Hydroxy, Bonded Directly To Carbon, Or Ether In Substituent Q (h Of -oh May Be Replaced By A Substituted Or Unsubstituted Ammonium Ion Or A Group Ia Or Iia Light Metal) Patents (Class 564/89)
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Patent number: 5124462Abstract: A process for preparing a compound of Formula (I): ##STR1## wherein R' is optionally protected --CH.sub.2 OH or --COOH; R.sup.2 is phenyl or substituted phenyl; and Y is oxygen, methylene, or substituted methylene, which comprises treating a norbornyl acid amide of formula (II): ##STR2## wherein R is optionally protected --CH.sub.2 OH or --COOR.sup.1 ; R.sup.1 is hydrogen or ester-forming group; and Y is oxygen, methylene, or substituted methylene under the reaction conditions for the Hofmann Rearrangement, and then with a substituted sulfonyl halide of formula (III):R.sup.2 SO.sub.2 X (III)wherein R.sup.2 is phenyl or substituted phenyl; and X is halogen atom.Type: GrantFiled: June 18, 1991Date of Patent: June 23, 1992Assignee: Shiongi & Co., Ltd.Inventors: Mitsuaki Ohtani, Takaharu Matsuura, Yoshinori Hamada, Shoji Shinomoto
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Patent number: 5120865Abstract: 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: GrantFiled: August 30, 1991Date of Patent: June 9, 1992Assignee: Shionogi & Co., Ltd.Inventors: Masayuki Narisada, Mitsuaki Ohtani, Fumihiko Watanabe, Kyozo Kawata
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Patent number: 5068365Abstract: Disclosed is novel hexahydrophthalic anilide derivatives and herbicide compositions comprising the derivatives. The hexahydrophthalic anilide derivatives of this invention are represented by the formula [I], [II] or [III]. ##STR1## (wherein R.sup.1 represents non-substituted or substituted phenyl, R.sup.2 represents hydrogen or C.sub.1 -C.sub.4 alkyl, R.sup.3 represents C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkenyl) ##STR2## (wherein R.sup.4 and R.sup.5, the same or different, represent C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkenyl or C.sub.1 -C.sub.4 alkynyl, provided R.sup.4 and R.sup.5 are not C.sub.1 -C.sub.4 alkyl simultaneously) ##STR3## (wherein X.sup.1 and X.sup.2, the same or different, represent halogen, Y represents oxygen or sulfur, R.sup.6 represents C.sub.1 -C.sub.6 straight or cyclic alkyl which may be substituted with oxygen, R.sup.7 represents hydrogen or methyl, R.sup.8 represents cyano, C.sub.1 -C.sub.3 alkyl, C.sub.2 or C.sub.3 alkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.3 -C.sub.Type: GrantFiled: December 30, 1988Date of Patent: November 26, 1991Assignees: Tosoh Corporation, Agro-Kanesho Co., Ltd.Inventors: Takumi Tokunaga, Hiroyuki Watanabe, Kenji Tsuzuki, Sinzo Someya, Seigo Koura, Mikio Ito
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Patent number: 5047420Abstract: Novel 1,3-diaryl cyclopentanes of the following general formula were prepared. ##STR1## These compounds were found to have potent and specific PAF (Platelet Activating Factor) antagonistic activities and as such useful in the treatment or amelioration of various diseases or disorders mediate by the PAF, for example, hypotension, inflammation, nephritis, stroke and other cardiovascular disorders, asthma, allergic and skin diseases, peptic or stomach ulcer, shock, lung edema, psoriasis, adult respiratory distress syndrome, pain including dental pain, and aggregation of platelets.Type: GrantFiled: August 21, 1989Date of Patent: September 10, 1991Assignee: Merck & Co., Inc.Inventors: Donald W. Graham, Tesfaye Biftu, John C. Chabala, Michael N. Chang, Yuan-Ching P. Chiang, Kathryn L. Thompson, Shu S. Yang
