US 12,325,677 B2
Carboxylic acid-type lipid, and lipid particle and lipid membrane each comprising carboxylic acid-type lipid
Shinji Takeoka, Tokyo-to (JP); Keiko Nakahara, Tokyo-to (JP); Mamoru Nishiura, Tokyo-to (JP); Shinya Otsubo, Tokyo-to (JP); Hajimu Kurumatani, Tokyo-to (JP); and Toru Arakane, Tokyo-to (JP)
Assigned to Toray Industries, Inc., Tokyo-to (JP); and Nanotheta Co, Ltd., Tokyo-to (JP)
Appl. No. 17/286,448
Filed by Toray Industries, Inc., Tokyo-to (JP); and Nanotheta Co, Ltd., Tokyo-to (JP)
PCT Filed Oct. 17, 2019, PCT No. PCT/JP2019/040984
§ 371(c)(1), (2) Date Apr. 16, 2021,
PCT Pub. No. WO2020/080495, PCT Pub. Date Apr. 23, 2020.
Claims priority of application No. 2018-196222 (JP), filed on Oct. 17, 2018.
Prior Publication US 2021/0387943 A1, Dec. 16, 2021
Int. Cl. C07C 233/47 (2006.01); A61K 47/54 (2017.01); A61K 47/64 (2017.01)
CPC C07C 233/47 (2013.01) [A61K 47/543 (2017.08); A61K 47/64 (2017.08)] 12 Claims
OG exemplary drawing
 
1. A compound having a structure represented by one of formulas (I) to (VI):

OG Complex Work Unit Chemistry
wherein, in formulas (I) to (VI),
M represents an amino acid residue, an amino acid derivative residue, a peptide residue or a salt thereof, wherein the amino acid residue, the amino acid derivative residue, the peptide residue and the salt thereof can be negatively charged at physiological pH,
the amino acid residue represented by M is an acidic amino acid residue or a neutral amino acid residue,
the amino acid derivative represented by M is a residue of a basic amino acid derivative, and an introduced derivatization that the basic amino acid derivative comprises is amidation of an amino group of a side chain of a basic amino acid to a group represented by a formula: —NH—CO—R1 wherein —NH— is derived from the amino group of the side chain of the basic amino acid, and R1 represents a hydrocarbon group,
the peptide residue represented by M is a peptide residue comprising one or more acidic amino acid residues,
R represents a hydrocarbon group,
L represents —CO—O—, —O—CO—, —CO—NH—, —NH—CO—, —CO—S—, —S—CO— or —S—S—,
X represents a hydrocarbon group, a neutral amino acid residue or a polyalkylene glycol residue,
p represents an integer of 0 or more,
q represents an integer of 0 or more,
Y represents a branched chain composed of a branched chain body and one or more groups Y2 that are bonded to the branched chain body, or represents a straight chain composed of one group Y2, wherein the branched chain body is composed of one or more units Y1, wherein each unit Y1 is represented by formula (VII):

OG Complex Work Unit Chemistry
and wherein each group Y2 is represented by formula (VIII):
(*b4)-[L-X]p-L-R  (VIII)
wherein, in formulas (VII) and (VIII),
R, L, X, p and q are the same as defined above,
(*b1), (*b2) and (*b3) represent a bond of each unit Y1,
(*b4) represents a bond of each group Y2,
the bond (*b1) of each unit Y1 is bonded to (CH2)q in formula (III), (IV) or (VI), or is bonded to a bond (*b2) or (*b3) of another unit Y1 constituting the branched chain body, and
the bond (*b4) of each group Y2 is bonded to (CH2)q in formula (III), (IV) or (VI), or is bonded to a bond (*b2) or (*b3) of any unit Y1 constituting the branched chain body,
Z represents a branched chain composed of a branched chain body and one or more groups Z2 that are bonded to the branched chain body, or represents a straight chain composed of one group Z2, wherein the branched chain body is composed of one or more units Z1, wherein each unit Z1 is represented by formula (IX):

OG Complex Work Unit Chemistry
and wherein each group Z2 is selected from groups represented by formulas (X) and (XI):

OG Complex Work Unit Chemistry
wherein, in formulas (IX), (X) and (XI),
M, L, X, p and q are the same as defined above,
(*c1), (*c2) and (*c3) represent a bond of each unit Z1,
(*c4) and (*c5) represent a bond of each group Z2,
the bond (*c1) of each unit Z1 is bonded to (CH2)q in formula (V) or (VI), or is bonded to a bond (*c2) or (*c3) of another unit Z1 constituting the branched chain body, and
the bond (*c4) or (*c5) of each group Z2 is bonded to (CH2)q in formula (V) or (VI), or is bonded to a bond (*c2) or (*c3) of any unit Z1 constituting the branched chain body.