Bicyclo Ring System Patents (Class 568/374)
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Patent number: 6169212Abstract: 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: GrantFiled: October 22, 1999Date of Patent: January 2, 2001Assignee: Firmenich SAInventor: Wolfgang Klaus Giersch
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Patent number: 6160184Abstract: 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: GrantFiled: January 6, 2000Date of Patent: December 12, 2000Assignee: The Regents of the University of CaliforniaInventor: Trevor C. McMorris
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Patent number: 6111144Abstract: 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: GrantFiled: August 20, 1998Date of Patent: August 29, 2000Assignee: Florida State UniversityInventors: Robert A. Holton, Phong Vu, Tawfik Gharbaoui, Vincent Reboul
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Patent number: 6069283Abstract: 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: GrantFiled: February 1, 1999Date of Patent: May 30, 2000Assignee: The Regents of the University of CaliforniaInventors: Trevor C. McMorris, Michael J. Kelner
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Patent number: 6030962Abstract: 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: GrantFiled: April 16, 1998Date of Patent: February 29, 2000Assignee: Synttex (U.S.A.) Inc.Inventors: Percy Sarwood Manchand, Milan Radoje Uskokovic
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Patent number: 6025328Abstract: 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: GrantFiled: February 20, 1998Date of Patent: February 15, 2000Assignee: The Regents of the University of CaliforniaInventors: Trevor C. McMorris, Michael J. Kelner
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Patent number: 5972341Abstract: 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: GrantFiled: May 20, 1998Date of Patent: October 26, 1999Assignee: Parfums Christian DiorInventors: Patrice Andre, Stephane Lhermite, Fran.cedilla.oise Pellicier
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Patent number: 5948933Abstract: 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: GrantFiled: July 11, 1997Date of Patent: September 7, 1999Assignees: Organix, Inc., President and Fellows of Harvard CollegeInventors: Peter C. Meltzer, Bertha K. Madras, Paul Blundell, Zhengming Chen
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Patent number: 5932553Abstract: 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: GrantFiled: July 18, 1996Date of Patent: August 3, 1999Assignee: The Regents of the University of CaliforniaInventors: Trevor C. McMorris, Michael J. Kelner
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Patent number: 5929291Abstract: The invention relates to compounds of the general formula ##STR1## in which R.sup.1 to R.sup.7 are, independently, H, methyl or ethyl, R.sup.8 +R.sup.9 together form methylene (--CH.sub.2 --) or a single bond, or R.sup.1 +R.sup.2 together form --(CH.sub.2).sub.n --, with n being 3 or 4, or R.sup.3 +R.sup.5 or R.sup.5 +R.sup.7 represent methylene or a single bond; and the presence of at least one cyclopropane ring in the molecule is compulsory and the side chain can be saturated or contains one double bond in position .alpha.,.beta. or .beta., .gamma. a process for the manufacture of these compounds, compounds used to perform the process and the use of these compounds as an odorant or as an ingredient of an odorant composition.Type: GrantFiled: April 9, 1997Date of Patent: July 27, 1999Assignee: Givaudan Roure (International) SAInventors: Jerzy A. Bajgrowicz, Georg Frater
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Patent number: 5892124Abstract: 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: GrantFiled: December 29, 1997Date of Patent: April 6, 1999Assignee: Institut Fran.cedilla.ais du PetroleInventors: Helene Olivier, Andre Hirschauer
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Patent number: 5872113Abstract: 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: GrantFiled: May 16, 1997Date of Patent: February 16, 1999Assignee: Syntex (U.S.A.) Inc.Inventors: John J. Nestor, Jr., Percy S. Manchand, Milan R. Uskokovic, Brian H. Vickery
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Patent number: 5856580Abstract: 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: GrantFiled: October 31, 1997Date of Patent: January 5, 1999Assignee: The Regents of University of CaliforniaInventor: Trevor C. McMorris
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Patent number: 5834404Abstract: 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: GrantFiled: July 15, 1997Date of Patent: November 10, 1998Assignee: Nippon Soda Co., ltd.Inventors: Takahiro Sagae, Masao Yamaguchi, Hiroyuki Adachi, Kazuyuki Tomida, Akihiro Takahashi, Takashi Kawana
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Patent number: 5730960Abstract: 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: GrantFiled: July 21, 1995Date of Patent: March 24, 1998Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Inge Stein, Michael Schwarz, Ulrich Heywang, Michael Kompter