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Patent number: 5030652Abstract: Indan derivatives of the formula: ##STR1## wherein R.sup.1 is substituted or unsubstituted phenyl, naphthyl or sulfur-containing heterocyclic group, and R.sup.2 is hydroxy-methyl or a group of the formula: ##STR2## wherein R.sup.3 is hydrogen atom or lower alkyl and R.sup.4 is cycloalkyl, lower alkoxycarbonyl-phenyl, carboxy-phenyl, nitrogen-containing heterocyclic group, lower alkyl, or lower alkyl having a substituent selected from lower alkoxycarbonyl, carboxy, lower alkoxycarbonyl-phenyl, carboxy-phenyl, lower alkoxycarbonyl-cycloalkyl and carboxy-cycloalkyl, or a pharmaceutically acceptable salt thereof, which are useful as a platelet aggregation-inhibiting agent and as an agent for the treatment, amelioration and/or prophylaxis of a variety of thrombosis or embolism, coronary and cerebral vascular smooth muscle vellication, asthma, and the like, processes for the preparation thereof, and pharmaceutical composition containing said compound as an active ingredient.Type: GrantFiled: November 15, 1988Date of Patent: July 9, 1991Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Takeo Iwakuma, Harumichi Kohno, Yasuhiko Sasaki, Katsuo Ikezawa, Akio Odawara
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Patent number: 5030631Abstract: Novel tricyclic arylsulfonamides useful for treating hypertension and bronchoconstiction, as well as to their pharmaceutical compositions and methods for using the same.Type: GrantFiled: November 27, 1989Date of Patent: July 9, 1991Assignee: Schering CorporationInventor: Barr E. Bauer
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Patent number: 5002972Abstract: 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: GrantFiled: February 7, 1990Date of Patent: March 26, 1991Assignee: Shionogi & Co., Ltd.Inventors: Masayuki Narisada, Mitsuaki Ohtani, Fumihiko Watanabe, Takaharu Matsuura
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Patent number: 4971620Abstract: Disclosed herein is a sulfonamide compound represented by the formula (I): ##STR1## wherein A represents a phenyl group which may be substituted, B represents a phenyl group which may be substituted, R represents a lower alkyl group, a lower alkoxy group or a lower haloalkyl group, W represents a hydroxyl group or a halogen atom, and z represents a halogen atom, a lower alkysulfonyloxy group which may be substituted, or a phenylsulfonyloxy group which may be substituted, and a herbicidal composition containing the sulfonamide compound as an effective ingredient.Type: GrantFiled: January 27, 1989Date of Patent: November 20, 1990Assignee: Mitsubishi Kasei CorporationInventors: Tetsuo Jikihara, Manabu Katsurada, Toyohiko Shike, Osamu Ikeda, Hisao Watanabe, Tetsuo Takematsu, Koichi Yoneyama
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Patent number: 4965279Abstract: Novel cyclopropyl aza prostaglandin analogs are disclosed having the formula ##STR1## wherein A can be carbonyl, sulfonyl or a single bond. These compounds are useful, for example, as thromboxane antagonists.Type: GrantFiled: November 18, 1988Date of Patent: October 23, 1990Assignee: E. R. Squibb & Sons, Inc.Inventors: Raj N. Misra, David M. Floyd, Steven E. Hall
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Patent number: 4959501Abstract: In accordance with a novel process, 2-(2-chloroethoxy)-benzenesulfonamide of formula I ##STR1## is prepared by etherification of 4-chlorophenol of formula II ##STR2## with ethylene carbonate and chlorination of the resulting 4-(2-hydroxyethoxy)-chlorobenzene of formula III ##STR3## with phosgene or thionyl chloride to give 4-(2-chloroethoxy)-chlorobenzene of formula IV ##STR4## which is converted with chlorosulfonic acid ClSO.sub.3 H and sodium hydroxide to the sulfonic acid sodium salt of formula V ##STR5## which is hydrogenated to the compound of formula VI ##STR6## which is subsequently reacted with phosgene to the sulfonic acid chloride of formula VII ##STR7## which is reacted with amonia to the sulfonamide of formula I.Type: GrantFiled: May 23, 1988Date of Patent: September 25, 1990Assignee: Ciba-Geigy CorporationInventor: Reinhard G. Hanreich
