The Chalcogen, X, Is In A -c(=x)- Group Patents (Class 546/340)
-
Patent number: 4683239Abstract: Octahydroindolizine compounds of formula (I): ##STR1## wherein Q is --NR--, --(CH.sub.2).sub.z --, --CH.dbd.CH--, --C.tbd.C--, --OCH.sub.2 --, --SCH.sub.2 --, --SO.sub.2 --, --SO--, --CO--, or an oxygen or a sulfur atom and where R, R.sup.1 and R.sup.2 are substituents such as alkyl and x, y and z are independently the integers 0-3. Also, pharmaceutical compositions containing (I), intermediates and methods for treating pain.Type: GrantFiled: April 10, 1986Date of Patent: July 28, 1987Assignee: McNeilab, Inc.Inventors: Richard J. Carmosin, John R. Carson
-
Patent number: 4681944Abstract: There is described a novel process for preparing 4-pyridinylmethyl ketones of formula (I) ##STR1## wherein R is alkyl, aryl or aralkyl. The process involves hydrolysis of a compound ##STR2## generated by reaction of an acylating agent with 4-methylpyridine. The acylating agent may be selected from compounds of formula R-CO-X and R-CO-O-CO-R where R is as defined above and X represents halogen. Compounds of formula I have utility in the preparation of a variety of products, including pharmaceutically active 1,2-dihydro-6-R-2-oxo-5 pyridinyl compounds.Type: GrantFiled: June 11, 1985Date of Patent: July 21, 1987Inventors: Robert M. Ippolito, Stephen Vigmond
-
Patent number: 4678501Abstract: Novel aromatic heteromonocyclic-substituted 1,3-cycloalkanediones, enol ester derivatives and salts thereof, exhibit herbicidal activity against a variety of broadleaf and grassy weeds. Certain 2-(2-pyrazinyl) 1,3-cycloalkanediones and their enol esters were also found to be active as mite adulticides and ovicides.Type: GrantFiled: January 9, 1986Date of Patent: July 7, 1987Assignee: Union Carbide CorporationInventor: David T. Manning
-
Patent number: 4672066Abstract: The invention relates to compounds of the formula ##STR1## wherein R is hydrogen or lower alkyl, Y is alkylene; Z is alkylene, ##STR2## the asterisk herein denotes bonding to the substituted acetophenone; R.sub.2 is hydrogen or lower alkoxy; and n is an integer of 1 to 3; A is ##STR3## and HET is a 5-or 6- membered nitrogen containing heterocyclic group, and their acid addition salts. The compounds of formula I of the invention are useful for the treatment of allergic conditions, such as, asthma and cardiovascular diseases, such as, angina and arrhythmias.Type: GrantFiled: April 22, 1985Date of Patent: June 9, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Matthew Carson, Ru-Jen L. Han, Ronald A. LeMahieu
-
Patent number: 4645771Abstract: The disclosure concerns novel 1-benzyl-1,2,3,6-tetrahydropyridine derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen or a (1-4C)-alkyl radical, and benzene ring A bears one or two substituents selected from combinations of halogeno, (1-4C)-alkyl, (1-4C)-alkoxy, hydroxy, nitro, cyano, carboxamido, carboxyl, [(1-4C)-alkoxy]carbonyl, hydroxymethylene, amino, (1-4C)-alkanoylamino, (1-4C)-alkylsulphonamido, [(1-4C)-alkoxy]carbonyloxy, (1-4C)-alkanoyloxy and optionally substituted benzoyloxy radicals, and their pharmaceutically acceptable salts; pharmaceutical compositions thereof; analogy processes for their manufacture; and methods of medical treatment employing such derivatives.The compounds of formula I are inhibitors of the aggregation of blood platelets and are of application in the treatment or prophylaxis of thrombosis or occlusive vascular disease.Type: GrantFiled: September 30, 1982Date of Patent: February 24, 1987Assignee: Imperial Chemical Industries PLCInventor: Stuart D. Mills
-
