Bicyclo Ring System Patents (Class 568/819)
  • Patent number: 5508392
    Abstract: The present invention relates to methods for the treatment of prevention of osteoporosis by the administration of a vitamin D glycoside or vitamin D orthoester glycoside, or an analog thereof.
    Type: Grant
    Filed: April 20, 1994
    Date of Patent: April 16, 1996
    Inventor: Michael F. Holick
  • 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: 5457245
    Abstract: A process for synthesizing (23S,25R)-calcitriol lactone and related Vitamin D analogs comprises reacting protected enantiomerically pure glycidol or 2-alkylglycidol with protected De-A,B-8.beta.-hydroxy-24-nor-cholan-23-al, removing the protective groups from the epimeric product mixture and separating the epimers, to give a hydrindane tetrol product, followed by oxidation and protection of the hydrindane tetrol product, reacting the tetrol product with the lithium salt of (3S)-(3.alpha.,5.beta.,Z)-2-(2-methylene-3,5-bis-((1,1-dimethylethyl)dimet hylsilyloxy)cyclohexylidene)ethyl diphenyl phosphine oxide and removing the final protective groups. Certain intermediate compounds also show biological activity as angiostatic agents.
    Type: Grant
    Filed: July 11, 1994
    Date of Patent: October 10, 1995
    Assignee: Alcon Laboratories, Inc.
    Inventor: Raymond E. Conrow
  • 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: 5422365
    Abstract: A compound selected from those of formula (I): ##STR1## wherein: R.sub.1, R'.sub.1 and R.sub.2 are each selected, independently of the others, from hydrogen and an alkyl radical, the two R.sub.2 groups being in the cis position in relation to the rings,and R, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R'a and R'b are as defined in the description,useful therapeutically in the regulation of the secretion of insulin.
    Type: Grant
    Filed: August 12, 1994
    Date of Patent: June 6, 1995
    Assignee: Adir et Compagnie
    Inventors: David Billington, Francoise Perron-Sierra, Isabelle Picard, Jacques Duhault, Joseph Espinal
  • Patent number: 5420366
    Abstract: The present invention provides a process for preparing optically active 2-arylcyclohexanol and its esters and ethers and which process comprises the step of subjecting 1-aryl-cyclohexane-1,2 diol and its diethers and diesters to hydrogenolysis conditions to form said cyclohexanol and its esters and ethers.
    Type: Grant
    Filed: May 11, 1994
    Date of Patent: May 30, 1995
    Assignee: Hoechst Celanese Corporation
    Inventor: Shu-Hai Zhao
  • Patent number: 5405870
    Abstract: Compounds of formula (Ic): ##STR1## having valuable platelet-aggregation inhibitory activities useful for the prophylaxis and treatment of such diseases as thrombosis and pharmaceutical compositions containing said compounds.
    Type: Grant
    Filed: November 4, 1993
    Date of Patent: April 11, 1995
    Assignee: Sankyo Company, Limited
    Inventors: Kazuo Koyama, Shigeo Amemiya, Koichi Kojima, Shinsaku Kobayashi
  • Patent number: 5399587
    Abstract: The present invention relates to novel potassium channel agonists which are useful in activating the calcium activated Maxi-K potassium channel in mammalian neuronal and smooth muscle tissue. The claimed compounds are of the general formula: ##STR1## In addition, a novel microbiological process for producing the claimed compounds is described.
    Type: Grant
    Filed: December 13, 1993
    Date of Patent: March 21, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Maria L. Garcia, Robert A. Giacobbe, Otto D. Hensens, Gregory J. Kaczorowski, Seok H. Lee, Owen B. McManus, Deborah L. Zink
  • Patent number: 5292971
    Abstract: Fluorine-substituted vicinal glycols of the formula ##STR1## in which the substituents R.sub.1 to R.sub.4, independently of one another, have the following meanings: R.sub.1 to R.sub.4 =H, fluorine, C.sub.1 - to C.sub.18 -alkyl in which some or all of the hydrogens may be substituted by fluorine, and at least one of the substituents R.sub.1 to R.sub.4 is a completely fluorinated alkyl or an alkyl of the formula--(CH.sub.2).sub.m --(C.sub.n F.sub.2n+1),in which m is 1 or 2, and n is an integer from 1 to 17, and x is 0 or 1.Furthermore, a method for the preparation of the fluorinated vicinal glycols is described. If the fluorinated vicinal glycols are condensed together with dicarboxylic acids, products having enhanced thermal stability are obtained.
