Chalcogen Attached Indirectly To The Thiazole Ring By Nonionic Bonding Patents (Class 548/193)
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Patent number: 4647557Abstract: This invention relates to novel heterocyclic derivatives bearing an amino group and to processes for making said compounds.More particularly this invention provides novel heterocyclic compounds the hetero ring of which has two hetero atoms, the same or different, substituted with a free or substituted amino group.These compounds are useful as active ingredients of drugs.Type: GrantFiled: December 23, 1983Date of Patent: March 3, 1987Inventors: Gerard Moinet, Michel Schaeffer, Pierre Bessin, Jacqueline Bonnet
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Patent number: 4636516Abstract: Novel 3,5-di-tert-butyl-4-hydroxyphenyl-substituted heterocyclic compounds shown by the formula ##STR1## wherein .circle.Het -- represents a specific heterocyclic group and the salts thereof.The compounds have an anti-inflammatory, an anti-pyretic, an analgesic, an anti-arthritic, and an immunoregulatory activity. Hence, they are particularly useful as an antirheumatics.Type: GrantFiled: February 11, 1982Date of Patent: January 13, 1987Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Kazuo Kubo, Yasuo Isomura, Shuichi Sakamoto, Hiroshige Homma
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Patent number: 4622330Abstract: Novel 3-amino or substituted amino pyrazoles are disclosed as having antiprotozoal and antiparasitic activity in particular anticoccidial activity and are useful for controlling cecal and or intestinal coccidiosis when administered in minor quantities to animals, in particular to poultry usually in admixture with animal sustenance.Type: GrantFiled: June 19, 1984Date of Patent: November 11, 1986Assignee: Merck & Co., Inc.Inventors: Richard J. Bochis, Richard A. Dybas, Edward F. Rogers
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Patent number: 4616025Abstract: New thiazolidine compounds of the formula (I) having anti-ulcer activity are disclosed: ##STR1## wherein Ar is a 2-furyl or a phenyl, naphthyl or pyridyl group optionally substituted by one or more C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, halo-C.sub.1-4 -alkoxy, dihalomethyl, trihalomethyl, hydroxyl or nitro groups or by a group of the formula (II), ##STR2## wherein Y is nitrogen or CH;Z is cyano or carbamoyl if Y is nitrogen, and represents a nitro group if Y is CH.Also disclosed are several processes for preparing the new compounds as well as pharmaceutical compositions and method of treatment employing same.Type: GrantFiled: March 16, 1984Date of Patent: October 7, 1986Assignee: Richter Gedeon Vegyeszeti Gyar RTInventors: Elemer Ezer, Kalman Harsanyi, Gyorgy Domany, Laszlo Szporny, Judit Matuz, Bela Hegedus, Katalin Pallagi, Istvan Szabadkai, Peter Tetenyi
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Patent number: 4609737Abstract: Novel 2-guanidinothiazoline compounds of the general formula ##STR1## wherein R represents a hydrogen atom or a lower alkyl group, and X represents a halogen atom, and the acid addition salts thereof; they are important intermediate compounds for preparing famotidine and thiotidine which are medicaments useful as gastric acid secretion inhibitors.Type: GrantFiled: June 7, 1985Date of Patent: September 2, 1986Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Yasufumi Hirata, Isao Yanagisawa
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Patent number: 4600780Abstract: New N-cyano-formamidine are disclosed of the formula I: ##STR1## wherein R is 2-[[(5-methyl-1H-Imidazol-4-yl)methyl]thio]ethyl, 2-[[[5-[dimethylamino)methyl]-2-furanyl]methyl]thio]ethyl, 2-[[[2-[(aminoiminomethyl)amino]-4-thiazolyl]methyl]thio]ethyl or 3-[3-(1-piperidinylmethyl)phenoxy]propyl, as well as a process for its production, and pharmaceutical preparations containing the same. The compounds possess histamine--induced gastric acid secretion--inhibiting activity, and are indicated for use in the treatment of peptic ulcer and other pathologies caused or stimulated by gastric acidity.Type: GrantFiled: March 20, 1984Date of Patent: July 15, 1986Assignee: Ferrer International, S.A.Inventors: Rafael Foguet, Luis Anglada, Manuel M. Raga, Jose A. Ortiz, Aurelio Sacristan, Jose M. Castello
