IL31802A - (p-amino alkyl phenylsulphonyl)-2-imino-imidazolidine derivatives and process for their preparation - Google Patents

Description

alkyl imidazolidine derivatives and process for their preparation GEIGY SWITZERLAND The present invention relates to new derivatives of processes for their prepara medicaments containing the new compounds and their use More the invention concerns pounds in which m is 2 or is an group with not more than 12 carbon an alkenyl group with 3 to 5 carbon a or with not more than 7 carbon atoms or a phenylalkyl group with not more than 9 carbon is hydrogen or an alkyl group with not more than 2 carbon is an alkyl group or chloroalkyl group with not more than 7 carbon an alkenyl group with not more than 5 carbon a with not more than 8 carbon a phenyl group or a alkyl or phenylalkenyl group with not more than 10 carbon wherein the phenyl group can be to by halogen of atomic number trifluoromethyl alkyl groups with not more than 4 carbon hydroxyl alkoxy or alkylthio groups with not more than 2 carbon and is hydrogen or the methyl and their pharmaceutically acceptable acid addition The new compounds of the invention have been found to have hypoglycemic activities which are illustratively strated in rats by orally administering the test compound to groups of 5 to 6 animals which have not been fed for 24 Blood samples are taken from a vein of the animal and the blood sugar content is determined according to the method of with an autoanalyser Thus it is shown that amounts of from 20 to 400 of bodyweight has a pronounc blood sugar lowering Similar hypoglycemic activities are found with the preferred and The toxicity of the compounds of the invention on oral administration as demonstrated in rats is of favorable low These properties render the compounds of the invention suitable for the treatment of In the compounds of general formula can have the following as alkyl the 2 decyl or the dodecyl as alkenyl the butenyl or pentenyl or alkylcycloalkyl as the and cyclohexyl or the cycloheptyl or as group the or the as phenylalkyl the phene or the The substituent as alkyl group can be the methyl or ethyl group and the substituent as alkyl group can be the alkyl groups named under with not more than 7 carbon as chloroalkyl the or the or as the cyclobutylmethyl cycloheptylmethyl or the cyclooctyl group and as groups the or the cyclooc group as phenylalkyl or phenylalkenyl the phenylpropyl phenylbutyl the styryl The phenyl group appearing in the definition of may be to This substituent or these substituents can be the following as fluorine or as lower alkyl the butyl or the butyl as alkoxy or alkylthio the thio or the ethylthio According to the inventive method for preparation compounds of general formula I are prepared by reaction a reactive functional derivative of a sulfonic acid of general formula II in which and have the meaning given under formula I with a compound of general formula III in which and R have the meaning given under formula I if the reaction product can be converted with an inorganic or organic acid into an addition As reactive functional derivative of a sulfonic acid of general formula II are a particularly a or also an anhydride of general formula Ila 0 in which and have the meaning given under formula I The reaction is preferably carried out in the presence of an inert organic which is miscible or inmiscible with in the presence or the absence of able inert organic solvents are such as toluene or etherlike solvents such as dioxane or chlorinated hydrocarbons such as enechloride and lower ketones such as acetone or It is preferable to add an acid binding agent to the reaction As such are suitable inorganic bases or alkalimetal alkalimetal carbonates or alkalimetal such as the corresponding sodium or potassium there can also be used organic bases such as trimethyl or or collidine which are added in excess or which can also be used as Starting materials of general formula II are compounds in which and are as defined under corresponding to the sulfonic acids of formula One group of formula wherein is a lower can be prepared by reaction of lower aliphatic carboxamides which are substituted on the nitrogen atom by the phenylethyl or by the phenylpropyl group with sulfonic corresponding to the sulfonic acids A second group of sulfonyl general wherein is an optionally substituted phenyl group may be prepared by reacting an optionally substituted benzoylchloride with i or with to obtain the corresponding and These nitro compounds are reduced with iron powder in hydrochloric acid to the corresponding and The reaction products are finally diazotised with sodium rite in hydrochloric acid and the diazonium salt solution is added to a solution of cupric chloride in water and glacial acetic acid which is saturated with sulfur According to a second inventive method for the compounds of general formula I are prepared by the reaction of an acid of general formula IV in which has the meaning given under l or a reactive functional derivative of such an acid with a compound of general formula V in which R2 and have the meaning given under formula I if the compound obtained is converted with an inorganic or organic acid into an addition The acylation and benzoylation respec tively of compound V is carried out in a known by reaction of the corresponding acid halogenides or preferably in the presence of an acid binding or water binding agent or by treatment with reactive acid The reaction is preferably carried out in the presence of an inert organic Suitable inert organic solvents are hydrocarbons such as toluene or solvents such as dioxane or chlorinated hydrocarbons such as methylenechloride and lower such as acetone or It is preferable to add to the reaction solution an acid binding such as inorganic bases or alkalimetal alkalimetal hydrogencarbonates metal carbonates or alkalimetal such as the corresponding sodium or potassium there can be used organic bases such as or triethylamine ethylamine or collidine which can be used as solvent if added in To carry out these an acid of general formula IV is reacted with a compound of general formula V in the presence of a carbodiimide such as carbodiimide in an inert solvent such as Lower the methyl ester or the ethyl ester of the acids of general formula IV yield on heating with compounds of general formula the corresponding amides of general formula An alternative form of the method for the paration of a halogenide or in a mixed is to react a carbonic acid half ester with compound of general formula preferably in the presence of an acid binding a strong organic base like pyridine or if added in can also serve as the reaction Reactive esters of acids of general formula IV are the and the The starting materials of general formula V mentioned above are obtained hydrolysis of the pounds falling under the general formula la in which and have the meaning given under formula According to another method for one obtains starting materials of general formula V by tion of substituted of general formula VI in which the symbols m and have the meaning given under formula I with substituted in alkaline medium Miller et Soc 2101 According to a third method for compounds of general formula I are prepared by condensation of compound of general formula VII in which and have the meaning given und formula and is an or a triarylmethyl the methyl or the with a reactive cyanic acid derivative under ring closure and optionally under cleavage of a halogenide if the compound obtained is converted with an inorganic