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Patent number: 4948809Abstract: The present invention provides sulphonylphenylalkylamines of the general formula: ##STR1## wherein R.sub.1 is an alkyl radical containing up to 6 carbon atoms, a cycloalkyl radical containing 3-7 carbon atoms or an aralkyl, aralkenyl or aryl radical, the aryl moiety, in each case, being optionally substituted one or more times by halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, hydroxyl, trifluoromethyl, cyano, nitro, amino, C.sub.1 -C.sub.6 alkylamino, C.sub.2 -C.sub.12 dialkylamino, C.sub.1 -C.sub.6 acylamino, C.sub.1 -C.sub.16 acyl or azide, R.sub.2 is a hydrogen atom, an alkyl radical containing up to 6 carbon atoms, an acyl radical or an aralkyl or aralkenyl radical, the aryl moiety, in each case, optionally being substituted one or more times by halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, hydroxyl, trifluoromethyl, cyano, nitro, amino, C.sub.1 -C.sub.6 alkylamino, C.sub.1 -C.sub.12 dialkylamino, C.sub.1 -C.sub.6 acylamino, C.sub.1 -C.sub.Type: GrantFiled: December 5, 1988Date of Patent: August 14, 1990Assignee: Boehringer Mannheim GmbHInventors: Ernst-Christian Witte, Hans-Peter Wolff, Karlheinz Stegmeier, Johannes Pill
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Patent number: 4939147Abstract: Compounds of the formula, ##STR1## in which one of R.sub.30 and R.sub.40 represents a substituted phenylalkyl group and the other of R.sub.30 and R.sub.40 represents hydrogen or halogen, and R.sub.50 and R.sub.60 each independently represent hydrogen or alkyl.The compounds of the invention are useful for the treatment or prophylaxis of renal failure or cardiovascular disease.Type: GrantFiled: August 2, 1989Date of Patent: July 3, 1990Assignee: Fisons plc.Inventors: John Dixon, Brian Springthorpe, Francis Ince
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Patent number: 4920227Abstract: Certain specific substituted benzobicyclic carboxamides and their valuable use as 5-HT3 antagonists having CNS and gastric prokenetic activity void of any significant D.sub.2 receptor binding activity are disclosed.Type: GrantFiled: November 29, 1988Date of Patent: April 24, 1990Assignee: Rorer Pharmaceutical Corp.Inventors: Jeffrey C. Pelletier, Raymond D. Youssefyeh, Henry F. Campbell
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Patent number: 4908467Abstract: 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: GrantFiled: April 8, 1988Date of Patent: March 13, 1990Assignee: Ciba-Geigy CorporationInventors: Willy Meyer, Konrad Oertle
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Patent number: 4885027Abstract: Arylmethylenesulfonamidoacetamide and thioacetamide derivatives and arylmethylenesulfonamidoester intermediates therefor. The compounds are useful as selective herbicides especially with respect to the prevention and elimination of barnyardgrass in grass crops, especially in rice crops.Type: GrantFiled: November 14, 1986Date of Patent: December 5, 1989Assignee: Chevron Research CompanyInventor: Patricia B. Pomidor
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Patent number: 4883914Abstract: 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: GrantFiled: July 7, 1988Date of Patent: November 28, 1989Assignee: American Cyanamid CompanyInventors: Sergio I. Alvarado, Alvin D. Crews, Jr., Peter J. Wepplo, Robert F. Doehner, Jr., Thomas E. Brady, David M. Gange, Desiree L. Little
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Patent number: 4871756Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4, E.sub.4 and the slow reacting substance of anaphylaxis.As such, these compounds will be useful as anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.Type: GrantFiled: February 17, 1987Date of Patent: October 3, 1989Assignee: Merck Frosst Canada, Inc.Inventors: John Gillard, Joshua Rokach, Patrice C. Belanger
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Patent number: 4833252Abstract: Substituted N-phenylsulfonyl-N'-pyrimidinylureas and N-phenylsulfonyl-N'-triazinylureas of the general formula ##STR1## and the salts thereof with amines, alkali metal bases or alkaline earth metal bases, or with quaternary ammonium bases, have good pre- and postemergence selective herbicidal and growth regulating properties.In the above formula the symbols have the following meanings: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 alkylsulfonyl, C.sub.1 -C.sub.4 alkylsulfinyl, --CO--R.sup.8, --NR.sup.9 R.sup.10, --CO--NR.sup.11 R.sup.12 or --SO.sub.2 --NR.sup.13 R.sup.14,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 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or cyano,R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl,R.sup.5 is hydrogen, C.sub.Type: GrantFiled: September 28, 1988Date of Patent: May 23, 1989Assignee: Ciba-Geigy CorporationInventors: Werner Topfl, Georg Pissiotas
