Polycyclo-alicyclic Ring System In Alcohol Moiety Patents (Class 560/256)
  • Patent number: 5206415
    Abstract: Novel tricyclic steriod analogs are disclosed which are 1H-benz[e]indene dodecahydro compounds that are useful for enhancing GABA-induced chloride currents at the GABA receptor/chloride ionophore complex and can be represented by the following structural formulas: ##STR1## wherein R.sub.1 =H or C.sub.1 -C.sub.4 alkyl or fluoroalkyl;R.sub.2 =H or C.sub.1 -C.sub.4 alkyl or fluoroalkyl, in which R.sub.1 and R.sub.2 can be the same or different;R.sub.3 =H or CH.sub.3 ;R.sub.4 =H or CH.sub.3, in which R.sub.3 and R.sub.4 can be the same or different;R.sub.5 =H;R.sub.6 =H;R.sub.5,R.sub.6 =.dbd.O(carbonyl);R.sub.7 =H;R.sub.8 =a hydrogen bond accepting group.R.sub.7,R.sub.8 =.dbd.O(carbonyl); andR'=an ester group.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: April 27, 1993
    Assignee: Washington University
    Inventors: Douglas F. Covey, Yuefei Hu, Charles F. Zorumski
  • Patent number: 5175347
    Abstract: A process for preparing cis-dihydronopol and esters thereof in which corresponding esters of (-)nopol are stereoselectively hydrogenated by heterogeneous hydrogenation in the presence of a platinum, platinum oxide or ruthenium/carbon catalyst, and the resulting cis-dihydronopyl esters optionally may be converted into corresponding alcohols by hydrolysis.
    Type: Grant
    Filed: December 2, 1991
    Date of Patent: December 29, 1992
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Walter Heitmann, Uwe Maetzel
  • Patent number: 5175338
    Abstract: An isocarbacyclin derivative represented by the following formula [VII'] ##STR1## wherein A represents, a hydrocarbylcarboxylate group, a carboxymethoxycarbonyl group, an amide group, an acyloxymethyl group or a hydroxymethyl group; R.sup.4 represents H, a methyl group or a vinyl group; R.sup.5 represents a (substituted)alkyl group, a phenyl group, a phenoxy group or a cycloalkyl group; R.sup.e22 and R.sup.e32 represent H or a hydroxyprotecting group; n is 0 or 1;and a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: September 14, 1990
    Date of Patent: December 29, 1992
    Assignee: Teijin Limited
    Inventors: Atsuo Hazato, Toshio Tanaka, Noriaki Okamura, Kiyoshi Bannai, Seizi Kurozumi, Masaaki Suzuki, Ryoji Noyori
  • Patent number: 5173487
    Abstract: Antihypercholesterolemic activity, due to competitive inhibition of HMG CoA reductase, is exhibited by a compound of the formula ##STR1## m is 0 to 3; R is selected from:(1) alkyl;(2) substituted alkyl;(3) alkoxy;(4) alkenyl;(5) cycloalkyl;(6) phenyl; and(7) substituted aryl; andR.sup.1 and R.sup.2 are as defined in the specification.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: December 22, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jeffrey O. Saunders, Eric M. Gordon
  • Patent number: 5130306
    Abstract: Novel HMG-CoA reductase inhibitors are useful as antihypercholesterolemic agents and are represented by structural formulae (I) or (II): ##STR1## wherein position 5 of the polyhydronaphthyl ring is singly or doubly bonded to oxygen or incorporated into a C.sub.3-7 carbocyclic ring.
    Type: Grant
    Filed: June 6, 1990
    Date of Patent: July 14, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Mark E. Duggan, George D. Hartman
  • Patent number: 5116865
    Abstract: 15,16-Seco-19-nor progestins are provided which display elevated progestational activity with a minimum of ancillary hormonal activity. Processes for the preparation of the novel progestins are provided as are methods of use. A preferred method of use is in the suppression of ovulation in the human female.
    Type: Grant
    Filed: January 28, 1991
    Date of Patent: May 26, 1992
    Inventors: Richard H. Peters, Masato Tanabe
  • Patent number: 5102911
    Abstract: HMG-CoA reductase inhibitors of formulae (I) and (II) are disclosed.
