YU49474B - POSTUPAK ZA DOBIJANJE 2-β-D-RIBOFURANOZILTIAZOL -4-KARBOKSIAMIDA - Google Patents
POSTUPAK ZA DOBIJANJE 2-β-D-RIBOFURANOZILTIAZOL -4-KARBOKSIAMIDAInfo
- Publication number
- YU49474B YU49474B YU9695A YU9695A YU49474B YU 49474 B YU49474 B YU 49474B YU 9695 A YU9695 A YU 9695A YU 9695 A YU9695 A YU 9695A YU 49474 B YU49474 B YU 49474B
- Authority
- YU
- Yugoslavia
- Prior art keywords
- formula
- anhydro
- reaction
- ribofuranosylthiazole
- cooled
- Prior art date
Links
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Postupak za dobijanje 2--D-ribofuranoziltiazol-4-karboksiamida formule I koji se odvija u pet faza, naznačen time, što se u fazi (a) reagovanjem 1-O-acetil-2,3,5-tri-O-benzoil- -D-ribofuranoze formule II, rastvorene u metilen-hloridu i rastvor ohlađen na 0 do 2В°C, sa trimetilsilil-cijanidom, u prisustvu kalaj(IV)-hlorida kao katalizatora, pri čemu se reakcija odvija na -5 do 0 В°C u toku 90 minuta, dobija 2,3-anhidro-3,4,6-tri-O-benzoil--D-alononitril (cijano šećer) formule III, posle čega se dobijeni cijano šećer, u fazi (b), u smeši sa metanolom i natrijum-metoksidom, na temperaturi od 35 do 45 В°C, uz mešanje u atmosferi azota u toku tri sata prevodi u metil-2,5-anhidro-D-alonimidat formule IV; a dobijeni alonimidat, u sledećoj fazi (c), u etanolu u prisustvu trietilamina ohlađen na 0В°C sa gasovitim vodonik-sulfidom na temperaturi -5 do 2 В°C, uz mešanje, daje 2,5-anhidro-D-alontioamid formule V, posel čega se reakcija odvija još jedan sat na sobnoj temperaturi, do potupnog izdvajanja proizvoda tioamida, koji se u fazi (d) kondenzuje sa etil-α-brom-piruvatom, u toku 10-14 časova, na sobnoj temperaturi u tetrahidrofuranu, pri čemu dolazi do stvaranja etil-2--D-ribofuranozil-tiazol-4-karboksilata formule VI, koji se dodaje, u poseldnjoj fazi (e), u rastvor metanola zasićenog amonijakom, i ohlađenim na -20В°C, da bi se posle stajanja na 4 do 8 В°C, u toku dva dana dobio proizvod 2--D-ribofuranoziltiazol-4-karboksamid formuel I. Prijava sadrži još 4 zavisna patentna zahteva.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU9695A YU49474B (sh) | 1995-02-17 | 1995-02-17 | POSTUPAK ZA DOBIJANJE 2-β-D-RIBOFURANOZILTIAZOL -4-KARBOKSIAMIDA |
| US08/603,106 US5907036A (en) | 1995-02-17 | 1996-02-20 | Procedures for obtaining ribo-C-nucleosides |
| AU52980/96A AU5298096A (en) | 1995-02-17 | 1996-02-20 | Procedures for obtaining ribo-c-nucleosides |
| PCT/US1996/002512 WO1996026212A1 (en) | 1995-02-17 | 1996-02-20 | Procedures for obtaining ribo-c-nucleosides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU9695A YU49474B (sh) | 1995-02-17 | 1995-02-17 | POSTUPAK ZA DOBIJANJE 2-β-D-RIBOFURANOZILTIAZOL -4-KARBOKSIAMIDA |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| YU9695A YU9695A (sh) | 1997-12-05 |
| YU49474B true YU49474B (sh) | 2006-05-25 |
Family
ID=47595144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU9695A YU49474B (sh) | 1995-02-17 | 1995-02-17 | POSTUPAK ZA DOBIJANJE 2-β-D-RIBOFURANOZILTIAZOL -4-KARBOKSIAMIDA |
Country Status (1)
| Country | Link |
|---|---|
| YU (1) | YU49474B (sh) |
-
1995
- 1995-02-17 YU YU9695A patent/YU49474B/sh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU9695A (sh) | 1997-12-05 |
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