Remedies for allergic eye diseases

Abstract

An agent for the treatment of allergic eye disease containing a 3-anilino-2-cycloalkenone derivative having the formula (I): wherein R 1 is an unsubstituted or substituted C 1 to C 8 alkyl group provided that an unsubstituted methyl group is excluded, a C 3 to C 7 cycloalkyl group, a C 6 to C 10 bicycloalkyl group or an indanyl group, etc., R 2 is a C 1 to C 4 alkyl group, R 3 is a hydrogen atom, a C 1 to C 5 alkyl group, a C 3 to C 7 cycloalkyl group, etc., R 4 is a hydrogen atom, an unsubstituted or substituted C 1 to C 5 alkyl group, a halogen atom, etc., R 5 , R 6 , R 7 and R 8 are independently a hydrogen atom, a C 1 to C 5 alkyl group, etc., X is —(CR 11 R 12 )n- or NR 13 —, wherein n is 0 to 2, R 11 , R 12 and R 13 are independently a hydrogen atom, a C 1 to C 5 alkyl group, etc.

1 . An agent for the treatment of an allergic eye disease comprising a 3-anilino-2-cycloalkenone derivative having the formula (I):  
       
         
           
           
               
               
           
         
       
       wherein R 1  is an unsubstituted or substituted C 1  to C 8  alkyl group provided that an unsubstituted methyl group is excluded, a C 3  to C 7  cycloalkyl group, a C 6  to C 10  bicycloalkyl group, a 3-tetrahydrofuryl group or an indanyl group, R 2  is a C 1  to C 4  alkyl group, R 3  is a hydrogen atom, an unsubstituted or substituted C 1  to C 5  alkyl group, a C 3  to C 7  cycloalkyl group or an acyl group, R 4  is a hydrogen atom, an unsubstituted or substituted C 1  to C 5  alkyl group, a halogen atom, a group having the formula (II):  
       
         
           
           
               
               
           
         
       
       wherein R 9  and R 10  are independently a C 1  to C 5  alkyl group, or group having the formula (III):  
       
         
           
           
               
               
           
         
       
       wherein n is an integer of 2 to 6, provided that one CH 2  group may be substituted with one hetero atom selected from the group consisting of an oxygen atom, nitrogen atom and sulfur atom, R 5 , R 6 , R 7  and R 8  are independently a hydrogen atom, an unsubstituted or substituted C 1  to C 5  alkyl group or an unsubstituted or substituted phenyl group, X is —(CR 11 R 12 ) n —, wherein R 11  and R 12  are independently a hydrogen atom, an unsubstituted or substituted C 1  to C 5  alkyl group or an unsubstituted or substituted phenyl group, n is an integer of 0 to 2, where, when n is 0, the carbonylcarbon atom adjacent to X and the other carbon atom are directly bonded to form a 5-member ring, or —NR_— wherein R 13  is a hydrogen atom or unsubstituted or substituted C 1  to C 5  alkyl group, or a stereoisomer or optical isomer thereof, or pharmacologically acceptable salt thereof, or a hydrate or solvate thereof.  
     
     
         2 . An agent for the treatment of an allergic eye disease comprising the 3-anilino-2-cycloalkenone derivative according to  claim 1 , or, stereoisomer or optical isomer thereof, pharmacologically acceptable salt thereof, or a hydrate or solvate thereof, wherein, in the formula (I), R 1  is butyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, (1-phenylcyclopropyl)methyl, benzyl, phenethyl, 2-(1-naphthyl)ethyl, 2-(2-indanyl)ethyl, bicyclo[2,2,1]hept-2-yl, 3-tetrahydrofuryl, or 2-indanyl, R 2  is methyl, R 3  is a hydrogen atom, methyl, ethyl, propyl, butyl, pentyl, 2-pyridylmethyl, 3-pyridylmethyl, 4-pyridylmethyl, benzyl, 1-naphthylmethyl, 2-naphthylmethyl, 2-quinolylmethyl, cyclopentyl, or acetyl, R 4  is a hydrogen atom, halogen atom, methyl, ethyl, dimethylaminomethyl, morpholinomethyl or benzyl, R 5 , R 6 , R 7  and R 8  are independently a hydrogen atom or methyl, X is —(CR 11 R 12 ) n — wherein R 11  and R 12  are independently a hydrogen atom or methyl, and n is 0 or 1, or NR 13 — wherein R 13  is a hydrogen atom, a C 1  to C 3  alkyl group, or benzyl.  
     
     
         3 . An agent for the treatment of an allergic eye disease comprising the 3-anilino-2-cycloalkenone derivative according to  claim 1 , or a stereoisomer or optical isomer thereof, a pharmacologically acceptable salt, or a hydrate or solvate, wherein the 3-anilino-2-cycloalkenone derivative is 3-(3-cyclohexyloxy-4-methoxyanilino)-2-methyl-2-cyclopenten-1-one, 1-benzyl-4-(3-cyclopentyloxy-4-methoxyanilino)-1,2,5,6-tetrahydropyridin-2-one, 3-(3-cyclopentyloxy-4-methoxy-N-methylanilino)-2-cyclopenten-1-one, 3-[3-cyclopentyloxy-4-methoxy-N-(4-pyridylmethyl)-anilino]-2-cyclopenten-1-one, 3-[3-[(1RS,2RS,4SR)-bicyclo[2,2,1]hept-2-yloxy]-4-methoxyanilino]-2-methyl-2-cyclopenten-1-one, 3-[3-[(1RS,2RS,4SR)-bicyclo[2,2,1]hept-2-yloxy]-4-methoxyanilino]-2-ethyl-2-cyclopenten-1-one, 3-(N-benzyl-3-cyclohexyloxy-4-methoxyanilino)-2-cyclopenten-1-one, 3-[3-cyclohexyloxy-4-methoxy-N-2-naphthylmethyl)anilino]-2-cyclopenten-1-one, 3-(N-cyclopentyl-3-cyclopentyloxy-4-methoxyanilino)-2-cyclopenten-1-one, 3-[3-cyclopentyloxy-4-methoxy-N-(2-naphthylmethyl)anilino]-2-cyclopenten-1-one, 3-[3-cyclopentyloxy-4-methoxy-N-(3-pyridylmethyl)anilino]-2-cyclopenten-1-one, 3-[N-benzyl-3-(2-indanyloxy)-4-methoxyanilino]-2-cyclohexen-1-one, 3-[3-(2-indanyloxy)-4-methoxy-N-(4-pyridylmethyl)anilino]-2-cyclopenten-1-one, 3-[3-(2-indanyloxy)-4-methoxy-N-(2-naphthylmethyl)anilino]-2-cyclopenten-1-one, 3-[N-benzyl-3-[(1RS,2RS,4SR)-bicyclo[2,2,1]hept-2-yloxy]-4-methoxyanilino]-2-cyclopenten-1-one, 3-[N-benzyl-3-[(1RS,2RS,4SR)-bicyclo[2,2,1]hept-2-yloxy]-4-methoxyanilino]-2-cyclohexen-1-one, 3-[3-[(1RS,2RS,4SR)-bicyclo[2,2,1]hept-2-yloxy]-4-methoxy-N-4-pyridylmethyl)anilino]-2-cyclohexen-1-one, (−)-3-[3-[(1R,2R,4S)-bicyclo[2,2,1]hept-2-yloxy]-4-methoxyanilino]-2-methyl-2-cyclopenten-1-one, or (+)-3-[3-[(1S,2S,4R)-bicyclo[2,2,1]hept-2-yloxy]-4-methoxyanilino]-2-methyl-2-cyclopenten-1-one.  
     
     
         4 . An agent for the treatment of an allergic eye disease as claimed in any one of  claims 1  to  3 , wherein the allergic eye disease is allergic conjunctivitis.  
     
     
         5 . An agent for the treatment of an allergic eye disease as claimed in  claim 1 , wherein the form of administration is topical administration.  
     
     
         6 . An agent for the treatment of an allergic eye disease as claimed in  claim 5 , wherein the form of administration is an eye drop.