Casr agonist
A technology of substituents, glutamic acid, applied in the field of CaSR agonists
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment
[0171] Examples are given below to illustrate the present invention in more detail, but these examples do not limit the present invention.
[0172] In the present specification, the conventional method refers to a method generally used as a chemical operation represented by liquid separation operation, drying, filtration, and concentration.
[0173] In this specification, purification step A means that the crude product obtained by a conventional method is supplied to reversed-phase high-performance liquid chromatography using octadecyl chemically bonded silica gel (ODS) as a filler, and is purified with 0.1% trifluoroacetic acid ( The mixed solution of water and acetonitrile of v / v) is eluted, the method for concentrating, freeze-drying target component.
[0174] Hereinafter, examples are given for the synthesis of typical compounds of the present invention shown in Table 1 for further details, but the compounds of the present invention are not limited to these Examples.
[...
Synthetic example 1
[0180] (Synthesis Example 1) N 5 Synthesis of -(3-sulfophenyl)-L-glutamine (Compound No.1)
[0181] 75 mg (0.247 mmol) Boc-Glu-OtBu, 112 mg (0.296 mmol) HATU, 41 mg (0.296 mmol) HOAt were dissolved in 1 ml DMF, 52 μl triethylamine was added, and stirred at room temperature for 10 minutes. 43 mg (0.247 mmol) of 3-sulfoaniline was added thereto, followed by stirring at room temperature overnight. After distilling off the solvent, the obtained intermediate was purified by purification step A, dissolved in 2 ml of trifluoroacetic acid, stirred at room temperature for 3 hours, and then the solvent was distilled off. The product was purified by Purification Step A to afford the title compound.
[0182] Yield: 30.8 mg (0.10 mmol), yield: 41%.
[0183] 1H-NMR (D2O, 300MHz): δ7.89(s, 1H), 7.67-7.62(m, 2H), 7.58-7.53(m, 1H), 3.99(t, 1H, J=6.4Hz), 2.73- 2.66(m, 2H), 2.33-2.25(m, 2H)ESI(m / z): 303[M+H]+, 301[M-H]-
Synthetic example 2
[0184] (Synthesis Example 2) N 5 Synthesis of -(4-methoxy-3-sulfophenyl)-L-glutamine (Compound No.2)
[0185] Using p-anisidine-3-sulfonic acid instead of 3-sulfoaniline in Synthesis Example 1, the same operation was carried out to obtain the title compound.
[0186] Yield: 24.7 mg, yield: 23%.
[0187] 1H-NMR (D2O, 300MHz): δ7.96(s, 1H), 7.53(d, 1H), 7.04(d, 1H), 3.98(t, 1H), 3.78(s, 3H), 2.63-2.52( m, 2H), 2.30-2.05 (m, 2H)
[0188] ESI(m / z): 333[M+H]+
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More 
PatSnap Eureka turns technology decisions into work you can execute. Powered by our Innovation Knowledge Graph, it runs expert workflows across engineering, life sciences, materials and intellectual property. Get your review-ready output in minutes.
