US 12,478,615 B2
Prolyl hydroxylase inhibitors and methods of use
Richard Masaru Kawamoto, Divide, CO (US); Shengde Wu, West Chester, OH (US); Artem G. Evdokimov, Foristell, MO (US); Kenneth D. Greis, Fort Thomas, KY (US); Angelique Sun Boyer, West Chester, OH (US); and Namal C. Warshakoon, Cary, NC (US)
Assigned to Akebia Therapeutics, Inc., Cambridge, MA (US)
Filed by Akebia Therapeutics, Inc., Cambridge, MA (US)
Filed on Dec. 12, 2023, as Appl. No. 18/537,481.
Application 14/062,011 is a division of application No. 13/681,876, filed on Nov. 20, 2012, granted, now 8,598,210, issued on Dec. 3, 2013.
Application 18/537,481 is a continuation of application No. 17/815,391, filed on Jul. 27, 2022, granted, now 11,883,386.
Application 17/815,391 is a continuation of application No. 16/908,092, filed on Jun. 22, 2020, granted, now 11,426,393, issued on Aug. 30, 2022.
Application 16/908,092 is a continuation of application No. 16/119,146, filed on Aug. 31, 2018, granted, now 10,729,681, issued on Aug. 4, 2020.
Application 16/119,146 is a continuation of application No. 15/420,617, filed on Jan. 31, 2017, abandoned.
Application 15/420,617 is a continuation of application No. 14/854,080, filed on Sep. 15, 2015, granted, now 9,598,370, issued on Mar. 21, 2017.
Application 14/854,080 is a continuation of application No. 14/568,200, filed on Dec. 12, 2014, abandoned.
Application 14/568,200 is a continuation of application No. 14/062,011, filed on Oct. 24, 2013, granted, now 8,940,773, issued on Jan. 27, 2015.
Application 13/681,876 is a continuation of application No. 12/860,073, filed on Aug. 20, 2010, granted, now 8,343,952, issued on Jan. 1, 2013.
Application 12/860,073 is a continuation of application No. 11/821,936, filed on Jun. 26, 2007, granted, now 7,811,595, issued on Oct. 12, 2010.
Claims priority of provisional application 60/816,522, filed on Jun. 26, 2006.
Prior Publication US 2024/0358691 A1, Oct. 31, 2024
Int. Cl. C07D 213/81 (2006.01); A61K 31/4418 (2006.01); A61K 31/4433 (2006.01); C07C 235/60 (2006.01); C07C 237/42 (2006.01); C07C 255/57 (2006.01); C07D 213/65 (2006.01); C07D 295/192 (2006.01); C07D 401/04 (2006.01); C07D 401/10 (2006.01); C07D 405/04 (2006.01); C07D 405/10 (2006.01); C07D 417/04 (2006.01)
CPC A61K 31/4418 (2013.01) [A61K 31/4433 (2013.01); C07C 235/60 (2013.01); C07C 237/42 (2013.01); C07C 255/57 (2013.01); C07D 213/65 (2013.01); C07D 213/81 (2013.01); C07D 295/192 (2013.01); C07D 401/04 (2013.01); C07D 401/10 (2013.01); C07D 405/04 (2013.01); C07D 405/10 (2013.01); C07D 417/04 (2013.01); Y02A 50/30 (2018.01)] 8 Claims
 
1. A process for preparing a compound having the formula:

OG Complex Work Unit Chemistry
comprising:
(a) reacting a 4-iodo-picolinic acid:

OG Complex Work Unit Chemistry
with a glycine methyl ester hydrochloride:

OG Complex Work Unit Chemistry
in the presence of coupling agents to form [(4-iodo-pyridine-2-carbonyl)-amino]-acetic acid methyl ester:

OG Complex Work Unit Chemistry
 and
(b) reacting the [(4-iodo-pyridine-2-carbonyl)-amino]-acetic acid methyl ester obtained from step (a) with a 4-methylphenyl boronic acid:

OG Complex Work Unit Chemistry
in the presence of a catalyst to form [(4-(4-methylphenyl)pyridine-2-carbonyl)amino]-acetic acid methyl ester:

OG Complex Work Unit Chemistry