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Embodiment 1
[0050] Example 1: Preparation Step A of N-ethyl-4-oxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-carboxamide: 3-(thiophene-2 - Preparation of thio)propionic acid
[0051] Add 0.04mol 2-mercaptothiophene, 0.04mol acrylic acid, and 80mL tetrahydrofuran into a 250mL round-bottomed flask, add 11mL triethylamine dropwise with stirring, and heat to reflux for 12 hours. After the reaction is complete, the tetrahydrofuran is evaporated after cooling slightly. After cooling, 40 mL of ethyl acetate and 20 mL of water were added, and the pH value of the solution was adjusted to 2 with 18% hydrochloric acid. The organic layer was collected, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrousmagnesiumsulfate. After suction filtration, the filtrate was evaporated to remove the solvent, and a brown solid was precipitated after cooling, which was recrystallized from petroleumether to obtain a white solid with a yield of 5.82 g and a yi...
[0061] According to the synthesis method of Example 1, a white solid was obtained with a yield of 52.6%; mp 192~195°C; IR (KBr, cm -1 ):3441.8, 3350.7, 3073.8, 2970.5, 2919.3, 1660.6, 1628.8, 1544.7, 1511.9, 1413.3, 1395.5, 1385.7, 1273.8, 1242.5, 1127.1, 893.0; 1 H-NMR (600MHz, CDCl 3 )δ: 7.74(s, 1H), 6.04(d, J=6.6Hz, 1H), 4.17~4.25(m, 1H), 3.38(t, J=6.0Hz, 2H), 2.86(t, J=6.0 Hz, 2H), 1.24 (d, J = 6.6Hz, 6H); ESI-MS m / z: 256.1 ([M+H] + ),278.0([M+Na] + ),293.9([M+K] + ),510.8([2M+H] + ),533.0([2M+Na] + ).
Embodiment 3
[0062] Example 3: Preparation of N-butyl-4-oxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-carboxamide
[0063] According to the synthesis method of Example 1, a white solid was obtained with a yield of 32.5%; mp 223~225°C; IR (KBr, cm -1 ):3440.7, 3365.6, 3072.3, 2952.3, 2926.9, 2860.1, 1658.3, 1627.7, 1545.7, 1511.4, 1397.6, 1288.1, 1243.5, 1041.9, 887.8, 705.8; 1 H-NMR (600MHz, CDCl 3 )δ: 7.72(s, 1H), 6.07(s, 1H), 3.38~3.43(m, 4H), 2.86(t, J=6.0Hz, 2H), 1.55~1.60(m, 2H), 1.36~1.42 (m,2H),0.95(t,J=7.2 Hz,3H); ESI-MS m / z:270.1([M+H] + ),292.1([M+Na] + ),538.9([2M+H] + ),561.0([2M+Na] + ).
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Abstract
The invention belongs to the field of medicine technology, and relates to a trimethylamine and apreparation method thereof and an application as the epidermal growth factorreceptortyrosinekinase inhibitor. The compounds, a prodrugs of the compounds, a pharmaceutically active metabolites and the pharmaceutically acceptable salts have the structure of formula (I) : R may be independently selectedfrom the group consisting of hydrogen, C1-C6 alkyl; R', R'' are independently selected from the group consisting of hydrogen, C1-C6 alkyl, substituted or unsubstituted phenyl, wherein the substituentis C1-C4 alkyl, C1-C4 alkoxy, halogen, halogenated C1-C4 alkyl, halogenated C1-C4 alkoxy, substituted or unsubstituted C1-C6 alkyl, wherein the substituent is dimethylamino, morpholinyl, methoxyphenoxy, methoxyphenyl; R', and R'', together with a nitrogen atom to which they are attached, form a morpholinyl or a cycloaliphatic radical. The formula is shown in the formula.
Description
technical field [0001] The invention belongs to the technical field of medicine, and relates to thienothiopyranamide compounds, a preparation method thereof and an application as an epidermal growth factorreceptortyrosinekinase inhibitor. Background technique [0002] In recent years, the morbidity and mortality of various tumors in my country have shown a significant upward trend. At present, the tumor with the highest morbidity and mortality rate is lungcancer in men, and breast cancer and lungcancer in women. Smoking, excessive drinking, lack of physical activity and other unhealthy living habits, smog, and the rapid economic and social development and social transformation have brought people work and life pressure. The impact on health cannot be ignored. Lungcancer related to the environment and lifestyle , Liver cancer, colorectal cancer, and breast cancer mortality rates are on the rise, among which lung cancer and breast cancer have the largest increase, rising...
Claims
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