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 dioxide

Info

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
Application number
ES9001982A
Other languages
Spanish (es)
Inventor
Ponce Andres Molina
Pablo Bueno M Soledad De
Lopez Juan Jose Vaquero
Navio Jose Luis Garcia
Builla Julio Alvarez
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ELMUQUIMICA FARMACEUTICA, S.L.
Original Assignee
Aliana S A
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 Aliana S A filed Critical Aliana S A
Priority to ES9001982A priority Critical patent/ES2021557A6/en
Publication of ES2021557A6 publication Critical patent/ES2021557A6/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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.
ES9001982A 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 Expired - Fee Related ES2021557A6 (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (2)

* Cited by examiner, † Cited by third party
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