HRP20230657T1 - Spojevi i pripravci za liječenje hematoloških poremećaja - Google Patents
Spojevi i pripravci za liječenje hematoloških poremećaja Download PDFInfo
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- HRP20230657T1 HRP20230657T1 HRP20230657TT HRP20230657T HRP20230657T1 HR P20230657 T1 HRP20230657 T1 HR P20230657T1 HR P20230657T T HRP20230657T T HR P20230657TT HR P20230657 T HRP20230657 T HR P20230657T HR P20230657 T1 HRP20230657 T1 HR P20230657T1
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- HR
- Croatia
- Prior art keywords
- pyridin
- carboxamide
- methylpyridin
- oxazole
- piperidin
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims 30
- 208000014951 hematologic disease Diseases 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 19
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000001475 halogen functional group Chemical group 0.000 claims 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- 229910003827 NRaRb Inorganic materials 0.000 claims 13
- 125000001424 substituent group Chemical group 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 150000002431 hydrogen Chemical group 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims 6
- 230000035772 mutation Effects 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- -1 oxazolyl 1 ,4-dioxanyl Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 2
- FBMVUIPXGQVFOB-UHFFFAOYSA-N N-[5-(4-hydroxypiperidin-1-yl)-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-5-(2-methylpyridin-4-yl)furan-2-carboxamide Chemical compound OC1CCN(CC1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2OC(=CC2)C2=CC(=NC=C2)C FBMVUIPXGQVFOB-UHFFFAOYSA-N 0.000 claims 2
- 102100020718 Receptor-type tyrosine-protein kinase FLT3 Human genes 0.000 claims 2
- 108010003374 fms-Like Tyrosine Kinase 3 Proteins 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- VAELWSLNTRVXQS-UHFFFAOYSA-N 1,3-oxazole-4-carboxamide Chemical compound NC(=O)C1=COC=N1 VAELWSLNTRVXQS-UHFFFAOYSA-N 0.000 claims 1
- RILQOQOJAWSOEM-UHFFFAOYSA-N 2-(2-acetamidopyridin-4-yl)-N-[5-(3-hydroxypiperidin-1-yl)-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-1,3-oxazole-4-carboxamide Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CC(CCC1)O)N=C(S2)N2CCOCC2 RILQOQOJAWSOEM-UHFFFAOYSA-N 0.000 claims 1
- DYHJSFZYZJZUDK-UHFFFAOYSA-N 2-(2-acetamidopyridin-4-yl)-N-[5-(4-hydroxypiperidin-1-yl)-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-1,3-oxazole-4-carboxamide Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1OC=C(N=1)C(=O)NC=1C=C2C(=NC=1N1CCC(CC1)O)N=C(S2)N1CCOCC1 DYHJSFZYZJZUDK-UHFFFAOYSA-N 0.000 claims 1
- ZARPDGXZRSSCQL-UHFFFAOYSA-N 2-(2-aminopyridin-4-yl)-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide hydrochloride Chemical compound Cl.NC1=NC=CC(=C1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(S2)N2CCOCC2 ZARPDGXZRSSCQL-UHFFFAOYSA-N 0.000 claims 1
- INYCIZZBVRYRBP-UHFFFAOYSA-N 2-(2-aminopyridin-4-yl)-N-[5-(3-hydroxypiperidin-1-yl)-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-1,3-oxazole-4-carboxamide hydrochloride Chemical compound Cl.NC1=NC=CC(=C1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CC(CCC1)O)N=C(S2)N2CCOCC2 INYCIZZBVRYRBP-UHFFFAOYSA-N 0.000 claims 1
- KEODCHRHTWJGKZ-UHFFFAOYSA-N 2-(2-aminopyridin-4-yl)-N-[5-(4-fluoropiperidin-1-yl)-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-1,3-oxazole-4-carboxamide hydrochloride Chemical compound Cl.Nc1cc(ccn1)-c1nc(co1)C(=O)Nc1cc2sc(nc2nc1N1CCC(F)CC1)N1CCOCC1 KEODCHRHTWJGKZ-UHFFFAOYSA-N 0.000 claims 1
- GKUUFRSTVBIKIO-UHFFFAOYSA-N 2-(2-aminopyridin-4-yl)-N-[5-(4-hydroxypiperidin-1-yl)-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-1,3-oxazole-4-carboxamide hydrochloride Chemical compound Cl.NC1=NC=CC(=C1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCC(CC1)O)N=C(S2)N2CCOCC2 GKUUFRSTVBIKIO-UHFFFAOYSA-N 0.000 claims 1
- OMHKBKTUCLMDHO-UHFFFAOYSA-N 2-(2-chloropyridin-4-yl)-N-[2,5-di(piperidin-1-yl)-[1,3]oxazolo[4,5-b]pyridin-6-yl]-1,3-oxazole-4-carboxamide Chemical compound ClC1=NC=CC(=C1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(O2)N2CCCCC2 OMHKBKTUCLMDHO-UHFFFAOYSA-N 0.000 claims 1
- AHNTYFBQZDKVJT-UHFFFAOYSA-N 2-(2-methoxypyridin-4-yl)-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound COC1=NC=CC(=C1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(O2)N2CCOCC2 AHNTYFBQZDKVJT-UHFFFAOYSA-N 0.000 claims 1
- MBKMUOMGBRBNHT-UHFFFAOYSA-N 2-(2-methoxypyridin-4-yl)-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound COC1=NC=CC(=C1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(S2)N2CCOCC2 MBKMUOMGBRBNHT-UHFFFAOYSA-N 0.000 claims 1
- JQIRTTNZYNJXLA-UHFFFAOYSA-N 2-(2-methylpyridin-3-yl)-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound CC1=NC=CC=C1C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(O2)N2CCOCC2 JQIRTTNZYNJXLA-UHFFFAOYSA-N 0.000 claims 1
- HNQWLUFTCQHTSD-UHFFFAOYSA-N 2-(2-methylpyridin-3-yl)-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound CC1=NC=CC=C1C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(S2)N2CCOCC2 HNQWLUFTCQHTSD-UHFFFAOYSA-N 0.000 claims 1
- QRCFVLZQXUUWQU-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound CC1=NC=CC(=C1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(O2)N2CCOCC2 QRCFVLZQXUUWQU-UHFFFAOYSA-N 0.000 claims 1