Patent number: 4603208Abstract: Novel polyprenyl compounds have the general formula: ##STR1## represents a cis-isoprene unit, n is an integer of 11-19, Z.sup.1 is --CH.sub.2 OH or a functional precursor thereof, and either one of R.sup.1 and R.sup.2 is a hydrogen atom and the other is --S(O).sub.m R.sup.3 in which m is an integer of 0 (zero), 1 or 2 and R.sup.3 is a phenyl, naphthyl, pyridyl or thiazolinyl group or such group substituted with at least one lower alkyl and/or halogen substituent. The topic novel polyprenyl compounds can be synthesized from derivatives of the polyprenol which is obtainable from leaves of Ginkgo biloba or Cedrus deodara, among others, by extraction, if necessary followed by hydrolytic treatment. The novel polyprenyl compounds can be converted to mammalian dolichols or precursors thereof by reductive elimination of the --S(O).sub.m R.sup.3 group.Type: GrantFiled: February 10, 1983Date of Patent: July 29, 1986Assignee: Kuraray Co., Ltd.Inventors: Takashi Onishi, Shigeaki Suzuki, Fumio Mori, Tetsuo Takigawa, Yoshiji Fujita, Masao Mizuno, Takashi Nishida
-
Patent number: 4590195Abstract: 1,4-Dihydropyridine derivatives of the formula: ##STR1## wherein R is aryl or heteroaryl; R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.4 alkyl or 2-methoxyethyl; n is 2, 3 or 4; R.sup.3 is H, C.sub.1 -C.sub.4 alkyl, CH.sub.2 CO.sub.2 (C.sub.1 -C.sub.4 alkyl) or CH.sub.2 CN; and R.sup.4 is a group of the formula COR.sup.5, CSR.sup.5, C(.dbd.NR.sup.6)R.sup.7 or SO.sub.2 R.sup.5, wherein R.sup.5 is C.sub.1 -C.sub.4 alkyl, NH.sub.2, NH(C.sub.1 -C.sub.4 alkyl), NH(C.sub.3 -C.sub.6 cycloalkyl), N(C.sub.1 -C.sub.4 alkyl).sub.2, NHCH.sub.2 CO.sub.2 (C.sub.1 -C.sub.4 alkyl), NHCH.sub.2 CONH.sub.2, NHCH.sub.2 CO.sub.2 H, NH(CH.sub.2).sub.2 NH.sub.2, NHNH.sub.2, NHNRCO.sub.2 (C.sub.1 -C.sub.4 alkyl), NH-aryl, NHCO-aryl or a heterocyclic, NH-heterocyclic or NHCO-heterocyclic group, or when R.sup.4 is C(.dbd.O)R.sup.5, R.sup.5 may be H or CF.sub.3 ; R.sup.6 is H, CN, CO.sub.2 (C.sub.1 -C.sub.4 alkyl), CO(C.sub.1 -C.sub.4 alkyl), SO.sub.2 (C.sub.1 -C.sub.4 alkyl), SO.sub.2 -aryl, SO.sub.2 NH.sub.2, SO.sub.2 N(C.sub.1 -C.Type: GrantFiled: March 5, 1984Date of Patent: May 20, 1986Assignee: Pfizer Inc.Inventors: David Alker, Peter E. Cross, Simon F. Campbell
-
Patent number: 4579952Abstract: Process for preparing analgesic and narcotic antagonistic isoquinolines comprising:(a) contacting and reacting a lithiated anisole or alkyl phenyl ether, optionally substituted at the 3-position to the lithium atom, with a 4-piperidone to yield a 4-aryl-4-piperidinol;(b) dehydrating the piperidinol to a 4-aryl-1,2,3,6-tetrahydropyridine;(c) metalating and acylating the 1,2,3,6-tetrahydropyridine to yield a 1-(4-aryl-1,2,3,4-tetrahydropyrid-4-yl)-4-hydroxy-1-butanone;(d) reducing the ketone moiety of the butanone to yield a 5-aryl-7-oxa-2-azabicyclo[3.2.1]octane-6-propanol;(e) converting the alcohol moiety of the propanol to L to yield a 5-aryl-6-[3-(L)propyl]-7-oxa-2-azabicyclo[3.2.1]octane in which L is a leaving group selected from the group consisting of --Cl, --Br, --I, p-MeC.sub.6 H.sub.4 SO.sub.3 -- and MeSO.sub.3 --.Type: GrantFiled: July 25, 1983Date of Patent: April 1, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventors: Engelbert Ciganek, Ashokkumar B. Shenvi
-
Patent number: 4563446Abstract: Novel compounds of the formula: ##STR1## wherein R.sup.2 is an aromatic or heterocyclic group, which may optionally be substituted, R.sup.2 is a methyl group, a hydroxymethyl group, a nitroxymethyl group, a formyl group, a nitrogen-containing five-membered ring-methyl group, an acetal-methyl group, a trialkylsilyloxymethyl group, an alkyl- or aryl-sulfonyloxymethyl group, an alkyl- or aryl-sulfonylaminocarbonyloxymethyl group, an acyloxymethyl group, an alkoxycarbonyloxymethyl group, a halogenomethyl group, an alkoxymethyl group, an aryloxymethyl group, a cyano group, a carbamoyl group which may optionally be substituted, a carbamoyloxymethyl group which may optionally be substituted, a thiocarbamoyloxymethyl group which may optionally be substituted, and an alkoxycarbonyl group, n is an integer of 1 to 20, and ##STR2## provided that n is an integer of 9 to 20 when ##STR3## and, at the same time, R.sup.Type: GrantFiled: July 19, 1984Date of Patent: January 7, 1986Assignee: Takeda Chemical Industries, Ltd.Inventors: Shinji Terao, Kohei Nishikawa
-
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
-
