Alicyclic Acid Moiety Containing N, S, P, B Or Halogen Patents (Class 560/125)
  • 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: 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: 4935444
    Abstract: Esterified ephedrine derivatives with prolonged antiulcer activity and low toxicity, having the following general formula: ##STR1## in which R is: ##STR2## The invention also describes a process for preparing derivatives of formula (I) and compositions containing them as active principle.
    Type: Grant
    Filed: October 6, 1988
    Date of Patent: June 19, 1990
    Assignee: Etablissement Texcontour
    Inventor: Federico Butelman
  • Patent number: 4931582
    Abstract: Novel fluorinated, acrylamide monomers are prepared from 2-alkenyl azlactones reacted with fluorinated alcohols. The novel monomers have the formula ##STR1## wherein R.sup.1 and R.sup.6 are independently hydrogen or methyl;R.sup.2 and R.sup.3 independently can be an alkyl, cycloalkyl, or aryl group, or R.sup.2 and R.sup.3 taken together with the carbon to which they are joined can form a carbocyclic ring containing 4 to 12 ring atoms;R.sup.4 and R.sup.5 are independently hydrogen or lower alkyl;a is 0 or 1;b is 1 or 2;X is a single bond, CH.sub.2, CH.sub.2 OCH.sub.2, and CH.sub.2 CH.sub.2 OCH.sub.2 ; andR.sub.F is a substantially perfluorinated alkyl, cycloalkyl, or aryl group when b is 1 and perfluorinated alkylene when b is 2.Novel polymers and copolymers can be prepared from the monomers of the invention.
    Type: Grant
    Filed: November 4, 1988
    Date of Patent: June 5, 1990
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Steven M. Heilmann, Larry R. Krepski, Dean M. Moren, Jerald K. Rasmussen, Howell K. Smith, II
  • 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: 4927964
    Abstract: An advantageous method of producing in large amounts on a commercial scale 2-substituted oxyimino-3-oxobutyric acids, which are useful as intermediates in the synthesis of e.g. aminothiazole cephalosporins, is characterized by reacting a tert-butyl 2-substituted oxyimino-3-oxobutyrate with a hydrogen halide in an anhydrous organic solvent.
    Type: Grant
    Filed: January 11, 1989
    Date of Patent: May 22, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kenzo Naito, Yukio Ishibashi, Haruo Shinbo
  • 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: 4908475
    Abstract: New compounds which have potent V.sub.2 -vasopressin antagonistic activity are prepared by a 1,6-cyclization using peptide bond formation. The structures of the compounds are characterized by a Pas.sup.1,6 or Tas.sup.1,6 cyclized unit. Also a chiral synthesis of the optically pure Pas intermediates is described.
    Type: Grant
    Filed: May 9, 1988
    Date of Patent: March 13, 1990
    Assignee: SmithKline Beckman Corporation
    Inventors: James F. Callahan, William F. Huffman, Kenneth A. Newlander, Nelson C. F. Yim
  • Patent number: 4902818
    Abstract: The manufacture of optically active bifunctional compounds of the general formula ##STR1## wherein R represents protected hydroxymethyl, protected formyl or alkoxycarbonyl and R.sup.1 represents a group of the formula ##STR2## in which R.sup.2 and R.sup.3 represents lower alkyl or cycloalkyl or R.sup.2 and R.sup.3 together with the nitrogen atom represent a heterocyclic ring, by isomerizing compounds of the general formula ##STR3## wherein R, R.sup.2 and R.sup.3 have the above significance and R.sup.3 can additionally signify hydrogen, is described.The compounds of formula I are potential intermediates in the manufacture of, interalia, natural vitamin E and natural vitamin K.sub.1.
