KR900011775A - Imidazopyridazine, its preparation and uses - Google Patents

Abstract

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Description

Imidazopyridazine, its preparation and uses

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Claims (24)

The imidazo [1,2-b] pyridazine compound of the following general formula (I) or its salt. [Wherein, R ₁ is hydrogen or a halogen atom or a lower alkyl group which may optionally have a substituent, and R ₂ and R ₃ are independently a hydrogen atom, a lower alkyl group which may optionally have a substituent, a cycloalkyl group, or optionally a substituent May be a phenyl group, or R ₂ and R ₃ together with the adjacent nitrogen atoms may form a heterocyclic ring which may optionally have a substituent, X is an oxygen atom or S (O) n (n is 0 to 2), and Alk is a linear or branched alkylene group having 1 to 10 carbon atoms which may optionally have a substituent. (Wherein R ₁ is a hydrogen atom, any one of R ₂ and R ₃ is a hydrogen atom, the other is a hydrogen atom or a lower alkyl group, and Alk is a straight alkylene group having 2 to 4 carbon atoms, X is an oxygen atom) Should be 2. A compound according to claim 1, wherein R ₁ is a hydrogen atom or a lower alkyl group substituted at the 2 position of the imidazo [1,2-b] pyridazine ring, and R ₂ and R ₃ independently have a hydrogen atom, optionally a substituent A lower alkyl group, a cycloalkyl group, or a phenyl group, which may optionally have a substituent, or R ₂ and R ₃ together with their adjacent nitrogen atoms form a heterocyclic ring which may optionally have a substituent, and X is oxygen or sulfur An atom, Alk is a C1-C6 linear alkylene group. 2. A compound according to claim 1, wherein (i) R ₁ is a lower alkyl group substituted at the 3-position of the imidazo [1,2-b] pyridazine ring, or (ii) R ₁ is a lower alkyl group or halogen atom having a substituent, (iii) x is SO or SO ₂ or (iv) Alk may have a linear alkylene group having 1 to 6 carbon atoms having a substituent, a linear alkylene group having 7 to 10 carbon atoms which may optionally have a substituent or optionally a substituent. A compound which is a C2-C10 branched alkylene group. The compound of claim 1, wherein R ₁ is a hydrogen atom. The compound of claim 1, wherein x is an oxygen atom. A compound according to claim 1, wherein Alk is a branched alkylene group having 2 to 6 carbon atoms. The compound of claim 1, wherein R ₂ and R ₃ are hydrogen atoms. A compound according to claim 1, wherein Alk is a molecular chain alkylene group having 4 to 5 carbon atoms. The compound or a salt thereof according to claim 1, represented by the following formula. [In formula, Alk ¹ is a C1-C6 linear or branched alkylene group.] The compound or a salt thereof according to claim 1, represented by the following formula. [Wherein, Alk ² is a branched alkylene group having 2 to 6 carbon atoms and X ¹ is an oxygen or sulfur atom.] The compound or a salt thereof according to claim 1, represented by the following formula. [Wherein, Alk ³ is a straight-chain or branched-chain alkylene group having a carbon number of 3~5, X ¹ is an oxygen or sulfur atom.] The compound according to claim 1, wherein the lower alkyl group which may optionally have a substituent is an alkyl group having 1 to 6 carbon atoms which is unsubstituted or substituted by hydroxy. The compound according to claim 1, wherein the cycloalkyl group is a cycloalkyl group having 3 to 6 carbon atoms. The compound according to claim 1, wherein the phenyl group which may optionally have a substituent is an unsubstituted or a phenyl group substituted by 1 to 3 halogens or lower alkoxy. The compound of claim 1, wherein the heterocyclic ring is a 5 or 6 membered heterocyclic ring. The 6-[(2,2-dimethyl-3-sulfamoyl propyl) oxy] imidazo [1,2-b] pyridazine or salt thereof according to claim 1. The 6-[(2-methyl-3-sulfamoyl propyl) thio] imidazo [1,2-b] pyridazine or salt thereof according to claim 1. Imidazo [1,2-b] characterized by reacting a compound of formula (II) or a salt thereof with a compound of formula (III) or a salt thereof to obtain a compound of formula (I) or a salt thereof Process for the preparation of pyridazine compounds. Wherein R ¹ is hydrogen or a halogen atom or a lower alkyl group which may optionally have a substituent, and R ₂ and R ₃ may independently have a hydrogen atom, a lower alkyl group which may optionally have a substituent, a cycloalkyl group, or optionally a substituent Phenyl group, or R ₂ and R ₃ together with the adjacent nitrogen atom, may form a heterocyclic ring which may optionally have a substituent, X is an oxygen atom or S (O) n (n is 0 to 2) Alk is a linear or branched alkylene group having 1 to 10 carbon atoms which may optionally have a substituent, provided that R ₁ is a hydrogen atom, one of R ₂ and R ₃ is a hydrogen atom and the other is a hydrogen atom Or a lower alkyl group, where Alk is a linear alkylene group having 2 to 4 carbon atoms, X should be an oxygen atom), and Y is a reactive group.] Imidazo [1,2-b] characterized by reacting a compound of formula (IV) or a salt thereof with a compound of formula (V) or a salt thereof to obtain a compound of formula (I ′) or a salt thereof The manufacturing method of a pyridazine compound. [Wherein, R ₁ is hydrogen or a halogen atom or a lower alkyl group which may optionally have a substituent, and R ₂ and R ₃ may independently have a hydrogen atom, a lower alkyl group which may optionally have a substituent, a cycloalkyl group or an optionally substituent Phenyl group, or R ₂ and R ₃ together with the adjacent nitrogen atoms form a heterocyclic ring which may optionally have a substituent, X is an oxygen atom or S (O) n (n = 0 to 2) , Z is a reactive group, and Alk is a linear or branched alkylene group having 1 to 10 carbon atoms which may optionally have a substituent.] Imidazo [1,2-b] characterized by reacting a compound of formula (VI) or a salt thereof with an amine of formula (i) or a salt thereof to obtain a compound of formula (I ′) or a salt thereof ] The manufacturing method of a pyridazine compound. [Wherein, R ₁ is hydrogen or a halogen atom or a lower alkyl group which may optionally have a substituent, and R ₂ and R ₃ may independently have a hydrogen atom, a lower alkyl group which may optionally have a substituent, a cycloalkyl group or an optionally substituent Phenyl group, or R ₂ and R ₃ together with their adjacent nitrogen atoms form a heterocyclic ring which may optionally have a substituent, X is an oxygen atom or S (O) n (n = 0 to 2) and Alk Is a C1-C10 linear or branched alkylene group which may optionally have a substituent, and W is a halogen atom.] An anti-asthmatic composition comprising a compound of formula (I ′) or a salt thereof, and a pharmaceutically acceptable carrier or diluent. [Wherein, R ₁ is hydrogen or a halogen atom or a lower alkyl group which may optionally have a substituent, and R ₂ and R ₃ may independently have a hydrogen atom, a lower alkyl group which may optionally have a substituent, a cycloalkyl group or an optionally substituent Phenyl group, or R ₂ and R ₃ together with their adjacent nitrogen atoms form a heterocyclic ring which may optionally have a substituent, X is an oxygen atom or S (O) n (n = 0 to 2) and Alk Is a C1-C10 linear or branched alkylene group which may optionally have a substituent.] The anti-asthmatic composition according to claim 21, wherein compound (I ') is 6- (3-sulfamoylpropylthio) imidazo [1,2-b] pyridazine. An anti-asthmatic composition comprising a compound of formula (I) according to claim 1 or a salt thereof and a pharmaceutically acceptable carrier or diluent. The anti-asthmatic composition according to claim 23, which contains a compound according to any one of claims 2 to 17 or a salt thereof. ※ Note: The disclosure is based on the initial application.