RU95113154A - 1-фенил-3-диметиламино-пропановые соединения фармакологического действия - Google Patents
1-фенил-3-диметиламино-пропановые соединения фармакологического действияInfo
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- RU95113154A RU95113154A RU95113154/04A RU95113154A RU95113154A RU 95113154 A RU95113154 A RU 95113154A RU 95113154/04 A RU95113154/04 A RU 95113154/04A RU 95113154 A RU95113154 A RU 95113154A RU 95113154 A RU95113154 A RU 95113154A
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Abstract
1. 1-Фенил-3-диметиламино-пропановые соединения формулы 1где X обозначает OH, F, Cl, H либо OCOR-группу с Rсо значением C-алкил,Rпредставляет собой C-алкильную группу,Rобозначает H либо C-алкильную группу,Rобозначает H либо линейную C-алкильную группуилиRи Rоба вместе представляют собой C-циклоалкильный остаток,и если Rявляется H, тоRобозначает мета-O-Z с Z, имеющим значение H, С-алкил, PO(OC-алкил), CO(OC-алкил), CONH-CH-(C-алкил), CO-CH-R, причем Rпредставляет собой орто-OCOC-алкил или мета- либо пара-CHN(R)с R, имеющим значение C-алкил либо 4-морфолино, или же Rобозначает мета-S-C-алкил, мета-Cl, мета-F, мета-CRRRс R, Rи R, имеющими значение H либо F, орто-OH, орто-O-C-алкил, пара-F либо пара-CRRR,или если Rобозначает находящийся всегда в пара-положении Cl, F, OH либо O-C-алкил, тоRобозначает находящийся всегда в мета-положении Cl, F, OH либо O-C-алкил,илиRи Rоба вместе обозначают 3,4-OCH=CH- либо 3,4-OCH=CHO-, в качестве диастереомеров или энантиомеров в виде их оснований либо солей физиологически совместимых кислот.2. Соединения по п. 1, отличающиеся тем, что X представляет собой OH, F, Cl либо H, Rобозначает C-алкильную группу, Rобозначает H либо CHи Rобозначает H либо CH, и если Rявляется H, то Rобозначает мета-O-C-алкил, мета-OH, мета-S-C-алкил, мета-F, мета-Cl, мета-СН, мета-CFH, мета-CFлибо пара-CFили если Rпредставляет собой находящийся всегда в пара-положении Cl либо F, то Rобозначает находящийся всегда в мета-положении Cl либо F, или же Rи Rоба вместе обозначают 3,4-OCH=CH-.Соединения по одному из пп. 1 - 2, отличающиеся тем, что соединения формулы I, в которой Rи Rимеют разные значения, представлены в виде их диастереомеров с конфигурацией Ia4. Способ получения 1-фенил-3-диметиламино-пропановых соединений формулы I с X, представляющим собо
Claims (1)
1. 1-Фенил-3-диметиламино-пропановые соединения формулы 1
где X обозначает OH, F, Cl, H либо OCOR6-группу с R6 со значением C1-3-алкил,
R1 представляет собой C1-4-алкильную группу,
R2 обозначает H либо C1-4-алкильную группу,
R3 обозначает H либо линейную C1-4-алкильную группу
или
R2 и R3 оба вместе представляют собой C4-7-циклоалкильный остаток,
и если R5 является H, то
R4 обозначает мета-O-Z с Z, имеющим значение H, С1-3-алкил, PO(OC1-4-алкил)2, CO(OC1-5-алкил), CONH-C6H4-(C1-3-алкил), CO-C6H4-R7, причем R7 представляет собой орто-OCOC1-3-алкил или мета- либо пара-CH2N(R8)2 с R8, имеющим значение C1-4-алкил либо 4-морфолино, или же R4 обозначает мета-S-C1-3-алкил, мета-Cl, мета-F, мета-CR9R10R11 с R9, R10 и R11, имеющими значение H либо F, орто-OH, орто-O-C2-3-алкил, пара-F либо пара-CR9R10R11,
или если R5 обозначает находящийся всегда в пара-положении Cl, F, OH либо O-C1-3-алкил, то
R4 обозначает находящийся всегда в мета-положении Cl, F, OH либо O-C1-3-алкил,
или
R4 и R5 оба вместе обозначают 3,4-OCH=CH- либо 3,4-OCH=CHO-, в качестве диастереомеров или энантиомеров в виде их оснований либо солей физиологически совместимых кислот.