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Patent number: 5707961Abstract: 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: GrantFiled: April 25, 1996Date of Patent: January 13, 1998Assignee: Givaudan-Roure (International) SAInventors: Jerzy A. Bajgrowicz, Alain Bringhen, Georg Frater, Urs Muller
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Patent number: 5581004Abstract: 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: GrantFiled: October 17, 1994Date of Patent: December 3, 1996Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5563176Abstract: 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: GrantFiled: July 15, 1994Date of Patent: October 8, 1996Assignee: The Regents of the University of CaliforniaInventors: Michael J. Kelner, Trevor C. McMorris, Raymond Taetle
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Patent number: 5523490Abstract: 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: GrantFiled: November 1, 1994Date of Patent: June 4, 1996Assignee: The Regents of the University of CaliforniaInventors: Michael J. Kelner, Trevor C. McMorris, Raymond Taetle
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Patent number: 5498734Abstract: 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: GrantFiled: July 30, 1993Date of Patent: March 12, 1996Assignee: University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5468905Abstract: 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: GrantFiled: May 25, 1994Date of Patent: November 21, 1995Assignee: Nippon Soda Co., Ltd.Inventors: Junji Suzuki, Masami Hatano, Shinichi Imaizumi
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Patent number: 5441987Abstract: 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: GrantFiled: August 12, 1994Date of Patent: August 15, 1995Assignee: 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
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Patent number: 5437686Abstract: 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: GrantFiled: May 18, 1994Date of Patent: August 1, 1995Assignee: Colgate-Palmolive Co.Inventors: Robert J. Heffner, Robert J. Steltenkamp
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Patent number: 5430196Abstract: 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: GrantFiled: September 8, 1994Date of Patent: July 4, 1995Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Heinrich K. Schnoes, Fariba Aria
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Patent number: 5354915Abstract: 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: GrantFiled: December 21, 1992Date of Patent: October 11, 1994Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Walter T. Reichle
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Patent number: 5283349Abstract: 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: GrantFiled: September 11, 1986Date of Patent: February 1, 1994Assignee: Teijin LimitedInventors: Toshio Tanaka, Kiyoshi Bannai, Seizi Kurozumi
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Patent number: 5276055Abstract: 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: GrantFiled: October 19, 1992Date of Patent: January 4, 1994Assignee: 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
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Patent number: 5266600Abstract: 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: GrantFiled: October 30, 1992Date of Patent: November 30, 1993Assignee: Bristol-Myers Squibb CompanyInventors: Osamu Tenmyo, Yosuke Sawada, Toshikazu Oki, Masahisa Oka, Masaru Sugawara, Noriyuki Ohkusa
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Patent number: 5231205Abstract: 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: GrantFiled: September 23, 1991Date of Patent: July 27, 1993Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5180709Abstract: 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: GrantFiled: May 31, 1991Date of Patent: January 19, 1993Assignee: Givaudan-Roure CorporationInventors: Franz Etzweiler, Daniel Helmlinger, Cornelius Nussbaumer, Mario Pesaro
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Patent number: 5163453Abstract: 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: GrantFiled: January 18, 1990Date of Patent: November 17, 1992Assignee: Givaudan CorporationInventors: Jean-Pierre Bachmann, Mario Pesaro
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Patent number: 5164365Abstract: 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: GrantFiled: February 26, 1991Date of Patent: November 17, 1992Assignee: Givaudan CorporationInventors: Jean-Pierre Bachmann, Daniel Helmlinger, Mario Pesaro
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Patent number: 5149846Abstract: 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: GrantFiled: November 16, 1989Date of Patent: September 22, 1992Assignee: Hoffmann-La Roche Inc.Inventors: Enrico G. Baggiolini, Bernard M. Hennessy, Milan R. Uskokovic
