Chalcogen Attached Indirectly To The Six-membered Hetero Ring By Nonionic Bonding (e.g., Sulfato Betaines, Etc.) Patents (Class 546/339)
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Patent number: 4642199Abstract: A novel pyridine derivative capable of increasing the dielectric anisotropy value (.DELTA..epsilon.) or optical anisotropy value (.DELTA.n) of liquid crystal compositions including the derivative and lowering the driving voltages of liquid crystal display elements using the composition, and also a liquid crystal composition containing the pyridine derivative are provided, which pyridine derivative is expressed by the formulaR--X--COO--Y--CH.sub.2 CH.sub.2 --Z--Awherein R represents an alkyl group or an alkoxy group each of 1-10 carbon atoms; X represents ##STR1## Y represents ##STR2## when Y is ##STR3## Z represents ##STR4## and A represents F, Cl or cyano group; and when Y is ##STR5## Z represents ##STR6## and A represents an alkyl group or an alkoxy group each of 1-10 carbon atoms.Type: GrantFiled: June 13, 1985Date of Patent: February 10, 1987Assignee: Chisso CorporationInventors: Shigeru Sugimori, Kazunori Nigorikawa
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Patent number: 4631279Abstract: This invention provides certain pyridazinone derivatives, their pharmaceutical formulations, and their use as positive inotropic agents.Type: GrantFiled: October 15, 1984Date of Patent: December 23, 1986Assignee: Eli Lilly and CompanyInventor: David W. Robertson
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Patent number: 4626593Abstract: Vinyl pyridines including vinyl stilbazole materials and vinyl styrylpyridine oligomer materials are disclosed. These vinylpyridines form copolymers with bismaleimides which copolymers have good fire retardancy and decreased brittleness. The cure temperatures of the copolymers are substantially below the cure temperatures of the bismaleimides alone. Reinforced composites made from the cured copolymers are disclosed as well.Type: GrantFiled: April 22, 1985Date of Patent: December 2, 1986Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: John A. Parker, Alvin H. Heimbuch, Ming-Ta S. Hsu, Timothy S. Chen
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Patent number: 4607035Abstract: There are described 1-phenoxy(phenylthio)-4-aryl-alkynyloxy-benzene derivatives endowed with a juvenile hormonic activity towards insects and with an acaricide activity. The use of these compounds for controlling insects infestations in both the agrarian and civil field and the processes for preparing said compounds are described too.Type: GrantFiled: July 22, 1983Date of Patent: August 19, 1986Assignee: Montedison S.p.A.Inventors: Franco Bettarini, Pietro Massardo, Paolo Piccardi, Franca Reggiori, Angelo Longoni
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Patent number: 4606757Abstract: Disclosed are diphenoxymethylpyridines, their preparation and their use as herbicides.Type: GrantFiled: October 2, 1984Date of Patent: August 19, 1986Assignee: The Dow Chemical CompanyInventors: Sudarshan K. Malhotra, Ingrid L. Evoy
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Patent number: 4598080Abstract: The invention relates to new pyridine derivatives of the formula (I) ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen, halogen, trihalomethyl, alkyl having from one to 4 carbon atoms or alkoxy having from one to 4 carbon atoms,and acid addition and quaternary ammonium salts thereof.According to another aspect of the invention there are provided processes for the preparation of these compounds.The compounds of the formula (I) are pharmacologically active. In particular, they inhibit the microsomal monooxigenase enzyme system of the liver. Pharmaceutical compositions containing them as active ingredient are also within the scope of the invention.Type: GrantFiled: December 27, 1983Date of Patent: July 1, 1986Assignee: Richter Gedeon Vegyeszeti Gyar RtInventors: Edit Toth, Jozsef Torley, Eva Palosi, Szabolcs Szebereneyi, Laszlo Szporny, Sandor Gorog, Istvan Hajdu
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Patent number: 4579862Abstract: Compounds of the general formula ##STR1## and pharmaceutically acceptable salts thereof have antithrombotic activity. Het represents 1-[1H-imidazolyl], 1-N-morpholinyl or pyridyl. A representative compound is 6-[2-(1H-Imidazol-1-yl)-1-yl-1-[[(4-methoxyphenyl)methoxy]methyl]ethoxy]he xanoic acid.Type: GrantFiled: July 5, 1983Date of Patent: April 1, 1986Assignee: G. D. Searle & Co.Inventors: Paul W. Manley, Lai M. Fook
