Substituent Q Is Monocyclic Patents (Class 564/90)
  • Patent number: 5552419
    Abstract: The invention relates to the compounds of formula I ##STR1## pharmaceutically acceptable prodrug derivatives and pharmaceutically acceptable salts thereof; methods for preparation thereof; pharmaceutical compositions comprising said compounds; and a method of inhibiting matrix-degrading metalloproteinase and of treating matrix-degrading metalloproteinase dependent conditions in mammals using such compounds.
    Type: Grant
    Filed: November 3, 1994
    Date of Patent: September 3, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Lawrence J. MacPherson, David T. Parker
  • Patent number: 5534654
    Abstract: A novel hydroxamic acid compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof having cell growth inhibition, vascularization inhibition activities and the like.The compounds of the present invention possess inhibitory activities against the growth of vascular endothelial cells and the expression of lymphocyte adhesive factors and the detransforming activity of cells transformed by ras gene, and inhibit the cell growth and are effective on inflammation and tumor.
    Type: Grant
    Filed: August 3, 1993
    Date of Patent: July 9, 1996
    Assignee: Shionogi & Co., Ltd.
    Inventors: Mitsuaki Ohtani, Hitoshi Arita, Kenji Sugita, Takaharu Matsuura, Kazuhiro Shirahase
  • Patent number: 5521219
    Abstract: Sulfonamide-containing hydroxyethylamine compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.
    Type: Grant
    Filed: August 24, 1993
    Date of Patent: May 28, 1996
    Assignee: G. D. Searle & Co.
    Inventors: Michael L. Vazquez, Richard A. Mueller, John J. Talley, Daniel Getman, Gary A. DeCrescenzo, John N. Freskos
  • Patent number: 5510388
    Abstract: Sulfonamide-containing hydroxyethylamine compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: April 23, 1996
    Assignee: G. D. Searle & Co.
    Inventors: Michael L. Vazquez, Richard A. Mueller, John J. Talley, Daniel Getman, Gary A. DeCrescenzo, John N. Freskos
  • Patent number: 5506242
    Abstract: The invention relates to a method of inhibiting metalloellastase activity, of inhibiting the degradation of elastin, or of treating macrophage metalloelastase dependent conditions in mammals which comprises administering to a mammal in need thereof an effective macrophage metalloelastase inhibiting amount of a compound of formula I ##STR1## wherein Ar, R, R.sub.1 and R.sub.2 have meanings as defined, or of a pharmaceutically acceptable prodrug derivative thereof, or of a pharmaceutically acceptable salt thereof, or of pharmaceutical compositions comprising a said compound.
    Type: Grant
    Filed: June 24, 1994
    Date of Patent: April 9, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Lawrence J. MacPherson, David T. Parker, Arco Y. Jeng
  • Patent number: 5478941
    Abstract: Levorotatory and dextrorotatory enantiomers of 1-[(4-chlorophenyl)phenylmethyl]-4-[(4-methylphenyl)sulfonyl]piperazine of the formula ##STR1## their preparation and use for the preparation of substantially optically pure enantiomers of 1-[(4-chlorophenyl)phenylmethyl]piperazine, which are themselves valuable intermediate products for the preparation of optically active therapeutic compounds having a very high degree of optical purity.
    Type: Grant
    Filed: March 8, 1994
    Date of Patent: December 26, 1995
    Assignee: U C B, S.A.
    Inventors: Eric Cossement, Guy Bodson, Jean Gobert
  • Patent number: 5466712
    Abstract: The compound of the formula (I) or a pharmaceutically acceptable salt thereof, are smooth muscle relaxants ##STR1##
    Type: Grant
    Filed: November 4, 1994
    Date of Patent: November 14, 1995
    Assignee: American Home Products Corporation
    Inventors: John A. Butera, Schuyler A. Antane, Bradford H. Hirth
  • Patent number: 5464867
    Abstract: The compound of the formula (I) or a pharmaceutically acceptable salt thereof, are smooth muscle relaxants.
    Type: Grant
    Filed: November 16, 1994
    Date of Patent: November 7, 1995
    Assignee: American Home Products Corporation
    Inventors: Madelene M. Antane, John A. Butera, Bradford H. Hirth, Schuyler A. Antane
  • Patent number: 5457131
    Abstract: The present invention relates to cyclopentane heptanoic or cyclopentane heptenoic acid, 2-hydrocarbyl sulfonamidomethyl, and derivatives thereof, useful as therapeutic agents. In particular, the therapeutic agents of this invention are useful as ocular hypotensives.
    Type: Grant
    Filed: August 18, 1994
    Date of Patent: October 10, 1995
    Assignee: Allergan, Inc.
