Four Or More Ring Nitrogens In The Tricyclo Ring System Patents (Class 544/251)
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Patent number: 4713383Abstract: [1,2,4]triazolo[1,5-c]quinazoline compounds of the formula ##STR1## wherein R.sub.1 is optionally substituted phenyl, pyridyl, furyl thienyl, dihydro or tetrahydro furanyl or thienyl, pyranyl, or 0-ribofuranosyl; R.sub.2 is hydrogen or lower alkyl; X is oxygen or NR.sub.3, R.sub.3 is as defined in the claims, and ring A is unsubstituted or substituted as set forth in the claims. The compounds wherein X is N--R.sub.3 are especially useful as adenosine antagonists and for the treatment of asthma. The compounds wherein X is oxygen are useful as benzodiazepine antagonists and as intermediates in the synthesis of the compounds wherein X is N--R.sub.3.Type: GrantFiled: March 26, 1986Date of Patent: December 15, 1987Assignee: Ciba-Geigy CorporationInventors: John E. Francis, Karl O. Gelotte
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Patent number: 4701526Abstract: There is disclosed a process for preparing 9-(2-hydroxyethoxymethyl)-guanine (acyclovir) of the formula IV ##STR1## wherein a novel compound of the formula I ##STR2## wherein R and R' may be the same or different and represent hydrogen, (C.sub.1 -C.sub.8)acyl or benzyl and R.sub.1 represents (C.sub.1 -C.sub.8)acyl, is hydrolyzed under mild basic conditions. Also disclosed is the novel compound of the formula I, a process for the preparation thereof by condensing a novel compound of the formula II ##STR3## with a compound A--CH.sub.2 --O--CH.sub.2 CH.sub.Type: GrantFiled: December 11, 1985Date of Patent: October 20, 1987Assignee: KRKA, tovarna zdravil, n.sol.o.Inventors: Joze Kobe, Joze Gnidovec, Pavle Zupet
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Patent number: 4687847Abstract: Very pure riboflavin (I) is obtained by a process in which the riboflavin is dissolved in dilute aqueous alkali metal hydroxide solution, if necessary the alkaline solution is purified by treatment with active carbon or with a solvent which is insoluble or only slightly soluble in water, the resulting alkaline solution of I is introduced into water which is at 90.degree.-100.degree. C. and to which an acid has been added in an amount such that the reaction mixture is brought to a pH of from 6.5 to 0.8, the temperature being maintained at from 40.degree. to 100.degree. C., the reaction mixture is kept at from 90.degree. to 100.degree. C. for from 10 to 80 minutes and cooled, and I is then isolated.Type: GrantFiled: June 10, 1985Date of Patent: August 18, 1987Assignee: BASF AktiengesellschaftInventors: Johannes Grimmer, Hans C. Horn
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Patent number: 4678499Abstract: Benzenesulfonamide compounds such as N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-1,4-dihydro-3-methyl-4 -oxo-1-phenyl-indeno[1,2-C]-pyrazole-5-sulfonamide and N-[(4-methoxy-6-methyl-pyrimidin-2-yl)aminocarbonyl]-1,4-dihydro-3-methyl- 4-oxo-1-phenyl-indeno[1,2-C]pyrazole-5-sulfonamide, agricultural compositions containing them, and their herbicidal utility are disclosed.Type: GrantFiled: January 30, 1986Date of Patent: July 7, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventors: Robert J. Pasteris, Ramaurthi Muthukrishnan
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Patent number: 4675172Abstract: Metal values, particularly copper values, are extracted from aqueous solutions containing halide or pseudohalide anion using 6,7 substituted triazolopyrimidine wherein the 6-substituent is a group --CO--OR1 where R1 is a hydrocarbyl group containing from 1 to 35 carbon atoms, preferably an alkyl group and wherein the 7-substituent (R2) is hydrogen or a hydrocarbyl group containing from 1 to 35 atoms wherein R1 and R2 taken together contain a total of from 5 to 35 saturated carbon atoms.Type: GrantFiled: December 9, 1985Date of Patent: June 23, 1987Assignee: Imperial Chemical Industries PLCInventors: Peter M. Quan, Anthony J. Nelson
