DE2607789A1 - PROCESS FOR THE PREPARATION OF 1-METHYL-2-(ALKYLSULFONYL)-PHENOXY-METHYL)-5-NITRO-IMIDAZOLE - Google Patents

PROCESS FOR THE PREPARATION OF 1-METHYL-2-(ALKYLSULFONYL)-PHENOXY-METHYL)-5-NITRO-IMIDAZOLE

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Publication number
DE2607789A1
DE2607789A1 DE19762607789 DE2607789A DE2607789A1 DE 2607789 A1 DE2607789 A1 DE 2607789A1 DE 19762607789 DE19762607789 DE 19762607789 DE 2607789 A DE2607789 A DE 2607789A DE 2607789 A1 DE2607789 A1 DE 2607789A1
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methyl
nitro
imidazole
phenoxymethyl
formula
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DE19762607789
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German (de)
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Erhardt Dipl Chem D Winkelmann
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Hoechst AG
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Hoechst AG
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Priority to DE2459395A priority Critical patent/DE2459395C2/en
Application filed by Hoechst AG filed Critical Hoechst AG
Priority to DE19762607789 priority patent/DE2607789A1/en
Priority to NL7701838A priority patent/NL7701838A/en
Priority to ES456117A priority patent/ES456117A2/en
Priority to EG111/77A priority patent/EG13828A/en
Priority to FI770599A priority patent/FI770599A/fi
Priority to GR52838A priority patent/GR62437B7/en
Priority to IT20658/77A priority patent/IT1115608B/en
Priority to LU76834A priority patent/LU76834A1/xx
Priority to CA272,551A priority patent/CA1079738A/en
Priority to CH231377A priority patent/CH624942A5/en
Priority to SE7702126A priority patent/SE7702126L/en
Priority to AT128477A priority patent/AT361468B/en
Priority to NO770648A priority patent/NO770648L/en
Priority to DK84177A priority patent/DK144524C/en
Publication of DE2607789A1 publication Critical patent/DE2607789A1/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Pharmaceutically utilisable 1-methyl-2-(4-methylsulphonylphenoxymethyl)-5-nitroimidazoles and 1-methyl-2-(4-ethylsulphonylphenoxymethyl)-5-nitroimidazoles of the formula I are prepared by oxidation of the corresponding 4-methylthio, 4-ethylthio, 4-methylsulphinyl or 4-ethylsulphinyl compounds. The substituents in formula I have the meaning stated in the claim. <IMAGE>

Description

Verfahren zur Herstellung von 1-Methyl-2-(alkylsul funyl )-phen-Process for the preparation of 1-methyl-2- (alkylsulfuryl) -phen-

oxy-methyl)-5-nitro-imidazolen Gegenstand der Patentanmeldung P 24 59 395.1 (HOE 74/F 374) sind 1-Alkyl-2-(phenoxymethyl)-5-nitro-imidazole der Formel worin R1 Methyl oder Äthyl, R2 Trifluormethyl, Trichlormethyl, Nitro, Cyan, Methylsulfonyl oder Äthylsulfonyl und Wasserstoff, Fluor, Chlor, Brom, Jod, Trifluormethyl, Trichiormethyl, Nitro oder Cyan bedeuten, Verfahren zur llerstellung dieser Verbindungen, sie enthaltende pharmazeutische Mittel und ihre Verwendung.oxy-methyl) -5-nitro-imidazoles The subject of patent application P 24 59 395.1 (HOE 74 / F 374) are 1-alkyl-2- (phenoxymethyl) -5-nitro-imidazoles of the formula where R1 is methyl or ethyl, R2 is trifluoromethyl, trichloromethyl, nitro, cyano, methylsulfonyl or ethylsulfonyl and hydrogen, fluorine, chlorine, bromine, iodine, trifluoromethyl, trichloromethyl, nitro or cyano, processes for the preparation of these compounds, pharmaceutical agents containing them and their Use.

