Chalcogen Bonded Directly To Ring Carbon Of The Quinuclidine Ring System Patents (Class 546/137)
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Patent number: 4983600Abstract: Aroyl ureas and carbamic acid derivatives of formulaA--CO--NHCW--Y--Band pharmaceutically acceptable salts thereof whereinA is a specified aromatic radical including optionally substituted phenylW is O or SY is NH or S andB is a specified saturated azacyclic ring, eg tropan-3-yl or quinuclidin-3-yl,possess 5-HT.sub.3 -antagonistic activity and are, for example, useful in treatment of migraine, emesis, anxiety, gastro-intestinal disorders and as anti-psychotics.Type: GrantFiled: October 16, 1989Date of Patent: January 8, 1991Assignee: John Wyeth & Brother LimitedInventors: Terence J. Ward, Janet C. White, Gerald Bradley
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Patent number: 4975437Abstract: The four stereoisomers are disclosed having the formula: ##STR1## in which the asymmetric centers a and b are the same or different. The compounds are derived from the (+) and (-) alcohols and the (+) and (-) dihydropyridines and have either the absolute R or S configuration. Also disclosed are pharmaceutical compositions comprising an effective amount of the compounds in a pharmaceutically acceptable carrier and methods for producing cardiotonic activity using the compositions.Type: GrantFiled: December 14, 1989Date of Patent: December 4, 1990Assignee: Marion Laboratories, Inc.Inventors: John P. Carter, Waclaw J. Rzeszotarski
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Patent number: 4970315Abstract: Compounds of formula I ##STR1## wherein X.sup..crclbar. is Cl.sup..crclbar. or Br.sup..crclbar.,M is Cu.sup.2.sbsb..sym. or Ni.sup.2.sbsb..sym.,Z is a halogen atom, --NH.sub.2, C.sub.1 -C.sub.4 alkyl or C.sub.2 -C.sub.4 alkoxy,R.sup.1 is H, methyl methoxy, halogen or --NH.sub.2, andA is a group ##STR2## wherein R.sup.2 and R.sup.3 each independently have the same meaning as R.sup.1.The compounds are simultaneously cryochromic or thermochromic and are suitable as warning indicators for cooled or heated structural elements.Type: GrantFiled: July 26, 1989Date of Patent: November 13, 1990Assignee: Ciba-Geigy CorporationInventor: Beat Schmidhalter
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Patent number: 4966973Abstract: The present invention relates to a compound of the formula ##STR1## wherein R.sup.1 stands for hydrogen or a lower alkyl; n denotes an integer of 1 to 6; X stands for an optionally oxidized sulphur atom, oxygen atom or an optionally substituted imino; R.sup.2 stands for methyl or an organic residual group bonded through methylene, methine a quaternary carbon; R.sup.3 stands for a lower alkyl; R.sup.4 stands for hydrogen or acyl; R.sup.5 and R.sup.6 each stand for a lower alkoxy or a lower alkyl, or R.sup.5 and R.sup.6 combinedly stand for butadienylene, and salts thereof.The compound (I) of the present invention has a strong 5-lipoxygenase inhibiting action, is of high safety and is useful as, among others, an agent for ameliorating dysfunction of circulatory system, an anti-allergic agent and a pharmaceutical agent for central nervous system.Type: GrantFiled: June 9, 1989Date of Patent: October 30, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Giichi Goto, Shigenori Ohkawa, Naohisa Fukuda