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Patent number: 4673742Abstract: Riboflavin of the formula I ##STR1## is prepared by condensation of a 4,5-dimethyl-N-(D)-ribityl-2-phenylazoaniline of the formula II ##STR2## where X is H, --Cl, --NO.sub.2 or --CH.sub.3 in the o- or p-position, with barbituric acid of the formula III ##STR3## in the presence of an acidic condensing agent in an inert organic solvent by an improved process in which the reaction is carried out in an aliphatic diol or triol derivative of the general formula IV ##STR4## where R.sup.1 is H or CH.sub.3, R.sup.2 is H or CH.sub.3 -- or, when n is 0, is CH.sub.3 --CO--O--CH.sub.2 --, R.sup.3 is CH.sub.3 --, C.sub.2 H.sub.5 -- or CH.sub.3 --, R.sup.4 is CH.sub.3 --CO--, or is H when R.sup.3 is CH.sub.3 -- or C.sub.2 H.sub.5 --, and n is 0 or 2, preferably 0, having a boiling point of 80.degree.-180.degree. C., or in a mixture of these as a solvent. In this process, the riboflavin is obtained in particularly pure form and in very good yields.Type: GrantFiled: February 20, 1985Date of Patent: June 16, 1987Assignee: BASF AktiengesellschaftInventors: Johannes Grimmer, Hans C. Horn
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Patent number: 4666914Abstract: Substituted 2,3-dihydro-6-(hydroxy)pyrimido[2,1-f]purine-4,8(1H,9H)-diones their tautomers and salts, are anti-inflammatory and anti-allergy agents.Methods for their preparation and use are described.Type: GrantFiled: May 13, 1985Date of Patent: May 19, 1987Assignee: Schering CorporationInventors: Daniel M. Solomon, James J. Kaminski, David J. Conn
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Patent number: 4656275Abstract: An improved process for the preparation of riboflavin by condensation of a 4,5-dimethyl-N-(D)-ribityl-2-phenylazoaniline derivative with barbituric acid in the presence of an acidic condensing agent in an organic solvent, wherein a 4,5-dimethyl-N-(D)-ribityl-2-(o-alkoxyphenylazo)-aniline of the formula IIa ##STR1## where R is alkyl of 1 to 4 carbon atoms, in particular methyl, is reacted with barbituric acid, as well as the novel intermediates of the formula IIa.Type: GrantFiled: May 3, 1985Date of Patent: April 7, 1987Assignee: BASF AktiengesellschaftInventors: Hansgeorg Ernst, Heinz Eckhardt, Joachim Paust
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Patent number: 4652646Abstract: Novel triazolopyrimidine compounds represented by the formula (I) and physiologically acceptable salts thereof are disclosed. These compounds have an excellent anti-allergic activity in oral administration and are useful for treatment and prophylaxis of allergic diseases such as bronchial asthma, allergic gastro-intestinal disorders, allergic rhinitis, hay fever, urticaria and the like.Type: GrantFiled: April 25, 1985Date of Patent: March 24, 1987Assignee: Daiichi Seiyaku Co., Ltd.Inventors: Sumiro Isoda, Norio Suzuki, Tamotsu Miwa, Shunzo Aibara
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Patent number: 4650892Abstract: Sulfonamides derived from substituted 2-amino-1,2,4-triazolo[1,5-a]pyrimidines are prepared by reacting a desired sulfonamide with dimethyl N-cyanodithioiminocarbonate in the presence of a base followed by reaction with an excess of hydrazine and then a 1,3-dicarbonyl compound.The resulting products have a variety of herbicidal uses.Type: GrantFiled: December 23, 1985Date of Patent: March 17, 1987Assignee: The Dow Chemical CompanyInventors: William A. Kleschick, Anna P. Vinogradoff, Joseph E. Dunbar
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Patent number: 4642345Abstract: Imidazopyrimidinones and other diazaheterocyclopyrimidinones having an additional fused imidazole or triazole ring have utility as bronchodilators, mediator release inhibitors, phosphodiesterase inhibitors, and peripheral vasodilators. They are orally active and useful in the prophylaxis and treatment of asthma. A preferred compound is 4-[(4-chlorophenyl)methyl]-6,7-dihydro-3H-imidazo[1,2-a]-purin-9(4H)-one.Type: GrantFiled: September 6, 1983Date of Patent: February 10, 1987Assignee: Mead Johnson & CompanyInventor: Davis L. Temple, Jr.
