Chalcogen Bonded Directly To Ring Carbon Of The Thiazole Ring Patents (Class 548/213)
  • Patent number: 5629265
    Abstract: Disclosed herein are cyanoketone derivatives of the following formula (1) ##STR1## such as 1-cyano-1-piperidinocarbonyl-3-[4-(2-chloro-4-trifluoromethylphenoxy)pheno xy]-2-butanone, 1-cyano-1-piperidinocarbonyl-3-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy )phenoxy]-2-butanone, 1-cyano-1-(N-methyl-N-dichlorophenyl)aminocarbonyl-3-[4-(2-quinoxalyloxy)p henoxy]-2-butanone, 1-cyano-1-(N,N-dibutyl)aminocarbonyl-3-[4-(3-chloro-5-trifluoromethyl-2-py ridyloxy)phenoxy-2-butanone, and the like, which are characterized by excellent herbicidal activity and effectiveness against a variety of gramineous weeds.
    Type: Grant
    Filed: June 22, 1994
    Date of Patent: May 13, 1997
    Assignee: Tokuyama Corporation
    Inventors: Masahiko Ishizaki, Seiji Nagata, Junji Takenaka
  • Patent number: 5621109
    Abstract: A retroviral protease inhibiting compound of the formula: ##STR1## is disclosed wherein the terms R.sub.1, R.sub.2, R.sub.5, R.sub.6, Y, Y', m and n are herein defined.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: April 15, 1997
    Assignee: Abbott Laboratories
    Inventors: Daniel W. Norbeck, Hing L. Sham, Dale J. Kempf, Chen Zhao
  • Patent number: 5603866
    Abstract: A composition comprising A) an aqueous solution wherein the total content of 3-isothiazolinones is below 8 wt/%, and B) a stabilizing compound of the formula:[R.sub.x A--C.sub.6 H.sub.2 R.sup.1 R.sup.2 ].sub.y --Zwherein:R, R.sup.1 and R.sup.2 each independently represents hydrogen, a straight-chained or branched or cyclic alkyl radical, aralkyl or aryl;A is oxygen or nitrogen;Z represents AR.sub.x, R.sup.1, R.sup.2, alkoxy methylene, methylene or alkylidene;provided that when A is oxygen, x is 0 or 1 and when A is nitrogen, x is 1 or 2; and y is 1 or 2;exhibits improved stability.
    Type: Grant
    Filed: May 17, 1995
    Date of Patent: February 18, 1997
    Assignee: Bromine Compounds, Ltd.
    Inventors: Jeane Segall, Leonard M. Shorr
  • Patent number: 5599827
    Abstract: Dilute solutions of 0.5 to about 5% by weight of at least one 3-isothiazolone selected from the group consisting of 5-chloro-2-methyl-4-isothazolin-3-one and 2-methyl-4-isothazolin-3-one are stabilized without using inorganic metal salts or hydrogen peroxide by forming a microemulsion composition with organic solvent(s) having less than 6 percent by weight solubility in water; anionic surfactant(s); and optionally, non-ionic surfactant(s).
    Type: Grant
    Filed: May 16, 1995
    Date of Patent: February 4, 1997
    Assignee: Rohm and Haas Company
    Inventor: Kevin F. Gironda
  • Patent number: 5594021
    Abstract: Thienyl-, furyl- and pyrrolyl-sulfonamides and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, N-(isoxazolyl)thienylsulfonamides, N-(isoxazolyl)furylsulfonamides and N-(isoxazolyl)pyrrolylsulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: January 14, 1997
    Assignee: Texas Biotechnology Corporation
    Inventors: Ming F. Chan, Bore G. Raju, Adam Kois, Erik J. Verner, Chengde Wu, Rosario S. Castillo, Venkatachalapathi Yalamoori, Vitukudi N. Balaji
  • Patent number: 5594017
    Abstract: Compositions comprising water, microbicidally active 3-isothiazolone compound, and an effective stabilizing amount of unsaturated, cyclic iodosyl or iodyl compound of formula I and II ##STR1## wherein: X=C(O), SO.sub.2, OPO.sub.3 H, CH.sub.2 C(O);Y=O, NR.sup.3 ;R.sup.1 =H, Cl, Br, I, substituted or unsubstituted C.sub.1 -C.sub.18 alkyl, substituted or unsubstituted C.sub.2 -C.sub.18 alkenyl, substituted or unsubstituted C.sub.4 -C.sub.6 aryl, substituted or unsubstituted C.sub.7 -C.sub.10 aralkyl;R.sup.2 =H, Cl, Br, I, substituted or unsubstituted C.sub.1 -C.sub.18 alkyl, substituted or unsubstituted C.sub.2 -C.sub.18 alkenyl, substituted or unsubstituted C.sub.4 -C.sub.6 aryl, substituted or unsubstituted C.sub.7 -C.sub.10 aralkyl, SO.sub.3 H, CO.sub.2 R.sup.4, C(O)NR.sup.5 R.sup.6 ;R.sup.1 and R.sup.2 may by joined to form a substituted or unsubstituted 5 or 6 membered ring, optionally fused to another 5 or 6 membered aromatic ring;R.sup.3 =H, C(O)R.sup.7, substituted or unsubstituted C.sub.1 -C.sub.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: January 14, 1997
    Assignee: Rohm and Haas Company
    Inventor: John R. Mattox
  • Patent number: 5583230
    Abstract: A novel mildew resistant polymerizable compound of the formula: ##STR1## wherein X is --0-- or --S--; and Y is a residue of a known mildew proofing compound, preferably, a residue of a compound selected from the group consisting of phenol substituted with 1 to 5 halogen atoms, p-chloro-m-cresol, o-phenylphenol, p-chloro-m-xylenol, salicylanilide, 8-hydroxyquinoline, 2-(4'-thiazolyl)benzimidazole, 2,5-dibromo-4-methylaniline, 1,2-benzoisothiazolin-3-one and 2-pyridinethiol-1-oxide. A polymer of the compound [I] and polyurethane composition containing the polymer are also disclosed.
