Benzoxa condensed ring compounds, process for producing the same and pharmaceutical composition comprising the same

A 2,3-dihydrobenzofurane compound represented by the following formula (Ia-2) or its pharmaceutically acceptable salt:

• ##STR223## wherein P.sub.a, Q.sub.a and R.sub.a each independently stands for a hydrogen atom, a halogen atom, an amino, nitro, cyano, carboxyl or hydroxyl group, a C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 alkoxy, C.sub.1 -C.sub.20 alkanoylamino, C.sub.1 -C.sub.20 monoalkylamino, C.sub.1 -C.sub.20 alkyloxycarbonyl, C.sub.1 -C.sub.20 alkanoyl or C.sub.1 -C.sub.20 alkanoyloxy group, or a C.sub.2 -C.sub.26 dialkylamino group, provided that, two or more of P.sub.a, Q.sub.a and R.sub.a are not halogen atoms at the same time;
• and
• the alkyl portion of said groups may be interrupted by:
• ##STR224## phenylene or phenyleneoxy, wherein R.sub.13 stands for a hydrogen atom, a lower alkyl, or lower alkanoyl group,
• or 1 to 3 hydrogen atoms on the carbon atoms of the alkyl portion may be substituted with a phenyl group or phenyloxy group, a halogen atom or a cyano group, and the phenyl portion as the substituent may be substituted with a halogen atom, an amino, nitro, cyano, carboxyl or hydroxyl group, a C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 alkoxy, C.sub.1 -C.sub.20 monoalkylamino, C.sub.1 -C.sub.20 alkanoylamino, C.sub.1 -C.sub.20 alkyloxycarbonyl, C.sub.1 -C.sub.20 alkanoyl or C.sub.1 -C.sub.20 alkanoyloxy group, or a C.sub.2 -C.sub.26 dialkylamino group;
• and
• R.sub.1 stands for a group selected from the group consisting of:
• (i) an unsubstituted C.sub.5 -C.sub.7 cycloalkyl or C.sub.6 cycloalkenyl group or a C.sub.5 -C.sub.7 cycloalkyl or C.sub.6 cycloalkenyl group substituted at a position other than the 1-position with a substituent being a C.sub.1 -C.sub.14 alkyl, C.sub.1 -C.sub.14 alkoxy, C.sub.1 -C.sub.14 alkanoylamino, C.sub.1 -C.sub.14 monoalkylamino, C.sub.1 -C.sub.14 alkyloxycarbonyl, C.sub.1 -C.sub.14 alkanoyl or C.sub.1 -C.sub.14 alkanoyloxy group or a C.sub.2 -C.sub.26 dialkylamino group;
• (ii) a group represented by the formula:
• ##STR225## wherein R.sub.9 and R.sub.10 each independently stands for a hydrogen atom or a lower alkyl group, or may combine with each other to form a C.sub.3 -C.sub.7 carbon ring;
• and
• R.sub.11 stands for a substituted or unsubstituted C.sub.1 -C.sub.19 alkyl, C.sub.2 -C.sub.19 alkenyl, C.sub.6 to C.sub.10 aryl, C.sub.7 -C.sub.19 arylalkyl, C.sub.1 -C.sub.19 alkanoyl or C.sub.1 -C.sub.19 alkanoyl group having a C.sub.4 -C.sub.19 aromatic ring, provided that the substituent when said groups are substituted by a halogen atom, an amino, nitro, cyano, carboxyl or hydroxyl group, a C.sub.1 -C.sub.16 alkyl, C.sub.1 -C.sub.16 alkoxy, C.sub.1 -C.sub.16 alkanoylamino, C.sub.1 -C.sub.16 monoalkylamino, C.sub.1 -C.sub.16 alkyloxycarbonyl, C.sub.1 -C.sub.16 alkyanoyl or C.sub.1 -C.sub.16 alkanoyloxy group, or a C.sub.2 -C.sub.26 dialkylamino group;
• or
• R.sub.11 stands for a group represented by the formula:
• --A--X--B
• wherein A stands for a C.sub.1 -C.sub.12 alkylene chain;
• X stands for an oxygen atom, a sulfur atom, or a group represented by the formula:
