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Benzimidazothiazole carboxamide compound and application thereof
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A kind of imidazo, formamide technology, applied in the field of medicine, can solve the problem of serious drug resistance and other problems
Inactive Publication Date: 2018-05-11
SHENYANG PHARMA UNIVERSITY
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However, the research and development of this type of drug is also facing many challenges: the problem of drug resistance caused by tumor cellgenemutation is becoming more and more serious; a balance should be sought between multi-target inhibitory effects and highly selective inhibitory effects; preclinical experiments Accurately predict compound toxicity, pharmacokinetic characteristics, etc.
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Embodiment 1
[0022] Example 1: Preparation of N-(2-methylphenyl)-3-methylbenzo[4,5]imidazo[2,1-b]thiazole-2-carboxamide (compound X01)
[0023] Step A: Preparation of 2-Mercaptobenzimidazole
[0024] Place o-phenylenediamine (21.61g, 0.20mol), carbon disulfide (18.24g, 0.24mol), sodiumcarbonate (14.84g, 0.14mol) and 300mL of water in a 500mL eggplant-shaped bottle, and heat to reflux for 7 hours. Cool to room temperature, suction filter, and dry to obtain 29.4 g of white solid, yield 98.0%, m.p.290-292°C (lit.: 303-305°C), ESI-MS (m / z): 151.1 ([M+H ] + );IR(KBr):υ3441,3153,3114,2979,2877,1618,1513,1467,1215; 1 H-NMR (400MHz, DMSO): δ7.10~7.15 (m, 4H), 12.51 (s, 2H).
[0025] Step B: Preparation of ethyl 2-((1H-benzo[d]imidazol-2-yl)mercapto)-3-oxybutanoate
[0026] Put 2-mercaptobenzimidazole (18.00g, 0.12mol), sodiumbicarbonate (30.24g, 0.36mol), ethyl 2-chloroacetoacetate (22.96g, 0.14mol) and 200mL of ethanol in a 1000mL eggplant-shaped flask , after stirring at room temperature ...
Embodiment 2
[0032] Example 2: Preparation of N,3-dimethyl-N-phenylbenzo[4,5]imidazo[2,1-b]thiazole-2-carboxamide (compound X02)
[0033] Referring to the preparation method of Example 1, 0.16 g of a white solid was obtained, with a yield of 49%, m.p.: 167-169° C.; IR: (KBr, cm -1 )3444(s), 2924(s), 2854(s), 1638(s), 1455(m), 1383(s), 741(s), 700(s); 1 HNMR(400MHz,DMSO):δ2.75(s,3H,CH 3 ),3.40(s,3H,CH 3 ),7.22-7.26(m,1H,Ar-H),7.28-7.31(m,1H,Ar-H),7.32-7.36(m,1H,Ar-H),7.38(d,4H,Ar-H , J=4.3Hz), 7.64 (d, 1H, Ar-H, J=8.0Hz), 7.93 (d, 1H, Ar-H, J=8.0Hz); ESI-MS (m / z): 322.0 ( [M+H] + ).
Embodiment 3
[0034] Example 3: Preparation of 3-methyl-N-(3-nitrophenyl)benzo[4,5]imidazo[2,1-b]thiazole-2-carboxamide (compound X03)
[0035] Referring to the preparation method of Example 1, 0.07 g of a white solid was obtained, with a yield of 20%, m.p.: 258-260° C.; IR: (KBr, cm -1 )3441(s), 2924(s), 2853(s), 1637(s), 1456(m), 1384(s), 736(s), 620(s); 1 HNMR(400MHz,DMSO):δ3.09(s,3H,CH 3 ),7.32-7.36(m,1H,Ar-H),7.41-7.45(m,1H,Ar-H),7.69(t,1H,Ar-H,J=8.2Hz),7.75(d,1H, Ar-H, J=8.1Hz), 8.01(dd, 1H, Ar-H, J=8.1, 1.8Hz), 8.11(dd, 2H, Ar-H, J=8.1, 2.4Hz), 8.68(t, 1H, Ar-H, J=2.1Hz), 10.74 (s, 1H, NH); ESI-MS (m / z): 350.7 ([M-H] - ).
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Abstract
The invention relates to the technical field of medicines, and relates to benzimidazothiazole carboxamide compound and application thereof. The benzimidazothiazole carboxamide compound comprises derivatives and pharmaceutically acceptable salts of the benzimidazothiazole carboxamide compound, and the general structure of benzimidazothiazole carboxamide compound is as shown in the description, wherein R1 and R2 are as described in the claims and the description. The benzimidazothiazole carboxamide compound and pharmaceutically acceptable acid addition salts of the benzimidazothiazole carboxamide compound can be combined with existing drugs or used alone as an epidermal growth factortyrosinekinase inhibitor for treating associated diseases caused by transduction disorder of epidermal growth factorreceptor signals such as small celllungcancer, squamous cellcarcinoma, adenocarcinoma, large cellcarcinoma, colorectal cancer, mammary cancer, ovarian cancer and renal cell carcinoma.
Description
technical field [0001] The invention belongs to the technical field of medicine, and relates to benzimidazolothiazole carboxamide compounds and their application as epidermal growth factorreceptortyrosinekinase inhibitors, and a preparation method thereof. Background technique [0002] For a long time, tumor treatment has been a worldwide problem and has become an important challenge in the field of medical research. In recent years, with the further elucidation of tumor pathogenesis and the continuous discovery of anti-tumor targets, proteintyrosinekinase (PTK) has become one of the most effective and promising anti-tumor drug targets. [0003] Epidermal growth factorreceptor (EGFR) is a transmembrane protein with both an extramembrane ligand receptor binding domain and an intracellulartyrosine kinase activity domain. The EGFR family mainly includes four types of members: EGFR / ErbB-1, HER-2 / ErbB-2, HER-3 / ErbB-3 and HER-4 / ErbB-4. EGFR is widely distributed in the ep...
Claims
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