Polycyclo-alicyclic Ring System Patents (Class 568/445)
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Patent number: 6515137Abstract: Acid addition salts of imidazolidinones are provided as catalysts for transforming a functional group within a first reactant by reaction with a second reactant. Exemplary first reactants are &agr;,&bgr;-unsaturated carbonyl compounds such as &agr;,&bgr;-unsaturated ketones and &agr;,&bgr;-unsaturated aldehydes. Chiral imidazolidinone salts can be used to catalyze enantioselective reactions, such that a chiral product is obtained from a chiral or achiral starting material in enantiomerically pure form.Type: GrantFiled: July 30, 2001Date of Patent: February 4, 2003Assignee: The Regents of the University of CaliforniaInventors: David W. C. MacMillan, Kateri A. Ahrendt
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Patent number: 6414167Abstract: The invention relates to a novel octafluorotricyclodecane derivative represented by the general formula (1), where R1 is a hydrogen atom, a halogen atom, a hydrocarbon group or a halogenated hydrocarbon group, m is 0 or 1, and R2 is represented by the general formula (2), where R3 is a hydrogen atom or a hydrocarbon group optionally having a substituent. This octafluorotricyclodecane derivative may be useful as a monomer for producing various functional polymers or as a raw material of the same.Type: GrantFiled: June 19, 2001Date of Patent: July 2, 2002Assignee: Central Glass Company, LimitedInventors: Satoru Miyazawa, Michitaka Ootani, Kentaro Tsutsumi
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Patent number: 6369243Abstract: A method is provided for catalytically transforming a functional group within a first reactant by reaction with a second reactant in the presence of a nonmetallic, organic catalyst composition composed of a heteroatom-containing activator and an acid, or a salt of a heteroatom-containing activator and an acid. Exemplary first reactants are &agr;,&bgr;-unsaturated carbonyl compounds such as &agr;,&bgr;-unsaturated ketones and &agr;,&bgr;-unsaturated aldehydes. The heteroatom of the activator is a Group 15 or Group 16 element such as nitrogen, oxygen, sulfur or phosphorus, and exemplary heteroatom-containing activators are amines. Chiral heteroatom-containing activators can be used to catalyze enantioselective reactions, such that a chiral product is obtained from a chiral or achiral starting material in enantiomerically pure form.Type: GrantFiled: January 18, 2000Date of Patent: April 9, 2002Assignee: The Regents of the Univerisity of CaliforniaInventors: David W. C. MacMillan, Kateri A. Ahrendt
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Patent number: 6365782Abstract: A method of producing tricyclodecane dicarbaldehyde and/or pentacyclopentadecane dicarbaldehyde by the hydroformylation of dicyclopentadiene and/or tricyclopentadiene. The tricyclodecane dicarbaldehyde and/or pentacyclopentadecane dicarbaldehyde in the hydroformylation product liquid are extracted with an extraction solvent comprising a polyhydric alcohol having 2 to 6 carbon atoms. With such extraction, the tricyclodecane dicarbaldehyde and/or pentacyclopentadecane dicarbaldehyde transfer into the extraction solvent while retaining the catalyst components in the hydroformylation solvent. The controlled extraction atmosphere with an oxygen concentration of 1000 ppm or lower prevents the rhodium compound from transferring into the extraction solvent, thereby avoiding the loss of expensive rhodium.Type: GrantFiled: July 3, 2000Date of Patent: April 2, 2002Assignee: Mitsbushi Gas Chemical Company, Inc.Inventors: Kenichi Nakamura, Kazuhiro Yamada, Takashi Fujii, Takashi Motoi
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Patent number: 6284929Abstract: The invention relates to compounds of the general formula in which R1 to R7 are, independently, H, methyl or ethyl, R8+R9 together form methylene (—CH2—) or a single bond, or R1+R2 together form —(CH2)n—, with n being 3 or 4, or R3+R5 or R5+R7 represent methylene or a single bond; and the presence of at least one cyclopropane ring in the molecule is compulsory and the side chain can be saturated or contains one double bond in position &agr;,&bgr; or &bgr;,&ggr;, a process for the manufacture of these compounds, compounds used to perform the process and the use of these compounds as an odorant or as an ingredient of an odorant composition.Type: GrantFiled: October 5, 2000Date of Patent: September 4, 2001Assignee: Givaudan Roure (International) SAInventors: Jerzy A. Baigrowicz, Georg Frater
