Bicyclo Ring System Patents (Class 568/374)
  • Patent number: 4847392
    Abstract: 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: Grant
    Filed: March 17, 1987
    Date of Patent: July 11, 1989
    Assignee: Regents of the University of Minnesota
    Inventors: Paul G. Gassman, Daniel A. Singleton
  • Patent number: 4794193
    Abstract: 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: Grant
    Filed: April 15, 1982
    Date of Patent: December 27, 1988
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Myrna L. Hagedorn
  • Patent number: 4728747
    Abstract: 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: Grant
    Filed: December 30, 1985
    Date of Patent: March 1, 1988
    Assignee: Basf Aktiengesellschaft
    Inventors: Werner Hoffmann, Lothar Janitschke
  • Patent number: 4721729
    Abstract: 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: Grant
    Filed: February 8, 1985
    Date of Patent: January 26, 1988
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Robert Nickolson, Martin Haberey, Olaf Loge, Claus-Steffen Stuerzebecher
  • Patent number: 4707295
    Abstract: 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: Grant
    Filed: March 24, 1986
    Date of Patent: November 17, 1987
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Ludwig Pohl, Bernhard Scheuble, Andreas Wachtler, Reinhard Hittich, Peter Fuss
  • Patent number: 4700008
    Abstract: 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: Grant
    Filed: November 25, 1983
    Date of Patent: October 13, 1987
    Assignee: Mitsubishi Yuka Fine Chemicals Co., Ltd.
    Inventors: Makoto Takeda, Hiroshi Iwane, Akira Yoshida, Teruo Mori
  • Patent number: 4693845
    Abstract: 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: Grant
    Filed: June 18, 1986
    Date of Patent: September 15, 1987
    Assignee: KAO Corporation
    Inventors: Yoshiaki Fujikura, Akira Yamamuro, Motoki Nakajima
  • Patent number: 4689349
    Abstract: 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: Grant
    Filed: March 12, 1986
    Date of Patent: August 25, 1987
    Assignee: CBD Corporation
    Inventors: Walter J. Kasha, Chantal S. Burnison
  • Patent number: 4680142
    Abstract: 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: Grant
    Filed: October 17, 1986
    Date of Patent: July 14, 1987
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Myrna L. Hagedorn
  • Patent number: 4671798
    Abstract: Bicyclic carbinol of formula ##STR1## or 1,2,3,4,4a,5,8,8a-octahydro-2,2,6,8-tetramethyl-1-naphthalenol possesses useful odorous properties and it can be used advantageously as perfuming ingredient. A two-step process for its synthesis is disclosed starting from 2-methylpenta-1,3-diene and 6,6-dimethyl-cyclohex-2-en-1-one.
    Type: Grant
    Filed: March 26, 1985
    Date of Patent: June 9, 1987
    Assignee: Firmenich SA
    Inventor: Claudio Tarchini
  • Patent number: 4644068
    Abstract: 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: Grant
    Filed: August 17, 1984
    Date of Patent: February 17, 1987
    Assignee: Sagami Chemical Research Center
    Inventors: Masakatsu Shibasaki, Mikiko Sodeoka, Yuji Ogawa
  • Patent number: 4639532
    Abstract: Disclosed is an improved process for synthesizing periplanone-B, the sex attractant and sex excitant pheromone of the American cockroach, Periplaneta americana.