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Patent number: 4598154Abstract: A cephalosporin compound of the formula: ##STR1## wherein R.sup.1 is hydrogen or lower alkyl;R.sup.2 is acetoxy or (1-methyl-1H-tetrazol-5-yl)thio, andR.sup.3 is carboxy; orR.sup.2 is a group of the formula ##STR2## R.sup.3 is --COO.sup.- and Y is hydrogen, hydroxymethyl or carbamoyl; andn is an integer of 2 or 3,or a pharmaceutically acceptable salt thereof and processes for their preparation are disclosed. Said cephalosporin compound is useful as an antimicrobial agent.Type: GrantFiled: January 18, 1985Date of Patent: July 1, 1986Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Toyonari Oine, Hiroshi Sugano, Yoshihisa Yamada, Totaro Yamaguchi, Satoshi Ohshima
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Patent number: 4585781Abstract: This invention relates to compounds of the general formula (I) ##STR1## and physiologically acceptable salts and hydrates thereof, in which R.sub.1 represents a hydrogen atom or an alkyl, alkanoyl, aroyl or trifluoroalkyl group;R.sub.2 represents a hydrogen atom or an alkyl or alkenyl group or C.sub.2-6 alkyl group substituted by a hydroxy or alkoxy group;X represents a sulphur atom or NH;Y represents an oxygen or sulphur atom or a bond;m represents 1, 2 or 3; andn represents 2, 3 or 4.The compounds show pharmacological activity as selective histamine H.sub.2 -antagonists.Type: GrantFiled: December 30, 1983Date of Patent: April 29, 1986Assignee: Glaxo Group LimitedInventors: David Bays, Roger Hayes, Philip Blatcher
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Patent number: 4578478Abstract: A series of new 2,4-substituted thiazole derivatives are disclosed. These compounds have anti-histaminergic activity, especially, outstanding gastric anti-secretory activity.The compounds of this invention are obtained mainly by reacting 2-substituted-4-aminoalkyl-thiomethyl thiazole with a compound having methylthio or hydroxy group corresponding thereto.Type: GrantFiled: November 18, 1983Date of Patent: March 25, 1986Assignee: Kotobuki Seiyaku Company LimitedInventor: Tsuyoshi Tomiyama
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Patent number: 4578470Abstract: Phthalimides and the like in which the substituent on the imide nitrogen is a highly electron-deficient group may be prepared by the reaction of the appropriate amine with phthalic anhydride. These imides are useful for the preparation of polyimides by reaction with diamines.Type: GrantFiled: June 20, 1983Date of Patent: March 25, 1986Assignee: General Electric CompanyInventor: Jimmy L. Webb
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Patent number: 4575501Abstract: 2-Arylhydrazino-2-thiazolines, acyl derivatives of these compounds and 2-arylazo-2-thiazolines, of the general formula ##STR1## and salts thereof, are new, are prepared as described and find use for combating ectoparasites and endoparasites, such as cattle and sheep ticks, and gastric and intestinal nematodes in ruminants and carnivors.Type: GrantFiled: August 6, 1982Date of Patent: March 11, 1986Assignee: Bayer AktiengesellschaftInventors: Otto Behner, Wilhelm Stendel, Peter Andrews
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Patent number: 4570000Abstract: The invention relates to nitrogen heterocycles which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I:- ##STR1## in which R.sup.1 and R.sup.2, same or different, are hydrogen or 1-lOC alkyl, 3-8C cycloalkyl or 4-14C cycloalkylalkyl, each alkyl, cycloalkyl or cycloalkylalkyl optionally carrying one or more F, Cl or Br atoms, provided that one of R.sup.1 and R.sup.2 is halogen substituted, or R.sup.2 is hydrogen and R.sup.1 is R.sup.3 --E--W is which W is 2-6C alkylene optionally substituted by 1 or 2 1-4C alkyls, E is O, S, SO, SO.sub.2 or NR.sup.4 in which R.sup.4 is H or 1-6C alkyl, R.sup.3 is H or 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls, or R.sup.3 and R.sup.4 are joined to form a pyrrolidine, piperidine, morpholine, piperazine or N-methylpiperazine ring, or R.sup.2 is H and R.sup.Type: GrantFiled: July 13, 1984Date of Patent: February 11, 1986Assignee: Imperial Chemical Industries, PLCInventors: Derrick F. Jones, Keith Oldham
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Patent number: 4563476Abstract: Substituted 5-hydroxy-2,3-dihydrobenzofuran and analogs such as the substituted 6-hydroxy-2,3-dihydrobenzopyrans were prepared from an appropriately substituted (5-hydroxy-2,3-dihydrobenzofuran-6-yl) formaldehyde or analog thereof with an aryl amine followed by reduction. These compounds were found to be potent topical anti-inflammatory agents.Type: GrantFiled: November 21, 1983Date of Patent: January 7, 1986Assignee: Merck & Co., Inc.Inventors: Michael N. Chang, Milton L. Hammond, Norman P. Jensen, Robert A. Zambias