or organic acid into an addition is preferably the benzhydryl or the trityl As reactive cyanic acid there are most suitable cyanogenhalides such as cyanogenchloride or cyanogenbromide or cyanic acid particularly cyanic acid phenyl The reaction is preferably carried out in the presence of an inert organic solvent which is or with in the presence or absence of Suitable inert organic solvents are hydrocarbons such toluene or lower such as methanol or solvents such as dioxane or chlorinated j carbons such as lower such as acetone or carbonic acid esters such as ethyl carbonic acid nitriles such as or such as The reaction can be carried out in the presence or absence of an acid binding As acid binding agents there are suitable inorganic bases or salts such as alkalimetal alkalimetal gencarbonates alkalimetal carbonates or alkalimetal the corresponding sodium or potassium there can also be used calcium carbonate calcium phosphate and magnesium As starting materials of general formula there are most suitable such compounds in which the symbols are in accordance with the symbols which are named after formula to A group of such starting materials are the benzene ring of which is substituted in carboxamidoalkyl position by the group According to a fourth inventive method for compounds of general formula I are prepared by condensing a compound of general formula VIII in which and have the same meaning as defined under formula with a reactive ester of a hydroxy compound of general formula IX in which and R2 have the same meaning given under formula I under ring closure if the compound obtained is converted with inorganic or organic acid into an addition Suitable reactive esters of hydroxy compounds of general formula IX particularly chlorides or additional sulfonic acid the or sulfonic acid ester or the methane sulfonic acid The condensation is preferably carried out in a solvent which is miscible or inmiscible with in the presence or absence of As there can be used solvents diethyleneglycolmonomethyl carbonic acid amides such as or such as It is preferable to carry out the condensation in the presence of an acid binding As such can be used compounds which are named after the third method for also there can be used organic bases such As starting materials for the fourth method for preparation there can be used reactive esters which have been named before of a hydroxy compound of general formula IX which symbols and are in accordance with the symbols which are named after formula A group of bromides of general formula IX may be prepared if a Heterocyclic Compounds with Three and Part John Wiley Sons London is reacted with cyanogen bromide in According to a fifth inventive method for compounds of general formula I are prepared by condensation and cyclization of a reactive ester of which have the meaning given under formula I with an amine of general formula XI H2 in which has the same meaning given under formula if desired the compound obtained can be converted with inorganic or organic acids into an acid addition Suitable reactive esters of a hydroxy compound of general formula X particularly chlorides or or sulfonic acid larly a benzene sulfonic acid ester which is substituted carbox in by group The condensation is preferably done in a As such there are suitable the same solvents which are named in the fourth method for The reaction is preferably carried out in the presence of an acid binding As an acid binding agent there is most suitable an excess of bases of general formula As starting materials for this method for there are suitable reactive esters which have been named before of hydroxy compounds of general formula which syiabols and are in accordance with the symbols which are named after formula A group of such compounds can be prepared in the following One starts with aziridine and reacts this with cyanogen bromide in ether to obtain the this cyanamide is condensed in acetone with a benzenesulfonylchlorxde which is substituted in by the group in the presence of diluted sodium hydroxide under separation of hydrogen chloride to yield the corresponding According to a sixth compounds of general formula I which is only hydrogen are prepared by tion of compounds of general formula XII in which and have the same meaning given under formula I with chloral if the compounds obtained can be converted with an inorganic or organic acid into an addition The formylation is done according to 3933 in an inert in toluene or chlorinated hydrocarbons Starting materials of general formula XII are prepared according to the methods as they are described after the second method for preferably by hydrolysis of the corresponding substituted of general formula The compounds of general formula I which are prepared according to the inventive method for preparation are converted if desired into the salts with inorganic or organic The preparation of these salts can be done by reaction of compounds of general formula I with an equivalent amount of acid in a suitable or inorganic solvent like chloroform or For use as medicaments instead of the free compounds of the general formula their pharmaceutically acceptable salts with acids may be Suitable addition salts are salts with hydrochloric hydrobromic sulfuric phosphoric methanesulfonic ethanesulfonic sulfonic acetic lactic oxalic succinic fumaric maleic hydrox succinic tartaric citric salicylic acetic mandelic acid and embonic addition salts with blood sugar depressing sulfonyl ureas and The new compounds are preferably administered The daily doses are between 30 and 300 mg for adult patients with normal Suitable dosage forms like and contain preferably 30 to 300 mg of a compound of the 20 to of a compound of general formula or a pharmaceutically acceptable acid addition salt For their the active compound is with a solid powdery carrier like such as potato corn starch or also laminaria powder or citrus pulp cellulose derivatives or if desired under addition of sliding agents like magnesium or calcium stearate or polyethylene glycols to form tablets or dragees The are coated with concentrated solutions of sugar which may also contain some arabic talc or titan dioxide or with a volatile organic solvent or mixtures of soluble solvents which It is possible to add to these coatings pigments to mark different doses of the active As other oral dosage forms there are suitable capsules of gelatine and a softening agent like Plugged capsules contain the active ingredient preferably as granulate in mixture with fillers like corn starch or sliding agents like talc or magnesium stearate if stabilizers like sodium or ascorbic In the soft capsules the active ingredient is ferably dissolved or suspended in suitable solvents like liquid polyethyleneglycols whereby if desired stabilizers can be The following methods for preparation describe the preparation of tablets and dragees in more 1000 g of are mixed together with 500 g lactose and 270 g of potato The mixture is moistened with an aqueous solution of g gelatine and granulated through a After it is mixed together with g potato g g magnesium stearate and g colloidal silicon After the mixture is pressed into each of which has a weight of 200 and contains 100 active if the tablets may be grooved for better adaptation to From g g lactose and the aqueous solution of g a late is prepared which after drying is mixed together with g colloidal silicon g g potato starch and g magnesium stearate and pressed into dragee These are coated afterwards with a concentrated syrup of g crystalline g g gummi 