US 11,807,664 B2
Method for producing cyclic organic compound
Akie Homma, Tokyo (JP); Zengye Hou, Tokyo (JP); Hisashi Ito, Tokyo (JP); and Kiyoshi Sasakura, Tokyo (JP)
Assigned to Chugai Seiyaku Kabushiki Kaisha, Tokyo (JP)
Appl. No. 16/612,212
Filed by Chugai Seiyaku Kabushiki Kaisha, Tokyo (JP)
PCT Filed May 11, 2018, PCT No. PCT/JP2018/018265
§ 371(c)(1), (2) Date Nov. 8, 2019,
PCT Pub. No. WO2018/207904, PCT Pub. Date Nov. 15, 2018.
Claims priority of application No. 2017-095261 (JP), filed on May 12, 2017.
Prior Publication US 2021/0147475 A1, May 20, 2021
Int. Cl. C07K 1/06 (2006.01); B01J 19/00 (2006.01); B01J 19/18 (2006.01); C07K 1/02 (2006.01); C07K 7/64 (2006.01); C07D 513/08 (2006.01)
CPC C07K 1/06 (2013.01) [B01J 19/0033 (2013.01); B01J 19/18 (2013.01); C07K 1/02 (2013.01); C07K 7/645 (2013.01); B01J 2219/002 (2013.01); B01J 2219/00006 (2013.01); C07D 513/08 (2013.01)] 19 Claims
 
1. A method of producing a peptide compound, wherein the peptide compound is composed of natural amino acids and/or amino acid analogs, and wherein the peptide compound comprises a cyclic portion consisting of 4 to 14 natural amino acid and/or amino acid analog residues,
wherein the amino acid analog is a hydroxycarboxylic acid or an amino acid represented by the following formula: X-A-C(═O)—OH,
wherein:
X is —NH2 or —NHRN;
A is —C(R1)(R2)—, —C(R1)(R2)—C(R3)(R4)—, or —C(R1)(R2)—C(R3)(R4)—C(R5)(R6)—, wherein the carbon atom attached to R1 and R2 is bonded to X;
RN is an alkyl, an alkenyl, an alkynyl, an aryl, a heteroaryl, an aralkyl, or a cycloalkyl, each of which is optionally substituted;
R1, R2, R3, R4, R5, and R6 are each independently a hydrogen atom or an optional substituted group selected from an alkyl, an alkenyl, an alkynyl, an aryl, a heteroaryl, an aralkyl, or a cycloalkyl;
or RN and R1 together represent a carbon chain bonded to the N atom and the carbon atom at the α position thereby forming a ring;
provided that the amino acid analog is not a natural amino acid,
the method comprises a cyclization reaction step of cyclizing a cyclization precursor of the peptide compound in at least one continuous stirred tank reactor (CSTR).