    Type: Grant
    Filed: July 7, 1993
    Date of Patent: December 10, 1996
    Assignee: Toyo Boseki Kabushiki Kaisha
    Inventors: Hideyuki Mitamura, Yoshikazu Arimatsu
  • Patent number: 5578622
    Abstract: As isothiazole derivative represented by the formula (I), ##STR1## wherein R.sup.1, R.sup.2, Y and Z have the same meanings as defined in the description of the specification, and it is useful as an active ingredient for fungicidal and/or bactericidal compositions for use in industry, agriculture and medical treatment.
    Type: Grant
    Filed: June 29, 1995
    Date of Patent: November 26, 1996
    Assignee: Asamura Patent Office
    Inventors: Kenichi Ikeda, Katsutoshi Endo, Tsutomu Nishiguchi, Yoshimi Niwano
  • Patent number: 5571821
    Abstract: Sulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided. The sulfonamides have formula I: ##STR1## in which Ar.sup.1 is a 3- or 5-isoxazolyl and Ar.sup.2 is selected from among alkyl, including straight and branched chains, aromatic rings, fused aromatic rings and heterocyclic rings, including 5-membered heterocycles with one, two or more heteroatoms and fused ring analogs thereof and 6-membered rings with one, two or more heteroatoms and fused ring analogs thereof. Ar.sup.2 is preferably thiophenyl, furyl, pyrrolyl, naphthyl, and phenyl. Compounds in which Ar.sup.
    Type: Grant
    Filed: May 20, 1994
    Date of Patent: November 5, 1996
    Assignee: Texas Biotechnology Corporation
    Inventors: Ming Fai Chan, Bore G. Raju, Adam Kois, Erik J. Verner, Chengde Wu, Rosario S. Castillo, Venkatachalapathi Yalamoori, Vitukudi N. Balaji, Kalyanaraman Ramnarayan
  • Patent number: 5559083
    Abstract: A composition comprising an isothiazolone compound mixed with a branched cyclodextrine, wherein the isothiazolone compound can be stabilized to water, so that it is possible to provide an aqueous solution comprising an isothiazolone compound which is excellent in storage stability and aqueous solution stability.
    Type: Grant
    Filed: April 3, 1995
    Date of Patent: September 24, 1996
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Naoki Kubota, Taiki Kusaka
  • Patent number: 5554627
    Abstract: Compounds of formula (I), wherein Q.sup.1 represents an aryl group; the dotted line represents an optional covalent bond; one of X and Y represents H and the other represents hydroxy or C.sub.1-6 alkoxy, or X and Y together form a group .dbd.O or .dbd.NOR.sup.5 where R.sup.5 is H or C.sub.1-6 alkyl; Z represents O, S or NR.sup.2, where R.sup.2 is H or C.sub.1-6 alkyl; W represents a bond or a saturated or unsaturated hydrocarbon chain of 1, 2, 3, 4, 5 or 6 carbon atoms; R.sup.1 represents H or C.sub.1-6 alkyl. R.sup.3 represents H, C.sub.1-6 alkyl or C.sub.2-6 alkenyl; R.sup.4 represents an optionally substituted phenyl group; and R.sup.6 represents a specified amino group or an optionally substituted aromatic or non-aromatic azacyclic or azabicyclic group; and salts and prodrugs are tachykinin receptor antagonists.
    Type: Grant
    Filed: April 27, 1995
    Date of Patent: September 10, 1996
    Assignee: Merck, Sharp & Dohme Ltd.
