Preparation of (4-Amino-1-Hydroxybutylidene)bisphosphonic Acid Sodium Salt, MK-217 (Alendronate Sodium). An Improved Procedure for the Preparation of 1-Hydroxy-1,1-bisphosphonic Acids

KIECZYKOWSKI, G. R.; Jobson, Ronald B.; Melillo, David G.; Reinhold, Donald F.; Grenda, Victor J.; Shinkai, I.

doi:10.1021/jo00130a036

Cited by 197 publications

(156 citation statements)

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“…[2][3][4][5][6] In all these methods (Scheme 1), it was obtained by the reaction of 3-pyridylacetic acid with phosphorous acid and phosphorous trichloride in a solvent such as chlorobenzene, 2 methanesulfonic acid, 3 sulfolane, 4 ionic liquids, 5 and diphenyl ether. 6 All the above processes have some disadvantages associated with their use such as solid mass formation which prevents uniform mixing.…”

Section: Resultsmentioning

confidence: 99%

“…The synthesis of 1-hydroxyalkylidene-1,1-bisphosphonic acids (bisphosphonates) is based on reacting a carboxylic acid (1) with a mixture of phosphorous acid and phosphorous chloride such as PCl 3 or PCl 5 , then quenching the reaction mixture with water followed by heating to hydrolyze the phosphonated reaction mass to get required product (2). 1-Hydroxyalkylidene-1,1 bisphosphonic acids were prepared using a solvent such as chlorobenzene, 2 methanesulphonic acid, 3 sulfolane, 4 ionic liquids 5 and diphenyl ether 6 as shown in Scheme 1. Our present work…”

Section: Introductionmentioning

confidence: 99%

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A facile one pot synthesis of bisphosphonic acids and their sodium salts from nitriles

Rao¹,

Dandala²,

Lenin³

et al. 2007

Arkivoc

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A general and one pot synthesis for the preparation of bisphosphonic acids and their sodium salts (2a-e) from nitriles (3a-e) is described. This method involves hydrolysis of nitriles (3a-e) to the corresponding acids and subsequent bisphosphonation in a single solvent to produce bisphonates (2a-e). Preparations of some of bisphosphonates, which are presently in clinical use like risedronate (2a) sodium, ibandronate sodium (2d) are synthesized by following this new method. This method is useful for the preparation of other bisphosphonate compounds.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A facile one pot synthesis of bisphosphonic acids and their sodium salts from nitriles

Rao¹,

Dandala²,

Lenin³

et al. 2007

Arkivoc

View full text Add to dashboard Cite

show abstract

“…They are standardly prepared by a large-scale, one-step reaction of carboxylic acids with phosphorus trichloride and phosphorous or phosphoric acids, followed by hydrolysis with water; the procedure was optimized by Kieczykowski et al [14]. The reaction is carried out in selected solvents (phenylsulphonic acid, various phenols, chlorobenzene, diphenyl ether or ionic liquids) with sulfone and methanesulphonic acid being preferred choices [11,[15][16][17][18][19][20].…”

Section: Synthesis From Carboxylic Acidsmentioning

confidence: 99%

Synthetic Procedures Leading towards Aminobisphosphonates

Chmielewska

Kafarski

2016

Molecules

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Abstract:Growing interest in the biological activity of aminobisphosphonates has stimulated the development of methods for their synthesis. Although several general procedures were previously elaborated to reach this goal, aminobisphosphonate chemistry is still developing quite substantially. Thus, innovative modifications of the existing commonly used reactions, as well as development of new procedures, are presented in this review, concentrating on recent achievements. Additionally, selected examples of aminobisphosphonate derivatization illustrate their usefulness for obtaining new diagnostic and therapeutic agents.

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“…CMI was a commercial product from ThermPhos, Switzerland. PAA(PO 3 H 2 ) 2 was synthesized by a reaction of PAA with PCl 3 /H 3 PO 3 in water, as published before [33]. PCH was synthesized according to literature procedures [34].…”

Section: Reagents and Chemicalsmentioning

confidence: 99%

The interplay between cationic polyethyleneimine and anionic polyelectrolytes for the control of silica scale formation in process waters

Spinthaki¹,

Stathoulopoulou²,

Demadis³

2015

Int. J. Corros. Scale Inhib.

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Stabilization of mono-and disilicic acids is accomplished by using a cationic polymeric chemical additive, polyethyleneimine (PEI), in supersaturated silica solutions (the starting solution contained 500 ppm/8.3 mM sodium orthosilicate, Na 2 SiO 3 ·5H 2 O, expressed as SiO 2 ) at pH = 7. The PEI polymeric system contains an excess of amine groups (~25% primary amines, ~50% secondary amines and ~25% tertiary amines) that become protonated at circumneutral pH, hence charging the molecules positively. PEI was found to be efficient as a silica scale inhibitor only at the low dosage of 10 ppm. Its inhibitory activity was found to drop as its concentration increased. It was hypothesized that PEI is entrapped into the colloidal silica matrix and deactivated. Thus, one way to maintain its activity was to create blends of PEI and anionic polymers. Anionic polyelectrolytes that were tested included polyacrylic acid (PAA), phosphonated polyacrylic acid (PAA(PO 3 H 2 ) 2 ), carboxymethylinulin (CMI), poly(acrylamide-co-acrylic acid) (PAM-co-AA), phosphonomethylated chitosan (PCH) are also studied for their silica scale inhibition efficiency. It is observed that the silica inhibitory activity of PEI was improved upon its combination with anionic polyelectrolytes.

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Preparation of (4-Amino-1-Hydroxybutylidene)bisphosphonic Acid Sodium Salt, MK-217 (Alendronate Sodium). An Improved Procedure for the Preparation of 1-Hydroxy-1,1-bisphosphonic Acids

Cited by 197 publications

References 0 publications

A facile one pot synthesis of bisphosphonic acids and their sodium salts from nitriles

A facile one pot synthesis of bisphosphonic acids and their sodium salts from nitriles

Synthetic Procedures Leading towards Aminobisphosphonates

The interplay between cationic polyethyleneimine and anionic polyelectrolytes for the control of silica scale formation in process waters

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