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Patent number: 4827032Abstract: 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: GrantFiled: June 29, 1988Date of Patent: May 2, 1989Assignee: Bayer AktiengesellschaftInventors: Horst Boshagen, Ulrich Rosentreter, Folker Lieb, Hermann Oediger, Friedel Seuter, Elisabeth Perzborn, Volker-Bernd Fiedler
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Patent number: 4812512Abstract: Novel supports useful in solid phase synthesis of oligonucleotides of the formula ##STR1## wherein .circle.P is a material selected from the group consisting of functionalized glass micropellets, silica functionalized by aminoalkyl trialkoxysilane capable of to obtain for ##STR2## Kieselguhr, polytetrafluoroethylene, cellulose and metallic oxides, m is an integer from 1 to 20, A is selected from the group consisting of alkyl of 1 to 20 carbon atoms, saturated cycloalkyl of 3 to 12 carbon atoms, phenyl and 5 to 6 member heterocycles, x and y are an integer from 0 to 20, x.sub.1 is an integer from 1 to 20 and y.sub.1 is an integer from 0 to 10, a process for the preparation of said supports, the use of said supports and intermediates.Type: GrantFiled: June 26, 1986Date of Patent: March 14, 1989Assignee: Roussel UclafInventors: Jean Buendia, Jeanine Nierat
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Patent number: 4812463Abstract: Alkane sulfonamides with an electron withdrawing function .beta. to the sulfonamide group are topically effective carbonic anhydrase inhibitors useful in the treatment of elevated intraocular pressure and glaucoma.Type: GrantFiled: December 10, 1987Date of Patent: March 14, 1989Assignee: Merck & Co., Inc.Inventors: Samuel L. Graham, Thomas H. Scholz
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Patent number: 4806528Abstract: In accordance with a novel process, 2-(2-chloroethoxy)-benzene-sulfonamide of formula I ##STR1## is prepared by etherification of 4-chlorophenol of formula II ##STR2## with ethylene carbonate and chlorination of the resulting 2-(2-hydroxyethoxy)-chlorobenzene of formula III ##STR3## with phosgene to give 2-(2-chloroethoxy)-chlorobenzene of formula IV ##STR4## which is converted with chlorosulfonic acid ClSO.sub.3 H and sodium hydroxide to the sulfonic acid sodium salt of formula V ##STR5## which is hydrogenated to the compound of formula VI ##STR6## which is subsequently reacted with phosgene to the sulfonic acid chloride of formula VII ##STR7## which is reacted with ammonia to the sulfonamide of formula I.Type: GrantFiled: September 4, 1987Date of Patent: February 21, 1989Inventor: Reinhard G. Hanreich
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Patent number: 4780504Abstract: Novel supports useful in solid phase synthesis of oligonucleotides of the formula ##STR1## wherein .circle. is micro pellets of a material selected from the group consisting of glass, silica, Kieselguhr, polytetrafluoroethylene, cellulose and metallic oxides, m is an integer from 1 to 20, A is selected from the group consisting of alkylene of 1 to 20 carbon atoms, saturated cycloalkylene of 3 to 12 carbon atoms, phenyl and 5 to 6 member heterocycles, x is an integer from 0 to 20, x.sub.1 is an integer from 0 to 10 and the amino group may be in the m-, p- or o-position, a process for the preparation of said supports, the use of said supports and intermediates.Type: GrantFiled: June 5, 1986Date of Patent: October 25, 1988Assignee: Roussel UclafInventors: Jean Buendia, Jeanine Nierat
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Patent number: 4766241Abstract: The invention relates to 2-aminomethylphenols of the formula I ##STR1## in which R.sup.1 and R.sup.2 represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or benzyl which is optionally substituted by alkyl, alkoxy or halogen, R.sup.3 and R.sup.5 denote hydrogen, halogen, alkyl or alkoxy, R.sup.4 denotes halogen, alkyl or cycloalkyl and R.sup.6 and R.sup.7 represent hydrogen or alkyl, it being possible for the radicals R.sup.1 and R.sup.2, R.sup.6 R.sup.7 and/or two of the radicals R.sup.3, R.sup.4 and R.sup.5 to form an alkylene chain which is optionally substituted by methyl groups and which, in the case of the radicals R.sup.1, R.sup.2, R.sup.6 and R.sup.7, can also be interrupted by oxygen atoms, sulfur atoms and/or imino groups, and to physiologically acceptable salts thereof, a process for their preparation, and their use and to pharmaceutical formulations based on these compounds.Type: GrantFiled: September 23, 1987Date of Patent: August 23, 1988Assignee: Hoechst AktiengesellschaftInventors: Heinrich C. Englert, Dieter Mania, Roman Muschaweck, Max Hropot
