TWI715901B - 作為ｆｇｆｒ抑制劑之雙環雜環 - Google Patents

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Publication number

TWI715901B

TWI715901B TW107146498A TW107146498A TWI715901B TW I715901 B TWI715901 B TW I715901B TW 107146498 A TW107146498 A TW 107146498A TW 107146498 A TW107146498 A TW 107146498A TW I715901 B TWI715901 B TW I715901B

Authority

TW

Taiwan

Prior art keywords

alkyl

methyl

cycloalkyl

aryl

independently selected

Prior art date

2013-04-19

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• 239000003112 inhibitor Substances 0.000 title abstract description 30
• 125000002618 bicyclic heterocycle group Chemical group 0.000 title abstract description 3
• 108091008794 FGF receptors Proteins 0.000 claims abstract description 54
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 38
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 31
• 238000011282 treatment Methods 0.000 claims abstract description 25
• 201000011510 cancer Diseases 0.000 claims abstract description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
• 102000052178 fibroblast growth factor receptor activity proteins Human genes 0.000 claims abstract description 4
• 125000000217 alkyl group Chemical group 0.000 claims description 320
• 150000001875 compounds Chemical class 0.000 claims description 258
• -1 ethoxy, methoxyethoxy, phenoxy, 2-(4 -Methylpiperazin-1-yl)ethoxy, phenyl Chemical group 0.000 claims description 159
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 156
• 125000003118 aryl group Chemical group 0.000 claims description 125
• 125000001424 substituent group Chemical group 0.000 claims description 114
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 110
• 125000005843 halogen group Chemical group 0.000 claims description 109
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 108
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 80
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 68
• 150000003839 salts Chemical class 0.000 claims description 55
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 51
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 50
• 229910052799 carbon Inorganic materials 0.000 claims description 42
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 38
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 36
• 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 33
• 239000000460 chlorine Substances 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 125000001072 heteroaryl group Chemical group 0.000 claims description 24
• 238000006467 substitution reaction Methods 0.000 claims description 22
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
• 239000003814 drug Substances 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 14
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 10
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
• 239000011737 fluorine Substances 0.000 claims description 9
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
• 125000003282 alkyl amino group Chemical group 0.000 claims description 8
• HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 7
• VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 7
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• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 6
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
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• HNGHJAMSLIQBLE-UHFFFAOYSA-N 7-amino-3-(2,6-difluoro-3,5-dimethoxyphenyl)-1,8-dimethyl-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound COC1=CC(OC)=C(F)C(N2C(N(C)C3=C(C)C(N)=NC=C3C2)=O)=C1F HNGHJAMSLIQBLE-UHFFFAOYSA-N 0.000 claims description 5
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• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
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• HYJHWTKYITXECK-UHFFFAOYSA-N 7-amino-3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-(2-fluorophenyl)-8-methyl-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound COC1=CC(OC)=C(F)C(N2C(N(C3=C(C)C(N)=NC=C3C2)C=2C(=CC=CC=2)F)=O)=C1F HYJHWTKYITXECK-UHFFFAOYSA-N 0.000 claims description 3
• OYKZXTUASRSYSR-UHFFFAOYSA-N 7-amino-3-(2,6-difluoro-3,5-dimethoxyphenyl)-8-(1-ethylpyrazol-4-yl)-1-methyl-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound C1=NN(CC)C=C1C1=C(N)N=CC2=C1N(C)C(=O)N(C=1C(=C(OC)C=C(OC)C=1F)F)C2 OYKZXTUASRSYSR-UHFFFAOYSA-N 0.000 claims description 3
• AVXXXQCONUHJLB-UHFFFAOYSA-N 7-amino-8-chloro-3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-methyl-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound COC1=CC(OC)=C(F)C(N2C(N(C)C3=C(Cl)C(N)=NC=C3C2)=O)=C1F AVXXXQCONUHJLB-UHFFFAOYSA-N 0.000 claims description 3
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 3
• 208000009746 Adult T-Cell Leukemia-Lymphoma Diseases 0.000 claims description 3