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Patent number: 4639518Abstract: The synthesis of 5,6-dioxy substituted quinazolinediones is described. The novel quinazolinediones are useful as cardiotonic agents.Type: GrantFiled: September 24, 1984Date of Patent: January 27, 1987Assignee: Ortho Pharmaceutical CorporationInventors: Victor T. Bandurco, Stanley C. Bell, Donald W. Combs, Robert Falotico, Alfonso J. Tobia
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Patent number: 4638075Abstract: Sulfonamides derived from substituted 2-amino-1,2,4-triazolo[1,5-a]pyrimidines are prepared by reacting a desired sulfonamide with dimethyl N-cyanodithioiminocarbonate in the presence of a base followed by reaction with an excess of hydrazine and then a 1,3-dicarbonyl compound.The resulting products have a variety of herbicidal uses.Type: GrantFiled: December 23, 1985Date of Patent: January 20, 1987Assignee: The Dow Chemical CompanyInventors: William A. Kleschick, Anna P. Vinogradoff, Joseph E. Dunbar
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Patent number: 4585772Abstract: The invention relates to pharmaceutical compositions containing active ingredients of Formula (I) and methods for the use of said compositions to treat cardiac insufficiencies. Also included in the invention are methods of the manufacture of said active ingredients of Formula (I). The invention includes, additionally, compounds of Formula (I).Type: GrantFiled: July 11, 1983Date of Patent: April 29, 1986Assignee: Bayer AktiengesellschaftInventors: Bodo Junge, Siegfried Goldmann, Gunter Thomas, Bernward Garthoff
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Patent number: 4577018Abstract: Platinum chelates of 2,3-diamino-substituted-4(3H)-pyrimidinones which are useful as antitumor agents.Type: GrantFiled: August 22, 1983Date of Patent: March 18, 1986Assignee: American Cyanamid CompanyInventors: Joseph J. Hlavka, Panayota Bitha, Yang-i Lin
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Patent number: 4569936Abstract: Substituted 9H-8-oxo-pyrimido[2,1-f]purine-2,4-diones their tautomers and salts are anti-inflammatory agents.Methods for their preparation and use are described.Type: GrantFiled: October 21, 1983Date of Patent: February 11, 1986Assignee: Schering CorporationInventor: David J. Blythin
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Patent number: 4567262Abstract: An improved process for the purification of crude riboflavin which has been prepared by condensation of an N-(D)-ribityl-2-arylazo-4,5-dimethylaniline and barbituric acid or another N-(D)-ribityl-4,5-dimethyl-aniline derivative with a barbituric acid derivative, by dissolving the crude riboflavin in sulfuric acid or phosphoric acid which has been diluted with water and oxidizing the impurities by treating the solution with hydrogen peroxide, or by dissolving the riboflavin in dilute nitric acid at elevated temperature and then isolating the pure riboflavin by precipitation with water, wherein the mineral acid solution of the riboflavin and the oxidizing agent or the solution of the riboflavin in 20 to 70% strength by weight nitric acid is heated extremely rapidly to a temperature at which the solution clearly changes color from greenish to yellow-orange, the solution is kept at this temperature for from 1 to 50, seconds and the oxidation reaction is then interrupted by addition of water.Type: GrantFiled: December 14, 1983Date of Patent: January 28, 1986Assignee: BASF AktiengesellschaftInventors: Johannes Grimmer, Hans C. Horn
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Patent number: 4567261Abstract: Riboflavin of the formula I ##STR1## is prepared by condensing a 4,5-dimethyl-N-(D)-ribityl-2-phenylazoaniline of the formula II ##STR2## where R is H or --Cl, --NO.sub.2 or --CH.sub.3 in the o- or p-position, with barbituric acid of the formula III ##STR3## in the presence of an acid as the condensing agent, by an improved process in which the acidic condensing agent used is an aliphatic or cycloaliphatic/aliphatic tertiary carboxylic acid of the general formula IV ##STR4## where R.sup.1, R.sup.2 and R.sup.3 are each a lower alkyl group, R.sup.1, R.sup.2 and R.sup.3 together containing 3 to 20, preferably 3 to 10, carbon atoms, or R.sup.1 is a lower alkyl group, in particular methyl, and R.sup.2 and R.sup.3 together form a tetramethylene or pentamethylene group.The process can be particularly advantageously carried out using trimethylacetic acid or a commercial mixture of saturated tertiary carboxylic acids, e.g. Versatic .sup.R 10-acid.Type: GrantFiled: January 13, 1984Date of Patent: January 28, 1986Assignee: BASF AktiengesellschaftInventors: Hansgeorg Ernst, Wolfram Schmidt, Joachim Paust