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Patent number: 4749407Abstract: 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: GrantFiled: June 23, 1986Date of Patent: June 7, 1988Assignees: Sagami Chemical Research Center, Central Glass Co, Ltd.Inventors: Daiei Tunemoto, Hideko Sakai, Kiyosi Kondo, Kaoru Mori, Masahiro Watanabe, Takeo Komata, Kenji Motojima
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Patent number: 4735959Abstract: There are described novel carboxylic acid derivatives of the formula ##STR1## and derivatives of the formula ##STR2## and the addition salts thereof, which exhibit an effect on the intermediary metabolism. Furthermore, the compounds of Formula Ia as well as the compounds of Formula I possess blood-sugar lowering properties.Type: GrantFiled: May 14, 1985Date of Patent: April 5, 1988Assignee: Dr. Karl Thomae GmbHInventors: Wolfgang Grell, Gerhart Griss, Robert Sauter, Rudolf Hurnaus, Eckhard Rupprecht, Nikolaus Kaubisch, Joachim Kahling, Bernhard Eisele
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Patent number: 4734444Abstract: Mixtures which are curable by heating or irradiation with actinic light contain one or more cationically curable compounds, such as an epoxy, an olefinically unsaturated monomer, amino resin or phenolic resin, and as a cationically active curing catalyst one or more N-sulfonylamino-sulfonium salts of the formula ##STR1## such as N-p-toluenesulfonyl-N-methylaminodiphenylsulfonium hexafluorophosphate with or without quinones or peroxides are suitable, inter alia, for producing moldings, coatings, relief images and resist patterns.Type: GrantFiled: February 12, 1987Date of Patent: March 29, 1988Assignee: BASF AktiengesellschaftInventors: Andreas Henne, Wolfram Ochs, Helmut Tesch, Gunnar Schornick, Reinhold J. Leyrer
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Patent number: 4727187Abstract: The present invention relates to a novel process for the preparation of an .alpha.,.alpha.-difluoroalkyl phenyl ether of formula I ##STR1## wherein R.sup.1 is hydrogen, halogen, amino, nitro, --SO.sub.2 --R.sup.4, --S--R.sup.5, --SO--R.sup.6 or --S--S--R.sup.7,R.sup.2 is hydrogen, halogen, nitro, hydroxy or --SO.sub.2 --R.sup.8,R.sup.3 is C.sub.1 -C.sub.5 haloalkyl,X is oxygen, sulfur, --SO-- or --SO.sub.2 --,R.sup.4 is hydroxy, halogen, amino, --N.dbd.C.dbd.O, --NH--CO--Cl, --NH--CO--Br, --NR.sup.9 R.sup.10, benzyl, phenyl, C.sub.1 -C.sub.4 alkyl or --NH'CO--NR.sup.11 R.sup.12,R.sup.5 and R.sup.6 are C.sub.1 -C.sub.4 alkyl, phenyl or benzyl,R.sup.7 is C.sub.1 -C.sub.4 alkyl, phenyl or benzyl,R.sup.8 is hydroxy or halogen,R.sup.9 and R.sup.10 are each independently of the other C.sub.1 -C.sub.4 alkyl or benzyl andR.sup.11 and R.sup.12 are each independently of the other hydrogen, C.sub.1 -C.sub.Type: GrantFiled: June 5, 1985Date of Patent: February 23, 1988Assignee: Ciba-Geigy CorporationInventors: Urs Siegrist, Jean Indermuhle, Peter Baumeister
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Patent number: 4727186Abstract: Phenylsulfonamides of Formula II ##STR1## wherein A is a radical of the formula --C.tbd.C--R;R is H, or an optionally substituted (i) C.sub.1 -C.sub.9 alkyl, (ii) C.sub.3 -C.sub.9 cycloalkyl, (iii) phenyl, or (iv) 5-or-6 membered heterocyclic ring;m is one or two;R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, or --Y--R.sub.5 ;R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, C.sub.1 -C.sub.4 haloalkenyl, --Y--R.sub.5, --COOR.sub.6, --NO.sub.2, or --CO--NR.sub.7 --R.sub.8 ;R.sub.5 and R.sub.6 are each independently C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.1 -C.sub.5 haloalkyl, C.sub.2 -C.sub.5 haloalkenyl, or C.sub.2 -C.sub.6 alkoxyalkyl;R.sub.7 and R.sub.8 are each independently hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, or C.sub.2 -C.sub.6 alkynyl; andY is oxygen, sulfur, sulfinyl or sulfonyl bridge; or a salt thereof.Type: GrantFiled: June 17, 1985Date of Patent: February 23, 1988Assignee: Ciba-Geigy CorporationInventors: Rolf Schurter, Werner Fury, Willy Meyer