- NHBOYGLZBVDETG-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound CC1=NC=CC(=C1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(S2)N2CCOCC2 NHBOYGLZBVDETG-UHFFFAOYSA-N 0.000 claims 1
- HTGMKKXWSFLGCF-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-N-(2-morpholin-4-yl-5-pyrrolidin-1-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound CC1=NC=CC(=C1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCC1)N=C(O2)N2CCOCC2 HTGMKKXWSFLGCF-UHFFFAOYSA-N 0.000 claims 1
- IRCQDDKBAHPDHZ-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-N-(2-morpholin-4-yl-5-pyrrolidin-1-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound CC1=NC=CC(=C1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCC1)N=C(S2)N2CCOCC2 IRCQDDKBAHPDHZ-UHFFFAOYSA-N 0.000 claims 1
- VUIMAGJRVUTCRD-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-N-(2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound CC1=NC=CC(=C1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1)N=C(S2)N2CCOCC2 VUIMAGJRVUTCRD-UHFFFAOYSA-N 0.000 claims 1
- HGVDQGFZTPIRKZ-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-N-(2-piperidin-1-yl-5-pyrrolidin-1-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound CC1=NC=CC(=C1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCC1)N=C(O2)N2CCCCC2 HGVDQGFZTPIRKZ-UHFFFAOYSA-N 0.000 claims 1
- XYYVKPLUHNLZSN-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-N-(2-piperidin-1-yl-5-pyrrolidin-1-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound CC1=NC=CC(=C1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCC1)N=C(S2)N2CCCCC2 XYYVKPLUHNLZSN-UHFFFAOYSA-N 0.000 claims 1
- BUCFDTXFTKXLSJ-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-N-(5-piperidin-1-yl-2-pyrrolidin-1-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide hydrochloride Chemical compound Cl.CC1=NC=CC(=C1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(O2)N2CCCC2 BUCFDTXFTKXLSJ-UHFFFAOYSA-N 0.000 claims 1
- BKXPKYMCEMZNIE-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-N-[2-morpholin-4-yl-5-(1H-pyrazol-4-yl)-[1,3]thiazolo[4,5-b]pyridin-6-yl]-1,3-oxazole-4-carboxamide Chemical compound CC1=NC=CC(=C1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1C=1C=NNC1)N=C(S2)N2CCOCC2 BKXPKYMCEMZNIE-UHFFFAOYSA-N 0.000 claims 1
- DNDCUNFBWVSONT-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-N-[2-morpholin-4-yl-5-(2-oxo-1H-pyridin-4-yl)-[1,3]thiazolo[4,5-b]pyridin-6-yl]-1,3-oxazole-4-carboxamide hydrochloride Chemical compound Cl.OC1=NC=CC(=C1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C DNDCUNFBWVSONT-UHFFFAOYSA-N 0.000 claims 1
- FBWOURBOGWSANT-INIZCTEOSA-N 2-(2-methylpyridin-4-yl)-N-[2-morpholin-4-yl-5-[[(3S)-pyrrolidin-3-yl]amino]-[1,3]oxazolo[4,5-b]pyridin-6-yl]-1,3-oxazole-4-carboxamide Chemical compound CC1=NC=CC(=C1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N[C@@H]1CNCC1)N=C(O2)N2CCOCC2 FBWOURBOGWSANT-INIZCTEOSA-N 0.000 claims 1
- AXAVUYCRUKQRHG-UHFFFAOYSA-N 2-(3-methylpyridin-4-yl)-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound CC=1C=NC=CC1C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(O2)N2CCOCC2 AXAVUYCRUKQRHG-UHFFFAOYSA-N 0.000 claims 1
- MROOTSIVNDBMLK-UHFFFAOYSA-N 2-(3-methylpyridin-4-yl)-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound CC=1C=NC=CC1C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(S2)N2CCOCC2 MROOTSIVNDBMLK-UHFFFAOYSA-N 0.000 claims 1
- IORKCZNYSADFLD-UHFFFAOYSA-N 2-(6-methoxypyridin-3-yl)-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound COC1=CC=C(C=N1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(S2)N2CCOCC2 IORKCZNYSADFLD-UHFFFAOYSA-N 0.000 claims 1
- KQBXIXQWJDOSPK-UHFFFAOYSA-N 2-(6-methylpyridin-3-yl)-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound CC1=CC=C(C=N1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(O2)N2CCOCC2 KQBXIXQWJDOSPK-UHFFFAOYSA-N 0.000 claims 1
- IYBDTFIQINOUPK-UHFFFAOYSA-N 2-(6-methylpyridin-3-yl)-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound CC1=CC=C(C=N1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(S2)N2CCOCC2 IYBDTFIQINOUPK-UHFFFAOYSA-N 0.000 claims 1
- VYPNVBLQPKYSJB-HNNXBMFYSA-N 2-[(3S)-3-aminopyrrolidin-1-yl]-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound N[C@@H]1CN(CC1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(O2)N2CCOCC2 VYPNVBLQPKYSJB-HNNXBMFYSA-N 0.000 claims 1
- VHPUKAIUYBULHC-HNNXBMFYSA-N 2-[(3S)-3-aminopyrrolidin-1-yl]-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound N[C@@H]1CN(CC1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(S2)N2CCOCC2 VHPUKAIUYBULHC-HNNXBMFYSA-N 0.000 claims 1
- YGEBHHZIEJVDMJ-ZDUSSCGKSA-N 2-[(3S)-3-aminopyrrolidin-1-yl]-N-(5-cyclopropyl-2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound N[C@@H]1CN(CC1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1C1CC1)N=C(O2)N2CCOCC2 YGEBHHZIEJVDMJ-ZDUSSCGKSA-N 0.000 claims 1
- IDIAQKSXLFXBPK-ZDUSSCGKSA-N 2-[(3S)-3-aminopyrrolidin-1-yl]-N-(5-cyclopropyl-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound N[C@@H]1CN(CC1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1C1CC1)N=C(S2)N2CCOCC2 IDIAQKSXLFXBPK-ZDUSSCGKSA-N 0.000 claims 1
- ZUBOTURLHQKUOS-HNNXBMFYSA-N 2-[(3S)-3-hydroxypyrrolidin-1-yl]-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound O[C@@H]1CN(CC1)C=1OC=C(N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(O2)N2CCOCC2 ZUBOTURLHQKUOS-HNNXBMFYSA-N 0.000 claims 1
