Carboxyl, Or Salt Thereof, Nitrogen And Oxygen All Bonded Directly To The Same Benzene Ring Patents (Class 562/453)
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Patent number: 4788331Abstract: The disclosure relates to a method of producing 5-amino salicylic acid from salicylic acid, with sulphanilic acid as the recyclable auxiliary chemical.The method according to the present invention includes linking between the diazonium salt of the sulphanilic acid and the salicylic acid, followed by a splitting by hydrogenation with hydrogen gas and catalyst, and selective precipitation of the desired product.Type: GrantFiled: July 7, 1987Date of Patent: November 29, 1988Assignee: Nobel Kemi ABInventor: Ulf Sjostrand
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Patent number: 4783487Abstract: Amide derivatives of non-steroidal anti-inflammatory carboxylic acids which have anti-inflammatory activity in their own right as well as being effective as pro-drugs of the carboxylic acids.Type: GrantFiled: March 13, 1986Date of Patent: November 8, 1988Assignee: Smith Kline Dauelsberg GmbHInventor: Kay Brune
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Patent number: 4772614Abstract: Quinolones with antihypertensive activity have the general formula I, ##STR1## wherein X is the residue of an optionally substituted benzene ring; R is lower alkyl; R.sub.3 is hydrogen or lower alkyl; R.sub.1 and R.sub.2, which may be the same or different, are hydrogen, lower alkyl, or, together with the nitrogen atom to which they are attached, form a 5 to 7 membered saturated heterocyclic ring optionally containing an additional hetero atom selected from nitrogen, oxygen and sulphur and optionally substituted by 1 or more lower alkyl groups; and the dotted line between positions 2 and 3 of the quinolone nucleus represents an optional bond. The compounds are useful as antihypertensive agents. They are also indicated for use in treating heart failure and ischaemic heart disease.Type: GrantFiled: June 13, 1986Date of Patent: September 20, 1988Assignee: The Boots CompanyInventors: Roy V. Davies, James Fraser, Kenneth J. Nichol
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Patent number: 4720505Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic and anti-inflammatory agents.Type: GrantFiled: November 13, 1984Date of Patent: January 19, 1988Assignee: Merck Frosst Canada, Inc.Inventors: Patrice C. Belanger, John W. Gillard, Joshua Rokach
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Patent number: 4683330Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.Type: GrantFiled: January 11, 1985Date of Patent: July 28, 1987Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4670604Abstract: 4-Acylresorcinol ethers of the formula ##STR1## in which R.sub.1 is lower alkyl, R.sub.2 is fluorinated lower alkyl, R.sub.3 is hydrogen, lower alkoxy, trifluoromethyl or halogen, alk is an alkylene or hydroxyalkylene radical which is uninterrupted or interrupted by oxygen, one of the radicals R.sub.4, R.sub.5 and R.sub.7 is a group of the formula --NH--C(.dbd.O)--R.sub.8, a radical R.sub.4 or R.sub.5 which differs from this is a radical R.sub.9 and a radical R.sub.7 which differs from this is a radical R.sub.10, R.sub.6 is hydrogen, lower alkyl, trifluoromethyl, halogen, carboxyl which is free, esterified or amidated, cyano or lower alkanoyl, R.sub.8 is carboxyl which is free, esterified or amidated or 5-tetrazolyl, R.sub.9 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl and R.sub.10 is hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl, cyano or carboxyl which is free, esterified or amidated, and their salts have antiallergic and antiinflammatory properties.Type: GrantFiled: November 22, 1985Date of Patent: June 2, 1987Assignee: Ciba-Geigy CorporationInventors: Andreas Beck, Alfred Sallmann, Robert W. Lang, Paul Wenk
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Patent number: 4668814Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.Type: GrantFiled: January 11, 1985Date of Patent: May 26, 1987Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4658054Abstract: A process for the preparation of 5,6-dialkoxyanthranilic acids is described. The 5,6-dialkoxyanthranilic acids are useful in the preparation of substituted quinazolinediones which are active cardiotonic agents.Type: GrantFiled: July 29, 1985Date of Patent: April 14, 1987Assignee: Ortho Pharmaceutical CorporationInventor: Richard A. Conley
