Polycyclo Ring System Having One Of The Two Rings Which Form The Spiro As One Of The Cyclos Patents (Class 549/336)
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Patent number: 6680332Abstract: Disclosed is a method for treating a disorder responsive to the positive modulation of AMPA receptors in animals suffering therefrom, comprising administering to an animal in need thereof a compound of Formula I: or a pharmaceutically acceptable salt or prodrug thereof, wherein: Y is NH2, NHR, and NHCOR; Z is O and S; and R1, R2, R3, R4, and X are defined herein. These compounds can be used as cognitive enhancers, for the treatment of neurodegenerative diseases, including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease, Parkinson's disease, AIDS associated dementia and Down's syndrome as well as for the treatment of schizophrenia and myoclonus. Also disclosed are pharmaceutical compositions useful for treating disorders responsive to the positive modulation of AMPA receptors, and novel compounds of Formula I.Type: GrantFiled: May 20, 2002Date of Patent: January 20, 2004Assignee: Euro-Celtique S.A.Inventors: Christopher S. Konkoy, David B. Fick, Sui Xiong Cai, Nancy C. Lan, John F. W. Keana
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Patent number: 6673937Abstract: Oxidative cyclization of bis-naphthyl ethers allows concise total syntheses of palmarumycin CP1 and deoxypreussomerin A in 8-9 steps and 15-35% overall yield from 5-hydroxy-8-methoxy-1-tetralone. A small library of palmarumycin analogs was created. Biological evaluation of these naphthoquinone spiroketals against MCF-7 and MDA-MB-231 human breast cancer cells revealed several low-micromolar growth inhibitors. A number of the analogs inhibit the thioredoxin—thioredoxin reductase system.Type: GrantFiled: July 19, 2001Date of Patent: January 6, 2004Assignee: The University of PittsburghInventors: John S. Lazo, Peter Wipf, Billy W. Day
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Publication number: 20030171585Abstract: This invention relates to anti-inflammatory compounds, methods of making such compounds and methods of using such compounds having the following structure: 1Type: ApplicationFiled: November 18, 2002Publication date: September 11, 2003Inventors: Malcolm K. Scott, Pauline J. Sanfilippo, Louis J. Fitzpatrick, Richard Cordova, Kevin Pan, Joseph Meschino
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Patent number: 6528538Abstract: The present invention relates to cyclic compounds which are of the class of compounds of formula I wherein X and Y represent an oxygen atom and to processes for preparing such compounds. The compounds are useful in the treatment of dyslipidemia, atherosclerosis, and diabetes.Type: GrantFiled: January 16, 2001Date of Patent: March 4, 2003Assignee: Merck PatentgesellschaftInventors: Jean-Jacques Zeiller, Jean-Jacques Berthelon, Eric Raspé, Daniel Guerrier
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Patent number: 6384251Abstract: A procedure for oxidizing organic compounds having allylic hydrogen atom(s) involving the steps of reactively contacting the organic compound with a combination of an N-hydroxy dicarboxylic acid imide and a chromium-containing oxidant. The reaction can conveniently be conducted under ambient temperature and pressure conditions, and is conveniently conducted in a co-solvent system of water and organic solvent(s).Type: GrantFiled: November 8, 1999Date of Patent: May 7, 2002Assignee: Humanetics CorporationInventors: Padma Marwah, Henry A. Lardy
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Patent number: 6315928Abstract: The present invention relates to specific photochromic 3H-naphtho[2,1-b]pyran derivatives and to their use in plastics of all types, especially for ophthalmic purposes. In particular, the present invention relates to spiro compounds derived from naphthopyrans and having a fluorene structure, referred to as spirofluorenopyrans, in which an annelated ring system is joined by a spiro bond to the central carbon atom of the fluorene structure.Type: GrantFiled: March 2, 2001Date of Patent: November 13, 2001Assignee: Optische Werke G. RodenstockInventors: Claudia Mann, Manfred Melzig, Udo Weigand