Patent number: 4524210Abstract: 3,5-Di(t-butyl)-4-hydroxyphenyl and 3,5-di(t-butyl)-4-hydroxybenzoyl-substituted pyridines have pharmacological activity as antiinflammatory agents.Type: GrantFiled: August 12, 1983Date of Patent: June 18, 1985Assignee: Riker Laboratories, Inc.Inventor: George G. I. Moore
-
Patent number: 4513137Abstract: Mono- or bis(iodonium salts) are produced in neutral organic solvents by the reaction of an [hydroxy (organosulfonyloxy)iodo]arene with a bis(triorganosilyl)arene, a bis(trihalosilyl)arene, or with a mono- or bis(triorganosilyl)heterocyclic compound, or a mono- or bis(trihalosilyl)heterocyclic. The iodonium salts are made under conditions of regiospecific control.Type: GrantFiled: April 9, 1981Date of Patent: April 23, 1985Assignee: The University of AkronInventors: Gerald F. Koser, Carol S. Carman
-
Patent number: 4504663Abstract: The present invention concerns novel heterocyclic aminoalcoyl derivatives having the formula: ##STR1## wherein n=1, 2 or 3; A represents a nitrogen atom or the CH group, X=CH.sub.2 or CH.sub.2 O; R represents a phenyl nucleus possibly substituted; NR.sub.1 R.sub.2 =amino, methylamino, N,N-dialkylamino or an heterocyclic radical; and R.sub.3 =H, halogen, alkyl, alkyloxy or methoxy.These derivatives are useful as drugs, especially as analgesics and antidepressants.Type: GrantFiled: November 15, 1983Date of Patent: March 12, 1985Assignee: Delalande S.A.Inventors: Gerard H. Moinet, Philippe L. Dostert, Guy R. Bourgery
-
Patent number: 4500535Abstract: A series of 4-(2-carboxymethylthiomethyl)pyridines and related compounds, and their pharmaceutically acceptable salts, are disclosed as having immunoregulatory activity. Preferred compounds include 4-(2-carboxymethylthiomethyl)pyridine [alternatively named 2-(4-picolylthio)acetic acid] and (C.sub.1 -C.sub.4)alkyl esters thereof, and 4-(1-formylmethylthiomethyl)-pyridine [alternatively named 2-(4-picolylthio)acetaldehyde] and bis(C.sub.1 -C.sub.4)alkyl or cyclic acetals thereof. These acids, esters, aldehydes and acetals also have utility as intermediates in the synthesis of the corresponding 4-(2-hydroxyethylthiomethyl)pyridines.Type: GrantFiled: March 7, 1983Date of Patent: February 19, 1985Assignee: Pfizer Inc.Inventors: Joseph G. Lombardino, Charles A. Harbert
-
Patent number: 4472408Abstract: The invention relates to 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridines of formula ##STR1## in which R represents a cyano, acetyl or cycloalkyl group of from 3 to 7 carbon atoms and Alk represents a straight or branched alkylene of from 1 to 4 carbon atoms, as well as to the salts thereof, having an anorectic activity, to a process for preparing same and to pharmaceutical compositions containing said compounds, useful in the treatment of obesity.Type: GrantFiled: March 3, 1982Date of Patent: September 18, 1984Assignee: SanofiInventors: Dino Nisato, Emilio Crisafulli, Alberto Bianchetti, Paolo Carminati
-
Patent number: 4435330Abstract: Amphoteric branched sulfatobetaines of the formula ##STR1## wherein R.sub.f is perfluoroalkyl or perfluoroxyperfluoroalkyl; R.sub.1 is a direct bond or a divalent connecting group; R.sub.2, R.sub.3, and R.sub.4 are independently hydrogen or lower alkyl; R.sub.5, R.sub.6 and R.sub.7 are independently lower alkyl, and R.sub.6 may additionally represent aralkyl, and R.sub.6 and R.sub.7 taken together with the nitrogen to which they are attached may also represent piperidino or morpholino and R.sub.5, R.sub.6 and R.sub.7 taken together may also represent pyridyl, acridyl or quinolyl and salts thereof, their preparation and use as surfactants are disclosed.Type: GrantFiled: December 29, 1982Date of Patent: March 6, 1984Assignee: Ciba-Geigy CorporationInventor: Robert A. Falk
-
Patent number: 4431851Abstract: The present invention concerns compounds of the formula ##STR1## wherein n=1, 2 or 3; and R' represents phenyl or orthofluorophenyl. Said compounds are used as intermediates in the preparation of heterocyclic aminoalkyl derivatives which are useful as analgesics and antidepressants.Type: GrantFiled: March 8, 1983Date of Patent: February 14, 1984Assignee: Delalande S.A.Inventors: Gerard H. Moinet, Philippe L. Dostert, Guy R. Bourgery
-