    Type: Grant
    Filed: February 12, 1993
    Date of Patent: March 8, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Kulpe, Heinz Strutz
  • Patent number: 5283345
    Abstract: There are disclosed novel compounds that can be used to derive therefrom a fragment that corresponds to an A-ring which is to be comined with fragments which respectively correspond to C- and D-rings in synthetic formation of vitamin D.sub.3 derivatives by cleaving the 7,8-bondings by means of oxidizing agents following any known process. According to the invention, there is provided an industrially efficient and effective method of manufacturing above compounds that utilizes chemical reaction of allylic acid to add an oxygen function group to position C(1), a method which is completely different from any existing synthetic methods.
    Type: Grant
    Filed: May 6, 1992
    Date of Patent: February 1, 1994
    Assignee: Hoxan Corporation
    Inventor: Yuji Tahara
  • Patent number: 5241089
    Abstract: Described are polyhydrodimethylnaphthalene spirofuran derivatives defined according to the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond a process for preparing same and uses thereof in augmenting, enhancing or imparting an aroma in or to perfume compositions, colognes and perfumed articles including but not limited to solid or liquid, anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles and hair preparations.
    Type: Grant
    Filed: February 26, 1993
    Date of Patent: August 31, 1993
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Wilhelmus J. Wiegers, Marie R. Hanna
  • Patent number: 5232836
    Abstract: Vitamin D derivatives corresponding to the following formula I ##STR1## in which R.sub.1 denotes a substituted alkyl group having 1 to 15 carbon atoms, in particular the side chains of vitamin D.sub.2 (C.sup.20 to C.sup.28) or D.sub.3 (C.sup.20 to C.sup.
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: August 3, 1993
    Assignee: Ire-Medgenix S.A.
    Inventors: Roger Bouillon, Pierre J. De Clerco, Pierre Eliard, Maurits Vanderwalle
  • 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: 5196601
    Abstract: Disclosed herein is a process for producing an alcohol or an amine by reducing a compound having a formyl, keto, nitro, oxirane, ester, nitrile, amide or halogenated carboxyl group with an alkali metal boro-hydride in the presence of a compound having a hydroxyl group and ether linkage. According to the present invention, a functional group having a great steric hindrance can be reduced, and a corresponding alcohol or amine can efficiently be produced under very mild conditions on an industrial scale.
    Type: Grant
    Filed: June 17, 1992
    Date of Patent: March 23, 1993
    Assignee: Kao Corporation
    Inventors: Tomohito Kitsuki, Yoshiaki Fujikura
  • Patent number: 5196613
    Abstract: The invention concerns a novel process for the manufacture of 2-hydroxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene, 1, commonly known as .alpha.-ambrinol. ##STR1## The process comprises reducing either an 8-halo-2-hydroxy-2,5,5-trimethyl-2,3,4,4a,5,6,7,8-ociahydronaphihalene (11a), alone or in admixture with a 1-halo-2-hydroxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (11b), or reducing the 1,2-epoxide which can be formed therefrom, namely, 1,2-epoxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphihalene (111). The halohydrins 11 are prepared from 1,1,6-trimethyl-1,2,3,7,8,8a-hexahydronaphihalene, IV.The compounds of formulas II and III are novel and form part of the present invention. The formula III epoxide possesses valuable odorant properties and its use as an odorant also forms part of the invention.
