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US4122251A
Expired / Lapsed
US
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Process for production of 5-fluorouracil and its derivatives
Assignee: Daikin Industries Ltd
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Filing: 1977-06-09
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Granted: 1978-10-24
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Expires: 1997-06-09
Abstract
Abstract A process for production of 5-fluorouracil and its derivatives which comprises reacting a cytosine compound of the formula: ##STR1## wherein R is a hydrogen atom or a saccharide residue with fluorine or fluorine fluorosulfonate (FOSO 2 F) in an aqueous medium to give the corresponding 5-fluorouracil compound of the formula: ##STR2## wherein R is as defined above.
Inventors
- 👤 Susumu Misaki
- 👤 Sadamu Ishii
- 👤 Nobuyuki Suzuki
- 👤 Mikio Wakabayashi
- 👤 Tsuneo Sowa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 15:48
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/46; C07D239/52; C07D239/54; C07D239/545; C07D239/553
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
66 words
A process for the production of 5-fluorouracil and derivatives thereof which comprises the step of reacting a cytosine compound of the formula: ##STR5## wherein R is a hydrogen atom or a saccharide residue with fluorine in the presence of a hydrogen sulfite or with fluorine fluorosulfonate in an aqueous medium to give the corresponding 5-fluorouracil compound of the formula: ##STR6## wherein R is as defined above.
Claim 2
Dependent Claim
66 words
A process for the production of 5-fluorouracil and derivatives thereof which comprises the step of reacting a cytosine compound of the formula: ##STR5## wherein R is a hydrogen atom or a saccharide residue with fluorine in the presence of a hydrogen sulfite or with fluorine fluorosulfonate in an aqueous medium to give the corresponding 5-fluorouracil compound of the formula: ##STR6## wherein R is as defined above.
Claim 3
Dependent Claim
12 words
The process according to claim 1, wherein R is a hydrogen atom.
Claim 4
Dependent Claim
12 words
The process according to claim 1, wherein R is a saccharide residue.
Claim 5
Dependent Claim
17 words
The process according to claim 3, wherein the saccharide residue is the residue of pentose or hexose.
Claim 6
Dependent Claim
19 words
The process according to claim 4, wherein the hydroxyl groups in the residue of pentose or hexose are protected.
Claim 7
Dependent Claim
18 words
The process according to claim 5, wherein the protective group for the hydroxyl groups is acetyl or benzoyl.
Claim 8
Dependent Claim
40 words
The process according to claim 1, wherein the aqueous medium consists of water alone or a mixture of water and at least one member selected from the group consisting of inorganic acids, organic acids, alcohols, halogenated ketones and halogenated hydrocarbons.
Claim 9
Dependent Claim
12 words
The process according to claim 7, wherein the aqueous medium is water.
Claim 10
Dependent Claim
21 words
The process according to claim 1, wherein the water in the aqueous medium is present from the beginning of the reaction.
Claim 11
Dependent Claim
21 words
The process according to claim 1, wherein the water in the aqueous medium is added during the course of the reaction.
Claim 12
Dependent Claim
25 words
The process according to claim 1, wherein the fluorine or fluorine fluorosulfonate is used for the reaction in a dilute form with an inert gas.
Claim 13
Dependent Claim
12 words
The process according to claim 11, wherein the inert gas is nitrogen.
Claim 14
Dependent Claim
18 words
The process according to claim 1, wherein the cytosine compound is used in the form of a salt.
Claim 15
Dependent Claim
30 words
The process according to claim 1, wherein the fluorine or fluorine fluorosulfonate is used in an amount of not less than 1 mol to 1 mol of the cytosine compound.
Claim 16
Dependent Claim
15 words
The process according to claim 1, wherein said cytosine compound is reacted with fluorine fluorosulfonate.
Claim 17
Dependent Claim
32 words
The process according to claim 1, wherein the reaction is followed by heating the reaction mixture at a temperature higher than that as adopted in the reaction with fluorine or fluorine fluorosulfonate.
Claim 18
Dependent Claim
17 words
The process according to claim 16, wherein the temperature of heating is from 60° to 100° C.
Claim 19
Dependent Claim
20 words
The process according to claim 17, wherein the heating is carried out for a period of 1 to 6 hours.
Claim 20
Dependent Claim
19 words
The process according to claim 16, wherein the heating is carried out at a pH of 1 to 9.
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) | 1981-10-23 | 1982-04-24 | 1982-10-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-10-23 | 1986-04-24 | 1986-10-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-10-23 | 1990-04-24 | 1990-10-24 | $7700.00 | Window Closed / Lapsed |