Patent number: 4420434Abstract: The instant invention relates to the use of ion-pair complexes derived from anionic perfluoroalkyl sulfonates, carboxylates, phosphates and phosphonates and cationic perfluoroalkyl surfactants. Such complexes are capable of reducing the surface tension of aqueous solutions dramatically even at extremely low concentrations, and are useful as wetting, spreading and leveling agents and are especially preferred as components in so-called aqueous film forming foam compositions for fighting polar and non-polar solvent and fuel fires.Type: GrantFiled: January 9, 1981Date of Patent: December 13, 1983Assignee: Ciba-Geigy CorporationInventor: Robert A. Falk
-
Patent number: 4417054Abstract: One aspect of the invention resides in the three step process for preparing cardiotonically active 1,2-dihydro-6-(lower-alkyl)-2-oxo-5-(pyridinyl)nicotinonitriles (III, Q is CN) or 1,2-dihydro-6-(lower-alkyl)-2-oxo-5-(pyridinyl)nicotinamides (III, Q is CONH.sub.2) which comprises reacting a pyridinylmethyl lower-alkyl ketone (I) with tri-(lower-alkyl) orthoformate, acetic anhydride and acetic acid to produce 2-(lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketone (II), reacting II with cyanoacetamide or malonamide in the presence of a basic condensing agent and neutralizing the reaction mixture, where pyridinyl is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents. Other aspects of the invention resides in the intermediate 2-(lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketones (II) and its two step conversion, as described above, to said compounds (III, Q is CN or CONH.sub.2).Type: GrantFiled: May 24, 1982Date of Patent: November 22, 1983Assignee: Sterling Drug Inc.Inventor: Karl O. Gelotte
-
Patent number: 4415736Abstract: Process for preparing analgesic and narcotic antagonistic isoquinolines comprising:(a) contacting and reacting a lithiated anisole or alkyl phenyl ether, optionally substituted at the 3-position to the lithium atom, with a 4-piperidone to yield a 4-aryl-4-piperidinol;(b) dehydrating the piperidinol to a 4-aryl-1,2,3,6-tetrahydropyridine;(c) metalating and acylating the 1,2,3,6-tetrahydropyridine to yield a 1-(4-aryl-1,2,3,4-tetrahydropyrid-4-yl)-4-hydroxy-1-butanone;(d) reducing the ketone moiety of the butanone to yield a 5-aryl-7-oxa-2-azabicyclo[3.2.1]-octane-6-propanol;(e) converting the alcohol moiety of the propanol to L to yield a 5-aryl-6-[3-(L)propyl]-7-oxa-2-azabicyclo[3.2.1]octane in which L is a leaving group selected from the group consisting of -Cl, -Br, -I, p-MeC.sub.6 H.sub.4 SO.sub.3 - and MeSO.sub.3 -.Type: GrantFiled: December 28, 1981Date of Patent: November 15, 1983Assignee: E. I. Du Pont de Nemours & Co.Inventors: Engelbert Ciganek, Ashokkumar B. Shenvi
-
Patent number: 4403100Abstract: The present invention provides novel (11R)-11-deoxy-11-alkyl-6-oxo-prostaglandins which are useful for curing and preventing duodenal ulcers and for preventing or treating gastrointestinal cell damage caused by the use of other pharmacological agents.Type: GrantFiled: October 30, 1981Date of Patent: September 6, 1983Assignee: The Upjohn CompanyInventor: Douglas R. Morton, Jr.
-
Patent number: 4393068Abstract: Novel compounds having the formula ##STR1## in which R is alkyl, cycloalkyl, aralkyl, chlorophenyl or chlorobenzyl, R.sub.1 is hydrogen or lower alkyl and n is 1, 2, or 3, are insect repellents.Type: GrantFiled: January 4, 1982Date of Patent: July 12, 1983Inventor: Rayman Y. Wong
-
Patent number: 4390537Abstract: 1-(Substituted-aminoalkoxyphenyl)-2-methylene-1-alkanones, a class of compounds possessing anti-allergic properties for use in the treatment of allergic conditions, such as asthma prepared by etherifying an alkanoylphenol with an aminoalkyl halide, converting the ether formed to a salt of Mannich base by reacting it with a salt of a secondary amine in the presence of formaldehyde or paraformaldehyde and treating the Mannich salt with a weak base to deaminate the same and form the final product.Type: GrantFiled: May 19, 1982Date of Patent: June 28, 1983Assignee: Merck & Co., Inc.Inventor: Edward J. Cragoe, Jr.
