TN2010000384A1 - Method for preparing combretastatin - Google Patents
Method for preparing combretastatinInfo
- Publication number
- TN2010000384A1 TN2010000384A1 TNP2010000384A TN2010000384A TN2010000384A1 TN 2010000384 A1 TN2010000384 A1 TN 2010000384A1 TN P2010000384 A TNP2010000384 A TN P2010000384A TN 2010000384 A TN2010000384 A TN 2010000384A TN 2010000384 A1 TN2010000384 A1 TN 2010000384A1
- Authority
- TN
- Tunisia
- Prior art keywords
- salt
- combretastatin
- formula
- base
- amino compound
- Prior art date
Links
- LGZKGOGODCLQHG-CYBMUJFWSA-N 5-[(2r)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C[C@@H](O)C1=CC(OC)=C(OC)C(OC)=C1 LGZKGOGODCLQHG-CYBMUJFWSA-N 0.000 title abstract 4
- LGZKGOGODCLQHG-UHFFFAOYSA-N combretastatin Natural products C1=C(O)C(OC)=CC=C1CC(O)C1=CC(OC)=C(OC)C(OC)=C1 LGZKGOGODCLQHG-UHFFFAOYSA-N 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 2
- 125000002842 L-seryl group Chemical class O=C([*])[C@](N([H])[H])([H])C([H])([H])O[H] 0.000 abstract 1
- -1 amino compound Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for preparing a combretastatin (A) in the form of a base or of an addition salt with an acid, which comprises coupling, in the presence of a base and ofT3P, the salt of the (Z)-amino compound of formula (I) with a doubly protected L-serine derivative of formula (II) in which PG denotes a group protecting the amine function, so as to obtain the compound of formula (Z)-(lb), then deprotecting and opening the ring of (Z)-(lb) in the presence of an acid, so as to obtain the combretastatin (A) in the form of a salt; and, optionally, adding a base, so as to obtain the combretastatin (A) in the form of a base, the salt of the (Z)-amino compound having been obtained by enrichment of the salt of the amino compound of formula (II) in (Z) isomer.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/FR2009/000215 WO2009118474A1 (en) | 2008-02-28 | 2009-02-27 | Method for preparing combretastatin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TN2010000384A1 true TN2010000384A1 (en) | 2011-12-29 |
Family
ID=55024509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TNP2010000384A TN2010000384A1 (en) | 2009-02-27 | 2010-08-19 | Method for preparing combretastatin |
Country Status (1)
| Country | Link |
|---|---|
| TN (1) | TN2010000384A1 (en) |
-
2010
- 2010-08-19 TN TNP2010000384A patent/TN2010000384A1/en unknown
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