NO171910B - Fremgangsmaate for fremstilling av 1-alkyl-5-nitroimidazoler - Google Patents
Fremgangsmaate for fremstilling av 1-alkyl-5-nitroimidazoler Download PDFInfo
- Publication number
- NO171910B NO171910B NO890159A NO890159A NO171910B NO 171910 B NO171910 B NO 171910B NO 890159 A NO890159 A NO 890159A NO 890159 A NO890159 A NO 890159A NO 171910 B NO171910 B NO 171910B
- Authority
- NO
- Norway
- Prior art keywords
- groups
- alkyl
- general formula
- group
- phenoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000005042 acyloxymethyl group Chemical group 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 239000002635 aromatic organic solvent Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- FFYTTYVSDVWNMY-UHFFFAOYSA-N 2-Methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1 FFYTTYVSDVWNMY-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- IBXPYPUJPLLOIN-UHFFFAOYSA-N dimetridazole Chemical compound CC1=NC=C(N(=O)=O)N1C IBXPYPUJPLLOIN-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QDODOGHRBVRKDO-UHFFFAOYSA-N (2-methyl-4-nitroimidazol-1-yl)methyl acetate Chemical compound CC(=O)OCN1C=C([N+]([O-])=O)N=C1C QDODOGHRBVRKDO-UHFFFAOYSA-N 0.000 description 1
- RCIOGWIAQZYOJE-UHFFFAOYSA-N (4-nitroimidazol-1-yl)methyl acetate Chemical compound CC(=O)OCN1C=NC([N+]([O-])=O)=C1 RCIOGWIAQZYOJE-UHFFFAOYSA-N 0.000 description 1
- MBSXIUYLWVLRNB-UHFFFAOYSA-N (5-nitro-1h-imidazol-2-yl)methyl acetate Chemical compound CC(=O)OCC1=NC=C([N+]([O-])=O)N1 MBSXIUYLWVLRNB-UHFFFAOYSA-N 0.000 description 1
- JLZXSFPSJJMRIX-UHFFFAOYSA-N 1-methyl-5-nitroimidazole Chemical compound CN1C=NC=C1[N+]([O-])=O JLZXSFPSJJMRIX-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Fremgangsmåte for fremstilling av l-alkyl-5-nitroimidazoler med den generelle formel
der R betyr et hydrogenatom, en Ci_4-alkylgruppe eller en C2_4-alkenylgruppe, der alkyl- og alkenylgruppene eventuelt er substituert med en eller flere, like eller forskjellige grupper valgt blant fenylgrupper, fenoksygrupper og 5- eller 6-leddede oksygenerte heterocykliske grupper, eller betyr en Cfc.iQ-arylgruppe, eventuelt substituert med en eller flere, like eller forskjellige atomer eller grupper valgt blant halogenatomer, C1_4-alkylgrupper, alkoksygrupper hvis alkyldel inneholder 1-4 karbonatomer, fenylgrupper, fenoksygrupper og nitrogrupper, eller betyr en Cs.^-cykloalkylgruppe, hvorved fenylgruppene, fenoksygruppene og de heterocykliske grupper eventuelt kan være substituert med en eller flere, like eller forskjellige atomer eller grupper valgt blant halogenatomer, C1_4-alkylgrupper, alkoksygrupper hvis alkyldel inneholder 1-4 karbonatomer, fenylgrupper, fenoksygrupper og nitrogrupper, og R^ betyr en rett eller forgrenet C^.^-alkylgruppe. I FR-PS 2 265 743 beskrives en fremgangsmåte for fremstilling av imidazolderivater med den generelle formel I hvorved et alkylsulfat med den generelle formel der Ri har den ovenfor angitte betydning, omsettes med et lmldazolderivat med den generelle formel der R har den ovenfor angitte betydning, i nærvær av en karboksylsyre. Ifølge foreliggende oppfinnelse er det nu funnet at for-bindelsene med formel I kan fremstilles ved en fremgangsmåte som karakteriseres ved at et alkylsulfat med den generelle formel der Ri har den ovenfor angitte betydning, omsettes med et imidazolderivat med den generelle formel
der R har den ovenfor angitte betydning og X betyr en laverealkanoyloksymetylgruppe i et aromatisk organisk opp-løsningsmiddel, hvorefter den oppnådde forbindelse hydrolyseres eller alkoholiseres ved en temperatur mellom 60° og 120<*>C.
Fremgangsmåten gjennomføres vanligvis ved en temperatur mellom 60° og 120°C og fortrinnsvis nær 80°C.
Som organisk oppløsningsmiddel anvender man fortrinnsvis estere som metylacetat eller etylacetat, etere som metyltert-butyleter eller alifatiske eller aromatiske hydrokarboner, eventuelt av halogenert type, for eksempel xylen eller metylenklorid.
