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Teniloxazine

Chemical compound

Teniloxazine

Chemical compound

62473-80-7 (maleate) | elimination_half-life =

Teniloxazine (Lucelan, Metatone), also known as sufoxazine and sulfoxazine, is a drug which is marketed in Japan. Though initially investigated as a neuroprotective and nootropic agent for the treatment of cerebrovascular insufficiency in the 1980s, it was ultimately developed and approved as an antidepressant instead. It acts as a potent norepinephrine reuptake inhibitor, with fair selectivity over the serotonin and dopamine transporters, and also behaves as an antagonist of the 5-HT2A receptor.

Synthesis

4005084}} (1977 to Welfide Corp).</ref><ref>Muro Tomio, Chihara Yasuaki, et al. DE2530860, (1977 to Yoshitomi Pharmaceutical).</ref> Cerebrovascular dementia usage:<ref>Michihide Setoguchi, Koretake Anami, & Hiroshi Yasuda, EP0193637 (1986 to Welfide Corp).</ref>

Amide formation between 1-(Benzylamino)-3-{2-[(thiophen-2-yl)methyl]phenoxy}propan-2-ol [62473-86-3] (1) and Chloroacetylchloride [79-04-9] (2) gives PC13682456 (3). In the presence of sodium metal closing of the ring morpholine occurs to give PC13682470 (4). Lactam reduction with lithium aluminium hydride affords 4-Benzyl-2-({2-[(thiophen-2-yl)methyl]phenoxy}methyl)morpholine [62473-77-2] (5). Treatment with Ethyl chloroformate [541-41-3] (6) gives the urethane and hence 4-Ethoxycarbonyl-2-[2-(2-thenyl)-phenoxymethyl]morpholine, PC21482171 (7). Hydrolysis of the carbamate in the presence of barium hydroxide completes the synthesis of Teniloxazine (8).

Alternately, base reaction between 1-[2-(2-thenyl)phenoxy]-2,3-epoxypropane [55506-46-2] (9) and 2-Aminoethyl hydrogen sulfate [926-39-6] (10) is another way to perform the synthesis.

References

References

  1. (1997). "Dictionary of pharmacological agents". CRC Press.
  2. (February 1985). "[Pharmacological studies on sufoxazine (Y-8894). (I) Effects on experimental amnesia in mice]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica.
  3. (October 1985). "[Pharmacological studies on sufoxazine (Y-8894). (II). Anti-anoxic effect]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica.
  4. (October 1986). "[Pharmacological studies on Y-8894. (III). Its effect on the abnormal electrocorticogram induced by destruction of the internal capsule]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica.
  5. (November 1986). "[Pharmacological studies on Y-8894. (IV). Ameliorative effect on a cerebral energy metabolism disorder induced by KCN]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica.
  6. (March 1987). "[Pharmacological studies on Y-8894. (V) Effect on learning and memory in intact and experimentally amnesic rats]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica.
  7. (July 1987). "[Pharmacological studies on Y-8894 (VI). The effect on monoamine uptake and turnover in mouse brain]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica.
  8. (December 1987). "[Pharmacological studies on Y-8894. (VII). Effects on transient cerebral ischemia-induced amnesia in rats]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica.
  9. (August 1988). "[Pharmacological studies on Y-8894. (VIII). Effects on learning and memory in the radial maze task in mice]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica.
  10. (May 1987). "Clinical pharmacology of a new antidepressant, Y-8894 in healthy young and elderly volunteers". British Journal of Clinical Pharmacology.
  11. "Therapeutic Agent for Attention-Deficit Hyperactivity Disorder".
  12. Serradell, MN; Blancafort, P.; Castaer, J.; Y-8894. Drugs Fut 1981, 6, 7, 423.
  13. Muro, Tomio; Yuki, Hiroshi; Kawakita, Takeshi; Chihara, Yasuaki; Yasumoto, Mitsuyoshi; Setoguchi, Shinro; Anami, Koretake; Setoguchi, Michihide (1986). "Syntheses and Pharmacological Activities of 2-(Substituted Phenoxymethyl) morpholine Derivatives". YAKUGAKU ZASSHI. 106 (9): 764–774. doi:10.1248/yakushi1947.106.9_764.
  14. Tomio Muro, et al. {{US patent. 4005084 (1977 to Welfide Corp).
  15. Muro Tomio, Chihara Yasuaki, et al. DE2530860, (1977 to Yoshitomi Pharmaceutical).
  16. Michihide Setoguchi, Koretake Anami, & Hiroshi Yasuda, EP0193637 (1986 to Welfide Corp).
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antidepressants morpholines thiophenes phenol-ethers
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