U-47700: Difference between revisions

This compound was initially developed by a team at Upjohn in the 1970s.<ref> Jacob Szmuszkovicz (4 July 1978). "Patent US4098904 - Analgesic n-(2-aminocycloaliphatic)benzamides" | http://www.google.com/patents/US4098904</ref> Upjohn created over a dozen patents on related compounds<ref>Darrell D Mullins (28 June 1966). "Patent US US3258489 - N-(1-aminocyclohexylmethyl)anilines and n-(1-nitrocyclohexylmethyl)an-ilines". | http://www.google.com/patents/US3258489</ref><ref>Norman James Harper, George Bryan Austin Veitch (17 August 1976). "Patent US3975443 - 1-(3,4-dichlorobenzamidomethyl)-cyclohexyldimethylamine". | http://www.google.com/patents/US3975443</ref><ref>http://www.google.com/patents/US3510492</ref><ref>Jacob Szmuszkovicz (5 May 1970). "Patent US3510492 - 2-anilino and 2-anilinomethyl cycloalkylamines". | http://www.google.com/patents/US3510492</ref><ref> Ronald H Rynbrandt, Louis L Skaletzky (7 March 1972). "Patent US3647804 - Cycloalkanecarboxamides". | http://www.google.com/patents/US3510492</ref><ref>W. Roll (23 July 1974). "Patent US3825595 - N-cyclopentyl-n-2-hydroxyalkyl-ring-substituted benzamides". | http://www.google.com/patents/US3825595</ref><ref>Norman James Harper, George Bryan Austin Veitch (20 September 1977). "Patent US4049663 - Ethylene diamine derivatives".</ref><ref> Alan F. Casy, Robert T. Parfitt (1986). Opioid Analgesics, Chemistry and Receptors. Springer US. p. 395. ISBN 978-1-4899-0587-1 | http://www.google.com/patents/US4049663</ref> until they discovered that U-47700 was the most active.<ref>Alan F. Casy, Robert T. Parfitt (1986). Opioid Analgesics, Chemistry and Receptors. Springer US. p. 395. ISBN 978-1-4899-0587-1. | http://link.springer.com/book/10.1007%2F978-1-4899-0585-7</ref> This was done by looking for the key functional groups which gave the greatest activity.<ref>Medicinal agents incorporating the 1,2-diamine functionality. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/2687936</ref>

==Chemistry==

U-47700 is an atypical opioid of the benzamide class. It features core phenyl ring with two chlorine atoms at carbons R₃ and R₄. This ring is connected to an amine group through a carboxyl group (C=O). The terminal nitrogen atom of the amide group is bonded to a methyl carbon and substituted cyclohexane ring. The cyclohexane ring is further substituted at R₂ with a dimethylamino group, thus forming the structure of U-47700.