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US 7,683,200 B2Granted
Compounds for preparing immunological adjuvant
AssigneeEisai R&D Management Co., Ltd.
InventorsFrancis G. Fang, James E. Foy, Lynn Hawkins, Charles Lemelin, Andre Lescarbeau, Xiang Nu, Kuo-Ming Wu
Life of this patent
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Abstract
The present invention provides methods for preparing TLR-4 receptor agonist E6020: and stereoisomers thereof, which compounds are useful as an immunological adjuvants when co-administered with antigens such as vaccines for bacterial and viral diseases. Also provided are synthetic intermediates.
Claims11
A compound of formula (16):
- wherein:
- n is 0 or 1;
- R1a is a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a phosphite oxygen protecting group, or a phosphate oxygen protecting group trimethylsilyl ether, triethylsilylether, triisopropylsilyl ether, t-butyldimethylsilyl ether, t-butyldiphenyl silyl ether, 2-trimethylsilylprop-2-enyl, 2-(trimethylsilyl)ethyl, or trimethylsilyl;
- in each occurrence of R2a and R2c, one of R2a and R2c is H and the other is selected from the group consisting of tert-butyloxycarbonyl (Boc), fluorenylmethyloxycarbonyl(Fmoc), 2,2,2-trichloroethoxycarbonyl (TROC), trimethylsilylethyloxycarbonyl (TMS-ethyloxycarbonyl), cyanoethyloxycarbonyl, allyloxycarbonyl, tetrachlorophthalimide, —C(O)ORx and —C(O)CH2C(O)R6;
- or R2a and R2c taken together are a divalent nitrogen protecting group;
- R4 is a C5-C12 alkyl group or a C5-C12 alkenyl group;
- R5 and R6 are independently a C5-C15 alkyl group or a C5-C15 alkenyl group;
- and
- Rx is a substituted or unsubstituted lower alkyl;
- or a salt thereof.
7 more elements
Dependencies are inferred from the claim text.