Compounds exhibiting thrombopoietin-like activities

A compound production process which comprises a first step of reacting a compound represented by the following general formula (2):

• wherein E represents one selected from the group consisting of a methylidyne group and a nitrilo group and R1 represents one selected from the group consisting of a hydrogen atom and alky groups,
• with at least one selected from the group consisting of Nα-9-fluorenylmethoxycarbonylamino acid derivatives represented by the following general formula (3):
• Fmoc-W1 (3)
• wherein W1 represents an amino acid residue and Fmoc represents a 9-fluorenylmethoxycarbonyl group bonded to the α-amino group of said amino acid residue, with the proviso that when said amino acid residue has a side chain functional group, said side chain function group may be protected,
• and an Nα-t-butoxycarbonylamino acid derivative represented by the following gereral formula (4):
• Boc-Wt (4)
• wherein Wt represents an amino acid residue and Boc represents a t-butoxycarbonyl group bonded to the α-amino group of said amino acid residue, with the proviso that when said amino acid residue has a side chain functional group, said side chain functional group may be protected, in the presence of a condensation agent;
• a second step of deprotecting the Fmoc group or Boc group of the compound obtained in said first step;
• and
• a third step of reacting the compound obtained in said second step with a compound represented by the following general formula (5):
• R1—(X1)p—A—Z (5)
• wherein R1 represents one selected from the group consisting of a hydrogen atom, a hydroxy group, a carboxy group, optionally substituted amino groups, optionally substituted aryl groups and optionally substituted heterocyclic groups, X1 represents one selected from the group consisting of optionally substituted alkylene groups and optionally substituted alkenylene groups, p represents 0 or 1, A represents one selected from the group consisting of a carbonyl group and a sulfonyl group, and Z represents one selected from the group consisting of a hydroxy group and halogen groups,
• in the presence of a condensation agent or a base, to obtain a compound represented by the following formula (1):
• wherein E represents one selected from the group consisting of a methylidyne group and a nitrilo group, R1 represents one selected from the group consisting of a hydrogen atom, a hydroxy group, a carboxy group, optionally substituted amino groups, optionally substituted aryl groups and optionally substituted heterocyclic groups, R2 represents one selected from the group consisting of a hydrogen atom and alkyl groups, W1 presents an amino acid residue, A represents one selected from the group consisting of a carbonyl group and a sulfonyl group, Xt represents one selected from the group consisting of optionally substituted alkylene groups and optionally substituted alkenylene groups, and p represents 0 or 1.

A compound production process which comprises a fourth step of reacting a amino acid derivative and a silylating agent;

• a fifth step of reacting the compound obtained in said fourth step with a compound represented by the following general formula (5)
• R1—(X1)p—A—Z (5)
• wherein R1 represents one selected from the group consisting of a hydrogen atom, a hydroxy group, a carboxy group, optionally substituted amino groups, optionally substituted aryl groups and optionally substituted heterocyclic groups, X1 represents one selected from the group consisting of optionally substituted alkylene groups and optionally substituted alkenylene groups, p represents 0 or 1, A represents one selected from the group consisting of a carbonyl group and a sulfonyl group, and Z represents one selected from the group consisting of a hydroxy group and halogen groups;
• and
• a sixth step of reacting the compound obtained in said fifth step with a compound represented by the following general formula (2):
• wherein E represents one selected from the group consisting of a methylidyne group and a nitrilo group and R2 represents one selected from the group consisting of a hydrogen atom and alkyl groups,
• in the presence of a condensation agent, to obtain a compound represented by the following formula (1):
• wherein E represents one selected from the group consisting of a methylidyne group and a nitrilo group, R1 represents one selected from the group consisting of a hydrogen group, a hydroxy group, a carboxy group, optionally substituted amino groups, optionally substituted aryl groups and optionally substituted heterocyclic groups, R2 represents one selected from the group consisting of a hydrogen atom and alkyl groups, W1 represents an amino acid residue, A represents one selected from the group consisting of a carbonyl group and a sulfonyl group, X1 represents one selected from the group consisting of optionally substituted alkylene groups and optionally substituted alkenylene groups, and p represents 0 or 1.