Hydrolysen eller alkoholysen av kondensasjonsproduktene gjennomføres vanligvis ved oppvarming i vann eller en alkohol som metanol eller etanol ved en temperatur mellom 60° og 100°C. Det er ikke nødvendig å isolere kondensasjonsproduktene før hydrolysen. Imidazolderivatene med den generelle formel IV kan fremstilles under de betingelser som er beskrevet i GB-PS 1 026 631.
Imidazolderivatene med den generelle formel I oppviser terapautiske egenskaper eller utgjør mellomprodukter for fremstilling av fargestoffer, tekstiltilsetningsmidler eller insektisider.
Oppfinnelsen skal illustreres ved de følgende ikke-begrens-ende eksempler.
Eksempel 1
Til en kolbe utstyr med rørverk og tilførselstrakt settes 3,98 gram (0,02 mol) l-acetoksymetyl-2-metyl-4-nitroimidazol og 10 cm5 xylen. Blandingen oppvarmes til 80°C og derefter tilsettes 3,2 gram (0,024 mol) dimetylsulfat. Reaksjonsblandingen oppvarmes til 80°C i 2 timer. Efter tilsetning av 25 cm5 vann oppvarmes blandingen til 80" C i 2,5 time.
Efter fortynning analyseres reaksjonsblandingen ved HPLC som viser at blandingen inneholder 2,8 gram 1,2-dimetyl-5-nitroimidazol.
Omdanningsgraden for 2-metyl-4- nitroimidazol er nær 100 %.
Utbyttet av 1,2-dimetyl-5-nitrolimidazol er over 95 £, beregnet på anvendt 2-metyl-4- nitroimidazol.
Eksempel 2
Til en trehalskolbe med 50 cm<J> volum settes 20 cm<5> xylen og derefter 3,7 gram l-acetoksymetyl-4-nitroimidazol. Reaksjonsblandingen oppvarmes til 40"C. Man observerer "smelt-ing" av l-acetoksymetyl-4-nitroimidazolet og dannelse av to faser. 2,52 gram dimetylsulfat tilsettes i løpet av 30 minutter ved 80°C. Reaksjonsblandingen som består av farveløse faser oppvarmes til 80'C i 1 time. Efter avkjøling til 70°C tilsettes 20 cm<J> vann og omrøringen fortsettes i 3,5 time ved denne temperatur.
Analyse av reaksjonsblandingen ved HPLC viser at omdanningsgraden for l-acetoksymetyl-4-nitroimidazol er 92 % og at utbyttet av l-metyl-5-nitroimidazol er 83 %.
Eksempel 3
Man arbeider på samme måte som i eksempel 2 men ved en temperatur på 100°C. Efter hydrolyse under tilbakeløpskoking i 1 time og 30 minutter med efterfølgende avkjøling til en temperatur nær 20° C separeres vannfasene ved dekantering og xylenfasen vaskes med 3 ganger 20 cm<J> vann.
Vannfasene forenes og analyseres ved HPLC. Man finner herved at omdanningsgraden for en acetoksymetyl-4-nitroimidazol er 94,6 <& og at utbyttet av l-metyl-5-nitroimidazol er 87,2 %.
Claims (2)
1.
Fremgangsmåte for fremstilling av l-alkyl-5-nitroimidazoler med den generelle formel
der R betyr et hydrogenatom, en Ci_4-alkylgruppe eller en C2_4~alkenylgruppe, der alkyl- og alkenylgruppene eventuelt er substituert med en eller flere, like eller forskjellige grupper valgt blant fenylgrupper, fenoksygrupper og 5- eller 6-leddede oksygenerte heterocykliske grupper, eller betyr en c6-10_arvl6ruPPe» eventuelt substituert med en eller flere, like eller forskjellige atomer eller grupper valgt blant halogenatomer, Ci_4~alkylgrupper, alkoksygrupper hvis alkyldel inneholder 1-4 karbonatomer, fenylgrupper, fenoksygrupper og nitrogrupper, eller betyr en C5_£-cykloalkylgruppe, hvorved fenylgruppene, fenoksygruppene og de heterocykliske grupper eventuelt kan være substituert med en eller flere, like eller forskjellige atomer eller grupper valgt blant halogenatomer, Ci_4~alkylgrupper, alkoksygrupper hvis alkyldel inneholder 1-4 karbonatomer, fenylgrupper, fenoksygrupper og nitrogrupper, og R^ betyr en rett eller forgrenet Ci_i2-alkylgruPPe»karakterisert ved at et alkylsulfat med den generelle formel
der Ri har den ovenfor angitte betydning, omsettes med et lmldazolderivat med den generelle formel
der R har den ovenfor angitte betydning og X betyr en laverealkanoyloksymetylgruppe i et aromatisk organisk opp-løsningsmiddel, hvorefter den oppnådde forbindelse hydrolyseres eller alkoholiseres ved en temperatur mellom 60° og 120°C.