-
Patent number: 4377691Abstract: A process for the preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1-propanol (i.e. ifenprodil) and acid-addition salts thereof, characterized by brominating 4'-hydroxypropiophenone in a single or mixed solvent selected from the group consisting of methanol, ethanol and a saturated aliphatic ether, removing hydrogen bromide formed in the course of the bromination, adding 4-benzylpyridine to the reaction mixture, heating the reaction mixture under reflux in a single or mixed solvent selected from the group consisting of methanol and ethanol, and then subjecting the resultant reaction mixture to catalytic reduction to form 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1-propanol hydrobromide in the reaction mixture. The end product (i.e.Type: GrantFiled: December 4, 1980Date of Patent: March 22, 1983Assignee: Kabushiki Kaisha Cosmos EnterpriseInventors: Bompei Yasui, Tomohisa Miyamoto, Katsuyuki Hiraoka, Yoshitaka Sako
-
Patent number: 4371696Abstract: A series of 4-(2-carboxymethylthiomethyl)pyridines and related compounds, and their pharmaceutically acceptable salts, are disclosed as having antiinflammatory and immunoregulatory activity. Preferred compounds include 4-(2-carboxymethylthiomethyl)pyridine [alternatively named 2-(4-picolylthio)acetic acid] and (C.sub.1 -C.sub.4)alkyl esters thereof, and 4-(1-formylmethylthiomethyl)pyridine [alternatively named 2-(4-picolylthio)-acetaldehyde] and bis(C.sub.1 -C.sub.4)alkyl or cyclic acetals thereof. These acids, esters, aldehydes and acetals also have utility as intermediates in the synthesis of the corresponding 4-(2-hydroxyethylthiomethyl)pyridines.Type: GrantFiled: June 26, 1981Date of Patent: February 1, 1983Assignee: Pfizer Inc.Inventors: Joseph G. Lombardino, Charles A. Harbert
-
Patent number: 4355034Abstract: Mercaptoalkylpyridines carrying an ethenyl or ethynyl substituent are prepared from known pyridine compounds, principally pyridoxine, by known chemical procedures, and are useful in the treatment of rheumatoid arthritis and related inflammatory diseases.Type: GrantFiled: July 25, 1980Date of Patent: October 19, 1982Assignee: Merck & Co., Inc.Inventors: Tsung-Ying Shen, Howard Jones, Conrad P. Dorn
-
Patent number: 4352760Abstract: The present invention provides novel substituted heptadeca-5,9- and 5,10-dienoic acid and similar fatty acid compounds which are derivatives of certain prostaglandins and are potent thromboxane A.sub.2 inhibitors. By virtue of this pharmacological property, they represent useful pharmacological agents for a wide variety of purposes.Type: GrantFiled: December 29, 1980Date of Patent: October 5, 1982Assignee: The Upjohn CompanyInventor: Kirk M. Maxey
-
Patent number: 4350518Abstract: Substituted alkylammonium salts of the formula ##STR1## where Ar denotes substituted phenyl, X denotes oxygen or sulfur, n denotes one of the integers 0, 1 and 2, B denotes bicyclic quinuclidine, bicyclic pyrrolizidine or substituted ammonium, and Z denotes the anion of a nonphytotoxic acid, the manufacture of these compounds, and their use as plant growth regulators.Type: GrantFiled: February 23, 1981Date of Patent: September 21, 1982Assignee: BASF AktiengesellschaftInventors: Hubert Sauter, Bernd Zeeh, Ernst Buschmann, Johann Jung
-
Patent number: 4342782Abstract: 1-(Substituted-aminoalkoxyphenyl)-2-methylene-1-alkanones, a class of compounds possessing antiallergic propertiesfor use in the treatment of allergic conditions, such as asthma prepared by etherifying an alkanoylphenol with an aminoalkyl halide, converting the ether formed to a salt of Mannich base by reacting it with a salt of a secondary amine in the presence of formaldehyde or paraformaldehyde and treating the Mannich salt with a weak base todeaminate the same and form the final product.Type: GrantFiled: November 16, 1978Date of Patent: August 3, 1982Assignee: Merck & Co., Inc.Inventor: Edward J. Cragoe, Jr.