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Patent number: 6271193Abstract: Described are carbon-containing functional groups substituted 4,5,6,7-tetrahydro-polyalkylated-4-indanes, isomers thereof, process for processes for preparing same, and uses thereof. The 4,5,6,7-tetrahydro-polyalkylated-4-indanes have the generic structure: Wherein G and R1-5 are as defined in the specification. The aforementioned materials have fragrance properties or are intermediates for materials which have fragrance properties. Also described are processes for producing the aforementioned substances.Type: GrantFiled: October 11, 2000Date of Patent: August 7, 2001Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Richard A. Weiss, Anthony T. Levorse, Jr., Howard H. Heinsohn, Jr., Charles E. J. Beck, Marie R. Hanna
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Patent number: 6242413Abstract: The invention relates to bicyclic aldehydes and ketones of formula (I): wherein n is 1 or 2; R1 and R4 are independently H or CH3; and R2 and R3 are independently H, CH3 or CH2CH3 The invention also provides odorant compositions containing at least one compound of formula (I). A process for the manufacture of R1-methyl substituted compounds of formula (I) having a bridgehead-positioned double bond, as well as intermediates thereof is also provided.Type: GrantFiled: June 2, 1999Date of Patent: June 5, 2001Assignee: Givaudan Roure (International) S.A.Inventors: Georg Frater, Philip Kraft
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Patent number: 6235943Abstract: The invention relates to compounds of the general formula in which R1 to R7 are, independently, H, methyl or ethyl, R8+R9 together form methylene (—CH2—) or a single bond, or R1+R2 together form —(CH2)n—, with n being 3 or 4, or R3+R5 or R5+R7 represent methylene or a single bond; and the presence of at least one cyclopropane ring in the molecule is compulsory and the side chain can be saturated or contains one double bond in position &agr;,&bgr; or &bgr;,&ggr;, a process for the manufacture of these compounds, compounds used to perform the process and the use of these compounds as an odorant or as an ingredient of an odorant composition.Type: GrantFiled: October 5, 2000Date of Patent: May 22, 2001Assignee: Givaudan Roure (International) SAInventors: Jerzy A. Bajgrowicz, Georg Frater
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Patent number: 6087296Abstract: The present invention relates to a Raney catalyst comprising iron, cobalt, a third metal wherein the third metal is selected from the group consisting of nickel, rhodium, ruthenium, palladium, platinum, osmium, iridium and mixtures of any of these metals.Type: GrantFiled: November 5, 1998Date of Patent: July 11, 2000Assignee: E. I. du Pont de Nemours & Co.Inventor: Mark Jay Harper
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Patent number: 5929291Abstract: The invention relates to compounds of the general formula ##STR1## in which R.sup.1 to R.sup.7 are, independently, H, methyl or ethyl, R.sup.8 +R.sup.9 together form methylene (--CH.sub.2 --) or a single bond, or R.sup.1 +R.sup.2 together form --(CH.sub.2).sub.n --, with n being 3 or 4, or R.sup.3 +R.sup.5 or R.sup.5 +R.sup.7 represent methylene or a single bond; and the presence of at least one cyclopropane ring in the molecule is compulsory and the side chain can be saturated or contains one double bond in position .alpha.,.beta. or .beta., .gamma. a process for the manufacture of these compounds, compounds used to perform the process and the use of these compounds as an odorant or as an ingredient of an odorant composition.Type: GrantFiled: April 9, 1997Date of Patent: July 27, 1999Assignee: Givaudan Roure (International) SAInventors: Jerzy A. Bajgrowicz, Georg Frater
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Patent number: 5886234Abstract: A process for producing a cyclic unsaturated aldehyde is herein disclosed which comprises the step of reacting a cyclic conjugated diene compound with an aldehyde represented by the general formula (I)R--CH.dbd.CH--CHO (I)wherein R is an alkyl group having 1 to 3 carbon atoms,in the presence of a solid acid catalyst in accordance with the Diels-Alder reaction.According to the process of the present invention, the cyclic unsaturated aldehydes useful as the raw materials of traction oils and the like can efficiently and industrially advantageously be produced through the Diels-Alder reaction at a low cost without causing the corrosion of an apparatus and without requiring any treatment after the reaction.Type: GrantFiled: December 22, 1997Date of Patent: March 23, 1999Assignee: Idemitsu Kosan Co., Ltd.Inventors: Takashi Ohno, Toshiyuki Tsubouchi
