Bicyclo Ring System Patents (Class 568/374)
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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: 4794193Abstract: Described is a process for preparing 4,4A,5,6-tetrahydro-7-methyl-2-(3H)-naphthalenone having the structure: ##STR1## and intermediates useful in such process defined according to the structure: ##STR2## wherein one of R.sub.3 or R.sub.4 is hydrogen and the other of R.sub.3 or R.sub.4 is acetyl; and one of R.sub.1 or R.sub.2 is methyl and the other of R.sub.1 or R.sub.2 is acetoxy, said compound defined according to the structure: ##STR3## being useful in augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, medicinal products, chewing tobaccos, toothpastes, smoking tobaccos, smoking tobacco articles, perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, fabric softener articles and perfumed polymers.Type: GrantFiled: April 15, 1982Date of Patent: December 27, 1988Assignee: International Flavors & Fragrances Inc.Inventors: Alan O. Pittet, Ranya Muralidhara, Myrna L. Hagedorn
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Patent number: 4728747Abstract: Novel disubstituted bicyclo[2.2.1]heptanes of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.3 -alkyl, R.sup.2 is C.sub.1 -C.sub.8 -alkyl or-alkenyl, R.sup.3 and R.sup.4 together are .dbd.O, .dbd.CH--CN, .dbd.CH--CO--OCH.sub.3 or .dbd.CH--CO--OC.sub.2 H.sup.5, or R.sup.3 is hydrogen, --CH.sub.3, --CH.dbd.CH.sub.2 or --C.tbd.CH when R.sup.4 is --OH or --O--CO--CH.sub.3, or R.sup.3 is H when R.sup.4 is --CH.sub.2 --CO--OCH.sub.3, --CH.sub.2 --CO--OC.sub.2 H.sub.5 or --CH.sub.2 --C.tbd.N and one or both of the dashed lines may be a further bond, are obtained by subjecting cyclopentadiene to a Diels-Alder reaction with an unsaturated ketone, this reaction being catalyzed by a Lewis acid, and then subjecting the compound of the formula Ia ##STR2## initially formed to a reduction, a Grignard reaction or a reaction with diethylphosphonoacetonitrile or ethyl phosphonoacetate and NaH.They can be used as scents and/or aromas or as intermediates for scents.Type: GrantFiled: December 30, 1985Date of Patent: March 1, 1988Assignee: Basf AktiengesellschaftInventors: Werner Hoffmann, Lothar Janitschke
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Patent number: 4721729Abstract: Carbacyclins of Formula I ##STR1## wherein R.sub.1 is an alkyl, cycloalkyl, aryl, aralkyl, or heterocyclic group,Y is a keto group or a hydroxymethylene group,X is a --CH.sub.2 -- group or an oxygen atom,A is a --CH.sub.2 --CH.sub.2 --, a trans--CH.dbd.CH-- or a --C.tbd.C-- group,W is a hydroxymethylene group or a ##STR2## D is the group ##STR3## a straight-chain or branched, saturated alkylene group or unsaturated alkylene group of up to 5 carbon atoms which can optionally be substituted by 1-2 fluorine atoms,n is 1, 2 or 3,E is a direct bond, a --C.tbd.C-- group or a --CR.sub.4 .dbd.CR.sub.5 -- group wherein R.sub.4 is hydrogen or an alkyl group and R.sub.5 is hydrogen, halogen or an alkyl group,R.sub.2 is an alkyl, cycloalkyl, aryl, or heterocyclic group, andR.sub.3 is a hydroxy group,are valuable, e.g., as cytoprotective agents.Type: GrantFiled: February 8, 1985Date of Patent: January 26, 1988Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Robert Nickolson, Martin Haberey, Olaf Loge, Claus-Steffen Stuerzebecher
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Patent number: 4707295Abstract: Bicyclooctane derivatives of the formula IR.sup.1 --A.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 independently of one another are each an alkyl group which has 1-12 C atoms and in which it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by O atoms and/or CO groups and/or --O13 CO groups and/or --CO--O groups and/or --CH.dbd.CH-- groups, one of the radicals R.sup.1 and R.sup.2 being also --A.sup.3 --R.sup.3,A.sup.1 is a 1,4-cyclohexylene group which is unsubstituted or substituted in the 1-position and/or 2-position and/or 3-position and/or 4-position by alkyl which has in each case 1-5 C atoms and is unsubstituted or substituted or fluorinated, and in which it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by one or two different groupings from the group --O--, --CO--, --CH.dbd.CH--, --S--, --SO-- or --SO.sub.2 --, or is substituted by F, Cl, Br, CN and/or CHO,A.sup.2 is a 1,4-bicyclo[2.2.2] octylene group,--A.sup.3 --R.sup.3 is --Cy--R.sup.Type: GrantFiled: March 24, 1986Date of Patent: November 17, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ludwig Pohl, Bernhard Scheuble, Andreas Wachtler, Reinhard Hittich, Peter Fuss
