Alicyclic Acid Moiety Containing Oxy, Aldehyde Or Ketone Group Patents (Class 560/126)
  • Patent number: 5191104
    Abstract: This invention relates to a process for the alkoxylation of a carboxylated compound comprising contacting the carboxylated compound with an alkylene oxide in the presence of a mixed metal oxide catalyst or a modified bimetallic or polymetallic catalyst under conditions effective to alkoxylate the carboxylated compound.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: March 2, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Stephen W. King
  • Patent number: 5187286
    Type: Grant
    Filed: March 25, 1991
    Date of Patent: February 16, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Buchmann, Josef Heindl, Wolfgang Frohlich, Roland Ekerdt
  • Patent number: 5187304
    Abstract: Provided are 1,5-bis(4-carboxycyclohexyl)-3-pentanol and its esters and processes for their preparation. Also provided are polyester compositions containing this residue, thermosetting coating compositions containing the polyesters, and coatings and casted or molded articles made therefrom.
    Type: Grant
    Filed: May 1, 1992
    Date of Patent: February 16, 1993
    Assignee: Eastman Kodak Company
    Inventors: William W. Blount, Jr., Joseph R. Zoeller
  • Patent number: 5185446
    Abstract: This invention encompasses compounds of the formula: ##STR1## and pharmaceutically acceptable non-toxic salts thereof wherein n is 0,1 or 2 and X is --N.dbd.C--R.sub.9 or NR.sub.10 --C.dbd.Twhere R.sub.1, R.sub.2, R.sub.3, and R.sub.9 and R.sub.10 and X, Y, W and T are variables.These compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs thereof and are useful in the diagnosis and treatment of anxiety, sleep, and seizure disorders, overdoes with benzodiazepine type drugs, and enhancement of alertness.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: February 9, 1993
    Assignee: Neurogen Corporation
    Inventors: Kenneth Shaw, Alan J. Hutchison
  • Patent number: 5180709
    Abstract: The invention concerns novel odorants of formula I wherein R is hydrogen or methyl. ##STR1## The invention also concerns fragrance compositions containing I. Formula I is intended to particularly embrace as the racemates, (.+-.)-3.alpha.-acetyl-3.beta.,4.beta.,5,5-tetramethyl-2,3,4,4a.beta.,5,6, 7,8-octahydronapthalene and (.+-.)-3.alpha.-acetyl-4.beta.,5,5-trimethyl-2,3.beta.,4,4a.beta.,5,6,7,8- octahydronapthalene.
    Type: Grant
    Filed: May 31, 1991
    Date of Patent: January 19, 1993
    Assignee: Givaudan-Roure Corporation
    Inventors: Franz Etzweiler, Daniel Helmlinger, Cornelius Nussbaumer, Mario Pesaro
  • Patent number: 5175348
    Abstract: The invention relates to a novel process for the preparation of halogenated carboxylic acid esters of formula I ##STR1## wherein R.sub.1 is alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl or aryl, R.sub.2 hydrogen is alkyl or cycloalkyl, and R.sub.3 is halogen having an atomic number of from 9 up to and including 53, which process comprises reacting an acylal of formula II ##STR2## with a hydrogen halide of the formula H--R.sub.3 (III).
    Type: Grant
    Filed: March 10, 1992
    Date of Patent: December 29, 1992
    Assignee: Saurefabrik Schweizerhall
    Inventors: Pasquale Gallegra, Gerhard Degischer
  • Patent number: 5171879
    Abstract: The invention relates to a novel process for the preparation of chlorinated carboxylic acid esters of formula I ##STR1## wherein R.sub.1 is alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl or aryl and R.sub.2 hydrogen is alkyl or cycloalkyl, which process comprises reacting an acylal of formula II ##STR2## with thionyl chloride.
    Type: Grant
    Filed: March 10, 1992
    Date of Patent: December 15, 1992
    Assignee: Saurefabrik Schweizerhall
    Inventors: Pasquale Gallegra, Gerhard Degischer
  • Patent number: 5144057
    Abstract: 3-Oxocarboxylic acid esters are produced by acylation of the magnesium enolates of acetoacetic acid esters with carboxylic acid chlorides and cleavage of the acetyl group from the acylacetoacetic acid esters formed as the intermediate product. The yields and purity of the products are considerably improved by adding a tertiary amine during the acylation.