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Patent number: 4562201Abstract: The present invention relates to new compounds of the formula ##STR1## where X is ##STR2## alkylene, or --S-- where R.sub.1 is hydrogen, alkyl, or aryl; W is hydrogen, hydroxy, amino, alkyloxy, aryloxy, O-alkyl, or O-aralkyl; (Y).sub.A is --CH.sub.2 NR.sub.2 R.sub.3 where R.sub.2 and R.sub.3 may be hydrogen, substituted alkyls, aryls, or together with N form a 5 to 7 membered heterocyclic group; and Ar is a substituted or unsubstituted aryl. These compounds are useful in the treatment of various cardiac arrhythmias.Type: GrantFiled: July 26, 1982Date of Patent: December 31, 1985Assignee: American Hospital Supply CorporationInventors: David M. Stout, William L. Matier
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Patent number: 4562261Abstract: Novel 2-guanidinothiazoline compounds of the general formula ##STR1## wherein R represents a hydrogen atom or a lower alkyl group, and X represents a halogen atom, and the acid addition salts thereof; they are important intermediate compounds for preparing famotidine and thiotidine which are medicaments useful as gastric acid secretion inhibitors.Type: GrantFiled: April 5, 1984Date of Patent: December 31, 1985Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Yasufumi Hirata, Isao Yanagisawa
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Patent number: 4560690Abstract: 2,4-Disubstituted thiazole compounds of the formula ##STR1## or a pharmaceutically acceptable acid addition salt thereof wherein X is NH and Y is CH or N, orX is S and Y is CH;R.sup.1 is certain straight or branched chain alkyl groups, (R.sup.3).sub.2 C.sub.6 H.sub.3, or (R.sup.3).sub.2 Ar(CH.sub.2).sub.n where n is an integer from 1 to 4, R.sup.3 is H or certain substituent groups and Ar is phenylene, naphthalene or the residue of certain heteroaromatic groups;R.sup.2 is H or (C.sub.1 -C.sub.4)alkyl; orR.sup.1 and R.sup.2 taken together with the nitrogen atom to which they are attached form certain heterocyclic groups; andR.sup.4 is H, (C.sub.1 -C.sub.5)alkyl, NH.sub.2 or CH.sub.2 OH; a method for their use in treatment of gastric ulcers in mammals and pharmaceutical compositions containing said compounds.Type: GrantFiled: April 30, 1984Date of Patent: December 24, 1985Assignee: Pfizer Inc.Inventor: Lawrence A. Reiter
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Patent number: 4548944Abstract: Compounds of the tautomeric formula ##STR1## wherein R, R.sub.1 and R.sub.2, which may be identical to or different from each other, are each hydrogen or alkyl of 1 to 4 carbon atoms;R.sub.3 is straight or branched alkyl, optionally interrupted by heteroatoms such as oxygen, sulfur or nitrogen; straight or branched alkenyl; alkynyl; cyano; cycloalkyl or cycloaliphatic alkyl; a bicyclic group; aryl; or a heterocyclic group; orR.sub.2 and R.sub.3, together with each other and the nitrogen atoms to which they are attached, form a heterocyclic group;R.sub.4 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; andHet is a substituted or unsubstituted heterocycle containing two or three heteroatoms;tautomers thereof, and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as anti-ulcerogenics.Type: GrantFiled: February 10, 1983Date of Patent: October 22, 1985Assignee: Istituto de Angeli S.p.A.Inventors: Giuseppe Bietti, Enzo Cereda, Arturo Donetti, Piero del Soldato, Antonio Giachetti, Rosamaria Micheletti
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Patent number: 4535088Abstract: New 2-(2-propynylamino)thiazole and 2-(3-iodo-2-propynylamino)thiazole derivatives having anti-microbial activity which are used as an active ingredient in anti-microbial compositions for medical and agricultural use.Type: GrantFiled: December 2, 1983Date of Patent: August 13, 1985Assignee: Shionogi & Co., Ltd.Inventors: Yasuo Makisumi, Akira Murabayashi, Katsuya Tawara, Yoshihachi Watanabe, Toshio Takahashi
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Patent number: 4525477Abstract: 2,3-Unsaturated nitrogen-containing heterocyclic compounds with a 3-nitro group and a 2-heterocyclyl alkylamino group. The alkyl group of 2-position substituents is preferably interrupted by sulfur or oxygen. The compounds of the invention are preferably dihydropyrroles or tetrahydropyrridines or pyrimidines. The compounds of the invention are histamine H.sub.2 -receptor antagonists.Type: GrantFiled: April 25, 1983Date of Patent: June 25, 1985Assignee: Smith Kline & French Laboratories LimitedInventors: Michael L. Roantree, Rodney C. Young
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Patent number: 4521418Abstract: The compounds are guanidinothiazolyl derivatives which are histamine H.sub.2 -antagonists. A specific compound of the present invention is 2-[2-(2-guanidino-4-thiazolylmethylthio)ethylamino]-5-(6-methyl-3-pyridylm ethyl)-4-pyrimidone.Type: GrantFiled: February 12, 1980Date of Patent: June 4, 1985Assignee: Smith Kline & French Laboratories LimitedInventors: Thomas H. Brown, Graham J. Durant
