Chalcogen Attached Indirectly To The Thiazole Ring By Nonionic Bonding Patents (Class 548/169)
  • Patent number: 5716756
    Abstract: Sulfonic acid esters are used as (a) compounds for forming a strong acid on irradiation in radiation-sensitive, positive or negative working mixtures also comprising (b) either a compound with at least one acid-decomposable C--O--C or C--O--Si bond (for positive working mixtures) or a compound with at least acid-cross-linkable groups (for negative working mixtures) and c) a binder which is insoluble in water but soluble or at least swellable in aqueous alkaline solutions, wherein said sulfonic acid esters are formula?R.sup.1 --CR.sup.2 (CF.sub.3)--O--SO.sub.2 --!.sub.n R.sup.3(I)orR.sup.1 ?--CR.sup.2 (CF.sub.3)--O--SO.sub.2 --R.sup.3 !m (II)wherein R.sup.1, R.sup.2, R.sup.3, n and n are defined with the body of the disclosure. These mixtures are particularly suitable for exposure to deep UV radiation in the formation of recording materials suitable for the production of photoresists, electronic components, and printing plates.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: February 10, 1998
    Assignees: Hoechst Aktiengesellschaft, Herberts GmbH
    Inventors: Georg Pawlowski, Walter Spiess, Horst Roeschert, Wolfgang Appel, Walter Herr
  • Patent number: 5691366
    Abstract: A new nitro compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each lower alkyl or lower alkoxy(lower)-alkyl, or ##STR2## is cyclized to form ##STR3## X is --O--, --S-- or --NH--, m is an integer 0 or 1, andR.sup.3 is carbamoyl, lower alkylcarbamoyl, lower alkanoyl, di-lower alkylaminosulfonyl, lower alkylsulfonyl, oxamoyl or a group of the formula: --(Y).sub.n --R.sup.4 wherein Y is --CO--, --SO.sub.2 --, --COCH.sub.2 -- or ##STR4## n is an integer of 0 or 1, and R.sup.4 is heterocyclic group which is optionally substituted with one or more substituents selected from lower alkyl, lower alkoxy, phenyl, carbamoyl, halogen, amino, lower alkylthio, hydroxy, lower alkylsulfonylamino and carbamoylmethyl, and pharmaceutically acceptable salt thereof, which are useful as vasodilators.
    Type: Grant
    Filed: October 31, 1995
    Date of Patent: November 25, 1997
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Masayuki Kato, Shigetaka Nishino, Mitsuko Hamano, Hisashi Takasugi
  • Patent number: 5648370
    Abstract: There are disclosed compounds of formula I,Ar--CH.sub.2 CH.sub.2 --NH--CR.sup.1 R.sup.2 --X--Y Iin whichAr represents a group, ##STR1## X represents a C.sub.1-12 alkylene chain optionally interrupted or terminated by one or more groups selected from --S(O).sub.n --, --O--, --C(Z)--, CR.sup.6 R.sup.7, phenylmethyne, --NR.sup.8 --, --CONH--, --NHCO-- and --NHCONH--,Y represents an optionally substituted aryl or cycloalkyl group,Z represents O or S,R.sup.1, R.sup.2, R.sup.5 and R.sup.9 each independently represent hydrogen or alkyl C.sub.1-6,R.sup.3 and R.sup.4 represent hydrogen, or R.sup.3 and R.sup.4 together form a group --S--, --NR.sup.9 -- or --CH.sub.2 --,R.sup.6 and R.sup.7 independently represent hydrogen, alkyl C.sub.1-6, fluoro, cyano, or CF.sub.3, provided that at least one of R.sup.6 and R.sup.7 is other than hydrogen,R.sup.8 represents hydrogen or alkyl C.sub.1-6, or when X is interrupted or terminated by more than one --NR.sup.8 -- group may together with another R.sup.8 group form the chain --CH.
    Type: Grant
    Filed: November 28, 1994
    Date of Patent: July 15, 1997
    Assignee: Astra Pharmaceuticals Limited
    Inventors: Roger V. Bonnert, Roger C. Brown, David R. Cheshire, Francis Ince, John Dixon
  • Patent number: 5643932
    Abstract: A superoxide radical inhibitor containing, as an effective ingredient, an azole derivative represented by the general formula (1), ##STR1## [wherein R.sup.1 represents a phenyl group which may have 1-3 lower alkoxy groups as substituent(s) on the phenyl ring, a phenyl group having a lower alkylenedioxy group, or the like; R.sup.2 represents a hydrogen atom, a phenyl group, a halogen atom, a lower alkoxycarbonyl group, a lower alkyl group, an amino-lower alkyl group which may have a lower alkyl group as a substituent, a dihydrocarbostyril group, or the like; R.sup.3 represents a group of the formula, ##STR2## (R.sup.4B represents a hydroxyl group, a carboxy group, a lower alkenyl group or a lower alkyl group. m represents 0, 1 or 2); X represents a sulfur atom or an oxygen atom] or a salt thereof.
    Type: Grant
    Filed: May 19, 1995
    Date of Patent: July 1, 1997
    Assignee: Otsuka Pharmaceutical Co., Ltd.