Gegenstand der Zusatzanmeldung P (HOE 76/F 035) sind) 1-Methyl-2-(phenoxymethyl)-5-nitro-imidazole der Formel worin R¹ Nitro, Cyan, Methylsulfonyl oder Äthylsulfonyl und R² methyl oder Halogen bedeuten, Verfahren zur Herstellung dieser Verbindungen, sie enthaltende pharmazeutische Mittel und ihre Verwendung.Subject of the additional application P (HOE 76 / F 035) are) 1-methyl-2- (phenoxymethyl) -5-nitro-imidazoles of the formula wherein R¹ denotes nitro, cyano, methylsulfonyl or ethylsulfonyl and R² denotes methyl or halogen, a process for the preparation of these compounds, pharmaceutical compositions containing them and their use.

in Weiterentwicklung des Gegenstandes der Patentanmeldung P 24 59 395.1 wurde nun ein Verfahren zur Herstellung von 1-Alkyl-2-(phenoymethyl)-5-nitro-imidazolen der Formel I gefunden, worin R¹ Methyl, R² Methylsulfonyl oder Äthylsulfonyl und R³ Wasserstoff, Retnyl oder Halogen wie Fiuor, Chlui', brom oder Jod bedeuten, das dadurch gekennzeichnet ist, daß man 1-Methyl-2-(phenoxymethyl)-5-nitro-imidazole der Formel II worin A ein Schwefelatom oder eine Sulfoxidgruppe (-SO-), R Methyl oder Äthyl, R1 Methyl und R3 Wasserstoff, Methyl oder Halogen wie Fluor, Chlor, Brom oder Jod bedeuten, oxidiert.In a further development of the subject matter of patent application P 24 59 395.1, a process for the preparation of 1-alkyl-2- (phenoymethyl) -5-nitro-imidazoles of the formula I has now been found, wherein R¹ is methyl, R² is methylsulphonyl or ethylsulphonyl and R³ is hydrogen, retnyl or halogen such as fluorine, chlorine ', bromine or iodine, which is characterized in that 1-methyl-2- (phenoxymethyl) -5-nitro-imidazoles of the formula II where A is a sulfur atom or a sulfoxide group (-SO-), R is methyl or ethyl, R1 is methyl and R3 is hydrogen, methyl or halogen such as fluorine, chlorine, bromine or iodine, is oxidized.

Die als Ausgangsstoffe verwendeten 1-Methyl-2-(phenoxyulethyl)-5-nitro-imidazole der Formel II sind Gegenstand der Patentanmeldung P 25 31 303.5 (HOE 75/F 183) und der Zusatzanmeldung P26 05 222.2 (HOE76/F 019). Sie können aus 1-Methyl-2-chlormethyl-5-nitro-imidazol (erhältlich nach DOS 1.595.929 und DOS 1.470.102) und gegebenenfalls substituierten AlKylmercaptophenolen oder Alkylsulfinylphenolen (erhältlich aus den entsprechenden Merkaptophenolen und Dialkylsulfat und gegebenenfalls anschließende Oxydation mit Perbenzoesäure) In Dimethylformamid und in Gegenwart von Kaliumcarbonat erhalten werden.The 1-methyl-2- (phenoxyulethyl) -5-nitro-imidazoles used as starting materials of formula II are the subject of patent application P 25 31 303.5 (HOE 75 / F 183) and the additional registration P26 05 222.2 (HOE76 / F 019). You can choose from 1-methyl-2-chloromethyl-5-nitro-imidazole (available according to DOS 1.595.929 and DOS 1.470.102) and optionally substituted AlKylmercaptophenols or Alkylsulfinylphenolen (available from the corresponding Mercaptophenols and dialkyl sulfate and optionally subsequent oxidation with Perbenzoic acid) Obtained in dimethylformamide and in the presence of potassium carbonate will.

