32545-64-5

Usage

Uses

Used in Pharmaceutical Industry:
[(Cyclohexylamino)methanediyl]bis(phosphonic acid) is used as an antiviral agent for the treatment of cytomegalovirus retinitis in patients with AIDS. It is effective in inhibiting the replication of the virus, which helps slow down the progression of the disease.
Used in Antiviral Applications:
Cymevene is employed as an antiviral medication, specifically targeting cytomegalovirus retinitis in patients with AIDS. By inhibiting the replication of the virus, it helps to control the disease's progression and provides relief to the patients.
Used in Medical Treatments:
As a part of medical treatments for patients with AIDS, [(cyclohexylamino)methanediyl]bis(phosphonic acid) is used to manage and treat cytomegalovirus retinitis, a potentially severe ocular complication that can lead to vision loss if left untreated.

Upstream product

• 766-93-8 N-cyclohexylformamide 
• 108-91-8 cyclohexylamine 
• 931-53-3 Cyclohexyl isocyanide 
• 124351-93-5 tetraethyl (cyclohexylamino)methyl-1,1-bisphosphonate 

Relevant academic research and scientific papers

Synthesis and biological evaluation of 1-alkylaminomethyl-1,1-bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii

As an extension of our project aimed at the search for new chemotherapeutic agents against Chagas disease and toxoplasmosis, several 1,1-bisphosphonates were designed, synthesized and biologically evaluated against Trypanosoma cruzi and Toxoplasma gondii,

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.

Convenient synthesis of analogs of aminomethylene gem-diphosphonic acid from amines without catalyst

A simple, novel, and convenient synthesis of analogs of aminomethylene gem-diphosphonic acids in one-pot from primary and secondary amines in moderate yields was reported without catalyst.

Effects of Bisphosphonates on the Growth of Entamoeba histolytica and Plasmodium Species in Vitro and in Vivo

The effects of a series of 102 bisphosphonates on the inhibition of growth of Entamoeba histolytica and Plasmodium falciparum in vitro have been determined, and selected compounds were further investigated for their in vivo activity. Forty-seven compounds tested were active (IC50 50 ～ 4-9 μM) were nitrogen-containing bisphosphonates with relatively large aromatic side chains. Simple n-alkyl-1-hydroxy-1,1-bisphosphonates, known inhibitors of the enzyme farnesylpyrophosphate (FPP) synthase, were also active, with optimal activity being found with C9-C10 side chains. However, numerous other nitrogen-containing bisphosphonates known to be potent FPP synthase inhibitors, such as risedronate or pamidronate, had little or no activity. Several pyridine-derived bisphosphonates were quite active (IC50 ～ 10-20 μM), and this activity was shown to correlate with the basicity of the aromatic group, with activity decreasing with increasing pKa values. The activities of all compounds were tested versus a human nasopharyngeal carcinoma (KB) cell line to enable an estimate of the therapeutic index (TI). Five bisphosphonates were selected and then screened for their ability to delay the development of amebic liver abscess formation in an E. histolytica infected hamster model. Two compounds were found to decrease liver abscess formation at 10 mg/kg ip with little or no effect on normal liver mass. With P. falciparum, 35 compounds had IC50 values 50 values around 1 μM. Five compounds were again selected for in vivo investigation in a Plasmodium berghei ANKA BALB/c mouse suppressive test. The most active compound, a C9 n-alkyl side chain containing bisphosphonate, caused an 80% reduction in parasitemia with no overt toxicity. Taken together, these results show that bisphosphonates appear to be useful lead compounds for the development of novel antiamebic and antimalarial drugs.

Studies on novel bone resorption inhibitors. I. Synthesis and pharmacological activities of aminomethylenebisphosphonate derivatives

A series of aminomethylenebisphosphonate derivatives was synthesized and evaluated for their antiresorptive activities using a parathyroid hormone (PTH)-induced hypercalcemia model in rats (PIH model). Among these compounds, (cycloheptylamino)methylenebis(phosphonic acid) (3j) was finally selected for further investigation, proving 10-fold as potent as pamidronate in the PIH model and an immobilization bone atrophy model in rats (DA model). The structure-activity relationships of this series of bisphosphonates are discussed.