    Inventor: Steven W. Andrews
  • Patent number: 5455258
    Abstract: Particularly the invention relates to the compounds of formula I ##STR1## (a) wherein Ar is carbocyclic or heterocyclic aryl;R is hydrogen, lower alkyl, carbocyclic aryl-lower alkyl, carbocyclic aryl, heterocyclic aryl, biaryl, biaryl-lower alkyl, heterocyclic aryl-lower alkyl, mono- or poly-halo-lower alkyl, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.7 -cycloalkyl-lower alkyl, hydroxy-lower alkyl, acyloxy-lower alkyl, lower alkoxy-lower alkyl, lower alkyl-(thio, sulfinyl or sulfonyl)-lower alkyl, amino, mono- or di-lower alkylamino)-lower alkyl, acylamino-lower alkyl, (N-lower alkyl-piperazino or N-aryl-lower alkylpiperazino)-lower alkyl, or (morpholino, thiomorpholino, piperidino, pyrrolidino, piperidyl or N-lower alkylpiperidyl)-lower alkyl;R.sub.1 is hydrogen, lower alkyl, carbocyclic aryl-lower alkyl, carbocyclic aryl, heterocyclic aryl, biaryl, biaryl-lower alkyl, heterocyclic aryl-lower alkyl, mono- or poly-halo-lower alkyl, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.
    Type: Grant
    Filed: January 6, 1993
    Date of Patent: October 3, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Lawrence J. MacPherson, David T. Parker
  • Patent number: 5451677
    Abstract: Substituted phenylsulfonamides are selective .beta..sub.3 adrenergic receptor agonists with very little .beta..sub.1 and .beta..sub.2 adrenergic receptor activity and as such the compounds are capable of increasing lipolysis and energy expenditure in cells. The compounds thus have potent activity in the treatment of Type II diabetes and obesity. The compounds can also be used to lower triglyceride levels and cholesterol levels or raise high density lipoprotein levels or to decrease gut motility. In addition, the compounds can be used to reduced neurogenic inflammation or as antidepressant agents. The compounds are prepared by coupling an aminoalkylphenyl-sulfonamide with an appropriately substituted alkyl epoxide. Compositions and methods for the use of the compounds in the treatment of diabetes and obesity and for lowering triglyceride levels and cholesterol levels or raising high density lipoprotein levels or for increasing gut motility are also disclosed.
    Type: Grant
    Filed: December 15, 1993
    Date of Patent: September 19, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Michael H. Fisher, Robert J. Mathvink, Hyun O. Ok, Emma R. Parmee, Ann E. Weber
  • Patent number: 5414120
    Abstract: The present invention relates to novel polyether-substituted compounds of imides and their use as surface-active agents.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: May 9, 1995
    Assignee: Bayer AG
    Inventors: Klaus Pohmer, Rainer Weber, Cornelia Dorzbach-Lange, Reinhard Haida, Hans-Heinrich Moretto
  • Patent number: 5407951
    Abstract: The present invention provides sulphonamides of the general formula: ##STR1## wherein R.sup.1 and R.sup.2, which can be the same or different, are hydrogen or halogen atoms or C.sub.1 -C.sub.6 -alkyl, trifluoro-methyl, cyano, carboxyl, alkoxycarbonyl, aminocarbonyl, N-alkylaminocarbonyl or N,N-dialkylaminocarbonyl radicals or, when R.sup.1 and R.sup.2 are alkyl radicals ortho to one another, R.sup.1 and R.sup.2 together with the carbon atoms to which they are attached, form a saturated or unsaturated C.sub.5-C.sub.7 -alkylene ring, R.sup.3 is a hydrogen atom, an alkyl radical containing up to 6 carbon atoms, an acyl radical, a phenylalkyl or phenylalkenyl radical, the phenyl moiety of which can be substituted by halogen, alkyl or trifluoromethyl, C is a --(CH.sub.2).sub.m --radical, in which m is 0, 1, 2 or 3, or a branched C.sub.2 -C.sub.5 -alkylene radical, whereby a methylene radical --CH.sub.
