Chalcogen Attached Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 549/374)
  • Patent number: 5571931
    Abstract: An improved process for preparing a vinyl-substituted dioxo compound, in which process a vinyl aldehyde is reacted with a compound having three or more hydroxyl groups. In particular, the reaction is carried out, using an acid catalyst, in an organic solvent comprising an aliphatic solvent which forms a binary azeotrope with water as the reaction is driven to completion.
    Type: Grant
    Filed: May 5, 1995
    Date of Patent: November 5, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Basil V. Gregorovich
  • Patent number: 5565583
    Abstract: Hemiacetals of glyoxal monoacetals are useful as intermediates to prepare 2-substituted but-2-en-1,4-dial-4-acetals of the general formula I; ##STR1##
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: October 15, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: J urgen Frank, Johann-Peter Melder, Franz Merger, Tom Witzel
  • Patent number: 5559201
    Abstract: A cycloaliphatic acrylic monomer having the general formula ##STR1## wherein R.sub.1 is hydrogen, methyl, hydroxyl, HO--(R.sub.3).sub.n or ##STR2## R.sub.2 is ##STR3## R.sub.3 is C.sub.2 H.sub.4 O, C.sub.3 H.sub.6 O, C.sub.4 H.sub.8 O, C.sub.8 H.sub.8 O or mixtures thereof; R.sub.4 is hydrogen or methyl; and n is 1-24. The acrylic monomer is useful as a component in compositions which are radiation curable.
    Type: Grant
    Filed: July 19, 1995
    Date of Patent: September 24, 1996
    Assignee: Perstorp AB
    Inventor: Kent S orensen
  • Patent number: 5523010
    Abstract: A process of lubricating or releasing comprising disposing a lubricant release composition between frictional contacting parts or between parts to be released from each other, respectively, wherein the composition includes 5-alkyl-1,3-dioxane-5-methanol and esters and/or ethers thereof, the alkyl in the aforementioned compounds being methyl or ethyl.
    Type: Grant
    Filed: December 22, 1994
    Date of Patent: June 4, 1996
    Assignee: Perstorp AB
    Inventors: Kent Sorensen, Lars-Olof Garpvall, Mats Johansson
  • Patent number: 5508275
    Abstract: Lipid-selective antioxidants of the formula I(A).sub.a (L)(X).sub.a, (I),in whichA=an antioxidative component,L=a bridging member,X=a lipophilic componenta and a'=independently of one another the numbers 1 or 2.The compounds are used for the protection of lipid-containing substances against oxidation and in pharmaceuticals for the prophylaxis and treatment of diseases in which bioradicals are involved, in particular of coronary, circulatory and vascular diseases.
    Type: Grant
    Filed: March 15, 1994
    Date of Patent: April 16, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Klaus-Ulrich Weithmann, Gunther Wess, Dirk Seiffge
  • Patent number: 5474705
    Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) an aliphatic fluorocarbon terminal portion containing at least two catenary ether oxygen atoms; (b) a chiral, aliphatic hydrocarbon terminal portion; and (c) a central core connecting the terminal portions. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.
    Type: Grant
    Filed: November 14, 1994
    Date of Patent: December 12, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Eugene P. Janulis, Gilbert C. Johnson, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
  • Patent number: 5449793
    Abstract: A novel optically active erythro-1-alkanoyloxy-2,4-O-isopropylidene-2,4-dihydroxy-5-substituted pentane expressed by the formula ##STR1## wherein R.sup.1 represents a halogen atom or cyano group and R.sup.2 represents an alkyl group of 1 to 6 carbon atoms, and a process for producing the above compound are provided, the compound being preferably usable as an intermediate for preparing a HMG-CoA reductase inhibitor and the process being practiced under mild conditions and with a high yield.
    Type: Grant
    Filed: May 12, 1994
    Date of Patent: September 12, 1995
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Teruyo Sugiura, Yasuyuki Koizumi, Naoyuki Yoshida
  • Patent number: 5447657
    Abstract: The present invention provides compounds of the general formula: ##STR1## wherein R is an alkyl group with 1 to 12 carbon atoms or a group of the formula ##STR2## Ring A.sup.1 is 1,4-phenylene, which is unsubstituted or substituted with fluorine, pyridine-2,5-diyl or pyrimidine-2,5-diyl;Ring A.sup.2 is trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl;R.sup.1 is an alkyl, alkenyl or alkoxyalkyl group with 1 to 12 and, respectively, 2 to 12 carbon atoms;X.sup.1 is fluorine, chlorine, bromine, trifluoromethyl, trifluoromethoxy or difluoromethoxy; andX.sup.2, X.sup.3 each independently are hydrogen or fluorine.The invention is also concerned with liquid crystal mixtures which contain these compounds and with the use of these compounds and mixtures for electro-optical purposes.