    Type: Grant
    Filed: October 11, 1991
    Date of Patent: September 1, 1992
    Assignee: Lonza Ltd.
    Inventor: Martin Eyer
  • Patent number: 5131945
    Abstract: Compounds of formula I ##STR1## are useful as herbicides, effective against dicotyledonous weeds.
    Type: Grant
    Filed: July 13, 1990
    Date of Patent: July 21, 1992
    Assignee: Shell Research Limited
    Inventors: Hans-Joachim Bissinger, Ludwig Schoeder, Helmut Baltruschat, Manfred Garrecht, Erich Raddatz, Wolfgang Fruhstorfer
  • Patent number: 5124083
    Abstract: There are disclosed 3-substituted and 3,3-disubstituted all-trans-4-oxoretinoic acids and 3-substituted and 3,3-disubstituted 13-cis-4-oxoretinoic acids and their lower alkyl esters.
    Type: Grant
    Filed: August 30, 1990
    Date of Patent: June 23, 1992
    Assignee: Southern Research Institute
    Inventor: Y. Fulmer Shealy
  • Patent number: 5118833
    Abstract: The invention provides a novel process for produing .alpha. -keto-carboxylic acid esters that are useful as intermediates for the preparation of pharmaceutical drugs in high yield by oxidizing .alpha. -hydroxycarbocylic acid esters with hypochlorous acid in the presence of nitroxy radical.
    Type: Grant
    Filed: June 14, 1990
    Date of Patent: June 2, 1992
    Assignee: Kuraray Company, Ltd.
    Inventors: Toshiki Mori, Shigeaki Suzuki, Takashi Onishi, Kazuo Yamamoto
  • Patent number: 5102911
    Abstract: HMG-CoA reductase inhibitors of formulae (I) and (II) are disclosed.
    Type: Grant
    Filed: July 6, 1990
    Date of Patent: April 7, 1992
    Assignee: Merck & Co, Inc.
    Inventors: Ta J. Lee, Wilbur J. Holtz
  • Patent number: 5091567
    Abstract: The instant invention concerns a novel process for the preparation of 1-aminomethyl-1-cyclohexaneacetic acid (gabapentin), a known compound useful for treating certain cerebral diseases such as epilepsy and dizziness.
    Type: Grant
    Filed: August 21, 1990
    Date of Patent: February 25, 1992
    Assignee: Godecke Aktiengesellschaft
    Inventors: Wolfram Geibel, Johannes Hartenstein, Wolfgang Herrmann, Joachim Witzke
  • Patent number: 5077309
    Abstract: Novel compounds have the formula (I) ##STR1## where ##STR2## represents one of the divalent cyclic groups ##STR3## the letters a and b indicating in each case the points of attachment of the substituents R.sup.1 and CV(R.sup.2)-NV'R, respectively; R.sup.1 is a group --(CH.sub.2).sub.b --(A).sub.a --(CH.sub.2).sub.c --B--CH.sub.2 --CO.sub.2 R' in which A and B are each separately oxygen or sulphur, a is 0, b is 0 and c is an integer from 3 to 10, or a is 1, b is 0 or an integer from 1 to 7 and c is an integer from 2 to 9 with the sum of b and c being from 2 to 9, and CO.sub.2 R' is a carboxy group or an amide, ester or salt derivative thereof; V and V' either each separately is hydrogen or together are the second bond of a carbon-nitrogen double bond; R.sup.2 is hydrogen, an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted by an aromatic group directly or through an oxygen or sulphur atom; and R is a group --OR.sup.3, --OR.sup.4, --D--R.sup.3, --N.dbd. R.sup.5 or --NW.G.
    Type: Grant
    Filed: March 28, 1990
    Date of Patent: December 31, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 5049696
    Abstract: Novel 3-hydroxy-3-methylglutaryl-Coenzyme A(HMG-CoA) reductase inhibitors, which are useful as antihypercholesterolemic agents and are represented by the following general structural formulae (I) and (II) ##STR1## and pharmaceutically acceptable salts of the compound (II) in which Z is hydrogen are disclosed.