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Publication number: 20010029303Abstract: The present invention provides a method of synthesizing compounds of formula (I): 1Type: ApplicationFiled: June 5, 2001Publication date: October 11, 2001Applicant: Regents of the University of CaliforniaInventor: Trevor C. McMorris
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Patent number: 6194586Abstract: This invention discloses an efficient process for selectively sulfonating the primary alcohol of a diol containing both primary and secondary alcohols.Type: GrantFiled: February 25, 1998Date of Patent: February 27, 2001Assignees: Eli Lilly and Company, Wayne State University, University of HawaiiInventors: Michael J. Martinelli, Eric D Moher
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Patent number: 6100268Abstract: The present invention is concerned with compounds of formula ##STR1## the pharmaceutically acceptable acid addition salts thereof, and the stereochemically isomeric forms thereof, wherein R.sup.1 is hydrogen or C.sub.1-6 alkyl; R.sup.2 is hydrogen or C.sub.1-6 alkyl; R.sup.3 is hydrogen or C.sub.1-6 -alkyl; R.sup.4 is hydrogen, halo, C.sub.1-6 alkyl, hydroxy, C.sub.1-6 alkyloxy, aryloxy or arylmethoxy; R.sup.5 and R.sup.6 designate R.sup.5a and R.sup.6a wherein R.sup.5a and R.sup.6a taken together form a bivalent radical; or R.sup.5 and R.sup.6 can designate R.sup.5b and R.sup.6b wherein R.sup.5b is hydrogen and R.sup.6b is a heterocycle or an optionally substituted alkenyl or alkynyl group; or R.sup.5 and R.sup.6 designate R.sup.5c and R.sup.6c, wherein R.sup.5c and R.sup.6c are hydrogen, halo, C.sub.1-6 alkyl, C.sub.3-6 alkenyl, C.sub.3-6 alkynyl, hydroxy, C.sub.1-6 alkyloxy, cyano, aminoC.sub.1-6 alkyl, carboxyl, C.sub.1-6 alkyloxycarbonyl, nitro, amino, aminocarbonyl, C.sub.Type: GrantFiled: July 28, 1998Date of Patent: August 8, 2000Assignee: Janssen Pharmaceutica, N.V.Inventors: Guy Rosalia Eugene Van Lommen, Piet Tom Bert Paul Wigerinck, Marcel Frans Leopold De Bruyn, Wim Gaston Verschueren, Marc Francis Josephine Schroven
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Patent number: 6075155Abstract: Disclosed are compounds of the formulas ##STR1## which are useful as monomers in photopolymerizable compositions. Also disclosed are methods of polymerizing these monomers, and polymers produced thereby.Type: GrantFiled: June 22, 1998Date of Patent: June 13, 2000Assignee: Rensselaer Polytechnic InstituteInventor: James V. Crivello
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Patent number: 5908944Abstract: This invention describes a new methylation or ethylation agent containing trimethyl aluminum or dimethyl zinc or triethyl aluminum as methyl or ethyl source, which additionally contains catalytic amounts of one or more copper(I) and/or copper(II) compounds as well as a process for the 1,4-addition of a methyl or ethyl group to an .alpha.,.beta.-unsaturated or an .alpha.,.beta.-double unsaturated ketone or an .alpha.,.beta.-unsaturated aldehyde using the agent according to the invention.By using only catalytic amounts of copper and a CKW (chlorinatedhydrocarbon)-free reaction medium, the new methylation/ethylation agent/process is distinguished by its environmental compatibility and it is, for example, suitable for the production of initial products for the synthesis of biologically effective compounds.Type: GrantFiled: September 30, 1994Date of Patent: June 1, 1999Assignee: Schering AktiengesellschaftInventors: Jurgen Westermann, Klaus Nickisch
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Patent number: 5789604Abstract: New antibacterial agents produced by fungal culture 07F275, of which the compound designated 07F275 alpha having the following structure: ##STR1## is representative. Methods for the fermentation, recovery and purification from crude solutions are also disclosed.Type: GrantFiled: May 12, 1993Date of Patent: August 4, 1998Assignee: American Cyanamid CompanyInventors: Cedric John Pearce, Robert West, Gerhard Schlingmann
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Patent number: 5670664Abstract: The present invention relates to acetal derivatives of bicyclo?2.2.1!hepta-2,5-diene-7-one (norbornadienone) which are capable of releasing carbon monoxide upon irradiation with ultraviolet light, and a method for producing carbon monoxide employing the same.Type: GrantFiled: September 8, 1995Date of Patent: September 23, 1997Assignee: University Of Maryland Biotechnology InstituteInventors: Joseph P. Y. Kao, Paul F. Keitz
