Having -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Six-membered Hetero Ring Patents (Class 546/298)
  • Patent number: 5541203
    Abstract: The invention provides antifungal compounds of the formula: ##STR1## and the pharmaceutically acceptable salts thereof, wherein R is phenyl substituted by up to 3 substituents each independently selected from halo and trifluoromethyl;R.sup.1 is C.sub.1 -C.sub.4 alkyl;R.sup.2 is ##STR2## R.sup.3 is --S(O).sub.m R.sup.4 ; R.sup.4 is C.sub.1 -C.sub.4 alkyl; andm is 0, 1 or 2, together with pharmaceutical compositions containing, and processes and intermediates for preparing, said compounds.
    Type: Grant
    Filed: April 8, 1994
    Date of Patent: July 30, 1996
    Assignee: Pfizer Inc.
    Inventors: Andrew S. Bell, Kenneth Richardson, Peter J. Whittle
  • Patent number: 5516784
    Abstract: Compounds of formula ##STR1## wherein Ar, W, Z, Q, R.sub.1, U, and T are as set forth herein, are described. These compounds are active as agents against retroviruses and in particular against HIV.
    Type: Grant
    Filed: February 10, 1994
    Date of Patent: May 14, 1996
    Assignee: Schering Corporation
    Inventors: Frank Bennett, Ashit Ganguly, Viyyoor Girijavallabhan, Naginbhai Patel
  • Patent number: 5516776
    Abstract: A process and intermediates for the enantioselective synthesis of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid are disclosed.
    Type: Grant
    Filed: September 12, 1994
    Date of Patent: May 14, 1996
    Assignee: Eli Lilly and Company
    Inventors: Charles J. Barnett, Thomas M. Wilson
  • Patent number: 5512536
    Abstract: Disclosed herein are herbicidal pyridine compounds substituted at the 2- or 6-position with an OR.sub.2 moiety where R.sub.2 is hydrogen, lower alkyl, halomethyl, lower cyanoalkyl, alkenyl or alkynyl, as well as herbicidal compositions and herbicidal use of these compounds.
    Type: Grant
    Filed: November 15, 1994
    Date of Patent: April 30, 1996
    Assignee: Rohn and Haas Company
    Inventors: Donald E. Korte, Len F. Lee
  • Patent number: 5503639
    Abstract: Laundry detergents and bleaching systems comprising acyl verolactam bleach activators having the formula: ##STR1## wherein R.sup.1 is a substituted or unsubstituted alkyl or alkoxy group containing from about 1 to about 18 carbon atoms wherein the longest linear alkyl or alkoxy chain extending from and including the carbonyl carbon contains from about 2 to about 12 carbon atoms; ##STR2## wherein R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6 are members selected from the group consisting of H, halogen, nitro, alkyl, alkoxy, alkoxyaryl, alkaryl, and alkaryloxy moieties containing from about 1 to about 12 carbon atoms, and substituents having the structures: ##STR3## wherein R.sup.7 is selected from the group consisting of H, alkyl, alkaryl, alkoxy, alkoxyaryl, alkaryloxy, and aminoalkyl; X is O, NH, or NR.sup.9, wherein R.sup.9 is H or a C.sub.1 -C.sub.4 alkyl group; and R.sup.8 is an alkyl, cycloalkyl, or aryl group containing from 3 to 11 carbon atoms; orc) mixtures of a) and b)are provided.
    Type: Grant
    Filed: February 6, 1995
    Date of Patent: April 2, 1996
    Assignee: The Procter & Gamble Company
    Inventors: Alan D. Willey, Michael E. Burns, Shuichi Tsunetsugu
  • Patent number: 5481013
    Abstract: Compounds of the formula ##STR1## in which A is oxygen, sulfur or --NR.sub.1 --;B is C.sub.2 -C.sub.6 alkylene,D-E is --O--E, --S--E, --O--CH.sub.2 --E, --O--C(.dbd.O)--E, --O--C(.dbd.O)--O--E, --O--C(.dbd.O)--N(H)--E or --O--C(.dbd.S)--N(H)--E;E is phenyl; phenyl which is substituted by one to three substituents; a five-membered aromatic heterocycle having one to three hetero atoms; a five-membered aromatic heterocycle which has one to three hetero atoms and which is substituted by one or two substituents; a six-membered aromatic heterocycle which has one to three nitrogen atoms; or a six-membered aromatic heterocycle which has one to three nitrogen atoms and which is substituted by one or two substituents;L is halogen or methyl;X is fluorine;Y is chlorine or fluorine;Z is hydrogen, fluorine or methyl;m is the number zero, one, two, three, four or five;n is the number zero, one or two andR.sub.1 is hydrogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: June 23, 1993
    Date of Patent: January 2, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Maienfisch, Thomas Pitterna, Manfred Boger
  • Patent number: 5476939
    Abstract: The present invention relates to the field of immunoassays for metal ions. The invention presents: metal ion-ligand coordination complexes ("MLC"), novel ligands, antibodies specific for MLC, immunoassays utiliizing the foregoing, and methods for selecting said antibodies.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: December 19, 1995
    Assignee: Abbott Laboratories
    Inventor: David K. Johnson
  • Patent number: 5455348
    Abstract: The invention relates to cyclic imino derivatives of general formulaB--X.sub.5 --X.sub.4 --X.sub.3 --X.sub.2 --X.sub.1 --A--Y--E(I)whereinA, B, E, X.sub.2 to X.sub.5 and Y are defined as in claim 1, the stereoisomers, tautomers, mixtures and salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable pharmacological properties, preferably aggregation-inhibiting effects, pharmaceutical compositions which contain these compounds and processes for preparing them.