Als Ausgangsstoffe der Formel II kommen beispielsweise in Frage: 1-Methyl-2-(4-methylthio-phenoxymethyl)-5-nitro-imidazol 1-Methyl-2-(4-äthylthio-phenoxymethyl)-5-nitro-imidazol 1-Methyl-2-(3-methyl-4-methylthio)-phenoxymethyl)-5-nitro-imidazol 1-Methyl-2-(3-methyl-4-äthylthio)-phenoxymethyl)-5-nitro-imidazol 1-Methyl-2-(3-fluor-, -chlor-, -brom-, -jod-4-methylthio-phenoxymethyl)-5-nitro-imidazol 1-Methyl-2-(3-fluor-, -chlor-, -brom-, -jod-4-äthylthio-phenoxymethyl)-5-nitro-imidazol 1-Methyl-2-(4-methylsulfinyl-phenoxymethyl)-5-nitro-1 i i i dazo 1 1-Methyl-2-(4-äthylsulfinyl-phenoxymethyl)-5-nitro-imidazol 1-Methyl-2-(3-methyl-4-methylsulfinyl-phenoxymethyl)-5-nitroimidazol 1-Methyl-2-(3-methyl-4-äthysulfinyl-phenoxymethyl)-5-nitroimidazol 1-Methyl-2-(3-fluor-, -chlor-, -brom-, -jod-4-methylsulfinylphenoxymethyl)-5-nitro-imidazol 1-Methyl-2-(3-fluor-, -chlor-, -brom-, -jod-4-äthylsulfinylphenoxymethyl)-5-nitro-imidazol Zur Oxidation werden zweckmäßig ein- oder zweifach ulolare Mengen eines Oxydattonsmittels verwendet. Oft kann vorteilhaft sin Überschuß des Oxydationsmlttels verwendet werden.Possible starting materials of the formula II are, for example: 1-methyl-2- (4-methylthio-phenoxymethyl) -5-nitro-imidazole 1-methyl-2- (4-ethylthio-phenoxymethyl) -5-nitro-imidazole 1-methyl-2- (3-methyl-4-methylthio) -phenoxymethyl) -5-nitro-imidazole 1-methyl-2- (3-methyl-4-ethylthio) -phenoxymethyl) -5-nitro-imidazole 1-methyl-2- (3-fluoro-, -chlor-, -bromo-, -iodo-4-methylthio-phenoxymethyl) -5-nitro-imidazole 1-methyl-2- (3-fluoro-, -chlor-, -bromo-, -iodo-4-ethylthio-phenoxymethyl) -5-nitro-imidazole 1-methyl-2- (4-methylsulfinyl-phenoxymethyl) -5-nitro-1 i i i dazo 1 1-methyl-2- (4-ethylsulfinyl-phenoxymethyl) -5-nitro-imidazole 1-methyl-2- (3-methyl-4-methylsulfinyl-phenoxymethyl) -5-nitroimidazole 1-methyl-2- (3-methyl-4-ethysulfinyl-phenoxymethyl) -5-nitroimidazole 1-methyl-2- (3-fluoro-, -chlor-, -bromo-, -iodo-4-methylsulfinylphenoxymethyl) -5-nitro-imidazole 1-methyl-2- (3-fluoro-, -chlor-, -bromo-, -iodo-4-ethylsulfinylphenoxymethyl) -5-nitro-imidazole For oxidation one or two times ulolar amounts of an oxidizing agent are expediently used. An excess of the oxidizing agent can often advantageously be used.

Verweridet man als Ausgangsstoffe die entsprechenden Sulfide (A = -S- in Formel II), so benötigt man mindestens zwei Moiäquivalente Oxyaationsmittel. Verwendet man als ausgangsstoff die entsprechenden Sulfoxide (A = -SO- in Formel II). so benötigt man ein Moläquivalent Oxydationsmittel.If the corresponding sulfides (A = -S- in formula II), at least two molar equivalents of oxidizing agent are required. If you use the corresponding sulfoxides as the starting material (A = -SO- in the formula II). so one needs a molar equivalent of oxidizing agent.