250 g 20 g colloidal silicon dioxide and g dye and The dragees obtained each weigh 240 mg and each contain 100 mg active ingredient The following examples describe the preparation of the new compounds of formula I and of intermediates which are not known so but they are not the only way to prepare The temperatures are given in Example 1 One adds g ride to g sodium hydroxide in 85 ml To the obtained clear solution are added g dissolved in 100 whereby the shows a rise in is heated for an hour to and then evaporated in e residue is from ethyl acetate and the pure is obtained a Accordingly one obtains g 1 and 24 g the 1 g g the 1 tyraraidoethyl g 1 and g e the 1 hyl 1 g 1 and g i the 1 1 0 g he 1 yrarai henyl s ulf 2 in g and g ethyl 2 or i o e t hyl 1 2 g 1 and g onyl the g and g onylchloride the 1 f 1 ine p g and g e opyl ene s ulf onyl c hi or id e the 1 g 1 and g onylchloride the 1 g and g onylchloride the 1 buty and g d o e thyl ene c the 1 g 1 and G ethy ene s c hi id e the 1 g 1 and g i the 1 g and 55 g the 1 as g 1 and g the 1 g and g e the 1 g 1 and ox 0 g chloride the 1 g and g he1 g and g o i enesulf onyl i the op olid g and g onylchloride the 1 b u t yr am i d o e t hyl p h e nyl ul 2 i n o 3 ol g 1 and g onylchloride the g 1 g onylchloride the 1 g 1 and g l c o r i e e imidasoiidine g 1 and g the 1 g 1 a g e pent 1 and g the 1 g and g lfonylchloride the 1 g 1 and g chloride the 1 c o i 21 g c or id e and g the 1 ol id ine g and g the d t hyl enyl onyl y g and g de the 1 2 i oval e d o e t hyl s ulf i n g 1 inidas ol id oc hi or id e and 0 g o c the 1 d e t 3 c oh e im i da s ol id ine g 1 and g chloride the g ne and g the 1 g 1 and the 1 o g 1 and 29j0 g the 1 o g 1 and g the 1 2 etani d o ethyl i ra i n g 1 and g the g 1 ana g the 1 g 1 and g 1 g and the 1 g and 2 t 1 hydrochloride g the ide which is used as starting material is obtained according the following g ide are given portionswise while stirring to chlorosulfonic thereafter the mixture is stirred for 2 hours at and then poured on crystals are filtered washed water and dried in obtained is as crude In way one obtains the used as starting material are worked up as crude Prom g and acid the from g and g chlorosnl acid the g cetamide and g chloro sulfonic acid the from g and 35 0 gchlorosulf onic acid the g and gchlorosulf onic acid the op i onanid e hy ens ene or id g and Og chloro sulf p 2 t am i d o e t b e n s e n e s f o 1 c o r i d e from g ethyl and g ac id the hyl from g e and ac t 2 s 1 e am i o e t hyl e s o c hi d from g e and g x chlorosulf acid ony 2 According 1 one obtains from g in sodium hydroxide and g the sulfonyl chloride used as starting material is prepared according the following g are added to g e in 30 ml sodium hydroxi and g de crystall It is suctioned washed with and used as crude to g of the obtained nitro compound according method suspended in 85 ml ethanol are ml hydrochloric acid with g iron powder it is refluxed for 12 Then the reaction mixture is and washed with filtrate is evaporated in vacuo and to the residue is added hydrochloric One obtains the which is used as cru e g of the obtained according are added glacial acetic acid and 34 concentrated hydrochloric The at g sodium nitrite which is in 30 ml The obtained diasoni m salt solution is given to ur a solution saturated de of g cupric 7 ml water and glacial acetic A slight exothermic reaction at nitrogen is split off The reaction is for 2 The e The crystals are snotional off and washed with water and used as crude Example According example 1 one obtains from g and g ioride e 4 According example 1 one obtains from g 1 in sodium hydroxide and g chloride the The used as starting material is prepared 5 accordin the following Accordin example 2 one obtains starting with g with g the bensamide of acetic acid ethyleste g of this nitro compound are reduced with g iron powder to yield the of of which are g diazotized in acid with g sodium the diazonium salt solution yields with a solution of cupric chloride in water and glacial acetic acid which is saturated wit chloride which melts at According example 1 one obtains from g in sodium hydroxide and g ony 33 chloride the ethyl sul onylchloride used as starting material is prepared according the following According 2 one starting with g with g phenethylanine the enzanide ethyl g of this compound are reduced with g iron powder to yield the of which g are in concentrated acid with g itrite the diazonium salt solution yields with a solution of cupric chloride in water and glacial acetic acid which is saturated with the sul onylchloride E 5 According example 1 one obtains from g in sodium hydroxide and g o 2 libra e 7 According 1 one obtains g in sodium hydroxide and g enzanid o e benzenesulf onylchloride the i ine of ethyl l e 8 According example 1 obtains fron g 1 hydrochloride in sodium hydroxide and g benzenesulf onylchloride the id ine of chloride used as starting material is prepared according to the following According example 2 one obtains starting with g with g the e g of this nitro compound are reduced with g iron powder to yield t e hydrochloride of g are diazotized in hydrochloride acid with g the diazonium salt solution yields with a solution of cupric chloride in water and glacial acetic acid which is saturated with the 9 According example 1 one obtains from g in sodium hydroxide and g sulfonylchloride the enyls e of ethyl The sulfonylchloride as starting material is prepared according to the following According example 2 one obtains starting with g with g the g of this nitro compound are reduced with g iron powder to yield the o e chloride of which are diazotized in hydrochloride acid with g sodium the solution yields ith a solution of chloride in water and acetic acid which is saturated with lfurdioxide the 0 According 1 one ains from g in sodium hydroxide and g the of ethyl According example 1 one obtains from g in sodium hydroxide and g the p of The end product is purified by elution on silicagel c as elution From the first fractions one recovers unchanged starting material from last fractions the 12 According 1 obtains g ochioride in and g the o ox According one obtains from g 1 in sodium hydroxide chloride the 4 of ethyl acetate She is used as starting material is prepared according example le 1 butyl According example 1 one obtains from g 1 in sodium hydrcxide and g the 1 olidine of ethyl 1 pro are dissolved in 200 water and the is liberated with 300 nl It is e tracted with the e solution which has dried sodium sulfate are g thereafter to the reaction mixture is dropped at room temperature the solution of g propionic acid chloride in 100 ml chloride within 20 After stirring the solution for one hour at room emperature it is washed with ml hydroxide twice with 00 ml aqueous phases are extracted twice with combined phases yield after drying with sodium sulfate filtrating and evaporating 1 melts at after from ethyl In analcgus one obt from hydrochlo g the 1 g the 1 g the g isovaleric acid chloride the 1 ethyl xylic g cyclopro acid chloride the 1 xylic g acid chloride the 1 zol g oluoylchloride the g the idine g r ol id g the 1 i d o e p h e n yl s u 1 o n yl 2 i i h o 3 so i g acid chloride e 1 e g the 1 g 1 the 1 h e t o 2 i n i n o 3 g the 1 or o cnyl 46 The starting material j is obtained according two g are dissolved in 370 ml hydrochloric acid and the solution is refluxed for 6 The solution is then evaporated in vacuo to dryness and the obtained oil dissolved in On cooling the sulfonyl A mixture of 100 ml g pulverised potassium 65 g E