US 12,071,413 B2
Azole derivatives as apelin receptor agonist
Takuya Ikeda, Tokyo (JP); Yoshiyuki Kobayashi, Tokyo (JP); Naoki Miyoshi, Tokyo (JP); Osamu Suzuki, Tokyo (JP); Takahiro Nagayama, Tokyo (JP); Takashi Tsuji, Tokyo (JP); Layton H. Smith, Orlando, FL (US); and Anthony B. Pinkerton, Rancho Santa Fe, CA (US)
Assigned to SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE, La Jolla, CA (US)
Filed by Sanford Burnham Prebys Medical Discovery Institute, La Jolla, CA (US)
Filed on Oct. 20, 2021, as Appl. No. 17/506,497.
Application 16/853,604 is a division of application No. 15/778,168, granted, now 10,626,096, issued on Apr. 21, 2020, previously published as PCT/US2016/063152, filed on Nov. 21, 2016.
Application 17/506,497 is a continuation of application No. 16/853,604, filed on Apr. 20, 2020, granted, now 11,155,525, issued on Oct. 26, 2021.
Claims priority of provisional application 62/259,336, filed on Nov. 24, 2015.
Prior Publication US 2022/0144784 A1, May 12, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 249/12 (2006.01); A61P 3/10 (2006.01); A61P 9/04 (2006.01); A61P 9/10 (2006.01); A61P 9/12 (2006.01); A61P 13/12 (2006.01); C07D 401/04 (2006.01); C07D 403/06 (2006.01); C07D 403/12 (2006.01); C07D 405/04 (2006.01); C07D 405/14 (2006.01); C07D 409/04 (2006.01); C07D 409/14 (2006.01); C07D 413/14 (2006.01); C07D 417/14 (2006.01); C07D 487/04 (2006.01); G16B 25/00 (2019.01); G16C 20/50 (2019.01); G16C 99/00 (2019.01)
CPC C07D 249/12 (2013.01) [A61P 3/10 (2018.01); A61P 9/04 (2018.01); A61P 9/10 (2018.01); A61P 9/12 (2018.01); A61P 13/12 (2018.01); C07D 401/04 (2013.01); C07D 403/06 (2013.01); C07D 403/12 (2013.01); C07D 405/04 (2013.01); C07D 405/14 (2013.01); C07D 409/04 (2013.01); C07D 409/14 (2013.01); C07D 413/14 (2013.01); C07D 417/14 (2013.01); C07D 487/04 (2013.01); G16B 25/00 (2019.02); G16C 20/50 (2019.02); G16C 99/00 (2019.02)] 20 Claims
 
1. A pharmaceutical composition comprising a compound represented by formula (I), or a pharmacologically acceptable salt thereof:

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wherein
X1 is —N═ or —CH═,
X2 is —CH═ or —N═,
R1 and R2 are each independently a C1 to C6 alkyl group, a C1 to C6 alkoxy group, or a halogeno group, wherein the C1 to C6 alkyl group and the C1 to C6 alkoxy group are each optionally substituted by 1 to 3 fluoro groups;
R3 is a furyl group, a thienyl group, a pyridyl group, a phenyl group, a n-butyl group, or a cyclopentyl group (the furyl group, the thienyl group, the pyridyl group, and the phenyl group are each optionally substituted by 1 or 2 identical or different groups selected from a methyl group and a halogeno group); and
R4 is

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an active ingredient.