    Inventors: Richard T. Lewis, Angus M. MacLeod, Kevin J. Merchant
  • Patent number: 5554635
    Abstract: A liquid concentrate comprises between about 4 and about 10 wt % of an isothiazolinone compound or mixture of isothiazolinone compounds, between about 25 and about 92 wt % of a plasticizer in which said isothiazolinone compound is soluble and between about 4 and about 50 wt % of 2,4,4'-trichloro-2'-hydroxydiphenyl ether. The 2,4,4'-trichloro-2'-hydroxydiphenyl ether stabilizes the concentrate against crystallization and/or freezing at sub-freezing conditions, particularly when the isothiazolinone compound has a melting point of 30.degree. C. or above. 2,4,4'-trichloro-2'-hydroxydiphenyl ether also enhances the anti-microbial properties of an isothiazolinone-containing concentrate.
    Type: Grant
    Filed: February 7, 1995
    Date of Patent: September 10, 1996
    Assignee: Morton International, Inc.
    Inventors: Nuno M. Rei, Roger G. Hamel
  • Patent number: 5552423
    Abstract: There is disclosed a novel isothiazolone derivative of the formula: ##STR1## wherein X.sup.1 and X.sup.2 are the same or different and are independently hydrogen, chlorine or bromine; and R is haloalkoxy. The isothiazolone derivative is effective as a microbicide. Also disclosed are a microbicidal composition containing the isothiazolone derivative as an active ingredient, and an intermediate compound for use in the production of the isothiazolone derivative.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: September 3, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Akiko Kakimizu, Kenji Arai, Norio Kimura, Tomohiro Teramae
  • Patent number: 5550139
    Abstract: Isothiazolidin-3-one-1,1 dioxide, 3-oxo-1,2,5-thiadiazolidine-1,1,-dioxide and derivatives thereof, reduce or inhibit the activity of serine proteases. Such compounds are useful as anti-inflammatory and anti-metastatic agents.
    Type: Grant
    Filed: January 3, 1994
    Date of Patent: August 27, 1996
    Assignee: The Wichita State University
    Inventor: William C. Groutas
  • Patent number: 5534487
    Abstract: The present invention provides a method of stabilizing solutions of 3-isothiazolone compounds using a stabilizing compound of the formula: ##STR1## wherein R is C.sub.1 -C.sub.6 alkyl; and compositions which comprise 3-isothiazolone compound, solvent and stabilizing compound.
    Type: Grant
    Filed: May 16, 1995
    Date of Patent: July 9, 1996
    Assignee: Rohm and Haas Company
    Inventor: Kevin F. Gironda
  • Patent number: 5534533
    Abstract: Novel carboxylate derivatives exhibiting phospholipase A.sub.2 inhibitory activity are disclosed, Specifically, the following compounds of the formula and pharmaceutically acceptable salts thereof are disclosed: ##STR1## wherein A is hydroxy, amino, or lower alkylamino; R.sup.1 to R.sup.12 are independently hydrogen, methyl, methoxy, or hydroxy, provided that all of R.sup.1 to R.sup.12 are not hydrogen; G.sup.1 is a single bond, or a group of --(CH.sub.2).sub.x O(CH.sub.2).sub.y -- wherein x and y are independently 0-5; G.sup.2 is a single bond, oxygen, sulfur, carbonyl, etc.; G.sup.3 is alkyl, aryl, or a group of the formula: ##STR2## wherein R.sup.13 and R.sup.14 are independently hydrogen, alkyl, aryl, etc.; or R.sup.13 and R.sup.14 may be taken together with the adjacent nitrogen atom to form a heterocyclic group or a group of the formula: ##STR3## wherein Z is a carbon atom or a nitrogen atom, J, K, and L are independently hydrogen or aryl, etc.
    Type: Grant
    Filed: September 28, 1994
    Date of Patent: July 9, 1996
    Assignee: Shionogi & Co., Ltd.
    Inventors: Mitsuaki Ohtani, Toshiyuki Kato, Yozo Hori
  • Patent number: 5523020
    Abstract: A clathrate compound composed of a water-soluble microbicide and a phenolic compound of formula (1) or (2): ##STR1##
    Type: Grant
    Filed: September 20, 1994
    Date of Patent: June 4, 1996
    Assignee: Kurita Water Industries Ltd.
    Inventors: Minoru Yagi, Kazumi Nakane, Yuriko Hiyane
  • Patent number: 5523312
    Abstract: Disclosed herein are compounds and pharmaceutical compositions useful for combating picornaviruses and preventing or treating picornaviral infections. The compounds have the formula: ##STR1## wherein Het.sub.1 is chosen from the group consisting of oxazolyl, isoxazolyl, oxadiazolyl;Y is an alkylene bridge of 3 to 9 carbon atoms;Het.sub.2 is benzofuranyl or indolyl;R.sub.1 and R.sub.2 are each independently chosen from hydrogen, halo, acetyl, alkyl, alkenyl, amino, alkylthio, hydroxy, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinyl alkyl, alkylsulfonylalkyl, alkoxy, nitro, carboxy, alkoxycarbonyl, dialkylaminoalkyl, alkylaminoalkyl, aminoalkyl, difluoromethyl, trifluromethyl, or cyano; andR.sub.3 is oxazolyl, oxadiazolyl, isoxazolyl or any of these substituted with alkyl, halo, alkoxyalkyl, cycloalkyl, haloalkyl, hydroxyalkyl, alkoxy, hydroxy, furyl, thienyl, or fluoroalkyl;the N-oxide thereof or a pharmaceutically acceptable acid addition salt thereof.