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Patent number: 4952587Abstract: The present invention provides a compound of formula I or a salt or prodrug thereof: ##STR1## wherein the dotted circle represents one or two double bonds in any position in the 5-membered ring;X, Y and Z independently represent oxygen, sulphur, nitrogen or carbon, provided that at least one of X, Y and Z represents oxygen, sulphur or nitrogen;A represents a group of formula II: ##STR2## in which R.sup.1 represents hydrogen, hydroxy, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-6 alkoxy, hydroxy(C.sub.1-6)alkyl, halogen, amino, cyano, --CONR.sup.6 R.sup.7 or --SO.sub.2 NR.sup.6 R.sup.7, in which R.sup.6 and R.sup.7 independently represent hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl;R.sup.2 represents hydrogen, halogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or C.sub.1-6 alkylcarbonyl;V represents nitrogen, ##STR3## and W represents oxygen, sulphur or ##STR4## in which R.sup.8 represents hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl or C.sub.Type: GrantFiled: February 3, 1989Date of Patent: August 28, 1990Assignee: Merck Sharp & Dohme Ltd.Inventors: Raymond Baker, John Saunders, Christopher Swain
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Patent number: 4937239Abstract: Novel 1-azabicycloalkane- and alkene-oximes (Ia) and 8-azabicyclo[3.2.1]octane- and octene-oximes (Ib) are provided, these compounds being useful as agents for treating pain or for treating the symptoms of senile cognitive decline. Also provided are pharmaceutical compositions containing the compounds and methods of treatment using the compounds in dosage form.Type: GrantFiled: February 13, 1989Date of Patent: June 26, 1990Assignee: Warner-Lambert CompanyInventors: David J. Lauffer, Walter H. Moos, Hasile Tecle
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Patent number: 4921982Abstract: This invention provides bicyclic carboxylic esters and amides, their pharmaceutical formulations, and a method for their use in treating migraine, emesis, gastrointestinal disorders, schizophrenia, or anxiety in mammals.Type: GrantFiled: June 14, 1989Date of Patent: May 1, 1990Assignee: Eli Lilly and CompanyInventors: Marlene L. Cohen, William B. Lacefield, David W. Robertson
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Patent number: 4882327Abstract: Compounds of formula (I), or a pharmaceutically acceptable salt thereof:Y-CO-L-Z (I)whereinL is NH or O; Y is a group of formula (a), (b) or (c): ##STR1## wherein R.sub.1 and R.sub.2, R.sub.5 and R.sub.6, R.sub.9 and R.sub.10, are independently selected from hydrogen or halogen;X is N or CR.sub.3whereinR.sub.3 is hydrogen or C.sub.1-6 alkoxy;R.sub.4 is hydrogen, halogen, CH.sub.3, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkylsulphinyl, C.sub.1-7 acyl, cyano, C.sub.1-6 alkoxycarbonyl, C.sub.1-7 acylamino, hydroxy, nitro or amino, aminocarbonyl, or aminosulphonyl, optionally N-substituted by one or two groups selected from C.sub.1-6 alkyl, C.sub.3-8 cycloalkyl, and C.sub.3-8 cycloalkyl C.sub.1-4 alkyl or disubstituted by C.sub.4 or C.sub.5 polymethylene; phenyl or phenyl C.sub.1-4 alkyl group optionally substituted in the phenyl ring by one or two of halogen, C.sub.1-6 alkoxy or C.sub.1-6 alkyl groups;one of R.sub.7 and R.sub.8 is C.sub.Type: GrantFiled: April 22, 1988Date of Patent: November 21, 1989Assignee: Beecham Group p.l.c.Inventor: Francis D. King