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Patent number: 5597932Abstract: The invention is drawn to a compound having the following formula ##STR1## in which X.sup.1 and X.sup.2, which may be the same or different, represent hydrogen or a hydroxy-protecting group, X.sup.4 is hydrogen, A is selected from --COOAlkyl and CH.sub.2 OH, and B is a hydroxy group, or A and B, when taken together, represent an oxo group. These compounds are useful as intermediates in the production of 19-nor vitamin D derivatives.Type: GrantFiled: May 16, 1995Date of Patent: January 28, 1997Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rolf E. Swenson
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Patent number: 5525745Abstract: The invention describes intermediates for use in the synthesis of 1.alpha.-hydroxy-19-nor-vitamin D compounds. The intermediates have the following formula: ##STR1## The disclosed process includes (a) the construction of a 5,8-diol-6-yne intermediate by joining ring-A and ring-C/D portions of the desired end product via the condensation of an acetylenic derivative containing the C/D-ring portion of the desired end product with a cyclic dihydroxy ketone representing the A-ring of the desired end product; (b) the partial reduction of the 6,7 acetylenic triple bond linkage between the A and C/D ring portions to obtain a 5,8-diol-6-ene intermediate; and (c) the reductive removal of the 5,8-oxygen functions to generate the required 5,7-diene end product from which the desired 7-trans(7E)-isomer is purified directly, or after optional double bond isomerization of the 7-cis(7Z)-isomer employing a novel thiophenol-promoted isomerization step.Type: GrantFiled: March 27, 1995Date of Patent: June 11, 1996Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Heinrich K. Schnoes, Fariba Aria
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Patent number: 5492887Abstract: It was found that 8-exo-formyl-2,6-exo-tricyclo[5.2.1.0.sup.2,6 ]decane having the constitution and stereochemistry of formula (I) possesses particularly useful olfactory properties which are clearly superior to those of the 8-endo-epimer and which already have an effect if compound (I) is enriched with mixtures of 8-exo- and 8-endo-epimers. Compound (I) can therefore be advantageously used, in pure or enriched form, as a scent or as a component of perfume compositions. To prepare an enriched epimer mixture, a mixture obtained in a known manner (U.S. Pat. No. 3,270,061) and having an exo/endo ratio of 1.45:1 is brought into equilibrium by base catalysis, preferably by the action of alkali hydroxides in alcoholic solution, to give an exo/endo ratio of 5.25:1. Alternatively, the enriched epimer mixture can be prepared starting from 8-formyl-2,6-exo-tricyclo[5.2.1.0.sup.2,6 ]decene-3(4), catalytically hydrogenated for example with palladium coal and then optionally brought into equilibrium.Type: GrantFiled: December 11, 1992Date of Patent: February 20, 1996Assignee: Dragoco Gerberding & Co. GmbHInventors: Ernst-Joachim Brunke, Claus-Hermann Kappey, Bernd Holscher, Hartmut Struwe
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Patent number: 5367092Abstract: Described are substituted 2,6-dimethylbicyclo[3,3,1]- non-6-enes defined according to the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond and wherein "R" represents one of the moieties: ##STR2## processes for preparing same and uses thereof in augmenting or enhancing the aroma of consumable materials including perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, hair preparations, fabric softeners, fabric softener articles, cosmetic powders and perfumed polymers).Type: GrantFiled: December 17, 1993Date of Patent: November 22, 1994Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, Matthew J. McGinnis, Charles E. J. Beck, Marie R. Hanna, Franc T. Schiet
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Patent number: 5346884Abstract: Described are substituted 2,6-dimethylbicyclo[3,3,1]-non-6-enes defined according to the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond and wherein "R" represents one of the moieties: ##STR2## processes for preparing same and uses thereof in augmenting or enhancing the aroma of consumable materials including perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, hair preparations, fabric softeners, fabric softener articles, cosmetic powders and perfumed polymers).Type: GrantFiled: October 1, 1993Date of Patent: September 13, 1994Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, Matthew J. McGinnis, Charles E. J. Beck, Marie R. Hanna, Franc T. Schiet