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Patent number: 4700008Abstract: There is disclosed a novel 4,8-dimethylbicyclo[3.3.1]nonane derivative represented by the formula [I]: ##STR1## wherein X and Y have the same meanings as defined in the specification. The compound of the present invention has an unique and strong perfume and hence is expected to be useful as perfumery.Type: GrantFiled: November 25, 1983Date of Patent: October 13, 1987Assignee: Mitsubishi Yuka Fine Chemicals Co., Ltd.Inventors: Makoto Takeda, Hiroshi Iwane, Akira Yoshida, Teruo Mori
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Patent number: 4693845Abstract: Novel bornane-3-spiro-1'-cylopentane derivatives of the following formula (I) ##STR1## in which R.sub.1 and R.sub.2 are defined such that when R.sub.1 is a hydrogen atom, R.sub.2 is a hydroxyl group, or R.sub.1 and R.sub.2 are joined to form a ketone are obtained from camphor.The derivatives are synthesized in a simple process from an economical starting material, camphor. The derivatives have woody-note and can be widely used in perfumes, soaps, shampoos, hair rinses, cosmetics and the like.Type: GrantFiled: June 18, 1986Date of Patent: September 15, 1987Assignee: KAO CorporationInventors: Yoshiaki Fujikura, Akira Yamamuro, Motoki Nakajima
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Patent number: 4689349Abstract: Potent tumor inhibitors are prepared which are compounds of the formula: ##STR1## wherein Q is CO, CH(OH) or C(OH)CH.sub.3,M.sub.1 is halogen,M.sub.2 is halogen or hydrogen,c is one or twop is 0 or 1, andone of X and X' is H and the other is hydroxy-C.sup.2-9 alkyl, methoxy-C.sup.2-9 -alkyl, ethoxy-C.sup.2-9 -alkyl, oxo-C.sup.2-9 -alkyl, formyl-C.sup.2-9 -alkyl, carboxy-C.sup.2-9 -alkyl or (C.sub.1-2 -alkyl)oxycarbonyl-C.sup.2-9 -alkyl.Type: GrantFiled: March 12, 1986Date of Patent: August 25, 1987Assignee: CBD CorporationInventors: Walter J. Kasha, Chantal S. Burnison
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Patent number: 4680142Abstract: Described is a process for preparing 4,4A,5,6-tetrahydro-7-methyl-2-(3H)-naphthalenone having the structure: ##STR1## and intermediates useful in such process defined according to the structure: ##STR2## wherein one of R.sub.3 or R.sub.4 is hydrogen and the other of R.sub.3 or R.sub.4 is acetyl; and one of R.sub.1 or R.sub.2 is methyl and the other of R.sub.1 or R.sub.2 is acetoxy, said compound defined according to the structure: ##STR3## being useful in augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, medicinal products, chewing tobaccos, toothpastes, smoking tobaccos, smoking tobacco articles, perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, fabric softener articles and perfumed polymers.Type: GrantFiled: October 17, 1986Date of Patent: July 14, 1987Assignee: International Flavors & Fragrances Inc.Inventors: Alan O. Pittet, Ranya Muralidhara, Myrna L. Hagedorn
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Patent number: 4671798Abstract: Bicyclic carbinol of formula ##STR1## or 1,2,3,4,4a,5,8,8a-octahydro-2,2,6,8-tetramethyl-1-naphthalenol possesses useful odorous properties and it can be used advantageously as perfuming ingredient. A two-step process for its synthesis is disclosed starting from 2-methylpenta-1,3-diene and 6,6-dimethyl-cyclohex-2-en-1-one.Type: GrantFiled: March 26, 1985Date of Patent: June 9, 1987Assignee: Firmenich SAInventor: Claudio Tarchini
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Patent number: 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: 4639532Abstract: Disclosed is an improved process for synthesizing periplanone-B, the sex attractant and sex excitant pheromone of the American cockroach, Periplaneta americana.Type: GrantFiled: June 18, 1984Date of Patent: January 27, 1987Assignee: Yale UniversityInventor: Stuart L. Schreiber
