Bicyclo Ring System Patents (Class 568/374)
  • Patent number: 6169212
    Abstract: The compounds of formula wherein the acetyl substituting group is either in position 2 or in position 3 of the cycle, or any mixture of compounds of formula (I) are novel compounds which can namely confer a natural odor of the leather type to products or compositions to which they are added.
    Type: Grant
    Filed: October 22, 1999
    Date of Patent: January 2, 2001
    Assignee: Firmenich SA
    Inventor: Wolfgang Klaus Giersch
  • Patent number: 6160184
    Abstract: The present invention provides a method of synthesizing compounds of ##STR1## wherein R and R' are independently (C.sub.1 -C.sub.4)alkyl.
    Type: Grant
    Filed: January 6, 2000
    Date of Patent: December 12, 2000
    Assignee: The Regents of the University of California
    Inventor: Trevor C. McMorris
  • Patent number: 6111144
    Abstract: A process for the preparation of a compound having the formula: ##STR1## in which a compound having the formula: ##STR2## is treated with a base and a silylating agent.
    Type: Grant
    Filed: August 20, 1998
    Date of Patent: August 29, 2000
    Assignee: Florida State University
    Inventors: Robert A. Holton, Phong Vu, Tawfik Gharbaoui, Vincent Reboul
  • Patent number: 6069283
    Abstract: The present invention provides illudin analogs of the general formula (I): ##STR1## where R.sub.1 is (CH.sub.2).sub.n --X--Y or H; n is 0 to 4; X is O or S or N or absent; and Y is an optionally substituted (C.sub.1 -C.sub.8)alkyl, (C.sub.6 -C.sub.10)aryl, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.4)alkyl or cyclo(C.sub.3 -C.sub.6)alkyl optionally comprising one or more heteroatoms; a monosaccharide, an amino acid residue, or H when n is 2-4;R.sub.2 is absent; or R.sub.1 and R.sub.2 together comprise a 5-7 membered cyclic ring;R.sub.3 is (C.sub.1 -C.sub.4)alkyl or H; R.sub.4 is H, SCH.sub.2 CO.sub.2 (C.sub.1 -C.sub.4)alkyl, O--(C.sub.5 -C.sub.12)aryl or --S--(C.sub.5 -C.sub.12)aryl; R.sub.5 is H, OH or absent; R.sub.6 is (C.sub.1 -C.sub.4)alkyl or absent; R.sub.7 is OH or OSi((C.sub.1 -C.sub.4)alkyl).sub.3 ; orR.sub.6 and R.sub.7 together are ethylenedioxy;R.sub.8 is optionally substituted (C.sub.1 -C.sub.4)alkyl; andthe bonds represented by ----- are individually present or absent.
    Type: Grant
    Filed: February 1, 1999
    Date of Patent: May 30, 2000
    Assignee: The Regents of the University of California
    Inventors: Trevor C. McMorris, Michael J. Kelner
  • Patent number: 6030962
    Abstract: This invention provides Vitamin D.sub.3 analogs of the Formula I ##STR1## wherein: X is H.sub.2 or CH.sub.2 ;Y is hydrogen, hydroxy or fluorine;Z is hydroxy;R.sub.1 and R.sub.2 are a (C.sub.1 -C.sub.4) alkyl or fluoroalkyl, or R.sub.1 and R.sub.2 together with C.sub.25 form a (C.sub.3 -C.sub.6) cycloalkyl or cyclofluoroalkyl;R.sub.3 and R.sub.4 are a (C.sub.1 -C.sub.4) alkyl or fluoroalkyl, or R.sub.3 and R.sub.4 together with C.sub.25, form a (C.sub.3 -C.sub.6)cycloalkyl or cyclofluoroalkyl;A is a single bond or a double bond;B.sub.1 is a single bond, an E-double bond, a Z-double bond or a triple bond; andB.sub.2 is a single bond, an E-double bond, a Z-double bond or a triple bond; and prodrugs thereof, intermediates and methods for preparation of these analogs, pharmaceutical compositions containing such analogs and methods for treatment of osteoporosis, hyperparathyroidism and autoimmune diseases.
    Type: Grant
    Filed: April 16, 1998
    Date of Patent: February 29, 2000
    Assignee: Synttex (U.S.A.) Inc.
    Inventors: Percy Sarwood Manchand, Milan Radoje Uskokovic
  • Patent number: 6025328
    Abstract: The present invention provides illudin analogs of the general formula I: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, as well as pharmaceutical compositions comprising compounds of formula I, intermediates and processes useful for preparing compounds of formula I, and methods comprising inhibiting tumor growth or treating cancer by administering one or more compounds of formula I.
