Nitrogen, Other Than As Nitro Or Nitroso, Attached Indirectly To The Quinoline Ring System By Nonionic Bonding Patents (Class 546/176)
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Patent number: 4692445Abstract: A class of bicyclic benzenoid aminoalkylene ether and thioether compounds exhibiting pharmacological activity, including anti-secretory and anti-ulcerogenic activity, pharmaceutical compositions comprising these compounds, and methods for the treatment of gastrointestinal hyperacidity and ulcerogenic disorders in mammals using said compositions.Type: GrantFiled: November 12, 1986Date of Patent: September 8, 1987Assignee: Rorer Pharmaceutical CorporationInventors: Donald E. Kuhla, Henry F. Campbell, William L. Studt
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Patent number: 4681940Abstract: There are disclosed compounds of the formula ##STR1## wherein X is N or CR.sup.2Y is O, S, NR.sup.2, CHR.sup.2 or C(R.sup.2).sub.2 when n=0, or N or CR.sup.2 when n=1;p is 0-3;R.sup.1 is ##STR2## R.sup.2 is hydrogen or lower alkyl; R.sup.3 is hydrogen, lower alkyl, phenyl, thienyl, furyl, pyridyl, ##STR3## --C(R.sup.4).sub.3 or --(CH.sub.2).sub.p COOR.sup.2 ; R.sup.4 is halo;Z is O or S;and the pharmaceutically acceptable salts thereof, and their use in the treatment of luekotriene-mediated naso-bronchial obstructive airpassageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like, in psoriasis, ulcerative colitis, rheumatoid arthritis as well as in other immediate hypersensitivity reactions.Type: GrantFiled: November 19, 1985Date of Patent: July 21, 1987Assignee: American Home Products CorporationInventors: John H. Musser, Reinhold H. W. Bender
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Patent number: 4677210Abstract: Z is a chemical bond or an alkylene chain containing up to 5 carbons in the principal chain and up to a total of 7 carbons;X is O or S;R and R.sub.1 are independently hydrogen, hydroxy, lower alkoxy, lower alkanoyloxy, halo, cyano, carboloweralkoxy, carboxyloweralkyl, aryloxy or benzyloxy;R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are independently hydrogen, lower alkyl, lower aralkyl, lower alkenyl, lower alkynyl, aryl or carboxyloweralkyl;and pharmaceutically acceptable salts thereof have pharmaceutical activity, particularly as lipoxygenase inhibitors possessing anti-inflammatory and anti-allergic properties.Type: GrantFiled: June 19, 1985Date of Patent: June 30, 1987Assignee: Rorer Pharmaceutical CorporationInventor: Fu-chih Huang
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Patent number: 4670446Abstract: The invention provides the compounds of formula ##STR1## in which n equals 1 or 2,R denotes hydrogen, alkyl of 1 to 4 carbon atoms or phenyl,R.sub.1 denotes hydrogen, alkyl of 1 to 4 carbon atoms or alkenyl of 2 to 4 carbon atoms, X and Y, which may be identical or different, are each attached to the quinoline ring system in position 5, 6, 7 or 8, and each denote hydrogen or alkoxy of 1 to 3 carbon atoms. These compounds are useful in the treatment of cardiac arrhythmias.Type: GrantFiled: March 6, 1985Date of Patent: June 2, 1987Assignee: Rhone-Poulenc SanteInventors: Michel Mestre, Christian Renault
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Patent number: 4659720Abstract: 5-Amino or substituted amino imidazoles are disclosed as having anticoccidial activity. The compounds are useful for controlling cecal and or intestinal coccidiosis when administered in minor quantitites to animals, in particular to poultry, usually in admixture with animal sustenance.Type: GrantFiled: November 16, 1983Date of Patent: April 21, 1987Assignee: Merck & Co., Inc.Inventors: John C. Chabala, Michael H. Fisher, Arthur A. Patchett
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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: 4640708Abstract: Compounds of the formula ##STR1## wherein: R.sup.5 is a bicyclic aryl or nitrogen-containing heteroaryl ring system such as naphthyl, quinolyl, isoquinolyl or tetrahydroisoquinolyl, optionally substituted by a wide variety of groups;R.sup.4 and R.sup.1 are preferably hydrogen but may be other groups andR.sup.2 and R.sup.3 are selected from alkyl, haloalkyl, alkenyl, haloalkenyl and alkynyl, show high general grass-killing activity with good selectivity to many broad-leaf crops and in some instances selectivity to small-grain cereals. Processes for the preparation of compounds of formula I, intermediates in the preparation of compounds I and the herbicidal properties of compounds I are described.Type: GrantFiled: March 20, 1984Date of Patent: February 3, 1987Assignee: ICI Australia LimitedInventors: Graham J. Bird, Graeme J. Farquharson, Keith G. Watson