    Type: Grant
    Filed: October 5, 1988
    Date of Patent: February 20, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Hans-Jurgen Hansen, Rudolf Schmid, Max Schmid
  • 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: 4898930
    Abstract: Peptide ester and amide derivatives of the general formula I: ##STR1## in which X is H or an acyl, A and B are structurally defined amino acid residues, n is an integer of from 1 to 3, R.sup.1 is H or a lower alkyl and either R.sup.2 or C is a defined optionally modified amino acid residue and the other is a lower alkoxyl, an amino group or a direct chemical bond, are converted under physiologic conditions, by enzymic hydrolysis in pathologically altered tissues and subsequent spontaneous cyclization, into pharmacodynamically active spirocyclic peptide derivatives of the general formula III: ##STR2## in which R.sup.3 and R.sup.4 are H atoms, optionally substituted alkyl groups or jointly an aliphatic chain forming preferably a 2,5- piperazinedione ring, and hence can act as pro-farmaca (drug precursors) of prolonged biological effect.
    Type: Grant
    Filed: June 12, 1987
    Date of Patent: February 6, 1990
    Assignee: Spofa, spojene podniky pro
    Inventors: Evzen Kasafirek, Miroslav Rybak, Ivan Krejci, Antonin Sturc, Alena Roubalova, Jiri Vanzura, Evzen Krepela, Michal Bartik
  • 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: 4882341
    Abstract: The invention relates to amino substituted propenoates and their use against fungi.
    Type: Grant
    Filed: September 9, 1988
    Date of Patent: November 21, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Ian T. Kay
  • Patent number: 4879403
    Abstract: Compounds of the formula I ##STR1## in which the carboxyl group on carbon atom 3 is orientated in the endo-position relative to the bicyclic ring system of cis-configuration, and in which R.sup.1 denotes hydrogen, allyl, vinyl or a side-chain of a naturally occurring .alpha.-aminoacid, which may be protected, R.sup.2 denotes hydrogen, alkyl, alkenyl or aralkyl, Y denotes hydrogen or hydroxyl and Z denotes hydrogen, or Y and Z together denote oxygen, and X denotes alkyl, alkenyl or cycloalkyl, or aryl which is optionally mono-, di- or tri-substituted by alkyl, alkoxy, hydroxyl, halogen, nitro, amino, alkylamino, dialkylamino or methylenedioxy, or denotes indol-3-yl, a process for their preparation, agents containing these compounds and their use.
    Type: Grant
    Filed: November 2, 1988
    Date of Patent: November 7, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Volker Teetz, Rolf Geiger, Hansjorg Urbach, Reinhard Becker, Bernward Scholkens
  • 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: 4876343
    Abstract: An improved process for the preparation of statine, the phenyl analog of statine, the cyclohexyl analog of statine and derivatives thereof is described, as well as other valuable intermediates used in the process.
    Type: Grant
    Filed: June 15, 1988
    Date of Patent: October 24, 1989
    Assignee: Warner-Lambert Company
    Inventors: John C. Hodges, Sylvester Klutchko
  • Patent number: 4874822
    Abstract: The present invention provides a dramatically improved process for the preparation of acrylamide and methacrylamide functional monomers, oligomers, and polymers that avoids the use of acidic catalysts which can cause undesired side reactions. The present invention process involves reacting an alkenyl azlactone with a hydroxy functional compound in the presence of a catalytic amount of either a bicyclic amidine or a trivalent phosphorus compound. These efficient basic catalysts provide unexpectedly increased reaction rates under mild conditions.
    Type: Grant
    Filed: April 7, 1988
    Date of Patent: October 17, 1989
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Jerald K. Rasmussen, Steven M. Heilmann, Larry R. Krepski, Dean M. Moren
  • Patent number: 4835304
    Abstract: Esters having the general formula: ##STR1## where X is a halogen, n is 1-5, Y is an alkyl, ether, ester, or nitro substituent, m is 0-2, Z is an ester linkage --OCO-- or --CO.sub.2 --, R' is a haloalkyl group, and p is 1-3, constitute high density flotation fluids for inertial instruments such as gyroscopes and accelerometers. Synthetic methods are disclosed for production of such fluids from available starting materials.