    Type: Grant
    Filed: January 21, 1991
    Date of Patent: March 23, 1993
    Assignee: Givaudan Corporation
    Inventor: Peter Naegeli
  • Patent number: 5190964
    Abstract: 5-fluorocarbacyclin derivatives of the Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH orA 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 free or functionally modified ##STR2## in which the OH group can be in the .alpha.-- or .beta.-position, D is ##STR3## a C.sub.1-10 -aliphatic group (e.g., alkyl or alkenyl) which optionally can be substituted by fluorine atoms,n is 1, 2 or 3,E is a direct bond, --C.tbd.C-- or --CR.sub.6 .tbd.CR.sub.7 -- in which R.sub.6 represents a hydrogen atom or an alkyl group with 1-5 atoms and R.sub.7 represents a hydrogen atom, a halogen atom or an alkyl group with 1-5 C atoms,R.sub.4 is alkyl, cycloalkyl or optionally substituted aryl or a heterocyclic group,R.sub.5 is a free or functionally modified hydroxy groupand, when R.sub.2 is a hydrogen atom, its salts with physiologically compatible bases,have valuable pharmacological properties.
    Type: Grant
    Filed: February 15, 1990
    Date of Patent: March 2, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Martin Haberey, Claus-Steffen Sturzebecher, Michael-Harold Town
  • Patent number: 5169993
    Abstract: The invention provides cyclohexenol derivatives of the general formula ##STR1## in which n represents an integer from 0 to 5; each R represents a halogen atom, nitro, cyano, hydroxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, alkoxycarbonyl, carboxyl, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, alkylamido, cycloalkyl or phenyl group; and R.sup.1, R.sup.2 and R.sup.3 independently represent a hydrogen atom or an alkyl group, with the provisos that when R.sup.1, R.sup.2 and R.sup.3 all represent a hydrogen atom then n is not 0 and, when R.sup.1, R.sup.2 and R.sup.3 all represent a hydrogen atom and n is 1, R does not represent a fluorine atom substituted at the 4-position of the phenyl ring; and a process for their preparation. Compounds of formula I are useful as intermediates in the preparation of certain fungicidal active cyclopentane derivatives.
    Type: Grant
    Filed: August 19, 1991
    Date of Patent: December 8, 1992
    Assignee: Shell Research Limited
    Inventor: Paul H. Briner
  • 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: 5136112
    Abstract: A process for preparing 2-hydroxy-2, 5, 5, 9-tetramethyldecalyl ethanol of formula (II): ##STR1## which comprises reducing 3a, 6, 6, 9a-tetramethyldecahydro-naphto[2, 1-b]furan-2(1H)-one of formula (I): ##STR2## with an alkali metal boron hydride in the presence of a hydroxyl ether compound.
    Type: Grant
    Filed: July 29, 1991
    Date of Patent: August 4, 1992
    Assignee: Kao Corporation
    Inventors: Tomohito Kitsuki, Yoshiaki Fujikura
  • Patent number: 5124343
    Abstract: The invention relates to carbacyclins of general Formula I ##STR1## wherein R.sub.1 is the residue CH.sub.2 OH or ##STR2## with R.sub.2 meaning a hydrogen atom, an alkyl, cycloalkyl, aryl residue, a ##STR3## or heterocyclic residue, or R.sub.1 is the residue ##STR4## with R.sub.3 meaning an alkanoyl or alkanesulfonyl residue of respectively 1-10 carbon atoms or the residue R.sub.2, orR.sub.1 is the residue ##STR5## wherein m is the number 1 or 2, X is an oxygen atom or a CH.sub.2 -group,A is a trans--CH.dbd.CH- or --.tbd.C--group,W is a free or functionally modified hydroxymethylene group wherein the OH-group can be in the .alpha.- or .beta.- position,n is the number 1, 2, or 3,D is a straight-chain alkylene group of 1-5 carbon atoms,E is a --C.tbd.C---bond or a --CR.sub.6 =CR.sub.7 --group wherein R.sub.6 and R.sub.7 are different from each other and mean a hydrogen atom or an alkyl group of 1-5 carbon atoms or a hydrogen atom or a halogen atom, preferably chlorine,R.sub.