    Type: Grant
    Filed: September 27, 1994
    Date of Patent: June 4, 1996
    Assignee: Sterling Winthrop Inc.
    Inventors: David J. Aldous, Thomas R. Bailey, Guy D. Diana, Gee-Hong Kuo, Theodore J. Nitz, Michael Reuman
  • Patent number: 5521186
    Abstract: The present invention provides novel compounds of formula ##STR1## the stereochemically isomeric forms thereof, and the pharmaceutically acceptable acid addition salts thereof, wherein A and B taken together form a bivalent radical of formula: --N.dbd.CH-- (a), --CH.dbd.N-- (b), --CH.sub.2 --CH.sub.2 -- (c), --CH.dbd.CH-- (d) --C(.dbd.O)--CH.sub.2 -- (e), --CH.sub.2 --C(.dbd.O)-- (f); R.sup.1 is hydrogen, C.sub.1-6 alkyl, or halo; R.sup.2 is hydrogen or halo; R.sup.3 is hydrogen; C.sub.1-8 alkyl; C.sub.3-6 cycloalkyl or C.sub.1-8 alkyl substituted with hydroxy, oxo, C.sub.3-6 cycloalkyl or aryl. Het is five- or six-membered optionally substituted heterocyclic ring. The use as a medicine, especially as a lipid lowering agent is disclosed as well as pharmaceutical compositions and processes for preparing compounds and compositions.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: May 28, 1996
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Jan Heeres, Leo J. J. Backx, Robert J. M. Hendrickx, Luc A. L. Van Der Eycken, Didier R. G. G. De Chaffoy De Courcelles
  • Patent number: 5519141
    Abstract: An intermolecular compound of dichloroglyoxime and 5-chloro-2-methyl-3-isothiazolone as a novel compound obtained by reacting dichloroglyoxime with 5-chloro-2-methyl-3-isothiazolone. The intermolecular compound is useful as an antibacterial agent.
    Type: Grant
    Filed: July 20, 1994
    Date of Patent: May 21, 1996
    Assignee: Junsei Chemical Co., Ltd.
    Inventors: Kyoji Nita, Hideki Kanno, Mayumi Odagiri, Nobuyasu Takahashi
  • Patent number: 5512213
    Abstract: A treatment for stabilizing an isothiazolone compound comprising adding to the compound a stabilizing amount of a metal salt, wherein the cation of the metal salt is an alkali metal, and the anion is selected from the group consisting of acetate, citrate, phosphate and borate.
    Type: Grant
    Filed: March 1, 1995
    Date of Patent: April 30, 1996
    Assignee: Betz Laboratories, Inc.
    Inventor: Donald J. Paterson
  • Patent number: 5510379
    Abstract: .beta.-Carboxy sulfonates of the formula ##STR1## wherein R.sub.1 is aryl, R.sub.3 and R.sub.4 are hydrogen or alkyl, Y is -O-, -S-, or -NR.sub.2 -, and R.sub.5 is alkyl or aryl are potent inhibitors of the enzyme acyl CoA:cholesterol acyltransferase (ACAT) and are thus useful for treating hypercholesterolemia and atherosclerosis.
    Type: Grant
    Filed: December 19, 1994
    Date of Patent: April 23, 1996
    Assignee: Warner-Lambert Company
    Inventors: Helen T. Lee, Joseph A. Picard, Drago R. Sliskovic
  • Patent number: 5508450
    Abstract: Benzopyran derivatives which have an inhibitory effect on the Maillard reaction as well as an antioxidizing effect are described herein. These derivatives may be utilized in the treatment and/or prevention of diabetic complications such as, for example, coronary heart disease, peripheral circulatory insufficiency or failure, cerebrovascular hindrance, neurogenous diabetes, nephropathy, arteriosclerosis, arthrosclerosis, cataracts and retinopathy. Further, the derivatives may also be used in the treatment and/or prevention of diseases induced by aging and in the treatment and/or prevention of diseases caused by the formation of peroxidized fat.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: April 16, 1996
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Shuichi Ohuchida, Masaaki Toda, Tsumoru Miyamoto
  • Patent number: 5508417
    Abstract: This invention relates to antimicrobial compounds of formula I, II, or III ##STR1## wherein R.sub.1 and R.sub.2 are independently selected from hydrogen, halogen, or (C.sub.1 -C.sub.4)alkyl;R.sub.1 and R.sub.2 may be taken together with the carbons to which they are attached to form a 5 to 7-membered carbocyclic ring and the ring may be aromatic;R.sub.3 is hydrogen, (C.sub.1 -C.sub.8)alkyl, (C.sub.2 -C.sub.8)alkenyl, (C.sub.5 -C.sub.8)alkynyl, (C.sub.5 -C.sub.7)cycloalkyl or cycloalkenyl, phenyl or substituted phenyl, (C.sub.7 -C.sub.10)aralkyl or substituted (C.sub.7 -C.sub.10)aralkyl, or a 5 to 8-membered heteroaryl having one or more heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen;R.sub.4 is an electron-withdrawing group selected from CN, NO.sub.2, P(O)(OR.sub.7).sub.2, P(S)(OR.sub.7).sub.2, COOR.sub.6, COR.sub.6, CONHR.sub.6, SOR.sub.6, SO.sub.2 R.sub.6, where R.sub.6 is hydrogen, (C.sub.1 -C.sub.8)alkyl, phenyl or substituted phenyl, (C.sub.7 -C.sub.