    Type: Grant
    Filed: June 14, 1989
    Date of Patent: September 17, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Ta J. Lee, Clarence S. Rooney, William F. Hoffman
  • Patent number: 5047582
    Abstract: A process for oxidation of a tetrahydro compound of the formula ##STR1## wherein R and R' independently are H, alkyl, aryl or halo, to a glycol of the formula ##STR2## comprises treating the tetrahydro compound with hydrogen peroxide at an elevated temperature in the absence of a catalyst.The thus-formed glycol can be further oxidized in a butanetetracarboxylic acid of the formula ##STR3## with hydrogen peroxide in the presence of a catalyst selected from the group consisting of a manganese salt, an iron salt, a chromium salt, a cerium salt, a persulfate, a perborate, a silicate, tungstic acid or an ammonium or alkali metal salt or heteropolyacid thereof, or molybdic acid or an ammonium or alkali metal salt or heteropolyacid thereof.
    Type: Grant
    Filed: October 2, 1989
    Date of Patent: September 10, 1991
    Assignee: Ortec, Inc.
    Inventors: David L. Brotherton, Kwok W. Fung
  • Patent number: 5047261
    Abstract: The invention relates to a process for the manufacture of coatings by radiocrosslinking. A radio-crosslinkable composition (C) is produced first of all by mixing at least one (meth)acrylic compound (A) with a reactive diluent system comprising at least one mono(meth)acrylic carbonate (B) corresponding to the general formula (I): ##STR1## in which: R.sub.1 denotes H or CH.sub.3R.sub.2 denotes an alkylene ether or alkylene chain which has a total number of carbon atoms of between 2 and 6,n denotes an integer between 1 and 6.The composition (C) is next applied onto a substrate and is then radiocrosslinked, preferably using UV radiation.Another subject of the invention is the crosslinkable compositions (C) in which the compound (A) and the carbonate (B) are not simultaneously 2,3-carbonyldioxypropyl 2-methacryloyloxyethyl carbonate, and carbonates of general formula (I) in which R.sub.2 denotes (CH.sub.2).sub.m and in which m and n are integers such that 2.ltoreq.m.ltoreq.6, 1.ltoreq.n.ltoreq.6 and n.noteq.
    Type: Grant
    Filed: June 19, 1990
    Date of Patent: September 10, 1991
    Assignee: Societe Nationale des Pourdres et Explosifs
    Inventors: Khalil Moussa, Christian Decker, Jean-Claude Brosse, Sammy Chevalier, Denis Couvert
  • Patent number: 5041613
    Abstract: Processes, intermediates, and products involved in preparing cyclohexanediones of the formula ##STR1## are disclosed. An aldehyde of the formula R--CHO is reacted with a ketone type compound of the formula (R.sub.1)(R.sub.2)C.dbd.C.dbd.O at a temperature below about 110.degree. C. to give a polymer having the repeating unit --OCH(R)C(R.sub.1)(R.sub.2)CO].sub.n wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed with alcoholic or aqueous base to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: August 20, 1991
    Assignee: Eastman Kodak Company
    Inventor: Charles A. McCombs
  • Patent number: 5041694
    Abstract: Compounds of formula I ##STR1## are described which are useful to inhibit the formation of serum cholesterol by virtue of their ability to inhibit .beta.-hydroxy-.beta.-methylglutaryl-CoA(HMG CoA), the rate-controlling substance in the synthesis of serum cholesterol.
    Type: Grant
    Filed: October 13, 1989
    Date of Patent: August 20, 1991
    Assignee: G. D. Searle & Co.
    Inventors: John S. Baran, Thomas J. Lindberg, Harman S. Lowrie
  • Patent number: 5025017
    Abstract: Seco-mevinic acid derivatives are provided which has 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: September 28, 1989
    Date of Patent: June 18, 1991
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Donald S. Karanewsky
  • Patent number: 5015645
    Abstract: Disclosed are the compounds of formula I ##STR1## wherein R and R.sub.1 -R.sub.3 independently represent hydrogen or lower alkyl, and m represents the integer 2 or 3; their methods of preparation; pharmaceutical compositions thereof, and their use for treating cognitive disorders in mammals.