    Type: Grant
    Filed: February 20, 1998
    Date of Patent: February 15, 2000
    Assignee: The Regents of the University of California
    Inventors: Trevor C. McMorris, Michael J. Kelner
  • Patent number: 5972341
    Abstract: Extracts of the plant Commiphora mukul are used as pigmenting agents and melanocyte culture agents, and for the manufacture of cosmetic and pharmaceutical compositions. Particularly preferred are extracts of the formula IIa, designated Commipherol, and abstracts of the formula IIb designated Commipherin.
    Type: Grant
    Filed: May 20, 1998
    Date of Patent: October 26, 1999
    Assignee: Parfums Christian Dior
    Inventors: Patrice Andre, Stephane Lhermite, Fran.cedilla.oise Pellicier
  • Patent number: 5948933
    Abstract: New tropane analogs that bind to monoamine transporters are described, particularly, 8-aza, 8carbo and 8-oxo tropanes having 6- or 7-substituents. The compounds of the present invention can be racemic, pure R-enantiomers, or pure S-enantiomers. Certain preferred compounds of the present invention have a high selectivity for the DAT versus the SERT. Also described are pharmaceutical therapeutic compositions comprising the compounds formulated in a pharmaceutically acceptable carrier and a method for inhibiting 5-hydroxy-tryptamine reuptake of a monoamine transporter by contacting the monoamine transporter with a 5-hydroxytryptamine reuptake inhibiting amount of a compound of the present invention. Preferred monoamine transporters for the practice of the present invention include the dopamine transporter, the serotonin transporter and the norepinephrine transporter.
    Type: Grant
    Filed: July 11, 1997
    Date of Patent: September 7, 1999
    Assignees: Organix, Inc., President and Fellows of Harvard College
    Inventors: Peter C. Meltzer, Bertha K. Madras, Paul Blundell, Zhengming Chen
  • Patent number: 5932553
    Abstract: The present invention provides illudin analogs of the general formula (I): ##STR1## where R.sub.1 is (CH.sub.2).sub.n --X--Y or H; n is 0 to 4; X is O or S or N or absent; and Y is an optionally substituted (C.sub.1 -C.sub.8)alkyl, (C.sub.6 -C.sub.10)aryl, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.4)alkyl or cyclo(C.sub.3 -C.sub.6)alkyl optionally comprising one or more heteroatoms; a monosaccharide, an amino acid residue, or H when n is 2-4; R.sub.2 is absent; or R.sub.1 and R.sub.2 together comprise a 5-7 membered cyclic ring;R.sub.3 is (C.sub.1 -C.sub.4)alkyl or H; R.sub.4 is H, SCH.sub.2 CO.sub.2 (C.sub.1 -C.sub.4)alkyl, O--(C.sub.5 --C.sub.12)aryl or --S--(C.sub.5 -C.sub.12)aryl; R.sub.5 is H, OH or absent; R.sub.6 is (C.sub.1 -C.sub.4)alkyl or absent; R.sub.7 is OH or OSi((C.sub.1 -C.sub.4)alkyl).sub.3 ; orR.sub.6 and R.sub.7 together are ethylenedioxy;R.sub.8 is optionally substituted (C.sub.1 -C.sub.4)alkyl; andthe bonds represented by -- are individually present or absent.
    Type: Grant
    Filed: July 18, 1996
    Date of Patent: August 3, 1999
    Assignee: The Regents of the University of California
    Inventors: Trevor C. McMorris, Michael J. Kelner
  • Patent number: 5929291
    Abstract: The invention relates to compounds of the general formula ##STR1## in which R.sup.1 to R.sup.7 are, independently, H, methyl or ethyl, R.sup.8 +R.sup.9 together form methylene (--CH.sub.2 --) or a single bond, or R.sup.1 +R.sup.2 together form --(CH.sub.2).sub.n --, with n being 3 or 4, or R.sup.3 +R.sup.5 or R.sup.5 +R.sup.7 represent methylene or a single bond; and the presence of at least one cyclopropane ring in the molecule is compulsory and the side chain can be saturated or contains one double bond in position .alpha.,.beta. or .beta., .gamma. a process for the manufacture of these compounds, compounds used to perform the process and the use of these compounds as an odorant or as an ingredient of an odorant composition.
    Type: Grant
    Filed: April 9, 1997
    Date of Patent: July 27, 1999
    Assignee: Givaudan Roure (International) SA
    Inventors: Jerzy A. Bajgrowicz, Georg Frater
  • Patent number: 5892124
    Abstract: Improved process for implementing the Diels-Alder reaction that consists in using reagents in the presence of at least one liquid salt of general formula Q.sup.+ A.sup.-, in which Q.sup.+ represents a quaternary ammonium and/or phosphonium and A.sup.- represents an anion and optionally at least one Lewis acid. The anion is preferably selected from the group that is formed by tetrafluoroborate, hexafluorophosphate, hexafluoroantimonate, hexafluoroarsenate, perfluoroalkylsulfonate, fluorosulfonate or else dichlorocuprate, tetrachloroborate, tetrachloroaluminate, and trichlorozincate. At the end of the reaction, the organic phase is separated, and the polar phase is reused.
    Type: Grant
    Filed: December 29, 1997
    Date of Patent: April 6, 1999
    Assignee: Institut Fran.cedilla.ais du Petrole
    Inventors: Helene Olivier, Andre Hirschauer
  • Patent number: 5872113
    Abstract: Fluorinated Vitamin D.sub.3 analogs, intermediates for their preparation, compositions comprising the analogs and methods of treatment of osteoporosis and related conditions with these and related analogs are provided.
    Type: Grant
    Filed: May 16, 1997
    Date of Patent: February 16, 1999
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: John J. Nestor, Jr., Percy S. Manchand, Milan R. Uskokovic, Brian H. Vickery
  • Patent number: 5856580
    Abstract: The present invention provides a method of synthesizing compounds of formula (I): ##STR1## wherein R and R' are independently (C.sub.1 -C.sub.4)alkyl.
    Type: Grant
    Filed: October 31, 1997
    Date of Patent: January 5, 1999
    Assignee: The Regents of University of California
    Inventor: Trevor C. McMorris
  • Patent number: 5834404
    Abstract: The present invention is directed to substituted bicycloheptanedion e derivatives represented by a general formula ?I!; ##STR1## wherein R represents C.sub.1 -C.sub.4 alkyl, R.sup.1 represents hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, aralkyl, C.sub.2 -C.sub.4 haloalkynyl, C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 haloalkenyl, etc. and R.sup.2 represents optionally substituted phenyl or optionally substituted pyridyl, the salts thereof and herbicides comprising the same as the active ingredient.
    Type: Grant
    Filed: July 15, 1997
    Date of Patent: November 10, 1998
    Assignee: Nippon Soda Co., ltd.
    Inventors: Takahiro Sagae, Masao Yamaguchi, Hiroyuki Adachi, Kazuyuki Tomida, Akihiro Takahashi, Takashi Kawana
  • Patent number: 5730960
    Abstract: The use of a benzylidenenorcamphor compound of the formula I ##STR1## wherein Phe is a phenyl group which is unsubstituted or substituted by 1 to 5 hydroxyl, alkyl or alkoxy groups having 1 to 10 C atoms, andn is 1 or 2.as sunscreen filters,and also novel compounds of the formula I, their preparation and use as UV filters, in particular in cosmetic or pharmaceutical preparations.
    Type: Grant
    Filed: July 21, 1995
    Date of Patent: March 24, 1998
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Inge Stein, Michael Schwarz, Ulrich Heywang, Michael Kompter
  • Patent number: 5707961
    Abstract: The invention is concerned with novel odorants, including the compounds of the formula ##STR1## wherein R.sup.1 .dbd.R.sup.4 .dbd.CH.sub.3 and R.sup.2 .dbd.R.sup.3 .dbd.H orR.sup.1 .dbd.R.sup.2 .dbd.R.sup.3 .dbd.H and R.sup.4 .dbd.CH.sub.3, orR.sup.1 +R.sup.2 .dbd.--CH.sub.2 CH.sub.2 -- and R.sup.3 .dbd.H and R.sup.4 .dbd.CH.sub.3, orR.sup.1 .dbd.R.sup.4 .dbd.CH.sub.3 and R.sup.2 +R.sup.3 .dbd.--CH.sub.2 -- orR.sup.1 .dbd.CH.sub.3 and R.sup.2 .dbd.R.sup.3 .dbd.H and R.sup.4 .dbd.CH.sub.2 CH.sub.3 orR.sup.1 .dbd.R.sup.2 .dbd.R.sup.4 .dbd.CH.sub.3 and R.sup.3 .dbd.H and R.sup.5 .dbd.H (preferred) or CH.sub.3.
    Type: Grant
    Filed: April 25, 1996
    Date of Patent: January 13, 1998
    Assignee: Givaudan-Roure (International) SA
    Inventors: Jerzy A. Bajgrowicz, Alain Bringhen, Georg Frater, Urs Muller
  • Patent number: 5581004
    Abstract: The magnesium complexes of cyclic hydrocarbons and conjugated dienes, such as 1,2-dimethylenecycloalkanes and 1,3-butadienes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4-diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, alkylditriflates, bromoalkylnitriles, esters, or amides serve as a convenient method for synthesizing carbocyclic systems. Significantly, carbocycles prepared by this method contain functional groups such as the exocyclic double bond or a keto group in one of the rings which could be used for further elaboration of these molecules. Furthermore, fused bicyclic systems containing a substituted five-membered ring can be conveniently prepared at high temperatures by the reactions of (2-butene-1,4-diyl)magnesium complexes with carboxylic esters or acid halides whereas low temperatures lead to regioselective synthesis of .beta.,.gamma.-unsaturated ketones. Additionally, .gamma.-lactones, including spiro .
