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Difluoro methylene piperidine carboxamide derivative as well as preparation method and application thereof

A technology of difluoromethylene piperidine carboxamide and derivatives, which is applied in the field of compound synthesis, can solve the problems of toxicity, cost, adverse reactions and the like of anti-HIV drugs, and achieve the effect of strong CCR5 antagonistic activity

Active Publication Date: 2015-03-04
SHANGHAI AQ BIOPHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, although AIDS has been controlled to a certain extent due to the introduction of some drugs to the market, the problem of drug resistance of HIV virus, the toxicity and adverse reactions of anti-HIV drugs, and the cost of long-term medication force the pharmaceutical industry to continue to seek safer and more efficient drugs. effective anti-HIV drug

Method used

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  • Difluoro methylene piperidine carboxamide derivative as well as preparation method and application thereof
  • Difluoro methylene piperidine carboxamide derivative as well as preparation method and application thereof
  • Difluoro methylene piperidine carboxamide derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Preparation of Compound 3:

[0046]

[0047] Preparation method: compound 1-a (0.1g, 0.38mmol, 1.0eq), compound 2 (0.139g, 0.38mmol, 1.0eq), EDCI (0.11g, 1.5eq), HOBT (0.077g, 1.5eq) were dissolved in 10ml dry THF, N 2 Stir overnight at room temperature under protection. TLC showed that the reaction of the raw materials was complete. Concentrate directly, and the mixture was directly separated and purified by silica gel column chromatography to obtain the product compound 3.

[0048] 1 H NMR (400MHz, CDCl3) δ7.38~7.27(m,5H),5.13~5.09(br,1H),4.78(br,1H),4.28~4.27(br,2H),3.38(br,2H), 3.01~2.97(br,2H),2.51(s,3H),2.42~2.38(m,2H),2.28~1.86(m,11H),1.64~1.62(br,4H),1.49~1.41(m,15H ).MS-ESI(+):cal.614,found:615(M+H).

Embodiment 2

[0050] Preparation of Compound 4:

[0051]

[0052] Preparation method: using compound 1-b and compound 2 as raw materials, the preparation method is the same as in Example 1.

[0053] 1 H NMR (400MHz, CDCl3) δ7.38~7.27(m,5H), 5.13~5.09(br,1H), 4.28~4.27(br,3H), 3.41~3.30(br,4H), 3.19(br,1H) ),3.01(br,1H).2.52~2.48(m,6H),2.23~2.14(m,5H),2.05~1.96(m,7H),1.46(br,9H),1.39~1.38(dd,6H ).MS-ESI(+):cal.614,found:615(M+H).

Embodiment 3

[0055] Preparation of Compound 6:

[0056]

[0057] Preparation method: using compound 1-c and compound 2 as raw materials, the preparation method is the same as in Example 1,

[0058] 1 H NMR (400MHz, CDCl3) δ7.65(br,1H),7.45~7.35(m,2H),7.29~7.24(m,3H),5.13~5.09(br,1H),4.16~4.13(m,3H ), 3.41~3.38(br,2H), 2.99~2.97(br,3H), 2.50~2.45(dd,3H), 2.44~1.99(m,11H), 1.67~1.63(br,4H), 1.47~ 1.44(dd,9H),1.39~1.38(dd,6H).MS-ESI(+):cal.614,found:615(M+H).

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Abstract

The invention relates to the field of compound synthesis, and mainly relates to a difluoro methylene piperidine carboxamide derivative (I), a medicament composition containing the difluoro methylene piperidine carboxamide derivative (I), and a preparation method and application thereof. The definition of R<1> is shown in the specification. Proved by pharmacodynamic tests, a compound disclosed by the invention has a CCR5 antagonistic action, can be used as an entry inhibitor of HIV virus, and can also be developed to be anti-AIDS medicines.

Description

technical field [0001] The present invention relates to the field of compound synthesis, and mainly relates to a class of difluoromethylene piperidine carboxamide derivatives, pharmaceutical compositions containing them, preparation methods and applications. The compounds can be used as CCR5 antagonists. Background technique [0002] Acquired Immunodeficiency Syndrome (also known as AIDS, AIDS) is a group of syndromes mainly caused by human immunodeficiency virus (HIV). According to the statistics of the World Health Organization, there are currently about 40 million AIDS patients in the world, accounting for about 1 / 150 of the world's total population, and the number is still increasing at a rate of 16,000 per day (Luo M. et al, J Chromatogr B Analyt Technol Biomed Life Sci 2011;879(28):2971-7). Therefore, the development of anti-AIDS drugs is imminent. [0003] Currently, more than 20 anti-HIV chemical drugs have been approved by the FDA. Drugs can be roughly divided in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D451/04A61K31/46A61P31/18
CPCC07D451/04A61K31/46
Inventor 卢寿福张会利于建明于新民
Owner SHANGHAI AQ BIOPHARMA CO LTD
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