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Patent number: 4634777Abstract: Compounds of the general formula: ##STR1## wherein A and B are both hydrogen, or one of A and B is a group (G) of the formula: ##STR2## and the other is a group R.sup.5 wherein R.sup.1 is an aryl group or a heterocyclic group, both of them being optionally substituted, and R.sup.4 and R.sup.5 are both hydrogen or together form a single chemical bond,R.sup.2 and R.sup.2 ' are independently hydrogen, halogen, nitro, lower alkyl or lower alkoxy, andR.sup.3 and R.sup.3 ' are independently carboxy or its functional derivative, with the proviso that (a) when A and B are both hydrogen, then R.sup.2 and R.sup.2 ' cannot be both hydrogen,and, where applicable, pharmaceuticably acceptable salts thereof are hyaluronidase inhibitors, and useful as anti-allergic agent and anti-ulcerous agent. Among the compound (I'), those wherein when one of A and B is the group (G) and the other is the group R.sup.5 wherein R.sup.4 and R.sup.5 together form a single chemical bond, R.sup.1 is unsubstituted aryl and R.sup.2 and R.sup.Type: GrantFiled: February 1, 1985Date of Patent: January 6, 1987Assignee: Sawai Pharmaceutical Co., Ltd.Inventors: Toshio Satoh, Hitoshi Matsumoto, Hisao Kakegawa, Yoshiko Kato, Juichi Riku, Junji Yoshinaga, Yoshifumi Kanamoto
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Patent number: 4622379Abstract: A composition comprising an aromatic copolyester-carbonate having flexural modulus, flexural yield and secondary transition temperature improvement over a corresponding aromatic polycarbonate effective amount of ester units of the structure ##STR1## or mixtures of the above two structures wherein R.sub.1 and R.sub.2 are the same or different and are alkyl of one to six carbon atoms, inclusive, cycloalkyl of four to seven carbon atoms, inclusive, phenyl, one to three alkyl substituted phenyl each alkyl having one to three carbon atoms, inclusive, and R.sub.1 and R.sub.2 taken together with the nitrogen to which they are attached form a ring of four to six carbon atoms, inclusive, or carbazole.Type: GrantFiled: October 5, 1984Date of Patent: November 11, 1986Assignee: General Electric CompanyInventor: Niles R. Rosenquist
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Patent number: 4587356Abstract: The present invention provides an improved method for producing a nuclear substituted cinnamoylanthranilic acid compound.Illustrative of the process is the reaction of 3-hydroxy-4-methoxybenzaldehyde with 2-carboxymalonanilic acid in an inert solvent medium in the presence of a molar excess of piperidine to provide a high purity intermediate salt precipitate, and the salt is treated with an acidic reagent to yeild N-(3-hydroxy-4-methoxycinnamoyl)anthranilic acid product.Type: GrantFiled: September 25, 1984Date of Patent: May 6, 1986Assignee: Kissei Pharmaceutical Co., Ltd.Inventors: Kinji Iizuka, Tetsuhide Kamijo, Ryoji Yamamoto, Hiromu Harada
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Patent number: 4517130Abstract: An improved process for preparing substituted amino acids and lower alkyl esters thereof, and intermediates therefor, comprising reacting a substituted aniline, HCN and an aldehyde to form a nitrile, converting the nitrile to an imidate salt with a strong acid and an alcohol, hydrolyzing in situ the imidate salt to the ester with addition of water, and optionally converting the ester to the salt or free acid. The acids are useful intermediates in the synthesis of pesticides.Type: GrantFiled: February 17, 1984Date of Patent: May 14, 1985Assignee: Zoecon CorporationInventor: Ted A. Baer
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Patent number: 4408059Abstract: Milbemycin and avermectin macrolides are synthesized by the cyclized linking of separately synthesized northern and southern hemisphere intermediates. The northern hemisphere intermediate is a spiroketal alkenyl aldehyde, and the southern hemisphere intermediate is an aryl alkenyl phosphine oxide anion.Type: GrantFiled: December 4, 1981Date of Patent: October 4, 1983Assignee: University Patents, Inc.Inventors: Amos B. Smith, III, Steven R. Schow
