Carbonyl, Cyano, Nitro, Nitroso, Halogen, Or Sulfur Attached Directly To The Sulfonamide Nitrogen Or To An Amino Nitrogen In A Substituent E By Nonionic Bonding Patents (Class 564/91)
  • Patent number: 4430345
    Abstract: Novel bicyclo [2,2,1] heptanes and hept-2Z-enes are substituted at the 5-position by a 6-carboxyhex-2-enyl group or a modification thereof, and at the 6-position by an aldoxime or ketoxime group which is O-substituted by an aliphatic hydrocarbon residue, an aromatic residue, or an aliphatic hydrocarbon residue substituted directly or through an oxygen or sulphur atom by an aromatic residue. Such compounds may be prepared by the action of an oximating agent on an intermediate which is substituted at the 6-position by an aldehydic or ketonic carbonyl group. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: February 7, 1984
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 4427685
    Abstract: Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein: a is 1 to 3;b is 0 to 2;c is 2 to 4;d is 1 to 5;X is sulphur, oxygen or --CH.sub.2 --;Y is oxygen, sulphur, NR.sub.4 or CHR.sub.5 wherein R.sub.4 is hydrogen, C.sub.1-4 alkyl, NO.sub.2 or CN, C.sub.1-4 alkylsulphonyl or phenylsulphonyl optionally substituted in the phenyl moiety by one or two substituents selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy, fluorine, chlorine or bromine, and R.sub.5 is NO.sub.2, C.sub.1-4 alkylsulphonyl or optionally substituted phenylsulphonyl as defined for R.sub.4 ;R.sub.1 and R.sub.2 are independently hydrogen, C.sub.1-4 alkyl, or C.sub.3-6 cycloalkyl; or R.sub.1 and R.sub.2 taken together with the nitrogen to which they are attached represent a pyrrolidino or piperidino ring;R.sub.6 and R.sub.7 are independently hydrogen or C.sub.
    Type: Grant
    Filed: February 3, 1982
    Date of Patent: January 24, 1984
    Assignee: Beecham Group P.L.C.
    Inventor: Geoffrey Stemp
  • Patent number: 4424377
    Abstract: This invention relates to a novel class of N-(heterocyclicaminocarbonyl)-o-alkoxymethylbenzene sulfonamide herbicides.
    Type: Grant
    Filed: May 14, 1982
    Date of Patent: January 3, 1984
    Assignee: E. I. Du Pont de Nemours & Co.
    Inventor: Gregory W. Schwing
  • Patent number: 4420632
    Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet antiaggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: December 13, 1983
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4413013
    Abstract: Novel pesticidal N-[[[arylformimidoyl]methylamino]thio]-N-substituted sulfonamides are disclosed with novel compositions thereof and methods for their use in controlling invertebrate arthropod pests, particularly insects, mites, and ticks.
    Type: Grant
    Filed: December 14, 1981
    Date of Patent: November 1, 1983
    Assignee: The Upjohn Company
    Inventor: Victor L. Rizzo
  • Patent number: 4359467
    Abstract: Prostanoic acid derivatives of the formula ##STR1## wherein R.sub.1 is an acid, ester, amide or hydroxyalkylene group; R.sub.2 and R.sub.3 are H or alkyl; R.sub.4 and R.sub.5 are both CH.sub.3 or one is Cl and the other is CH.sub.3 ; A is CH.sub.2 CH.sub.2 or --CH.dbd.CH; B is CH.sub.2 CH.sub.2, trans- ##STR2## W is free or functionally modified hydroxyalkylene or carbonyl; Z is free or functionally modified hydroxymethylene or carbonyl; X Y is either ##STR3## or, when Z is free or functionally modified hydroxymethylene, ##STR4## or, when Z is free or functionally modified carbonyl, --CH.dbd.CH--, R.sub.12 being H, CH.sub.3, CN or free or functionally modified hydroxy; and physiologically acceptable salts thereof when R.sub.1 is an acid group, possess pharmacological activity, including abortion triggering activity.
