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Application of Pirfenidone Derivatives in Pharmaceuticals
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A drug and pharmacy technology, applied in the application field of pirfenidone derivatives in pharmacy, can solve the problems of no anti-fibrotic drugs, anti-tumor drugs, poor anti-fibrotic activity, etc., and achieve a good industrialization prospect. Effect
Inactive Publication Date: 2020-08-11
SICHUAN UNIV
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[0003] Anti-fibrotic drugs refer to the medicines for the treatment and / or prevention of fibrotic diseases, such as: pirfenidone (pharmaceutical product listed on the market), however, the inhibitory rate of this compound to fibroblast proliferation can only reach 8.15%, anti-fibrotic poor activity
[0004] At present, there is no relevant report that the compound represented by formula I of the present invention or its pharmaceutically acceptable salt, crystal form, hydrate or solvate is used for the preparation of anti-fibrosis drugs and / or anti-tumor drugs
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Embodiment 1
[0043] Embodiment 1, the synthesis of compound 5f of the present invention
[0044] synthetic route:
[0045]
[0046] 1. Synthesis of compound 3 (5-methyl-2-(1H)-pyridone)
[0047] First add 3.40mL of 50% sulfuric acid (v / v) to a 25mL reaction flask, then add 1.00g (10mmol) of 2-amino-5-picoline (compound 1), cool to below 10°C in an ice-salt bath, and stir for several After 10 minutes, the reaction solution turned milky white; then slowly added dropwise 1.72g (25mmol) NaNO 2 with 3mL H 2 The mixed solution composed of O has brown-yellow gas with pungent odor during the dropwise addition process. After the addition, the reaction solution turns light yellow. Use 10% dilute sulfuric acid to adjust the pH to 7-8, reflux and stir for about 20 minutes, and spin Most of the water was removed, an appropriate amount of 300 mesh silica gel was added thereto, spin-dried, poured into a glass sand core funnel, rinsed with ethyl acetate and suction-filtered, and the filtrate was spi...
Embodiment 2
[0056] Embodiment 2, the synthesis of compound 5g of the present invention
[0057] According to the method similar to Example 1, using phenylhydrazine or phenylhydrazine hydrochloride as raw material in step 3, compound 5g was prepared, and the single-step yield of step 3 was 72%.
[0062] HRMS (ESI) calcd for C 19 h 17 N 3 O[M+H] + 304.1451, found 304.1447; [M+Na] + 326.1270, found 326.1268.
Embodiment 3
[0063] Embodiment 3, the synthesis of compound 5h of the present invention
[0064] According to the method similar to Example 1, using semicarbazide hydrochloride as raw material in step 3, compound 5h was prepared, and the single-step yield of step 3 was 75%.
[0065]
[0066] Compound 5h: N-(4-(5-methyl-2-oxo-pyridin-1(2H)-yl)benzylidene)semicarbazide, white powder, m.p.192-194°C;
[0067] 1 H NMR (400MHz, DMSO) δ10.40(s,1H),7.90(s,1H),7.84(d,J=8.5Hz,2H),7.45(s,1H),7.42–7.35(m,3H) ,6.58(s,2H),6.42(d,J=9.3Hz,1H),2.04(s,3H);
[0069] HRMS (ESI) calcd for C 14 h 14 N 4 o 2 [M+H] + 271.1196, found 271.1188; [M+Na] + 293.1015, found 293.1009.
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Abstract
The invention discloses application of a compound as shown in a formula (I) (the formula can be seen in specification) or medically acceptable salt, the crystal form, aquo-complex or solvent thereof to preparation of anti-fibrosis drugs and / or antineoplastic drugs; wherein R1, R2, R3, R4 and R5 are separately or simultaneously selected from H, halogen, hydroxyl, nitro, carbonyl or a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group, a C6 alkyl group, a C7 alkyl group or a C8 alkyl group; R6 and R7 are separately or simultaneously selected from H, O=C-NH<2>, S=C-NH<2>, phenyl, methyl-substituted phenyl, ethyl-substituted phenyl, methoxyl-substituted phenyl and ethyoxyl-substituted phenyl. The invention provides application of the novel compound as shown in the formula (I) (the formula can be seen in specification) or medically acceptable salt, the crystal form, aquo-complex or solvent thereof to preparation of anti-fibrosis drugs and / or antineoplastic drugs, compared with pirfenidone, the novel compound has a specific C=N-N structure, anti-fibrosis activity of the novel compound is remarkably better than that of pirfenidone, and the novel compound has good industrialized prospect.
Description
technical field [0001] The invention relates to the application of pirfenidone derivatives in pharmacy. Background technique [0002] Fibrosis refers to the pathological process of reduction or necrosis of parenchymal cells in patients' organs, increase of extracellular matrix in tissues and diffuse excessive deposition caused by various pathogenic factors. Continuous progress can lead to destruction of organ structure and functional decline, until failure. Fibrosis can occur in many organs, and the most common clinical fibrosis mainly includes: (1) pulmonary fibrosis; (2) liver fibrosis; (3) cardiac fibrosis; (4) renal fibrosis and (5) Fibrosis of the pancreas; in addition, fibrosis of the eye, blood vessels, and nervous system may also occur. [0003] Anti-fibrotic drugs refer to the medicines for the treatment and / or prevention of fibrotic diseases, such as: pirfenidone (pharmaceutical product listed on the market), however, the inhibitory rate of this compound to fibrob...
Claims
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Application Information
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