et and 16 g is heated while stirring for one hour in an oil bath of After cooling one pours on The obtained cloudy solution is made alkaline with sodium saturated with sodium chloride and extracted three times with methylenechloridej the organic phases are dried over filtrated and The obtained oil is dissolved in ethanol and made acidic with saturated ethanolic hydrochloric On cooling and if desired diluting with ether the of 1 g are dissolved in N 200 water and is 300 2 sodium It is extrac ed with the methylenehioride solution which has been dried over sodiumsulfate are added g er one drops at room temperature a solution of g chloride in 100 ml wi hin 20 minutes to the reaction After stirring for one hour at room N it is washed with 100 ml sodium hydroxide and twice with ml phases are extracted twice combined ne yl phases yield after drying with filtrating eva the 1 which melts after crystallisation from ethyl acetate at 1 g are dissolved in 200 ml N water and the base is liberated with 300 ml sodium It is extracted with io the methylene solution which over sulfate are added g triethyla o this solution one drops at room temperature a solution of g propionic acid It is extracted with To the methylenchloride solution which has been dried over sodium sulfate are added g Thereafter one drops to the solution at room temperature a solution of g butyric acid chloride in 100 ml methylenchloride within 20 After stirring the solution for one hour at room temperature it is washed with 100 ml sodium hydroxide and twice with 100 ml The aqueous phases are extracted twice with methylenchloride The combined methylenchloride phases yield after drying with sodium filtering and evaporating the which after recrystallisation acetate at In one from 1 g 1 c io lcride the acid chloride the xylic acid chloride the g the 1 y g the 1 g 1 the 1 1 asolidine 1 starting material 1 s ed according g l N are dissolved in 370 nl ydrochloric acid and the solution is refluxed for 6 solution is then evaporated in vacuo to and the oil obtained dissolved in On cooling the A of nl g pulverised g hydrochloride et Soc and 16 g e are for one hour in oil bath of After cooling one pours on obtained cloudy solution is made alhaline with sodium saturated With sodium chloride and extracted three the organic phases are dried over sodium filtrated and She obtained oil in ethanol and made acidic wi saturated hydrochlorid On cooling and if desired diluting ether the 1 ethyl dihydrochloride of Example 19 g are dissolved in 200 ml N water and the base is liberated 300 ml sodium It is extracted with methylene To the methylene chloride solution cried over sodium sulfateare added g triethyla ine Thereafter one drops to the solution at room temperature the solution of g acetyl chloride in 100 ml methylene chloride within 2o After stirring the solution for 1 hour at room N temperature it is washed with 100 ml sodium hydroxide and twice with 100 ml The aqueous phases are tracted twice with methylene The combinded methylene chloride phases yield after drying with sodium filtrating and evaporating which after st from ethyl acetate melts at In analogous way one obtains from g hydrcchlcride and g butyrylchloride the 1 g the g valeric acid chloride the g isovaleric acid chloride the g caproyl chloride the g caprylic acid chloride the 1 g chloride the 1 g chloride the 1 amido ine g chloride the pheny1 imidazolidine g chloride the but imidazolidine ionyl chloride the imidazolidine g acrylolyl chloride the g chloride the g chloride the xylic g acid chloride the 1 the hen The starting material chloride is obtained accordingly after two g N are dissolved in 370 ml 2 hydrochloric acid and the solution is refluxed for 6 The solution is then evaporated in vacuum to dryness and the obtained oil dissolved in et On cooling the A mixture of 100 ml dimethylsulfoxide g pulverized potassium g hydrochloride et and 16 g are heated in an oil bath of while stirring for 1 After cooling one pours on The obtained cloudy solution is made alkaline with concentraded sodium saturated with sodium chloride and extracted three times with methylene the organic phases are dried over sodium sulfate filtrated and The obtained oil is dissolved in ethanol and made acetic with saturated ethanolic hydrochloric On cooling and if desired diluting with ether the of Example 20 5 g are dissolved in 200 ml water and the base is liberated with 300 ml sodium It is extracted with methylene To the methylene chloride solution which has been dried over sodium sulfate are added g triethyl after one drops at room temperature the solution of 10 g propionic acid chloride in 100 ml methylene chloride within 20 minutes to the After stirring the solution for 1 hour at rooum temperature it is washed with 100 ml sodium and twice with 100 ml The aqueous phases are extracted twice with methylene The combined methylene chloride phases yield after drying with sodium filtrating and evaporating the s which melts at after recrystallisation from ethyl In analogous way one obtains from g g butyric acid chloride the g valeric acid chloride the p g isovaleric acid chloride the 1 g pivaloyl chloride the 1 1 4 4 g hexanoyl choride the xylic g acid chloride the 5 g chloride the 1 1 7 g chloride the hyl g chloride the 1 benzamido g chloride the en δ chloride the imidazolidine g chloride the 1 benzamido iraidazolidine g chloride the imidazolidine o g chloride the imidazolidine acetic g acetanhydriue the The starting material 1 is obtained after two d 1 36 65 g are dissolved in 370 ml hydrochloric acid and the solution is refluxed for 6 The solution is then evaporated in vacuum to dryness and the obtained oil solved in On cooling the e h l 1 51 A mixture of 100 ml dimethyl 1 g pulverized 23 65 g Tit Miller et o 21 01 1 and 20 5 g are heated while stirring for 1 hour in an oil bath of 1 1 After cooling one pours on The obtained cloudy solution is made alkaline with concentrated sodium saturated with sodium chloride and extracted three times with methylene the organic phases are dried over sodium filtrated and The obtained oil is dissolved in and made acidic saturated ethanolic hydrochloric On cooling and if desired diluting with ether the 1 51 Example 21 39 7 g are dissolved in 200 ml N water and the base is liberated with 300 ml sodium hydroxid It is extracted with methylene To the methylene chloride solution which has been dried over sodium sulfate are added g triethyl Thereafter one drops to the solution at room temperature the solution of g valeric acid chloride in 1 00 ml methylene chloride within 20 After stirring the solution for 1 hour at room N temperature it is washed with 100 ml sodium hydroxide and twice with 1 00 ml The aqueous phases are extracted with methylene The combined methylene chloride phases yield after drying with sodium filtrating and evapora ting the melts at 1 after recrystallisation from ethyl In analogous one obtains from g ethyl dihydro chloride g acetyl chloride the i g propionyl chloride the 11 g butyryl chloride the g chloride g chloride the g benzoyl chloride the imidazolidine g acid chloride the g chloride the 1 g benzoyl chloride the The starting material is obtained after two methods for d g 1 are dissolved in 370 hydrochloric acid the solution is refluxed for 6 The solution is then evaporated in vacuum to dryness and the obtained oil solved in On cooling the A mixture of dimethyl 2 g pulverized potassium g et and g ethyl cyanamide is heaxed while stirring for 1 hour in an oil bath of After cooling one pours on The obtained cloudy solution is