    Inventors: Masatoshi Chihiro, Hajime Komatsu, Michiaki Tominaga, Yoichi Yabuuchi
  • Patent number: 5597819
    Abstract: New benzothiazine derivatives corresponding to the general formula I: ##STR1## in which: X represents halogen,n represents 0, 1, or 2,B represents the following formula: ##STR2## in which: R.sub.1 & R.sub.2 together with the carbons to which they are attached form a 6-carbon-atom aromatic ring which is optionally substituted by a group X' representing halogen, andY represents the radical --(SO.sub.2).sub.x --Alk--Z, x, Alk, and Z are as defined in the specification;as well as their possible stereoisomers, epimers, N-oxides and pharmaceutically-acceptable acid or base addition salts; and medicinal products containing the same, useful in the treatment of inflammatory disorders requiring an inhibitor of cytokines.
    Type: Grant
    Filed: February 13, 1995
    Date of Patent: January 28, 1997
    Assignee: Adir Et Compagnie
    Inventors: Jean-Daniel Brion, Anne-Marie Chollet, Luc Demuynck, Lucy De Montarby, Yves Rolland, Jacqueline Bonnet, Pietro Ghezzi, Armel Fradin
  • Patent number: 5529998
    Abstract: The invention relates to benzoxazolyl- and benzothiazolyloxazolidinones, processes for their preparation and their use as medicaments, in particular as antibacterial medicaments.
    Type: Grant
    Filed: July 27, 1995
    Date of Patent: June 25, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter Habich, Bernd Riedl, Martin Ruppelt, Andreas Stolle, Hanno Wild, Rainer Endermann, Klaus D. Bremm, Hein-Peter Kroll, Harald Labischinski, Klaus Schaller, Hans-Otto Werling
  • Patent number: 5521145
    Abstract: There is disclosed an iminothiazoline derivative of the general formula: ##STR1## wherein R.sub.1 is (halo)alkyl, (halo)alkenyl, (halo)alkynyl or the like; R.sub.2 is (halo)alkyl, optionally substituted aryl, formyl, cyano or the like; R.sub.3 is hydrogen, (halo)alkyl or the like; and Q is a group of the particular general formula. Also disclosed are a herbicide containing a herbicidally effective amount of the iminothiazoline derivative and a method for controlling unfavorable weeds, which includes applying a herbicidally effective amount of the iminothiazoline derivative to an area where the unfavorable weeds grow or will grow.
    Type: Grant
    Filed: April 3, 1995
    Date of Patent: May 28, 1996
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Minoru Takano, Masayuki Enomoto, Kazuo Saito, Satoru Kizawa
  • Patent number: 5495023
    Abstract: A new nitro compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each lower alkyl or lower alkoxy(lower)alkyl, or ##STR2## is cyclized to form ##STR3## X is --O--, --S-- or --NH--, m is an integer 0 or 1, andR.sup.3 is carbamoyl, lower alkylcarbamoyl, lower alkanoyl, di-lower alkylaminosulfonyl, lower alkylsulfonyl, oxamoyl or a group of the formula: --(Y).sub.n --R.sup.4whereinY is --CO--, --SO.sub.2 --, --COCH.sub.2 -- or ##STR4## n is an integer of 0 or 1, and R.sup.4 is heterocyclic group which is optionally substituted with one or more substituents selected from lower alkyl, lower alkoxy, phenyl, carbamoyl, halogen, amino, lower alkylthio, hydroxy, lower alkylsulfonylamino and carbamoylmethyl, and pharmaceutically acceptable salt thereof, which are useful as vasodilators.
    Type: Grant
    Filed: May 3, 1994
    Date of Patent: February 27, 1996
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Masayuki Kato, Shigetaka Nishino, Mitsuko Hamano, Hisashi Takasugi
  • Patent number: 5492925
    Abstract: There are provided thienyl- and furylpyrrole compounds of formula I ##STR1## and their use for the control of insects and acarina. Further provided are compositions and methods comprising those compounds for the protection of plants from attack by insects and acarina.
    Type: Grant
    Filed: August 31, 1993
    Date of Patent: February 20, 1996
    Assignee: American Cyanamid Company
    Inventors: Roger W. Addor, Joseph A. Furch, III, Laurelee A. Duncan, Jack K. Siddens, deceased
  • Patent number: 5455260
    Abstract: This invention relates to a class of novel aliphatic amino bis-aryl compounds containing at least four carbon atoms and an amino group either substituted thereon or incorporated therein and is further linked or bridged to two mono- and/or bicyclic rings. Compounds of this invention reduce levels of serum cholesterol in the body without significantly reducing mevalonic metabolite synthesis. This invention relates also to pharmacological compositions and method of treatment for lowering serum cholesterol levels using the compounds of this invention.
    Type: Grant
    Filed: May 21, 1993
    Date of Patent: October 3, 1995
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: Robert A. Groneberg, John R. Regan, Kent W. Neuenschwander, Anthony C. Scotese
  • Patent number: 5451596
    Abstract: This invention relates to a class of novel polycyclic compounds containing a cycloalkyl ring having substituted thereon a primary amine and which is further linked or bridged to two mono- and/or bicyclic rings and which reduces levels of serum cholesterol in the body without significantly reducing mevalonic metabolite synthesis. This invention relates also to pharmacological compositions and method of treatment for lowering serum cholesterol levels using the compounds of this invention.
    Type: Grant
    Filed: December 29, 1992
    Date of Patent: September 19, 1995
    Assignee: Rhone Poulenc Rorer Pharmaceuticals Inc.
    Inventors: John W. Ullrich, Terence J. Kiesow, Kent W. Neuenschwander, Keith S. Learn, William P. Dankulich, Anthony C. Scotese
  • Patent number: 5386034
    Abstract: Compounds of general formula (I): ##STR1## where R, X, A, B and p are defined in the description. Medicinal products. Useful for treating sleep disorders comprising the same.
