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US4599404A
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2-deoxy-5-fluorouridine derivative and a process for producing the same and an antitumor agent comprising the same
Assignee: Funai Pharmaceutical Industries Ltd
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Filing: 1979-08-21
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Granted: 1986-07-08
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Expires: 1999-08-21
Abstract
Abstract Novel 2 min -deoxy-5- fluorouridine derivatives represented by the formula; <CHEM> wherein R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an acetyloxy group or a halogen atom, and n is an a integer in the range of 1 to 3 are provided. These have good antitumor activities and low toxicities and are suitable for use as antitumor agents. The new compounds may be prepared by reacting 2 min -deoxy-3 min ,5 min -di-0-acetyl-5- fluorouridine with a benzoyl halide of the formula; <CHEM> where hal is a halogen atom and R and n are as before, preferably in the presence of an organic base, particularly triethylamine and a solvent, particularly dioxane.
Inventors
- 👤 Setsuro Fujii
- 👤 Eiichi Sakakibara
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 17:10
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; A; A61; A61P; A61P35/00
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
50 words
A 2'-deoxy-5-fluorouridine derivative represented by the general formula (I); ##STR7## wherein R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an acetyloxy group or a halogen atom, and n is an integer of 1 to 3.
Claim 2
Dependent Claim
50 words
A 2'-deoxy-5-fluorouridine derivative represented by the general formula (I); ##STR7## wherein R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an acetyloxy group or a halogen atom, and n is an integer of 1 to 3.
Claim 3
Dependent Claim
19 words
The 2'-deoxy-5-fluorouridine derivative according to claim 1, wherein R is an alkyl group having 1 to 5 carbon atoms.
Claim 4
Dependent Claim
19 words
The 2'-deoxy-5-fluorouridine derivative according to claim 1, wherein R is an alkoxy group having 1 to 4 carbon atoms.
Claim 5
Dependent Claim
13 words
The 2'-deoxy-5-fluorouridine derivative according to claim 1, wherein R is a halogen atom.
Claim 6
Dependent Claim
13 words
The 2'-deoxy-5-fluorouridine derivative according to claim 1, wherein R is an acetyloxy group.
Claim 7
Dependent Claim
13 words
The 2'-deoxy-5-fluorouridine derivative according to claim 1, wherein R is a hydrogen atom.
Claim 8
Dependent Claim
15 words
The 2'-deoxy-5-fluorouridine derivative according to claim 2, wherein the alkyl group is a methyl group.
Claim 9
Dependent Claim
15 words
The 2'-deoxy-5-fluorouridine derivative according to claim 3, wherein the alkoxy group is a methoxy group.
Claim 10
Dependent Claim
15 words
The 2'-deoxy-5-fluorouridine derivative according to claim 3, wherein the alkoxy group is a propoxy group.
Claim 11
Dependent Claim
15 words
The 2'-deoxy-5-fluorouridine derivative according to claim 3, wherein the alkoxy group is a butoxy group.
Claim 12
Dependent Claim
15 words
The 2'-deoxy-5-fluorouridine derivative according to claim 4, wherein the halogen atom is a fluorine atom.
Claim 13
Dependent Claim
16 words
The 2'-deoxy-5-fluorouridine derivative according to claim 7, wherein the methyl group is substituted at the 3-position.
Claim 14
Dependent Claim
16 words
The 2'-deoxy-5-fluorouridine derivative according to claim 7, wherein the methyl group is substitued at the 2-position.
Claim 15
Dependent Claim
13 words
The 2'-deoxy-5-fluorouridine derivative according to claim 8, wherein 2,3-disubstituent groups are methoxy groups.
Claim 16
Dependent Claim
15 words
The 2'-deoxy-5-fluorouridine derivative according to claim 11, wherein a 3-substituent group is a fluorine atom.
Claim 17
Dependent Claim
84 words
The process for producing a 2'-deoxy-5-fluorouridine derivative represented by the formula (I); ##STR8## wherein R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an acetyloxy group or a halogen atom, and n is an integer of 1 to 3, which comprises reacting 2'-deoxy-3',5'-di-O-acetyl-5-fluorouridine with a benzoyl halide represented by the general formula (II); ##STR9## wherein hal represents a halogen atom, and R and n are the same as defined above.
Claim 18
Dependent Claim
84 words
The process for producing a 2'-deoxy-5-fluorouridine derivative represented by the formula (I); ##STR8## wherein R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an acetyloxy group or a halogen atom, and n is an integer of 1 to 3, which comprises reacting 2'-deoxy-3',5'-di-O-acetyl-5-fluorouridine with a benzoyl halide represented by the general formula (II); ##STR9## wherein hal represents a halogen atom, and R and n are the same as defined above.
Claim 19
Dependent Claim
52 words
The process for producing a 2'deoxy-5-fluorouridine derivative according to claim 16, wherein the reaction is conducted with the use of the benzoyl halide wherein hal in the formula (II) is a chlorine atom, which is the benzoyl chloride, in the presence of triethylamine in dioxane from with ice-cooling to at 60° C.
Claim 20
Dependent Claim
32 words
A 5-fluoro-(2'-deoxy-β-uridine) derivative of the formula: ##STR10## wherein R represents hydrogen or optionally at least one substituent selected from the group consisting of halogen, acetyloxy, C 1-5 alkyl and C 1-4 alkoxy.
Claim 21
Dependent Claim
32 words
A 5-fluoro-(2'-deoxy-β-uridine) derivative of the formula: ##STR10## wherein R represents hydrogen or optionally at least one substituent selected from the group consisting of halogen, acetyloxy, C 1-5 alkyl and C 1-4 alkoxy.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-07-07 | 1990-01-06 | 1990-07-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-07-07 | 1994-01-06 | 1994-07-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-07-07 | 1998-01-06 | 1998-07-08 | $7700.00 | Window Closed / Lapsed |