SU432712A3 - - Google Patents

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SU432712A3
SU432712A3 SU1701181A SU1701181A SU432712A3 SU 432712 A3 SU432712 A3 SU 432712A3 SU 1701181 A SU1701181 A SU 1701181A SU 1701181 A SU1701181 A SU 1701181A SU 432712 A3 SU432712 A3 SU 432712A3
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radical
lower alkyl
substituted
solution
general formula
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SU1701181A
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    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
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    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P25/00—Drugs for disorders of the nervous system
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    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/18—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring
    • C07C39/19—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring containing carbon-to-carbon double bonds but no carbon-to-carbon triple bonds
    • C07C39/20—Hydroxy-styrenes
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    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4056—Esters of arylalkanephosphonic acids

Description

(72) Авторы изобретени  ( 71) За витель Эрих Мюллер, Роланд Майер и Вилли Дидерен Иностранцы Иностранна  фирма ВП Т 5 «Д-р Карл Томэ ГмбХ апнд  нппьрт(72) Authors of the invention (71) Applicant Erich Müller, Roland Meyer and Willy Diederin Foreigners Foreign company VP T 5 “Dr. Karl Tome GmbH and nppt

Изобретение относитс  к способу получени  новых р-арил-2-аминоалкоксистиролов, которые обладают фармакологической активностью и могут найти применение в медицине. Получение этих соединений основано на известной реакции амина и галоидного алкила. Р1спользование этой реакции в данном способе позвол ет получить новые, не описанные ранее соединени , обладающие фармакологической активностью. В соответствии с изобретением получены арил-2-аминоалкоксистиролы общей формулы I Rj 0-СН-СН-(СНг) 111 7 или их соли с неорганическими и органическими кислотами. В формуле I Аг обозначает фениловый радикал , 2-, или 3-, или 4-пиридиловый радикал, который может быть замещен низшей алкильной группой; 2-хинолил- или 2-пИразиииловый радикал, который может быть замещеп низщим алкилом; пиримидиловый радикал, который может быть замещен низщим алкилом; 2-бензимидазолильный радикал, который может быть замещен атомом галогена, низщим алкилом или трифторметильной группой; 2фурил- или 2-тиенильный радикал; 5-изоксазолиловый радикал, который может быть замещен низшим алкильным или фенильиым радикалом; 5- (1,2,4-оксадиазолил) -радикал, замещенный при необходимости низщим алкилом; RI, Й2, R4 и RS, которые могут быть одинаковыми или различными, обозначают атомы водорода или низшне алкильные радикалы; RS - атом водорода, низща  алкоксигрупла; Re и Ry, которые могут быть одинаковыми или различными, обозначают атомы водорода или низщие алкил-, алкенилоксиалкил-, алкоксиалкиловые или аралкиловые радикалы, причем радикалы Re и R вместе с наход щимс  между ними атомом азота могут образовать насыщенное моноциклическое или гетероциклическое 5-7-членное кольцо, которое может содержать атом кислорода или атом азота; п - целое число О или 1. В соответствии с изобретением новые соединени  формулы I получают путем реакции обменного разложени  стирола общей формулы IIThe invention relates to a process for the preparation of novel p-aryl-2-aminoalkoxystyrenes, which have pharmacological activity and can be used in medicine. The preparation of these compounds is based on the known reaction of an amine and alkyl halide. Using this reaction in this method allows to obtain new, not previously described compounds with pharmacological activity. In accordance with the invention, aryl-2-aminoalkoxystyrenes of the general formula I Rj 0-CH-CH- (CHg) 111 7 or their salts with inorganic and organic acids are obtained. In formula I, Ar means a phenyl radical, a 2-, or 3-, or 4-pyridyl radical, which may be substituted by a lower alkyl group; A 2-quinolyl or 2-pyraziiyl radical, which may be substituted by lower alkyl; a pyrimidyl radical which may be substituted with lower alkyl; 2-benzimidazolyl radical, which may be substituted by a halogen atom, a lower alkyl or trifluoromethyl group; 2-furyl or 2-thienyl radical; 5-isoxazolyl radical, which may be substituted by a lower alkyl or phenyl radical; A 5- (1,2,4-oxadiazolyl) radical, optionally substituted by lower alkyl; RI, H2, R4 and RS, which may be the same or different, denote hydrogen atoms or lower alkyl radicals; RS is a hydrogen atom, a lower alkoxy group; Re and Ry, which may be the same or different, denote hydrogen atoms or lower alkyl, alkenyloxyalkyl, alkoxyalkyl or aralkyl radicals, and Re and R radicals together with the nitrogen atom between them can form a saturated monocyclic or heterocyclic 5-7- a member ring which may contain an oxygen atom or a nitrogen atom; p is an integer of 0 or 1. In accordance with the invention, new compounds of formula I are obtained by the reaction of the exchange decomposition of styrene of general formula II

