J-113,397

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search

Template:Short description Template:Drugbox

J-113,397 is an opioid drug which was the first compound found to be a highly selective antagonist for the nociceptin receptor, also known as the ORL-1 receptor.[1][2] It is several hundred times selective for the ORL-1 receptor over other opioid receptors,[3][4] and its effects in animals include preventing the development of tolerance to morphine,[5] the prevention of hyperalgesia induced by intracerebroventricular administration of nociceptin (orphanin FQ),[6] as well as the stimulation of dopamine release in the striatum,[7] which increases the rewarding effects of cocaine,[8] but may have clinical application in the treatment of Parkinson's disease.[9][10][11]

Synthesis

Patents for treating arrhythmia:[12]

File:J-113,397 synthesis (2007).svg
Improved synthesis:[13] Additional patents:[14][15]

Condensation between 1-Benzyl-3-methoxycarbonyl-4-piperidone [57611-47-9] (1) and O-Phenylenediamine (2) gives CID:16726310 (3). Reaction with boc anhydride followed by treatment with trifluoroacetic acid gives CID:16726358 (4). Reaction with iodoethane in the presence of base alkylates the urea nitrogen giving CID:16726359 (5). Reduction of the enamine by treatment with magnesium metal in methanol solvent occurs to give predominantly the trans isomer, CID:16726360 (6). Catalytic removal of the benzyl group gives CID:16726362 (7). Reductive amination with Cyclooctanecarbaldehyde [6688-11-5] (7) gives CID:16726364 (9). Lastly, reduction of the ester with lithium aluminium hydride completed the synthesis of J-113397 (10).

See also

References

<templatestyles src="Reflist/styles.css" />

  1. ↑ Script error: No such module "Citation/CS1".
  2. ↑ Script error: No such module "Citation/CS1".
  3. ↑ Script error: No such module "Citation/CS1".
  4. ↑ Script error: No such module "Citation/CS1".
  5. ↑ Script error: No such module "Citation/CS1".
  6. ↑ Script error: No such module "Citation/CS1".
  7. ↑ Script error: No such module "Citation/CS1".
  8. ↑ Script error: No such module "Citation/CS1".
  9. ↑ Script error: No such module "Citation/CS1".
  10. ↑ Script error: No such module "Citation/CS1".
  11. ↑ Script error: No such module "Citation/CS1".
  12. ↑ Guo Zheng, et al. <templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters". & <templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters". (2020).
  13. ↑ Script error: No such module "Citation/CS1".
  14. ↑ Satoshi Ozaki, et al. <templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters". (to MSD KK).
  15. ↑ Hiroshi Kawamoto, et al. <templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters". (to MSD KK).

Script error: No such module "Check for unknown parameters".

Template:Opioidergics

Retrieved from "http://debianws.lexgopc.com/wiki143/index.php?title=J-113,397&oldid=7559690"