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Biliverdin compound as well as preparation method and application thereof

A compound and biliverdin technology, applied in the field of drug synthesis, can solve the problems of difficult separation, many by-products and high cost, and achieve the effects of simple preparation process, low cost and mild conditions

Pending Publication Date: 2021-03-12
POSEIDON PHARM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Aiming at the problems of low yield, many by-products, high cost and difficult separation in the synthesis of biliverdin in the literature, the present invention aims to solve the problems existing in the prior art to a certain extent, and therefore, a new biliverdin is provided. Chlorophyll intermediate

Method used

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  • Biliverdin compound as well as preparation method and application thereof
  • Biliverdin compound as well as preparation method and application thereof
  • Biliverdin compound as well as preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0056]Method for preparation of chlorinated compounds

[0057]The present invention also provides a method of preparation of the above-mentioned chlorophyll intermediate, which is obtained by condensation by the compound of formula 2 and the compound of formula 3, and the reaction formula is as follows:

[0058]

[0059]Among them, R is selected from hydrogen, c1~ C5One of alkyl and benzyl groups;Indicates the two-button or single key, the position shown in A, BIndependently selected from one of the single bonds and double bonds,When it is a single bond, R is connected to the single button.1Or R2The toluene group is selected from the group consisting of toluene groups, toluene sulfonyl, phenyl sulfone group, benzulfonyl;When the double button is connected to the double button1Or R2One of hydrogen, R3 and R4 is aldehyde group, R3R4Another one selected from the group consisting of tert-butoxycarbonyl, hydrogen.

[0060]In the technical solution of the invention, the condensation reaction is carri...

Embodiment 1

[0088]Examples 1: 3, 3 '- (3,18 - 2 (2 - Toluealesulfonylthyl) -2, 7, 13, 17-tetramethyl-1, 19-dioxidation-1,19 , 22, 24-tetrahydro-21H-8, 12-porphyrin group) - Synthesis of dimethyl propionate (compound of formula 2)

[0089]

[0090]Weigh 1.00 gram of 9-tert-butoxycarbonyl-3,7-dimethyl-8- (2-methoxycarbonylthyl) -2- (2-p-tolueraulfonylthyl)-dipyrid Ethylene-1-keto (compound of formula 9), dissolved with 5 ml of trifluoroacetic acid, stirred at a temperature of 25 ° C for 30 minutes, add 0.87 grams of compound 9-formyl-2,7-dimethyl-8 - (2-methoxycarbonyl) -3- (2-piocarbylsulfonylthyl) - dipyrrolidate-1-ketone (compound of formula 10), stirred at a temperature of 25 ° C for 10 hours , 20 ml of dichloromethane was added, washed out of the organic layer, saturated sodium hydrogencarbonate to neutral, dried over anhydrous sodium sulfate, filtration, ethanol refined crystal blue green solid 0.85 grams, 3, 3, 3, 3, 18 - Second (2-p-toluenesulfonylthyl) -2, 7, 13, 17-tetramethyl-1,19-dioxo-1, 1...

Embodiment 2

[0091]Example 2: 3, 3 '- (3,18-2 (2-p-tolueraulfonylthyl) -2, 7, 13, 17-tetramethyl-1, 19-dioxide-1,19 , 22, 24-tetrahydro-21H-8, 12-porphyrin group) - Synthesis of dimethyl propionate (compound of formula 2)

[0092]

[0093]1.00 grams of compound-3,7-dimethyl-8- (2-methoxycarbonylthyl) -2- (2-p-toluenesulfonylthyl)-dipyridolin-1-ketone ( 11 compound compounds) and 0.87 g of 9-formyl-2,7-dimethyl-8- (2-methoxycarbonylthyl) -3- (2-p-toluearsulfonylthyl)-dipyrid Ethylene-1-ketone (shown in Formula 10), after mixing, dissolved with 50 ml of methanol, then add 1.5 ml of 1M hydrochloride solution, stirring at a temperature of 15 ° C for 10 hours, concentrated under reduced pressure, dichloromethane dissolved, Wash the saturated sodium bicarbonate to neutral, dry dry, filtrate, filtration, and ethanol, crystal crystal, 5,3 '- (2 - 2 - 2 - 2 - 2-p-Toluene) Sulfonylthyl) -2, 7, 13, 17-tetramethyl-1, 19-dioxo-1, 19, 22, 24-tetrahydro-21H-8, 12-porphyrin group) -bu Dimethyl propionate (compound of...

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Abstract

The invention provides a biliverdin compound. The structural formula of the biliverdin compound is shown as a formula 1, R is selected from one of hydrogen, C1-C5 alkyl and benzyl, 'what is describedin the specification' represents a double bond or a single bond, 'what is described in the specification' at positions A and B is independently selected from one of a single bond and a double bond, and when 'what is described in the specification' is a single bond, R1 or R2 linked to the single bond is selected from p-toluenesulfonyl, p-toluenesulfinyl, phenylsulfonyl, and benzenesulfinyl; when 'what is described in the specification' is a double bond, R1 or R2 linked to the double bond is hydrogen. The invention provides a novel intermediate of biliverdin or analogues thereof, which can be used for preparing biliverdin or analogues thereof, and is simple in preparation process, efficient, low in cost and easy to industrialize; in addition, the invention also provides a new preparation method of the intermediate of the biliverdin or the analogue thereof, and the preparation method is simple in preparation process, mild in condition, capable of being carried out at room temperature andlow in cost.

Description

Technical field[0001]The present invention relates to the field of drug synthesis, and more particularly, the present invention relates to a chlorinated compound and a method and use thereof.Background technique[0002]Biliverdin is a tetrapyrrole loop material obtained by hemoglin hypogin oxygenase (HO-1) hydrolyzed ring (shown in the formula 4 compound), due to its Be deep green. Chlorophyll is not only a middle metabolite of heme metabolic circulatory, which can also initiate a physiological role such as anti-inflammatory and immune regulation, such as improving liver function, reducing the alanine transaminase, reducing ischemia / reperfusion caused by liver transplantation. Damage, inhibiting blood vessel reshaping formed by neovascularized blood vessels, and inhibiting the function of auto diarrhea virus replication. Therefore, the huge potential for chlorophyll use of clinical drug use.[0003]In addition, biliary is a major raw material to cultivate bovine yellow in vitro, using...

Claims

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Application Information

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IPC IPC(8): C07D207/44
CPCC07D207/44Y02P20/55C07D403/14
Inventor 陈发普石聿新陈发凯
Owner POSEIDON PHARM CO LTD
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