    Type: Grant
    Filed: March 8, 1994
    Date of Patent: September 5, 1995
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Martin Schadt, Alois Villiger
  • Patent number: 5399673
    Abstract: Compounds containing at least one alkenyl group, at least one maleimide group and at least one rodlike mesogenic moiety are prepared by reacting one or more aminophenols containing one or more rodlike mesogenic moieties with a stoichiometric quantity of a maleic anhydride per amine group of said aminophenol and then alkenylating the resulting phenolic functional maleimide.
    Type: Grant
    Filed: February 9, 1993
    Date of Patent: March 21, 1995
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 5399291
    Abstract: Fluorine-containing, chiral and achiral liquid crystal compounds comprise (a) an aliphatic fluorocarbon terminal portion comprising a perfluorinated or partially-fluorinated alkylene group and a terminal hydrocarbon alkyl group, the groups optionally containing at least one catenary ether oxygen atom; (b) an aliphatic hydrocarbon terminal portion; and (c) a central core connecting the terminal portions. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.
    Type: Grant
    Filed: September 30, 1993
    Date of Patent: March 21, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Eugene P. Janulis, Gilbert C. Johnson, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
  • Patent number: 5374654
    Abstract: The invention relates to carbacyclin derivatives of Formula I ##STR1## wherein the various substituents are defined herein, including, inter alia,if R.sub.2 is a hydrogen atom, their salts with physiologically compatible bases, their cyclodextrin clathrates, and their use as medicinal agents.
    Type: Grant
    Filed: April 21, 1993
    Date of Patent: December 20, 1994
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Ulrich Klar, Bob Nieuweboer, Claus-Steffen Sturzebecher
  • Patent number: 5372746
    Abstract: Compounds of the general formula ##STR1## wherein ring A represents 1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl;Z signifies a single covalent bond, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 O-- or, where ring A represents a saturated ring, also the trans form of --CH.dbd.CH(CH.sub.2).sub.2 -- or --CH.dbd.CHCH.sub.2 O--;X signifies fluorine, chlorine, cyano, --CF.sub.3, --OCF.sub.3 or --OCHF.sub.2 ;Y.sup.1, Y.sup.2 each independently signify fluorine or hydrogen; andR signifies alkyl, alkoxy, alkenyl or alkenyloxy with 1 or, respectively, 2 to 12 carbon atoms in which one CH.sub.2 group or two non-adjacent CH.sub.
    Type: Grant
    Filed: November 17, 1992
    Date of Patent: December 13, 1994
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Buchecker, Martin Schadt
  • Patent number: 5278318
    Abstract: Retinold-like activity is exhibited by compounds of the formula ##STR1## where X is S, O; R.sub.1, R.sub.2 and R.sub.3 are hydrogen or lower alkyl; R.sub.4 and R.sub.5 are hydrogen or lower alkyl with the proviso that R.sub.4 and R.sub.5 cannot both be hydrogen, R.sub.6 is hydrogen, lower alkyl, lower alkenyl, lower cycloalkyl or halogen; n is 0-5, and B is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or --COR.sub.1 or a ketal derivative where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4, or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: October 21, 1992
    Date of Patent: January 11, 1994
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5268491
    Abstract: A process for the selective dehalogenation in position 5 of the naphthalenic nucleus of compounds of formula ##STR1## (wherein X, X.sub.1 and R have the meanings reported in the description) by treatment with a dehalogenating agent selected among hydrogen sulfide, aliphatic thiols or mixtures thereof in an inert anhydrous solvent at acid pH.
    Type: Grant
    Filed: October 16, 1992
    Date of Patent: December 7, 1993
    Assignee: Zambon Group S.p.A.
    Inventors: Marco Villa, Paolo Cavalleri
  • Patent number: 5266708
    Abstract: New intermediates and processes for the preparation of vitamins A and E, which are the acetals of 5,6-dihalo-3-methyl-3-hydroxyhexanal or of 6-halo-3-hydroxy-3-methyl-5-hexenal or 3-methyl-3-hydroxy-5-hexenal, as well as processes for making the intermediates. After dehydrohalogenation and dehydration these intermediates are condensed directly with .beta.-ionone or with 2-methyl-2-heptene-6-one to synthesize vitamins A and E respectively.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: November 30, 1993
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre F. Charbardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
  • Patent number: 5262082
    Abstract: Fluorine-containing liquid crystal compounds are provided. The compounds comprise a fluorocarbon terminal portion having at least one catenary ether oxygen and a hydrocarbon terminal portion, the terminal portion being connected by a central core, the compounds having smectic mesophases or having latent smectic mesophases.