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Patent number: 4633011Abstract: 3a,6,6,9a-Tetramethylperhydronaphto[2,1-b]furan, a typical ambergris perfume ingredient is prepared via a novel process from 1.beta.-(2-hydroxyethyl)-perhydro-2,5,5,8a.beta.-tetramethyl-2.beta.-trans -naphthalenol by cyclization with an acidic cyclization agent in the presence of nitromethane.Type: GrantFiled: March 10, 1986Date of Patent: December 30, 1986Assignee: Firmenich SAInventors: George H. Buchi, Hans Wuest
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Patent number: 4617146Abstract: This invention is concerned with novel substituted bicyclo[4.3.0]non-1(6)-en-8-yl methyl ketones, a process for their manufacture and novel fragrance and flavor compositions containing same.Type: GrantFiled: January 9, 1984Date of Patent: October 14, 1986Assignee: Givaudan CorporationInventors: Daniel Helmlinger, Mario Pesaro, Michael Klaus
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Patent number: 4607109Abstract: Nitrogen containing compounds of formula ##STR1## wherein symbol R designates a C.sub.1 -C.sub.3 alkyl group, each of R.sup.1 and R.sup.2 represents, when taken separately, a C.sub.1 -C.sub.6 alkyl radical or, when taken together, a polymethylene and R.sup.3 represents a C.sub.1 -C.sub.3 alkyl group, preferably a methyl radical, or a hydrogen atom.Process for their preparation comprising the addition of an amine of formula ##STR2## to an aldehyde of formula ##STR3## Use of said compounds (I) as starting materials for the preparation of decalin ketone derivatives of general formula ##STR4## containing a double bond in one of the positions indicated by the dotted lines and wherein R.sup.4 designates a hydrogen atom or a methyl radical, and symbols R and R.sup.3 have the meaning indicated for formula (I).Type: GrantFiled: September 10, 1985Date of Patent: August 19, 1986Assignee: Firmenich SAInventor: Roger L. Snowden
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Patent number: 4595776Abstract: 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: December 17, 1984Date of Patent: June 17, 1986Assignee: Hoffmann-La Roche Inc.Inventors: Enrico G. Baggiolini, Andrew D. Batcho, Alfred Boris, Milan R. Uskokovic
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Patent number: 4590297Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: March 8, 1985Date of Patent: May 20, 1986Assignee: The Upjohn CompanyInventors: Paul A. Aristoff, John C. Sih
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Patent number: 4588823Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: September 27, 1984Date of Patent: May 13, 1986Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4576962Abstract: The 13,14-didehydro-15-oxo analogues of natural prostaglandins possess high cytoprotective activity and low diarrheogenic activity, low anti-hemostatic activity and low smooth muscle contraction activity.Type: GrantFiled: May 4, 1984Date of Patent: March 18, 1986Assignee: The Procter & Gamble CompanyInventor: Randall S. Matthews
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Patent number: 4549982Abstract: Described are 1-oxoalkyl-2-isopropylnorbornane derivatives defined according to the generic structure: ##STR1## wherein X represents a moiety selected from the group consisting of: ##STR2## wherein the dashed line represents a carbon-carbon double bond or a carbon-carbon single bond and wherein R.sub.1 and R.sub.2 represent hydrogen or methyl with the proviso that R.sub.1 and R.sub.2 are not both methyl, and uses thereof in augmenting or enhancing the aroma of consumable materials selected from the group consisting of perfume compositions, colognes and perfumed articles. Also described are processes for preparing said 1-oxoalkyl-2-isopropylnorbornane derivatives by means of a low temperature catalytic Diels Alder reaction or high temperature thermal Diels Alder reaction between a bicyclopentadiene derivative and 2-methyl-3- buten-5-one according to the reaction: ##STR3## wherein R represents methyl or hydrogen.Type: GrantFiled: August 24, 1984Date of Patent: October 29, 1985Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, Mark A. Sprecker, Robert P. Belko, Augustinus G. Van Loveren, Marie R. Hanna
