Benzothiazines (including Hydrogenated) Patents (Class 544/49)
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Patent number: 4829062Abstract: A series of novel oxyalkyl ether derivatives of various enolic oxicam compounds have been prepared, including certain novel enol oxyalkyl ethers of 4-hydroxy-2-methyl-N-(2-pyridinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide (piroxicam). These particular compounds are useful in theraphy as prodrug forms of the known anti-inflammatory and analgesic oxicams.Type: GrantFiled: December 22, 1987Date of Patent: May 9, 1989Assignee: Pfizer Inc.Inventors: Joseph G. Lombardino, Anthony Marfat
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Patent number: 4820842Abstract: The present invention provides a process for preparing a 5-cyano-2-substituted-1,4-dihydropyridine compound having cardiovascular activity.Type: GrantFiled: September 11, 1987Date of Patent: April 11, 1989Assignee: Warner-Lambert CompanyInventors: Kevin R. Anderson, Ila Sircar
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Patent number: 4818756Abstract: The invention relates to substituted 2-pyrimidinyl-1-piperazine derivatives defined herein by formula (I), processes for their manufacture, compositions containing said substituted 2-pyrimidinyl-1-piperazine derivatives as active materials and the use of said compounds and compositions as agents effecting the central nervous system. Also included in the invention are intermediates of formula (VIII) for making the active formula (I) compounds.Type: GrantFiled: March 10, 1986Date of Patent: April 4, 1989Assignee: Troponwerke GmbH & Co., KGInventors: Peter-Rudolf Seidel, Harald Horstmann, Jorg Traber, Wolfgang Dompert, Thomas Glaser, Teunis Schuurman
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Patent number: 4797483Abstract: A process for obtaining 4-hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide, which may be used as a non-steroidal analgesic and anti-inflammatory drug. The process comprises reacting saccharin sodium with isopropyl chloroacetate in dimethylformamide, reacting the resultant isopropyl 3-oxo-1,2-benzoisothiazoline-2-acetate 1,1-dioxide with sodium isopropylate in isopropanol to produce an intermediate which, when methylated in an aqueous-alcoholic basic medium with dimethyl sulfate, gives an intermediate compound which when condensed with 2-aminopyridine in xylene, yields 4-hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazone-3-carboxamide 1,1-dioxide.Type: GrantFiled: June 24, 1987Date of Patent: January 10, 1989Assignee: Induspol, S.A.Inventors: Jordi Frigola Constansa, Jose M. Ribalta Baro, Julio Campon Pardo
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Patent number: 4750930Abstract: Novel N-hydroxy-N'-sulfonylguanidine compounds are described which possess significant herbicidal and plant growth regulant activity for control of undesired vegetation.Type: GrantFiled: June 10, 1987Date of Patent: June 14, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventor: Rafael Shapiro
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Patent number: 4748174Abstract: The water soluble acid addition salts of an NSAID, such as acetylsalicylic acid, fenbufen, diflunisal, piroxicam, naproxen, or the like, with either glucamine or meglumine (N-methylglucamine) are useful anti-inflammatory and analgesic drugs, well adopted for parenteral, oral, rectal or topical administration.Type: GrantFiled: January 5, 1987Date of Patent: May 31, 1988Assignee: Therapicon s.r.l.Inventor: Paolo A. Veronesi
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Patent number: 4746355Abstract: Benzylsulfonylureas and arylsulfamoylureas are useful as pre-emergent and post-emergent herbicides and as plant growth regulants.Type: GrantFiled: July 16, 1986Date of Patent: May 24, 1988Assignee: E. I. Du Pont De Nemours and CompanyInventors: Robert J. Pasteris, Mark E. Thompson
