CA1079738A - Process for the manufacture of 1-alkyl-2-(phenoxymethyl)-5-nitroimidazoles - Google Patents
Process for the manufacture of 1-alkyl-2-(phenoxymethyl)-5-nitroimidazolesInfo
- Publication number
- CA1079738A CA1079738A CA272,551A CA272551A CA1079738A CA 1079738 A CA1079738 A CA 1079738A CA 272551 A CA272551 A CA 272551A CA 1079738 A CA1079738 A CA 1079738A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- nitro
- phenoxymethyl
- imidazole
- oxidation
- 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.)
- Expired
Links
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
A process for the manufacture of 1-alkyl-2-(phenoxymethyl)-5-nitro-imidazoles of the formula I
I
wherein R1 is methyl, R2 is methylsulfonyl or ethylsulfonyl, and R3 is hydrogen, methyl or halogen, which comprises oxidising 1-methyl-2-(phenoxymethyl)-5-nitro-imidazoles of the formula II
II
wherein A is a sulfur atom or a sulfonix group (-SO-), R is methyl or ethyl, R1 methyl and R3 is hydrogen, methyl or halogen.
A process for the manufacture of 1-alkyl-2-(phenoxymethyl)-5-nitro-imidazoles of the formula I
I
wherein R1 is methyl, R2 is methylsulfonyl or ethylsulfonyl, and R3 is hydrogen, methyl or halogen, which comprises oxidising 1-methyl-2-(phenoxymethyl)-5-nitro-imidazoles of the formula II
II
wherein A is a sulfur atom or a sulfonix group (-SO-), R is methyl or ethyl, R1 methyl and R3 is hydrogen, methyl or halogen.
Description
` 1079~3~ HOE 76/F 034 Subject of German Of~enlegungsschrift No. 2,459,395 are l-alkyl-2-(phenoxymethyl)-5-nitro-.imidazoles of the formula ~2 ~R3 H2-0_ 0 2N l ~ ' wherein Rl is methyl or ethyl, R2 is trifluoromethyl, trichlo-romethyl, nitro, cyano, methylsulfonyl or ethylsulfonyl, and R3 is hydrogen, fluorine, chlorine, brom~ne, iodine, trifuoro-methyl, trichloromethyl, nitro or cyano, a process for the manufacture of these compounds, pharmaceutical products con-taining them and the use thereof.
Subject of our application filed in the Federal Republic of Germany on February 26, 1976 and laid open to public inspection as DE-OS 26 07 790 on September 8, 1977 are l-methyl-
Subject of our application filed in the Federal Republic of Germany on February 26, 1976 and laid open to public inspection as DE-OS 26 07 790 on September 8, 1977 are l-methyl-
2-~phenoxymethyl)-5-nitro-imidazoles of the formula D~ ~CH2-0 ~ F~
~ 3 ~ R2 wherein Rl is nitro, cyano, methylsulfonyl or ethylsulfonyl, and R2 is methyl or halogen, a process for the manufacture of these compounds, pharmaceutical products containing them and the use thereof.
In further development of the subject of German Offen-legungsschrift No. 2,459,395, there has now been found a pro-cess for the manufacture of l-alkyl-2-(phenoxymethyl)-5-nitro-imidazoles of the formula 1 . .
- 2 - .
', ' - ' ~ , .
:. ' . ' - ', ' . '' ,.
:: . .. . ., .. : ~ .
.... . .. . .
10 79738 ~IOE 76~F 0~4 ¢ /~ --CH2-0 ~ - R2 ~1 R
wherein R1 i8 methyl, R2 i9 methylsulfonyl or ethylsulfonyl, and R3 i8 hydrogen, methyl or halogen ~uch a~ fluorine, chlo-rine, bromine or iodine, which compri~e~ oxidi~ing 1-methyl- ~ .
2-(phenoxymethyl)-5-nitro-imidazole~ of the formula II
CH2-O~A - R II
02N ~1 R3 wherein A i~ a sulfur ~tom or a ~ulfoxide group ( -SO- ), R i~
methyl or ethyl, R1 methyl ~nd R3 l~ hydrogen, methyl or halogen such as fluorlne J chlorine, bromine or iodine.