    Type: Grant
    Filed: June 30, 1992
    Date of Patent: April 18, 1995
    Assignee: Boehringer Mannheim GmbH
    Inventors: Ernst-Christian Witte, Karlheinz Stegmeier, Liesel Doerge
  • Patent number: 5403853
    Abstract: The compounds of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are, independently, hydrogen, straight or branched chain alkyl or mono- or bi-cyclic alkyl;A is a substituted phenyl group containing one or two substituents selected from cyano, nitro, alkyl, perfluoroalkyl, alkoxy, perfluoroalkoxy, amino, alkylamino, dialkylamino, sulfamyl, alkylsulfonamido, arylsulfonamido, alkylcarboxamido, arylcarboxamido, alkylsulfone, perfluoroalkylsulfone, arylsulfone, chloro, bromo, fluoro, iodo, 1-imidazolyl or carboxyl; or a pharmaceutically acceptable salt thereof, are smooth muscle relaxants.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: April 4, 1995
    Assignee: American Home Products Corporation
    Inventors: John A. Butera, Schuyler A. Antane
  • Patent number: 5393790
    Abstract: A class of substituted spiro compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula III: ##STR1## wherein n is a number selected from 0, 1 and 2; wherein R.sup.3 is methylsulfonyl or sulfamyl; and wherein R.sup.8 is selected from hydrido, fluoro, chloro, bromo, iodo, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, isobutyl, methoxy, ethoxy, propoxy, butoxy, hydroxyl, mercapto, methylthio, ethylthio, cyano, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, difluorochloromethyl, dichlorofluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, trifluoromethoxy, hydroxymethyl, methoxymethyl and ethoxymethyl; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: February 10, 1994
    Date of Patent: February 28, 1995
    Assignee: G.D. Searle & Co.
    Inventors: David B. Reitz, Robert E. Manning, Horng-Chi Huang, Jinglin Li
  • Patent number: 5387608
    Abstract: The present invention relates to cyclopentane heptanoic or cyclopentane heptenoic acid, 2-hydrocarbyl sulfonamidomethyl, and derivatives thereof, useful as therapeutic agents. In particular, the therapeutic agents of this invention are useful as ocular hypotensives.
    Type: Grant
    Filed: August 17, 1993
    Date of Patent: February 7, 1995
    Assignee: Allergan, Inc.
    Inventor: Steven W. Andrews
  • Patent number: 5356893
    Abstract: The invention provides compounds of formula (I): ##STR1## or a physiologically acceptable salt or solvate thereof wherein R.sup.1 represents a halogen or hydrogen atom or a C.sub.1-6 alkyl or C.sub.1-6 alkoxy group;R.sup.2 represents a phenyl group optionally substituted by one or two substituents;R.sup.3 represents the group ##STR2## R.sup.4 and R.sup.5, which may be the same or different, each independently represent a hydrogen atom or a halogen atom, or a group selected from hydroxy, C.sub.1-6 alkoxy or C.sub.1-6 alkyl.The compounds may be used in the treatment or prophylaxis of depression and other CNS disorders.
    Type: Grant
    Filed: September 17, 1992
    Date of Patent: October 18, 1994
    Assignee: Glaxo Group Limited
    Inventors: John Bradshaw, John W. Clitherow, Ian B. Campbell
  • Patent number: 5338883
    Abstract: There are provided novel benzenesulfonyl carboxamide compounds and novel intermediate benzenesulfonyl-2-imidazolin-5-one compounds, novel intermediates and methods for the preparation of said compounds, and a method for controlling a variety of annual and perennial plant species utilizing novel benzenesulfonyl carboxamide compounds and novel intermediate benzenesulfonyl 2-imidazolin-5-one compounds.
    Type: Grant
    Filed: July 6, 1993
    Date of Patent: August 16, 1994
    Assignee: American Cyanamid Company
    Inventors: Sergio I. Alvarado, Alvin D. Crews, Jr., Peter J. Wepplo, Robert F. Doehner, Jr., Thomas E. Brady, David M. Gange, Desiree L. Little
  • Patent number: 5318770
    Abstract: Methods and compositions are disclosed for enhancing .sup.19 F magnetic resonance imaging which utilize trifluorometyl derivatives of iodinated X-ray contrast media. Typical magnetic resonance contrast media within the scope of the present invention include bis(trifluoromethyl)benzene derivatives, tris(trifluoromethyl)benzene derivatives, tetrakis(trifluoromethyl)benzene derivatives, and other related trifluoromethylated benzene derivatives.
    Type: Grant
    Filed: October 25, 1991
    Date of Patent: June 7, 1994
    Assignee: Mallinckrodt Medical, Inc.
    Inventors: David H. White, Steven R. Woulfe, Youlin Lin, Mills T. Kneller
  • Patent number: 5302724
    Abstract: This invention provides certain sulfonamide compounds, formulations and method of use of certain sulfonamide compounds in treating susceptible neoplasms.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: April 12, 1994
    Assignee: Eli Lilly and Company
    Inventors: J. Jeffry Howbert, Fariborz Mohamadi, Michael M. Spees
  • Patent number: 5260285
    Abstract: Novel substituted imidazopyridazines of formula (I) which are useful as angiotensin II antagonists, are disclosed.