    Type: Grant
    Filed: May 1, 1987
    Date of Patent: May 30, 1989
    Assignee: Charles Stark Draper Laboratory
    Inventor: John R. Williams
  • 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: 4830470
    Abstract: Compounds of the formula ##STR1## wherein m represents is the number 0 or 1; A is a single covalent bond, --CH.sub.2 --CH.sub.2 --, --OCH.sub.2 --, --COO-- or --OOC--; rings B, C and D are 1,4-phenylene optionally substituted with cyano, halogen or lower alkyl; Y.sup.1 and Y.sup.2 are hydrogen or one of them also is cyano; and R.sup.1 and R.sup.2 each represents C.sub.1 -C.sub.18 -alkyl or C.sub.2 -C.sub.18 alkenyl, either of which is optionally halogen-substituted, in which one CH.sub.2 group or two non-adjacent CH.sub.2 groups is/are optionally replaced by oxygen; with the provisos that at least one of R.sup.1 and R.sup.2 has a chiral carbon atom or a C--C double bond or both when A is --COO-- and at least one of R.sup.1 and R.sup.2 has a C--C double bond when A is a single covalent bond, their preparation, liquid crystalline mixtures containing these compounds and their use for electro-optical purposes are described.
    Type: Grant
    Filed: May 20, 1987
    Date of Patent: May 16, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Buchecker, Hans-Jurgen Fromm, Stephen Kelly, Martin Schadt
  • Patent number: 4826620
    Abstract: The new esters derived from a chiral compound containing two OH groups and at least one mesogenic carboxylic acid which have the general formula (I) ##STR1## in which X.sup.1 =O--H or O--CO--(C.sub.1 to C.sub.12)alkyl and X.sup.2 =O--MC or X.sup.1 and X.sup.2 denote O-MC independently of each other, where MC is the molecular radical of a mesogenic monocarboxylic acid after splitting off an OH group.The esters or esters substituted in the aromatic part of the phenolic part preferably find application as an admixture intwistable liquid crystal phases in which they produce a temperature compensation and a high degree of twisting.
    Type: Grant
    Filed: January 21, 1988
    Date of Patent: May 2, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerd Heppke, Detlef Lotzsch, Feodor Oestreicher, Gunter Scherowsky
  • Patent number: 4816598
    Abstract: The invention relates to 4-amino-butanoic acid derivatives of general formula: ##STR1## in which: M represents an alkali metal atom,R represents a protected amino group,R.sub.1 represents a labile group,R.sub.2 represents hydrogen, a branched- or straight-chain alkyl radical having from 1 to 6 carbon atoms, a lower methyloxyalkyl, a lower methylthioalkyl, a lower (lower alkyl)-aminoalkyl, a lower di-(lower alkyl)-aminoalkyl or a lower hydroxyalkyl radical or R.sub.2 represents one of the radicals of general formulae:Cy--A--, Cy--O--A'--, R--A'-- or R.sub.
    Type: Grant
    Filed: June 16, 1987
    Date of Patent: March 28, 1989
    Assignee: Sanofi
    Inventors: Marcel Descamps, Walter Verstraeten
  • Patent number: 4814485
    Abstract: The invention relates to new (4S)-4-aminobutanoic acid derivatives of general formula: ##STR1## in which: R represents an N-protective group,R.sub.1 represents hydrogen, an alkali metal atom such as lithium, sodium or potassium or a liabile group,R.sub.2 represents a group of formula: ##STR2## in which W represents hydrogen, a hydroxy group or an alkyl radical containing from 1 to 4 carbon atoms or an alkoxy radical containing from 1 to 4 carbon atoms, and to a process for the preparation of the said derivatives.The 4-aminobutanoic acid derivatives according to the invention are useful as synthesis intermediates for the preparation of peptides derived from statin analogues.
    Type: Grant
    Filed: December 2, 1986
    Date of Patent: March 21, 1989
    Assignee: Sanofi
    Inventors: Marcel Descamps, Dino Nisato, Walter Verstraeten
  • Patent number: 4806677
    Abstract: Hardeners are described for synthetic resins which contain groups which are capable of ester or amide formation and, if appropriate, polymerizable double bonds. The new hardeners, which allow lower crosslinking temperatures, are products (A) of the Michael addition of compounds (B), containing Michael addition-capable ester groups, to compounds (C) which contain at least two Michael addition-capable double bonds, the products (A) having an average of at least one polymerization-capable double bond and at least two transesterification- or transamidation-capable ester groups per molecule and the compound (B) representing products of the reaction of (b1) CH-active alkyl esters and (b2) polyisocyanates.