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Patent number: 5670501Abstract: Optically active or racemic compounds represented by the formula ##STR1## where R.sub.1 is C.sub.1 to C.sub.4 straight chain or branched alkyl; R.sub.2 is selected from the group consisting of H, --OR.sub.1, --SR.sub.1, --NH(R.sub.1), --N(R.sub.4)(R.sub.5), aminocarbonyl, halogen, and --CN, where R.sub.4 and R.sub.5 are independently C.sub.1 to C.sub.6 straight chain or branched alkyl, or taken together form a 3- to 7-membered heterocycloalkyl substituent, such heteroatom selected from the group consisting of oxygen, nitrogen and sulfur, optionally including an additional heteroatom which is selected from the group consisting of nitrogen, oxygen, and sulfur; R.sub.3 is cyclopentyl or: ##STR2## where R' and R" are independently H, .dbd.O, --OH, or --NH.sub.2, with the proviso that R' and R" can be taken together form the following structure as R.sub.3 : ##STR3## where R'" is --OH or --NH.sub.2 ; and with the further proviso that when R.sub.3 is cyclopentyl or norbornyl, then R.sub.Type: GrantFiled: September 1, 1994Date of Patent: September 23, 1997Assignee: Discovery Therapeutics, Inc.Inventors: James V. Peck, Ronald J. Wysocki, Ibrahim M. Uwaydah, Noel J. Cusack
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Patent number: 5648505Abstract: The present invention relates to a process for the preparation of a compound of the formula (VIII) or (IX) useful as precursor for the C-ring in taxanes ##STR1## wherein R' is a C.sub.1 -C.sub.6 -alkyl. The invention further relates to the novel compounds (VIII) and (IX) and to novel intermediates in said process.Type: GrantFiled: May 23, 1995Date of Patent: July 15, 1997Inventors: Zhi-Qiang Xia, Esko Karvinen, Ari Koskinen
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Patent number: 5608086Abstract: Cyclohexane derivatives of the formula I ##STR1## in which the radicals are as defined in the description, and processes for the preparation of these compounds, are described. Also described are novel intermediates for the preparation of the compounds of the formula I.Type: GrantFiled: April 14, 1995Date of Patent: March 4, 1997Assignee: Hoechst AktiengesellschaftInventor: Horst Hemmerle
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Patent number: 5591848Abstract: New intramolecular charge-transfer organic dyes are described. The design of these molecules is based on the phenomenon of spiroconjugation, and it provides a modular approach to the preparation of unique materials with interesting optical properties. In the dyes of the invention, the lowest unoccupied molecular orbital (LUMO) of the acceptor part (based on indandione) is spiroconjugated with the highest unoccupied molecular orbital (HOMO) of the donor part (amines, alcohols and thiols). The interaction between the donor and acceptor is controlled by the energy and symmetry of the frontier orbitals. The novel dyes described herein, with predictable and tunable optical properties, can be used in many optical applications including nonlinear optics (NLO).Type: GrantFiled: October 7, 1994Date of Patent: January 7, 1997Assignee: The Penn State Research FoundationInventor: Przemyslaw B. Maslak
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Patent number: 5574178Abstract: Compounds represented by the general formula as well as intermediates for the synthesis of thereof: ##STR1## where R.sup.1 is a hydrogen atom or an acyl group; R.sup.2 is a lower alkyl group; R.sup.3 is a hydrogen atom or a lower alkyl group; R.sup.4, R.sup.5 and R.sup.6, which may be the same or different, are a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl or aryl group; R.sup.2 and R.sup.4, when taken together, may form a 5-membered ring; R.sup.5 and R.sup.6, when taken together, may form a cycloalkyl group or a heterocyclic group in which at least one methylene on the ring of a cycloalkyl group is substituted by an oxygen atom, a sulfur atom or an alkyl-substituted nitrogen atom, provided that R.sup.6 is not present if the ring formed by R.sup.2 and R.sup.4 taken together is a benzofuran ring.Type: GrantFiled: April 17, 1995Date of Patent: November 12, 1996Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Kunio Tamura, Yoshiaki Kato, Mitsutaka Yoshida, Osamu Cynshi, Yasuhiro Ohba