    Type: Grant
    Filed: October 17, 1994
    Date of Patent: December 3, 1996
    Assignee: Board of Regents of the University of Nebraska
    Inventor: Reuben D. Rieke
  • Patent number: 5563176
    Abstract: Antineoplastic illudin analogs are provided of the formula: wherein R.sub.4, R.sub.5 and R.sub.6 are (C.sub.1 -C.sub.4)alkyl, Y is H, (C.sub.1 -C.sub.3)alkyl, (R.sub.4)R.sub.5)(R.sub.6)Si or alkanoyl ((C.sub.1 -C.sub.4)alkylC(O)) and R is CH.sub.2 OH, halo, benzyl optionally substituted with OY, or alkanoylmethyl (CH.sub.2 OC(O)R.sub.7), wherein R.sub.7 is (C.sub.1 -C.sub.4)alkyl, (C.sub.6 -C.sub.2)aryl or N(X).sub.2, wherein each X is H or (C.sub.1 -C.sub.4)alkyl, and the pharmaceutically-acceptable salts thereof.
    Type: Grant
    Filed: July 15, 1994
    Date of Patent: October 8, 1996
    Assignee: The Regents of the University of California
    Inventors: Michael J. Kelner, Trevor C. McMorris, Raymond Taetle
  • Patent number: 5523490
    Abstract: A compound to inhibit tumor cell growth in a subject in need of said therapy is provided, wherein said compound has the structure: ##STR1## wherein R is selected from the group consisting of: ##STR2## Tumor cells sensitive to inhibition by said compound are selected from the group consisting of a myeloid leukemia cell, a T-cell leukemia cell, a lung carcinoma cell, an ovarian carcinoma cell, and a breast carcinoma cell.
    Type: Grant
    Filed: November 1, 1994
    Date of Patent: June 4, 1996
    Assignee: The Regents of the University of California
    Inventors: Michael J. Kelner, Trevor C. McMorris, Raymond Taetle
  • Patent number: 5498734
    Abstract: The magnesium complexes of cyclic hydrocarbons containing conjugated dienes, such as 1,2-dimethylenecycloalkanes, and 1,3-butadienes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4 diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, alkylditriflates, bromoalkylnitriles, esters, or amides serve as a convenient method for synthesizing carbocyclic systems. Significantly, carbocycles prepared by this method contain functional groups such as the exocyclic double bond or a keto group in one of the rings which could be used for further elaboration of these molecules. Furthermore, fused bicyclic systems containing a substituted five-membered ring can be conveniently prepared at high temperatures by the reactions of (2-butene-1,4-diyl)magnesium complexes with carboxylic esters or acid halides whereas low temperatures lead to regioselective synthesis of .beta.,.gamma.-unsaturated ketones. Additionally, .gamma.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: March 12, 1996
    Assignee: University of Nebraska
    Inventor: Reuben D. Rieke
  • Patent number: 5468905
    Abstract: Compounds represented by general formulas (I) and (II), useful as the intermediates for agricultural chemicals, particularly herbicidal compounds, wherein R.sup.1 and R.sup.2 represent each hydrogen, alkyl or COOR.sup.3 :R.sup.3 represents alkyl: and R.sup.4 represents alkyl.
    Type: Grant
    Filed: May 25, 1994
    Date of Patent: November 21, 1995
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Junji Suzuki, Masami Hatano, Shinichi Imaizumi
  • Patent number: 5441987
    Abstract: A compound having the formula ##STR1## which is useful as an antifungal agent and for the treatment and control of several agricultural phytopathogens, including Phytophthora infestans, is disclosed.
    Type: Grant
    Filed: August 12, 1994
    Date of Patent: August 15, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Guy H. Harris, James E. Curotto, Robert A. Giacobbe, Suzanne M. Mandala, Richard L. Monaghan, Richard K. Jansson, Joan A. Lasota
  • Patent number: 5437686
    Abstract: Bleaching compositions comprising an inorganic peroxygen compound and a bicyclic or tricyclic diketone as an activator for the peroxygen compound. The composition preferably comprises about 1 to about 75% of the peroxygen bleaching compound and about 1 to about 75% of the bicyclic or tricyclic diketone bleaching compound activator. The conventional additives such as surfactants, antifoaming agents, fabric softeners, stablizers, inorganic builder salts, buffers, enzymes and the like may be present as indicated. The compositions can be formulated as dry concentrated, aqueous solutions, aqueous solutions containing non-aqueous solvents, etc. The compositions are environmentally safe, effective as bleaching agents from below room temperature to higher temperatures, biodegradable and otherwise highly desirable.