    Type: Grant
    Filed: December 23, 1993
    Date of Patent: October 3, 1995
    Assignee: Karl Thomae
    Inventors: Volkhard Austel, Wolfgang Eisert, Frank Himmelsbach, Guenter Linz, Thomas Mueller, Helmut Pieper, Johannes Weisenberger
  • Patent number: 5453509
    Abstract: This invention relates to a method of preparation of 1,2-dihydropyridine compounds having the structure: ##STR1## which comprises reacting a compound having the structure: ##STR2## The reaction is performed under suitable reaction conditions and in an appropriate solvent so as to form the 1,2-dihydropyridine compound. In a similar manner 1,2-dihydroquinolines, dihydroisoquinolines, dihydropyridones, dihydroquinolones and dihydroisoquinolones may also be prepared. The invention is also directed to compounds prepared by this method.
    Type: Grant
    Filed: October 8, 1993
    Date of Patent: September 26, 1995
    Assignee: Synaptic Pharmaceutical Corporation
    Inventors: T. G. Murali Dhar, Charles Gluchowski
  • Patent number: 5440043
    Abstract: The present invention relates to novel substituted pyridine compounds useful as intermediates in the preparation of herbicidal compounds and the process for the preparation of said pyridine compounds.
    Type: Grant
    Filed: April 19, 1994
    Date of Patent: August 8, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Charles D. Adams, Greg A. Bullock, George C. Chiang
  • Patent number: 5418245
    Abstract: Methods of inhibiting cell proliferation in a patient suffering from such disorder comprising the use of a styryl-substituted heteroaryl compound wherein the heteroaryl group is a monocyclic ring with 1 or 2 heteroatoms, or a bicyclic ring with 1 to about 4 heteroatoms, said compound optionally substituted or polysubstituted, with the proviso that when said ring is polysubstituted, the substituents do not have a common point of attachment to said ring, and those compounds wherein no substituent on the heteroaryl group is a carboxy group or an ester group, and pharmaceutical compositions comprising such compounds.
    Type: Grant
    Filed: March 17, 1994
    Date of Patent: May 23, 1995
    Assignee: Rhone-Poulenc Rorer International (Holdings) Inc.
    Inventors: Alfred P. Spada, Paul E. Persons
  • Patent number: 5418244
    Abstract: Compounds of the formula ##STR1## wherein the variables are defined in the specification. The compounds and their salts are soft anticholinergic/antisecretory agents especially useful as mydriatics and as antiperspirants.
    Type: Grant
    Filed: August 11, 1993
    Date of Patent: May 23, 1995
    Assignee: University of Florida
    Inventors: Richard H. Hammer, Nicholas S. Bodor
  • Patent number: 5405413
    Abstract: Laundry detergents and bleaching systems comprise acyl valerolactam bleach activators. The bleach activators are effective under mixed soil conditions, especially mixtures of hydrophobic and hydrophilic soils and stains.
    Type: Grant
    Filed: June 24, 1993
    Date of Patent: April 11, 1995
    Assignee: The Procter & Gamble Co.
    Inventors: Alan D. Willey, Michael E. Burns, Shuichi Tsunetsugu
  • Patent number: 5399701
    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: July 15, 1993
    Date of Patent: March 21, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Eugene P. Janulis
  • Patent number: 5366982
    Abstract: This invention relates to compounds having selective LTB.sub.4 antagonist properties, compositions comprising said compounds and methods for the treatment of disorders involving LTB.sub.4 agonist-mediated activity utilizing said compositions wherein the compounds are described by the general formula ##STR1## and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: February 17, 1993
    Date of Patent: November 22, 1994
    Assignee: Rhone-Poulenc Rorer S.A.
    Inventors: Norbert Dereu, Wolfram Hendel, Richard Labaudiniere
  • Patent number: 5366956
    Abstract: Herbicidal compounds ##STR1## in which Q represents a group --C(O)--C(CN).dbd.CH--NR.sup.1 R.sup.2, R.sup.1 and R.sup.2 each independently represents alkyl, or together represent alkylene optionally interrupted by oxygen, m is O or m is an integer from 1 to 3 and the or each Y independently represents halogen or alkyl and n is O or n is an integer from 1 to 5 and the or each X independently represents halogen, alkyl, haloalkyl, cyanoalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, haloalkylthio, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, cyano, nitro, alkylsulphonyl, alkysulphinyl, sulphonamido, or phenyl optionally substituted by alkyl, haloalkyl, alkoxy or halogen.
