US4503045A
Expired / Lapsed
US
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2'-Deoxy-3',5'-di-O-alkylcarbonyl-5-fluorouridine derivatives, a process for the preparation of the derivatives and anti-tumor agents containing the derivatives
Assignee: Funai Pharmaceutical Industries Ltd
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Filing: 1981-02-13
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Granted: 1985-03-05
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Expires: 2001-02-13
Abstract
Abstract 2'-Deoxy-3',5'-di-O-alkylcarbonyl-5-fluorouridine derivatives possessing strong anti-tumor activity with weak toxicity and represented by the general formula: ##STR1## wherein R stands for an alkyl group, an alkoxy group or a halogen atom, m for zero or an integer of 1-3, and n for an integer of 1-14, with the proviso that when m is 2 or 3, R's may be the same or different and that when m is 2 and the adjacent two R's are alkoxy groups, the two alkyl moieties of the alkoxy groups may be combined to form together with the two adjacent oxa bridging members an alkylenedioxy group as a whole. These derivatives are prepared by acylating a 2'-deoxy-3',5'-di-O-alkylcarbonyl-5-fluorouridine with corresponding benzoyl halides and are useful as active ingredients for anti-tumor agents, especially for oral administration.
Inventors
- 👤 Setsuro Fujii
- 👤 Bompei Yasui
- 👤 Tomohisa Miyamoto
- 👤 Masatoshi Shiga
- 👤 Kazuko Ando
- 👤 Iwao Hashimoto
- 👤 Masahiro Kawasaki
- 👤 Yoichiro Kawai
- 👤 Yuji Mino
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 09:33
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; A; A61; A61P; A61P35/00
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
96 words
2'-Deoxy-3',5'-di-O-alkylcarbonyl-5-fluorouridine derivatives of the general formula: ##STR7## wherein R stands for an alkyl group, an alkoxy group or a halogen atom, m for zero or an integer of 1-3, and n for an integer of 1-2 or 5-14, with the proviso that when m is 2 or 3, R's may be the same or different and that when m is 2 and the adjacent two R's are alkoxy groups, the two alkyl moieties of the alkoxy groups may be combined to form together with the two adjacent oxa bridging members an alkylenedioxy group as a whole.
Claim 2
Dependent Claim
96 words
2'-Deoxy-3',5'-di-O-alkylcarbonyl-5-fluorouridine derivatives of the general formula: ##STR7## wherein R stands for an alkyl group, an alkoxy group or a halogen atom, m for zero or an integer of 1-3, and n for an integer of 1-2 or 5-14, with the proviso that when m is 2 or 3, R's may be the same or different and that when m is 2 and the adjacent two R's are alkoxy groups, the two alkyl moieties of the alkoxy groups may be combined to form together with the two adjacent oxa bridging members an alkylenedioxy group as a whole.
Claim 3
Dependent Claim
16 words
2'-Deoxy-3',5'-di-O-alkylcarbonyl-5-fluorouridine derivatives according to claim 1, wherein m in the general formula (1) stands for zero.
Claim 4
Dependent Claim
17 words
2'-Deoxy-3',5'-di-O-alkylcarbonyl-5-fluorouridine derivatives according to claim 1, wherein R in the general formula (1) stands for methyl group.
Claim 5
Dependent Claim
21 words
2'-Deoxy-3',5'-di-O-alkylcarbonyl-5-fluorouridine derivatives according to claim 1, wherein R in the general formula (1) stands for methoxy group and m is 2.
Claim 6
Dependent Claim
17 words
2'-Deoxy-3',5'-di-O-alkylcarbonyl-5-fluorouridine derivatives according to claim 1, wherein R in the general formula (1) stands for fluorine atom.
Claim 7
Dependent Claim
10 words
2'-Deoxy-3',5'-di-O-alkylcarbonyl-5-fluorouridine derivatives according to claim 1, wherein n is 2.
Claim 8
Dependent Claim
10 words
2'-Deoxy-3',5'-di-O-alkylcarbonyl-5-fluorouridine derivatives according to claim 1, wherein n is 1.
Claim 9
Dependent Claim
10 words
2'-Deoxy-3',5'-di-O-alkylcarbonyl-5-fluorouridine derivatives according to claim 1, wherein n is 5.
Claim 10
Dependent Claim
115 words
A pharmaceutical composition comprising an effective anti-tumor amount of at least one 2'-deoxy-3',5'-di-O-alkylcarbonyl-5-fluorouridine derivative of the general formula: ##STR8## wherein R stands for an alkyl group, an alkoxy group or a halogen atom, m for zero or an integer of 1-3, and n for an integer of 1-2 or 5-14, with the proviso that when m is 2 or 3, R's may be the same or different and that when m is 2 and the adjacent two R's are alkoxy groups, the two alkyl moieties of the alkoxy groups may be combined to form together with the two adjacent oxa bridging members an alkylenedioxy groups as a whole and a pharmaceutically acceptable carrier or excipient.