    Type: Grant
    Filed: May 18, 1994
    Date of Patent: August 1, 1995
    Assignee: Colgate-Palmolive Co.
    Inventors: Robert J. Heffner, Robert J. Steltenkamp
  • Patent number: 5430196
    Abstract: A synthesis of 1.alpha.-hydroxy-19-nor-vitamin D compounds comprises (a) the construction of a 5,8-diol-6-yne intermediate by joining ring-A and ring-C/D portions of the desired end product via the condensation of an acetylenic derivative containing the C/D-ring portion of the desired end product with a cyclic dihydroxy ketone representing the A-ring of the desired end product; (b) the partial reduction of the 6,7 acetylenic triple bond linkage between the A and C/D ring potions to obtain a 5,8-diol-6-ene intermediate; and (c) the reductive removal of the 5,8-oxygen functions to generate the required 5,7-diene end product from which the desired 7-trans(7E)-isomer is purified directly, or after optional double bond isomerization of the 7-cis(7Z)-isomer employing a novel thiophenol-promoted isomerization step.
    Type: Grant
    Filed: September 8, 1994
    Date of Patent: July 4, 1995
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Fariba Aria
  • Patent number: 5354915
    Abstract: This invention provides an improved process for converting .alpha.,.beta.-olefinically unsaturated aldehydic or ketonic compounds into the corresponding allylic alcohol using an alcohol as a hydrogen donor. This process is conducted in the presence of a supported tetragonal zirconium oxide catalyst or supported HfO.sub.2, V.sub.2 O.sub.5, NbO.sub.5, TiO.sub.2 and Ta.sub.2 O.sub.5 catalysts.
    Type: Grant
    Filed: December 21, 1992
    Date of Patent: October 11, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Walter T. Reichle
  • Patent number: 5283349
    Abstract: A 2,6,7-trisubstituted-3-methylenebicyclo-[3.3.0]octane of formula (I) or an enantiomer thereof, or a mixture of these in an arbitrary ratio. The compound is a key intermediate for preparation of isocarbacyclins which are useful as medicines for the circulatory system such as an antithrombotic agent, an antilipidemic agent, a hypotensive agent or an antiarterosclerotic agent.
    Type: Grant
    Filed: September 11, 1986
    Date of Patent: February 1, 1994
    Assignee: Teijin Limited
    Inventors: Toshio Tanaka, Kiyoshi Bannai, Seizi Kurozumi
  • Patent number: 5276055
    Abstract: Compounds having the formula ##STR1## wherein R and R.sup.1 may be H or COCH.sub.3 provided that when R.sup.1 is COCH.sub.3, R is COCH.sub.3 are described.
    Type: Grant
    Filed: October 19, 1992
    Date of Patent: January 4, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Angeles Cabello, Guy Harris, Robert A. Giacobbe, Gregory L. Helms, Otto D. Hensens, Suzanne M. Mandala, E. Tracy T. Jones, Isabel Martin, Walter Rozdilsky
  • Patent number: 5266600
    Abstract: The present invention provides BU-4641V of the formula: ##STR1## This invention also provides a biologically pure culture of BU-4641V producing Arthrinium sp. FA1744. Another aspect of the invention provides a process for preparing BU-4641V. Yet further aspect of the present invention provides a method for treating mammalian tumors and bacterial or viral infections.
    Type: Grant
    Filed: October 30, 1992
    Date of Patent: November 30, 1993
    Assignee: Bristol-Myers Squibb Company
    Inventors: Osamu Tenmyo, Yosuke Sawada, Toshikazu Oki, Masahisa Oka, Masaru Sugawara, Noriyuki Ohkusa
  • Patent number: 5231205
    Abstract: The magnesium complexes of cyclic hydrocarbons, such as 1,2-dimethylenecycloalkanes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4-diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, or bromoalkylnitriles serve as a convenient method for synthesizing spirocyclic systems. Significantly, spirocarbocycles prepared by thisThe present invention was made with Government support under Contract No. GM35153 awarded by the National Institute of Health. The Government has certain rights in the invention.
    Type: Grant
    Filed: September 23, 1991
    Date of Patent: July 27, 1993
    Assignee: Board of Regents of the University of Nebraska
    Inventor: Reuben D. Rieke
  • Patent number: 5180709
    Abstract: The invention concerns novel odorants of formula I wherein R is hydrogen or methyl. ##STR1## The invention also concerns fragrance compositions containing I. Formula I is intended to particularly embrace as the racemates, (.+-.)-3.alpha.-acetyl-3.beta.,4.beta.,5,5-tetramethyl-2,3,4,4a.beta.,5,6, 7,8-octahydronapthalene and (.+-.)-3.alpha.-acetyl-4.beta.,5,5-trimethyl-2,3.beta.,4,4a.beta.,5,6,7,8- octahydronapthalene.