ALs Oxydationsmittel kommen beispielsweise in Frage Wasserstoffperoxid oder Persäuren, wie z.B. Peressigsäure, Hertrifluoressigsäure, Chlorperbenzoesäuren, insbesondere 5-Chlorperbenzoesäure, Salpetersäure, Chromsäure und ihre Salze, Chromsäureanhydrid, Permanganate, Hypochlorite, Chlorate, Perchlorate, Perjodate und Stickoxide, insbesonder Distickstoffte troxid.Hydrogen peroxide, for example, can be used as an oxidizing agent or peracids, such as peracetic acid, hertrifluoroacetic acid, chloroperbenzoic acids, in particular 5-chloroperbenzoic acid, nitric acid, chromic acid and its salts, chromic anhydride, Permanganates, hypochlorites, chlorates, perchlorates, periodates and nitrogen oxides, in particular Dinitrogen troxid.

Die Oxydationsreaktionen werden vorteilhaft in einem Lösungs-oder Verteilungsmittel durchgeführt.The oxidation reactions are advantageous in a solution or Distribution means carried out.

Hierbei eignen sich besonaers solche Lösungsmittel, die von dem Oxydationslnitiel nicht angegriffen werden, wi z.B. Esstgsäure, Trifluoressigsäure. Bei Verwendung von Perbenzoesäure eignen sich auch Methylenchlorid und Chlorform als Lösungsmittel.Solvents from the oxidizing agent are particularly suitable for this purpose are not attacked, such as e.g. ethyl acetate, trifluoroacetic acid. Using of perbenzoic acid, methylene chloride and chloroform are also suitable solvents.

Die Oxydationsreaktionen werden im allgemeinen bei Temperaturen zwische 0 und 100°C, insbesondere bei 40-60°C durchgeführt.The oxidation reactions are generally carried out at temperatures between 0 and 100 ° C, especially at 40-60 ° C.

Die Reaktionszeiten betragen je nach den Reaktionsbedingungen wenige Minuten bis zu einigen Stunden.The reaction times are a few depending on the reaction conditions Minutes to a few hours.

Die Isolierung der Verfahrenserzeugnisse erfolgt durch Verdünnen der Reaktionslösung mit Wasser unter gleichzeitiger Ausfallung, oder durch Eindampfen des organischen Lösungsmittel im Vakuum. Gegebenenfalls kann eine Reinigung durch Umkristal-Lisation aus einem geeigneten Lösungsmittel oder Lösungsmittelgemisch erfolgen.The process products are isolated by diluting the Reaction solution with water with simultaneous precipitation, or by evaporation of the organic solvent in vacuo. If necessary, cleaning can be carried out Recrystallization from a suitable solvent or solvent mixture take place.