2.
Fremgangsmåte ifølge krav 1, karakterisert ved at reaksjonen gjennomføres i et organisk oppløsning-middel valgt blant estere, etere og alifatiske eller aromatiske hydrokarboner, eventuelt halogenerte slike.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8800414A FR2625997B1 (fr) | 1988-01-15 | 1988-01-15 | Procede de preparation du dimethyl-1,2 nitro-5 imidazole |
| FR8807773A FR2632640B1 (fr) | 1988-06-10 | 1988-06-10 | Procede de preparation d'alkyl-1 nitro-5 imidazoles |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO890159D0 NO890159D0 (no) | 1989-01-13 |
| NO890159L NO890159L (no) | 1989-07-17 |
| NO171910B true NO171910B (no) | 1993-02-08 |
| NO171910C NO171910C (no) | 1993-05-19 |
Family
ID=26226445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO890159A NO171910C (no) | 1988-01-15 | 1989-01-13 | Fremgangsmaate for fremstilling av 1-alkyl-5-nitroimidazoler |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4925949A (no) |
| EP (1) | EP0325512B1 (no) |
| JP (1) | JP2539022B2 (no) |
| KR (1) | KR890011856A (no) |
| CN (1) | CN1023221C (no) |
| AR (1) | AR245935A1 (no) |
| AU (1) | AU608932B2 (no) |
| CA (1) | CA1310325C (no) |
| DE (1) | DE68904436T2 (no) |
| DK (1) | DK14589A (no) |
| ES (1) | ES2054035T3 (no) |
| FI (1) | FI890185A (no) |
| GR (1) | GR3006827T3 (no) |
| HU (1) | HU200446B (no) |
| IE (1) | IE890090L (no) |
| IL (1) | IL88943A (no) |
| MX (1) | MX169215B (no) |
| NO (1) | NO171910C (no) |
| PT (1) | PT89442B (no) |
| SU (1) | SU1648249A3 (no) |
| YU (1) | YU46966B (no) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2625998B1 (fr) * | 1988-01-15 | 1990-06-08 | Rhone Poulenc Sante | Procede de preparation d'hydroxyalkyl-1 methyl-2 nitro-5 imidazoles |
| FR2625999B1 (fr) * | 1988-01-15 | 1990-06-08 | Rhone Poulenc Sante | Procede de preparation d'hydroxyalkyl-1 methyl-2 nitro-5 imidazoles |
| FR2659326A1 (fr) * | 1990-03-12 | 1991-09-13 | Rhone Poulenc Sante | Procede de preparation d'hydroxyalkyl-1 nitro-5 imidazoles. |
| US5344937A (en) * | 1993-04-20 | 1994-09-06 | Eli Lilly And Company | Alkyl substituted nitroimidazole acetic acids |
| CN1046040C (zh) * | 1994-11-29 | 1999-10-27 | 联华电子股份有限公司 | 与总线位数相匹配的存贮器直接存取结构 |
| UA80839C2 (en) * | 2002-10-15 | 2007-11-12 | 1-substituted 4-nitroimidazole compound and process for producing the same | |
| US7368579B2 (en) * | 2002-10-15 | 2008-05-06 | Otsuka Pharmaceutical Co., Ltd. | 1-substituted-4-nitroimidazole compound and process for producing the same |
| TWI300409B (en) * | 2004-02-18 | 2008-09-01 | Otsuka Pharma Co Ltd | Method for producing 4-nitroimidazole compound |
| RU2528025C1 (ru) * | 2013-03-29 | 2014-09-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Национальный исследовательский Томский государственный университет" (ТГУ) | Способ получения диметридазола |
| CN108689941B (zh) * | 2018-06-08 | 2023-05-16 | 湖北省宏源药业科技股份有限公司 | 一种合成1,2-二甲基-5-硝基咪唑的方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1216238A (fr) * | 1957-09-14 | 1960-04-22 | Rhone Poulenc Sa | Nouveaux dérivés du nitro-5 imidazole et leur préparation |
| IT1051571B (it) * | 1974-03-07 | 1981-05-20 | Finotto Martino | Procedimento di fabbricazione di i 2 dimetil 5 nitro imidazolo |
| DE2414280C2 (de) * | 1974-03-25 | 1981-12-17 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 1-Methyl-5-nitroimidazolen |
| IT1098864B (it) * | 1978-09-19 | 1985-09-18 | Farchemia Spa | Processo per la preparazione di nitroimidazoli |
