Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A kind of preparation method of bimatoprost pharmaceutical intermediate

A bimeteriprost and intermediate technology is applied in the field of synthesis of bimeteriprost pharmaceutical intermediates, and achieves the effects of high stereoselectivity, easy acquisition of raw materials, and easy industrial production.

Active Publication Date: 2022-04-22
JIANGSU ALPHA PHARM CO LTD
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The object of the present invention is to provide a kind of preparation method of bimatoprost drug intermediate with higher stereoselectivity and more economical, to solve the cis-trans isomer selection in the preparation of bimatoprost drug intermediate in the prior art sexual conundrum

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of preparation method of bimatoprost pharmaceutical intermediate
  • A kind of preparation method of bimatoprost pharmaceutical intermediate
  • A kind of preparation method of bimatoprost pharmaceutical intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022]

[0023] Pre-prepared solution: under the protection of nitrogen, dissolve 2.69g potassium tert-butoxide (0.024mol) in 14g tert-butanol, stir until dissolved and seal it for use. 2.93g (0.0107mol) of compound I and 4.21g (0.0118mol) of compound II were dropped into a 250ml three-necked flask successively, and the nitrogen gas was replaced in vacuum 5 times, and then 130g of DCM (dichloromethane) was injected inwardly under the protection of nitrogen gas, and the temperature was lowered to -60°C.

[0024] Inject all the potassium tert-butoxide / tert-butanol solution prepared above, control the temperature not to exceed -50°C, and finish the injection in about 10 minutes. After the injection, keep it at -60~-55°C for 5-6 hours, and then heat up naturally to room temperature. Transfer the above reaction solution into a 250ml single-necked bottle and spin dry. The spin-dried solid was slurried with 80 g of water at room temperature for 2 hours, and filtered. The solid ...

Embodiment 2

[0026]

[0027] Pre-prepared solution: under the protection of nitrogen, dissolve 5.38g potassium tert-butoxide (0.048mol) in 14g tert-butanol, stir until dissolved and seal it for use. 2.93 g (0.0107 mol) of compound I and 8.42 g (0.0118 mol) of compound II were sequentially put into a 250 ml three-necked flask, replaced by nitrogen vacuum for 5 times, and then 130 g of DCM was injected inward under the protection of nitrogen, and the temperature was lowered to -60°C with stirring.

[0028] Inject all the potassium tert-butoxide / tert-butanol solution prepared above, control the temperature not to exceed -50°C, and finish the injection in about 10 minutes. After the injection, keep it at -60~-55°C for 5-6 hours, and then heat up naturally to room temperature. Transfer the above reaction solution into a 250ml single-necked bottle and spin dry. The spin-dried solid was slurried with 80 g of water at room temperature for 2 hours, and filtered. The solid was slurried with 80 ...

Embodiment 3

[0030]

[0031] Pre-prepared solution: under the protection of nitrogen, dissolve 2.31g sodium tert-butoxide (0.024mol) in 14g tert-butanol, stir until dissolved and seal it for use. 2.93g (0.0107mol) of compound I and 4.21g (0.0118mol) of compound II were dropped into a 250ml three-necked flask successively, and the nitrogen gas was replaced in vacuum 5 times, and then 130g of DCM (dichloromethane) was injected inwardly under the protection of nitrogen gas, and the temperature was lowered to -60°C.

[0032] Inject all the potassium tert-butoxide / tert-butanol solution prepared above, control the temperature not to exceed -50°C, and finish the injection in about 10 minutes. After the injection, keep it at -60~-55°C for 5-6 hours, and then heat up naturally to room temperature. Transfer the above reaction solution into a 250ml single-necked bottle and spin dry. The spin-dried solid was slurried with 80 g of water at room temperature for 2 hours, and filtered. The solid was...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to a method for preparing bimatoprost pharmaceutical intermediates. The method takes compound I as a raw material and reacts with compound II under the action of a base to obtain bimatoprost Pharmaceutical intermediates: (3aR,4R,5R,6aS)‑5‑(benzoyloxy)hexahydro‑4‑[(1E)‑3‑oxo‑5‑phenyl‑1‑pentenyl]‑ 2H-cyclopenta[b]furan-2-one. The preparation method has the advantages of easy acquisition of raw materials, higher stereoselectivity, higher yield and higher purity, and easier industrial production of bimatoprost pharmaceutical intermediates.

Description

technical field [0001] The invention relates to the field of synthesis of pharmaceutical intermediates, in particular to a method for synthesizing bimatoprost pharmaceutical intermediates. Background technique [0002] Bimatoprost (Bimatoprost) is a prostaglandin analog, clinically used to reduce intraocular pressure in patients with open-angle glaucoma or ocular hypertension; Bimatoprost has the effect of promoting eyelash growth and is used to promote eyelash growth. The growth of eyelashes in rare patients; bimatoprost also has the effect of activating prostaglandin F2a receptors in hair follicles and promoting the growth of hair. This mechanism of action is expected to achieve curative effect in the field of male baldness. The chemical name of bimatoprost is (Z)-7-[(1R,2R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1- Pentenyl]cyclopentyl]-5-N-ethylheptenamide, the chemical structure is as follows: [0003] [0004] (3aR,4R,5R,6aS)-5-(Benzoyloxy)hexahydro-4-[(1E...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/935
CPCC07D307/935C07B2200/07
Inventor 陈本顺石利平叶金星李大伟徐春涛张维冰郭炳华马骧钱若灿刘春河陆波
Owner JIANGSU ALPHA PHARM CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com