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Patent number: 4562192Abstract: This disclosure relates to a class of novel 6-substituted-5-phenyltetrazolo[1,5-a][1,2,4]triazole [1,5-c]pyrimidines and to pharmaceutical compositions containing such compounds. The compounds and compositions disclosed are useful as renal vasodilators, diuretics and/or anti-hypertensive agents for the treatment of hypertensive disorders in humans.Type: GrantFiled: February 3, 1984Date of Patent: December 31, 1985Assignee: G. D. Searle & Co.Inventor: Hans Wagner
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Patent number: 4560689Abstract: Disclosed are heterocyclic-fused pyrazolo[3,4-d]pyridin-3-ones useful as benzodiazepine receptor modulators.Type: GrantFiled: August 6, 1984Date of Patent: December 24, 1985Assignee: Ciba-Geigy CorporationInventor: Naokata Yokoyama
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Patent number: 4535081Abstract: Antiallergy and antiulcer agents having the formula (I), ##STR1## and their pharmaceutically acceptable salts, wherein R.sub.1 and R.sub.2 taken separately are each hydrogen or lower alkyl; and R.sub.1 and R.sub.2 taken together are alkylene of 3-9 carbon atoms or phenylalkylene of 9-11 carbon atoms, with the proviso that the ring so formed is between 5- and 8-membered; acids of the formula (II), ##STR2## wherein R.sub.1 and R.sub.2 are as defined above and R.sub.3 is hydrogen, which are useful as intermediates for compounds of the formula (I), but in many instances also possess the same useful biological activity as do formula I compounds; and intermediates of the formula II wherein R.sub.1 and R.sub.2 are defined as above, and R.sub.3 is alkyl of 1 to 4 carbon atoms, carbalkoxy of 2 to 5 carbon atoms, carbophenoxy or carbobenzoxy, are also described.Type: GrantFiled: August 17, 1983Date of Patent: August 13, 1985Assignee: Pfizer Inc.Inventor: Saul B. Kadin
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Patent number: 4520196Abstract: .alpha.-Mercaptobenzylacetic acid derivatives of imidazole-containing compounds and analogues thereof, and their use as immunomodulating agents are disclosed.Type: GrantFiled: August 18, 1983Date of Patent: May 28, 1985Assignee: American Home Products CorporationInventor: Peter H. L. Wei
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Patent number: 4517183Abstract: The present invention provides pharmaceutical compositions containing N-substituted aziridine-2-carboxylic acid derivatives of the general formula: ##STR1## wherein X is a carboxyl, a cyano, an alkoxycarbonyl or an optionally substituted carbamoyl radical, R is a hydrogen atom, an aliphatic hydrocarbon radical which is saturated or can contain one or more unsaturations and can be substituted one or more times by halogen, alkoxy, hydroxyl, dialkylamino, dialkylaminoxy, cycloalkylamino, acylamino, acyl, nitro, alkylthio, alkylsulphinyl, alkylsulphonyl, cyano, carboxyl, alkoxycarbonyl or carbamoyl or by cycloalkyl or cycloalkenyl radicals optionally carrying alkyl, alkoxy or alkoxycarbonyl radicals, optionally interrupted by hetero atoms and optionally bridged, or by an aryl, hetaryl, aryloxy, arylthio, acyloxy, alkoxycarbonylamino or isothioureido radical, or R is a cycloalkyl or cycloalkenyl radical optionally substituted by alkyl, alkoxy or oxo groups, optionally interrupted by hetero atoms and optionally briType: GrantFiled: May 17, 1983Date of Patent: May 14, 1985Assignee: Boehringer Mannheim GmbHInventors: Elmar Bosies, Wolfgang Kampe, Max Thiel, Uwe Bicker, Dietmar Boerner
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Patent number: 4479955Abstract: Disclosed are e.g. 2-aryl-pyrazolo[4,3-c][1,6]naphthyridin-3(5H)-ones, 2-aryl-thieno[2,3-b]pyrazolo[4,3-d]pyridin-3(5H)-ones, 2-aryl-pyrazolo[4,3-c][1,7]naphthyridin-3(5H)-ones, useful as benzodiazepine receptor modulators.Type: GrantFiled: January 10, 1983Date of Patent: October 30, 1984Assignee: Ciba-Geigy CorporationInventor: Naokata Yokoyama
