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Novel galactoside inhibitors of galectin
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A technology of galactopyranose and halogen, applied in the field of new compounds
Pending Publication Date: 2022-05-17
GALECTO BIOTECH
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However, despite exhibiting higher affinity for galectins, 3,3'-derivatized thiodigalactosides in their multistep synthesis involving double inversion reactions to obtain 3-N-derivatized galactose building blocks has some disadvantages
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[0478] Example 35 Intravenous (IV) administration of 1 mg / kg and oral (PO) administration of 10 mg / kg resulted in excellent systemic bioavailability, Figure 1 . Furthermore, good exposure was observed in the brain, Figure 2. After oral administration, the ratio of the exposure in the brain of Example 35 to the exposure in the plasma was determined as the AUC 脑 / AUC 血浆 = 0.19. (AUC = area under the curve)
[0530]3-Chlorophenyl-3-(4-bromo-1H-1,2-pyrazol-1-yl)-3-deoxy-1-thio-α-D-galactopyranoside (30mg, 0.069 mmol), (3-fluorophenyl)boronic acid (19mg, 0.14mmol), K 2 CO 3 (38mg, 0.28mmol) and Pd(dppf)Cl 2 (7.6 mg, 0.010 mmol) in dioxane / water (1 mL, 2:1) was stirred at 60°C for 3 hours. The mixture was concentrated and analyzed by preparative HPLC (C 18 ,H 2 O / MeCN / 0.1% TFA) to give the title compound (5 mg, 16%). [C 21 h 20 ClFN 2 o 4 S][M+H] + ESI-MS m / z calculated for: 451.1; found: 450.7. 1 H NMR (400Mhz, methanol-d 4 )δ8.17(s,1H),7.92(s,1H),7.64(s,1H),7.55–7.51(m,1H),7.42–7.27(m,5H),6.93(t,J=7.8Hz ,1H),5.81(d,J=5.4Hz,1H),4.89–4.86(m,1H),4.57(dd,J=11.4,2.7Hz,1H),4.47(t,J=6.1Hz,1H) , 4.21 (d, J=1.9Hz, 1H), 3.75 (dd, J=11.4, 5.8Hz, 1H), 3.65 (dd, J=11.4, 6.6Hz, 1H).
[0534] 5-chloropyridin-3-yl-3-(4-bromo-1H-1,2-pyrazol-1-yl)-3-deoxy-1-thio-α-D-galactopyranoside ( 49mg, 0.11mmol), (4-chloro-3,5-difluorophenyl) boric acid (43mg, 0.22mmol), K 2 CO 3 (78mg, 0.56mg) and Pd(dppf)Cl 2 (12mg, 0.017mmol) solution was dissolved in 1,4-dioxane / water (1mL, 2:1) and stirred at 90°C for 4 hours. The mixture was partitioned between EtOAc and water, the organic phase was dried and concentrated. The residue was passed through preparative HPLC (C 18 ,H 2 O / MeCN / 0.1% TFA) to give the title compound (5 mg, 9%). [C 20 h 17 Cl 2 f 2 N 3 o 4 S][M+H] + ESI-MS m / z calculated: 504.0; found: 503.8. 1 H NMR (400Mhz, methanol-d 4 )δ8.64(d, J=1.7Hz, 1H), 8.47(d, J=2.1Hz, 1H), 8.24(s, 1H), 8.20(t, J=2.0Hz, 1H), 7.97(s, 1H), 7.38(d, J=8.3Hz, 2H), 5.91(d, J=5.4Hz, 1H), 4.91–4.86(m, 1H), 4.61(dd, J=11.3, 2.7Hz, 1H...
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technical field [0001] The present invention relates to novel compounds, their use as medicaments and for their production in the treatment of cancer in mammals; fibrosis; scarring; keloid formation; abnormal scarring; surgical adhesions; pathologicalangiogenesis; eye diseases; HIV- 1 Disease; use of a drug for inflammation or transplant rejection. In addition, some compounds may cross the blood-brain barrier and may be useful in the treatment of central nervous system (CNS) disorders. In addition, some compounds are suitable as oral medicines. The invention also relates to pharmaceutical compositions comprising said novel compounds. Background technique [0002] Galectins are proteins with a characteristic carbohydrate recognition domain (CRD) (Leffler et al., 2004). It is a tightly folded β-sandwich structure of approximately 130 amino acids (approximately 15 kDa) with two defining features: 1) a β-galactosebinding site and 2) a sequence motif of approximately 7 amino...
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