    Type: Grant
    Filed: July 6, 1990
    Date of Patent: April 7, 1992
    Assignee: Merck & Co, Inc.
    Inventors: Ta J. Lee, Wilbur J. Holtz
  • Patent number: 5095155
    Abstract: Closely boiling diastereomeric isomer alcohols are separated by converting them to esters having disparate boiling points, separating the ester isomers by distillation and saponifying the separate ester isomers to obtain the individual alcohol isomers.
    Type: Grant
    Filed: June 7, 1990
    Date of Patent: March 10, 1992
    Assignee: Union Camp Corporation
    Inventor: Peter W. D. Mitchell
  • Patent number: 5051409
    Abstract: 2-Aminodecalin derivatives of the formula I ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are H or methyl,A is H, OH, O-alkylcarbonyl, O-benzoyl or O-CH.sub.3,R.sup.4 is H, cyclopropyl, alkyl, alkenyl, or alkynyl,R.sup.5 is alkyl, alkenyl or alkynyl which is substituted or unsubstituted,cycloalkyl or cycloalkenyl whic is substituted or unsubstituted, substituted phenylalkyl, substituted cycloalkyl-alkyl, substituted 5-membered heterocyclic ring, bicycloalkyl-alkyl orR.sup.4 and R.sup.5, together with the nitrogen atom, are a substituted or unsubstituted, saturated or unsaturated piperidine radical,their plant-tolerated salts and N-oxides, and fungicides containing these compounds.
    Type: Grant
    Filed: November 1, 1989
    Date of Patent: September 24, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Zipplies, Bernhard Zipperer, Hubert Sauter, Norbert Goetz, Franz Roehl, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5021453
    Abstract: Compounds of formula (I) and (II): ##STR1## are HMG-CoA reductase inhibitors.
    Type: Grant
    Filed: June 6, 1990
    Date of Patent: June 4, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Henry Joshua, Kenneth E. Wilson, Michael S. Schwartz, Ta J. Lee, Gerald E. Stokker
  • Patent number: 5021184
    Abstract: Described are adamantane derivatives defined according to the generic structure: ##STR1## wherein R.sub.1 ' is hydrogen or acetyl; R.sub.2 ' is hydrogen or lower alkyl and the dashed line is a carbon-carbon single bond or a carbon-carbon double bond as well as uses thereof for augmenting or enhancing the aroma or taste of consumable materials selected from the group consisting of perfume compositions, perfumed articles, colognes, smoking tobacco compositions, smoking tobacco articles, deodorizing articles, doedorizing compositions and malodor maskants.
    Type: Grant
    Filed: September 29, 1989
    Date of Patent: June 4, 1991
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William Gillaspey, Myrna L. Hagedorn, Marie R. Hanna, Kathleen E. Boardwick, Charles E. J. Beck, Futoshi Fujioka, Anthony G. Branco, Anubhav Narula, Richard M. Boden
  • Patent number: 5015761
    Abstract: Novel tricycloundecanones are disclosed having the general formula ##STR1## wherein R.sub.1, R.sub.2, and R.sub.3 are hydrogen or 1 to 3 carbon alkyl groups having a total carbon number of six or less. These compounds are useful perfumery ingredients characterized by odors of the woody type.Useful derivatives of the compounds are also disclosed as well as a novel procedure for preparation thereof.
    Type: Grant
    Filed: December 5, 1988
    Date of Patent: May 14, 1991
    Assignee: PFW(Nederland)B.V.
    Inventors: Willem Lenselink, Gerben Sipma
  • Patent number: 5010105
    Abstract: Compounds of Formula (I) and (II): ##STR1## are HMG-CoA reductase inhibitors.
    Type: Grant
    Filed: May 9, 1990
    Date of Patent: April 23, 1991
    Assignee: Merck & Co., Inc.
    Inventor: Ta J. Lee
  • Patent number: 4997848
    Abstract: Compounds of formula (I): ##STR1## in which: R represents hydrogen, methyl of hydroxy; X represents an alkyl, alkenyl, cycloalkyl, aryl, aralkyl, or heterocyclic group; A represents a single bond, or an alkylene, alkenylene, alkynylene or alkadienylene group; Y represents hydrogen, or an aryl, cycloalkyl or heterocyclic group] have valuable antihypercholesteremic activities and may be used in the treatment of disorders arising from a blood cholesterol imbalance in humans and other animals.