| DE3026846A1 (de) * | 1980-07-16 | 1982-02-11 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 1,2-dimethyl-5-nitroimidazol |
| DE3132025A1 (de) * | 1981-08-13 | 1983-03-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur gewinnung von 1,2-dimethyl-5-nitroimidazol von hoher reinheit |
| EP0126183A1 (de) * | 1982-12-23 | 1984-11-28 | A. Nattermann & Cie. GmbH | Substituierte 5(4)-Nitroimidazole sowie Verfahren zu ihrer Herstellung |
| FR2625998B1 (fr) * | 1988-01-15 | 1990-06-08 | Rhone Poulenc Sante | Procede de preparation d'hydroxyalkyl-1 methyl-2 nitro-5 imidazoles |
| FR2625999B1 (fr) * | 1988-01-15 | 1990-06-08 | Rhone Poulenc Sante | Procede de preparation d'hydroxyalkyl-1 methyl-2 nitro-5 imidazoles |
-
1989
- 1989-01-12 CN CN89101402A patent/CN1023221C/zh not_active Expired - Fee Related
- 1989-01-12 DE DE8989400094T patent/DE68904436T2/de not_active Expired - Lifetime
- 1989-01-12 ES ES89400094T patent/ES2054035T3/es not_active Expired - Lifetime
- 1989-01-12 IL IL8894389A patent/IL88943A/en not_active IP Right Cessation
- 1989-01-12 AR AR89312974A patent/AR245935A1/es active
- 1989-01-12 EP EP89400094A patent/EP0325512B1/fr not_active Expired - Lifetime
- 1989-01-13 FI FI890185A patent/FI890185A/fi not_active Application Discontinuation
- 1989-01-13 MX MX014536A patent/MX169215B/es unknown
- 1989-01-13 US US07/296,709 patent/US4925949A/en not_active Expired - Lifetime
- 1989-01-13 SU SU894613254A patent/SU1648249A3/ru active
- 1989-01-13 IE IE890090A patent/IE890090L/xx unknown
- 1989-01-13 DK DK014589A patent/DK14589A/da not_active Application Discontinuation
- 1989-01-13 CA CA000588180A patent/CA1310325C/fr not_active Expired - Lifetime
- 1989-01-13 YU YU7189A patent/YU46966B/sh unknown
- 1989-01-13 AU AU28451/89A patent/AU608932B2/en not_active Ceased
- 1989-01-13 JP JP1005079A patent/JP2539022B2/ja not_active Expired - Lifetime
- 1989-01-13 PT PT89442A patent/PT89442B/pt not_active IP Right Cessation
- 1989-01-13 NO NO890159A patent/NO171910C/no unknown
- 1989-01-13 HU HU89127A patent/HU200446B/hu not_active IP Right Cessation
- 1989-01-14 KR KR1019890000396A patent/KR890011856A/ko not_active Application Discontinuation
-
1993
- 1993-01-21 GR GR920402815T patent/GR3006827T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1310325C (fr) | 1992-11-17 |
| KR890011856A (ko) | 1989-08-22 |
| DE68904436D1 (de) | 1993-03-04 |
| ES2054035T3 (es) | 1994-08-01 |
| JPH01213268A (ja) | 1989-08-28 |
| IL88943A0 (en) | 1989-08-15 |
| DK14589A (da) | 1989-07-16 |
| US4925949A (en) | 1990-05-15 |
| NO171910C (no) | 1993-05-19 |
| JP2539022B2 (ja) | 1996-10-02 |
| DK14589D0 (da) | 1989-01-13 |
| AR245935A1 (es) | 1994-03-30 |
| YU46966B (sh) | 1994-09-09 |
| NO890159D0 (no) | 1989-01-13 |
| FI890185A0 (fi) | 1989-01-13 |
| IE890090L (en) | 1989-07-15 |
| EP0325512A1 (fr) | 1989-07-26 |
| HU200446B (en) | 1990-06-28 |
| HUT49585A (en) | 1989-10-30 |
| PT89442A (pt) | 1990-02-08 |
| NO890159L (no) | 1989-07-17 |
| IL88943A (en) | 1994-05-30 |
| FI890185A (fi) | 1989-07-16 |
| AU608932B2 (en) | 1991-04-18 |
| DE68904436T2 (de) | 1993-07-29 |
| MX169215B (es) | 1993-06-24 |
| CN1023221C (zh) | 1993-12-22 |
| AU2845189A (en) | 1989-07-20 |
| CN1035824A (zh) | 1989-09-27 |
| PT89442B (pt) | 1993-09-30 |
| YU7189A (en) | 1990-12-31 |
| SU1648249A3 (ru) | 1991-05-07 |
| EP0325512B1 (fr) | 1993-01-20 |
| GR3006827T3 (no) | 1993-06-30 |
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