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US5032680A
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2'-deoxy-5-fluorouridine derivatives
Assignee: Taiho Pharmaceutical Co Ltd
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Filing: 1989-02-24
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Granted: 1991-07-16
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Expires: 2009-02-24
Abstract
Abstract 2 min -Deoxy-5-fluorouridine derivatives of the formula <CHEM> wherein, R<1> is hydrogen atom or an acyl group and R<2> and R<3> are respectively hydrogen atom, an acyl group or a group of the formula <CHEM> wherein X<1> and X<2> are respectively oxygen atom or sulfur atom; R<4> is a phenyl group, a benzyl group or a naphthyl group each of which may be substituted by an alkyl group, an alkoxyl group, an alkoxycarbonyl group, an alkylthio group, an acyl group, a halogen atom, trifluoromethyl group, nitro group, cyano group, carboxyl group and/or methylenedioxy group and R<5> is an alkyl group, an alkenyl group or one of the groups represented by R<4> which is the same as or different from R<4>, at least one of R<2> and R<3> being a group of the formula <CHEM> which exhibit excellent antitumour activities and have lower toxicity, methods of the production thereof and antitumour compositions containing said 2 min -deoxy-5-fluorouridine derivatives.
Inventors
- 👤 Tsutomu Kawai
- 👤 Fumio Mori
- 👤 Setsuo Takeda
- 👤 Hitoshi Saito
- 👤 Norio Unemi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 08:58
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; C07H19/067; C07H19/10
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
145 words
A 2'-deoxy-5-fluorouridine derivative of the formula ##STR36## wherein, R 1 is hydrogen atom or an acyl group and R 2 and R 3 are respectively hydrogen atom, an acyl group or a group of the formula ##STR37## wherein X 1 and X 2 are respectively oxygen atom or sulfur atom; R 4 is a phenyl group, a benzyl group or a naphthyl group each of which may be substituted by an alkyl group, an alkoxyl group, an alkoxycarbonyl group, an alkylthio group, an acyl group, a halogen atom, trifluoromethyl group, nitro group, cyano group, carboxyl group and/or methylenedioxy group and R 5 is an alkyl group, an alkenyl group or one of the groups represented by R 4 which is the same as or different from R 4 , at least one of R 2 and R 3 being a group of the formula ##STR38##
Claim 2
Dependent Claim
145 words
A 2'-deoxy-5-fluorouridine derivative of the formula ##STR36## wherein, R 1 is hydrogen atom or an acyl group and R 2 and R 3 are respectively hydrogen atom, an acyl group or a group of the formula ##STR37## wherein X 1 and X 2 are respectively oxygen atom or sulfur atom; R 4 is a phenyl group, a benzyl group or a naphthyl group each of which may be substituted by an alkyl group, an alkoxyl group, an alkoxycarbonyl group, an alkylthio group, an acyl group, a halogen atom, trifluoromethyl group, nitro group, cyano group, carboxyl group and/or methylenedioxy group and R 5 is an alkyl group, an alkenyl group or one of the groups represented by R 4 which is the same as or different from R 4 , at least one of R 2 and R 3 being a group of the formula ##STR38##
Claim 3
Dependent Claim
27 words
The 2'-deoxy-5-fluorouridine derivative as claimed in claim 1 wherein R 2 is a group of the formula ##STR39## wherein the symbols are as defined in claim 1.
Claim 4
Dependent Claim
22 words
The 2'-deoxy-5-fluorouridine derivative as claimed in claim 1 wherein R 1 and R 3 are respectively hydrogen atom or an acyl group.
Claim 5
Dependent Claim
54 words
The 2'-deoxy-5-fluorouridine derivative as claimed in claim 1 wherein R 2 is a group of the formula ##STR40## wherein each of X 1 and X 2 is oxygen atom and R 4 and R 5 are respectively a phenyl group substituted by one or two chlorine atom, fluorine atom, bromine atom and/or trifluoromethyl group.
Claim 6
Dependent Claim
69 words
The 2'-deoxy-5-fluorouridine derivative as claimed in claim 1, wherein R 1 is a hydrogen atom; R 2 is a group of the formula ##STR41## wherein each of X 1 and X 2 is oxygen atom and R 4 and R 5 are respectively a phenyl group substituted by one or two chlorine atom, fluorine atom, bromine atom and/or trifluoromethyl group; R 3 is hydrogen atom or an acyl group.
Claim 7
Dependent Claim
29 words
The 2'-deoxy-5-fluorouridine derivative as claimed in claim 1 selected from the group consisting of di-p-chlorophenyl 2'-deoxy-5-fluoro-5'-uridylate, di-m-chlorophenyl 2'-deoxy-5-fluoro-5'-uridylate, di(2,4-dichlorophenyl) 2'-deoxy-5-fluoro-5'-uridylate, di-p-fluorophenyl 2'-deoxy-5-fluoro-5'-uridylate, di-p-bromophenyl 2'-deoxy-5-fluoro-5'-uridylate, de-p-trifluoromethylphenyl 2'-deoxy-5-fluoro-5'-uridylate and di-p-chlorophenyl 3'-acetyl-2'-deoxy-5-fluoro-5'-uridylate.
Claim 8
Dependent Claim
29 words
A composition comprising an amount of a 2'-deoxy-5-fluorouridine derivative, as claimed in claim 1, effective to treat Sarcoma 180 tumor cells transplanted to mice, and a pharmaceutically acceptable carrier.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1994-07-15 | 1995-01-14 | 1995-07-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-07-15 | 1999-01-14 | 1999-07-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-07-15 | 2003-01-14 | 2003-07-16 | $7700.00 | Window Closed / Lapsed |