    Type: Grant
    Filed: October 21, 1988
    Date of Patent: March 5, 1991
    Assignee: Sankyo Company, Limited
    Inventors: Masaaki Kurabayashi, Hiroshi Kogen, Hiroshi Kadokawa, Hideshi Kurihara, Kazuo Hasegawa, Masao Kuroda
  • Patent number: 4985403
    Abstract: Described are adamantane derivatives defined according to the structure: ##STR1## wherein R.sub.1 is hydrogen or acetyl; R.sub.2 is hydrogen or methyl; and R.sub.3 is hydrogen or methylene (CH.sub.2) and wherein the dashed line represents a carbon-hydrogen single bond or a carbon-methylene double bond with the provisos that when R.sub.2 is methyl R.sub.1 and R.sub.3 are both hydrogen and when R.sub.2 is hydrogen, R.sub.3 is methylene and the dashed line is a carbon-methylene double bond and uses thereof in augmenting or enhancing the aroma of consumable materials selected from the group consisting of perfume compositions, colognes and perfumed articles.
    Type: Grant
    Filed: June 29, 1990
    Date of Patent: January 15, 1991
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, Charles E. J. Beck, Marie R. Hanna
  • Patent number: 4963292
    Abstract: The novel compound provided by the invention is a higher carboxylic acid triester of adamantane triol such as adamamtane-1,3,5-triol tricaprylate not known in the prior art. The compound has a high kinematic viscosity at elevated temperatures despite the low pour point and has high thermal stability in an oxidizing atmosphere so that it is useful as an ingredient of a high-performance lubricating oil.
    Type: Grant
    Filed: September 27, 1989
    Date of Patent: October 16, 1990
    Assignee: Idemitsu Kosan Company, Limited
    Inventors: Kosaku Honna, Hiromichi Seiki
  • Patent number: 4963585
    Abstract: The invention relates to a compound of antimicrobial activity of the formula ##STR1## wherein R.sup.1 is hydrogen or lower alkanoyl,R.sup.2 is hydrogen or ##STR2## in which R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are hydrogen or lower alkanoyl,R.sup.3 is carboxy or a protected carboxy, and pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: February 14, 1989
    Date of Patent: October 16, 1990
    Assignee: Fujisawa Pharmaceutical Company, Ltd.
    Inventors: Masanori Okamoto, Eisaku Tsujii, Tsutomu Kaizu, Hiroshi Hatanaka, Masakuni Okuhara, Kozo Sawada, Hirokazu Tanaka
  • Patent number: 4959349
    Abstract: Indane derivatives useful as fragrance-imparting components are disclosed. The represented indane derivatives by the formula (I), ##STR1## wherein ring A is a benzene or cyclohexane ring and R.sup.1 is a hydrogen atom, an alkyl group having 1-4 carbon atoms, or an alkanoyl group having 1-6 carbon atoms, provided that when ring A is benzene, R.sup.1 is a group other than hydrogen atom.
    Type: Grant
    Filed: February 23, 1990
    Date of Patent: September 25, 1990
    Assignee: KAO Corporation
    Inventors: Hiroaki Ohnuma, Yoshiaki Fujikura, Manabu Fujita, Nao Toi
  • Patent number: 4956124
    Abstract: Bicyclic decanedioic acids corresponding to the following general formula ##STR1## in which R represents a C.sub.1 -C.sub.22 alkyl radical, a C.sub.2 -C.sub.34 alkylcarbonyl radical, or a residue of a polyalkoxylated C.sub.2 -C.sub.22 fatty alcohol, represent a new class of dicarboxylic acids which are useful as flotation aids in the flotation of non-sulfidic ores.