    Type: Grant
    Filed: March 1, 1993
    Date of Patent: November 22, 1994
    Assignee: Shell Research Limited
    Inventors: Christopher J. Foster, Terence Gilkerson, Richard Stocker
  • Patent number: 5364939
    Abstract: The process for the production of the carboxylic acid chlorides of the aromatic nitrogen heterocycles of the series of the compounds of the general formulas: ##STR1## The hydroxy carboxylic acids of the aromatic nitrogen heterocycles from the series of the compounds of the general formulas: ##STR2## In the general formulas I to VI, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are the same or different and each is a hydrogen atom or a halogen atom. The chlorination is performed with a solution of phosphorous pentachloride in phosphoroxy chloride. The excess phosphorous pentachloride is converted into phosphoroxy chloride either with a C.sub.1 -C.sub.4 -carboxylic acid or with a silane of the general formula:(CH.sub.3).sub.3 --Si--OR.sub.9 VIIThen the product according to one of the general formulas I to III is isolated.
    Type: Grant
    Filed: March 17, 1993
    Date of Patent: November 15, 1994
    Inventor: Jean-Paul Roduit
  • Patent number: 5364940
    Abstract: A new microbiological process for the production of hydroxy-nitrogen-heterocyclic-carboxylic acids or their soluble salts of the general formula: ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and each is a hydrogen atom, a halogen atom or a C.sub.1 -C.sub.4 alkyl group and X is a nitrogen atom or a CR.sub.3 function, wherein R.sub.3 is a hydrogen atom or a halogen atom, starting from the corresponding nitrogen-heterocyclic-carboxylic acids, as well as new microorganisms suitable for use in the process.
    Type: Grant
    Filed: July 13, 1993
    Date of Patent: November 15, 1994
    Assignee: Lonza Ltd.
    Inventors: Andreas Kiener, Andreas Tschech, Andreas Tinschert, Klaus Heinzmann
  • Patent number: 5360808
    Abstract: Arylcarbonylaminoalkyl-dihydro-oxo-pyridines of Formula I ##STR1## are disclosed wherein aryl is an aromatic or heteroaromatic system, n is zero through 5; R and R(1), are hydrogen, or loweralkyl; W is hydrogen, (hetero)-(aryl)-loweralkyl; Z is hydrogen, CH.sub.2 OR(2.sub.), CHO, (CO)OR(2), (CO)NR(2).sub.2.Processes for the preparation of compound I are also disclosed.Compounds I are suitable for the treatment of disorders of the cardiovascular system, for example of hypertension, of cardiac insufficiency or of disturbances of blood flow in the coronary systems such as, for example, angina. Disturbances of cerebral and peripheral blood flow are likewise influenced beneficially. Furthermore, compounds I are able to influence smooth-muscle organs such as uterus, bronchi, intestines and biliary system, the urinary tract (ureter, bladder and urethra) in the sense of spasmolysis.
    Type: Grant
    Filed: February 18, 1993
    Date of Patent: November 1, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinrich Englert, Dieter Mania, David Wettlaufer, Erik Klaus
  • Patent number: 5352793
    Abstract: The invention relates to sunscreen compounds of formula I ##STR1## wherein R.sup.1 is selected from alkyl, alkenyl, alkynyl substituted alkyl, substituted alkenyl, phenyl, substituted phenyl, substituted benzyl, cycloalkyl, cycloalkenyl, substituted cycloalkyl, substituted cycloalkenyl;R.sup.2 is selected from hydrogen, alkyl and alkoxy;R.sup.3 is selected from alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, phenyl, benzoyl, substituted phenyl, substituted benzyl, substituted benzoyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, alkanyoyl, substituted alkanoyl, the group OROROR.sup.9 wherein R is a bivalent hydrocarbon radical and R.sup.9 is alkyl, alkenyl, phenyl benzyl, substituted phenyl, substituted benzyl;R.sup.4 is alkyl or alkoxy;n is an integer from 0 to 4; andR.sup.5 and R.sup.6 are independently selected from alkyl, alkoxy, alkanoyl, alkanoyl substituted by hydroxyl or alkoxycarbonyl.
    Type: Grant
    Filed: November 27, 1990
    Date of Patent: October 4, 1994
    Assignee: ICI Australia Operations Proprietary Limited
    Inventors: Graham Bird, Neil Fitzmaurice, Walter C. Dunlap, Bruce E. Chalker, Wickramasinghe M. Bandaranayake
  • Patent number: 5336772
    Abstract: N-fluoropyridinium salts of the following formula are prepared by reacting a pyridine compound with a Br nsted acid and fluorine, wherein the reaction solvent contains a greater than equimolar amount of the pyridine compound relative to an amount of the Br nsted acid. ##STR1## The method can produce N-fluoropyridinium salts with a high yield.
    Type: Grant
    Filed: December 26, 1991
    Date of Patent: August 9, 1994
    Assignee: Onoda Cement Co., Ltd.