    Type: Grant
    Filed: February 23, 1994
    Date of Patent: April 16, 1996
    Assignee: Rohm and Haas Company
    Inventors: Peter Osei-Gyimah, Barry C. Lange
  • Patent number: 5506243
    Abstract: Since sulfonamide derivatives of the present invention show strong inhibitory activity against cysteine protease such as calpain papain, cathepsin B, cathepsin H, cathepsin L, they can be used as remedies for muscular dystrophy, cataract, myocardial infarction, stroke, Alzheimer's disease, amyotrophia, osteoporosis, hypercalcemia or the like.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: April 9, 1996
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Ryoichi Ando, Toshiro Sakaki, Chizuko Takahashi, Yoshiyuki Fujimura
  • Patent number: 5500425
    Abstract: Compounds of the formula I ##STR1## processes for their preparation, pharmaceutical preparations, use of and method of treatment of disorders in CNS by using compounds of formula I.
    Type: Grant
    Filed: September 9, 1994
    Date of Patent: March 19, 1996
    Assignee: Aktiebolaget Astra
    Inventors: Lars-Gunnar Larsson, Lucy A. Renyl, Svante B. Ross, Daniel D. Sohn, Seth-Olov Thorberg
  • Patent number: 5498344
    Abstract: A liquid concentrate comprises between about 4 and about 25 wt % of an isothiazolinone compound or mixture of isothiazolinone compounds between about 25 and about 88 wt % of a plasticizer in which said isothiazolinone compound is soluble and between about 8 and about 50 wt % of a C.sub.6 -C.sub.12 monoalkylphenol(s) which stabilizes the concentrate against crystallization and/or freezing at sub-freezing conditions.
    Type: Grant
    Filed: February 2, 1995
    Date of Patent: March 12, 1996
    Assignee: Morton International, Inc.
    Inventors: Nuno M. Rei, Roger G. Hamel
  • Patent number: 5494925
    Abstract: 2-Heterocyclyloxymethyl and 2-heterocyclylthiomethyL-1,2,5-thiadiazolidin-3-one 1,1-dioxides, pharmaceutical compositions containing them and methods for the treatment of degenerative diseases utilizing them.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: February 27, 1996
    Assignee: Sterling Winthrop Inc.
    Inventors: John J. Court, Ranjit C. Desai, Dennis J. Hlasta
  • Patent number: 5484934
    Abstract: An isothiazole derivative represented by the general formula (I): ##STR1## (wherein R and R.sup.1 are as defined in the general description, and n is an integer of 1 or 2), a process for producing the same, and the usage thereof.
    Type: Grant
    Filed: December 18, 1993
    Date of Patent: January 16, 1996
    Assignee: Nihon Nohyaku Co., Ltd.
    Inventors: Kenichi Ikeda, Shin'ichi Ueyama, Katsutoshi Endo, Chiaki Kato
  • Patent number: 5482966
    Abstract: The invention concerns oxime derivatives of the formula I ##STR1## wherein R.sup.4 includes hydrogen, carboxy, carbamoyl, amino, cyano, trifluoromethyl, (1-4C)alkylamino, di-(1-4C)alkylamino and (1-4C)alkyl;R.sup.5 includes hydrogen, (1-4C)alkyl, (3-4C)alkenyl, (3-4C)alkynyl, (2-5C)alkanoyl, halogeno-(2-4C)alkyl and hydroxy-(2-4C)alkyl;Ar.sup.1 is phenylene or a heteroaryl diradical;A.sup.1 is a direct link to X.sup.1, or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene or a heteroaryl diradical;R.sup.1 is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which together with the carbon atom to which A.sup.2 and A.sup.3 are attached define a ring having 5 or 6 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1-3C)alkylene and X.sup.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: January 9, 1996
    Assignees: Zeneca Limited, Zeneca Pharma S.A.
    Inventors: Thomas G. C. Bird, Patrick Ple
  • Patent number: 5480898
    Abstract: The present invention relates to a storage-stable aqueous solution of one or more compounds of the general formula I ##STR1## wherein Y, R and R.sup.1 are as defined in claim 1, which comprises a noble metal ion.
