DE2164412A1 - Nitroimidazole - Google Patents
NitroimidazoleInfo
- Publication number
- DE2164412A1 DE2164412A1 DE2164412A DE2164412A DE2164412A1 DE 2164412 A1 DE2164412 A1 DE 2164412A1 DE 2164412 A DE2164412 A DE 2164412A DE 2164412 A DE2164412 A DE 2164412A DE 2164412 A1 DE2164412 A1 DE 2164412A1
- Authority
- DE
- Germany
- Prior art keywords
- vinyl
- imidazole
- nitro
- dimethylamino
- group
- 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.)
- Ceased
Links
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 title 1
- -1 benzoyloxy, 2-tetrahydropyranyloxy Chemical group 0.000 claims description 50
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000012285 osmium tetroxide Substances 0.000 claims description 6
- 229910000489 osmium tetroxide Inorganic materials 0.000 claims description 6
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical class OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 3
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000002130 sulfonic acid ester group Chemical group 0.000 claims description 2
- WOFBJKCXVVFQKU-UHFFFAOYSA-N 2-[2-[2-(dimethylamino)ethenyl]-5-nitroimidazol-1-yl]ethyl acetate Chemical compound CN(C)C=CC1=NC=C([N+]([O-])=O)N1CCOC(C)=O WOFBJKCXVVFQKU-UHFFFAOYSA-N 0.000 claims 1
- NVKJOXRVEKMMHS-UHFFFAOYSA-N 5-nitro-1,2,4-triazol-3-one Chemical compound [O-][N+](=O)C1=NC(=O)N=N1 NVKJOXRVEKMMHS-UHFFFAOYSA-N 0.000 claims 1
- 101100141312 Mus musculus Ripk1 gene Proteins 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 238000010008 shearing Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 3
- IBXPYPUJPLLOIN-UHFFFAOYSA-N dimetridazole Chemical compound CC1=NC=C(N(=O)=O)N1C IBXPYPUJPLLOIN-UHFFFAOYSA-N 0.000 description 3
- 150000004957 nitroimidazoles Chemical class 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 229940058965 antiprotozoal agent against amoebiasis and other protozoal diseases nitroimidazole derivative Drugs 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- HXRAMSFGUAOAJR-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine Chemical compound CN(C)C(N(C)C)OC(C)(C)C HXRAMSFGUAOAJR-UHFFFAOYSA-N 0.000 description 2
- SCYMXRCVXLEBFH-UHFFFAOYSA-N n,n-dimethyl-2-(1-methyl-5-nitroimidazol-2-yl)ethenamine Chemical compound CN(C)C=CC1=NC=C([N+]([O-])=O)N1C SCYMXRCVXLEBFH-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- BWKAYBPLDRWMCJ-UHFFFAOYSA-N 1,1-diethoxy-n,n-dimethylmethanamine Chemical compound CCOC(N(C)C)OCC BWKAYBPLDRWMCJ-UHFFFAOYSA-N 0.000 description 1
- BLRDXAFJHDJPPE-UHFFFAOYSA-N 1-butyl-2-methyl-5-nitroimidazole Chemical compound CCCCN1C(C)=NC=C1[N+]([O-])=O BLRDXAFJHDJPPE-UHFFFAOYSA-N 0.000 description 1
- ATIJWZXWXNXVOY-UHFFFAOYSA-N 1-ethoxy-n,n,n',n'-tetramethylmethanediamine Chemical compound CCOC(N(C)C)N(C)C ATIJWZXWXNXVOY-UHFFFAOYSA-N 0.000 description 1
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
- MBJUWIMKTGMPRF-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-n,n-dimethylethanamine Chemical compound CN(C)CCC1=NC=CN1 MBJUWIMKTGMPRF-UHFFFAOYSA-N 0.000 description 1
- VDZJVXFACHQYKK-UHFFFAOYSA-N 2-(2-formyl-5-nitroimidazol-1-yl)ethyl acetate Chemical compound CC(=O)OCCN1C(C=O)=NC=C1[N+]([O-])=O VDZJVXFACHQYKK-UHFFFAOYSA-N 0.000 description 1
- WDOBEGMTPLDNHO-UHFFFAOYSA-N 2-(2-methyl-5-nitroimidazol-1-yl)ethyl 4-methylbenzenesulfonate Chemical compound CC1=NC=C([N+]([O-])=O)N1CCOS(=O)(=O)C1=CC=C(C)C=C1 WDOBEGMTPLDNHO-UHFFFAOYSA-N 0.000 description 1
