PL397204A1 - Sposób syntezy i izolacji des azytromycyny - Google Patents
Sposób syntezy i izolacji des azytromycynyInfo
- Publication number
- PL397204A1 PL397204A1 PL397204A PL39720411A PL397204A1 PL 397204 A1 PL397204 A1 PL 397204A1 PL 397204 A PL397204 A PL 397204A PL 39720411 A PL39720411 A PL 39720411A PL 397204 A1 PL397204 A1 PL 397204A1
- Authority
- PL
- Poland
- Prior art keywords
- azithromycin
- temperature
- complex
- des
- homoerythromycin
- Prior art date
Links
- 229960004099 azithromycin Drugs 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000002955 isolation Methods 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 238000002425 crystallisation Methods 0.000 abstract 2
- 230000008025 crystallization Effects 0.000 abstract 2
- 239000011780 sodium chloride Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- HRKNNHYKWGYTEN-HOQMJRDDSA-N (2r,3s,4r,5r,8r,10r,11r,12s,13s,14r)-11-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecan-15-one Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)NC[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 HRKNNHYKWGYTEN-HOQMJRDDSA-N 0.000 abstract 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000008103 glucose Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 238000009938 salting Methods 0.000 abstract 1
- -1 sodium carboxyborohydride Chemical compound 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
Landscapes
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Sposób wytwarzania des azytromycyny, wedlug wynalazku polega na tym, ze 9-deoksy-6-dezoksy-6,9-epoksy-9,9a-didehydro-9a-aza- homoerytromycyne A, poddaje sie reakcji redukcji nadmiarem wodoru, wydzielajacym sie in situ w reakcji borowodorku z kwasem karboksylowym z utworzeniem pojedynczego lub potrójnego kompleksu karboksyborowodorku sodu, przy czym reakcje prowadzi sie w alkoholu alifatycznym, korzystnie metanolu, w temperaturze od -10°C do 60°C, a produkt reakcji w postaci kompleksu des azytromycyny z borowodorkiem, zakwasza sie kwasem, korzystnie kwasem solnym, z dodatkiem cukru, korzystnie glukozy, w roztworze wodnym do rozkladu kompleksu do wolnej des azytromycyny i izolacje 9-deokso-9a-aza-9a-homoerytromycyny A poprzez wysalanie roztworem wodnym chlorku sodu do rozpuszczalnika organicznego mieszajacego sie z woda, korzystnie acetonu, w temperaturze 10°C÷25°C, przy wysokim pH od 9 do 11, a nastepnie bezposrednia krystalizacje w temperaturze 10°C÷25°C, poprzez dodawanie wody do mieszaniny acetonowej. Wlasciwe stezenie roztworu chlorku sodu oraz temperatura krystalizacji wplywaja na zwiekszenie wydajnosci procesu, czystosc produktu oraz powstanie odpowiedniej postaci krystalicznej.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL397204A PL217775B1 (pl) | 2011-12-01 | 2011-12-01 | Sposób syntezy i izolacji N-demetylo-azytromycyny |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL397204A PL217775B1 (pl) | 2011-12-01 | 2011-12-01 | Sposób syntezy i izolacji N-demetylo-azytromycyny |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL397204A1 true PL397204A1 (pl) | 2013-06-10 |
| PL217775B1 PL217775B1 (pl) | 2014-08-29 |
Family
ID=48539527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL397204A PL217775B1 (pl) | 2011-12-01 | 2011-12-01 | Sposób syntezy i izolacji N-demetylo-azytromycyny |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL217775B1 (pl) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104177456A (zh) * | 2013-05-23 | 2014-12-03 | 长春海悦药业有限公司 | 一种阿奇霉素药物原料及制剂和用途 |
-
2011
- 2011-12-01 PL PL397204A patent/PL217775B1/pl unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104177456A (zh) * | 2013-05-23 | 2014-12-03 | 长春海悦药业有限公司 | 一种阿奇霉素药物原料及制剂和用途 |
| CN104177456B (zh) * | 2013-05-23 | 2016-07-13 | 长春海悦药业有限公司 | 一种阿奇霉素药物原料及制剂和用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| PL217775B1 (pl) | 2014-08-29 |
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