    Type: Grant
    Filed: October 19, 1989
    Date of Patent: May 14, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Jan W. F. Wasley
  • Patent number: 5010105
    Abstract: Compounds of Formula (I) and (II): ##STR1## are HMG-CoA reductase inhibitors.
    Type: Grant
    Filed: May 9, 1990
    Date of Patent: April 23, 1991
    Assignee: Merck & Co., Inc.
    Inventor: Ta J. Lee
  • Patent number: 4996301
    Abstract: Polyfunctional .alpha.-diazo-.beta.-keto esters of the general formula I are described ##STR1## in which R.sup.1 denotes an aliphatic, cycloaliphatic or araliphatic or aromatic radical having 4 to 20 carbon atoms, in which individual CH.sub.2 groups can be replaced by oxygen or sulfur atoms or by N-- or NH groups and/or contain keto groups,X denotes an aliphatic, cycloaliphatic, carbocyclic, heterocyclic or araliphatic radical having 2 to 22 carbon atoms, in which individual CH.sub.2 groups can be replaced by oxygen or sulfur atoms or by the groups ##STR2## in which R.sup.2 and R.sup.3 independently of one another represent hydrogen or an aliphatic, carbocyclic or araliphatic radical,m denotes an integer from 2 to 10 andn denotes an integer from 0 to 2,whereinm-n is .gtoreq.2.The compounds mentioned are used as photoactive components in radiation-sensitive mixtures.
    Type: Grant
    Filed: January 12, 1990
    Date of Patent: February 26, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Peter Wilharm, Hans-Joachim Merrem, Georg Pawlowski
  • Patent number: 4990633
    Abstract: New fluorinated bisaryloxy-substituted alkenes are prepared by reaction of substituted phenols with perhaloalkenes and can be used as electrical insulating agents.
    Type: Grant
    Filed: May 4, 1989
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Negele, Dietmar Beilefeldt, Thomas Himmler, Albrecht Marhold
  • Patent number: 4966915
    Abstract: An L-dopa derivative represented by formula (I) ##STR1## wherein one of R.sup.1 and R.sup.2 denotes a hydrogen atom and the other denotes a group of formula R--CO-- in which R denotes an alkyl, alkenyl, optionally substituted cycloalkyl, optionally substituted phenyl, optionally substituted aralkyl, lower alkoxy or optionally substituted aralkyloxy group,and its acid addition salt. The compounds are useful in the medical field, especially in the treatment of a series of diseases called Parkinson's disease or Parkinsonism.
    Type: Grant
    Filed: September 16, 1988
    Date of Patent: October 30, 1990
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Yoshimi Tsuchiya, Masahiro Hayashi, Hiroshi Takehana, Akihiro Hisaka, Yoshio Sawasaki, Masaki Ihara
  • Patent number: 4966726
    Abstract: The new compounds produced from a molecular structural element with two chirality centers and at least one mesogenic structural element are defined by the general formula (I) ##STR1## in which the symbols have the following meaning: Y.sup.1 =H, (C.sub.1 -C.sub.10)alkyl, MC--CH.sub.2 or MC--CO, MC denoting the molecular radical of a mesogenic carboxylic acid after splitting off a COOH group,Y.sup.2 =(C.sub.1 -C.sub.10)alkyl, MC--CH.sub.2 or MC--CO, it being possible for Y.sup.1 and Y.sup.2 to jointly represent a MC--CH group, which is then part of a dioxolane ring,X=COOR.sup.1, CONH.sub.2, CONR.sup.2 R.sup.3 or C.tbd.N,R.sup.1 =(C.sub.1 -C.sub.10)alkyl or MC--CH.sub.2, andR.sup.2, R.sup.3 =H and (C.sub.1 -C.sub.4)alkyl or, independently of each other, (C.sub.1 -C.sub.4)alkyl.Said esters preferably find application as dopants in twistable liquid crystal phases in which they produce temperature compensation and twisting.
