US 12,171,777 B2
Methods of making a cyclic dinucleotide
Masato Yoshikawa, Fujisawa Kanagawa (JP); Morihisa Saitoh, Fujisawa Kanagawa (JP); Taisuke Kato, Fujisawa Kanagawa (JP); Yayoi Nakayama, Fujisawa Kanagawa (JP); Tomohiro Seki, Fujisawa Kanagawa (JP); Yasuo Nakagawa, Fujisawa Kanagawa (JP); Yusuke Tominari, Fujisawa Kanagawa (JP); Masaki Seto, Fujisawa Kanagawa (JP); Yusuke Sasaki, Fujisawa Kanagawa (JP); Masanori Okaniwa, Fujisawa Kanagawa (JP); Tsuneo Oda, Fujisawa Kanagawa (JP); Akito Shibuya, Fujisawa Kanagawa (JP); Kosuke Hidaka, Fujisawa Kanagawa (JP); Zenyu Shiokawa, Fujisawa Kanagawa (JP); Shumpei Murata, Fujisawa Kanagawa (JP); Atsutoshi Okabe, Fujisawa Kanagawa (JP); Yoshihisa Nakada, Fujisawa Kanagawa (JP); Michiyo Mochizuki, Fujisawa Kanagawa (JP); Brian Scott Freeze, Boston, MA (US); Taisuke Tawaraishi, Fujisawa Kanagawa (JP); Yasufumi Wada, Fujisawa Kanagawa (JP); and Paul D. Greenspan, Acton, MA (US)
Assigned to Takeda Pharmaceutical Company Limited, Osaka (JP)
Filed by TAKEDA PHARMACEUTICAL COMPANY LIMITED, Osaka (JP)
Filed on May 1, 2023, as Appl. No. 18/310,467.
Application 17/065,242 is a division of application No. 16/185,258, filed on Nov. 9, 2018, granted, now 10,980,825.
Application 18/310,467 is a continuation of application No. 17/065,242, filed on Oct. 7, 2020, granted, now 11,666,594.
Application 16/185,258 is a continuation of application No. PCT/IB2017/057588, filed on Dec. 1, 2017.
Claims priority of provisional application 62/589,300, filed on Nov. 21, 2017.
Claims priority of application No. 2016-234553 (JP), filed on Dec. 1, 2016; and application No. 2017-107216 (JP), filed on May 30, 2017.
Prior Publication US 2024/0066047 A1, Feb. 29, 2024
Int. Cl. A61K 31/7084 (2006.01); A61K 31/7076 (2006.01); A61K 47/68 (2017.01); A61P 35/00 (2006.01); C07H 21/00 (2006.01); C07H 21/02 (2006.01)
CPC A61K 31/7084 (2013.01) [A61K 31/7076 (2013.01); A61K 47/6807 (2017.08); A61P 35/00 (2018.01); C07H 21/00 (2013.01); C07H 21/02 (2013.01)] 20 Claims
 
1. A method of preparing a compound having Formula (IA):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, the method comprising deprotecting a compound having Formula (7):

OG Complex Work Unit Chemistry
wherein:
X1 and X2 are each independently an oxygen atom or a sulfur atom;
R1 and R2 are each independently a hydroxy group, a protected hydroxy group, or a halogen atom;
B1 is:

OG Complex Work Unit Chemistry
R18 is hydrogen or C1-6 alkyl;
R19 is a halogen atom;
B2 is:

OG Complex Work Unit Chemistry
wherein the —NH2 group is optionally protected, or

OG Complex Work Unit Chemistry
wherein the —NH2 group is optionally protected; and
Q1, Q2, Q3 and Q4 are each independently an oxygen atom or a sulfur atom,
wherein the compound having Formula (IA), or a pharmaceutically acceptable salt thereof, is selected from the group consisting of:

OG Complex Work Unit Chemistry