    Type: Grant
    Filed: January 29, 1987
    Date of Patent: February 21, 1989
    Assignee: Hoechst AG
    Inventors: Gerd Walz, Helmut Plum
  • Patent number: 4803268
    Abstract: The present invention relates to a novel, optimized process for the preparation of cyclohexanedionecarboxylic acid derivatives of formula I which can be carried out in a single vessel affording a very good yield, which process comprises heating a reactive carboxylic acid derivative of formula III ##STR1## wherein X is a halide, an alkylsulfonic or arylsulfonic acid radical or the molecular radical ##STR2## which is necessary to form an anhydride and R.sub.1 is alkyl or cycloalkyl, with an alkali metal cyanide or copper cyanide, in an inert organic solvent, to give a mixture, then adding in succession to said mixture, at a temperature in the range from 0.degree. C.
    Type: Grant
    Filed: January 29, 1987
    Date of Patent: February 7, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Georg Brunner, Urs Muller
  • Patent number: 4794197
    Abstract: All-cis-1,3,5-Triamino-2,4,6-trihydroxycyclohexane derivatives corresponding to the general formula I ##STR1## wherein the symbols R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are identical or different and represent hydrogen atoms, alkyl groups or --CO-alkyl groups wherein the alkyl in the alkyl or --CO-alkyl group has 1 to 18 carbon atoms and the alkyl and --CO-alkyl groups may contain, independently of one another, one or more identical or different functional groups, and at least one of the groups R.sub.1 to R.sub.6 is one of the above mentioned unsubstituted or substituted alkyl groups or --CO-alkyl groups, and their salts with pharmacologically conventionally used inorganic or organic acids and their quaternary ammonium salts, processes for their preparation and their use, and pharmaceutical preparations containing these compounds.
    Type: Grant
    Filed: January 31, 1986
    Date of Patent: December 27, 1988
    Inventors: Walter Schneider, Isidor Erni, Hans K. Hegetschweiler
  • Patent number: 4789681
    Abstract: Compounds of the general formula I ##STR1## wherein R.sub.1 is hydrogen or methyl;R.sub.2 and R.sub.3, which are the same or different, represent hydrogen or methyl, or taken together, form the amidine system to which an imidazole or imidazoline ring is bound;R.sub.4 is a linear or branched C.sub.1 -C.sub.10 alkyl group; cycloalkyl, aryl, aralkyl or hetaryl group;R.sub.5 is hydrogen or methyl;A is a propylene chain optionally substituted by one or two methyl groups in one or more of the positions thereof; a chain of formula --HN--CH.sub.2 --CH.sub.2 -- or of formula --N.dbd.CH--CH.sub.2 --; a 1,4-cyclohexylene group optionally substituted by one or more methyl groups; a 1,4- phenylene group optionally substituted by one or more halogen atoms, alkyl groups or C.sub.1 -C.sub.4 alkoxy group with the proviso that, when R.sub.4 is methyl or ethyl and R.sub.1 =R.sub.2 =R.sub.3 =R.sub.
    Type: Grant
    Filed: December 22, 1986
    Date of Patent: December 6, 1988
    Assignee: Italfarmaco S.p.A.
    Inventors: Giancarlo Sportoletti, Pietro Cremonesi, Moniquet Sarret
  • Patent number: 4780129
    Abstract: Cyclohexenone derivatves of the formula ##STR1## where R.sup.1 is alkyl, R.sup.2 is alkyl, unsubstituted or substituted alkenyl or alkynyl, A is alkoxycarbonyl, carboxyl, cyano or trifluoromethyl, B is hydrogen or methyl, X is straight-chain, branched or cyclic alkylene, Z is hydrogen or alkoxycarbonyl and n is 0 or 1, and salts thereof, and their use for combatting unwanted plant growth.