The 1-methyl-2-(pheno~ymethyl)-5-nitro-imidazole~ of formula II used as ~tarting compounds are the sub~ect o~
German Offenlegungs~chrift No. 2,531,303. They may be ob-tained from 1-methyl-2-chloromathyl-5-nitro-imidazole (in turn obtainable aocording to German Offenlegung~chri~ten Noa, 1,595,929 and 1,470,102) and optionally ~ubstituted alkyl-mercaptophenol~ or alkyl~ul~inylphenol~ (in turn obtainable ~rom the corre~ponding mercaptophenol~ and dialkyl sul~ate with optionally ~ub~equent oxidation with perbenzolc acid) in dimethyl formamide and ln the presence of pota~ium carbonate. ~;
Suitable starting compound~ of formula II are for example 1-methyl-2-(4-methylthio-phenoxymethyl)-5-nitro-imidazole 1-methyl-2-(4-ethylthio-phenoxymethyl)-5-nltro-imidazole , : . , . , , :
.. ', . , .;",...... , : . .
.
'~.' ' ,', ~ ~
.. . . .
1079738 HOE 7S~F_o~4 t-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-, -chloro-, -bromo-, -iodo-4-methylthio phenoxymethyl)-5-nitro-imidazole 1-methyl-2-(3-fluoro-, -chloro-, -bromo-, -iodo-4-ethylthio-phenoxymethyl)-5~nitro-imidazole 1-methyl-2-(4-methyl3ulfinyl-phenoxymethyl)-5-nitro-imidazole 1-methyl-2-(4-ethyl~ulfinyl-phenoxymethyl)-5-nitro-imidazole 1-methyl-2~(3-methyl-4-methylsulfinyl-phenoxymethyl)-5-nitro-imldazole 1-methyl-2-(3-mothyl-ll-ethylsul~inyl-phenoxymethyl)-5-nltro-imidazole 1-methyl-2-(3-fluoro-, -chloro-, -bromo-, -iodo-4-methyl-sulfinyl-phenoxymethyl)-5-nitro-imidazole 1-~ethyl-2-(3-fluoro-, -chloro-, -bromo-, -iodo-4-ethylsulfinyl-phenoxymethyl)-5-nitro-imidazole.
For the oxidation, there are advantageously used molar or doubly molar amounts of an oxidation agent. In many ca4es, an excess o~ oxidation agent i~ advantageously employed.
When the correaponding sulfides (A = -S- in formuia II) are u~ed as starting materials, at least 2 molar equivalents of oxidation agent are required. When the corresponding ~ulf-oxides (A = -SO- in formula II) are used as starting compounds, one molar equivalent of oxidation agent must be employed.
Suitable oxidation agents are for example hydrogen per-oxide or peracids, for example peracetic, pertrifluoroacetic 29 acid, chloroperbenzoic acid~, eRpecially 3-chloroperbenzoic . , ' 1079738 ~!OE 76/F 034 acid, nitric acid, chromic acid and the ~alt~ thereof, chro-mic acid anhydride, permanganates, hypochlorites, chlorate~, perchlorates, periodate~ or nitric oxide~, especially dlnitro-gen tetroxide.
The oxidation reaction i~ advantageou~ly carrled out in a YolYent or di~per~ing agent. Suitable are especially tho~e solvents which are not adversely affected by the oxidation agent, ~or example scetic or trifluoroacetic acid. When per-benzoic acid i8 used, alternatively, methylene chloride or chloroform are appropriate solvent~.
The oxidation reaction i~ generally carried out at temperatures o~ rrom O to 100C, e~pecially l~o to 60C. The reaction time may vary from a few minute~ to ~ev0ral hours, depending on tho reactlon condltlon~.
The products of` the proces~ of the invention are iso-lated by diluting the reaction solution in water with simul-taneous precipitation, or by evaporating the oxganic sol~ent under reduced pres~ure. Optionally, a ~ub~equent purification may be carried out by recry~tallization from a suitable ~ol-vent or 301Yent mixture.
The following Examples illuotrate the invention.
X A M P L E ls l-methYl-Z-(4-methylsulfon~l-pheno~YmethYl)-5-nitro-imidazole 27.9 g (0.1 mol) of 1-methyl-2-(4-methylthio-phenoxy-mathyl)-5-nitro-imidazole (melting point 116 C) are dis~olved in 250 ml o~ glacial acetic acid, and 24.3 g (0.25 mol) of 35 % hydrogen peroxide are added dropwi~e with agitation at room temperature. The exothermic reaction cau~es the tempera-- 29 ture to riYe to about 45C. Subsequently, the batch iY
. . . . . .
