29712-28-5

Usage

Uses

Used in Pharmaceutical Industry:
(Aminomethylene)bisphosphonic acid is used as a bone-preserving medication for the treatment of osteoporosis and Paget's disease of bone. It is utilized to inhibit bone resorption and increase bone density, which helps in reducing the risk of fractures and maintaining overall bone health.
Used in Orthopedics:
In the field of orthopedics, (aminomethylene)bisphosphonic acid is used as an adjunct therapy to support bone health and prevent bone loss in patients with various bone-related conditions. Its ability to inhibit bone breakdown and increase bone density makes it a valuable treatment option for improving bone strength and reducing the risk of fractures.
Used in Geriatrics:
(Aminomethylene)bisphosphonic acid is used as a preventive and therapeutic agent in geriatrics to address age-related bone loss and osteoporosis. By increasing bone density and reducing the risk of fractures, it helps in maintaining the mobility and independence of elderly patients.
Used in Oncology:
In oncology, (aminomethylene)bisphosphonic acid is used to manage bone metastases and reduce the risk of skeletal-related events in patients with cancer. Its bone-preserving properties help in improving the quality of life and overall prognosis of cancer patients with bone involvement.
Used in Drug Delivery Systems:
To enhance the efficacy and bioavailability of (aminomethylene)bisphonic acid, various drug delivery systems have been developed. These systems, including organic and metallic nanoparticles, serve as carriers for the drug, improving its delivery to target sites and therapeutic outcomes while minimizing side effects.

InChI:InChI=1/CH7NO6P2/c2-1(9(3,4)5)10(6,7)8/h1H,2H2,(H2,3,4,5)(H2,6,7,8)

Upstream product

• 81292-84-4 Amidinomethylendiphosphonsaeure Tetra-Natriumsalz 
• 106-49-0 p-toluidine 
• 77287-34-4 formamide 
• 1259009-07-8 N,O,O,O,O-penta(trimethylsilyl)aminomethylenediphosphonate 
• 122-51-0 orthoformic acid triethyl ester 
• 618-36-0 rac-methylbenzylamine 
• 103-67-3 benzyl-methyl-amine 
• 80474-99-3 tetraethyl (aminomethylene)bis(phosphonate) 

Downstream Products

• 116448-59-0 disodium [(3-phenylureido)methylene]bisphosphonate trihydrate 
• 140846-24-8 N₃-phenylthioureidomethylenebisphosphonic acid disodium salt 
• 70008-50-3 N-(diphosphonomethyl)-L-aspartic acid 
• 1094322-72-1 {3-[4-(dimethylamino)phenyl]thioureido}methylenebisphosphonic acid 

Relevant academic research and scientific papers

Biologically active pyridine mono- and bis-phosphonates: Efficient ligands for co-ordination of Cu2+ ions

Potentiometric and spectroscopic studies on the co-ordination ability of biologically important pyridine mono- and bis-phosphonates have shown that when sterically possible these compounds undergo tridentate co-ordination with Cu2+ ions. The complexes obtained are very stable. When the position of the nitrogen donor is sterically unfavourable the major binding occurs at the bis(phosphonate) site.

Synthesis of aminobisphosphonate

A new facile synthesis of aminobisphosphonate was reported. Dibenzylamine bisphosphonate (1) is prepared from dibenzylamine, triethyl orthoformate and diethyl phosphite. Deprotection by hydrogen transfer reaction and acid hydrolysis afforded aminobisphosphonate (2).

Syntheses and evaluation of 68Ga- and 153Sm-labeled DOTA-conjugated bisphosphonate ligand for potential use in detection of skeletal metastases and management of pain arising from skeletal metastases