- QQGCHSAGAAAFHC-HNNXBMFYSA-N 2-[(3S)-3-hydroxypyrrolidin-1-yl]-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)-1,3-oxazole-4-carboxamide Chemical compound O[C@@H]1CN(CC1)C=1OC=C(N=1)C(=O)NC=1C=C2C(=NC=1N1CCCCC1)N=C(S2)N1CCOCC1 QQGCHSAGAAAFHC-HNNXBMFYSA-N 0.000 claims 1
- MPUNEURROABVFW-UHFFFAOYSA-N 2-[4-(aminomethyl)piperidin-1-yl]-5-fluoro-N-(2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)benzamide Chemical compound NCC1CCN(CC1)C1=C(C(=O)NC=2C=C3C(=NC2)N=C(S3)N3CCOCC3)C=C(C=C1)F MPUNEURROABVFW-UHFFFAOYSA-N 0.000 claims 1
- ONYIKKSYBMJKLP-UHFFFAOYSA-N 3-[4-(aminomethyl)piperidin-1-yl]-5-fluoro-N-(2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)benzamide Chemical compound NCC1CCN(CC1)C=1C=C(C(=O)NC=2C=C3C(=NC2)N=C(S3)N3CCOCC3)C=C(C1)F ONYIKKSYBMJKLP-UHFFFAOYSA-N 0.000 claims 1
- HTQFQERFALFEDK-UHFFFAOYSA-N 5-(2-aminopyridin-4-yl)-N-[5-(4-hydroxypiperidin-1-yl)-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]furan-3-carboxamide hydrochloride Chemical compound Cl.Nc1cc(ccn1)-c1cc(co1)C(=O)Nc1cc2sc(nc2nc1N1CCC(O)CC1)N1CCOCC1 HTQFQERFALFEDK-UHFFFAOYSA-N 0.000 claims 1
- BAOQRBHLMIBNFN-UHFFFAOYSA-N 5-(2-methylpyridin-4-yl)-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl)furan-2-carboxamide Chemical compound CC1=NC=CC(=C1)C1=CC=C(O1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(O2)N2CCOCC2 BAOQRBHLMIBNFN-UHFFFAOYSA-N 0.000 claims 1
- FRGAKYVHFUAKJR-UHFFFAOYSA-N 5-(2-methylpyridin-4-yl)-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)furan-2-carboxamide Chemical compound CC1=NC=CC(=C1)C1=CC=C(O1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(S2)N2CCOCC2 FRGAKYVHFUAKJR-UHFFFAOYSA-N 0.000 claims 1
- IWTQNUCXXJOVNM-UHFFFAOYSA-N 6-(1-methylpyrazol-4-yl)-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl)pyridine-2-carboxamide Chemical compound CN1N=CC(=C1)C1=CC=CC(=N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(O2)N2CCOCC2 IWTQNUCXXJOVNM-UHFFFAOYSA-N 0.000 claims 1
- NVQBQXUBXWICTQ-UHFFFAOYSA-N 6-(1-methylpyrazol-4-yl)-N-(2-morpholin-4-yl-5-piperidin-1-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)pyridine-2-carboxamide Chemical compound CN1N=CC(=C1)C1=CC=CC(=N1)C(=O)NC=1C=C2C(=NC1N1CCCCC1)N=C(S2)N2CCOCC2 NVQBQXUBXWICTQ-UHFFFAOYSA-N 0.000 claims 1
- RWIMETUXCNDSLE-UHFFFAOYSA-N 6-(6-aminopyridin-3-yl)-N-(2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl)pyridine-2-carboxamide Chemical compound NC1=CC=C(C=N1)C1=NC(=CC=C1)C(=O)NC=1C=C2C(=NC1)N=C(O2)N2CCOCC2 RWIMETUXCNDSLE-UHFFFAOYSA-N 0.000 claims 1
- HIDYWAGOMSFXRB-UHFFFAOYSA-N 6-(6-aminopyridin-3-yl)-N-(2-morpholin-4-yl-[1,3]oxazolo[5,4-b]pyridin-5-yl)pyridine-2-carboxamide Chemical compound NC1=CC=C(C=N1)C1=NC(=CC=C1)C(=O)NC1=CC=C2C(=N1)OC(=N2)N2CCOCC2 HIDYWAGOMSFXRB-UHFFFAOYSA-N 0.000 claims 1
- RAZCOWGWICRRJV-UHFFFAOYSA-N 6-(6-aminopyridin-3-yl)-N-(2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)pyridine-2-carboxamide Chemical compound NC1=CC=C(C=N1)C1=NC(=CC=C1)C(=O)NC=1C=C2C(=NC1)N=C(S2)N2CCOCC2 RAZCOWGWICRRJV-UHFFFAOYSA-N 0.000 claims 1
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- HGTIDIMJQHHRTR-HNNXBMFYSA-N N-(5-cyclopropyl-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl)-6-[1-[(2S)-2-hydroxypropyl]pyrazol-4-yl]pyridine-2-carboxamide Chemical compound C1(CC1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(C2=NC(=CC=C2)C=2C=NN(C2)C[C@H](C)O)=O HGTIDIMJQHHRTR-HNNXBMFYSA-N 0.000 claims 1
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- HXECBJUGQJREAN-UHFFFAOYSA-N N-[5-(3-fluoropiperidin-1-yl)-2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound FC1CN(CCC1)C1=C(C=C2C(=N1)N=C(O2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C HXECBJUGQJREAN-UHFFFAOYSA-N 0.000 claims 1
- GEFPFULKCUXXFX-UHFFFAOYSA-N N-[5-(3-fluoropiperidin-1-yl)-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-5-(2-methylpyridin-4-yl)furan-2-carboxamide Chemical compound FC1CN(CCC1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2OC(=CC2)C2=CC(=NC=C2)C GEFPFULKCUXXFX-UHFFFAOYSA-N 0.000 claims 1
- MLHCFKHURSHBIL-UHFFFAOYSA-N N-[5-(3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound OC1CC2CCC(C1)N2C2=C(C=C1C(=N2)N=C(S1)N1CCOCC1)NC(=O)C=1N=C(OC1)C1=CC(=NC=C1)C MLHCFKHURSHBIL-UHFFFAOYSA-N 0.000 claims 1
- DUVSHSPQVYPBOF-UHFFFAOYSA-N N-[5-(3-hydroxyazetidin-1-yl)-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound OC1CN(C1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C DUVSHSPQVYPBOF-UHFFFAOYSA-N 0.000 claims 1
- SJHNWSAWWOAWJH-UHFFFAOYSA-N N-[5-(3-hydroxypyrrolidin-1-yl)-2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound OC1CN(CC1)C1=C(C=C2C(=N1)N=C(O2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C SJHNWSAWWOAWJH-UHFFFAOYSA-N 0.000 claims 1
- YUHOQYQOIGBKKN-UHFFFAOYSA-N N-[5-(3-hydroxypyrrolidin-1-yl)-2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl]-2-(6-methoxypyridin-3-yl)-1,3-oxazole-4-carboxamide Chemical compound OC1CN(CC1)C1=C(C=C2C(=N1)N=C(O2)N2CCOCC2)NC(=O)C=2N=C(OC2)C=2C=NC(=CC2)OC YUHOQYQOIGBKKN-UHFFFAOYSA-N 0.000 claims 1