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Patent number: 5463087Abstract: A process for the preparation of a compound. That compound is converted to a novel compound of the formula ##STR1## in which R.sup.1, R.sup.2 and R.sup.5 each independently is alkyl of 3 to 14 carbon atoms, which is used to make novel anti-inflammatories.Type: GrantFiled: January 13, 1995Date of Patent: October 31, 1995Assignee: Bayer PharmaInventors: Erwin Bischoff, Zhan Gao, Stefan Wohlfeil, Gabriele Hecker, Jeannine Cleophax, Didier Dubreuil, Stephane Gero, Alice Olesker, Catherine Verre-Sebrie, Mauro Vieira de Almeida, Georges Vass
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Patent number: 5446174Abstract: There are disclosed novel compounds that can be used to derive therefrom a fragment that corresponds to an A-ring which is to he combined 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 allylic hydroxylation to add an oxygen function group to position C(1), a method which is completely different from any existing synthetic methods.Type: GrantFiled: August 11, 1993Date of Patent: August 29, 1995Assignee: Hoxan CorporationInventor: Yuji Tahara
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Patent number: 5434274Abstract: Neuroactive benz[e]indene compounds ##STR1## are prepared by a total synthesis from the following three starting materials ##STR2##Type: GrantFiled: March 2, 1994Date of Patent: July 18, 1995Assignee: Washington UniversityInventors: Douglas F. Covey, Yuefei Hu, Mingcheng Han, Charles F. Zorumski
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Patent number: 5407902Abstract: A methoxyiminoacetic acid derivative represented by the following formula (I): ##STR1## wherein X represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; A represents a methoxy group or a methylamino group; when A is a methoxy group, B represents --O--CO-- or --N=C(R.sup.1)-- and when A is a methylamino group, B represents --O--CR.sup.1 R.sup.2 --, wherein R.sup.1 and R.sup.2 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a trifluoromethyl group; and Ar represents an optionally substituted aryl group or an optionally substituted heteroaryl group, and an agricultural/horticultural fungicide containing the same as an active ingredient.Type: GrantFiled: October 1, 1993Date of Patent: April 18, 1995Assignee: Mitsubishi Kasei CorporationInventors: Masatsugu Oda, Manabu Katsurada, Hirofumi Tomita
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Patent number: 5403846Abstract: Compounds of the general formula: ##STR1## or a pharmaceutically acceptable salt, hydrate or crystal form enantiomer, diastereomer or mixtures thereof are Class III antiarrhythmic agents.Type: GrantFiled: November 22, 1993Date of Patent: April 4, 1995Assignee: Merck & Co., Inc.Inventors: John J. Baldwin, David A. Claremon, Gerald S. Ponticello, Harold G. Selnick
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Patent number: 5387700Abstract: A process for producing chlorosulfate and sulfamate esters of 2,3:4,5-bis-O-(1-methylethylidene)-.beta.-D-fructopyranose and (1-methylcyclohexyl)methanol is disclosed. The process involves a two step procedure involving in the first step reacting of an alcohol with sulfuryl chloride in the presence of a tertiary or heterocyclic amine base in a solvent selected from the group consisting of toluene, t-butyl methyl ether or tetrahydrofuran to produce a chlorosulfate intermediate, which is preferably stabilized by an aqueous wash and/or treatment with a base, and in the second step reacting of the resulting intermediate with an amine in a solvent selected from the group consisting of t-butyl methyl ether, tetrahydrofuran and lower alkanol.Type: GrantFiled: August 12, 1993Date of Patent: February 7, 1995Assignee: McNeilab, Inc.Inventors: Cynthia A. Maryanoff, Lorraine Scott, Kirk L. Sorgi
