KR830002719A - Method for producing 2-imidazoline derivatives - Google Patents

Abstract

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Description

Method for producing 2-imidazoline derivatives

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Claims (55)

The following structural compounds and their pharmaceutically acceptable salts In the above structural formula R ¹ is halogen, lower alkyl, lower alkoxy, lower alkanesulfonamido, mono (or di or tri)-halo (lower) alkyl, carbamoyl, hydroxy, nitro, amino, cyano, sulfamoyl, N, 1 to 5 substituents selected from the group consisting of N-di (lower) alkylsulfamoyl and di(lower) alkylamino with or without oxygen or nitrogen atoms, which can form a 3 to 7-corner. Aryl having; R ² and R ³ are each hydrogen, halogen, lower alkyl, lower alkoxy, lower alkanesulfone amido, mono (or di or tri)-halo (lower) alkyl, carbamoyl, hydroxy, nitro, amino, cyano sulfa Moyl, N, N-di(lower)alkyl sulfa moyl, or di(lower)alkyl amino capable of forming 3 to 7-rings with or without oxygen or other nitrogen atoms. A is -0-, -s- or -CH ₂ -and n is an integer of 0 or 1. This halogen, lower alkyl, lower alkoxy, lower alkanesulfonamido, mono (or di or tri)-halo (lower) alkyl, carbamoyl, hydroxy, nitro, aminocyano, sulfamoyl, N, N-di ( Phenyl which may have 1 to 5 substituents selected from the group consisting of di(lower) alkylamino with 3 to 7-membered rings, with or without oxygen, or with or without oxygen or other nitrogen atoms. Or a naphthyl compound of claim 1. A compound of claim 2 in which n is 1. A compound of claim 3 wherein A is -0-. A compound of claim 4 which is 2-(2-phenoxyphenyl) amino-2-imidazoline. 2-[2-(4-Chlorophenoxy)phenyl] amino-2-imidazoline or a sulfate of these compounds of claim 4 Compound of claim 4, which is 2-[2-(4-chlorophenoxy)-5-chlorophenyl] amino-2-imidazoline A compound of claim 4 which is 2-(2-phenoxy-5-chlorophenyl) amino-2-imidazoline. A compound of claim 4 which is 2-(2-phenoxy-5-methylphenyl) amino-2-imidazoline. A compound of claim 4 which is 2-(2-phenoxy-3-methylphenyl) amino-2-imidazoline. A compound of claim 4 which is 2-(2-phenoxy-4-methylphenyl) amino-2-imidazoline. A compound of claim 4 which is 2-(2-phenoxy-5-prefluoromethylphenyl) amino-2-imidazoline. A compound of claim 4 which is 2-(2-phenoxy-5-nitrophenyl) amino-2-imidazoline. 2-[2-(3, 4, 5-trimethoxyphenoxy)phenyl] A compound of claim 4 that is amino-2-imidazoline. A compound of claim 4 which is 2-(2-phenoxy-5-dimethylaminophenyl) amino-2-imidazoline. A compound of claim 3 wherein A is -S-. A compound of claim 16 which is 2-(2-phenylthiophenyl) amino-2-imidazoline. A compound of claim 3 wherein A is -CH ₂ -. A compound of claim 2 in which n is 0. A compound of claim 19 which is 2-(2-biphenyl) amino-2-imidazoline. A compound of claim 19 which is 2-[2-(2-chlorophenyl)phenyl] amino-2-imidazoline. A compound of claim 19 which is 2-[2-(2-fluorophenyl)phenyl] amino-2-imidazoline. A compound of claim 19 which is 2-[2-(4-fluorophenyl)phenyl] amino-2-imidazoline. It consists of the following steps 1) The following structural compound or a salt thereof is reacted with ethylenediamine or a salt thereof to obtain compound (I), or In the above structural formula R ¹ , R ² , R ³ , A and n are defined above. 2) The following structural compound or a salt thereof is reacted with ethylenediamine or a salt thereof to obtain compound (I), or In the above structural formula R ¹ , R ² , R ³ , A and n are defined above. 3) the following structural compounds or salts thereof Structural compounds Or by reacting with these salts to obtain a compound of formula (I) or R ¹ , R ² , R ³ , A and n in the above formula are defined above. 4) the following structural compounds or salts thereof To obtain the following structural compounds or salts thereof In the structural formula R ^2, A and n is an exemplary each as defined above R ¹ a is the same as R ¹ (R ¹ is as defined above) R ³ a is hydrogen or nitro, R ¹ a is R ³ a is hydrogen Aryl substituted with nitro at one time, R ¹ b is the same as R ¹ (R ¹ is as defined above. R ³ b is hydrogen or amino R ¹ b is aryl substituted with amino when R ³ b is hydrogen A method for preparing 2-imidazoline derivatives of the following structural formula and their pharmaceutically acceptable salts. In the above structural formula R ¹ is halogen, lower alkyl, lower alkoxy, lower alkanesulfonamino, mono (or di or tri)-halo (lower) alkyl, carbamoyl, hydroxy, nitro, amino, cyano, sulfamoyl, N, N- Is an aryl having 1 to 5 substituents selected from the group consisting of di(lower)-alkylsulfamoyl and di(lower)alkylamino with or without oxygen or with nitrogen or with a nitrogen to form a 3- to 7-membered ring. ; R ² and R ³ are each hydrogen, halogen, lower alkyl, lower alkoxy, lower alkanesulfonamido, mono (or di or tri)-halo (lower) alkyl, carbamoyl, hydroxy, nitro, amino, cyano, Sulfamoyl, N, N-di(lower) alkylsulfamoyl or di(lower)alkyl amino with or without oxygen or with a nitrogen or other nitrogen atom to form a 3 to 7-membered ring; A is -0-, -s- or -CH _2- ; And n is 0 or 1 integer. A pharmaceutical composition comprising a compound of claim 1 in admixture with an overall non-carrier carrier and excipients that may be pharmaceutically acceptable. A method of treating hypertension, inflammation and gastrointestinal failure and pain of various causes by administering an effective amount of a compound of claim 1 to a human. ※ Note: Disclosure is based on the original application.