    Type: Grant
    Filed: July 18, 1988
    Date of Patent: October 30, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Scherowsky, Manel Gunaratne
  • Patent number: 4965398
    Abstract: A process for preparing an .alpha.-hydroxycarboxylate represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a lower alkyl group; R.sup.2 represents a lower alkyl group, a phenyl group or a cycloalkyl group, or R.sup.1 and R.sup.2 are bonded to each other to form a five- to seven-membered cycloalkenyl or bicycloalkenyl ring which may be substituted with a lower alkyl group; and R.sup.3 represents a lower alkyl group,which comprises reacting an olefin compound represented by formula (II): ##STR2## wherein R.sup.1 ' represents a hydrogen atom or a lower alkyl group; and R.sup.2 ' represents a lower alkyl group, a phenyl group or a cycloalkyl group, or R.sup.1 ' and R.sup.2 ' are bonded to each other to form a five- to seven-membered cycloalkyl or bicycloalkyl ring which may be substituted with a lower alkyl group,with a glyoxylate represented by formula (III): ##STR3## wherein R.sup.
    Type: Grant
    Filed: July 28, 1989
    Date of Patent: October 23, 1990
    Assignee: Takasago International Corporation
    Inventors: Koichi Mikami, Masahiro Terada, Takeshi Nakai, Noboru Sayo, Hidenori Kumobayashi
  • Patent number: 4963285
    Abstract: Described are 2,4,4-trisubstituted tetrahydro pyranyl esters defined according to the structure: ##STR1## wherein R.sub.1 represents methyl or ethyl and R.sub.2 represents C.sub.2 -C.sub.4 straight chain or branched chain alkyl or alkenyl and organoleptic used thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including, but not limited to bleach compositions, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softener compositions, fabric softener articles, cosmetic powders and hair preparations.
    Type: Grant
    Filed: February 9, 1989
    Date of Patent: October 16, 1990
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Roger E. Greene
  • Patent number: 4950774
    Abstract: A 2,5-disubstituted-7,7,8,8-tetracyanoquinodimethane of the general formula ##STR1## wherein R.sup.1 is hydrogen or methyl, X is COOR.sup.2 (in which R.sup.2 is hydrogen or C.sub.1-10 alkyl), --CONR.sup.3 R.sup.4 (in which R.sup.3 and R.sup.4 each is hydrogen or C.sub.1-4 alkyl) or --CN, provided that when R.sup.1 is hydrogen, X is --CN or --CONR.sup.3 R.sup.4. The tetracyanoquinodimethane derivatives are starting materials for the production of polyamides, polyurethanes or organic semiconductor devices.
    Type: Grant
    Filed: October 23, 1987
    Date of Patent: August 21, 1990
    Assignee: Nippon Gohsei Kagaku Kogyo Kabushiki
    Inventor: Takeo Kawabata
  • Patent number: 4950797
    Abstract: A process for the preparation of carbonyl compounds by catalyzed isomerization of allyl alcohols in a tertiary phosphine or phosphite ester in the presence of a rhodium compound at a temperature of from 80.degree. C. to 180.degree. C., a carrier gas being passed through the reaction mixture and the carbonyl compound being separated from the emergent gas mixture by cooling.
    Type: Grant
    Filed: June 1, 1988
    Date of Patent: August 21, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Rudolf Kummer, Werner Bertleff, Michael Roeper
  • Patent number: 4945178
    Abstract: Acetoacetic esters of the formula R--OOCCH.sub.2 COCH.sub.3 are reacted with an unsaturated ester of the formula R.sup.1 R.sup.2 C.dbd.CHCOOR.sup.3 in the presence of basic catalyst such as ethanolic sodium ethoxide to give compound I of the formula ##STR1## and the alcohol by-product HOR.sup.3. By known hydrolysis and decarboxylation procedures, compound I is convertible to compound II of the formula ##STR2## In the above formulas, R is alkyl, R.sup.1 and R.sup.2 are each selected independently from H, alkyl, alkylthioalkyl, cycloalkyl, alkyl substituted cycloalkyl, aryl, substituted aryl, heterocyclic, or substituted heterocyclic, and R.sup.3 is alkyl or cycloalkyl. These compounds I and II are intermediates in the preparation of known herbicides.
