Sulfonamide compounds and pharmaceutical use thereof

A method for producing a compound of the formula (I)

• R1—SO2NHCO—A—X—R2 (I)
• wherein R1 is an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cyclo(lower)alkyl, an optionally substituted aryl or an optionally substituted heterocyclic group;
• A is an optionally substituted heteropolycyclic group having 1-3 oxygen atoms as the only heteroatom(s);
• X is an alkylene, an oxa, an oxa(lower)alkylene, a lower alkylene-oxa, a carbonyl, a lower alkenylene, an optionally substituted imino, an optionally N-substituted imino(lower)alkylene, an N-substituted lower alkyleneimino, a thioxa(lower)alkylene or a lower alkylenethioxa;
• and
• R2 is an optionally substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl;
• or
• a salt thereof,
• provided that when X is oxamethylene and A is chromanyl, then R2 is not quinolyl or substituted quinolyl and
• provided that when X is oxamethylene, then A is an unsaturated heteropolycyclic group having at least one oxygen atom as a heteroatom, or a saturated heteropolycyclic group having at least 2 oxygen atoms as heteroatoms;
• comprising:
• (1) reacting a compound of the formula (II):
• R1—SO2NH2 (II)
• wherein each symbol is as defined above, or a salt thereof, and a compound of the formula (III):
• HOOC—A—X—R2 (III)
• wherein each symbol is as defined above, or a reactive derivative thereof at carboxy or a salt thereof, to give a compound of the formula (I):
• R1—SO2NHCO—A—X—R2 (I)
• wherein each symbol is as defined above, or a salt thereof;
• or
• (2) reducing a compound of the formula (I-1):
• R1—SO2NHCO—A—X—R201 (I-1)
• wherein R201 is an optionally substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl, all of which having at least alkynyl, aryl(lower)alkenyl, terminal nitro or terminal formyl and other symbols are as defined above, or a salt thereof, to give a compound of the formula (I-2):
• R1—SO2NHCO—A—X—R202 (I-2)
• wherein R202 is an optionally substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl, all of which having at least alkyl, aryl(lower)alkyl, terminal amino or hydroxymethyl, and other symbols are as defined above, or a salt thereof;
• or
• (3) oxidizing a compound of the formula (I-3):
• R1—SO2NHCO—A—X—R203 (I-3)
• wherein R203 is an optionally substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl, all of which having at least terminal formyl, and other symbols are as defined above, or a salt thereof, to give a compound of the formula (I-4):
• R1-SO2NHCO—A—X—R204 (I-4)
• wherein R204 is an optionally substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl, all of which having at least carboxy, and other symbols are as defined above, or a salt thereof;
• or
• (4) acylating a compound of the formula (I-5):
• R1—SO2NHCO—A—X—R205 (I-5)
• wherein R205 is an optionally substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl, all of which having at least hydroxy(lower)alkyl, and other symbols are as defined above, or a salt thereof, to give a compound of the formula (I-6):
• R1—SO2NHCO—A—X—R206 (I-6)
• wherein R206 is an optionally substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl, all of which having at least acyloxy(lower)alkyl, and other symbols are as defined above, or a salt thereof;
• or
• (5) introducing an aryloxy group into a compound of the formula (I-6):
• R1—SO2NHCO—A—X—R206 (I-6)
• wherein each symbol is as defined above, or a salt thereof, to give a compound of the formula (I-7):
• R1—SO2NHCO—A—X—R207
• wherein R207 is an optionally substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl, all of which having at least aryloxy(lower)alkyl, and other symbols are as defined above, or a salt thereof;
• or
• (6) introducing a carboxy-protecting group into a compound of the formula (I-4):
• R1—SO2NHCO—A—X—R204 (I-4)
• wherein each symbol is as defined above, or a reactive derivative thereof, to give a compound of the formula (I-8):
• R1—SO2NHCO—A—X—R208 (I-8)
• wherein R208 is an optionally substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl, all of which having at least protected carboxy, and other symbols are as defined above, or a salt thereof;
• or
• (7) amidating a compound of the formula (I-4):
• R1-SO2NHCO—A—X—R204 (I-4)
• wherein each symbol is as defined above, or a reactive derivative thereof, to give a compound of the formula (I-9):
• R1—SO2NHCO—A—X—R209 (I-9)
• wherein R209 is an optionally substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl, all of which having at least optionally substituted amide, and other symbols are as defined above, or a salt thereof;
• or
• (8) adding a nitrogen-containing heterocyclic group to a compound of the formula (I-10):
• R1—SO2NHCO—A—X—R210 (I-10)
• wherein R210 is an optionally substituted aryl having at least a halogen atom, and other symbols are as defined above, or a salt thereof, to give a compound of the formula (I-11):
• R1—SO2NHCO—A—X—R211 (I-11)
• wherein R211 is an aryl substituted by at least heterocyclic group having nitrogen, and other symbols are as defined above,
• or a salt thereof.