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Patent number: 4518598Abstract: The invention relates to compounds of the general formula (I) ##STR1## and physiologically acceptable salts, and hydrates thereof. The substituents are defined in the specification.The compounds show pharmacological activity as selective histamine H.sub.2 -antagonists.Type: GrantFiled: January 9, 1984Date of Patent: May 21, 1985Assignee: Glaxo Group LimitedInventors: Roger Hayes, David E. Bays, John W. M. Mackinnon, Linda Carey, Philip Blatcher
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Patent number: 4505919Abstract: Compounds of the formula: ##STR1## wherein Ar is phenyl substituted by from 1 to 3 substituents, each substituent being independently halo or CF.sub.3 ;n is 0 or 1; andR is a phenyl or a phenyl group substituted by from 1 to 3 substituents, each substituent being independently halo, CF.sub.3, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkoxy-carbonyl or C.sub.1 -C.sub.4 alkylthio, or a 5 or 6 membered aromatic heterocyclic group which may optionally be substituted;and their pharmaceutically acceptable salts are antifungal agents useful in combatting fungal infections in humans.Type: GrantFiled: March 28, 1983Date of Patent: March 19, 1985Assignee: Pfizer Inc.Inventors: Kevin Cooper, Kenneth Richardson, Peter J. Whittle
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Patent number: 4496737Abstract: A process is disclosed for preparing intermediates which are useful for obtaining sulfamylamidine antisecretory agents.Type: GrantFiled: September 27, 1982Date of Patent: January 29, 1985Assignee: Merck & Co., Inc.Inventor: Jacob M. Hoffman, Jr.
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Patent number: 4492794Abstract: A compound of the formula: ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.5 alkanoyl or substituted sulfonyl, which is useful as a synthetic intermediate to 2-guanidino-4-[2-(formamido)ethylthiomethyl]thiazole, histamine H.sub.2 receptor antagonist.Type: GrantFiled: April 26, 1983Date of Patent: January 8, 1985Assignee: Shionogi & Co., Ltd.Inventor: Kentaro Hirai
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Patent number: 4489084Abstract: Described are oxazolyl (or thiazolyl) hydrazinoalkyl nitrile compounds of the formula ##STR1## wherein R is hydrogen or loweralkyl, R.sub.1 and R.sub.2 independently of one another denote hydrogen, loweralkyl, or phenyl or naphthyl substituted with halo, loweralkyl or loweralkoxy, X is oxygen or sulfur, n and m are each an integer from 0 to 3 inclusive, or pharmaceutically acceptable salts thereof. The compounds are useful as anti-inflammatory agents.Type: GrantFiled: June 30, 1983Date of Patent: December 18, 1984Assignee: Abbott LaboratoriesInventors: Fortuna Haviv, Francis A. J. Kerdesky
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Patent number: 4464374Abstract: The invention relates to a guanidine derivative of the formula: ##STR1## in which W is a 2-6C alkylene chain optionally substituted by 1 or 2 1-4C alkyls; E is O, S, SO, SO.sub.2 or NR.sup.3 in which R.sup.3 is H or 1-6C alkyl; R.sup.1 is H or a straight chain 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls; or R.sup.1 and R.sup.3 are joined to form a morpholine, pyrrolidine, piperidine or piperazine ring; X, P, Y, Q and R.sup.2 are as defined in the specification, and the pharmaceutically-acceptable acid-addition salts thereof. Manufacturing process, pharmaceutical compositions and intermediates are also described. The compounds of the formula I are histamine H-2 antagonists.Type: GrantFiled: July 23, 1981Date of Patent: August 7, 1984Assignees: ICI Americas Inc., Imperial Chemical Industries PLCInventors: Tobias O. Yellin, David J. Gilman, Derrick F. Jones, Keith Oldham
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Patent number: 4460584Abstract: The invention relates to nitrogen heterocycles which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 and R.sup.2, same or different, are hydrogen or 1-10C alkyl, 3-8C cycloalkyl or 4-14C cycloalkylalkyl, each alkyl, cycloalkyl or cycloalkylalkyl optionally carrying one or more F, Cl or Br atoms, provided that one of R.sup.1 and R.sup.2 is halogen substituted, or R.sup.2 is hydrogen and R.sup.1 is R.sup.3 -E-W in which W is 2-6C alkylene optionally substituted by 1 or 2 1-4C alkyls, E is O, S, SO, SO.sub.2 or NR.sup.4 in which R.sup.4 is H or 1-6C alkyl, R.sup.3 is H or 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls, or R.sup.3 R.sup.4 are joined to form a pyrrolidine, piperidine, morpholine, piperazine or N-methylpiperazine ring, or R.sup.2 is H and R.sup.Type: GrantFiled: March 9, 1982Date of Patent: July 17, 1984Assignee: Imperial Chemical Industries PLCInventors: Derrick F. Jones, Keith Oldham