    Inventors: Yukinori Saiki, Kazunori Nukui
  • Patent number: 5334723
    Abstract: A novel 2-piperidinecarboxylic acid derivative represented by the formula: ##STR1## wherein X represents an oxygen atom, a sulfur atom or a nitrogen atom to which a hydrogen atom is bound; and * represents that the configuration of the carbon atom binding to the carboxyl group is (S), (R) or a mixture of (S) and (R); and a pharmaceutically acceptable salt thereof which exerts an antitumor effect over a wide range of tumor cells.
    Type: Grant
    Filed: August 31, 1992
    Date of Patent: August 2, 1994
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Tsuneo Okonogi, Osamu Makabe, Yuichi Yamamoto, Osamu Itoh, Tsutomu Tsuruoka, Takayuki Usui, Seiji Shibahara, Kozo Nagaoka, Shigeharu Inouye, Nobuko Okada, Susumu Nishimura
  • Patent number: 5332823
    Abstract: The present invention relates to novel substituted pyridine compounds useful as intermediates in the preparation of herbicidal compounds and the process for the preparation of said pyridine compounds.
    Type: Grant
    Filed: May 13, 1993
    Date of Patent: July 26, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Charles D. Adams, Greg A. Bullock, George C. Chiang
  • Patent number: 5322845
    Abstract: An acrylic acid compound useful for fungicides is provided. The compound has the following formula (I) ##STR1## wherein X represents a phenyl group which may be substituted, or a methylene group, n represents 0 or 1, Y represents an oxygen atom or a sulfur atom, Z represents a phenyl group, an aralkyl group, an aromatic heterocyclyl group or an aromatic heterocyclylmethylene group and Z may be substituted.
    Type: Grant
    Filed: October 1, 1992
    Date of Patent: June 21, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tsuguhiro Katoh, Atsuo Mizuguchi, Hirotaka Takano
  • Patent number: 5321140
    Abstract: Compounds of Formula I ##STR1## are made in accordance with the following scheme: ##STR2## wherein R may be loweralkyl; R.sub.1 may be H, loweralkyl, loweralkoxy, or halo; R.sub.2, R.sub.3, R.sub.4, and R.sub.5 may each independently be H, amino, hydroxy, loweralkyl, loweralkoxy, loweralkylthio, di(loweralkyl)amino, cyano, methylenedioxy, formyl, nitro, halo, trifluoromethyl, aminomethyl, azido, amido, hydrazino, or any of the twenty standard amino acids bonded to the A ring via the amino-nitrogen atom; Y is H and W and X are halogen. Also disclosed are novel processes for making starting materials for the scheme given above, and novel intermediates employed in these processes.
    Type: Grant
    Filed: February 12, 1993
    Date of Patent: June 14, 1994
    Assignee: North Carolina State University
    Inventors: Daniel L. Comins, Matthew F. Baevsky
  • Patent number: 5308520
    Abstract: Various heterocyclic compounds have been discovered that impart improved fuel economy and friction modification to lubricant and fuel compositions. These heterocyclic compounds of the invention preferably contain nitrogen and may be further reacted with hydrocarbyl carboxylic acid acylating reactants or hydrocarbyl phenolic reactants to give higher molecular materials. These higher molecular weight materials have higher oil-solubility and impart dispersancy properties to lubricant and fuel compositions.
    Type: Grant
    Filed: July 31, 1989
    Date of Patent: May 3, 1994
    Assignee: The Lubrizol Corporation
    Inventors: Joseph W. Pialet, Paul E. Adams
  • Patent number: 5304565
    Abstract: Nitrogen-containing heterocyclic compounds of the formula (I): ##STR1## wherein Y is N or CH; R.sup.1, which may be optionally bound through a hetero atom, is a hydrocarbon residue which may be substituted; R.sup.2 and R.sup.3 which may be same or different, are each independently hydrogen, cyano, nitro, optionally substituted lower alkyl, or --COD wherein D is alkoxy, hydroxy, halogen, or optionally substituted amino: or R.sup.2 and R.sup.3 are taken together to form a benzene ring which may be substituted; the dotted line is a chemical bond; Z is bound to a hetero nitrogen atom and is a group having the formula: ##STR2## wherein R.sup.4 is hydrogen, halogen or nitro, and R.sup.
    Type: Grant
    Filed: March 7, 1991
    Date of Patent: April 19, 1994
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Akira Morimoto, Kohei Nishikawa
  • Patent number: 5294597
    Abstract: Compounds of formula ##STR1## wherein Z is oxygen or sulphur;R.sup.1 is hydrogen, halogen, alkyl or haloalkyl;R.sup.2 is hydrogen, or alkyl;q is 0 or 1;R.sup.3 is hydrogen, alkyl or alkenyl; the or each X independently is halogen, optionally substituted alkyl or alkoxy, alkenyloxy, alkynyloxy, cyano, carboxy, alkoxycarbonyl, (alkylthio)carbonyl, alkylcarbonyl, amido, alkylamido, nitro, alkylthio, haloalkylthio, alkenylthio, alkynylthio, alkylsulphinyl, alkylsulphonyl, alkyloximinoalkyl or alkenyloximinoalkyl;n is 0 or an integer from 1 to 5; the or each Y independently is a halogen, alkyl, nitro, cyano, haloalkyl, alkoxy or haloalkoxy; and m is 0 or an integer from 1 to 5, their preparation and use as herbicides.