KI в которой радикалы Лг, Ri--Из нмсют указанные значени  и X обозначает ато.А водорода или ацетильную грзату, с амином общей формулы ГП Y-CH-:;H-tCn.),;-( в которой радикалы 1.-R имеют указанные значени  и Y обозначает атом галогена, в присутствии основани . Реакцию провод т в инертном растворителе , например в бензоле, хлорбензоле, толуоле , ксилоле, и при повышенных температурах, вплоть до точки кипени  нриме:: емого растворител . В качестве основани  используют гидроокиси, карбонаты или алкогол ты щелочного металла. Соединени  формулы I образуютс  в виде смеси их иис- и гранс-изомероз. Цис- и транссоединени  могут быть разделены путем фракционной кристаллизации. Соединени  формулы I обычным способом можно переводить в соли при участии неорганических или органических кислот. В качестве кислот используютс  сол на , бромистоводородна , серна , фосфорна , винна , паратолуолсульфонова  кислоты. Пример 1. К раствору 400 г 2-(2-аце-:оксистирил )-пиридина в 1250 мл хлорбензола прибавл ют 235,5 г метилата кали  и нри размешивании нагревают до 110°С, при этом образуетс  желта  суспензи , 483 г диметиламиноэтилхлорид-гидрохлорида в вибрационной воронке смешивают встр хиванием со 1000 мл лед ного 30%-ного раствора едкого натра, отдел ют освобождаюш.еес  масл нистое основание и шестью одппаковыми дозалги ввод т по капл м в суспензию. Pa3MeiJiKBJ,OT еще в течение 30 мин при ilG°C, зачем охлаждают и прибавл5 ют лед. После эхсграгировани  простым эфиром, сушки с безвод);ым сульфатом натри  и упаривани  растзори:сл  остаетс  масло, которое дистиллируют з БЯкууме; т. кип. 15G-161°С. Гю- учают 376 г масла с цветом меда (выход 83% теории). 123 г масл нистого реакционного продукта раствор ют в смеси 750 мл уксусного эфира и 330 мл абсолютного этанола, при интенсивном перемешивании постепенно добавл ю 430 мл раствора, 132 мл этанольного раствора сол ной кислоты (12,7%-на ; все/объем) в 638 мл уксусного эфира. Затем добавл ют 600 мл уксусного эфира и охлаждают до 0°С. Выдел ющиес  кристаллы (2-диметиламиноэтокси ) -стирил -пиридин-моногидрохло рида отсасывают, промывают уксусным эфиром и сушат в эксикаторе над концентрированной серной кислотой и гидроокисью каjiHK; т. г(л. )о5- -187.5°С; вь.ход при солеобраьсли примен ют избыток этанольного раствора сол ной кислоты, в общем 300 мл сол ной кислоты указанной концентрации, то раствор окрашиваетс  в темно-желтый цвет и тогда изолируют дигидрохлорид (2-диметиламиноэтокси )-стирил -ниридина с т. нл. 218-220° С. Аналогично описанному в примере 1 способу получают вещества, приведенные в следующих примерах. Пример 2. Из 1-(2-ацетоксифенил) - 2 (пиридил-2)-нропена-1 (т. кип. 140°С) и диметиламиноэтилхлорида получают 1-(2-диметиламиноэтоксифенил )-2-(пиридил-2) - пропен 1 - моногидрохлорид; т. пл. 128-133°С; выход 85% теории. Пример 3. Из 2-(2-ацетоксистирил) -пиридина (т. пл. 162-175°С) и 2-хлор-Н,М-диметилпропиламина получают (3-диметиламинопропан - 2 - окси) - стирил - пиридин; т. кип. 158-159°С; выход 86% теории. Пример 4. Из 2-(2-оксистирил)-хинолина (т. пл. 274-278°С) и диметиламиноэтилхлорида нолучают (2-диметиламиноэтокси ) - стирил - хинолин - моногидрохлорид; т. нл. 188°С; выход 86% теории. Предмет изобретени  1. Способ нолучени  |3-арил-2-аминоалкоксистпролов общей формулы I 2 0-CH-CH-(CH,), Дл R 5 где Аг - фенил, 2-, 3-, 4-пиридиловый радикал , котооый может быть за мещен низшим алкилом, 2-хи1,)лиловый радикал или 2-пиразпниловый радикал, который .ожет быть заз меп.ен низшим алкилом. пиримидиловый ра; ,1кал, когорый быть замещен низшим алг:илом, 2-бензимидазолильный радикал, ког (5рый может быть замещен атомом галогена, низшим алкилом или трифторметильной группой , 2-фурил-, 2-гиенильный радикал, 5-изоксазолиловый радикал, который может быть замещеи низп1им алкилом или фенилом, замеш ,енный низшим алкилом 5-(1,2,4-оксадиазолил )-радикал; RI, R2, R4, Ro - одинаковые или различные - водород или алкил; Нз - водород или алкоксигруппа; Кб и R - одинаковые или различные - водород , алкил-, алкенилоксиалкил-, алкоксиалкиловый или аралкиловый радикал, причем радикалы Re и Rr вместе с наход щимс  между ними атомом азота могут образовывать 5-7-членное насыщенное моноциклическое, гетероциклическое кольцо, которое может содержать еще атом кислорода или другой атом азота;KI in which the radicals Лг, Ri - Of the specified values are nsut and X denotes ato.A hydrogen or acetyl carbonate, with an amine of the general formula GP Y-CH - :; H-tCn.), ;-( in which radicals 1.