US 12,264,132 B2
3-phosphoglycerate dehydrogenase inhibitors and uses thereof
Nello Mainolfi, Belmont, MA (US)
Assigned to Raze Therapeutics, Inc., Cambridge, MA (US)
Filed by Raze Therapeutics, Inc., Cambridge, MA (US)
Filed on Nov. 22, 2022, as Appl. No. 17/992,284.
Application 17/221,514 is a division of application No. 16/082,665, granted, now 11,014,882, issued on May 25, 2021, previously published as PCT/US2017/021436, filed on Mar. 8, 2017.
Application 17/992,284 is a continuation of application No. 17/221,514, filed on Apr. 2, 2021, granted, now 11,535,593.
Claims priority of provisional application 62/305,940, filed on Mar. 9, 2016.
Prior Publication US 2023/0348386 A1, Nov. 2, 2023
Int. Cl. C07D 209/42 (2006.01); A61P 35/00 (2006.01); C07D 405/12 (2006.01); C07D 413/12 (2006.01)
CPC C07D 209/42 (2013.01) [A61P 35/00 (2018.01); C07D 405/12 (2013.01); C07D 413/12 (2013.01)] 16 Claims
 
1. A compound of formula I:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
R1 is hydrogen or C1-4 alkyl;
each of R2 and R3 is independently halogen, —OR, —CN, C1-6 aliphatic optionally substituted with 1, 2, or 3 halogens, or -L-R′; or R2 and R3 are optionally taken together with the carbon atoms to which they are attached and any intervening atoms to form a 5-8 membered partially unsaturated ring having 0-2 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
R4 is hydrogen, halogen, —OR5, —CN, C1-6 aliphatic optionally substituted with 1, 2, or 3 halogens, or -L-R′;
each R is independently hydrogen or an optionally substituted group selected from C1-6 aliphatic, a 3-8 membered saturated or partially unsaturated monocyclic carbocyclic ring, phenyl, an 8-10 membered bicyclic aromatic carbocyclic ring, a 4-8 membered saturated or partially unsaturated monocyclic heterocyclic ring having 1-2 heteroatoms independently selected from nitrogen, oxygen, or sulfur, a 5-6 membered monocyclic heteroaromatic ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or an 8-10 membered bicyclic heteroaromatic ring having 1-5 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
R5 is hydrogen, —(CH2)n-phenyl, or C1-6 alkyl optionally substituted with 1, 2, or 3 halogens;
each L is independently a C1-6 bivalent straight or branched hydrocarbon chain wherein 1-4 methylene units of the chain are independently and optionally replaced with —O—, —C(O)—, —C(O)O—, —OC(O)—, —OC(O)N(R)—, —(R)NC(O)O—, —C(O)N(R)—, —(R)NC(O)—, —N(R)—, —N(R)C(O)N(R)—, —S—, —SO—, or —SO2—;
each R′ is independently hydrogen, C1-6 aliphatic, or an optionally substituted 4-8 membered saturated or partially unsaturated monocyclic heterocyclic ring having 1-2 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
R6 is hydrogen or C1-4 alkyl;
R7 is a bivalent 3-7 membered heterocyclic ring;
L′ of —CONH-L1- is

OG Complex Work Unit Chemistry
L1 of -L1R7 is a covalent bond;
n is independently 0, 1, 2, 3, 4, or 5.