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Patent number: 4477455Abstract: 1,3,7,9-Tetramethylpyrimido[5,4-g]pteridine-2,4,6,8-(1H,3H,7H,9H)-tetraone is an active ingredient in pharmaceutical compositions useful for inducing kaliuresis. It, also, can be used in combination with a distal tubule acting diuretic to give an improved diuretic effect.Type: GrantFiled: February 4, 1983Date of Patent: October 16, 1984Assignee: SmithKline Beckman CorporationInventors: Joseph Weinstock, Virgil D. Wiebelhaus
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Patent number: 4476304Abstract: A process for the purification of riboflavine-5'-monophosphate comprising subjecting crude riboflavine-5'-monophosphate to chromatography using a column packed with a weakly basic anion-exchange resin having a skeleton of a crosslinked polyacrylic acid ester or polymethacrylic acid ester in which at least a part of the ester linkages thereof are converted into amide linkages represented by the following formula (1): ##STR1## to obtain a fraction of riboflavine-5'-monophosphate containing a reduced amount of impurities from an eluate of the column is disclosed.Type: GrantFiled: August 20, 1982Date of Patent: October 9, 1984Assignees: Mitsubishi Chemical Industries Limited, Wakamoto Pharmaceutical Co., Ltd.Inventors: Kenji Yokota, Hiroshi Kusano, Ryuichi Sugimoto
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Patent number: 4472400Abstract: Novel triazoloquinazolones of the formula ##STR1## wherein R and R' are individually selected from the group consisting of hydrogen, halogen, nitro and alkyl and alkoxy of 1 to 3 carbon atoms, Y is selected from the group consisting of alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, aryl of 6 to 8 carbon atoms and aralkyl of 7 to 8 carbon atoms, B is an alkylene of 1 to 3 carbon atoms, X is selected from the group consisting of ##STR2## R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, aryl of 6 to 8 carbon atoms, aralkyl of 7 to 8 carbon atoms, aminoalkyl of 2 to 4 carbon atoms, mono- and dialkylaminoalkyl with each alkyl having 2 to 4 carbon atoms, piperidinoalkyl of 1 to 4 alkyl carbon atoms, morpholinoalkyl of 1 to 4 alkyl carbon atoms and piperazinylalkyl of 1 to 4 alkyl carbon atoms or R.sub.1 and R.sub.Type: GrantFiled: September 21, 1982Date of Patent: September 18, 1984Assignee: Roussel UclafInventors: Wilfred R. Tully, Robert Westwood, David A. Rowlands, Stephen Clements-Jewery
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Patent number: 4469868Abstract: Alkylimidazo[1,2-c]pyrazolo[3,4-e]pyrimidines and pharmaceutically acceptable salts are described. These compounds are antipsychotic agents. Methods for their preparation, pharmaceutical compositions which contain them and methods for using said compositions are also described.Type: GrantFiled: May 24, 1982Date of Patent: September 4, 1984Assignee: Warner-Lambert CompanyInventor: Horace A. DeWald
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Patent number: 4463006Abstract: Diglycidyl-substituted pteridine compounds of the general formula: ##STR1## wherein n is the whole number 1 or 2, R.sub.2 and R.sub.2 are the same or different, and are either hydrogen, a hydrocarbon radical, or together form a 5- or 6-membered carbocyclic or heterocyclic ring; processes for their preparation; and compositions and methods for their use as cytostatic agents.Type: GrantFiled: June 23, 1982Date of Patent: July 31, 1984Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Hinrich Moller, Brigitte Hase, Gunther Konrad, Hans-Christoph Wilk, Ulrich Zeidler
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Patent number: 4463007Abstract: 1,2,4-Triazolo[1,5-c]-quinazolinones of the general formula I ##STR1## and their pharmaceutically tolerated salts, processes for their preparation and pharmaceutical formulations which contain these compounds and are useful drugs in the treatment of allergic disorders.Type: GrantFiled: November 15, 1982Date of Patent: July 31, 1984Assignee: BASF AktiengesellschaftInventors: Rainer Schlecker, Ludwig Friedrich, Dieter Lenke
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Patent number: 4404380Abstract: Imidazopyrimidinones and other diazaheterocyclopyrimidinones having an additional fused imidazole or triazole ring have utility as bronchodilators, mediator release inhibitors, phosphodiesterase inhibitors, and peripheral vasodilators. They are orally active and useful in the prophylaxis and treatment of asthma. A preferred compound is 4-[(4-chlorophenyl)methyl]-6,7-dihydro-3H-imidazo[1,2-a]-purin-9(4H)-one.Type: GrantFiled: August 14, 1980Date of Patent: September 13, 1983Assignee: Mead Johnson & CompanyInventor: Davis L. Temple, Jr.