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Patent number: 4543428Abstract: The compound 6-acetyl-4a,5,6,7,8,8a-hexahydro-1(4H)-naphthalenone, and preparation thereof beginning from 2-(2-hydroxyethyl)bicyclo[2.2.2] oct-5-ene.Type: GrantFiled: June 8, 1984Date of Patent: September 24, 1985Assignee: Oregon Graduate Center for Study & ResearchInventors: Frank M. Hauser, Dipakranjan Mal
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Patent number: 4471135Abstract: Described is 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol as a mixture of isomers and in its isomeric forms having the structures: ##STR1## and the uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles, and colognes. Also described is a novel process for preparing 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol.Type: GrantFiled: September 26, 1983Date of Patent: September 11, 1984Assignee: International Flavors & Fragrances Inc.Inventors: William J. Evers, Braja D. Mookherjee, Anton Van Ouwerkerk, Augustinus G. Van Loveren
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Patent number: 4454352Abstract: New bicyclo[2.2.2]oct-5-en-2-ones of the formula 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: July 26, 1982Date of Patent: June 12, 1984Assignee: Studiengesellschaft Kohle mbHInventors: Martin Demuth, Kurt Schaffner
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Patent number: 4452988Abstract: Novel compounds, 1-ethenyl-6-(4-R'-phenyl)-3,4,9,9a-tetrahydro-9a-methyl-6H-naphtho[2,3-c]p yrazoles, wherein R' is hydrogen or fluoro, are useful as intermediates in the preparation of anti-inflammatory agents.Type: GrantFiled: December 6, 1982Date of Patent: June 5, 1984Assignee: Sterling Drug Inc.Inventor: Malcolm R. Bell
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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: 4431843Abstract: Described are compounds having the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond; wherein X represents the moieties: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.8 and R.sub.9 represent hydrogen or methyl with the proviso that (i) at least three of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen and (ii) when the dashed line is a carbon-carbon single bond and X is: ##STR3## then one of R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is methyl and the other represents hydrogen; wherein R.sub.5 represents hydrogen, MgZ or Li; wherein Z represents chloro, bromo or iodo and wherein R.sub.Type: GrantFiled: April 26, 1982Date of Patent: February 14, 1984Assignee: International Flavors & Fragrances Inc.Inventor: Takao Yoshida
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Patent number: 4429166Abstract: Stable biologically active thromboxane A.sub.2 analogues having the formula: ##STR1## wherein R.sup.1 is OR.sup.3, where R.sup.3 represents hydrogen or a pharmaceutically acceptable cation or lower alkyl group; orR.sup.1 is NR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 are the same or different substituents selected from the group consisting of hydrogen and lower alkyl group; andR.sup.2 is hydrogen or an --OH group.The thromboxane analogues are potent thrombotic agents, useful in cardiovascular treatment.Type: GrantFiled: August 4, 1981Date of Patent: January 31, 1984Assignee: Research CorporationInventors: Kyriacos C. Nicolaou, Ronald L. Magolda, David A. Claremon
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Patent number: 4424378Abstract: Described are methyl substituted pinyl oxopentenes and mixtures of same and uses thereof in augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, perfume compositions, perfumed articles (including perfumed polymers, solid or liquid cationic, anionic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, optical brightener compositions, and cosmetic powders), colognes, smoking tobacco compositions and smoking tobacco articles including cigars, cigarettes and integrated and separated filters therefor.Type: GrantFiled: July 8, 1982Date of Patent: January 3, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Braja D. Mookherjee, Robert W. Trenkle, Robin K. Wolff, Richard M. Boden, Takao Yoshida