    Type: Grant
    Filed: May 11, 1988
    Date of Patent: September 11, 1990
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Horst Eierdanz, Paul Schulz, Wolfgang von Rybinski, Rita Koester
  • Patent number: 4954524
    Abstract: Carbacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is hydrogen or OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, ##STR2## or a heterocyclic residue; or R.sub.1 is NHR.sub.3 wherein R.sub.3 is an acid residue (acyl) or R.sub.2,n is 2, 3, 4, or 5,X is hydrogen or fluorine,A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--,W is a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR3## wherein the OH-group can be in the .alpha.- or .beta.-position, D is ##STR4## a straight-chain, saturated aliphatic group of 1-10 carbon atoms, a branched, saturated or a straight-chain or branched, unsaturated aliphatic group of 2-10 carbon atoms, all of which can optionally be substituted by fluorine atoms,m is 1, 2, or 3,E is a direct bond, --C.tbd.C--, or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 are different from each other and are hydrogen or alkyl or 1-5 carbon atoms, or are hydrogen or halogen,R.sub.
    Type: Grant
    Filed: April 6, 1989
    Date of Patent: September 4, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Jorge Casals-Stenzel, Gerda Mannesmann, Ekkehard Schillinger, Michael H. Town
  • Patent number: 4929599
    Abstract: The bicyclic ester represented by the formula ##STR1## or 2-(2,3,4,5,6,7-hexahydro-1,1,4,4-tetramethyl-2(1H)-indenyl)-ethyl acetate, develops odor characters of the woody, slightly amber and musky type, and can therefore be advantageously used for the preparation of perfuming compositions or perfumes, and for perfuming products such as soaps, cosmetic preparations, detergents, fabric softeners or air deodorizers.
    Type: Grant
    Filed: April 12, 1989
    Date of Patent: May 29, 1990
    Assignee: Firmenich SA
    Inventors: Wolfgang K. Giersch, Karl-Heinrich Schulte-Elte
  • Patent number: 4927975
    Abstract: Novel antiandrogenic compositions comprising an antiandrogenically effective amount of at least one compound of the formula ##STR1## wherein R is alkyl of 1 to 4 carbon atoms, R.sub.1 is alkyl of 1 to 2 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms optionally interrupted with a heteroatom, alkenyl and alkynyl of 2 to 8 carbon atoms optionally interrupted with a heteroatom, formyl and acyl of an organic carboxylic acid of 2 to 18 carbon atoms, R.sub.3 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and alkenyl and alkynyl of 2 to 4 carbon atoms, R.sub.4 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, the dotted lines indicate optional presence of a double bond between the 4(5) and 5a(6) carbons and the wavy line indicates that R.sub.4 may be in the .alpha.- or .beta.
    Type: Grant
    Filed: July 25, 1988
    Date of Patent: May 22, 1990
    Assignee: Roussel Uclaf
    Inventors: Marie-Madeleine Bouton, Jean Jacques, Andre Pierdet
  • Patent number: 4895908
    Abstract: Novel esters and polyesters are prepared by reacting cyclopentadienylethanol, bis(2-hydroxyethyl)dicyclopentadiene, or mixtures of the two with monobasic acid esters and dibasic acid diesters. These esters and polyesters are characterized by a reversible cross-linking mechanism and have utility as superior coatings and adhesives. High molecular weight, cross-linked polymers are also prepared in the present invention by reacting cyclopentdienylethanol with a polyolefin wax having an ester, acid or anhydride functional group.
    Type: Grant
    Filed: December 30, 1988
    Date of Patent: January 23, 1990
    Assignee: Eastman Kodak Company
    Inventors: Jerome L. Stavinoha, Anthony W. McColllum
  • Patent number: 4886619
    Abstract: Compounds are provided which comprise a fluorocarbon terminal portion and a chiral hydrocarbon terminal portion, said terminal portions being connected by a central core, said compounds having tilted smectic mesophases or having latent tilted smectic mesophases which develop when said compounds having said latent mesophases are in admixture with said compounds having tilted smectic mesophases or said compounds having latent tilted smectic mesophases.
    Type: Grant
    Filed: May 29, 1987
    Date of Patent: December 12, 1989
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Eugene P. Janulis
  • Patent number: 4883816
    Abstract: Antihypertensive sulfonyl derivatives having the following formula are described: ##STR1## where R" is a C.sub.2 -C.sub.20 alkyl group,R".sub.1 is a C.sub.1 to C.sub.4 alkyl group,y is an integer from 2 to 10 andJ.sup.- is a pharmocologically acceptable anion.
