Tricyclo Ring System Patents (Class 568/373)
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Patent number: 5151411Abstract: A compound of the formula ##STR1## wherein the dotted line signifies an optional bond, as racemates or individual enantiomers, odorant compositions containing the same, and a process for the manufacture of the compounds of formula I which comprises rearranging sclareolide, episclareolide or isosclareolide at an elevated temperature in acidic medium with dehydration and, if desired, reducing the carbon-carbon double bond present in the reaction product.Type: GrantFiled: August 20, 1991Date of Patent: September 29, 1992Assignee: Givaudan CorporationInventors: Georg Frater, Daniel Helmlinger
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Patent number: 5116865Abstract: 15,16-Seco-19-nor progestins are provided which display elevated progestational activity with a minimum of ancillary hormonal activity. Processes for the preparation of the novel progestins are provided as are methods of use. A preferred method of use is in the suppression of ovulation in the human female.Type: GrantFiled: January 28, 1991Date of Patent: May 26, 1992Inventors: Richard H. Peters, Masato Tanabe
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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: 4947002Abstract: Novel compounds of the formula ##STR1## wherein: the symbols R.sup.1, R.sup.2, R.sup.4, R.sup.5 and R.sup.6 represent hydrogen or methyl, with the proviso that only one of R.sup.1, R.sup.2 and R.sup.4 represents methyl, and, when either or both R.sup.5 and R.sup.6 represent methyl, then R.sup.1, R.sup.2 and R.sup.4 represent hydrogen; and,either the symbol (.dbd.O) on the carbon designated by the number 1 or the symbol (.dbd.O) on the carbon designated by the number 3, represents a keto group, such that when the group is present on carbon 1, then carbon 3 may contain a methyl group.and their use as odorants are described.Type: GrantFiled: November 2, 1988Date of Patent: August 7, 1990Assignee: Givaudan CorporationInventors: Georg Frater, Urs Muller
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Patent number: 4927975Abstract: Novel antiandrogenic compositions comprising an antiandrogenically effective amount of at least one compound of the formula ##STR1## wherein R is alkyl of 1 to 4 carbon atoms, R.sub.1 is alkyl of 1 to 2 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms optionally interrupted with a heteroatom, alkenyl and alkynyl of 2 to 8 carbon atoms optionally interrupted with a heteroatom, formyl and acyl of an organic carboxylic acid of 2 to 18 carbon atoms, R.sub.3 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and alkenyl and alkynyl of 2 to 4 carbon atoms, R.sub.4 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, the dotted lines indicate optional presence of a double bond between the 4(5) and 5a(6) carbons and the wavy line indicates that R.sub.4 may be in the .alpha.- or .beta.Type: GrantFiled: July 25, 1988Date of Patent: May 22, 1990Assignee: Roussel UclafInventors: Marie-Madeleine Bouton, Jean Jacques, Andre Pierdet
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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: 4874891Abstract: Compounds of the formula: ##STR1## and the pharmaceutically acceptable esters thereof, wherein rings A and B are selected from the group consisting of ##STR2## wherein x represents an aromatic ring, or the presence or absence of 0, 1, or 2 conjugated or unconjugated .pi. bond(s), andwherein x represents the presence or absence of 0, 1, or 2 conjugated or unconjugated .pi. bond(s), andwherein a non-aromatic .pi. bond, if present, may optionally be converted to an epoxide;and wherein the dotted line represents the presence or absence of a .pi. bond,and wherein:R.sup.1 is H, acyl(1-6), or alkyl(1-6);R.sup.2 is H, alkyl(1.varies.6), 2-propynyl, or allenyl;R.sup.3 and R.sup.4 is each independently H or OR.sup.5, wherein R.sup.5 is H, acyl(1-6), or alkyl(1-6); andwherein R.sub.1 and R.sub.2 is each independently H, alkyl(1-6) or is --C.tbd.CR.sub.3, --CH.dbd.CHR.sub.3, or --CH.dbd.C.dbd.CHR.sub.3, wherein R.sub.3 is selected from the group consisting of H, halo, CF.sub.Type: GrantFiled: May 1, 1986Date of Patent: October 17, 1989Assignee: Washington UniversityInventors: Douglas F. Covey, Ricahrd J. Auchus
