Type: GrantFiled: February 21, 1974Date of Patent: November 7, 1978Assignee: Societe Anonyme des Etablissements Roure-Bertrand Fils & Justin DupontInventors: Pierre Pesnelle, Paul J. Teisseire
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Patent number: 4124771Abstract: 8-Allyl-8-hydroxytricyclo[5,2,1,0.sup.2,6 ] decane.Type: GrantFiled: August 22, 1977Date of Patent: November 7, 1978Assignee: Naarden International, N.V.Inventors: Harmannus Boelens, Hendrik J. Wobben
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Patent number: 4123394Abstract: Processes and compositions are described for improving, enhancing and modifying the fragrance of products including perfumes, perfume compositions and perfumed articles utilizing as effective ingredients tricyclo[5.2.1.0.sup.2,6 ]decane-methylol or one of its lower alkyl or alkenyl ester or ether derivatives.Type: GrantFiled: December 1, 1976Date of Patent: October 31, 1978Assignee: Firmenich SAInventors: Werner Skorianetz, Khurshid P. Dastur, Hugo Strickler
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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: 4117245Abstract: A novel process for the production of the valuable perfume material norpatchoulenol is disclosed which involves oxidatively decarboxylating an acid precursor according to the following reaction scheme: ##STR1##Type: GrantFiled: February 10, 1977Date of Patent: September 26, 1978Inventor: Paul Jose Teisseire