US4241060A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Nitroimidazoles and compositions thereof
Assignee: Hoffmann La Roche Inc
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Filing: 1978-08-03
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Granted: 1980-12-23
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Expires: 1998-08-03
Abstract
Abstract Nitroimidazoles of the formula ##STR1## wherein R 1 and R 2 are as hereinafter set forth, are described. The nitroimidazoles are useful as hypoxic-cell radiosensitizers, as well as being useful as antiprotozoal agents.
Inventors
- 👤 Carey E. Smithen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 13:53
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/66; C07D233/91; A; A61; A61P; A61P31/00; A61P31/04; A61P33/00; A61P33/02; A61P43/00
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
112 words
A compound of the formula ##STR11## wherein R 1 is hydrogen, lower alkyl, hydroxy-(lower alkyl), lower cycloalkyl, aryl or lower aralkyl and R 2 is lower alkyl, hydroxy-(lower alkyl), lower cycloalkyl, aryl or lower aralkyl or a grouping of the formula ##STR12## wherein m is zero and n is 1 or m is 1 and n is zero and R 3 is hydrogen, methyl or hydroxy, or R 1 and R 2 taken together with the nitrogen atom to which they are attached are a 5-membered, 6-membered or 7-membered saturated heteromonocyclic ring selected from pyrrolidino, piperidino, 3-hydroxypyrrolidino, 4-hydroxy-piperidino, 3-hydroxy-hexahydro-1H-azepino, piperazino, N-methylpiperazino, N-(2-hydroxyethyl)piperazino, morpholino, hexahydro-1H-azepino, and thiamorpholino, or an acid addition salt thereof.
Claim 2
Dependent Claim
112 words
A compound of the formula ##STR11## wherein R 1 is hydrogen, lower alkyl, hydroxy-(lower alkyl), lower cycloalkyl, aryl or lower aralkyl and R 2 is lower alkyl, hydroxy-(lower alkyl), lower cycloalkyl, aryl or lower aralkyl or a grouping of the formula ##STR12## wherein m is zero and n is 1 or m is 1 and n is zero and R 3 is hydrogen, methyl or hydroxy, or R 1 and R 2 taken together with the nitrogen atom to which they are attached are a 5-membered, 6-membered or 7-membered saturated heteromonocyclic ring selected from pyrrolidino, piperidino, 3-hydroxypyrrolidino, 4-hydroxy-piperidino, 3-hydroxy-hexahydro-1H-azepino, piperazino, N-methylpiperazino, N-(2-hydroxyethyl)piperazino, morpholino, hexahydro-1H-azepino, and thiamorpholino, or an acid addition salt thereof.
Claim 3
Dependent Claim
75 words
A compound in accordance with claim 1, wherein R 1 is hydrogen, lower alkyl, hydroxy-(lower alkyl), aryl or lower aralkyl and R 2 is lower alkyl, hydroxy-(lower alkyl), aryl or lower aralkyl or R 1 and R 2 taken together with the nitrogen atom to which they are attached are a 5-membered, 6-membered or 7-membered saturated heteromonocyclic ring selected from pyrrolidino, piperidino, piperazino, N-methylpiperazino, N-(2-hydroxyethyl)piperazino, morpholino, hexahydro-1H-azepino and thiamorpholino, or an acid addition salt thereof.
Claim 4
Dependent Claim
43 words
A compound in accordance with claim 1, wherein R 1 and R 2 taken together with the nitrogen atom to which they are attached are a 6-membered heteromonocyclic ring selected from piperidino, piperazino, N-methylpiperazino, morpholino and thiamorpholino, or an acid addition salt thereof.
Claim 5
Dependent Claim
8 words
A compound in accordance with claim 1, 2-nitro-α-(piperidino)methyl-1-imidazole-ethanol.
Claim 6
Dependent Claim
8 words
A compound in accordance with claim 1, α-(morpholino)methyl-2-nitro-1-imidazole-ethanol.
Claim 7
Dependent Claim
8 words
A compound in accordance with claim 1, α-(4-methylpiperazino)methyl-2-nitro-1-imidazole-ethanol.
Claim 8
Dependent Claim
8 words
A compound in accordance with claim 1, 2-nitro-α-(pyrrolidino)methyl-1-imidazole-ethanol.
Claim 9
Dependent Claim
8 words
A compound in accordance with claim 1, α-(diethylamino)methyl-2-nitro-1-imidazole-ethanol.
Claim 10
Dependent Claim
8 words
A compound in accordance with claim 1, α-[di-(2-hydroxyethyl)amino]-methyl-2-nitro-1-imidazole-ethanol.