    Type: Grant
    Filed: November 25, 1991
    Date of Patent: November 9, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Eric E. Allen, William J. Greenlee, Prasun K. Chakravarty, Malcolm MacCoss, Arthur A. Patchett, Thomas F. Walsh
  • Patent number: 5233074
    Abstract: The invention describes a process for selectively preparing ortho-fluorinated substituted aromatic compounds wherein an aromatic compound containing a substituent capable of directing ortho metalation is contacted with a metalating reagent under reaction conditions sufficient to form an ortho-metalated substituted aromatic compound. The ortho-metalated substituted aromatic compound is reacted with an electrophilic fluorinating reagent under reaction conditions sufficient to form the desired ortho-fluorinated substituted aromatic compound which is then recovered from the reaction mixture. The process which utilizes a metalation intermediate prior to effecting the electrophilic fluorination step overcomes problems associated with prior art electrophilic fluorination processes which do not proceed through a regiospecifically controlled intermediate.
    Type: Grant
    Filed: June 1, 1992
    Date of Patent: August 3, 1993
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Gauri S. Lal
  • Patent number: 5220062
    Abstract: There is disclosed a multi-step process for the preparation of benzenesulfonamides of general formula ##STR1## wherein R is 3,3-difluorobutyl or 3,3-difluorobuten-1-yl. The benzenesulfonamides obtainable by the process of the invention are intermediates for the synthesis of herbicidally active sulfonyl ureas.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: June 15, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Willy Meyer, Urs Siegrist
  • Patent number: 5166430
    Abstract: A 2-(2-halogenoethylthio)-phenylsulfonamide of the formula I ##STR1## in which Z.sub.1 and Z.sub.2 independently of one another are hydrogen, fluorine or chlorine, is prepared by a process wherein:a) a 2-halogenophenylsulfonamide of the formula II ##STR2## in which X is fluorine, chlorine or bromine, is converted, in the presence of a base, together with a mercaptan of the formula IIIR-SH (III)in which R is C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkyl substituted by phenyl, into a 2-sulfenylphenylsulfonamide,b) this compound is oxidized to give the 2-sulfinylphenylsulfonamide,c) the resulting 2-sulfinylphenylsulfonamide is converted, in the presence of an acid, into the disulfide of the formula VI ##STR3## d) the disulfide of the formula VI is reduced to the 2-mercaptophenylsulfonamide,e) this compound is then converted, by means of a trialkylamine of the formula X(R.sub.1).sub.3 N (X)in which R.sub.1 is C.sub.1 -C.sub.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: November 24, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Henry Szczepanski, Willy Meyer, Franz Weibel
  • Patent number: 5120865
    Abstract: A process suitable for industrially preparing 2,3-trans-1,4-bridged cyclohexane sulfonamide derivatives, especially useful as an intermediate for the synthesis of a trans bicyclo[2,2,1] heptane carboxylic acid derivative, a clinically important thromboxane A.sub.2 antagonist, comprising: allowing to react corresponding a cis/trans mixture of sulfonamide derivatives with an anionoid or water-soluble carbonyl reagent at pH3-7 so that the trans isomer may form a water-soluble adduct with the anionoid or carbonyl reagent, separating the resulting adduct dissolved in an aqueous layer, and recovering the trans isomer by treating the adduct with a base or an acid. Also provided is an alkali metal hydrogen sulfite adduct of 2,3-trans 1,4-bridged cyclohexane sulfonamide derivative.
    Type: Grant
    Filed: August 30, 1991
    Date of Patent: June 9, 1992
    Assignee: Shionogi & Co., Ltd.
    Inventors: Masayuki Narisada, Mitsuaki Ohtani, Fumihiko Watanabe, Kyozo Kawata
  • Patent number: 5106407
    Abstract: The present invention discloses the antimicrobial utility of certain iodonium ylide compounds. The particular iodonium ylide compounds are phenyl iodonium ylides having an ortho substituent that stabilizes the positive charge on the polyvalent iodine by a nonbonded electrostatic interaction. The polyvalent iodine is further stabilized by a cyclic 1,3-dicarbonyl anion.
    Type: Grant
    Filed: December 4, 1989
    Date of Patent: April 21, 1992
    Assignee: The Dow Chemical Company
    Inventors: Attila G. Relenyi, Gerald F. Koser, Richard W. Walter, Jr., William J. Kruper, Jr., Ravi B. Shankar, Anthony P. Zelinko
  • Patent number: 5087749
    Abstract: 2-(2-haloethylthio)-phenylsulfonamides of formula I ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.5 alkyl or C.sub.2 -C.sub.5 alkenyl and Z is hydrogen, fluorine or chlorine, are prepared by converting a phenylsulfonamide of formula II ##STR2## wherein Y is a tertiary alkyl group or a silyl group in succession and without isolating intermediates, witha) a strong base MeA, wherein Me is sodium or potassium, A is hydrogen, OH, NH.sub.2 or OR.sub.5 and R.sub.5 is C.sub.1 -C.sub.5 alkyl, into the compound of formula III ##STR3## converting that compound with b) one equivalent of n-butyllithium andc) sulfurinto the compound of formula IV ##STR4## reacting that compound with d) a 2-halofluoroethane of the formula X--CH.sub.2 CHF--Z wherein X is chlorine or bromine, to form a phenylsulfonamide of formula VI ##STR5## and then removing the group Y.