    Type: Grant
    Filed: January 6, 1988
    Date of Patent: June 23, 1992
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbrueggen, Hernd Raduechel, Werner Skuballa, Norbert Schwarz, Jorge Casals-Stenzel, Gerda Mannesmann, Michael H. Town
  • Patent number: 5107037
    Abstract: The invention concerns a novel process for the manufacture of 2-hydroxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene, I, commonly known as .alpha.-ambrinol. ##STR1## The process comprises reducing either an 8-halo-2-hydroxy-2,5,5-trimethyl-2,3,4,4a,5,6,7,8-octahydronaphthalene (IIa), alone or in a mixture with a 1-halo-2-hydroxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (IIb), or reduced the 1,2-epoxide which can be formed therefrom, namely, 1,2-epoxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octanhydronaphthalene (III). The halohydrins II are prepared from 1,1,6-trimethyl-1,2,3,7,8,8a-hexahydronaphthalene, IV.The compounds of formulas II and III are novel and form part of the present invention. The formula III epoxide possesses valuable odorant properties and its use as an odorant also forms part of the invention.
    Type: Grant
    Filed: June 6, 1990
    Date of Patent: April 21, 1992
    Assignee: Givaudan Corporation
    Inventor: Peter Naegeli
  • Patent number: 5104851
    Abstract: A 2-(alkyl-cyclohexyl)-1-propanol is disclosed. The compound is represented by formula (I): ##STR1## wherein R.sub.1 and R.sub.2 individually represent a group selected from the members consisting of methyl-, ethyl-, n-propyl-, i-propyl-, t-butyl-, and sec-butyl groups, provided that the total carbon atoms of the R.sub.1 and R.sub.2 groups are 4 to 7; either R.sub.1 and R.sub.2 is a hydrogen atom, the other being a cyclohexyl group; or R.sub.1 and R.sub.2 together form a hexamethylene ring together with 2 carbon atoms in the cyclohexane ring. The compound possesses a long-lasting, woody, floral odor, and can be widely used as perfumery materials such as perfumes, soaps, shampoos, aromatic goods, and detergents.
    Type: Grant
    Filed: January 25, 1991
    Date of Patent: April 14, 1992
    Assignee: Kao Corporation
    Inventors: Yoshiaki Fujikura, Hiroaki Ohnuma, Manabu Fujita, Nao Toi
  • Patent number: 4983627
    Abstract: Compounds useful in treating or preventing gastrointestinal ulcers and in treating cardiovascular disorders such as thrombosis, hypertension and atherosclerosis are depicted in formulas (1), (2) and (3): ##STR1## wherein: A is --C.tbd.C--, trans --HC.dbd.CH--, trans --CH.dbd.CHCH.sub.2 -- or --CH.sub.2 CH.sub.2 --;X is lower alkyl of 1-6 carbon atoms;Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl);n is an integer from 2-4;R.sub.1 is --CH.sub.2 OH, --CHO, --CO.sub.2 R or --CO.sub.2 H, and the olefin formed by the R.sub.1 (CH.sub.2).sub.n CH.dbd. moiety is either (E) or (Z);R.sub.2 is hydrogen or methyl, or optionally --CH.dbd.CH.sub.2 when A is trans --CH.dbd.CHCH.sub.2 --; andR.sub.3 is linear or branched alkyl, alkenyl or alkynyl having 5-10 carbon atoms, ##STR2## --(CH.sub.2).sub.m -phenyl or CH.sub.2 O-phenyl; in which each phenyl may be optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen.