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Patent number: 4452985Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, cyano or cyano(lower)alkyl;R.sup.2 is hydrogen, cyano, carboxy, carbamoyl, guanyl, (lower)alkoxyimino, hydrazinocarbonyl, (lower)alkylaminoimino, ##STR2## with the proviso that one but never both of R.sup.1 and R.sup.2 is hydrogen; and the pharmacologically acceptable salts thereof exhibit H.sub.2 -receptor antagonist and gastric secretion inhibition activity.Type: GrantFiled: February 14, 1983Date of Patent: June 5, 1984Assignee: American Home Products CorporationInventors: Arthur A. Santilli, Anthony C. Scotese, Robert L. Morris, Stanley C. Bell
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Patent number: 4451463Abstract: This invention relates to alcohol derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 and R.sup.2, same or different, are hydrogen or 1-10C alkyl, 3-8C cycloalkyl or 4-14C cycloalkylalkyl, each alkyl, cycloalkyl or cycloalkylalkyl optionally carrying one or more F, Cl or Br atoms, provided that one of R.sup.1 and R.sup.2 is halogen-substituted, or R.sup.2 is hydrogen and R.sup.1 is R.sup.5 --E--W-- in which W is 2-6C alkylene optionally substituted by 1 or 2 1-4C alkyl, E is O, S, SO, SO.sub.2 or NR.sup.6 in which R.sup.6 is H or 1-6C alkyl, R.sup.5 is H or 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls, or R.sup.5 and R.sup.6 are joined to form a pyrrolidine, piperidine, morpholine, piperazine or N-methylpiperazine ring, or R.sup.2 is hydrogen and R.sup.Type: GrantFiled: March 1, 1982Date of Patent: May 29, 1984Assignee: Imperial Chemical Industries PLCInventor: Michael S. Large
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Patent number: 4435396Abstract: Heretofore unavailable 2-guanidino-4-(2-substituted-amino-4-imidazolyl)thiazoles; a novel process therefor, also advantageous for the preparation of known antiulcer 2-guanidino-4-(2-substituted-amino-4-imidazolyl)thiazoles; intermediate compounds therefor; and a method for treatment of ulcers in mammals therewith.Type: GrantFiled: May 10, 1982Date of Patent: March 6, 1984Assignee: Pfizer Inc.Inventors: John L. LaMattina, Christopher A. Lipinski
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Patent number: 4414211Abstract: 5-Membered, 6-membered and 7-membered heterocyclic derivatives of guanidine having hypoglycemic activity.Type: GrantFiled: March 14, 1980Date of Patent: November 8, 1983Assignee: McNeilab, Inc.Inventor: Chris R. Rasmussen
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Patent number: 4412856Abstract: The novel compounds of the formula I are useful selective herbicides for postemergence application in crops of cereals, maize and rice.In formula I, ##STR1## A is an unsubstituted or substituted amino group, Q is a C.sub.2 -C.sub.6 alkylene bridge, Y is an oxygen or sulfur atom or an unsubstituted or substituted nitrogen atom, and Z is an unsubstituted or substituted phenyl, naphthyl or heterocyclic radical, which phenyl radical, containing the bridge member Y, can additionally carry one to four further substituents.Type: GrantFiled: May 22, 1981Date of Patent: November 1, 1983Assignee: Ciba-Geigy CorporationInventors: Hans-Georg Brunner, Rolf Schurter, Henry Szczepanski
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Patent number: 4409216Abstract: A compound, with hypoglycaemic activity, having formula (II) or a pharmaceutically acceptable acid addition salt thereof: ##STR1## wherein X represents oxygen or sulphur;R.sup.1 R.sup.2 are the same or different and represent hydrogen, halogen, C.sub.1-6 alkyl, phenyl, benzyl,C.sub.3-6 cycloalkyl, carbo-C.sub.1-6 alkoxy or C.sub.1-6 carboxy or R.sup.1 and R.sup.2 represent the remaining members of a benzene ring;R.sup.3 represents hydrogen, C.sub.1-6 alkyl, phenyl or benzyl;R.sup.4 represents hydrogen or C.sub.1-6 alkyl;R.sup.5 represents C.sub.1-6 alkyl, phenyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl, and C.sub.1-6 alkoxy; or benzyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.1-6 alkoxy; or R.sup.4 and R.sup.5 together represent the remaining members of a 5- or 6- membered ring optionally containing an oxygen, sulphur or additional nitrogen atom and being optionally substituted with C.sub.1-6 alkyl; andR.sup.Type: GrantFiled: April 11, 1980Date of Patent: October 11, 1983Assignee: Beecham Group LimitedInventor: Barrie C. C. Cantello