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Patent number: 4634776Abstract: 3-Arylcarbonyl- and 3-cycloalkylcarbonyl-1-aminoalkyl-1H-indoles, useful as analgesic, anti-rheumatic and anti-inflammatory agents, are prepared by reacting a 3-arylcarbonyl- or 3-cycloalkylcarbonylindole with an aminoalkyl halide in the presence of an acid-acceptor; by reacting a 1-aminoalkyl-1H-indole with an arylcarboxylic acid halide or a cycloalkanecarboxylic acid halide in the presence of a Lewis acid; or by reacting a 3-arylcarbonyl- or 3-cycloalkanecarbonyl-1-tosyloxyalkyl- or haloalkyl-1H-indole with an amine.Type: GrantFiled: December 19, 1985Date of Patent: January 6, 1987Assignee: Sterling Drug, Inc.Inventor: Malcolm R. Bell
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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: 4617395Abstract: Quinoline and substituted quinolines are prepared by reacting aniline or a substituted aniline with an .alpha., .beta.-monounsaturated aldehyde in a high-boiling mineral oil by a method in which the high-boiling mineral oil is replaced when it becomes enriched with by-products, and the said mineral oil enriched with by-products is removed.Type: GrantFiled: October 15, 1984Date of Patent: October 14, 1986Assignee: BASF AktiengesellschaftInventors: Toni Dockner, Helmut Hagen, Herbert Krug
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Patent number: 4613607Abstract: Antiarhythmic medicaments containing, as active substance, a compound of the formula: ##STR1## in which n is 1 or 2, X and Y are fixed in positions 5, 6, 7 or 8 on the quinoline cycle and each represents a hydrogen atom or an alkoxy group having 1 to 3 carbons, R is a hydrogen atom or an alkyl group having 1 to 4 carbons, cycloalkyl having 3 to 8 carbons, phenyl or phenyl substituted by alkoxy having 1 to 4 carbons, R.sub.1 is a hydrogen atom or an alkyl group having 1 to 4 carbons or a phenylalkyl group of which the alkyl part has 1 to 3 carbons, R.sub.2 is a hydrogen atom, an alkyl group having 1 to 2 carbons or an alkenyl group having 2 to 4 carbons.Type: GrantFiled: September 30, 1983Date of Patent: September 23, 1986Assignee: Pharmuka LaboratoiresInventors: Claude G. A. Gueremy, Michel A. P. Mestre, Christian L. A. Renault
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Patent number: 4600776Abstract: Cationic enamine dyestuffs of the general formula ##STR1## in which the symbols have the meaning given in the description, are used for dyeing natural and synthetic substrates and compositions which can be dyed with cationic dyestuffs, in particular paper.Type: GrantFiled: June 11, 1984Date of Patent: July 15, 1986Assignee: Bayer AktiengesellschaftInventors: Karlheinrich Meisel, Roderich Raue
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Patent number: 4587341Abstract: Compounds of the formula (II) ##STR1## or a salt, N-oxide or acyl derivative thereof, wherein Y is a group ##STR2## which is optionaly substituted and which optionally contain a nitrogen atom at one of positions A, B, C, D or E, in which the dotted line represents aromatic rings unless one of the rings contains a nitrogen atom in which case this ring is either aromatic or partially saturated, have antimicrobial properties. Processes for making these compounds, pharmaceutical compositions containing them and the medical use of the compounds are also disclosed.Type: GrantFiled: April 29, 1983Date of Patent: May 6, 1986Assignee: Burroughs Wellcome Co.Inventors: Barbara Roth, Barbara S. Rauckman
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Patent number: 4581178Abstract: Low valent transition metal complexes containing small cone angle phosphine or arsine ligands efficiently catalyze addition of aldehydes to compounds or groups having a C--H bond activated by a nitro or nitrile group, to provide nitroalcohols or cyanohydrins, respectively.Type: GrantFiled: February 28, 1985Date of Patent: April 8, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: David Milstein
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Patent number: 4579855Abstract: Mefloquin hydrochloride in the form of modification E as characterized by IR spectrum and X-ray diffraction pattern, as well as a process for the preparation thereof by treating mefloquin hydrochloride, comprising at least partially another modification, that is, mefloquin hydrochloride which is not pure mefloquin hydrochloride in the form of modification E, with methanol and/or ethanol, in the presence of less than 30 volume/percent of water.Type: GrantFiled: October 1, 1984Date of Patent: April 1, 1986Assignee: Hoffmann-La Roche Inc.Inventors: Helmut Bomches, Bruno Hardegger