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Patent number: 5235076Abstract: Novel azulenic retinoid compounds and therapeutic compositions are disclosed, along with method for their production and use as anti-cancer and cancer-prevention agents. The compositions of the present invention will also find use in treating dermatological disorders such as acne and psoriasis, as well as dermatologically-related conditions such as repair and effacement of wrinkles.Type: GrantFiled: May 28, 1991Date of Patent: August 10, 1993Assignee: University of HawaiiInventors: Alfred E. Asato, Robert S. H. Liu
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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: 4992416Abstract: Isomeric formyl trimethylbicyclo[2.2.2]oct-7-enes, their use as perfumes, and a process for their preparation comprising a Diels-Alder reaction of acrolein with either 1,5,5-trimethylcyclohexa-1,3-diene, 3,5,5-trimethylcyclohexa-1,3-diene, 5,5-dimethyl-3-methylene-cyclohex-1-ene or mixtures thereof.Type: GrantFiled: May 5, 1989Date of Patent: February 12, 1991Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Klaus Bruns, Thomas Gerke, Michael Virnig
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Patent number: 4983627Abstract: Compounds useful in treating or preventing gastrointestinal ulcers and in treating cardiovascular disorders such as thrombosis, hypertension and atherosclerosis are depicted in formulas (1), (2) and (3): ##STR1## wherein: A is --C.tbd.C--, trans --HC.dbd.CH--, trans --CH.dbd.CHCH.sub.2 -- or --CH.sub.2 CH.sub.2 --;X is lower alkyl of 1-6 carbon atoms;Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl);n is an integer from 2-4;R.sub.1 is --CH.sub.2 OH, --CHO, --CO.sub.2 R or --CO.sub.2 H, and the olefin formed by the R.sub.1 (CH.sub.2).sub.n CH.dbd. moiety is either (E) or (Z);R.sub.2 is hydrogen or methyl, or optionally --CH.dbd.CH.sub.2 when A is trans --CH.dbd.CHCH.sub.2 --; andR.sub.3 is linear or branched alkyl, alkenyl or alkynyl having 5-10 carbon atoms, ##STR2## --(CH.sub.2).sub.m -phenyl or CH.sub.2 O-phenyl; in which each phenyl may be optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen.Type: GrantFiled: November 10, 1988Date of Patent: January 8, 1991Assignee: Syntex (U.S.A.) Inc.Inventors: Counde O'Yang, Walter Kurz, Keith A. M. Walker, Helen Y. Wu
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Patent number: 4925956Abstract: The invention relates to a process for manufacturing optically active carbacyclin intermediate products from racemic cis-bicyclo[3.3.0]octane-2-carboxylic acids. This process makes it possible in an advantageous way to produce important intermediates for the synthesis of stable and pharmacologically active carbacyclin derivatives.Type: GrantFiled: July 13, 1988Date of Patent: May 15, 1990Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Helmut Dahl
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Patent number: 4922027Abstract: The cycloaliphatic aldehydes of formula ##STR1## wherein R.sup.0, R.sup.1 and R.sup.2 represent independently a hydrogen atom or a lower alkyl from C.sub.1 to C.sub.6 and X stands for a group of formula ##STR2## wherein R.sup.3 and R.sup.4 represent independenly a lower alkyl radical from C.sub.1 to C.sub.3 and R.sup.5 represents a lower alkyl radical or hydrogen, provided that R.sup.1, R.sup.3 and R.sup.4 do not represent simulataneously a methyl radical whenever R.sup.0 and R.sup.2 represent each a hydrogen atom, are prepared from enol esters of formula ##STR3## wherein the wavy line stands for a --C--O-- bond of cis or trans configuration, Y represents an acyl group or P(O)(OR).sub.2, wherein R stands for a lower alkyl monovalent radical or an aryl, and Z defines a group of formula ##STR4## wherein R.sup.3, R.sup.4 and R.sup.5 are defined as above, by cyclisation carried out by means of an acidic cyclisation agent.Type: GrantFiled: January 4, 1989Date of Patent: May 1, 1990Assignee: Firmenich SAInventors: Dana P. Simmons, Christian Chapuis
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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: 4847392Abstract: A method of conducting a Diels-Alder reaction is provided comprising reacting a Diels-Alder diene comprising a 1,3-conjugated diene with a dienophile comprising an alpha,beta-unsaturated acetal or ketal in the presence of a protonating acid to yield a [4+2] cycloadduct.Type: GrantFiled: March 17, 1987Date of Patent: July 11, 1989Assignee: Regents of the University of MinnesotaInventors: Paul G. Gassman, Daniel A. Singleton