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Patent number: 4849454Abstract: Novel antiandrogenic compositions comprising an anti-androgenically effective amount of at least one compound of the formula ##STR1## wherein R is alkyl of 1 to 4 carbon atoms, R.sub.1 is alkyl of 1 to 2 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms optionally interrupted with a heteroatom, alkenyl and alkynyl of 2 to 8 carbon atoms optionally interrupted with a heteroatom, formyl and acyl of an organic carboxylic acid of 2 to 18 carbon atoms, R.sub.3 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and alkenyl and alkynyl of 2 to 4 carbon atoms, R.sub.4 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, the dotted lines indicate optional presence of a double bond between the 4(5) and 5a(6) carbons and the wavy line indicates that R.sub.4 may be in the .alpha.- or .beta.Type: GrantFiled: April 24, 1986Date of Patent: July 18, 1989Assignee: Roussel UclafInventors: Marie-Madeleine Bouton, Jean Jacques, Andre Pierdet
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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: 4756764Abstract: 3,10-Diacetyl-11-isopropylidene-7,7-dimethyl-tricyclo[6.2.1.0.sup.2,6 ]undeca-2,5,9-triene is a flavoring ingredient useful for the aromatization of smoking articles. It develops upon smoking green, slightly floral, metallic, astringent, fatty, slightly bitter and earthy notes.It is prepared by a two-step process from 1-(4-isopropylidene-1-cyclopent-1-enyl)-1-ethanone.Type: GrantFiled: February 26, 1987Date of Patent: July 12, 1988Assignee: Firmenich SAInventors: Alan F. Thomas, Alistair Y. Smith
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Patent number: 4607054Abstract: Novel antiandrogenic compositions comprising an antiandrogenically effective amount of at least one compound of the formula ##STR1## wherein R is alkyl of 1 to 4 carbon atoms, R.sub.1 is alkyl of 1 to 2 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms optionally interrupted with a heteroatom, alkenyl and alkynyl of 2 to 8 carbon atoms optionally interrupted with a heteroatom, formyl and acyl of an organic carboxylic acid of 2 to 18 carbon atoms, R.sub.3 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and alkenyl and alkynyl of 2 to 4 carbon atoms, R.sub.4 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, the dotted lines indicate optional presence of a double bond between the 4(5) and 5a(6) carbons and the wavy line indicates that R.sub.4 may be in the .alpha.- or .beta.Type: GrantFiled: October 19, 1983Date of Patent: August 19, 1986Assignee: Roussel UclafInventors: Marie-Madeleine Bouton, Jean Jacques, Andre Pierdet
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Patent number: 4603223Abstract: A novel process for the manufacture of quinone derivatives is described.In this process a compound of the formula ##STR1## is reacted with a compound of the formula ##STR2## and the resulting compound of the formula ##STR3## is subjected to a retro-Diels-Alder reaction. The substituents R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the significance given in the description.Type: GrantFiled: July 24, 1984Date of Patent: July 29, 1986Assignee: Hoffmann-La Roche Inc.Inventors: August Ruttimann, George H. Buchi
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Patent number: 4466971Abstract: Novel antiandrogenic compositions comprising an antiandrogenically effective amount of at least one compound of the formula ##STR1## wherein R is alkyl of 1 to 4 carbon atoms, R.sub.1 is alkyl of 1 to 2 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms optionally interrupted with a heteroatom, alkenyl and alkynyl of 2 to 8 carbon atoms optionally interrupted with a heteroatom, formyl and acyl of an organic carboxylic acid of 2 to 18 carbon atoms, R.sub.3 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and alkenyl and alkynyl of 2 to 4 carbon atoms, R.sub.4 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, the dotted lines indicate optional presence of a double bond between the 4(5) and 5a(6) carbons and the wavy line indicates that R.sub.4 may be in the .alpha.-or .beta.Type: GrantFiled: February 19, 1982Date of Patent: August 21, 1984Assignee: Roussel UclafInventors: Marie-Madeleine Bouton, Jean Jacques, Andre Pierdet
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Patent number: 4453014Abstract: Perfume compositions, perfumed materials and perfumed articles containing one or more isomers of substituted 1.4.4.8-tetramethyl-tricyclo[6.3.0.0.sup.2.5 ]-undecanes as perfume base.Use of one or more isomers of 9-alkanoyl-1.4.4.8-tetramethyl-tricyclo[6.3.0.0.sup.2.5 ]undecanes having formula ##STR1## wherein R is methyl, ethyl or n-propyl as a perfume component in perfume compositions and in imparting fragrance to materials and articles for example soaps, cleaning preparations and cosmetic preparations.Type: GrantFiled: September 13, 1982Date of Patent: June 5, 1984Assignee: Naarden International N.V.Inventor: Antonius J. A. Van der Weerdt