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Patent number: 4576949Abstract: The present invention also provides novel compositions of matter. In particular, the present invention provides novel 3-substituted compounds of formula I which are from among the selected 5,6,7,8-tetrahydroquinolines and 5,6-dihydropyrindines having use as inhibitors of the synthesis of leukotrienes and as inhibitors of the action of lipoxygenase in mammalian metabolism.Type: GrantFiled: May 7, 1984Date of Patent: March 18, 1986Assignee: The Upjohn CompanyInventor: Herman W. Smith
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Patent number: 4569933Abstract: This invention relates to new chemical compounds which are derivatives of 2,5-diaminodiazoles.It relates more particularly to new 2-amino 5-(aralkylamino piperidino alkyl) diazoles.These compounds and the acid addition salts thereof have interesting therapeutical properties, particularly anti-hypertensive properties which make them useful as active ingredient of pharmaceutical compositions.Type: GrantFiled: April 13, 1984Date of Patent: February 11, 1986Inventors: Pierre-Jean Cornu, Claude Perrin, Bernard Dumaitre, Gilles Streichenberger
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Patent number: 4567269Abstract: 5-isothiocyanato-2-methylquinolines, N-(2,2-dialkoxyethyl)-N'-(2-methylquinolin-5-yl)thioureas, 5-(2-mercaptoimidazol-1-yl)-2-methylquinolines, 5-(imidazol-1-yl)-2-methylquinolines, 5-(imidazol-1-yl)-1,2,3,4-tetrahydro-2-methylquinolines and dialkoxy 2-[N-(5-(imidazol-1-yl)-1,2,3,4-tetrahydro-2-methylquinolinyl)]methylenema lonates are described as intermediates for antimicrobial 6,7-dihydro-8-(imidazol-1-yl)-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2- carboxylic acids.Type: GrantFiled: June 25, 1984Date of Patent: January 28, 1986Assignee: Riker Laboratories, Inc.Inventor: John F. Gerster
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Patent number: 4565872Abstract: A process for preparing 8-cyano-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acids from substituted benzoic acids. Intermediates involved in the process are also described. 8-cyano-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acids are antimicrobial agents.Type: GrantFiled: October 26, 1983Date of Patent: January 21, 1986Assignee: Riker Laboratories, Inc.Inventor: Charles M. Leir
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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: 4551460Abstract: Pyrido[2,1-b]quinazoline derivatives of the formulas ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are as hereinafter set forth, are described. The compounds of formulas I and II are useful as agents for the treatment of allergic conditions as well as for the treatment of vascular disorders involving thrombosis.Type: GrantFiled: March 2, 1983Date of Patent: November 5, 1985Assignee: Hoffmann-La Roche Inc.Inventor: Jefferson W. Tilley
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Patent number: 4547509Abstract: Compounds of the structure ##STR1## and pharmaceutically acceptable salts thereof wherein: R.sub.1 is H, alkyl, alkoxy, carboxyl, alkylcarboxy, acylamino, dialkyl amino, trihalomethyl, halogen, nitro, hydroxy or cyano;X is in the 5, 6 or 7 position and is O(CH.sub.2).sub.n, N(CH.sub.2).sub.n --R.sub.3, S(CH.sub.2).sub.n or (CH.sub.2).sub.n ;Y is O(CH.sub.2).sub.n, S(CH.sub.2).sub.n, N(CH.sub.2).sub.n --R.sub.3 where R.sub.3 is H, alkyl or (CH.sub.2).sub.n ;R.sub.2 is monosubstituted or independently disubstituted H, hydroxy, alkyl, halogen, nitro, alkoxy, carboxyl, alkylcarboxy, trihalomethyl, cyano, trifluoromethyl, dialkylamino or acylamino;Z is O, S or (NR.sub.3).sub.2 where R.sub.3 is H, alkyl or aryl; andn is 0 to 10 inclusiveuseful in the treatment of ischemic heart disease and hypertriglyceridemia.Type: GrantFiled: January 3, 1983Date of Patent: October 15, 1985Assignee: USV Pharmaceutical Corp.Inventors: John H. Musser, Charles A. Sutherland
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Patent number: 4544748Abstract: A process for the preparation of mefloquin and its physiologically compatible acid addition salts by reacting 6-phthalimido-1-hexene with a 4-halo-2,8-bis-(trifluoromethyl)-quinoline in the presence of a base, epoxidizing the resulting N-[6-<2,8-bis-(trifluoromethyl)-4-quinolyl>-5-hexenyl]-phthalimide to give N-[4-{3-<2,8-bis-(trifluoromethyl)-4-quinolyl>-2-oxiranyl}-butyl]-phthalim ide, treating the latter with hydrazine hydrate and, where applicable, converting the product into an acid addition salt as well as intermediates obtained in this process.Type: GrantFiled: August 22, 1983Date of Patent: October 1, 1985Assignee: Hoffmann-La Roche Inc.Inventor: Solange Adam-Molina