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Patent number: 4395544Abstract: The present invention relates to compounds obtained by condensing a compound of formula I, ##STR1## or a salt thereof, in which R is a primary, secondary or tertiary amino group,with a Vilsmeier reagent,and derivatives of such aldehydes.Type: GrantFiled: May 15, 1981Date of Patent: July 26, 1983Assignee: Sandoz Ltd.Inventor: Robert Egli
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Patent number: 4393006Abstract: Novel diazidosulfonyl-N-substituted aniline compounds are disclosed. These compounds are useful in pretreating cellulosic materials to thereby photolytically develop colored images on said materials.Type: GrantFiled: July 7, 1982Date of Patent: July 12, 1983Assignee: Armstrong World Industries, Inc.Inventors: Charles E. Hoyle, Ronald S. Lenox
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Patent number: 4388319Abstract: The compounds are N,N'-substituted thioureas, ureas and guanidines which are H-2 histamine receptor inhibitors. A compound of this invention is N-cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-N"-[2-(2-thiazolyl methylthio)ethyl]guanidine.Type: GrantFiled: December 11, 1980Date of Patent: June 14, 1983Assignee: Smith Kline & French Laboratories LimitedInventors: Graham J. Durant, Charon R. Ganellin
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Patent number: 4375472Abstract: Amidinosulphonic acid derivatives carrying an unsaturated nitrogen heterocycle-containing substituent, representative of which are N-methyl-N'[2-(5-methyl-4-imidazolylmethylthio)- ethyl] amidinosulphonic acid and N-methyl-N'-[2-(3-chloropyrid-2-ylmethylthio) ethyl] amidinosulphonic acid, are histamine H.sub.2 -receptor antagonists.Type: GrantFiled: November 24, 1980Date of Patent: March 1, 1983Assignee: Smith Kline & French Laboratories LimitedInventors: Graham J. Durant, Rodney C. Young, Zev Tashma
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Patent number: 4374843Abstract: A series of 2-guanidino-4-heteroarylthiazoles, wherein the heteroaryl substituent is selected from thiazolyl, triazolyl, imidazolyl, and 2-alkyl, 2-amino and 2-carboxamido derivatives thereof, are disclosed. The novel compounds have activity as antisecretory agents and histamine H.sub.2 antagonists and are useful for the treatment of gastric hyperacidity and peptic ulcers. Also disclosed are pharmaceutical compositions containing the novel compounds of this invention and a method of using the compounds in the treatment of gastric hyperacidity and peptic ulcers. Novel intermediates useful in the preparation of the novel antisecretory compounds are also described.Type: GrantFiled: August 20, 1981Date of Patent: February 22, 1983Assignee: Pfizer Inc.Inventors: John L. La Mattina, Christopher A. Lipinski
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Patent number: 4374248Abstract: Histamine H.sub.2 -antagonists of the formula ##STR1## wherein p is 1 or 2; R.sup.1 is hydroxy, amino, substituted amino or a 5- to 9-membered fully saturated nitrogen-containing heterocyclic ring attached via its nitrogen atom; m is an integer of from 0 to 2; n is an integer of from 2 to 4; Z is sulfur, oxygen or methylene; and A is an optionally substituted phenyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, thiadiazolyl, oxadiazolyl, furyl, thienyl or pyridyl ring; and nontoxic pharmaceutically acceptable salts, hydrates, solvates or N-oxides thereof are novel anit-ulcer agents. Intermediates and processes for their preparation are disclosed.Type: GrantFiled: June 23, 1981Date of Patent: February 15, 1983Assignee: Bristol-Myers CompanyInventors: Ronnie R. Crenshaw, Aldo A. Algieri
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Patent number: 4362736Abstract: Novel guanidinothiazole compounds of the general formula ##STR1## wherein R represents a hydrogen atom or a lower alkyl group, Y represents a sulfur atom or a methylene group, m and n each represents an integer of 1-3, A represents the group shown by ##STR2## (wherein R.sub.1 represents a hydrogen atom, a cyano group, a carbamoyl group, a ureido group, a hydroxyl group, a lower alkoxy group, a lower acyl group, an acylamino group, an arylsulfamoyl group, an aralkyl group or a carboxymethyl group, an arylsulfamoyl group, an aralkyl group or a carboxymethyl group, R.sub.2 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a cyano group or a lower acyl group, and R.sub.3 represents a hydrogen atom, a lower alkyl group, a hydroxyl group or a sulfamoyl group), and the pharmacologically acceptable acid addition salts thereof; these compounds are useful as gastric acid secretion inhibitors.Type: GrantFiled: March 6, 1980Date of Patent: December 7, 1982Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Yasufumi Hirata, Isao Yanagisawa, Yoshio Ishii, Masaaki Takeda
