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Benzo cyclohepten derivate, and preparation and medical use thereof

A technology for benzocycloheptene and medicinal salts, applied in the fields of benzocycloheptene derivatives, their preparation and medical use, can solve problems such as high toxicity and many complications

Inactive Publication Date: 2013-11-20
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The anti-AIDS drugs currently used in clinic not only have high toxicity and many complications, but also develop drug resistance in patients, so it is still necessary to find a safer and more effective way to control the virus

Method used

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  • Benzo cyclohepten derivate, and preparation and medical use thereof
  • Benzo cyclohepten derivate, and preparation and medical use thereof
  • Benzo cyclohepten derivate, and preparation and medical use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0190] Example 1: N-[3-(2-diethylaminoethoxy)-4-methylphenyl]-3-(4-methylphenyl)-8,9-dihydro-7H-benzene Preparation of cycloheptene-6-carboxamide

[0191]

[0192] a. Methyl 4-(4-bromobenzoyl)butyrate

[0193] Bromobenzene (150ml) and aluminum chloride (0.3mol) were placed in a 250ml three-necked flask, and glutaric acid monomethyl chloride (0.14mol) was slowly added dropwise under ice-cooling, and reacted at room temperature for 3.5 hours, and the reaction mixture was poured into a mixture of hydrochloric acid and ice, and the organic phase was separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phases were washed with water and saturated brine. Dry over anhydrous magnesium sulfate, filter, and evaporate most of the bromobenzene under reduced pressure to obtain 39.1 g of a yellow oil with a yield of 98%. It was directly used in the next reaction without purification.

[0194] b. 4-(4-Bromobenzoyl)butanoic acid

[0195] The yellow...

Embodiment 2

[0216] Example 2: N-[3-(2-diisopropylaminoethoxy)-4-methylphenyl]-3-(4-methylphenyl)-8,9-dihydro-7H- Preparation of Benzocycloheptene-6-Carboxamide

[0217]

[0218] a. Diisopropyl-[2-(2-methyl-5-nitrophenoxy)ethyl]amine

[0219] Using the method for preparing diethyl-[2-(2-methyl-5-nitrophenoxy)ethyl]amine in Example 1, the N,N-diethylethylamine in Step j of Example 1 The amine hydrochloride was replaced with N,N-diisopropylethylamine hydrochloride to give a yellow oil. MS [M] + = 280.4 m / e.

[0220] b. 3-(2-Diisopropylaminoethoxy)-4-methylamine

[0221] Using the method for preparing 3-(2-diethylaminoethoxy)-4-methylaniline in Example 1, diethyl-[2-(2-methyl-5 -Nitrophenoxy)ethyl]amine was replaced by diisopropyl-[2-(2-methyl-5-nitrophenoxy)ethyl]amine from step a above to give a colorless oil . MS [M] + = 250.4 m / e.

[0222] c. N-[3-(2-Diisopropylaminoethoxy)-4-methylphenyl]-3-(4-methylbenzene base)-8,9-dihydro-7H-benzocycloheptene-6-carboxamide

[0223] ...

Embodiment 3

[0224] Example 3: N-[3-(2-dimethylaminoethoxy)-4-methylphenyl]-3-(4-methylphenyl)-8,9-dihydro-7H-benzene Preparation of cycloheptene-6-carboxamide

[0225]

[0226] a. Dimethyl-[2-(2-methyl-5-nitrophenoxy)ethyl]amine

[0227] Using the method for preparing diethyl-[2-(2-methyl-5-nitrophenoxy)ethyl]amine in Example 1, the N,N-diethylethylamine in Step j of Example 1 The amine hydrochloride was replaced with N,N-dimethylethylamine hydrochloride to give a yellow oil. MS[M]+=224.3m / e

[0228] b. 3-(2-Dimethylaminoethoxy)-4-methylaniline

[0229] Using the method for preparing 3-(2-diethylaminoethoxy)-4-methylaniline in Example 1, diethyl-[2-(2-methyl-5 -Nitrophenoxy)ethyl]amine was replaced with dimethyl-[2-(2-methyl-5-nitrophenoxy)ethyl]amine from step a above to give a colorless oil. MS[M]+=194.3m / e

[0230] c. N-[3-(2-Dimethylethoxy)-4-methylphenyl]-3-(4-methylphenyl)-8,9- Dihydro-7H-benzocycloheptene-6-carboxamide

[0231] Using the preparation method of step...

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Abstract

Benzocycloheptene derivatives, preparing processes and pharmaceutical uses thereof. More particularly, the compounds of formula I or their pharmaceutically acceptable salts or hydrates which have activity of anti-HIV, wherein the definition of each group is defined in the description, their preparing processes, the pharmaceutical compositions comprising the compounds of formula I or the pharmaceutically acceptable salts or hydrates, and the uses thereof for preparation of the medicine for treating and preventing AIDS and diseases or disorders related to CCR5.

Description

technical field [0001] The present invention relates to benzocycloheptene derivatives with antagonizing CCR5 activity or pharmaceutically acceptable salts thereof, their preparation methods, pharmaceutical compositions containing the compounds, and the compounds used to prepare medicines for treating or preventing HIV infection Use of a drug for a disease or other disease associated with its CCR5 antagonism. Background technique [0002] Acquired Immune Deficiency Syndrome (AIDS) is a disease caused by HIV. Currently, anti-AIDS drugs used clinically are not only highly toxic and have many complications, but also develop drug resistance in patients, so it is still necessary to find a safer and more effective way to control the virus. [0003] It has been reported that CCR5 is a receptor required for HIV to enter cells and plays an important role in the establishment and spread of HIV infection (J Immunol, 1998, 160(8): 4018-4025.). CCR5 is a G protein-coupled chemokine rece...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/60C07C231/02A61K31/167A61P29/00A61P31/18A61P35/00A61P37/06A61P9/00
CPCC07C233/60C07D405/14C07C2102/12C07D405/12C07D295/155C07D207/06C07D407/12C07D313/08C07D401/04A61P1/04A61P3/10A61P9/00A61P9/10A61P11/06A61P13/12A61P17/00A61P17/06A61P19/02A61P29/00A61P31/00A61P31/18A61P35/00A61P37/06A61P37/08A61P43/00C07C2602/12
Inventor 李松刘瑶苏靖肖军海王莉莉钟武郑志兵谢云德李行舟赵国明王晓奎周辛波刘洪英
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A