- GGCAAZFAPVQNFZ-UHFFFAOYSA-N N-[5-(3-hydroxypyrrolidin-1-yl)-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(6-methoxypyridin-3-yl)-1,3-oxazole-4-carboxamide Chemical compound OC1CN(CC1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2N=C(OC2)C=2C=NC(=CC2)OC GGCAAZFAPVQNFZ-UHFFFAOYSA-N 0.000 claims 1
- ITGXBJQZEOXRKZ-UHFFFAOYSA-N N-[5-(4-aminopiperidin-1-yl)-2-(3-hydroxypiperidin-1-yl)-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide hydrochloride Chemical compound Cl.NC1CCN(CC1)C1=C(C=C2C(=N1)N=C(S2)N2CC(CCC2)O)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C ITGXBJQZEOXRKZ-UHFFFAOYSA-N 0.000 claims 1
- IFYMBKMLEOTQOH-UHFFFAOYSA-N N-[5-(4-fluoropiperidin-1-yl)-2-(3-hydroxypiperidin-1-yl)-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound FC1CCN(CC1)C1=C(C=C2C(=N1)N=C(S2)N2CC(CCC2)O)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C IFYMBKMLEOTQOH-UHFFFAOYSA-N 0.000 claims 1
- RCRXLMTZSKNLAP-UHFFFAOYSA-N N-[5-(4-fluoropiperidin-1-yl)-2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound FC1CCN(CC1)C1=C(C=C2C(=N1)N=C(O2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C RCRXLMTZSKNLAP-UHFFFAOYSA-N 0.000 claims 1
- IUDPMQIWAFRELA-UHFFFAOYSA-N N-[5-(4-fluoropiperidin-1-yl)-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide hydrochloride Chemical compound Cl.Cc1cc(ccn1)-c1nc(co1)C(=O)Nc1cc2sc(nc2nc1N1CCC(F)CC1)N1CCOCC1 IUDPMQIWAFRELA-UHFFFAOYSA-N 0.000 claims 1
- UFSUSPPLIAMAMD-UHFFFAOYSA-N N-[5-(4-hydroxypiperidin-1-yl)-2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound OC1CCN(CC1)C1=C(C=C2C(=N1)N=C(O2)N1CCOCC1)NC(=O)C=1N=C(OC=1)C1=CC(=NC=C1)C UFSUSPPLIAMAMD-UHFFFAOYSA-N 0.000 claims 1
- LTGOMUVXQZPWME-UHFFFAOYSA-N N-[5-(4-hydroxypiperidin-1-yl)-2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl]-5-(2-methylpyridin-4-yl)furan-2-carboxamide Chemical compound OC1CCN(CC1)C1=C(C=C2C(=N1)N=C(O2)N2CCOCC2)NC(=O)C=2OC(=CC2)C2=CC(=NC=C2)C LTGOMUVXQZPWME-UHFFFAOYSA-N 0.000 claims 1
- QPGHOGMRNUYOLJ-UHFFFAOYSA-N N-[5-(4-hydroxypiperidin-1-yl)-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound OC1CCN(CC1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C QPGHOGMRNUYOLJ-UHFFFAOYSA-N 0.000 claims 1
- DPUFEEZXAGAWNK-UHFFFAOYSA-N N-[5-(4-methylpiperazin-1-yl)-2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound CN1CCN(CC1)C1=C(C=C2C(=N1)N=C(O2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C DPUFEEZXAGAWNK-UHFFFAOYSA-N 0.000 claims 1
- QLEBVOXYIMDFDW-UHFFFAOYSA-N N-[5-(6-fluoropyridin-3-yl)-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound FC1=CC=C(C=N1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C QLEBVOXYIMDFDW-UHFFFAOYSA-N 0.000 claims 1
- UUQYIABHHXCGDI-UHFFFAOYSA-N N-[5-(azepan-1-yl)-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound N1(CCCCCC1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C UUQYIABHHXCGDI-UHFFFAOYSA-N 0.000 claims 1
- XEYZWQLPUPPXOA-UHFFFAOYSA-N N-[5-(azetidin-1-yl)-2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound N1(CCC1)C1=C(C=C2C(=N1)N=C(O2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C XEYZWQLPUPPXOA-UHFFFAOYSA-N 0.000 claims 1
- FKGUUFRZOYHUSN-UHFFFAOYSA-N N-[5-(azetidin-1-yl)-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound N1(CCC1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C FKGUUFRZOYHUSN-UHFFFAOYSA-N 0.000 claims 1
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- WKZJFDYGUKSZEB-UHFFFAOYSA-N N-[5-(azetidin-1-yl)-2-piperidin-1-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound N1(CCC1)C1=C(C=C2C(=N1)N=C(O2)N2CCCCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C WKZJFDYGUKSZEB-UHFFFAOYSA-N 0.000 claims 1
- HJJVFLYRXARIOL-UHFFFAOYSA-N N-[5-(azetidin-1-yl)-2-piperidin-1-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound N1(CCC1)C1=C(C=C2C(=N1)N=C(S2)N2CCCCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C HJJVFLYRXARIOL-UHFFFAOYSA-N 0.000 claims 1
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- APVNUCPUMXEUKZ-MRXNPFEDSA-N N-[5-[(3R)-3-aminopyrrolidin-1-yl]-2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound N[C@H]1CN(CC1)C1=C(C=C2C(=N1)N=C(O2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C APVNUCPUMXEUKZ-MRXNPFEDSA-N 0.000 claims 1
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- TZYSUFGDLAPQFN-QGZVFWFLSA-N N-[5-[(3R)-3-hydroxypiperidin-1-yl]-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound O[C@H]1CN(CCC1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C TZYSUFGDLAPQFN-QGZVFWFLSA-N 0.000 claims 1
- IFSSDFDCLSRTPT-GOSISDBHSA-N N-[5-[(3R)-3-hydroxypiperidin-1-yl]-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-5-(2-methylpyridin-4-yl)furan-2-carboxamide Chemical compound O[C@H]1CN(CCC1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2OC(=CC2)C2=CC(=NC=C2)C IFSSDFDCLSRTPT-GOSISDBHSA-N 0.000 claims 1
- SJHNWSAWWOAWJH-MRXNPFEDSA-N N-[5-[(3R)-3-hydroxypyrrolidin-1-yl]-2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound O[C@H]1CN(CC1)C1=C(C=C2C(=N1)N=C(O2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C SJHNWSAWWOAWJH-MRXNPFEDSA-N 0.000 claims 1
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- ZGHKIBFOFCWJIS-MRXNPFEDSA-N N-[5-[(3R)-3-hydroxypyrrolidin-1-yl]-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound O[C@H]1CN(CC1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C ZGHKIBFOFCWJIS-MRXNPFEDSA-N 0.000 claims 1