    Type: Grant
    Filed: April 28, 1992
    Date of Patent: November 16, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Eugene P. Janulis, Gilbert C. Johnson, Patricia M. Savu, Terence D. Spawn
  • Patent number: 5254698
    Abstract: Phenyldioxanes of the formula I ##STR1## wherein R.sup.1 is an alkyl or alkenyl residue each with up to 16 C atoms, wherein one or two non-adjacent CH.sub.2 groups of these residues may be replaced by --CO--O-- or --O--CO--,Q.sup.1 and Q.sup.2 are each independently ##STR2## L.sup.1 and L.sup.2 are each independently F or H, and Y is Cl, F, CN, CF.sub.3, OCF.sub.3 or OCF.sub.2 H,m and n is 0 or 1,are suitable as components of liquid crystal media.
    Type: Grant
    Filed: February 12, 1991
    Date of Patent: October 19, 1993
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: David Coates, Simon Greenfield, Graham Smith, Volker Reiffenrath, Joachim Krause, Herbert Plach
  • Patent number: 5250220
    Abstract: Novel 2,5-disubstituted heterocyclic compounds of the formula I ##STR1## in which n is 1 to 10,Het is ##STR2## Ring A is trans-1,4-cyclohexylene or, in the case where Het= ##STR3## X=--OCF.sub.3 or --OCHF.sub.2 and/or Y=Z=F, is alternatively 1,4-phenylene,X is CN, F, Cl, --CF.sub.3, --OCF.sub.3 or --OCHF.sub.2, andY and Z are each, independently of one another, H or F, can be used as components of liquid-crystalline media.
    Type: Grant
    Filed: September 18, 1992
    Date of Patent: October 5, 1993
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Andreas Wachtler, Reinhard Hittich, Eike Poetsch, Joachim Krause, Ulrich Finkenzeller, David Coates
  • Patent number: 5250715
    Abstract: The present invention provides an optically active 2-methylenepentane derivative represented by the general formula ##STR1## (wherein R.sup.1 is a protective group for hydroxyl, R.sup.3 is a protective group for hydroxyl, X is a halogen atom or R.sup.4 SO.sub.3 group (wherein R.sup.4 is an alkyl or an aryl), and the symbol * represents an asymmetric carbon atom).
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: October 5, 1993
    Assignee: Daiso Co., Ltd.
    Inventors: Takashi Takahashi, Yoshikazu Takehira
  • Patent number: 5219881
    Abstract: The invention concerns a cyclic ether derivative of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl or naphthyl;A.sup.1 is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo-(3-6C)alkylene;Ar.sup.2 is optionally substituted phenylene, or a 6 membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 and R.sup.2 together form a group of the formula --A.sup.2 --X--A.sup.3 -- wherein each of A.sup.2 and A.sup.3 is (1-6C)alkylene and X is oxy, thio, sulphinyl, sulphonyl or imino; andR.sup.3 is (1-6C)alkyl, (2-6C)alkenyl, (2-6C)alkynyl or substituted (1-4C)alkyl;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: December 10, 1991
    Date of Patent: June 15, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventor: Annie Hamon
  • Patent number: 5189180
    Abstract: Seco-mevinic acid derivatives are provided which have the structure ##STR1## including all stereoisomers thereof, wherein Z is ##STR2## R is H, alkali metal or lower alkyl, R.sup.1 is H, lower alkyl, aryl, lower alkoxy, cycloalkyl, heteroaryl, aralkyl, heteroaralkyl or heterocyclic; R.sup.2 is lower alkyl, cycloalkyl or aralkyl, and X is O or NR.sup.5 wherein R.sup.5 is H or lower alkyl, and are HMG CoA reductase inhibitors and thus are useful as antihypercholesterolemic agents and in treating atherosclerosis.New intermediates for preparing the above seco-mevinic acid derivatives are also provided.
    Type: Grant
    Filed: May 1, 1991
    Date of Patent: February 23, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Donald S. Karanewsky
  • Patent number: 5171472
    Abstract: A compound represented by formula (I). ##STR1## wherein R represents a straight chain alkyl group having 1 to 7 carbon atoms; n is an integer of 1 to 5; X represents F, Cl or CN; Y represents H or F; and a dioxane ring in a trans configuration with respect to a cyyclohexane ring.
    Type: Grant
    Filed: April 10, 1991
    Date of Patent: December 15, 1992
    Assignees: Dainippon Ink and Chemicals, Inc., Hoffman-La Roche Inc.
    Inventors: Yasuyuki Tanaka, Haruyoshi Takatsu, Kiyofumi Takeuchi, Martin Schadt, Richard Buchecker
  • Patent number: 5164518
    Abstract: The present invention provides a method for the alpha,omega-arylation/alkylation of a non-conjugated diene in one step by reacting the diene with an aryl iodide or an aryl bromide and a carbon nucleophile in the presence of an amount of a Pd(O) complex effective to catalyze the reaction.