-
Patent number: 4342771Abstract: Hypoglycemic 5-chromanyl, 2,3-dihydro-5-benzo[b]furanyl, 5-pyridyl, 5-quinolyl, 5-pyrrolyl, 5-indolyl, 5-thiazolyl, 5-oxazolyl, 5-isothiazolyl and 5-isoxazolyl oxazolidine-2,4-diones and the pharmaceutically acceptable salts thereof; certain 3-acylated derivatives thereof; a method of treating hyperglycemic animals therewith; and intermediates useful in the preparation of said compounds.Type: GrantFiled: April 23, 1981Date of Patent: August 3, 1982Assignee: Pfizer Inc.Inventor: Rodney C. Schnur
-
Patent number: 4341906Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrollo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl;R.sub.3 is selected from hydrogen, methyl and ethyl;R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl;Z is selected from:(a) alkylene having from one to nine carbon atoms;(b) -(alk.sub.1).sub.m -X-(alk.sub.2).sub.n - wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.Type: GrantFiled: December 22, 1980Date of Patent: July 27, 1982Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
-
Patent number: 4334087Abstract: A novel process for the manufacture of .alpha.-ketocarboxylic acids which comprises the reaction of oximinohalide with cyanide ion to form oximinonitrile which is reacted with hydroxide ion to form oximinoacid and hydrolysis thereof to the .alpha.-ketoacid.Type: GrantFiled: September 11, 1980Date of Patent: June 8, 1982Assignee: Zoecon CorporationInventors: Ted A. Baer, Jeffrey N. Labovitz
-
Patent number: 4328169Abstract: This invention provides a convenient and commercially adaptable process for the preparation of vinylcyclopropane derivatives in high yield. For the process an alkylating agent and activated methylene compound are reacted in the presence of an alkylene oxide derivative and alkali metal compound. Water can also be present and/or the reaction may be carried out in an inert organic diluent.Type: GrantFiled: October 27, 1980Date of Patent: May 4, 1982Assignee: Emery Industries, Inc.Inventor: Allen L. Hall
-
Patent number: 4328168Abstract: This invention provides a convenient and commercially adaptable process for the preparation of vinylcyclopropane derivatives in high yield. For the process an alkylating agent and activated methylene compound are reacted in the presence of a cyclic polyether compound and alkali metal compound. Water can also be present and/or the reaction may be carried out in an inert organic diluent.Type: GrantFiled: October 27, 1980Date of Patent: May 4, 1982Assignee: Emery Industries, Inc.Inventor: Richard G. Fayter, Jr.
-
Patent number: 4325959Abstract: 4-(((Heterocyclo)thio)methyl)benzoic acids, esters, amides and pharmaceutically-acceptable salts thereof having hypoglycemic activity in mammals, including a method of use and pharmaceutically-acceptable compositions.Type: GrantFiled: August 9, 1979Date of Patent: April 20, 1982Assignee: The Dow Chemical CompanyInventor: Donald P. Matthews
-
Patent number: 4317828Abstract: The pyridine derivatives of the general formula: ##STR1## [wherein A represents an alkylene group containing from 1 to 5 carbon atoms unsubstituted or substituted by a hydroxy group, B represents a single bond, or an oxygen or sulphur atom, or an alkylene group containing from 1 to 5 carbon atoms, D represents a single bond, or an alkylene group containing from 1 to 5 carbon atoms, E represents a grouping of the formula: ##STR2## (in which R.sup.6 represents a hydrogen atom, or an alkyl group containing from 1 to 4 carbon atoms), Z represents a single bond, or an ethynylene group, or a grouping of the formula: ##STR3## in which R.sup.2 represents a hydrogen atom, or an alkyl group containing from 1 to 4 carbon atoms, R.sup.3 represents a hydrogen, bromine or chlorine atom, or an alkyl group containing from 1 to 4 carbon atoms, the symbol represents a single or double bond, the carbon atom attached to R.sup.2 binds to B, and the carbon atom attached to R.sup.3 binds to D, R.sup.Type: GrantFiled: February 12, 1981Date of Patent: March 2, 1982Assignees: Ono Pharmaceutical Co., Ltd., Kissei Pharmaceutical Co., Ltd.Inventors: Tadao Tanouchi, Masanori Kawamura, Masaki Hayashi
-
Patent number: 4310669Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrrolo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl;R.sub.3 is selected from hydrogen, methyl and ethyl;R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl;Z is selected from:(a) alkylene having from one to nine carbon atoms;(b) -(alk.sub.1).sub.m -X-(alk.sub.2).sub.n - wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.Type: GrantFiled: December 22, 1980Date of Patent: January 12, 1982Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
