ES2021557A6 - Process for obtaining 4-hydroxy-methyl-N-2-pyridinyl-2H- thiene[2,3c]-1,2-thiazine-3-carboxamide 1,1 dioxide - Google Patents
Process for obtaining 4-hydroxy-methyl-N-2-pyridinyl-2H- thiene[2,3c]-1,2-thiazine-3-carboxamide 1,1 dioxideInfo
- Publication number
- ES2021557A6 ES2021557A6 ES9001982A ES9001982A ES2021557A6 ES 2021557 A6 ES2021557 A6 ES 2021557A6 ES 9001982 A ES9001982 A ES 9001982A ES 9001982 A ES9001982 A ES 9001982A ES 2021557 A6 ES2021557 A6 ES 2021557A6
- Authority
- ES
- Spain
- Prior art keywords
- stage
- thiazine
- methyl
- dioxide
- thiene
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
Abstract
New process for obtaining 4-hydroxy-methyl-N-2-pyridinyl- 2H-thiene[2,3c]-1,2-thiazine-3-carboxamide 1,1 dioxide, taking place in 5 stages: In the first stage 2-thiophene carboxylic acid chloride reacts with methyl acetate isocyanate in the presence of triethylamine. In the second stage the oxazole obtained in methanol is treated with concentrated hydrochloric acid at 45-50 degree C for 4 hours. In the third stage the ketoester obtained is treated with thionyl chloride in acetonitrile in the presence of traces of SbCl5 as catalyst. In a first step in the fourth stage the compound obtained in stage 3 is treated with sodium hydride in anhydrous dimethyl formamide and in a second step methyl iodide is added to obtain 3-methoxycarbonyl-4- acetoxy-2-methylthiene [2,3c]-1,2-thiazine -1,1-dioxide, this compound reacts in a fifth stage with 2- aminopyridine in dry xylene to finally yield 4-hydroxy- methyl-N-2-pyridinyl-2H-thiene[2,3c]-1,2-thiazine-3- carboxamide 1,1 dioxide. Application: starts from commercially available reagents. Subdivides the synthesis into five stages. Eliminates problems of regional selectivity in methylation of the N of the thiazine.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES9001982A ES2021557A6 (en) | 1990-07-23 | 1990-07-23 | Process for obtaining 4-hydroxy-methyl-N-2-pyridinyl-2H- thiene[2,3c]-1,2-thiazine-3-carboxamide 1,1 dioxide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES9001982A ES2021557A6 (en) | 1990-07-23 | 1990-07-23 | Process for obtaining 4-hydroxy-methyl-N-2-pyridinyl-2H- thiene[2,3c]-1,2-thiazine-3-carboxamide 1,1 dioxide |
Publications (1)
Publication Number | Publication Date |
---|---|
ES2021557A6 true ES2021557A6 (en) | 1991-11-01 |
Family
ID=8268269
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES9001982A Expired - Fee Related ES2021557A6 (en) | 1990-07-23 | 1990-07-23 | Process for obtaining 4-hydroxy-methyl-N-2-pyridinyl-2H- thiene[2,3c]-1,2-thiazine-3-carboxamide 1,1 dioxide |
Country Status (1)
Country | Link |
---|---|
ES (1) | ES2021557A6 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005061443A2 (en) | 2003-12-19 | 2005-07-07 | Basf Aktiengesellschaft | Benzoyl-substituted phenylalanine amides |
US7879761B2 (en) | 2005-05-25 | 2011-02-01 | Basf Aktiengesellschaft | Heteroaroyl-substituted serineamides |
-
1990
- 1990-07-23 ES ES9001982A patent/ES2021557A6/en not_active Expired - Fee Related
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005061443A2 (en) | 2003-12-19 | 2005-07-07 | Basf Aktiengesellschaft | Benzoyl-substituted phenylalanine amides |
US7879761B2 (en) | 2005-05-25 | 2011-02-01 | Basf Aktiengesellschaft | Heteroaroyl-substituted serineamides |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PC1A | Transfer granted |
Owner name: ELMUQUIMICA FARMACEUTICA, S.L. |
|
FD1A | Patent lapsed |
Effective date: 20001102 |