CA2180444A1 - Water soluble onium salt of taxo-diterpenoid - Google Patents

Water soluble onium salt of taxo-diterpenoid

Info

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
Application number
CA002180444A
Other languages
French (fr)
Other versions
CA2180444C (en
Inventor
K.C. Nicolaou
Wolfgang Wrasidlo
Rodney K. Guy
Emmanuel Pitsinos
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.)
Scripps Research Institute
Original Assignee
K.C. Nicolaou
Wolfgang Wrasidlo
Rodney K. Guy
Emmanuel Pitsinos
The Scripps Research Institute
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 K.C. Nicolaou, Wolfgang Wrasidlo, Rodney K. Guy, Emmanuel Pitsinos, The Scripps Research Institute filed Critical K.C. Nicolaou
Priority claimed from PCT/US1995/000478 external-priority patent/WO1995018804A1/en
Publication of CA2180444A1 publication Critical patent/CA2180444A1/en
Application granted granted Critical
Publication of CA2180444C publication Critical patent/CA2180444C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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.
CA002180444A 1994-01-11 1995-01-10 Water soluble onium salt of taxo-diterpenoid Expired - Lifetime CA2180444C (en)

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)

Also Published As

Publication number Publication date
CA2180444C (en) 2006-02-28

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Effective date: 20150112