immunomodulator
A pharmacy and compound technology, applied in antiviral agents, allergic diseases, extracellular fluid diseases, etc., can solve problems such as the lack of MYPPY motifs
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[0349] Preparation of INT-1300Z
[0350]
[0351] The following peptides were synthesized according to the above procedure on a 0.4 mmol scale. The underlined steps employ a double-coupling procedure, and a 30 min single-coupling was used to couple the italicized residues. ClAc- Tyr -[N-Me]Ala- Asn -Pro-Dap- Leu -Hyp-Trp-Dab-[(S)-2-Amino-3-(1-(carboxymethyl)-1H-indol-3-yl)propionic acid]-[ N-Me]Nle -[N-Me]Nle-Leu-Cys-Gly; wherein Gly is added to 2-chlorotrityl resin. Cleavage from the resin was achieved by shaking the resin in 20% hexafluoroisopropanol / DCM for 5 min, followed by filtration. The filtrate was concentrated in vacuo to provide the desired product. HPLCRT = 2.21 min, column: Waters Aquity UPLC BEH C18 2.1 x 50 mm 1.7-μm particles; mobile phase A: acetonitrile with 0.05% TFA; mobile phase B: water with 0.05% TFA; gradient: 2- in 1.5 minutes 98% B, then held at 98% B for 1.55 minutes; flow rate: 0.8 mL / min.
[0352] Preparation of INT-130AA
[0353] ...
Embodiment 13080
[0363] Preparation of Example 13080
[0364]
[0365] Step 1 : To a solution of Intermediate 1300Z (61.8 mg, 0.021 mmol) in DMF (537 μl) was added HATU (12.25 mg, 0.032 mmol) followed by Hünich base (11.25 μl, 0.064 mmol). Finally, benzylamine (3.52 μl, 0.032 mmol) was added and the resulting solution was stirred at room temperature. Within 3h, the product had formed as shown by LC / MS. Water was added, and the resulting mixture was filtered to provide solid 3-((7R,10S,13S,16S,19S,22S,25S)-25-((2S,4R)-4-(tert-butoxy)-1-( (S)-2-((S)-2-((S)-1-((S)-2-((S)-2-((S)-3-(4-(tert-butoxy) Phenyl)-2-(2-chloroacetamido)-N-methylpropionamido)propionamido)-4-oxo-4-(tritylamino)butyryl)pyrrolidine-2-methyl Acylamino)-3-((tert-butoxycarbonyl)amino)propionylamino)-4-methylpentanoyl)pyrrolidine-2-carboxamido)-19-((1-(2-(tert-butyl) Oxy)-2-oxoethyl)-1H-indol-3-yl)methyl)-22-(2-((tert-butoxycarbonyl)amino)ethyl)-13,16-dibutyl Base-10-isobutyl-14,17-dimethyl-3,6,9,12,15,18,21,24-octaoxo-1-ph...
Embodiment 13081
[0370] Preparation of Example 13081
[0371]
[0372] To 2-((6S,9S,12S,18R,21S,24S,27S,30S,33S,36S,38aS,40R,44S,47S,49aS)-30,36-Double(( in DMF (289 μl) 1H-Indol-3-yl)methyl)-6-(2-amino-2-oxoethyl)-44-(3-amino-3-oxopropyl)-24,27-dibutyl -40-Hydroxy-12-(4-hydroxybenzyl)-33,47-bis(hydroxymethyl)-21-isobutyl-9,10,25,28-tetramethyl-5,8,11, 14,20,23,26,29,32,35,38,43,46,49-tetradecoxotetraoctahydrodipyrrolo[2,1-g 1 :2',1'-x][1,4,7,10,13,16,19,22,25,28,31,34,37,40,43]thiatetradecazacyclopentane To a solution of alkane-18-carboxamido)acetic acid (21.2 mg, 0.012 mmol) was added HATU (5.72 mg, 0.015 mmol), followed by Hünich's base (8.08 μl, 0.046 mmol) in DMF and 5- A mixture of azidopentan-1-amine (14.82 mg, 0.116 mmol). The mixture was stirred at room temperature. After about 1 h, a small amount of product was seen and most of the SM remained. After another hour, the LC / MS did not change much. Additional HATU and amine mixture were added sequentially, and the yellow soluti...
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