    Type: Grant
    Filed: December 3, 1990
    Date of Patent: February 11, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Bernard Wirz, Willy Meyer, Wolfgang Stutz
  • Patent number: 5081284
    Abstract: A novel N-substituted peptidyl compound represented by the general formula (1): ##STR1## where R.sub.1 is a straight-chained or branched acyl group having 2-10 carbon atoms, a branched, cyclic or partly branched cyclic alkyloxycarbonyl group having 4-15 carbon atoms, a substituted or unsubstituted benzyloxycarbonyl group, a 2,2,2-trichloroethyloxycarbonyl group, a 2-(trimethylsilyl)ethyloxycarbonyl group, a p-toluensulfonyl group, an o-nitrophenylsulfenyl group, a diphenylphosphonothioyl group, a triphenylmethyl group, a 2-benzoyl-1-methylvinyl group or a 4-phenylbutyryl group; R.sub.2 is a hydrogen atom or when taken together with R.sub.1, may form a phthaloyl group; R.sub.3 is an isobutyl group, a n-butyl group or an isopropyl group; R.sub.4 is a butyl group, a benzyl group or a methylthioethyl group; and R.sub.5 is a hydrogen atom or a chloromethyl group, which inhibits the activity of cysteine proteinases.
    Type: Grant
    Filed: June 29, 1989
    Date of Patent: January 14, 1992
    Assignee: Suntory Limited
    Inventors: Naoki Higuchi, Masayuki Saitoh, Norio Iwasawa, Motoo Sumida, Hiroshi Shibata
  • Patent number: 5068427
    Abstract: A process for the preparation of alkane- and arenesulfonamides in high purity and yield is provided. Ammonia or alkylamine is reacted under boiling conditions with an alkane- or arenesulfonyl halide in the absence of an added solvent. The heat of reaction is dissipated by the heat of vaporization of the ammonia or alkylamine.
    Type: Grant
    Filed: November 16, 1989
    Date of Patent: November 26, 1991
    Assignee: Atochem North America, Inc.
    Inventors: Stanley R. Sandler, Steven G. Schon, David M. Gardner
  • Patent number: 5057623
    Abstract: An organic fluorine compound represented by the general formulaR.sub.f -(X).sub.h -R-Mwherein R.sub.f is a group selected from the following (a) and (b); ##STR1## X denotes a linking group selected from --O--, --S--, and --COO--, h denotes 0 or 1, R is a hydrocarbon chain comprising a phenylene group having an alkylene group with a total carbon number of 10 or more, or the derivative thereof, or an aliphatic alkylene group of a carbon number of 10 or more, and M is a group selected from --OH, --COOH, --SH, and --CONH.sub.2.The organic fluorine compound of the present invention greatly improves the dispersibility of magnetic powders in magnetic coating materials, has also an excellent rust prevention effect on metallic magnetic powders, and exhibits a marked dispersing effect even on fluorocarbon resin fine powders, which can be difficultly dispersed with conventional dispersing agents.
    Type: Grant
    Filed: October 13, 1989
    Date of Patent: October 15, 1991
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Yoshiaki Kai, Takashi Suzuki
  • Patent number: 5053430
    Abstract: Novel compounds having the general formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined herein. These compounds are useful in the treatment of schizophrenia.
    Type: Grant
    Filed: September 22, 1989
    Date of Patent: October 1, 1991
    Assignee: Boehringer Ingelheim KG
    Inventors: Matthias Grauert, Herbert Merz, Joachim Mierau, Gunter Schingnitz, Claus Schneider
  • Patent number: 5041603
    Abstract: The invention relates to N-phenylsulfonyl-N'-pyrimidinylureas and N-phenylsulfonyl-N-triazinylureas of the general formula ##STR1## wherein R.sub.1 is hydrogen, halogen, nitro, amino, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.4 haloalkyl or a --Q--R.sub.7, --CO--OR.sub.8 or --(CO).sub.n --NR.sub.9 R.sub.10 radical,R.sub.2 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, halogen or alkoxyalkyl containing not more than 4 carbon atoms,R.sub.3 is C.sub.2 -C.sub.10 alkenyl which is substituted by one or more fluorine or bromine atoms or by one or more hydroxyl, cyano, nitro, --(Y).sub.m --CO--(Z).sub.n --R.sub.8, --SO.sub.2 --NR.sub.11 R.sub.12, --S(O).sub.p --C.sub.1 -C.sub.3 haloalkyl or --S(O).sub.n --C.sub.1 -C.sub.3 alkyl groups and which may additionally be substituted by one or more chlorine atoms,R.sub.4 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.
