US4038410A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Nitroimidazole derivatives and process for the preparation thereof
Assignee: Bayer Pharma AG
•
Filing: 1975-03-12
•
Granted: 1977-07-26
•
Expires: 1995-03-12
Abstract
Abstract Nitroimidazoles of the formula ##STR1## wherein R is dialkylaminoacryloyl; 3-, 4-, or 5-pyrazolyl or a mixture thereof which is unsubstituted or substituted by alkyl or, at the 1-position, by hydroxyalkyl or a nitro ester thereof, acyloxyalkyl, nitro, phenyl or phenyl p-substituted by halo, alkoxy or nitro, or, in the 3- or 5-position or a mixture thereof by nitro; 3- or 5-alkyl-4-isooxazolyl or a mixture thereof; or 4-alkyl-5-pyrimidinyl, unsubstituted or substituted by alkyl, amino, 2-furyl or 5-nitro-2-furyl, and the physiologically acceptable acid addition salts thereof, possess anti-protozoal activity, e.g., against trichomonas vaginalis and Entamoeba histolytica.
Inventors
- 👤 Clemens Rufer
- 👤 Katica Schwarz
- 👤 Hans-Joachim Kessler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 21:40
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/66; C07D233/91; C07D233/92; C07D233/94; C07D233/95
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
132 words
A member of the group consisting of 1. a 5-nitroimidazole of the formula ##STR10## wherein X is alkyl of 1-4 carbon atoms and R is a. 3-dialkylamino-acryloyl of 1-4 carbon atoms in each alkyl group; b. 3-, 4-, or 5-pyrazolyl which is unsubstituted or which is (i) mono- or di- substituted by alkyl of 1-4 carbon atoms on 1-2 ring carbon atoms, (ii) substituted at the 1-position by alkyl of 1-4 carbon atoms, hydroxyalkyl of 2-5 carbon atoms or a nitric acid ester thereof or a hydrocarbon-carboxylic acid ester thereof of a total of 4-9 carbon atoms, nitro, phenyl or phenyl substituted by a p-halogen atom, p-alkoxy of 1-4 carbon atoms, or p- or m-nitro, or (iii) substituted both on 1-2 ring carbon atoms and at the 1-position as defined hereinabove; 2.
Claim 2
Dependent Claim
132 words
A member of the group consisting of 1. a 5-nitroimidazole of the formula ##STR10## wherein X is alkyl of 1-4 carbon atoms and R is a. 3-dialkylamino-acryloyl of 1-4 carbon atoms in each alkyl group; b. 3-, 4-, or 5-pyrazolyl which is unsubstituted or which is (i) mono- or di- substituted by alkyl of 1-4 carbon atoms on 1-2 ring carbon atoms, (ii) substituted at the 1-position by alkyl of 1-4 carbon atoms, hydroxyalkyl of 2-5 carbon atoms or a nitric acid ester thereof or a hydrocarbon-carboxylic acid ester thereof of a total of 4-9 carbon atoms, nitro, phenyl or phenyl substituted by a p-halogen atom, p-alkoxy of 1-4 carbon atoms, or p- or m-nitro, or (iii) substituted both on 1-2 ring carbon atoms and at the 1-position as defined hereinabove; 2.
Claim 3
Dependent Claim
29 words
a position isomer mixture of pyrazolyl-substituted 5-nitroimidazoles as defined in (1) (b) whose respective pyrazolyl rings are attached at different ring carbon atoms thereof to the 5-nitroimidazole ring; and
Claim 4
Dependent Claim
29 words
a position isomer mixture of pyrazolyl-substituted 5-nitroimidazoles as defined in (1) (b) whose respective pyrazolyl rings are attached at different ring carbon atoms thereof to the 5-nitroimidazole ring; and
Claim 5
Dependent Claim
17 words
physiologically acceptable acid addition salts of each of the above. 2. 3-Dimethylamino-1-(1-methyl-5-nitro-2-imidazolyl)-2-propenone, a compound of claim 1.
Claim 6
Dependent Claim
6 words
3-(1-Methyl-5-nitro-2-imidazolyl)-pyrazole, a compound of claim 1.
Claim 7
Dependent Claim
6 words
1-Methyl-3-(1-methyl-5-nitro-2-imidazolyl)-pyrazole, a compound of claim 1.
