Novel isoxazolylalkylpiperazine derivatives having selective biological activity at dopamine D3 or D4 receptor, and preparation thereof
AssigneesKorea Institute of Science and Technology, Korea Research Institute of Chemical Technology, Korea Advanced Institute of Science and Technology
InventorsHun Yeong Koh, Kyung II Choi, Yong Seo Cho, Ae Nim Pae, Kyung Ho Kang, Mi Young Cha, Jae Yang Kong, Dae Young Jeong, Hee-Yoon Lee
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Abstract
The present invention relates to a novel isoxazolylalkylpiperazine derivatives having selective biological activity at dopamine D3 or D4 receptors represented by the following formula (1), and its preparation method through reductive amination reaction in the presence of reducing agent, 1 wherein R1, R2, R3, R4, R5, R6, X and n are the same as defined in the specification.
Claims9
Isoxazolylalkylpiperazine derivative represented by the following formula (1), and pharmaceutically acceptable addition salt thereof,
- 115
- wherein R1, R2, R3, R4 and R5 may be identical or different which are a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, hydroxyl, hydroxymethyl, aryl, heteroaryl, amino, C1-C6 alkylamino, carbonyl, C3-C8 cycloalkyl or C3-C8 heterocyclic group;
- R6 represents a hydrogen atom, a halogen atom, alkyl, C1-C6 alkoxy, aryl, pyridyl, heterocyclic or pyrimidyl group;
- X represents CH or a nitrogen atom;
- and
- n represents 3 or 4.
A preparation method of the compound represented by the following formula (1), wherein amine compound represented by the following formula (2) and aldehyde compound represented by the following formula (3) are reductively aminated in the presence of a reducing agent,
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- wherein R1, R2, R3, R4 and R5 may be identical or different, which represents a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, hydroxyl, hydroxymethyl, aryl, heteroaryl, amino, C1-C6 alkylamino, carbonlyl, C3-C8 cycloalkyl or C3-C8 heterocyclic group;
- R6 represents a hydrogen atom, a halogen atom, alkyl, C1-C6 alkoxy, aryl, pyridyl, heterocyclic or pyrimidyl group;
- X represents CH or a nitrogen atom;
- and
- n represents 3 or 4.
Dopamine antagonists which contains isoxazolylalkylpiperazine derivatives represented by the following formula (1) or its pharmaceutically acceptable addition salts,
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- wherein R1, R2, R3, R4 and R5 are identical or different, which represents a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, hydroxyl, hydroxymethyl, aryl, heteroaryl, amino, C1-C6 alkylamino, carbonyl, C3-C8 cycloalkyl or C3-C8 heterocyclic group;
- R6 represents a hydrogen atom, halogen atom, alkyl, C1-C6 alkoxy, aryl, pyridyl, heterocyclic or pyrimidyl group;
- X represents CH or a nitrogen atom;
- and
- n represents 3 or 4.
Dependencies are inferred from the claim text.