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Patent number: 5326784Abstract: New cycloalkylalkylamines which are sigma-receptor ligands of formule (I) ##STR1## in which: R.sub.1 is H or lower alkyl; X and Y are H, OH, lower alkyl, lower alkoxy, halogen or nitrile; V.sub.1 and V.sub.2 together form a double bond attached to an oxygen atom or to a hydroxyimino radical, or are linked as an ethylenedioxy chain; A represents a valency bond, an oxygen atom, a methylene or an ethylene group; m is equal to 0, 1 or 2; n has the value of an integer from 1 to 5. Psychotropic drug which is also useful in gastroenterology.Type: GrantFiled: July 29, 1993Date of Patent: July 5, 1994Assignee: Institut de Recherche JouveinalInventors: Jean-Louis Junien, Alain Calvet, Henri Jacobelli, Francois Roman
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Patent number: 5283345Abstract: 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: GrantFiled: May 6, 1992Date of Patent: February 1, 1994Assignee: Hoxan CorporationInventor: Yuji Tahara
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Patent number: 5273997Abstract: The invention provides compounds of general formula ##STR1## wherein m is 0 or 1; each of R.sup.1 and R.sup.2, and R.sup.3 and R.sup.4 if present, independently represents a hydrogen or halogen atom or an optionally substituted alkyl, cycloalkyl or aryl group, or R.sup.1 and R.sup.2 together or R.sup.3 and R.sup.4 together represent an optionally substituted alkylene chain; X represents a cyano group, a group --COOH or a salt, ester or amido derivative thereof; Y represents an alkyl group or a halogen atom; and n represents 0, 1, 2 or 3; a process for their preparation; compositions containing such compounds and their use as fungicides.Type: GrantFiled: June 12, 1992Date of Patent: December 28, 1993Assignee: Shell Research LimitedInventors: Thomas W. Naisby, William W. Wood, Werner E. J. Simon
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Patent number: 5260472Abstract: Multigram quantities of Ins(1,4,5) P.sub.3, Ins(1,3,4) P.sub.3, and Ins(1,3,4,5)P.sub.4 are prepared in their enantiomerically pure forms from the two enantiomers of 1,2:5,6-di-O-cyclohexylidene myo-inositol. Also, a facile enzymatic preparation is also described of these chiral precursors through enantiospecific deacylation of the corresponding racemic esters is disclosed.Type: GrantFiled: January 29, 1992Date of Patent: November 9, 1993Assignee: The Board of Governors for Higher Education State of Rhode Island and Providence PlantationsInventor: Ching-Shih Chen
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Patent number: 5260459Abstract: The cyclic Isolongifolanone ketals of the general formula A wherein the wavy lines mean .alpha. and .beta.-configuration and R,R' mean radicals of hydrogen, methyl or ethyl, are new. With preference they are used either as odorants or as components of perfume compositions. They are manufactured from Isolongifolene which is itself produced from Longifolene as is well known. Isolongifolene is oxydized to Isolongifolene-3-on and this is reacted with aliphatic 1,2-diols in apolar solvents with the separation of water.Type: GrantFiled: November 18, 1992Date of Patent: November 9, 1993Inventors: Ernst-Joachim Brunke, Dietmar Schatkowski
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Patent number: 5242942Abstract: Compounds of the general formula (I): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, n and p are as herein defined; exhibit anticonvulsant activity and are thus useful in the treatment of conditions such as epilepsy. Compounds of this class are also useful for the treatment of glaucoma, peptic ulcers, hypertension, congestive heart failure and other types of edema. Furthermore, pharmaceutical compositions containing a compound of formula (I) as well as methods for their use and novel intermediates are disclosed.Type: GrantFiled: April 28, 1992Date of Patent: September 7, 1993Assignee: McNeilab, Inc.Inventors: Michael J. Costanzo, Bruce E. Maryanoff
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Patent number: 5239090Abstract: The (3S,4R)-isomer of a compound of formula (E) is disclosed.Type: GrantFiled: February 24, 1992Date of Patent: August 24, 1993Assignee: Beecham Group p.l.c.Inventor: Erol A. Faruk
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Patent number: 5200530Abstract: The invention relates to a new process for the reduction of 15-keto carbacyclin intermediates in the presence of cerium(III) Salts.Type: GrantFiled: July 31, 1991Date of Patent: April 6, 1993Assignee: Schering AktiengesellschaftInventors: Helmut Dahl, Gabriela Buttner, Dieter Peschel