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Patent number: 4421689Abstract: Derivative compounds of 1,5-dimethylbicyclo [3,2,1] octane of the general formula ##STR1## and perfume compositions containing these derivatives, wherein X represents a C.dbd.O group, a ##STR2## group or a ##STR3## group, in which R.sub.1 and R.sub.2 are alkyl groups and R.sub.3 is an ethylene or trimethylene group which may be substituted with one or more alkyl groups. These derivative compounds may be prepared by oxidation of 1,5-dimethylbicyclo [3,2,1] octan-8-ol or an ester thereof optionally followed by reaction with an alkanol or a 1,2- or 1,3-alkane-diol.Type: GrantFiled: November 5, 1979Date of Patent: December 20, 1983Inventor: Albertus J. Mulder
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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: 4385073Abstract: Described is the use of 4,4A,5,6-tetrahydro-7-methyl-2-(3H)-naphthalenone having the structure: ##STR1## in substantially pure liquid or pure crystalline form for augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, medicinal products, toothpastes, chewing tobaccos, smoking tobaccos, smoking tobacco articles, perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, fabric softener articles, perfumed polymers, hair preparations and the like.Type: GrantFiled: March 26, 1982Date of Patent: May 24, 1983Assignee: International Flavors & Fragrances Inc.Inventors: Alan O. Pittet, Ranya Muralidhara, Manfred H. Vock, Domenick Luccarelli, Jr., Frederick L. Schmitt, Joaquin F. Vinals, Jacob Kiwala
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Patent number: 4371460Abstract: Kentones of the formula ##STR1## wherein each of the symbols R.sup.1, R.sup.2, and R.sup.3 identical or different, represent a hydrogen atom or a lower alkyl radical containing 1 to 3 carbon atoms are disclosed useful as perfuming agents and in the preparation of perfume products.Type: GrantFiled: December 22, 1981Date of Patent: February 1, 1983Assignee: Firmenich SAInventors: Ferdinand Naf, Rene Decorzant, Karl H. Schulte-Elte
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Patent number: 4346041Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet antiaggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.Type: GrantFiled: December 22, 1980Date of Patent: August 24, 1982Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4339467Abstract: Described are compounds having the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond; wherein X represents the moieties: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.8 and R.sub.9 represent hydrogen or methyl with the proviso that (i) at least three of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen and (ii) when the dashed line is a carbon-carbon single bond and X is: ##STR3## then one of R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is methyl and the other represents hydrogen; wherein R.sub.5 represents hydrogen, MgZ or Li; wherein Z represents chloro, bromo or iodo and wherein R.sub.Type: GrantFiled: June 25, 1981Date of Patent: July 13, 1982Assignee: International Flavors & Fragrances Inc.Inventor: Takao Yoshida
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Patent number: 4335138Abstract: Novel carbamates derived from substituted cyclic .beta.-keto-alcohols, their preparation, and pharmaceutical formulations which contain these compounds and which may be used as hypnotics in the treatment of sleep disturbance and as sedatives.Type: GrantFiled: September 15, 1980Date of Patent: June 15, 1982Assignee: BASF AktiengesellschaftInventors: Walter-Wielant Wiersdorff, Karl-Heinz Geiss, Harald Weifenbach, Wolfgang Worstmann, Dieter Lenke, Rolf Kretzschmar