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Patent number: 4746357Abstract: Sulfonylureas derived from acetylenic pyrimidines and triazines, useful as pre- and postemergence herbicides. Typical of this group is 2-[[(4-ethynyl-6-methylpyrimidine-2-yl)aminocarbonyl]-aminosulfonyl]-benzo ic acid, methyl ester.Type: GrantFiled: May 21, 1987Date of Patent: May 24, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventor: Steven P. Artz
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Patent number: 4744816Abstract: Herbicidal sulfonamides such as 2-[[[4-(methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]aminocar bonyl]aminosulfonyl]benzoic acid, methyl ester are useful as herbicides and plant growth regulants.Type: GrantFiled: June 11, 1987Date of Patent: May 17, 1988Assignee: E. I. DuPont de Nemours and CompanyInventors: Martha M. Bolinski, Donald J. Dumas
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Patent number: 4732898Abstract: The present invention are 2-(2-aryl-2-oxo-alkylidene) analogs of 1,2,3,4-tetrahydropyridine-3,5-pyridinecarboxylic acids and particularly esters thereof having valuable calcium antagonist and positive inotropic activity useful in the treatment of cardiovascular disorders, pharmaceutical compositions and methods of use therefor.Type: GrantFiled: March 3, 1987Date of Patent: March 22, 1988Assignee: Warner-Lambert CompanyInventors: Edward W. Badger, Michael D. Taylor
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Patent number: 4705555Abstract: Aryl and heteroaryl sulfonimidamides which also contain a pyrimidine or triazine heterocycle are useful as general or selective preemergent and postemergent herbicides.Type: GrantFiled: February 20, 1987Date of Patent: November 10, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Craig L. Hillemann
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Patent number: 4694080Abstract: Certain substituted-4-hydroxy-(or 4-acyloxy-)2H-1,2-benzothiazine 1,1-dioxides having at the 3-position a 2-substituted-1,3,4-oxadiazol-5-yl, a 2-substituted-tetrazol-5-yl or a 1-substituted-tetrazol-5-yl group useful as selective 5-lipoxygenase pathway inhibitors; and methods for their preparation.Type: GrantFiled: March 19, 1986Date of Patent: September 15, 1987Assignee: Pfizer Inc.Inventors: Susumu Nakanishi, Isao Nagakura
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Patent number: 4689069Abstract: Sulfonylureas derived from acetylenic pyrimidines and triazines, useful as pre- and postemergence herbicides. Typical of this group is 2-[[(4-ethynyl-6-methylpyrimidine-2-yl)aminocarbonyl]-aminosulfonyl]-benzo ic acid, methyl ester.Type: GrantFiled: June 27, 1985Date of Patent: August 25, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Steven P. Artz
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Patent number: 4683306Abstract: Process for the preparation of 3,4-dihydro-2-substituted-4(or 3)-oxo-2H-1,2-thiazine-3(or 4)-carboxylic acid 1,1,-dioxide magnesium chelate derivatives and its acids by reacting appropriately 3,4-dihydro-2-substituted-4(or 3)-oxo-2H-1,2-thiazine 1,1-dixoides with alkylmagnesiumcarbonate and then hydrolyzing and its use as intermediates for the preparation of N-substituted-2-substituted-2H-1,2-thiazine-3(or 4)-carboxamide-1,1-dioxide derivatives, effective antiinflammatory agents.Type: GrantFiled: July 13, 1984Date of Patent: July 28, 1987Assignee: YuHan Corporation Co., Ltd.Inventors: Jung J. Suh, You H. Hong
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Patent number: 4666506Abstract: Aryl and heteroaryl sulfonimidamides which also contain a pyrimidine or triazine heterocycle are useful as general or selective preemergent and postemergent herbicides.Type: GrantFiled: July 11, 1985Date of Patent: May 19, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Craig L. Hillemann
