US4414215A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N-Acyl derivatives of 6-alkylamino 5-chloro-3-nitropyrazinamines for radiation therapy
Assignee: Merck and Co Inc
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Filing: 1982-07-19
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Granted: 1983-11-08
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Expires: 2002-07-19
Abstract
Abstract N-Acyl derivatives of 6-(alkylamino)-5-chloro-3-nitro-pyrazinamines are disclosed to have activity in increasing the sensitivity of tumor cells to radiation. Also disclosed are methods of preparing such compounds and pharmaceutical compositions including such compounds.
Inventors
- 👤 George D. Hartman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 13:35
CPC Classifications
C; C07; C07D; C07D241/00; C07D241/02; C07D241/10; C07D241/14; C07D241/20
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
155 words
A pharmaceutical composition useful in enhancing the therapeutic effect of radiation treatment comprising an effective amount of a radiation enhancing compound of the formula: ##STR14## wherein R and R 1 are each hydrogen, C 1 -C 6 lower-alkyl and substituted lower alkyl having one or two amino C 1-6 loweralkylamino or dialkylamino, lower alkoxy, hydroxy or halo C 1 -C 6 lower alkenyl, and substituted lower alkenyl having one or two amino, C 1 -C 6 alkylamino or dialkylamino, lower alkoxy, or hydroxy groups or when taken together and linked through an additional nitrogen or oxygen constitute a 5-7 member saturated heterocyclic ring comprising a morpholine, a piperazine or an N-substituted piperazine wherein the N-substituent is either hydrogen, C 1 -C 6 alkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkoxyalkyl; and R 2 is a lower alkyl substituent; and a pharmaceutical carrier.
Claim 2
Dependent Claim
155 words
A pharmaceutical composition useful in enhancing the therapeutic effect of radiation treatment comprising an effective amount of a radiation enhancing compound of the formula: ##STR14## wherein R and R 1 are each hydrogen, C 1 -C 6 lower-alkyl and substituted lower alkyl having one or two amino C 1-6 loweralkylamino or dialkylamino, lower alkoxy, hydroxy or halo C 1 -C 6 lower alkenyl, and substituted lower alkenyl having one or two amino, C 1 -C 6 alkylamino or dialkylamino, lower alkoxy, or hydroxy groups or when taken together and linked through an additional nitrogen or oxygen constitute a 5-7 member saturated heterocyclic ring comprising a morpholine, a piperazine or an N-substituted piperazine wherein the N-substituent is either hydrogen, C 1 -C 6 alkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkoxyalkyl; and R 2 is a lower alkyl substituent; and a pharmaceutical carrier.
Claim 3
Dependent Claim
13 words
A composition according to claim 1 wherein the radiation enhancing compound is N-[5-chloro-6-(2-hydroxyethyl)amino-3-nitropyrazinyl]acetamide.
Claim 4
Dependent Claim
13 words
A composition according to claim 1 wherein the radiation enhancing compound is N-[5-chloro-6(bis-2-hydroxyethyl)amino-3-nitropyrazinyl]acetamide.
Claim 5
Dependent Claim
13 words
A composition according to claim 1 wherein the radiation enhancing compound is N-[5-chloro-6(2,3-dihydroxypropyl)amino-3-nitropyrazinyl]acetamide.
Claim 6
Dependent Claim
13 words
A composition according to claim 1 wherein the radiation enhancing compound is N-[5-chloro-6(2,3-dihydroxypropyl)amino-3-nitropyrazinyl]propionamide.
Claim 7
Dependent Claim
13 words
A composition according to claim 1 wherein the radiation enhancing compound is N-[5-chloro-6(2,3-dihydroxypropyl)amino-3-nitropyrazinyl]butyramide.
Claim 8
Dependent Claim
13 words
A composition according to claim 1 wherein the radiation enhancing compound is N-[5-chloro-6-(4-methyl-1-piperazinyl)-3-nitropyrazinyl]acetamide.
Claim 9
Dependent Claim
13 words
A composition according to claim 1 wherein the radiation enhancing compound is N-[5-chloro-6-(dimethylaminoethyl)-3-nitropyrazinyl]acetamide.
Claim 10
Dependent Claim
28 words
A chloronitropyrazine compound of the formula: ##STR15## wherein R is hydroxyloweralkyl, dihydroxyloweralkyl, or haloloweralkyl, and R 1 is hydrogen or R; R 2 is a lower alkyl radical.
Claim 11
Dependent Claim
28 words
A chloronitropyrazine compound of the formula: ##STR15## wherein R is hydroxyloweralkyl, dihydroxyloweralkyl, or haloloweralkyl, and R 1 is hydrogen or R; R 2 is a lower alkyl radical.
Claim 12
Dependent Claim
10 words
A chloronitropyrazine compound according to claim 9 which is N-[5-chloro-6(2,3-dihydroxypropyl)amino-3-nitropyrazinyl]acetamide.
Claim 13
Dependent Claim
10 words
A chloronitropyrazine compound according to claim 9 which is N-[5-chloro-6(2,3-dihydroxypropyl)amino-3-nitropyrazinyl]butyramide.
Claim 14
Dependent Claim
46 words
A method of enhancing the therapeutic effect of radiation treatment which comprises administering to a patient in need of such radiation treatment an effective sensitizing amount of a compound of the formula: ##STR16## wherein R, R 1 and R 2 are defined as in claim 1.
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) | 1986-11-07 | 1987-05-09 | 1987-11-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-11-07 | 1991-05-09 | 1991-11-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-11-07 | 1995-05-09 | 1995-11-08 | $7700.00 | Window Closed / Lapsed |