- R has the indicated meanings and Y represents a halogen atom, in the presence of a base.The reaction is carried out in an inert solvent, for example, in benzene, chlorobenzene, toluene, xylene, and at elevated temperatures, up to the boiling point of neutral :: solvent. alkali metal hydroxides, carbonates or alkoxides. Compounds of formula I are formed in as a mixture of their iis- and granous isomerism. Cis and trans compounds can be separated by fractional crystallization. Compounds of formula I can be converted into salts with the participation of inorganic or organic acids in the usual manner. Salt, hydrobromic, sulfuric, phosphoric, tartaric, para-toluenesulfonic acid. Example 1. To a solution of 400 g of 2- (2-ace-: oxystiryl) -pyridine in 1250 ml of chlorobenzene, 235.5 g of potassium methylate are added and the mixture is heated to 110 ° C to form a yellow suspension. , 483 g dimethylamine The ethyl chloride hydrochloride in the vibrating funnel is mixed by shaking with 1000 ml of ice-cold 30% sodium hydroxide solution, the oily base oil is separated, and oily base is added dropwise into six suspension. Pa3MeiJiKBJ, OT for another 30 min at ilG ° C, why is ice cooled and added. After etching with ether, drying with anhydrous solution; sulphate of sodium sulphate and evaporation of the solution: after that, an oil remains that is distilled from the condensate; m.p. 15G-161 ° C. Hu- 376 g of oil with the color of honey (yield 83% of theory). 123 g of the oily reaction product was dissolved in a mixture of 750 ml of ethyl acetate and 330 ml of absolute ethanol, while vigorously stirring, 430 ml of solution was gradually added, 132 ml of ethanolic hydrochloric acid solution (12.7%; all / volume) in 638 ml of ethyl acetate. Then 600 ml of ethyl acetate are added and cooled to 0 ° C. The released crystals (2-dimethylaminoethoxy) -styryl-pyridine-monohydrochloride are filtered off with suction, washed with ethyl acetate, and dried in a desiccator over concentrated sulfuric acid and kajiHK hydroxide; T. g (l.) o5- -187.5 ° C; If salt water is used, if an excess of ethanolic hydrochloric acid solution is used, a total of 300 ml of hydrochloric acid of the indicated concentration, the solution is colored dark yellow and then the (2-dimethylaminoethoxy) -styryl-nyridine dihydrochloride salt is isolated. 218-220 ° C. In a manner similar to that described in Example 1, the substances given in the following examples are obtained. Example 2. From 1- (2-acetoxyphenyl) -2 (pyridyl-2) -noprene-1 (bp 140 ° C) and dimethylaminoethyl chloride, 1- (2-dimethylaminoethoxyphenyl) -2- (pyridyl-2) - propene 1 - monohydrochloride; m.p. 128-133 ° C; yield 85% of theory. Example 3. From 2- (2-acetoxystyryl) -pyridine (mp 162-175 ° C) and 2-chloro-H, M-dimethylpropylamine, (3-dimethylaminopropane-2-hydroxy) -stil-pyridine is obtained; m.p. 158-159 ° C; yield 86% of theory. Example 4. From 2- (2-oxystiryl) -quinoline (mp. 274-278 ° C) and dimethylaminoethyl chloride, (2-dimethylaminoethoxy) - styryl-quinoline-monohydrochloride is obtained; so nl 188 ° C; yield 86% of theory. The subject matter of the invention 1. Method for producing | 3-aryl-2-aminoalkoxypros of the general formula I 2 0-CH-CH- (CH,), for R 5 where Ar is a phenyl, 2-, 3-, 4-pyridyl radical, which can be substituted by lower alkyl, 2-xi1, a) lilac radical or 2-pyrazpnyl radical, which can be more or less lower alkyl. pyrimidyl ra; , 1kal, which must be substituted by a lower alg: yl, 2-benzimidazolyl radical, which (5th may be replaced by a halogen atom, a lower alkyl or trifluoromethyl group, 2-furyl-, 2-hyenyl, 5-isoxazolyl radical, which may be lower alkyl or phenyl mixed with a lower alkyl 5- (1,2,4-oxadiazolyl) radical; RI, R2, R4, Ro are the same or different - hydrogen or alkyl; Hz - hydrogen or alkoxy; KB and R - same or different - hydrogen, alkyl-, alkenyloxyalkyl-, alkoxyalkyl or aralkyl radical, moreover Re and Rr, together with the nitrogen atom between them, can form a 5–7-membered saturated monocyclic, heterocyclic ring, which may also contain an oxygen atom or another nitrogen atom;

