Heterocyclic compounds for the treatment of pain and use thereof

US6054474A · kind A · utility

Assignee

• BioChem Pharma Inc. · CA

Inventors

• John DiMaio · Montréal, CA
• Dilip Dixit · Calgary, CA

Key dates

• Filing date: Mar 25, 1998
• Grant date: Apr 25, 2000
• Expiry date: Mar 25, 2018

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D337/16
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Polycyclic alkaloids of formula (I), ##STR1## wherein R.sub.1 is H, C.sub.1-6 alkyl, or C.sub.6-12 aryl optionally substituted with polar groups; R.sub.2 and R.sub.3 are independently H, OH, C.sub.1-6 alkyl, --C(NH)--NH.sub.2, a positively charged group, or C.sub.7-13 aralkyl optionally substituted with NH.sub.2, OH, C.sub.1-6 alkyl, or halogen; or R.sub.2 and R.sub.3 together form a 5 to 6 member ring optionally incorporating a heteroatom; R.sub.4 is H, C.sub.1-6 alkyl, OR.sub.6, SR.sub.6 or N(R.sub.6).sub.2, wherein each R.sub.6 is independently H, C.sub.1-3 alkyl; X is O, S, SO, SO.sub.2, N--R.sub.5, or C--(R.sub.5).sub.2, wherein each R.sub.5 is independently H, C.sub.1-6 alkyl, or C.sub.7-13 aralkyl optionally interrupted with one or more heteroatom; n is an integer from 0 to 2; m is an integer from 0 to 3; with the proviso that when X is CH.sub.2 then R1 is not CH.sub.3, R.sub.2 and R.sub.3 are not both H, R.sub.4 is not OH, m is not 3 and n is not 0. For the treatment of pain and pharmaceutically acceptable compositions comprising those compounds. The compounds of this invention acts as agonists at the opiate receptor.