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Patent number: 4371547Abstract: 2-Benzylideneglutaraldehydes of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently are hydrogen or a substituent selected from the group consisting of halo, lower-alkyl, phenyl, carboxy, lower-alkoxycarbonyl, phenoxycarbonyl, aminocarbonyl, hydroxysulfonyl, nitro, cyano, hydroxy, lower-alkoxy and phenoxy, a method of use thereof as disinfectants, disinfectant compositions comprising them, and 2,6-dialkoxy-3-(.alpha.-alkoxybenzyl)tetrahydropyrans of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are as defined above and R.sup.4 and R.sup.5 independently are alkyl of one to four carbon atoms, which are intermediates for their preparation are disclosed.Type: GrantFiled: August 21, 1981Date of Patent: February 1, 1983Assignee: Sterling Drug Inc.Inventors: Wolfgang Munzenmaier, Heinz Eggensperger, Helmut H. Ehlers, Wolfgang Beilfuss, Lothar Bucklers, Hans-Peter Harke
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Patent number: 4349689Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.Type: GrantFiled: December 22, 1980Date of Patent: September 14, 1982Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4337270Abstract: Novel anthranilic acid derivatives of the general formula: ##STR1## wherein X is a halogen atom, an alkoxyl group having 1-3 carbon atoms, an alkyl group having 1-3 carbon atoms or a nitro group, n is an integer of 1-2, Y is an alkoxyl group having 1-3 carbon atoms, m is an integer of 2-3, Z is --COCH.dbd.CH-- or --CO--, R.sub.1 is a hydrogen atom or an alkyl group having 1-4 carbon atoms, and pharmaceutically acceptable salts thereof, which derivatives and salts possess a strong antiallergic action and are thus useful as therapeutically active agents for diseases caused by allergies, such as asthma, hay fever, urticaria and atopic dermatitis; an antiallergic composition comprising the same; and a method of alleviating diseases caused by allergies using the same.Type: GrantFiled: May 21, 1980Date of Patent: June 29, 1982Assignee: Hisamitsu Pharmaceutical Co., Inc.Inventors: Kanji Noda, Akira Nakagawa, Toshiharu Motomura, Masayoshi Tsuji, Hidetoshi Amano, Hiroyuki Ide
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Patent number: 4304728Abstract: Compounds are described of the formula ##STR1## in which R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano, 5-tetrazolyl or R.sup.6, where R.sup.5 is hydrogen or C.sub.1-8 alkyl and R.sup.6 is phenyl or naphthyl, the phenyl or naphthyl group being optionally substituted by one or more group selected from halogen, C.sub.1-6 alkyl, C.sub.1-4 alkoxy, hydroxy, benzyloxy, nitro, trifluoromethyl, carboxyl, C.sub.1-4 alkylsulphinyl, C.sub.1-4 alkylsulphonyl, N(R.sup.5).sub.2, NHCOR.sup.5 and SR.sup.5 ; R.sup.2 is R.sup.6 or --CH.dbd.CH--R.sup.6 when R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano or 5-tetrazolyl, or R.sup.2 is --CH.dbd.CH--R.sup.6 when R.sup.1 is R.sup.6 ; R.sup.3 is hydrogen, C.sub.1-6 alkyl, halogen, hydroxy or --OCH.sub.2 R.sup.6 ; and R.sup.4 is hydrogen, C.sub.1-6 alkyl or halogen; and salts thereof. The compounds have pharmaceutical properties and in particular are useful in the treatment of immediate hypersensitivity conditions such as asthma.Type: GrantFiled: March 27, 1980Date of Patent: December 8, 1981Assignee: Lilly Industries LimitedInventors: Barry P. Clark, William J. Ross, Alec Todd
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Patent number: 4299747Abstract: Coating compositions which may be applied by conventional techniques as well as by electrodeposition are provided by reacting a polyglycidyl ether of a polyphenol with an amino acid containing at least one amine group and one carboxyl group, wherein the amine group of the acid is preferentially reactive with the epoxy groups of the polyglycidyl ether. The resultant product can then be solubilized by neutralizing at least a portion of the acid functionality thereof with an amine or other base. Especially useful amino acids are the aminobenzoic acids.Type: GrantFiled: March 8, 1977Date of Patent: November 10, 1981Assignee: PPG Industries, Inc.Inventor: William J. Birkmeyer
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Patent number: 4287341Abstract: 2,4-Diaminoquinazolines of the formula ##STR1## wherein Y.sup.1 is hydrogen or chloro, Y.sup.2 is OR, Y.sup.3 is hydrogen or OR such that when Y.sup.1 is hydrogen, Y.sup.3 is OR and when Y.sup.1 is chloro, Y.sup.3 is hydrogen or OR, and the pharmaceutically acceptable salts thereof; R represents an alkyl group having from one to three carbon atoms;taken separately, R.sup.1 and R.sup.2 are each hydrogen, alkyl having from one to five carbon atoms, cycloalkyl having from three to eight carbon atoms, alkenyl or alkynyl each having from three to five carbon atoms or hydroxy substituted alkyl having from two to five carbon atoms, when taken together with the nitrogen atom to which they are attached R.sup.1 and R.sup.2 form a substituted or unsubstituted heterocyclic group optionally containing an atom of oxygen, sulfur or a second atom of nitrogen as a ring member; their use as antihypertensive agents, pharmaceutical compositions containing them and intermediates for their production.Type: GrantFiled: March 3, 1980Date of Patent: September 1, 1981Assignee: Pfizer Inc.Inventors: Hans-Jurgen E. Hess, Jasjit S. Bindra, Praful K. Shah
