US 6,251,897 B1Granted

6-phenyltetrahydro-1,3-oxazin-2-one derivative and pharmaceutical composition containing the same

AssigneeNikken Chemicals Co., Ltd.

InventorsShinji Ina, Kenjirou Yamana, Kyoji Noda

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Abstract

A 6-phenyltetrahydro-1,3-oxazin-2-one derivative having the formula (I): wherein, R1 is an unsubstituted or substituted C1 to C8 alkyl group; an unsubstituted or substituted C3 to C7 cycloalkyl group;, etc., R2 is a C1 to C4 alkyl group, R3 is H; an unsubstituted or substituted C1 to C5 alkyl group; etc., R4 is H; an unsubstituted or substituted C1 to C6 alkyl group, and R5 and R6 are independently a hydrogen atom; an unsubstituted or substituted C1 to C5 alkyl group; etc. an optical isomer thereof, or a pharmacologically acceptable salt thereof, or a hydrate or a solvate thereof and pharmaceutical compositions containing the same, in particular a drug for the prevention or treatment of inflammatory diseases and a drug for asthma. The above 6-phenyltetrahydro-1,3-oxazin-2-one derivative has a strong type IV PDE inhibitory activity and has a bronchiodilator and antiinflammatory effects.

Claims20

Dependent claims

A 6-phenyltetrahydro-1,3-oxazin-2-one derivative having the formula (I):

wherein:
R1 represents an unsubstituted or substituted C1 to C8 alkyl group, an unsubstituted or substituted C3 to C7 cycloalkyl group, an unsubstituted or substituted heterocycle, or a polycyclic hydrocarbon;
R2 represents a C1 to C4 alkyl group;
R3 is a hydrogen atom, an unsubstituted or substituted C1 to C5 alkyl group, an unsubstituted or substituted C3 to C7 cycloalkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heteroaryl group, or an acyl group;
R4 is a hydrogen atom, an unsubstituted or substituted C1 to C6 alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted heteroaryl group;
and
R5 and R6 are each independently a hydrogen atom, an unsubstituted or substituted C1 to C5 alkyl group, an unsubstituted or substituted C3 to C7 cycloalkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted heteroaryl group;
an optical isomer or a pharmacologically acceptable salt thereof, a hydrate thereof or a solvate thereof with a solvent selected from the group consisting of methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate and chloroform.

5 more elements

A 6-phenyltetrahydro-1,3-oxazin-2-one derivative having the formula (I):

wherein:
R1 represents a C1 to C8 alkyl group which may be substituted with one substituent, a C3 to C7 cycloalkyl group which may be substituted with one substituent, a 5- or 6-membered heterocyclic group containing at least one heteroatom selected from the group consisting of oxygen, nitrogen and sulfur atoms which may be substituted with one substituent, or a C9 to C15 bicyclic or tricyclic hydrocarbon;
R2 represents a C1 to C4 alkyl group;
R3 represents a hydrogen atom, a C1 to C5 alkyl group which may be substituted with one substituent, a C3 to C7 cycloalkyl group which may be substituted with one substituent, a C6 to C10 monocyclic or bicyclic aromatic group which may be substituted with one substituent, a 5- or 6-membered heteroaryl group containing at least one hetero atom selected from oxygen, nitrogen, and sulfur atoms which may be substituted with one substituent, or an acyl group;
R4 represents a hydrogen atom, a C1 to C6 alkyl group which may be substituted with one substituent, a C6 to C10 monocyclic or bicyclic aromatic group which may be substituted with one substituent, or a 5- or 6-membered heteroaryl group containing at least one hetero atom selected from oxygen, nitrogen, and sulfur atoms which may be substituted with one substituent;
and
R5 and R6 each independently represent a hydrogen atom, a C1 to C5 alkyl group which may be substituted with one substituent, a C3 to C7 cycloalkyl group which may be substituted with one substituent, a C6 to C10 monocyclic or bicyclic aromatic group which may be substituted with one substituent, or a 5- or 6-membered heteroaryl group containing at least one hetero atom selected from oxygen, nitrogen, and sulfur atoms which may be substituted with one substituent;
an optical isomer or a pharmacologically acceptable salt thereof, a hydrate thereof or a solvate thereof with a solvent selected from the group consisting of methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate and chloroform.

5 more elements

Dependencies are inferred from the claim text.