A facile preparation of N-methylpentan-l-amine: A key intermediate for ibandronate sodium
A facile preparation of N-methylpentan-l-amine, which is a key intermediate for the synthesis ibandronate sodium, an anti-osteoclast agent is described. This route is cost effective over the previous methods. Part of this work could be an easy access for the preparation of various N,N-alkyl or aryl amine derivatives.
Reddyab, V V R M Krishna,Chintamani,Udaykiran,Madhusudhan,Mukkanti
experimental part
p. 1257 - 1260
(2010/12/24)
A NEW AND IMPROVED PROCESS FOR THE PREPARATION OF IBANDRONATE SODIUM MONOHYDRATE
The present invention discloses a new and an improved process for preparation of Ibandronate sodium monohydrate. According to the process pentylamine is reacted with ethylacrylate to give N-pentyl-β-alanine ethyl ester (XXIV), which on methylation provided N-methyl-N-pentyl-β-alanine ethylester formula (XXV). The reresulting ester on hydrolysis and subsequent treatment with hydrochloric acid furnished 3-(N-methyl-N-pentylamino)propionic acid hydrochloride formula (II). Bisphosphorylation of 3-(N-methyl-N-pentylamino)propionic acid hydrochloride formula (II) with phosphorous acid and phosphorous trichloride followed by hydrolysis and subsequent treatment with a base provided Ibandronate monosodium monohydrate of formula (I).
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Page/Page column 5; 9-10
(2009/09/05)
CRYSTALLINE FORM A OF IBANDRONIC ACID AND PROCESS FOR THE PREPARATION
The present invention relates crystalline Form A of Ibandronic acid having Formula (I) and a process for the preparation thereof.
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Page/Page column 28
(2008/06/13)
REAGENT AND USE THEREOF FOR THE PRODUCTION OF BISPHOSPHONATES
A new liquid reagent is disclosed in form of an ionic liquid containing phosphorous acid and a tertiary amine. The reagent can be used as a replacement of phosphorous acid, where the new reagent as a liquid reagent can be handled using usual equipment for handling liquids and the dosing of the reagent can therefore be controlled more precisely in industrial plants compared to phosphorous acid, which is a solid at ambient temperature. The new liquid reagent is particular suitable for the synthesis of bisphosphonates.
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Page/Page column 10
(2008/12/05)
IMPROVED PROCESS FOR THE PREPARATION OF IBANDRONATE SODIUM
Present invention discloses an improved and commercial process for the preparation of ibandronic acid or its monosodium salt. According to the process 3-N-methylaminopropionitrile is reacted with n-pentylbromide to get the tertiary amine of formula-II. Hydrolysis of the nitrile compound of formula-II with hydrochloric acid gave the b-alanine derivative of formula-X. Bis-phosphonylation of the acid compound of formula-X with phorphorous trichloride and phosphorous acid, followed by water hydrolysis gave aqueous ibandronic acid. Treatment of this with sodium hydroxide, followed by dilution of the aqueous solution with methanol gave ibandronate monosodium of formula-Ia as white crystalline solid. Present process utilizes simple raw materials and avoids the column chromatography technique used in the prior art process for isolation of ibandronic acid. Overall yield of ibandronate is more than 60% from the nitrile intermediate of formula-II. Ibandronate is widely used as bone resorption inhibitor.
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Page/Page column 7-9
(2008/06/13)
Method for synthesizing bisphosphonate
The invention relates to a novel multi step synthesis of 3-(N-methyl-N-pentyl) amino-1-hydroxypropane-1,1-diphosphonic acid, monosodium salt, monohydrate, of the formula
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Page/Page column 3
(2008/06/13)
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