Claim 8
Dependent Claim
6 words
1-Methyl-5-(1-methyl-5-nitro-2-imidazolyl)-pyrazole, a compound of claim 1.
Claim 9
Dependent Claim
6 words
5-(1-Methyl-5-nitro-2-imidazolyl)-1-phenyl-pyrazole, a compound of claim 1.
Claim 10
Dependent Claim
6 words
3(5)-Methyl-4-(1-methyl-5-nitro-2-imidazolyl)-pyrazole, a compound of claim 1.
Claim 11
Dependent Claim
6 words
3-Methyl-4-(1-methyl-5-nitro-2-imidazolyl)-1-nitropyrazole, a compound of claim 1.
Claim 12
Dependent Claim
6 words
3-Methyl-4-(1-methyl-5-nitro-2-imidazolyl)-5-nitropyrazole, a compound of claim 1.
Claim 13
Dependent Claim
6 words
1,3-Dimethyl-4-(1-methyl-5-nitro-2-imidazolyl)-pyrazole, a compound of claim 1.
Claim 14
Dependent Claim
6 words
1,5-Dimethyl-4-(1-methyl-5-nitro-2-imidazolyl)-pyrazole, a compound of claim 1.
Claim 15
Dependent Claim
6 words
2-[5-Methyl-4-(1-methyl-5-nitro-2-imidazolyl)-pyrazolyl]-ethanol, a compound of claim 1.
Claim 16
Dependent Claim
6 words
1-(2-Acetoxyethyl)-5-methyl-4-(1-methyl-5-nitro-2-imidazolyl)-pyrazole, a compound of claim 1.
Claim 17
Dependent Claim
8 words
2-[5-Methyl-4-(1-methyl-5-nitro-2-imidazolyl)-pyrazolyl]-ethanol-nitric acid ester, a compound of claim 1.
Claim 18
Dependent Claim
6 words
5-Methyl-4-(1-methyl-5-nitro-2-imidazolyl)-1-phenylpyrazole, a compound of claim 1.
Claim 19
Dependent Claim
6 words
1-(4-Chlorophenyl)-5-methyl-4-(1-methyl-5-nitro-2-imidazolyl)-pyrazole, a compound of claim 1.
Claim 20
Dependent Claim
6 words
1-p-Anisyl-5-methyl-4-(1-methyl-5-nitro-2-imidazolyl)-pyrazole, a compound of claim 1.
Claim 21
Dependent Claim
6 words
5-Methyl-4-(1-methyl-5-nitro-2-imidazolyl)-1-(4-nitrophenyl)-pyrazole, a compound of claim 1.
Claim 22
Dependent Claim
9 words
A compound of claim 1 wherein R is 3-dialkylaminoacryloyl.
Claim 23
Dependent Claim
100 words
A compound of claim 1 wherein R is 3-, 4-, or 5-pyrazolyl which is unsubstituted or which is (i) substituted by alkyl of 1-4 carbon atoms on 1-2 ring carbon atoms, (ii) substituted at the 1-position by alkyl of 1-4 carbon atoms, hydroxyalkyl of 2-5 carbon atoms or a nitric acid ester thereof or a hydrocarboncarboxylic acid ester thereof of a total of 4-9 carbon atoms, nitro, phenyl or phenyl substituted by a p-halogen atom, p-alkoxy of 1-4 carbon atoms, or p- or m-nitro, or (iii) substituted both on 1-2 ring carbon atoms and at the 1-position as defined hereinabove.
Claim 24
Dependent Claim
14 words
A position isomer mixture of compounds of claim 1 as defined in (c) thereof.
Claim 25
Dependent Claim
37 words
A pharmaceutical composition comprising, in unit dosage form, an anti-protozoal effective amount per unit dosage of a compound of claim 1 or a mixture of position isomers as defined therein, in admixture with a pharmaceutically acceptable carrier.
Claim 26
Dependent Claim
38 words
A method of treating protozoal infections which comprises administering systemically or to applying topically to the infected area of a patient with such infection an amount of a compound of claim 1 effective to manifest an anti-protozoal effect.
References Cited (Backward Citations)
US3798232A
Cited
US3883549A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-07-25 | 1981-01-24 | 1981-07-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-25 | 1985-01-24 | 1985-07-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-25 | 1989-01-24 | 1989-07-26 | $7700.00 | Window Closed / Lapsed |