    Type: Grant
    Filed: February 13, 1987
    Date of Patent: October 25, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Dieter Jahn, Ulrich Schirmer, Michael Keil, Bruno Wuerzer, Norbert Meyer
  • Patent number: 4766246
    Abstract: Sweeteners of the formula: ##STR1## and food-acceptable salts thereof, where the substituents are disclosed herein.
    Type: Grant
    Filed: August 19, 1986
    Date of Patent: August 23, 1988
    Assignee: General Foods Corporation
    Inventors: Paul R. Zanno, Ronald E. Barnett, Glenn M. Roy
  • Patent number: 4764366
    Abstract: Novel lower alkyl esters of iodo-trans-2-methylcyclohexanecarboxylic acid are useful to attract the Mediterranean Fruit Fly, "Medfly," for prolonged periods of time. The esters are competitive in attraction with the current "standard" attractant, Trimedlure, but are much more persistent. The esters may be economically produced and possess the dual properties required for effective use in Medfly control programs.
    Type: Grant
    Filed: April 27, 1987
    Date of Patent: August 16, 1988
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Terrence P. McGovern, Roy T. Cunningham
  • Patent number: 4764619
    Abstract: An optically active compound having the formula: ##STR1## wherein each of Z and Z' is a single bond, --COO--, --OCO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 -- or --CH.sub.2 O--, R is an alkyl group having from 1 to 12 carbon atoms, an alkoxyl group having from 1 to 12 carbon atoms, a cyano group or a halogen atom, each of rings A and B is a 1,4-di-substituted phenylene group or a trans-1,4-di-substituted cyclohexylene group, n is 0 or 1, X is ##STR2## wherein * indicates an optical center, and R' is an alkyl group having from 2 to 12 carbon atoms or ##STR3## where R" is a hydrogen atom, an alkyl or alkoxy group having from 1 to 12 carbon atoms, provided that when X is ##STR4## R is the alkyl group or the alkoxy group.
    Type: Grant
    Filed: March 21, 1986
    Date of Patent: August 16, 1988
    Assignee: Asahi Glass Company Ltd.
    Inventors: Tomoki Gunjima, Ryutaro Takei, Eriko Aoyama
  • Patent number: 4760167
    Abstract: A polymerizable compound of the formula: ##STR1## where R.sup.1 is H or CH.sub.3, R.sup.2 is an aliphatic group and R.sup.3 is a cycloaliphatic group and the polymer has a molecular weight of about 2,000 to 50,000;The compound is useful for forming polymers used in coating compositions for finishing the exterior of automobiles and trucks.
    Type: Grant
    Filed: September 19, 1986
    Date of Patent: July 26, 1988
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Joseph A. Vasta
  • Patent number: 4748274
    Abstract: The present invention relates to compounds which are 4-hydroxy-4-alkenylcyclohexanecarboxylic acid derivatives possessing leukotriene antagonist activity. The compounds are useful in the treatment of allergic diseases, particularly in the treatment of human asthma. They are prepared by the reaction of an appropriate oxaspiro compound with a mercaptoalkanoic acid derivative.
    Type: Grant
    Filed: November 7, 1986
    Date of Patent: May 31, 1988
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Robert J. Cregge, Nelsen L. Lentz
  • Patent number: 4748266
    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-carbazole-1-acetic acid derivatives having useful analgesic and anti-inflammatory activity.
    Type: Grant
    Filed: March 2, 1987
    Date of Patent: May 31, 1988
    Assignee: American Home Products Corporation
    Inventors: Philip F. Hughes, Dominick Mobilio, Leslie G. Humber
  • Patent number: 4744918
    Abstract: Liquid crystal phases containing at least one optically active compound of the formula IR.sup.1 --X.sup.1 --CHR.sup.o (CH.sub.2).sub.p X.sup.2 --R.sup.2 Iwherein X.sup.1 and X.sup.2 independently of one another are each --CO--O-- or --O--CO--, one of X.sup.1 and X.sup.2 may also be --O--, R.sup.1 and R.sup.2 independently of one another are each a group --(A.sup.1 --Z).sub.m --(A.sup.2).sub.n -Y, whereinA.sup.1 and A.sup.2 in each case independently of one another are a 1,4-phenylene, pyrimidine-2,5-diyl, pyrazine-2,5-diyl, pyridine-2,5-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl or 1,4-bicyclo(2,2,2)-octylene group, it also being possible for this to be monosubstituted or polysubstituted by F, Cl, Br, CN and/or alkyl groups with up to 12 C atoms, and it being possible for 1 or 2 non-adjacent CH.sub.2 groups in the alkyl groups to be replaced by O atoms,Z is --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --CH.dbd.N--, --N.dbd.CH--, --N.dbd.N--, --N(O).