    Type: Grant
    Filed: November 10, 1988
    Date of Patent: January 8, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Counde O'Yang, Walter Kurz, Keith A. M. Walker, Helen Y. Wu
  • 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: 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: 4894181
    Abstract: Carbocyclic compounds of the formula I ##STR1## wherein Q is a benzene or cyclohexane ring or a naphthalene system, X is in each case --CH.sub.2 --(CH.sub.2).sub.p -- where it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by --O--, --S--, --CO--, --O--CO--, --CO--O-- or --CH.dbd.CH--,p is 0, 1 or 2,A.sup.1 and A.sup.2 independently of one another are each a 1,4-phenylene group which is unsubstituted or monosubstituted or polysubstituted by halogen atoms and/or CH.sub.3 groups and/or CN groups and in which it would also be possible for one or more CH groups to be replaced by N atoms, a 1,4-cyclohexylene group wherein it would also be possible for one or two non-adjacent CH.sub.2 groups to be replaced by --O-- and/or --S--, a piperidine-1,4-diyl group or a 1,4-bicyclo[2.2.2]octylene group,Z is --CO--O--, --O--CO--, --O--, --CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CHCN--CH.sub.2 --, --CH.sub.2 --CHCN--, --CH.dbd.CH--, --CH.dbd.N--, --N.dbd.CH--, --NO.
    Type: Grant
    Filed: May 16, 1988
    Date of Patent: January 16, 1990
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Klaus Praefcke, Bernd Kohne, Eike Poetsch
  • Patent number: 4885409
    Abstract: Process for the hydrogenation of bis-phenols by reacting bis-phenols with hydrogen in the presence of a catalytic system consisting of palladium supported on activated carbon.
    Type: Grant
    Filed: May 4, 1988
    Date of Patent: December 5, 1989
    Assignee: Montedison S.p.A.
    Inventors: Andrea Gardano, Francesco Casagrande, Marco Foa, Guido Petrini, Riccardo Barisone, Lawrence Chapoy
  • 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
  • Patent number: 4818747
    Abstract: Bicyclic aliphatic alcohols or formula ##STR1## wherein substituents CH.sub.2 OH and CH.sub.3 are geminally bound to the carbon atom in position 2 or 3 of the hexanic ring and wherein the wavy line stands for a C-H bond of cis or trans configuration. Use of same as perfuming ingredients.
    Type: Grant
    Filed: March 17, 1988
    Date of Patent: April 4, 1989
    Assignee: Firmenich SA
    Inventors: Wolfgang K. Giersch, Gunther Ohloff
  • Patent number: 4782188
    Abstract: The invention is a process for the hydroformylation of C.sub.2-4 alkenes, formyl-substituted C.sub.2-4 alkenes, aryl-substituted alkenes, unsaturated norbornane ring-containing compounds, and .alpha.-unsaturated acetals which comprises contacting a C.sub.2-4 alkene, a formyl-substituted C.sub.2-4 alkene, aryl-substituted alkene, an unsaturated norbornane ring-containing compound or an .alpha.-unsaturated acetal in a polar organic solvent with water and carbon monoxide in the presence of a catalytic amount of a catalyst which comprises a mixture of (a) an alkali metal iron carbonyl or alkaline earth metal iron carbonyl which corresponds to the formula M.sub.a Fe.sub.x (CO).sub.y and (b) iron pentacarbonyl under conditions such that an alcohol or aldehyde derivative of a C.sub.2-4 alkene, a formyl-substituted C.sub.2-4 alkene, an aryl-substituted alkene, unsaturated norbornane ring-containing compound or an .alpha.
    Type: Grant
    Filed: November 14, 1983
    Date of Patent: November 1, 1988
    Assignee: The Dow Chemical Company
    Inventor: Susan B. Butts
  • Patent number: 4777184
    Abstract: Prostaglandin derivatives, and specifically derivatives of isocarbacyclin, have an optionally substituted methylene group as a substituent on the .alpha.-carbon atom of the .alpha.-side chain. They have a variety of physiological effects, notably a strong ability to inhibit blood platelet aggregation and a strong anti-ulcer activity.