Claim 11
Dependent Claim
115 words
A pharmaceutical composition comprising an effective anti-tumor amount of at least one 2'-deoxy-3',5'-di-O-alkylcarbonyl-5-fluorouridine derivative of the general formula: ##STR8## wherein R stands for an alkyl group, an alkoxy group or a halogen atom, m for zero or an integer of 1-3, and n for an integer of 1-2 or 5-14, with the proviso that when m is 2 or 3, R's may be the same or different and that when m is 2 and the adjacent two R's are alkoxy groups, the two alkyl moieties of the alkoxy groups may be combined to form together with the two adjacent oxa bridging members an alkylenedioxy groups as a whole and a pharmaceutically acceptable carrier or excipient.
Claim 12
Dependent Claim
22 words
A pharmaceutical composition as in claim 9, wherein R in the general formula (I) stands for methyl group and n is 2.
Claim 13
Dependent Claim
25 words
A pharmaceutical composition as in claim 9, wherein R in the general formula (I) stands for methoxy group, m is 2 and n is 1.
Claim 14
Dependent Claim
22 words
A pharmaceutical composition as in claim 9, wherein R in the general formula (I) stands for fluorine atom and n is 5.
Claim 15
Dependent Claim
18 words
A pharmaceutical composition as in claim 9, wherein R is methyl, m is 1 and n is 2.
Claim 16
Dependent Claim
20 words
A pharmaceutical composition as in claim 9, wherein the carrier is polyethylene glycol and cane sugar esters of fatty acids.
Claim 17
Dependent Claim
18 words
A pharmaceutical composition as in claim 9, wherein R is methoxy, m is 2 and n is 14.
Claim 18
Dependent Claim
15 words
A pharmaceutical composition as in claim 9, wherein m is zero and n is 2.
Claim 19
Dependent Claim
18 words
A pharmaceutical composition as in claim 9, wherein R is methyl, m is 1 and n is 5.
Claim 20
Dependent Claim
18 words
A pharmaceutical composition as in claim 9, wherein R is methoxy, m is 2 and n is 5.
Claim 21
Dependent Claim
18 words
A pharmaceutical composition as in claim 9, wherein R is methoxy, m is 2 and n is 6.
Claim 22
Dependent Claim
18 words
A pharmaceutical composition as in claim 9, wherein R is fluorine, m is 1 and n is 6.
Claim 23
Independent Claim
111 words
A method for treating tumors comprising administering an effective anti-tumor amount of at least one 2'-deoxy-3',5'-di-O-alkylcarbonyl-5-fluorouridine derivative of the general formula: ##STR9## wherein R stands for an alkyl group, an alkoxy group or a halogen atom, m for zero or an integer of 1-3, and n for an integer of 1-2 or 5-14, with the proviso that when m is 2 or 3, R's may be the same or different and that when m is 2 and the adjacent two R's are alkoxy groups, the two alkyl moieties of the alkoxy groups may be combined to form together with the two adjacent oxa bridging members an alkylenedioxy group as a whole.
Claim 24
Independent Claim
111 words
A method for treating tumors comprising administering an effective anti-tumor amount of at least one 2'-deoxy-3',5'-di-O-alkylcarbonyl-5-fluorouridine derivative of the general formula: ##STR9## wherein R stands for an alkyl group, an alkoxy group or a halogen atom, m for zero or an integer of 1-3, and n for an integer of 1-2 or 5-14, with the proviso that when m is 2 or 3, R's may be the same or different and that when m is 2 and the adjacent two R's are alkoxy groups, the two alkyl moieties of the alkoxy groups may be combined to form together with the two adjacent oxa bridging members an alkylenedioxy group as a whole.
Claim 25
Dependent Claim
17 words
A method for treating tumors as in claim 21, wherein R is methyl and n is 2.
Claim 26
Dependent Claim
20 words
A method for treating tumors as in claim 21, wherein R is methoxy, m is 2 and n is 1.
Claim 27
Dependent Claim
17 words
A method for treating tumors as in claim 21, wherein R is fluorine and n is 5.
Claim 28
Dependent Claim
20 words
A method for treating tumors as in claim 21, wherein R is methyl, m is 1 and n is 2.
Claim 29
Dependent Claim
20 words
A method for treating tumors as in claim 21, wherein R is methoxy, m is 2 and n is 14.
Claim 30
Dependent Claim
17 words
A method for treating tumors as in claim 21, wherein m is zero and n is 2.
Claim 31
Dependent Claim
20 words
A method for treating tumors as in claim 21, wherein R is methyl, m is 1 and n is 5.
Claim 32
Dependent Claim
20 words
A method for treating tumors as in claim 21, wherein R is methoxy, m is 2 and n is 5.
Claim 33
Dependent Claim
20 words
A method for treating tumors as in claim 21, wherein R is methoxy, m is 2 and n is 6.
Claim 34
Dependent Claim
20 words
A method for treating tumors as in claim 21, wherein R is fluorine, m is 1 and n is 6.
References Cited (Backward Citations)
US3853845A
Cited
GB2025401A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-03-04 | 1988-09-03 | 1989-03-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-03-04 | 1992-09-03 | 1993-03-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-03-04 | 1996-09-03 | 1997-03-05 | $7700.00 | Window Closed / Lapsed |