    Type: Grant
    Filed: July 12, 1991
    Date of Patent: November 17, 1992
    Assignee: Iowa State University Research Fondation Inc.
    Inventor: Richard C. Larock
  • Patent number: 5162365
    Abstract: This invention encompasses compounds and methods for inhibiting lipoxygenase and includes a pharmaceutical composition comprising a pharmaceutical carrier and an effective lipoxygenase inhibiting amount of a compound of the formula: ##STR1## wherein the substituents are defined below. The compounds and pharmaceutical formulations of the present invention are 5-lipoxygenase inhibitors and, therefore, are useful in the treatment of local and systemic inflammation, allergy and hypersensitivity reactions and other disorders in which agents formed in the 5-lipoxygenase metabolic pathway are involved.
    Type: Grant
    Filed: May 10, 1991
    Date of Patent: November 10, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Leland J. Chinn, Bipinchandra N. Desai, Richard A. Mueller
  • Patent number: 5162353
    Abstract: The invention relates to carbacyclin derivatives with general formula I: ##STR1## in which Y.sub.1 stands for the radical --CH.sub.2 --X--(CH.sub.2).sub.n --R.sub.1 or the radical ##STR2## n, 1 or 3, R.sub.1, the radical ##STR3## the radical ##STR4## R.sub.9 stands for the radical --(CH.sub.2).sub.m --R.sub.6 or the radical --(CH.sub.2).sub.m-o --[Z.sub.1 --(CH.sub.2).sub.m-p ].sub.x --[Z.sub.2 --(CH.sub.2).sub.m-q ].sub.y --R.sub.6,m=2-20,o, p, and q are less than or equal to 19,x, y=0, 1 or 2,Z.sub.1 stands for a cis--CH.dbd.CH group, a trans--CH.dbd.CH group of a --C.dbd.C group, and each of these groups must be separated at least by a methylene group from the C-9 carbon atom of the carbacyclin bicyclic compound,Z.sub.2 stands for oxygen, sulfur, an NH or an N methyl group,R.sub.6 stands for amino, methylamino, hydroxy, carboxy or mercapto,X an oxygen atom or a methylene group,Y.sub.2 hydrogen or fluorine,A a --CH.sub.2 --CH.sub.2, trans--CH.dbd.CH or --C.dbd.
    Type: Grant
    Filed: August 21, 1990
    Date of Patent: November 10, 1992
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbrueggen, Bob Nieuweboer, Claus-Steffen Stuerzebecher
  • Patent number: 5162546
    Abstract: Retinold-like activity is exhibited by compounds of the formula ##STR1## where X is S, O; R.sub.1, R.sub.2 and R.sub.3 are hydrogen or lower alkyl; R.sub.4 and R.sub.5 are hydrogen or lower alkyl with the proviso that R.sub.4 and R.sub.5 cannot both be hydrogen, R.sub.6 is hydrogen, lower alkyl, lower alkenyl, lower cycloalkyl or halogen; n is 0-5, and B is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or --COR.sub.1 or a ketal derivative where R.sub.1 l is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4, or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: August 26, 1991
    Date of Patent: November 10, 1992
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5137913
    Abstract: The invention concerns a diaryl ether cyclic ether of the formula I, or a pharmaceutically-acceptable salt thereof, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl or naphthyl;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is optionally substituted phenylene, or a 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 and R.sup.2 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- wherein each of A.sup.2 and A.sup.3 is (1-4C) alkylene and X.sup.2 is oxy, thio, sulphinyl, sulphonyl or imino; andR.sup.3 is (1-6C)alkyl, (2-6C)alkenyl, (2-6C)alkynyl and substituted (1-4C)alkyl.The invention also concerns processes for the manufacture of a diaryl ether cyclic ether of the formula I, or a pharmaceutically-acceptable salt thereof, and pharmaceutical compositions containing said cyclic ether. The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: December 12, 1991
    Date of Patent: August 11, 1992
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Thomas G. C. Bird, Philip N. Edwards
  • Patent number: 5128479
    Abstract: Oxidized diphenylheteroalkanes of the formula I ##STR1## where R.sup.1 to R.sup.6 and A have the meanings specified in the description, and the preparation thereof are described. The substances are suitable for controlling diseases and as cosmetic agents.