    Type: Grant
    Filed: April 29, 1986
    Date of Patent: October 11, 1988
    Assignee: Sankyo Company Limited
    Inventors: Koichi Kojima, Shigeo Amemiya, Kazuo Koyama, Nobuyoshi Iwata, Takeshi Oshima
  • Patent number: 4762936
    Abstract: There are disclosed a bicyclo[3.3.0]octene derivatives having the following formula: ##STR1## wherein R.sup.1 : a straight, branched or cyclic alkyl group or alkenyl group each having 5 to 10 carbon atoms;R.sup.2 and R.sup.3 : each represent a hydrogen atom or a protective group of a hydroxy group; andR.sup.4 : --CH.dbd.CH--(CH.sub.2).sub.2 --COOR.sup.5 or --CH.sub.2 R.sup.6 ; whereR.sup.5 : a hydrogen atom or an alkyl group; andR.sup.6 : a hydroxy group, an acetyloxy group or a butenyl group,and process for producing the same. These compounds and the process for producing them are available for producing a 9(0)-methano-.DELTA..sup.6 (9.alpha.)-PGI.sub.1.
    Type: Grant
    Filed: December 11, 1986
    Date of Patent: August 9, 1988
    Assignee: Sagami Chemical Research Center
    Inventors: Masakatsu Shibasaki, Toshiaki Mase, Mikiko Sodeoka, Yuji Ogawa
  • Patent number: 4739112
    Abstract: Perfluoropolycycloalkanes are provided. These perfluoropolycycloalkanes are ring assemblies having (a) at least two perfluorinated cyclohexane rings, (b) at least two perfluorinated fused ring systems, or (c) combinations of at least one perfluorinated cyclohexane ring with at least one perfluorinated fused ring system, each perfluorinated ring or fused ring system being directly joined to another perfluorinated ring or ring system by a single bond and the ring assemblies having a total of at least 13 carbon atoms.
    Type: Grant
    Filed: February 1, 1985
    Date of Patent: April 19, 1988
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Patricia M. Savu
  • Patent number: 4739103
    Abstract: Di- and tri-substituted perfluorocycloalkane compounds which have a cyclohexane or decahydronaphthalene nucleus are provided. These perfluorocycloalkane compounds are carbonyl fluorides and derivatives thereof.
    Type: Grant
    Filed: February 1, 1985
    Date of Patent: April 19, 1988
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: John C. Hansen, Patricia M. Savu
  • Patent number: 4735966
    Abstract: Compounds useful in treating cardiovascular disorders such as thrombosis, hypertension and atherosclerosis are depicted in formulas (1), (2) and (3): ##STR1## wherein: A is --C.tbd.C--, trans --HC.dbd.CH--, --CH.sub.2 CH.sub.2 -- or --CH.dbd.CHCH.sub.2 --;X is lower alkoxy, hydroxy, or (2,2,2)-trifluoroethoxy;Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl);is an integer of 2-4;R.sub.1 is --CH.sub.2 OH, --CHO, --CO.sub.2 R or --CO.sub.2 H, and the olefin formed by the R.sub.1 (CH.sub.2).sub.n CH.dbd. moiety is either (E) or (Z);R.sub.2 is hydrogen or methyl, or optionally --CH.dbd.CH.sub.2 when A is --CH.dbd.CHCH.sub.2 --; andR.sub.3 is linear or branched alkyl, alkenyl or alkynyl having 5-10 carbon atoms, ##STR2## --(CH.sub.2).sub.m -phenyl or CH.sub.