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Patent number: 4656273Abstract: There is described a novel process for producing sulfonylureas of formula I ##STR1## wherein R.sub.1 is hydrogen or alkyl,R.sub.2 is ##STR2## E is .dbd.N-- or .dbd.CH--, R.sub.3 is alkyl, alkoxy or halogen,R.sub.4 is alkyl, cycloalkyl, alkoxy, halogen, alkoxy-alkyl, halo-alkyl or halo-alkoxy,R.sub.5 is hydrogen or alkyl,T is a substituted phenyl group ##STR3## Y is hydrogen or halogen, X is hydrogen, halogen, alkyl, halo-alkyl, alkenyl, halo-alkenyl, alkynyl, alkoxy, halo-alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, halo-alkylthio, alkylsulfonyloxy, phenylsulfonyloxy, phenylsulfonyloxy mono- or polysubstituted by alkyl, or is di-alkylsulfamoyl, andA is a bridge member which has 3 or 4 atoms and which contains 1 or 2 hetero atoms, selected from the group consisting of oxygen, sulfur and nitrogen,the said process comprising reacting a silfonamide of the formula IIT--SO.sub.2 --NH.sub.Type: GrantFiled: December 16, 1985Date of Patent: April 7, 1987Assignee: Ciba-Geigy CorporationInventor: Werner Topfl
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Patent number: 4623486Abstract: Certain novel p-aminomethylbenzoyl derivatives of 4-hydroxy-2-methyl-N-(2-pyridinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide and several other closely-related known oxicams have been prepared. These particular compounds are useful in therapy as prodrug forms of the known anti-inflammatory and analgesic oxicams. Preferred member compounds include 2-methyl-4-[4-(morpholinomethyl)benzoyloxy]-N-(2-pyridinyl)-2H-1,2-benzoth iazine-3-carboxamide 1,1-dioxide, 2-methyl-4-[4-(piperidinomethyl)benzoyloxy]-N-(2-pyridinyl)-2H-1,2-benzoth iazine-3-carboxamide 1,1-dioxide, 2-methyl-N-(6-methyl-2-pyridinyl)-4-[4-(piperidinomethyl)benzoyloxy]-2H-1, 2-benzothiazine-3-carboxamide 1,1-dioxide, 2-methyl-4-[4-(4-methylpiperazinomethyl)benzoyloxy]-N-(2-pyridinyl)-2H-1,2 -benzothiazine-3-carboxamide 1,1-dioxide and 2-methyl-4-[4-(pyridiniummethyl)benzoyloxy]-N-(2-pyridinyl)-2H-1,2-benzoth iazine-3-carboxamide 1,1-dioxide chloride. Methods for preparing these compounds from known starting materials are provided.Type: GrantFiled: May 29, 1985Date of Patent: November 18, 1986Assignee: Pfizer Inc.Inventor: Joseph G. Lombardino
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Patent number: 4610982Abstract: Certain novel 2-acetoxybenzoyl and ring-substituted .alpha.-arylpropionyl derivatives of 4-hydroxy-2-methyl-N-(2-pyridinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide and several other closely-related known oxicams have been prepared. These particular compounds are useful in therapy as non-steroidal anti-arthritic agents. Typical member compounds include 4-(2-acetoxybenzoyloxy)-2-methyl-N-(2-pyridinyl)-2H-1,2-benzothiazine-3-ca rboxamide 1,1-dioxide, 4-[.alpha.-(4-isobutylphenyl)propionyloxy]-2-methyl-N-(2-pyridinyl)-2H-1,2 -benzothiazine-3-carboxyamide N-(2-pyridinyl)-2H-1,2-benzothiazine-3-carboxyamide 1,1-dioxide, 4-[.alpha.-(3-benzoylphenyl)propionyloxy]-2-methyl-N-(2-pyridinyl)-2H-1,2- benzothiazine-3-carboxamide 1,1-dioxide, "d-4-[.alpha.-6-methoxynaphth-2-yl)propionyloxy]-2-methyl-N-(2-pyridinyl)- 2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide" to -- d-4-[.alpha.-(6-methoxynaphth-2-yl)propionyloxy]-2-methyl-N-(2-pyridinyl)- 2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide.Type: GrantFiled: June 3, 1985Date of Patent: September 9, 1986Assignee: Pfizer Inc.Inventor: Joseph G. Lombardino
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Patent number: 4599406Abstract: The process for the preparation of derivatives of 2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide of the formula ##STR1## wherein R represents hydroxy (Ia) or substituted hydroxy OR.sub.1 in which R.sub.1 is the cinnamoyl radical --CO--CH.dbd.CH--C.sub.6 H.sub.5 (Ib) consists in reacting a strong base salt of 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxide with an acyl chloride R.sub.1 Cl, in which R.sub.1 is the cinnamoyl radical, or R.sub.2 Cl, in which R.sub.2 is an aromatic or aliphatic C.sub.2 -C.sub.6 acyl radical to give the corresponding mixed anhydride, optionally esterified at position 4, which is then reacted with 2-aminopyridine to give the desired amide.Type: GrantFiled: December 13, 1984Date of Patent: July 8, 1986Assignee: SPA-Societa Prodotti Antibiotici spaInventors: Tiberio Bruzzese, Ernani Dell'Acqua, Franco Ottoni, Holger H. van den Heuvel