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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
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Patent number: 4563526Abstract: Novel substituted 2-(arylmethoxy)phenol compounds having the structural formula: ##STR1## where X is selected from the group consisting of: (a) napthyl, pyridyl, quinolyl and 2-benzimidazolyl; and(b) a substituted alkyl or alkoxy phenyl.Type: GrantFiled: June 14, 1983Date of Patent: January 7, 1986Assignee: Forsyth Dental Infirmary for ChildrenInventor: Floyd E. Dewhirst
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Patent number: 4540699Abstract: This invention relates to N-substituted pyridinone compounds which have histamine H.sub.2 -antagonist activity. A specific compound of this invention is 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(1-methyl-2-oxopyridin -4-ylmethyl)pyrimidin-4-one.Type: GrantFiled: November 29, 1983Date of Patent: September 10, 1985Assignee: Smith Kline & French Laboratories LimitedInventors: Thomas H. Brown, Derek A. Rawlings
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Patent number: 4539408Abstract: Quaternary sulfoalkyl or sulfoalkenyl salts of tertiary amine bases are prepared by reacting the tertiary amine bases at elevated temperatures with a hydroxy alkane sulfonic acid or a hydroxyalkene sulphonic acid.Type: GrantFiled: April 28, 1978Date of Patent: September 3, 1985Assignee: Agfa-Gevaert AktiengesellschaftInventors: Helmut Kampfer, Marie Hase, Max Glass
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Patent number: 4537963Abstract: 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[3.3.1]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: August 11, 1983Date of Patent: August 27, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ashokkumar B. Shenvi
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Patent number: 4535086Abstract: Heterocyclic compounds of the formula ##STR1## wherein X is --CH.dbd.CH--, --O-- or --S--; R.sup.1 is a group Ar--R.sup.2 or --CH.dbd.CH--C(CH.sub.3).dbd.CH--R.sup.21 ; Ar is phenyl, pyridyl, furyl or thienyl; R.sup.2 is a group --CO.sub.2 R.sup.3, --C(O)R.sup.4, --CH.sub.2 OR.sup.3, lower-alkylsulphonyl or formyl; R.sup.21 is a group--CO.sub.2 R.sup.3, --C(O)R.sup.4, --CH.sub.2 OR.sup.3 or formyl; R.sup.3 is hydrogen or lower-alkyl and R.sup.4 is hydrogen, hydroxy, amino, lower alkylamino, di-(lower alkyl)amino or lower-alkyl; at least one ring of the molecule being heterocyclic, salts thereof, processes for their preparation, rodenticidal compositions containing these compounds as the active ingredient and methods of use of the rodenticidal compositions are disclosed.Type: GrantFiled: June 27, 1983Date of Patent: August 13, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Michael Klaus, Peter Loeliger, Harald Weiser
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Patent number: 4535084Abstract: A series of 4-(2-hydroxyethylthiomethyl)pyridines and related compounds, and their pharmaceutically acceptable acid addition salts, having immunoregulatory activity are disclosed. Preferred compounds include 4-(2-hydroxyethylthiomethyl)pyridine itself, as well as 4-(2-hydroxy-1-propylthiomethyl)pyridine, 4-(3-hydroxy-2-butylthiomethyl)pyridine, the acetate esters corresponding to the above compounds, and 4-(2,3-dihydroxy-1-propylthiomethyl)pyridine.Type: GrantFiled: March 18, 1983Date of Patent: August 13, 1985Assignee: Pfizer Inc.Inventors: Joseph G. Lombardino, Charles A. Harbert
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Patent number: 4533666Abstract: This invention provides for certain novel 2,3,6-triaryl pyridine derivatives, their pharmaceutical formulations, and a method of treating pain, fever, thrombosis, inflammation, and arthritis.Type: GrantFiled: June 22, 1983Date of Patent: August 6, 1985Assignee: Eli Lilly and CompanyInventors: Ken Matsumoto, John S. Ward
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Patent number: 4526968Abstract: A aqueous electroplating bath for nickel, cobalt, nickel-cobalt, nickel-iron, cobalt-iron or nickel-cobalt-iron is described which contains, as a brightening agent, a quaternary amine sulfobetaine of the formula ##STR1## wherein N.sup.+ is a heterocyclic tertiary amine group,R is a halogen or lower alkyl group,R' is a hydrogen, lower alkyl or R"C(O)-- groupR" is a lower alkyl group anda is 0-5.These brighteners may be prepared by the reaction of a heterocyclic tertiary amine with an alkali metal halohydrin sulfonate.Type: GrantFiled: July 16, 1982Date of Patent: July 2, 1985Assignee: M&T Chemicals Inc.Inventors: Kenneth W. Lemke, Maynard W. McNeil