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Patent number: 4843074Abstract: Novel 1-azabicyclo[2.2.2]octan-3-yl 2-aryl-3-azacyclo-2-hydroxypropionates and their quaternary salts and their use as antimuscarinic agents having antisecretory activity selective for the gastrointestinal tract are disclosed. The compounds have the formula: ##STR1## wherein: X=H, halogen, lower alkyl, lower alkoxy, hydroxy, andR=morpholinyl, thiomorpholinyl, piperidinyl, 1,4-dioxa-8-azaspiro[4.5]decanyl, 4-(2,6-dimethylmorpholinyl), 4-ketopiperidinyl, 4-hydroxypiperidinyl, 4-substituted piperazinyl (wherein the substituent is lower alkyl, hydroxyalkyl, acetoxyalkyl, or acyl).Also disclosed are pharmaceutical compositions for treatment of irritable bowel syndrome and methods for using such compounds.Type: GrantFiled: May 17, 1988Date of Patent: June 27, 1989Assignee: Marion Laboratories, Inc.Inventors: Waclaw J. Rzeszotarski, Vicki H. Audia, Moshe Weitzberg
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Patent number: 4808588Abstract: Compounds of formula (I), or a pharmaceutically acceptable salt thereof: ##STR1## wherein: Het is monocyclic heteroaryl having two adjacent carbon atoms, a and b, depicted in formula (I); p1 R.sub.1 and R.sub.2 are independently selected from hydrogen, halogen, CF.sub.3, C.sub.1-6 alkyl and C.sub.1-6 Alkoxy;R.sub.3 is hydroxy, C.sub.1-6 alkoxy, C.sub.3-7 alkenyl-methoxy, phenoxy or phenyl C.sub.1-4 alkoxy in which either phenyl moiety may be substituted by one or two C.sub.1-6 alkyl, C.sub.1-6 alkoxy or halo; CO.sub.2 R.sub.6 wherein R.sub.6 is hydrogen or C.sub.1-6 alkyl, CONR.sub.7 R.sub.8 or SO.sub.2 NR.sub.7 R.sub.8 wherein R.sub.7 and R.sub.8 are independently hydrogen or C.sub.1-6 alkyl or together are C.sub.4-6 polymethylene, NO.sub.2, (CH.sub.2).sub.m OR.sub.9 wherein m is 1 or 2 and R.sub.9 is C.sub.1-6 alkyl or S(O).sub.n R.sub.10 wherein n is 0, 1 or 2 and R.sub.10 is C.sub.Type: GrantFiled: July 30, 1987Date of Patent: February 28, 1989Assignee: Beecham Group, p.l.c.Inventor: Francis D. King
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Patent number: 4803199Abstract: The dicarboxylic, heterocyclic and substituted benzoic acid alkylene bridged piperidyl amides and esters are serotonin M antagonists.Type: GrantFiled: November 25, 1987Date of Patent: February 7, 1989Inventors: Peter Donatsch, Gunter Engel, Bruno Hugi, Brian P. Richardson, Paul A. Stadler, deceased, by Hildegard R. Stadler, heir, by Brigitte M. Stadler, heir, by Sigrid A. Stadler, heir, by Gerald Breuleux, legal representative
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Patent number: 4789673Abstract: The dicarboxylic, heterocyclic and substituted benzoic acid alkylene bridged piperidyl amides and esters are serotonin M antagonists.Type: GrantFiled: November 10, 1987Date of Patent: December 6, 1988Inventors: Peter Donatsch, Gunter Engel, Bruno Hugi, Brian P. Richardson, Hildegard R. Stadler, Brigitte M. Stadler, Sigrid A. Stadler, Gerald Breuleux
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Patent number: 4720495Abstract: Benzo[ij]quinolizine-2-carboxylic acid derivatives of the general formula [I] and the salts, and their hydrates are provided: ##STR1## wherein A is a methylene group and B is a carbonyl group when A and B are linked by a single bond, or A and B unite together to form a vinylene group when A and B are linked by a double bond, R.sup.1 is a hydrogen atom, a C.sub.1-3 alkyl group or a 2-hydroxyethyl group, R.sup.2 and R.sup.3 are hydrogen atoms, methyl groups or ethyl groups and may be identical to or different from each other, R.sup.3 may be attached to the same carbon atom as R.sup.2, R.sup.4 is a methyl or ethyl group, and X is a halogen atom. The benzo[ij]quinolizine-2-carboxylic acid derivatives and the salts, and their hydrates have good adsorbability from the digestive tract into the circulating blood and exhibit excellent and long-lasting antibacterial activity.Type: GrantFiled: May 20, 1986Date of Patent: January 19, 1988Assignee: Tokyo Tanabe Co. LimitedInventors: Atsushi Takagi, Masao Yajima, Toshiaki Kikuchi, Masaki Saeki
