Compounds for inducing antigen-specific immune tolerance
A technology of immune tolerance and compounds, applied in the directions of allergen antigen components, carrier-bound antigen/hapten components, drug combinations, etc., can solve problems such as inducing immune response
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Embodiment 1
[0704] Example 1: Chemical synthesis of monomers
[0705] Exemplary procedures for synthesizing various monomers for the preparation of certain embodiments as disclosed herein are provided below.
[0706]
[0707] Galactosamine pentaacetate (3). D-Galactosamine HCl (6.73 g, 31.2 mmol) was suspended in pyridine (30 mL) and acetic anhydride (22 mL, 0.23 mol). The flask was cooled to 0°C in an ice bath, and DMAP and triethylamine were charged to the mixture. Allow the contents of the flask to be in N 2 Warm to room temperature under atmosphere. After stirring for 16 hours, the reaction mixture was diluted with EtOAc, at which point additional solids were evident. The solid product 3 was collected by filtration on a sintered glass filter and placed under high vacuum (11.23 g, 92%). This material was determined to be sufficiently pure by NMR and used directly in the next procedural step.
[0708]
[0709] Glucosamine pentaacetate (3'). D-Glucosamine HCl (20 g, 92.7 ...
Embodiment 2
[0734] Example 2: RAFT reagent synthesis
[0735] Exemplary procedures for the synthesis of specific RAFT reagents are provided below.
[0736]
[0737] Tetrakis(ethylene glycol)mono-p-toluenesulfonate (14). CH in tetraethylene glycol 12 (26.6 g, 137 mmol) 2 Cl 2 (400 mL) was added 29.0 mL of triethylamine. The reaction was cooled to 0 °C and 4-methylbenzene-1-sulfonyl chloride (24.8 g, 130 mmol, 0.95 equiv) was added. The reaction was allowed to warm to room temperature and stirred for an additional 12 hours. The reaction mixture was washed with saturated NaHCO 3 , washed with brine, washed with Na 2 SO 4 Dry, filter, and concentrate in vacuo. The crude material was purified on a silica gel column eluting with a 0-60% acetone:hexane system. The pure product 14 (16.3 g, 34%) was collected as a pale yellow oil.
[0738]
[0739] Tetrakis(ethylene glycol) monothioacetate (16). To a suspension of potassium thioacetate (10.7 g, 93.6 mmol, 2 equiv) in 680 mL of ace...
Embodiment 3
[0751] Example 3: Poly(GalNAc-co-HEMA)-PDS and dithioester-free (eg DTB-free) poly (GalNAc-co-HEMA)-PDS polymer synthesis
[0752] Exemplary procedures for the synthesis of specific thiol-terminated Y(Z)-EU units (eg, disulfide-terminated polymers) are provided below.
[0753]
[0754] Synthesis of Polymer A
[0755]
[0756] Poly(GalNAc-co-HEMA)-PDS (Polymer A). Poly(GalNAc-co-HEMA) with a target molecular weight of 21.0 kDa, a target degree of polymerization of 100 monomers, and a target GalNAc:HEMA monomer composition of 30:70 A typical example of )-PDS was synthesized as follows: A 10 mL single-neck Schlenk flask equipped with a PTFE valve and located in a low light region was purged with ultra-high purity argon (grade 5), placed in an ice bath, and charged with a magnetic Stir bar, compound 9 (300 mg, 0.80 mmol, solid), compound 11 (240 mg, 1.86 mmol, added as 240 μL neat oil), compound 20 (15.4 mg, 30 μmol, added as a 283 μL stock solution at 54.53 mg / mL) , 2...
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