NO342357B1 - Pyrido-(2,3-d)-pyrimidinonforbindelser, farmasøytisk sammensetning og deres anvendelse som PI3-inhibitorer - Google Patents

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Publication number

NO342357B1

NO342357B1 NO20091141A NO20091141A NO342357B1 NO 342357 B1 NO342357 B1 NO 342357B1 NO 20091141 A NO20091141 A NO 20091141A NO 20091141 A NO20091141 A NO 20091141A NO 342357 B1 NO342357 B1 NO 342357B1

Authority

NO

Norway

Prior art keywords

methyl

amino

pyrimidin

trans

cyclohexyl

Prior art date

2006-09-15

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• 239000008194 pharmaceutical composition Substances 0.000 title claims description 17
• 239000003112 inhibitor Substances 0.000 title abstract description 34
• MHHOMHMNIRXARC-UHFFFAOYSA-N 1h-pyrido[2,3-d]pyrimidin-2-one Chemical class C1=CN=C2NC(=O)N=CC2=C1 MHHOMHMNIRXARC-UHFFFAOYSA-N 0.000 title 1
• 150000003839 salts Chemical class 0.000 claims abstract description 70
• 150000001875 compounds Chemical class 0.000 claims description 287
• -1 amino, carbonyl Chemical group 0.000 claims description 113
• 125000000217 alkyl group Chemical group 0.000 claims description 62
• 125000003118 aryl group Chemical group 0.000 claims description 55
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 48
• 125000001072 heteroaryl group Chemical group 0.000 claims description 44
• 238000011282 treatment Methods 0.000 claims description 31
• 125000003342 alkenyl group Chemical group 0.000 claims description 29
• 230000002159 abnormal effect Effects 0.000 claims description 24
• 125000000304 alkynyl group Chemical group 0.000 claims description 23
• 230000010261 cell growth Effects 0.000 claims description 23
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 239000003814 drug Substances 0.000 claims description 20
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
• 125000003545 alkoxy group Chemical group 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• 241000124008 Mammalia Species 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• LPJUKWATMDFWDN-UHFFFAOYSA-N 2-amino-6-bromo-8-[4-(2-hydroxyethoxy)cyclohexyl]-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1C(Br)=CC=2C(C)=NC(N)=NC=2N1C1CCC(OCCO)CC1 LPJUKWATMDFWDN-UHFFFAOYSA-N 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 6
• XDLYKKIQACFMJG-UHFFFAOYSA-N 2-amino-8-[4-(2-hydroxyethoxy)cyclohexyl]-6-(6-methoxypyridin-3-yl)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1C1CCC(OCCO)CC1 XDLYKKIQACFMJG-UHFFFAOYSA-N 0.000 claims description 5
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000000623 heterocyclic group Chemical group 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• IWYRRPAYAHUCKP-UHFFFAOYSA-N 8-cyclopentyl-4-methyl-2-(methylamino)-7-oxo-n-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidine-6-carboxamide Chemical compound O=C1N(C2CCCC2)C2=NC(NC)=NC(C)=C2C=C1C(=O)NC=1C=CNN=1 IWYRRPAYAHUCKP-UHFFFAOYSA-N 0.000 claims description 3
• WOMVHFKOGGCXMG-SHTZXODSSA-N C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCCO)CC1 Chemical compound C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCCO)CC1 WOMVHFKOGGCXMG-SHTZXODSSA-N 0.000 claims description 3