    Type: Grant
    Filed: February 24, 1989
    Date of Patent: July 31, 1990
    Assignee: Eastman Kodak Company
    Inventor: Charles A. McCombs
  • 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: 4936906
    Abstract: Agents for regulating plant growth containing an effective amount of at least one cyclohexanone derivative of the formula I ##STR1## where A, X, n, Y, Z and R have the meanings given in the disclosure, or salts of these compounds, and a process for regulating plant growth.
    Type: Grant
    Filed: July 2, 1986
    Date of Patent: June 26, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Jahn, Michael Keil, Dieter Kolassa, Ulrich Schirmer, Rainer Becker, Johann Jung, Wilhelm Rademacher
  • Patent number: 4933482
    Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a .beta.-keto acid derivative in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.
    Type: Grant
    Filed: June 9, 1988
    Date of Patent: June 12, 1990
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
  • Patent number: 4929751
    Abstract: A vinyl tricarbonyl compound of the formula ##STR1## or its monohydrate of the formula ##STR2## wherein R.sub.1 is a hydrogen, halogen, unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, and cycloalkyl with 3 to 7 carbon atoms,R.sub.2 is hydrogen, halogen, unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, cycloalkyl with 3 to 7 carbon atoms, cyano, nitro, or a heterocyclic,R.sub.3 is hydrogen, halogen, unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, cycloalkyl with 3 to 7 carbon atoms, cyano, nitro, or a heterocyclic, andR.sub.4 is unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, cycloalkyl are 3 to 7 carbon atoms. Such vinyl tricarbonyl compound is effective against tumor cells.
    Type: Grant
    Filed: October 19, 1987
    Date of Patent: May 29, 1990
    Assignee: Yale University
    Inventors: Harry H. Wasserman, Natesan Murugesan, John H. Van Duzer
  • Patent number: 4925970
    Abstract: A process for production of an alkylthiobenzoate comprising reacting a cyclohexenone having the formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.6 alkyl; X is alkyl or unsubstituted alkyl; and Y is hydrogen, halogen or alkyl, with a mercaptan having the formula R.sub.2 SH in which R.sub.2 is C.sub.1 -C.sub.4 alkyl, preferably in the presence of an acid catalyst, to form a cyclohexadiene thioether, and dehydrogenating the thioether to produce a thioalkylbenzoate.The thioalkylbenzoate may be further converted by oxidation and/or hydrolysis to a corresponding thioalkyl, alkylsulfinyl or alkylsulfonyl benzoic acid.
    Type: Grant
    Filed: December 22, 1988
    Date of Patent: May 15, 1990
    Inventor: Richard W. Brown
  • Patent number: 4916156
    Abstract: The present invention relates to aromatic derivatives of the formula: ##STR1## in which: n represents an integer between 2 and 10;R.sub.1 and R.sub.2 are identical or different and represent a cycloalkyl containing 3 to 6 carbon atoms or an alkyl containing from 1 to 6 carbon atoms which is unsubstituted or substituted by a phenyl or benzyl group; orR.sub.1 and R.sub.2, together with the nitrogen atom to which they are bonded, form a heterocycle selected from pyrrolidin-1-yl, piperidino, azepin-1-yl, hexamethyleneimino, 4-methylpiperidino, 4-benzylpiperidino, 4-phenylpiperidino, 1,2,3,4-tetrahydroisoquinol-2-yl, morpholino and imidazol-1-yl groups;R.sub.3 represents a hydrogen, a halogen, a methyl or a phenyl;R.sub.4 represents a hydrogen, a halogen or a methyl; or R.sub.3 and R.sub.4, taken together with the benzene ring to which they are bonded, form a naphth-1-yl or naphth-2-yl group;Y represents a direct bond, a methyleneoxy group, a methylenethio group or a vinylene group; andR.sub.
    Type: Grant
    Filed: April 6, 1988
    Date of Patent: April 10, 1990
    Assignee: Sanofi
    Inventors: Madeleine Mosse, Vincenzo Proietto
  • Patent number: 4916252
    Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a 1,3-diketone in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.
    Type: Grant
    Filed: June 16, 1988
    Date of Patent: April 10, 1990
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
  • Patent number: 4898967
    Abstract: Process for the production of substituted 2-oxocyclohexaneacetic acid esters and intermediates used for their production. The substituted 2-oxocyclohexaneacetic acid esters are themselves useful intermediates for the manufacture of substituted 2,3,4,9-tetrahydro-1H-carabazole-1-acetic acid derivatives having useful analgesic and anti-inflammatory activity.