    Type: Grant
    Filed: February 16, 1988
    Date of Patent: November 28, 1989
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Phaik E. Sum, Robert E. Schaub
  • Patent number: 4876399
    Abstract: The present invention is directed to novel taxols useful as a chemotherapeutic agent. Moreover, the present invention is directed to the process of preparing taxols and various intermediates in said process. A key intermediate is this process is 2,5-dihydroxy-2-patchoulenes. Therefore the present invention is also related to said intermediate and the process for its preparation.
    Type: Grant
    Filed: November 2, 1987
    Date of Patent: October 24, 1989
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Robert A. Holton, Rouh-Rong Juo, Richard Lowenthal
  • Patent number: 4874891
    Abstract: 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: Grant
    Filed: May 1, 1986
    Date of Patent: October 17, 1989
    Assignee: Washington University
    Inventors: Douglas F. Covey, Ricahrd J. Auchus
  • Patent number: 4866093
    Abstract: The dihydro-M-4 and dihydro-IsoM-4 hydroxy carboxylic acids of the formula (II): ##STR1## wherein one of R.sup.1 represents a hydrogen atom and the other represents a hydroxy group and wherein the structure shown as ##STR2## represents a structure of formula ##STR3## and the salts and esters of said acids. The invention also provides pharmaceutical compositions containing said acids, salts and/or esters which are useful for inhibiting cholesterol biosynthesis in the liver.
    Type: Grant
    Filed: March 19, 1984
    Date of Patent: September 12, 1989
    Assignee: Sankyo Company Limited
    Inventors: Akira Terahara, Minoru Tanaka
  • Patent number: 4855488
    Abstract: A process for the preparation of a dicyclopentenol ester of the formula: ##STR1## wherein R is a C.sub.1-12 alkyl group, a C.sub.6-12 aryl group or a C.sub.6-12 substituted aryl group is disclosed. In this process dicyclopentadiene is reacted with an organic carboxylic acid of the formula:R--CO--OHin the presence of a catalyst. The catalyst comprises a readily volatile addition compound of BF.sub.3.
    Type: Grant
    Filed: May 25, 1988
    Date of Patent: August 8, 1989
    Assignee: Huels Aktiengesellschaft
    Inventors: Fritz Gude, Hans Bellut
  • Patent number: 4853151
    Abstract: Dispirotetradecanes of the formula I ##STR1## wherein R.sup.1 and R.sup.2 are each independently of each other alkyl containing 1 to 12 carbon atoms wherein one or more non-adjacent CH.sub.2 groups may also be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--COO-- and/or --CH.dbd.CH-- (trans), one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, I, CN, NO.sub.2, NCS,A.sup.1 and A.sup.2 are each independently of each other trans-1,4-cyclohexylene wherein one or two non-adjacent CH.sub.2 groups may be replaced by --O-- and/or --S--, or 1,4-phenylene wherein one or more CH groups may also be replaced by N, with it also being possible optionally for A.sup.1 and A.sup.2 to be substituted laterally or axially by F, Cl, CN, CH.sub.3,Z.sup.1 and Z.sup.2 are each independently of each other --C--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or a single bond,m and n are each 0, 1 or 2,(m+n) 0, 1 or 2,X.sup.1, X.sup.2, X.sup.3 and X.sup.
    Type: Grant
    Filed: August 11, 1987
    Date of Patent: August 1, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankfter Haftung
    Inventors: Fritz Vogtle, Wolfgang Calaminus
  • Patent number: 4851436
    Abstract: Novel 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors which are useful as antihypercholesterolemic agents and are represented by the following general structural formulae (I) or (II): ##STR1## wherein: n is 1 to 5;R is hydrogen or ##STR2## R.sup.1 is hydrogen or methyl; R.sup.2 is hydrogen or methyl; andR.sup.3 is hydrogen, C.sub.1-5 alkyl or C.sub.1-5 alkyl substituted with a member of the group consisting of phenyl, dimethylamino, or acetylamino; andthe dotted lines at a, b and c represent optional double bonds and pharmaceutically acceptable salts of the compounds (II) in which R.sup.3 is hydrogen are disclosed.
