[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
0 Cites 1 Cited by

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, ...
View more

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

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

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

no PUM

Description & Claims & Application Information

We can also present the details of the Description, Claims and Application information to help users get a comprehensive understanding of the technical details of the patent, such as background art, summary of invention, brief description of drawings, description of embodiments, and other original content. On the other hand, users can also determine the specific scope of protection of the technology through the list of claims; as well as understand the changes in the life cycle of the technology with the presentation of the patent timeline. Login to view more.
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products