    Type: Grant
    Filed: November 7, 1994
    Date of Patent: January 2, 1996
    Assignee: Riedel-de Haen Aktiengesellschaft
    Inventor: Wolfgang Lindner
  • Patent number: 5466818
    Abstract: Process for producing substantially separated 5-chloro-2-methyl-3-isothiazolone (CMI) and 2-methyl-3-isothiazolone (MI) from a mixture of their hydrochloride salts, or in a special mixture having a higher ratio of CMI to MI, comprising heating a mixture of CMI.HCl and MI.HCl for a period of time necessary to fully dissociate said CMI.HCl and form substantially pure CMI, but insufficient to fully dissociate said MI.HCl.
    Type: Grant
    Filed: March 31, 1994
    Date of Patent: November 14, 1995
    Assignee: Rohm and Haas Company
    Inventor: Ramesh B. Petigara
  • Patent number: 5461067
    Abstract: A retroviral protease inhibiting compound of the formula: ##STR1## is disclosed wherein R.sub.1, R.sub.2, R.sub.5, R.sub.6, Y.sub.m and Y'.sub.n are herein defined.
    Type: Grant
    Filed: February 1, 1994
    Date of Patent: October 24, 1995
    Assignee: Abbott Laboratories
    Inventors: Daniel W. Norbeck, Hing L. Sham, Dale J. Kempf, Chen Zhao
  • Patent number: 5461150
    Abstract: The present invention provides a method of stabilizing solutions of 3-isothiazolone compound(s) selected from the group consisting of 5-chloro-2-methyl-3-isothiazolone, 2-methyl-3-isothiazolone, and mixtures thereof in water free of nitrate or nitrite by the use of extremely low levels of copper ion, and compositions comprising water solutions of 3-isothiazolone compound(s) selected from the group consisting of 5-chloro-2-methyl-3-isothiazolone, 2-methyl-3-isothiazolone, and mixtures thereof, and extremely low levels copper ion.
    Type: Grant
    Filed: December 14, 1994
    Date of Patent: October 24, 1995
    Assignee: Rohm and Haas Company
    Inventors: Kevin F. Gironda, George H. Redlich
  • Patent number: 5457125
    Abstract: The invention concerns oxime derivatives of the formula I ##STR1## wherein R.sup.4 is hydrogen, (1-4C)alkyl, halogeno-(2-4C)alkyl, hydroxy-(2-4C)alkyl, cyano-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl;R.sup.5 is hydrogen, (1-4C)alkyl, halogeno-(2-4C)alkyl, hydroxy-(2-4C)alkyl, cyano-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl, or a heteroaryl moiety selected from pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, furyl, thienyl, oxazolyl and thiazolyl;A.sup.4 is (1-4C)alkylene;Ar.sup.1 is phenylene, pyridinediyl or pyrimidinediyl;A.sup.1 is a direct link to X.sup.1, or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene, pyridinediyl, pyrimidinediyl, thiophenediyl, furandiyl or thiazolediyl;R.sup.1 is hydrogen, (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- wherein each of A.sup.2 and A.sup.3 is independently (1-3C)alkylene and X.sup.
    Type: Grant
    Filed: August 19, 1994
    Date of Patent: October 10, 1995
    Assignees: Zeneca Limited, Zeneca Pharma S.A.
    Inventors: Philip N. Edwards, Michael S. Large
  • Patent number: 5453507
    Abstract: The present invention relates to an improved process for selectively preparing 4-isothiazolin-3-one having the following structural formula(I), consisted of preparing 3,3'-dithiodipropionyldichloride by reacting 3,3'-dithiodipropionic acid with thionylchloride, reacting with amine compound to prepare 3,3'-dithiodipropioneamide, and herein adding sulfrylchloride in organic solvent to cyclize, which is useful as antiseptic or anti-infectives for cooling water, metal processing oils, paints, cosmetics, surfactants, sensitizers, etc. ##STR1## wherein, R.sup.1 is methyl or n-octyl group;R.sup.2 is hydrogen or chlorine atom.
    Type: Grant
    Filed: February 4, 1994
    Date of Patent: September 26, 1995
    Assignee: Sunkyong Industries Co., Ltd.
    Inventors: Soon Jang Hahn, Jin Man Kim, Young Park
  • Patent number: 5434267
    Abstract: Process for the preparation of compounds of the formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, X and n have the meaning given in the description, by reacting acetates with carbon monoxide in the presence of a basic auxiliary, followed by alkylation. The products are intermediates for fungicidal acrylates.
    Type: Grant
    Filed: March 14, 1994
    Date of Patent: July 18, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Helmut Kraus, Alexander Klausener, Hans-Joachim Diehr
  • Patent number: 5430046
    Abstract: Composition as a highly useful concentrated biocide, said composition being solid at 20.degree. C., easily meltable and solidifyable, capable of undergoing remelt and resolidification without loss of homogeneity and method.