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Patent number: 4777184Abstract: Prostaglandin derivatives, and specifically derivatives of isocarbacyclin, have an optionally substituted methylene group as a substituent on the .alpha.-carbon atom of the .alpha.-side chain. They have a variety of physiological effects, notably a strong ability to inhibit blood platelet aggregation and a strong anti-ulcer activity.Type: GrantFiled: April 29, 1986Date of Patent: October 11, 1988Assignee: Sankyo Company LimitedInventors: Koichi Kojima, Shigeo Amemiya, Kazuo Koyama, Nobuyoshi Iwata, Takeshi Oshima
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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: 4735966Abstract: Compounds useful in treating cardiovascular disorders such as thrombosis, hypertension and atherosclerosis are depicted in formulas (1), (2) and (3): ##STR1## wherein: A is --C.tbd.C--, trans --HC.dbd.CH--, --CH.sub.2 CH.sub.2 -- or --CH.dbd.CHCH.sub.2 --;X is lower alkoxy, hydroxy, or (2,2,2)-trifluoroethoxy;Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl);is an integer of 2-4;R.sub.1 is --CH.sub.2 OH, --CHO, --CO.sub.2 R or --CO.sub.2 H, and the olefin formed by the R.sub.1 (CH.sub.2).sub.n CH.dbd. moiety is either (E) or (Z);R.sub.2 is hydrogen or methyl, or optionally --CH.dbd.CH.sub.2 when A is --CH.dbd.CHCH.sub.2 --; andR.sub.3 is linear or branched alkyl, alkenyl or alkynyl having 5-10 carbon atoms, ##STR2## --(CH.sub.2).sub.m -phenyl or CH.sub.Type: GrantFiled: August 25, 1986Date of Patent: April 5, 1988Assignee: Syntex (U.S.A.) Inc.Inventors: Helen Y. Wu, Walter Kurz
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Patent number: 4701543Abstract: Oxygenated decaline derivatives of formula ##STR1## wherein X represents a COOH or a CHO group are obtained according to a process which consists in the oxidation of a ketone of formula ##STR2## by means of oxygen in a basic medium constituted by potassium tert-butoxide in 1,2-dimethoxyethane.Compounds (I) are useful starting materials for the preparation of AMBROX.RTM. (registered tradename of Firmenich SA, Geneva, Switzerland) which is an ingredient in perfumes.Type: GrantFiled: July 18, 1986Date of Patent: October 20, 1987Assignee: Firmenich S.A.Inventors: Ferdinand Naef, Christian Vial
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Patent number: 4681951Abstract: There are disclosed bicyclo[3.3.0]octene derivatives having the following formula: ##STR1## wherein R.sup.1 is a straight, branched or cyclic alkyl group or alkenyl group each having 5 to 10 carbon atoms; andR.sup.2 and R.sup.3 are each separately a hydrogen atom or a protective group of a hydroxy group,and process for producing the same. These compounds and the process for producing them are available for producing a 9(0)-methano-.DELTA.6(9.alpha.)-PGI.sub.1.Type: GrantFiled: August 17, 1984Date of Patent: July 21, 1987Assignee: Sagami Chemical Research CenterInventors: Masakatsu Shibasaki, Toshiaki Mase, Mikiko Sodeoka, Yuji Ogawa
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Patent number: 4656194Abstract: An azulene derivative capable of exerting a hypocholesterolemic effect on a mammal which is represented by the formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and are selected from the group consisting of hydrogen, C.sub.1 -C.sub.12 alkyl groups and C.sub.2 -C.sub.12 alkenyl groups.Type: GrantFiled: October 9, 1985Date of Patent: April 7, 1987Assignee: Ajinomoto Co., Inc.Inventors: Masabumi Yasunami, Kahei Takase, Akira Shinji, Toru Mimura, Kunio Torii, Takaaki Kobayashi, Masaru Okutsu, Takashi Meguro
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Patent number: 4644068Abstract: Bicyclo[3.3.0]octenylaldehyde derivatives represented by the formula: ##STR1## wherein R.sup.1 is a substituent selected from the group consisting of a hydrogen atom and a protective group of a hydroxy group;R.sup.2 is a substituent selected from the group consisting of --CH.sub.2 OR.sup.5, ##STR2## where R.sup.5 is a substituent selected from the group consisting of a hydrogen atom and a protective group of a hydroxy group,R.sup.6 is a substituent selected from the group consisting of an alkyl group, an alkenyl group and an alkynyl group, said substituent being straight, branched or cyclic and having 5 to 10 carbon atoms,X is a substituent selected from the group consisting of a vinylene group and an acetylene group, andR.sup.7 is a substituent selected from the group consisting of an alkyl, an alkenyl group, and an alkynyl group, said substituent being straight, branched or cyclic and having 5 to 10 carbon atoms; andR.sup.Type: GrantFiled: August 17, 1984Date of Patent: February 17, 1987Assignee: Sagami Chemical Research CenterInventors: Masakatsu Shibasaki, Mikiko Sodeoka, Yuji Ogawa