    Type: Grant
    Filed: June 15, 1993
    Date of Patent: January 31, 1995
    Assignee: Adir et Compagnie
    Inventors: Said Yous, Isabelle Lesieur, Patrick Depreux, Daniel H. Caignard, Beatrice Guardiola, Gerard Adam, Pierre Renard
  • Patent number: 5294629
    Abstract: A novel benzothiazole or benzimidazole derivative represented by formula (I) ##STR1## wherein X represents a sulfur atom or a NH group; R.sup.1 represents a hydrogen atom, a lower alkoxy group, a chlorine atom, a bromine atom or an iodine atom; R.sup.2 represents a hydrogen atom a substituted or unsubstituted lower alkyl group, a vinyl group, an aryl group or an acyl group; m is an integer of 1, 2 or 3; and n is an integer of 0, 1 or 2, which shows an excellent acid secretion suppressing effect and gastric mucosa protecting effect, and an antiulcer agent containing the same as an active ingredient.
    Type: Grant
    Filed: March 25, 1993
    Date of Patent: March 15, 1994
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Tomoya Machinami, Kazue Yasufuku, Seiji Shibahara, Fumiya Hirano, Yasukatsu Yuda, Motohiro Nishio, Yuji Matsuhashi, Takashi Tsuruoka, Kiyoaki Katano, Shigeharu Inoye
  • Patent number: 5288749
    Abstract: The present invention provides tertiary and secondary amine compounds of the formula ##STR1## and the pharmaceutically acceptable salts thereof which are antagonists for alpha-2 adrenoreceptors and which inhibit serotonin (5-hydroxytryptamine, 5-HT) uptake.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: February 22, 1994
    Assignee: Abbott Laboratories
    Inventors: Michael D. Meyer, John F. DeBernardis, Rajnandan Prasad, Kevin B. Sippy, Karin R. Tietje
  • Patent number: 5284599
    Abstract: A mesomorphic compound represented by the following formula (I):R.sub.1 --A.sub.1 --B.sub.1 --A.sub.2 --R.sub.2 (I),wherein R.sub.1 and R.sub.2 respectively denote a linear or branched alkyl group having 3-18 carbon atoms capable of including one or non-neighboring two or more methylene groups which can be replaced with at least one species of --Z--, ##STR1## CH.dbd.CH-- and --C.tbd.C--, wherein Z denotes --O-- or --S-- and R.sub.3 denotes hydrogen or an alkyl group having 1-5 carbon atoms; B.sub.1 denotes ##STR2## A.sub.1 denotes a single bond, ##STR3## A.sub.2 denotes a single bond, --A.sub.3 -- or --A.sub.3 --A.sub.4 -- wherein A.sub.3 and A.sub.4 respectively denote any one of ##STR4## and Y.sub.1 and Y.sub.2 respectively denote any one of hydrogen, fluorine, chlorine, bromine, --CH.sub.3, --CN and --CF.sub.3.
    Type: Grant
    Filed: July 20, 1992
    Date of Patent: February 8, 1994
    Assignee: Canon Kabushiki Kaisha
    Inventors: Takashi Iwaki, Takao Takiguchi, Takeshi Togano, Yoko Yamada, Shinichi Nakamura
  • Patent number: 5278177
    Abstract: The invention concerns a bicyclic heterocyclic derivative of the formula I ##STR1## wherein Q is an optionally substituted 9-membered bicyclic heterocyclic moiety containing 1 or 2 N's and optionally a further N, O or S heteroatom;A.sup.1 is a direct link to X.sup.1 or 1- 3C)alkylene;X.sup.1 is oxy, thio, sulphinyl, sulphonyl or imino;Ar is optionally substituted phenylene or pyridylene;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, defines a ring having 5 to 7 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1- 3C)alkylene and X.sup.2 is oxy, thio, sulphinyl or sulphonyl; or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: September 24, 1992
    Date of Patent: January 11, 1994
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Pierre A. R. Bruneau, Graham C. Crawley, Keith Oldham
  • Patent number: 5240949
    Abstract: Compounds of general formula (I): ##STR1## in which: R.sub.1 represents a hydrogen atom or a lower alkyl group,R.sub.2 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted thienyl, furyl, pyrrolyl or pyridinyl group,X represents a hydrogen atom,Y represents a hydroxyl group,or else X and Y together represent an oxygen atom, their enantiomers, diastereoisomers and epimers. Medicaments.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: August 31, 1993
    Assignee: Adir et Compagnie
    Inventors: Daniel Lesieur, Charles Lespagnol, Said Yous
  • Patent number: 5236619
    Abstract: A mesomorphic compound represented by the following formula (I):R.sub.1 --A.sub.1 --B.sub.1 --A.sub.2 --R.sub.2 (I),wherein R.sub.1 and R.sub.2 respectively denote a linear or branched alkyl group having 3-18 carbon atoms capable of including one or non-neighboring two or more methylene groups which can be replaced with at least one species of ##STR1## wherein Z denotes --O-- or --S-- and R.sub.3 denotes hydrogen or an alkyl group having 1-5 carbon atoms; B.sub.1 denotes ##STR2## A.sub.1 denotes a single bond, ##STR3## A.sub.2 denotes a single bond, --A.sub.3 -- or --A.sub.3 --A.sub.4 -- wherein A.sub.3 and A.sub.4 respectively denote any one of ##STR4## and Y.sub.1 and Y.sub.2 respectively denote any one of hydrogen, fluorine, chlorine, bromine, --CH.sub.3, --CN and --CF.sub.3.
