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Novel prostaglandin derivative

A drug and configuration technology, applied in the field of cyclodextrin inclusion compounds, can solve the problems of PGE chemical and metabolic instability

Active Publication Date: 2018-12-21
AGC INC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

PGEs can also be used for other indications. However, natural PGEs are extremely unstable chemically and metabolically. Therefore, more stable PGE derivatives with higher efficacy and fewer side effects have been intensively researched.

Method used

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  • Novel prostaglandin derivative
  • Novel prostaglandin derivative
  • Novel prostaglandin derivative

Examples

Experimental program
Comparison scheme
Effect test

reference example 1

[0317] Reference Example 1: (S)-5-cyclopropyl-2-methylpent-4-ynoic acid methyl ester

[0318]

[0319] After drying lithium chloride (4.24g) and zinc powder (9.15g) under reduced pressure, tetrahydrofuran (THF) (100mL), 1,2-dibromoethane (0.433mL) and trimethylchlorosilane were added at room temperature (0.127 mL). A THF (30 mL) solution of (R)-3-iodo-2-methylpropionic acid methyl ester (22.8 g) was added dropwise to the mixture, followed by stirring at 40° C. for 1.5 hours to prepare an organozinc reactant. Lithium chloride (7.63 g), copper(I) cyanide (8.06 g) and THF (90 mL) were added to a separate reaction vessel, and the mixture was stirred for 1 hour. The mixture was cooled at -10°C, and the aforementioned organozinc reactant was added dropwise thereto. The reaction mixture was stirred at -10°C for 10 minutes, then cooled at -78°C, a THF (50 mL) solution of 2-(bromoethynyl)cyclopropane (14.5 g) was added dropwise, and stirred at the same temperature for 15 hours Th...

reference example 2

[0321] Reference Example 2: Dimethyl (S)-(+)-(6-cyclopropyl-3-methyl-2-oxohex-5-yn-1-yl)phosphonate

[0322]

[0323] THF (25 mL) was added to dimethyl methylphosphonate (4.34 mL), and 1.6M n-butyllithium (23.7 mL) was added dropwise at -78°C. After the reaction mixture was stirred at -78°C for 1 hour, a THF (10 mL) solution of (S)-5-cyclopropyl-2-methylpent-4-ynoic acid methyl ester obtained in Reference Example 1 was added, Stir at the same temperature for 4 hours. Aqueous ammonium chloride solution was added to the reaction mixture, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3 to ethyl acetate only) to obtain the title compound (2.36 g). Yield 61%.

[0324] 1 H NMR (400MHz, CDCl 3 )δ3.81(s,3H),3.78(s,3H),3.20(ddd,J=14.4,22.8,28.4Hz,2H),2.91(q,J=6.8Hz,1H),2.33(dddd,J =2.0,6.8,16.8,44.4Hz,2H),1.18(d,J=7.2Hz,3H),1.18(...

reference example 3

[0325] Reference example 3: 7-((1R,2R,3R,5S)-5-acetoxy-2-hydroxymethyl-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentene base) methyl heptanoate

[0326]

[0327]To a suspension of 4-(carboxybutyl)triphenylphosphine bromide (14.06 g) in THF (86 mL) was added 1M potassium bis(trimethylsilyl)amide (64 mL), followed by stirring for 1 hour. The mixture was cooled at -78°C, and (3aR, 4S, 5R, 6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)hexahydro-5-((tetra Hydrogen-2H-pyran-2-yl)oxy)-2H-cyclopenta[b]furan-2-ol (3.92g) in THF (50mL) solution, stirred at the same temperature for 30 minutes, then warmed to room temperature and stir overnight. Water was added to the reaction mixture, extracted with t-butyl methyl ether, acidified with disodium citrate, and extracted with ethyl acetate. Dry the organic layer with anhydrous sodium sulfate, concentrate under reduced pressure, add acetone (390 mL), add diisopropylethylamine (9.16 mL), iodomethane (2.95 mL) and 1,8-di Azacyclo[5.4.0]undec...

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PUM

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Abstract

The present invention relates to: a novel prostaglandin derivative having an alkynyl group in a [omega]-chain, particularly a novel prostaglandin derivative having a double bond at position-2 and alsohaving an alkynyl group in a [omega]-chain; and a medicine containing the compound as an active ingredient. According to the present invention, it becomes possible to provide: a compound representedby formula (1) [wherein each symbol is as defined in the description], a pharmaceutically acceptable salt of the compound, or a cyclodextrin inclusion complex of the compound or the pharmaceutically acceptable salt; and a medicine which contains the compound as an active ingredient, particularly which can be used for the prevention or treatment of a blood flow disturbance associated with spinal canal stenosis or chronic arterial occlusive disease.

Description

technical field [0001] The present invention relates to novel prostaglandin derivatives having an alkyne group in the omega chain of prostaglandins or their pharmaceutically acceptable salts or their cyclodextrin inclusion compounds, especially having a double bond at the 2-position of prostaglandins and Novel prostaglandin derivatives with alkyne groups in the omega chain. In addition, the present invention relates to a drug containing at least one of the prostaglandin derivative or its pharmaceutically acceptable salt or their cyclodextrin inclusion compound as an active ingredient, especially a drug for preventing or treating blood flow disorder drug. Background technique [0002] Peripheral arterial occlusive disease is a disease caused by arterial stenosis / occlusion due to arteriosclerosis and thrombosis, resulting in peripheral ischemia, especially lower extremities, showing symptoms such as chills, intermittent claudication, pain, and ulceration / necrosis of lower ext...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C405/00A61K31/5575A61K47/40A61P7/02A61P9/08A61P9/10A61P43/00
CPCA61K47/40A61K31/5575C07C405/00A61P9/10A61P9/08A61P9/12C07C2601/08A61K47/6951A61P9/00C07C405/0016C07C405/0041C07H3/06
Inventor 安田新松村靖泽田和好难波宏好田口一贵
Owner AGC INC
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