NZ758641B2 - Pyridin-2(1h)-one quinolinone derivatives as mutant-isocitrate dehydrogenase inhibitors - Google Patents

Pyridin-2(1h)-one quinolinone derivatives as mutant-isocitrate dehydrogenase inhibitors

Info

Publication number
NZ758641B2
NZ758641B2 NZ758641A NZ75864115A NZ758641B2 NZ 758641 B2 NZ758641 B2 NZ 758641B2 NZ 758641 A NZ758641 A NZ 758641A NZ 75864115 A NZ75864115 A NZ 75864115A NZ 758641 B2 NZ758641 B2 NZ 758641B2
Authority
NZ
New Zealand
Prior art keywords
compound
amino
chloro
oxo
methyloxo
Prior art date
Application number
NZ758641A
Other versions
NZ758641A (en
Inventor
Susan Ashwell
Ann Marie Campbell
Justin Andrew Caravella
R Bruce Diebold
Anna Ericsson
Gary Gustafson
Jr David R Lancia
Jian Lin
Wei Lu
Zhongguo Wang
Original Assignee
Forma Therapeutics Inc
Filing date
Publication date
Application filed by Forma Therapeutics Inc filed Critical Forma Therapeutics Inc
Priority claimed from NZ73037315A external-priority patent/NZ730373A/en
Publication of NZ758641A publication Critical patent/NZ758641A/en
Publication of NZ758641B2 publication Critical patent/NZ758641B2/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/472—Non-condensed isoquinolines, e.g. papaverine
    • A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Abstract

The invention relates to inhibitors of mutant isocitrate dehydrogenase (mt-IDH) proteins with neomorphic activity useful in the treatment of cell-proliferation disorders and cancers, having the Formula (I), where A, U, W1, W2, W3, R1-R6, and R9 are described herein.

Claims (12)

CLAIMS :
1. A compound selected from: 6-chloro{[(1,6-dimethyloxo-1,2-dihydropyridinyl)amino]methyl}-1,2-dihydroquinolin- 2-one; 6-chloro({[2-oxo(trifluoromethyl)-1,2-dihydropyridinyl]amino}methyl)-1,2- dihydroquinolinone; 6-chloro({[1-methyloxo(trifluoromethyl)-1,2-dihydropyridinyl]amino}methyl)-1,2- dihydroquinolinone; methyl 5-{[(6-chlorooxo-1,2-dihydroquinolinyl)methyl]amino}oxo-1,6- dihydropyridinecarboxylate; 5-{[(1S)[6-chloro(2-hydroxypropanyl)oxo-1,2-dihydroquinolinyl]ethyl]amino} methyloxo-1,6-dihydropyridinecarbonitrile; 5-{[(1S)(6-chlorocyclopropyloxo-1,2-dihydro-1,8-naphthyridinyl)ethyl]amino} methyloxo-1,6-dihydropyridinecarbonitrile; 5-{[(1S){6-chloro[(2-hydroxymethylpropyl)amino]oxo-1,2-dihydroquinolin yl}ethyl]amino}methyloxo-1,6-dihydropyridinecarbonitrile; and 5-{[(1S)[6-chloro(3,3-difluoroazetidinyl)oxo-1,2-dihydroquinolinyl]ethyl]amino}- 1-methyloxo-1,6-dihydropyridinecarbonitrile.
2. The compound of claim 1, wherein the compound is 6-chloro{[(1,6-dimethyloxo- 1,2-dihydropyridinyl)amino]methyl}-1,2-dihydroquinolinone.
3. The compound of claim 1, wherein the compound is 6-chloro({[2-oxo (trifluoromethyl)-1,2-dihydropyridinyl]amino}methyl)-1,2-dihydroquinolinone.
4. The compound of claim 1, wherein the compound is 6-chloro({[1-methyloxo (trifluoromethyl)-1,2-dihydropyridinyl]amino}methyl)-1,2-dihydroquinolinone.
5. The compound of claim 1, wherein the compound is methyl 5-{[(6-chlorooxo-1,2- dihydroquinolinyl)methyl]amino}oxo-1,6-dihydropyridinecarboxylate.
6. The compound of claim 1, wherein the compound is 5-{[(1S)[6-chloro(2- hydroxypropanyl)oxo-1,2-dihydroquinolinyl]ethyl]amino}methyloxo-1,6- dihydropyridinecarbonitrile.
7. The compound of claim 1, wherein the compound is 5-{[(1S)(6-chlorocyclopropyl- 2-oxo-1,2-dihydro-1,8-naphthyridinyl)ethyl]amino}methyloxo-1,6-dihydropyridine carbonitrile.
8. The compound of claim 1, wherein the compound is 5-{[(1S){6-chloro[(2-hydroxy- 2-methylpropyl)amino]oxo-1,2-dihydroquinolinyl}ethyl]amino}methyloxo-1,6- dihydropyridinecarbonitrile.
9. The compound of claim 1, wherein the compound is 5-{[(1S)[6-chloro(3,3- difluoroazetidinyl)oxo-1,2-dihydroquinolinyl]ethyl]amino}methyloxo-1,6- dihydropyridinecarbonitrile.
10. A pharmaceutical composition comprising a compound of the compound of any one of claims 1-9 and a pharmaceutically acceptable carrier.
11. A compound according to any one of claims 1 to 9 substantially as herein described with reference to any example thereof.
12. A pharmaceutical composition according to claim 10 substantially as herein described with reference to any example thereof.
NZ758641A 2015-09-18 Pyridin-2(1h)-one quinolinone derivatives as mutant-isocitrate dehydrogenase inhibitors NZ758641B2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201462053006P 2014-09-19 2014-09-19
US201562128089P 2015-03-04 2015-03-04
US201562150812P 2015-04-21 2015-04-21
NZ73037315A NZ730373A (en) 2014-09-19 2015-09-18 Pyridin-2(1h)-one quinolinone derivatives as mutant-isocitrate dehydrogenase inhibitors

Publications (2)

Publication Number Publication Date
NZ758641A NZ758641A (en) 2023-12-22
NZ758641B2 true NZ758641B2 (en) 2024-03-26

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