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Patent number: 5137869Abstract: 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: GrantFiled: September 13, 1991Date of Patent: August 11, 1992Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, Eleanor Fox, Alphonsus P. M. Maas, Djurre S. Postma
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Patent number: 5131945Abstract: Compounds of formula I ##STR1## are useful as herbicides, effective against dicotyledonous weeds.Type: GrantFiled: July 13, 1990Date of Patent: July 21, 1992Assignee: Shell Research LimitedInventors: Hans-Joachim Bissinger, Ludwig Schoeder, Helmut Baltruschat, Manfred Garrecht, Erich Raddatz, Wolfgang Fruhstorfer
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Patent number: 5118856Abstract: 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: GrantFiled: August 2, 1990Date of Patent: June 2, 1992Assignee: BASF AktiengesellschaftInventors: Gernot Reissenweber, Winfried Richarz
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Patent number: 5114960Abstract: 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: GrantFiled: June 26, 1990Date of Patent: May 19, 1992Assignee: Hoffmann-La Roche Inc.Inventors: Geoffrey Lawton, John M. Osbond, Christopher R. Self
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Patent number: 5084592Abstract: 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: GrantFiled: September 30, 1988Date of Patent: January 28, 1992Assignee: BASF AktiengesellschaftInventors: Wolfgang Schrott, Peter Neumann, Sibylle Brosius, Helmut Barzynski, Klaus D. Schomann, Harald Kuppelmaier
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Patent number: 5077275Abstract: 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: GrantFiled: May 17, 1991Date of Patent: December 31, 1991Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Joseph A. McGhie
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Patent number: 5077274Abstract: 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: GrantFiled: October 12, 1990Date of Patent: December 31, 1991Assignee: International Flavors & Fragrances Inc.Inventors: William J. Evers, Howard H. Heinsohn, Jr.
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Patent number: 5030739Abstract: 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: GrantFiled: August 31, 1990Date of Patent: July 9, 1991Assignee: Hoffman-La Roche Inc.Inventors: Joseph Foricher, Claude Furbringer, Karlheinz Pfoertner
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Patent number: 5019590Abstract: 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: GrantFiled: September 27, 1989Date of Patent: May 28, 1991Assignee: SRI InternationalInventors: Mitchell A. Avery, Wesley K. M. Chong
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Patent number: 5002929Abstract: 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: GrantFiled: October 12, 1989Date of Patent: March 26, 1991Assignee: Henkel Kommadnitgesellschaft auf AktienInventors: Klaus Bruns, Thomas Gerke, Ursula Schmitz
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Patent number: 4971987Abstract: 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: GrantFiled: March 7, 1988Date of Patent: November 20, 1990Assignee: Schering AktiengesellschaftInventors: Helmut Vorbrueggen, Bob Nieuweboer, Claus-Steffen Stuerzebecher, Ulrich Klar
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Patent number: 4943384Abstract: 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: GrantFiled: November 21, 1986Date of Patent: July 24, 1990Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Wolfgang Sucrow, Herbert Wolter, Rudolf Eidenschink
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Patent number: 4927963Abstract: 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: GrantFiled: April 28, 1989Date of Patent: May 22, 1990Assignee: Syntex (U.S.A.) Inc.Inventors: Keith A. M. Walker, Denis J. Kertesz
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Patent number: 4906785Abstract: 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: GrantFiled: January 22, 1986Date of Patent: March 6, 1990Assignee: Hoffmann-La Roche Inc.Inventors: Enrico G. Baggiolini, Giacomo Pizzolato, Gary A. Truitt, Milan R. Uskovic
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Patent number: 4898855Abstract: 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: GrantFiled: September 14, 1987Date of Patent: February 6, 1990Assignee: Hoffman-La Roche Inc.Inventors: Enrico G. Baggiolini, Bernard M. Hennessy, Milan R. Uskokovic
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Patent number: 4877904Abstract: 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: GrantFiled: September 9, 1987Date of Patent: October 31, 1989Assignee: Givaudan CorporationInventor: Peter Naegeli
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Patent number: 4855322Abstract: 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: GrantFiled: June 1, 1987Date of Patent: August 8, 1989Assignee: CBD CorporationInventors: Walter J. Kasha, Chantal S. Burnison