This article reports the syntheses and evaluation of 68Ga- and 153Sm-complexes of a new DOTA (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid)-conjugated geminal bisphosphonate, DOTA-Bn-SCN-BP, for their potential uses in the early detection of skeletal metastases by imaging and palliation of pain arising from skeletal metastases, respectively. The conjugate was synthesized in high purity following an easily adaptable three-step reaction scheme. Gallium-68- and 153Sm-complexes were prepared in high yield (>98%) and showed excellent in vitro stability in phosphate-buffered saline (PBS) and human serum. Both the complexes showed high affinity for hydroxyapatite particles in in vitro binding study. In biodistribution studies carried out in normal Wistar rats, both the complexes exhibited rapid skeletal accumulation with almost no retention in any other major organ. The newly synthesized molecule DOTA-Bn-SCN-BP would therefore be a promising targeting ligand for the development of radiopharmaceuticals for both imaging skeletal metastases and palliation of pain arising out of it in patients with cancer when radiolabeled with 68Ga and 153Sm, respectively. A systematic comparative evaluation, however, showed that there was no significant improvement of skeletal accumulation of the 153Sm-DOTA-Bn-SCN-BP complex over 153Sm-DOTMP (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetramethylenephosphonic acid) as the later itself demonstrated optimal properties required for an agent for bone pain palliation.

Synthesis of tetradentate mixed bisphosphonates - New hydroxypyridinonate ligands for metal chelation therapy

In a general study for developing better drugs suitable for Fe, Al, Co or lanthanide chelation therapy experiments, new mixed bisphosphonate-hydroxy pyridonates were synthesized. We demonstrate that the method using amidation reaction and dealkylation by concentrated hydrochloric acid gives excellent results for amino bisphosphonic acid ligands having at least two carbons between the amino group and the methylene bisphosphonic acid group.

An Improved Synthesis of the Antibiotic Dehydrophos

Within this work an efficient procedure for the synthesis of the vinyl phosphonate tripeptide dehydrophos is described. This procedure constitutes a significant improvement over previously described strategies, since critical transformations in the synthesis of dehydrophos were carried out in only two synthetic steps, with higher yields and under smooth conditions. Thus, the dehydrophosphoalanine residue was generated by means of the Horner–Wadsworth–Emmons reaction of formaldehyde with a peptide bearing an aminomethylbis(phosphonate) moiety, whereas deprotection of the N-terminal position of the thus-obtained dehydrophosphonopeptide and partial hydrolysis of the dimethyl phosphonate residue took place simultaneously. In addition, we confirmed that the chiral integrity of the leucine residue was preserved throughout these transformations.

Hree-component reaction of benzylamines, diethyl phosphite and triethyl orthoformate: Dependence of the reaction course on the structural features of the substrates and reaction conditions

The reaction between benzyl amines, triethyl orthoformate, and diethyl phosphite affords either bisphosphonic (compound 1) or N-benzylaminobenzylphosphonic (compound 2) acid depending on the reaction conditions. The final output of the reaction can be manipulated by the choice of reaction conditions, particularly the molar ratio of substrates.

NOVEL BISPHOSPHONATES AND THEIR USE

We disclose novel diphosphonic acids or their physiologically admissible salts as well as their use in the production of a drug for inhibiting bone resorption, for the prevention or treatment of osteoporosis.

Synthesis of the new types of N-unsubstituted aminomethylenebisorganophosphorus acids and their derivatives

The interaction of trimethylsilyl esters of trivalent organophosphorus acids containing PH and POSiMe3 groups with hydrochlorides of ethoxymethylene imines is a convenient method for the synthesis of new trimethylsilyl esters of N-unsubstituted aminomethylenebisorganophosphorus acids with three and four coordinated phosphorus. Also trimethylsilyl trifluoromethanesulfonate as effective catalyst is used for the similar interaction of hydrochlorides of ethoxymethylene imines with tris(trimethylsilyl)phosphite. The corresponding bisorganophosphorus acids and their derivatives are presented.

Synthesis of new types of aminomethylenediphosphorus-containing acids and their derivatives

Convenient methods for synthesis of various aminomethylenediphosphorus-containing acids and their derivatives starting from available trimethylsilyl esters of hypophosphorous and phosphorous acids, ethoxymethyleneimine hydrochlorides, and N-substituted formamides have been proposed. Selected properties of the obtained compounds have been examined.

The preparation of N-substituted aminomethylidenebisphosphonates and their tetraalkyl esters via reaction of isonitriles with trialkyl phosphites and hydrogen chloride. Part 1

The reaction of isonitriles with trialkyl phosphites in the presence of hydrogen chloride gives tetraalkyl N-substituted aminomethylidenebisphosphonates via N-methylideneaminium (isonitrilium) salts. Hydrolysis or dealkylation of these tetraalkyl esters gives N-substituted aminomethylidenebisphosphonic acids in high yields.