    Type: Grant
    Filed: April 22, 1981
    Date of Patent: November 16, 1982
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Walter Elger
  • Patent number: 4352760
    Abstract: The present invention provides novel substituted heptadeca-5,9- and 5,10-dienoic acid and similar fatty acid compounds which are derivatives of certain prostaglandins and are potent thromboxane A.sub.2 inhibitors. By virtue of this pharmacological property, they represent useful pharmacological agents for a wide variety of purposes.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: October 5, 1982
    Assignee: The Upjohn Company
    Inventor: Kirk M. Maxey
  • Patent number: 4347380
    Abstract: Described herein are herbicidal compositions comprised of a thiocarbamate or haloacetanilide herbicide and an antidotally effective amount of an N-acylsulfonamide compound corresponding to the formula ##STR1## in which R is selected from the group consisting of hydrogen, methyl, chloro, acetamido, and 1-4 carbon alkoxyamido;R.sub.1 is selected from the group consisting of hydrogen, allyl, and metal ion;R.sub.2 is selected from the group consisting of 1-10 carbon alkyl, 1-4 carbon haloalkyl, 2-4 carbon alkenyl, 2-4 carbon haloalkenyl, acetonyl, 1-6 carbon alkoxy, 1-4 carbon alkoxycarbonyl, 1-4 carbon alkylthioalkyl, alkoxyalkyl, O,O-dialkylphosphorodithioylalkyl, phenyl, halophenyl, halophenylthioalkyl, cyclohexanedione, and dimethyl barbituric acid; orR.sub.1 and R.sub.2 together with the carbonyl group to which R.sub.2 is attached are selected from the group consisting of succinimide, substituted succinimide, phthalimide, and substituted phthalimide.
    Type: Grant
    Filed: November 21, 1980
    Date of Patent: August 31, 1982
    Assignee: Stauffer Chemical Company
    Inventor: Ferenc M. Pallos
  • Patent number: 4338457
    Abstract: The present invention relates to novel compositions of matter and novel processes for preparing these compositions of matter. Moreover, there are provided novel methods by which certain of these novel compositions of matter are employed for pharmacologically useful purposes.
    Type: Grant
    Filed: February 28, 1980
    Date of Patent: July 6, 1982
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4324730
    Abstract: Prostaglandin and prostacyclin compounds which are fluorine substituted in any one or more of the following positions, 4,4; 7,7; 10,10; and 5.
    Type: Grant
    Filed: October 8, 1980
    Date of Patent: April 13, 1982
    Assignee: The University of Chicago
    Inventor: Josef Fried
  • Patent number: 4318921
    Abstract: Novel 1-aryloxy-3-amidoamidoalkylamino-2-propanol derivatives, processes for their manufacture, pharmaceutical compositions containing them and methods of using them in the treatment of heart diseases. Representative of the compounds disclosed is 1-(o-cyanophenoxy)-3-.beta.-(benzamidoacetamido)ethylaminopropan-2-ol.
    Type: Grant
    Filed: November 30, 1979
    Date of Patent: March 9, 1982
    Assignee: Imperial Chemical Industries Limited
    Inventor: Leslie H. Smith
  • Patent number: 4317819
    Abstract: The invention provides compounds of general formula ##STR1## and physiologically acceptable salts, hydrates and bioprecursors thereof, in whichY and Z, which may be the same or different, each represent oxygen, sulphur, .dbd.CHNO.sub.2 or .dbd.NR.sub.3 where R.sub.3 is hydrogen, nitro, cyano, lower alkyl, aryl, alkylsulphonyl or arylsulphonyl;p has a value from 2 to 12;R.sub.1 represents ##STR2## in which R.sub.4 and R.sub.5 which may be the same or different, each represent hydrogen, lower alkyl, cycloalkyl, lower alkenyl, aralkyl or lower alkyl interrupted by an oxygen atom or a group >N-R.sub.6 in which R.sub.6 represents hydrogen or lower alkyl, or R.sub.4 and R.sub.5 together with the nitrogen atom to which they are attached form a 5 to 7-membered saturated heterocyclic ring which may contain an additional oxygen atom or the group >NR.sub.
