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Process for the preparation of benzotriazepine derivatives

A compound, CH2 technology, applied in the direction of active ingredients of heterocyclic compounds, drug combination, organic chemistry, etc., can solve the problems of high price, slow reaction steps, disadvantages, etc.

Inactive Publication Date: 2008-11-12
JANSSEN PHARMA NV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method involves a slow reaction step and requires the use of excess ethyl hydrazine acetate (an expensive reagent), which is a disadvantage for large scale / commercial production

Method used

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  • Process for the preparation of benzotriazepine derivatives
  • Process for the preparation of benzotriazepine derivatives
  • Process for the preparation of benzotriazepine derivatives

Examples

Experimental program
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preparation example Construction

[0079] The present invention relates to the preparation method of following formula (X) compound:

[0080]

[0081] where R 1 , R 5 , R 2 , R 4 , a and R 9 as defined herein. The compound of formula (I) is benzotriazepine Derivatives for use in the treatment of diseases mediated by gastrin and cholecystokinin receptors, as disclosed in PCT publication WO 2003 / 041714.

[0082] The term "hydrocarbyl" as used herein refers to a monovalent group consisting of carbon and hydrogen. Hydrocarbyl groups include alkyl, alkenyl and alkynyl groups (in both straight and branched chain forms), cycloalkyl groups (including polycyclic alkyl groups such as bicyclooctyl and adamantyl), cycloalkenyl and aryl groups and the aforementioned Combinations of groups such as alkylcycloalkyl, alkylpolycycloalkyl, alkylaryl, alkenylaryl, alkynylaryl, cycloalkylaryl, and cycloalkenylaryl.

[0083] Where reference is made to a carbon atom of a hydrocarbyl group replaced by a N, O or S atom, it ...

Embodiment 1

[0198] [3-(2-Cyclohexanecarbonyl-phenyl)-1-amino-ureido]-ethyl acetate

[0199]

[0200] To a solution of (2-amino-phenyl)-cyclohexyl-methanone (1.0 g, 5 mmol) in DCM (15 ml) was added triethylamine (3.6 ml) and cooled to -50°C. At this temperature, a solution of triphosgene (also known as bis(trichloromethyl carbonate)) (0.5 g) in DCM (5 ml) was added all at once, and after the temperature was observed to rise to -10 ° C, the resulting solution was heated at -10 ° C and Matured at -20°C for about 15 minutes, then slowly transferred to a flask via a syringe containing ethyl hydrazinoacetate hydrochloride (0.5g, 3.2mmol) and triethylamine (1ml) with DCM (10ml) syrup. A rise in temperature from 23°C to 26°C was noted during the addition. After the reaction mixture was aged at ambient temperature for 2 hours, the insoluble material (triethylamine hydrochloride) was removed by filtration. The filtrate was concentrated in vacuo and the resulting residue was dissolved in iso...

Embodiment 2

[0205] (5-cyclohexyl-2-oxo-1,2-dihydro-benzo[e][1,2,4]triazepine -3-yl)-ethyl acetate

[0206]

[0207] Dissolve ethyl [1-[[[2-(cyclohexylcarbonyl)phenyl]amino]carbonyl]hydrazino]-acetate (20 mg) in TFA (0.2 ml) and mature for about 15 minutes. At this point HPLC analysis showed the disappearance of the signal corresponding to starting material at 10.5 minutes and the appearance of a signal corresponding to product at 11.01 minutes. The material was characterized by comparison with the signal from the HPLC trace of real samples.

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Abstract

The present invention is directed to a novel process for the preparation of benzo[e][1,2,4]triazepin-2-one derivatives, useful in the preparation of gastrin and cholecystokinin receptor ligands.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of US Provisional Application 60 / 717,658, filed September 16, 2005, which is hereby incorporated by reference in its entirety. field of invention [0003] The present invention relates to benzotriazepines Novel preparation method of derivatives, said benzotriazepine Derivatives are used as gastrin and cholecystokinin receptor ligands. Background of the invention [0004] PCT Publication WO 2003 / 041714, which specification is incorporated herein by reference, discloses benzotriazepines as ligands for the gastrin and cholecystokinin receptors derivative. PCT publication WO 2003 / 041714 also discloses benzotriazepine Methods for the preparation of derivatives. However, this method involves a slow reaction step and requires the use of excess ethyl hydrazine acetate (an expensive reagent), which is a disadvantage for large scale / commercial production. [0005] The process of the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D255/04C07D413/12A61K31/55A61P1/00C07D271/06C07C281/06
CPCC07D271/07C07D255/04C07D413/12A61P1/00A61P1/04A61P25/00A61P35/00A61P43/00
Inventor A·F·阿布德尔-马吉德L·安扎洛恩J·科恩S·梅尔曼F·维拉尼
Owner JANSSEN PHARMA NV
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