• PDCGXSKEKLYDRP-SHTZXODSSA-N C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCCO)CC1 Chemical compound C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCCO)CC1 PDCGXSKEKLYDRP-SHTZXODSSA-N 0.000 claims description 3
• LOYNAYXFINASCA-HDJSIYSDSA-N chembl2375954 Chemical compound O=C1C(C2=CN(C)N=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCC(N)=O)CC1 LOYNAYXFINASCA-HDJSIYSDSA-N 0.000 claims description 3
• NNXNZTDFLLHLOS-JOCQHMNTSA-N chembl2375955 Chemical compound O=C1C(C2=CNN=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCC(N)=O)CC1 NNXNZTDFLLHLOS-JOCQHMNTSA-N 0.000 claims description 3
• VNSCNWLXUYATCI-HDJSIYSDSA-N chembl2375956 Chemical compound C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCC(N)=O)CC1 VNSCNWLXUYATCI-HDJSIYSDSA-N 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
• FWILAFBSYLISCN-UHFFFAOYSA-N 2-amino-4-methyl-7-oxo-8-propan-2-yl-n-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidine-6-carboxamide Chemical compound O=C1N(C(C)C)C2=NC(N)=NC(C)=C2C=C1C(=O)NC1=CC=NN1 FWILAFBSYLISCN-UHFFFAOYSA-N 0.000 claims description 2
• KFWMEJZHEAZFMS-UHFFFAOYSA-N 2-amino-n-(2-ethylpyrazol-3-yl)-4-methyl-7-oxo-8-propan-2-ylpyrido[2,3-d]pyrimidine-6-carboxamide Chemical compound CCN1N=CC=C1NC(=O)C1=CC2=C(C)N=C(N)N=C2N(C(C)C)C1=O KFWMEJZHEAZFMS-UHFFFAOYSA-N 0.000 claims description 2
• SPZLNUYSXWJTDI-UHFFFAOYSA-N 8-cyclopentyl-4-methyl-2-(methylamino)-7-oxo-n-pyridin-2-ylpyrido[2,3-d]pyrimidine-6-carboxamide Chemical compound O=C1N(C2CCCC2)C2=NC(NC)=NC(C)=C2C=C1C(=O)NC1=CC=CC=N1 SPZLNUYSXWJTDI-UHFFFAOYSA-N 0.000 claims description 2
• MOWFUTLFKBZDFZ-UHFFFAOYSA-N 8-cyclopentyl-4-methyl-2-(methylamino)-n-(1,2-oxazol-3-yl)-7-oxopyrido[2,3-d]pyrimidine-6-carboxamide Chemical compound O=C1N(C2CCCC2)C2=NC(NC)=NC(C)=C2C=C1C(=O)NC=1C=CON=1 MOWFUTLFKBZDFZ-UHFFFAOYSA-N 0.000 claims description 2
• HKEYODYWKVJZML-UHFFFAOYSA-N 8-cyclopentyl-n-[(1-ethylpyrazol-4-yl)methyl]-4-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidine-6-carboxamide Chemical compound C1=NN(CC)C=C1CNC(=O)C(C1=O)=CC2=C(C)N=C(NC)N=C2N1C1CCCC1 HKEYODYWKVJZML-UHFFFAOYSA-N 0.000 claims description 2
• JVQZXWSJZFSIQS-HAQNSBGRSA-N C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCC(N)=O)C1 Chemical compound C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCC(N)=O)C1 JVQZXWSJZFSIQS-HAQNSBGRSA-N 0.000 claims description 2
• MQYKSHFHKJXVCJ-JOCQHMNTSA-N C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCCO)C1 Chemical compound C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCCO)C1 MQYKSHFHKJXVCJ-JOCQHMNTSA-N 0.000 claims description 2
• WOMVHFKOGGCXMG-GASCZTMLSA-N C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@H]1CC[C@@H](OCCO)CC1 Chemical compound C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@H]1CC[C@@H](OCCO)CC1 WOMVHFKOGGCXMG-GASCZTMLSA-N 0.000 claims description 2
• KMYHNHSRXMFXAJ-QAQDUYKDSA-N C1=NC(N(C)C)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCCO)CC1 Chemical compound C1=NC(N(C)C)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCCO)CC1 KMYHNHSRXMFXAJ-QAQDUYKDSA-N 0.000 claims description 2
• PCOJUVWPYNNKBZ-ULQDDVLXSA-N C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OC[C@@H](O)CO)CC1 Chemical compound C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OC[C@@H](O)CO)CC1 PCOJUVWPYNNKBZ-ULQDDVLXSA-N 0.000 claims description 2
• UTGVSQLUEPNLMK-JOCQHMNTSA-N C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCC(N)=O)C1 Chemical compound C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCC(N)=O)C1 UTGVSQLUEPNLMK-JOCQHMNTSA-N 0.000 claims description 2
• KEANLVNTCDMYDG-HDJSIYSDSA-N C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCCO)C1 Chemical compound C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCCO)C1 KEANLVNTCDMYDG-HDJSIYSDSA-N 0.000 claims description 2
• IIFFBBBKGQXRDI-HAQNSBGRSA-N C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCC(N)=O)C1 Chemical compound C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCC(N)=O)C1 IIFFBBBKGQXRDI-HAQNSBGRSA-N 0.000 claims description 2
• ISROHHNFTMLKES-JOCQHMNTSA-N C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCCO)C1 Chemical compound C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCCO)C1 ISROHHNFTMLKES-JOCQHMNTSA-N 0.000 claims description 2
• PDCGXSKEKLYDRP-GASCZTMLSA-N C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@H]1CC[C@@H](OCCO)CC1 Chemical compound C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@H]1CC[C@@H](OCCO)CC1 PDCGXSKEKLYDRP-GASCZTMLSA-N 0.000 claims description 2
• FMHCGDSGNZNXMH-SHTZXODSSA-N C1C[C@@H](OCC(=O)OC)CC[C@@H]1N1C(=O)C(C=2C=C(F)C(OC)=NC=2)=CC2=C(C)N=C(N)N=C21 Chemical compound C1C[C@@H](OCC(=O)OC)CC[C@@H]1N1C(=O)C(C=2C=C(F)C(OC)=NC=2)=CC2=C(C)N=C(N)N=C21 FMHCGDSGNZNXMH-SHTZXODSSA-N 0.000 claims description 2
• UAADDCZXGPRVQO-OKILXGFUSA-N O=C1C(C2=CNN=C2)=CC=2C(C)=NC(N)=NC=2N1[C@@H]1CC[C@H](OCCO)CC1 Chemical compound O=C1C(C2=CNN=C2)=CC=2C(C)=NC(N)=NC=2N1[C@@H]1CC[C@H](OCCO)CC1 UAADDCZXGPRVQO-OKILXGFUSA-N 0.000 claims description 2
• UAADDCZXGPRVQO-HDJSIYSDSA-N O=C1C(C2=CNN=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 Chemical compound O=C1C(C2=CNN=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 UAADDCZXGPRVQO-HDJSIYSDSA-N 0.000 claims description 2
• GPUZESZBHMOJPX-JOCQHMNTSA-N O=C1C(C2=NNC=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 Chemical compound O=C1C(C2=NNC=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 GPUZESZBHMOJPX-JOCQHMNTSA-N 0.000 claims description 2
• OHDMKRUUAMWKJE-KDURUIRLSA-N O=C1C(C=2C=C3C=CC=CC3=NC=2)=CC=2C(C)=NC(N)=NC=2N1[C@@H]1CC[C@H](OCCO)CC1 Chemical compound O=C1C(C=2C=C3C=CC=CC3=NC=2)=CC=2C(C)=NC(N)=NC=2N1[C@@H]1CC[C@H](OCCO)CC1 OHDMKRUUAMWKJE-KDURUIRLSA-N 0.000 claims description 2
• OHDMKRUUAMWKJE-WGSAOQKQSA-N O=C1C(C=2C=C3C=CC=CC3=NC=2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 Chemical compound O=C1C(C=2C=C3C=CC=CC3=NC=2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 OHDMKRUUAMWKJE-WGSAOQKQSA-N 0.000 claims description 2
• 125000005631 S-sulfonamido group Chemical group 0.000 claims description 2
• GRHRLQVZBUMCGW-IYARVYRRSA-N chembl2375953 Chemical compound O=C1C(C=2C=C3C=CC=CC3=NC=2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCC(N)=O)CC1 GRHRLQVZBUMCGW-IYARVYRRSA-N 0.000 claims description 2
• OKZQPXUPXMKTBL-HDJSIYSDSA-N chembl2375957 Chemical compound C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCC(N)=O)CC1 OKZQPXUPXMKTBL-HDJSIYSDSA-N 0.000 claims description 2
• AICMEPHIKCWYDQ-SHTZXODSSA-N chembl2375958 Chemical compound C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCC(N)=O)CC1 AICMEPHIKCWYDQ-SHTZXODSSA-N 0.000 claims description 2
• GRHRLQVZBUMCGW-HDICACEKSA-N chembl2375959 Chemical compound O=C1C(C=2C=C3C=CC=CC3=NC=2)=CC=2C(C)=NC(N)=NC=2N1[C@@H]1CC[C@H](OCC(N)=O)CC1 GRHRLQVZBUMCGW-HDICACEKSA-N 0.000 claims description 2
• LOYNAYXFINASCA-OKILXGFUSA-N chembl2375960 Chemical compound O=C1C(C2=CN(C)N=C2)=CC=2C(C)=NC(N)=NC=2N1[C@@H]1CC[C@H](OCC(N)=O)CC1 LOYNAYXFINASCA-OKILXGFUSA-N 0.000 claims description 2
• VNSCNWLXUYATCI-OKILXGFUSA-N chembl2375961 Chemical compound C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@H]1CC[C@@H](OCC(N)=O)CC1 VNSCNWLXUYATCI-OKILXGFUSA-N 0.000 claims description 2
• NNXNZTDFLLHLOS-BETUJISGSA-N chembl2375962 Chemical compound O=C1C(C2=CNN=C2)=CC=2C(C)=NC(N)=NC=2N1[C@@H]1CC[C@H](OCC(N)=O)CC1 NNXNZTDFLLHLOS-BETUJISGSA-N 0.000 claims description 2
• OKZQPXUPXMKTBL-OKILXGFUSA-N chembl2375963 Chemical compound C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@H]1CC[C@@H](OCC(N)=O)CC1 OKZQPXUPXMKTBL-OKILXGFUSA-N 0.000 claims description 2
• AICMEPHIKCWYDQ-GASCZTMLSA-N chembl2375964 Chemical compound C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@H]1CC[C@@H](OCC(N)=O)CC1 AICMEPHIKCWYDQ-GASCZTMLSA-N 0.000 claims description 2
• 125000004803 chlorobenzyl group Chemical group 0.000 claims description 2
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• XDLYKKIQACFMJG-WKILWMFISA-N chembl1234354 Chemical compound C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCCO)CC1 XDLYKKIQACFMJG-WKILWMFISA-N 0.000 claims 1
• 230000015572 biosynthetic process Effects 0.000 abstract description 9
• 238000003786 synthesis reaction Methods 0.000 abstract description 8
• 108091007960 PI3Ks Proteins 0.000 abstract description 4
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 abstract description 4
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 abstract description 4
• FQIOVOFFAYUEJN-UHFFFAOYSA-N 4-methyl-3h-pyrido[3,2-d]pyrimidin-2-one Chemical class C1=CN=C2C(C)=NC(=O)NC2=C1 FQIOVOFFAYUEJN-UHFFFAOYSA-N 0.000 abstract description 2
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 150
• 239000000203 mixture Substances 0.000 description 134
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• 239000000243 solution Substances 0.000 description 120
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• 238000005160 1H NMR spectroscopy Methods 0.000 description 87
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 84
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• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 42
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