    Type: Grant
    Filed: December 5, 1980
    Date of Patent: March 2, 1982
    Assignee: Glaxo Group Limited
    Inventors: John W. Clitherow, Barry J. Price, John Bradshaw, Michael Martin-Smith
  • Patent number: 4316910
    Abstract: Substituted 2-carbamoyloximino-butanes of the formula ##STR1## in which R is alkyl or alkylthioalkyl,R.sup.1 is alkyl, alkoxyalkyl, alkenyl or alkynyl,R.sup.2 is hydrogen, alkyl or --SR.sup.3,R.sup.3 is alkyl, halogenoalkyl, optionally substituted phenyl, alkoxycarbonyl, --N(CH.sub.3)R.sup.4, or a radical identical to that to which --SR.sup.3 is bonded,R.sup.4 is alkyl, alkoxycarbonyl or optionally substituted phenylsulphonyl,X is hydrogen or halogen,Y is hydrogen or halogen,Z is halogen, andn is 0, 1 or 2,which possess arthropodicidal activity.
    Type: Grant
    Filed: August 11, 1980
    Date of Patent: February 23, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jorg Stetter, Bernhard Homeyer, Ingeborg Hammann, Hans-Ludwig Elbe
  • Patent number: 4309425
    Abstract: Sulfonamides, such as N-[N-(2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethy l)phenyl]aminothio]-N,4-dimethylbenzenesulfonamide, are useful for control of arthropod pests of plants and animals and fungus disease of plants.
    Type: Grant
    Filed: April 11, 1980
    Date of Patent: January 5, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Jiin-Duey Cheng
  • Patent number: 4289904
    Abstract: The present invention provides novel 19-hydroxy-6a-carba-PGI.sub.2 sulfonylamides which are useful for pharmacological purposes, e.g., anti-asthmatic indications.
    Type: Grant
    Filed: March 3, 1980
    Date of Patent: September 15, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4283416
    Abstract: Fungi, mites and mite eggs are killed by applying thereto sulfonamides of the formula ##STR1## wherein R and R.sup.1 individually are alkyl, cycloalkyl, aryl, carbamylalkyl, or alkoxycarbonylalkyl and R.sup.2 is haloalkyl, with the proviso that one R or R.sup.1 group is carbamylalkyl or alkoxycarbonylalkyl.
    Type: Grant
    Filed: February 19, 1980
    Date of Patent: August 11, 1981
    Assignee: Chevron Research Company
    Inventor: David C. K. Chan
  • Patent number: 4281150
    Abstract: The present invention provides novel 19-hydroxy-19-methyl-6a-carba-PGI.sub.1 sulfonylamides which are useful for pharmacological purposes, e.g., anti-asthmatic indications.
    Type: Grant
    Filed: March 3, 1980
    Date of Patent: July 28, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4281011
    Abstract: N-methyl-N-(benzene sulfonic acid methylamide-N'-sulfenyl)-carbamic acid esters of the formula ##STR1## in which X is halogen, C.sub.1 -C.sub.6 alkyl or hydrogen, andR is a phenyl, naphthyl, benzodioxolanyl or indanyl radical optionally carrying at least one alkyl, alkenyl, alkynyl, alkoxy, alkenoxy, alkynoxy, alkylmercapto, alkenylmercapto, alkynylmercapto, dialkylamino, trihalogenemethyl, halogeno, nitro, nitrile, cycloalkyl, formamidino, dioxanyl or dioxolanyl radical; or an oxime radical of the formula ##STR2## in which R.sup.1 and R.sup.2 each individually is alkyl, alkoxy, alkylthio or alkoxycarbonyl, the alkyl moieties of R.sup.1 and R.sup.2 optionally being linked to one another,which possess insecticidal and acaricidal properties.
    Type: Grant
    Filed: January 27, 1976
    Date of Patent: July 28, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Siegle, Engelbert Kuhle, Ingeborg Hammann, Wolfgang Behrenz
  • Patent number: 4276436
    Abstract: The present invention provides novel 19-keto-PG sulfonylamides, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: June 30, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4267352
    Abstract: The present invention provides novel 19-hydroxy-19-methyl-6-oxo-PGF.sub.1 sulfonylamides which are useful for pharmacological purposes, e.g., anti-asthmatic indications.