    Type: Grant
    Filed: March 11, 1987
    Date of Patent: July 25, 1989
    Assignee: Merck & Co., Inc.
    Inventors: William F. Hoffman, Edward Scolnick, Robert L. Smith
  • Patent number: 4849454
    Abstract: Novel antiandrogenic compositions comprising an anti-androgenically effective amount of at least one compound of the formula ##STR1## wherein R is alkyl of 1 to 4 carbon atoms, R.sub.1 is alkyl of 1 to 2 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms optionally interrupted with a heteroatom, alkenyl and alkynyl of 2 to 8 carbon atoms optionally interrupted with a heteroatom, formyl and acyl of an organic carboxylic acid of 2 to 18 carbon atoms, R.sub.3 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and alkenyl and alkynyl of 2 to 4 carbon atoms, R.sub.4 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, the dotted lines indicate optional presence of a double bond between the 4(5) and 5a(6) carbons and the wavy line indicates that R.sub.4 may be in the .alpha.- or .beta.
    Type: Grant
    Filed: April 24, 1986
    Date of Patent: July 18, 1989
    Assignee: Roussel Uclaf
    Inventors: Marie-Madeleine Bouton, Jean Jacques, Andre Pierdet
  • Patent number: 4839340
    Abstract: The invention provides derivatives of bornane-3-spiro-1'-cyclopentane with woody note scent useful as a base component in perfumery formulations which comprises those having a substituting group selected from a methoxyl, ethoxyl, formyloxyl and acetoxyl groups or two of substituting groups being either a hydroxyl group and a methyl group or a hydroxyl group and an ethyl group at the 2-position synthesized by any of the reactions of borane-3-spiro-1'-cyclopentan-2--ol or bornane-3-spiro-1'-cyclopentan-2-one with any of the reagents selected in accordance with the substituting group(s) to be introduced.The invention also provides perfumery compositions containing the above.
    Type: Grant
    Filed: June 29, 1988
    Date of Patent: June 13, 1989
    Assignee: Kao Corporation
    Inventors: Yoshiaki Fujikura, Tomohito Kitsuki, Manabu Fujita, Nao Toi
  • Patent number: 4820865
    Abstract: Compounds of formula (I): ##STR1## wherein R.sup.1 represents a group of formula ##STR2## or a group of formula ##STR3## (wherein R.sup.2 represents a C.sub.1 --C.sub.10 alkyl group) and their corresponding free hydroxy-carboxylic acids and salts and esters of said acids may be prepared by the enzymatic hydroxylation of an MB-530B compound (which may be the lactone, the carboxylic acid or a salt or ester of MB-530B or a corresponding compound in which the 2-methylbutyryloxy group at the 1-position of these compounds has been replaced by another C.sub.2 --C.sub.11 acyloxy group), preferably using a microorganism of the genus Syncephalastrum, Mucor, Rhizopus, Zygorinchus, Circinella, Actinomucor, Gongronella, Phycomyces, Streptomyces, Absidia, Cunninghamella, Mortierella, Pycnoporus or Rhizoctonia, or a cell-free enzyme-containing extract from the microorganism.
    Type: Grant
    Filed: September 17, 1986
    Date of Patent: April 11, 1989
    Assignee: Sankyo Company, Limited
    Inventors: Akira Terahara, Minoru Tanaka
  • Patent number: 4812509
    Abstract: Novel esters and polyesters are prepared by reacting cyclopentadienylethanol, bis(2-hydroxyethyl)dicyclopentadiene, or mixtures of the two with monobasic acid esters and dibasic acid diesters. These esters and polyesters are characterized by a reversible cross-linking mechanism and have utility as superior coatings and adhesives. High molecular weight, cross-linked polymers are also prepared in the present invention by reacting cyclopentadienylethanol with a polyolefin wax having an ester, acid or anhydride functional group.
    Type: Grant
    Filed: September 28, 1987
    Date of Patent: March 14, 1989
    Assignee: Eastman Kodak Company
    Inventors: Jerome L. Stavinoha, Anthony W. McCollum
  • 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: 4738982
    Abstract: Novel 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors which are useful as antihypercholesterolemic agents and are represented by the following general structural formulae (I) or (II): ##STR1## and pharmaceutically acceptable salts thereof the compounds of the formula (II) in which R is hydrogen are disclosed.