    Type: Grant
    Filed: August 25, 1986
    Date of Patent: April 5, 1988
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Helen Y. Wu, Walter Kurz
  • Patent number: 4721729
    Abstract: Carbacyclins of Formula I ##STR1## wherein R.sub.1 is an alkyl, cycloalkyl, aryl, aralkyl, or heterocyclic group,Y is a keto group or a hydroxymethylene group,X is a --CH.sub.2 -- group or an oxygen atom,A is a --CH.sub.2 --CH.sub.2 --, a trans--CH.dbd.CH-- or a --C.tbd.C-- group,W is a hydroxymethylene group or a ##STR2## D is the group ##STR3## a straight-chain or branched, saturated alkylene group or unsaturated alkylene group of up to 5 carbon atoms which can optionally be substituted by 1-2 fluorine atoms,n is 1, 2 or 3,E is a direct bond, a --C.tbd.C-- group or a --CR.sub.4 .dbd.CR.sub.5 -- group wherein R.sub.4 is hydrogen or an alkyl group and R.sub.5 is hydrogen, halogen or an alkyl group,R.sub.2 is an alkyl, cycloalkyl, aryl, or heterocyclic group, andR.sub.3 is a hydroxy group,are valuable, e.g., as cytoprotective agents.
    Type: Grant
    Filed: February 8, 1985
    Date of Patent: January 26, 1988
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Robert Nickolson, Martin Haberey, Olaf Loge, Claus-Steffen Stuerzebecher
  • Patent number: 4701543
    Abstract: Oxygenated decaline derivatives of formula ##STR1## wherein X represents a COOH or a CHO group are obtained according to a process which consists in the oxidation of a ketone of formula ##STR2## by means of oxygen in a basic medium constituted by potassium tert-butoxide in 1,2-dimethoxyethane.Compounds (I) are useful starting materials for the preparation of AMBROX.RTM. (registered tradename of Firmenich SA, Geneva, Switzerland) which is an ingredient in perfumes.
    Type: Grant
    Filed: July 18, 1986
    Date of Patent: October 20, 1987
    Assignee: Firmenich S.A.
    Inventors: Ferdinand Naef, Christian Vial
  • Patent number: 4677233
    Abstract: 3a,6,6,9a-Tetramethylperhydronaphto[2,1-b]furan, a typical ambergris perfume ingredient is prepared via a novel process from 1.beta.-(2-hydroxyethyl)-perhydro-2,5,5,8a.beta.-tetramethyl-2.beta.-trans -napthalenol by cyclization with an acidic cyclization agent in the presence of nitromethane.
    Type: Grant
    Filed: June 23, 1986
    Date of Patent: June 30, 1987
    Assignee: Firmenich SA
    Inventors: George H. Buchi, Hans Wuest
  • Patent number: 4671798
    Abstract: Bicyclic carbinol of formula ##STR1## or 1,2,3,4,4a,5,8,8a-octahydro-2,2,6,8-tetramethyl-1-naphthalenol possesses useful odorous properties and it can be used advantageously as perfuming ingredient. A two-step process for its synthesis is disclosed starting from 2-methylpenta-1,3-diene and 6,6-dimethyl-cyclohex-2-en-1-one.
    Type: Grant
    Filed: March 26, 1985
    Date of Patent: June 9, 1987
    Assignee: Firmenich SA
    Inventor: Claudio Tarchini
  • Patent number: 4659509
    Abstract: There is provided an aroma composition containing a sesquiterpene alcohol having the hexahydroindane skeleton. Such sesquiterpene alcohol has a fantastic aroma reminiscent of a variety of odors based on the woody note and powdery green note and furthermore has high diffusivity and retentivity and accords well with a number of perfume and fragrance materials and flavor materials.
    Type: Grant
    Filed: April 17, 1985
    Date of Patent: April 21, 1987
    Assignee: Kuraray Co., Ltd.
    Inventor: Yoshinori Asakawa
  • Patent number: 4639532
    Abstract: Disclosed is an improved process for synthesizing periplanone-B, the sex attractant and sex excitant pheromone of the American cockroach, Periplaneta americana.
    Type: Grant
    Filed: June 18, 1984
    Date of Patent: January 27, 1987
    Assignee: Yale University
    Inventor: Stuart L. Schreiber
  • Patent number: 4633011
    Abstract: 3a,6,6,9a-Tetramethylperhydronaphto[2,1-b]furan, a typical ambergris perfume ingredient is prepared via a novel process from 1.beta.-(2-hydroxyethyl)-perhydro-2,5,5,8a.beta.-tetramethyl-2.beta.-trans -naphthalenol by cyclization with an acidic cyclization agent in the presence of nitromethane.