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Patent number: 5158597Abstract: Dibenzo[d,g][1,3]dioxocin-6-carboxylic acids substituted by methyl or ethyl or a moiety --CH.sub.2 CH.sub.2 -- at the 12-position and optionally substituted at other positions, such as methyl 4'-chlorospiro(cyclopropane-1,12'(12'H)-dibenzo[d,g][1,3]dioxocin)-6'-carb oxylic acid, and their agriculturally acceptable esters, amides, and salts are useful for the control of undesirable vegetation. The 1,1-diarylcyclopropane intermediates required for the spirocyclopropane compounds can be prepared from appropriately substituted 1,1-diarylethene procursors by reaction with phenylthiomethyl lithium reagent.Type: GrantFiled: September 21, 1990Date of Patent: October 27, 1992Assignee: The Dow Chemical CompanyInventors: Michael G. Smith, James M. Renga, Brian K. Riley, Patricia G. Ray, Charles Marlowe
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Patent number: 5011950Abstract: Novel aromatic amine derivatives of specific structure are useful intermediates for herbicides. The aromatic amine compounds have the structure shown by formula [I]: ##STR1## wherein Ar and A are as defined herein.Type: GrantFiled: February 2, 1988Date of Patent: April 30, 1991Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Daisuke Fukuoka, Katsuya Takahashi, Isao Hashimoto
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Patent number: 4964846Abstract: This invention comprises a process for the production of unsymmetrical olefins from prochiral symmetrical ketones by addition of lithiosulfoximine from n-butyllithium and N-substituted S-methyl-S-phenyl-sulfoximine derivatives and then reaction with n-butyllithium/trimethychlorosilane.Type: GrantFiled: November 21, 1988Date of Patent: October 23, 1990Assignee: Schering AktiengesellschaftInventors: Hans-Joachim Gais, Irene Erdelmeier, Rolf Birk
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Patent number: 4960907Abstract: The invention relates to a process for the production of D,L-bicyclo[3.3.0]octane-3,7-dione-2-carboxylic acid esters of Formula I ##STR1## wherein R is methyl or ethyl, andZ isoxygen or the ketal residue ##STR2## wherein X means ethylene, trimethylene or 2,2-dimethyltrimethylene, characterized in that D,L-bicyclo[3.3.0]octane-3,7-dione-2,6-dicarboxylic acid esters of Formula II ##STR3## wherein R has the meanings given above, are partially saponified and decarboxylated in an aqueous or water-containing medium in the presence of acids, and are optionally selectively ketalized.Type: GrantFiled: July 24, 1989Date of Patent: October 2, 1990Assignee: Schering AktiengesellschaftInventors: Helmut Vorbrueggen, Konrad Krolikiewicz
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Patent number: 4942173Abstract: The present invention relates to a compound of the formula (I): ##STR1## wherein R is C.sub.2-10 alkyl, alkenyl or alkynyl, each optionally substituted by or methyl substituted by cyano, C.sub.3-4 cycloalkyl, halo, C.sub.1-4 alkoxy or a group S(O)m R.sup.4 where R.sup.4 is C.sub.1-4 alkyl and m is 0, 1 or 2, or Ris C.sub.3-10 cycloalkyl, C.sub.4-10 cycloalkenyl or phenyl, each optionally substituted by C.sub.1-4 alkoxy, C.sub.1-3 alkyl, C.sub.2-4 alkynyl, halo, cyano or a group S(O)m R.sup.4 as defined hereinbefore; R.sup.1 is halo, C.sub.1-3 alkyl, C.sub.2-3 alkenyl or alkynyl each optionally substituted by halo, cyano, C.sub.1-4 alkoxy, alkyl carbalkoxy containing up to 6 carbon atoms, a group S(O)m R.sup.4 as defined hereinbefore or alkynyl substituted by tri-C.sub.1-4 alkylsilyl, or R.sup.1 is cyano, spiro-cyclopropyl, gem dimethyl, gem dicyano, gem diethynyl, oxo or methylene optionally substituted by cyano of C.sub.1-3 alkyl optionally substituted by fluorine, or R.sup.Type: GrantFiled: February 24, 1989Date of Patent: July 17, 1990Assignee: The Regents of the University of CaliforniaInventors: John E. Casida, Christopher J. Palmer, John P. Larkin, Ian H. Smith
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Patent number: 4933475Abstract: Compounds having the formula ##STR1## R.sub.1 is hydrogen, benzyl or alkanoyl, X is C.sub.2-4 alkylene; andZ-W is alkyl, phenylalkyl or pyridylalkyl which can have an oxygen atom as part of the alkyl chain and their use as CNS agents, antidiarrheals and antiemetics. Processes for their preparation and intermediates therefor are described.Type: GrantFiled: February 28, 1989Date of Patent: June 12, 1990Assignee: Pfizer, Inc.Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