.
., :
, ~ I
.
~79~3~ HOE 76~ 0~4 heated for 1 hour at 60 C with agitation. After cooling to room temperature, the batch i9 poured onto 800 ml of an ice/
water mixture, the precipitate i~ suction-filtQred, washed with water and recrystallized from isopropanol with addition of active charcoal. 29 g (= 93 % of the theoretical yield) of 1-methyl-2-(4-methylsulfonyl-phenoxymethyl)-5-nitro-imida20le are obtaln0d in the form of yellowish crystals having a mel-ting point (m.p.) of 157C.
In~tead of the 8 tarting product 1-methyl-2-(4-methyltio-phenoxymethyl)-5-nitro-imidazole, the corresponding -4ulfoxide, that is, 1-methyl-2-(4-methylsulfinyl-phenoxymethyl)-5-nitro-imidazole (m.p. 130C) may be employed, The u~e o~ half the amount Or hydrogen peroxide l~ ~uf`floient in thL~ ca~e, In the ~me manner, there mny be prepared~
l-methyl-2-(4-ethylsulfonyl~phenoxymethyl)-5-nitro-irnidazole m.p. 132C by oxidation of 1-methyl-2-(4-ethylthio-phenoxy-methyl)-5-nitro-imidazole (m.p. 90 C) or 1-methyl-2-(4-ethyl-sulfinyl-phenoxymethyl)-5-nitro-imidazole (m.p. tO3 C).
1-methyl-2-(3-methyl-4-methylsulfonyl-phenoxymethyl)-5-nitro-imidazole m.p. 141C by oxidation of 1-methyl-2-(3-methyl-4-methylthio-phenoxymethyl)-5~nitro-imldazole (m.p. 108C) or 1-methyl-2-(3-methyl-4-methyl~ulfinyl-phenoxymethyl)-5-nitro-lmidazole (m,p. 121C).
1-methyl-2-(3-methyl-4-ethylsulfonyl-phenoxymethyl)-5-nitro-imidazole m.p. 115C by oxidation of 1-methyl-Z-(3-methyl-4-ethylthio-phenoxymethyl)-g-nitro-imidazole (m.p. 80 C) or 1-methyl-2-(3-methyl 4-ethyl~ulfonyl-phenoxymethyl)-5-nitro--imidazole (m.p. 95C).
' 29 1-methyl-2-(3-chlero-4-methylsulfonyl-phenoxymethyl)-5-nitro-'' -; ~
~79738 HOE 76~ ~ 0~4 imidazole by oxida-tion of l-methyl-2-(3-chloro-4-methylthio-pheno~ymethyl)-5-nitro-imidazole or l-methyl-2-(3-chloro-4-methyl~ulfinyl-phenoxymethyl)-5-nitro-imidazole.
1-methyl-2-(3-chloro-4-ethylsulfonrl-phenoxymethyl)-$-nitro-imida~ole by oxidation of 1-methyl-Z-(3-chloro-4-ethylthio-pheno~ymethyl ~nitro-imidazole or 1-methyl-2-(3-chloro-4-ethylsulfinyl-pheno~y-methyl)-5-nitro-imidazola.
; ~' ' '' . :.. ,, . ' .
:. . ......... : .
.. ' , ' ' . .. ' ~, ' '
~ 3 ~ R2 wherein Rl is nitro, cyano, methylsulfonyl or ethylsulfonyl, and R2 is methyl or halogen, a process for the manufacture of these compounds, pharmaceutical products containing them and the use thereof.
In further development of the subject of German Offen-legungsschrift No. 2,459,395, there has now been found a pro-cess for the manufacture of l-alkyl-2-(phenoxymethyl)-5-nitro-imidazoles of the formula 1 . .
- 2 - .
', ' - ' ~ , .
:. ' . ' - ', ' . '' ,.
:: . .. . ., .. : ~ .
.... . .. . .
10 79738 ~IOE 76~F 0~4 ¢ /~ --CH2-0 ~ - R2 ~1 R
wherein R1 i8 methyl, R2 i9 methylsulfonyl or ethylsulfonyl, and R3 i8 hydrogen, methyl or halogen ~uch a~ fluorine, chlo-rine, bromine or iodine, which compri~e~ oxidi~ing 1-methyl- ~ .
2-(phenoxymethyl)-5-nitro-imidazole~ of the formula II
CH2-O~A - R II
02N ~1 R3 wherein A i~ a sulfur ~tom or a ~ulfoxide group ( -SO- ), R i~
methyl or ethyl, R1 methyl ~nd R3 l~ hydrogen, methyl or halogen such as fluorlne J chlorine, bromine or iodine.
The 1-methyl-2-(pheno~ymethyl)-5-nitro-imidazole~ of formula II used as ~tarting compounds are the sub~ect o~
German Offenlegungs~chrift No. 2,531,303. They may be ob-tained from 1-methyl-2-chloromathyl-5-nitro-imidazole (in turn obtainable aocording to German Offenlegung~chri~ten Noa, 1,595,929 and 1,470,102) and optionally ~ubstituted alkyl-mercaptophenol~ or alkyl~ul~inylphenol~ (in turn obtainable ~rom the corre~ponding mercaptophenol~ and dialkyl sul~ate with optionally ~ub~equent oxidation with perbenzolc acid) in dimethyl formamide and ln the presence of pota~ium carbonate. ~;
Suitable starting compound~ of formula II are for example 1-methyl-2-(4-methylthio-phenoxymethyl)-5-nitro-imidazole 1-methyl-2-(4-ethylthio-phenoxymethyl)-5-nltro-imidazole , : . , . , , :
.. ', . , .;",...... , : . .
.
'~.' ' ,', ~ ~
.. . . .
1079738 HOE 7S~F_o~4 t-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-, -chloro-, -bromo-, -iodo-4-methylthio phenoxymethyl)-5-nitro-imidazole 1-methyl-2-(3-fluoro-, -chloro-, -bromo-, -iodo-4-ethylthio-phenoxymethyl)-5~nitro-imidazole 1-methyl-2-(4-methyl3ulfinyl-phenoxymethyl)-5-nitro-imidazole 1-methyl-2-(4-ethyl~ulfinyl-phenoxymethyl)-5-nitro-imidazole 1-methyl-2~(3-methyl-4-methylsulfinyl-phenoxymethyl)-5-nitro-imldazole 1-methyl-2-(3-mothyl-ll-ethylsul~inyl-phenoxymethyl)-5-nltro-imidazole 1-methyl-2-(3-fluoro-, -chloro-, -bromo-, -iodo-4-methyl-sulfinyl-phenoxymethyl)-5-nitro-imidazole 1-~ethyl-2-(3-fluoro-, -chloro-, -bromo-, -iodo-4-ethylsulfinyl-phenoxymethyl)-5-nitro-imidazole.
For the oxidation, there are advantageously used molar or doubly molar amounts of an oxidation agent. In many ca4es, an excess o~ oxidation agent i~ advantageously employed.
When the correaponding sulfides (A = -S- in formuia II) are u~ed as starting materials, at least 2 molar equivalents of oxidation agent are required. When the corresponding ~ulf-oxides (A = -SO- in formula II) are used as starting compounds, one molar equivalent of oxidation agent must be employed.
Suitable oxidation agents are for example hydrogen per-oxide or peracids, for example peracetic, pertrifluoroacetic 29 acid, chloroperbenzoic acid~, eRpecially 3-chloroperbenzoic . , ' 1079738 ~!OE 76/F 034 acid, nitric acid, chromic acid and the ~alt~ thereof, chro-mic acid anhydride, permanganates, hypochlorites, chlorate~, perchlorates, periodate~ or nitric oxide~, especially dlnitro-gen tetroxide.
The oxidation reaction i~ advantageou~ly carrled out in a YolYent or di~per~ing agent. Suitable are especially tho~e solvents which are not adversely affected by the oxidation agent, ~or example scetic or trifluoroacetic acid. When per-benzoic acid i8 used, alternatively, methylene chloride or chloroform are appropriate solvent~.
The oxidation reaction i~ generally carried out at temperatures o~ rrom O to 100C, e~pecially l~o to 60C. The reaction time may vary from a few minute~ to ~ev0ral hours, depending on tho reactlon condltlon~.
The products of` the proces~ of the invention are iso-lated by diluting the reaction solution in water with simul-taneous precipitation, or by evaporating the oxganic sol~ent under reduced pres~ure. Optionally, a ~ub~equent purification may be carried out by recry~tallization from a suitable ~ol-vent or 301Yent mixture.
The following Examples illuotrate the invention.
X A M P L E ls l-methYl-Z-(4-methylsulfon~l-pheno~YmethYl)-5-nitro-imidazole 27.9 g (0.1 mol) of 1-methyl-2-(4-methylthio-phenoxy-mathyl)-5-nitro-imidazole (melting point 116 C) are dis~olved in 250 ml o~ glacial acetic acid, and 24.3 g (0.25 mol) of 35 % hydrogen peroxide are added dropwi~e with agitation at room temperature. The exothermic reaction cau~es the tempera-- 29 ture to riYe to about 45C. Subsequently, the batch iY
. . . . . .
.
., :
, ~ I
.
~79~3~ HOE 76~ 0~4 heated for 1 hour at 60 C with agitation. After cooling to room temperature, the batch i9 poured onto 800 ml of an ice/
water mixture, the precipitate i~ suction-filtQred, washed with water and recrystallized from isopropanol with addition of active charcoal. 29 g (= 93 % of the theoretical yield) of 1-methyl-2-(4-methylsulfonyl-phenoxymethyl)-5-nitro-imida20le are obtaln0d in the form of yellowish crystals having a mel-ting point (m.p.) of 157C.
In~tead of the 8 tarting product 1-methyl-2-(4-methyltio-phenoxymethyl)-5-nitro-imidazole, the corresponding -4ulfoxide, that is, 1-methyl-2-(4-methylsulfinyl-phenoxymethyl)-5-nitro-imidazole (m.p. 130C) may be employed, The u~e o~ half the amount Or hydrogen peroxide l~ ~uf`floient in thL~ ca~e, In the ~me manner, there mny be prepared~
l-methyl-2-(4-ethylsulfonyl~phenoxymethyl)-5-nitro-irnidazole m.p. 132C by oxidation of 1-methyl-2-(4-ethylthio-phenoxy-methyl)-5-nitro-imidazole (m.p. 90 C) or 1-methyl-2-(4-ethyl-sulfinyl-phenoxymethyl)-5-nitro-imidazole (m.p. tO3 C).
1-methyl-2-(3-methyl-4-methylsulfonyl-phenoxymethyl)-5-nitro-imidazole m.p. 141C by oxidation of 1-methyl-2-(3-methyl-4-methylthio-phenoxymethyl)-5~nitro-imldazole (m.p. 108C) or 1-methyl-2-(3-methyl-4-methyl~ulfinyl-phenoxymethyl)-5-nitro-lmidazole (m,p. 121C).
1-methyl-2-(3-methyl-4-ethylsulfonyl-phenoxymethyl)-5-nitro-imidazole m.p. 115C by oxidation of 1-methyl-Z-(3-methyl-4-ethylthio-phenoxymethyl)-g-nitro-imidazole (m.p. 80 C) or 1-methyl-2-(3-methyl 4-ethyl~ulfonyl-phenoxymethyl)-5-nitro--imidazole (m.p. 95C).
' 29 1-methyl-2-(3-chlero-4-methylsulfonyl-phenoxymethyl)-5-nitro-'' -; ~
~79738 HOE 76~ ~ 0~4 imidazole by oxida-tion of l-methyl-2-(3-chloro-4-methylthio-pheno~ymethyl)-5-nitro-imidazole or l-methyl-2-(3-chloro-4-methyl~ulfinyl-phenoxymethyl)-5-nitro-imidazole.
1-methyl-2-(3-chloro-4-ethylsulfonrl-phenoxymethyl)-$-nitro-imida~ole by oxidation of 1-methyl-Z-(3-chloro-4-ethylthio-pheno~ymethyl ~nitro-imidazole or 1-methyl-2-(3-chloro-4-ethylsulfinyl-pheno~y-methyl)-5-nitro-imidazola.
; ~' ' '' . :.. ,, . ' .
:. . ......... : .
.. ' , ' ' . .. ' ~, ' '
Claims (7)
PROPERTY OR PRIVILEGE IS CLAIMED OR DEFINED AS FOLLOWS:
1. A process for the preparation of a 1-alkyl-2-(phenoxy-methyl)-5-nitro-imidazole of the formula I
I
wherein R1 is methyl, R2 is methylsulfonyl or ethylsulfonyl, and R3 is hydrogen, methyl or halogen, in which a 1-methyl-2-(phenoxymethyl)-5-nitro-imidazole of the formula II
II
wherein 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, is oxidized with an oxidizing agent.