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Patent number: 4589911Abstract: Fused N-phenylsulfonyl-N'-triazinylurea of formula I ##STR1## wherein Z is oxygen or sulfur,R.sup.1 is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, cyano, or a --X--R.sup.5, --CO--X--R.sup.6, --CO--NR.sup.7 R.sup.8, --SO--R.sup.9 or --SO.sub.2 --R.sup.10 group,R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy,R.sup.3 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy or C.sub.3 -C.sub.6 cycloalkyl,R.sup.4 is hydrogen, halogen, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.2 -C.sub.4 alkoxyalkoxy, C.sub.3 -C.sub.6 cycloalkyl or --NR.sup.11 R.sup.12,R.sup.5 is C.sub.3 -C.sub.5 alkynyl or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.4 -alkoxy, or is C.sub.3 -C.sub.5 alkenyl, which is unsubstituted or is substituted by halogen or C.sub.1 -C.sub.4 -alkoxy,R.sup.6 and R.sup.9 are each independently C.sub.1 -C.sub.Type: GrantFiled: May 1, 1984Date of Patent: May 20, 1986Assignee: Ciba-Geigy CorporationInventors: Josef Ehrenfreund, Werner Fory
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Patent number: 4587335Abstract: The present invention refers to a new process for preparing 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-[N-(2-pyridinyl)carboxamide]-1,1 -dioxide, its phosphoric ester and the obtained phosphoric ester.Type: GrantFiled: July 17, 1984Date of Patent: May 6, 1986Inventor: Vincenzo Iannella
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Patent number: 4586950Abstract: Herbicidal sulfonamides are useful as general or selective herbicides, both pre-emergence and post-emergence.Type: GrantFiled: September 20, 1983Date of Patent: May 6, 1986Assignee: E. I. Du Pont de Nemours & CompanyInventor: Robert J. Pasteris
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Patent number: 4582831Abstract: A novel crystalline form of the monoethanolamine salt of N-(2-pyridyl)-2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide has been prepared. This novel crystalline form is designated as polymorph I and is useful in therapy as a non-steroidal anti-arthritic agent. Methods for preparing this polymorph from readily available materials are provided.Type: GrantFiled: November 16, 1984Date of Patent: April 15, 1986Assignee: Pfizer Inc.Inventor: Robert L. Robertson
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Patent number: 4581178Abstract: Low valent transition metal complexes containing small cone angle phosphine or arsine ligands efficiently catalyze addition of aldehydes to compounds or groups having a C--H bond activated by a nitro or nitrile group, to provide nitroalcohols or cyanohydrins, respectively.Type: GrantFiled: February 28, 1985Date of Patent: April 8, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: David Milstein
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Patent number: 4581356Abstract: New triazine derivatives represented by the formula: ##STR1## wherein R.sup.1 is a 1,2,3,4-tetrahydroquinolyl, 2-oxo-1,2,3,4-tetrahydroquinolyl, 2-oxo-1,2-dihydroquinolyl, indolyl, 2-oxoindolinyl, benzothiazolyl, 2-oxobenzothiazolinyl, 3,4-dihydro-1H-2,1-benzothiazinyl in which the S atom being optionally oxidized, or 3-oxo-2,3-dihydro-4H-1,4-benzoxazinyl, each of which may have one or more substituent(s) selected from lower alkyl, hydroxy(lower)alkyl, lower alkylamino, lower alkanoyl, cyclic lower alkanoyl, lower alkoxy(lower)alkyl, lower alkylamino(lower)alkanoyl, benzyl, benzyloxy(lower)alkyl, lower alkoxycarbonyl(lower)alkyl and 4-(2-hydroxyethyl)piperazin-1-yl-carbonylmethyl;R.sup.2 is a hydrogen, lower alkenyl, benzyl, carboxy(lower)alkyl or lower alkoxycarbonyl(lower)alkyl;R.sup.3 and R.sup.4, which may be the same or different, are each hydrogen or lower alkyl or together represent a bond;provided that when R.sup.Type: GrantFiled: March 12, 1984Date of Patent: April 8, 1986Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Tsutomu Teraji, Youichi Shiokawa, Kazuo Okumura, Yoshinari Sato
