WO2001040208A3 - Process for synthesis of 4-hydroxy-2h-1,2-benzothiazine-3-carboxamides - Google Patents

Process for synthesis of 4-hydroxy-2h-1,2-benzothiazine-3-carboxamides Download PDF

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Publication number
WO2001040208A3
WO2001040208A3 PCT/YU2000/000009 YU0000009W WO0140208A3 WO 2001040208 A3 WO2001040208 A3 WO 2001040208A3 YU 0000009 W YU0000009 W YU 0000009W WO 0140208 A3 WO0140208 A3 WO 0140208A3
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
benzothiazine
hydroxy
pyridyl
dioxide
Prior art date
Application number
PCT/YU2000/000009
Other languages
French (fr)
Other versions
WO2001040208A2 (en
Inventor
Slobodan Stankovic
Nebojsa Stojanovic
Snezana Milosevic
Dejan Nikolic
Original Assignee
Ad Zdravlje
Slobodan Stankovic
Nebojsa Stojanovic
Snezana Milosevic
Dejan Nikolic
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ad Zdravlje, Slobodan Stankovic, Nebojsa Stojanovic, Snezana Milosevic, Dejan Nikolic filed Critical Ad Zdravlje
Priority to AU36333/00A priority Critical patent/AU3633300A/en
Publication of WO2001040208A2 publication Critical patent/WO2001040208A2/en
Publication of WO2001040208A3 publication Critical patent/WO2001040208A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/02—1,2-Thiazines; Hydrogenated 1,2-thiazines

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Suggested invention is related to the field of organic chemistry technology, specifically to the process for preparation of the compound 4-hydroxy - 2 - methyl - 2 H - 1 , 2 - benzothiazine - 3 - carboxamide - 1 , 1 -dioxide, of general formula (I), wherein R denotes one of the following radicals: alkyl group (C2-C6), cycloalkyl, benzyl, phenyl, pyridyl, methyl-pyridyl, pyrimidyl, thiazole, isothiazole. Concerning clinical practice, the special interest, as non-steroidal antirheumatics characterized by anti-inflammatory and analgesic properties, belongs to: piroxicam (4-hydroxy-2-methyl-N-(2-pyridinyl-2H-1,2-benzothiazine-3-carboxamid-1,1-dioxide)), isoxicam (4-hydroxy-2-methyl-N-(5-methyl-3-isoxazolyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide)) and sudoxicam (4-hydroxy-2-methyl-N-2-thiazolyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide). Individual characteristics of the present invention are: the use of ethylester and dimethyl formamide with sodium ethoxide for opening of the cycle and for work at low temperatures in the mentioned phase; afterwards, methylation and final condensation with an amine of general formula NH2-Retard tablete, wherein R denotes: 2-pyridyl, alkyl substituted 2-pyridyl, 2-thiazole, 2-thiazole substituted with one or two alkyl groups, while each alkyl has from 1 to 4 carbon atoms or 5-methyl-3- isoxazolyl, using specific catalysts and adsorbents in an inert solvent and inert atmosphere.
PCT/YU2000/000009 1999-12-06 2000-04-06 Process for synthesis of 4-hydroxy-2h-1,2-benzothiazine-3-carboxamides WO2001040208A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU36333/00A AU3633300A (en) 1999-12-06 2000-04-06 Process for synthesis 4-hydroxy-2h-1,2-benzothiazine-3-carboxamides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
YUP-634/99 1999-12-06
YUP-634/99A RS49867B (en) 1999-12-06 1999-12-06 Process of synthessis 4-hidroxy -1 ,2-benzothiazine-3carboxamides

Publications (2)

Publication Number Publication Date
WO2001040208A2 WO2001040208A2 (en) 2001-06-08
WO2001040208A3 true WO2001040208A3 (en) 2001-11-29

Family

ID=25550782

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/YU2000/000009 WO2001040208A2 (en) 1999-12-06 2000-04-06 Process for synthesis of 4-hydroxy-2h-1,2-benzothiazine-3-carboxamides

Country Status (3)

Country Link
AU (1) AU3633300A (en)
RS (1) RS49867B (en)
WO (1) WO2001040208A2 (en)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3957772A (en) * 1975-05-21 1976-05-18 Warner-Lambert Company Process for the preparation of 4-hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2-methyl-2h-1,2-benzothiazine 1,1-dioxide
DE3212485A1 (en) * 1982-04-03 1983-10-13 Gödecke AG, 1000 Berlin METHOD FOR PRODUCING 4-HYDROXY-3- (HETEROCYCLOCARBAMOYL) -2H-1,2-BENZOTHIAZINE-1,1-DIOXIDES
EP0146102A2 (en) * 1983-12-16 1985-06-26 SPA SOCIETA' PRODOTTI ANTIBIOTICI S.p.A. Process for preparing benzothiazine compounds
EP0284514A1 (en) * 1987-03-27 1988-09-28 Esteve Quimica, S.A. Process for obtaining 4-hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3957772A (en) * 1975-05-21 1976-05-18 Warner-Lambert Company Process for the preparation of 4-hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2-methyl-2h-1,2-benzothiazine 1,1-dioxide
DE3212485A1 (en) * 1982-04-03 1983-10-13 Gödecke AG, 1000 Berlin METHOD FOR PRODUCING 4-HYDROXY-3- (HETEROCYCLOCARBAMOYL) -2H-1,2-BENZOTHIAZINE-1,1-DIOXIDES
EP0146102A2 (en) * 1983-12-16 1985-06-26 SPA SOCIETA' PRODOTTI ANTIBIOTICI S.p.A. Process for preparing benzothiazine compounds
EP0284514A1 (en) * 1987-03-27 1988-09-28 Esteve Quimica, S.A. Process for obtaining 4-hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 130, no. 13, 29 March 1999, Columbus, Ohio, US; abstract no. 162937r, page 46; XP002148246 *
H. ZINNES, JOURNAL OF ORGANIC CHEMISTRY, vol. 30, 1965, pages 2241 - 2246, XP000938873 *
J. G. LOMBARDINO ET AL., JOURNAL OF MEDICINAL CHEMISTRY, vol. 14, no. 12, 1971, pages 1171 - 1175, XP000938874 *
K. ABE ET AL., J. PHARM. SOC. JAPAN, vol. 76, 1956, pages 1058 - 63, XP000925889 *
Y. MA ET AL.: "Synthesis of cinnoxicamas antiinflammatory and antirheumatic drug", GUANGDONG YAOXUEYUAN XUEBAO, vol. 14, no. 3, 1998, pages 164 - 5 *

Also Published As

Publication number Publication date
WO2001040208A2 (en) 2001-06-08
YU63499A (en) 2002-06-19
RS49867B (en) 2008-08-07
AU3633300A (en) 2001-06-12

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