    Type: Grant
    Filed: January 29, 1990
    Date of Patent: July 7, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5120864
    Abstract: New intermediates and processes for the preparation of vitamins A and E, which are the acetals of 5,6-dihalo-3-methyl-3-hydroxyhexanal or of 6-halo-3-hydroxy-3-methyl-5-hexenal or 3-methyl-3-hydroxy-5-hexenal, as well as processes for making the intermediates. After dehydrohalogenation and dehydration these intermediates are condensed directly with .beta.-ionone or with 2-methyl-2-heptene-6-one to synthesize vitamins A and E respectively.
    Type: Grant
    Filed: December 3, 1990
    Date of Patent: June 9, 1992
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre F. Charbardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
  • Patent number: 5100577
    Abstract: A ferroelectric liquid crystalline mixture containing at least one optically active compound of the general formula ##STR1## wherein X.sup.1 denotes a single covalent bond, --COO--, --OOC--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 -- or --CH.sub.2 O--; one of rings A.sup.1, A.sup.2 and A.sup.3 represents trans-m-dioxan-2,5-diyl and the other two of rings A.sup.1, A.sup.2 and A.sup.3 each independently represent unsubstituted 1,4-phenylene or 1,4-phenylene substituted with cyano, halogen or lower alkyl; R.sup.1 and R.sup.2 each independently signify an optionally halogen-substituted alkyl group with up to 18 carbon atoms in which optionally 1 CH.sub.2 group or 2 non-adjacent CH.sub.2 groups is/are replaced by --O--, --CO--, --COO-- and/or --OOC--,as well as novel compounds falling under formula I and ferroelectric electrode-optical indicating devices including same.
    Type: Grant
    Filed: January 11, 1990
    Date of Patent: March 31, 1992
    Assignee: Hoffman-La Roche Inc.
    Inventors: Richard Buchecker, Hans-Jurgen Fromm, Stephen Kelly, Martin Schadt, Alois Villiger
  • Patent number: 5072002
    Abstract: Processes of synthesizing compounds of the formula: ##STR1## wherein R.sub.1 is H, lower alkyl (1 to 6 C), lower dialkyl (1 to 6 C), lower cycloalkyl (3 to 7 C), or lower dicycloalkyl (3 to 7 C);R.sub.2 is H, lower alkyl (1 to 6 C), or lower cycloalkyl (3 to 7 C);R.sub.5 C(O) is an acyl group with R.sub.5 being alkyl (1 to 18 C), cycloalkyl, bicycloalkyl, tricycloalkyl, alkenyl (1 to 18 C), alkadienyl (1 to 18 C), aryloxy-, alkoxy-, substituted alkyl, wherein the substituents are acetoxy-, acyl-, alkoxy-, alkoxycarbonyl-, alkylamido-, alkylsulfonyl-, alkylsulfoxido-, alkylthio-, alkylthiocarbonyl-, amino-, aroyl-, aryl-, aryloxy-, arylthio-, azido-, carboxy-, dialkylamido-, dialkylamino-, dihalogeno-, hydroxy-, monohalogeno-, trihalogeno-, or arylalkylthio-.Compounds of the above formula are capable of appreciably lowering blood levels of cholesterol in human beings.
    Type: Grant
    Filed: July 18, 1989
    Date of Patent: December 10, 1991
    Assignee: The Governors of the University of Alberta
    Inventors: Derrick L. J. Clive, Andrew G. H. Wee, Kammaralli S. K. Murthy
  • Patent number: 5011943
    Abstract: A process is described for the improved synthesis of the optically pure C.sub.10 -C.sub.24 fragment of the macrolide structure of the immunosuppressant FK-506. This compound is also useful as an intermediate for preparing FK-506 derivatives.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: April 30, 1991
    Assignee: Merck Frosst Canada, Inc.
    Inventor: Zhaoyin Wang
  • Patent number: 4985546
    Abstract: A substituted colorant which may be copolymerized with a condensation polymer to provide a covalently bound, nonextractable coloring, having the formula ##STR1## wherein R and R.sub.1 are independently selected from hydrogen or lower alkyl; R.sub.4 is selected from hydrogen or lower alkyl; x is 0 or 1; N and M are each integers of from 1 to about 100 and the sum of N and M is from 3 to about 100. The hydroxyl groups are protected by formation of a ring structure during alkoxylation and amination of the substituent.
    Type: Grant
    Filed: June 19, 1989
    Date of Patent: January 15, 1991
    Assignee: Milliken Research Corporation
    Inventors: John W. Miley, John W. Rekers
  • Patent number: 4983629
    Abstract: 11-Haloprostane derivatives of general Formula I ##STR1## wherein X is F, Cl or Br,R.sub.1 is the residue CH.sub.2 OH or ##STR2## wherein R.sub.2 means a hydrogen atom, an alkyl, cycloalkyl, aryl, phenacyl or heterocyclic residue,A is a --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--group,B is a --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH-- or a --C.tbd.C--group,W is an ethylenedioxymethylene group or a hydroxymethylene group,D and E together mean a direct bond orD is a C.sub.1-10 -alkylene group,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C--bond or a --CR.sub.6 .dbd.CR.sub.7 -group with R.sub.6 and R.sub.7 meaning a hydrogen atom, a chlorine atom or an alkyl group,R.sub.4 is a hydroxy group,R.sub.5 is a hydrogen atom, an alkyl, a cycloalkyl, an aryl or a heterocyclic group, andthe salts thereof with physiologically compatible bases, processes for their preparation, and use thereof as agents inhibiting gastric acid secretion.