    Type: Grant
    Filed: March 3, 1980
    Date of Patent: May 12, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4266078
    Abstract: Described herein are herbicidal compositions comprised of a thiocarbamate or haloacetanilide herbicide and an antidotally effective amount of an N-acylsulfonamide compound corresponding to the formula ##STR1## in which R is selected from the group consisting of hydrogen, methyl, chloro, acetamido, and 1-4 carbon alkoxyamido;R.sub.1 is selected from the group consisting of hydrogen, allyl, and metal ion;R.sub.2 is selected from the group consisting of 1-10 carbon alkyl, 1-4 carbon haloalkyl, 2-4 carbon alkenyl, 2-4 carbon haloalkenyl, acetonyl, 1-6 carbon alkoxy, 1-4 carbon alkoxycarbonyl, 1-4 carbon alkylthioalkyl, alkoxyalkyl, O,O-dialkylphosphorodithioylalkyl, phenyl, halophenyl, halophenylthioalkyl, cyclohexanedione, and dimethyl barbituric acid; orR.sub.1 and R.sub.2 together with the carbonyl group to which R.sub.2 is attached are selected from the group consisting of succinimide, substituted succinimide, phthalimide, and substituted phthalimide.
    Type: Grant
    Filed: April 20, 1979
    Date of Patent: May 5, 1981
    Assignee: Stauffer Chemical Company
    Inventor: Ferenc M. Pallos
  • Patent number: 4265825
    Abstract: N-(haloalkyl)sulfonamides represented by the formula ##STR1## wherein R.sub.1 is a C.sub.1 -C.sub.20 aryl, alkaryl, aralkyl or alkyl group; R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen or methyl groups; n is the integer 0 or 1 and X is a chloro, bromo or iodo group, are prepared by reacting an N-(haloalkyl)sulfonyl imide with a C.sub.1 -C.sub.6 alkanol.
    Type: Grant
    Filed: September 17, 1979
    Date of Patent: May 5, 1981
    Assignee: The Dow Chemical Company
    Inventors: Peter W. Owen, Zita K. Harmon, Donald A. Tomalia
  • Patent number: 4264522
    Abstract: The present invention provides novel 19-hydroxy-PG amides methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: October 26, 1979
    Date of Patent: April 28, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4258058
    Abstract: Phenoxyalkylcarboxylic acid compounds of the formula ##STR1## wherein R is hydrogen or lower alkylR.sub.1 is alkyl or aryl, aralkyl or aralkenyl radical, the aryl moiety of which can be substituted one or more times by halogen, hydroxyl, trifluoromethyl or lower alkyl, alkoxy or acylR.sub.2 and R.sub.3 are individually selected from hydrogen or lower alkyl, andn is 0, 1, 2 or 3and the physiologically acceptable salts, esters and amides thereof; are outstandingly effective in inhibiting thrombocyte aggregation.
    Type: Grant
    Filed: February 26, 1979
    Date of Patent: March 24, 1981
    Assignee: Boehringer Mannheim GmbH
    Inventors: Ernst-Christian Witte, Hans P. Wolff, Max Thiel, Karlheinz Stegmeier, Egon Roesch
  • Patent number: 4257970
    Abstract: Novel N-(haloalkyl)sulfonyl imides represented by the formula ##STR1## are prepared by the reaction of a 2-alkyl- or 2-aryl-oxazoline or oxazine with an arylene or alkane sulfonyl halide. In the formula for the novel sulfonyl imide, R.sub.1 and R.sub.2 are each independently C.sub.1 -C.sub.20 aryl, alkaryl or alkyl groups; R.sub.3, R.sub.4 and R.sub.5 are each hydrogen or methyl groups; n is the integer 0 or 1 and X is a chloro, bromo or iodo group. These novel sulfonyl imides are particularly useful in the preparation of N-(2-chloroethyl)- and N-(3-chloropropyl)sulfonamides.