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• 208000025490 Apert syndrome Diseases 0.000 claims description 3
• 206010008342 Cervix carcinoma Diseases 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
• 206010008723 Chondrodystrophy Diseases 0.000 claims description 3
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• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 3
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• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 3
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• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 3
• 208000008919 achondroplasia Diseases 0.000 claims description 3
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• 210000000988 bone and bone Anatomy 0.000 claims description 3
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• 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 2
• PAXUHUCWTQNTSC-UHFFFAOYSA-N 7-amino-3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-methyl-8-(1-methylpyrazol-4-yl)-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound COC1=CC(OC)=C(F)C(N2C(N(C)C3=C(C4=CN(C)N=C4)C(N)=NC=C3C2)=O)=C1F PAXUHUCWTQNTSC-UHFFFAOYSA-N 0.000 claims description 2
• AHDQQWCKEPPDPT-UHFFFAOYSA-N 7-amino-3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-methyl-8-(1h-pyrazol-4-yl)-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound COC1=CC(OC)=C(F)C(N2C(N(C)C3=C(C4=CNN=C4)C(N)=NC=C3C2)=O)=C1F AHDQQWCKEPPDPT-UHFFFAOYSA-N 0.000 claims description 2
• XUUXVWVJQMMRGG-UHFFFAOYSA-N 7-amino-3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-methyl-8-(2-methylpyrazol-3-yl)-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound COC1=CC(OC)=C(F)C(N2C(N(C)C3=C(C=4N(N=CC=4)C)C(N)=NC=C3C2)=O)=C1F XUUXVWVJQMMRGG-UHFFFAOYSA-N 0.000 claims description 2
• YKBROVXUBANFCS-MDZDMXLPSA-N 7-amino-3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-methyl-8-[(e)-2-phenylethenyl]-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound COC1=CC(OC)=C(F)C(N2C(N(C)C3=C(\C=C\C=4C=CC=CC=4)C(N)=NC=C3C2)=O)=C1F YKBROVXUBANFCS-MDZDMXLPSA-N 0.000 claims description 2
• DZMWVLAGFIMXPL-UHFFFAOYSA-N 7-amino-3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-methyl-8-pyridin-3-yl-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound COC1=CC(OC)=C(F)C(N2C(N(C)C3=C(C=4C=NC=CC=4)C(N)=NC=C3C2)=O)=C1F DZMWVLAGFIMXPL-UHFFFAOYSA-N 0.000 claims description 2
• ZXZYUVSUMVHXPF-UHFFFAOYSA-N 7-amino-3-(2,6-difluoro-3,5-dimethoxyphenyl)-8-(2-methoxyethoxy)-1-methyl-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound O=C1N(C)C=2C(OCCOC)=C(N)N=CC=2CN1C1=C(F)C(OC)=CC(OC)=C1F ZXZYUVSUMVHXPF-UHFFFAOYSA-N 0.000 claims description 2
• WMBAQRVNANHKCB-UHFFFAOYSA-N 7-amino-3-(2,6-difluoro-3,5-dimethoxyphenyl)-8-[1-(2-hydroxyethyl)pyrazol-4-yl]-1-methyl-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound COC1=CC(OC)=C(F)C(N2C(N(C)C3=C(C4=CN(CCO)N=C4)C(N)=NC=C3C2)=O)=C1F WMBAQRVNANHKCB-UHFFFAOYSA-N 0.000 claims description 2
• WORXVHLKINLMRW-UHFFFAOYSA-N 7-amino-3-(2,6-difluoro-3,5-dimethoxyphenyl)-8-ethyl-1-methyl-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound O=C1N(C)C=2C(CC)=C(N)N=CC=2CN1C1=C(F)C(OC)=CC(OC)=C1F WORXVHLKINLMRW-UHFFFAOYSA-N 0.000 claims description 2
• BCKHPUUCWIEEGJ-UHFFFAOYSA-N 7-amino-3-(2,6-difluoro-3,5-dimethoxyphenyl)-8-methyl-1-(2-methyltetrazol-5-yl)-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound COC1=CC(OC)=C(F)C(N2C(N(C3=NN(C)N=N3)C3=C(C)C(N)=NC=C3C2)=O)=C1F BCKHPUUCWIEEGJ-UHFFFAOYSA-N 0.000 claims description 2
• XJDWLJXIEVLSPK-UHFFFAOYSA-N 7-amino-3-(2,6-difluoro-3,5-dimethoxyphenyl)-8-methyl-1-[(1-methylpyrazol-4-yl)methyl]-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound COC1=CC(OC)=C(F)C(N2C(N(CC3=CN(C)N=C3)C3=C(C)C(N)=NC=C3C2)=O)=C1F XJDWLJXIEVLSPK-UHFFFAOYSA-N 0.000 claims description 2
• MRZKEVZACCCOPD-UHFFFAOYSA-N 7-amino-8-benzyl-3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-methyl-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound COC1=CC(OC)=C(F)C(N2C(N(C)C3=C(CC=4C=CC=CC=4)C(N)=NC=C3C2)=O)=C1F MRZKEVZACCCOPD-UHFFFAOYSA-N 0.000 claims description 2
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• LTNBGNHAYQWWAD-UHFFFAOYSA-N 7-amino-3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-methyl-8-phenyl-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound COC1=CC(OC)=C(F)C(N2C(N(C)C3=C(C=4C=CC=CC=4)C(N)=NC=C3C2)=O)=C1F LTNBGNHAYQWWAD-UHFFFAOYSA-N 0.000 claims 1
• WSHPHXSKUFJZEO-UHFFFAOYSA-N 7-amino-3-(2,6-difluoro-3,5-dimethoxyphenyl)-8-(4-fluorophenyl)-1-methyl-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound COC1=CC(OC)=C(F)C(N2C(N(C)C3=C(C=4C=CC(F)=CC=4)C(N)=NC=C3C2)=O)=C1F WSHPHXSKUFJZEO-UHFFFAOYSA-N 0.000 claims 1
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