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Patent number: 4390697Abstract: A novel process for the preparation of triazoloquinazolinones of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, --NO.sub.2, --CF.sub.3, --CH.sub.3 and --OCH.sub.3, n is an integer from 2 to 5, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms and hydroxyalkyl of 1 to 5 carbon atoms or taken together with the nitrogen atom which they are attached form a saturated heterocycle optionally containing another heteroatom and optionally substituted with at least one member of the group consisting of hydroxy, alkyl and hydroxy alkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, acyl of an aliphatic carboxylic acid of 1 to 5 carbon atoms, alkoxycarbonyl of 2 to 6 carbon atoms, aryl and aryl substituted with halogen or --CF.sub.3 and their non-toxic, pharmaceutically acceptable acid addition salts having antihistaminic and bronchospasmolytic activity and novel intermediates.Type: GrantFiled: November 3, 1981Date of Patent: June 28, 1983Assignee: Roussel UclafInventor: Wilfred R. Tully
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Patent number: 4387223Abstract: 2(1H)-Quinazolinone and quinazolinethione derivatives having excellent pharmacological activities are produced in high yield with high purity by heating the corresponding 3,4-dihydro-2(1H)-quinazolinone or quinazolinethione derivatives together with sulfur in an inert solvent.Type: GrantFiled: December 6, 1976Date of Patent: June 7, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Michihiro Yamamoto, Shigenari Katayama, Masao Koshiba, Hisao Yamamoto
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Patent number: 4387226Abstract: There are prepared compound of the formulae ##STR1## Where R.sup.1 is H, lower alkyl S--, lower alkyl ##STR2## NH.sub.2 or halogen, R.sup.2 is OH, lower alkyl S--, halogen, NH.sub.2 or SHR is OH, SH, lower alkyl S--, or halogen andR.sup.3 is OH, SH, lower alkyl S--, halogen or NH.sub.2.The compounds have antiviral and immunomodulating activity.Type: GrantFiled: August 26, 1981Date of Patent: June 7, 1983Assignees: Newport Pharmaceuticals International, Inc., Sloan-Kettering Institute For Cancer ResearchInventors: John W. Hadden, Lionel N. Simon, Alfredo Giner-Sorolla
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Patent number: 4366231Abstract: Pyrazoles of the formula ##STR1## are useful as stabilisers in photographic materials.Type: GrantFiled: January 9, 1981Date of Patent: December 28, 1982Assignee: Agfa Gevaert AktiengesellschaftInventors: Karl H. Mayer, deceased, Klaus Sasse, Anita von Konig
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Patent number: 4352931Abstract: Novel benzologs or pyrazolo-quinazoline derivatives of the formula (I) ##STR1## wherein X and Y are independently selected from oxygen, sulphur and imino and wherein ring (C) is a pyrazole ring fused to ring (B) via one of the three ortho positions or sides of ring (B); the fused pyrazole ring (C) is either in the 4,3- or the 3,4-arrangement; and tautomers of formula (I) compounds; when X is not oxygen, i.e. stands for sulphur or imino, Y may stand for a covalent bond that links the hydrogen directly to the carbon atom in position 2.Two methods for producing the novel formula (I) compounds are disclosed. The first or indazole method starts from a precursor having a benzene moiety (ring B) and a pyrazolo moiety (ring C) fused therewith, i.e. the indazole structure; ring (B) carries two vicinal substituents for forming the pyrimidine moiety or ring (A) by cyclization. The second or quinazoline method starts from a precursor having the pyrimidine moiety (A) and the benzene moiety (B) fused therewith, i.e.Type: GrantFiled: May 22, 1980Date of Patent: October 5, 1982Assignee: Siegfried AktiengesellschaftInventors: Eckehard K. T. Cuny, Frieder W. Lichtenthaler, Alfred R. Moser
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Patent number: 4350695Abstract: Novel triazoloquinazolinones of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, halogen, --NO.sub.2, methyl, methoxy and --CF.sub.3, n is an integer from 2 to 5, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen and alkyl and hydroxyalkyl of 1 to 5 carbon atoms and taken together with the nitrogen atom to which they are attached form a saturated heterocycle optionally containing another heteroatom and optionally substituted with at least one member of the group consisting of hydroxy, alkyl and hydroxyalkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, acyl of an aliphatic carboxylic acid of 1 to 5 carbon atoms, alkoxycarbonyl of 2 to 6 carbon atoms and aryl optionally substituted with a halogen or --CF.sub.3 and their non-toxic, pharmaceutically acceptable acid addition salts having antihistaminic and bronchospasmolytic activity and their preparation.Type: GrantFiled: February 13, 1981Date of Patent: September 21, 1982Assignee: Roussel UclafInventors: Robert Westwood, Wilfred R. Tully, Robert Murdoch
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Patent number: 4323503Abstract: Novel substituted 2,3-alkylene bis (oxy) benzamides and derivatives thereof are disclosed. Also disclosed is a method for producing said compounds. The compounds have anxiolytic, psychostimulant, disinhibiting and thymoanaleptic properties useful therapeutically in the psychofunctional field, particularly in gastro-enterology, cardiology, urology, rheumatology and gynaecology.Type: GrantFiled: June 12, 1979Date of Patent: April 6, 1982Assignee: Societe d'Etudes Scientifiques et Industrielles de L'ile-de-FranceInventors: Michel Thominet, Gerard Bulteau, Jacques Acher, Claude Collignon
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Patent number: 4298734Abstract: Imidazopyrimidinones and other diazaheterocyclopyrimidinones having an additional fused imidazole or triazole ring have utility as bronchodilators, mediator release inhibitors, phosphodiesterase inhibitors, and peripheral vasodilators. They are orally active and useful in the prophylaxis and treatment of asthma. A preferred compound is 4-[(4-chlorophenyl)methyl]-6,7-dihydro-3H-imidazo[1,2-a]-purin-9(4H)-one.Type: GrantFiled: March 5, 1979Date of Patent: November 3, 1981Assignee: Mead Johnson & CompanyInventor: Davis L. Temple, Jr.