    Type: Grant
    Filed: January 22, 1991
    Date of Patent: August 17, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Takashi Iwaki, Takao Takiguchi, Takeshi Togano, Yoko Yamada, Shinichi Nakamura
  • Patent number: 5196434
    Abstract: Compound of general formula (I): ##STR1## where R.sub.1, R.sub.2, R.sub.3, n, X and A are defined in the description.Medicinal products.
    Type: Grant
    Filed: September 26, 1991
    Date of Patent: March 23, 1993
    Assignee: Adir et Compagnie
    Inventors: Thierry Taverne, Isabelle Lesieur, Patrick Depreux, Daniel H. Caignard, Beatrice Guardiola, Gerard Adam, Pierre Renard
  • Patent number: 5180417
    Abstract: Disclosed herein are derivatives of 4-((aryloxy)phenoxy)fluoroalkanoic acid and their use as active herbicides for the pre- and postemergent control of grassy weeds, especially in the presence of broadleaf crops.
    Type: Grant
    Filed: April 12, 1991
    Date of Patent: January 19, 1993
    Assignee: DowElanco
    Inventor: James A. Turner
  • Patent number: 5171746
    Abstract: A thiazole or imidazole derivative having the general formula (I): ##STR1## wherein: R.sup.1 and R.sup.2, which may be the same or different, each independently represent a hydrogen atom, or a phenyl or heteroaryl group, or R.sup.1 and R.sup.2 may together form a benzene ring which may be optionally substituted by a halogen atom or a lower alkyl optionally substituted by a halogen atom, lower alkoxy or nitro group;A represents a sulfur atom or --NH--;B represents a lower alkoxy group optionally substituted by a halogen atom; a five- or six-membered saturated heterocyclic ring containing one nitrogen or oxygen atom which ring may be optionally substituted; a six-membered saturated heterocyclic ring containing one oxygen atom plus one nitrogen atom; a group --XR.sup.3 where X represents a group --NR.sup.4 wherein R.sup.3 and R.sup.4, which may be the same or different, each independently represent a lower alkyl group; or a group --NHC(.dbd.Y)R.sup.5 where Y represents an oxygen or sulfur atom or a group .dbd.
    Type: Grant
    Filed: April 9, 1991
    Date of Patent: December 15, 1992
    Assignee: Meiji Seika Kabushiki Kaisha
    Inventors: Tomoya Machinami, Kazue Yasufuku, Seiji Shibahara, Yasukatsu Yuda, Fumiya Hirano
  • Patent number: 5169950
    Abstract: Compounds of the formula I ##STR1## wherein R, R.sup.1, R.sup.2, R.sup.3, and R.sup.5 have the meaning given in claim 1 are formed by thermal rearrangement of the isomers of formula V ##STR2## especially in the presence of basic catalysts. The compounds are corrosion inhibitors for organic materials, in particular coating materials and lubricants. In these substrates they also act as antioxidants and light-stabilizers and are very stable to heat.
    Type: Grant
    Filed: August 19, 1991
    Date of Patent: December 8, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Adalbert Braig, Hans-Rudolf Meier, David G. Leppard, Robert C. Wasson, Emyr Phillips
  • Patent number: 5166167
    Abstract: A compound of the formula ##STR1## wherein Ar is phenyl optionally substituted with at least one member of the group consisting of halogen, methylenedioxy, phenoxy, phenyl, --CF.sub.3 and alkyl, alkoxy and alkylthio of 1 to 6 carbon atoms, Z is selected from the group consisting of hydrogen, chlorine, --CF.sub.3 and alkyl, alkoxy and alkylthio of 1 to 6 carbon atoms, R.sub.1 and R.sub.2 are individually alkyl of 1 to 6 carbon atoms and the exocyclic double bond has (Z) or (E) configuration having fungicidal activity.
    Type: Grant
    Filed: March 16, 1992
    Date of Patent: November 24, 1992
    Assignee: Roussel Uclaf
    Inventors: Jean-Louis Brayer, Jean-Pierre Demoute, Gilles Mourioux
  • Patent number: 5103007
    Abstract: Lipid derivatives represented by the formula: ##STR1## wherein R.sup.1 stands for an optionally substituted higher alkyl group, R.sup.2 stands for an optionally substituted lower alkyl group or an optionally substituted nitrogen-containing heterocyclic group, R.sup.3 stands for a tertiary amino group or a quaternary ammonium group, J stands for oxygen atom or S(O)t (where t deontes 0, 1 or 2), m and n respectively denotes 1 or 2, p denotes 0, 1 or 2, q and r respectively denote an integer of 2 to 5.and salts thereof have antitumor activities including differentiation-inducing activity and are useful as antitumor agents.
    Type: Grant
    Filed: October 27, 1989
    Date of Patent: April 7, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Keizo Inoue
  • Patent number: 5097039
    Abstract: Compounds of the formula I ##STR1## wherein R, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the meaning given in claim 1 are formed by thermal rearrangement of the isomers of formula V ##STR2## especially in the presence of basic catalysts. The compounds are corrosion inhibitors for organic materials, in particular coating materials and lubricants. In these substrates they also act as antioxidants and light-stabilizers and are very stable to heat.