- GGCAAZFAPVQNFZ-OAHLLOKOSA-N N-[5-[(3R)-3-hydroxypyrrolidin-1-yl]-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(6-methoxypyridin-3-yl)-1,3-oxazole-4-carboxamide Chemical compound O[C@H]1CN(CC1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2N=C(OC2)C=2C=NC(=CC2)OC GGCAAZFAPVQNFZ-OAHLLOKOSA-N 0.000 claims 1
- XBXOZNSESLDIRR-KRWDZBQOSA-N N-[5-[(3S)-3-aminopiperidin-1-yl]-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound N[C@@H]1CN(CCC1)C1=C(C=C2C(=N1)N=C(S2)N1CCOCC1)NC(=O)C=1N=C(OC=1)C1=CC(=NC=C1)C XBXOZNSESLDIRR-KRWDZBQOSA-N 0.000 claims 1
- APVNUCPUMXEUKZ-INIZCTEOSA-N N-[5-[(3S)-3-aminopyrrolidin-1-yl]-2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound N[C@@H]1CN(CC1)C1=C(C=C2C(=N1)N=C(O2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C APVNUCPUMXEUKZ-INIZCTEOSA-N 0.000 claims 1
- CIGNEPODKAIGQB-INIZCTEOSA-N N-[5-[(3S)-3-aminopyrrolidin-1-yl]-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound N[C@@H]1CN(CC1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C CIGNEPODKAIGQB-INIZCTEOSA-N 0.000 claims 1
- AAXCALBHKQONJE-KRWDZBQOSA-N N-[5-[(3S)-3-fluoropiperidin-1-yl]-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound F[C@@H]1CN(CCC1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C AAXCALBHKQONJE-KRWDZBQOSA-N 0.000 claims 1
- TZYSUFGDLAPQFN-KRWDZBQOSA-N N-[5-[(3S)-3-hydroxypiperidin-1-yl]-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound O[C@@H]1CN(CCC1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C TZYSUFGDLAPQFN-KRWDZBQOSA-N 0.000 claims 1
- SJHNWSAWWOAWJH-INIZCTEOSA-N N-[5-[(3S)-3-hydroxypyrrolidin-1-yl]-2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound O[C@@H]1CN(CC1)C1=C(C=C2C(=N1)N=C(O2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C SJHNWSAWWOAWJH-INIZCTEOSA-N 0.000 claims 1
- YUHOQYQOIGBKKN-HNNXBMFYSA-N N-[5-[(3S)-3-hydroxypyrrolidin-1-yl]-2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl]-2-(6-methoxypyridin-3-yl)-1,3-oxazole-4-carboxamide Chemical compound O[C@@H]1CN(CC1)C1=C(C=C2C(=N1)N=C(O2)N1CCOCC1)NC(=O)C=1N=C(OC=1)C=1C=NC(=CC=1)OC YUHOQYQOIGBKKN-HNNXBMFYSA-N 0.000 claims 1
- UWLBLBMPFDEFEE-KRWDZBQOSA-N N-[5-[(3S)-3-hydroxypyrrolidin-1-yl]-2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl]-5-(2-methylpyridin-4-yl)furan-2-carboxamide Chemical compound O[C@@H]1CN(CC1)C1=C(C=C2C(=N1)N=C(O2)N2CCOCC2)NC(=O)C=2OC(=CC2)C2=CC(=NC=C2)C UWLBLBMPFDEFEE-KRWDZBQOSA-N 0.000 claims 1
- WSPQYRIZFPASFH-KRWDZBQOSA-N N-[5-[(3S)-3-hydroxypyrrolidin-1-yl]-2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl]-5-(2-methylpyridin-4-yl)thiophene-2-carboxamide Chemical compound O[C@@H]1CN(CC1)C1=C(C=C2C(=N1)N=C(O2)N1CCOCC1)NC(=O)C=1SC(=CC=1)C1=CC(=NC=C1)C WSPQYRIZFPASFH-KRWDZBQOSA-N 0.000 claims 1
- ZGHKIBFOFCWJIS-INIZCTEOSA-N N-[5-[(3S)-3-hydroxypyrrolidin-1-yl]-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide Chemical compound O[C@@H]1CN(CC1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2N=C(OC2)C2=CC(=NC=C2)C ZGHKIBFOFCWJIS-INIZCTEOSA-N 0.000 claims 1
- GGCAAZFAPVQNFZ-HNNXBMFYSA-N N-[5-[(3S)-3-hydroxypyrrolidin-1-yl]-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-2-(6-methoxypyridin-3-yl)-1,3-oxazole-4-carboxamide Chemical compound O[C@@H]1CN(CC1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2N=C(OC2)C=2C=NC(=CC2)OC GGCAAZFAPVQNFZ-HNNXBMFYSA-N 0.000 claims 1
- UOIUBLZGHLGIFX-KRWDZBQOSA-N N-[5-[(3S)-3-hydroxypyrrolidin-1-yl]-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-5-(2-methylpyridin-4-yl)furan-2-carboxamide Chemical compound O[C@@H]1CN(CC1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2OC(=CC2)C2=CC(=NC=C2)C UOIUBLZGHLGIFX-KRWDZBQOSA-N 0.000 claims 1
- CIROKYGHOZOYQL-KRWDZBQOSA-N N-[5-[(3S)-3-hydroxypyrrolidin-1-yl]-2-morpholin-4-yl-[1,3]thiazolo[4,5-b]pyridin-6-yl]-5-(2-methylpyridin-4-yl)thiophene-2-carboxamide Chemical compound O[C@@H]1CN(CC1)C1=C(C=C2C(=N1)N=C(S2)N2CCOCC2)NC(=O)C=2SC(=CC2)C2=CC(=NC=C2)C CIROKYGHOZOYQL-KRWDZBQOSA-N 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Classifications
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
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- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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- A61K31/5355—Non-condensed oxazines and containing further heterocyclic rings
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Claims (23)
1. Spoj formule II, ili njegova farmaceutski prihvatljiva sol, za uporabu u liječenju ili prevenciji akutne mijeloične leukemije (AML), pri čemu je AML otporan na liječenje inhibitorom tirozin kinaze 3 (FLT-3) sličnom FMS-u;
[image]
pri čemu
X1 i X3 su nezavisno CH ili N; X2 je CR2 ili N; ukoliko jedan i ne više od jednog X1, X2 ili X3 je N;
A je O ili S;
Y je -CH2- ili O;
Z je aril ili heterociklil;
Ri, pri svakoj pojavnosti, je nezavisno halo ili opcionalno supstituirani heterociklil; pri čemu supstituent je alkil, alkoksi, aminoalkil, halo, hidroksil, hidroksi alkil ili -NRaRb;
R2 je hidrogen, opcionalno supstituirani cikloalkil, opcionalno supstituirani aril, opcionalno supstituirani heterociklil ili -NRaRb; pri čemu supstituent je alkil, amino, halo ili hidroksil;
R3, pri svakoj pojavnosti, je alkil ili hidroksil;
Ra iRb su nezavisno hidrogen, alkil, acil ili heterociklil;
'm' i 'n' su nezavisno 0, 1 ili 2; i
'p' je 0 ili 1.
