KR890002021A - Benzasecin derivatives - Google Patents

Abstract

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Description

Benzasecin derivatives

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Claims (38)

Benzasecin derivatives of general formula (I) Wherein R ¹ and R ² are each hydrogen or chlorine; R ³ is hydrogen, fluorine, chlorine, bromine or methoxy; R ⁴ is hydrogen, chlorine or methoxy; R ⁵ is hydrogen, acetyl, propionyl, benzoyl, chloro, benzoyl, methoxy, benzoyl or phenyl acetyl; Provided that two or three of R ¹ to R ⁴ are hydrogen. The benzasecin derivative of claim 1, wherein R ¹ is chlorine and R ² , R ³ and R ⁴ are each hydrogen. The benzasecin derivative of claim 1, wherein R ² is chlorine and R ¹ , R ³ and R ⁴ are each hydrogen. The benzasecin derivative according to claim 1, wherein R ³ is fluorine, chlorine, bromine or methoxy and R ¹ , R ² and R ⁴ are each hydrogen. The benzasecin derivative of claim 1, wherein R ⁴ is chlorine and R ¹ , R ² and R ⁴ are each hydrogen. The benzasecin derivative according to claim ¹ , wherein R ¹ and R ³ are each chlorine and R ² and R ⁴ are each hydrogen. The benzasecin derivative according to any one of claims 1 to 6, which is R ⁵ acetyl. 4-acetyl-9-chloro-1,2,4,5,6,7-hexahydro-4-benazasecin-3,8-dione. 4-acetyl-11-chloro-1,2,4,5,6,7-hexahydro-4-benazasecin-3,8-dione. 4-acetyl-11-fluoro-1,2,4,5,6,7-hexahydro-4-benazasecin-3,8-dione. 4-acetyl-9,11-dichloro-1,2,4,5,6,7-hexahydro-4-benzeazin-3,8-dione. 4-acetyl-11-methoxy-1,2,4,5,6,7-hexahydro-4-benzeazin-3,8-dione. 11-Chloro-1,2,4,5,6,7-hexahydro-4-propionyl-benazasecin-3,8-dione. 4-benzoyl-11-chloro-1,2,4,5,6,7-hexahydro-4-benazasecin-3,8-dione. 4- (o-methoxybenzoyl) -11-chloro-1,2,4,5,6,7-hexahydro-4-benazasecin-3,8-dione. 4- (m-methoxybenzoyl) -11-chloro-1,2,4,5,6,7-hexahydro-4-benazasecin-3,8-dione. 4- (p-methoxybenzoyl) -11-chloro-1,2,4,5,6,7-hexahydro-4-benazasecin-3,8-dione. 11-chloro-4- (p-chlorobenzoyl) -1,2,4,5,6,7-hexahydro-4-benzeazin-3,8-dione. 4-acetyl-1,2,4,5,6,7-hexahydro-12-methoxy-4-benazasecin-3,8-dione. 9-Chloro-1,2,4,5,6,7-hexahydro-4-benzeazin-3,8-dione: 4-acetyl-10-chloro-1,2,4,5,6,7 Hexahydro-4-benzeazine-3,8-dione: 11-chloro-1,2,4,5,6,7-hexahydro-4- (phenylacetyl) -4-benzeazine-3, 8-dione: 11-chloro-1,2,4,5,6,7-hexahydro-4-benzasecin-3,8-dione: 4-acetyl-11-bromo-1,2,4, 5,6,7-hexahydro-4-benzasecin-3,8-dione: and 4-acetyl-12-chloro-1,2,4,5,6,7-hexahydro-4-benzasecin -3,8-dion. Benzoquinoline derivatives of general formula (II). Wherein R ¹ , R ² , R ³ , R ⁴ , and R ⁵ are as defined in claim 1. 4-acetyl-8-chloro-1,2,3,4,5,6-hexahydrobenzo [f] quinoline. 4-acetyl-10-chloro-1,2,3,4,5,6-hexahydrobenzo [f] quinoline. 8-chloro-4- (p-chlorobenzoyl) -1,2,3,4,5,6-hexahydrobenzo [f] quinoline. Benzasecin derivatives of general formula (III) Wherein R ¹ , R ² , R ³ , and R ⁴ are as defined in claim 1; Z is a separable group; Except acetyl, propionyl, benzoyl, chloro benzoyl, methoxy benzoyl or phenylacetyl. The compound according to any one of claims 1 to 20 and 22 to 24 for use as a therapeutically active substance. The compound according to any one of claims 1 to 20 and 24 for use as a therapeutically active substance which inhibits brain failure or improves cognitive function. The benzoquinoline derivative of formula (II) is oxidized or the group Z is removed from the benzasecin derivative of formula (III), and the formula (I) according to any one of claims 1 to 20. Method for preparing a benzasecin derivative of. Wherein R ¹ , R ² , R ³ , R ⁴ , and R ⁵ are as defined in claim 1 and: Z is a separable group. To reduce the benzo quinolinone derivative of formula (Ⅳ), or if necessary, reacted with a compound represented by the general formula (Ⅴ) Formula (Ⅵ) under strongly basic presence of a compound of and, in the general formula the obtained R ⁵ is hydrogen N-substituted compound of (II) with acetyl, propionyl, benzoyl, chloro benzoyl, methoxy benzoyl or phenylacetyl, wherein the benzoquinoline derivative of formula (II) according to any one of claims 21 to 24 How to prepare. Wherein R ¹ , R ² , R ³ , and R ⁴ are as defined in claim 1 and X is a leaving group. A medicament containing a compound according to any one of claims 1 to 20 and 22 to 24 and a therapeutically inert excipient. An agent for inhibiting or improving cognitive function of brain failure, which comprises the compound according to any one of claims 1 to 20 and 22 to 24 and a therapeutically inactive excipient. Use of a compound according to any one of claims 1 to 20 and 22 to 24 for the inhibition or prevention of a disease or for the improvement of health. Use of a compound according to any one of claims 1 to 20 and 22 to 24 for the inhibition or prevention of brain failure or for the improvement of cognitive function. Use of a compound according to any one of claims 1 to 20 and 22 to 24 for the manufacture of a medicament for inhibiting or preventing brain failure or improving cognitive function. The benzasecin derivative according to any one of claims 1 to 20, prepared by the method of claim 28 or a similar chemical method. The benzoquinoline derivative according to any one of claims 21 to 24 prepared by the method of claim 29 or a similar chemical method. The present invention as described above. The method of claim 1, wherein the compound according to any one of claims 1 to 20 and 22 to 24 is administered to the mammal in an amount sufficient to inhibit brain failure and / or improve cognitive function. To inhibit and / or improve cognition. ※ Note: The disclosure is based on the initial application.