made alkaline concentrated sodium saturated with sodium chloride and extracted three times methylene the organic phases are dried over sodium filtrated and The obtained oil is dissolved in ethanol and made acidic saturated ethanclic hydrochloric On cooling and if desired diluting with ether the 1 precipitates Example 22 g l are dissolved in 200 ml N water and the base liberated with 300 ml 2fi sodium hydroxide It is extracted with methylene To the methylene chloride solution which has been dried over sodium sulfate are added g triethyl Thereafter one drops at temperature to the solution a solution of g acetyl chloride in 100 ml methylene chloride within 20 After stirring the solution for 1 hour at room temperature N it is with 100 ml sodium hydroxide and twice with 100 ml The aqueous phases are extracted with methylene The combined methylene chloride phases yield after drying with sodium filtrating and porating the which melts at after recrystallisation from ethyl Example 25 41 g are dissolved N in 200 ml water and the base is with ml sodium It is extracted with methylene To the methylene chloride solution which has been dried over sodium sulfate are added g triethyl Thereafter one drops to this solution at room temperature the solution of 13 g isovaleric acid chloride in 100 ml methylene chloride within 20 After stirring the solution for 1 hour at room temperature it is washed with 100 ml sodium hydroxide and twice with 100 ml The aqueous phases are extracted twice with methylene The combined methylene chloride phases yield after drying with sodium filtrating and porating the melts at after recrystallisation from ethyl In analogous way one obtains from g g pivaloylchloride the g a 0 Ρ g tyryl chloride the ethyl xylic g acid chloride the iraidazolidine g chloride the g chloride the o g chloride the o g chloride the o o g chloride the 1 imidazolidine g benzoyl chloride the 1 4 trimethoxybenzamido chloride the i g butyryl chloride the g chloride the benzamido midazolidine The starting material te is obtained after two methods for g are dissolved in 370 ml hydrochloric acid and the solution is refluxed for 6 The solution is then evaporated in vacuum to dryness and the obtained oil solved in On cooling the monohydrate mixture of 100 ml dimethyl g pulverized potassium g et Soc and 16 g are heated for 1 hour while stirring in an oil bath After cooling one pours on The obtained cloudy solution is made alkaline with concentrated sodium saturated with sodium chloride and extracted three times with methylene the organic phases are dried over sodium filtrated and The obtained oil is dissolved in ethanol and acetic with ethanolic chloric On cooling and if desired diluting with ether the precipitates Example 24 g are dissolved in 200 ml water and the base is liberated with 300 ml hydroxi It is extracted with methylene To the methylene chloride solution wihich has been dried over sodium sulfate are added g triethyl Thereafter one drops to the solution at room temperature a solution of 1 3 0 g chloride in 100 ml methylene chloride within 20 Afte stirring the solution for 1 hour at room temperature it is N washed with 1 00 ml 2r sodium hydroxide and twice with 100 ml The aqueous phases are extracted twice with methylene The combined methylene chloride phases yield after drying with sodium filtrating and evaporating the hyl idazolidine which after recrystallisation from acetone melts at 1 In analogous way one obtains from g chloride 1 g butyryl chloride the g the xylic g cyclohexan acid chloride the 1 e 81 g acetyl chloride the g enzoyl chloride the benzamido g benzoyl chloride the iinidazolidine 151 xylic 5 g acid the the 31 the the The starting material is obtained after two methods of d g are dissolved in 370 ml hydrochloric acid and the solution is refluxed for b The solution is then evaporated in vacuum to dryness and the obtained oil dissolved in un cooling the i mixutre of TOO ml dimethyl g pulverized potassium g hydrochloride et and g heated while stirring for hour in an oil bath of cooling one pours on The obtained cloudy solution is made alkaline with concentrated sodium saturated with chloride and extracted three times with methylene the organic phases are dried over soldium filtrated and The oil is dissolved in and made acidic with saturated ethanolic hydrochloric On cooling and if desired diluting with ether the Example 25 g are dissolved in N 200 ml water and the base is liberated with ml sodium It is extracted with e To the methyleni h loride solution which has been dried with sodium sulfate g triethylamine are To this solution are dropped at room temperature a solution of g propionic acid chloride in 100 ml methyl enchloride within 20 After stirring the solution for 1 hour at room N temperature it is washed with 100 ml hydroxide and twice with 100 ml The aqueous phases are extracted twice with methylen The combined methyl ench loride phases yield after drying with sodium filtrating and evaporating the semihycrate which melts at 110 to if recrystallized from ethyl Accordingly one obtains from g fo chloride g acetylchloride the sulfonyl g butyrylchloride the hydrate g loride the g isovalerylchloride the phenyl chloride g carboxamidoethy1 azolidine g the g cinnarnic acid chloride the azolidine o g the ethyl sulfonyl g the phenylsu p g the a ido azolidine O g loride the sulfonyl azolidine g the sulfonyl azolidine g the 2 g the eny azolidine g the ethyl g the amido azolidine g the sulfcnyl g the benzarnido sulfcnyl irnidazolidine g the sulfonyl azolidine g 3 the 3 azolidine g the ido xylic g acid chloride the phenvlsulfonyl xylic g acid chloride the phenyl yl xylic g cyclo exane acid chloride the su Ifonyl xylic g acid chloride the the 3 7 The starting material sulf nyl is prepared according two different g sulfonyl are dissolved 370 ml chloric and the solution is refluxed for 6 The solution is evaporated in vacuo and the oil obtained dissolved in eth On cooling the sulfonyl crys A mixture of 100 dimethyl g pulverized potassium g sulfonamide hydrochloride et al and g are heated while stirring for 1 hour in an oil bath of After cooling one pours on The tained cloudy solution is made with concentrated sodium saturated with sodium chloride and three e times extracted with methylenchloride the organic phases are dried over sodium filtrated and The obtained oil is dissolved ethanol and made acidic with saturated hydrochloric acid in On ing and if desired diluting with ether the ethyl sulfonyl dihydrochloride Example 26 According example 25 one obtains from g ethyl sulfcnyl dihydrochloride and g acetylchloride the azolidine From the same amino compound one obtains g butyrylchloride the sulfonyl g valerylchlcride the g loride the amido azolidine g 2 loride the azolidine the 3 suifonyl The starting material chloride is according example 25 from g phenyl sulfonyl chloride Example 27 g are dissolved in ml water and the base is liberated 300 ml sodium It is extracted with methylenchlor To the methyl en hlorice solution which has been dried over sodium sulfate are added g Thereafter one drops to this solution at room temperature the solution of 13 g isovalerylchlorice e in 100 ml loride within 20 After the solut ion has been stirred for 1 hour at room temperature it is N washed with 10O ml sodium hvdroxide and twice with CO ml ene The aoueous phases are extracted twice with methyl hlo e The combined methyl phases yield after drying with sodium filtrating and evaporating the azolidine which melts at if recrystallized from ethyl In method one obtains from g propyl