Sumonerimod
CAS 2433782-42-2
MFC25H26F3NO3 MW445.5
3-(5-((4-cyclopentyl-3-(trifluoromethyl)benzyl)oxy)-3-methyl-1H-indol-2-yl)propanoic acid,
- 1H-Indole-2-propanoic acid, 5-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-3-methyl-
- 5-[[4-Cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-3-methyl-1H-indole-2-propanoic acid
- 3-[5-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-3-methyl-1H-indol-2-yl]propanoic acid
3-(5-{[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy}-3-methyl-1Hindol-2-yl)propanoic acid
sphingosine-1-phosphate receptor 1 agonist, immunomodulator, S1P1 agonist 6, 49KZ2L5DUV, CBP-307, Icanbelimod, CBP 307
Sumonerimod is a selective Sphingosine-1-phosphate receptor 1 ($\text{S1P}_1$) agonist developed primarily for autoimmune and inflammatory diseases (such as ulcerative colitis and Crohn's disease).
PAT
WO2020114475A1
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020114475&_cid=P12-MUZ8I1-71620-1
Reference Example 72: Preparation of Intermediate I-74
ntermediate I-73 (4.3 g) was dissolved in dichloromethane (30 mL). The reaction mixture was cooled to -40 °C, and a dichloromethane solution (50 mL) of N-bromosuccinimide (NBS, 1.98 g, 11.1 mmol) was slowly added dropwise. After the addition was complete, the reaction mixture was heated to 0 °C and stirred at 0 °C for 2 h. The reaction mixture was washed with water (20 mL), the organic phase was separated, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the residue. The residue was purified by silica gel chromatography to obtain intermediate I-74.
[0395]
[0396]Reference Example 73: Preparation of Intermediate I-75
Intermediate I-74 (1.0 g, 2.15 mmol) was dissolved in a mixture of 1,4-dioxane and water (10 mL, 4:1) at room temperature, followed by the addition of methylboric acid (1.29 g, 21.46 mmol), potassium carbonate (0.89 g, 6.44 mmol), and tetrakis(triphenylphosphine)palladium (243 mg, 0.21 mmol). The reaction mixture was stirred at 90 °C for 7 h under argon protection. The reaction mixture was cooled to room temperature, filtered, and concentrated under reduced pressure to obtain the residue. The residue was dissolved in dichloromethane (20 mL), and water (10 mL) was added. The aqueous phase was separated and extracted with dichloromethane (20 mL × 2). The combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the residue. The residue was purified by silica gel chromatography to obtain intermediate I-75.
[0399]
[0400]Reference Example 74: Preparation of Intermediate I-76
Intermediate I-75 (470 mg, 1.17 mmol) was dissolved in tetrahydrofuran (10 mL) at room temperature, and ethoxycarbonylmethylene triphenylphosphine (490 mg, 1.41 mmol) was added. The reaction mixture was stirred at 80 °C for 15 h. After cooling the reaction solution to room temperature, the organic solvent was removed by concentration under reduced pressure to obtain the residue. The residue was purified by reversed-phase preparative liquid chromatography to obtain intermediate I-76.
[0403]
[0404]Reference Example 75: Preparation of Intermediate I-77
Intermediate I-76 (110 mg, 0.23 mmol) was dissolved in ethyl acetate (2 mL), and PtO₂ (50 mg) was added
. The reaction mixture was stirred at room temperature for 2 h under a hydrogen atmosphere. After filtration, the filtrate was concentrated under reduced pressure to give intermediate I-77.
[0407]
LC-MS(ESI)[M+H] +474.2.
Example 16: Preparation of Compound 16
Intermediate I-77 (110 mg) was dissolved in tetrahydrofuran (2 mL), and lithium hydroxide monohydrate (29 mg, 0.70 mmol) and water (0.5 mL) were added. After stirring at room temperature for 3 h, the reaction solution was purified by preparative liquid chromatography to obtain compound 16.
[0809]
[0810]
1H NMR(400MHz,MeOH-d 4)δ7.71(s,1H),7.66(d,J＝8.2Hz,1H),7.57(d,J＝8.2Hz,1H),7.13(d,J＝8.7Hz,1H),6.98(d,J＝2.3Hz,1H),6.76(dd,J＝8.7,2.4Hz,1H),5.10(s,2H),3.41–3.35(m,1H),3.00(t,J＝7.7Hz,2H),2.63(t,J＝7.7Hz,2H),2.18(s,3H),2.10–2.02(m,2H),1.95–1.86(m,2H),1.78–1.60(m,4H).
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References
///////////sumonerimod, anax labs, sphingosine-1-phosphate receptor 1 agonist, immunomodulator, S1P1 agonist 6, 49KZ2L5DUV, CBP-307, Icanbelimod, CBP 307
#sumonerimod, #anax labs, #sphingosine-1-phosphate receptor 1 agonist, #immunomodulator, #S1P1 agonist 6, #49KZ2L5DUV, #CBP-307, #Icanbelimod, #CBP 307