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Patent number: 4720580Abstract: This invention provides a group of anti-arrhythmic agents of the formula: ##STR1## in which R.sup.1 is hydrogen, hydroxy, alkoxy or halo;R.sup.2 is hydrogen, alkoxy, halo or trifluoromethyl, with the proviso that R.sup.2 is not hydrogen when R.sup.1 is hydrogen;R.sup.3 is alkyl or, when R.sup.2 is trifluoromethyl and R.sup.1 is hydrogen, R.sup.3 may be hydrogen;R.sup.4 is alkyl, cycloalkyl or cycloalkylmethyl;R.sup.5 is hydrogen or alkyl;n is 2-4;or a pharmaceutically acceptable salt thereof.Type: GrantFiled: April 11, 1986Date of Patent: January 19, 1988Assignee: American Home Products CorporationInventor: George C. Buzby, Jr.
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Patent number: 4714700Abstract: The invention relates to new N-substituted benzenesulfonamides, the process for their preparation and their use.The compounds according to the invention correspond to the general formula (I): ##STR1## in which: n and m have values from 0 to 4;R.sub.3 and R.sub.4 represent in particular a lower alkyl radical;R.sub.1 and R.sub.2 represent in particular hydrogen atoms, linear or branched alkyl groups having from 1 to 4 carbon atoms;R.sub.5 represents particularly a hydrogen atom, a halogen, the NO.sub.2, NH.sub.2, or CF.sub.3 group;R.sub.6 and R.sub.7 represent in particular a hydrogen atom, an alkyl radical of 1 to 6 carbon atoms.The invention is useful in the preparation of tranquilizing or anxiolytic medicines.Type: GrantFiled: February 12, 1985Date of Patent: December 22, 1987Assignee: Choay S.A.Inventors: Jean-Paul Fournier, Patrick Choay
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Patent number: 4709092Abstract: In accordance with a novel process, 2-alkoxybenzosulfonamides of formula I ##STR1## wherein R is chloromethyl, methoxymethyl, C.sub.1 -C.sub.4 alkyl or trifluoromethyl, are prepared by reacting a 4-alkoxychlorobenzene of formula II ##STR2## with chlorosulfonic acid ClSO.sub.3 H, converting the resultant sulfonyl chloride of formula III ##STR3## by reaction with ammonia into the sulfonamide of formula IV ##STR4## and hydrogenating said sulfonamide with hydrogen, in the presence of a precious metal catalyst.Type: GrantFiled: March 5, 1986Date of Patent: November 24, 1987Assignee: Ciba-Geigy CorporationInventor: Franz-Josef Jaeggi
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Patent number: 4683330Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.Type: GrantFiled: January 11, 1985Date of Patent: July 28, 1987Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4672139Abstract: Benzoylurea compounds of the formula ##STR1## wherein the meaning of each of the symbols is described in the specification.Type: GrantFiled: July 21, 1986Date of Patent: June 9, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Martin Anderson
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Patent number: 4668814Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.Type: GrantFiled: January 11, 1985Date of Patent: May 26, 1987Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4661601Abstract: New compounds having the formula 1 ##STR1## wherein W is hydrogen, halogen, n-alkyl, --NHCOR.sup.1, --COR.sup.1, or phenoxyacetylamino optionally substituted by one or two C.sub.1-12 straight- or branched chain alkyl, X is a substituent in the coupling position and is selected from hydrogen, chlorine, bromine, --SR.sup.11 or a nitrogen-containing heterocyclic residue attached at a ring nitrogen atom, and Y is a group having the formula 2 ##STR2## wherein Q is selected from the residues: --COOR.sup.4 or --CONR.sup.4 R.sup.5, --OM, --NR.sup.7 R.sup.8, --PO(OR.sup.9)[O].sub.x R.sup.10 with X=0 or 1, --SO.sub.2 OH, --SO.sub.2 NR.sup.4 R.sup.5 or CN. The groups R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, M, k and n are defined hereinafter.These compounds are used as black color couplers in photographic materials.Type: GrantFiled: April 3, 1985Date of Patent: April 28, 1987Assignee: Ciba-Geigy AGInventor: Frederick H. Howell