g the lidine as g the The staring material can be obtained according two different d g are dissolved in 370 ml hydrochloride acid and the solution is refluxed for 6 The solution is evaporated in vacuo to dryness and the oil obtained is dissolved in On cooling the sulfonyl crystal ve hydroscopic A mixture of ml dimethyl sulfoxide g pulverized potassium 250 g 7 and 16 g ethyl mide is heated for 1 hour in an oil bath of while After cooling one pours on The obtained cloudy solution is made alkaline with concentrated sodium saturated with sodium chloride and extracted with three the organic phases are dried over sodium filtrated and The obtained oil is dissolved in and made acidic with saturated ethanolic hydrochloric On cooling and if desired dilution with ether the propyl chloride precipitates as very hygroscopic Example 28 g are dissolved in 2C0 ml N water and the base is liberated with 300 ml sodium It is extracted with To the methyl ench lor ce solution which has been dried over sodium sulfate are added triethyl To this solution is dropped at temperature a solution of 13 g in 100 ml methyl lor ice within 20 After the solution has been stirred at room N temperature for it is washed with ml sodium hydroxide and twice with 100 ml The aqueous phases are e tracted twice with The combinde methyl phases yield after drying with sodium filtrating and evaporating the phenyl ine which melts after recrystallizatxon from ethyl acetate at The starting material can be obtained according two d g N are dissolved in 370 ml hydrochloric acid and the solution is refluxed for 6 The solution is evaporated in vacuo and the oil obtained the propyl hydrochlorice used A mixture of CO ml dimethyl g pulverized potassium hydroxide g o and g is heated while stirring for 1 hour in an oil bath of After cooling one pours on The obtained cloudy solution is extracted with concentrated the organic phases are dried over sodium filtrated and The obtained oil is dissolved in ethanol and made acidic with saturated ethanolic hydrochloric After evaporating one obtains the as an 29 g loride are dissolved in 2C0 water and the base is liberated with 300 sodium It is extracted To the ethyl en6nloride solution which has been dried over sodium sulfate are added g To this solution is dropped at temperature the solution of g e in 100 ml methyl within 20 After the ion has been stirred for 1 hour at room it is N washed with 100 ml sodium hydroxide and twice with 100 ml The aqueous phases are extracted twice methylene e The combined methyl phases yield after drying with sodium filtrating and evaporating the 3 th dazolidine which melts after recrystal from ethyl acetate at The starting material lo ide is according two d g are dissolved in 370 ml 2n chloric acid and the solution is refluxed for 6 The solution is then evaporated in vacuo to dryness and the oil obtained the used A mixture of 1Q0 ml g pulverized potassium g 7 and 16 g is heated while stirring for 1 hour in an oil bath of After cooling one pours on The obtained cloudy solution is made alkaline with concentrated sodium saturated with sodium chloride and extracted three times with The organic phases are dried over sodium filtrated and The obtained oil is solved in ethanol and made acidic with saturated hydrochloric After evaporating one obtains the dihydrochlorice as an Example 30 g loride are dissolved 200 ml and the base is liberated with SCO ml sodium It is extracted with To e the meth solution which has been dried over sodium sulfate are added g triethyl To this ion is dropped at room temperature the solution of g valeryl chloride in ml methylenchloride within 20 minutes After the solution has been stirred at room temoerature for 1 hour it is washed 100 ml 2m sodium hydroxide and twice with 100 ml The aqueous phases are extracted twice e e with The combined methylenchloride phases yield after crying with sodium filtrating and evaporating the which melts after crystallization from ethyl acetate at Accordingly one obtains from g ol hydroc loride g isovalerylchloride the phenyl su ne acid g the g the phenyl hemihydrate g the ethyl sulfonyl g 3 the 3 g the g 2 the 2 The starting material prepared according the following g sulfonyl N are dissolved in 370 ml hydrochloric acid and the solution is refluxed for 6 The solution is then evaporated in vacuo to dryness and the oil obtained digsolved in On cooling the ethyl dihydroch loride crystallizes Example According example 30 one obtains from g sulfonyl azolidine g acetylchloride the sulfonyl g valerylchlorice the g isovalerylchloride dine g the ethyl g the g the e acid g cyclohexane the cyclo The starting prepared according 29 g Example 32 According 30 one obtains g and g butyrylchicrice th v The starting material i obtained according example 29 g onyl as Example 33 g sul are dissolved in 2C0 ml water and the base is liberated with 300 ml sodium hydroxi e It is extracted with To the solution has been dried with sodium sulfate are added g To this solution is dropped at room temperature the solution of 13 g valeryl hloride in 100 ml methylenchloride within 20 After the solution has been stirred for one hour at room temperature it is washed N with 100 ml sodium hydroxide and twice with 100 ml e The aqueous phases are extracted twice with e The combined methyl phases yield after drying with sodium filtrating and evaporating the er azolidine from it melts at In way one obtains g ethyl dihydrochloride g isobutyrylchlor ide the as an oil g pivaloylchloride the o g the sulfonyl azolidine as an o g 2 the 2 sulfonyl azolidine as The starting de is obtained according the following g are dissolved in 370 ml chloric acid and the solution is refluxed for 6 The V solution is evaporated in vacuo to dryness and the oil tained dissolved in On cooling the ethyl sulfonyl dihydrochloride crystallizes 34 28 ml sodium hydroxide and g are cooled to To this solution is then added a suspension of g in 100 acetone while stirring and cooling so that the temperature does not rise above After adding is finished stirring is continued for 30 minutes at Therafter the cooling bath is and to the solution of the obtained are added 100 ml The temperature rises to 40 The reaction mixture is stirred for another hour and finely the excess of amine is i distilled off on the rotary The crystalline paste containing beside sodium chloride the desired lfonyl ine is dissolved in 56 ml sodium hydroxide and to this solution cyanogenbromide is added portion wise while stirring g whereby the temperature is not allowed to rise above After 1 hour the obtained compound is extracted with washed with 20 ml 2n sodium hydroxide and twice with 100 ml After crying and evaporating the oride solution the residue is recrystallized from ethyl acetate and yields the Example 35 28 ml 4n sodium hydroxide and g ethylenimine are cooled to Therafter a suspension of g amidoethyl sulfochloride in 100 ml acetone is given to the solution stirring and cooling whereby the temperature is not allowed to rise over After dropping to the solution is finished it is stirred for another 30 minutes at Thereafter the cooling bath is removed and to the the solution obtained sulfonyl are added 100 ml The temperature rises to The reaction mixture is stirred for another hour and thereafter the excess of amine is stined off on the rotary The crystalline paste which contains beside sodium chloride the desired is dissolved in ml 2 hydroxide and to this solution c omide are added portion wise stirring g whereby the temperature is not allowed to rise above After 1 the obtained