US 8,148,371 B2 · Adenine compound and use thereof

Abstract

A drug for topically administration which is effective as an antiallergic agent. The drug for topically administration contains as an active ingredient an adenine compound represented by the general formula (1): [wherein ring A represents a 6 to 10 membered, mono or bicyclic, aromatic hydrocarbon or a 5 to 10 membered, mono or bicyclic, aromatic heterocycle containing one to three heteroatoms selected among 0 to 2 nitrogen atoms, 0 or 1 oxygen atom, and 0 or 1 sulfur atom; n is an integer of 0 to 2; m is an integer of 0 to 2; R represents halogeno, (un)substituted alkyl, etc.; X1 represents oxygen, sulfur, NR1 (R1 represents hydrogen or alkyl), or a single bond; Y1 represents a single bond, alkylene, etc.; Y2 represents a single bond, alkylene, etc.; Z represents alkylene; and at least one of Q1 and Q2 represents —COOR10 (wherein R10 represents (un)substituted alkyl, etc.), etc.] or a pharmaceutically acceptable salt of the compound.

Claims12

Dependent claims

An adenine compound represented by a general formula (1):

wherein
Ring A is benzene or naphthalene,
n is an integer selected from 0 to 2, m is an integer selected from 1 or 2,
R is halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, or substituted or unsubstituted amino group, and when n is 2, R(s) may be the same or different,
X1 is oxygen atom, sulfur atom, NR1 (wherein RI is hydrogen atom or alkyl group) or a single bond,
Y1 is a single bond, or alkylene which may be substituted by oxo group,
Y2 is alkylene or oxyalkylene,
Z is alkylene,
Q1 is hydrogen atom, halogen atom, hydroxy group, alkoxy group, or a group selected from the group consisting of Substituents set forth below,
Q2 is a group selected from the group consisting of Substituents set forth below,
Substituents:
—COOR10;
—COSR10
wherein R10 is substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkenyl group, or substituted or unsubstituted alkynyl group,
and when m is 2, (Y2-Q2)(s) may be the same or different,
its tautomer or its pharmaceutically acceptable salt.

13 more elements

A compound selected from the group consisting of

2-Butoxy-8-hydroxy-9-{(6-ethoxycarbonylmethoxy-2-naphthyl)methyl}adenine),
2-Butoxy-8-hydroxy-9-{4-(S-methylthiocarbonyl)methylbenzyl}adenine,
2-Butoxy-9-{4-(S-ethylthiocarbonyl)methylbenzyl}-8-hydroxyadenine,
2-Butoxy-8-hydroxy-9-{(6-methoxycarbonylmethoxy-2-naphthyl)methyl}adenine,
2-Butoxy-8-hydroxy-9-{3-(2-hydroxyethoxycarbonyl)benzyl}adenine,
2-Butoxy-8-hydroxy-9-{3-(2-dimethylaminoethoxycarbonyl)benzyl}adenine,
2-Butoxy-8-hydroxy-9-{3-(2-morpholinoethoxycarbonyl)benzyl}adenine,
2-Butoxy-8-hydroxy-9-(3-methoxycarbonylmethylbenzyl)adenine,
2-Butoxy-8-hydroxy-9-(4-methoxycarbonylmethylbenzyl)adenine,
2-Butoxy-8-hydroxy-9-(4-isopropoxycarbonylmethylbenzyl)adenine,
2-Butoxy-8-hydroxy-9-(4-methoxycarbonylmethoxybenzyl)adenine,
2-Butoxy-8-hydroxy-9-{3-bromo-4-(methoxycarbonylmethoxy)benzyl}adenine,
8-Hydroxy-2-(2-methoxycarbonylethyl)-9-(4-methoxycarbonylmethylbenzyl)adenine,
2-Butoxy-8-hydroxy-9-(4-ethoxycarbonylmethylbenzyl)adenine,
2-Butoxy-8-hydroxy-9-{3-(2,2,2-trifluoroethoxycarbonyl)methylbenzyl}adenine,
2-Butoxy-8-hydroxy-9-{3-(2-fluoroethoxycarbonyl)methylbenzyl}adenine,
2-Butoxy-8-hydroxy-9-{4-(2-hydroxyethoxycarbonyl)methylbenzyl}adenine,
2-Butoxy-8-hydroxy-9-{4-(2-dimethylaminoethoxycarbonyl)methylbenzyl}adenine hydrochloride,
2-Butoxy-8-hydroxy-9-{4-(2-morpholinoethoxycarbonyl)methylbenzyl}adenine,
2-Butoxy-9-(3-ethoxycarbonylmethylbenzyl)-8-hydroxyadenine,
2-Butoxy-8-hydroxy-9-(3-methoxycarbonylethylbenzyl)adenine,
2-Butoxy-8-hydroxy-9-(4-methoxycarbonylethylbenzyl)adenine,
2-Butoxy-9-(4-ethoxycarbonylethylbenzyl)-8-hydroxyadenine,
2-Butoxy-9-{4-(1-hydroxy-3-methoxycarbonylpropoxy)benzyl}-8-hydroxyadenine,
8-Hydroxy-9-(3-methoxycarbonylmethylbenzyl)-2-(2-methoxyethoxy)adenine,
2-Butylamino-8-hydroxy-9-(3-methoxycarbonylmethylbenzyl)adenine,
2-Chloro-8-hydroxy-9-(3-methoxycarbonylmethylbenzyl)adenine,
8-Hydroxy-2-(2-hydroxyethylthio)-9-(3-methoxycarbonylmethylbenzyl)adenine,
2-Butoxy-8-hydroxy-9-[4-(1-methoxycarbonylethyl)benzyl]adenine,
2-Butoxy-8-hydroxy-9-[3-(2-methoxycarbonyl-2-propyl)benzyl]adenine,
2-Butoxy-8-hydroxy-9-(4-methoxycarbonylphenylethyl)adenine,
2-Butoxy-8-hydroxy-9-[(2-methoxycarbonylmethyl)benzyl]adenine,
2-Butoxy-8-hydroxy-9-[4-(2-methoxycarbonyl-2-methylethyl)benzyl]adenine,
2-Butoxy-8-hydroxy-9-[3-((2R,S)-methoxycarbonylethyl)benzyl]adenine, and
9-{3,5-Bis (methoxycarbonylmethyl)benzyl}-2-butoxy-8-hydroxyadenine.

32 more elements

Dependencies are inferred from the claim text.

Adenine compound and use thereof

Life of this patent

Adenine compound and use thereof

Life of this patent

Abstract

Claims12