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United States Patent Office Patented July 19, 1960

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United States Patent Office Patented July 19, 1960 . 2,945,860 United States Patent Office Patented July 19, 1960 2 formic acid carbethoxy-methyl ester, chloro-formic acid 2,945,860 butoxy-ethyl ester, chloro-formic acid chlorethyl ester, chloro-formic acid phenyl ester, chloro-formic acid NEW PIPERAZENE-CARBOXYLIC ACID ESTERs methoxy-phenyl ester, chloro-formic acid propoxy-phenyl AND PROCESS OF PREPARNG THEM ester, chloro-formic acid benzyloxy-phenyl ester, chloro Dieter Schmidt-Barbo, Hofheim (Taunus), Friedrich formic acid carbo-benzyloxyphenyl ester, chloro-formic Hampe, Bad Soden (Taunus), and Manfred Schorraid acid tolyl ester, chloro-formic acid nonyl-phenyl ester and Georg Lämmler, Frankfurt am Main, Germany, assig chloro-formic acid chloro-phenyl ester. ors to Farb werke Hoechst Aktiengesellschaft vormals The process according to the invention can be carried Meister Lucius & Bruning, Frankfurt an Main, Ger O -out by reacting 1-(3'-halogeno-4'-methyl-phenyl)piper many, a corporation of Germany azines with halogen-formic acid esters. In this case it is No Drawing. Filed Mar. 7, 1958, Ser, No. 719,757 advisable to operate in the presence of a solvent. As such there may for example be used hydrocarbons such Claims priority, application Germany Mar. 8, 1957 as benzine or benzene, halogen hydrocarbons such as 5 methylene chloride or chloroform, ethers such as diethyl 7 Claims. (CI. 260-268) - ether or di-isopropyl ether or ketones such as acetone. It is known that certain piperazine derivatives have In order to obtain the end products in good yields, it is of gained special importance for the control of blood para advantage to add basic compounds such as alkali metal sites. The 1-diethyl-carbamino-4-methyl-piperazine, for carbonates, alkali metal bicarbonates or tertiary amines example, is effective against filariae. In addition, certain 20 for binding the hydrohalic acid that is set free. The re 2-halogeno-4-amino-alkylamino-toluenes are active against action can be carried out at slightly reduced or slightly schistosome infections. Furthermore, basically substi raised temperatures. It is of advantage to operate tuted 4-halogeno-2-amino-1,3,5-trimethyl-benzenes have attemperatures ranging between -10 C. and H10 already been recommended as medicaments against C. and to remove the reaction heat set free by means of schistosome infections. ... 25 a cooling bath. - - The present invention relates to new piperazine-car If the hydrocarbon radical R. of the piperazine-car boxylic acid esters which are active against schisto boxylic acid esters thus obtained is substituted by one or somiasis and correspond to the general formula several reactive groups, further reactions can be carried out with these. Thus, it is for example possible to trans Hall. 30 form a benzyl ester or benzyl ether by catalytic hydro genation into a free carboxyl or hydroxyl group or to re-K -N ... aN-C-O-O-O-R ... replace a halogen atom by an arnino group by treatment in which Hal stands for a halogen atom, preferably with ammonia or a primary or secondary amine. chlorine, and R for an aliphatic, aromatic or mixed ali The piperazine-carboxylic acid esters obtained accord phatic-aromatic hydrocarbon radical which may also be 35 ing to the invention represent colorless crystalline sub substituted by halogen atoms, amino, ether and/or free stances or very viscous oils which are practically insolu or esterified carboxyl groups. ble in water but are as a rule easily soluble in organic The present invention relates also to a process for the solvents, in oils and in fats. However, if the Substances preparation of such piperazine-carboxylic acid esters by contain a basic or acid group, it is possible to obtain reacting 1 - (3'-halogeno-4'-methyl-phenyl)-piperazines 40 water-soluble substances by salt formation, for example with halogen-formic acid esters of the general formula with alkali metal hydroxides or inorganic or organic acids. X-CO-O-R, in which R has the indicated significa According to the process of the present invention there tion and X stands for a halogenatom, preferably chlorine, is obtained a new group of compounds which are valuable and by transforming any benzyl ester or benzyl ether medicaments. They are particularly suitable for the groupings by catalytic hydrogenation into carboxyl or 45 control of schistosome infections in warm-blooded ani hydroxyl groups or by replacing any halogen atoms that mals. As compared with other substances being active may be present by a corresponding amino group by treat against schistosomiasis, they are very well tolerable and ment with ammonia, primary or secondary amines. can be administered parenterally. The 1-(3'-halogeno-4'-methyl-phenyl)-piperazines used The products of the present