RU2000103445A - DERIVATIVES OF 5-SUBSTITUTE-3-OXADIAZOLYL-1,6-NAFTYRIDIN-2 (1H) -OH - Google Patents

Claims (7)

1. A derivative of 5-substituted-3-oxadiazolyl-1,6-naphthyridine-2 (1H) -one, having the following formula (I)

where Het is an oxadiazolyl group;
R ¹ is a hydrogen atom, a lower alkyl group, a cyclo lower alkyl group, a trifluoromethyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxy group, a lower alkoxy-lower alkyl group, a hydroxy lower alkyl group, a substituted or unsubstituted aryl group or substituted or unsubstituted heteroaromatic group, and
R ² is a hydrogen atom, a lower alkyl group, a cyclo lower alkyl group, a cyclo lower alkyl methyl group, a lower alkenyl group, a cyclo lower alkenyl group, a lower alkynyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaromatic group,
or its pharmaceutically acceptable additive acid salt. 2. The derivative of the 5-substituted-3-oxadiazolyl-1,6-naphthyridin-2 (1H) -one according to claim 1, where R ¹ is a C ₁ -C ₃ alkyl group, a C ₃ -C ₄ cycloalkyl group or A C ₂ -C ₃ alkenyl group and R ² is a hydrogen atom, a C ₁ -C ₄ alkyl group, a C ₃ -C ₆ cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaromatic group or a pharmaceutically acceptable acid addition thereof salt. 3. A derivative of the 5-substituted-3-oxadiazolyl-1,6-naphthyridin-2 (1H) -one according to claim 1, wherein R ¹ is a C ₁ -C ₃ alkyl group or a C ₃ -C ₄ cycloalkyl group and R ² is a hydrogen atom, a C ₁ -C ₃ alkyl group, a C ₃ -C ₄ cycloalkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted heteroaromatic group or a pharmaceutically acceptable acid addition salt thereof. 4. A derivative of 5-substituted-3-oxadiazolyl-1,6-naphthyridin-2 (1H) -one according to claim 1, selected from the following compounds or its pharmaceutically acceptable acid addition salts:
3- (5-ethyl-1,2,4-oxadiazol-3-yl) -5- (2-methylcyclopropyl) -1,6-naphthyridin-2 (1H) -one,
3- (5-methyl-1,2,4-oxadiazol-3-yl) -5- (2-methylphenyl) -1,6-naphthyridin-2 (1H) -one,
3- (5-methyl-1,2,4-oxadiazol-3-yl) -5- (4-methoxyphenyl) -1,6-naphthyridin-2 (1H) -one,
3- (5-ethyl-1,2,4-oxadiazol-3-yl) -5- (2-thienyl) -1,6-naphthyridin-2 (1H) -one,
3- (5-methyl-1,2,4-oxadiazol-3-yl) -5 (4-pyridyl) -1,6-naphthyridin-2 (1H) -one,
3- (3-ethyl-1,2,4-oxadiazol-5-yl) -5-methyl-1,6-naphthyridin-2 (1H) -one,
3- (3-ethyl-1,2,4-oxadiazol-5-yl) -5- (3-fluorophenyl) -1,6-naphthyridin-2 (1H) -one,
3- (3-methyl-1,2,4-oxadiazol-5-yl) -5 (3-methylphenyl) -1,6-naphthyridin-2 (1H) -one,
3- (3-methyl-1,2,4-oxadiazol-5-yl) -5- (3-methoxyphenyl) -1,6-naphthyridin-2 (1H) -one,
3- (3-ethyl-1,2,4-oxadiazol-5-yl) -5 (4-methoxyphenyl) -1,6-naphthyridin-2 (1H) -one,
3- (3-ethyl-1,2,4-oxadiazol-5-yl) -5- (4-pyridyl) -1,6-naphthyridin-2 (1H) -one and
3- (3-cyclopropyl-1,2,4-oxadiazol-5-yl) -5- (3-thienyl) -1,6-naphthyridin-2 (1H) -one.  5. The compound according to claim 1, which is 3- (5-methyl-1,2,4-oxadiazol-3-yl) -5- (3-methoxyphenyl) -1,6-naphthyridin-2 (1H) -one or a pharmaceutically acceptable acid addition salt thereof.  6. A pharmaceutical composition acting on a benzodiazepine receptor, comprising as an active ingredient an effective amount of a compound according to any one of claims 1 to 5 in a mixture with a pharmaceutically acceptable carrier or diluent. 7. Derived 1,6-naphthyridine-2 (1H) -one of formula (I ')

where R is a cyano group, a carbamoyl group, a carboxyl group, a lower alkoxycarbonyl group or a substituted or unsubstituted benzyloxycarbonyl group, and
R ² is a cyclo-lower alkyl group, a lower alkenyl group, a cyclo-lower alkenyl group, a lower alkynyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaromatic group, provided that R ^{2 is} not a pyridyl group.