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Patent number: 4578460Abstract: The invention relates to a derivative of 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide of the formula: ##STR1## in which X is 6-aminopurinyl. The above compound exhibits anti-inflammatory activity.Type: GrantFiled: October 4, 1983Date of Patent: March 25, 1986Assignee: Francia Farmaceutici s.r.l.Inventor: Giorgio A. Francia
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Patent number: 4567179Abstract: Improved antiinflammatory salts of piroxicam with antidepressant doxepin, with bronchodilator pirbuterol or isoproterenol, with H.sub.2 -antagonist inhibitor 2-guanidino-4-(2-methyl-4-imidazolyl)thiazole, with pyridoxine, a member of the vitamin B.sub.6 complex, or with antihypertensive trimazosin.Type: GrantFiled: October 11, 1984Date of Patent: January 28, 1986Assignee: Pfizer, Inc.Inventor: Joseph G. Lombardino
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Patent number: 4563211Abstract: Certain sulfonylurea compounds such as 2-[[[4-methoxy-6-(methylselenylmethyl)pyrimidin-2-yl]aminocarbonyl]aminosu lfonyl]benzoic acid, methyl ester and 2-[[[4-methoxy-6-(phenylthiomethyl)pyrimidin-2-yl]-aminocarbonyl]aminosulf onyl]benzoic acid, methyl ester provide herbicidal activity.Type: GrantFiled: March 19, 1984Date of Patent: January 7, 1986Assignee: E. I. Du Pont De Nemours and CompanyInventors: Barry A. Wexler, William T. Zimmerman
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Patent number: 4551525Abstract: A process for preparing N-(2-pyridyl)-2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-di oxide which comprises reacting an alkyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide with P-phenyl-N,N'-di-2-pyridylphosphonium diamide.Type: GrantFiled: October 2, 1984Date of Patent: November 5, 1985Assignee: KRKA, tovarna zdravil, n.sol.o.Inventors: Natasa Zupancic, Boris Sket, Pavel Zupet, Marko Zupan
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Patent number: 4551452Abstract: Certain enol ether derivatives of oxicams (1,1-dioxides of N-heteroaryl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamides and N-heteroaryl-4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamid es) are useful as prodrugs of these antiinflammatory compounds.Type: GrantFiled: May 2, 1984Date of Patent: November 5, 1985Assignee: Pfizer Inc.Inventor: Anthony Marfat
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Patent number: 4540692Abstract: The invention relates to novel tropone derivatives, of antiinflammatory, analgesic and antirheumatic activity, of the formula: ##STR1## wherein R.sup.1 is hydrogen or lower alkyl,R.sup.2 is hydrogen, hydroxy, halogen, lower alkyl, or lower alkoxy, andR.sup.3 is hydrogen or acyl,and pharmaceutically acceptable salts thereof.Type: GrantFiled: March 14, 1984Date of Patent: September 10, 1985Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Ikuo Ueda, Masayuki Kato, Yoshiharu Kasai
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Patent number: 4536573Abstract: A novel compound of the formula ##STR1## wherein R is hydrogen, benzyl or (C.sub.1 -C.sub.3)alkyl; R.sup.1 is benzyl or (C.sub.1 -C.sub.4)alkyl and Z.sup.1 taken together with --C.dbd.Type: GrantFiled: May 11, 1984Date of Patent: August 20, 1985Assignee: Pfizer Inc.Inventor: Joseph A. Kardys