    Type: Grant
    Filed: January 12, 1990
    Date of Patent: August 20, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Willy Meyer, Dieter Reinehr, Konrad Oertle, Rolf Schurter
  • Patent number: 5006523
    Abstract: Novel compounds of the formula ##STR1## and tautomers thereof are disclosed. These compounds possess potassium channel blocking activity and, as such, are useful as antiarrhythmic agents.
    Type: Grant
    Filed: October 26, 1989
    Date of Patent: April 9, 1991
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Karnail Atwal
  • Patent number: 5002972
    Abstract: Pharmaceutical compounds and compositions for injectable use in the treatment of thromboxane A.sub.2 mediating diseases, comprising a pharmaceutical carrier and a pharmacologically effective amount of a compound of the formula: ##STR1## wherein R.sup.1 is carboxyl or 5-tetrazolyl; R.sup.2 is hydrogen, methyl, hydroxy, chloro, or bromo; or a pharmaceutically acceptable ester or salt thereof, together with one or more non-toxic pharmaceutically acceptable carriers; and methods for treating thromboxane A.sub.2 mediating diseases.
    Type: Grant
    Filed: February 7, 1990
    Date of Patent: March 26, 1991
    Assignee: Shionogi & Co., Ltd.
    Inventors: Masayuki Narisada, Mitsuaki Ohtani, Fumihiko Watanabe, Takaharu Matsuura
  • Patent number: 4996360
    Abstract: The arylsulfonyl(alkyl)amides, notably N-(n-butyl)benzenesulfonamide, well adopted as heat-stable plasticizers for polyamides, e.g., nylon 11 and nylon 12, are directly prepared by (a) intimately contacting an arylsulfonyl halide with a stoichiometric excess of both an alkylamine and an alkaline agent, with the alkaline agent being present in aqueous solution, (b) eliminating water and excess alkylamine from the organic phase produced in stage (a), and (c) separating final product arylsulfonyl(alkyl)amide from the residual organic phase remaining after stage (b).
    Type: Grant
    Filed: March 15, 1989
    Date of Patent: February 26, 1991
    Assignee: Atochem
    Inventors: Raymond Commandeur, Elie Ghenassia
  • Patent number: 4990637
    Abstract: Herbicidally active novel substituted 1-benzylsulphonyl-3-heteroaryl(thio)-ureas of the formula ##STR1## in whichQ.sub.1 represents oxygen or sulphur,R.sup.1 represents hydrogen, or represents optionally substituted radicals from the series comprising alkyl, alkenyl, alkynyl and aralkyl,R.sup.2 represents hydrogen, halogen, hydroxyl, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, amino, alkylamino or dialkylamino,R.sup.3 represents hydrogen or alkyl,R.sup.4 represents halogenoalkyl,X represents nitrogen or a --CH grouping,Y represents nitrogen or a --CR.sup.5 grouping,R.sup.5 represents hydrogen, halogen, cyano, alkyl, formyl, alkyl-carbonyl or alkoxy-carbonyl,Z represents nitrogen or a --CR.sup.6 grouping, andR.sup.6 represents hydrogen, halogen, hydroxyl, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, alkylamino or dialkylamino,and salts thereof with metals and basic organic nitrogen compounds. The benzylsulphonyl moieties are also new.
    Type: Grant
    Filed: January 30, 1990
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christa Fest, Klaus-Helmut Muller, Theodor Pfister, Hans-Jochem Riebel, Ernst Kysela, Hans-Joachim Santel, Robert R. Schmidt, Robert H. Strang
  • Patent number: 4973733
    Abstract: Polymers, such as polyisobutylene or ethylene-propylene copolymers, are functionalized by reaction with an activated imine to yield novel polymers.
    Type: Grant
    Filed: February 9, 1987
    Date of Patent: November 27, 1990
    Assignee: Texaco Inc.
    Inventors: Phillip B. Valkovich, Kechia J. Chou
  • Patent number: 4973732
    Abstract: Polymers, such as polysiobutylene or ethylene-propylene copolymers, are functionalized by reaction with an activated imine to yield novel polymers.
    Type: Grant
    Filed: February 9, 1987
    Date of Patent: November 27, 1990
    Assignee: Texaco Inc.