    Type: Grant
    Filed: September 17, 1979
    Date of Patent: March 24, 1981
    Assignee: The Dow Chemical Company
    Inventor: Donald A. Tomalia
  • Patent number: 4252978
    Abstract: The present invention provides novel 19-hydroxy-6-oxo-PGF.sub.1 sulfonylamides which are useful for pharmacological purposes, e.g., anti-asthmatic indications.
    Type: Grant
    Filed: March 3, 1980
    Date of Patent: February 24, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4246283
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is methyl or ethyl, R.sub.2 is C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl or cyclopropylmethyl, R.sub.3 is C.sub.1 -C.sub.4 -alkyl or phenyl optionally mono-, or di- or trisubstituted by halogen and/or methyl and either (i) X.sub.1 is methyl, chlorine, bromine or hydrogen and X.sub.2 is methyl or (ii) X.sub.1 is methyl, chlorine or bromine and X.sub.2 is hydrogen exhibit valuable pesticidal, in particular acaricidal and insecticidal, properties.
    Type: Grant
    Filed: June 1, 1977
    Date of Patent: January 20, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Manfred Boger, Jozef Drabek
  • Patent number: 4244887
    Abstract: Substituted novel .omega.-pentanorprostaglandins and various novel intermediates and reagents used in their preparation.
    Type: Grant
    Filed: August 20, 1979
    Date of Patent: January 13, 1981
    Assignee: Pfizer Inc.
    Inventors: Jasjit S. Bindra, Michael R. Johnson
  • Patent number: 4243609
    Abstract: The present invention relates to certain ring-fluorinated 4-(hexadecyl-amino) N-substituted benzamide compounds as hypolipidemic and antiatherosclerotic agents together with their pharmacologically acceptable acid-addition and cationic salts. The amino functions of the benzamide groups are selected from the groups consisting of loweralkanesulfonylamino, phenylsulfonylamino, loweralkanoylamino, benzoylamino and carboxyalkylamino.
    Type: Grant
    Filed: February 2, 1978
    Date of Patent: January 6, 1981
    Assignee: American Cyanamid Company
    Inventor: Robert G. Shepherd
  • Patent number: 4242273
    Abstract: This disclosure describes 4-(monoalkylamino)benzoic acid amides and imidates useful as hypolipidemic and antiatherosclerotic agents.
    Type: Grant
    Filed: October 12, 1978
    Date of Patent: December 30, 1980
    Assignee: American Cyanamid Company
    Inventor: Robert G. Shepherd
  • Patent number: 4242267
    Abstract: A novel process for the preparation of xanthane-2-carboxylic acids of the formula ##STR1## wherein R is selected from the group consisting of hydrogen and alkyl of 1 to 9 carbon atoms and R.sub.1 is alkyl of 1 to 5 carbon atoms which possess an antiallergic activity and are particularly useful for treating asthma and asthmatic form bronchitisis of allergic origin.
    Type: Grant
    Filed: February 4, 1980
    Date of Patent: December 30, 1980
    Assignee: Roussel Uclaf
    Inventors: Alan C. Barnes, Peter D. Kennewell
  • Patent number: T100403
    Abstract: Hypolipidemic and anti-atherosclerotic 2- or 3-(monosubstituted-amino) phenyl compounds of the formulae: ##STR1## wherein R.sub.1 is a saturated or unsaturated hydrocarbon radical of 8-19 carbon atoms which may be branched or unbranched and which may contain one or more radicals selected from the group consisting of saturated or unsaturated cycloalkyl, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl; J is ##STR2## wherein Z is inter alia hydrogen, loweralkyl, hydroxy, loweralkoxy and loweralkoxyalkoxy, or J is carboxyloweralkyl, carboxyloweralkenyl, carboxyloweralkynyl, carboalkoxyloweralkyl, carboalkoxyloweralkenyl or carboalkoxyloweralkynyl.
    Type: Grant
    Filed: October 17, 1979
    Date of Patent: March 3, 1981
    Assignee: American Cyanamid Company
    Inventor: Robert G. Shepherd