Triazole compound as well as preparation method and medical application thereof

A technology for compounds and medicinal salts, applied in the field of medicinal chemistry, can solve the problems of undisclosed compound 1 implementation method, activity data, etc.

Pending Publication Date: 2022-01-04
HEFEI IND PHARMA INST CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, the patent does not disclose the implementation method and activity data of Compound 1, etc.

Method used

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  • Triazole compound as well as preparation method and medical application thereof
  • Triazole compound as well as preparation method and medical application thereof
  • Triazole compound as well as preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] 8-chloro-11- (1 - (5-methyl-1H-imidazole-4-yl) methyl) piperidine-4-subunit) -6,11-dihydro-5H-benzo [5, 6] Huan Geng [1,22-B] pyridine synthesis

[0062] Compoundllarrene (310 mg, 1 mmol), 5-methyl-1H-imidazole-4-formaldehyde (330 mg, 3 mmol) is dissolved in 1.2-dichloroethane (50 mL), and the mixture is stirred at room temperature for 10 min, then add Sodium triacetoxyborohydride (626 mg, 3 mmol), acetic acid (3 droplets). The reaction to 25 ° C was stirred overnight. LC (DCM: MeOH = 10: 1) The detection of the feedstock reaction is complete. Concentration, mixed, column layers were analyzed. Compound (190 mg, 47% yield), white solid. 1 H NMR (400MHz, CDCL 3 : ΔPPM 8.36 (DD, J 1 = 1.2Hz, J 2 = 4.8Hz, 1H), 7.74 (S, 1H), 7.47 (DD, J 1 = 0.8Hz, J 2 = 7.8 Hz, 1H), 7.47 (D, J = 2.0 Hz, 1H), 7.10-7.14 (m, 2H), 7.04 (D, J = 8.0 Hz, 1H), 4.09 (S, 2H), 3.31-3.39 (M, 2H), 3.06-3.20 (m, 4H), 2.61-2.89 (m, 6H), 2.28 (s, 3h).

Embodiment 2

[0064] Step 1 2- (4- (8-chloro-5,6-dihydro-11H-benzo [5,6] cyclohepta [1,2-B] pyridine-11-subunit) piperidine-1-yl ) Synthesis of ethane-1-alcohol (2)

[0065]

[0066] The raw material 1 (400 mg, 1.29 mmol) and N, N-diisopropylethylamine (417 mg, 3.23 mmol) were dissolved in DCM (7 mL). After stirring at room temperature for 30 min, 2-bromoethanol (404 mg, 3.23 mmol) was added. The reaction was stirred at room temperature for 22 h. TLC (V Acetone: V Dichloromethane: V Triethylamine = 1: 2: 0.1) The detection of the feedstock 1 reaction is complete. The reaction was stopped, and the carnovic solvent was stopped, and the column chromatography (V dichloromethane: v-triethylamine = 2: 1: 0.05) was isolated, and the white solid was 412 mg, the yield was 90.0%. 1 H-NMR (300MHz, CDCL 3 δ (PPM): 8.42 (D, J = 4.2 Hz, 1H, ARH), 7.46 (D, J = 7.5 Hz, 1H, ARH), 7.19-7.12 (M, 4H, ARH), 3.78-3.75 (M , 2h, ch 2 OH), 3.45-3.34 (m, 2h, Ar CH 2 ), 2.97-2.57 (M, 12H, Ar CH 2 , N (CH) 2 ) 3 , C ...

Embodiment 3

[0081] 1- (2- (4- (8-chloro-5,6-dihydro-11H-benzo [5,6] cyclohepta [1,2-b] pyridine-11-subunit) piperidine-1- Synthesis of Base) Ethyl) -1H-1,2,3-triazole-5-formate

[0082] Referring to the synthesis method of Example 2, the column chromatography (eluent: V dichloromethane: V methanol = 200: 1 ~ 50: 1) is separated, a light brown solid 210 mg compound, yield: 43.1%, MP186.2 ~ 188.1 ° C.

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PUM

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Abstract

The invention provides a triazole compound as well as a preparation method and medical application thereof. The triazole compound has a structure as shown in a formula (I). The triazole compound as shown in the formula (I) or pharmaceutically acceptable salts, compound salts, prodrugs, tautomers, stereoisomers or stereoisomer mixtures of the triazole compound are claimed in the invention. The compound disclosed by the invention has remarkable activity of antagonizing a histamine H1 receptor, lower M-choline side effect and lower Herg toxicity.

Description

(A) Technical Field [0001] The present invention relates to pharmaceutical chemistry, specifically relates to a class of triazole compounds, preparation method and medical use, a compound of the present invention compared with the prior art, with significant antihistaminic activity and low inhibitory cholinergic effect while Herg significantly reduced toxicity. The present invention also provides their use in the preparation of a medicament allergic disease prevention and treatment. (B) Background Art [0002] Hide 1 Receptor antagonists competitively block the histamine H1 receptor binding and H 1 Receptor, the inhibition of histamine into the biological effects play, play a role in allergy [Zolaly MA.Histamine H 1 antagonists andclinical characteristics of febrile seizures [J] .Int J Gen Med.2012,5: 277-281]. However, currently we are used clinically third-generation H 1 Receptor antagonist, desloratadine, etc., although no significant cardiac toxicity, but there is significant...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14A61K31/4545A61P37/08A61P11/02A61P17/00A61P11/06A61P27/02
CPCC07D401/14A61P37/08A61P11/02A61P17/00A61P11/06A61P27/02
Inventor 何广卫储昭兴许勤龙莫佳佳朱启华徐云根李家明
Owner HEFEI IND PHARMA INST CO LTD
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