Polycyclo Ring System Patents (Class 568/817)
  • Patent number: 5107037
    Abstract: 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: Grant
    Filed: June 6, 1990
    Date of Patent: April 21, 1992
    Assignee: Givaudan Corporation
    Inventor: Peter Naegeli
  • Patent number: 5039710
    Abstract: 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: Grant
    Filed: September 17, 1990
    Date of Patent: August 13, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventor: Arnold H. Ratcliffe
  • Patent number: 5030772
    Abstract: 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: Grant
    Filed: February 14, 1990
    Date of Patent: July 9, 1991
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Shigeya Okada
  • Patent number: 5028631
    Abstract: 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: Grant
    Filed: November 25, 1987
    Date of Patent: July 2, 1991
    Inventors: Arthur G. Schwartz, Marvin L. Lewbart
  • Patent number: 5015761
    Abstract: 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: Grant
    Filed: December 5, 1988
    Date of Patent: May 14, 1991
    Assignee: PFW(Nederland)B.V.
    Inventors: Willem Lenselink, Gerben Sipma
  • Patent number: 5004843
    Abstract: 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: Grant
    Filed: May 29, 1990
    Date of Patent: April 2, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mitsuhisa Tamura, Gohu Suzukamo, Ken-ichi Hirose
  • Patent number: 5001120
    Abstract: 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: Grant
    Filed: May 10, 1989
    Date of Patent: March 19, 1991
    Assignee: Natural Pharmacia International, Inc.
    Inventors: Rui-Lin Li, David Y. Lee, Qi-Lu Cheng
  • Patent number: 4952737
    Abstract: 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: Grant
    Filed: October 11, 1988
    Date of Patent: August 28, 1990
    Assignee: Phillips Petroleum Company
    Inventor: Kenneth E. Inkrott
  • Patent number: 4876399
    Abstract: 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: Grant
    Filed: November 2, 1987
    Date of Patent: October 24, 1989
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Robert A. Holton, Rouh-Rong Juo, Richard Lowenthal
  • Patent number: 4866181
    Abstract: A process for preparing optically active alcohols by reducing ketones using mono- or diisopinocampheylhaloboranes as reducing agents.
    Type: Grant
    Filed: December 17, 1987
    Date of Patent: September 12, 1989
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4863932
    Abstract: 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: Grant
    Filed: March 11, 1988
    Date of Patent: September 5, 1989
    Assignees: Somatogenetics International, Inc., Dartmouth College
    Inventors: Michael Sinensky, Thomas A. Spencer
  • Patent number: 4841005
    Abstract: 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: Grant
    Filed: February 12, 1988
    Date of Patent: June 20, 1989
    Assignee: Daikin Industries, Ltd.
    Inventors: Sinji Tamaru, Motonobu Kubo
  • Patent number: 4783558
    Abstract: 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: Grant
    Filed: April 10, 1987
    Date of Patent: November 8, 1988
    Assignee: Naarden International N.V.
    Inventors: Leendert M. van der Linde, Franciscus P. van Lier, Antonius J. A. van der Weerdt
  • Patent number: 4762819
    Abstract: 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: Grant
    Filed: May 5, 1987
    Date of Patent: August 9, 1988
    Assignee: Dragoco Gerberding & Co. GmbH
    Inventor: Ernst-Joachim Brunke
  • Patent number: 4704232
    Abstract: 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: Grant
    Filed: November 27, 1984
    Date of Patent: November 3, 1987
    Assignee: Naarden International N.V.
    Inventors: Leendert M. van der Linde, Franciscus P. van Lier, Antonius J. A. van der Weerdt
  • Patent number: 4683083
    Abstract: 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: Grant
    Filed: January 10, 1985
    Date of Patent: July 28, 1987
    Assignee: Dragoco Gerberding and Co. GmbH
    Inventors: Ernst-Joachim Brunke, Hartmut Struwe
  • Patent number: 4683330
    Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.