    Type: Grant
    Filed: August 14, 1989
    Date of Patent: March 17, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Adalbert Braig, Hans-Rudolf Meier, David G. Leppard, Robert C. Wasson, Emyr Phillips
  • Patent number: 5081245
    Abstract: A compound represented by the formula: ##STR1## wherein R represents a hydrogen atom or a lower alkyl group;R.sup.1 represents a higher alkyl group which may be substituted;R.sup.2 represents a hydrogen atom or a lower alkyl group, a lower alkanoyl group or a nitrogen-containing 5- to 7-membered heterocyclic group each of which may be substituted; X represents a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --wherein p represents an integer of 1 to 5, a divalent group represented by the formula:--O(CH.sub.2).sub.q --wherein q represents an integer of 3 to 8, or a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --J--(CH.sub.2).sub.q --wherein J represents an oxygen atom or a group represented by the formula: --S(O).sub.
    Type: Grant
    Filed: August 18, 1989
    Date of Patent: January 14, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Eiko Imamiya, Keizo Inoue
  • Patent number: 5077412
    Abstract: The invention relates to novel substituted phenylthioureas, phenylisothioureas and phenylcarbodiimides of formula I ##STR1## wherein Z is ##STR2## or --N.dbd.C.dbd.N--; R.sub.1 is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.10 alkenyl, C.sub.3 -C.sub.10 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.3 alkyl substituted by 1 or 2 C.sub.3 -C.sub.6 cycloalkyl radicals, or is alkoxyalkyl containing a total of 3 to 10 carbon atoms, halogen-substituted C.sub.1 -C.sub.12 alkyl, polycyclic C.sub.7 -C.sub.10 cycloalkyl, or phenyl(C.sub.1 -C.sub.5)alkyl which may be substituted in the phenyl moiety by 1 or 2 identical or different members selected from the group consisting of halogen, methoxy, ethoxy and C.sub.1 -C.sub.5 alkyl,R.sub.2 is hydrogen or C.sub.1 -C.sub.5 alkyl,R.sub.3 is C.sub.1 -C.sub.5 alkyl or C.sub.3 -C.sub.6 cycloalkyl,R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl,R.sub.
    Type: Grant
    Filed: September 29, 1989
    Date of Patent: December 31, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Josef Ehrenfreund, Manfred Boger, Odd Kristiansen, Jozef Drabek, Haukur Kristinsson
  • Patent number: 5073638
    Abstract: A process for the manufacture of 2-thiocyanomethylthiobenzothiazole. 2-Chloromethylthiobenzothiazole is reacted, in the presence of at least one glycol ether as a solvent for the reaction, with either an alkali metal or an ammonium thiocyanate at a temperature and for a time sufficient to produce the 2-thiocyanomethylthiobenzothiazole.
    Type: Grant
    Filed: September 26, 1990
    Date of Patent: December 17, 1991
    Assignee: Buckman Laboratores International, Inc.
    Inventors: Lawrence S. Conaway, Marc F. Nagel, John D. Pera
  • Patent number: 5071860
    Abstract: Insecticidally active substituted heteroaryl phenyl ethers of the formula ##STR1## in which Het represents an optionally substituted heteroaromatic radical,X represents O, S, --CH.sub.2 --, --O--CH.sub.2 --, --S--CH.sub.2 --, --CH.sub.2 --O--, ##STR2## Y represents O, --O--CH.sub.2 -- or S, Z represents an optionally substituted aromatic or heteroaromatic radical;m represents integers from 1-4n represents 0, 1, 2, 3, 4O represents 0, 1, 2, 3, 4, provided than n and o do not simultaneously represent 0p represents integers from 1-4,R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently of one another represent hydrogen, C.sub.1 -C.sub.6 -alkyl which is optionally substituted; two radicals adjacent to one another can also, together with the C atoms to which they are bonded, form a saturated carbocyclic 5- or 6-ring,R.sup.1 represents identical or different radicals hydrogen, halogen, CN, C.sub.1-4 -alkyl, 1-5-halogeno-C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylthio, 1-5-halogeno-C.sub.
    Type: Grant
    Filed: March 7, 1990
    Date of Patent: December 10, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Alig, Wilhelm Stendel, Michael Londershausen
  • Patent number: 5055477
    Abstract: A pyrazolyl acrylic acid derivative having plant fungicidal activity of formula (I): ##STR1## wherein: R.sub.1 and R.sub.2 are independently hydrogen or C.sub.1 -C.sub.5 alkyl;A is a group of the formula: ##STR2## wherein X is independently hydrogen; halogen; cyano; nitro; C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.11 alkenyl, C.sub.1 -C.sub.10 alkoxy, C.sub.2 -C.sub.11 alkenyloxy, C.sub.2 -C.sub.11 alkynyloxy, C.sub.2 -C.sub.11 alkylcarbonyl or C.sub.2 -C.sub.11 alkylcarbonyloxy optionally substituted with one or more substituents selected from halogen, nitro, cyano, trifluoromethyl and C.sub.1 -C.sub.5 alkoxy; or C.sub.7 -C.sub.13 arylcarbonyl, C.sub.4 -C.sub.9 cycloalkylcarbonyloxy, C.sub.7 -C.sub.13 arylcarbonyloxy, C.sub.6 -C.sub.12 aryl, C.sub.6 -C.sub.12 aryloxy, C.sub.2 -C.sub.13 heteroaryl having 1-3 heteroatom(s) selected from oxygen, sulfur, and nitrogen, C.sub.2 -C.sub.13 heteroaryloxy having 1-3 heteroatom(s) selected from oxygen, sulfur, and nitrogen, C.sub.7 -C.sub.12 aralkyl or C.sub.7 -C.sub.
