Substituted dihydropyrrolopyrazole derivative

A method for producing a compound represented by the formula (I):

• wherein
• two R moieties each independently are a C1-3 alkyl group or are groups bonded to each other to form a C2-5 alkylene group,
• A is an optionally substituted C6-10 aryl group or an optionally substituted heteroaryl group, and
• R1, R2 and R3 each independently are an optionally substituted linear or branched C1-4 alkyl group,
• or a pharmacologically acceptable salt thereof, the method comprising
• a step of reacting a compound represented by the formula (1):
• wherein R, R1, R2 and R3 are defined as above and P1 is a protecting group for an amino group,
• with a compound represented by the formula (6):
• OCN-A (6)
• wherein A is defined as above,
• to obtain a compound represented by the formula (4):
• wherein R, R1, R2, R3, A and P1 are defined as above;
• and
• a step of removing the protecting group P1 from the compound represented by the formula (4) to obtain a compound represented by the formula (I).

A method for producing a compound represented by the formula (I):

• wherein
• two R moieties each independently are a C1-3 alkyl group or are groups bonded to each other to form a C2-5 alkylene group,
• A is an optionally substituted C6-10 aryl group or an optionally substituted heteroaryl group, and
• R1, R2 and R3 each independently are an optionally substituted linear or branched C1-4 alkyl group,
• or a pharmacologically acceptable salt thereof, the method comprising
• a step of reacting a compound represented by the formula (5):
• wherein A is defined as above,
• with diphenylphosphorylazide and a base to obtain a compound represented by the formula (6):
• OCN-A (6)
• wherein A is defined as above;
• a step of reacting the compound represented by the formula (6) with a compound represented by the formula (1):
• wherein R, R1, R2 and R3 are defined as above, and P1 is a protecting group for an amino group,
• to obtain a compound represented by the formula (4):
• wherein R, R1, R2, R3, A and P1 are defined as above;
• and
• a step of removing the protecting group P1 from the compound represented by the formula (4) to obtain a compound represented by the formula (I).

A method for producing a compound represented by the formula (I):

• wherein
• two R moieties each independently are a C1-3 alkyl group or are groups bonded to each other to form a C2-5 alkylene group,
• A is an optionally substituted C6-10 aryl group or an optionally substituted heteroaryl group, and
• R1, R2 and R3 each independently are an optionally substituted linear or branched C1-4 alkyl group,
• or a pharmacologically acceptable salt thereof, the method comprising
• a step of reacting a compound represented by the formula (7):
• wherein A is defined as above,
• with an oxidizing agent to obtain the compound represented by the formula (6):
• OCN-A (6)
• wherein A is defined as above;
• a step for reacting the compound represented by the formula (6) with a compound represented by the formula (1):
• wherein R, R1, R2 and R3 are defined as above, and P1 is a protecting group for an amino group,
• to obtain a compound represented by the formula (4):
• wherein R, R1, R2, R3, A and P1 are defined as above;
• and
• a step of removing the protecting group P1 from the compound represented by the formula (4) to obtain a compound represented by the formula (I).

A compound represented by the formula (4):

• wherein
• two R moieties each independently are a C1-3 alkyl group or are groups bonded to each other to form a C2-5 alkylene group;
• A is an optionally substituted C6-10 aryl group or an optionally substituted heteroaryl group;
• R1, R2 and R3 each independently are an optionally substituted linear or branched C1-4 alkyl group;
• and
• P1 is a protecting group for an amino group.

A compound represented by the formula (4a):

• wherein
• two R moieties each independently are a C1-3 alkyl group or are groups bonded to each other to form a C2-5 alkylene group;
• A is an optionally substituted C6-10 aryl group or an optionally substituted heteroaryl group, and Z is a hydrogen atom or an optionally substituted C1-6 alkyl group, or a group represented by Z—N-A forms an optionally substituted bicyclic fused heterocyclic group through the bonding between A and Z;
• R1, R2 and R3 each independently are an optionally substituted linear or branched C1-4 alkyl group;
• and
• P1 is a protecting group for an amino group.