2. Spoj za uporabu prema zahtjevu 1, pri čemu
A je O ili S;
Y je -CH2- ili O;
Z je aril ili heterociklil;
Ri, pri svakoj pojavnosti, je nezavisno halo ili opcionalno supstituirani heterociklil;
pri čemu supstituent je alkil, alkoksi, aminoalkil, halo, hidroksil ili -NRaRb; gdje Ra i Rb su nezavisno hidrogen, alkil, ili heterociklil;
R2 je hidrogen, cikloalkil, opcionalno supstituirani heterociklil ili -NRaRb, gdje supstituent je odabran od amino, halo ili hidroksil;
'm' i 'n' su nezavisno 0, 1 ili 2; i
'p' je 0 ili 1.
3. Spoj za uporabu prema zahtjevu 1, pri čemu
[image]
Je
[image]
[image]
4. Spoj za uporabu prema bilo kojem od zahtjeva 1-3, pri čemu Z je (a) aril ili 5-ili 6-člani heterociklil, ili (b) odabran od fenil, furanil, tienil, pirrolil, pirazolil, imidazolil, oksazolil, isoksazolil, tiazolil, isotiazolil, 1H-tetrazolil, oksadiazolil, triazolil, piridil, pirimidinil, pirazinil, piridazinil, azetidinil, oxetanil, imidazolidinil, pirrolidinil, oksazolidinil, tiazolidinil, pirazolidinil, tetrahidrofuranil, piperidinil, piperazinil, tetrahidropiranil, morfolinil, tiomorfolinil, 1,4-dioksanil, dioksidotiomorfolinil, oksapiperazinil, oksapiperidinil, tetrahidrofuril, tetrahidropiranil, tetrahidrotiofenil, dihidropiranil i azabiciklo[3.2.1]oktanil; svaki od kojih je opcionalno supstituiran sa alkil, alkoksi, halo, hidroksil, hidroksi alkil ili -NRaRb; i Ra i Rb su nezavisno hidrogen, alkil ili acil.
5. Spoj za uporabu prema zahtjevu 1 predstavljen formulom (IIA):
[image]
ili njegova farmaceutski prihvatljiva sol.
6. Spoj za uporabu prema zahtjevu 5, pri čemu
A je O ili S;
Y je -CH2- ili O;
Ri, pri svakoj pojavnosti, je nezavisno halo ili opcionalno supstituirani heterociklil; pri čemu supstituent je alkil, alkoksi, aminoalkil, halo, hidroksil ili -NRaRb; gdje Ra i Rb su nezavisno hidrogen, alkil, ili heterociklil;
R2 je hidrogen, cikloalkil, opcionalno supstituirani heterociklil ili -NRaRb, gdje supstituent je odabran od amino, halo ili hidroksil; i
'm' i 'n' su nezavisno 0, 1 ili 2.
7. Spoj za uporabu prema zahtjevu 1, predstavljen (IIB):
[image]
ili njegova farmaceutski prihvatljiva sol.
8. Spoj za uporabu prema zahtjevu 7, pri čemu
A je O ili S;
Y je -CH2- ili O;
Ri, pri svakoj pojavnosti, je nezavisno halo ili opcionalno supstituirani heterociklil; pri čemu supstituent je alkil, alkoksi, aminoalkil, halo, hidroksil ili -NRaRb; gdje Ra i Rb su nezavisno hidrogen, alkil, ili heterociklil;
R2 je hidrogen, cikloalkil, opcionalno supstituirani heterociklil ili -NRaRb, gdje supstituent je odabran od amino, halo ili hidroksil; i
'm' i 'n' su nezavisno 0, 1 ili 2.
9. Spoj za uporabu prema zahtjevu 1, pri čemu spoj je spoj formule (IIC)
[image]
ili njegova farmaceutski prihvatljiva sol.
10. Spoj za uporabu prema bilo kojem od zahtjeva 1-9, pri čemu R1 je opcionalno supstituirani heterociklil; pri čemu supstituent je alkil, alkoksi, aminoalkil, halo, hidroksil, hidroksi alkil ili -NRaRb; iRa iRb su nezavisno hidrogen ili acil, ili
pri čemu R1 je opcionalno supstituirani heterociklil; i supstituent je alkil, alkoksi, aminoalkil, halo, hidroksil ili -NRaRb; gdje Ra i Rb su nezavisno hidrogen, alkil, ili heterociklil; ili
pri čemu R1 je halo.
11. Spoj za uporabu prema zahtjevu 10, pri čemu R1 je opcionalno supstituirani pirazolil, pri čemu opcionalni supstituent je alkil, hidroksil ili -NRaRb.
12. Spoj za uporabu prema bilo kojem od zahtjeva 1-11, pri čemu R2 je hidrogen, cikloalkil, poput ciklopropila; opcionalno supstituirani heterociklil, poput piperidinila, pirrolidinila, morfolinila, piperazinila, azetidinila, pirazolila, furanila ili azabiciklo[3.2.1]oktanila; pri čemu supstituent je hidroksil, halo, alkil ili amino; ili -NRaRb, gdje supstituent je odabran od amino, halo ili hidroksil.