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Patent number: 4353833Abstract: Compounds of the general formula I ##STR1## where the radicals A, A.sup.1 and B are identical or different andA is unsubstituted or substituted benzene or heteroaromatic,A.sup.1, if n=1, is unsubstituted or substituted heteroaromatic or is aryl which is unsubstituted or substituted by alkyl, aryl, cycloalkyl, chlorine, bromine, hydroxyl, alkoxy, aryloxy, nitro, hydroxycarbonyl, alkoxycarbonyl, or aminocarbonyl, and, if n>1, A.sup.1 may also be aryl substituted by unsubstituted or substituted amino,B is a bridge member of the formula ##STR2## B.sup.1 is a bridge member which may or may not be quaternized, R.sup.1 and R.sup.2 are hydrogen, unsubstituted or substituted alkyl, cycloalkyl, aryl, alkoxy or amino,n is an integer equal to or greater than 1 andX.sup..theta. is an anion.The compounds according to the invention are preferably used for coloring paper pulp.Type: GrantFiled: November 12, 1980Date of Patent: October 12, 1982Assignee: BASF AktiengesellschaftInventors: Horst Bruder, Hans-Juergen Degen, Franz Feichtmayr, Klaus Grychtol, Udo Mayer
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Patent number: 4348403Abstract: 2-Amino-4-(4-benzyloxyphenyl)thiazole compounds of the formula: ##STR1## wherein X is hydrogen, a halogen, a lower alkyl having 1 to 4 carbon atoms or trifluoromethyl; R is hydrogen, a lower alkyl having 1 to 4 carbon atoms, a lower alkenyl having 2 to 4 carbon atoms or a carboxylic acyl having 1 to 6 carbon atoms; and n is 1 or 2, or pharmaceutically acceptable salts thereof, are novel compounds and are useful as a prophylactic agent or therapeutic agent against hyperlipemia in mammals including human beings.Type: GrantFiled: October 16, 1980Date of Patent: September 7, 1982Assignee: Takeda Chemical Industries, Ltd.Inventors: Yutaka Kawamatsu, Takashi Sohda, Yoshio Imai
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Patent number: 4347370Abstract: The invention relates to guanidine derivatives of imidazoles and thiazoles which are histamine H-2 antogonists and which inhibit the secretion of gastric acid, to methods for their manufacture, to pharmaceutical compositions containing them and to methods of using such guanidine derivatives and compositions. The guanidine derivatives are of the general formula I: ##STR1## in which X is S or NH, Y is O, S, or SO, m is 1 to 4 and n is suitably 1 to 4, R.sup.1 is hydrogen, halogen or alkyl, R.sup.2 is hydrogen, alkyl, alkanoyl or aroyl, A is a 3,4-dioxocyclobuten-1,2-diyl radical or C.dbd.Z in which Z is O, S, NCN, NNO.sub.2, CHNO.sub.2, NCONH.sub.2, C(CN).sub.2, NCOR.sup.3, NCO.sub.2 R.sup.3, NSO.sub.2 R.sup.3 or NR.sup.4 in which R.sup.3 is alkyl or aryl and R.sup.4 is hydrogen or alkyl, B is alkoxy or alkylthio or NR.sup.5 R.sup.6 in which R.sup.5 and R.sup.6 are independently hydrogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, alkoxyalkyl, alkylaminoalkyl or dialkylaminoalkyl; and the salts thereof.Type: GrantFiled: July 25, 1980Date of Patent: August 31, 1982Assignees: Imperial Chemical Industries Ltd., ICI Americas Inc.Inventors: David J. Gilman, James M. Wardleworth, Tobias O. Yellin
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Patent number: 4340537Abstract: Dyes of the thiazole series, having the general formula I ##STR1## where D is the radical of an aromatic diazo component,R is a heterocyclic radical andR.sup.1 and R.sup.2 are hydrogen or unsubstituted or substituted hydrocarbon radicals, which may also together form a ring, which may or may not be heterocyclic.The dyes according to the invention are particularly suitable for dyeing synthetic polyesters.Type: GrantFiled: February 26, 1980Date of Patent: July 20, 1982Assignee: BASF AktiengesellschaftInventors: Heinz Eilingsfeld, Guenter Hansen, Guenther Seybold
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Patent number: 4335133Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are alkyl or --CH.sub.2 --.sub.n wherein n=4 through 7; X is sulfur or NR.sup.3 wherein R.sup.3 is alkyl, alkenyl, alkynyl or cycloalkyl; Ar is an aromatic group of 6 to 12 carbon atoms substituted with 1 to 5 halo groups, 2 nitro groups, or 1 to 5 haloalkyl groups have bactericidal and fungicidal activity.Type: GrantFiled: November 6, 1980Date of Patent: June 15, 1982Assignee: Chevron Research CompanyInventor: Edward I. Aoyagi