    Type: Grant
    Filed: January 11, 1985
    Date of Patent: July 28, 1987
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4671798
    Abstract: 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: Grant
    Filed: March 26, 1985
    Date of Patent: June 9, 1987
    Assignee: Firmenich SA
    Inventor: Claudio Tarchini
  • Patent number: 4668814
    Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.
    Type: Grant
    Filed: January 11, 1985
    Date of Patent: May 26, 1987
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4622430
    Abstract: 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: Grant
    Filed: December 21, 1982
    Date of Patent: November 11, 1986
    Assignee: Noristan Limited
    Inventors: Theodor G. Dekker, Douglas W. Oliver, Friedrich O. Snyckers, Cornelis J. van der Schyf
  • Patent number: 4533770
    Abstract: 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: Grant
    Filed: July 3, 1984
    Date of Patent: August 6, 1985
    Assignee: Kao Corporation
    Inventors: Naotake Takaishi, Hitoshi Takahashi, Yoshiaki Inamoto
  • Patent number: 4460795
    Abstract: 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: Grant
    Filed: March 24, 1983
    Date of Patent: July 17, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Marie R. Hanna, Richard J. Tokarzewski, Robert P. Belko, Hugh Watkins, Manfred H. Vock
  • Patent number: 4453000
    Abstract: New tricyclic compounds and use thereof as perfume ingredients. Perfume compositions and perfumed articles containing same.
    Type: Grant
    Filed: May 19, 1983
    Date of Patent: June 5, 1984
    Assignee: Firmenich, S.A.
    Inventors: Karl-Heinrich Schulte-Elte, Herve Pamingle
  • Patent number: 4444982
    Abstract: (+)- or (-)-7-hydroxymethyl-2,6,6-trimethyltricyclo[6,2,1,0.sup.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: April 24, 1984
    Assignee: Takasago Perfumery Co., Ltd.
    Inventors: Tsukasa Nagashima, Toshio Yoshida
  • Patent number: 4439354
    Abstract: 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: Grant
    Filed: October 13, 1981
    Date of Patent: March 27, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Kenneth K. Light, Joseph A. McGhie, Futoshi Fujioka, Takao Yoshida
  • Patent number: 4430508
    Abstract: 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: Grant
    Filed: December 29, 1981
    Date of Patent: February 7, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, John B. Hall
  • Patent number: 4426505
    Abstract: 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: Grant
    Filed: February 25, 1982
    Date of Patent: January 17, 1984
    Assignee: Polaroid Corporation
    Inventor: Richard A. Minns
  • Patent number: 4410740
    Abstract: 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: Grant
    Filed: September 23, 1982
    Date of Patent: October 18, 1983
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, John B. Hall
  • Patent number: 4410515
    Abstract: 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: Grant
    Filed: April 1, 1981
    Date of Patent: October 18, 1983
    Assignee: Massachusetts General Hospital
    Inventors: Sally A. Holick, Michael F. Holick
  • Patent number: 4374284
    Abstract: 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: Grant
    Filed: March 27, 1981
    Date of Patent: February 15, 1983
    Assignee: Minophagen Pharmaceutical Company
    Inventors: Shoji Shibata, Akira Kumagai, Masatoshi Harada, Singo Yano, Hiroshi Saito, Kunio Takahashi
  • Patent number: 4373108
    Abstract: 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: Grant
    Filed: July 29, 1981
    Date of Patent: February 8, 1983
    Assignee: International Flavors & Fragrances, Inc.