    Type: Grant
    Filed: May 31, 1991
    Date of Patent: January 19, 1993
    Assignee: Givaudan-Roure Corporation
    Inventors: Franz Etzweiler, Daniel Helmlinger, Cornelius Nussbaumer, Mario Pesaro
  • Patent number: 5163453
    Abstract: The invention concerns the novel compound 3,5,5,6,8,8,-hexamethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalenone, a process for its manufacture, and fragrance and flavor compositions containing same.
    Type: Grant
    Filed: January 18, 1990
    Date of Patent: November 17, 1992
    Assignee: Givaudan Corporation
    Inventors: Jean-Pierre Bachmann, Mario Pesaro
  • Patent number: 5164365
    Abstract: The present invention concerns the novel odorant 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone, I, a process for the manufacture of I, novel intermediates used in the process and fragrance compositions containing I. ##STR1## The process for the manufacture of 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone comprises hydroborating 1,1,2,3,3,6-hexamethyl-4,7-dihydroindane and oxidizing the hydroboration product to 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone, or reductively alkylating, especially methylating, 5-nitro-1,1,2,3,3,6-hexamethylindane and converting the resulting 5-dialkyl-amino-1,1,2,3,3,6-hexamethylindane into 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone by reduction of the benzene ring and hydrolysis of the resulting enamine.
    Type: Grant
    Filed: February 26, 1991
    Date of Patent: November 17, 1992
    Assignee: Givaudan Corporation
    Inventors: Jean-Pierre Bachmann, Daniel Helmlinger, Mario Pesaro
  • Patent number: 5149846
    Abstract: The invention is directed to deuterated vitamin D analogs, and processes and intermediates for their preparation. The end products, that is the deuterated vitamin D analogs, are useful for the treatment osteoporosis and cutaneous inflammations such as psoriasis, and contact dermatitis.
    Type: Grant
    Filed: November 16, 1989
    Date of Patent: September 22, 1992
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Enrico G. Baggiolini, Bernard M. Hennessy, Milan R. Uskokovic
  • Patent number: 5137869
    Abstract: Described is the methyl substituted tetrahydroindanone having the structure: ##STR1## 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: September 13, 1991
    Date of Patent: August 11, 1992
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, Eleanor Fox, Alphonsus P. M. Maas, Djurre S. Postma
  • Patent number: 5131945
    Abstract: Compounds of formula I ##STR1## are useful as herbicides, effective against dicotyledonous weeds.
    Type: Grant
    Filed: July 13, 1990
    Date of Patent: July 21, 1992
    Assignee: Shell Research Limited
    Inventors: Hans-Joachim Bissinger, Ludwig Schoeder, Helmut Baltruschat, Manfred Garrecht, Erich Raddatz, Wolfgang Fruhstorfer
  • Patent number: 5118856
    Abstract: A process for the preparation of cyclohexanedione derivatives of the general formula I ##STR1## where R.sup.1 is C.sub.2 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.5 -C.sub.12 -cycloalkyl with 0-4 olefinically unsaturated bonds, C.sub.2 -C.sub.8 -alkylthioalkyl, C.sub.6 -C.sub.12 -bicycloalkyl with 0-3 olefinically unsaturated bonds, unsubstituted or substituted aryl or hetaryl, or a heterocyclic radical of 4 to 7 atoms of which not more than 3 may be hetero-atoms chosen from O, S and N, the radical being saturated or olefinically unsaturated, by reacting an .alpha.,.beta.-unsaturated ketone (II) with a dialkyl malonate in the presence of a base to give the alkoxycarbonylcyclohexenolone or its salt (III) ##STR2## and acylation, hydrolysis and decarboxylation of (III), wherein the .alpha.,.beta.
    Type: Grant
    Filed: August 2, 1990
    Date of Patent: June 2, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Gernot Reissenweber, Winfried Richarz
  • Patent number: 5114960
    Abstract: Compounds of the formula ##STR1## wherein A taken together with the two carbon atoms denoted as .alpha. and .beta. is a group of the formula ##STR2## and the dotted line is the double bond present in formulas (i) and (iii); and wherein n is zero, 1, 2 or 3, one of R.sup.1 and R.sup.2 is carboxy or alkoxycarbonyl and the other is hydrogen, R.sup.3 is hydrogen, alkyl, alkoxy, aryloxy, azido, cyano or alkylthio, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 each, independently, is hydrogen or alkyl or, when R.sup.1 is carboxy or alkoxycarbonyl and n stands for 1, R.sup.4 and R.sup.6 taken together can be a carbon-carbon bond or, when R.sup.2 is carboxy or alkoxycarbonyl, R.sup.5 and R.sup.7 taken together can be a carbon-carbon bond, R.sup.8 is halogen, alkyl, haloalkyl or alkoxy and R.sup.9 is hydrogen, halogen, alkyl or alkoxy, and pharmaceutically acceptable salts of the compounds of formula I in which one of R.sup.1 and R.sup.