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- OPKYQJHODRBCCR-UHFFFAOYSA-N 2-ethyl-1-methyl-5-nitroimidazole Chemical compound CCC1=NC=C([N+]([O-])=O)N1C OPKYQJHODRBCCR-UHFFFAOYSA-N 0.000 description 1
- SLWQEEUXJOYWHA-UHFFFAOYSA-N 4-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]morpholine Chemical compound CC1=NC=C([N+]([O-])=O)N1CCN1CCOCC1 SLWQEEUXJOYWHA-UHFFFAOYSA-N 0.000 description 1
- 150000004958 5-nitroimidazoles Chemical class 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QBJFUWLILCHAPI-UHFFFAOYSA-N CN(C=CC=1NC=CN1)C Chemical compound CN(C=CC=1NC=CN1)C QBJFUWLILCHAPI-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical compound Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- VKHLWDJFNHNESM-UHFFFAOYSA-N n,n-diethyl-2-(1-methyl-5-nitroimidazol-2-yl)ethenamine Chemical compound CCN(CC)C=CC1=NC=C([N+]([O-])=O)N1C VKHLWDJFNHNESM-UHFFFAOYSA-N 0.000 description 1
- AYZXEGOJMRKZCV-UHFFFAOYSA-N n-(diethoxymethyl)-n-ethylethanamine Chemical compound CCOC(OCC)N(CC)CC AYZXEGOJMRKZCV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000006385 ozonation reaction Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([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
- C07D233/95—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by nitrogen atoms, attached to other ring members
-
- 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
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE793142D BE793142A (fr) | 1971-12-21 | Nitroimidazoles, et leur procede de preparation | |
| DE2164412A DE2164412A1 (de) | 1971-12-21 | 1971-12-21 | Nitroimidazole |
| CH1608272A CH587829A5 (OSRAM) | 1971-12-21 | 1972-11-03 | |
| DD166893A DD104791A5 (OSRAM) | 1971-12-21 | 1972-11-16 | |
| DK608672A DK133242C (da) | 1971-12-21 | 1972-12-06 | 5-nitro-imidazoler til anvendelse som mellemprodukter til fremstilling af 2-formyl- og 2-alkanoyl-5-nitroimidazoler samt fremgangsmade til deres fremstilling |
| CS8481A CS177831B2 (OSRAM) | 1971-12-21 | 1972-12-11 | |
| AU50183/72A AU473933B2 (en) | 1971-12-21 | 1972-12-15 | New nitro-imidazoles and their manufacture and use |
| GB5829972A GB1419529A (en) | 1971-12-21 | 1972-12-18 | 5-nitro-2-2-dialkylamino-vinyl-imidazoles and their 'manufacture and use |
| NL7217330A NL7217330A (OSRAM) | 1971-12-21 | 1972-12-19 | |
| US05/316,928 US3952007A (en) | 1971-12-21 | 1972-12-20 | Processes for preparing 5-nitro-1-methyl-2-(2-dialkylaminovinyl)-imidazole and 5-nitro-1-methyl-2-imidazolyl carboxaldehyde |
| AT1094472A AT319233B (de) | 1971-12-21 | 1972-12-21 | Verfahren zur Herstellung von Nitroimidazolderivaten und ihren Salzen |
| CA159,698A CA982572A (en) | 1971-12-21 | 1972-12-21 | Nitro-imidazoles and their manufacture and use |
| FR7245633A FR2164791B1 (OSRAM) | 1971-12-21 | 1972-12-21 | |
| ZA729044A ZA729044B (en) | 1971-12-21 | 1972-12-21 | Nitroimidazole |
| JP47128753A JPS4868572A (OSRAM) | 1971-12-21 | 1972-12-21 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2164412A DE2164412A1 (de) | 1971-12-21 | 1971-12-21 | Nitroimidazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2164412A1 true DE2164412A1 (de) | 1973-07-05 |
Family
ID=5829117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2164412A Ceased DE2164412A1 (de) | 1971-12-21 | 1971-12-21 | Nitroimidazole |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3952007A (OSRAM) |