-
Patent number: 4294841Abstract: A drug useful as antiarhythmic, antidepressant and anxiolytic containing as an active agent a compound of the formula ##STR1## wherein X and Y are the same or different and represent hydrogen or halogen atoms, or 1-4C alkyl groups, 1-4C alkoxy groups, 1-4C alkylthio groups, CF.sub.3, OH, NH.sub.2, 1-4C monoalkylamino or amino groups substituted by a 1-4C alkylsulfonyl group, a 1-5C alkylcarbonyl group or an aroyl group and A is a CO, CHOH or CH.sub.2 group, or a salt of said compound with a pharmaceutically acceptable acid, is disclosed together with methods for the preparation thereof and its use in human therapy.Type: GrantFiled: November 27, 1979Date of Patent: October 13, 1981Assignee: PharmindustrieInventors: Alain A. Champseix, Gerard R. Le Fur
-
Patent number: 4285867Abstract: Compounds having the formula ##STR1## wherein ##STR2## R.sub.1 is hydrogen, benzyl or alkanoyl, X is C.sub.2-4 alkylene; andZ-W is alkyl, phenylalkyl or pyridylalkyl which can have an oxygen atom as part of the alkyl chain and their use as CNS agents, antidiarrheals and antiemetics. Processes for their preparation and intermediates therefor are described.Type: GrantFiled: September 19, 1980Date of Patent: August 25, 1981Assignee: Pfizer Inc.Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
-
Patent number: 4283569Abstract: Compounds useful for pharmacological and medicinal purposes having the formulae ##STR1## wherein R is H, C.sub.1 -C.sub.5 alkanoyl; R.sub.1 is H, benzyl, C.sub.1 -C.sub.5 alkanoyl, P(O)(OH).sub.2, --CO(CH.sub.2).sub.2 COOH or a basic acyl group; each of R.sub.2 and R.sub.4 is H, C.sub.1 -C.sub.6 alkyl, phenyl, pyridyl or (CH.sub.2).sub.y C.sub.6 H.sub.5 ; y is 1-4; R.sub.3 is H or CH.sub.3 ; Z is C.sub.1 -C.sub.13 alkylene or --(alk.sub.1).sub.m --O--(alk.sub.2).sub.n --; each of (alk.sub.1) and (alk.sub.2) is C.sub.1 -C.sub.13 alkylene with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 13; each of m and n is 0 or 1; and W is H, pyridyl, phenyl, fluorophenyl or chlorophenyl; intermediates therefor and methods for their preparation and use.Type: GrantFiled: September 13, 1977Date of Patent: August 11, 1981Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
-
Patent number: 4271170Abstract: The pyridine derivatives of the general formula: ##STR1## [wherein A represents an alkylene group containing from 1 to 5 carbon atoms unsubstituted or substituted by a hydroxy group, B represents a single bond, or an oxygen or sulphur atom, or an alkylene group containing from 1 to 5 carbon atoms, D represents a single bond, or an alkylene group containing from 1 to 5 carbon atoms, R represents a grouping of the formula: ##STR2## (in which R.sup.6 represents a hydrogen atom, or an alkyl group containing from 1 to 4 carbon atoms), Z represents a single bond, or an ethynylene group, or a grouping of the formula: ##STR3## in which R.sup.2 represents a hydrogen atom, or an alkyl group containing from 1 to 4 carbon atoms, R.sup.3 represents a hydrogen, bromine or chlorine atom, or an alkyl group containing from 1 to 4 carbom atoms; the symbol represents a single or double bond, the carbon atom attached to R.sup.2 binds to B, and the carbon atom attached to R.sup.3 binds to D, R.sup.Type: GrantFiled: December 20, 1979Date of Patent: June 2, 1981Assignees: Ono Pharmaceutical Co., Ltd.,, Kissei Pharmaceutical Co., Ltd.Inventors: Tadao Tanouchi, Masanori Kawamura, Masaki Hayashi
-
Patent number: 4268688Abstract: This invention relates to a process for the preparation of optically active aldehydes by the asymmetric catalytic hydroformylation of olefins. The process comprises the hydroformylation of olefinically unsaturated prochiral compounds in the presence of an optically active coordination compound containing a metal which is selected from the group consisting of rhodium, iridium, and cobalt.This invention describes a generalized process for the asymmetric hydroformylation of a wide variety of olefins in which a preponderance of one optical isomer is produced. It is especially useful for the preparation of natural products which may require the presence of only one optical isomer for their utilization, for example, as flavors, fragrances, and medications.The catalyst systems for the process of this invention are formed in the presence of carbon monoxide and hydrogen, from coordination compounds consisting of a central metal atom, rhodium, iridium, or cobalt, and at least one optically active ligand, e.g.Type: GrantFiled: February 16, 1973Date of Patent: May 19, 1981Assignee: Monsanto CompanyInventors: Harold B. Tinker, Arthur J. Solodar