    Type: Grant
    Filed: February 13, 1989
    Date of Patent: February 6, 1990
    Assignee: American Home Products Corp.
    Inventors: Philip F. Hughes, Dominick Mobilio, Leslie G. Humber
  • Patent number: 4898977
    Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonisation of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.
    Type: Grant
    Filed: August 13, 1987
    Date of Patent: February 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Herold, Christof Angst
  • Patent number: 4895973
    Abstract: Compounds of formula I ##STR1## are described which are useful to inhibit the formation of serum cholesterol by virtue of their ability to inhibit .beta.-hydroxy-.beta.-methylglutaryl-CoA(HMG CoA), the rate-controlling substance in the synthesis of serum cholesterol.
    Type: Grant
    Filed: December 21, 1988
    Date of Patent: January 23, 1990
    Assignee: G. D. Searle & Company
    Inventors: John S. Baran, Thomas J. Lindberg, Harman S. Lowrie
  • Patent number: 4886619
    Abstract: Compounds are provided which comprise a fluorocarbon terminal portion and a chiral hydrocarbon terminal portion, said terminal portions being connected by a central core, said compounds having tilted smectic mesophases or having latent tilted smectic mesophases which develop when said compounds having said latent mesophases are in admixture with said compounds having tilted smectic mesophases or said compounds having latent tilted smectic mesophases.
    Type: Grant
    Filed: May 29, 1987
    Date of Patent: December 12, 1989
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Eugene P. Janulis
  • Patent number: 4875930
    Abstract: As new compound is provided a cyclohexane derivative of the formula ##STR1## wherein R.sup.1 is a hydrogen or a lower alkyl; R.sup.2 is a lower alkyl; R.sup.3 is a hydrogen, an alkyl, an alkenyl, a hydroxyalkyl, a cycloalkyl, a morpholino, an aminoalkyl, an N-alkylaminoalkyl, an N,N-di-alkylaminoalkyl, an alkoxycarbonylalkyl, a group of the formula --(CH.sub.2).sub.l --R.sup.4 where R.sup.4 is a lower alkoxy, a lower alkylthio, a benzylthio, an anilino, a morpholino, a piperazino, a piperidino or a lower alkyl-substituted piperidino and l is 2 or 3, a group of the formula ##STR2## where X is a halogen, a lower alkyl, a lower alkoxy, a phenoxy or an alkoxycarbonylalkyloxy, m is zero or 1 and n is an integer of zero to 2, inclusive, a group of the formula --CH.sub.2 --R.sup.5 where R.sup.5 is a furyl, a thenyl or a pyridyl, or a group of the formula ##STR3## where R.sup.5 is as defined above; or a salt of said cyclohexane derivative.
    Type: Grant
    Filed: April 26, 1988
    Date of Patent: October 24, 1989
    Inventors: Masafumi Matsuzawa, Hiroshi Hokari, Shoji Kusano, Takeshige Miyazawa, Yasufumi Toyokawa
  • Patent number: 4872902
    Abstract: The invention relates to the novel cyclohexanediones of formula I ##STR1## in which R is hydrogen or C.sub.1 -C.sub.6 -alkyl,A is R.sub.2, OR.sub.3 or NR.sub.3 R.sub.4,R.sub.2 is C.sub.1 -C.sub.6 -alkyl that is unsubstituted or is mono-substituted by C.sub.1 -C.sub.4 -alkoxy or mono- or poly-substituted by halogen, or is C.sub.3 -C.sub.6 -cycloalkyl,R.sub.3 is C.sub.1 -C.sub.6 -alkyl or C.sub.3 -C.sub.6 -cycloalkyl, or is phenyl or benzyl each of which is unsubstituted or is mono-, di- or tri-substituted by R.sub.5,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.3 -C.sub.6 -cycloalkyl,R.sub.3 and R.sub.4 are, in addition, together with the nitrogen atom to which they are bonded, a pyrrolidine, morpholine or piperidine radical,B is one of the radicals ##STR2## m is 0, 1, 2 or 3, R.sub.5 is halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.