    Type: Grant
    Filed: March 4, 1991
    Date of Patent: March 15, 1994
    Assignee: Shell Research Limited
    Inventors: Christopher J. Foster, Terence Gilkerson, Richard Stocker
  • Patent number: 5254571
    Abstract: This invention relates to phenylpyridone derivatives which have bronchodilator and anti-allergic activities. A compound of the invention is 6-(2-propoxyphenyl)-1,2-dihydro-2-oxopyridine-3-carboxamide.
    Type: Grant
    Filed: September 25, 1992
    Date of Patent: October 19, 1993
    Assignee: Smith Kline & French Laboratories Ltd.
    Inventors: William J. Coates, Sean T. Flynn
  • Patent number: 5238908
    Abstract: This invention relates to glutaramic acids and derivatives exhibiting herbicidal activity having the structure ##STR1## wherein A is a carboxylic acid or a derivative thereof, D is CH or N, and R, R.sup.1, R.sup.2, T, X, Y, and Z are as defined within, compositions containing these compounds and methods of controlling weeds with these compounds.
    Type: Grant
    Filed: August 9, 1990
    Date of Patent: August 24, 1993
    Assignee: Rohm and Haas Company
    Inventors: Barry C. Lange, John W. Ashmore, Jane Wissinger-Cornille
  • Patent number: 5236936
    Abstract: The invention concerns pharmaceutically useful compounds of the formula I, in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, X and Z have the various meanings defined herein, and their non-toxic salts, and pharmaceutical compositions containing them. The novel compounds are of value in treating conditions such as hypertension and congestive heart failure. The invention further concerns processes for the manufacture of the novel compounds and the use of the compounds in medical treatment.
    Type: Grant
    Filed: February 11, 1992
    Date of Patent: August 17, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: David A. Roberts, Robert H. Bradbury, Martin P. Edwards, Arnold H. Ratcliffe
  • Patent number: 5235060
    Abstract: The present invention relates to novel substituted pyridine compounds useful as intermediates in the preparation of herbicidal compounds and the process for the preparation of said pyridine compounds. ##STR1## wherein: R.sup.1 is selected from the group C.sub.1 -C.sub.4 alkyl;R.sup.2 is selected from the group hydrogen, C.sub.1 -C.sub.3 alkyl optionally substituted with methoxy or 1-3 fluorine and C.sub.1 -C.sub.2 alkoxy optionally substituted with 1-3 fluorine;R.sup.3 is selected from the group C.sub.1 -C.sub.3 alkyl substituted with methoxy or 1-3 fluorine;R.sup.4 is selected from the group SO.sub.2 R.sup.5, CO.sub.2 R.sup.5 and C(O)N(R.sup.6).sub.2 ;R.sup.5 is selected from the group C.sub.1 -C.sub.2 alkyl optionally substituted with C.sub.1 -C.sub.2 alkoxy or 1-3 halogens independently selected from the group chlorine and fluorine;R.sup.6 is C.sub.1 -C.sub.2 alkyl;M is selected from the group Li, Na, K, Mg, Ca, NH.sub.4, and alkyl substituted NH.sub.4.
    Type: Grant
    Filed: July 11, 1991
    Date of Patent: August 10, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Charles D. Adams, Greg A. Bullock, George C. Chiang
  • Patent number: 5228897
    Abstract: Disclosed herein are herbicidal pyridine compounds substituted at the 2- or 6-position with an OR.sub.2 moiety where R.sub.2 is hydrogen, lower alkyl, halomethyl, lower cyanoalkyl, alkenyl or alkynyl, as well as herbicidal compositions and herbicidal use of these compounds.
    Type: Grant
    Filed: April 20, 1992
    Date of Patent: July 20, 1993
    Assignee: Monsanto Company
    Inventors: Donald E. Korte, Len F. Lee
  • Patent number: 5217981
    Abstract: This invention relates to a compound of the formula ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, --CH.dbd.CH--or --CH.dbd.N--; wherein R.sub.1 is alkyl, alkenyl or alkynyl of about 1 to 20 carbon atoms; wherein R is --CO.sub.2 R.sup.2, tetrazole, methylsulfonamide or benzenesulfonamide, wherein R.sup.2 is hydrogen, alkyl of 1 to 6 carbon atoms or a pharmaceutically acceptable cation and R.sup.3 is hydroxyl or halogen, having utility as LTB.sub.4 synthesis inhibitors.
