US 12,221,461 B2
Saponin adjuvant and evaluation method thereof
Cheng-Der Tony Yu, Taipei (TW); Yih-Huang Hsieh, Taipei (TW); Wei Han Lee, Taipei (TW); Yu Chen Lin, Taipei (TW); and Nan Hsuan Wang, Taipei (TW)
Assigned to OBI PHARMA, INC., Taipei (TW)
Appl. No. 17/041,175
Filed by OBI PHARMA, INC., Taipei (TW)
PCT Filed Mar. 27, 2019, PCT No. PCT/US2019/024414
§ 371(c)(1), (2) Date Sep. 24, 2020,
PCT Pub. No. WO2019/191317, PCT Pub. Date Oct. 3, 2019.
Claims priority of provisional application 62/649,091, filed on Mar. 28, 2018.
Prior Publication US 2021/0024569 A1, Jan. 28, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07J 63/00 (2006.01); A61K 39/39 (2006.01); G01N 30/14 (2006.01); G01N 30/60 (2006.01); G01N 30/74 (2006.01); G01N 30/86 (2006.01); G01N 33/15 (2006.01); A61K 39/00 (2006.01); G01N 30/02 (2006.01)
CPC C07J 63/008 (2013.01) [A61K 39/39 (2013.01); G01N 30/14 (2013.01); G01N 30/60 (2013.01); G01N 30/74 (2013.01); G01N 30/8631 (2013.01); G01N 30/8675 (2013.01); G01N 33/15 (2013.01); A61K 2039/55577 (2013.01); G01N 2030/027 (2013.01)] 15 Claims
 
1. A saponin composition, comprising, by the total weight of the saponin composition:
45 to 65 wt % of the Compound 1990-V1A;
19.31 to 27.99 wt % of the Compound 1990-V2A;
0.29 to 7.71 wt % of the Compound 1990-V1B;
0.11 to 3.11 wt % of the Compound 1990-V2B;
11.94 to 21.25 wt % of the Compound 1858-A;
0.06 to 2.44 wt % of the Compound 1858-B; and
a pharmaceutically acceptable carrier,
wherein the mixture of Compound 1990 comprises Compound 1990-V1A, Compound 1990-V1B, Compound 1990-V2A, Compound 1990-V2B, or a mixture thereof; and the mixture of Compound 1858 comprises Compound 1858-A, Compound 1858-B, or a mixture thereof;
wherein the Compound 1990-V1A, Compound 1990-V1B, Compound 1990-V2A, Compound 1990-V2B, Compound 1858-A, Compound 1858-B, are of the following formula respectively:

OG Complex Work Unit Chemistry
Compound 1990-V1A: R1 is β-D-Apiose, R2 is

OG Complex Work Unit Chemistry
and R3 is H;
Compound 1990-V1B: R1 is β-D-Apiose, R2 is H, and R3 is

OG Complex Work Unit Chemistry
Compound 1990-V2A: R1 is β-D-Xylose, R2 is

OG Complex Work Unit Chemistry
and R3 is H;
Compound 1990-V2B: R1 is β-D-Xylose, R2 is H, and R3 is

OG Complex Work Unit Chemistry
Compound 1858-A: R1 is H, R2 is

OG Complex Work Unit Chemistry
and R3 is H;
and
Compound 1858-B: R1 is H, R2 is Hand R3 is

OG Complex Work Unit Chemistry