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US4472386A
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US
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5-Fluoro-(β-uridine or 2'-deoxy-β-uridine) derivatives, a process for producing the same and a carcinostatic agent containing the same
Assignee: Toyama Chemical Co Ltd
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Filing: 1979-06-06
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Granted: 1984-09-18
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Expires: 1999-06-06
Abstract
Abstract 5-Fluoro-( beta -uridine or 2'-deoxy- beta -uridine) derivatives having an acyl group at the 3-position of the molecule. These compounds are useful as carcinostatic agent. This disclosure relates to such compounds, a process for producing the same and a carcinostatic agent comprising such a compound.
Inventors
- 👤 Tsutomu Kodama
- 👤 Masaakira Senoura
- 👤 Hajime Aoyama
- 👤 Tomonobu Yamaguchi
- 👤 Isao Kitayama
- 👤 Minako Yotsuji
- 👤 Toru Hiraiwa
- 👤 Masaharu Omori
- 👤 Nobuo Terashima
- 👤 Yutaka Kodama
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 07:08
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; A; A61; A61P; A61P35/00
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
143 words
A 5-fluoro(2'-deoxy-β-uridine)derivative of the formula ##STR99## wherein R 1 is aroyl, C 1-18 alkanoyl, heterocyclic carbonyl the heterocyclic ring of which contains 1-4 hetero atoms or C 3-5 alkenoyl, said R 1 substituents optionally being substituted with at least one substituent selected from the group consisting of halogen, hydroxyl, nitro, cyano, amino, carboxyl, C 1-12 acyl, C 1-12 acyloxy, C 1-5 alkylamino, di-C 1-5 alkylamino, C 1-12 acylamino, C 1-5 alkyl, C 1-10 alkoxy, C 1-5 alkoxycarbonyl, aryl, heterocyclic group wherein the heterocyclic ring contains from one to four hetero atoms and halogen substituted derivatives of said C 1-12 acyl, C 1-12 acyloxy, C 1-5 alkylamino, di-C 1-5 alkylamino, C 1-12 acylamino, C 1-5 alkyl, C 1-10 alkoxy, C 1-5 alkoxycarbonyl, aryl and heterocyclic groups; and R 2 and R 3 , which may be identical or different represent protected or unprotected hydroxyl.
Claim 2
Dependent Claim
143 words
A 5-fluoro(2'-deoxy-β-uridine)derivative of the formula ##STR99## wherein R 1 is aroyl, C 1-18 alkanoyl, heterocyclic carbonyl the heterocyclic ring of which contains 1-4 hetero atoms or C 3-5 alkenoyl, said R 1 substituents optionally being substituted with at least one substituent selected from the group consisting of halogen, hydroxyl, nitro, cyano, amino, carboxyl, C 1-12 acyl, C 1-12 acyloxy, C 1-5 alkylamino, di-C 1-5 alkylamino, C 1-12 acylamino, C 1-5 alkyl, C 1-10 alkoxy, C 1-5 alkoxycarbonyl, aryl, heterocyclic group wherein the heterocyclic ring contains from one to four hetero atoms and halogen substituted derivatives of said C 1-12 acyl, C 1-12 acyloxy, C 1-5 alkylamino, di-C 1-5 alkylamino, C 1-12 acylamino, C 1-5 alkyl, C 1-10 alkoxy, C 1-5 alkoxycarbonyl, aryl and heterocyclic groups; and R 2 and R 3 , which may be identical or different represent protected or unprotected hydroxyl.
Claim 3
Dependent Claim
13 words
The 5-fluoro-(2'-deoxy-β-uridine)derivative of claim 1, wherein said aroyl substituent is benzoyl or 3,4-methylenedioxybenzoyl.
Claim 4
Dependent Claim
17 words
The 5-fluoro-(2'-deoxy-β-uridine)derivative of claim 1, wherein said heterocyclic carbonyl is furoyl, theonyl, thiazolylcarbonyl, oxazolylcarbonyl, isoxazolylcarbonyl or nicotinoyl.
Claim 5
Dependent Claim
50 words
The 5-fluoro-(2'-deoxy-β-uridine)derivative of claim 1, wherein said protecting group for said hydroxyl substituent at R 2 and R 3 is a member selected from the group consisting of C 1-10 alkanoyl, C 1-10 alkoxycarbonyl, C 1-12 acyloxy-C 1-12 acyl, p-chlorobenzoyl, p-methylbenzoyl, p-nitrobenzoyl, m,p-dinitrobenzoyl and mono-, di- or trihalogeno-C 1-10 alkanoyl.
Claim 6
Dependent Claim
31 words
The 5-fluoro-(β-uridine or 2'-deoxy-β-uridine)derivative according to claim 2, wherein R 1 is benzoyl substituted by fluorine, chlorine, bromine or iodine or fluorine, chlorine, bromine or iodine substituted acetylamino, or 3, 4-methylenedioxybenzoyl.
Claim 7
Dependent Claim
19 words
The 5-fluoro-(2'-deoxy-β-uridine) derivative according to claim 5, wherein R 1 is benzoyl substituted by fluorine or chloroacetylamino, or 3,4-methylenedioxybenzoyl.
Claim 8
Dependent Claim
20 words
The 5-fluoro-2'-deoxy-β-uridine derivative of claim 1, 2, 3 5 or 6, wherein R 2 and R 3 are both hydroxyl.
Claim 9
Dependent Claim
1 words
3-(3,4-Methylenedioxybenzoyl)-5-fluoro-2'-deoxy-β-uridine.
Claim 10
Dependent Claim
1 words
3-(3,4-Methylenedioxybenzoyl)-5-fluoro-2'-deoxy-β-uridine.
Claim 11
Dependent Claim
1 words
3-(3,4-Methylenedioxybenzoyl)-3',5'-di-O-acetyl-5-fluoro-2'-deoxy-β-uridine.
Claim 12
Dependent Claim
1 words
3-(3,4-Methylenedioxybenzoyl)-3',5'-di-O-acetyl-5-fluoro-2'-deoxy-β-uridine.
Claim 13
Dependent Claim
1 words
3-p-Monochloroacetylaminobenzoyl-5-fluoro-2'-deoxy-β-uridine.
Claim 14
Dependent Claim
1 words
3-p-Monochloroacetylaminobenzoyl-5-fluoro-2'-deoxy-β-uridine.
Claim 15
Dependent Claim
1 words
3-p-Fluorobenzoyl-5-fluoro-2'-deoxy-β-uridine.
Claim 16
Dependent Claim
1 words
3-p-Fluorobenzoyl-5-fluoro-2'-deoxy-β-uridine.
Claim 17
Dependent Claim
33 words
A pharmaceutical composition having carcinostatic activity on tumors transplanted into animals, which comprises: a carcinostatically effective amount of the compound in claim 1, in combination with a pharmaceutically acceptable inert excipient or diluent.
References Cited (Backward Citations)
US3309359A
Cited
US3975367A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-09-18 | 1988-03-19 | 1988-09-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-09-18 | 1992-03-19 | 1992-09-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-09-18 | 1996-03-19 | 1996-09-18 | $7700.00 | Window Closed / Lapsed |