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Patent number: 4544661Abstract: Compounds of the formula: ##STR1## wherein X is oxygen or sulfur;R is pyridyl optionally substituted with 1 to 3 substituents independently selected from halogen, lower alkyl or lower alkoxy optionally substituted with 1 to 3 of the same or different halogen atoms or nitro, R.sup.1 is lower alkyl; and R.sup.2 is a 5- or 6-membered heterocyclic ring containing 1- to 3-ring nitrogens and the remainder of the ring atoms carbon atoms, a quinoline ring or a phenyl ring, all optionally substituted with 1 to 3 substituents independently selected from halogen, trihalomethyl, lower alkyl or lower alkoxy, provided that R.sup.2 is not bonded to the --CH.sub.2 -- group by a ring nitrogen and compatible salts thereof, are fungicidal.Type: GrantFiled: September 23, 1983Date of Patent: October 1, 1985Assignee: Chevron Research CompanyInventor: David C. K. Chan
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Patent number: 4539406Abstract: An improved process for preparing fused carbocyclic ring derivatives of pyridine especially 5,6,7,8-tetrahydroquinoline 8-nitriles, amides and thioamides is described. The nitriles and thioamides are anti-ulcer and/or anti-secretory agents. Typically a compound of formula A ##STR1## wherein M is sodium, potassium, lithium or MgHal where Hal is chlorine, bromine or iodine, is reacted with a silyl compound R.sub.x.sup.a Si(NCY).sub.4-x III, wherein R.sup.a is selected from electron donating substituents, e.g. alkoxy or dialkylamino, and hydrocarbon substituents e.g. alkyl, at least one R.sup.a being an electron donating substituent, Y is oxygen or sulphur, x has a value from 1 to 3, then subjecting the product to hydrolysis or alcoholysis to obtain the corresponding nitrile, amide or thioamide, provided that when a nitrile is desired the molar ratio of compound III to compound A is at least 2:1 and x is 3 and Y is S. The products may be isolated as acid addition salts.Type: GrantFiled: June 21, 1983Date of Patent: September 3, 1985Assignee: John Wyeth & Brother LimitedInventor: Roger Crossley
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Patent number: 4529798Abstract: Fused carbocyclic ring derivatives of pyridine which contain a nitrile or thioamide group on the carbocyclic ring e.g. 8-cyano or thiocarboxamido-5,6,7,8-tetrahydroquinolines are prepared by a process in which a sodium, potassium, lithium or magnesium halide derivative of the pyridine compound is treated with a compound RaRbNCN wherein Ra and Rb are the same or different and represent alkyl, cycloalkyl, or aralkyl, or Ra and Rb are joined to form a heterocyclic ring with the nitrogen, and the product is treated with a proton source to obtain the nitrile which is optionally treated with a sulphurizing agent to form the thioamide. The nitriles or thioamides may be isolated as their acid addition salts.Type: GrantFiled: December 2, 1981Date of Patent: July 16, 1985Assignee: John Wyeth & Brother LimitedInventor: Robin G. Shephard
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Patent number: 4526970Abstract: An improved process for preparing tetrahydroquinolines and related compounds especially 5,6,7,8-tetrahydroquinoline-8-nitriles, amides and thioamides is described. The nitriles and thioamides are anti-ulcer and/or anti-secretory agents. Typically a compound of formula A ##STR1## where M is sodium, potassium, lithium or MgHal where Hal is chlorine, bromine or iodine, is reacted, e.g., in an ether solvent, with a silyl compound R.sub.x.sup.a Si(NCY).sub.4-x (III) wherein R.sup.a is alkyl, cycloalkyl, aralkyl, or aryl, at least one group R.sup.a being a branched chain alkyl, cycloalkyl, aryl or branched chain aralkyl, Y is oxygen or sulphur, x has a value from 1 to 3, then subjecting the product to hydrolysis or alcoholysis, to obtain the corresponding nitrile, amide or thioamide, provided that when a nitrile is desired the molar ratio of compound III to compound A is at least 2:1 and x is 3 and Y is S. The products may be obtained as acid addition salts.Compound A may contain various substituents, e.g.Type: GrantFiled: June 21, 1983Date of Patent: July 2, 1985Assignee: John Wyeth & Brother LimitedInventor: Robin G. Shepherd