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Patent number: 4525360Abstract: The present invention relates to novel phenylindene derivatives having interesting pharmacodynamic properties which make them useful as psychopharmacologicals in the treatment especially of psychoses such as schizophrenia, having a low degree of undesired side effects such as cataleptic effects, methods for the preparation of said phenylindene derivatives, pharmaceutical compositions containing same, and methods for the treatment of psychic disorders, such as psychoses and depressions and pain, by administering a therapeutically active amount of one of said derivatives to a living animal body, including human beings.Type: GrantFiled: October 5, 1983Date of Patent: June 25, 1985Assignee: Kefalas A/SInventor: Jens K. Perregaard
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Patent number: 4518600Abstract: 1-Phenoxy-2-pyridinyl(pyrimidinyl)-alkanols of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl,X represents a nitrogen atom or the CH group,Y represents halogen, alkyl, cycloalkyl, alkoxy, halogenoalkyl, alkylthio, or an optionally substituted phenyl, phenoxy, phenylalkoxy or phenylalkyl radical, andn represents 0 or an integer from 1 to 5, the Y's being selected independently of one another when n is 2, 3, 4 or 5,in the form of the free base, a salt or a metal salt complex thereof, which possess fungicidal properties.Type: GrantFiled: June 20, 1980Date of Patent: May 21, 1985Assignee: Bayer AktiengesellschaftInventors: Graham Holmwood, Paul-Ernst Frohberger, Wilhelm Brandes, Volker Paul
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Patent number: 4512995Abstract: 3-[2-aryloxy-3-hydroxy-3-phenyl or 3-t-butylprop-1-enyl]pyridine and derivatives thereof are disclosed. These compounds are useful as fungicides, especially agricultural fungicides.Type: GrantFiled: January 3, 1983Date of Patent: April 23, 1985Assignee: Chevron Research CompanyInventor: Allan F. Rose
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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
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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
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Patent number: 4474602Abstract: Substituted pyridyl compounds, e.g. 2,6-dichloro-4(2-(2,2,2-trichloroethyl)oxiranyl) pyridine; herbicidal compositions containing such compounds and method for the control of undesired vegetation using these compositions.Type: GrantFiled: January 19, 1982Date of Patent: October 2, 1984Assignee: The Dow Chemical CompanyInventors: Lowell D. Markley, John M. Soper
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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
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Patent number: 4430171Abstract: An aqueous electroplating bath for nickel, cobalt, nickel-cobalt, nickel-iron, cobalt-iron or nickel-cobalt-iron is described which contains, as a brightening agent, a quaternary amine sulfobetaine of the formula ##STR1## wherein N.sup.+ is a heterocyclic tertiary amine group,R is a halogen or lower alkyl group,R' is a hydrogen, lower alkyl or R"C(O)--groupR" is a lower alkyl group anda is 0-5.These brighteners may be prepared by the reaction of a heterocyclic tertiary amine with an alkali metal halohydrin sulfonate.Type: GrantFiled: August 24, 1981Date of Patent: February 7, 1984Assignee: M&T Chemicals Inc.Inventors: Kenneth W. Lemke, Maynard W. McNeil
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Patent number: 4429162Abstract: The instant invention relates to compounds of the formula ##STR1## wherein each R.sub.f is independently straight or branched chain perfluoroalkyl of 2 to 18 carbon atoms or perfluoroalkoxy-perfluoroalkyl of 4 to 18 carbon atoms;each R.sub.1 is independently straight or branched chain alkylene of 1 to 12 carbon atoms, alkylenethioalkylene of 2 to 12 carbon atoms, alkyleneoxyalkylene of 2 to 12 carbon atoms, or alkyleneiminoalkylene of 2 to 12 carbon atoms where the imino nitrogen atom contains as a third substituent, hydrogen or alkyl of 1 to 6 carbon atoms;R.sub.2, R.sub.3 and R.sub.4 are independently hydrogen, chloro, bromo, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, hydroxyalkyl of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms, and R.sub.2 and R.sub.3 additionally may, together with the carbon atoms to which they are attached, form a fused benzo ring;R.sub.Type: GrantFiled: February 1, 1982Date of Patent: January 31, 1984Assignee: Ciba-Geigy CorporationInventors: Thomas W. Cooke, Robert A. Falk
