US 12,448,367 B2
Phthalazine derivatives as pyruvate kinase modulators
David Cousin, Nottingham (GB); and Oscar Barba, Oxford (GB)
Assigned to Sitryx Therapeutics Limited, Oxford (GB)
Filed by Sitryx Therapeutics Limited, Oxford (GB)
Filed on Feb. 20, 2025, as Appl. No. 19/058,521.
Application 19/058,521 is a continuation of application No. PCT/GB2023/052875, filed on Nov. 3, 2023.
Claims priority of application No. PCT/GB2022/052781 (WO), filed on Nov. 4, 2022.
Prior Publication US 2025/0230143 A1, Jul. 17, 2025
Int. Cl. C07D 401/14 (2006.01); A61K 31/502 (2006.01); C07D 403/14 (2006.01); C07D 491/048 (2006.01); C07D 498/04 (2006.01)
CPC C07D 401/14 (2013.01) [A61K 31/502 (2013.01); C07D 403/14 (2013.01); C07D 491/048 (2013.01); C07D 498/04 (2013.01)] 26 Claims
 
1. A compound selected from the group consisting of:
(a) 6-((1H-pyrazol-4-yl)sulfonyl)-2-((5-methoxypyridin-2-yl)methyl)phthalazin-1 (2H)-one

OG Complex Work Unit Chemistry
(b) 2-((1H-pyrazol-3-yl)methyl)-6-((1-(difluoromethyl)-1H-pyrazol-4-yl)sulfonyl)phthalazin-1 (2H)-one

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(c) 2-((2,3-dihydrofuro[3,2-b]pyridin-5-yl)methyl)-6-((1-(2-hydroxyethyl)-1H-pyrazol-4-yl)sulfonyl)phthalazin-1 (2H)-one

OG Complex Work Unit Chemistry
(d) 6-((1H-pyrazol-4-yl)sulfonyl)-2-((2,3-dihydropyrazolo[5,1-b]oxazol-6-yl)methyl)phthalazin-1 (2H)-one

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(e) 2-((2,3-dihydropyrazolo[5,1-b]oxazol-6-yl)methyl)-6-((1-methyl-1H-pyrazol-4-yl)sulfonyl)phthalazin-1 (2H)-one

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or
(f) 6-((1H-pyrazol-3-yl)sulfonyl)-2-((4-chloro-5-methyl-1H-pyrazol-3-yl)methyl)phthalazin-1(2H)-one

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and a pharmaceutically acceptable salt and/or solvate thereof.