US 11,858,889 B2
Compound for modulating DDAH and ADMA levels, as well as methods of using thereof to treat disease
Jaipal Singh, Carmel, IN (US); and Kerry Fowler, Seattle, WA (US)
Assigned to THE TRUSTEES OF INDIANA UNIVERSITY, Bloomington, IN (US)
Filed by THE TRUSTEES OF INDIANA UNIVERSITY, Bloomington, IN (US)
Filed on Dec. 30, 2021, as Appl. No. 17/565,981.
Application 17/565,981 is a continuation of application No. 17/040,832, granted, now 11,267,780, previously published as PCT/US2019/030020, filed on Apr. 30, 2019.
Claims priority of provisional application 62/664,580, filed on Apr. 30, 2018.
Prior Publication US 2022/0144795 A1, May 12, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 333/24 (2006.01); C07D 263/32 (2006.01); C07D 213/55 (2006.01); C07D 277/30 (2006.01); C07C 63/49 (2006.01); C07C 65/17 (2006.01); C07D 295/088 (2006.01); C07C 65/19 (2006.01); C07C 49/513 (2006.01); C07C 63/64 (2006.01); C07C 65/10 (2006.01); C07C 65/24 (2006.01); C07C 65/40 (2006.01); C07C 211/55 (2006.01); C07C 215/74 (2006.01); C07C 233/65 (2006.01); C07C 233/81 (2006.01); C07C 317/32 (2006.01); C07C 323/62 (2006.01); C07D 209/18 (2006.01); C07D 257/04 (2006.01); C07D 295/16 (2006.01)
CPC C07C 65/19 (2013.01) [C07C 49/513 (2013.01); C07C 63/49 (2013.01); C07C 63/64 (2013.01); C07C 65/10 (2013.01); C07C 65/17 (2013.01); C07C 65/24 (2013.01); C07C 65/40 (2013.01); C07C 211/55 (2013.01); C07C 215/74 (2013.01); C07C 233/65 (2013.01); C07C 233/81 (2013.01); C07C 317/32 (2013.01); C07C 323/62 (2013.01); C07D 209/18 (2013.01); C07D 213/55 (2013.01); C07D 257/04 (2013.01); C07D 263/32 (2013.01); C07D 277/30 (2013.01); C07D 295/088 (2013.01); C07D 295/16 (2013.01); C07D 333/24 (2013.01); C07C 2601/16 (2017.05); C07C 2602/08 (2017.05)] 4 Claims
 
1. A compound defined by the formula:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt, wherein
i) R8, R9, R10, R11, R5 and R4 are hydrogen and R6 is methyl; or
ii) R8, R9, R10, R11, R6, and R5 are hydrogen and R4 is methyl; or
iii) R8, R9, R10, R11, R6, and R5 are hydrogen and R4 is chloro or floro; or
iv) R8, R9, R10, R11, and R6 are hydrogen, R5 is methyl and R4 is methoxy; or
v) R8, R9, R10, R11, and R5 are hydrogen, R6 is methyl and R4 is hydroxy; or
vi) R8, R9, R10, R11, R6, and R5 are hydrogen and R4 is 2-(morpholin-4-yl)ethoxy; or
vii) R8, R9, R10, R11, R6, and R4 are hydrogen and R5 is 2-(morpholin-4-yl)ethoxy; or
viii) R8, R9, R10, R11, R5, and R4 are hydrogen and R6 is 2-(morpholin-4-yl)ethoxy.