    Type: Grant
    Filed: December 13, 1990
    Date of Patent: October 8, 1991
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Masatsugu Oda, Toshiro Sakaki, Kazuhiko Kikutake
  • Patent number: 5006541
    Abstract: Compounds of the formula ##STR1## where Y is alkyl, aryl or heterocyclic, n is 1-7, R is hydrogen, alkyl, aralkyl or carboxymethyl, R.sub.1 is acetoxy, thiophenoxy, hydrogen, halo, alkyl, alkoxy or trifluoromethyl, R.sub.2 is hydrogen, alkyl or alkanoyl and X is C.dbd.O, CH.sub.2, NH, O or S as antiallergy and antiinflammatory agents.
    Type: Grant
    Filed: October 25, 1989
    Date of Patent: April 9, 1991
    Assignee: Pfizer Inc.
    Inventors: Yoshihiko Kitaura, Fumitaka Ito, Rodney W. Stevens, Nobuko Asai
  • Patent number: 4996218
    Abstract: Compounds of the general formula (I) ##STR1## and physiologically acceptable salts and solvates thereof, which have .beta..sub.2 -adrenoreceptor stimulant activity. They may be used in the treatment of diseases associated with reversible airways obstruction, such as asthma and chronic bronchitis.In preferred embodiments, Q represents a chlorine atom or a trifluoromethyl group, X represents a C.sub.3-4 alkylene chain, Y a C.sub.1-5 alkylene chain, R, R.sup.1 and R.sup.2 are each preferably a hydrogen atom or a methyl group and Het represents a pyrimidinyl pyrazinyl, triazinyl, thiazolyl, quinolinyl, benzimidazolyl, benzothiazolyl, benzoxazolyl or pyridyl group.
    Type: Grant
    Filed: August 10, 1988
    Date of Patent: February 26, 1991
    Assignee: Glaxo Group Limited
    Inventor: Lawrence H. C. Lunts
  • Patent number: 4987146
    Abstract: N-hetaryl imidazole derivatives of general Formula I ##STR1##are disclosed in whichHet represents an optionally substituted monocyclic or bicyclic heteroaromate,R.sup.3 represents hydrogen, a straight or branched C.sub.1-6 -alkyl group, or a C.sub.1-6 -alkoxy-alkyl group, andR.sup.4 represents --COOR.sup.5 --CONR.sup.6 R.sup.7 --CN, ##STR2##with R.sup.5 meaning hydrogen, a straight or branched C.sub.1-6 -alkyl group, R.sup.6 and R.sup.7 are the same of different and represent hydrogen or a straight, branched, or cyclic alkyl group with up to 7 carbon atoms or, together with the nitrogen atom, form a saturated five or six ring optionally containing another heteroatom and R.sup.8 means hydrogen or a straight, branched or cyclic alkyl group with up to 7 carbon atoms.
    Type: Grant
    Filed: July 14, 1989
    Date of Patent: January 22, 1991
    Assignee: Schering Aktiengesellschaft
    Inventors: Ralph Rohde, Helmut Biere, Ralph Schmiechen, John S. Andrews, David N. Stephens
  • Patent number: 4968844
    Abstract: Retinal is prepared by condensing a C.sub.15 sulphide of formula: ##STR1## in which R.sub.1 denotes aryl, aralkyl, pyridyl, 2-thiazolyl, 2-benzothiazolyl, 2-benzimidazolyl or 2-benzoxazolyl, with a haloacetal of formula: ##STR2## in which X denotes a halogen atom and R denotes an alkyl radical containing 1 to 4 carbon atoms, to give a C.sub.20 sulphide acetal of formula: ##STR3## in which R.sub.1 and R are defined as above, hydrolysing the said sulphide acetal to give a C.sub.20 sulphide aldehyde of formula: ##STR4## in which R.sub.1 is defined as above, desulphurizing the said sulphide aldehyde to give retinal, and isolating the retinal obtained.
    Type: Grant
    Filed: October 27, 1988
    Date of Patent: November 6, 1990
    Assignee: Centre National de la Recherche Scientifique (C. N. R. S.)
    Inventor: Marc Julia
  • Patent number: 4963576
    Abstract: The invention relates to dithioacetal compounds having 5-lipoxygenase-inhibiting activity, of the formula: ##STR1## wherein R.sup.1 is lower alkyl, di-(lower)alkylamino, aryl, or heterocyclic group which may have one or more substituents selected from halogen, lower alkyl, lower alkoxy and phenyl,R.sup.2 and R.sup.3 are each lower alkyl, aryl or ar-(lower)alkyl, or R.sup.2 and R.sup.3 are together to form 1,3-dithian ring,R.sup.4 is hydrogen or lower alkoxy, andn is O or an integer 1 to 4 and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: May 6, 1988
    Date of Patent: October 16, 1990
    Assignee: Fujisawa Pharmaceutical Company, Ltd.