compound is extracted with washed with 20 ml 2n sodium hydroxide and twice with OC ml After drying and evaporating of the methyl solution the residue is recrystal ethyl acetate and yields the In manner one obtains from CC propylamine and 29 g the azolidine 36 N 28 ml sodium hydroxide g are cooled to Thereafter a suspension of g sulfcchlorice in CC ml acetone while stirring and cooling is added so that the does not rise above C After dropping to is inued for 30 minutes at C Thereafter the cooling bath is removed of the and to the phenylsul are added CO ml The temperature to The reaction mixture is stirred for another hour and thereafter the excess of amine is stilled off on the rotary The crystalline vhich contains beside sodium chloride the desired diamine is dissolved in 56 ml 2n sodium hydroxide and to this cyanogen solution is added while stirring portion wise g whereby the temperature does rise above After 1 hour the obtained is extracted with methyl washed 20 2ri sodium hydroxide and twice with CO ml After drying and evaporating of the solution the residue is recrystallized ethyl acetate and the phenylsulfonyl In manner one obtains from g ethylenirnine 100 ml i and g the 100 and g loride the 100 ml isopropylamine and 29 g sulfochlorice the 100 butylamine and g chloride the fcn 2 CO ml b and g 100 and g chloride the 100 isobutylarrrine and g sulfochloride the 100 and g CO isobutylamine and g ethyl the ethyl s 100 sec and g sulfochloride the r 100 ml utylamine end g phenylsulfochloride 100 ml and g n sul och loride sulfonyl 100 ml and g och the 100 ml tert and g phenylsulfochloride the th e s Example 37 28 ml sodium hydroxide and g are cooled Thereafter a suspension of g ethyl in 100 ml acetone is stirring and cooling so that the temperature does not rise above After dropping to is finished it is stirred for another 30 minutes at Thereafter the cooling bath is and to the solution of the obtained ethyl are added 100 ml The to The reaction is stirred for another hour and thereafter the excess of is distilled off on the rotary The crystalline paste which contains besides sodium chloride the desired ethyl endi in ml hydroxide and to this solution are added while stirring portion wise g cyanogen bromide whereby the temperature is not allowed to rise above After i hour the obtained compound is extracted with washed with 20 ml sodium hydroxide and twice with 100 ml After drying and evaporating of the methylenchloride solution the residue is from ethyl acetate and yields the phenylsulfonyl tert In way one obtains g and 100 and g ethyl sulfochloride the ethyl 100 ml and g phenylsulfochloride the tert 100 ter and 5 g the hy1 enyl bu ml ter and g the 100 cyclopen tyl and g sulfochlorice the cyclopentyl and g phenyl sulfochlorice the 100 ml cyclopentylamine and g sul the ony1 azolidine 100 ml and 24 g sulfochlorice the lsulfonyl 100 ml cyclohexylamine and g phenylsulfochloride th e 100 ml and g ethylacetamico propyl ochloride the propyl enyl e 100 ml cyclohexvlamine and g phenylsulfochloride the V2 100 ml cyclohexylamine and g phenylsulfochloride the 100 cyclohexylamine and g sulfoch loride the 1V 100 ml cyclohexylamine and g phenylsulfochloride the enyl sulfonyl 7 100 ml eye1ohexy1amine a d g ethyl the amico enyl 100 and g ethyl the ethyl e 100 ml cycloheptylamine g phenylsulfochlorice the ml and g phenylsulfochlorice the 38 28 ml sodium hydroxide propylenimine are cooled to Thereafter a suspension of g ethyl in 100 ml acetone is added wh stirring and cooling so that the temperature does rise above After dropping to is the reaction stirred for 30 minutes at Then the cooling bat is removed to the solution of the obtained are added 100 The temperature rises to The reaction mixture is stirred for 1 hour and thereafter the excess of amine distilled off on the rotary The crystalli paste which contains besides chloride the desired rop is dissolved in 56 ml sodi and to this cyanogen bromide is added while stirring portion wise g whereby the temperature is not allowed to rise above After 1 hour the obtained compound is extracted with washed with 20 ml sodium hydroxide and twice with 100 ml After drying and evaporating of the methyl solution the residue is recryst aliized from ethyl acetate and yields the Example 3 N 28 ml sodium hydroxide and g propyleni ine are cooled to Thereafter a suspension of g ethyl ochloride in 100 ml acetone is added while stirring cooling so that the temperature does not rise above After dropping to is finished the reaction mixture is stirred for 30 minutes at Then the cooling bath is removed and to the solution of the obtained are added ICO ml The temperature rises to The reaction is stirred for 1 hour and t ereafter the excess of ist destillec off on the rotary The crystalline paste which contains besides chloride the desired 1 is dissolved in 56 sodium hydroxide and to this solution is added while portion wise cyanogen bromide g whereby the temperature is not allowed to rise above After 1 hour the obtained compound is tracted washed with ml 2n sodium hydroxide and with 100 ml After drying and evaporating of methylenchloride solution the residue is recrysta from ethyl acetate and yields the sul fonyl 40 To a mixture of 4 g sodium 15 ml water and 300 ml foxi one dissolves g ethyl and 16 g The obtained solution is refluxed for 1 The is distilled off in vacuo and the a brown oil is taken up in methyl The organic phase is washed three times with dried and filtrated and yields after evapora brown After recrystal ligation from ethyl acetate the In one obtains g and g the ethyl sulfonyl 0 g and g the sulfonyl imidazolidine and g the g and c the and g e the ethyl su g and g meth the 3 imidazolidine g and g the g and g the lorobenzamido imidazolidine g and g the as an g and the r su sobu g and g the lorobenzamido g and the sulfonyl g and g the e g loroethyl and g the propic sulfonyl azolidine g and g the sulfonyl g and g the a g and g the azolidine To a mixture of 4 g sodium 15 ml water and 300 ml dimethyl sulfoxide one dissolves g ethyl and 15 g The obtained solution is refluxed for 1 hour The dimethyl sulfoxide is distilled off in vacuo and the a brown oil is taken up in methyl The organic phase is washed three times with dried and filtrated and yields after evaporating brown After from ethyl acetate one obtains the e ananalogous one obtains g loroethy1 and g the g d the i g an and g en e the l g and g the azolidine c and c the g and g fcnamide the ami et onyl cyclop en g end g 1 f the do onyl azolidine g and 9 g t sulf g and g the ethyl azolidine 8 g and g the azolidine g end g the f onyl g loroethyl end g e g amide and g t en g loroethyl and g the g e and g z e i so imidazolidine g 1 or e and g ide the 8 g 1 the g loroethyl and g the ethyl enyl sulfonyl g and the l 42 g enyl sulfcnyl dissolved in 2C0 ml ethanol and refluxed with 12 g for 1 Thereafter the reaction mixture is evaporated on a rotary The residue is dilutee with 50 ml ethyl acetate and extracted with 80 ml 2n hydrochloric The aqueous phase is alkaline with 2n sodium hydroxide and extracted with 100 ml methy1 The is washed with dried and The residue is crystallized from ethyl acetate and yields the pure imicazolidine way one obtains 2 g and g propylamine l sulfonyl 1 H20 g and g the sulfo yl o S g ide and g amine the propicn imidazolidine g rcmc and g isopropyla g and g the e hyl sulfonyl zolidine 1 g and b t e sulfonyl g sul g the 1 g and g the g and g the s 0 g and g isobutyl t e sulfonyl g and g isobuty1amine the g sulfonyl ide and g the 8 g and g the idine g ethyl and g