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Patent number: 4622171Abstract: Described is the genus of polyhydroindan carboxaldehydes defined according to the structure: ##STR1## wherein each of the dashed lines represent carbon-carbon single bonds or carbon-carbon double bonds with the proviso that at least one of the dashed lines represents a carbon-carbon single bond; wherein one of R.sub.1, R.sub.2 and R.sub.3 is hydrogen or methyl and each of the other of R.sub.1, R.sub.2 and R.sub.3 represents hydrogen; wherein one of R.sub.4, R.sub.5 and R.sub.6 represents hydrogen or methyl and each of the other of R.sub.4, R.sub.5 and R.sub.6 represents hydrogen; wherein m is 0 or 1 and n is 0 or 1 and the sum of m+n=1; wherein X' represents one of the moieties: ##STR2## wherein R.sub.7 represents C.sub.1 -C.sub.3 alkyl or acetyl; and wherein R.sub.8 represents C.sub.1 -C.sub.Type: GrantFiled: March 15, 1985Date of Patent: November 11, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, William L. Schreiber, Futoshi Fujioka, Richard M. Boden, Manfred H. Vock, Patrick Whelan, Marie R. Hanna
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Patent number: 4620039Abstract: Described is a genus of norbornylbutadiene-acrolein adducts defined according to the structure: ##STR1## wherein one of X.sub.1 or X.sub.2 represents carboxaldehyde and the other of X.sub.1 or X.sub.2 represents hydrogen; wherein R.sub.1 and R.sub.2 taken together represent vinyl or ethylidene and R.sub.3 represents hydrogen or R.sub.2 and R.sub.3 taken together completes a cyclopenteno moiety and R.sub.1 represents hydrogen and uses thereof in augmenting or enhancing the aroma of consumable materials selected from the group consisting of perfume compositions, colognes and perfumed articles (e.g., perfumed polymers, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, dryer-added fabric softener articles, hair preparations, hair sprays, bath preparations and the like).Type: GrantFiled: June 7, 1985Date of Patent: October 28, 1986Assignee: International Flavors & Fragrances Inc.Inventor: Wilhelmus J. Wiegers
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Patent number: 4554384Abstract: Described are tertiary hydroxyl carboxaldehydes defined according to the generic structure: ##STR1## represent covalent carbon-carbon bonds when m does not=0; and wherein the lines ##STR2## do not represent any bonds when m=0; wherein R represents hydrogen or methyl; wherein p and q each represents 0 or 1 with the proviso that p=1 when q=0 and p=0 when q=1; wherein X and Z each represent one or more carbon atoms required to complete a bicyclo ring with the lines ##STR3## representing carbon-carbon bonds; wherein X and Z complete a phenyl moiety when the line ##STR4## represents no bond; wherein X and Z complete a cycloalkyl ring moiety with the lines ##STR5## represent carbon-carbon bonds and with the line ##STR6## representing no bond; and wherein when m is 0, X represents an alkylene moiety, processes for preparing same by means of reacting carbon monoxide and hydrogen with an unsaturated tertiary alcohol defined according to the structure: ##STR7## by means of an oxo reaction, and uses thereof in augmentinType: GrantFiled: October 1, 1984Date of Patent: November 19, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4541949Abstract: Described is the composition of matter defined according to the structure: ##STR1## as well as components of such composition having the structures: ##STR2## and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles.Type: GrantFiled: September 1, 1983Date of Patent: September 17, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, William L. Schreiber, Futoshi Fujioka, Richard M. Boden, Manfred H. Vock, Patrick Whelan, Marie R. Hanna
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Patent number: 4532364Abstract: Described are ether carboxaldehydes defined according to the generic structure: ##STR1## wherein X represents aryl, alkaryl, hydroxyalkyl, alkenyl, cycloalkenyl, lower alkyl or bicycloalkyl; wherein Y represents C.sub.1 -C.sub.3 lower alkylene; wherein Z completes an alkyl substituted C.sub.6 cycloalkyl ring or represents no moiety; wherein R represents hydrogen or methyl; wherein m represents 0 or 1; wherein n represents 0 or 1; wherein p represents 0 or 1 and wherein q represents 0 or 1 with the provisos that when m is 1, Z completes the alkyl substituted or unsubstituted C.sub.Type: GrantFiled: September 19, 1983Date of Patent: July 30, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4528402Abstract: Described are hydrocarbyloxy alkanals defined according to the generic structure: ##STR1## wherein R.sub.1 represents one of the moieties: ##STR2## and R.sub.2 represents hydrogen or methyl prepared according to the process of first reacting an allyl alcohol defined