    Type: Grant
    Filed: October 27, 1992
    Date of Patent: June 8, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
  • Patent number: 5216169
    Abstract: A 3-hydroxypyridineazomethine dye represented by general formula (I) ##STR1## wherein R.sub.1 represents an aliphatic group, an aromatic group, or a heterocyclic group; R.sub.2 represents an aliphatic group, an aromatic group, a heterocyclic group, an alkoxy group, an aryloxy group, an alkenyloxy group, an amino group, an acyl group, an ester group, an amido group, a carbamoylamino group, a sulfamoylamino group, a sulfamido group, an imido group, a ureido group, an aliphatic or an aromatic sulfonyl group, an aliphatic or an aromatic thio group, a hydroxyl group, a cyano group, a carboxy group, or a halogen atom; R.sub.3 represents an aryl group; Y represents a bivalent linking group containing at least one of amide bond and ester bond; n represents 0, 1 or 2; where n is 2, the two R.sub.2 groups may be the same group or atom or may be mutually different groups or atoms, or the two R.sub.2 groups may form a ring; where n is 1 or more, R.sub.1 and R.sub.2 may form a ring; and at least one of R.sub.1 and R.sub.
    Type: Grant
    Filed: September 18, 1990
    Date of Patent: June 1, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Shigeru Yamazaki
  • Patent number: 5204357
    Abstract: The invention relates to compounds of the formula I ##STR1## in which A represents a substituted thio-, sulfinyl- or sulfonyl-alkanoyl radical or a four- to eleven-membered heterocycle, B is an amino acid residue, R.sup.1 denotes hydrogen (substituted) alkyl, (substituted)cycloalkyl or aryl, R.sup.2 represents hydrogen, (substituted)alkyl or aryl, R.sup.3 denotes a radical of the formula --(CH.sub.2).sub.q --(X).sub.r --(CH.sub.2).sub.s --R.sup.6 with X denoting CF.sub.2, CO or CHR.sup.8, R.sup.6 denoting a (substituted)heteroaromatic, R.sup.8 denoting alkyl, alkoxy, alkylthio, alkylamino, hydroxyl, azide or halogen, q and s denoting 1 to 4, and r denoting 0 or 1, and R.sup.9 is hydrogen, (substituted)alkyl, alkanoyl, cycloalkanoyl, (substituted) aroyl or (substituted)aryl, and to the salts thereof. In addition, processes for the preparation of these compounds, and the use thereof as renin inhibitors are described.
    Type: Grant
    Filed: February 14, 1989
    Date of Patent: April 20, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rainer Henning, Hansjorg Urbach, Dieter Ruppert, Bernward Scholkens
  • Patent number: 5198439
    Abstract: The invention concerns pharmaceutically useful novel compounds of the formula I, in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, X and Z have the various meanings defined herein, and their non-toxic salts, and pharmaceutical compositions containing them. The novel compounds are of value in treating conditions such as hypertension and congestive heart failure. The invention further concerns processes for the manufacture of the novel compounds and the use of the compounds in medical treatment.
    Type: Grant
    Filed: April 27, 1992
    Date of Patent: March 30, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: David A. Roberts, Arnold H. Ratcliffe, Robert H. Bradbury
  • Patent number: 5196045
    Abstract: A compound having the structural formula ##STR1## wherein: Y is selected from O and S;R.sub.1 and R.sub.4 are independently selected from fluorinated methyl, chlorofluorinated methyl, and C.sub.1 -C.sub.4 alkyl, provided that not both R.sub.1 and R.sub.4 may be C.sub.1 -C.sub.4 alkyl;R.sub.2 is selected from hydrogen, lower alkyl, haloalkyl, alkenyl, alkynyl, haloalkenyl, and a cation;R.sub.3 is selected from C.sub.1 -C.sub.5 alkyl, cycloalkyl, cycloalkylalkyl, hydroxy, and alkoxy; andX is selected from ##STR2## in which R.sub.8 is selected from H, alkyl and CF.sub.3 and R.sub.10 is selected from F, Cl, --OR.sup.1, --SR.sup.1, --NHR.sup.1, --N(R.sup.1).sub.2, phenyl, substituted phenyl, and --P(OR.sup.1).sub.2where R.sup.1 is as defined above; ##STR3## wherein R.sup.1 is as defined above; ##STR4## wherein R.sub.14 and R.sub.15 are independently selected from hydrogen and alkyl; and --N.dbd.C.dbd.O and their use as herbicides.
    Type: Grant
    Filed: March 20, 1991
    Date of Patent: March 23, 1993
    Assignee: Monsanto Company
    Inventors: Len F. Lee, Mark G. Dolson
  • Patent number: 5190723
    Abstract: A process for inhibiting corrosion involves new compositions which comprise an organic material and, a corrosion inhibitor which is a compound having the formula: ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different and each is hydrogen, C.sub.1 -C.sub.15 alkyl, C.sub.3 -C.sub.15 alkenyl, C.sub.7 -C.sub.10 phenylalkyl, C.sub.6 -C.sub.18 aryl having 6 or 10 aromatic ring carbon atoms; or C.sub.5 -C.sub.12 cycloalkyl;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; n is 0 or 1;A is a residue of a heterocyclic ring having 5-7 ring members and 1-4 nitrogen atoms, or A is a residue of a heterocyclic ring having 5-7 ring members and 1-4 nitrogen atoms and is fused to a further heterocyclic ring or to a carbocyclic ring, or A is a carbocyclic ring, in particular a phenyl or naphthyl ring, and wherein R is one or more of hydrogen, C.sub.1 -C.sub.15 alkyl, C.sub.1 -C.sub.4 halogenoalkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.12 alkylthio, phenylthio, benzylthio, C.sub.1 -C.sub.