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Patent number: 4521424Abstract: The compound of formula (I) ##STR1## possesses markedly increased solubility under aqueous conditions and improved pharmacokinetic profile against malaria-causing parasites. Pharmaceutical compositions and method of treatment of subjects with malaria are also disclosed.Type: GrantFiled: February 27, 1984Date of Patent: June 4, 1985Assignee: SmithKline Beckman CorporationInventor: Jean F. Rossignol
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Patent number: 4521606Abstract: Herein is disclosed bicyclic-substituted aminoethanol derivatives, therapeutically acceptable acid addition salts thereof, processes for their preparation, methods of using the derivatives and pharmaceutical compositions. The derivatives are useful for treating hypertension in a mammal.Type: GrantFiled: June 30, 1983Date of Patent: June 4, 1985Assignee: American Home Products Corp.Inventors: Andre A. Asselin, Danilo A. Crosilla, Leslie G. Humber
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Patent number: 4507482Abstract: A method for obtaining mefloquin hydrochloride, erythro-.alpha.-2-piperidyl-2,8-bis-(trifluoromethyl)-4-quinolinemethanol hydrochloride, from mixtures of erythro-and threo-.alpha.-2-piperidyl-2,8-bis-(trifluoromethyl)-4-quinolinemethanol hydrochloride by treatment with aqueous methanol or ethanol. The thermodynamically most stable form is obtained by treatment with an alcohol/water mixture for a long period of time.Type: GrantFiled: April 4, 1983Date of Patent: March 26, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Helmut Bomches, Bruno Hardegger
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Patent number: 4497651Abstract: Dichloroquinoline derivatives of the formula ##STR1## are prepared as described, and are used as herbicides.Type: GrantFiled: February 17, 1982Date of Patent: February 5, 1985Assignee: BASF AktiengesellschaftInventors: Helmut Hagen, Juergen Markert, Bruno Wuerzer
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Patent number: 4496569Abstract: (1H-Tetrazol-5-yl)tetrazolo[1,5-a]quinolines and related compounds which are useful as antiallergic agents are described herein. The compounds are prepared by the reaction of an appropriate halocyanoquinoline or isoquinoline with ammonium chloride and an azide such as sodium azide in an inert solvent such dimethylformamide.Type: GrantFiled: March 25, 1983Date of Patent: January 29, 1985Assignee: The Dow Chemical CompanyInventor: Terry L. Wright
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Patent number: 4479950Abstract: Compounds of the structure ##STR1## wherein: P and Q are independently hydrogen, halo, CF.sub.3, OR.sub.1, SR.sub.1, sulfamoyl, alkyl and NR.sub.1 R.sub.2 ;R.sub.1, and R.sub.2 are independently hydrogen, alkyl, aminoalky, aryl, aralkyl, heteroaryl or cycloalkyl;Y is OH, OR.sub.1, NH.sub.2, or, N(R.sub.1 R.sub.2); andM is alkyl, cycloalkyl, aryl, aminoalkyl, aralkyl, heteroaryl or heterocyclicwherein:the alkyl groups and the alkyl moieties of aminoalkyl, alkoxy and thioalkyl contain from 1 to 6 carbon atoms; the cycloalkyl group contains from 3 to 8 carbon atoms; the aryl group contains from 6 to 10 carbon atoms; the aralkyl group contains from 7 to 16 carbon atoms; and the hetero group is selected from pyrrolidyl, piperidinyl, morpholinyl, pyridyl, quinolinyl, furyl, furfuryl and thienyl; and where Y is a hydroxy, their pharmaceutically acceptable, non-toxic alkali, alkaline earth and amine salts, have angiotensin converting enzyme inhibitory activity.Type: GrantFiled: November 5, 1982Date of Patent: October 30, 1984Assignee: USV Pharmaceutical CorporationInventors: Paul R. Menard, Howard Jones, John T. Suh
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Patent number: 4472403Abstract: The invention is concerned with novel quinicine and cinchonicine derivatives having cardiovascular activities of the formula or a salt thereof, ##STR1## in which A--B is --CH.sub.2 --CH.sub.2, --CHOH--CH.sub.2 --, --CH.sub.2 --CHOH--, --C(O)--CH.sub.2 --, --CH.sub.2 --C(O)--, --C(NOR.sup.4)--CH.sub.2 -- or --CH.sub.2 --C(NOR.sup.4)--; R.sup.1 is hydrogen, hydroxy or lower alkoxy; R.sup.2 is ethyl or vinyl; R.sup.3 is C.sub.2-8 alkyl, C.sub.1-8 hydroxyalkyl, lower alkoxy-alkyl or lower alkanoyloxyalkyl, C.sub.Type: GrantFiled: October 28, 1980Date of Patent: September 18, 1984Assignee: A.C.F. Chemiefarma N.V.Inventors: Hans B. Trijzelaar, Ronus de Bode, Hendricus B. A. Welle