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Patent number: 4684727Abstract: Zwitterionic bicyclic compounds are disclosed which are useful as anti-allergic, anti-inflammatory and/or cytoprotective agents. Pharmaceutical compositions and methods of treatment employing such compounds are also disclosed.Type: GrantFiled: July 29, 1985Date of Patent: August 4, 1987Assignee: Schering CorporationInventors: David J. Blythin, Ho-Jane Shue
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Patent number: 4675326Abstract: A novel series of antidotes against organophosphorus poisoning having both anti-muscarinic activity and reactivation potency, were synthesized and evaluated for their pharmacological efficacy.The compounds are bisquarternary oxybismethylene(or:trimethylene)-bis-N-heterocycles.The N-heterocycles are comprised of 2,3 or 4 mono-substituted pyridines, 3-substituted quinuclidines and 4-substituted N-methylpiperidines (exclusive of both groups in one molecule designating a substituted pyridine ring). Some of the compounds display a remarkably low acute toxicity in mice.These antidotes have been shown to be effective against poisoning by a variety of organophosphorus compounds as well as carbamates. The compounds are also of value as active ingredients in ophthalmic preparations.Type: GrantFiled: May 8, 1985Date of Patent: June 23, 1987Inventors: Gabriel Amitai, David Balderman, Rachel Bruckstein-Davidovici, Michael Spiegelstein
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Patent number: 4672119Abstract: New chemical compounds, bis quaternary carbamates, having the generic fora: ##STR1## wherein NRR.sub.1 R.sub.2 is a radical selected from the group consisting of N-methylpyrrolidinio, N-methylpiperidinio, N-methyl-3-hydroxypiperidinio, quinuclidinio, 3-hydroxyquinuclidinio, and 3-oxoquinuclidinio and wherein X is one equivalent of a monovalent or polyvalent anion.Type: GrantFiled: July 26, 1967Date of Patent: June 9, 1987Assignee: The United States of America as represented by the Secretary of the ArmyInventors: Harold Z. Sommer, George E. Wicks, Jr.
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Patent number: 4644003Abstract: The present invention relates to antagonists of muscarinic acetylcholine receptors. More specifically, this invention contemplates highly selective antimuscarinic agents which are characterized as esters of 3-quinuclidinol and unsymmetrical alpha-disubstituted glycolic acids.These highly selective antimuscarinic agents permit efficacy at particular sites designated m.sub.1 -AChR without affecting the muscarinic acetylcholine receptors of other tissues characterized by sites designated m.sub.2 -AChR. Such efficacy requires lower quantities of the antagonist thereby lowering toxicity and other undesirable side effects.Type: GrantFiled: April 3, 1985Date of Patent: February 17, 1987Assignee: Research CorporationInventors: Waclaw J. Rzeszotarski, Raymond E. Gibson, William C. Eckelman, Richard C. Reba
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Patent number: 4599344Abstract: Novel quinuclidines, their acid addition, quaternary ammonium and inner salts are described. Also provided is the method of using these compounds as antiarrhythmic agents and pharmaceutical formulations containing such compounds.Type: GrantFiled: October 31, 1984Date of Patent: July 8, 1986Assignee: Schering A.G.Inventor: Thomas K. Morgan, Jr.