    Type: Grant
    Filed: December 3, 1990
    Date of Patent: March 2, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Emyr Phillips, Robert C. Wasson
  • Patent number: 5187176
    Abstract: Phenyl substituted heterocyclic compounds having insecticidal activity have the formula (I): ##STR1## wherein R.sup.1 is an optionally substituted pyridone, thiopyridone, pyrimidinthione, pyrimidinone, pyrazole, imidazole or triazole group; R.sup.2 is hydrogen, halogen, haloalkyl, nitro, cyano or a group --CX--NY.sup.1 Y.sup.2 ; R.sup.3 and R.sup.5 are hydrogen, halogen, alkyl or cycloalkyl; R.sup.4 is halogen, haloalkyl, haloalkoxy or S(O).sub.n R.sup.6 ; and Y.sup.1 and Y.sup.2 are independently selected from hydrogen, nitro, amino or optionally substituted alkyl or Y.sup.1 and Y.sup.2 together with the nitrogen to which they are attached form an aliphatic heterocyclic group or form the group .dbd.CHY.sup.3 or Y.sup.1 is hydrogen and Y.sup.2 is alkoxycarbonyl, alkylcarbonyl, optionally substituted aralkyl or --S(O).sub.n R.sup.6.
    Type: Grant
    Filed: October 9, 1991
    Date of Patent: February 16, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Roger Salmon, Raymond L. Sunley, Alan J. Whittle
  • Patent number: 5185319
    Abstract: Admixture of insulin and a hydroxypyridone being: (1) a 3-hydroxypyrid-4-one in which the hydrogen atom attached to the nitrogen atom is replaced by an aliphatic acyl group, by an aliphatic hydrocarbon group, or by an aliphatic hydrocarbon group substituted by one or more substituents selected from aliphatic acyl, alkoxy, cycloalkoxy, aliphatic amide, aliphatic ester, halogen and hydroxy groups and, optionally, in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by an aliphatic acyl, alkoxy, cycloalkoxy, aliphatic amide, aliphatic ester, halogen or hydroxy group, by an aliphatic hydrocarbon group, or by an aliphatic hydrocarbon group substituted by an alkoxy, cycloalkoxy, aliphatic ester, halogen or hydroxy group, or a salt thereof.
    Type: Grant
    Filed: May 3, 1990
    Date of Patent: February 9, 1993
    Assignee: National Research Development Corporation
    Inventors: Robert C. Hider, Michael A. Stockham
  • Patent number: 5182401
    Abstract: A process for the preparation of a 3-amino-2-(het)aroyl-acrylic acid derivative fo the formula ##STR1## in which Y represents a nitrile, or an ester group, --COOR.sub.1, or an acetyl group, whereR.sup.1 denotes C.sub.1 -C.sub.4 -alkyl, andR denotes optionally substituted alkyl, cyclopropyl, alkoxy, phenyl or amino,A represents nitrogen or C--R.sub.2, whereR.sub.2 denotes hydrogen, methyl, halogen, nitro, methoxy or cyano,X.sub.1 and X.sub.2 are identical or different and denote halogen, andX.sub.3 denotes hydrogen, halogen or nitro andX.sub.4 denotes halogen, nitro, methoxy or methylthio, which comprises reacting a 3-dialkylamino-2-(het)aroyl-acrylic acid derivative of the formula ##STR2## in which R.sub.3 and R.sub.4 are the same or different and represent an alkyl group having 1 to 4 carbon atoms, or, together with the nitrogen atom to which they are bonded, form a ring,with a primary amine of the formula R--NH.sub.2 in the presence of at least one equivalent of an acid HX in a solvent or in excess acid.
    Type: Grant
    Filed: May 2, 1991
    Date of Patent: January 26, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Grohe
  • Patent number: 5180730
    Abstract: This invention relates to novel heterocyclic compounds structurally characterized by containing a specific heterocyclic group and by the presence of --CH.sub.2 --S--directly bound to the specific heterocyclic group. These heterocyclic compounds are useful as medicines, particularly as antagonists of SRS-A (slow reacting substance of anaphylaxis).
    Type: Grant
    Filed: April 5, 1991
    Date of Patent: January 19, 1993
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Toshiyasu Mase, Ryuji Tsuzuki, Hiromu Hara, Kiyoshi Murase, Kenichi Tomioka
  • Patent number: 5168113
    Abstract: A mercapto-substituted pyridine compound having formula (I): ##STR1## where R.sub.1 and R.sub.2 are alkyl groups, and n is 0 or 1, and salts thereof and a process for preparing the same are disclosed. The mercapto-substituted pyridine compound is useful as an intermediate for preparing a herbicidal compound.The present invention further provides aminocarbonyl-substituted pyridinesulfinic acid (ACPS) or salts thereof as the precursor of aminosulfonyl-substituted pyridinecarbonic acid amide compound (APCA) which is useful as the starting material for agricultural chemicals, medicine, etc. Moreover, the preparation process of the present invention is an industrially advantageous preparation process which is capable of preparing in a series of steps from mercapto-substituted pyridinecarboxylic acid amide compound (MPCA) or aminocarbonyl-substituted halogenopyridine compound (ACHP) to ACPS or salts thereof, and further to APCA.