    Type: Grant
    Filed: June 26, 1990
    Date of Patent: May 19, 1992
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Geoffrey Lawton, John M. Osbond, Christopher R. Self
  • Patent number: 5084592
    Abstract: Azulenesquaric acid dyes of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each have specified meanings are prepared from azulene derivatives of the formula ##STR2## where R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each have specified meanings as intermediates, and used in an optical recording medium.
    Type: Grant
    Filed: September 30, 1988
    Date of Patent: January 28, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Schrott, Peter Neumann, Sibylle Brosius, Helmut Barzynski, Klaus D. Schomann, Harald Kuppelmaier
  • Patent number: 5077275
    Abstract: Described are acylated bicycloalkadiene-compound-containing compositions of matter, mixtures of compounds containing predominantly compounds having the structures: ##STR1## with the compositions of matter containing from 50 up to 100% of the compound having the structure: prepared by reacting the compound having the structure: ##STR2## or a mixture containing, predominently, the compound having the structure: with acetic anhydride in the presence of a Lewis acid catalyst such as boron trifluoride etherate.Also described are perfumery uses of such compositions of matter for augmenting or enhancing the aroma of perfume compositions, colognes or perfumed articles such as solid or liquid anionic, cationic, nonionic or zwitterionic detergents, cosmetic powders, hair preparations and the like.
    Type: Grant
    Filed: May 17, 1991
    Date of Patent: December 31, 1991
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Joseph A. McGhie
  • Patent number: 5077274
    Abstract: Described is the novel compound, bicyclo[10.2.0]tetradecan-13-one having the structure: ##STR1## as well as the use thereof in augmenting or enhancing the aroma of consumable materials including perfume compositions, colognes and perfumed articles (including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, cosmetic powders and hair preparations). Also described is a process for preparing said bicyclo[10.2.
    Type: Grant
    Filed: October 12, 1990
    Date of Patent: December 31, 1991
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William J. Evers, Howard H. Heinsohn, Jr.
  • Patent number: 5030739
    Abstract: The invention is directed to a process for the catalytic oxidation of an isoprenoid containing at least one allylic hydrogen atom, which process comprises reacting the isoprenoid with oxygen or an oxygen-containing gas in an inert solvent in the presence of a N-hydroxydicarboxylic acid imide of the formula ##STR1## wherein A-B stands for CH.sub.2 -CH.sub.2, CH.dbd.CH, an aromatic hydrocarbon residue or a group derived from one of these groups in which one or more hydrogen atoms is/are replaced by alkyl or halogen,to produce a primary of secondary hydroperoxide.The process of the invention is suitable for the manufacture of steroids, vitamins, odorant substances, carotinoids and the like.
    Type: Grant
    Filed: August 31, 1990
    Date of Patent: July 9, 1991
    Assignee: Hoffman-La Roche Inc.
    Inventors: Joseph Foricher, Claude Furbringer, Karlheinz Pfoertner
  • Patent number: 5019590
    Abstract: A process for synthesizing oxygen-containing polyoxatetracycle compounds and in particular analogs of the antimalarial agent known as qinghaosu or artemisinin is disclosed. The process employs as a reactant an olefinically unsaturated bicyclic bridging ketone having nonenolizable bridgehead moieties for both of its alpha positions. This ketone is converted to a vinylsilane that is subjected to ozonolytic cleavage of its olefinic bond to yield a member of a family of unique carboxyl/carbonyl-substituted vinylsilanes which may in turn optionally be subjected to a wide range of reactions prior to a final ozonolysis/acidification step which closes the oxygen-containing ring structure. The various intermediates are claimed as aspects of this invention as are novel tetracycles and their use as antimalarials.
    Type: Grant
    Filed: September 27, 1989
    Date of Patent: May 28, 1991
    Assignee: SRI International
    Inventors: Mitchell A. Avery, Wesley K. M. Chong
  • Patent number: 5002929
    Abstract: Certain trimethylbicylo-[4.3.0]-nonane derivatives, particularly those having a single acetyl substituent on the six membered ring, are novel compounds useful as perfumes to give highly persistent iris butter, methyl ionone, tobacco, and wood odor notes.
    Type: Grant
    Filed: October 12, 1989
    Date of Patent: March 26, 1991
    Assignee: Henkel Kommadnitgesellschaft auf Aktien
    Inventors: Klaus Bruns, Thomas Gerke, Ursula Schmitz
  • Patent number: 4971987
    Abstract: The invention also relates to carbacyclin derivatives of general formula I' ##STR1## wherein R.sub.9 is an alkyl group of 1-10 carbon atoms or the group --C.dbd.C--(CH.sub.2).sub.m --R.sub.6 whereinm is 1 to 16 andR.sub.6 is hydroxy on amino.