according to the structure: ##STR3## with a hydrocarbon or hydrocarbyl halide defined according to the structure:R.sub.1 '--Xhaving an electrophilic center wherein R.sub.1 ' is saturated or unsaturated hydrocarbyl and X represents halogen or hydrogen with the provisos that:R.sub.1 ' is saturated hydrocarbyl when X is halogen andR.sub.1 ' is unsaturated hydrocarbyl when X is hydrogen.Also described are organoleptic uses of such hydrocarbyloxy alkanals in the field of perfumery, colognes and perfumed articles, (e.g. perfumed plastics, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions or drier-added fabric softener articles).Type: GrantFiled: September 26, 1983Date of Patent: July 9, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, William L. Schreiber, Futoshi Fujioka, Patrick Chant, Lambert Dekker
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Patent number: 4524017Abstract: Norbornane derivatives having hydrocarbon side chains, the processes for preparing the same and perfume compositions containing the same. The norbornane derivatives are represented by the following general formula (I) ##STR1## wherein C.sub.2 is an ethyl group, an ethylidene group or a vinyl group each connected to 5 or 6 position of the norbornane ring, each of R.sub.1 and R.sub.2 is a hydrogen atom or a methyl group, and R.sub.3 is a formyl group or a group represented by the following general formula (II) ##STR2## wherein R.sub.4 is a methyl group, an ethyl group, a n-propyl group or an isopropyl group, and X is a carbon atom of the norbornane ring. The above norbornane derivatives give a wide variety of woody fragrances and are useful as components for various perfume products.Type: GrantFiled: February 24, 1982Date of Patent: June 18, 1985Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Yoshiharu Inoue, Fumio Tanimoto, Hisao Kitano
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Patent number: 4522748Abstract: Bicyclic aldehydes of formula ##STR1## possess useful organoleptic properties and can be used advantageously as perfume and flavor ingredients. Compounds (I) develop woody and ambery odor notes and woody, musky and earthy gustative characteristics. They are prepared by a multistep process starting from (E)-13-norcaryophyll-4-en-8-one.Type: GrantFiled: August 19, 1983Date of Patent: June 11, 1985Assignee: Firmenich SAInventors: Bruno Maurer, Arnold Hauser
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Patent number: 4519943Abstract: Described are 5-alkoxybicyclo[2.2.1]heptane-2-oxypropane derivatives defined according to the structure: ##STR1## (wherein R represents C.sub.1 -C.sub.3 alkyl and wherein Z represents one of the moieties, carbinol having the structure: ##STR2## or carboxaldehyde having the structure: ##STR3## and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes or perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders, hair preparations, perfumed polymers and the like).Type: GrantFiled: September 26, 1983Date of Patent: May 28, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber, Patrick Whelan, Marie R. Hanna
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Patent number: 4508651Abstract: The invention is directed to a process and intermediates for the preparation of 1.alpha.,25-dihydroxyergocalciferol as well as substantially pure and crystalline 1.alpha.,25-dihydroxyergocolciferol. The end-product 1.alpha.,25-dihydroxyergocalciferol is useful in the treatment of disease states which are characterized by insufficient amounts of 1.alpha.,25-dihydroxycholecalciferol.Type: GrantFiled: March 21, 1983Date of Patent: April 2, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Enrico G. Baggiolini, Andrew D. Batcho, Alfred Boris, Milan R. Uskokovic
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Patent number: 4486218Abstract: 1-Vinyltriazole compounds of the formula ##STR1## wherein R.sup.1 is alkyl, substituted alkyl, cycloalkyl, aryl or substituted aryl;R.sup.2 is alkyl;R.sup.3 is alkyl, cycloalkyl, cycloalkenyl, substituted cycloalkenyl, alkenyl, aryl or substituted aryl; orR.sup.2 and R.sup.3, together with the carbon to which they are bonded, represent cycloalkenyl, substituted cycloalkenyl, cycloalkyl or substituted cycloalkyl;X is the group ##STR2## or, alternatively, X may represent a keto group provided that when X is a keto group, R.sup.1 is alkyl, substituted alkyl, cycloalkyl, or substituted cycloalkyl;R.sup.4 is hydrogen, alkyl, aralkyl, substituted aralkyl, acyl, carbamoyl or substituted carbamoyl;R.sup.5 is hydrogen, alkyl, aralkyl or substituted aralkyl;and acid addition salts and metal salt complexes thereof; are outstandingly effective plant growth regulants and as fungicides.Type: GrantFiled: August 20, 1981Date of Patent: December 4, 1984Assignee: Bayer AktiengesellschaftInventors: Wolf Reiser, Wilfried Draber, Karl H. Buchel, Klaus Lurssen, Paul-Ernst Frohberger, Volker Paul
