US 11,752,204 B2
Vaccines with higher carbohydrate antigen density and novel saponin adjuvant
Wei-Han Lee, Taipei (TW); Nan-Hsuan Wang, Taipei (TW); Chung-Hao Chang, Taipei (TW); Yih-Huang Hsieh, Taipei (TW); Cheng-Der Tony Yu, Anaheim, CA (US); Cheng-Chi Wang, Taipei (TW); Yu-Hsin Lin, Taipei (TW); Yu-Chen Lin, Taipei (TW); and I-Ju Chen, Taipei (TW)
Assigned to OBI PHARMA INC., Taipei (TW)
Filed by OBI PHARMA, INC., Taipei (TW)
Filed on Nov. 1, 2019, as Appl. No. 16/671,395.
Application 16/671,395 is a division of application No. 14/758,319, granted, now 10,517,936, previously published as PCT/US2014/010310, filed on Jan. 6, 2014.
Claims priority of provisional application 61/748,880, filed on Jan. 4, 2013.
Prior Publication US 2020/0061169 A1, Feb. 27, 2020
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 39/00 (2006.01); C07H 15/24 (2006.01); A61K 39/39 (2006.01)
CPC A61K 39/001169 (2018.08) [A61K 39/39 (2013.01); C07H 15/24 (2013.01); A61K 2039/55577 (2013.01); A61K 2039/6037 (2013.01); A61K 2039/6081 (2013.01)] 5 Claims
 
1. A saponin mixture comprising:
(i) 1 to 15 mole % of a 1857 compound mixture, wherein the 1857 compound mixture comprises each of the following isolated compound of formula (I):

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(a) wherein R1 is β-D-Apiose, R2 is

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and R3 is H the 1857 compound V1A;
(b) wherein R1 is β-D-Apiose, R2 is H, and R3 is

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the 1857 compound V1B;
(c) wherein R1 is β-D-Xylose, R2 is

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and R3 is H, the 1857 compound V2A; and
(d) wherein R1 is β-D-Xylose, R2 is H, and R3 is

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the 1857 compound V2B; and
(ii) 85 to 99 mole % of a 1989 compound mixture, wherein the 1989 compound mixture comprises each of the following isolated compound of formula (I):
(a) wherein R1 is β-D-Apiose, R2 is

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and R3 is H, the 1989 compound V1B;
(b) wherein R1 is β-D-Apiose, R2 is H, and R3 is

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the 1989 compound V2A;
(c) wherein R1 is β-D-Xylose, R2 is

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and R3 is H, the 1989 compound V2B; and
(d) wherein R1 is β-D- Xylose, R2 is H, and R3 is

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the 1989 compound V2B,
wherein the 1857 compound mixture comprises about 60-70 mole % of the 1857 compound V1A; 1-5 mole % of the 1857 compound V1B, about 30-40 mole % of the 1857 compound V2A, and 0.1-3 mole % of the 1857 compound V2B; and
wherein the 1989 compound mixture comprises about about 60-70 mole % of the 1989 compound V1A, 1-5 mole % of the 1989 compound V1B, about 30-40 mole % of the 1989 compound V2A, and 0.1-3 mole % of the 1989 compound V2B.