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Patent number: 4533664Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, methyl, methoxy, fluorine or chlorine; andR.sub.2 is hydrogen, methyl, ethyl or n-propyl;and non-toxic, pharmacologically acceptable salts thereof formed with an inorganic or organic base. The compounds as well as the salts are useful as antithrombotics.Type: GrantFiled: September 30, 1983Date of Patent: August 6, 1985Assignee: Dr. Karl Thomae Gesellschaft mit beschrankter HaftungInventors: Gunter Trummlitz, Wolfhard Engel, Ernst Seeger, Walter Haarmann
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Patent number: 4506071Abstract: A new process for the preparation of microcrystalline isoxicam having a particle size of about 1-30 .mu.m which comprises dissolving isoxicam in a mixture consisting of a solvent miscible with water and of an aqueous base where the resulting basic solution is neutralized with dilute acid to a pH of 4-6 with vigorous agitation precipitating the microcrystalline product is herein described.Type: GrantFiled: March 12, 1984Date of Patent: March 19, 1985Assignee: Warner-Lambert CompanyInventors: Wolfgang Herrmann, Uwe Gebhardt
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Patent number: 4489077Abstract: 4-Hydroxy-N-[5-[(substituted hetero)methyl]-3-isoxazolyl]-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxides as agents for treating pain in mammals resulting from inflammation.Type: GrantFiled: February 2, 1984Date of Patent: December 18, 1984Assignee: Warner-Lambert CompanyInventors: Jagadish C. Sircar, Thomas Capiris
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Patent number: 4483982Abstract: Processes for the preparation of the antiinflammatory agent piroxicam and intermediates leading thereto, the first of which comprises reacting N-methylsaccharin with (N-2-pyridyl)haloacetamides and alkyl haloacetates in the presence of an appropriate base to give, respectively, piroxicam and alkyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxides, intermediates which can be converted into piroxicam; and the second of which comprises reacting a novel alkyl 2-(2-methyl-3-hydroxy-2,3-dihydro-1,2-benzisosulfonazol-3-yl)-2-haloacetat e with a metal hydride to give alkyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxides, intermediates leading to piroxicam.Type: GrantFiled: April 5, 1984Date of Patent: November 20, 1984Assignee: Pfizer Inc.Inventor: Paul D. Weeks
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Patent number: 4478996Abstract: A process for the preparation of 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxides, of the formula: ##STR1## in which R may be phenyl, aryl substituted with halogen (Cl, Br or I) or with C.sub.1 -C.sub.6 alkyl groups, 2, 3 or 4-pyridyl or pyridyls substituted with halogen (Cl, Br or I) or with C.sub.1 -C.sub.6 alkyl groups, 5-methyl-isoxazolyl or 2-thiazolyl.In the process a C.sub.1 -C.sub.6 alkyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide is reacted with a magnesium derivative of formula:R-NH-Mg-Xin which X is halogen, preferably Br and R is the same as defined for formula (I). The compounds produced by the described process have analgesic and antiinflammatory properties.Type: GrantFiled: March 7, 1983Date of Patent: October 23, 1984Assignee: Medichem, S.A.Inventor: Manuel A. Almenara
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Patent number: 4477661Abstract: The present invention provides a process for the preparation of 4-hydroxy-3-(heterocyclocarbamoyl)-2H-1,2-benzothiazine-1,1-dioxides of the general formula: ##STR1## wherein R.sub.1 is a hydrogen atom or a methyl radical, R.sub.2 is a nitrogen-containing heterocyclic radical and R.sub.3 is a hydrogen or halogen atom or a methyl radical, and of the alkali metal, alkaline earth metal and amine salts thereof, by the reaction of an amine-substituted, nitrogen-containing heterocyclic compound with a halo-acetyl halide, reaction of the intermediate thus obtained with sodium benzoic acid sulphimide, ring expansion of the benzoisothiazole ring to give a benzothiazine ring and, in case R.sub.Type: GrantFiled: March 25, 1983Date of Patent: October 16, 1984Assignee: Warner-Lambert CompanyInventors: Wolfgang Herrmann, Wolfram Geibel, Gerhard Satzinger
