IP Library › Granted Patent US 12,440,560
Granted Patent B2
US 12,440,560 · App. 18/420,017 · Granted Oct 14, 2025

Substituted pyrimidines as vaccine adjuvants

Inventors: Hidenori Kimura (Tokyo, JP); Hitoshi Ban (Osaka, JP); Yoshiaki Isobe (Osaka, JP); Hitoshi Watanabe (Osaka, JP)
Assignee: Sumitomo Pharma Co., Ltd.
A61K39/39A61K39/00A61P37/04C07D239/49A61K2039/505
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Quick Facts
Patent No.
US 12,440,560
App. No.
18/420,017
Granted
Oct 14, 2025
Kind
B2
Abstract

The present invention provides a compound of the formula (1): wherein X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Y 1 , Y 2 , L, and m are as defined in the description, and a pharmaceutically acceptable salt thereof, which are useful as a vaccine adjuvant.

Claims (11)

1. A pharmaceutical composition comprising at least one pharmaceutically acceptable carrier or excipient and a compound selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

2. The pharmaceutical composition according to claim 1 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

3. The pharmaceutical composition according to claim 1 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

4. The pharmaceutical composition according to claim 1 , wherein the compound is selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

5. The pharmaceutical composition according to claim 1 , wherein the pharmaceutical composition further comprises an antigen.

6. The pharmaceutical composition according to claim 5 , wherein the antigen is a pathogen-derived antigen or a tumor antigen.

7. The pharmaceutical composition according to claim 5 , wherein the antigen is a peptide or a protein.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 19, 2024
From: KIMURA, HIDENORI; BAN, HITOSHI; ISOBE, YOSHIAKI; WATANABE, HITOSHI
To: SUMITOMO DAINIPPON PHARMA CO., LTD.
Reel/Frame 067169/0643 →
CHANGE OF NAME Recorded Apr 19, 2024
From: SUMITOMO DAINIPPON PHARMA CO., LTD.
To: SUMITOMO PHARMA CO., LTD.
Reel/Frame 067169/0698 →
Priority Claims (1)
JP 2015-199750 · Oct 7, 2015 · national
Continuity (4)
Division 17583933 · Jan 25, 2022
Division 16822894 · Mar 18, 2020
Continuation 15766560
Related Publication 20240245766A1 · Jul 25, 2024
References Cited (41)
US 4689338A · Gerster · 1987 [cited by applicant]
US 10632192B2 · Kimura et al. · 2020 [cited by applicant]
US 20180280499A1 · Kimura · 2018 [cited by applicant]
EP 3360864 · 2018 [cited by applicant]
JP 2011506276 · 2011 [cited by applicant]
JP 2012507502 · 2012 [cited by applicant]
JP 2013534248 · 2013 [cited by applicant]
JP 2015520729 · 2015 [cited by applicant]
RU 2014113236 · 2015 [cited by applicant]
WO WO200012487 · 2000 [cited by applicant]
WO WO2005001022 · 2005 [cited by applicant]
WO WO2005018555 · 2005 [cited by applicant]
WO WO2009067081 · 2009 [cited by applicant]
WO WO2010048520 · 2010 [cited by applicant]
WO WO2010093436 · 2010 [cited by applicant]
WO WO2010133885 · 2010 [cited by applicant]
WO WO2011017611 · 2011 [cited by applicant]
WO WO2011139348 · 2011 [cited by applicant]
WO WO2012024284 · 2012 [cited by applicant]
WO WO2012066335 · 2012 [cited by applicant]
WO WO2012066336 · 2012 [cited by applicant]
WO WO2012067268 · 2012 [cited by applicant]
WO WO2012067269 · 2012 [cited by applicant]
WO WO2013172479 · 2013 [cited by applicant]
Arias et al., “Squalene Based Nanocomposites: A New Platform for the Design of Multifunctional Pharmaceutical Theragnostics”, ACS Nano, vol. 5, No. 2, 1513-1521, 2011. [cited by applicant]
Dorwald, F. Zaragoza, Side Reactions in Organic Synthesis: A Guide to Successful Synthesis Design, Weinheinn: WILEY-VCH Verlag GmbH & Co. KGaA, 2005, Preface, 6 pages. [cited by applicant]
EP Extended European Search Report in European Appln. No. 16853686.0, dated Apr. 30, 2019, 4 pages. [cited by applicant]
Extended European Search Report in European Appln. No. 21164640.1, dated Jul. 22, 2021, 10 pages. [cited by applicant]
Fox, “Squalene Emulsions for Parenteral Vaccine and Drug Delivery”, Molecules, 14, 3286-3312, 2009. [cited by applicant]
Goff et al., “Synthetic Toll-Like Receptor 4 (TLR4) and TLR7 Ligands as Influenza Virus Vaccine Adjuvants Induce Rapid, Sustained, and Broadly Protective Responses”, Journal of Virology, vol. 89, No. 6, 3221-3235, 2015. [cited by applicant]
International Search Report and Written Opinion in International Application No. PCT/JP2016/079756, dated Dec. 20, 2016, 8 pages. [cited by applicant]
Iwasaki et al., “Toll-like receptor control of the adaptive immune responses”, Nature Immunology, vol. 5, No. 10, 987-995, 2004. [cited by applicant]
Jordan, V. C. Nature Reviews: Drug Discovery, 2, 2003, 205. [cited by applicant]
Office Action in Canadian Appln. No. 3,001,283, dated Nov. 9, 2022, 7 pages. [cited by applicant]
O'Hagan et al., “The mechanism of action of MF59—An innately attractive adjuvant formulation”, Vaccine, 30, 4341-4348, 2012. [cited by applicant]
Ott et al., “The Adjuvant MF59: A 10-Year Perspective”, Methods in Molecular Medicine, vol. 42, 211-228, 2000. [cited by applicant]
RU Office Action and Search Report in Russian Appln. No. 2018116351, dated Feb. 25, 2020, 11 pages. [cited by applicant]
Smirnov et al., “Vaccine adjuvant activity of 3M-052: An imidazoquinoline designed for local activity without systemic cytokine induction”, Vaccine, 29, 5434-5442, 2011. [cited by applicant]
Steinhagen et al., “TLR-based immune adjuvants”, Vaccine, 29, 3341-3355, 2011. [cited by applicant]
Tomai et al., “Resiquimod and other immune response modifiers as vaccine adjuvants”, Expert Rev. Vaccines, 6(5), 835-847, 2007. [cited by applicant]
Valetti et al., “Peptide Conjugation: Before or After Nanoparticle Formation?”, Bioconjugate Chemistry, 25, 1971-1983, 2014. [cited by applicant]