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Patent number: 4421916Abstract: 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: December 20, 1983Assignee: E. I. Du Pont de Nemours & Co.Inventor: Ashokkumar B. Shenvi
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Patent number: 4415579Abstract: The invention relates to a pharmaceutical composition comprising an anti-ulcer effective amount of a compound of formula I ##STR1## wherein R represents hydrogen, lower alkyl, phenyl, halophenyl, loweralkylphenyl, loweralkoxyphenyl, or aralkyl of 7 to 12 carbon atoms, R.sup.1 represents hydrogen or lower alkoxy, R.sup.2 represents hydrogen, chlorine or trifluoromethyl and n is 1 or 2, or a pharmaceutically acceptable acid addition salt thereof, and a pharmaceutically acceptable carrier.A method of treating ulcers or hypersecretion in a mammal which comprises administering a compound of formula I is also disclosed. Some compounds of formula I are novel and within the scope of the invention.Type: GrantFiled: March 1, 1982Date of Patent: November 15, 1983Assignee: John Wyeth and Brother LimitedInventor: Roger Crossley
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Patent number: 4407806Abstract: 3-Pyridyl ethers of this invention possess good fungicidal, herbicidal and plantgrowth regulating activity.Type: GrantFiled: November 23, 1981Date of Patent: October 4, 1983Assignee: Chevron Research CompanyInventor: Richard E. Cherpeck
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Patent number: 4408057Abstract: Disclosed are novel compounds of the formula ##STR1## wherein R.sup.1 is a heterocyclic radical selected from furanyl, thienyl, pyridyl, pyrimidyl, oxazolyl, pyrrolyl, isoxazolyl, thiazolyl, and isothiazolyl, and R.sup.2 is hydrogen, a tetramethylcyclopropanecarbonyl group, a 1-(substituted-phenyl)-2-methylpropyl-1-carbonyl group, a 1-(4-ethoxyphenyl)-2,2-dichlorocyclopropanecarbonyl group, or a substituted-vinylcyclopropanecarbonyl group. The compounds wherein R.sup.2 is other than hydrogen are insecticides.Type: GrantFiled: December 20, 1982Date of Patent: October 4, 1983Assignee: FMC CorporationInventor: John F. Engel
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Patent number: 4394509Abstract: The invention provides a compound of formula I ##STR1## wherein R represents hydrogen, lower alkyl, phenyl, halophenyl, loweralkylphenyl, loweralkoxyphenyl or aralkyl of 7 to 12 carbon atoms, R.sup.1 represents hydrogen or fluorine, R.sup.2 represents hydrogen, fluorine, chlorine or trifluoromethyl, n is 1 or 2 or pharmaceutically acceptable acid addition salt thereof.Pharmaceutical compositions containing the compounds are also covered as are methods of treating ulcers or hypersecretion using the compounds. Corresponding thiocompounds, useful as intermediates, are also disclosed.Type: GrantFiled: January 21, 1982Date of Patent: July 19, 1983Assignee: John Wyeth and Brother LimitedInventor: Roger Crossley
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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
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Patent number: 4368205Abstract: Disclosed are novel compounds of the formula ##STR1## wherein R.sup.1 is a heterocyclic radical selected from furanyl, thienyl, pyridyl, pyrimidyl, oxazolyl, pyrrolyl, isoxazolyl, thiazolyl, and isothiazolyl, and R.sup.2 is hydrogen, a tetramethylcylopropanecarbonyl group, a 1-(substituted-phenyl)-2-methylpropyl-1-carbonyl group, a 1-(4-ethoxyphenyl)-2-dichlorocyclopropanecarbonyl group, or a substituted-vinyl-cyclopropanecarbonyl group. The compounds wherein R.sup.2 is other than hydrogen are insecticides.Type: GrantFiled: September 17, 1981Date of Patent: January 11, 1983Assignee: FMC CorporationInventor: John F. Engel