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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: 4925956Abstract: The invention relates to a process for manufacturing optically active carbacyclin intermediate products from racemic cis-bicyclo[3.3.0]octane-2-carboxylic acids. This process makes it possible in an advantageous way to produce important intermediates for the synthesis of stable and pharmacologically active carbacyclin derivatives.Type: GrantFiled: July 13, 1988Date of Patent: May 15, 1990Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Helmut Dahl
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Patent number: 4910350Abstract: A compound represented by formula (I): ##STR1## wherein R represents a straight chain alkyl group having from 1 to 9 carbon atoms; ##STR2## represents ##STR3## represents a hydrogen atom or a fluorine atom; and ##STR4## has a trans (equatorial-equatorial) configuration, is disclosed. The compound of formula (I) exhibits a nematic phase in the vicinity of room temperature or in a temperature range higher than room temperature and has a small optical anisotropy and a positive dielectric anisotropy and is, therefore, useful in preparing a liquid crystal display cell excellent in viewing-angle characteristics.Type: GrantFiled: September 28, 1988Date of Patent: March 20, 1990Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Yasuyuki Tanaka, Haruyoshi Takatsu, Kiyohumi Takeuchi, Yuuji Tamura
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Patent number: 4894336Abstract: Process for the production of optically active (+)-bicyclo[3.3.0]octanol derivatives of formula (+)-I, in which R.sub.1 and R.sub.2 represent jointly an oxygen atom or the double-bond residue --O--X--O-- with X as a straight or branched-chain alkylene with 1-7 C-atoms, or R.sub.1 and R.sub.2 represent separately the residue OR.sub.5 with R.sub.5 as a straight or branched-chain alkyl with 1-7 C-atoms, and R.sub.3 the residue COOZ with Z as a hydrogen atom, straight or branched chain alkyl with 1-7 C atoms, cycloalkyl with 3-6 C atoms, phenyl or aralkyl with 7-10 atoms or R.sub.3 is the residue --(CH.sub.2).sub.n --O--COR.sub.4 with n having the meaning 1-4 and R.sub.4 as a straight or branched-chain alkyl with 1-7 C atoms, cycloalkyl with 3-6 C atoms, phenyl or aralkyl with 7-10 C atoms. The process is characterized in that racemic 3.alpha.-cyloxy-cis-bicyclo[3.3.0]-octane derivatives of formula (+)-II, wherein R.sub.1, R.sub.2 R.sub.3 and R.sub.Type: GrantFiled: July 13, 1988Date of Patent: January 16, 1990Assignee: Schering AktiengesellschaftInventors: Karl Petzoldt, Helmut Dahl, Werner Skuballa
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Patent number: 4885246Abstract: New intermediate, an optically active (1S,5R)-7,7-alkylenedioxy-2-alkoxycarbonylbicyclo[3.3.0]octan-3-one which is useful for the synthesis of an optically active carbacyclin. This intermediate is prepared, as a non-reduced compound, from a racemic compound, (1SR,5RS)-7,7-alkylenedioxy-2-alkoxycarbonyl-cis-bicyclo[3.3.0]octan-3-one , by treatment of the racemic compound with a microorganism. The microorganism has an ability of specifically reducing the keto group of the (1R,5S) epimer of the racemic compound.Type: GrantFiled: December 19, 1988Date of Patent: December 5, 1989Assignee: Nisshin Flour Milling Co., Ltd.Inventors: Kenji Mori, Masahiro Tsuji
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Patent number: 4882439Abstract: Total synthesis of steroids with substitution in the 2,3, 6, 11 or 17 positions comprising the step of cyclization of a compound having the formula ##STR1## or analogues thereof, where X represents .dbd.O, ##STR2## or .beta.-substituted ##STR3## Y represents .dbd.O, .beta.-oriented ##STR4## or .beta.-orientated OH, R' and R.sup.2 may be the same or different and R' represents alkyl or aryl and R.sup.Type: GrantFiled: September 19, 1986Date of Patent: November 21, 1989Assignee: The University of SheffieldInventor: David N. Jones