13. Spoj za uporabu prema bilo kojem od zahtjeva 1-12, pri čemu R3 je alkil.
14. Spoj za uporabu prema bilo kojem od zahtjeva 1-13, pri čemu m je 0 ili 2, i p je 0 ili 1.
15. Spoj za uporabu prema zahtjevu 1, pri čemu je spoj formule (II) odabran od:
6'-amino-N-(2-morfolinooksazolo[4,5-b]piridin-6-il)-[2,3'-bipiridin]-6-karboksamid;
6'-amino-N-(5-ciklopropil-2-morfolinooksazolo[4,5-b]piridin-6-il)-[2,3'-bipiridin]-6-karboksamid hidroklorid;
N-(5-ciklopropil-2-morfolinooksazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid hidroklorid;
N-(2,5-di(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)-6-(1H-pirazol-4-il)pikolinamid hidroklorid;
N-(2, 5-di(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
N-(2-morfolino-5-(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)-6-(1H-pirazol-4-il)pikolinamid;
2-(2-metilpiridin-4-il)-N-(2-morfolino-5-(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
6-kloro-N-(2-morfolino-5-(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)pikolinamid;
N-(2,5-di(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)-6-(1-metil-1H-pirazol-4-il)pikolinamid;
2-(2-kloropiridin-4-il)-N-(2,5-di(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
(S)-2-(2-metilpiridin-4-il)-N-(2-morfolino-5-(pirrolidin-3-ilamino)oksazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
6'-amino-N-(2-morfolinooksazolo[5,4-b]piridin-5-il)-[2,3'-bipiridin]-6-karboksamid;
6'-amino-N-(2-morfolinotiazolo[4,5-c]piridin-6-il)-[2,3'-bipiridin]-6-karboksamid;
6'-amino-N-(2-morfolinotiazolo[5,4-b]piridin-5-il)-[2,3'-bipiridin]-6-karboksamid;
2-(2-metilpiridin-4-il)-N-(2-morfolinotiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
6'-amino-N-(2-morfolinotiazolo[4,5-b]piridin-6-il)-[2,3'-bipiridin]-6-karboksamid;
N-(2-morfolinotiazolo[4,5-b]piridin-6-il)-6-(1H-pirazol-4-il)pikolinamid;
3-(4-(aminometil)piperidin-1-il)-5-fluoro-N-(2-morfolinotiazolo[4,5-b]piridin-6-il)benzamid;
2-(4-(aminometil)piperidin-1-il)-5-fluoro-N-(2-morfolinotiazolo[4,5-b]piridin-6-il)benzamid;
2-(2-metilpiridin-4-il)-N-(2-morfolino-5-(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
N-(2-morfolino-5-(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)-6-(1H-pirazol-4-il)pikolinamid;
N-(2,5-di(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)-6-(1H-pirazol-4-il)pikolinamid;
N-(2,5-di(piperidin-1-il)tiazolo[4, 5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
N-(2,5-dimorfolinooksazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
N-(5-(4-metilpiperazin-1-il)-2-morfolinooksazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
N-(2,5-di(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)-2-(6-metoksipiridin-3-il)oksazol-4-karboksamid;
N-(2,5-di(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-3-il)oksazol-4-karboksamid;
N-(2, 5-di(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)-2-(2-hidroksipiridin-3-il)oksazol-4-karboksamid;
2-(2-hidroksipiridin-3-il)-N-(2-morfolino-5-(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
N-(2, 5-di(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)-2-(6-hidroksipiridin-3-il)oksazol-4-karboksamid;
2-(2-metoksipiridin-4-il)-N-(2-morfolino-5-(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
2-(2-metilpiridin-3-il)-N-(2-morfolino-5-(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
2-(3-metilpiridin-4-il)-N-(2-morfolino-5-(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
N-(2, 5-di(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)-2-(3-metilpiridin-4-il)oksazol-4-karboksamid;
2-(6-metilpiridin-3-il)-N-(2-morfolino-5-(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
6-(1-metil-1H-pirazol-4-il)-N-(2-morfolino-5-(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)pikolinamid;
N-(2,5-di(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)-2-(6-metilpiridin-3-il)oksazol-4-karboksamid;
(S)-N-(5-(3-aminopirrolidin-1-il)-2-morfolinooksazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
(S)-N-(5-(3-hidroksipirrolidin-1-il)-2-morfolinooksazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
(R)-N-(5-(3-aminopirrolidin-1-il)-2-morfolinooksazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
(R)-N-(5-(3-hidroksipirrolidin-1-il)-2-morfolinooksazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
(S)-2-(3-aminopirrolidin-1-il)-N-(2-morfolino-5-(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
(S)-6-(3-hidroksipirrolidin-1-il)-N-(2-morfolino-5-(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)pikolinamid;
(S)-6-(3-aminopirrolidin-1-il)-N-(2-morfolino-5-(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)pikolinamid;
(S)-2-(3-hidroksipirrolidin-1-il)-N-(2-morfolino-5-(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
(S)-N-(5-ciklopropil-2-morfolinooksazolo[4,5-b]piridin-6-il)-2-(3-hidroksipirrolidin-1-il)oksazol-4-karboksamid;
(S)-2-(3-aminopirrolidin-1-il)-N-(5-ciklopropil-2-morfolinooksazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
2-(2-metilpiridin-4-il)-N-(5-(piperidin-1-il)-2-(pirrolidin-1-il)oksazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid hidroklorid;
N-(2-(2,6-dimetilmorfolino)-5-(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid hidroklorid;
N-(2,5-di(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)-6-(1-metil-1H-pirazol-4-il)pikolinamid hidroklorid;
6-(1-metil-1H-pirazol-4-il)-N-(2-morfolino-5-(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)pikolinamid;
N-(2,5-di(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-3-il)oksazol-4-karboksamid hidroklorid;
N-(2-((2S,6R)-2,6-dimetilmorfolino)-5-(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
2-(2-metilpiridin-3-il)-N-(2-morfolino-5-(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
2-(2-hidroksipiridin-3-il)-N-(2-morfolino-5-(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
N-(2,5-di(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)-2-(2-metoksipiridin-4-il)oksazol-4-karboksamid;
2-(6-metoksipiridin-3-il)-N-(2-morfolino-5-(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
2-(2-metoksipiridin-4-il)-N-(2-morfolino-5-(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
(S)-N-(5-(3-fluoropiperidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
2-(6-metilpiridin-3-il)-N-(2-morfolino-5-(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
2-(3-metilpiridin-4-il)-N-(2-morfolino-5-(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
(S)-6-(3-aminopirrolidin-1-il)-N-(2-morfolino-5-(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)pikolinamid;
(S)-6-(3-hidroksipirrolidin-1-il)-N-(2-morfolino-5-(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)pikolinamid;
(S)-6-(3-aminopirrolidin-1-il)-N-(2,5-di(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)pikolinamid;
(S)-N-(2, 5-di(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)-6-(3-hidroksipirrolidin-1-il)pikolinamid;
(S)-2-(3-aminopirrolidin-1-il)-N-(2-morfolino-5-(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
(S)-N-(5-(3-aminopirrolidin-1-il)-2-morfolinotiazolo[4, 5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
(S)-2-(3-aminopirrolidin-1-il)-N-(5-ciklopropil-2-morfolinotiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
N-(5-ciklopropil-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
(S)-2-(3-hidroksipirrolidin-1-il)-N-(2-morfolino-5-(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
(S)-N-(5-(3-hidroksipirrolidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
(S)-N-(5-ciklopropil-2-morfolinotiazolo[4,5-b]piridin-6-il)-6-(3-hidroksipirrolidin-1-il)pikolinamid;
