WO2005111056B1 - New esters of adenosine nucleosides and carboxylic acid - Google Patents
New esters of adenosine nucleosides and carboxylic acidInfo
- Publication number
- WO2005111056B1 WO2005111056B1 PCT/PL2005/000031 PL2005000031W WO2005111056B1 WO 2005111056 B1 WO2005111056 B1 WO 2005111056B1 PL 2005000031 W PL2005000031 W PL 2005000031W WO 2005111056 B1 WO2005111056 B1 WO 2005111056B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- chloroethyl
- bis
- deoxyadenosine
- esters
- formula
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Abstract
Novel esters of adenosine nucleosides and carboxylic acid, of formula 1, wherein R1 is hydrogen or chlorine atom, R2 is acylic group of carboxylic acid and an ester bond is located between carboxyl group of an acid and hydroxyl group in 5' position of 2'-deoxyadenosine and method of their preparation.
Claims
AMENDED CLAIMS received by the International Bureau on 12 December 2005 (12.12.2005) original claims 1-12 have been replaced by amended claims 1-9 (2 pages).
5 1. Novel esters of 2'-deoxyadenosine or 2-chloro-2'-deoxyadenosine and 4-bis(2- chloroethyl)-p- aminobenzenebutanoic acid, of formula 1 , wherein Ri is hydrogen or chlorine atom, R2 is 4-bis(2-chloroethyl)-p-aminobenzenobutyryl group and an ester bond is located between carboxyl group of an acid and hydroxyl group in 5' position of mentioned above nucleosides.
Formula 1.
2. An ester according to claim 1 which is 5'-0-[4-bis(2-chloroethyl)-p-arninobenzeno- butyryl]-2'-deoxyadenosine.
3. An ester according to claim 1 which is 5'-O-[4-bis(2-chloroethyl)-p-aminobenzenebutyryl]- 5 2-chloro-2'-deoxyadenosine.
4. A method of preparation of the esters of formula 1 wherein Ri is hydrogen or chlorine atom, R2 is 4-bis(2-chloroethyl)-p-aminobenzenobutyryl group according to claim 1, wherein the regioselective esterification reaction of 2'-deoxyadenosine or its derivative with 4-bis(2-chloroethyl)-p-aminobenzenebutanoic acid is carried out in the environment 0 of mixture of triphenylphosphine and esters of azodicarboxylate acid in a polar organic solvent at a temperature close to the room temperature, then the resulting final product in a form of ester is isolated from the reaction mixture.
5. A method of preparation of the esters of formula 1 according to claim 4 wherein the regio¬ selective esterification reaction is carried out in a polar aprotic organic solvent such as 5 dimetyloformamide or pyridine.
6. A method of preparation of esters according to claim 4 wherein the esterification reaction is carried out at the temperature of 20-370C.
7. A method of preparation of esters according to claim 4 wherein the product is isolated from the reaction mixture by adsorption or high performance liquid chromatography.
8. A pharmaceutical composition indicated for the treatment of neoplastic diseases, especially, proliferative diseases of hematopoietic system, wherein 5'-O-[4-bis(2- chloroethyl)-p-aminobenzenobutyryl]-2'-deoxyadenosine as an active compound at a dose necessary to exert the cytotoxic effect, with at least one neutral pharmaceutically acceptable carrier, solvent or vehicle is included.
9. A pharmaceutical composition indicated for the treatment of neoplastic diseases, especially proliferative diseases of hematopoietic system, wherein 5'-O-[4-bis(2- chloroethyl)-p-aminobenzenebutyryl]-2-chloro-2'-deoxyadenosine as an active compound at a dose necessary to exert the cytotoxic effect, with at least one neutral pharmaceutically acceptable carrier, solvent or vehicle is included.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PLP.368093 | 2004-05-19 | ||
| PL368093A PL201571B1 (en) | 2004-05-19 | 2004-05-19 | New esters of adenosine nucleosides and carboxylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2005111056A1 WO2005111056A1 (en) | 2005-11-24 |
| WO2005111056B1 true WO2005111056B1 (en) | 2006-02-02 |
Family
ID=34979268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/PL2005/000031 WO2005111056A1 (en) | 2004-05-19 | 2005-05-19 | New esters of adenosine nucleosides and carboxylic acid |
Country Status (2)
| Country | Link |
|---|---|
| PL (1) | PL201571B1 (en) |
| WO (1) | WO2005111056A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2010000424A (en) | 2007-07-09 | 2010-08-10 | Easter Virginia Medical School | Substituted nucleoside derivatives with antiviral and antimicrobial properties. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6348451B1 (en) * | 1987-10-28 | 2002-02-19 | Pro-Neuron, Inc. | Acyl deoxyribonucleoside derivatives and uses thereof |
| JPH0269191A (en) * | 1988-09-05 | 1990-03-08 | Taiho Yakuhin Kogyo Kk | Deacylation of nucleosides |
-
2004
- 2004-05-19 PL PL368093A patent/PL201571B1/en not_active IP Right Cessation
-
2005
- 2005-05-19 WO PCT/PL2005/000031 patent/WO2005111056A1/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| PL368093A1 (en) | 2005-11-28 |
| WO2005111056A1 (en) | 2005-11-24 |
| PL201571B1 (en) | 2009-04-30 |
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