KR830003488A - Process for preparing substituted tetraaza tricycle compound - Google Patents

Abstract

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Description

Process for preparing substituted tetraaza tricycle compound

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Claims (10)

Process for preparing substituted pyrazolobenzodiazepine of the following structural formula (I) In the above formula R ¹ is an alkyl group having ¹ to 4 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms or hydrogen; R ³ is a -CO-AR ⁴ group, R ⁴ is a -N (R ⁵ ) R ⁶ group, R ⁵ is an alkyl group having 1 to 4 carbon atoms or an alkenyl group having 1 to ⁵ carbon atoms, R ⁶ is R ⁵ or-(CH ₂ ) _m -N (R ⁷ ) R ⁸ , R ⁵ and R ⁶ both contain nitrogen atom and are morpholino group, pyrrolidino group, piperidino group, hexahydroazine -1-yl group, piperazin-1-yl group substituted with methyl or ethyl group or benzyl group in 4 position 2,4-dimethylpiperazin-1-yl group or hexahydro-1- substituted with methyl or ethyl group in position 4 1, 4-diazepin-1-yl group, R ⁷ is an alkyl group having 1 to 4 carbon atoms, R ⁸ is an alkyl group having 1 to 4 carbon atoms, A is a linear or cyclic alkylene group having 1 to 5 carbon atoms, m is 2 or 3, And acid addition salts in a halogena alkanoylpyrazolobenzyl diazepineone of the following structural formula. Where R ¹ , R ² and A are the same as above, Hal is a halogen atom, and reacts with the secondary amine of HN (R ⁵ ) R ⁶ (III) Wherein R ⁵ and R ⁶ are the same as above, and the resulting base is changed to an acid addition salt, or the resulting acid addition salt is changed to a free base or a pharmacologically useful acid addition salt. Process according to claim 1 characterized by a compound of formula I or a salt thereof, wherein R ¹ is a methyl group, R ² is a methyl group, R ³ is a -CO-AR ⁴ group, R ⁴ is a -N (R ⁵ ) R ⁶ group, R ⁵ is an alkyl group of 1-4 carbon atoms or an alkenyl group of 3-5 carbon atoms, R ^{6 also} represents R ⁵ or R ⁵ and R ⁶ together and includes linked nitrogen atoms. A pyrrolidino group, a piperidino group, a hexahydroazepine-1-, a diary, a piperazin-1-yl group substituted with a methyl or ethyl group at the 4 position, or a hexahydro substituted with a methyl or ethyl group at the 4 position 1H-1, 4-diazepin-1-yl group, etc. are included, and A is a C1-C1 linear alkylene group or their acid addition salt. A process according to claim 1 characterized by substituted pyrazolobenzodiazepinones of formula I ^* : In the above formula R ^{1 *} is a methyl or ethyl group, R ^{2 *} is hydrogen or methyl or ethyl group, R ^{3 *} is -CO-A ^* -R ^* , R ^{4 *} is -N (R ^{5 *} ) R ^{6 *} and R ^{5 *} is an alkyl group of 1-4 carbon atoms or an alkenyl group of 3-4 carbon atoms, R ^{6 *} represents R ^{5 *} or — (CH ₂ ) _m —N (R ^{7 *} ) R ^{8 *} , or R ^{5 *} and R ⁶ , a morpholino group, Pyridino group, piperidino group, hexahydroazin-1-yl group, piperazin-1-yl group in which 4-position is substituted with methyl, ethyl, benzene group, 2,4-dimethylpiperazin-1-yl group, 4- And a nitrogen atom whose position is linked to a hexahydro-1H-1, 4-diazepin-1-yl group substituted with a methyl, ethyl group. And acid addition salts prepared by the reaction of halogenoalkanoyl pyrazolobenzodiazepineone of the following structural formula II ^* , Wherein R ^{1 *} , R ^{2 *} and A ^* are the same as above and Hal ^* is a chlorine atom, and reacts with the secondary amine of formula III ^* HN (R ^{5 *} ) R ^{6 *} (III ^* ) Where R ^{5 *} and R ^{6 *} are the same as above. Process according to claim 3, characterized by a compound of formula I ^* or a pharmacologically useful acid addition salt thereof, wherein R ^{1 *} is a methyl or ethyl group, R ^{2 *} is a hydrogen atom or a methyl, ethyl group, R ^{5 *} represents a methyl or ethyl group, R ^{6 *} represents R ^{5 *} or (CH ₂ ) _m ^* -N (R ^{7 *} ) R ^{8 *} or R ^{6 *} and R ^{5 *} , and a nitrogen atom and includes pyrrolidino, Piperidino or hexahydroazin-1-yl groups, R ^{7 *} and R ^{8 *} are a methyl or ethyl group, m ^* is 2 and A ^* is a methylene group. Process according to claim 3, characterized by a compound of formula I ^* or a pharmacologically useful acid addition salt thereof, wherein R ^{1 *} is a methyl or ethyl group, R ^{2 *} is a hydrogen atom or a methyl or ethyl group, R ^{5 *} And R ^{6 *} , which are linked to a nitrogen atom, 4-position substituted with methyl, ethyl, benzyl, piperazin-1-yl, 2,4-dimethyl piperazin-1-yl or 4-position methyl or The hexahydro-1H-1, 4-diazepin-1-yl group substituted by the ethyl group and A ^* are methyl groups. Process according to claim 3, characterized by a compound of formula I ^* or an acid addition salt thereof, wherein R ^{1 *} is a methyl group, R ^{2 *} is a methyl group, R ⁵ is an alkyl group having 1-4 carbon atoms or 3-carbon number Alkenyl group of 4, R ^{6 *} is R ^{5 *} , or R ^{5 *} and R ^{6 *} , and includes a nitrogen atom connected, pyrrolidino group, piperidino group, hexahydroazin-1-yl group, 4-position is a piperazin-1-yl group etc. substituted by the methyl or ethyl group, and A ^* is a methylene group. Process according to claim 3, characterized by a compound of formula I ^* or a pharmacologically useful acid addition salt thereof, wherein R ^{1 *} is a methyl or ethyl group, R ^{2 *} is a hydrogen atom or a methyl or ethyl group, R ^{5 *} And R ^{6 *} , including nitrogen atom, 4-position substituted with methylene group as piperazin-1-yl group and A ^* is methylene group. A process according to claim 3 characterized by a compound of formula I ^* or a pharmacologically useful acid addition salt thereof, wherein R ^{1 *} and R ^{2 * are} methyl groups, R ^{5 *} and R ^{6 *} , nitrogen atoms Including piperazin-1-yl, the 4-position is a methyl group, and A ^* is a methylene group. Process for the preparation of substituted pyrazolo benzodiazepinones of formula I according to claim 1 for the specific examples above. In structural formula I ^* , R ^{1 *} is a methyl group, R ^{2 *} is a hydrogen atom, R ^{5 *} and R ^{6 *} and includes a nitrogen atom, which is a piperazin-1-yl group substituted with a methyl group at 4-position, A Is a methyl group or a pharmacologically useful addition salt thereof. ※ Note: The disclosure is based on the initial application.