    Inventors: Phillip B. Valkovich, Kechia J. Chou
  • Patent number: 4971990
    Abstract: Phenoxyethylamine derivatives represented by the general formula (I): ##STR1## wherein R.sub.1 and R.sub.5 represent lower-alkyl, R.sub.2 and R.sub.3, which may be the same or different, each represents hydrogen or lower-alkyl, or ##STR2## represents a 5- or 6-membered ring system which may include nitrogen, oxygen or sulfur as a ring membered atom, R.sub.4 represents hydrogen or lower-alkyl, and n represents an integer selected from 1 to 3, their optical isomers and pharmacologically-acceptable acid addition salts, which exhibit excellent .alpha..sub.1 -blocking activity, a process for their preparation, pharmaceutical compositions thereof, and a method for the treatment of a subject afflicted with hypertension or dysuria by administrating such a compound, are all disclosed.
    Type: Grant
    Filed: January 24, 1989
    Date of Patent: November 20, 1990
    Assignee: Hokuriku Pharmaceutical Co., Ltd.
    Inventors: Yasuo Itoh, Hideo Kato, Eiichi Koshinaka, Nobuo Ogawa, Kazuya Mitani, Shunichiro Sakurai
  • Patent number: 4920116
    Abstract: N-(aminoalkyl)-substituted(N or C alkyl)-aryl-4-(methylsylfonylamino)benzamides of the formula ##STR1## wherein R is C.sub.1 -C.sub.4 straight chain alkyl, one of R.sub.1, R.sub.2 and R.sub.3 is a phenyl or naphthyl group and the others are hydrogen, --NR.sub.4 R.sub.5 is a secondary or teritary amino group, X and X.sub.1 are hydrogen or alkyl and n is 0 or 1, are useful as antiarrhythmic agents in the treatment of cardiac arrhythmias especially as combination Class I/Class III agents.
    Type: Grant
    Filed: December 13, 1988
    Date of Patent: April 24, 1990
    Assignee: Schering A.G.
    Inventors: Thomas K. Morgan, Jr., Klaus Nickisch
  • Patent number: 4908467
    Abstract: N-Phenylsulfonyl-B'-pyrimidinyl- and -triazinylureas of the formula I ##STR1## wherein A is 3,3,3-trifluoropropyl or 3,3-difluorobutyl,R.sup.1 is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulfinyl, C.sub.1 -C.sub.4 -alkylsulfonyl, --CO--R.sup.6, --NR.sup.7 R.sup.8, --CO--NR.sup.9 R.sup.10 or --SO.sub.2 --NR.sup.11 R.sup.12,R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulfinyl or C.sub.1 -C.sub.4 -alkylsulfonyl,R.sup.3 and R.sup.4 independently of one another are each hydrogen, halogen C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.2 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, C.sub.2 -C.sub.4 -alkoxyalkyl, C.sub.1 -C.sub.4 -alkoxy or --NR.sup.12 R.sup.13,R.sup.5 is hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,R.sup.6 is C.sub.1 -C.
    Type: Grant
    Filed: April 8, 1988
    Date of Patent: March 13, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Willy Meyer, Konrad Oertle
  • Patent number: 4899249
    Abstract: A dielectric medium composition comprising a fluorine-containing amide or a fluorine-containing sulfonamide and capacitors or other electric devices incorporating said composition, are disclosed herein.
    Type: Grant
    Filed: April 21, 1988
    Date of Patent: February 6, 1990
    Assignee: Pennwalt Corporation
    Inventors: James L. Reilly, Ludwig K. Huber, Gordon R. Leader
  • Patent number: 4888043
    Abstract: The invention concerns compounds of the formula I ##STR1## wherein: Z is selected from hydrogen, alkyl, alkanoyl, sulfamoyl, carboxy and trifluoroacetamido;Y is selected from various carboxy or thiocarboxy groups, haloalkanoyl, alkylsulfonyl and haloalkylsulfonyl;R.sup.1 is selected from hydrogen, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl and alkynyl;R.sup.3 is selected from alkyl; andR.sup.4 is selected from hydrogen, alkyl, and alkoxycarbonyl.The compounds of the invention show herbicidal properties and plant growth regulating properties and in further embodiments and the invention provides processes for the preparation of compounds of formula I, intermediates useful in the preparation of the compounds of formula I, compositions containing as active ingredient a compound of formula I, and herbicidal and plant growth regulating processes utilizing compounds of formula I.
    Type: Grant
    Filed: June 20, 1986
    Date of Patent: December 19, 1989
    Assignee: ICI Australia Limited
    Inventors: Keith G. Watson, Craig G. Lovel
  • Patent number: 4874894
    Abstract: Process comprises the combination of two steps of interacting a R-benzene, sulfuric acid and phosphorus oxychloride to obtain 4-R-benzenesulfonyl chloride and amidating said sulfonyl chloride to produce 4-R-benzenesulfonamide.