    Inventors: Teruo Oku, Yoshio Kawai, Hiroshi Kayakiri, Kazuyoshi Kuratani, Masashi Hashimoto
  • Patent number: 4952599
    Abstract: Novel substituted phenylthioureas, phenylisothioureas and phenylcarbodiimides of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.10 alkyl, unsubstituted or substituted by one or more halogen atoms and/or C.sub.1 -C.sub.6 alkoxy groups; C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkyl which is substituted by one or more halogen atoms and/or C.sub.1 -C.sub.4 alkyl groups; C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl, di(C.sub.3 -C.sub.8)cycloalkyl-C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 phenylalkyl or C.sub.1 -C.sub.4 phenylalkyl which is substituted in the phenyl nucleus by one or more members selected from the group consisting of halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy and/or C.sub.1 -C.sub.4 haloalkyl; or is C.sub.5 -C.sub.6 cycloalkenyl,R.sub.2 is hydrogen, C.sub.1 -C.sub.5 alkyl or C.sub.5 -C.sub.6 cycloalkenyl,R.sub.3 is C.sub.1 -C.sub.5 alkyl or C.sub.5 -C.sub.6 cycloalkyl,R.sub.4 is hydrogen or C.sub.1 -C.sub.3 alkyl,R.sub.
    Type: Grant
    Filed: July 20, 1988
    Date of Patent: August 28, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Josef Ehrenfreund, Manfred Boger, Jozef Drabek
  • Patent number: 4888348
    Abstract: The invention relates to novel substituted phenylthioureas, phenylisothioureas and phenylcarbodiimides of formula I ##STR1## wherein Z is ##STR2## or --N.dbd.C.dbd.N--; R.sub.1 is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.10 alkenyl, C.sub.3 -C.sub.10 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.3 alkyl substituted by 1 or 2 C.sub.3 -C.sub.6 cycloalkyl radicals, or is alkoxyalkyl containing a total of 3 to 10 carbon atoms, halogen-substituted C.sub.1 -C.sub.12 alkyl, polycyclic C.sub.7 -C.sub.10 cycloalkyl, or phenyl(C.sub.1 -C.sub.5)alkyl which may be substituted in the phenyl moiety by 1 or 2 identical or different members selected from the group consisting of halogen, methoxy, ethoxy and C.sub.1 -C.sub.5 alkyl,R.sub.2 is hydrogen or C.sub.1 -C.sub.5 alkyl,R.sub.3 is C.sub.1 -C.sub.5 alkyl or C.sub.3 -C.sub.6 cycloalkyl,R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl,R.sub.
    Type: Grant
    Filed: August 28, 1987
    Date of Patent: December 19, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Josef Ehrenfreund, Manfred Boger, Odd Kristiansen, Jozef Drabek, Haukur Kristinsson
  • Patent number: 4873338
    Abstract: Compounds corresponding to Formula I ##STR1## wherein R.sup.1 denotes an acyl group andX denotes hydrogen, halogen, alkoxy, aroxy, SO.sub.3 H or a heterocyclic group attached through --O-- or --N<are prepared form a compound corresponding to Formula II ##STR2## wherein X has the meaning already indicated and Q denotes the group required for completing a dicarbonimide ringby reduction of the said compound to the amino compound and acylation into a compound corresponding to Formula III ##STR3## wherein X, Q and R.sup.1 have the meanings indicatedfollowed by conversion of the compound corresponding to Formula III into a compound corresponding to Formula I by hydrazinolytic or hydrolytic decomposition of the dicarbonimide ring.
    Type: Grant
    Filed: November 23, 1987
    Date of Patent: October 10, 1989
    Assignee: Agfa-Gevaert Aktiengesellschaft
    Inventors: Heinz Wiesen, Erich Wolff
  • Patent number: 4873346
    Abstract: The present invention provides certain novel substituted benzothiazoles, benzimidazoles and benzoxazoles which are useful as inhibitors of leukotriene biosynthesis and/or as inhibitors of the action of lipoxygenase and/or as inhibitors of mucus secretion in mammalian metabolism. They are thus employed wherever it is medically necessary or desirable to inhibit these systems.
    Type: Grant
    Filed: September 20, 1985
    Date of Patent: October 10, 1989
    Assignee: The Upjohn Company
    Inventor: David J. Anderson
  • Patent number: 4853149
    Abstract: Heterocyclic liquid crystal compounds containing the structural element ##STR1## wherein M is H, CN,, NCS, halogen or an alkyl group with 1-5 C atoms,X is CR.sup.4 or N,Y is CHR.sup.4, O, S or NR.sup.5,R.sup.4 is H, alkyl with 1-15 C atoms, halogen or cyano andR.sup.5 is H or alkyl with 1-15 C atoms,with the proviso that in the case where Y=CHR.sup.4, X is N, are suitable as components of liquid crystal phases.
    Type: Grant
    Filed: October 26, 1987
    Date of Patent: August 1, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Joachim Krause, Andreas Wachtler, Bernhard Scheuble, Georg Weber
  • Patent number: 4835166
    Abstract: Compounds of the formula ##STR1## where Y is alkyl, aryl or heterocyclic, n is 1-7, R is hydrogen, alkyl, aralkyl or carboxymethyl, R.sub.1 is acetoxy, thiophenoxy, hydrogen, halo, alkyl, alkoxy or trifluoromethyl, R.sub.2 is hydrogen, alkyl or alkanoyl and X is C.dbd.O, CH.sub.2, NH, O or S as antiallergy and antiinflammatory agents.
    Type: Grant
    Filed: December 7, 1987
    Date of Patent: May 30, 1989
    Assignee: Pfizer Inc.