    Type: Grant
    Filed: April 28, 1986
    Date of Patent: April 19, 1988
    Assignee: Merck & Co., Inc.
    Inventors: Byron H. Arison, Michael D. Greenspan, Joel B. Yudkovitz
  • Patent number: 4733003
    Abstract: Compounds of formula (I): ##STR1## [wherein X represents a hydrogen atom or a 2-methylbutyryl group, Y represents a hydrogen atom or a methyl group and R.sup.1 and R.sup.2 are the same or different and each represents an oxygen atom or a group of formula .dbd.N--OR.sup.3 (wherein R.sup.3 represents a hydrogen atom or an alkyl group)], the free hydroxy-carboxylic acids corresponding thereto and salts and esters of said acids may be prepared by oxidizing and, if necessary, oximating a corresponding ML-236A, ML-236B, MB-530A or MB-530B compound, and these compounds have valuable antihypercholesteraemic activity.
    Type: Grant
    Filed: May 6, 1986
    Date of Patent: March 22, 1988
    Assignee: Sankyo Company Limited
    Inventors: Junya Ide, Shigeki Muramatsu, Yoshio Tsujita, Msao Kuroda
  • 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: 4708963
    Abstract: Carbacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, a heterocyclic residue, or NHR.sub.3, wherein R.sub.3 is an acid residue or hydrogen;X is oxygen;A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--;W is free or functionally modified hydroxymethylene or free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position; D is a straight-chain or branched, saturated or unsaturated aliphatic group of 1-10 carbon atoms, which can optionally be substituted by fluorine atoms, 1,2-methylene, 1,1-trimethylene;E is --C.tbd.C-- or --CR.sub.6 .dbd.CH.sub.7 -- wherein R.sub.6 and R.sub.7 are hydrogen or alkyl of 1-5 carbon atoms;R.sub.4 is an aliphatic group, cycloalkyl, optionally substituted aryl, or a heterocyclic group;R.sub.5 is free or functionally modified hydroxy and,when R.sub.
    Type: Grant
    Filed: May 28, 1985
    Date of Patent: November 24, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Norbert Schwarz, Helmut Vorbruggen, Jorge Casals-Stenzel, Ekkehard Schillinger, Michael H. Town
  • 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: 4692464
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is (a) hydrogen, (b) C.sub.1-10 alkyl, (c) C.sub.1-10 alkyl substituted by halogen; C.sub.1-4 alkoxy; C.sub.6-10 aryl; C.sub.6-10 aryl substituted by 1-3 halogen atoms, a phenyl group, 1-3 C.sub.1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C.sub.1-4 alkoxy group; di-C.sub.1-4 -alkylamino; or tri-C.sub.1-4 -alkylammonium, (d) C.sub.4-10 cycloalkyl, (e) C.sub.4-10 cycloalkyl substituted by C.sub.1-4 alkyl, (f) C.sub.6-10 aryl, (g) C.sub.6-10 aryl substituted by 1-3 halogen atoms, a phenyl group 1-3 C.sub.1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C.sub.1-4 alkoxy group, or (h) an aromatic heterocycle of 5 or 6 ring atoms one of which is O, N or S;A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C--;W is hydroxymethylene, RO-methylene, CH.sub.3 or CH.sub.3, ##STR2## wherein OH or OR is in the .alpha.- or .beta.
