Substituted guanidine derivatives, process for production thereof, and pharmaceutical uses thereof

A method for treating ischemia which comprises administering an effective amount of a compound of formula (1) or a pharmaceutically acceptable acid addition salt thereof to a patient, wherein formula (1) is:

• wherein R1, R2, R3 and R4 are independently a hydrogen atom, an unsubstituted alkyl group, a substituted alkyl group, a cycloalkyl group, a cycloalkenyl group, a saturated heterocyclic group, a halogen atom, a nitro group, a carboxyl group, an alkoxycarbonyl group, an aromatic group, an acyl group, —OR5, —N(R6)R7, —CON(R6)R7, —SO2N(R6)R7, —S(O)nR8 wherein R8 is an unsubstituted alkyl group, a substituted alkyl group or an aromatic group, and n is an integer of 0, 1 or 2, —Q—Ra, or
• wherein A is an oxygen atom, —S(O)n— wherein n is defined above or —N(R10)—, R9 is a hydrogen atom, an unsubstituted alkyl group, a substituted alkyl group, an acyl group or —Q—RA, and the ring is a 3- to 8-membered saturated heterocyclic group composed of a nitrogen atom and carbon atoms;
• Y1, Y2, Y3, Y4, Y5, Y6 and Y7, which may be the same or different, are independently a singe bond, —CH2—, —CO—, —C(‥C(R11)R12)—, or —N(R10)—, adjacent members of a group consisting of Y1 through Y7 being able to be taken together to represent —CH═CH—, provided that (a) four of Y1 through Y7 are independently a group other than a single bond or —NR10—, (b) two of Y1 through Y7 are independently a single bond, and (c) the remaining one is —N(R10)—;
• Z may be absent, or one or more Zs may be present and are, the same or different, independently the following substituent for hydrogen atom bonded to any of the carbon atoms constituting the ring formed by Y1 through Y7;
• an unsubstituted alkyl group, a substituted alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group, a saturated heterocyclic group, a halogen atom, a carboxyl group, an alkoxycarbonyl group, an aromatic group, an acyl group, —OR5, —N(R6)R7, —S(O)nR8, —C(O)N(R6)R7, or —Q—Ra, provided that when Z is a substituent for the hydrogen atom of —CH═CH—, Z is not —N(R6)R7 or —S(O)nR8;
• Q is a substituted or unsubstituted lower alkylene group;
• Ra is a substituted or unsubstituted vinyl group, or a substituted or unsubstituted ethynyl group;
• R5 is a hydrogen atom, an unsubstituted alkyl group, a substituted alkyl group, a cycloalkyl group, a cycloalkenyl group, a saturated heterocyclic group or an aromatic group;
• R6 and R7 are independently a hydrogen atom, an unsubstituted alkyl group, a substituted alkyl group, a cycloalkyl group, a cycloalkenyl group, a saturated heterocyclic group, an aromatic group, an acyl group or —Q—Ra, or R6 and R7, when taken together with the nitrogen atom to which they are bonded, form a saturated 5- to 7-membered cyclic amino group which may contain an oxygen atom or a sulfur atom in the ring and may be substituted by one or more unsubstituted alkyl groups, substituted alkyl groups, hydroxyl groups or —OR5 groups;
• R8 is an unsubstituted alkyl group, a substituted alkyl group or an aromatic group;
• R10 is a hydrogen atom, an unsubstituted alkyl group, a substituted alkyl group, a cycloalkyl group, a saturated heterocyclic group, an aromatic group, an acyl group or —Q—Ra;
• and
• R11 and R12 and independently a hydrogen atom, an unsubstituted alkyl group, a substituted alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group, a saturated heterocyclic group, a halogen atom, a carboxyl group, an alkoxycarbonyl group, an aromatic group, an acyl group, —OR5, —N(R6)R7, —CON(R6)R7, —S(O)nR8 or —Q—Ra.