Aptiganel

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Aptiganel (Cerestat; CNS-1102) is an unsuccessful drug candidate which acts as a noncompetitive NMDA antagonist, and that was under development by Cambridge Neuroscience, Inc as a treatment for stroke.[1] It has neuroprotective effects and was researched for potential use in the treatment of stroke,[2] but despite positive results in animal studies,[3] human trials showed limited efficacy,[4] as well as undesirable side effects such as sedation and hallucinations,[5][6] and clinical development was ultimately not continued.[7]

The drug's failure led to the collapse of Cambridge Neuroscience in 1998[8] and its eventual sale to CeNeS Pharmaceuticals in 2000.[9]

Other guanidine substances that the company had been bowling on was Cns-1145 & CNS1237.

Synthesis

File:Aptiganel synthesis.svg
Aptiganel synthesis:[10][11]

1-Naphthylamine is reacted with cyanogen bromide 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.

See also

  • Ditolylguanidine
  • CNS1237 shares predominantly most of the same structural entities.

References

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  8. Staff, Boston Business Journal. May 7, 1998. CNSI appoints new president, CEO
  9. Staff, ICIS. 23 May 2000 CeNeS to buy US neuroscience firm CNSI for $44m
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