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Patent number: 4331602Abstract: Compounds having the formula ##STR1## wherein ##STR2## R.sub.1 is hydrogen, benzyl or alkanoyl, X is C.sub.2-4 alkylene; andZ-W is alkyl, phenylalkyl or pyridylalkyl which can have an oxygen atom as part of the alkyl chain and their use as CNS agents, antidiarrheals and antiemetics. Processes for their preparation and intermediates therefor are described.Type: GrantFiled: March 16, 1981Date of Patent: May 25, 1982Assignee: Pfizer Inc.Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4322435Abstract: Prostacyclin derivatives of formula (I): ##STR1## (wherein R.sup.1 represents a hydrogen atom or a lower alkyl group; R.sup.2 represents an alkenyl group having from 8 to 12 carbon atoms; and n represents an integer of from 1 to 8, inclusive) and pharmaceutically acceptable salts thereof, are valuable pharmaceuticals, showing excellent thrombocyte agglutination inhibitory, coronary blood vessel dilatory and bronchodilatory effects, and may be prepared by introducing the .dbd.CH(CH.sub.2).sub.n COOR.sup.1 side chain onto an appropriate compound by means of a Wittig reaction.Type: GrantFiled: May 27, 1980Date of Patent: March 30, 1982Assignee: Sankyo Company LimitedInventors: Koichi Kojima, Kiyoshi Sakai, Shinsaku Kobayashi
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Patent number: 4304944Abstract: Novel bicyclic ketones having the structure: ##STR1## wherein R is a C.sub.1 -C.sub.5 alkyl group, either straight-chain or branched, and saturated analogs have been prepared. These compounds exhibit floral and woody odors and/or desirable flavor properties, and are useful as fragrance and/or flavor materials. The compounds are conveniently prepared from alkylidene cyclopentanones by Michael addition with alkyl metalloacetoacetates and subsequent decarboxylative cyclization of the adducts. The saturated analogs may then be prepared by hydrogenation.Type: GrantFiled: February 25, 1980Date of Patent: December 8, 1981Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Brian J. Willis, Robert G. Eilerman
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Patent number: 4303674Abstract: A compound of formula (I): ##STR1## wherein the dotted line indicates an optional double bond and R is a hydrogen atom or a methyl group has topical anti-inflammatory activity.Type: GrantFiled: May 27, 1980Date of Patent: December 1, 1981Assignee: Beecham Group LimitedInventor: Alexander C. Goudie
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Patent number: 4302363Abstract: This invention is directed to the isomer mixture 4(5)-acetyl-7,7,9(7,9,9)-trimethylbicyclo[4.3.0]non-1-ene, the preparation thereof, and the use of said mixture as a perfuming agent. The isomer mixture represents a valuable new perfuming agent having strong, warm ambergris scent with woody tobacco leaf, methyl ionone, and arborvitae notes and having exceptional persistence as well.Type: GrantFiled: June 9, 1980Date of Patent: November 24, 1981Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Klaus Bruns, Ursula Weber
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Patent number: 4296036Abstract: A method for the preparation of 3,3,7-trimethyl-2,9-dioxatricyclo[3.3.1.0.sup.4,7 ]nonane (lineatin, a general name), an aggregation pheromone of an ambrosia beetle, represented by the formula (I), ##STR1## which comprises reacting a keto lactone represented by the formula (II), ##STR2## with diisobutylaluminum hydride and subsequently, treating with an acid; and a method for the preparation of said keto lactone represented by the above formula (II), which comprises oxidizing a hydroxy lactone represented by the formula (III), ##STR3## with chromic acid.Type: GrantFiled: March 31, 1980Date of Patent: October 20, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Kenji Mori, Mitsuru Sasaki
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Patent number: 4292432Abstract: A process for producing novel aldol derivatives of the formula, ##STR1## wherein C=W is a carbonyl group or a protected carbonyl group which comprises reacting a compound of the formula: ##STR2## wherein C=W is as defined above in the presence of an acid or a base at a temperature ranging from -70.degree. C. to room temperature. The novel aldol derivatives of the above formula are useful as intermediate for producing methanoprostacyclin derivatives which are useful medicines for prevention of thrombosis.Type: GrantFiled: February 4, 1980Date of Patent: September 29, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Keiichi Ono, Akihiko Sugie, Hajime Kawakami, Junki Katsube
