IP Library › Granted Patent US 10,351,582
Granted Patent B2
US 10,351,582 · App. 15/781,905 · Granted Jul 16, 2019

Pegylated imidazoquinolines

Inventors: Helene G. Bazin-Lee (Hamilton, MT); David A. Johnson (Hamilton, MT)
Assignee: GLAXOSMITHKLINE BIOLOGICALS, S.A.
C07F9/6561A61P17/12A61P31/14A61P31/20A61P35/00
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Quick Facts
Patent No.
US 10,351,582
App. No.
15/781,905
Granted
Jul 16, 2019
Kind
B2
Abstract

The present invention provides novel phospholipidated imidazoquinolines of formula (I) as TLR7 and TLR8 agonists, pharmaceutical compositions, therapeutic uses and processes for preparing the same.

Claims (18)

1. A compound selected from the group consisting of:

a) 4-amino-1-[2-(1,2-dipalmitoyl-sn-glycero-3-ethyleneglycol-phospho)ethyl]-2-n-butyl-1H-imidazo[4,5-c]quinoline;

b) 4-amino-1-[2-(1,2-dipalmitoyl-sn-glycero-3-triethyleneglycol-phospho)ethyl]-2-n-butyl-1H-imidazo[4,5-c]quinoline;

c) 4-amino-1-[2-(1,2-dipalmitoyl-sn-glycero-3-hexaethyleneglycol-phospho)ethyl]-2-n-butyl-1H-imidazo[4,5-c]quinoline; and

d) 4-amino-1-[2-(1,2-dipalmitoyl-sn-glycero-3-nonaethyleneglycol-phospho)ethyl]-2-n-butyl-1H-imidazo[4,5-c]quinoline;

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , wherein the compound is (b) 4-amino-1-[2-(1,2-dipalmitoyl-sn-glycero-3-triethyleneglycol-phospho)ethyl]-2-n-butyl-1H-imidazo[4,5-c]quinoline:

or a pharmaceutically acceptable salt thereof.

3. The compound of claim 1 , wherein the compound is (c) 4-amino-1-[2-(1,2-dipalmitoyl-sn-glycero-3-hexaethyleneglycol-phospho)ethyl]-2-n-butyl-1H-imidazo[4,5-c]quinoline:

or a pharmaceutically acceptable salt thereof.

4. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier or diluent.

5. The pharmaceutical composition according to claim 4 , wherein the compound is (b) 4-amino-1-[2-(1,2-dipalmitoyl-sn-glycero-3-triethyleneglycol-phospho)ethyl]-2-n-butyl-1H-imidazo[4,5-c]quinoline:

or a pharmaceutically acceptable salt thereof.

6. The pharmaceutical composition according to claim 4 , wherein the compound is (c) 4-amino-1-[2-(1,2-dipalmitoyl-sn-glycero-3-hexaethyleneglycol-phospho)ethyl]-2-n-butyl-1H-imidazo[4,5-c]quinoline:

or a pharmaceutically acceptable salt thereof.

7. The pharmaceutical composition of claim 4 , wherein the composition further comprises an aluminum salt.

8. The pharmaceutical composition of claim 5 , wherein the composition further comprises an aluminum salt.

9. The pharmaceutical composition of claim 6 , wherein the composition further comprises an aluminum salt.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 7, 2018
From: BAZIN-LEE, HELENE G.; JOHNSON, DAVID A.
To: GLAXOSMITHKLINE BIOLOGICALS, S.A.
Reel/Frame 046010/0631 →
Continuity (2)
Provisional Application 62266880 · Dec 14, 2015
Related Publication 20180362560A1 · Dec 20, 2018