    Inventors: Kenneth K. Light, Joseph A. McGhie, Futoshi Fujioka, Takao Yoshida
  • Patent number: 4357360
    Abstract: 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: Grant
    Filed: October 13, 1981
    Date of Patent: November 2, 1982
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Kenneth K. Light, Joseph A. McGhie, Futoshi Fujioka, Takao Yoshida
  • Patent number: 4349689
    Abstract: 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: Grant
    Filed: December 22, 1980
    Date of Patent: September 14, 1982
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4318863
    Abstract: 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: Grant
    Filed: December 29, 1980
    Date of Patent: March 9, 1982
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, John B. Hall
  • 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: 4311852
    Abstract: 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: Grant
    Filed: July 2, 1979
    Date of Patent: January 19, 1982
    Assignee: Firmenich SA
    Inventors: Werner Skorianetz, Gunther Ohloff
  • Patent number: 4301302
    Abstract: 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: Grant
    Filed: November 13, 1980
    Date of Patent: November 17, 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: 4300002
    Abstract: 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: Grant
    Filed: February 29, 1980
    Date of Patent: November 10, 1981
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Haruo Shibatani, Yuji Ogomori, Takashi Kameda, Yoshio Yanagi
  • Patent number: 4277631
    Abstract: 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: Grant
    Filed: August 6, 1979
    Date of Patent: July 7, 1981
    Assignee: Givaudan Corporation
    Inventor: Wolfgang Oppolzer
  • Patent number: 4275251
    Abstract: 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: Grant
    Filed: April 29, 1980
    Date of Patent: June 23, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, John B. Hall
  • Patent number: 4262147
    Abstract: 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: Grant
    Filed: March 16, 1979
    Date of Patent: April 14, 1981
    Assignee: The Dow Chemical Company
    Inventors: Philip E. Garrou, George E. Hartwell
  • Patent number: 4229323
    Abstract: 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: Grant
    Filed: August 23, 1972
    Date of Patent: October 21, 1980
    Assignee: Societe Anonyme Roure Bertrand Dupont
    Inventors: Paul J. Teisseire, Pierre Maupetit
  • Patent number: 4163737
    Abstract: 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: Grant
    Filed: June 8, 1978
    Date of Patent: August 7, 1979
    Assignee: International Flavors & Fragrances Inc.
    Inventors: James M. Sanders, Joaquin F. Vinals, Frederick L. Schmitt
  • Patent number: 4151194
    Abstract: 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: Grant
    Filed: December 12, 1977
    Date of Patent: April 24, 1979
    Assignee: Gulf Research & Development Company
    Inventors: Ching-Yong Wu, Harold E. Swift
  • Patent number: 4146740
    Abstract: 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: Grant
    Filed: February 10, 1977
    Date of Patent: March 27, 1979
    Assignee: Societe Anonyme Roure Bertrand Dupont
    Inventor: Paul J. Teisseire
  • Patent number: 4124648
    Abstract: 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: Grant
    Filed: February 21, 1974
    Date of Patent: November 7, 1978
    Assignee: Societe Anonyme des Etablissements Roure-Bertrand Fils & Justin Dupont
    Inventors: Pierre Pesnelle, Paul J. Teisseire
  • Patent number: 4124771
    Abstract: 8-Allyl-8-hydroxytricyclo[5,2,1,0.sup.2,6 ] decane.
    Type: Grant
    Filed: August 22, 1977
    Date of Patent: November 7, 1978
    Assignee: Naarden International, N.V.
    Inventors: Harmannus Boelens, Hendrik J. Wobben
  • Patent number: 4123394
    Abstract: 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: Grant
    Filed: December 1, 1976
    Date of Patent: October 31, 1978
    Assignee: Firmenich SA
    Inventors: Werner Skorianetz, Khurshid P. Dastur, Hugo Strickler
  • Patent number: 4119575
    Abstract: 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: Grant
    Filed: February 28, 1977
    Date of Patent: October 10, 1978
    Assignee: Monsanto Company
    Inventors: Jordan J. Bloomfield, Dennis C. Owsley
  • Patent number: 4117245
    Abstract: 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: Grant
    Filed: February 10, 1977
    Date of Patent: September 26, 1978
    Inventor: Paul Jose Teisseire