    Type: Grant
    Filed: April 29, 1987
    Date of Patent: October 17, 1989
    Assignee: Hilton Davis Co.
    Inventor: Ramamurthi Kannan
  • Patent number: 4837307
    Abstract: A 2,2'-bridged[1,1'-biphenyl]-3-ylmethyl compound of the following formula is an intermediate to insecticidal esters. ##STR1## wherein n is 1-4 and Y is a leaving group readily displaced by carboxylate anions.
    Type: Grant
    Filed: January 16, 1984
    Date of Patent: June 6, 1989
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • Patent number: 4835272
    Abstract: A process for formation of a base, which comprises reacting an acetylide compound with a salt. The acetylide compound has the following formula:(R--C.tbd.C--).sub.n Mwherein R is a monovalent group selected from the group consisting of an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an aryl group and a heterocyclic group, each of which may have one or more substituent groups; M is an n-valent transition metal atom; and n is 1, 2 or 3. The salt is composed of an anion having an affinity for the transition metal (M) (the affinity of the anion for the transition metal is more than that of the acetylide anion (R--C.tbd.C.crclbar.)), and a cation derived from one selected from the group consisting of an alkali metal, an alkaline earth metal, ammonia and an organic base. A light-sensitive material containing the acetylide compound and the salt is also disclosed.
    Type: Grant
    Filed: July 16, 1987
    Date of Patent: May 30, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kozo Sato, Shunichi Ishikawa, Ken Kawata
  • Patent number: 4826528
    Abstract: This invention relates to sulfonylureas of the formula ##STR1## These compounds are useful in killing weeds and in regulating the growth of cultivated plants.
    Type: Grant
    Filed: June 20, 1985
    Date of Patent: May 2, 1989
    Assignee: Celamerck GmbH & Co. KG.
    Inventors: Rudolf Mengel, W. Pfleiderer, Gerbert Linden, Gerhart Schneider
  • Patent number: 4827032
    Abstract: Cycloalkanol[1,2-b]indole-sulphonamides of the formula ##STR1## where appropriate in an isomeric form, and their salts are disclosed. These compounds are useful to inhibit platelet aggregation and to antagonize thromboxane A.sub.2.
    Type: Grant
    Filed: June 29, 1988
    Date of Patent: May 2, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Boshagen, Ulrich Rosentreter, Folker Lieb, Hermann Oediger, Friedel Seuter, Elisabeth Perzborn, Volker-Bernd Fiedler
  • Patent number: 4749407
    Abstract: There are disclosed an N-propargyl-N-(2-trifluoromethylbenzoyl)-3-substituted benzenesulfonamide represented by the general formula: ##STR1## wherein R.sup.1 represents a halogen atom, a lower alkyl group, a lower alkoxy group, a perfluoro-lower alkyl group having 1 to 4 carbon atoms, a nitro group, a cyano group, a carboxyl group or a lower alkoxycarbonyl group; and R.sup.2 represents a hydrogen atom, a halogen atom, a lower alkyl group, a perfluoro-lower alkyl group having 1 to 4 carbon atoms, a lower alkoxy group, a nitro group, a cyano group, a carboxyl group or a lower alkoxycarbonyl group, and a selective herbicide containing the same as an active ingredient.
    Type: Grant
    Filed: June 23, 1986
    Date of Patent: June 7, 1988
    Assignees: Sagami Chemical Research Center, Central Glass Co, Ltd.
    Inventors: Daiei Tunemoto, Hideko Sakai, Kiyosi Kondo, Kaoru Mori, Masahiro Watanabe, Takeo Komata, Kenji Motojima
  • Patent number: 4739116
    Abstract: A process improvement for the preparation of arylsulfonamides that avoids the multistep arylsulfonyl chloride refining operation presently used and, in one step, neutralizes and removes all the acidic by-products of chlorosulfonation simultaneously with arylsulfonamide formation which comprises the steps of (a) reacting an aryl hydrocarbon with chlorosulfonic acid to form a crude chlorosulfonation reaction product, (b) combining in an aqueous media said crude reaction product and a source of ammonia to form an amidation reaction mixture, (c) maintaining the temperature of the amidation reaction mixture at between about 40.degree. C. and 70.degree. C. and the pH at above about 7 with stirring for a period of time sufficient to form an amidation reaction product containing an arylsulfonamide, and optionally (d) separating the resulting arylsulfonamide from the amidation reaction product.
    Type: Grant
    Filed: January 16, 1986
    Date of Patent: April 19, 1988
    Assignee: Akzo America Inc.
    Inventors: Gail H. Birum, Richard F. Jansen