[N-(3',4'methylenedioxy)phenylethyl] formamidobenzoic acid derivative, its preparation method and uses

A technology of methylenedioxy and phenylethyl, applied in the application field of liver protection drugs, can solve the problems of many side effects, high price and low efficiency

Active Publication Date: 2007-04-25

北京协和制药二厂有限公司

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AI-Extracted Technical Summary

Problems solved by technology

Interferon has a certain effect on anti-virus, but its efficiency is not high, there are many side effects, ...

Abstract

The invention discloses a compound (I) or stereomer or drug salt, wherein each group is defined in the introduction, which can be applied in the hepatitis drug.

Application Domain

Organic chemistryDigestive system +2

Technology Topic

DrugEthyl phosphate +7

Image

Examples

Experimental program(23)
Effect test(3)

Example Embodiment

[0081] Example 1

[0082] Sodium 2-[N-(3’,4’methylenedioxy)phenylethyl]carboxamidobenzoate

[0083]

[0084]Dissolve 20.02g of phthalic anhydride in 120mL of acetone. Add 22.3g of (3',4'methylenedioxy)phenethylamine dropwise under stirring at room temperature. After 10 minutes of dropping, continue to stir for 2 hours. The precipitate gradually precipitates. , Filtered, and the obtained white solid was recrystallized in 95% ethanol (w/v: 2g/mL). 38.0 g of 2-[N-(3',4'methylenedioxy)phenylethyl]carboxamidobenzoic acid was obtained as white needle crystals. m.p.142-143℃

[0085] 1 HNMR (300MHz, CD 3 OD, δppm): 2.76 (t, 2H, J = 6.9 Hz, H-9), 3.45 (t, 2H, J = 6.9 Hz, H-8), 5.83 (s, 2H, H-7'), 6.7 -7.9(m, 7H, Ar-H)

[0086] Elemental analysis: theoretical value: C65.17%, H4.79%, N4.47%; measured value: C65.23%, H4.69%, N4.60%

[0087] IR(KBr, cm -1 ): 3307, 3300-2500(br.), 1730, 1628, 1600, 1577, 1500, 1489, 1300, 1248, 1039, 937, 924, 876, 766, 700

[0088] Dissolve 939 mg of 2-[N-(3',4'methylenedioxy)phenylethyl]carboxamidobenzoic acid in 10 mL of methanol, add aqueous sodium hydroxide solution (containing 120 mg of sodium hydroxide), and concentrate to Dry, vacuum dry, and wash the obtained solid with hot absolute ethanol to obtain the desired compound as a white solid.

Example Embodiment

[0089] Example 2

[0090] 3-nitro-2-[N-(3’,4’methylenedioxy)phenylethyl]carboxamidobenzoic acid

[0091]

[0092] Dissolve 0.989 g of 3-nitrophthalic anhydride in acetone, add 0.99 ml of (3',4'methylenedioxy)phenethylamine dropwise under stirring at room temperature, drop it in 10 minutes, and continue to stir for 2 hours. The precipitate gradually separated out, filtered, and the white solid obtained was recrystallized in 95% ethanol. 1.35 g of the desired compound was obtained as a pale yellow solid. m.p.168-169℃

[0093] 1 HNMR (300MHz, CD 3 OD, δppm): 2.82 (t, 2H, J = 7.2 Hz, H-9), 3.50 (t, 2H, J = 7.2 Hz, H-8), 5.98 (s, 2H, H-7'), 6.74 (m+s, 3H, H-5', H-6', H-2'), 7.73-8.29 (m, 3H, H-4, H-5, H-6). ESIMS: 359(M+1)

Example Embodiment

[0094] Example 3

[0095] 6-Methyl-2-[N-(3’,4’methylenedioxy)phenylethyl]carboxamidobenzoic acid

[0096]

[0097] The method is the same as in Example 2. Use 0.908 g of 3-methylphthalic anhydride instead of 3-nitrophthalic anhydride. Using ether instead of acetone and filtering, the white solid obtained was recrystallized in 80% ethanol (w/v: 2g/ml). 1.3 g of the desired compound was obtained as white needle-like crystals. m.p.113-115℃

[0098] 1 HNMR (300MHz, CD 3 OD, ppm): 2..19(s, 3H, CH 3 -6), 2.82 (t, 2 H, J = 7.5 Hz, H-9), 3.48 (t, 2H, J = 7.5 Hz, H-8), 5.83 (s, 2H, H-7'), 6.70 (m+s, 3H, H-5', H-6', H-2'), 7.24-7.80 (m, 3H, H-3, H-4, H-5)

[0099] ESIMS: 328(M+1)

PUM

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