US 12,331,041 B2
GLP-1 receptor agonists and uses thereof
Gary Erik Aspnes, Biberach an der Riss (DE); Scott W. Bagley, Voluntown, CT (US); Edward L. Conn, Griswold, CT (US); John M. Curto, Mystic, CT (US); David J. Edmonds, Basel (CH); Mark E. Flanagan, Gales Ferry, CT (US); Kentaro Futatsugi, Sharon, MA (US); David A. Griffith, Sudbury, MA (US); Kim Huard, Berkeley, CA (US); Chris Limberakis, Pawcatuck, CT (US); Alan M. Mathiowetz, Waltham, MA (US); David W. Piotrowski, Waterford, CT (US); and Roger B. Ruggeri, Waterford, CT (US)
Assigned to Pfizer Inc., New York, NY (US)
Filed by Pfizer Inc., New York, NY (US)
Filed on Nov. 20, 2023, as Appl. No. 18/513,752.
Application 18/513,752 is a continuation of application No. 17/251,929, granted, now 11,858,916, previously published as PCT/IB2019/054961, filed on Jun. 13, 2019.
Claims priority of provisional application 62/685,656, filed on Jun. 15, 2018.
Prior Publication US 2024/0132483 A1, Apr. 25, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 405/14 (2006.01); C07D 401/14 (2006.01); C07D 403/14 (2006.01); C07D 413/14 (2006.01); C07D 471/04 (2006.01)
CPC C07D 405/14 (2013.01) [C07D 401/14 (2013.01); C07D 403/14 (2013.01); C07D 413/14 (2013.01); C07D 471/04 (2013.01)] 16 Claims
 
1. A compound of Formula I:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein A is A1 or A2,

OG Complex Work Unit Chemistry
and wherein
each R1 is independently halogen, —CN, —C1-3alkyl, or —OC1-3alkyl, wherein the alkyl of C1-3alkyl and OC1-3alkyl is substituted with 0 to 3 F atoms;
m is 0, 1, 2, or 3;
X-L is N—CH2, CHCH2, or cyclopropyl;
Y is CH or N;
ZA1 is CH or CR2;
ZA2 is CH, CR2, or N;
ZA3 is CH, CR2, or N, provided that ZA2 and ZA3 are not simultaneously N; and further provided that one of ZA2 and ZA3 is N when X-L is N—CH2;
each R2 is F;
each R3 is independently F, —OH, —CN, —C1-3alkyl, —OC1-3alkyl, or —C3-4cycloalkyl, or 2 R3s may together cyclize to form —C3-4spirocycloalkyl, wherein the alkyl of C1-3alkyl and OC1-3alkyl, cycloalkyl, or spirocycloalkyl may be substituted as valency allows with 0 to 3 F atoms and with 0 to 1-OH;
q is 0, 1, or 2;
R4 is-C1-3alkyl, —C0-3alkylene-C3-6cycloalkyl, —C0-3alkylene-R5, or —C1-3alkylene-R6, wherein said alkyl may be substituted as valency allows with 0 to 3 substituents independently selected from 0 to 3 F atoms and 0 to 1 substituent selected from —C0-1alkylene-CN, —C0-1alkylene-ORO, and —N(RN)2, and wherein said alkylene of —C0-3alkylene-C3-6cycloalkyl, —C0-3alkylene-R5, or —C1-3alkylene-R6 and said cycloalkyl may be independently substituted as valency allows with 0 to 2 substituents independently selected from 0 to 2 F atoms and 0 to 1 substituent selected from —C0-1alkylene-CN, —C0-1alkylene-ORO, and —N(RN)2;
R5 is a 4- to 6-membered heterocycloalkyl, wherein said heterocycloalkyl may be substituted with 0 to 2 substituents as valency allows independently selected from:
0 to 1 oxo (═O),
0 to 1 —CN,
0 to 2 F atoms, and
0 to 2 substituents independently selected from —C1-3alkyl and —OC1-3alkyl, wherein the alkyl of C1-3alkyl and OC1-3alkyl may be substituted with 0 to 3 substituents as valency allows independently selected from:
0 to 3 F atoms,
0 to 1 —CN, and
0 to 1 —ORO;
R6 is a 5- to 6-membered heteroaryl, wherein said heteroaryl may be substituted with 0 to 2 substituents as valency allows independently selected from:
0 to 2 halogens,
0 to 1 substituent selected from —ORO and —N(RN)2, and
0 to 2 -C1-3alkyl, wherein the alkyl may be substituted with 0 to 3 substituents as valency allows independently selected from:
0 to 3 F atoms, and
0 to 1 —ORO;
each RO is independently H, or —C1-3alkyl, wherein C1-3alkyl may be substituted with 0 to 3 F atoms;
each RN is independently H, or —C1-3alkyl;
Z1, Z2, and Z3 are each —CRZ, or
one of Z1, Z2, and Z3 is N and the other two are —CRZ; and
each RZ is independently H, F, Cl, or —CH3.