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Patent number: 4415756Abstract: New bicyclo[2.2.2]oct-5-en-2-ones of the formulae Ia and Ib in the form of pure enantiomers and processes for preparing them are described. The compounds are used for the preparation of pure enantiomers of the formula V by sensitized photoreaction or of compounds of the formula VI by unsensitized photoreaction.Type: GrantFiled: December 2, 1981Date of Patent: November 15, 1983Assignee: Studiengesellschaft Kohle mbHInventors: Martin Demuth, Kurt Schaffner
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Patent number: 4390721Abstract: A novel 3-endo-protected hydroxyl-tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is described which can be alkylated stereospecifically to give a 5-endo-protected hydroxyl-bicyclo[2,2,1]heptan-2-one which may then be converted via a sequence of reactions into prostaglandins of the F-series having a protecting group at the 9-position. The synthesis of the tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is also described.Type: GrantFiled: November 1, 1978Date of Patent: June 28, 1983Assignee: Allen & Hanburys LimitedInventor: Stanley M. Roberts
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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: 4358617Abstract: 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 25, 1981Date of Patent: November 9, 1982Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, John B. Hall
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Patent number: 4325967Abstract: Cyclopentane derivatives of the formula: ##STR1## wherein R.sup.1 represents hydrogen or a carboxylic acyl group, and either (i) R.sup.2 represents a group of the formula:--CR.sup.3 R.sup.4 R.sup.5 II(wherein R.sup.3 and R.sup.4 represent hydrogen or alkyl, and R.sup.5 represents hydrogen, or alkyl, alkoxy, cycloalkyl or adamantyl, or R.sup.5 represents alkyl substituted by alkoxy, or by cycloalkyl or by adamantyl, or the group --CR.sup.3 R.sup.4 R.sup.5 together forms a cycloalkyl or adamantyl group), X represents trans-vinylene or ethylene and Y represents carbonyl or a group of the formula: ##STR2## wherein R.sup.6 represents hydrogen or alkyl, and R.sup.7 represents hydrogen or a carboxylic acyl group, or else(ii) R.sup.2 represents a group of the formula:--A--Z--R.sup.8 IV(wherein A represents alkylene, Z represents a direct bond or oxygen or sulphur, and R.sup.Type: GrantFiled: May 7, 1979Date of Patent: April 20, 1982Assignee: May & Baker LimitedInventors: Michael P. L. Caton, Edward C. J. Coffee, Gordon L. Watkins
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Patent number: 4322559Abstract: 4(5)-acetyl-9,9-dimethyltricyclo-[4,4,0,1.sup.8,10 ]-undec-1-ene having the formula ##STR1## its synthesis, its use as a perfumery agent and as an olfactant component in perfumery compositions and as an odorant for technical products.Type: GrantFiled: August 14, 1980Date of Patent: March 30, 1982Assignee: Henkel Kommanditgesellschaft auf Aktien (Henkel KGaA)Inventors: Jens Conrad, Klaus Bruns, Horst Upadek
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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: 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: 4267376Abstract: A compound having the general formula ##STR1## wherein R.sup.1 is a lower alkyl group, R.sup.2 is hydrogen or a lower alkyl group and Y is a protected hydroxyl group, for example, (.+-.)-3.beta.-tert.butoxy-2,3,3a,4,5,7,8,9,9a.beta.,9b.alpha.-decahydro-3 a.beta.-methyl-6-(3-butenyl)-1H-benz(e)inden-7-one, which is an intermediate for steroids, is prepared by dehydrative cyclization of a compound of the general formula ##STR2## wherein the symbols of R.sup.1, Y and R.sup.2 are same as defined above.Type: GrantFiled: August 30, 1979Date of Patent: May 12, 1981Assignee: Takeda Chemical Industries, Ltd.Inventor: Jiro Tsuji
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Patent number: 4256742Abstract: Polycyclic aziridines, such as 0-[2-(dimethylamino)ethyl]oxime of 1a,10b-dihydrodibenzo-[3,4,6,7]cyclohept[1,2-b]-N-methylazirin-6(1H)-one, useful for alleviating depression in mammals.Type: GrantFiled: June 27, 1979Date of Patent: March 17, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Michael J. Haire