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Patent number: 4474955Abstract: The present invention refers to a new process for preparing 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-[N-(2-pyridinyl)carboxamide]-1,1 -dioxide, its phosphoric ester and the obtained phosphoric ester.Type: GrantFiled: June 4, 1982Date of Patent: October 2, 1984Inventor: Vincenzo Iannella
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Patent number: 4474956Abstract: In the preparation of 4-hydroxy-2-methyl-N-2-pyridyl-2H-benzothiazine-3-carboxamide 1,1-dioxide by reacting the corresponding 3-methoxycarbonyl compound with 2-aminopyridine, a dramatic increase in the yield is obtained if the reaction is carried out in the presence of 0.1 to 1.5 mole equivalent (based on the 3-methoxycarbonyl compound) of an alkyl- or arylsulfonic acid.Type: GrantFiled: June 29, 1983Date of Patent: October 2, 1984Assignee: Siegfried AktiengesellschaftInventors: Ludwig Zirngibl, Rene Gnehm
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Patent number: 4469866Abstract: A novel compound of the formula ##STR1## wherein R is hydrogen, benzyl or (C.sub.1 -C.sub.3)alkyl; R.sup.1 is benzyl or (C.sub.1 -C.sub.4)alkyl and Z.sup.1 taken together with --C.dbd.Type: GrantFiled: April 25, 1983Date of Patent: September 4, 1984Assignee: Pfizer Inc.Inventor: Joseph A. Kardys
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Patent number: 4461768Abstract: A new benzothiazine derivative, that is N-(2-pyridyl)-2-methyl-4-cinnamoyloxy-2H-1,2-benzothiazine-3-carboxamido 1,1-dioxide has been prepared. Owing to its peculiar ester structure, obtained by condensation with cinnamic acid, the new product is endowed with so outstanding pharmacological and toxicological activities, particularly with reference to its tolerableness, to make it a therapeutically valuable anti-inflammatory drug.Type: GrantFiled: November 4, 1982Date of Patent: July 24, 1984Assignee: SPA Societa Prodotti Antibiotici S.p.A.Inventors: Ernani Dell'Acqua, Tiberio Bruzzese, Lorenzo Ferrari
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Patent number: 4434163Abstract: The water-soluble lysine and arginine salts of N-(2-pyridyl)-2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide have been prepared. These novel salts are useful in therapy as non-steroidal anti-arthritic agents, especially when administered by the parenteral route. Methods for preparing these salts from the corresponding acidic starting material and the appropriate amine base are provided.Type: GrantFiled: April 13, 1982Date of Patent: February 28, 1984Assignee: Pfizer Inc.Inventor: Joseph G. Lombardino
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Patent number: 4434164Abstract: The water-soluble ethylenediamine, monoethanolamine and diethanolamine salts of N-(2-pyridyl)-2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide have been prepared. These novel crystalline salts are useful in therapy as non-steroidal anti-arthritic agents. Methods for preparing these salts from the corresponding acidic starting material and the appropriate amine base are provided.Type: GrantFiled: April 13, 1982Date of Patent: February 28, 1984Assignee: Pfizer Inc.Inventor: Joseph G. Lombardino
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Patent number: 4388105Abstract: There are provided herbicidal cyclic sulfonamides of phenoxybenzoic acids.Type: GrantFiled: July 27, 1981Date of Patent: June 14, 1983Assignee: Rhone-Poulenc AgrochimieInventor: James T. Bahr