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Patent number: 4281181Abstract: Novel L-.gamma.-glutamyl-3-carboxy-4-hydroxyanilide of the formula, ##STR1## an acid addition salt thereof, or an alkali metal or amine salt thereof, which is useful for determining the activity of .gamma.-glutamyl transpeptidase.Type: GrantFiled: November 14, 1979Date of Patent: July 28, 1981Assignees: Nitto Boseki Co., Ltd., Iatron Laboratories, Inc.Inventors: Takeshi Nagasawa, Katsumasa Kuroiwa, Katsuyuki Takabayashi, Norimasa Takizawa, Kazuyo Hagihara, Tadami Akatsuka
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Patent number: 4268669Abstract: The present invention particularly relates to novel 9-deoxy-9-methylene-5,6-didehydro-PGF.sub.1 amides and methods for their preparation in pharmacological use.Type: GrantFiled: January 28, 1980Date of Patent: May 19, 1981Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4260558Abstract: An improvement in the process for the preparation of an aromatic hydroxy compounds by reacting an aromatic nitroso compound of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently represent hydrogen, a lower alkyl radical, halogen, a carboxyl or sulfo group or the corresponding alkali metal salt thereof orR.sup.1, R.sup.2 or R.sup.3 individually represent an optionally substituted aromatic ring formed by linking two adjacent radicals,with hydrazine, the improvement residing in reacting the aromatic nitroso compound with the hydrazine in approximately equivalent amounts in an aqueous medium at temperatures from 10.degree. to 50.degree. C., in the absence of a catalyst the aromatic nitroso compound being initially introduced into a reaction chamber and the hydrazine being added thereto.Type: GrantFiled: October 23, 1978Date of Patent: April 7, 1981Assignee: Bayer AktiengesellschaftInventor: Theodor Pfister
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Patent number: 4243819Abstract: Esters and thiolesters of amino acids, intermediates therefor, synthesis thereof, and the use of said esters and thiolesters and compositions for the control of pests.Type: GrantFiled: February 16, 1978Date of Patent: January 6, 1981Assignee: Zoecon CorporationInventors: Clive A. Henrick, Barbara A. Garcia
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Patent number: 4243678Abstract: Compounds of the formula ##STR1## wherein R is (a) optionally-substituted and optionally-hydrogenated biphenylyl, (b) optionally-substituted and optionally-hydrogenated bicyclic aryl having from 8 to 12 ring carbon atoms or (c) a radical of the formula ##STR2## R.sup.1 is aliphatic hydrocarbyl, alicyclic hydrocarbyl or optionally-substituted phenyl;R.sup.2 is --H or lower aliphatic hydrocarbyl;R.sup.3 is --H, lower alkyl, cycloalkyl, optionally-substituted phenyl or, with R.sup.4, alkylene;R.sup.4 is lower alkyl, cycloalkyl, optionally-substituted phenyl, optionally-(nuclearly)-substituted phenalkyl or, with R.sup.3, alkylene;or R.sup.2,R.sup.3 and R.sup.4, together with the carbon to which each is bound, are adamantyl; andn is 3, 4 or 5;and salts thereof with a base are pharmacologically active. Esters thereof are valuable intermediates for the preparation of the pharmacologically-active compounds. Physiologically-acceptable embodiments are administered, e.g.Type: GrantFiled: December 15, 1978Date of Patent: January 6, 1981Assignee: Byk Gulden Lomberg Chemische Fabrik GmbHInventor: Walter Krastinat