    Type: Grant
    Filed: July 11, 1985
    Date of Patent: May 17, 1988
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Gerd Heppke, Feodor Oestreicher
  • Patent number: 4744811
    Abstract: Substituted oxime-ethers of the formulae ##STR1## where R.sup.1 and R.sup.2 independently of one another are C.sub.1 -C.sub.6 -alkyl, n is 2 or 3 and R.sup.3 is hydrogen or C.sub.1 -C.sub.6 -alkyl.
    Type: Grant
    Filed: April 8, 1987
    Date of Patent: May 17, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenter Schulz, Wolfgang Will, Johann Jung, Hansjoerg Fritsch
  • Patent number: 4739103
    Abstract: Di- and tri-substituted perfluorocycloalkane compounds which have a cyclohexane or decahydronaphthalene nucleus are provided. These perfluorocycloalkane compounds are carbonyl fluorides and derivatives thereof.
    Type: Grant
    Filed: February 1, 1985
    Date of Patent: April 19, 1988
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: John C. Hansen, Patricia M. Savu
  • Patent number: 4736055
    Abstract: Oxime sulfonates of formula I ##STR1## wherein Y is a polymerizable unsaturated group or epoxide group or an --OH, --NHR.sup.5, --COOH, COOR.sup.6, --COCl, --CH.sub.2 Hal, --SO.sub.2 Cl or --NCO group, Z is an (x+y)-valent connecting member, R.sup.1 and R.sup.2 are monovalent organic radicals, m is 0 or 1, x is 1 or 2 and y is 1 or 2, can be converted into polymers which can be thermally or photochemically dissociated to form free sulfonic acid groups. Said polymers can therefore be used as photoresists which can be developed with aqueous alkalis.
    Type: Grant
    Filed: April 11, 1986
    Date of Patent: April 5, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Kurt Dietliker, Werner Rutsch, Godwin Berner, Max Hunziker, Christopher G. Demmer
  • Patent number: 4736043
    Abstract: The present invention provides a process for the preparation of 4-hydroxyindole derivatives of the general formula: ##STR1## in which R.sub.1 is a hydrogen atom or an alkyl radical containing up to 6 carbon atoms and R.sub.2 is a hydrogen atom or an alkyl radical containing up to 6 carbon atoms, wherein a compound of the general formula: ##STR2## in which R.sub.2 has the same meaning as above, is reacted with a compound of the general formula:R.sub.3 --CH.sub.2 --CO--COOR.sub.1 (III)in which R.sub.1 has the same meaning as above and R.sub.3 is a reactive residue, to give a 2-(2-imino-6-oxocyclohexylidene)-propionic acid derivative of the general formula: ##STR3## in which R.sub.1, R.sub.2 and R.sub.3 have the same meanings as above, which is then cyclized in known manner to give a compound of the general formula: ##STR4## in which R.sub.1 and R.sub.2 have the same meaning as above, which is subsequently dehydrated.