Beispiel 1 1-Methyl-2-(4-methylsulfonyl-phenoxymethyl)-5-nitro-imidazol 27,9 g (0,1 Mol) 1-Methyl-2-(4-methylthio-phenoxymethyl)-5-nitro-imidazol (Fp. 116°C) werden in 250 ml Eisessig gelöst und unter Rühren bei Raumtemperatur 24,3 g (0,25 Mol) 35%iges Wasserstoffsuperoxid zugetropft. Durch die exotherme ReaKtion erfolgt Temperaturanstieg auf ca. 450C. Danach wird noch 1 Stunde auf 60°C unter Rühren erhitzt. Nach Abkühlen auf Raumtemperatur wird der Ansatz auf 800 mi Eis/Wasser-Gemisch gegossen, die Ausfälïung abgesaugt, mit Wasser gewaschen und aus Isopropanol unter Aktivkohlezusatz umkristallisiert. Man erhalt so 29 g = 93 Yó der Theorie 1-Methyl-2-(4-methylsulfonylphenoxymethyl)-5-nitro-imidazol in Form von gelblichen Kristallen mit einem Fp. 157°C.Example 1 1-Methyl-2- (4-methylsulfonyl-phenoxymethyl) -5-nitro-imidazole 27.9 g (0.1 mol) of 1-methyl-2- (4-methylthio-phenoxymethyl) -5-nitro-imidazole (melting point 116 ° C.) are dissolved in 250 ml of glacial acetic acid and, with stirring at room temperature, 24.3 g (0.25 Mol) 35% hydrogen peroxide was added dropwise. The exothermic reaction takes place Temperature rise to approx. 450C. This is followed by a further 1 hour at 60 ° C. with stirring heated. After cooling to room temperature, the batch is poured onto 800 ml of an ice / water mixture poured, sucked off the precipitate, washed with water and made of isopropanol Recrystallized activated charcoal. This gives 29 g = 93% of the theory 1-methyl-2- (4-methylsulfonylphenoxymethyl) -5-nitro-imidazole in the form of yellowish crystals with a melting point of 157 ° C.

An Stelle des Ausgangsstoffes 1-Methyl-2-(4-methylthio-phenoxymethyi)-5-nitro-imidazol kann auch das entsprechende Sulfoxid, 1-Methyl-2-(4-methylsulfinyl-phenoxymethyl)-5-nitro-imidazol (Fp. 130°C) verwendet werden. Es genügt dann die Verwendung der halben Menge Wasserstoffsuperoxid.Instead of the starting material 1-methyl-2- (4-methylthio-phenoxymethyi) -5-nitro-imidazole can also use the corresponding sulfoxide, 1-methyl-2- (4-methylsulfinyl-phenoxymethyl) -5-nitro-imidazole (M.p. 130 ° C) can be used. It is then sufficient to use half the amount of hydrogen peroxide.

Auf gleiche Weise können hergestellt werden: 1 -Methyl-2- ( 4-äthylsulfonyl-phenoxymethyl )-5-nitro-imidazol Fp. 132°C durch Oxydation von 1-Methyl-2-(4-äthylthio-phenoxymethyl)-5-nitro-imidazol (Fp. 90°C) oder 1-Methyl-2-(4-äthylsulfinyl-phenoxymethyl)-5-nitro-imidazol (Fp. 103°C).The following can be prepared in the same way: 1 -Methyl-2- (4-ethylsulfonyl-phenoxymethyl ) -5-nitro-imidazole mp. 132 ° C. by oxidation of 1-methyl-2- (4-ethylthio-phenoxymethyl) -5-nitro-imidazole (Mp. 90 ° C) or 1-methyl-2- (4-ethylsulfinyl-phenoxymethyl) -5-nitro-imidazole (mp. 103 ° C).

1 -Nethyl-2- ( 3-methyl-4-inethylsulfonyl-phenoxymethyl5-nitroimidazol Fp. 1410C durch Oxydation von 1-Methyl-2-(3-methyl-4-methylthio-phenoxymethyl)-5-nitro-imidazol (Fp. 108°C) oder 1 -Nethyl-2- ( 3-methyl-4-methylaulfinyl-phenoxymethyl )-5-nitroimidazol (Fp. 1210C).1-ethyl-2- (3-methyl-4-ynethylsulfonyl-phenoxymethyl-5-nitroimidazole M.p. 1410C by oxidation of 1-methyl-2- (3-methyl-4-methylthio-phenoxymethyl) -5-nitro-imidazole (M.p. 108 ° C) or 1-methyl-2- (3-methyl-4-methylaulfinyl-phenoxymethyl) -5-nitroimidazole (M.p. 1210C).