    Type: Grant
    Filed: June 18, 1984
    Date of Patent: January 27, 1987
    Assignee: Yale University
    Inventor: Stuart L. Schreiber
  • Patent number: 4633011
    Abstract: 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: Grant
    Filed: March 10, 1986
    Date of Patent: December 30, 1986
    Assignee: Firmenich SA
    Inventors: George H. Buchi, Hans Wuest
  • Patent number: 4617146
    Abstract: 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: Grant
    Filed: January 9, 1984
    Date of Patent: October 14, 1986
    Assignee: Givaudan Corporation
    Inventors: Daniel Helmlinger, Mario Pesaro, Michael Klaus
  • Patent number: 4607109
    Abstract: 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: Grant
    Filed: September 10, 1985
    Date of Patent: August 19, 1986
    Assignee: Firmenich SA
    Inventor: Roger L. Snowden
  • Patent number: 4595776
    Abstract: 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: Grant
    Filed: December 17, 1984
    Date of Patent: June 17, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Enrico G. Baggiolini, Andrew D. Batcho, Alfred Boris, Milan R. Uskokovic
  • Patent number: 4590297
    Abstract: Novel compounds of the following general formula: ##STR1##
    Type: Grant
    Filed: March 8, 1985
    Date of Patent: May 20, 1986
    Assignee: The Upjohn Company
    Inventors: Paul A. Aristoff, John C. Sih
  • Patent number: 4588823
    Abstract: Novel compounds of the following general formula: ##STR1##
    Type: Grant
    Filed: September 27, 1984
    Date of Patent: May 13, 1986
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4576962
    Abstract: 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: Grant
    Filed: May 4, 1984
    Date of Patent: March 18, 1986
    Assignee: The Procter & Gamble Company
    Inventor: Randall S. Matthews
  • Patent number: 4549982
    Abstract: 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: Grant
    Filed: August 24, 1984
    Date of Patent: October 29, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Mark A. Sprecker, Robert P. Belko, Augustinus G. Van Loveren, Marie R. Hanna
  • Patent number: 4543428
    Abstract: 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: Grant
    Filed: June 8, 1984
    Date of Patent: September 24, 1985
    Assignee: Oregon Graduate Center for Study & Research
    Inventors: Frank M. Hauser, Dipakranjan Mal
  • Patent number: 4471135
    Abstract: 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: Grant
    Filed: September 26, 1983
    Date of Patent: September 11, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William J. Evers, Braja D. Mookherjee, Anton Van Ouwerkerk, Augustinus G. Van Loveren
  • Patent number: 4454352
    Abstract: 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: Grant
    Filed: July 26, 1982
    Date of Patent: June 12, 1984
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Martin Demuth, Kurt Schaffner
  • Patent number: 4452988
    Abstract: 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: Grant
    Filed: December 6, 1982
    Date of Patent: June 5, 1984
    Assignee: Sterling Drug Inc.
    Inventor: Malcolm R. Bell
  • Patent number: 4439614
    Abstract: 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: Grant
    Filed: September 22, 1982
    Date of Patent: March 27, 1984
    Assignee: SRI International
    Inventors: Marcia I. Dawson, Rebecca Chan, Peter D. Hobbs
  • Patent number: 4431843
    Abstract: 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: Grant
    Filed: April 26, 1982
    Date of Patent: February 14, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventor: Takao Yoshida
  • Patent number: 4429166
    Abstract: 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: Grant
    Filed: August 4, 1981
    Date of Patent: January 31, 1984
    Assignee: Research Corporation
    Inventors: Kyriacos C. Nicolaou, Ronald L. Magolda, David A. Claremon
  • Patent number: 4424378
    Abstract: 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: Grant
    Filed: July 8, 1982
    Date of Patent: January 3, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Braja D. Mookherjee, Robert W. Trenkle, Robin K. Wolff, Richard M. Boden, Takao Yoshida
  • Patent number: 4421689
    Abstract: 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: Grant
    Filed: November 5, 1979
    Date of Patent: December 20, 1983
    Inventor: Albertus J. Mulder
  • Patent number: 4415756
    Abstract: 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: Grant
    Filed: December 2, 1981
    Date of Patent: November 15, 1983
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Martin Demuth, Kurt Schaffner
  • Patent number: 4385073
    Abstract: 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: Grant
    Filed: March 26, 1982
    Date of Patent: May 24, 1983
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Manfred H. Vock, Domenick Luccarelli, Jr., Frederick L. Schmitt, Joaquin F. Vinals, Jacob Kiwala
  • Patent number: 4371460
    Abstract: 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: Grant
    Filed: December 22, 1981
    Date of Patent: February 1, 1983
    Assignee: Firmenich SA
    Inventors: Ferdinand Naf, Rene Decorzant, Karl H. Schulte-Elte
  • Patent number: 4346041
    Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet 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: Grant
    Filed: December 22, 1980
    Date of Patent: August 24, 1982
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4339467
    Abstract: 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: Grant
    Filed: June 25, 1981
    Date of Patent: July 13, 1982
    Assignee: International Flavors & Fragrances Inc.
