DE2412656A1 - Neue nitroimidazolderivate und verfahren zu ihrer herstellung - Google Patents
Neue nitroimidazolderivate und verfahren zu ihrer herstellungInfo
- Publication number
- DE2412656A1 DE2412656A1 DE2412656A DE2412656A DE2412656A1 DE 2412656 A1 DE2412656 A1 DE 2412656A1 DE 2412656 A DE2412656 A DE 2412656A DE 2412656 A DE2412656 A DE 2412656A DE 2412656 A1 DE2412656 A1 DE 2412656A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- nitro
- imidazolyl
- pyrazole
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 241000224527 Trichomonas vaginalis Species 0.000 title abstract description 7
- 239000004599 antimicrobial Substances 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 150000004957 nitroimidazoles Chemical class 0.000 claims abstract description 8
- VJMZOGRNDICYEH-UHFFFAOYSA-N 1-methyl-2-(2-methylpyrazol-3-yl)-5-nitroimidazole Chemical compound CN1N=CC=C1C1=NC=C([N+]([O-])=O)N1C VJMZOGRNDICYEH-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229940058965 antiprotozoal agent against amoebiasis and other protozoal diseases nitroimidazole derivative Drugs 0.000 claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- -1 1-methyl-5-nitro-2-imidazolyl Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- IIEFDFBEXFLCRZ-UHFFFAOYSA-N 1-methyl-5-nitro-2-(1h-pyrazol-5-yl)imidazole Chemical compound C1=C([N+]([O-])=O)N(C)C(C2=NNC=C2)=N1 IIEFDFBEXFLCRZ-UHFFFAOYSA-N 0.000 claims description 3
- IPRLFIXLEWPZNW-UHFFFAOYSA-N 1-methyl-5-nitro-2-(2-phenylpyrazol-3-yl)imidazole Chemical compound C1=C([N+]([O-])=O)N(C)C(C=2N(N=CC=2)C=2C=CC=CC=2)=N1 IPRLFIXLEWPZNW-UHFFFAOYSA-N 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 3
- 229940067157 phenylhydrazine Drugs 0.000 claims description 3
- ALIPSNOCMRFOEG-UHFFFAOYSA-N 1-methyl-2-(1-methylpyrazol-3-yl)-5-nitroimidazole Chemical compound CN1C=CC(C=2N(C(=CN=2)[N+]([O-])=O)C)=N1 ALIPSNOCMRFOEG-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 abstract description 4
- 229960000282 metronidazole Drugs 0.000 abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000003 vaginal tablet Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- ANSCCMZPJWEICB-UHFFFAOYSA-N 1-(1-methyl-5-nitroimidazol-2-yl)ethanone Chemical compound CC(=O)C1=NC=C([N+]([O-])=O)N1C ANSCCMZPJWEICB-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
- C07D233/94—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to other ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2412656A DE2412656A1 (de) | 1974-03-14 | 1974-03-14 | Neue nitroimidazolderivate und verfahren zu ihrer herstellung |
| DK74275A DK74275A (enExample) | 1974-03-14 | 1975-02-26 | |
| US05/557,539 US4038410A (en) | 1974-03-14 | 1975-03-12 | Nitroimidazole derivatives and process for the preparation thereof |
| BE154294A BE826640A (fr) | 1974-03-14 | 1975-03-13 | Nouveaux derives de nitroimidazole et leur procede de preparation |
| FR7508013A FR2263768A1 (enExample) | 1974-03-14 | 1975-03-14 | |
| NL7503108A NL7503108A (nl) | 1974-03-14 | 1975-03-14 | Werkwijze voor de bereiding van een geneesmiddel met antimicroben-werking. |
| JP3100175A JPS50129559A (enExample) | 1974-03-14 | 1975-03-14 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2412656A DE2412656A1 (de) | 1974-03-14 | 1974-03-14 | Neue nitroimidazolderivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2412656A1 true DE2412656A1 (de) | 1975-09-25 |
Family
ID=5910235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2412656A Pending DE2412656A1 (de) | 1974-03-14 | 1974-03-14 | Neue nitroimidazolderivate und verfahren zu ihrer herstellung |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS50129559A (enExample) |
| BE (1) | BE826640A (enExample) |
| DE (1) | DE2412656A1 (enExample) |
| DK (1) | DK74275A (enExample) |
| NL (1) | NL7503108A (enExample) |
-
1974
- 1974-03-14 DE DE2412656A patent/DE2412656A1/de active Pending
-
1975
- 1975-02-26 DK DK74275A patent/DK74275A/da unknown
- 1975-03-13 BE BE154294A patent/BE826640A/xx unknown
- 1975-03-14 JP JP3100175A patent/JPS50129559A/ja active Pending
- 1975-03-14 NL NL7503108A patent/NL7503108A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE826640A (fr) | 1975-09-15 |
| DK74275A (enExample) | 1975-09-15 |
| JPS50129559A (enExample) | 1975-10-13 |
| NL7503108A (nl) | 1975-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |