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United States Patent Office Patiented July 5, 1960 2,944,061 United States Patent Office Patiented July 5, 1960 1. 2 sponding alcohols (X=H) by known methods of esteri 2,944,061 fication, in particular, by the action of an acid chloride in the presence of pyridine. CERTAIN INTRO MDAZOLEALKANOLS AND By the words “known methods” as used in this specifi ACYL DERVATIVES AND PROCESS cation and accompanying claims is meant methods hereto Robert Michel Jacob, Ablon-sur-Seine, Gilbert Louis fore employed or described in the chemical literature. Regnier, Paris, and Corne Crisan, Sceaux, France, The imidazole derivatives of the aforesaid formula pos assignors to Societe des Usines Chimiques Rhone sess valuable chemotherapeutic properties; in particular, Poulenc, Paris, France, a French body corporate they have utility in the treatment of infections due to path O ogenic protozoa such as certain species of amoebae (for No Drawing. Filled Jan. 8, 1959, Ser. No. 785,577 example Endamoeba histolytica) or trichomonas (for ex Claims priority, application France Sept. 20, 1957 ample Trichomonas vaginalis). They have a very low toxicity. 8 Claims. (C. 260-309) For therapeutic purposes, the new imidazoles are pref This invention relates to new imidazole derivatives and 5 erably employed as such or in the form of acid addition processes for their preparation. It is a continuation-in salts containing anions which are relatively innocuous part of application Serial No. 731,108, filed April 28, to the animal organism in therapeutic doses of the salts 1958, now abandoned. (such as hydrochlorides and other hydrohalides, phos According to the present invention there are provided phates, nitrates, sulphates, maleates, fumarates, citrates, 20 tartrates, methanesulphonates and ethanedisulphonates) new imidazoles conforming to the general formula: so that the beneficial physiological properties inherent in S the bases are not vitiated by side-effects ascribable to the C-R. anions. The following examples illustrate the invention. oN--y 25. Al-OX Example I wherein R represents a hydrogen atom or an alkyl group 2-methyl-4(or 5)-nitroimidazole (127 g.) is heated containing up to five carbon atoms (preferably methyl or with ethylene chlorohydrin (795 g.) for 18 hours at 128 ethyl), A represents a divalent saturated straight or 130 C. and the chlorohydrin (660 g.) is then distilled branched chain aliphatic hydrocarbon group containing 30 under reduced pressure (30 mm. Hg). The residue is two to four carbon atoms and X represents a hydrogen treated with water (300 cc.) and filtered, and the filtrate atom or an acyl residue of a monocarboxylic or dicar is made alkaline by the addition of sodium hydroxide boxylic aliphatic or aromatic acid, and acid addition salts solution (d=1.33, 100 cc.). It is then extracted with thereof. chloroform (1,000 cc.) and, after evaporation of the Since large numbers of monocarboxylic and dicar 35 chloroform in vacuo, there is obtained a pasty mass (77 boxylic aliphatic and aromatic acids are known it is im g.) which is recrystallised from ethyl acetate (450 cc.) possible to list them exhaustively. The general utility in the presence of animal charcoal. There is thus ob of acids in these classes is however exemplified by the tained 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole (24 examples which follow wherein the ester groupings are g.) as a creamy white crystalline powder melting at selected over a wide range of such acids, e.g. lower ali 40 158-160° C. phatic monocarboxylic acids such as acetic acid and di - Example II chloroacetic acid, higher aliphatic monocarboxylic acids 2-methyl-4(or 5)-nitroimidazole (12.7 g.) and 3-benzyl such as pivalic acid and stearic acid, aliphatic dicarboxylic oxypropyl toluene-p-sulphonate (32 g.) (M.P. 33 C.) acids such as succinic acid, aromatic monocarboxylic acids are heated for 2 hours at 135 C. When the reaction such as benzoic acid and its substitution derivatives such 45 is complete, the reaction mixture is cooled to 25 C. and as salicylic acid, chlorobenzoic acids, methoxy benzoic then agitated with hydrochloric acid (50 cc.). The 3 acids and nitrobenzoic acids, and aromatic dicarboxylic benzyloxypropyl toluene-p-Sulphonate which has not re acids, of which the phthalic acids are the most readily acted is extracted with ether and the acid liquors are available examples. made alkaline with potassium carbonate. According to a feature of the present invention, com 50 The suspension obtained is filtered to remove unreacted pounds of the aforesaid general formula in which X is a 2-methyl-4(or 5)-nitroimidazole starting material which hydrogen atom, are prepared by reacting in the absence is washed several times with water and then with chloro of a basic condensing agent a 4 (or 5)-nitroimidazole with form. The filtrate is then decanted and extracted with a compound of the general formula Z-A-OY wherein chloroform. The chloroformic extracts are combined, Z represents an acid residue of a reactive ester selected 55 dried over anhydrous potassium carbonate and then evap from a halogen atom and the acid residues of sulphuric orated under reduced pressure. A crude oily product and sulphonic esters, Y represents a hydrogen atom or a (22 g.) is obtained. radical which is readily replaceable by a hydrogen atom, The crude product is dissolved in 15% hydrochloric for example a tetrahydropyranyl or benzyl group, and acid (110 cc.) and debenzylation is effected by heating A is as hereinbefore defined and, where Y is other than 60 a hydrogen atom, liberating the hydroxyl group by known this solution for 5 hours under reflux. After cooling, the methods, e.g. by acid hydrolysis when Y is tetrahydro solution is extracted several times with chloroform and pyranyl or benzyl. the acid liquors are then made alkaline with potassium According to a further feature of the present inven carbonate. They are then extracted several times with tion, compounds of the aforesaid general formula in 65 chloroform and the chloroformic solutions are dried over which X is an acyl group, are prepared from the corre anhydrous potassium carbonate. After evaporation of 2,944,061 - - - - - - 3. 4. the solvent under reduced pressure a crude oily base (7 to the solution and a white precipitate is formed which g.) is obtained. is separated and some of the initial 1-(2-hydroxyethyl)- By the addition of ethereal hydrogen chloride to a solu 2-methyl-5-nitroimidazole is thus recovered. The filtrate tion of the base in acetone followed by recrystallisation is decanted and the chloroform solutions are washed from a mixture of ethanol and ether of the crystals ob 5 Several times with water and then with a 10% solution tained, there is finally obtained 1-(3-hydroxypropyl)-2- of sodium bicarbonate. After drying the chloroform methyl-5-nitroimidazole hydrochloride (4 g.), M.P. solution over anhydrous sodium sulphate and evaporat 115° C. ing the solvent, a crude oily base (9.7 g.) is obtained. Example III After dissolving the latter in benzene and repeatedly ex 0. tracting the solution with 15% hydrochloric acid, the 2-ethyl-4(or 5)-nitroimidazole (23.8 g.) and benzyl acid fractions are combined and made alkaline with oxyethyl toluene-p-sulphonate (51.7 g) (M.P. 43° C.) potassium carbonate. They are then extracted several are heated for 3 hours at 135°. C. After treatment of times with chloroform and the combined chloroformic the reaction products as in Example I a crude oily prod solutions are dried over anhydrous sodium sulphate. uct (26.2 g.) is obtained which is debenzylated by boiling After evaporation of the solvent, the crude base obtained in 15% hydrochloric acid (130 cc.). On treatment of 5 is purified by dissolving it in -ethanol and adding ethereal the hydrochloric acid solution a crude crystalline base hydrogen chloride. There is finally obtained 1-(2-sali (8.2 g.) is obtained which is purified by recrystallisation cyloyloxyethyl)-2-methyl-5-nitroimidazole hydrochloride, from a mixture of ethyl acetate and heptane. There is M.P. 154 C. ". - - - . finally isolated 1-(2-hydroxyethyl)-2-ethyl-5-nitroimidaz 20 Example IX ole (7.25 g.), M.P. 87-88 C. 14.7 g of benzoyl chloride dissolved in 30 cc. of Example IV chloroform are poured into a cold solution of 17.1 g. 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole (8.55g.) of 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole in 200 is suspended in anhydrous chloroform (100 cc.). - An cc. of chloroform, and 8.3 g. of pyridine are added so hydrous pyridine (4.15 g.) is added and, after cooling to 25 that the temperature remains in the neighbourhood of 5 5 C., dichloroacetyl chloride (7.75 g) is added drop C. The mixture is then agitated for 1 hour at room tem wise over 20 minutes. When the addition is complete, perature, 100 cc. of water are added and the insoluble the temperature is allowed to rise to 15° C. and the matter is filtered off. The organic layer is decanted and - i mixture is then boiled for 1 hour. The chloroform washed with 50 cc. of a 10% sodium bicarbonate solu Solution is then cooled and washed several times with 30 tion and then with 100 cc. of water. The solvent is Water. After evaporation of the solvent the crude ester driven off on the water bath and there are obtained 21 g. obtained is purified by successive recrystallisations from of a white crystalline residue, which is recrystallised from a mixture of benzene and heptane and then from di-iso cyclohexane. There are thus obtained 15 g. of 1-(2- propyl ether. - - benzoyloxyethyl)-2-methyl-5-nitroimidazole, which is a There is finally obtained 1-(2-dichloroacetoxyethyl)-2- 35 white crystalline powder, M.P.
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