    Type: Grant
    Filed: January 29, 1990
    Date of Patent: December 1, 1992
    Inventors: Takahiro Haga, Yasuhiro Tsujii, Tatsuo Isogai, Shigeo Murai, Hisayoshi Jonishi, Tokiya Kimura, Hiroshi Sasaki, Takao Awazu, Toshihiro Tanaka
  • Patent number: 5164506
    Abstract: For inhibiting HMG-CoA reductase and cholesterol synthesis, the novel 2-pyridones and pyrid-2-thiones of the formula ##STR1## in which A is optionally substituted aryl or heterocyclic,B is optionally substituted alkyl, cycloalkyl or aryl,D and E independently are optionally substituted aryl or heterocyclic, H, nitro, cyano, optionally substituted alkyl, alkenyl or imino, amino, alkoxy or acyl, or forms a ring with B,G is O or S,X is --CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--, andR represents a group of the formula ##STR2## and salts thereof.
    Type: Grant
    Filed: April 19, 1991
    Date of Patent: November 17, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Fey, Rolf Angerbauer, Walter Hubsch, Thomas Philipps, Hilmar Bischoff, Dieter Petzinna, Delf Schmidt, Gunter Thomas
  • Patent number: 5160662
    Abstract: Optically active compounds having the following formulae (1), (2) or (3) ##STR1## wherein R and R' are C.sub.1-20 alkyl groups; X and Y.sub.1 are --, O, S, or divalent groups such as COO, OOC and OCOO; m is 0 or 1; n is 0 to 5; A.sub.2 is a cyclic group, such as p,p'-biphenylene, 2,6-naphthylene, 2,5-pyrimidinylene-1,4-phenylene, A.sub.1 -Y.sub.2 -pyridylene or A.sub.4 -Y.sub.2 -A.sub.5 ; Y.sub.2 is CH.sub.2 CH.sub.2 or C.tbd.C; A.sub.3 is 2,6-naphthylene, A.sub.1 -Y.sub.2 -pyridylene or A.sub.6 -CH.sub.2 CH.sub.2 -A.sub.7 ; and A.sub.1, A.sub.4, A.sub.5, A.sub.6 and A.sub.7 are cyclic groups, such as 1,4-phenylene and/or 4,4'-biphenylene.
    Type: Grant
    Filed: February 27, 1990
    Date of Patent: November 3, 1992
    Assignee: Sanyo Chemical Industries, Ltd.
    Inventors: Masahiro Satoh, Tetsuya Watanabe, Kunikiyo Yoshio, Hiroshi Kishiki
  • Patent number: 5149359
    Abstract: The present invention relates to derivatives of 3,4-dehydropiperidin-5-one having herbicidal activity. The derivatives have the formula ##STR1## as defined in the claims. The present invention further relates to a herbicidal composition and a method for controlling weeds which grow among agricultural crops.
    Type: Grant
    Filed: February 21, 1990
    Date of Patent: September 22, 1992
    Assignee: Agrimont S.p.A.
    Inventors: Giovanni Camaggi, Giovanni Meazza, Ciro Preziuso
  • Patent number: 5144038
    Abstract: A process for the production of 2-hydroxy-3-halo-5-nitropyridines, in which a 5-halo-6-hydroxynicotinic acid is nitrated in the end product. The resultant pyridines form valuable intermediate products for active ingredient synthesis.
    Type: Grant
    Filed: July 17, 1991
    Date of Patent: September 1, 1992
    Assignee: Lonza Ltd.
    Inventor: Detlev Worsch
  • Patent number: 5132312
    Abstract: Disclosed are novel 3-hydroxy-3-methylglutarylcoenzyme A reductase inhibitors useful as antihypercholesterolemic agents represented by the formula ##STR1## and the corresponding ring-opened hydroxy acids derived therefrom and pharmaceutically acceptable salts thereof.Pharmaceutical compositions containing said compounds and method of inhibiting the biosynthesis of cholesterol therewith are also disclosed.
    Type: Grant
    Filed: November 27, 1990
    Date of Patent: July 21, 1992
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: John R. Regan, Kent E. Neuenschwander
  • Patent number: 5125956
    Abstract: Disclosed herein are herbicidal pyridine compounds substituted at the 2- or 6-position with an OR.sub.2 moiety where R.sub.2 is hydrogen, lower alkyl, halomethyl, lower cyanoalkyl, alkenyl or alkynyl, as well as herbicidal compositions and herbicidal use of these compounds.
    Type: Grant
    Filed: February 25, 1991
    Date of Patent: June 30, 1992
    Assignee: Monsanto Company
    Inventors: Donald E. Korte, Len F. Lee