где X обозначает OH, F, Cl, H либо OCOR6-группу с R6 со значением C1-3-алкил,
R1 представляет собой C1-4-алкильную группу,
R2 обозначает H либо C1-4-алкильную группу,
R3 обозначает H либо линейную C1-4-алкильную группу
или
R2 и R3 оба вместе представляют собой C4-7-циклоалкильный остаток,
и если R5 является H, то
R4 обозначает мета-O-Z с Z, имеющим значение H, С1-3-алкил, PO(OC1-4-алкил)2, CO(OC1-5-алкил), CONH-C6H4-(C1-3-алкил), CO-C6H4-R7, причем R7 представляет собой орто-OCOC1-3-алкил или мета- либо пара-CH2N(R8)2 с R8, имеющим значение C1-4-алкил либо 4-морфолино, или же R4 обозначает мета-S-C1-3-алкил, мета-Cl, мета-F, мета-CR9R10R11 с R9, R10 и R11, имеющими значение H либо F, орто-OH, орто-O-C2-3-алкил, пара-F либо пара-CR9R10R11,
или если R5 обозначает находящийся всегда в пара-положении Cl, F, OH либо O-C1-3-алкил, то
R4 обозначает находящийся всегда в мета-положении Cl, F, OH либо O-C1-3-алкил,
или
R4 и R5 оба вместе обозначают 3,4-OCH=CH- либо 3,4-OCH=CHO-, в качестве диастереомеров или энантиомеров в виде их оснований либо солей физиологически совместимых кислот.
2. Соединения по п. 1, отличающиеся тем, что X представляет собой OH, F, Cl либо H, R1 обозначает C1-4-алкильную группу, R2 обозначает H либо CH3 и R3 обозначает H либо CH3, и если R5 является H, то R4 обозначает мета-O-C1-3-алкил, мета-OH, мета-S-C1-3-алкил, мета-F, мета-Cl, мета-СН3, мета-CF2H, мета-CF3 либо пара-CF3 или если R5 представляет собой находящийся всегда в пара-положении Cl либо F, то R4 обозначает находящийся всегда в мета-положении Cl либо F, или же R4 и R5 оба вместе обозначают 3,4-OCH=CH-.
Соединения по одному из пп. 1 - 2, отличающиеся тем, что соединения формулы I, в которой R2 и R3 имеют разные значения, представлены в виде их диастереомеров с конфигурацией Ia
4. Способ получения 1-фенил-3-диметиламино-пропановых соединений формулы I с X, представляющим собой OH, по пп. 1 - 3, отличающийся тем, что β-диметиламинокетон формулы II
с помощью металлоорганического соединения формулы III,
в которой Z обозначает MgCl, MgBr, MgJ или Li, трансформируют в соединение формулы I, в которой X обозначает OH.
4. Способ получения 1-фенил-3-диметиламино-пропановых соединений формулы I с X, представляющим собой OH, по пп. 1 - 3, отличающийся тем, что β-диметиламинокетон формулы II
с помощью металлоорганического соединения формулы III,
в которой Z обозначает MgCl, MgBr, MgJ или Li, трансформируют в соединение формулы I, в которой X обозначает OH.
5. Способ получения 1-фенил-3-диметиламино-пропановых соединений формулы I с X, представляющим собой H, по пп. 1 - 3, отличающийся тем, что соединение формулы I, в которой X обозначает Cl, подвергают взаимодействию с боргидридом цинка, цинкцианоборгидридом и/или оловоцианоборгидридом.
6. Способ получения 1-фенил-3-диметиламино-пропановых соединений формулы I с X, представляющим собой F, по пп. 1 - 3, отличающийся тем, что соединение формулы I, в которой X обозначает OH, подвергают взаимодействию с диметиламино-сульфотрифторидом в растворителе.
7. Способ получения 1-фенил-3-диметиламино-пропановых соединений формулы I с X, представляющим собой Cl, по пп. 1 - 3, отличающийся тем, что соединение формулы I, в которой X обозначает OH, подвергают взаимодействию с тионилхлоридом.
8. Способ получения 1-фенил-3-диметиламино-пропановых соединений формулы I, в которой X обозначает OCOR6-группу с R6, представляющим собой C1-3-алкил, по пп. 1 - 3, отличающийся тем, что соединение формулы I, в которой X обозначает OH, подвергают взаимодействию с хлоридом кислоты Cl-COOR6.
9. Применение одного из 1-фенил-3-диметиламино-пропановых соединений формулы I по пп. 1 - 3 в качестве фармацевтического активного вещества.
10. Болеутоляющее лекарственное средство, содержащее в качестве активного вещества по крайней мере одно 1-фенил-3-диметиламино-пропановое соединение формулы I по пп. 1 - 3.
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DE4426245A DE4426245A1 (de) | 1994-07-23 | 1994-07-23 | 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung |
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