    Type: Grant
    Filed: November 2, 1982
    Date of Patent: April 5, 1988
    Assignee: Boehringer Manneheim GmbH
    Inventors: Helmut Michel, Roland Ofenloch
  • Patent number: 4734520
    Abstract: Crosslinking components for hydroxy and/or primary and/or secondary amino group containing paint binders for the crosslinking of synthetic resins carrying at least two groups capable of ester or amide formation with carboxylic acids. In particular there is disclosed the use of the crosslinking components in compositions for electrodeposition (ED) whereby at 120.degree. C. and above coatings with extraordinary paint performance are obtained. The use of methyl or ethyl esters gives extremely low condensation losses. The crosslinking components are obtained through reaction of one mole of a diisocyanate, preferably at room temperature, in the presence of sodium, or preferably sodium phenolate, as catalyst, with at least one mole of a CH-active alkyl ester of the general formula X--CH.sub.2 --COOR, wherein X is --COOR, --CN or CH.sub.3 --CO-- and R is an alkyl radical with 1 to 8 C-atoms and subsequent reaction of the free isocyanate groups with polyamines of the general formula H.sub.2 N--(R--NH).sub.n --R--NH.
    Type: Grant
    Filed: May 29, 1986
    Date of Patent: March 29, 1988
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Helmut Plum, Willibald Paar
  • Patent number: 4734120
    Abstract: Dipeptides containing C-terminal phosphinothricin of the formula ##STR1## in which phosphinothricin is attached to a--preferably natural--amino acids at the amino group are effective herbicides in the pre-emergence and post-emergence techniques. The compounds are obtained, for example, by reacting phosphinothricin with the hydroxysuccinimide ester of an amino acids which is protected at the amino group in the presence of a base and subsequently splitting off the protective groups.
    Type: Grant
    Filed: December 12, 1986
    Date of Patent: March 29, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinz Kehne, Klaus Bauer, Hermann Bieringer
  • Patent number: 4730075
    Abstract: A process for the production of (1) an ether or (2) a second amine comprises reacting an activated olefin with respectively an alcohol or first amine in the presence of a catalyst which is either (a) an amidine or (b) a Lewis base and epoxide. The same catalyst may also be used to carry out the reverse reaction in which an activated olefin and an alcohol or first amine are produced from the appropriate ether or second amine.
    Type: Grant
    Filed: June 20, 1986
    Date of Patent: March 8, 1988
    Assignee: BP Chemicals Limited
    Inventor: Michael J. Green
  • Patent number: 4723038
    Abstract: Processes for preparing compounds which exhibit seed germinating activity are disclosed. An ester of acetoacetic acid is condensed with a ketone to produce a substituted cyclohexenone which is reacted with a thiol to get a dithioketal which is then desulfurized to produce an ester of a substituted cyclohex-2-ene-1-carboxylic acid which exhibits seed germinating activity. The same compound can be produced by a different process which reacts the substituted cyclohexenone with a reducing agent. An exemplary reducing agent would be an organosilane and a Lewis acid.
    Type: Grant
    Filed: December 31, 1985
    Date of Patent: February 2, 1988
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventor: Oliver D. Dailey, Jr.
  • Patent number: 4723005
    Abstract: New anisotropic compounds of the formula (1) are useful in liquid crystal mixtures for electrooptical displays; at least one of the end groups of the compounds (1) is an alkyl group which carries cyano or halogen in a terminal or non-terminal position. This offers advantages for longitudinal polarization and/or cross-polarization of the anisotropic compounds with the aid of the comparatively highly polarizing cyano or halogen substituents, in particular high clear points, low .DELTA..epsilon./.epsilon..perp. values and/or negative .DELTA..epsilon. values.
    Type: Grant
    Filed: September 10, 1984
    Date of Patent: February 2, 1988
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Tuong Huynh-Ba, Maged A. Osman
  • Patent number: 4711958
    Abstract: Amino acid derivatives represented by formula ##STR1## wherein His represents an L-histidyl group, X represents a straight or branched alkoxy group having 1 to 7 carbon atoms, a straight or branched alkylamino group having 1 to 7 carbon atoms, a cycloalkyloxy group having 3 to 7 carbon atoms, a morpholino group, said alkoxy group having one or more halogen atoms as substituents; or a pharmaceutically acceptable salt, are useful in the treatment of hypertension.
    Type: Grant
    Filed: April 1, 1987
    Date of Patent: December 8, 1987
    Assignee: Kissei Pharmaceutical Co., Ltd.
