Pyrazolo[1,5-a]pyrimidine derivatives

Details Pyrazolo[1,5-a]pyrimidine derivatives Pyrazolo[1,5-a]pyrimidine derivatives

2000-11-20

2002-04-16

Ford, John M. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C544S281000

Reexamination Certificate

active

06372749

ABSTRACT:

TECHNICAL FIELD
The present invention relates to novel pyrazolo[1,5-a]pyrimidine derivatives.
BACKGROUND ART
The pyrazolo[1,5-a]pyrimidine derivatives of the invention are novel compounds that have never been described in the literature.
DISCLOSURE OF INVENTION
An object of the present invention is to provide compounds useful as medicine.
The present invention provides novel pyrazolo[1,5-a]pyrimidine derivatives represented by the following formula (1)
wherein
R
1
is lower alkyl, phenyl or thienyl;
one of R
2
and R
3
is hydrogen and the other is naphthyl, furyl, pyridyl, styryl, phenylethynyl, substituted phenyl having 1 to 3 substituents selected from the group consisting of lower alkoxy, phenyl-lower alkoxy and hydroxyl, or phenyl which may have a substituent selected from the group consisting of lower alkylthio, N,N-di-lower alkylamino, halogen-substituted lower alkyl, phenyl, nitro, methylenedioxy and halogen;
R
4
is hydrogen, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, carboxyl, lower alkoxy-carbonyl, lower alkyl, phenylthiomethoxycarbonyl, substituted benzyloxycarbonyl having 1 to 3 substituents selected from the group consisting of lower alkoxy, halogen and nitro, phenoxycarbonyl which may have halogen or nitro as a substituent, carbamoyl, N-lower alkyl-carbamoyl, N-benzylcarbamoyl, N-(lower alkoxy-carbonyl-lower alkyl)carbamoyl, N-(carboxy-lower alkyl)carbamoyl, N-halophenylcarbamoyl, N-(1-lower alkoxy-carbonyl-2-phenylethyl)carbamoyl, N-(1-carboxy-2-phenylethyl)carbamoyl, phenyl which may have halogen as a substituent, or the group
 wherein R
1
, R
2
and R
3
are as defined above.
When R
2
is hydrogen, R
3
and R
4
may conjointly form a group represented by
wherein the R
5
s are the same or different and independently represent hydrogen or lower alkoxy.
In the specification, the term “lower alkyl” includes alkyl groups having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, butyl, isobutyl, tert-butyl, pentyl, hexyl and the like.
The thienyl group include 2-thienyl and 3-thienyl.
The naphthyl group includes 1-naphthyl and 2-naphthyl.
The furyl group includes 2-furyl and 3-furyl.
The pyridyl group includes 2-pyridyl, 3-pyridyl and 4-pyridyl.
The lower alkoxy group includes alkoxy groups having 1 to 6 carbon atoms, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy and the like.
The phenyl-lower alkoxy group as a substituent of the substituted phenyl group includes phenyl-substituted alkoxy groups having 1 to 6 carbon atoms, for example, benzyloxy, 1-phenylethoxy, 2-phenylethoxy, 3-phenylpropoxy, 4-phenylbutoxy, 5-phenylpentyloxy, 6-phenylhexyloxy and the like.
The substituted phenyl group having 1 to 3 substituents selected from the group consisting of lower alkoxy, phenyl-lower alkoxy and hydroxyl include 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 4-ethoxyphenyl, 4-propoxyphenyl, 4-buthoxyphenyl, 4-pentyloxyphenyl, 4-hexyloxyphenyl, 2,3-dimethoxyphenyl, 2,4-dimethoxyphenyl, 2,5-dimethoxyphenyl, 2,6-dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,5-dimethoxyphenyl, 3,4-diethoxyphenyl, 3,4-dipropoxyphenyl, 3,4-dibutoxyphenyl, 3,4-dipentyloxyphenyl, 3,4-dihexyloxyphenyl, 3,4,5-trimethoxyphenyl, 2,3,4-trimethoxyphenyl, 2,3,5-trimethoxyphenyl, 2,3,6-trimethoxyphenyl, 2,4,6-trimethoxyphenyl, 2,4,5-trimethoxyphenyl, 3,4,5-triethoxyphenyl, 3,4,5-tripropoxyphenyl, 3,4,5-tributoxyphenyl, 3,4,5-tripentyloxyphenyl, 3,4,5-trihexyloxyphenyl, 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 2-benzyloxyphenyl, 3-benzyloxyphenyl, 4-benzyloxyphenyl, 4-(2-phenylethoxy)phenyl, 4-(3-phenylpropoxy)phenyl, 4-(4-phenylbutoxy)phenyl, 4-(5-phenylpentyloxy)phenyl, 4-(6-phenylhexyloxy)phenyl, 4-hydroxy-3-methoxyphenyl, 3-hydroxy-4-methoxyphenyl, 4-benzyloxy-3-methoxyphenyl, 3-benzyloxy-4-methoxyphenyl, 4-benzyloxy-3-hydroxyphenyl, 3-benzyloxy-4-hydroxyphenyl, 3-hydroxy-4,5-dimethoxyphenyl, 4-hydroxy-3,5-dimethoxyphenyl, 3-benzyloxy-4,5-dimethoxyphenyl, 4-benzyloxy-3,5-dimethoxyphenyl, 3,4-dihydroxyphenyl, 3,4-dibenzyloxyphenyl, 3,4,5-trihydroxyphenyl, 3,4,5-tribenzyloxyphenyl and the like.
The lower alkylthio group as a substituent on the phenyl group which may have a substituent selected from the group consisting of lower alkylthio, N,N-di-lower alkylamino, halogen-substituted lower alkyl, phenyl, nitro, methylenedioxy and halogen includes, for example, alkylthio groups having 1 to 6 carbon atoms, such as methylthio, ethylthio, propylthio, butylthio, pentylthio, hexylthio and the like.
The N,N-di-lower alkylamino group as a substituent on the phenyl group includes, for example, N,N-di-(C
1-6
-alkyl)amino groups such as N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino, N,N-dibutylamino, N,N-dipentylamino, N,N-dihexylamino and the like.
The halogen-substituted lower alkyl group as a substituent on the phenyl group includes, for example, perhalogeno-(C
1-6
-alkyl) groups (wherein halogeno is selected from fluorine, chlorine, bromine and iodine). Specific examples include trifluoromethyl, pentafluoroethyl, heptafluoropropyl, nonafluorobutyl, undecafluoropentyl, tridecafluorohexyl and the like.
The halogen atom as a substituent on the phenyl group includes fluorine, chlorine, bromine and iodine.
Examples of the phenyl group which may have a substituent selected from the group consisting of lower alkylthio, N,N-di-lower alkylamino, halogen-substituted lower alkyl, phenyl, nitro, methylenedioxy and halogen are unsubstituted phenyl, 2-methylthiophenyl, 3-methylthiophenyl, 4-methylthiophenyl, 4-ethylthiophenyl, 4-propylthiophenyl, 4-butylthiophenyl, 4-pentylthiophenyl, 4-hexylthiophenyl, 2-(N,N-dimethylamino)phenyl, 3-(N,N-dimethylamino)phenyl, 4-(N,N-dimethylamino)phenyl, 4-(N,N-diethylamino)phenyl, 4-(N,N-dipropylamino)phenyl, 4-(N,N-dibutylamino)phenyl, 4-(N,N-dipentylamino)phenyl, 4-(N,N-dihexylamino)phenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 4-pentafluoroethylphenyl, 4-heptafluoropropylphenyl, 4-nonafluorobutylphenyl, 4-undecafluoropentylphenyl, 4-tridecafluorohexylphenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 2,3-methylenedioxyphenyl, 3,4-methylenedioxyphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3-iodophenyl, 4-iodophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl and the like.
Examples of the lower alkylthio group include those mentioned above as a substituent on the phenyl group.
The lower alkylsulfinyl group includes, for example, (C
1-6
-alkyl)sulfinyl groups such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, butylsulfinyl, pentylsulfinyl, hexylsulfinyl and the like.
The lower alkylsulfonyl group includes, for example, (C
1-6
-alkyl)sulfonyl groups such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl and the like.
The lower alkoxy-carbonyl group includes (C
1-6
-alkoxy)carbonyl groups such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl and the like.
The substituted benzyloxycarbonyl group having 1 to 3 substituents selected from the group consisting of lower alkoxy, halogen and nitro includes, for example, 2-methoxybenzyloxycarbonyl, 3-methoxybenzyloxycarbonyl, 4-methoxybenzyloxycarbonyl, 3-ethoxybenzyloxycarbonyl, 3-propoxybenzyloxycarbonyl, 3-butoxybenzyloxycarbonyl, 3-pentyloxybenzyloxycarbonyl, 3-hexyloxybenzyloxycarbonyl, 2-chlorobenzyloxycarbonyl, 3-chlorobenzyloxycarbonyl, 4-chlorobenzyloxycarbonyl, 4-bromobenzyloxycarbonyl, 4-iodobenzyloxycarbonyl, 4-fluorobenzyloxycarbonyl, 2-nitrobenzyloxycarbonyl, 3-nitrobenzyloxycarbonyl, 4-nitrobenzyloxycarbonyl, 2,3-dimethoxybenzyloxycarbonyl, 2,4-dimethoxybenzyloxycarbonyl, 3,4-dimethoxybenzyloxycarbonyl, 3,5-dimethoxybenzyloxycarbonyl, 2,3-dichlorobenzyloxycarbonyl, 2,4-dichlorobenzyloxycarbonyl, 3,4-dichlorobenzyloxycarbonyl, 3,5-dichlorobenzyloxycarbonyl, 2,4-dinitrobenzyloxycarbonyl, 3,5-dinitrobenzyloxycarbonyl, 2,3,4-trimethoxybenzyloxycarbonyl, 2,3,5-trimethoxybenzyloxyca

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