-
Patent number: 4248875Abstract: Pyridyl esters and thiolesters of .alpha.-substituted unsaturated acids, intermediates therefor, synthesis thereof and the use of said esters and thiolesters and compositions for the control of pests.Type: GrantFiled: August 31, 1979Date of Patent: February 3, 1981Assignee: Zoecon CorporationInventor: Clive A. Henrick
-
Patent number: 4246263Abstract: A series of 4-(2-hydroxyethylthiomethyl)pyridines and related compounds, and their pharmaceutically acceptable acid addition salts, having antiinflammatory and immunoregulatory activity are disclosed. Preferred compounds include 4-(2-hydroxyethylthiomethyl)pyridine itself, as well as 4-(2-hydroxyphenylthiomethyl)pyridine, 4-(2-hydroxy-1-propylthiomethyl)pyridine, 4-(3-hydroxy-2-butylthiomethyl)pyridine, 4-(2-hydroxyethylthiomethyl)pyrimidine, the acetate esters corresponding to the above compounds, and 4-(2,3-dihydroxy-1-propylthiomethyl)pyridine.Type: GrantFiled: October 15, 1979Date of Patent: January 20, 1981Assignee: Pfizer Inc.Inventors: Joseph G. Lombardino, Charles A. Harbert
-
Patent number: 4241071Abstract: Novel azacycloalkanes, azacycloalkenes and derivatives thereof and methods of preparing same are described. These compounds are useful as antidepressants, anticonvulsants, tranquilizers and analgetics.Type: GrantFiled: January 25, 1979Date of Patent: December 23, 1980Assignee: American Hoechst CorporationInventors: Lawrence L. Martin, Helen H. Ong, Vernon B. Anderson, Charles A. Crichlow
-
Patent number: 4233060Abstract: The present invention concerns new .alpha.-phenoxy-thiolpropionic acids and salts of the formula ##STR1## wherein R is hydrogen a metal cation or the cation of an amino- or ammonio-group, Z is a substituted phenyl or a substituted pyrid-2-yl radical.These compounds have herbicidal activity by themselves but can be used as intermediats for the synthesis of more active derivatives.Type: GrantFiled: November 20, 1978Date of Patent: November 11, 1980Assignee: Ciba-Geigy CorporationInventors: Beat Bohner, Otto Rohr, Hermann Rempfler, Georg Pissiotas
-
Patent number: 4215215Abstract: Novel 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraenoic acid, tetraenal or tetraenol derivatives useful as anti-tumor agents.Type: GrantFiled: July 6, 1979Date of Patent: July 29, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
-
Patent number: 4183945Abstract: Substituted 2-vinyl-chromones are disclosed, wherein the chromone ring has an alkyl or alkenyl substituent at the 3-position, and a styryl substituent at the 2-position. The compounds exhibit anti-allergy activity and can be used to treat allergic conditions.Type: GrantFiled: July 24, 1978Date of Patent: January 15, 1980Assignee: Carlo Erba S.p.A.Inventors: Gianfederico Doria, Ciriaco Romeo, Francesco Lauria, Maria L. Corno, Piernicola Giraldi, Marcello Tibolla
-
Patent number: 4136102Abstract: Halogen onium salts, and onium salts of Group VA and V1A elements having an MF.sub.6.sup.- anion, where M is selected from P, As and Sb, have been found to exhibit unusual activity under ultraviolet light. These onium salts can be employed as cationic photoinitiators when used with a variety of organic resins and cyclic organic compounds.Type: GrantFiled: April 21, 1973Date of Patent: January 23, 1979Assignee: General Electric CompanyInventor: James V. Crivello
-
Patent number: 4127583Abstract: 3-(4- OR 3-Pyridinyl)-2-cyclohexen-1-ones (I) and their oxime derivatives are useful in preparing (3-aminophenyl)pyridines, in turn, useful in preparing known antibacterial agents. Also shown is the preparation of I by starting with the reaction of methyl vinyl ketone with either 1-(pyridinyl)-1-(lower-tertiary-amino)-ethylene (II) or lower-alkyl 3-(pyridinyl)-3-oxopropanoate. Also shown is the process of converting I to its oxime, acylating the oxime and heating the acylated oxime under acidic conditions to produce N-(lower-acyl)-3-(pyridinyl)-aniline (VII), and hydrolyzing VII under aqueous alkaline conditions to produce the corresponding 3-(pyridinyl)aniline.Type: GrantFiled: January 19, 1978Date of Patent: November 28, 1978Assignee: Sterling Drug Inc.Inventors: Karl O. Gelotte, Andrew W. Zalay, Malcolm R. Bell