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Patent number: 4468404Abstract: 3-Aralkyloxy-2,3-dihydro-2-(triazolylmethyl)benzo(b)thiophenes and related derivatives having antifungal, antibacterial, and antiprotozoal activity are prepared by the reaction of the corresponding 2,3-dihydro-3-hydroxy-2-(triazolylmethyl)benzo(b)thiophene or related derivative and an aralkyl halide.Preferred compounds are those where the aralkyl function is a hetercyclic aromatic, particularly 2-chloro-3-thenyl, and where the benzene nucleus is substituted by chlorine or fluorine.Pharmaceutical formulations comprising compounds of this invention are described, as well as the method for their use in treating microbial infections.Type: GrantFiled: July 29, 1982Date of Patent: August 28, 1984Assignee: Schering CorporationInventors: Dinanath F. Rane, John J. Wright, Russell E. Pike
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Patent number: 4460594Abstract: Compounds of the formula (I), and pharmaceutically acceptable salts thereof: ##STR1## wherein: R.sub.1 is hydroxy, C.sub.1-4 alkoxy or an in-vivo hydrolysable acyloxy group:R.sub.2 is hydrogen, C.sub.1-4 alkyl, hydroxy, C.sub.1-4 alkoxy or an in-vivo hydrolysable acyloxy group;R.sub.4 is benzofuryl, benzothienyl, indolyl, quinolyl, isoquinolyl,2,3-dihydrobenzofuryl, 2,3-dihydrobenzylthienyl or 2,3-dihydroindolyl optionally substituted by one or two substituents selected from C.sub.1-4 alkoxy, hydroxy or acyloxy, trifluoromethyl, halogen or nitro; andA is a bond or C.sub.1-6 alkylene,a process for their preparation, and pharmaceutical compositions containing them.Type: GrantFiled: September 15, 1982Date of Patent: July 17, 1984Assignee: Beecham Group p.l.c.Inventor: Roger E. Markwell
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Patent number: 4456758Abstract: New heterocyclic nitriles of the formula: ##STR1## wherein (i) Het represents a heterocyclic radical of aromatic character containing one or two nitrogen atoms selected from pyrid-3-yl, pyrid-4-yl, pyridazinyl, pyrazinyl, pyrimidinyl, quinolyl, imidazolyl, naphthyridinyl, quinoxalinyl and quinazolinyl, X represents an oxygen atom and Y represents a valency bond or a methylene radical, or altenatively X represents a sulphur atom and Y represents a sulphur atom, a valency bond or a methylene radical, or(ii) Het represents the pyrid-2-yl radical, X represents an oxygen atom and Y represents a valency bond or a methylene radical, or alternatively X represents a sulphur atom and Y represents a sulphur atom or a methylene radical, are useful, in particular, as intermediates for the preparation of therapeutically useful heterocyclic thioformamides by converting the depicted cyano radical into a grouping --CSNHR wherein R represents a hydrogen atom or an alkyl (C.sub.1-4) radical.Type: GrantFiled: August 10, 1982Date of Patent: June 26, 1984Assignee: Rhone-Poulenc SanteInventors: Jean-Claude Aloup, Jean Bouchaudon, Daniel Farge, Claude James
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Patent number: 4443453Abstract: The invention is concerned with novel quinoline derivatives of the formula ##STR1## or a salt thereof, in which A--B is --CH.sub.2 --CH.sub.2 --, --CHOH--CH.sub.2 --, --CH.sub.2 --CHOH--, --CH.sub.2 --C(O)--, --C(NOR.sup.4)--CH.sub.2 -- or --CH.sub.2 --C(NOR.sup.4)--, R.sup.1 is hydrogen, hydroxy or lower alkoxy, R.sup.2 is lower alkyl, R.sup.3 is ethyl or vinyl, R.sup.4 is lower alkyl, whereby the substituents at the 3- and 4-position of the piperidine ring are in the cis-position. The compounds of the formula may be in the form of the optically active enantiomers and/or their therapeutically acceptable salts. Furthermore the invention provides pharmaceutical compositions possessing cardiovascular activities in which as active compound at least a compound of the above formula is used. Methods for the preparation of the pharmaceutical compositions and of the active compounds are also included by the invention.Type: GrantFiled: March 5, 1981Date of Patent: April 17, 1984Assignee: ACF Chemiefarma N.V.Inventors: Hans B. Trijzelaar, Ronus de Bode, Handricus B. A. Welle
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Patent number: 4442106Abstract: The invention is concerned with novel quinoline derivatives having cardiovascular activities of formula 1 ##STR1## in which A--B is --CH.sub.2 --CH.sub.2 --, --CHOH--CH.sub.2, --CH.sub.2 --CHOH--, --C(O)--CH.sub.2 --, --CH.sub.2 --C(O)--, --C(NOR.sup.5)--CH.sub.2 -- or --CH.sub.2 --C(NOR.sup.5)--; R.sup.1 is hydrogen, hydroxy or lower alkoxy; R.sup.2 is lower alkyl, hydroxy, lower alkoxy or CF.sub.3 ; R.sup.3 is ethyl or vinyl; R.sup.4 is C.sub.1-9 alkyl, C.sub.2-9 hydroxyalkyl or lower alkoxyalkyl, C.sub.5-6 cycloalkyl, C.sub.3-6 cycloalkyl lower alkyl, cyano lower alkyl, lower alkenyl, lower alkynyl, tetrahydrofurfuryl, mono- or di-lower alkylamino lower alkyl; mono- or di-lower alkylamino lower hydroxyalkyl; phenyl C.sub.1-4 alkyl, phenyl C.sub.1-4 hydroxy-alkyl, diphenyl C.sub.1-4 alkyl, benzoyl C.sub.1-4 alkyl, furyl C.sub.1-4 alkyl, thienyl C.sub.1-4 alkyl, furoyl C.sub.1-4 alkyl or thienoyl C.sub.1-4 alkyl, which groups may be optionally substituted in the aromatic nucleus, and R.sup.Type: GrantFiled: March 5, 1981Date of Patent: April 10, 1984Assignee: ACF Chemiefarma N.V.Inventors: Hans B. Trijzelaar, Ronus de Bode, Hendricus B. A. Welle