    Type: Grant
    Filed: March 7, 1988
    Date of Patent: November 20, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbrueggen, Bob Nieuweboer, Claus-Steffen Stuerzebecher, Ulrich Klar
  • Patent number: 4943384
    Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 are each H or an alkyl group which has 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-groups, and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, or are F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --Z.sup.o --A-- or --A--Z.sup.o --A.sup.4 --,A is a trans-1,4-cyclohexylene or 1,4-cyclohexenylene group which is unsubstituted or is monosubstituted or polysubstituted in the 2-, 3-, 5- and/or 6-position by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group each of which has 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, which trans-1,4-cyclohexylene or 1,4-cyclohexenylene group can optionally also be substituted in the 1-position and/or 4-position and one or two CH.sub.
    Type: Grant
    Filed: November 21, 1986
    Date of Patent: July 24, 1990
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Wolfgang Sucrow, Herbert Wolter, Rudolf Eidenschink
  • Patent number: 4927963
    Abstract: A process for preparing compounds represented by the formula ##STR1## wherein: X is hydrogen or lower alkoxy;Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl);n is an integer from 2-4;R.sub.2 is hydrogen or methyl; andR.sub.3 is linear or branched alkyl, ##STR2## --(CH.sub.2).sub.m -phenyl or --CH.sub.2 O-phenyl; in which any phenyl may be optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen, anda is an integer of 0, 1 or 2;b is an integer of 3-7;m is an integer of 0, 1 or 2,as a mixture or separately in a sequence starting from an epoxide represented by the formula ##STR3## and processes for making the novel intermediates.
    Type: Grant
    Filed: April 28, 1989
    Date of Patent: May 22, 1990
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Keith A. M. Walker, Denis J. Kertesz
  • Patent number: 4906785
    Abstract: 26,26,26-Trifluoro-1.alpha.,25-dihydroxy-cholecalciferol, and the 25R or 25S epimer thereof, are described, as well as processes and intermediates utilized to prepare the same, as well as pharmaceutical compositions containing the same. 26,26,26-trifluoro 1.alpha.,25-dihydroxycholecalciferol and the 25R or 25S epimer thereof are useful agents in the treatment of disease states such as osteoporosis, osteodystrophy and leukemia.
    Type: Grant
    Filed: January 22, 1986
    Date of Patent: March 6, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Enrico G. Baggiolini, Giacomo Pizzolato, Gary A. Truitt, Milan R. Uskovic
  • Patent number: 4898855
    Abstract: The invention is directed to deuterated vitamin D analogs, and processes and intermediates for their preparation. The end products, that is the deuterated vitamin D analogs, are useful for the treatment osteoporosis and cutaneous inflammations such as psoriasis, and contact dermatitis.
    Type: Grant
    Filed: September 14, 1987
    Date of Patent: February 6, 1990
    Assignee: Hoffman-La Roche Inc.
    Inventors: Enrico G. Baggiolini, Bernard M. Hennessy, Milan R. Uskokovic
  • Patent number: 4877904
    Abstract: Novel odorant and/or flavoring substances are described. These are the compounds of the formula ##STR1## wherein: R.sup.1 represents methyl or ethyl,R.sup.2 represents hydrogen or methyl,the dotted line represents an optional carbon-carbon bond,n is 0 or 1, and,when n is O, R.sup.3 is hydrogen and R.sup.4 represents acetyl or propronyl, and,when n is 1, R.sup.3 represents methyl or ethyl and R.sup.4 represents hydrogen or methyl,with the exception of 1,4,4,7a-tetramethyl-3a,4,5,7a-tetrahydro-7(6H)-ind-1-enone.The compounds of formula I possess organoleptic properties which make them particularly suitable for use as odorant and/or flavoring substances.
    Type: Grant
    Filed: September 9, 1987
    Date of Patent: October 31, 1989
    Assignee: Givaudan Corporation
    Inventor: Peter Naegeli
  • Patent number: 4855322
    Abstract: A compound of the formula ##STR1## wherein Q is CO, CH(OR), CR(OH), or CR (OC)-lower alkyl); R is H, or C.sup.1-2 -alkyl;X is hydroxyalkyl,methoxy-C.sup.2-11 -alkyl, ethoxy-C.sup.2-11 -alkyl or oxo-C.sup.2-11 -alkyl, formyl-C.sup.2-11 -alkyl,carboxy-C.sup.2-11 -alkyl or (C.sub.1-2 -alkyl) oxycarbonyl-C.sup.2-11 -alkyl;c is 1 or 2;p or w are 0, 1 or 2 and the sum of p and w is 1 to 4;and a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: June 1, 1987
    Date of Patent: August 8, 1989
    Assignee: CBD Corporation
    Inventors: Walter J. Kasha, Chantal S. Burnison