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Patent number: 4250338Abstract: Described are compounds covered by the generic structure; ##STR1## where one, two or all of R.sub.1, R.sub.2 and R.sub.3 are the same or different and each represents hydrogen or lower alkyl of from 1 up to 3 carbon atoms; a process for preparing same using compounds having the generic structure; ##STR2## where one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines represents carbon-carbon single bonds and organoleptic uses thereof in perfumes, colognes, perfumed articles such as anionic, cationic and non-ionic detergents, cosmetic powders and dryer-added fabric softener articles, as well as in smoking tobaccos and smoking tobacco articles, e.g., the body of smoking tobacco, the wrapper or the filter therefor.Type: GrantFiled: November 16, 1979Date of Patent: February 10, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, James M. Sanders, William L. Schreiber, Hugh Watkins, Joaquin F. Vinals, Edward J. Shuster, Thomas J. O'Rourke, Myrna L. Hagedorn, Philip Klemarczyk
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Patent number: 4226745Abstract: New tricyclic carbonyl derivative, viz. cis-10,10-dimethyl-tricyclo[7.1.1.0.sup.2,7 ]undec-2-en-4-one, and its use as flavoring and perfuming material.Type: GrantFiled: December 14, 1978Date of Patent: October 7, 1980Assignee: Firmenich, S.A.Inventor: Alan F. Thomas
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Patent number: 4225508Abstract: Prostacyclin and prostacyclin-type derivatives having a 19-hydroxy feature are disclosed, including processes for preparing them and the appropriate intermediates. The compounds are useful for pharmacological purposes such as inhibition of blood platelate aggregation.Type: GrantFiled: July 5, 1979Date of Patent: September 30, 1980Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4219489Abstract: Method and compounds are provided for use in the synthesis of steroids wherein a polyolefin is provided having an initiating group having a chalcogen atom in juxtaposition to a double bond, so as to be capable of bond formation to close to form a ring and having a terminating group involving pi unsaturation (a double or triple bond) conjugated to an aromatic ring. Upon acid catalysis, sigma bonds are formed through the interaction of a carbocation formed at the carbon atom bonded to the chalcogen atom and the double bond intermediate the initiating group and the terminating group, which close to form rings of a steroid nucleus, the carbocation interacting with the pi unsaturation conjugated with the aromatic group and being captured by a nucleophile present in the acidic reaction medium. The resulting steroid product may then be modified in known ways to produce known steroids.Type: GrantFiled: September 5, 1978Date of Patent: August 26, 1980Assignee: The Board of Trustees of the Leland Stanford Junior UniversityInventors: William S. Johnson, Leonard A. Bunes
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Patent number: 4207240Abstract: Novel 4,5-seco-estrane-3,5,17-trione derivatives of the formula ##STR1## wherein R.sub.1 is alkyl of 1 to 3 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms and K and K' are individually blocked ketones in the form of ketals which are intermediates for the preparation of therapeutically active steroids and their preparation and novel intermediates.Type: GrantFiled: February 26, 1979Date of Patent: June 10, 1980Assignee: Roussel UclafInventors: Jean Jolly, Bernard Matra, Primo Rizzi
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Patent number: RE32721Abstract: Described are compounds covered by the generic structure. ##STR1## where one, two or all of R.sub.1, R.sub.2 and R.sub.3 are the same or different and each represents hydrogen or lower alkyl of from 1 up to 3 carbon atoms; a process for preparing same using compounds having the generic structure; ##STR2## where one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines represents carbon-carbon single bonds and organoleptic uses thereof in perfumes, colognes, perfumed articles such as anionic, cationic and non-ionic detergents, cosmetic powders and dryer-added fabric softener articles, as well as in smoking tobaccos and smoking tobacco articles, e.g., the body of smoking tobacco, the wrapper or the filter therefor.Type: GrantFiled: December 21, 1984Date of Patent: July 26, 1988Assignee: 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