Back to results
US 2025/0025550 A1Published application
Adjuvant compounds and formulations
OwnerJared William WENGER, Harsh Vardhan CHAUHANinventors
Life of this patent
Estimating the term…
Abstract
The present application relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, and intermediates thereto. The application also provides formulations and pharmaceutical compositions comprising compounds of the present invention and methods of using said compounds, formulations, or compositions in the treatment of and immunization for infectious diseases.
Claims20
A pharmaceutical formulation comprising:
- a cyclodextrin;
- and
- a pharmaceutically acceptable salt of compound of Formula I
- wherein
- is a single or double bond;
- W is CHO;
- V is hydrogen or ORx;
- Y is CH2, —O—, NR—, or NH;
- Z is hydrogen;
- a cyclic or acyclic, optionally substituted moiety selected from the group consisting of acyl, aliphatic, heteroaliphatic, aryl, arylalkyl, heteroacyl, and heteroaryl;
- or a carbohydrate domain having the structure:
- wherein each occurrence of R1 is Rx or a carbohydrate domain having the structure:
- wherein:
- each occurrence of a, b, and c is independently 0, 1, or 2;
- d is an integer from 1-5, wherein each d bracketed structure may be the same or different;
- with the proviso that the d bracketed structure represents a furanose or a pyranose moiety, and the sum of b and c is 1 or 2;
- R0 is hydrogen;
- an oxygen protecting group selected from the group consisting of alkyl ethers, benzyl ethers, silyl ethers, acetals, ketals, esters, carbamates, and carbonates;
- or an optionally substituted moiety selected from the group consisting of acyl, C1-10 aliphatic, C1-6 heteroaliphatic, 6-10-membered aryl, arylalkyl, 5-10 membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, 4-7 membered heterocyclyl having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
- each occurrence of Ra, Rb, Rc, and Rd is independently hydrogen, halogen, OH, OR, ORx, NR2, NHCOR, or an optionally substituted group selected from acyl, C1-10 aliphatic, C1-6 heteroaliphatic, 6-10-membered aryl, arylalkyl, 5-10-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, sulfur;
- 4-7-membered heterocyclyl having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
- R2 is hydrogen, halogen, OH, OR, OC(O)R4, OC(O)OR4, OC(O)NHR4, OC(O)NRR4, OC(O)SR4, NHC(O)R4, NRC(O)R4, NHC(O)OR4, NHC(O)NHR4, NHC(O)NRR4, NHR4, N(R4)2, NHR4, NRR4, N3, or an optionally substituted group selected from C1-10 aliphatic, C1-6 heteroaliphatic, 6-10-membered aryl, arylalkyl, 5-10 membered heteroaryl having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, 4-7-membered heterocyclyl having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
- R3 is hydrogen, halogen, CH2OR1, or an optionally substituted group selected from the group consisting of acyl, C1-10 aliphatic, C1-6 heteroaliphatic, 6-10-membered aryl, arylalkyl, 5-10-membered heteroaryl having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, 4-7-membered heterocyclyl having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, R4 is —T—Rz, —C(O)—T—Rz, —NH—T—Rz, —O—T—Rz, —S—T—Rz, —C(O)NH—T—Rz, C(O)O—T—Rz, C(O)S—T—Rz, C(O)NH—T—O—T—Rz, —O—T—Rz, —T—O—T—Rz, —T—S—T—Rz, or
- wherein
- X is —O—, —NR—, or T—Rz;
- T is a covalent bond or a bivalent C1-26 saturated or unsaturated, straight or branched, aliphatic or heteroaliphatic chain;
- and
- Rz is hydrogen, halogen, —OR, —ORx, —OR1, —SR, NR2, —C(O)OR, —C(O)R, —NHC(O)R, —NHC(O)OR, NC(O)OR, or an optionally substituted group selected from acyl, arylalkyl, heteroarylalkyl, C1-6 aliphatic, 6-10-membered aryl, 5-10-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, 4-7-membered heterocyclyl having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
- each occurrence of Rx is independently hydrogen or an oxygen protecting group selected from the group consisting of alkyl ethers, benzyl ethers, silyl ethers, acetals, ketals, esters, carbamates, and carbonates;
- each occurrence of R is independently hydrogen, an optionally substituted group selected from acyl, arylalkyl, 6-10-membered aryl, C1-6 aliphatic, or C1-6 heteroaliphatic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, or:
- two R on the same nitrogen atom are taken with the nitrogen atom to form a 4-7-membered heterocyclic ring having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur.
28 more elements
Dependencies are inferred from the claim text.