Intermediate for synthesizing prostaglandin drugs and its preparation method

A technology for prostaglandins and intermediates, which is applied in the field of intermediates for the synthesis of prostaglandins, and can solve the problems that prostaglandins cannot meet the needs of clinical medication and their content is low

Inactive Publication Date: 2016-01-27
SUNCADIA PHARM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Prostaglandins are trace components widely present in various tissues of humans and animals, and the content is extremely low. In addition, prostaglandin F-type derivatives have excellent therapeutic effects on glaucoma and intraocular hypertension and other diseases. Natural sources of prostaglandins cannot meet the requirements. clinical drug demand

Method used

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  • Intermediate for synthesizing prostaglandin drugs and its preparation method
  • Intermediate for synthesizing prostaglandin drugs and its preparation method
  • Intermediate for synthesizing prostaglandin drugs and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: Preparation of compound Iaa

[0032]

[0033] Compound Iaa is synthesized as follows:

[0034]

[0035] step 1):

[0036] Under a nitrogen atmosphere, triethylamine (2.5 mL) was added to a solution of compound IV (1.0 g, purchased from Shanghai Julong Pharmaceutical Research and Development Co., Ltd.) in dichloromethane (50 mL). The reaction system was cooled to -78°C, and a solution of triisopropylsilyl triflate (2.9 g) in dichloromethane (10 mL) was added. After two hours, the cooling bath was removed, and the reaction system was stirred at 20°C for 30 minutes. The reaction system was concentrated under reduced pressure, and the residue was purified by column chromatography to obtain compound Vaa.

[0037] 1 HNMR (400MHz, CDCl 3 ): δ4.94-4.89(m, 1H), 4.18-4.11(m, 1H), 3.84(dd, J=9.6, 5.2Hz, 1H), 3.69(dd, J=10.4, 7.2Hz, 1H), 2.79(dd, J=18, 10.8Hz, 1H), 2.63-2.60(m, 1H), 2.53-2.45(m, 2H), 2.70(s, 1H), 2.05-1.97(m, 2H), 1.14- 1.01(m, 21H)

[0...

Embodiment 2

[0044] Embodiment 2: preparation compound Iab

[0045]

[0046] Using a method similar to the synthesis of compound Iaa, compound Iab was synthesized.

[0047] 1 H-NMR (400MHz, CDCl 3 ( m, 4H), 2.39~2.33(m, 1H), 2.19~2.00(m, 5H), 1.89~1.85(m, 3H), 1.73~1.58(m, 3H), 1.13~1.09(m, 3H), 0.89~0.85(m, 9H), 0.07~0.02(m, 6H)

Embodiment 3

[0048] Embodiment 3: preparation compound Iac

[0049]

[0050] Compound lac was synthesized using a method similar to the synthesis of compound Iaa.

[0051] 1 H-NMR (400MHz, CDCl 3 )δ5.98~5.96(m, 1H), 5.41~5.34(m, 2H), 4.14~4.10(m, 2H), 3.76~3.72(m, 1H), 3.49~3.45(m, 1H), 3.34~ 3.28(m, 2H), 3.22~3.17(m, 2H), 2.40~2.32(m, 1H), 2.18~2.10(m, 4H), 2.05~1.99(m, 1H), 1.85~1.83(br, 3H ), 1.71~1.58(m, 3H), 1.48~1.40(m, 2H), 1.35~1.28(m, 2H), 0.90~0.85(m, 3H), 0.84~0.83(m, 9H), 0.05~0.01 (m, 6H)

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Abstract

Disclosed is an intermediate (structural formula I) for synthesizing prostaglandin medicines and preparation method therefor. The intermediate is used for synthesizing prostaglandin medicines, such as bimatoprost, travoprost, latanoprost, etc. The intermediate is prepared by means of hemiacetal Wittig reactions and derivatization thereof.

Description

technical field [0001] The invention relates to an intermediate for synthesizing prostaglandin drugs and a preparation method thereof. Background technique [0002] Prostaglandins are a class of fatty acid derivatives with 20 carbon atoms. Prostaglandins regulate various physiological functions of the human body at the level of hormone concentration, and have regulatory effects on blood pressure, smooth muscle contraction, gastric juice secretion and platelet aggregation. Among them, prostaglandin F-type derivatives are clinically used to treat open-angle glaucoma and ocular hypertension, so as to reduce the intraocular high pressure of patients. [0003] Prostaglandins are trace components widely present in various tissues of humans and animals, and the content is extremely low. In addition, prostaglandin F-type derivatives have excellent therapeutic effects on glaucoma and intraocular hypertension and other diseases. Natural sources of prostaglandins cannot meet the requi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/18C07D307/20C07C235/30C07C231/12C07C405/00
CPCC07D307/20C07C235/30C07C405/0041C07C2601/02C07C2601/08C07D295/108C07F7/1804
Inventor 张富尧江宏金青青孙飘扬
Owner SUNCADIA PHARM CO LTD
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