    Type: Grant
    Filed: June 21, 1989
    Date of Patent: January 8, 1991
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Claus-Steffen Sturzebecher, Walter Elger
  • Patent number: 4977281
    Abstract: Primary amino polyoxyalkylene 1,3-dioxane or 1,3-dioxolane compounds are provided of the formula: ##STR1## wherein R and R.sub.1 are independently selected from hydrogen or a lower alkyl group; R.sub.2 and R.sub.3 are independently selected from hydrogen, phenyl or lower alkyl groups; R.sub.4 is selected from hydrogen or a lower alkyl group; x is 0 or 1; N and M are each integers of from 1 to about 100 and the sum of N an M is from 2 to about 100; also disclosed are polyoxyalkylene amino alcohol compounds which may be derived from the compounds of Formula I above having the formula: ##STR2## wherein R, R.sub.1, R.sub.4, x, N and M all have the values given above. Also provided is a process for preparing a primary amino polyoxyalkylene 1,3-dioxane or 1,3-dioxolane.
    Type: Grant
    Filed: December 21, 1987
    Date of Patent: December 11, 1990
    Assignee: Milliken Research Corporation
    Inventors: John W. Miley, John W. Rekers
  • Patent number: 4971987
    Abstract: The invention also relates to carbacyclin derivatives of general formula I' ##STR1## wherein R.sub.9 is an alkyl group of 1-10 carbon atoms or the group --C.dbd.C--(CH.sub.2).sub.m --R.sub.6 whereinm is 1 to 16 andR.sub.6 is hydroxy on amino.
    Type: Grant
    Filed: March 7, 1988
    Date of Patent: November 20, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbrueggen, Bob Nieuweboer, Claus-Steffen Stuerzebecher, Ulrich Klar
  • Patent number: 4962207
    Abstract: The present application discloses novel potassium salts of particular tellurium and selenium compounds which are useful for the stimulation of the production of cytokines.
    Type: Grant
    Filed: October 9, 1987
    Date of Patent: October 9, 1990
    Assignee: Bar-Ilan University
    Inventors: Michael Albeck, Benjamin Sredni
  • Patent number: 4947005
    Abstract: 1,1,2-Trialkoxyethanes of the general formula I ##STR1## where R.sup.1 to R.sup.3 are each independently of the others C.sub.1 -C.sub.20 -alkyl or cycloalkyl, or R.sup.1 and R.sup.2 may be linked together to form a 5-, 6- or 7-membered ring, are prepared by reacting formaldehyde dialkyl acetals of the general formula II ##STR2## where R.sup.1 and R.sup.2 are each as defined above, or compounds which are capable of forming formaldehyde dialkyl acetals under the reaction conditions, with carbon monoxide, hydrogen and alkanols R.sup.3 OH under superatmospheric pressure at elevated temperature in the presence of a catalyst composed of a cobalt carbonyl compound and a promotor, wherein the promotor is an alkali metal, alkaline earth metal or ammonium salt of a protogenic compound having an acid constant K.sub.a of from 10.sup.-2 to 10.sup.-14, an alkali metal or alkaline earth metal hydroxide or an aminocarboxylic acid.
    Type: Grant
    Filed: August 25, 1989
    Date of Patent: August 7, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Koeffer, Werner Bertleff
  • Patent number: 4943384
    Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 are each H or an alkyl group which has 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-groups, and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, or are F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --Z.sup.o --A-- or --A--Z.sup.o --A.sup.4 --,A is a trans-1,4-cyclohexylene or 1,4-cyclohexenylene group which is unsubstituted or is monosubstituted or polysubstituted in the 2-, 3-, 5- and/or 6-position by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group each of which has 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, which trans-1,4-cyclohexylene or 1,4-cyclohexenylene group can optionally also be substituted in the 1-position and/or 4-position and one or two CH.sub.