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Patent number: 4191840Abstract: Anti-allergic agents of aromatic oxamic acid derivation present the following formula: ##STR1## in which A is a member selected from the group consisting of .alpha.-naphthyl, .beta.-napthtyl, phenyl, 2,6-di-chlorophenyl, and substituted phenyl moieties containing from one to three substituents in any of the 2,3,4 and 5 positions of the phenyl ring, independently selected from the group consisting of lower alkyl, lower alkylthio, lower alkylsulfinyl, lower alkoxy, hydroxy (lower)alkoxy, 2-(oxalyloxy) ethoxy, benzyloxy, N-mono- and di-lower alkylamino(lower)alkoxy, halo, sulfamyl, polyhalo(lower)alkyl, carbamyl, N-lower alkylcarbamyl, nitro, mono and di lower alkylamino, carboxy, lower alkylcarbonyl, carb(lower)alkoxy, phenoxy(lower)alkoxy, and oxalamidophenoxy radicals;and pharmaceutically acceptable salts thereof.Type: GrantFiled: February 7, 1979Date of Patent: March 4, 1980Assignee: American Home Products CorporationInventors: John H. Sellstedt, Charles J. Guinosso, Albert J. Begany
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Patent number: 4159278Abstract: Compounds represented below ##STR1## and pharmaceutical compositions thereof, the compositions including the non-substituted phenylene dioxamates are useful in the prophylactic treatment of sensitized mammals for allergy and all anaphylactic reactions of a reagin or non-reagin mediated nature.Type: GrantFiled: October 31, 1977Date of Patent: June 26, 1979Assignee: The Upjohn CompanyInventors: Charles M. Hall, John B. Wright
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Patent number: 4154961Abstract: Anti-allergic agents of aromatic oxamic acid derivation present the following formula: ##STR1## in which A is a member selected from the group consisting of .alpha.-naphthyl, .beta.-naphthyl, phenyl, 2,6-di-chlorophenyl, and substituted phenyl moieties containing from one to three substituents in any of the 2,3,4 and 5 positions of the phenyl ring, independently selected from the group consisting of lower alkyl, lower alkylthio, lower alkylsulfinyl, lower alkoxy, hydroxy (lower)alkoxy, 2-(oxalyloxy) ethoxy, benzyloxy, N-mono- and di-lower alkylamino(lower)alkoxy, halo, sulfamyl, polyhalo(lower)alkyl, carbamyl, N-lower alkylcarbamyl, nitro, mono and di lower alkylamino, carboxy, lower alkylcarbonyl, carb(lower)alkoxy, phenoxy(lower)alkoxy, and oxalamidophenoxy radicals;And pharmaceutically acceptable salts thereof.Type: GrantFiled: September 19, 1977Date of Patent: May 15, 1979Assignee: American Home Products CorporationInventors: John H. Sellstedt, Charles J. Guinosso, Albert J. Begany
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Patent number: 4152456Abstract: Tropone derivatives substituted with an amino-, thio- or oxy-derivative of oxalic acid or acetic acid are disclosed. In addition, the tropone nucleus can be optionally further substituted. The foregoing compounds are useful for preventing or treating allergic conditions in a mammal. Methods for the preparation and use of the compounds are disclosed.Type: GrantFiled: October 7, 1977Date of Patent: May 1, 1979Assignee: Ayerst, McKenna and Harrison LimitedInventors: Jehan F. Bagli, Tibor Bogri
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Patent number: 4146385Abstract: The invention provides novel phenoxyalkylcarboxylic acids which are useful in therapy as metabolic regulators and in agriculture as selective herbicides.Type: GrantFiled: August 16, 1976Date of Patent: March 27, 1979Assignee: Societe de Recherches Industrielles S.O.R.I.Inventor: Bernard Majoie
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Patent number: 4136192Abstract: Bicyclic compounds useful in the prophylaxis and treatment of allergic diseases, pharmaceutical compositions containing the same, methods of administration of the compositions, intermediates useful in preparing the compounds and conversion of the intermediates to the bicyclic compounds. Examples of compounds are substituted coumarins and indanediones and their pharmaceutically acceptable salts.Type: GrantFiled: March 22, 1977Date of Patent: January 23, 1979Assignee: Beecham Group LimitedInventors: Derek R. Buckle, Harry Smith
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Patent number: 4123455Abstract: Phenenyltris(carbonylimino) multi-anionic substituted triphenyl acids and salts useful as complement inhibitors.Type: GrantFiled: June 13, 1977Date of Patent: October 31, 1978Assignee: American Cyanamid CompanyInventors: Ransom B. Conrow, Seymour Bernstein
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Patent number: 4119609Abstract: Adducts of epoxy compounds with amino-substituted aromatic carboxylic acids are described. These carboxyl-containing adducts may be cured with conventional epoxy curing agents or solubilized to prepare aqueous coating systems.Type: GrantFiled: March 28, 1977Date of Patent: October 10, 1978Assignee: Shell Oil CompanyInventors: Roy A. Allen, LeRoy W. Scott