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Patent number: 4531967Abstract: Compounds are prepared which correspond to the formula ##STR1## wherein R represents methylene, ethylene or ethylidene;R.sup.1 represents hydrogen, hydroxy, chloro, bromo, fluoro, iodo, cyano, --COOR.sup.2, oxo or acetoxy;Y represents hydrogen, chloro, bromo, iodo or fluoro;X represents hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, cyano, trifluoromethyl, (trifluoromethyl)thio, (trifluoromethyl)sulfonyl, trifluoromethoxy, --COOR.sup.2 wherein R.sup.2 is alkyl of 1 to 6 carbon atoms, --C(O/S)NR.sup.3 R.sup.4 wherein R.sup.3 represents R.sup.2, alkenyl of 2 to 6 carbon atoms or alkynyl of 2 to 6 carbon atoms and R.sup.4 represents R.sup.3 or hydrogen, or --S(O).sub.2 NR.sup.2 R.sup.3 with the proviso that X and Y cannot both be hydrogen at the same time and A represents a non-phytotoxic anion. The compounds have been found to be active plant growth enhancers.Type: GrantFiled: October 13, 1983Date of Patent: July 30, 1985Assignee: The Dow Chemical CompanyInventors: John C. Van Heertum, Maria P. Herrero
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Patent number: 4465834Abstract: A class of anticholinergic drugs having the formula ##STR1## in which R.sup.1 is a carbocyclic or branched aliphatic group of 3 to 8 carbon atoms, R.sup.2 is a branched or linear aliphatic group containing 3 to 10 carbon atoms with 1 to 2 olefinic or acetylenic bonds and R.sup.3 is an alkyl or cyclic group of 4 to 12 carbon atoms containing a tertiary amino nitrogen, are described.Type: GrantFiled: September 20, 1965Date of Patent: August 14, 1984Assignee: FMC CorporationInventors: Burton M. Baum, Hugo Stange
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Patent number: 4431627Abstract: Compounds of the formula: ##STR1## wherein R is aryl, alkyl, cycloalkyl, phenyl, cyclopentyl, cyclohexyl, a ligand containing Tc-99m in chelated form or a ligand capable of chelating Tc-99m;R.sub.1 is H or lower alkyl;X is in the ortho-, meta or para- position, and is selected from the group consisting of .sup.125 I, .sup.123 I, .sup.127 I, I, .sup.18 F, .sup.75 Br, .sup.77 Br, NH.sub.2, and ##STR2## wherein R.sub.2 is in the 2,3, or 4 position and is selected from the group consisting of H and lower alkyl, provided that when R is a ligand capable of chelating Tc-99m or containing Tc-99m in chelated form, X is not a radioisotope and may also be H or lower alkyl;Z.sup..crclbar. is an anion; or the free amine thereof; anddenotes an asymmetric carbon atom.Type: GrantFiled: December 31, 1981Date of Patent: February 14, 1984Assignee: Research CorporationInventors: William C. Eckelman, Richard C. Reba, Waclaw J. Rzeszotarski, Raymond E. Gibson
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Patent number: 4355166Abstract: The invention relates to esters of 3-hydroxy-quinuclidine with phenoxycarboxylic acids, and their salts having general formula: ##STR1## wherein R.sub.1 represents H,CH.sub.3, and R.sub.2 represents H, Cl,Br or a radical of an acid of the group comprising oleic, pivalic, nicotinic, clofibric, pyridineacetic and teophyllineacetic acid.The compounds of the invention jointly show hypocholesteremizing and hypotriglyceridimizing activity, combined with other therapeutically interesting properties, such as beta-blocking, diuretic, anti-inflammatory activity.The invention furthermore relates to the pharmaceutical compositions containing the compounds of the invention as the active ingredients.Type: GrantFiled: March 19, 1981Date of Patent: October 19, 1982Assignee: D and D S.r.l.Inventor: Alberto Reiner
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Patent number: 4125531Abstract: This invention encompasses novel 2-(2,2-diphenyl-4-pentenyl-1-azabicyclo[2.2.2]octane and related compounds. These compounds are useful anti-diarrheal agents which possess little if any analgesic activity.Type: GrantFiled: April 18, 1977Date of Patent: November 14, 1978Assignee: G. D. Searle & Co.Inventor: Chung H. Yen