US4282232A
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Nitroimidazole radiosensitizers for hypoxic tumor cells and compositions thereof
Assignee: Research Corp
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Filing: 1979-04-26
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Granted: 1981-08-04
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Expires: 1999-04-26
Abstract
Abstract Biologically active hypoxic cell radiosensitizers of the formula <IMAGE> wherein Z is a C2-C4 alkylene group which may be substituted by OH; wherein R1 and R2 are same or different substituted or unsubstituted C1-C4 alkyl groups, or R1 and R2 taken together with the nitrogen atom form a heterocyclic ring of the formula <IMAGE> wherein n=0 or 1, with the condition that when n=0, m=2 or 3 and when n=1, m=1 or 2; X and Y are hydrogen, an electron withdrawing group or X and Y taken together form a six-membered carboxylic aromatic ring.
Inventors
- 👤 Krishna C. Agrawal
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 03:19
CPC Classifications
C; C07; C07D; C07D235/00; C07D235/02; C07D235/04; C07D235/24; C07D233/00; C07D233/54; C07D233/66; C07D233/91
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
100 words
Biologically active hypoxic cell radiosensitizers of the formula ##STR17## wherein Z is a C 2 -C 4 alkylene group; wherein R 1 and R 2 taken together with the nitrogen atom form a heterocyclic ring of the formula ##STR18## wherein m=1 or 2; X and Y are the same or different substituents selected from the group consisting of hydrogen, nitro; R 3 CO-- where R 3 is C 1 -C 4 alkyl; nitrile, carboxyamide; R 5 OCO-- where R 5 is C 1 -C 4 alkyl; R 6 --N(O)═CH-- where R 6 is C 1 -C 4 alkyl; and nitrilomethyl.
Claim 2
Dependent Claim
100 words
Biologically active hypoxic cell radiosensitizers of the formula ##STR17## wherein Z is a C 2 -C 4 alkylene group; wherein R 1 and R 2 taken together with the nitrogen atom form a heterocyclic ring of the formula ##STR18## wherein m=1 or 2; X and Y are the same or different substituents selected from the group consisting of hydrogen, nitro; R 3 CO-- where R 3 is C 1 -C 4 alkyl; nitrile, carboxyamide; R 5 OCO-- where R 5 is C 1 -C 4 alkyl; R 6 --N(O)═CH-- where R 6 is C 1 -C 4 alkyl; and nitrilomethyl.
Claim 3
Dependent Claim
11 words
The compounds of claim 1 wherein Z=--CH 2 --CH 2 --.
Claim 4
Dependent Claim
19 words
The compounds of claim 1 wherein R 1 and R 2 form a heterocyclic ring of the formula ##STR19##
Claim 5
Dependent Claim
8 words
The compound of claim 1 which is 1-(1'-oxido)piperidinoethyl-2-nitroimidazole.
Claim 6
Dependent Claim
12 words
The compounds of claim 1 wherein either X or Y is nitro.
Claim 7
Dependent Claim
8 words
The compound of claim 1 which is 1-(1'-oxido)piperidinoethyl-2,4-dinitroimidazole.
Claim 8
Dependent Claim
8 words
The compound of claim 1 which is 1-(1'-oxido)piperidinoethyl-2,5-dinitroimidazole.
Claim 9
Dependent Claim
120 words
A composition useful for the radiosensitization of hypoxic tumor cells which comprises a pharmaceutically active amount of a compound having the formula: ##STR20## wherein Z is a C 2 -C 4 alkylene group; wherein R 1 and R 2 taken together with the nitrogen atom form a heterocyclic ring of the formula ##STR21## wherein m=1 or 2; X and Y are the same or different substituents selected from the group consisting of hydrogen, nitro; R 3 CO-- where R 3 is C 1 -C 4 alkyl; nitrile; carboxyamide; R 5 OCO-- where R 5 is C 1 -C 4 alkyl; R 6 --N(O)═CH-- wherein R 6 is C 1 -C 4 alkyl; and nitrilomethyl; and an inert pharmaceutically acceptable carrier.
Claim 10
Dependent Claim
120 words
A composition useful for the radiosensitization of hypoxic tumor cells which comprises a pharmaceutically active amount of a compound having the formula: ##STR20## wherein Z is a C 2 -C 4 alkylene group; wherein R 1 and R 2 taken together with the nitrogen atom form a heterocyclic ring of the formula ##STR21## wherein m=1 or 2; X and Y are the same or different substituents selected from the group consisting of hydrogen, nitro; R 3 CO-- where R 3 is C 1 -C 4 alkyl; nitrile; carboxyamide; R 5 OCO-- where R 5 is C 1 -C 4 alkyl; R 6 --N(O)═CH-- wherein R 6 is C 1 -C 4 alkyl; and nitrilomethyl; and an inert pharmaceutically acceptable carrier.
Claim 11
Dependent Claim
11 words
The composition of claim 8 wherein Z=--CH 2 CH 2 .
Claim 12
Dependent Claim
11 words
The composition of claim 8 wherein X or Y is nitro.
Claim 13
Dependent Claim
21 words
The composition of claim 8 wherein R 1 and R 2 taken together form a heterocyclic ring of the formula: ##STR22##
References Cited (Backward Citations)
US3646057A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-08-03 | 1985-02-02 | 1985-08-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-08-03 | 1989-02-02 | 1989-08-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-08-03 | 1993-02-02 | 1993-08-04 | $7700.00 | Window Closed / Lapsed |