I
wherein R1 is methyl, R2 is methylsulfonyl or ethylsulfonyl, and R3 is hydrogen, methyl or halogen, in which a 1-methyl-2-(phenoxymethyl)-5-nitro-imidazole of the formula II
II
wherein 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, is oxidized with an oxidizing agent.
2. A process as claimed in claim 1 in which A represents sulfur and the oxidizing agent is used in an amount of two molar equivalents.
3. A process as claimed in claim 1 in which A represents a sulfoxide group and the oxidizing agent is used in an amount of one molar equivalent.
4. A process as claimed in claim 1, claim 2 or claim 3 in which the oxidizing agent is selected from the group of hydrogen peroxide, peracetic acid, pertrifluoroacetic acid, chloroperbenzoic acids, nitric acid, chromic acid and the salts thereof, chromic acid anhydride, permanganates, hypochlorites, chlorates, perchlorates, periodates and nitric oxides.
5. A process as claimed in claim 1, claim 2 or claim 3 in which the oxidation is carried out in the presence of an inert solvent or dispersing agent.
6. A process as claimed in claim 1, claim 2 or claim 3 in which the oxidation is carried out at a temperature of from 0 to 100°C.
7. A process as claimed in claim 1, claim 2 or claim 3 in which the oxidation is carried out at a temperature of from 40 to 60°C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762607789 DE2607789A1 (en) | 1974-12-16 | 1976-02-26 | PROCESS FOR THE PREPARATION OF 1-METHYL-2-(ALKYLSULFONYL)-PHENOXY-METHYL)-5-NITRO-IMIDAZOLE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1079738A true CA1079738A (en) | 1980-06-17 |
Family
ID=5970911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA272,551A Expired CA1079738A (en) | 1976-02-26 | 1977-02-24 | Process for the manufacture of 1-alkyl-2-(phenoxymethyl)-5-nitroimidazoles |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT361468B (en) |
| CA (1) | CA1079738A (en) |
| CH (1) | CH624942A5 (en) |
| DK (1) | DK144524C (en) |
| EG (1) | EG13828A (en) |
| ES (1) | ES456117A2 (en) |
| FI (1) | FI770599A (en) |
| IT (1) | IT1115608B (en) |
| LU (1) | LU76834A1 (en) |
| NL (1) | NL7701838A (en) |
| NO (1) | NO770648L (en) |
| SE (1) | SE7702126L (en) |
-
1977
- 1977-02-21 NL NL7701838A patent/NL7701838A/en not_active Application Discontinuation
- 1977-02-21 ES ES456117A patent/ES456117A2/en not_active Expired
- 1977-02-23 EG EG111/77A patent/EG13828A/en active
- 1977-02-24 CH CH231377A patent/CH624942A5/en not_active IP Right Cessation
- 1977-02-24 IT IT20658/77A patent/IT1115608B/en active
- 1977-02-24 CA CA272,551A patent/CA1079738A/en not_active Expired
- 1977-02-24 FI FI770599A patent/FI770599A/fi not_active Application Discontinuation
- 1977-02-24 LU LU76834A patent/LU76834A1/xx unknown
- 1977-02-25 DK DK84177A patent/DK144524C/en not_active IP Right Cessation
- 1977-02-25 AT AT128477A patent/AT361468B/en not_active IP Right Cessation
- 1977-02-25 SE SE7702126A patent/SE7702126L/en unknown
- 1977-02-25 NO NO770648A patent/NO770648L/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK84177A (en) | 1977-08-27 |
| ES456117A2 (en) | 1978-03-01 |
| LU76834A1 (en) | 1977-09-26 |
| ATA128477A (en) | 1980-08-15 |
| SE7702126L (en) | 1977-08-27 |
| DK144524C (en) | 1982-09-06 |
| AT361468B (en) | 1981-03-10 |
| NL7701838A (en) | 1977-08-30 |
| EG13828A (en) | 1982-09-30 |
| DK144524B (en) | 1982-03-22 |
| CH624942A5 (en) | 1981-08-31 |
| FI770599A (en) | 1977-08-27 |
| IT1115608B (en) | 1986-02-03 |
| NO770648L (en) | 1977-08-29 |
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