US 11,912,707 B2
Mitragynine alkaloids as opioid receptor modulators
Andrew Kruegel, Secaucus, NJ (US); Dalibor Sames, New York, NY (US); Madalee G. Wulf, Beverly, MA (US); and Jonathan A. Javitch, Dobbs Ferry, NY (US)
Assigned to THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK, New York, NY (US)
Filed by The Trustees of Columbia University in the City of New York, New York, NY (US)
Filed on Mar. 2, 2021, as Appl. No. 17/189,456.
Application 17/189,456 is a division of application No. 16/088,311, granted, now 10,961,244, previously published as PCT/US2017/023977, filed on Mar. 24, 2017.
Claims priority of provisional application 62/313,360, filed on Mar. 25, 2016.
Prior Publication US 2021/0179618 A1, Jun. 17, 2021
Int. Cl. C07D 471/14 (2006.01); A61K 45/06 (2006.01); A61K 31/4375 (2006.01); C07D 471/20 (2006.01); A61K 31/437 (2006.01); A61P 25/00 (2006.01); A61K 31/438 (2006.01)
CPC C07D 471/14 (2013.01) [A61K 31/437 (2013.01); A61K 31/438 (2013.01); A61K 31/4375 (2013.01); A61K 45/06 (2013.01); A61P 25/00 (2018.01); C07D 471/20 (2013.01)] 11 Claims
 
1. A compound having the structure:

OG Complex Work Unit Chemistry
wherein
X is N or NH;
R1 is —OH, —O-alkyl, —O(CO)-alkyl or is absent;
R2 is —H or -alkyl;
R3 is —H or -alkyl;
R4 is —H or -alkyl;
α is a bond and is absent or present;
β is a bond and is absent or present; and
χ is a bond and is absent or present,
wherein when α is absent, β is present, χ is absent, X is NH and R1 is absent, and
wherein when α is present, β is absent, χ is present, X is N and R1 is present,
or a pharmaceutically acceptable salt or ester thereof.