    Type: Grant
    Filed: March 11, 1994
    Date of Patent: July 4, 1995
    Assignee: Rohm and Haas Company
    Inventor: John R. Mattox
  • Patent number: 5420290
    Abstract: Nitrosamine-free 3-isothiazolone biocidal compositions suitable for applications where substantial human or animal contact is anticipated, their method of use and process of preparation are disclosed.
    Type: Grant
    Filed: November 18, 1993
    Date of Patent: May 30, 1995
    Assignee: Rohm and Haas Company
    Inventors: Horst O. Bayer, Barry C. Lange, Ramesh B. Petigara
  • Patent number: 5411977
    Abstract: The present invention relates to substituted 2, 5-diaryl-4-isothiazolin-3-ones, pharmaceutical preparations containing them, and their use in the treatment of, thrombosis and, especially inflammation.
    Type: Grant
    Filed: March 31, 1993
    Date of Patent: May 2, 1995
    Assignee: The Dupont Merck Pharmaceutical Company
    Inventors: Joseph J. Petraitis, Susan R. Sherk
  • Patent number: 5409944
    Abstract: Disclosed are compounds of Formula I useful in the treatment of cyclooxygenase mediated diseases such as pain, fever and inflammation of a variety of conditions including rheumatic fever, symptoms associated with influenza or other viral infections, common cold, low back and neck pain, dysmenorrhea, headache, toothache, sprains and strains, myositis, neuralgia, synovitis, arthritis, including rheumatoid arthritis degenerative joint diseases (osteoarthritis), gout and ankylosing spondylitis, bursitis, burns, injuries.
    Type: Grant
    Filed: March 12, 1993
    Date of Patent: April 25, 1995
    Assignee: Merck Frosst Canada, Inc.
    Inventors: W. Cameron Black, Chun-Sing Li, Daniel Guay, Petpiboon Prasit, Patrick Roy
  • Patent number: 5399544
    Abstract: Isoxazole- and isothiazole-5-carboxamides of the formula ##STR1## where X is oxygen or sulfur, R.sup.1 is hydrogen, substituted or unsubstituted alkyl, cycloalkyl, cycloalkenyl, alkenyl (may be epoxidized at the double bond), alkynyl, alkoxy, a heterocyclic radical or phenyl, R.sup.2 is a derivative carboxylic acid function and R.sup.3 and R.sup.4 have the meanings given in the disclosure, and herbicidal agents containing compounds I.
    Type: Grant
    Filed: September 14, 1993
    Date of Patent: March 21, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Volker Maywald, Peter Muenster, Hartmann Koenig, Gerhard Hamprecht, Thomas Kuekenhoehner, Wolfgang Rohr, Helmut Walter, Karl-Otto Westphalen, Matthias Gerber
  • Patent number: 5384326
    Abstract: Girondalones of the formula I useful as microbicides ##STR1## wherein A is a residue of a dialdehyde;R.sub.1 is independently selected from the group consisting of R.sub.2 and (C.sub.1 -C.sub.18)alkyl and;R.sub.2 is ##STR2## wherein (i) X.sub.1 and X.sub.2 can be joined to form a 5 or 6 membered fused carbocyclic ring, said ring being saturated, unsaturated, or aromatic; or(ii) X.sub.1 =Cl, H, methyl, or Br; andX.sub.2 =H, Cl, or Br.
    Type: Grant
    Filed: November 12, 1991
    Date of Patent: January 24, 1995
    Assignee: Rohm and Haas Company
    Inventors: Kevin F. Gironda, Peter Osei-Gyimah, Barry C. Lange
  • Patent number: 5376680
    Abstract: The invention concerns oxime derivatives of the formula I ##STR1## wherein R.sup.4 is hydrogen, (1-4C)alkyl, halogeno-(2-4C)alkyl, hydroxy-(2-4C)alkyl, cyano-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl; R.sup.5 is hydrogen, (1-4C)alkyl, halogeno-(2-4C)alkyl, hydroxy-(2-4C)alkyl, cyano-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl, or a heteroaryl moiety selected from pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, furyl, thienyl, oxazolyl and thiazolyl;A.sup.4 is (1-4C)alkylene;Ar.sup.1 is phenylene, pyridinediyl or pyrimidinediyl;A.sup.1 is a direct link to X.sup.1 or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene, pyridinediyl, pyrimidinediyl, thiophenediyl, furandiyl or thiazolediyl;R.sup.1 is hydrogen, (1-4C)alkyl, (3-C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- wherein each of A.sup.2 and A.sup.3 is independently (1-3C)alkylene and X.sup.
    Type: Grant
    Filed: May 11, 1993
    Date of Patent: December 27, 1994
    Assignees: Zeneca Limited, Zeneca Pharma, S.A.
    Inventors: Philip N. Edwards, Michael S. Large
  • Patent number: 5376657
    Abstract: Benzimidazolesulfonic acid derivatives of the formula I ##STR1## in which R.sub.1 is an unsaturated 5-membered heterocycle having not more than two hetero atoms N and/or S or is an unsaturated 6-membered heterocycle having not more than two N atoms, it being possible for each of the heterocycles to be substituted, and X is oxygen or sulfur, while R.sub.2, R.sub.3, R.sub.4 and n are as defined herein, are valuable microbicides. They can be used in crop protection in the form of suitable compositions, for example for controlling fungal disease.