    Type: Grant
    Filed: November 21, 1986
    Date of Patent: July 24, 1990
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Wolfgang Sucrow, Herbert Wolter, Rudolf Eidenschink
  • Patent number: 4940806
    Abstract: Novel substituted 2-(1H-1,2,4-triazolyl)-1-phenylethan-1-one ketals of the general formula ##STR1## wherein one of the two phenyl substituents is in 2-position and the other is in 4-position, and wherein R.sub.a is halogen, methyl or C.sub.1 -C.sub.3 haloalkoxy, and U and V are each independently of the other C.sub.1 -C.sub.12 alkyl, unsubstituted or substituted by halogen or C.sub.1 -C.sub.6 alkoxy, or together are an alkylene bridge selected from ##STR2## wherein R.sub.1 to R.sub.5 are as defined herein, and the acid addition salts and metal complex salts, have microbicidal properties and are especially suitable for controling phytopathogenic microorganisms. They can be used in the form of plant protective or seed dressing agents for preventing or controlling plant pathogens.
    Type: Grant
    Filed: June 21, 1989
    Date of Patent: July 10, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Adolf Hubele
  • Patent number: 4929739
    Abstract: A novel complex of a class of tellurium and selenium compounds is disclosed, which is based on a complexing agent and the particular compound to be complexed.
    Type: Grant
    Filed: March 24, 1988
    Date of Patent: May 29, 1990
    Assignee: Bar-Ilan University
    Inventors: Benjamin Sredni, Leo Pavliv, Michael Albeck
  • Patent number: 4877891
    Abstract: 1,1-dialkoxy- or 1,1-(.alpha.,.omega.-methylenedioxy)-non-2-yn-9-ol and their OH-protected derivatives of the general formula I ##STR1## where R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.6 -alkyl or together form an alkylene chain of 2 to 5 carbon atoms and X is hydrogen or a protective group which can be eliminated, their preparation and their use as intermediates.
    Type: Grant
    Filed: August 5, 1988
    Date of Patent: October 31, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Walter Seufert, Ernst Buschmann, Christiane Bruchner
  • Patent number: 4876368
    Abstract: A process is provided for the production of a monohydroxy monocyclic acetal, e.g., trimethylolpropane cyclic formal, of a trihydroxy alcohol, e.g., trimethylolpropane, and an aldehyde, e.g., formaldehyde, by subjecting a "heavier condensation product" of the trihydroxy alcohol and the aldehyde than the desired cyclic acetal, i.e., one having a higher molecular weight and boiling point, to acetal formation conditions. In a preferred embodiment, the product of reaction of the trihydroxy alcohol and aldehyde is treated to remove the desired monohydroxy monocyclic acetal product and at least part of the remainder comprising the heavier condensation product is recycled to the reaction together with a flesh supply of trihydroxy alcohol and aldehyde. The monohydroxy monocyclic acetal product may be further reacted to obtain a desired ester, e.g. trimethylolpropane cyclic formal acrylate, such as by transesterifying the acetal with a low boiling ester of the esterifying acid, e.g.
    Type: Grant
    Filed: May 24, 1988
    Date of Patent: October 24, 1989
    Assignee: Hoechst Celanese Corporation
    Inventors: Jerry A. Broussard, Wayne C. Fuqua, James H. George
  • Patent number: 4870104
    Abstract: 11-Haloprostane derivatives of general formula I ##STR1## wherein X is F, Cl or Br,R.sub.1 is the residue CH.sub.2 OH or ##STR2## wherein R.sub.2 means a hydrogen atom, an alkyl, cycloalkyl, aryl, phenacyl or heterocyclic residue,A is a --CH.sub.2 --CH.sub.2 -- or cis-CH.dbd.CH-group,B is a --CH.sub.2 --CH.sub.2 -- or trans-CH.dbd.CH-- or a --C.tbd.C-group,W is an ethylenedioxymethylene group or a hydroxymethylene group,D and E together mean a direct bond orD is a C.sub.1-10 -alkylene group,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C-bond or a --CR.sub.6 .dbd.CR.sub.7 -group with R.sub.6 and R.sub.7 meaning a hydrogen atom, a chlorine atom or an alkyl group,R.sub.4 is a hydroxy group,R.sub.5 is a hydrogen atom, an alkyl, a cycloalkyl, an aryl or a heterocyclic group, andthe salts thereof with physiologically compatible bases, processes for their preparation, and use thereof as agents inhibiting gastric acid secretion.
    Type: Grant
    Filed: November 12, 1986
    Date of Patent: September 26, 1989
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Claus-Steffen Sturzebecher, Walter Elger
  • Patent number: 4857539
    Abstract: Compounds of the formula ##STR1## wherein: Y is an alkylene bridge of 3-9 carbon atoms;Z is N or HC;R is hydrogen or lower-alkyl of 1-5 carbon atoms, with the proviso that when Z is N, R is lower-alkyl;R.sub.1 and R.sub.2 are hydrogen, halogen, lower-alkyl, lower-alkoxy, nitro, lower-alkoxycarbonyl or trifluoromethyl; andHet is selected from specified heterocyclic groups,are useful and antiviral agents, particularly against picornaviruses, including numerous strains of rhinovirus.