    Inventors: Yoshihiko Kitaura, Fumitaka Ito, Rodney W. Stevens, Nobuko Asai
  • Patent number: 4826989
    Abstract: The present invention provides a process for the preparation of compounds of the general formula: ##STR1## in which X is a hydroxyl group and X.sub.1 is a hydrogen atom or a hydroxyl group, and especially of luciferin, by the reaction of D-cysteine with 2-cyanomono- or -dihydroxybenzothiazole obtained from 2-chloromono- or -dimethoxybenzothiazole via a demethylation, wherein the demethylation is accomplished by reaction with iodotrimethylsilane or with a mixture of phenyltrimethylsilane and iodine and hydrolysis under mild conditions of the silyl derivative formed.
    Type: Grant
    Filed: September 10, 1987
    Date of Patent: May 2, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Hans-Georg Batz, Karl Wulff
  • Patent number: 4767775
    Abstract: Microbicidal substituted pyrazolin-5-ones of the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another each represent hydrogen, alkyl, alkenyl, alkinyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkoxycarbonyl, hydroxycarbonylalkyl, alkoxycarbonylalkyl, aminocarbonylalkyl, alkylaminocarbonylalkyl or dialkylaminocarbonylalkyl, or represent in each case optionally substituted oxiranylalkyl, aralkyl, heterocyclyl or aryl andHet represents an optionally substituted heterocyclic radical.Intermediates therefor of the formula ##STR2## in which R is alkyl, are also disclosed.
    Type: Grant
    Filed: July 24, 1986
    Date of Patent: August 30, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Jelich, Wilhelm Brandes, Gerd Hanssler, Paul Reinecke
  • Patent number: 4762848
    Abstract: Heterocyclic sulfides of the general formula heterocycle-S-R, a process for their preparation and, in particular, their use for immunostimulation, immunorestoration and cytostatic treatment, and pharmaceutical agents, which contain a sulfide of this type, for these indications.
    Type: Grant
    Filed: March 10, 1986
    Date of Patent: August 9, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karl-Heinz Scheunemann, Walter Durckheimer, Jurgen Blumbach, Michael Limbert, Hans-Ulrich Schorlemmer, Gerhard Dickneite, Hans-Harald Sedlacek
  • Patent number: 4755609
    Abstract: The present invention relates to the preparation of thiocyanatomethylthiobenzothiazoles by the reaction of halomethylthiobenzothiazoles with thiocyanates at elevated temperature in aqueous solution in the presence of a phase transfer catalyst.
    Type: Grant
    Filed: February 12, 1986
    Date of Patent: July 5, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerold Schade, Karlfried Wedemeyer, Herbert Diehl
  • Patent number: 4750931
    Abstract: Certain novel fluorophenoxy compounds, principally aryloxyfluorophenoxyalkanoic acids and derivatives thereof, are described. More specifically, these novel compounds bear 1 to 4 fluorine substituents on the phenyl ring. These novel compounds exhibit surprising preemergent and postemergent activity when used according to the method of the invention in the control of grassy weeds.
    Type: Grant
    Filed: October 15, 1985
    Date of Patent: June 14, 1988
    Assignee: The Dow Chemical Company
    Inventor: Richard B. Rogers
  • Patent number: 4678789
    Abstract: Compounds of the general formula: ##STR1## wherein Ar is naphthyl, biphenylyl, phenyl or substituted phenyl; n is 0, 1 or 2; and Het is a heterocyclic group which may optionally be substituted or fused to a phenyl, substituted phenyl or further heterocyclic ring; and their pharmaceutically acceptable salts are antifungal agents useful in combatting fungal infections in animals, including humans.
    Type: Grant
    Filed: March 28, 1983
    Date of Patent: July 7, 1987
    Assignee: Pfizer Inc.
    Inventors: Kenneth Richardson, Peter J. Whittle
  • Patent number: 4594425
    Abstract: There are disclosed compounds of the formula ##STR1## n is 0-6; A is O or S;B is OR.sup.2, SR.sup.2 or N(R.sup.2).sub.2 ;R.sup.1 is hydrogen, loweralkyl, loweralkoxy or halo;R.sup.2 is hydrogen or loweralkyl;and the pharmaceutically acceptable salts thereof, and their use in the treatment of leukotriene-mediated naso-bronchial obstructive airpassageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like.
    Type: Grant
    Filed: February 9, 1984
    Date of Patent: June 10, 1986
    Assignee: American Home Products Corporation
    Inventors: John H. Musser, Dennis M. Kubrak
  • Patent number: 4564682
    Abstract: A compound of the formula ##STR1## is reacted with a phenol of the formula ##STR2## in the presence of an acid to produce a heterocyclic phenyl ether of the formula ##STR3## wherein each R is independently selected from halogen, trifluoromethyl, nitro, cyano, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms or alkylthio having 1 to 4 carbon atoms;A is oxygen, sulfur or N-alkyl having 1 to 4 carbon atoms; andn is a number from 0 to 3.
    Type: Grant
    Filed: February 27, 1984
    Date of Patent: January 14, 1986
    Assignee: Cassella Aktiengesellschaft
    Inventors: Ulrich Kussmaul, Johannes Becherer, Reinhard Handte, Rolf Muller
  • Patent number: 4539408
    Abstract: Quaternary sulfoalkyl or sulfoalkenyl salts of tertiary amine bases are prepared by reacting the tertiary amine bases at elevated temperatures with a hydroxy alkane sulfonic acid or a hydroxyalkene sulphonic acid.
    Type: Grant
    Filed: April 28, 1978
    Date of Patent: September 3, 1985
    Assignee: Agfa-Gevaert Aktiengesellschaft
    Inventors: Helmut Kampfer, Marie Hase, Max Glass