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Patent number: 4442107Abstract: The invention is concerned with quinoline derivatives having cardiovascular activities of the formula ##STR1## or a salt thereof, in which A--B is --CH.sub.2 --CH.sub.2 --, --CHOH--CH.sub.2, --CH.sub.2 --CHOH--, --C(O)--CH.sub.2 --, --CH.sub.2 --C(O)--, --C(NOR.sup.4)--CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --C(NOR.sup.4), R.sup.1 is hydrogen, hydroxy or lower alkoxy, R.sup.2 is hydroxy, lower alkoxy, trifluoromethyl, R.sup.3 is ethyl or vinyl and R.sup.4 is lower alkyl. The compounds of the formula may be in the form of their optically active enantiomers and/or their therapeutically acceptable salts. Furthermore the invention provides pharmaceutical compositions possessing cardiovascular activities, in which as active compound at least a compound of the above formula is used. Methods for the preparation of the pharmaceutical compositions and of the active compounds are also disclosed and covered by the invention.Type: GrantFiled: March 5, 1981Date of Patent: April 10, 1984Assignee: ACF Chemiefarma N.V.Inventors: Hans B. Trijzelaar, Ronus de Bode, Hendricus B. A. Welle
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Patent number: 4440941Abstract: Compounds of the structure ##STR1## wherein: Q is oxygen, sulfur or imino.X and Y are hydrogen, halogen, hydroxy, alkoxy, trifluoromethyl, nitro, carboxy, cyano, sulfonamido, sulfhydryl, alkyl, alkenyl, alkynyl, alkanoyl, alkylmercapto, amino, alkylamino, dialkylamino, alkysulfinyl, and alkylsulfonyl and may be the same or different;R.sub.1 is hydrogen, alkanoyl, substituted alkanoyl wherein the substituent is hydroxy, amino or cycloalkyl, aroyl, arylalkanoyl, or cycloalkylcarbonyl,n is an integer from 1 to 4 inclusive,R.sub.2 and R.sub.Type: GrantFiled: December 22, 1980Date of Patent: April 3, 1984Assignee: USV Pharmaceutical CorporationInventors: John T. Suh, Paul R. Menard, Howard Jones
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Patent number: 4433150Abstract: Compounds, useful as medicaments, of the formula: ##STR1## in which R is hydrogen, alkyl, alkenyl or arylalkyl, R.sub.1 is hydrogen, alkyl or alkenyl, R.sub.2 is hydrogen, alkyl, arylalkyl, phenyl, pyridyl, thienyl or substituted phenyl, X is hydrogen, halogen, alkyl, alkoxy, alkylthio, trifluoromethyl, nitro, amino or amino substituted by one or two alkyl groups, and A represents a CO or CH.sub.2 group.Type: GrantFiled: December 2, 1980Date of Patent: February 21, 1984Assignee: PharmindustrieInventors: Alain A. Champseix, Gerard R. Le Fur, Christian L. A. Renault
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Patent number: 4405789Abstract: Compounds useful as medicaments, of the formula: ##STR1## in which X is hydrogen, halogen, alkyl containing 1 to 4 carbon atoms, alkoxy containing 1 to 4 carbon atoms or alkylthio containing 1 to 4 carbon atoms, one of the substituents R.sub.1 and R.sub.2 is hydrogen, alkyl containing 1 to 4 carbon atoms, phenyl or phenyl substituted by halogen, alkyl containing 1 to 4 carbon atoms, alkoxy containing 1 to 4 carbon atoms, alkylthio containing 1 to 4 carbon atoms, trifluoromethyl, nitro, unsubstituted amino or amino substituted by one or two alkyl containing 1 to 2 carbon atoms, and the other of the substituents R.sub.1 and R.sub.2 is a group of the formula: ##STR2## in which n is 1, 2 or 3 and R is hydrogen or alkyl containing 1 to 4 carbon atoms.Type: GrantFiled: February 24, 1981Date of Patent: September 20, 1983Assignee: PharmindustrieInventors: Alain A. Champseix, Gerard R. Le Fur
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Patent number: 4402961Abstract: Compounds, useful as medicaments, of the formula: ##STR1## in which R is fixed in position 2 or 4 on the cycle of the quinoline and indicates a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms, pyridyl, thienyl, phenyl or substituted phenyl group, X is fixed in position 5, 6, 7 or 8 on the cycle of the quinoline and indicates a hydrogen or halogen atom or an alkyl, alkoxy or alkylthio group containing 1 to 4 carbon atoms or CF.sub.3 group, R.sub.1 is a hydrogen atom or an alkyl containing 1 to 4 carbon atoms, alkenyl containing 3 to 4 carbon atoms or arylalkyl group, A is a CO, CHOH, or CH.sub.Type: GrantFiled: June 9, 1981Date of Patent: September 6, 1983Assignee: PharmindustrieInventors: Marie-Christine Dubroeucq, Claude G. A. Gueremy, Gerard R. Le Fur, Jacques Mizoule
