Pemetrexed thiocarbamide salt and preparation method thereof

A technology of pemetrexed thiourea salt and pemetrexed, which is applied in the field of pharmacy, can solve the problems of complex preparation process, poor stability, and low yield, and achieve the effect of easy preparation and good stability

A technology of pemetrexed thiourea salt and pemetrexed, which is applied in the field of pharmacy, can solve the problems of complex preparation process, poor stability, and low yield, and achieve the effect of easy preparation and good stability

CN101691371AActive Publication Date: 2010-04-07SHENZHEN NEPTUNUS PHARM CO LTD
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  • Pemetrexed thiocarbamide salt and preparation method thereof
  • Pemetrexed thiocarbamide salt and preparation method thereof
  • Pemetrexed thiocarbamide salt and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1 Preparation process 1 of pemetrexed thiourea salt

[0023] In a 100ml reaction bottle, put 2.50g (5.85mmol) of pemetrexed into it, add 25ml of deionized water, 0.668g (8.78mmol) of thiourea salt, stir and react at room temperature for 1 hour, filter, and the filtrate is distilled under reduced pressure to precipitate a solid, add Methanol, until most of the product was precipitated, filtered, and vacuum-dried to obtain 2.26g, yield 76.4%.

[0024] Elemental analysis: C: 49.90 (49.79% of theoretical value), H: 5.49 (5.57% of theoretical value), N: 19.53 (19.36% of theoretical value).

[0025] Infrared spectrum (KBr tablet): characteristic absorption peak (cm -1 ) and its attribution: 3330 (C-NH 2 , -NH, -OH), 3046 (C 6 h 4 , benzene ring hydrocarbon stretching vibration), 2929 (-CH 2 -), 2510(-NH 3 '), 1648 (C=O), 1500, 1392 (C 6 h 4 , benzene ring skeleton vibration).

[0026] 1 H NMR spectrum (DMSO-d 6 ), chemical shift δ (ppm) and assignment o...

Embodiment 2

[0027] Embodiment 2 The preparation process 2 of pemetrexed thiourea salt

[0028] In a 100ml reaction bottle, put 2.50g (5.85mmol) of pemetrexed, add 60ml of anhydrous methanol, stir to dissolve, add 0.445g (5.85mmol) of thiourea, stir and react at room temperature for 0.5 hours, filter, wash with methanol and water , dried in vacuum to obtain 1.64g, yield 55.3%.

Embodiment 3

[0029] Embodiment 3 The preparation process 3 of pemetrexed thiourea salt

[0030] In a 100ml reaction bottle, put 2.50g (5.85mmol) of pemetrexed, add 60ml of absolute ethanol, stir to dissolve, add 2.23g (29.27mmol) of thiourea, stir at room temperature for 1 hour, filter, wash with ethanol and water , dried in vacuo to obtain 1.90 g, yield 64.2%.

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Abstract

The invention discloses a pemetrexed thiocarbamide salt and a preparation method thereof, and a medicinal composition containing the pemetrexed thiocarbamide salt. The pemetrexed thiocarbamide salt is generated through the reaction of pemetrexed and thiocarbamide in water and / or an organic solvent. The preparation process is simple, the yield is high and the stability is good.

Description

technical field [0001] The invention belongs to the field of pharmacy, and in particular relates to pemetrexed thiourea salt and a preparation method thereof. Background technique [0002] Pemetrexed disodium is a second-line new drug developed by Eli Lily for the treatment of malignant pleural mesothelioma and non-small cell lung cancer. Its trade name is Alimta, and its structural formula is as follows: [0003] [0004] Alimta is an anti-folate-metabolizing antineoplastic drug that works by interfering with folate-dependent metabolic processes during cell replication. In vitro tests have shown that the drug can inhibit folate-dependent enzymes such as thymidylate synthase, dihydrofolate reductase, and glycine ribonucleoside formyltransferase. These enzymes are involved in the biosynthesis of thymidine and purine nucleosides, and when one or more of these enzymes are blocked, cancer cells cannot grow and multiply. Among the currently approved folic acid antagonists, e...

Claims

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Application Information

Patent Timeline
07 Apr 2010
Publication
CN101691371A
IPC
C07D487/04; A61K31/519; A61P35/00
Inventors
唐田; 王彦青