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Patent number: 4358594Abstract: Compounds are prepared corresponding to the formula ##STR1## wherein Y represents chloro or R'; R represents ##STR2## wherein X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkyl sulfonyl of 1 to 4 carbon atoms, trifluoromethyl, chloro, fluoro or bromo; n represents an integer of 0 to 2 or X.sub.n represents 3,4-methylenedioxy and R' represents R with the proviso that R and R' can be the same or different. The compounds are useful as intermediates for the preparation of insecticidal substituted pyridine methyl esters of cyclopropane carboxylic acids.Type: GrantFiled: October 30, 1981Date of Patent: November 9, 1982Assignee: The Dow Chemical Co.Inventor: Sudarshan K. Malhotra
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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
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Patent number: 4351943Abstract: Compounds are prepared corresponding to the formula ##STR1## wherein Y represents chloro or R'; R represents ##STR2## wherein X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkyl sulfonyl of 1 to 4 carbon atoms, trifluoromethyl, chloro, fluoro or bromo; n represents an integer of 0 to 2 or X.sub.n represents 3,4-methylenedioxy and R' represents R with the proviso that R and R' can be the same or different. The compounds are useful as intermediates for the preparation of insecticidal substituted pyridine methyl esters of cyclopropane carboxylic acids.Type: GrantFiled: October 30, 1981Date of Patent: September 28, 1982Assignee: The Dow Chemical Co.Inventor: Sudarshan K. Malhotra
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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
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Patent number: 4338316Abstract: The disclosure relates to 9.beta.-aryloxy prostane derivatives, for example 16-(3-chlorophenoxy)-11.alpha.,15.alpha.-dihydroxy-16-methyl-9.beta.-pheno xy-18,19,20-trinor-5-cis,13-trans-prostadienoic acid, which possess high activity as abortifacients, cervical softeners, inducers of parturition or inhibitors of gastric acid production in mammals. These properties are typical of prostaglandin analogues of the E series, but chemically the new 9.beta.-aryloxy prostane derivatives are prostaglandin F series analogues and are therefore more stable than the E series analogues previously used for the above purposes. The new derivatives are manufactured by known analogy processes, and are formulated in conventional manner.Type: GrantFiled: September 26, 1979Date of Patent: July 6, 1982Assignee: Imperial Chemical Industries LimitedInventor: Peter R. Marsham
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Patent number: 4337259Abstract: The invention relates to a pharmaceutical composition comprising an anti-ulcer effective amount of a compound of formula I ##STR1## wherein R represents hydrogen, lower alkyl, phenyl, halophenyl, loweralkylphenyl, loweralkoxyphenyl, or aralkyl of 7 to 12 carbon atoms, R.sup.1 represents hydrogen or lower alkoxy, R.sup.2 represents hydrogen, chlorine or trifluoromethyl and n is 1 or 2, or a pharmaceutically acceptable acid addition salt thereof, and a pharmaceutically acceptable carrier.A method of treating ulcers or hypersecretion in a mammal which comprises administering a compound of formula I is also disclosed. Some compounds of formula I are novel and within the scope of the invention.Type: GrantFiled: February 9, 1981Date of Patent: June 29, 1982Assignee: John Wyeth & Brother LimitedInventor: Roger Crossley
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Patent number: 4331602Abstract: 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: March 16, 1981Date of Patent: May 25, 1982Assignee: Pfizer Inc.Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4327102Abstract: The invention provides a compound of formula I ##STR1## wherein R represents hydrogen, lower alkyl, phenyl, halophenyl, loweralkylphenyl, loweralkoxyphenyl or aralkyl of 7 to 12 carbon atoms, R.sup.1 represents hydrogen or fluorine, R.sup.2 represents hydrogen, fluorine, chlorine or trifluoromethyl, n is 1 or 2 or pharmaceutically acceptable acid addition salt thereof.Pharmaceutical compositions containing the compounds are also covered as are methods of treating ulcers or hypersecretion using the compounds. Corresponding thiocompounds, useful as intermediates, are also disclosed.Type: GrantFiled: February 9, 1981Date of Patent: April 27, 1982Assignee: John Wyeth & Brother LimitedInventor: Roger Crossley
