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US 2019/0055245 A1Published application
Toll-like receptor 7 (tlr7) agonists having a pyridine or pyrazine moiety, conjugates thereof, and methods and uses therefor
AssigneeBristol-Myers Squibb Company
InventorsYam B. POUDEL, Liqi He, Sanjeev Gangwar, Shoshana L. Posy, Prasanna Sivaprakasam
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Abstract
Compounds having a structure according to formula (I) where R1 and Ar are as defined herein, are agonists for the Toll-like receptor 7 (TLR7) and can be used as adjuvants for stimulating the immune system. Some such compounds can be used in conjugates for targeted delivery to the organ or tissue of intended action.
Claims17
A compound having a structure according to formula (I)
- wherein
- Ar is
- R1— is (C1-C5 alkyl)O, (C1-C2 alkyl)O(CH2)2-3O, (C1-C5 alkyl)C(═O)O, (C1-C5 alkyl)NH, (C1-C2 alkyl)O(CH2)2-3NH, or (C1-C5 alkyl)C(═O)NH;
- R2 is, independently for each occurrence thereof, H, C1-C3 alkyl, halo, O(C1-C3 alkyl), CN, or NO2;
- and
- R3 and R4 are independently H;
- C1-C6 alkyl;
- (CH2)2-4OH;
- (CH2)2-4O(C1-C3 alkyl);
- (CH2)2-4NH2;
- (CH2)2-4NH(C1-C3 alkyl);
- (CH2)2-4N(C1-C3 alkyl)2;
- (CH2)1-3(aryl);
- (CH2)1-3(heteroaryl);
- (CH2)2-4(OCH2CH2)2-8(CH2)2-4NHBoc;
- wherein a CH2 group in the cycloaliphatic ring may be replaced by O, S, NH, or N(C1-C3 alkyl) and the cycloaliphatic ring may be substituted with C1-C3 alkyl, OH, O(C1-C3 alkyl), halo, (CH2)0-3NH2, or (CH2)0-3NH(C1-C3 alkyl);
- or R3 and R4 combine with the nitrogen to which they are bonded to form a cyclic amine of the structure
- wherein a CH2 group in the cycloaliphatic ring that is separated from the amine nitrogen by at least two CH2 groups may be replaced by O, S, NH, or N(C1-C3 alkyl) and the cyclic amine may be substituted with C1-C3 alkyl, OH, O(C1-C3 alkyl), halo, (CH2)0-3NH2, or (CH2)0-3NH(C1-C3 alkyl).
15 more elements
A compound having a structure according to formula (7):
A compound having a structure according to formula 14:
A compound having a structure according to formula 17:
Dependencies are inferred from the claim text.