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Patent number: 4284820Abstract: 4-Formyl-3,6,6-trimethylbicyclo[3.1.0]hex-3-ene is oxidized in one vessel by a peroxy acid via 3,4-epoxy-4-formyl-3,6,6-trimethylbicyclo[3.1.0]hexane and 3,4-epoxy-4-formyloxy-3,6,6-trimethylbicyclo[3.1.0]hexane to 3,6,6-trimethyl-3-hydroxybicyclo[3.1.0]hexan-4-one. The four compounds are novel and are intermediates to pyrethroid insecticides.Type: GrantFiled: September 23, 1980Date of Patent: August 18, 1981Assignee: Shell Oil CompanyInventor: Johannes L. M. Syrier
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Patent number: 4283575Abstract: The present invention provides novel 2-decarboxy-2-hydroxymethyl-19-hydroxy-6a-carba-PGI.sub.1 compounds which are useful for pharmacological purposes, e.g., anti-asthmatic indications.Type: GrantFiled: March 3, 1980Date of Patent: August 11, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4281204Abstract: The present invention relates to substituted spirocyclic derivatives having the general formula: ##STR1## wherein the dotted line represents a carbon-carbon double bond or a carbon-carbon single bond, wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are each the same or different, hydrogen or lower alkyl, wherein Z is one of the following: ##STR2## wherein R.sub.7 is either hydrogen or lower alkyl, wherein R.sub.8 and R.sub.9 are each lower alkyl; their methods of preparation and their use as odor-modifying ingredients in perfumes and perfumed products, and as flavor-modifying ingredients in the flavoring of foodstuffs and tobacco products.Type: GrantFiled: October 5, 1979Date of Patent: July 28, 1981Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Brian J. Willis, Robert G. Eilerman
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Patent number: 4278817Abstract: Novel prenyl 4-caranones of the general formula: ##STR1## wherein: one R group represents a 3-methyl-2-butenyl group andthe other a hydrogen atomare useful olfactory agents in the preparation of fragrance materials.Type: GrantFiled: November 21, 1979Date of Patent: July 14, 1981Assignee: Givaudan CorporationInventor: Dietmar Lamparsky
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Patent number: 4267377Abstract: A compound of the general formula: ##STR1## wherein R.sup.1 is a lower alkyl group; R.sup.2 is H or a lower alkyl group; Y is an oxo group, H or an unprotected or protected hydroxyl group; X is a methylene or ethylene group, for example, 7,7a-dihydro-7aS-methyl-4-(3-butenyl)-1-tert. butoxy-5(6H)-indanone, which is an intermediate for steroids, is prepared by dehydrative cyclization of a compound of the general formula of ##STR2## wherein R.sup.1, R.sup.2, X and Y are the same as above.Type: GrantFiled: August 30, 1979Date of Patent: May 12, 1981Assignee: Takeda Chemical Industries, Ltd.Inventor: Jiro Tsuji
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Patent number: 4267395Abstract: The present invention provides novel 2-decarboxy-2-hydroxymethyl-19-hydroxy-19-methyl-6a-carba-PGI.sub.1 compounds which are useful for pharmacological purposes, e.g., anti-asthmatic indications.Type: GrantFiled: March 3, 1980Date of Patent: May 12, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4256745Abstract: Prostan-1-ol esters and intermediates for their preparation are described; the former compounds exhibit improved organ specificity and a longer duration of activity at lower dosages than the corresponding non-esterified prostaglandins and are useful, inter alia, in triggering abortion, inducing labor and regulating the menstrual cycle.Type: GrantFiled: March 2, 1978Date of Patent: March 17, 1981Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Eckehard Schillinger
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Patent number: 4255351Abstract: Compounds of the formulae Ia, Ib, IIa and IIb ##STR1## are described, wherein R represents alkyl, haloalkyl, benzyl, naphthyl or substituted or unsubstituted phenyl and one of R.sub.1 and R.sub.2 represents methyl and the other represents hydrogen or methyl, or R.sub.1 and R.sub.2 together represent alkylene of 2 or 3 carbon atoms. The compound of the formulae Ia, Ib, IIa and IIb are valuable intermediates for the manufacture of pyrethroid pesticides or precursors thereof.Type: GrantFiled: March 5, 1979Date of Patent: March 10, 1981Assignee: Ciba-Geigy CorporationInventors: Pierre Martin, Hans Greuter, Daniel Bellus