1-Methyl-2-(3-methyl-4-äthylsulfonyl-phenoxymethyl)-5-nitroimidazol Fp. 115°C durch Oxydation von 1-Methyl-2-(5-methyl-4-äthylthio-phenoxymethyl)-5-nitro-imidazol (Fp. 800C) oder 1 -Methyl-2- ( 3-wethyl-4-äthylsulfinyl-phenoxymetfiyl )-5-nitroimidazol (E'p. 950C).1-methyl-2- (3-methyl-4-ethylsulfonyl-phenoxymethyl) -5-nitroimidazole Mp. 115 ° C by oxidation of 1-methyl-2- (5-methyl-4-ethylthio-phenoxymethyl) -5-nitro-imidazole (M.p. 800C) or 1-methyl-2- (3-wethyl-4-ethylsulfinyl-phenoxymethyl) -5-nitroimidazole (E'p. 950C).

1-Methyl-2-(3-chlor-4-methylsulfonyl-phenoxymethyl)-5-nitroimidazol durch Oxydation von 1-Methyl-2-(3-chlor-4-methylthxophenoxymethyl)-5-nitro-immidazol oder 1-Methyl-2-(3-chlor-4-methylsulfinyl-phenoxymethyl)-5-nitro-imidazol.1-methyl-2- (3-chloro-4-methylsulfonyl-phenoxymethyl) -5-nitroimidazole by oxidation of 1-methyl-2- (3-chloro-4-methylthxophenoxymethyl) -5-nitro-immidazole or 1-methyl-2- (3-chloro-4-methylsulfinyl-phenoxymethyl) -5-nitro-imidazole.

1-Methyl-2-(3-chlor-4-äthylsulfonyl-phenoxymethyl)-5-nitroimidazol durch Oxydation von 1-Methyl-2-(3-chlor-4-äthylthiophenoxymethyl)-nitro-imidazol oder 1-Methyl-2-(3-chlor-4-äthylsulfinyl-phenoxy-methyl)-5-nitro-imidazol.1-methyl-2- (3-chloro-4-ethylsulfonyl-phenoxymethyl) -5-nitroimidazole by oxidation of 1-methyl-2- (3-chloro-4-ethylthiophenoxymethyl) -nitro-imidazole or 1-methyl-2- (3-chloro-4-ethylsulfinyl-phenoxy-methyl) -5-nitro-imidazole.

Claims (1)

P a t e n t a n s p r u c h Verfahren zur erstellung von 1-Alkyl-2-(phenoxyrethyl)-5-nitro-imidazolen der Formel I worin R1 Methyl und R2 Methylsulfonyl oder Athylsulfonyl und R³ Wasserstoff, Methyl oder Halogen bedeuten, das dadurch gekennzeichnet ist, daß man 1-Methyl-2-(phenoxymethyl)-5-nitroimidazole der Formel II worin A ein Schwefelatos oder eine Sulfoxidgruppe (-SO-), R Methyl oder Äthyl, R1 Methyl und R3 Wasserstoff, Methyl oder Halogen bedeuten, oxidiert.P atent claim Process for the preparation of 1-alkyl-2- (phenoxyrethyl) -5-nitro-imidazoles of the formula I. wherein R1 is methyl and R2 is methylsulfonyl or ethylsulfonyl and R³ is hydrogen, methyl or halogen, which is characterized in that 1-methyl-2- (phenoxymethyl) -5-nitroimidazoles of the formula II where A is a sulfur atom or a sulfoxide group (-SO-), R is methyl or ethyl, R1 is methyl and R3 is hydrogen, methyl or halogen, oxidized.
DE19762607789 1974-12-16 1976-02-26 PROCESS FOR THE PREPARATION OF 1-METHYL-2-(ALKYLSULFONYL)-PHENOXY-METHYL)-5-NITRO-IMIDAZOLE Withdrawn DE2607789A1 (en)

Priority Applications (15)