(S)-N-(5-ciklopropil-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(3-hidroksipirrolidin-1-il)oksazol-4-karboksamid;
(S)-N-(5-ciklopropil-2-morfolinotiazolo[4,5-b]piridin-6-il)-6-(1-(2-hidroksipropil)-1H-pirazol-4-il)pikolinamid;
(S)-N-(5-ciklopropil-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(1-(2-hidroksipropil)-1H-pirazol-4-il)oksazol-4-karboksamid;
N-(5-(3-hidroksipirrolidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(6-metoksipiridin-3-il)oksazol-4-karboksamid;
(S)-N-(5-(3-hidroksipirrolidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(6-metoksipiridin-3-il)oksazol-4-karboksamid;
(R)-N-(5-(3-hidroksipirrolidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(6-metoksipiridin-3-il)oksazol-4-karboksamid;
(S)-N-(5-(azetidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-6-(3-hidroksipirrolidin-1-il)pikolinamid;
N-(5-(3-hidroksiazetidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
(S)-N-(5-(3-hidroksipirrolidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-5-(2-metilpiridin-4-il)tiofen-2-karboksamid;
(S)-N-(5-(3-hidroksipirrolidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-5-(2-metilpiridin-4-il)furan-2-karboksamid;
(S)-N-(5-(3-hidroksipiperidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
N-(5-(4-hidroksipiperidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid
(R)-N-(5-(3-hidroksipirrolidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
N-(5-(4-hidroksipiperidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-5-(2-metilpiridin-4-il)furan-2-karboksamid;
N-(5-(azetidin-1-il)-2-(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
2-(2-metilpiridin-4-il)-N-(2-(piperidin-1-il)-5-(pirrolidin-1-il)tiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
2-(2-metilpiridin-4-il)-N-(2-morfolino-5-(pirrolidin-1-il)tiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
5-(2-metilpiridin-4-il)-N-(2-morfolino-5-(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)furan-2-karboksamid;
N-(5-(azepan-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
2-(2-aminopiridin-4-il)-N-(2-morfolino-5-(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid hidroklorid;
N-(5-(azetidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
(R)-N-(5-(3-hidroksipiperidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
(R)-N-(5-(3-hidroksipiperidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-5-(2-metilpiridin-4-il)furan-2-karboksamid;
(S)-6-(1-(2-hidroksipropil)-1H-pirazol-4-il)-N-(2-morfolino-5-(piperidin-1-il)tiazolo[4, 5-b]piridin-6-il)pikolinamid
N-(5-(4-fluoropiperidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-5-(2-metilpiridin-4-il)furan-2-karboksamid
N-(5-(4-fluoropiperidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid hidroklorid
N-(5-(1-metil-1H-pirazol-4-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
N-(5-(3-fluorofenil)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
N-(5-(4-hidroksipiperidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-5-(2-metilpiridin-4-il)furan-2-karboksamid;
N-(5-(3-fluoropiperidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-5-(2-metilpiridin-4-il)furan-2-karboksamid;
(S)-N-(5-(3-hidroksipirrolidin-1-il)-2-morfolinooksazolo[4,5-b]piridin-6-il)-2-(6-metoksipiridin-3-il)oksazol-4-karboksamid;
N-(5-(3-hidroksipirrolidin-1-il)-2-morfolinooksazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
(R)-N-(5-(3-hidroksipirrolidin-1-il)-2-morfolinooksazolo[4,5-b]piridin-6-il)-2-(6-metoksipiridin-3-il)oksazol-4-karboksamid;
N-(5-(3-hidroksipirrolidin-1-il)-2-morfolinooksazolo[4,5-b]piridin-6-il)-2-(6-metoksipiridin-3-il)oksazol-4-karboksamid;
(S)-N-(5-(3-hidroksipirrolidin-1-il)-2-morfolinooksazolo[4,5-b]piridin-6-il)-5-(2-metilpiridin-4-il)furan-2-karboksamid;
(S)-N-(5-(3-hidroksipirrolidin-1-il)-2-morfolinooksazolo[4,5-b]piridin-6-il)-5-(2-metilpiridin-4-il)tiofen-2-karboksamid;
N-(5-(azetidin-1-il)-2-(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
2-(2-metilpiridin-4-il)-N-(2-(piperidin-1-il)-5-(pirrolidin-1-il)oksazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
5-(2-metilpiridin-4-il)-N-(2-morfolino-5-(piperidin-1-il)oksazolo[4,5-b]piridin-6-il)furan-2-karboksamid;
N-(5-(azetidin-1-il)-2-morfolinooksazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
2-(2-metilpiridin-4-il)-N-(2-morfolino-5-(pirrolidin-1-il)oksazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
N-(5-(4-hidroksipiperidin-1-il)-2-morfolinooksazolo[4,5-b]piridin-6-il)-5-(2-metilpiridin-4-il)furan-2-karboksamid;
(R)-N-(5-(3 -hidroksipiperidin-1-il)-2-morfolinooksazolo[4,5-b]piridin-6-il)-5-(2-metilpiridin-4-il)furan-2-karboksamid;
N-(5-(furan-3-il)-2-morfolinooksazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
N-(5-(3-fluoropiperidin-1-il)-2-morfolinooksazolo [4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
N-(5-(4-hidroksipiperidin-1-il)-2-morfolinooksazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
N-(5-(4-fluoropiperidin-1-il)-2-morfolinooksazolo [4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
(S)-N-(5-(3-aminopiperidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
2-(2-metilpiridin-4-il)-N-(2-morfolino-5-(1H-pirazol-4-il)tiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
N-(5-(6-fluoropiridin-3-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
N-(5-(3-hidroksi-8-azabiciklo[3.2.1]octan-8-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
N-(2-(3-hidroksipiperidin-1-il)-5-(piperidin-1-il)tiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
2-(2-acetamidopiridin-4-il)-N-(5-(4-hidroksipiperidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
N-(2-(3-hidroksipiperidin-1-il)-5-(4-hidroksipiperidin-1-il)tiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
2-(2-acetamidopiridin-4-il)-N-(5-(3-hidroksipiperidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid;
2-(2-aminopiridin-4-il)-N-(5-(3-hidroksipiperidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid hidroklorid;
5-(2-aminopiridin-4-il)-N-(5-(4-hidroksipiperidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)furan-3-karboksamid hidroklorid;
2-(2-aminopiridin-4-il)-N-(5-(4-hidroksipiperidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid hidroklorid;
2-(2-aminopiridin-4-il)-N-(5-(4-fluoropiperidin-1-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)oksazol-4-karboksamid hidroklorid;
N-(5-(2-fluoropiridin-4-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
N-(5-(4-fluoropiperidin-1-il)-2-(3-hidroksipiperidin-1-il)tiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid;
N-(5-(4-aminopiperidin-1-il)-2-(3-hidroksipiperidin-1-il)tiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid hidroklorid;i
N-(5-(2-hidroksipiridin-4-il)-2-morfolinotiazolo[4,5-b]piridin-6-il)-2-(2-metilpiridin-4-il)oksazol-4-karboksamid hidroklorid;
ili njegova farmaceutski prihvatljiva sol.
16. Spoj za uporabu prema zahtjevu 1, pri čemu je spoj
[image]
ili njegova farmaceutski prihvatljiva sol.
17. Spoj za uporabu prema zahtjevu 1, pri čemu je spoj
[image]
18. Spoj za uporabu prema zahtjevu 1, pri čemu je spoj
[image]
ili njegova farmaceutski prihvatljiva sol.
19. Spoj za uporabu prema zahtjevu 1, pri čemu je spoj
[image]
20. Spoj za uporabu prema bilo kojem od prethodnih zahtjeva, pri čemu je AML naznačen mutacijom u FLT3 genu.
21. Spoj za uporabu prema zahtjevu 20, pri čemu je mutacija interna tandem duplikacija (ITD).
22. Spoj za uporabu prema zahtjevu 20, pri čemu je mutacija D835H, D835V, D835Y, K663Q, N841L, ili F691L mutacija.
23. Spoj za uporabu prema zahtjevu 20, pri čemu mutacija je mutacija D835Y.
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