    Type: Grant
    Filed: June 16, 1987
    Date of Patent: August 15, 1989
    Assignee: Sterling Drug Inc.
    Inventors: Guy D. Diana, Philip M. Carabateas
  • Patent number: 4846998
    Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 Iin whichR.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, in which one or two non-adjacent CH.sub.2 groups can also be replaced by O atoms and/or --CO-- groups and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --A-- or --A--A.sup.4 --,A is a trans-1,4-cyclohexylene group which can be substituted in the 2-, 3-, 5- and/or 6-position one or more times by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group which each have 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 which may also be substituted in the 1- and/or 4-position,A.sup.2, A.sup.3 and A.sup.
    Type: Grant
    Filed: November 21, 1986
    Date of Patent: July 11, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Ludwig Pohl, Bernhard Scheuble, Reinhard Hittich, Rudolf Eidenschink, Hans A. Kurmeier, Andreas Wachtler
  • Patent number: 4847391
    Abstract: The invention relates to a process for preparing the ketals of 4-bromobutanal and of 5-bromopentanal of the formula ##STR1## which comprises reacting 2,3-dihydroguran and 3,4-dihydro-2H-pyran respectively in a solvent in the presence of a catalyst with neopentylglycol and then brominating the resulting product. The invention also relates to the said ketal of 5-bromobutanal as such.
    Type: Grant
    Filed: October 16, 1986
    Date of Patent: July 11, 1989
    Inventor: Gunter Bartels
  • Patent number: 4845119
    Abstract: A compound of the formula ##STR1## wherein X has the formula --CR.sup.5 .dbd.CR.sup.6 --, --C.tbd.C-- or ##STR2## wherein ring A is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl;wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent of each is hydrogen or alkyl, alkoxy or dialkylamino, provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substitutent;wherein R.sup.5 and R.sup.6, each is hydrogen, halogeno or alkyl;wherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 has the formula --Y--Q--R.sup.9 wherein Y is straight- or branched-chain alkylene or alkenylene; wherein Q is --O--, --S--, --SO-- or --SO.sub.2 --; andwherein R.sup.9 is alkyl or up to 6 carbon atoms which contains one or more defined substituents, processes for their manufacture and pharmaceutical compositions containing them.
    Type: Grant
    Filed: February 18, 1986
    Date of Patent: July 4, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Leslie R. Hughes, Howard Tucker
  • Patent number: 4834905
    Abstract: Compounds of the formulaR.sup.1 --Q.sup.1 --(CH.sub.2).sub.m --(COO).sub.n --(CH.sub.2).sub.p --Q.sup.2 --R.sup.2whereinR.sup.1 and R.sup.2 are each independently alkyl or alkoxy each of 1-12 C atoms, F, Cl, Br, CN or --Q.sup.3 --R.sup.3, or one of R.sup.1 and R.sup.2 can also be H;Q.sup.1, Q.sup.2 and Q.sup.3 are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-bicyclo(2,2,2)-octylene or 1,3-dioxane-2,5-diyl, each of which is unsubstituted or substituted by 1-4 fluorine, chlorine or bromine atoms;R.sup.3 is alkyl or alkoxy each of 1-8 C atoms, H, F, Cl, Br or CN;m is 1, 2, 3, 4, 5 or 6; n is 0 or 1; and p is 0, 1, 2, 3, 4 or 5; the sum of (m+p) being 2, 4 or 6 and the sum of (m+n+p) being at least 3;but with the proviso that Q.sup.3 is unsubstituted 1,4-phenylene or 1,4-phenylene substituted by a fluorine, chlorine or bromine atom, only when n=1 or (m+p)=6 or at least one of R.sup.1 to R.sup.3 is F, Cl or Br or none of R.sup.1 to R.sup.3 is CN or two of the radicals R.sup.1 to R.sup.
    Type: Grant
    Filed: October 3, 1986
    Date of Patent: May 30, 1989
    Assignees: Merck Patent Gesellschaft mit beschrankter Haftung, The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Rudolf Eidenschink, Joachim Krause, Beatrice M. Andrews, George W. Gray, Neil Carr
  • Patent number: 4833258
    Abstract: Novel intermediates and a novel process for their preparation, where said intermediates are useful in the preparation of 6-hydroxymethyl and related oxidation derivatives of mevinolin and analogs thereof, are disclosed.
    Type: Grant
    Filed: February 17, 1987
    Date of Patent: May 23, 1989
    Assignee: Merck & Co., Inc.
    Inventors: Robert L. Smith, Ta Jyh Lee