KR910006315A - Epi-grape pilotoxine altroside derivative - Google Patents

Abstract

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Description

Eppegthropyrotoxin altroside derivative

Since this is a trivial issue, I did not include the contents of the text.

Figures 1 to 3 illustrate the synthesis of the compounds of the present invention,

R in FIG. 2 is the same as R ⁵ in the general formula X.

Claims (25)

Compounds having the following general formula Wherein R ³ is a group selected from (C ₁ -C ₁₀ ) alkyl, phenyl, furyl and 2-thienyl; One of R ⁴ and R ⁵ is selected from hydroxy, C _1-5 alkoxy and C _1-5 acyloxy; And the other is selected from H, hydroxy, C _1-5 alkoxy, C _1-5 acyloxy, F, azido, and amino; Or one of R < ⁴ > and R < ⁵ > is F and the other is selected from azido and imino; R ⁶ is selected from hydrogen, P (O) (OH) ₂ and its alkali or alkaline earth metal salts. The method according to claim 1, wherein the 4'-demethyl-4-O- (3-O-acetyl-2-deoxy- ) ≪ / RTI > epubidophyllotoxin. The compound according to claim 1, wherein the compound is 4'-demethyl-4-O- (4,6-O-ethylidene- beta -D-altripyranosyl) epi-grape philatoxin. The compound according to claim 1, which is 4'-demethyl-4-O- (3-O-acetyl-4,6-0-ethylidene- beta -D-altripyranosyl) . 2. The method according to claim 1, which is 4'-demethyl-4-0- (2-amino-2-deoxy-4,6-0-ethylidene-beta-D-althropyranosyl) Lt; / RTI > The method according to claim 1, wherein the 4'-demethyl-4-O- (2-deoxy-4,6-O-ethylidene-2-fluoro-β-D-althropyranosyl) Lt; / RTI > The method according to claim 1, wherein the 4'-demethyl-4-O- (2,3-di-O-acetyl-4,6-0-ethylidene -? - D-althropyranosyl) Lt; / RTI > The method of claim 1, wherein the 4'-demethyl-4-0- (3-O-acetyl-2-azido-2-deoxy- ) ≪ / RTI > epubidophyllotoxin. The method of claim 1, wherein the 4'-demethyl-4-0- (3-O-acetyl-2-deoxy-4,6- ) ≪ / RTI > epubidophyllotoxin. The method according to claim 1, wherein the 4'-demethyl-4-0- (2-azido-2-deoxy-4,6-0-ethylidene-beta-D-althropyranosyl) Lt; / RTI > The compound according to claim 1, wherein the compound is 4'-demethyl-4-O- (2-deoxy-4,6-O-ethylidene-β-D-althropyranosyl) epiglucite. The compound according to claim 1, which is 4'-demethyl-4-O- (4,6-O-ethylidene-3-0-methyl- beta -D-altripyranosyl) . The method according to claim 1, wherein the 4'-demethyl-4-O- (3-0-acetyl-2-amino- Apo < / RTI > phosphatoxine. The compound according to claim 1, which is 4'-demethyl-4-0- (2-O-acetyl-4,6-0-ethylidene- beta -D-altripyranosyl) . The compound according to claim 1, which is 4'-demethyl-4-0- (4,6-O-ethylidene-2-O-methyl- beta -D-altripyranosyl) . The method according to claim 1, wherein the 4'-demethyl-4-0- (2,3-di-O-methyl-4,6-0-ethylidene- beta -D-altripyranosyl) Lt; / RTI > The method according to claim 1, wherein the disodium 4'-demethyl-4-O- (2-deoxy-4,6-O-ethylidene-2-fluoro- 4'-deoxy-4'-phosphate. The method of claim 1, wherein the 4'-benzyloxycarbonyl-4'-demethyl-4-0- (3-azido-2- fluoro-2,3-dideoxy- -.beta.-D-althropyranosyl) epi-phosphatoxin. 3. The compound according to claim 1, which is 4'-demethyl-4-O- (3-azido-2,3-dideoxy-4,6-0-ethylidene-2-fluoro- Lt; RTI ID = 0.0 > epitope < / RTI > 2. The method of claim 1, wherein the 4'-demethyl-4-O- (3-amino-2,3-dideoxy-4,6- ) ≪ / RTI > epubidophyllotoxin. Lt; RTI ID = 0.0 > pharmaceutically < / RTI > effective amount of the compound of claim 1 and a pharmaceutically acceptable carrier. Wherein the antineoplastic effective amount of the compound of claim 1 is administered to the mammalian host having the tumor. A. Compounds of the formula In the presence of boron trifluoride etherate with a compound of the general formula: (In the formula, R ^3, R ⁴ and R ⁵ are as described below) B. Hydrogenation of the product of step A to remove the phenol protecting group; C. The method optionally, by phosphorylation of phenol R ⁶ is PO ₃ H ₂ or a product or a salt thereof acceptable as claimed in obtaining a salt thereof, a compound or a pharmacologically less with the following formula. Wherein R ³ is selected from (C ₁ -C ₁₀ ) alkyl, phenyl, furyl and 2-thienyl; One of R ⁴ and R ⁵ is selected from C _1-5 alkoxy and C _1-5 acyloxy; And the other is selected from H, C _1-5 alkoxy, C _1-5 alkoxy, C _1-5 acyloxy, F and azido; Or one of R < ⁴ > and R < ⁵ > is F and the other is aryl; R ⁶ is H or PO ₃ H ₂ . Wherein one of R < ⁴ > and R < ⁵ > is a non-OH _C5 acyloxy and the other is a compound of the following formula, ≪ / RTI > or a pharmaceutically acceptable salt thereof. Wherein R ³ is (C ₁ -C ₁₀ ) alkyl, phenyl, furyl, and 2-thienyl; One of R ⁴ and R ⁵ is OH and the other is selected from O, OH, C _1-5 alkoxy, C _1-5 acyloxy, F and azido _; R ⁶ is H or PO ₃ H ₂ . In which one of R < ⁴ > and R < ⁵ > is not amino and the other is hydrogenation of a compound of the following general formula in the presence of a catalyst, Or a pharmaceutically acceptable salt thereof. Wherein R ³ is (C ₁ -C ₁₀ ) alkyl, phenyl, furyl, and 2-thienyl; One of R < ⁴ > and R < ⁵ > is amino; The other is selected from hydroxy, C _1-5 alkoxy, C _1-5 acyloxy, and fluoro; and R ⁶ is H or PO ₃ H ₂ . ※ Note: It is disclosed by the contents of the first application.