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Patent number: 4331680Abstract: Novel compounds are described which are substituted benzophenone hydrazones. They have pesticidal activity, especially against insects and acarids, and pesticidal compositions and methods are described. Methods of making the compounds, and novel intermediates, are also described.Type: GrantFiled: August 25, 1980Date of Patent: May 25, 1982Assignee: The Boots CompanyInventors: David P. Giles, John C. Kerry, Antonin Kozlik, Bryan H. Palmer, Stephen W. Shutler, Robert J. Willis
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Patent number: 4326876Abstract: Compounds of the following formula have herbicidal activity: ##STR1## wherein X and Y are hydrogen or halo; R.sup.2 and R.sup.3 are alkyl or are joined to form --CH.sub.2 --.sub.n, n=2 through 7; R is hydrogen, haloacetyl, alkyl, alkoxyalkyl or N-alkylcarbamoyl and R.sup.1 is alkyl, alkenyl, alkynyl, cycloalkyl, polycycloalkyl, alkoxy-alkyl, cyanoalkyl or cyanoalkenyl; with the proviso that when R and R.sup.1 are both alkyl, each contains at least 3 carbon atoms.Type: GrantFiled: January 28, 1980Date of Patent: April 27, 1982Assignee: Chevron Research CompanyInventor: Edward I. Aoyagi
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Patent number: 4324899Abstract: Disclosed are novel 2-amino-5-cyanothiazoles and the preparation thereof by a novel, two-step process. The cyanothiazoles have the formula ##STR1## wherein R.sup.1 is selected from hydrogen; straight or branched alkyl of 1-20 carbons which may be substituted with 1-3 halogens; phenyl and phenyl substituted with 1-3 halogens, straight or branched alkyl of 1-20 carbons, straight or branched alkoxy of 1-20 carbons, cyano, nitro or trifluoromethyl; 2-thiophene; and .alpha.-pyridine. These compounds are useful, for example, as the diazo moiety of azo dyes prepared through diazotization and coupling with compounds such as aniline type couplers. The process for their manufacture comprises reacting in substantially anhydrous formic acid at from about 50.degree. to about 110.degree. C., hydroxylamine, preferably the salts thereof such as [NH.sub.3 OH]Cl, [NH.sub.3 OH]HSO.sub.4, [NH.sub.3 OH].sub.2 SO.sub.4, and [NH.sub.3 OH]NO.sub.Type: GrantFiled: June 2, 1980Date of Patent: April 13, 1982Assignee: Eastman Kodak CompanyInventor: Mark D. Frishberg
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Patent number: 4316032Abstract: The present invention relates to the compounds of formula I ##STR1## and metal complexes thereof, in which both R.sub.1 's are hydrogen or halogen or form a condensed ring of the benzene series, or --S--CH.sub.2 CH.sub.2 --S--, andR.sub.3 is hydrogen, a mono- or dicyclic-aromatic group or is a divalent radical of the phenylene or naphthalene series linking one further compound of formula I, wherein R.sub.3 is a direct bond and the R.sub.1 groups are the same as or different from the R.sub.1 groups of the first compound of formula I,which metal complexes are either 1:1 metal complexes when R.sub.3 is a divalent linking radical, or 1:2 metal complexes of monomeric compounds of formula I such 1:2 complexes being symmetric or asymmetric and the metal is a divalent transition metal, the complexes are useful as pigments.Type: GrantFiled: April 28, 1980Date of Patent: February 16, 1982Assignee: Sandoz Ltd.Inventor: Peter Bitterli
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Patent number: 4315009Abstract: The guanidine derivative has the formula: ##STR1## where X is O or S: Y is N, CH or CCH.sub.3 : m is 0 or 1: R.sup.1 is hydrogen and R.sup.2 cyano, trifluoroacetyl, C.sub.1-6 alkanoyl, 4,5-dihydro-4-oxothiazol-2-yl or A-B where A is 3,4-dioxocyclobutene-1,2-diyl or C.dbd.Z where Z is oxygen, sulphur, NCN, NNO.sub.2, CHNO.sub.2, NCONH.sub.2, C(CN).sub.2, NCOR.sup.6, NCO.sub.2 R.sup.6, NSO.sub.2 R.sup.6 or NR.sup.7 where R.sup.6 is C.sub.1-6 alkyl and R.sup.7 is hydrogen or C.sub.1-6 alkyl and B is C.sub.1-6 alkyl, alkoxy or alkylthio or NR.sup.8 R.sup.9 where R.sup.8 and R.sup.9 are hydrogen, C.sub.1-10 alkyl, C.sub.3-10 -alkenyl, alkynyl or alkoxyalkyl, C.sub.2-6 (primary hydroxy)alkyl, or, when R.sup.9 is hydrogen, R.sup.8 is 2-[[5-dimethylaminomethylfuran-2-yl]methylthio]-ethylamino or R.sup.8 and R.sup.9 are together a 5- or 6-membered non-aromatic ring optionally containing an additional N or O; or R.sup.1 and R.sup.2 are together imidazolidin-2-ylidene: R.sup.3 is hydrogen or fluorine: R.sup.Type: GrantFiled: January 18, 1979Date of Patent: February 9, 1982Assignee: Imperial Chemical Industries LimitedInventors: Derrick F. Jones, Keith Oldham