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Patent number: 4857516Abstract: A compound of the formula ##STR1## wherein R is a lower alkyl group, R.sup.0 is hydrogen or an acyl group, R.sup.1 and R.sup.2 are lower alkyl groups which may optionally be substituted or wherein R.sup.1 and R.sup.2 are combined to form a butadienylene group which may optionally be substituted, R.sup.3 and R.sup.4 are hydrogen or alkyl groups which may optionally be substituted or wherein R.sup.3 and R.sup.4 are combined to form a polymethylene group, and R.sup.5 is a lower alkyl, aromatic or heterocyclic group which may optionally be substituted or a pharmaceutically acceptable salt thereof, exerts cardiovascular system improving action and antiallergic action and can be used as pharmaceutics, e.g. antithromotics, antiallergic agents etc.Type: GrantFiled: December 22, 1987Date of Patent: August 15, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Shinji Terao, Yoshitaka Maki
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Patent number: 4841075Abstract: A method of preparing an acetal or ketal from a corresponding aldehyde or ketone is disclosed. A hydrous oxide of an element of Group IV of the Periodic Table is used as a catalyst, and the aldehyde or ketone is caused to react with an alcohol. The hydrous oxide can be obtained by partially dehydrating a hydroxide of the corresponding element. The method does not require an acid catalyst and is applicable to a carbonyl compound which is not stable in acids.Type: GrantFiled: December 7, 1987Date of Patent: June 20, 1989Assignee: Japan Tobacco, Inc.Inventors: Hajime Matsushita, Makoto Shibagaki, Kyoko Takahashi, Hideyuki Kuno
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Patent number: 4824952Abstract: An isoquinoline derivative of the following formula: ##STR1## wherein R.sub.1 is a methyl or a methoxymethyl group and R.sub.2 and R.sub.3 are each a hydrogen atom or a methyl, ethyl, methoxy, a cyclohexyl, a phenyl, a 3,4-dimethoxyphenyl, a pyridyl or an oxo (.dbd.O) group;and therapeutically acceptable salts thereof which exhibit a low toxicity and a wide range of safety and are highly useful as a cardiotonic medication.Type: GrantFiled: July 12, 1985Date of Patent: April 25, 1989Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tsuneji Suzuki, Kunio Sannohe, Toshihiko Ito, Masahiko Maruyama, Joji Kamiya, Makoto Hirayama, Takafumi Kitano, Akira Awaya
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Patent number: 4814468Abstract: New intermediate, an optically active (1S,5R)-7,7-alkylenedioxy-2-alkoxycarbonylbicyclo[3.3.0]octan-3-one which is useful for the synthesis of an optically active carbacyclin. This intermediate is prepared, as a non-reduced compound, from a racemic compound, (1SR,5RS)-7,7-alkylenedioxy-2-alkoxycarbonyl-cis-bicyclo[3.3.0]octane-3-on e, by treatment of the racemic compound with a microorganism. The microorganism has an ability of specifically reducing the keto group of the (1R,5S) epimer of the racemic compound.Type: GrantFiled: May 30, 1986Date of Patent: March 21, 1989Assignee: Nisshin Flour Milling Co., Ltd.Inventors: Kenji Mori, Masahiro Tsuji
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Patent number: 4806285Abstract: Novel diterpene compounds are separated from dry biomass of Grindelia camporum. The separated compounds are then hydrogenated and esterified. Both the hydrogenated and ester products are useful as tackifiers.Type: GrantFiled: November 4, 1987Date of Patent: February 21, 1989Assignee: Arizona Technology Development Corp.Inventors: Joseph J. Hoffman, Louis K. Hutter
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Patent number: 4792606Abstract: A process for the preparation of a dimeric aromatic acyl cyanide of the formula ##STR1## in which Ar is optionally substituted phenyl, naphthyl or hetaryl,comprising reaction an acyl halide of the formulaAr--CO--Halin whichHal is fluorine, chlorine or bromine, with an alkali metal cyanide in a two-phase system comprising water and a water-immiscible or only sparingly water-miscible aliphatic ketone, and in the presence of a phase-transfer catalyst. The products are known intermediates for pesticides.Type: GrantFiled: July 16, 1987Date of Patent: December 20, 1988Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Hermann-Dieter Krall