secbutylamine the a onyl u g sulfonyl and c tert amine the sulfo yl azoliiine g sov and g the imidazolicine g and 17 g cyclopen the ethyl azolidine g sulfonyl and 17 g the ethyl g and 17 g the l fonyl cyclopentyl The starting material is obtained on the folloving o 6g cyanogen bronide in 40 ml ether are dropped at c ethylen in 20 ml To the in ether is added a suspension of q in 100 N To the reaction mixture are dropped thereafter 52 ml 2yf sodium hydroxide and it is stirred for 1 hour at room temperatu the ether and are removed in the rotary The is extracted with The solution is washed twice with dried and The residue the a light yellow The used not isolated starting materials are obtained in way from g cyanogen bromide and g imine g sul ochloride the g the sulfonyl l g the g lorice the g the er g the yl yl g loride the zamido g the a ido 43 in 200 ethancl and g are for 1 Thereafter the reaction mixture is evaporated on the rotary The residue is diluted with 50 ml ethyl acetate and extracted two tines with SO N hydrochloric The aqueous phase is mace alkaline h 2N sodium hydroxide and extracted twice with OC mi The solution is washed with dried and The residue crystallises from ethyl acetat and yields the pure ate In way one obtains g and g cyclohexylamine the a l sul g hyl and g cyclohexyiamine the 2 g and g the suIfonyl g e and g the sulfonyl 1 H20 g ethylcyanamide and cyclohexylamine the ethyl g and cyclohexylamine ethyl sulfonyl g sulfcnyl and the sulfonyl S g and the sulfonyl g 1 and cycloheptyla ine the ethyl 2 g su and cycloheptylamine the ethyl ci and g tert octyla ine the sulfonyl g and g amine i ethyl sulfonyl 2 g and g allylanine the ethyl a and g phenethylamine the hyl The used net isolated starting materials ere obtained according to example 42 from g cyanogen bromide and g ethylenimine g the su g the ethyl e g enyl suifochlori the enyl a ide To g are added ml hydroxide and the liberated is extracted methyl To the dried are added g After 30 minutes the solvent is The residue is heated at 12 to 15 10 to circa and thereafter dissolved in hot ethyl After the It at analogous way one obtains from g chloral g the g the sulfonyl g imidazolioine the 32 j 4 g the g the e g ethyl the phenyl ony g the suifon g cyclohexen the phenyl chexen 45 According to 15 to 33 one obtains by sulfonyl acet henyl sulfonyl onyl l imicazolidine imidazolidine imidazolicine cyclohexan 3 onyl hexen enyl sulfonyl eta opy idazolidine 1 1 5 f 3 th z ami s sulf 2 s th l 3 oh ex en c arbo sulf 3 su The are necessary for the reaction as starting are described examples 15 to 33 or are obtained according to examples 15 to 33 the hexen the cyclohexan the sul cyclohexan glass like molten ony azolidine s imicazolidine the the su imidazolidine insufficientOCRQuality

Claims (1)

1. What we claim New of general formula I in is 2 is an alkyl group with not more than carDon an alkenyl group with to 5 or cyclcalkenyl with not nore than 7 carbon atoms or a phenylal yl group with not than 9 carbon hydrogen or an group with not more than 2 carbon is an alkyl or chlo group with not than 7 carbon a a alkenyl group with not nore than carbon a cycloalkyl cyclcalkenyl or not more than carbon a phenyl group or a phenylalkyl or group not more than 10 carbon wherein the phenyl group can be mono to tri substituted by halogen of atomic number up to and including trifluoromethyl and its addition salts with inorganic and or ganic 1 and its addition salts with inorganic and organic 1 hyl and its addition salts with inorganic and organic 1 b and its addition with inorganic and organic acids 1 imidazolidine and its addition salts with inorganic and organic 1 snd its addition salts with inorganic and nic and its addition salts with inorganic and organic acids 1 and its addition salts with inorganic and organic acids 1 and its addition salts with inorganic and organic 1 y and its addition salts with ganic and organic 21 1 cl o and its addition salts with inorganic and organic acids 1 and its addition salts with inorganic and organic acids and its addition salts with inorganic and organic acids 1 hex ine and its addition salts with inorganic and nic and its addition salts with inorganic and organic acids butyl 1 on and its addition salts with inorganic and organic 1 0enzamido ol id ine and its addition salts with inorganic and organic acids imidazolidine and its addition salts with inorganic and organic acids 1 yc1 imidazolidine and its addition salts with inorganic and organic 1 its addition salts with inorganic and organic acid 1 yl and its addition salts with inorganic and organic acids 1 imidazolidine and its addition salts with inorganic and organic acids imidazolidine and its addition salts with inorganic and organic acids and its addition salts with inorganic and organic acids Process for the production of new derivatives of general formula I i in which m is 2 or is an alkyl group with not han 12 carbon alk an alkenyl group with 3 to 5 a or alk with not than 7 carbon or a group not than 9 carbon is hydrogen or an alkyl group with not mo than 2 is or group with not more than 7 carbon an alkenyl group wit not more than 5 carbon a c group not more carDon a pnenyl or a phenylalkyl or phenylalkenyl group with not more than 10 carbon wherein the phenyl group can be mono to tri substituted by halogen of atomic number up to and including trifluoro methyl alkyl groups with not more than 4 carbon hydroxyl alkoxy or alkylthio groups with not more than 2 carbon and is hydrogen or the methyl and their addition salts with inorganic or organic characterised by reacting a functional derivative of a sulfonic acid of general formula II in which and have the meaning given under formula a ox general which and 2 have the meaning given under formula I and if the reaction products obtained may be converted with inorganic or organic acids into their addition Process for the preparation of ben ene sulfonamide nf fpr derivatives of formula I in Claim comprises that an acid general formula IV in which has the meaning given under formula I or a reactive functional derivative of such an acid is reacted with a compound of general formula V in which and have the meaning given under formula I and if the reaction products obtained are converted with inorganic or organic acids into their addition salts GB Process for the of derivatives of formula I in Claim 1 which that of general and have the given under I and is an arylme diaryl ethyl or the methyl or the group cyanogen halide or ester is condensed a derivative under ring closure optionally under separation of a and if desired the compounds converted with inorganic or organic into tneir addition salts o d n w ch compr compounds of general formula in and have the meaning under formula I are condensed under ring closure a reactive ester of a hydroxy compound general formula IX 9 C HO C in and have the given under and if 1 desired the compound obtained are converted with inorganic or organic acids into their addition salts Process for the preparation of derivatives of formula I in Claim comprises that a re ester a com ound of general formula vmich and have the same meaning as given er is condensed and with an amine of general formula GB etc V a a aaa eat a aeyeaeas or 1 e or acids their addition for of of 1 I and at 1 art faraalaaad af eai a lata their addition i n a a a a a a a 1 a a a aa i a a r v v a g a a o a 1 i a a ar t a a a aaa as as 11 r area in any of the Processes go 37 in eases and aa of the foregoing active radical at least a of e aaa i 1 y insufficientOCRQuality