    Type: Grant
    Filed: March 10, 1986
    Date of Patent: December 30, 1986
    Assignee: Firmenich SA
    Inventors: George H. Buchi, Hans Wuest
  • Patent number: 4628110
    Abstract: Novel compounds of the following general formula: ##STR1##
    Type: Grant
    Filed: October 30, 1984
    Date of Patent: December 9, 1986
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4626603
    Abstract: Aliphatic or cyclic epoxides containing 3 to 8 carbon atoms which are present in aromatic hydrocarbons or halohydrocarbons are saponified continuously and directly to vicinal diols without the use of high temperatures and pressures which would otherwise be necessary. The saponification is acid catalyzed.
    Type: Grant
    Filed: November 15, 1985
    Date of Patent: December 2, 1986
    Assignee: Degussa Aktiengesellschaft
    Inventors: Rainer Siegmeier, Gunter Prescher, Helmut Maurer
  • Patent number: 4613710
    Abstract: 3a,6,6,9a-Tetramethylperhydronaphto[2,1-b]furan, a typical ambergris perfume ingredient is prepared via a novel process from 1.beta.-(2-hydroxyethyl)-perhydro-2,5,5,8a.beta.-tetramethyl-2.beta.-trans -naphthalenol by cyclization with an acidic cyclization agent in the presence of nitromethane.
    Type: Grant
    Filed: August 8, 1984
    Date of Patent: September 23, 1986
    Assignee: Firmenich SA
    Inventors: George H. Buchi, Hans Wuest
  • 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: 4604488
    Abstract: Fragrant cyclohexanol derivatives are produced by condensing 2-ethylidene-5-norbornene with a phenol compound, in the presence of a Friedel-Crafts catalyst; and hydrogenating the condensation product in the presence of a metal catalyst.The compounds so produced have a green-floral odor and are advantageously used in soaps, detergents, shampoos, hair rinse, cosmetics, colognes and perfumes.
    Type: Grant
    Filed: December 21, 1983
    Date of Patent: August 5, 1986
    Assignee: Kao Corporation
    Inventors: Yoshiaki Fujikura, Yasushi Kajihara, Naotake Takaishi, Yoshiaki Inamoto, Akio Kimura, Motoki Nakajima, Norioki Miyamoto
  • Patent number: 4595776
    Abstract: The invention is directed to a process and intermediates for the preparation of 1.alpha.,25-dihydroxyergocalciferol as well as substantially pure and crystalline 1.alpha.,25-dihydroxyergocolciferol. The end-product 1.alpha.,25-dihydroxyergocalciferol is useful in the treatment of disease states which are characterized by insufficient amounts of 1.alpha., 25-dihydroxycholecalciferol.
    Type: Grant
    Filed: December 17, 1984
    Date of Patent: June 17, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Enrico G. Baggiolini, Andrew D. Batcho, Alfred Boris, Milan R. Uskokovic
  • Patent number: 4594432
    Abstract: The invention is directed to a process and intermediates for the preparation of 1.alpha.,23(S),25-trihydroxycholecalciferol and 1.alpha.,23(R),25-trihydroxycholecalciferol. The end-products, 1.alpha.,23(S),25-trihydroxycholecalciferol and 1.alpha.,23(R),25-trihydroxycholecalciferol, are useful for the treatment of disease states which are characterized by insufficient amounts of 1,25 dihydroxycholecalciferol.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: June 10, 1986
    Assignee: Hoffman-La Roche Inc.
    Inventors: Enrico G. Baggiolini, Milan R. Uskokovic, Peter M. Wovkulich
  • Patent number: 4588823
    Abstract: Novel compounds of the following general formula: ##STR1##
    Type: Grant
    Filed: September 27, 1984
    Date of Patent: May 13, 1986
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff