Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...
Reexamination Certificate
2002-03-28
2004-02-03
Berch, Mark L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Phosphorus containing other than solely as part of an...
C514S267000, C544S244000, C544S251000
Reexamination Certificate
active
06686343
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a novel triazolopurine derivative which exhibits an adenosine A3 receptor affinity, a pharmaceutical composition containing the derivative, and an adenosine A3 receptor affinitive agent.
BACKGROUND ART
J. Heterocyclic Chem., 31, 1171 (1994) disclosed that 2-aryl-8-fluorobenzyl-1,2,4-triazolo[5,1-i]purine is useful as an adenosine A2 receptor antagonist.
An object of the present invention is to provide a novel compound which has an affinity to an adenosine A3 receptor.
DISCLOSURE OF THE INVENTION
The triazolopurine derivative of the present invention is represented by the general formula (1):
wherein R
1
represents a lower alkoxy lower alkyl group, a lower alkylsulfinyl lower alkyl group, a lower alkylsulfonyl lower alkyl group, a lower alkoxycarbonyl lower alkyl group, a carboxy lower alkyl group, a cycloalkyl group, a halogen-substituted lower alkyl group, a phosphono lower alkyl group, a lower alkylphosphono lower alkyl group, a di-lower alkylphosphono lower alkyl group, a lower alkanoyloxy lower alkyl group, a hydroxy lower alkyl group, a di-lower alkylamino lower alkyl group, a phenyl lower alkoxy lower alkyl group, or a lower alkylthio lower alkyl group; R
2
represents a phenyl group which may have, as a substituent, 1 to 3 groups selected from the group consisting of lower alkyl group, lower alkoxy group, halogen atom, halogen-substituted lower alkyl group, and phenyl group.
The triazolopurine derivative of the present invention is a novel compound which has never been described in reference documents.
In the present invention, R
1
is preferably a lower alkoxy lower alkyl group, a lower alkylthio lower alkyl group, a lower alkylsulfinyl lower alkyl group, a lower alkylsulfonyl lower alkyl group, or a carboxyl lower alkyl group.
R
1
is more preferably a methoxymethyl group, an ethoxymethyl group, a 2-methoxyethyl group, a 2-methylsulfinylethyl group, a 2-methylsulfonylethyl group, a 2-carboxyethyl group, a 3-carboxypropyl group, a 4-carboxybutyl group, or a 2-methylthioethyl group.
R
2
is preferably a phenyl group, a 4-biphenylyl group, a 4-n-propoxyphenyl group, a 4-t-butylphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, or a 3,4,5-trimethoxyphenyl group.
It is expected that the triazolopurine derivative of the present invention is applied to antihypertensive agent, antiallergic agent, anti-inflammatory agent, remedy for ischemic disease, remedy for leukemia, antipruritic agent, expectorants, antitussives, remedy for asthma, and analgesic, as a compound capable of binding with an adenosine A3 receptor, because of its excellent affinity to an adenosine A3 receptor.
Accordingly, the present invention also provides a pharmaceutical composition comprising the triazolopurine derivative described above and a pharmaceutically acceptable carrier.
Specifically, the present invention provides an adenosine A3 receptor affinitive agent comprising the triazolopurine derivative described above as an active ingredient.
BEST MODE FOR CARRYING OUT THE INVENTION
In the present invention, the lower alkyl group includes, for example, straight-chain or branched lower alkyl groups having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, isopropyl, isopentyl, neopentyl, and 1-ethylpropyl.
The lower alkoxy group includes, for example, straight-chain or branched lower alkoxy groups having 1 to 6 carbon atoms, such as methoxy, ethoxy, propoxy, butoxy, tert-butoxy, pentyloxy, and hexyloxy.
The lower alkoxy lower alkyl group includes, for example, lower alkoxy lower alkyl groups wherein both the alkoxy moiety and the alkyl moiety have 1 to 6 carbon atoms, such as methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, t-butoxymethyl, pentyloxymethyl, hexyloxymethyl, 1-methoxyethyl, 2-methoxyethyl, 3-methoxypropyl, 4-methoxybutyl, 5-methoxypentyl, 6-methoxyhexyl, 2-ethoxyethyl, and 3-propoxypropyl.
The lower alkylsulfinyl lower alkyl group includes, for example, lower alkylsulfinyl lower alkyl groups wherein the alkyl moiety has 1 to 6 carbon atoms, such as methylsulfinylmethyl, ethylsulfinylmethyl, propylsulfinylmethyl, butylsulfinylmethyl, t-butylsulfinylmethyl, pentylsulfinylmethyl, hexylsulfinylmethyl, 1-methylsulfinylethyl, 2-methylsulfinylethyl, 3-methylsulfinylpropyl, 4-methylsulfinylbutyl, 5-methylsulfinylpentyl, and 6-methylsulfinylhexyl.
The lower alkylsulfonyl lower alkyl group includes, for example, lower alkylsulfonyl lower alkyl groups wherein the alkyl moiety has 1 to 6 carbon atoms, such as methylsulfonylmethyl, ethylsulfonylmethyl, propylsulfonylmethyl, butylsulfonylmethyl, t-butylsulfonylmethyl, pentylsulfonylmethyl, hexylsulfonylmethyl, 1-methylsulfonylethyl, 2-methylsulfonylethyl, 3-methylsulfonylpropyl, 4-methylsulfonylbutyl, 5-methylsulfonylpentyl, and 6-methylsulfonylhexyl.
The lower alkoxycarbonyl lower alkyl group includes, for example, lower alkoxycarbonyl lower alkyl groups wherein both the alkoxy moiety and the alkyl moiety have 1 to 6 carbon atoms, such as methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, butoxycarbonylmethyl, pentyloxycarbonylmethyl, hexyloxycarbonylmethyl, 1-methoxycarbonylethyl, 2-methoxycarbonylethyl, 3-methoxycarbonylpropyl, 4-methoxycarbonylbutyl, 5-methoxycarbonylpentyl, 6-methoxycarbonylhexyl, 2-ethoxycarbonylethyl, 3-ethoxycarbonylpropyl, and 4-ethoxycarbonylbutyl.
The carboxy lower alkyl group includes, for example, carboxy lower alkyl groups wherein the alkyl moiety has 1 to 6 carbon atoms, such as carboxymethyl, 1-carboxyethyl, 2-carboxyethyl, 3-carboxypropyl, 4-carboxybutyl, 5-carboxypentyl, and 6-carboxyhexyl.
The lower alkylthio lower alkyl group includes, for examples, lower alkylthio lower alkyl groups wherein the alkyl moiety has 1 to 6 carbon atoms, such as methylthiomethyl, ethylthiomethyl, propylthiomethyl, butylthiomethyl, t-butylthiomethyl, pentylthiomethyl, hexylthiomethyl, 1-methylthioethyl, 2-methylthioethyl, 3-methylthiopropyl, 4-methylthiobutyl, 5-methylthiopentyl, 6-methylthiohexyl, 2-ethylthioethyl, and 3-propylthiopropyl.
The halogen-substituted lower alkyl group includes, for example, perfluoro lower alkyl groups wherein the alkyl moiety has 1 to 6 carbon atoms, such as trifluoromethyl, pentafluoroethyl, heptafluoropropyl, nonafluorobutyl, undecafluoropentyl, and tridecafluorohexyl.
The cycloalkyl group includes, for example, cycloalkyl groups having 3 to 8 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.
The phosphono lower alkyl group includes, for example, phosphono lower alkyl groups wherein the alkyl moiety has 1 to 6 carbon atoms, such as phosphonomethyl, 1-phosphonoethyl, 2-phosphonoethyl, 3-phosphonopropyl, 4-phosphonobutyl, 5-phosphonopentyl, and 6-phosphonohexyl.
The lower alkylphosphono lower alkyl group includes, for example, lower alkylphosphono lower alkyl groups wherein the alkyl moiety has 1 to 6 carbon atoms, such as methylphosphonomethyl, ethylphosphonomethyl, propylphosphonomethyl, butylphosphonomethyl, pentylphosphonomethyl, hexylphosphonomethyl, 2-ethylphosphonoethyl, 1-ethylphosphonoethyl, 3-ethylphosphonopropyl, 4-ethylphosphonobutyl, 5-ethylphosphonopentyl, and 6-ethylphosphonohexyl.
The di-lower alkylphosphono lower alkyl group includes, for example, di-lower alkylphosphono lower alkyl groups wherein the alkyl moiety has 1 to 6 carbon atoms, such as dimethylphosphonomethyl, diethylphosphonomethyl, dipropylphosphonomethyl, dibutylphosphonomethyl, dipentylphosphonomethyl, dihexylphosphonomethyl, ethylmethylphosphonomethyl, 2-diethylphosphonoethyl, 1-diethylphosphonoethyl, 3-diethylphosphonopropyl, 4-diethylphosphonobutyl, 5-diethylphosphonopentyl, and 6-diethylphosphonohexyl.
The lower alkanoyloxy lower alkyl group includes, for example, lower alkanoyloxy lower alkyl groups wherein both the alkanoyl moiety and the alkyl moiety have 1 to 6 carbon atoms, such as acetoxymethyl, propionyloxymethyl, butyryloxymethyl, valeryloxymethyl, hexanoyloxymethyl, heptanoyloxymethyl, 1-acetoxyethyl, 2-acetoxyethyl
Kurogi Yasuhisa
Nishikawa Hiroshi
Okamura Takashi
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