• ##STR226## wherein R.sub.12 stands for a hydrogen atom or a lower alkyl or lower alkanoyl group;
• and
• B stands for a substituted or unsubstituted C.sub.1 -C.sub.8 alkyl, C.sub.6 or C.sub.10 aryl or C.sub.7 -C.sub.8 arylalkyl group, provided that the substituent when said groups are substituted is a halogen atom, an amino, nitro, cyano, carboxyl or hydroxyl group, a C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.12 monoalkylamino, C.sub.1 -C.sub.12 alkanoylamino, C.sub.1 -C.sub.12 alkyloxycarbonyl, C.sub.1 -C.sub.12 alkanoyl acyl or C.sub.1 -C.sub.1 alkanoxyloxy group, or a C.sub.2 -C.sub.20 dialkylamino group;
• and
• (iii) a substituted or unsubstituted phenyl group or a group represented by the formula:
• ##STR227## wherein any one of P.sub.b, Q.sub.b, R.sub.b and S.sub.b represents a bond with the remaining three substituents independently standing for a group represented by the formula --R.sub.3, provided that, when the phenyl group is substituted, the substituent is present at the m- or p-position and the substituent is an amino, cyano, carboxyl or hydroxyl group, C.sub.1 -C.sub.16 alkoxy, C.sub.1 -C.sub.16 monoalkylamino, C.sub.1 -C.sub.16 alkanoylamino, C.sub.1 -C.sub.16 alkyloxycarbonyl, C.sub.1 -C.sub.16 alkanoyl or C.sub.1 -C.sub.16 alkanoyloxy groups, or a C.sub.2 -C.sub.26 dialkylamino group;
• and
• the alkyl portion of said groups may be interrupted by:
• ##STR228## phenylene or phenyleneoxy, wherein R.sub.13 stands for a hydrogen atom, a lower alkyl, or lower alkanoyl group,
• or 1 to 3 hydrogen atoms on the carbon atoms of the alkyl portion may be substituted with a phenyl or phenyloxy group, a halogen atom or a cyano group, or the phenyl portion as the substituent may be substituted with a halogen atom, an amino, nitro, cyano, carboxyl or hydroxyl group or a lower alkyl, lower alkoxy, lower monoalkylamino, lower dialkylamino, lower alkanoylamino, lower alkyloxycarbonyl, lower alkanoyl or lower alkanoyloxy group;
• R.sub.2 stands for a hydrogen atom or a C.sub.1 -C.sub.8 alkyl group;
• each R.sub.3 independently stands for a hydrogen atom, a halogen atom, an amino, nitro, cyano, carboxyl or hydroxyl group, C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 alkoxy, C.sub.1 -C.sub.20 monoalkylamino, C.sub.1 -C.sub.20 alkanoylamino, C.sub.1 -C.sub.20 alkyloxycarbonyl, C.sub.1 -C.sub.20 alkanoyl or C.sub.1 -C.sub.20 alkanoyloxy group, or a dialkylamino group, provided that, two or more of each R.sub.3 are not halogen atoms at the same time;
• and
• R.sub.5, R.sub.6, R.sub.7 and R.sub.8 each independently stands for a hydrogen atom or a C.sub.1 -C.sub.20 alkyl group, or R.sub.5 and R.sub.6 or R.sub.7 and R.sub.8 combine with a carbon atom bonded thereto to form a C.sub.5 -C.sub.7 carbon ring;
• and
• n is 0 or 1, provided that when any one of P.sub.a, O.sub.a and R.sub.a stands for an alkanoylamino group and R.sub.1 stands for:
• ##STR229## wherein R.sub.11 represents the unsubstituted or substituted C.sub.1 -C.sub.19 alkyl group, both of the alkyl group of the alkanoylamino group and the alkyl group R.sub.11 do not have carbon atoms of C.sub.6 or less at the same time.