Claim 11
Dependent Claim
8 words
A compound in accordance with claim 1, α-(tert.-butylamino)methyl-2-nitro-1-imidazole-ethanol.
Claim 12
Dependent Claim
8 words
A compound in accordance with claim 1, α-(benzylamino)methyl-2-nitro-1-imidazole-ethanol.
Claim 13
Dependent Claim
8 words
A compound in accordance with claim 1, α-[(4-methoxyphenyl)amino]methyl-2-nitro-1-imidazole-ethanol.
Claim 14
Dependent Claim
8 words
A compound in accordance with claim 1, α-(dimethylamino)methyl-2-nitro-1-imidazole-ethanol.
Claim 15
Dependent Claim
8 words
A compound in accordance with claim 1, α-(hexahydro-1H-azepino)methyl-2-nitro-1-imidazole-ethanol.
Claim 16
Dependent Claim
8 words
A compound in accordance with claim 1, 4-[2-hydroxy-3-(2-nitro-1-imidazolyl)propylamino]-2,2,6,6-tetramethylpiperidin-N-oxy.
Claim 17
Dependent Claim
8 words
A compound in accordance with claim 1, α-[(2,2,6,6-tetramethyl-4-piperidinyl)amino]methyl-2-nitro-1-imidazole-ethanol.
Claim 18
Dependent Claim
8 words
A compound in accordance with claim 1, α-(cyclohexylamino)methyl-2-nitro-1-imidazole-ethanol.
Claim 19
Dependent Claim
8 words
A compound in accordance with claim 1, α-(dicyclohexylamino)methyl-2-nitro-1-imidazole-ethanol.
Claim 20
Dependent Claim
8 words
A compound in accordance with claim 1, 1-[2-hydroxy-3-(2-nitro-1-imidazolyl)propyl]-3-pyrrolidinol.
Claim 21
Dependent Claim
142 words
A hypoxic cell radiosensitizing or antiprotozoal pharmaceutical preparation containing a hypoxic cell radiosensitizing amount or an antiprotozoal amount of a compound of the formula ##STR13## wherein R 1 is hydrogen, lower alkyl, hydroxy-(lower alkyl), lower cycloalkyl, aryl or lower aralkyl and R 2 is lower alkyl, hydroxy-(lower alkyl), lower cycloalkyl, aryl or lower aralkyl or a grouping of the formula ##STR14## wherein m is zero and n is 1 or m is 1 and n is zero, and R 3 is hydrogen, methyl or hydroxy, or R 1 and R 2 when taken together with the nitrogen atom to which they are attached are a 5-membered, 6-membered or 7-membered saturated heteromonocyclic ring selected from pyrrolidino, piperidino, 3-hydroxypyrrolidino, 4-hydroxypiperidino, 3-hydroxy-1H-azepino, piperazino, N-methylpiperazino, N-(2-hydroxyethyl)piperazino, morpholino, hexahydro-1H-azepino, and thiamorpholino, or a pharmaceutically acceptable acid addition salt thereof, in association with a compatible pharmaceutical carrier material.
Claim 22
Dependent Claim
142 words
A hypoxic cell radiosensitizing or antiprotozoal pharmaceutical preparation containing a hypoxic cell radiosensitizing amount or an antiprotozoal amount of a compound of the formula ##STR13## wherein R 1 is hydrogen, lower alkyl, hydroxy-(lower alkyl), lower cycloalkyl, aryl or lower aralkyl and R 2 is lower alkyl, hydroxy-(lower alkyl), lower cycloalkyl, aryl or lower aralkyl or a grouping of the formula ##STR14## wherein m is zero and n is 1 or m is 1 and n is zero, and R 3 is hydrogen, methyl or hydroxy, or R 1 and R 2 when taken together with the nitrogen atom to which they are attached are a 5-membered, 6-membered or 7-membered saturated heteromonocyclic ring selected from pyrrolidino, piperidino, 3-hydroxypyrrolidino, 4-hydroxypiperidino, 3-hydroxy-1H-azepino, piperazino, N-methylpiperazino, N-(2-hydroxyethyl)piperazino, morpholino, hexahydro-1H-azepino, and thiamorpholino, or a pharmaceutically acceptable acid addition salt thereof, in association with a compatible pharmaceutical carrier material.
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) | 1983-12-23 | 1984-06-23 | 1984-12-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-12-23 | 1988-06-23 | 1988-12-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-12-23 | 1992-06-23 | 1992-12-23 | $7700.00 | Window Closed / Lapsed |