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Patent number: 4376768Abstract: N-(6-chloro-2-pyridyl)-3,4-dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-3-ca rboxamide 1,1-dioxide that is a novel benzothiazine derivative. The compound is characterized by a low degree of toxicity and a low incidence of gastric disorders and useful as an anti-inflammatory agent.Type: GrantFiled: June 16, 1981Date of Patent: March 15, 1983Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Shoichiro Ozaki, Hideya Kobayashi, Haruki Mori, Takafumi Kitano, Hiroshi Kawazura, Yutaka Okazaki
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Patent number: 4376119Abstract: N-(6-fluoro-2-pyridyl)-3,4-dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-3-ca rboxamide 1,1-dioxide that is a novel benzothiazine derivative. The compound is characterized by a low degree of toxicity and a low incidence of gastric disorders and useful as an anti-inflammatory agent.Type: GrantFiled: June 16, 1981Date of Patent: March 8, 1983Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Shoichiro Ozaki, Hideya Kobayashi, Haruki Mori, Hiroshi Kawazura, Yutaka Okazaki, Takafumi Kitano, Mikio Kumakura, Takuo Nakano
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Patent number: 4342761Abstract: Compounds having the formula ##STR1## wherein Y represents --CHOH-- or ##STR2## Z and Z.sup.1 independently represent ##STR3## --SO.sub.2 --, --COCH.sub.2 --, or --CO(CH.sub.2).sub.2 --; Z may also represent --CH.sub.2 --, --(CH.sub.2).sub.2, --CHMe--, or --CMe.sub.2 --; R.sup.1 and R.sup.2 independently represent hydrogen or substituents selected from halogen, lower-alkoxy, nitro, amino, lower alkylamino, trifluoromethyl, hydroxy, aryl lower alkoxy and lower alkyl; or R.sup.1 and R.sup.2 when adjacent together with the carbon atoms to which they are attached form a six membered carbocyclic ring; R.sup.3 represents hydrogen, halogen, lower alkyl or lower alkoxy, R.sup.4 represents lower alkyl or hydrogen; .alpha. and .beta. each represent hydrogen or a direct bond between the carbon atoms to which they are attached, and acid addition quaternary ammonium salts thereof, are disclosed which possess antihypertensive activity.Type: GrantFiled: October 20, 1980Date of Patent: August 3, 1982Assignee: John Wyeth & Brother LimitedInventor: Terence J. Ward
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Patent number: 4327091Abstract: 3,4-Dihydro-2H-1,2-benzothiazine 1,1-dioxides of the formula ##STR1## wherein Ph represents a substituted or unsubstituted 1,2-phenylene radical, R represents a substituted or unsubstituted benzopyrone radical, and R.sub.1 represents hydrogen or a substituted or unsubstituted hydrocarbon radical of aliphatic character, and their salts, possess antiinflammatory properties and are useful as medicaments.Type: GrantFiled: January 28, 1980Date of Patent: April 27, 1982Assignee: Ciba-Geigy CorporationInventors: Alex Sele, Pier G. Ferrini, Georges Haas, Knut A. Jaeggi, Alberto Rossi
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Patent number: 4309427Abstract: Certain novel derivatives of N-(2-pyridyl)-2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide have been prepared, including N-(2-pyridyl)-2-methyl-4-acetoxy-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide, N-(2-pyridyl)-2-methyl-4-(n-butyryloxy)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide, N-(6-methyl-2-pyridyl)-2-methyl-4-acetoxy-2H-1,2-benzothiazine-3-carboxami de 1,1-dioxide, N-(2-pyridyl)-2-methyl-4-benzoyloxy-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide, N-(6-methyl-2-pyridyl)-2-methyl-4-benzoyloxy-2H-1,2-benzothiazine-3-carbox amide 1,1-dioxide, N-(2-pyridyl)-2-methyl-4-methanesulfonyloxy-2H-1,2-benzothiazine-3-carboxa mide 1,1-dioxide and N-(6-methyl-2-pyridyl)-2-methyl-4-methanesulfonyloxy-2H-1,2-benzothiazine- 3-carboxamide 1,1-dioxide. All these compounds are useful in therapy as non-steroidal anti-inflammatory agents, especially when administered by the topical route of administration. Methods for preparing these compounds from known starting materials are provided.Type: GrantFiled: January 15, 1981Date of Patent: January 5, 1982Assignee: Pfizer Inc.Inventor: Joseph G. Lombardino