invention are particularly as starting material may for example be prepared ac 50 suitable for parenteral administration and for this pur cording to the processes described in U.S. patent applica pose they can either be dissolved in oils, for example tion Ser. No. 522,858, now U.S. Patent 2,830,056, by olive oil or neat's-foot oil, or-as far as they form lieu reacting para-toluidines substituted in the nucleus With tral, water-soluble salts--also in water. reactive esters of diethanolamine or by reacting para In the following table there are compared two of the toluidines substituted in the nucleus with ethylene oxide 55 claimed compounds (Nos. 1 and 2) with 3 known com or ethylene halogen-hydrins and transforming the primary pounds (Nos. 3, 4 and 5) of comparable constitution as alcohol groups of the condensation products into reactive regards their activity in schistosome infections. The tests ester groups and reacting the esters with ammonia or by were carried out in the following way: reacting 3-nitro-4-halogen-toluenes substituted in the Albino mice are each infected subcutaneously with nucleus with piperazine, reducing the nitro-group to the 60 about 40 cercariae of the strain Liberia of Schistosoma amino group, transforming the latter into the diazonium manisoni. Upon termination of the period of pre-potency group, replacing this in usual manner by hydrogen or and determination of the discharge of eggs in the feces, subjecting it to the Sandmeyer reaction. - the mice are treated with the substance to be tested. As halogen-formic acid esters there may for example The result of the treatment is controlled by consecutive be used chloro-formic acid methyl ester, chloro-formic 65 examinations of the feces and on the 60th day after acid ethyl ester, chloro-formic acid isopropylester, chloro the treatment the mice are dissected. The dosis curativa formic acid amyl ester, chloro-formic acid isoamyl ester, is that dose of the compound which kills all worms in chloro-formic acid diethyl-amino-ethyl ester, chloro the mice infected with Schistosoma mansoni. -- - - 1. 2,945,860 Maximum Dosis tolerated curativa Chemo No Compound Administration dose per per 20 g. thera 20g. of of mouse, peutic mouse, Ing. index Ing. i------ 1-(3'-chloro-4'-methylphenyl)-piperazine-4-carboxylic acid-(2'- (Stegutaneously >40 2.0 >20 methoxy-4'-allyl-phenyl) ester. Per OS----------- >40 2.) >20 2------ 1-(3'-chloro-4'-methylphenyl)-piperazine-4-carboxylic acid-(3'- (Sigtaneously >40 3.0 >13 chloro-4'-methyl-phenyl) ester. Per OS----------- >40 2.0 >20 3------ 2-chloro-4-diethylamino-ethylamino-toluene hydrochloride.----- per OS-- 5-7 2.2 2.2-3.2 4------ 2-hletiethylamino-ethylamino-1,3,5-trimethyl-benzene hy- per os. 5-7 0.7 7-10 rochloride. - 5------ 1-(3'-chloro-4'-methyl-phenyl)-piperazine maleate.....----------. PCOS.----------- 4-6 0.5 8-2 The comparison of the test results clearly shows the EXAMPLE 4 improved schistosomicidal activity of the products of 15 the present invention. The superiority of these piperazine 1-(3'-chloro-4'-methyl-phenyl) - piperazine - 4-carboxylic carboxylic acid esters consists furthermore in the fact acid isoamyl ester that they are also very effective in mice, cotton rats By reacting 15 grams of chloroformic acid isoamyl and monkeys when administered parenterally and that ester according to the directions given in Example 1 the they are well tolerated locally when administered intra 20 1-(3'-chloro-4'-methyl-phenyl) - piperazine-4-carboxylic muscularly in the form of oily solutions or aqueous acid isoamyl ester is obtained in the form of an oil, suspensions. which cannot be distilled under a reduced pressure of The following examples serve to illustrate the invention 2 mm. Hg and up to 200 C. - but they are not intended to limit it thereto: 25 EXAMPLE 5 EXAMPLE 1. 1-(3'-chloro-4'-methyl-phenyl)-piperazine - 4 - carboxylic 1-(3'-chloro-4'-methyl-phenyl)piperazine-4-car acid phenyl ester boxylic acid methyl ester To a solution of 10.5 grams of 1-(3'-chloro-4'-methyl To a solution cooled to -5° C. of 21 grams of 1-(3' 30 phenyl)-piperazine and 5 grams of triethylamine in 50 chloro-4'-methyl-phenyl)-piperazine (colorless oil boil cc. of benzene there are added at 0-10 C., while stirring ing at 136-137 C, under a pressure of 0.5 mm. of mer and cooling, 7.5 grams of chloroformic acid phenyl ester. cury) in 100 cc. of benzene, to which 10 grams of tri A precipitate of triethylamine hydrochloride separates at ethyl amine have been added, there are added dropwise once. After stirring for another 2 hours, water is added within 45 minutes, while stirring and cooling with ice to the reaction mixture. The benzene layer is eliminated water, 10 grams of chloro-formic acid methyl ester. in the separating funnel, washed with water, dried and The whole is stirred for another 2 hours while the tem the benzene is distilled off.
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