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Patent number: 4252808Abstract: The compounds of the formula (I): ##STR1## wherein R.sup.1 is a hydrogen atom, a trityl group or an acyl group as found in known antibacterially active penicillins or cephalosporins; R.sup.2 is a hydrogen atom, a lower alkyl group or an aryl group; R.sup.3 is a hydrogen atom, a lower alkyl group, a substituted lower alkyl or a thiosubstituted lower alkyl group; and R.sup.4 is a group such that CO.sub.2 R.sup.4 is a carboxylic acid group or a salt or readily removable ester thereof; are antibiotics. The compounds may be formulated in pharmaceutical compositions.Processes for the preparation of the compounds (I) are also described.Type: GrantFiled: February 26, 1979Date of Patent: February 24, 1981Assignee: Beecham Group LimitedInventor: Michael J. Pearson
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Patent number: 4228164Abstract: A compound of the formula ##STR1## wherein R is hydroxy, alkoxy or acyloxyQ is sulfur or a .dbd.N--R.sup.1 group, wherein R.sup.1 ishydrogen, C.sub.1-5 alkyl or aralkyl or C.sub.2-4 acyl, or a pharmaceutically acceptable acid addition salt thereof.Type: GrantFiled: November 7, 1978Date of Patent: October 14, 1980Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.Inventors: Rudolf Szebeni, Dezso Korbonits, Kalman Harsanyi, Molnar Leventene, Laszlo Szekeres, Gyula Papp, Gyula Sebestyen
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Patent number: 4226994Abstract: In a process for preparing the compound 4-methyl-4,5-dihydrotetrazolo [1,5-a] quinazolin-5-one having the structural formula: ##STR1## which comprises the steps of (i) bringing anthranilic acid into reaction with cyanamide at a temperature in the range of 80.degree. to 100.degree. C.; (ii) bringing the reaction product obtained by the foregoing step (i) into reaction with hydrazine hydrate in the presence of an organic solvent; then (iii) diazotizing the hydrazino compound so formed to yield a tetrazole; and finally (iv) methylating the tetrazole, the improvement which comprises using n-butanol as the organic solvent in step (ii).Type: GrantFiled: June 19, 1979Date of Patent: October 7, 1980Assignee: Imperial Chemical Industries LimitedInventors: John H. Marsden, Norman Harrison
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Patent number: 4223143Abstract: Novel quinazoline derivatives of the formula (1) ##STR1## wherein ring C is a pyrazole ring fused to ring B in two vicinal positions thereof that are not fused with ring A. The novel formula (1) compounds or pyrazolo-quinazoline-ones are structurally related to allopurinol, a well known drug useful in the treatment of gout and are expected to replace or complement allopurinol in the therapeutic use thereof. The generic name Benzoallopurinol is suggested for the novel formula (1) compounds; formula (1) includes angular and linear structures of the interfused rings A, B and C.Two methods for producing the novel formula (1) compounds are disclosed. The first method starts from the indazole structure that includes the interfused rings B and C, and ring A is formed on the indazole moiety. The second method starts from the quinazoline structure that includes interfused rings A and B, and the pyrazole ring C is formed on the benzo moiety (ring B) of the quinazoline structure.Type: GrantFiled: December 11, 1978Date of Patent: September 16, 1980Assignee: Siegfried AktiengesellschaftInventors: Eckehard K. T. Cuny, Frieder W. Lichtenthaler
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Patent number: 4202974Abstract: 3,4-Dihydro-2(1H)-quinazolinones and quniazolinethiones such as 1-cyclopropylmethyl-4-phenyl-6-methoxy-3,4-dihydro-2(1H)-quinazolinone and its thione derivative, are prepared in high yield with high purity by heating the corresponding arylurea or thiourea such as N-cyclopropylmethyl-N-(p-methoxyphenyl) urea or its thiourea derivative, with the corresponding aldehyde such as benzaldehyde in the presence of hydrobromic acid in an inert solvent.Type: GrantFiled: October 12, 1976Date of Patent: May 13, 1980Assignee: Sumitomo Chemical Company, LimitedInventors: Michihiro Yamamoto, Shigenari Katayama, Masao Koshiba, Hisao Yamamoto