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Patent number: 4480136Abstract: Described is a compound having the structure: ##STR1## a norbornyl oxyacetaldehyde, prepared by oxidizing the norbornyl oxyethanol compound having the structure: ##STR2## using air or oxygen and a silver or copper chromite catalyst; and organoleptic uses of such oxidation product in the field of perfumery, colognes and perfumed articles (e.g. perfumed plastics, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions or drier-added fabric softener articles).Type: GrantFiled: January 10, 1983Date of Patent: October 30, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Robert P. Belko, Richard M. Boden, Marie R. Hanna
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Patent number: 4478743Abstract: Described is a compound having the structure: ##STR1## a norbornyl oxyacetaldehyde, prepared by oxidizing the norbornyl oxyethanol compound having the structure: ##STR2## using air or oxygen and a silver or copper chromite catalyst; and organoleptic uses of such oxidation product in the field of perfumery, colognes and perfumed articles (e.g. perfumed plastics, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions or drier-added fabric softener articles).Type: GrantFiled: February 23, 1984Date of Patent: October 23, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Robert P. Belko, Richard M. Boden, Marie R. Hanna
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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: 4443632Abstract: Compounds of formula ##STR1## having a double bond in one of the positions indicated by the dotted lines and wherein R represents a hydrogen atom or a methyl radical are utilized as starting materials for the preparation of bicyclic unsaturated hydrocarbons of formula ##STR2## (R=H, CH.sub.3). Conversion of (II) to (I) occurs via thermal treatment in the presence of a metal catalyst.Disclosed is also a process for the preparation of (II).Type: GrantFiled: June 22, 1982Date of Patent: April 17, 1984Assignee: Firmenich SAInventors: Karl H. Schulte-Elte, Bernard L. Muller, Eric Maillefer
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Patent number: 4443633Abstract: Described are hydrocarbyloxy alkanals defined according to the generic structure: ##STR1## wherein R.sub.1 represents one of the moieties: ##STR2## and R.sub.2 represents hydrogen or methyl prepared according to the process of first reacting an allyl alcohol defined according to the structure: ##STR3## with a hydrocarbon or hydrocarbyl halide defined according to the structureR.sub.1 '--Xhaving an electrophilic center wherein R.sub.1 ' is saturated or unsaturated hydrocarbyl and X represents halogen or hydrogen with the provisos that:R.sub.1 ' is saturated hydrocarbyl when X is halogen andR.sub.1 ' is unsaturated hydrocarbyl when X is hydrogen.Also described are organoleptic uses of such hydrocarbyloxy alkanals in the field of perfumery, colognes and perfumed articles, (e.g. perfumed plastics, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions or drier-added fabric softener articles).Type: GrantFiled: April 6, 1982Date of Patent: April 17, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, William L. Schreiber, Futoshi Fujioka, Patrick Chant, Lambert Dekker
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Patent number: 4439614Abstract: 5,6-Methano-5,6-dihydroretinoids such as ethyl (E)-5,6-methano-5,6-dihydroretinoate and (E)-1-(4-carbethoxyphenyl)-2-methyl-4-(2,2,6-trimethylbicyclo[4.1.0]hept-1 -yl)-1,3-butadiene are disclosed. These componds are useful as chemopreventive agents for inhibiting tumor promotion in epithelial cells and for treating nonmalignant skin disorders.Type: GrantFiled: September 22, 1982Date of Patent: March 27, 1984Assignee: SRI InternationalInventors: Marcia I. Dawson, Rebecca Chan, Peter D. Hobbs
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Patent number: 4438269Abstract: The novel compound 4-dimethylaminopyridinium chlorochromate has been found to be an effective oxidizing agent for converting alcohols to their respective aldehydes or ketones, especially for the selective conversion of allylic and benzylic alchols to their corresponding aldehydes and ketones.Type: GrantFiled: August 9, 1982Date of Patent: March 20, 1984Assignee: Thiokol CorporationInventor: Frank S. Guziec, Jr.
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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