CA2180444A1 - Water soluble onium salt of taxo-diterpenoid - Google Patents
Water soluble onium salt of taxo-diterpenoidInfo
- Publication number
- CA2180444A1 CA2180444A1 CA002180444A CA2180444A CA2180444A1 CA 2180444 A1 CA2180444 A1 CA 2180444A1 CA 002180444 A CA002180444 A CA 002180444A CA 2180444 A CA2180444 A CA 2180444A CA 2180444 A1 CA2180444 A1 CA 2180444A1
- Authority
- CA
- Canada
- Prior art keywords
- taxol
- arenes
- mpt
- aza
- taxo
- 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.)
- Granted
Links
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Pyridine Compounds (AREA)
Abstract
Onium salts of taxo-diterpenoid-Cn, 2-0-aza-arenes are employed as water soluble prodrugs. For example, taxol-2'-methylpyridinium tosylate (MPT) is characterized by an elevated aqueous solubility, rapid activation by serum protein, good stability in most other aqueous solutions, formation of a protein:taxol intermediate and good retension within the circulatory system.
The toxicity of the activated form is comparable or greater than underivatized taxol. Furthermore, taxol-2'-MPT can be synthesized by a simple one step reaction between taxol and 2-fluoro-1-MPT. The invention is applicable to taxol and taxol mimetics having hydroxyls that are reactive with onium salts of 2-halogenated-aza-arenes. For example, taxol, C-2 substituted analogs of taxol, and Taxotere each have reactive hydroxyls at the 2' and 7 positions.
The invention is also applicable to a wide array of 2-halogenated-aza-arenes.
The toxicity of the activated form is comparable or greater than underivatized taxol. Furthermore, taxol-2'-MPT can be synthesized by a simple one step reaction between taxol and 2-fluoro-1-MPT. The invention is applicable to taxol and taxol mimetics having hydroxyls that are reactive with onium salts of 2-halogenated-aza-arenes. For example, taxol, C-2 substituted analogs of taxol, and Taxotere each have reactive hydroxyls at the 2' and 7 positions.
The invention is also applicable to a wide array of 2-halogenated-aza-arenes.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US18003494A | 1994-01-11 | 1994-01-11 | |
US08/180,034 | 1994-01-11 | ||
PCT/US1995/000478 WO1995018804A1 (en) | 1994-01-11 | 1995-01-10 | Water soluble onium salt of taxo-diterpenoid |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2180444A1 true CA2180444A1 (en) | 1995-07-13 |
CA2180444C CA2180444C (en) | 2006-02-28 |
Family
ID=36011107
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002180444A Expired - Lifetime CA2180444C (en) | 1994-01-11 | 1995-01-10 | Water soluble onium salt of taxo-diterpenoid |
Country Status (1)
Country | Link |
---|---|
CA (1) | CA2180444C (en) |
-
1995
- 1995-01-10 CA CA002180444A patent/CA2180444C/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CA2180444C (en) | 2006-02-28 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKEX | Expiry |
Effective date: 20150112 |