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Patent number: 4629810Abstract: N-phenylsulfonyl-N'-pyrimidinyl- and -triazinylureas of the general formula ##STR1## and the salts thereof with amines, alkali metal or alkaline earth metal bases or with quaternary ammonium bases, have good pre- and postemergence selective herbicidal and growth regulating properties. In the above formulaA is a C.sub.1 -C.sub.6 alkyl radical which is substituted by 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, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 haloalkylsulfinyl or C.sub.1 -C.sub.4 haloalkylsulfonyl, or a C.sub.2 -C.sub.6 alkenyl radical which is unsubstituted or substituted by the above substituents, or is a C.sub.2 -C.sub.6 haloalkenyl radical,E is the methine group or nitrogen,X is oxygen, sulfur, a sulfinyl or sulfonyl bridge,Z is oxygen or sulfur,m is 1 or 2,R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl or a radical --Y--R.sub.5,R.sub.Type: GrantFiled: January 22, 1985Date of Patent: December 16, 1986Assignee: Ciba-Geigy CorporationInventors: Willy Meyer, Werner Fory
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Patent number: 4629739Abstract: Novel substituted sulfonamidobenzamides are described as useful antiarrhythmic agents. Their use in the treatment of cardiac arrhythmias, especially re-entrant arrhythmias, via the prolongation of the action potential of cardiac tissue is provided. Pharmaceutical formulations containing such compounds are also disclosed.Type: GrantFiled: September 23, 1985Date of Patent: December 16, 1986Assignee: Schering A.G.Inventors: David D. Davey, William C. Lumma, Jr., Ronald A. Wohl
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Patent number: 4628110Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: October 30, 1984Date of Patent: December 9, 1986Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4616082Abstract: New hydroquinone ether compounds of formula I are described: ##STR1## wherein p is 1 or 2 and Q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification,The new compounds are useful e.g. as stabilizers in photographic material.Type: GrantFiled: June 7, 1985Date of Patent: October 7, 1986Assignee: Ciba-Geigy AGInventor: Frederick H. Howell
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Patent number: 4602097Abstract: Photoinitiators of the formulaG--O--(CH.sub.2 CH.sub.2 O).sub.n --CH.sub.2 --CH.sub.2 --O--Qwherein G is a photoinitiator moiety, R is hydrogen or lower alkyl, n has a value of at least 10, and Q is G or a lower alkyl are soluble in water and common organic solvents and are useful in polymerization systems employed in coatings used in screen printing.Type: GrantFiled: June 11, 1984Date of Patent: July 22, 1986Assignee: Ulano CorporationInventor: John R. Curtis
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Patent number: 4588823Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: September 27, 1984Date of Patent: May 13, 1986Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4565887Abstract: N-Phenylsulfonyl-N'-pyrimidinyl- and -triazinylureas of the general formula ##STR1## and the salts of these compounds with amines, with alkali or alkaline-earth metal bases or with quaternary ammonium bases, have good pre- and post-emergence selective, herbicidal and growth-regulating properties.The symbols in this formula are as follows:A is a C.sub.3 -C.sub.6 -alkynyl group,E is the methine group or nitrogen,X is oxygen, sulfur or a sulfinyl or sulfonyl bridge,Z is oxygen or sulfur,m is the number one or two,R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.5 -alkyl or C.sub.2 -C.sub.5 -alkenyl or a group --Y--R.sub.5,R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.5 -alkyl, C.sub.2 -C.sub.5 -alkenyl or C.sub.1 -C.sub.4 -haloalkyl, or a group --Y--R.sub.5, --COOR.sub.6, --NO.sub.2 or --CO--NR.sub.7 --R.sub.8,R.sub.3 and R.sub.4 independently of one another are each 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.Type: GrantFiled: January 19, 1984Date of Patent: January 21, 1986Assignee: Ciba-Geigy Corp.Inventors: Werner Fory, Karl Gass, Willy Meyer, Rolf Schurter