| JP (1) | JPS4868572A (OSRAM) |
| AT (1) | AT319233B (OSRAM) |
| AU (1) | AU473933B2 (OSRAM) |
| BE (1) | BE793142A (OSRAM) |
| CA (1) | CA982572A (OSRAM) |
| CH (1) | CH587829A5 (OSRAM) |
| CS (1) | CS177831B2 (OSRAM) |
| DD (1) | DD104791A5 (OSRAM) |
| DE (1) | DE2164412A1 (OSRAM) |
| DK (1) | DK133242C (OSRAM) |
| FR (1) | FR2164791B1 (OSRAM) |
| GB (1) | GB1419529A (OSRAM) |
| NL (1) | NL7217330A (OSRAM) |
| ZA (1) | ZA729044B (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0006463A1 (de) * | 1978-06-22 | 1980-01-09 | BASF Aktiengesellschaft | Verfahren zur Herstellung von 2-substituierten 1-Alkyl-nitroimidazolen |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2553021A1 (de) * | 1974-12-06 | 1976-06-10 | Sandoz Ag | Organische verbindungen, ihre verwendung und herstellung |
| US4105763A (en) * | 1976-10-22 | 1978-08-08 | Hoechst Aktiengesellschaft | 1-Methyl-2-(phenyl-oxymethyl)-5-nitro-imidazoles |
| EP0055059B1 (en) * | 1980-12-12 | 1985-03-27 | Sankyo Company Limited | Diazole and triazole derivatives, processes for their preparation and anti-microbial compositions containing them |
| BR9405079A (pt) * | 1994-01-10 | 1995-09-26 | Santiago Abelardo Bojali Jaber | Produto químico antiamebiano e antiprotozário e processo para sua obtenção |
| EP3010345A4 (en) * | 2013-06-21 | 2017-04-12 | The Regents of The University of California | Expanded therapeutic potential in nitroheteroaryl antimicrobials |
-
0
- BE BE793142D patent/BE793142A/xx unknown
-
1971
- 1971-12-21 DE DE2164412A patent/DE2164412A1/de not_active Ceased
-
1972
- 1972-11-03 CH CH1608272A patent/CH587829A5/xx not_active IP Right Cessation
- 1972-11-16 DD DD166893A patent/DD104791A5/xx unknown
- 1972-12-06 DK DK608672A patent/DK133242C/da active
- 1972-12-11 CS CS8481A patent/CS177831B2/cs unknown
- 1972-12-15 AU AU50183/72A patent/AU473933B2/en not_active Expired
- 1972-12-18 GB GB5829972A patent/GB1419529A/en not_active Expired
- 1972-12-19 NL NL7217330A patent/NL7217330A/xx not_active Application Discontinuation
- 1972-12-20 US US05/316,928 patent/US3952007A/en not_active Expired - Lifetime
- 1972-12-21 CA CA159,698A patent/CA982572A/en not_active Expired
- 1972-12-21 FR FR7245633A patent/FR2164791B1/fr not_active Expired
- 1972-12-21 AT AT1094472A patent/AT319233B/de not_active IP Right Cessation
- 1972-12-21 ZA ZA729044A patent/ZA729044B/xx unknown
- 1972-12-21 JP JP47128753A patent/JPS4868572A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0006463A1 (de) * | 1978-06-22 | 1980-01-09 | BASF Aktiengesellschaft | Verfahren zur Herstellung von 2-substituierten 1-Alkyl-nitroimidazolen |
Also Published As
| Publication number | Publication date |
|---|---|
| DD104791A5 (OSRAM) | 1974-03-20 |
| AT319233B (de) | 1974-12-10 |
| CS177831B2 (OSRAM) | 1977-08-31 |
| BE793142A (fr) | 1973-06-21 |
| ZA729044B (en) | 1973-09-26 |
| AU5018372A (en) | 1974-06-20 |
| FR2164791A1 (OSRAM) | 1973-08-03 |
| DK133242C (da) | 1976-09-20 |
| NL7217330A (OSRAM) | 1973-06-25 |
| CA982572A (en) | 1976-01-27 |
| AU473933B2 (en) | 1976-07-08 |
| CH587829A5 (OSRAM) | 1977-05-13 |
| US3952007A (en) | 1976-04-20 |
| JPS4868572A (OSRAM) | 1973-09-18 |
| DK133242B (da) | 1976-04-12 |
| FR2164791B1 (OSRAM) | 1975-10-17 |
| GB1419529A (en) | 1975-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8131 | Rejection |