    Type: Grant
    Filed: February 26, 1982
    Date of Patent: September 8, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Gerda Mannesmann, Wolfgang Losert, Jorge Casals
  • Patent number: 4681951
    Abstract: 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: Grant
    Filed: August 17, 1984
    Date of Patent: July 21, 1987
    Assignee: Sagami Chemical Research Center
    Inventors: Masakatsu Shibasaki, Toshiaki Mase, Mikiko Sodeoka, Yuji Ogawa
  • Patent number: 4673533
    Abstract: Described are oxobicyclononane derivatives and mixtures of same having the generic structure: ##STR1## wherein X, Y, X' and Y' each represents the moiety having one of the structures: ##STR2## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond with the proviso that when X' and Y' are each the moiety: ##STR3## then the dashed line at the "2-3" position is a carbon-carbon double bond and the dashed line at the "6-7" position is a carbon-carbon single bond and one of X or Y has the structure: ##STR4## and the other of X or Y has the structure: ##STR5## and with the further proviso that when X and Y are the moieties: ##STR6## then the dashed line at the "6-7" position is a carbon-carbon double bond and the dashed line at the "2-3" position is a carbon-carbon single bond and one of X' or Y' has the structure: ##STR7## and the other of X' or Y' has the structure: ##STR8## and wherein R represents hydrogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: June 27, 1986
    Date of Patent: June 16, 1987
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, John R. Helm
  • Patent number: 4668699
    Abstract: Novel 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors which are useful as antihypercholesterolemic agents and are represented by the following general structural formulae (I) or (II): ##STR1## wherein: n is 1 to 5;R is hydrogen or ##STR2## R.sup.1 is hydrogen or methyl; R.sup.2 is hydrogen or methyl; andR.sup.3 is hydrogen, C.sub.1-5 alkyl or C.sub.1-5 alkyl substituted with a member of the group consisting of phenyl, dimethylamino, or acetylamino; andthe dotted lines at a, b and c represent optional double bonds and pharmaceutically acceptable salts of the compounds (II) in which R.sup.3 is hydrogen are disclosed.
    Type: Grant
    Filed: August 5, 1985
    Date of Patent: May 26, 1987
    Assignee: Merck & Co., Inc.
    Inventors: William F. Hoffman, Robert L. Smith, Edward Scolnick
  • 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: 4608194
    Abstract: Described are oxobicyclononane derivatives having the generic structure: ##STR1## wherein R represents methyl or ethyl; wherein one of the dashed lines represents a carbon-carbon single bond or a carbon-carbon double bond; wherein N and P each represents 0 or 1 with the proviso that when N represents 1 the dashed line at the "2-3" position is a single bond with the sum of N and P being equal to 1 and uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes.
    Type: Grant
    Filed: August 8, 1985
    Date of Patent: August 26, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, John R. Helm
  • Patent number: 4607054
    Abstract: Novel antiandrogenic compositions comprising an antiandrogenically effective amount of at least one compound of the formula ##STR1## wherein R is alkyl of 1 to 4 carbon atoms, R.sub.1 is alkyl of 1 to 2 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms optionally interrupted with a heteroatom, alkenyl and alkynyl of 2 to 8 carbon atoms optionally interrupted with a heteroatom, formyl and acyl of an organic carboxylic acid of 2 to 18 carbon atoms, R.sub.3 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and alkenyl and alkynyl of 2 to 4 carbon atoms, R.sub.4 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, the dotted lines indicate optional presence of a double bond between the 4(5) and 5a(6) carbons and the wavy line indicates that R.sub.4 may be in the .alpha.- or .beta.
    Type: Grant
    Filed: October 19, 1983
    Date of Patent: August 19, 1986
    Assignee: Roussel Uclaf
    Inventors: Marie-Madeleine Bouton, Jean Jacques, Andre Pierdet
  • Patent number: 4584389
    Abstract: The compound 6(R)-[2-8(S)(2,2-dimethylbutyryloxy)-2(S),6(S)-dimethyl-1,2,3,4,4a(S),5,6, 7,8,8a(S)-decahydronaphthyl-1(S)ethyl]-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-p yran-2-one is prepared in two steps from mevinolin and comprise reduction of the two double bonds and C-methylation of the 8(S)-(2-methylbutyryloxy) group to form the 2,2-dimethylbutyryloxy group. The two steps can be performed in either order.
    Type: Grant
    Filed: May 23, 1985
    Date of Patent: April 22, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Meyer Sletzinger, Thomas R. Verhoeven, Ralph P. Volante
  • Patent number: 4582915
    Abstract: Mevinolin, compactin and dihydro- and tetrahydro derivatives thereof are converted to more active HMG-CoA reductase inhibitors by C-methylation of the natural 2(S)-methylbutyryloxy side chain to form a 2,2-dimethylbutyryloxy side chain.
    Type: Grant
    Filed: May 23, 1985
    Date of Patent: April 15, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Meyer Sleteinger, Thomas R. Verhoeven, Ralph P. Volante