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US4542209A
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Fluorine-containing uridine derivative and preparation and use thereof
Assignee: Daikin Industries Ltd
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Filing: 1983-12-07
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Granted: 1985-09-17
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Expires: 2003-12-07
Abstract
Abstract A fluorine-containing uridine derivative of the formula: <IMAGE> (I) wherein R is lower acyl, fluorine-containing lower acyl or fluorine-containing lower alkyl; and X is hydrogen or hydroxyl, which is prepared by a process which comprises fluorinating 2', 3'-O-isopropylideneuridine with fluorine in a solvent selected from the group consisting of lower carboxylic acids, fluorine-containing lower carboxylic acids and fluorine-containing lower alcohols, and is converted to a 5-fluorouridine derivative of the formula: <IMAGE> (II) wherein R and X are as defined above by reacting the fluorine-containing uridine derivative of the formula (I) with a base in an organic solvent at a temperature of 0 DEG to 80 DEG C.
Inventors
- 👤 Takao Takahara
- 👤 Yorisato Hisanaga
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 15:11
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; C07H1/00; C07H19/067
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
26 words
A fluorine-containing uridine derivative of the formula: ##STR17## wherein R is lower acyl, fluorine-containing lower acyl or fluorine-containing lower alkyl; and X is hydrogen or hydroxyl.
Claim 2
Dependent Claim
26 words
A fluorine-containing uridine derivative of the formula: ##STR17## wherein R is lower acyl, fluorine-containing lower acyl or fluorine-containing lower alkyl; and X is hydrogen or hydroxyl.
Claim 3
Dependent Claim
13 words
A fluorine-containing uridine derivative according to claim 1, wherein R is lower acyl.
Claim 4
Dependent Claim
14 words
A fluorine-containing uridine derivative according to claim 1, wherein R is fluorinated lower acyl.
Claim 5
Dependent Claim
14 words
A fluorine-containing uridine derivative according to claim 1, wherein R is fluorinated lower alkyl.
Claim 6
Dependent Claim
12 words
A fluorine-containing uridine derivative according to claim 1, wherein X is hydrogen.
Claim 7
Dependent Claim
12 words
A fluorine-containing uridine derivative according to claim 1, wherein X is hydroxy.
Claim 8
Dependent Claim
16 words
A fluorine-containing uridine derivative according to claim 1, wherein R is acetyl and X is hydroxy.
Claim 9
Dependent Claim
16 words
A fluorine-containing uridine derivative according to claim 1, wherein R is acetyl and X is hydrogen.
Claim 10
Dependent Claim
42 words
A process for preparing a fluorine-containing uridine derivative of the formula (I) as defined in claim 1, comprising fluorinating 2°,3'-O-isopropylideneuridine with fluorine in a solvent selected from the group consisting of lower carboxylic acids, fluorine-containing lower carboxylic acids and fluorine-containing lower alcohols.
Claim 11
Dependent Claim
18 words
A process according to claim 9, wherein fluorination is effected at a temperature of 0° to 50° C.
Claim 12
Dependent Claim
26 words
A process according to claim 9, wherein fluorination is effected in the presence of a fluorination agent which comprises fluorine gas diluted with an inert gas.
Claim 13
Dependent Claim
27 words
A process according to claim 9, wherein the solvent is a lower carboxylic acid selected from the group consisting of acetic acid, propionic acid and butyric acid.
Claim 14
Dependent Claim
31 words
A process according to claim 9, wherein the solvent is a fluorine-containing lower carboxylic acid selected from the group consisting of fluorinated acetic acid, fluorinated propionic acid and fluorinated butyric acid.
Claim 15
Dependent Claim
29 words
A process according to claim 9, wherein the solvent is a fluorine-containing alcohol of the formula: H(CF.sub.2 CF.sub.2).sub.n CH.sub.2 OH wherein n is an integer of 1 to 5.
Claim 16
Dependent Claim
59 words
A process for preparing a 5-fluorouridine derivative of the formula: ##STR18## wherein R is lower acyl, fluorine-containing lower acyl or fluorine-containing lower alkyl; and X is hydrogen or hydroxyl comprising reacting the fluorine-containing uridine derivative of the formula (I) as defined in claim 1 with a base in an organic solvent at a temperature of 0° to 80° C.
Claim 17
Dependent Claim
25 words
A process according to claim 15, wherein the base is one selected from the group consisting of triethylamine, diethylamine, pyridine, picoline, ammonia and sodium bicarbonate.
Claim 18
Dependent Claim
35 words
A process according to claim 16, wherein the solvent is a mixture of an ester of a lower carboxylic acid, acetone, acetonitrile or dioxane and not more than 50% by volume of a lower alcohol.
Claim 19
Dependent Claim
15 words
A process according to claim 16, wherein the reaction temperature is 0° to 80° C.
Claim 20
Dependent Claim
18 words
A process according to claim 9, wherein fluorination is effected at a temperature of 5° to 20° C.
Claim 21
Dependent Claim
15 words
A process according to claim 16, wherein the reaction temperature is 10° to 30° C.
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) | 1988-09-16 | 1989-03-18 | 1989-09-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-09-16 | 1993-03-18 | 1993-09-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-09-16 | 1997-03-18 | 1997-09-17 | $7700.00 | Window Closed / Lapsed |