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Patent number: 4392968Abstract: The oxidation of a lubricating oil caused by metal components can be suppressed effectively by adding to the lubricating oil a compound represented by the formula ##STR1##Type: GrantFiled: July 30, 1981Date of Patent: July 12, 1983Assignee: Nippon Oil Company, LimitedInventors: Noboru Ishida, Harumichi Watanabe
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Patent number: 4383112Abstract: Chiral Schiff bases according to the general formula: ##STR1## and transition metal complexes thereof, wherein C.sup.* is an asymmetric carbon atom, R.sup.1 and R.sup.2, which may be the same or different are alkyl, aralkyl, aryl or alkaryl, R.sup.3 is hydrogen, alkyl, aralkyl, aryl or alkaryl, R.sup.4 and R.sup.5, which may be the same or different, are hydrogen or lower alkyl or, where n is 1, may with the cyclic ring to which CR.sup.4 R.sup.Type: GrantFiled: July 8, 1980Date of Patent: May 10, 1983Assignee: Imperial Chemical Industries LimitedInventors: Dale A. Laidler, David J. Milner
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Patent number: 4380633Abstract: Methine dyes from tetrahydroquinoline compounds containing N-thioether substituents, in general produce bright yellow shades when applied to polyester fabrics by conventional dyeing procedures, have improved properties such as dyeability, fastness to light, resistance to sublimation, insensitivity to pH changes, and dye at the boil and under pressure to the same depth of shade. These compounds are particularly useful in the thermal fixation technique for dyeing polyester materials.Type: GrantFiled: December 1, 1980Date of Patent: April 19, 1983Assignee: Eastman Kodak CompanyInventors: Clarence A. Coates, Jr., Max A. Weaver
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Patent number: 4379154Abstract: Thioformamide derivatives of the formula: ##STR1## wherein R represents hydrogen or alkyl of 1 through 4 carbon atoms, and (i) Het represents a heterocyclic radical selected from pyrid-3-yl, pyrid-4-yl, pyridazinyl, pyrazinyl, pyrimidinyl, quinolyl, imidazolyl, naphthyridinyl, quinoxalinyl and quinazolinyl, X represents sulphur or oxygen and Y represents sulphur or oxygen, a valency bond or methylene, or (ii) Het represents pyrid-2-yl, X represents sulphur or oxygen and Y represents sulphur or oxygen or methylene, or (iii) Het represents pyrid-2-yl, X represents oxygen and Y represents a valency bond, are new compounds possessing useful pharmacological properties. They are particularly useful in the treatment of gastrointestinal ulcers and in the treatment of hypertension, depending on the definition of the symbol Het.Type: GrantFiled: May 18, 1981Date of Patent: April 5, 1983Assignee: Rhone-Poulenc SanteInventors: Jean-Claude Aloup, Jean Bouchaudon, Daniel Farge, Claude James
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Patent number: 4379166Abstract: This invention relates to 5-(2-alkylamino-1-hydroxyethyl)salicylamides and 4-(2-alkylamino-1-hydroxyethyl)-2-(methylsulfinyl)phenols wherein the alkyl group is substituted by arylmethoxy, arylmethylthio, heteroarylmethoxy, or heteroarylmethylthio, pharmaceutical compositions thereof, and their use as cardiovascular agents.Type: GrantFiled: August 3, 1981Date of Patent: April 5, 1983Assignee: Schering CorporationInventors: Bernard R. Neustadt, Elijah H. Gold
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Patent number: 4372953Abstract: Tetrazole derivatives of the formula: ##STR1## wherein R.sup.1 is a lower alkykl, phenyl or a group of the formula: --S(O).sub.l --A--(X).sub.m --R.sup.3, and R.sup.2 is hydrogen, a lower alkyl, phenyl or a cycloalkyl when R.sup.1 is the group --S(O).sub.l --A--(X).sub.m --R.sup.3, or R.sup.2 is a group of the formula: --B--CO--R.sup.4 when R.sup.1 is a lower alkyl or phenyl and a pharmaceutically acceptable salt thereof, which have prophylactic or therapeutic activities against peptic and/or duodenal ulcers and are useful as an anti-ulcer drug; processes for the preparation of the tetrazole derivatives; and pharmaceutical composition containing said tetrazole derivatives.Type: GrantFiled: February 27, 1981Date of Patent: February 8, 1983Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Minoru Uchida, Takao Nishi, Kazuyuki Nakagawa