    Type: Grant
    Filed: May 21, 1993
    Date of Patent: December 27, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Adolf Hubele, Bernard Hostettler, Marius Sutter, Urs Muller
  • Patent number: 5373016
    Abstract: Biocidal isothiazolinone or isothiazolothione compounds are stabilized with an effective amount of a free-radical scavenger compound. Exemplary of the biocidal isothiazolones are 1,2-benzisothiazolin-3-one, 2-methyl-4-5-trimethylene-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one. Effective free-radical scavengers include 3,3-thiodipropionic acid.
    Type: Grant
    Filed: May 28, 1993
    Date of Patent: December 13, 1994
    Assignee: Zeneca, Inc.
    Inventors: Scott A. Brown, Terry Young
  • Patent number: 5358957
    Abstract: Compounds of the formula ##STR1## wherein A is a substituted or unsubstituted, aromatic or non-aromatic, monocyclic or bicyclic, heterocyclic radical that is bonded by way of a carbon atom to X; each of R.sub.1 and R.sub.2, independently of the other, is hydrogen or C.sub.1 -C.sub.6 alkyl; X is NR.sub.3, 0 or S; and R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl, in free form or in salt form, can be used as agrochemical active ingredients and can be prepared in a manner known per se.
    Type: Grant
    Filed: September 2, 1993
    Date of Patent: October 25, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Maienfisch, Manfred Boger, Thomas Pitterna
  • Patent number: 5336777
    Abstract: Compounds of the general formula ##STR1## are cyclised to the corresponding isothiazolinone using a carbonyl halide of the formula RCOX where R is halogen or alkyl and X is halogen. R.sup.3 and R.sup.4 are preferably such as to form a 5 or 6 membered ring. Useful carbonyl halides are phosgene and propionyl chloride.
    Type: Grant
    Filed: November 5, 1992
    Date of Patent: August 9, 1994
    Assignee: Zeneca Limited
    Inventors: Frank S. Moffatt, David Winstanley
  • Patent number: 5334614
    Abstract: The invention concerns hydroxylamine derivatives of the formula I ##STR1## wherein R.sup.4 is hydrogen, carbamoyl, (1-4C)alkyl, cyclopentyl, cyclohexyl, tetrahydrofuran-3-yl, tetrahydropyran-4-yl, piperidin-4-yl, N-(1-4C)alkylpiperidin-4-yl, (2-5C)alkanoyl, (1-4C)alkylsulphonyl, N-(1-4C)alkylcarbamoyl, N,N-di-(1-4C)alkylcarbamoyl, phenyl, phenyl-(1-4C)alkyl, di-phenyl-(1-4C)alkyl, benzoyl, phenylsulphonyl or a heteroarylmethyl group;R.sup.5 is hydrogen, (1-4C)alkyl, (3-4C)alkenyl, (3-4C)alkynyl, cyano-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl;A.sup.4 is (1-4C)alkylene;Ar.sup.1 is phenylene, pyridinediyl or pyrimidinediyl;A.sup.1 is a direct link to X.sup.1, or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene, pyridinediyl, pyrimidinediyl, thiophenediyl, furandiyl or thiazolediyl;R.sup.1 is hydrogen, (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula -A.sup.2 -X.sup.2 -A.sup.3 -wherein each of A.sup.2 and A.sup.
    Type: Grant
    Filed: May 11, 1993
    Date of Patent: August 2, 1994
    Assignees: Zeneca Ltd., Zeneca Pharma SA
    Inventors: Philip N. Edwards, Michael S. Large
  • Patent number: 5332757
    Abstract: The invention concerns oxime derivatives of the formula I ##STR1## wherein R.sup.4 includes hydrogen, carboxy, carbamoyl, amino, cyano, trifluoromethyl, (1-4C)alkylamino, di-(1-4C)alkylamino and (1-4C)alkyl;R.sup.5 includes hydrogen, (1-4C)alkyl, (3-4C)alkenyl, (3-4C)alkynyl, (2-5C)alkanoyl, halogeno-(2-4C)alkyl and hydroxy-(2-4C)alkyl;Ar.sup.1 is phenylene or a heteroaryl diradical;A.sup.1 is a direct link to X.sup.1, or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene or a heteroaryl diradical;R.sup.1 is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula -A.sup.2 -X.sup.2 -A.sup.3 - which together with the carbon atom to which A.sup.2 and A.sup.3 are attached define a ring having 5 or 6 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1-3C)alkylene and X.sup.
    Type: Grant
    Filed: February 8, 1993
    Date of Patent: July 26, 1994
    Assignees: Zeneca Limited, Zeneca PHARMA S A
    Inventors: Thomas G. C. Bird, Patrick Ple