Application Number Priority Date Filing Date Title
DE2459395A DE2459395C2 (en) 1974-12-16 1974-12-16 1-Alkyl-2- (phenoxymethyl) -5-nitro-imidazoles, process for their preparation and pharmaceutical agents
DE19762607789 DE2607789A1 (en) 1974-12-16 1976-02-26 PROCESS FOR THE PREPARATION OF 1-METHYL-2-(ALKYLSULFONYL)-PHENOXY-METHYL)-5-NITRO-IMIDAZOLE
NL7701838A NL7701838A (en) 1976-02-26 1977-02-21 PROCESS FOR PREPARING 1-METHYL-2- (ALKYLSULFONYL) PHENOXY-METHYL-5-NITRO-IMIDA SOLES.
ES456117A ES456117A2 (en) 1975-12-10 1977-02-21 Procedure for the preparation of 1-alcohil-2- (fenoxy-methyl-5-nitro-imidazoles) (Machine-translation by Google Translate, not legally binding)
EG111/77A EG13828A (en) 1976-02-26 1977-02-23 Process for the manufacture of 1-methyl-2-(alkyl-sulfonyl-phenoxy-methyl)5-nitro-imidazoles
IT20658/77A IT1115608B (en) 1976-02-26 1977-02-24 PROCESS FOR THE PREPARATION OF 1-METHYL-2- (ALCHYL-SULPHONYL-PHENOXYMETHYL) -5-NITRO-IMIDAZOLE
GR52838A GR62437B7 (en) 1975-12-15 1977-02-24 Preparation process of 1-methyl-2-(alkylsulfonyl)-phenoxy-methyl)-5-nitro-imidazoles
FI770599A FI770599A (en) 1976-02-26 1977-02-24
LU76834A LU76834A1 (en) 1976-02-26 1977-02-24
CA272,551A CA1079738A (en) 1976-02-26 1977-02-24 Process for the manufacture of 1-alkyl-2-(phenoxymethyl)-5-nitroimidazoles
CH231377A CH624942A5 (en) 1976-02-26 1977-02-24 Process for the preparation of 1-methyl-2-(alkylsulphonylphenoxymethyl)-5-nitroimidazoles
SE7702126A SE7702126L (en) 1976-02-26 1977-02-25 METHOD OF PREPARING 1-METHYL-2- (ALKYLSULPHONYL-PHENOXY-METHYL) -5-NITRO-IMIDAZOLES
AT128477A AT361468B (en) 1976-02-26 1977-02-25 METHOD FOR THE PRODUCTION OF NEW 1-METHYL-2- (ALKYLSULFONYL-PHENOXYMETHYL) -5-NITRO-IMIDACOLES
NO770648A NO770648L (en) 1976-02-26 1977-02-25 PROCEDURES FOR THE PREPARATION OF 1-METHYL-2- (ALKYL SULPHONYL) - (PHENOXYMETHYL) -5-NITRO-IMIDAZOLES
DK84177A DK144524C (en) 1976-02-26 1977-02-25 ANALOGY PROCEDURE FOR PREPARING 1-METHYL-2- (ALKYL SULPHONYL-PHENOXYMETHYL) -5-NITRO-IMIDAZOLES

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2459395A DE2459395C2 (en) 1974-12-16 1974-12-16 1-Alkyl-2- (phenoxymethyl) -5-nitro-imidazoles, process for their preparation and pharmaceutical agents
DE19762607789 DE2607789A1 (en) 1974-12-16 1976-02-26 PROCESS FOR THE PREPARATION OF 1-METHYL-2-(ALKYLSULFONYL)-PHENOXY-METHYL)-5-NITRO-IMIDAZOLE

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DE2607789A1 true DE2607789A1 (en) 1977-09-01

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DE19762607789 Withdrawn DE2607789A1 (en) 1974-12-16 1976-02-26 PROCESS FOR THE PREPARATION OF 1-METHYL-2-(ALKYLSULFONYL)-PHENOXY-METHYL)-5-NITRO-IMIDAZOLE

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US3700685A (en) * 1970-05-15 1972-10-24 Merck & Co Inc Nitroimidazole derivatives

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