    Type: Grant
    Filed: February 8, 1988
    Date of Patent: October 10, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans-Georg Brunner
  • Patent number: 4867903
    Abstract: A fluoroalkane derivative represented by the formula: ##STR1## wherein R denotes an alkyl group having 1-16 carbon atoms, C* denotes an asymmetric carbon atom, R.sup.1 denotes an alkyl or alkoxy group having 1-16 carbon atoms; ##STR2## respectively denote a phenylene group ##STR3## a cyclohexylene group ##STR4## or a pyrimidinylene group ##STR5## p is 0 or 1, q is 0 or 1 when p is 1, r is 0 or 1; and l, m and n are respectively 0 or a positive integer satisfying the relationship of l+m+n.gtoreq.1. The fluoroalkane derivative has a fluorine atom providing a large dipole moment and directly connected to an asymmetric carbon atom, so that it provides a high speed responsive characteristic through an increased spontaneous polarization when contained in a liquid crystal composition, especially a ferroelectric liquid crystal composition.
    Type: Grant
    Filed: March 6, 1987
    Date of Patent: September 19, 1989
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Shinichi Nakamura, Kazuharu Katagiri
  • Patent number: 4866201
    Abstract: A new compound is provided by a cyclohexane derivative of the formula ##STR1## wherein R represents a hydrogen atom or an alkyl group, an alkylthioalkyl group or an unsubstituted or substituted phenyl group; and R.sup.1 represents an alkyl group, an unsubstituted or substituted benzyl group, a phenethyl group, a phenoxymethyl group, a 2-thienylmethyl group, an alkoxymethyl group or an alkylthiomethyl group, or a salt of said cyclohexane compound.This cyclohexane compound exhibits useful plant-growth regulating effects on crop-plants and also non-crop plants such as lawn and may be prepared by cyclization of an acetonylsuccinic acid dialkyl ester, followed by reaction with an organic acid chloride and by intermolecular rearrangement.
    Type: Grant
    Filed: July 7, 1987
    Date of Patent: September 12, 1989
    Assignee: Kumiai Chemical Industry Co., Ltd.
    Inventors: Kenji Motojima, Takeshige Miyazawa, Yasufumi Toyokawa, Masafumi Matsuzawa, Hiroshi Hokari, Shoji Kusano
  • Patent number: 4861910
    Abstract: Process for the production of substituted 2-oxocyclohexaneacetic acid esters and intermediates used for their production. The substituted 2-oxocyclohexaneacetic acid esters are themselves useful intermediates for the manufacture of substituted 2,34,9-tetrahydro-1H-carbazole-1-acetic acid derivatives having useful analgesic and anti-inflammatory activity.
    Type: Grant
    Filed: December 11, 1987
    Date of Patent: August 29, 1989
    Assignee: American Home Products Corporation
    Inventors: Philip F. Hughes, Dominick Mobilio, Leslie G. Humber
  • Patent number: 4853463
    Abstract: Novel amino acid derivatives useful as a therapeutic agent are disclosed. These amino acid derivatives and the pharmaceutically acceptable salts thereof have a human renin inhibitory effect when administered orally and are useful for treatment of hypertension, especially renin-associated hypertension.
    Type: Grant
    Filed: December 13, 1988
    Date of Patent: August 1, 1989
    Assignee: Kissei Pharmaceutical Co., Ltd.
    Inventors: Kinji Iizuka, Tetsuhide Kamijo, Tetsuhiro Kubota, Kenji Akahane, Hideaki Umeyama, Yoshiaki Kiso
  • Patent number: 4841096
    Abstract: A cyclohexane-2,5-dione-1,4-ylene-bis (-3-propionic acid) derivative represented by the formula ##STR1## wherein R is hydrogen or alkyl. The derivative is prepared by heating a cyclohexane-2,5-dione derivative represented by the formula ##STR2## wherein R is as defined above, and R.sub.1 is alkyl, in the presence of water.
    Type: Grant
    Filed: December 8, 1987
    Date of Patent: June 20, 1989
    Assignee: Nippon Gosei Kaagaku Kogyo
    Inventor: Masahiko Miyashita
  • 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