US 11,746,091 B2
Cannabinoid receptor modulators
Robert M. Jones, San Diego, CA (US); Sangdon Han, San Diego, CA (US); Lars Thoresen, San Diego, CA (US); Jae-Kyu Jung, San Diego, CA (US); Sonja Strah-Pleynet, Newton, MA (US); Xiuwen Zhu, San Diego, CA (US); Yifeng Xiong, San Diego, CA (US); and Dawei Yue, San Diego, CA (US)
Assigned to Arena Pharmaceuticals, Inc., San Diego, CA (US)
Filed by Arena Pharmaceuticals, Inc., San Diego, CA (US)
Filed on Sep. 18, 2020, as Appl. No. 17/24,752.
Application 15/912,700 is a division of application No. 13/616,918, filed on Sep. 14, 2012, granted, now 9,944,606, issued on Apr. 17, 2018.
Application 13/616,918 is a division of application No. 13/392,074, granted, now 8,778,950, issued on Jul. 15, 2014, previously published as PCT/US2010/002360, filed on Aug. 27, 2010.
Application 17/024,752 is a continuation of application No. 15/912,700, filed on Mar. 6, 2018, abandoned.
Claims priority of provisional application 61/400,146, filed on Jul. 22, 2010.
Claims priority of provisional application 61/396,588, filed on May 28, 2010.
Claims priority of provisional application 61/275,506, filed on Aug. 28, 2009.
Prior Publication US 2021/0188781 A1, Jun. 24, 2021
Int. Cl. C07D 231/54 (2006.01); C07D 401/04 (2006.01); C07D 403/04 (2006.01); C07F 9/6558 (2006.01); C07D 401/12 (2006.01); C07D 403/12 (2006.01); C07D 413/12 (2006.01); C07D 401/14 (2006.01); C07D 405/14 (2006.01); C07D 413/14 (2006.01)
CPC C07D 231/54 (2013.01) [C07D 401/04 (2013.01); C07D 401/12 (2013.01); C07D 401/14 (2013.01); C07D 403/04 (2013.01); C07D 403/12 (2013.01); C07D 405/14 (2013.01); C07D 413/12 (2013.01); C07D 413/14 (2013.01); C07F 9/65583 (2013.01)] 12 Claims
 
1. A compound selected from the group consisting of:
(1aS,5aS)-2-(4-Oxy-pyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid (1-fluoromethyl-cyclobutyl)-amide (Compound 925);
(1aS,5 aS)-2-(4-Oxy-pyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid ((S)-1-fluoromethyl-2-methyl-propyl)-amide (Compound 915);
(1aS,5aS)-2-(4-Oxy-pyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid ((S)-1-fluoromethyl-2,2-dimethyl-propyl)-amide (Compound 916);
(1aS,5aS)-2-(4-Oxy-pyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid ((S)-3,3,3-trifluoro-1-hydroxymethyl-propyl)-amide (Compound 914);
(1aS,5aS)-2-(4-Oxy-pyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid [pyridin-2-yl-(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-amide (Compound 743); and
pharmaceutically acceptable salts thereof.