US 12,351,804 B2
Production method for bifurcated lipid-linked oligonucleotide, and intermediate
Tetsuya Tanino, Osaka (JP); Mitsuaki Sekiguchi, Hyogo (JP); Shunsuke Ochi, Hyogo (JP); and Nobuaki Fukui, Hyogo (JP)
Assigned to Shionogi & Co., Ltd., Osaka (JP)
Appl. No. 17/616,413
Filed by Shionogi & Co., Ltd., Osaka (JP)
PCT Filed Jun. 2, 2020, PCT No. PCT/JP2020/021676
§ 371(c)(1), (2) Date Dec. 3, 2021,
PCT Pub. No. WO2020/246443, PCT Pub. Date Dec. 10, 2020.
Claims priority of application No. 2019-103903 (JP), filed on Jun. 3, 2019.
Prior Publication US 2022/0267771 A1, Aug. 25, 2022
Int. Cl. A61K 39/00 (2006.01); A61K 39/12 (2006.01); A61K 39/39 (2006.01); A61P 31/04 (2006.01); A61P 35/00 (2006.01); C07F 9/572 (2006.01); C12N 15/117 (2010.01)
CPC C12N 15/117 (2013.01) [C07F 9/5728 (2013.01); C12N 2310/17 (2013.01); C12N 2310/315 (2013.01); C12N 2310/351 (2013.01)] 14 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Chemistry
wherein
A and B are each independently

OG Complex Work Unit Chemistry
X1, X2, X3, and X4 are each independently O or S;
q are each independently an integer of 0 to 4;
r and s are each independently an integer of 0 to 3;
R1, R2, and R3 are each independently halogen, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, or substituted or unsubstituted alkynyl;
provided that R1 of (R1)q, R2 of (R2)r, and R3 of (R3)s may be the same or different; and
m, n and p are each independently an integer of 0 to 5;
Y is
a group of formula (Y-1): —P(OR4)(N(R5)2), wherein R4 is substituted or unsubstituted alkyl, and R's are each independently substituted or unsubstituted alkyl,
a group of formula (Y-2): —P(═R6)(OR7)2, wherein R6 is O or S, and R7 are each independently a hydrogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkylcarbonyl, substituted or unsubstituted aromatic carbocyclyl, or substituted or unsubstituted aromatic carbocyclylcarbonyl, or
a group of formula (Y-3): —P(═R8)H(OR9), wherein R8 is O or S, and R9 is a hydrogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkylcarbonyl, substituted or unsubstituted aromatic carbocyclyl, or substituted or unsubstituted aromatic carbocyclylcarbonyl,
or its salt.