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Patent number: 4324896Abstract: Compounds are prepared corresponding to the formula ##STR1## wherein Y represents chloro or R'; R represents ##STR2## wherein X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkyl sulfonyl of 1 to 4 carbon atoms, trifluoromethyl, chloro, fluoro or bromo; n represents an integer of 0 to 2 or X.sub.n represents 3,4-methylenedioxy and R' represents R with the proviso that R and R' can be the same or different. The compounds are useful as intermediates for the preparation of insecticidal substituted pyridine methyl esters of cyclopropane carboxylic acids.Type: GrantFiled: September 18, 1980Date of Patent: April 13, 1982Assignee: The Dow Chemical CompanyInventor: Sudarshan K. Malhotra
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Patent number: 4311703Abstract: 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: August 1, 1980Date of Patent: January 19, 1982Assignee: American Hoechst CorporationInventors: Lawrence L. Martin, Helen H. Ong, Vernon B. Anderson, Charles A. Crichlow
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Patent number: 4284635Abstract: 4-Phenylpiperidines bearing substituents at the 1,2,4 and 5-positions are potent analgesics. Pharmaceutical formulations containing such compounds and a method for effecting analgesia are provided.Type: GrantFiled: November 29, 1978Date of Patent: August 18, 1981Assignee: Eli Lilly and CompanyInventor: Dennis M. Zimmerman
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Patent number: 4278797Abstract: Phenylmorphans having substituents at the 2, 3 and 7 positions and intermediates thereof are disclosed. The compounds exhibit potent analgesic activity. Formulations and a method of relieving pain are provided.Type: GrantFiled: May 19, 1980Date of Patent: July 14, 1981Assignee: Eli Lilly and CompanyInventor: Dennis M. Zimmerman
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Patent number: 4277608Abstract: 4a-Arylhexahydro-1H-2-pyrindines and 4a-aryloctahydroquinolines analgesic agonists and antagonists are prepared doubly alkylating a 4-aryltetrahydropyridine with an .alpha.,.omega.-dihaloalkane.Type: GrantFiled: April 18, 1980Date of Patent: July 7, 1981Assignee: Eli Lilly and CompanyInventors: Dennis M. Zimmerman, Roger L. Robey
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Patent number: 4270987Abstract: This invention is directed to N-(2,3-dihydroxypropyl)-pyridinium sulfates of the formula ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, are a hydrogen atom or a methyl radical; X is the acid radical SO.sub.4.sup.= or HSO.sub.4.sup.- ; and n is 1 or 2. This invention is also directed to the preparation of these compounds and their use in acid galvanic nickel baths.Type: GrantFiled: February 27, 1980Date of Patent: June 2, 1981Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Wolf-Dieter Willmund, Heinz Wagner
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Patent number: 4262000Abstract: 3-Substituted pyridine derivatives of the formula ##STR1## in which A is --CO-- or --CH(OH)--,R is alkyl or optionally substituted phenyl,X each independently is halogen, alkyl, cycloalkyl, alkoxy, alkylthio, halogenoalkyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenylalkyl or optionally substituted phenylalkoxy,n is 0, 1, 2 or 3, andm is 0 or 1,or a physiologically acceptable acid addition salt or metal salt complex thereof, which possess fungicidal activity.Type: GrantFiled: February 15, 1980Date of Patent: April 14, 1981Assignee: Bayer AktiengesellschaftInventors: Graham Holmwood, Paul-Ernst Frohberger
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Patent number: 4255428Abstract: The compounds are substituted 2-amino-4-pyrimidones with a 5-(hydroxypyridylalkyl) substituent which are histamine H.sub.2 -antagonists. Two specific compounds are 2-[2-(3-bromo-2-pyridylmethylthio)ethylamino]-5-(2-hydroxy-4-pyridylmethyl )-4-pyrimidone and 2-[4-(3-methoxy-2-pyridyl)butylamino]-5-(2-hydroxy-4-pyridylmethyl)-4-pyri midone.Type: GrantFiled: April 24, 1979Date of Patent: March 10, 1981Assignee: Smith Kline & French Laboratories LimitedInventors: Thomas H. Brown, Graham J. Durant, Charon R. Ganellin
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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
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Patent number: RE31624Abstract: A method of treating inflammation and inhibiting prostaglandin synthesis employing substituted 2-(arylmethoxy)phenol compounds.Type: GrantFiled: December 22, 1982Date of Patent: July 3, 1984Assignee: Forsyth Dental Infirmary for ChildrenInventor: Floyd E. Dewhirst