    Inventors: Kinji Iizuka, Tetsuhide Kamijo, Tetsuhiro Kubota, Kenji Akahane, Hideaki Umeyama, Yoshiaki Kiso
  • Patent number: 4708954
    Abstract: Pharmaceutical compositions containing an oxaluric acid derivative of the formula: ##STR1## wherein each of R.sub.1 and R.sub.2, which may be the same or different, is hydrogen; an alkyl group or a cycloalkyl group; or R.sub.1 and R.sub.2 are joined to form a heterocyclic ring with the nitrogen atom to which they are both attached; and R.sub.3 is hydrogen or an alkyl group. These compounds have excellent hypoglycemic effects with low toxcicity and safety.
    Type: Grant
    Filed: February 7, 1986
    Date of Patent: November 24, 1987
    Assignee: Nippon Zoki Pharmaceutical Co., Ltd.
    Inventors: Kazuharu Ienaga, Ko Nakamura, Akira Ishii
  • Patent number: 4708441
    Abstract: Compounds of the formula ##STR1## wherein X.sup.2 is a single covalent bond or --COO--; X.sup.1 is a single covalent bond, --COO--, --CH.sub.2 CH.sub.2 -- or when X.sup.2 is --COO--, X.sup.1 also can be p--C.sub.6 H.sub.4 --, p--C.sub.6 H.sub.4 --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --p--C.sub.6 H.sub.4, p--C.sub.6 H.sub.4 --COO-- or --COO--p--C.sub.6 H.sub.4 ; ring A is a benzene ring or trans-1,4-cyclohexylene; ring B is a benzene ring or when X.sup.2 is --COO-- and X.sup.1 is a single covalent bond, --COO-- or --CH.sub.2 CH.sub.2 --, ring B also can be trans-1,4-cyclohexylene; Z.sup.1, Z.sup.2 and Z.sup.3 individually are hydrogen or when positioned on a benzene ring which is not linked directly with a further ring via a single covalent bond, Z.sup.1, Z.sup.2 and Z.sup.3 also can be halogen, cyano or methyl; Y.sup.2 is cyano, nitro, 2,2-dicyanovinyl or when Y.sup.1 is hydrogen Y.sup.2 also can be 2,2-dicyano-1-methylvinyl; Y.sup.1 is halogen, cyano, C.sub.1 -C.sub.3 -alkyl or, when X.sup.
    Type: Grant
    Filed: August 16, 1985
    Date of Patent: November 24, 1987
    Assignee: Hoffman-La Roche Inc.
    Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
  • Patent number: 4701282
    Abstract: This invention provides smoking compositions which contain a .beta.-hydroxy-.gamma.-ketoester compound as a flavorant-release additive.In one of its embodiments, this invention provides tobacco compositions which contain a flavorant-release additive such as dodecyl 3-hydroxy-2,2,3-trimethyl-4-oxopentanoate: ##STR1## Under cigarette smoking conditions the above illustrated .beta.-hydroxy-.gamma.-keto ester pyrolyzes into 2,3-butanedione and other products which enhance the flavor of the mainstream smoke and the aroma of sidestream smoke.
    Type: Grant
    Filed: August 30, 1985
    Date of Patent: October 20, 1987
    Assignee: Philip Morris Incorporated
    Inventors: W. Geoffrey Chan, Yoram Houminer
  • Patent number: 4693745
    Abstract: Novel cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties. The cyclohexanedionecarboxylic acid derivatives have the formula I ##STR1## wherein A is an --OR.sub.2 or --NR.sub.3 R.sub.4 radical,R is C.sub.3 -C.sub.6 cycloalkyl,R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkylthioalkyl; C.sub.3 -C.sub.6 alkenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; C.sub.3 -C.sub.6 alkynyl; phenyl or C.sub.1 -C.sub.6 aralkyl, wherein the phenyl nucleus is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, nitro or cyano; one of R.sub.3 and R.sub.4 is methoxy; orR.sub.3 and R.sub.
    Type: Grant
    Filed: October 9, 1985
    Date of Patent: September 15, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans-Georg Brunner