    Inventor: Takao Yoshida
  • Patent number: 4335138
    Abstract: 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: Grant
    Filed: September 15, 1980
    Date of Patent: June 15, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter-Wielant Wiersdorff, Karl-Heinz Geiss, Harald Weifenbach, Wolfgang Worstmann, Dieter Lenke, Rolf Kretzschmar
  • Patent number: 4331602
    Abstract: 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: Grant
    Filed: March 16, 1981
    Date of Patent: May 25, 1982
    Assignee: Pfizer Inc.
    Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4322435
    Abstract: 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: Grant
    Filed: May 27, 1980
    Date of Patent: March 30, 1982
    Assignee: Sankyo Company Limited
    Inventors: Koichi Kojima, Kiyoshi Sakai, Shinsaku Kobayashi
  • Patent number: 4304944
    Abstract: 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: Grant
    Filed: February 25, 1980
    Date of Patent: December 8, 1981
    Assignee: Fritzsche Dodge & Olcott Inc.
    Inventors: Brian J. Willis, Robert G. Eilerman
  • Patent number: 4303674
    Abstract: 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: Grant
    Filed: May 27, 1980
    Date of Patent: December 1, 1981
    Assignee: Beecham Group Limited
    Inventor: Alexander C. Goudie
  • Patent number: 4302363
    Abstract: 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: Grant
    Filed: June 9, 1980
    Date of Patent: November 24, 1981
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Klaus Bruns, Ursula Weber
  • Patent number: 4296036
    Abstract: 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: Grant
    Filed: March 31, 1980
    Date of Patent: October 20, 1981
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kenji Mori, Mitsuru Sasaki
  • Patent number: 4292432
    Abstract: 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: Grant
    Filed: February 4, 1980
    Date of Patent: September 29, 1981
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keiichi Ono, Akihiko Sugie, Hajime Kawakami, Junki Katsube
  • Patent number: 4284820
    Abstract: 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: Grant
    Filed: September 23, 1980
    Date of Patent: August 18, 1981
    Assignee: Shell Oil Company
    Inventor: Johannes L. M. Syrier
  • Patent number: 4283575
    Abstract: 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: Grant
    Filed: March 3, 1980
    Date of Patent: August 11, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4281204
    Abstract: 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: Grant
    Filed: October 5, 1979
    Date of Patent: July 28, 1981
    Assignee: Fritzsche Dodge & Olcott Inc.
    Inventors: Brian J. Willis, Robert G. Eilerman
  • Patent number: 4278817
    Abstract: 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: Grant
    Filed: November 21, 1979
    Date of Patent: July 14, 1981
    Assignee: Givaudan Corporation
    Inventor: Dietmar Lamparsky
  • Patent number: 4267377
    Abstract: 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: Grant
    Filed: August 30, 1979
    Date of Patent: May 12, 1981
    Assignee: Takeda Chemical Industries, Ltd.
    Inventor: Jiro Tsuji
  • Patent number: 4267395
    Abstract: 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: Grant
    Filed: March 3, 1980
    Date of Patent: May 12, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4256745
    Abstract: 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: Grant
    Filed: March 2, 1978
    Date of Patent: March 17, 1981
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Eckehard Schillinger
  • Patent number: 4255351
    Abstract: 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: Grant
    Filed: March 5, 1979
    Date of Patent: March 10, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Pierre Martin, Hans Greuter, Daniel Bellus