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Patent number: 4560786Abstract: .DELTA..sup.8,9 -Prostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 ; A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH;B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C--W is a free or functionally modified hydroxymethylene group or free or functionally modified ##STR4## wherein the OH--group can be in the .alpha.-- or .beta.-- position; D and E jointly are a direct bond orD is straight chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen, sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 --, wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine or alkyl;R.sub.4 is free or functionally modified hydroxy andR.sub.Type: GrantFiled: June 24, 1982Date of Patent: December 24, 1985Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
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Patent number: 4556733Abstract: A three step process for preparing 2-hydroxybenzenesulfonamide from 2,4-dichlorophenol by treatment with chlorosulfonic acid followed by amination to form the dichlorohydroxysulfonamide and finally dehalogenation.Type: GrantFiled: June 11, 1984Date of Patent: December 3, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventors: Thomas A. Sullivan, Vincent G. Witterholt
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Patent number: 4549015Abstract: New hydroquinone ether compounds of formula I are described: ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification.The new compounds are useful e.g. as stabilizers in photographic material.Type: GrantFiled: June 14, 1983Date of Patent: October 22, 1985Assignee: Ciba-Geigy AGInventor: Frederick H. Howell
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Patent number: 4544654Abstract: Novel substituted sulfonamidobenzamides are described as useful antiarrhythmic agents. Their use in the treatment of cardiac arrhythmias, especially re-entrant arrhythmias, via the prolongation of the action potential of cardiac tissue is provided. Pharmaceutical formulations containing such compounds are also disclosed.Type: GrantFiled: March 20, 1984Date of Patent: October 1, 1985Assignee: Schering A.G.Inventors: David D. Davey, William C. Lumma, Jr., Ronald A. Wohl
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Patent number: 4539161Abstract: Novel amine oxide compounds of the formula ##STR1## in which m is the integer 1 or 2, A is a through-conjugated radical of a fluorescent brightener system, which radical contains unsubstituted or non-chromophorically substituted aromatic carbocyclic and/or heterocyclic rings, X is a direct bond between A and Y, an oxygen atom or sulfur atom or a group of the formula --SO.sub.2 --, --SO.sub.2 --O--, --COO--, --CON(R)-- or --SO.sub.2 N(R)--, in which R is hydrogen or unsubstituted or non-chromophorically substituted alkyl, Y is an unsubstituted or non-chromophorically substituted straight-chain or branched alkylene or alkyleneoxyalkylene group, and R.sub.1 and R.sub.2 independently of one another are cycloalkyl, unsubstituted or non-chromophorically substituted alkyl or phenyl, or R.sub.1 and R.sub.Type: GrantFiled: July 13, 1981Date of Patent: September 3, 1985Assignee: Ciba-Geigy CorporationInventor: Leonardo Guglielmetti
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Patent number: 4533749Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: February 16, 1982Date of Patent: August 6, 1985Assignee: The Upjohn CompanyInventors: Paul A. Aristoff, John C. Sih
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Patent number: 4525586Abstract: 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 anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), methano (C-6a,9), and an additional (olefinic) valence bond (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-methano)-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: GrantFiled: September 19, 1983Date of Patent: June 25, 1985Assignee: The Upjohn CompanyInventor: Paul A. Aristoff