Aptiganel (Cerestat; CNS-1102) is an unsuccessful drug candidate which acts as a noncompetitive

NMDA antagonist NMDA receptor antagonists are a class of drugs that work to antagonize, or inhibit the action of, the ''N''-Methyl-D-aspartate receptor ( NMDAR). They are commonly used as anesthetics for animals and humans; the state of anesthesia they induce ...

, and that was under development by Cambridge Neuroscience, Inc as a treatment for stroke. It has

neuroprotective Neuroprotection refers to the relative preservation of neuronal structure and/or function. In the case of an ongoing insult (a neurodegenerative insult) the relative preservation of neuronal integrity implies a reduction in the rate of neuronal los ...

effects and was researched for potential use in the treatment of stroke, but despite positive results in animal studies, human trials showed limited efficacy, as well as undesirable side effects such as sedation and hallucinations, and clinical development was ultimately not continued. The drug's failure led to the collapse of Cambridge Neuroscience in 1998 and its eventual sale to CeNeS Pharmaceuticals in 2000.Staff, ICIS. 23 May 200
CeNeS to buy US neuroscience firm CNSI for $44m
/ref> Other guanidine substances that the company had been bowling on was Cns-1145 & CNS1237.

Synthesis

1-Naphthylamine 1-Naphthylamine is an aromatic amine derived from naphthalene. It can cause bladder cancer (transitional cell carcinoma). It crystallizes in colorless needles which melt at 50 °C. It possesses a disagreeable odor, sublimes readily, and tur ...

is reacted with

cyanogen bromide Cyanogen bromide is the inorganic compound with the formula (CN)Br or BrCN. It is a colorless solid that is widely used to modify biopolymers, fragment proteins and peptides (cuts the C-terminus of methionine), and synthesize other compounds. ...

to give 2. Treatment of this intermediate with 3-ethyl-''N''-methylaniline leads to addition to the cyano group and formation of the corresponding diaryl guanidine, aptiganel, 3.

References

{{Ionotropic glutamate receptor modulators NMDA receptor antagonists Guanidines Naphthylamines Anilines

Synthesis

See also

References