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Patent number: 4183932Abstract: Tricyclic quinazolines of the formula, ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and A are as defined in the specification, such as 4,5-dihydro-5-arylimidazo[1,2-a]quinazolines, 4,5-dihydro-5-aryl-s-triazolo[4,3-a]quinazolines and 4,5-dihydro-5-aryltetrazolo[1,5-a]quinazolines having anti-inflammatory and analgesic activity are, for example, prepared by reducing the corresponding 4,5-unsaturated compounds, and then, if necessary, by alkylating the thus produced compounds.Type: GrantFiled: January 31, 1978Date of Patent: January 15, 1980Assignee: Sumitomo Chemical Company, LimitedInventors: Michihiro Yamamoto, Masao Koshiba, Hisao Yamamoto
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Patent number: 4179560Abstract: Imidazo- and pyrimido[2,1-b]quinazolines of the formula, ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen, halogen, trifluoromethyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, or R.sub.1 and R.sub.2 may together represent methylenedioxy; R.sub.3 is hydrogen, C.sub.1-4 alkyl, phenyl or substituted phenyl of the formula, ##STR2## (wherein R is halogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy); R.sub.4 is hydrogen, C.sub.1-4 alkyl or aralkyl; and A is C.sub.2-3 alkylene wich may be optionally substituted by one or two C.sub.1-2 alkyl radicals, and pharmaceutically acceptable acid addition salts thereof, are prepared by reacting a compound of the formula, ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and A are as defined above; and X is oxygen or sulfur, with a halogenating agent at a temperature of about 30.degree. C. to about 180.degree. C. In the above imidaxo- and pyrimido[2,1-b]quinazolines, those having C.sub.1-4 alkyl, or ##STR4## as R.sub.Type: GrantFiled: February 27, 1975Date of Patent: December 18, 1979Assignee: Sumitomo Chemical Company, LimitedInventors: Michihiro Yamamoto, Shigeaki Morooka, Masao Koshiba, Shigeho Inaba, Hisao Yamamoto
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Patent number: 4148999Abstract: Improved methods for the preparation and purification of citrovorum factor are disclosed. The method includes improved procedures for hydrogenation of 10-formylfolic acid as well as for the reduction of folic acid. Also disclosed are improved procedures for opening of the imidazoline ring, and a non-chromatographic method for the purification of crude samples of citrovorum factor.Type: GrantFiled: August 22, 1977Date of Patent: April 10, 1979Assignee: The Government of the United States of AmericaInventors: Carroll G. Temple, Jr., Robert D. Elliott, Jerry D. Rose, John A. Montgomery
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Patent number: 4141979Abstract: A series of tetrazolo[a]quinazol-5-ones, methods for their production and use as antiallergy agents and antiulcer agents.Type: GrantFiled: December 22, 1977Date of Patent: February 27, 1979Assignee: Pfizer Inc.Inventor: Jasjit S. Bindra
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Patent number: 4128646Abstract: Substituted pyrimido[5,6-b]quinoxaline-4(3H)-one-2-carboxylic acid compounds each represented by the formula ##STR1## wherein: R designates a member selected from the group consisting of hydrogen, alkyl groups having 1 to 4 carbon atoms, benzyl group, and phenyl group; and each of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 independently designates a member selected from the group consisting of hydrogen, alkyl group having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, halogens, benzyloxy group, hydroxyl group, alkylthio groups having 1 to 4 carbon atoms, and alkylenedioxy groups having 1 to 4 carbon atoms and formed by the bonding of two of R.sup.1, R.sup.2, R.sup.3, and R.sup.4, or pharmacologically acceptable salts of said compounds.Type: GrantFiled: December 28, 1977Date of Patent: December 5, 1978Assignee: Mitsubishi Yuka Pharmaceutical Co., Ltd.Inventors: Yasuhiro Morinaka, Kazuo Takahashi
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Patent number: 4124764Abstract: New 1,7-dihydro-1-substituted-3H-pyrazolo[4,3-e]-1,2,4-triazolo[4,3-c]pyrimidi ne-3-thione and 3-one mesoionic didehydro derivatives which have the formula ##STR1## wherein R.sub.1 is hydrogen, lower alkyl, phenyl-lower alkyl, cycloalkyl or hydroxy-lower alkyl;R.sub.2 is hydrogen or lower alkyl;R.sub.3 is lower alkyl, cycloalkyl or hydroxy-lower alkyl; andX is sulfur or oxygen,Are useful as anti-inflammatory agents.Type: GrantFiled: September 13, 1977Date of Patent: November 7, 1978Assignee: E. R. Squibb & Sons, Inc.Inventors: Uwe D. Treuner, Hermann Breuer