п - целое число О или 1,n is an integer O or 1,

отличающийс  тем, что стирол общей формулы IIcharacterized in that styrene of general formula II

где Аг, RI-Rs имеют указанные значени .Where Ar, RI-Rs have the indicated meanings.

X - атом водорода или ацетильна  группа, подвергают взаимодействию с амином общей формулы IIIX is a hydrogen atom or an acetyl group, reacted with an amine of the general formula III

/R/ R

Y - сн -сн - (сн,)п -N(Y - sn-sn - (ch,) n -N (

Claims (3)

I ,I, R R.R R. где имеют -хазанные значени , Y - атом галогена;where are —basic values, Y is a halogen atom; в присутствии основани  с последующим выделением целевого продукта в свободном виде или в виде соли.in the presence of a base, followed by isolation of the desired product in free form or as a salt. 2.Способ по п. 1, отличающийс  тем, что процесс провод т при нагревании до2. The method according to claim 1, characterized in that the process is carried out by heating to температуры кипени  растворител .boiling point of the solvent. 3.Способ по п. 1, отличающийс  тем, что смесь цис- и гранс-изомеров целевого продукта раздел ют, например, фракционной3. The method according to claim 1, characterized in that the mixture of cis and gras isomers of the target product is separated, for example, fractional кристаллизацией.crystallization.
SU1701181A 1969-08-05 1970-07-28 SU432712A3 (en)

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US4220603A (en) * 1977-10-07 1980-09-02 Mitsubishi Chemical Industries, Limited Pharmaceutically active (omega-aminoalkoxy)bibenzyls
JPS6045632B2 (en) * 1978-03-09 1985-10-11 三菱化学株式会社 ω-aminoalkoxystilbenes and their acid addition salts
DE2818765A1 (en) 1978-04-28 1979-11-08 Basf Ag AMINO DERIVATIVES OF 2-METHYL-5- (2-HYDROXYSTYRENE) -1,3,4-THIADIAZOLE
DE2818999A1 (en) * 1978-04-29 1979-11-15 Basf Ag AMINO DERIVATIVES OF 3-ALKYL-5- (2-HYDROXYSTYRYL) -ISOXAZOLES
DE2818998A1 (en) * 1978-04-29 1979-11-15 Basf Ag 3-ALKYL-5- (2-HYDROXY-STYRYL) -ISOXAZOLES AND METHOD FOR THE PRODUCTION THEREOF
JPS5629548A (en) * 1979-08-16 1981-03-24 Mitsubishi Chem Ind Ltd Omega-aminoalkoxystilbenes and their acid addition salts
DE2943405A1 (en) * 1979-10-26 1981-05-07 Basf Ag, 6700 Ludwigshafen NEW AMINO DERIVATIVES OF 5- (2-HYDROXYSTYRYL) -ISOXAZOLE
DE2943406A1 (en) 1979-10-26 1981-05-07 Basf Ag, 6700 Ludwigshafen AMINO DERIVATIVES OF 2-METHYL-5- (2-HYDROXYSTYRYL) -1,3,4-THIADIAZOL
DE3006809A1 (en) * 1980-02-23 1981-09-24 Basf Ag, 6700 Ludwigshafen 2 - ((3-AMINO-2-HYDROXY-PROPOXY) -STYRYL) -ISOXAZOLES, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL PREPARATIONS CONTAINING THEM
JPS5874379U (en) * 1981-11-16 1983-05-19 富士通株式会社 electronic equipment
NZ213986A (en) * 1984-10-30 1989-07-27 Usv Pharma Corp Heterocyclic or aromatic compounds, and pharmaceutical compositions containing such
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CA2838951C (en) 2011-06-10 2019-07-16 The Procter & Gamble Company An absorbent core for disposable diapers comprising longitudinal channels
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