JP6737533B2 - スピロ環式化合物 - Google Patents

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Publication number

JP6737533B2

JP6737533B2 JP2017552060A JP2017552060A JP6737533B2 JP 6737533 B2 JP6737533 B2 JP 6737533B2 JP 2017552060 A JP2017552060 A JP 2017552060A JP 2017552060 A JP2017552060 A JP 2017552060A JP 6737533 B2 JP6737533 B2 JP 6737533B2

Authority

JP

Japan

Prior art keywords

optionally substituted

alkyl

diazaspiro

mmol

indazol

Prior art date

2015-04-03

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• -1 Spiro cyclic compound Chemical class 0.000 title claims description 115
• 150000001875 compounds Chemical class 0.000 claims description 420
• 239000000203 mixture Substances 0.000 claims description 354
• 125000000217 alkyl group Chemical group 0.000 claims description 303
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 158
• 125000001072 heteroaryl group Chemical group 0.000 claims description 146
• 125000000623 heterocyclic group Chemical group 0.000 claims description 124
• 125000003107 substituted aryl group Chemical group 0.000 claims description 96
• 229910052739 hydrogen Inorganic materials 0.000 claims description 94
• 239000001257 hydrogen Substances 0.000 claims description 93
• 201000011510 cancer Diseases 0.000 claims description 90
• 150000003839 salts Chemical class 0.000 claims description 88
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 88
• 206010028980 Neoplasm Diseases 0.000 claims description 84
• 125000003118 aryl group Chemical group 0.000 claims description 58
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 47
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 44
• 229910052736 halogen Inorganic materials 0.000 claims description 38
• 150000002367 halogens Chemical class 0.000 claims description 38
• 102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 claims description 34
• 239000008194 pharmaceutical composition Substances 0.000 claims description 34
• 125000003277 amino group Chemical group 0.000 claims description 32
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 30
• 125000003342 alkenyl group Chemical group 0.000 claims description 29
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 29
• 125000000304 alkynyl group Chemical group 0.000 claims description 26
• 150000002431 hydrogen Chemical class 0.000 claims description 26
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 26
• 230000000694 effects Effects 0.000 claims description 23
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
• 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 22
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
• 230000002401 inhibitory effect Effects 0.000 claims description 20
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
• 108040008097 MAP kinase activity proteins Proteins 0.000 claims description 19
• 102000019149 MAP kinase activity proteins Human genes 0.000 claims description 19
• 229910052799 carbon Inorganic materials 0.000 claims description 19
• 101000876610 Dictyostelium discoideum Extracellular signal-regulated kinase 2 Proteins 0.000 claims description 18
• 101001052493 Homo sapiens Mitogen-activated protein kinase 1 Proteins 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 12
• 125000001188 haloalkyl group Chemical group 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
• 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 7
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 7
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 7
• 125000002252 acyl group Chemical group 0.000 claims description 7
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 7
• 201000005202 lung cancer Diseases 0.000 claims description 7
• 208000020816 lung neoplasm Diseases 0.000 claims description 7
• 230000010076 replication Effects 0.000 claims description 7
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 7
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
• 201000002510 thyroid cancer Diseases 0.000 claims description 7
• 206010009944 Colon cancer Diseases 0.000 claims description 6
• 239000004202 carbamide Substances 0.000 claims description 6
• 208000029742 colonic neoplasm Diseases 0.000 claims description 6
• 229910052805 deuterium Inorganic materials 0.000 claims description 6
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 6
• 201000001441 melanoma Diseases 0.000 claims description 6
• 201000002528 pancreatic cancer Diseases 0.000 claims description 6
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 6
• 229940124530 sulfonamide Drugs 0.000 claims description 6
• 150000003672 ureas Chemical class 0.000 claims description 6
• 206010005003 Bladder cancer Diseases 0.000 claims description 5
• 206010033128 Ovarian cancer Diseases 0.000 claims description 5
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 5
• 201000010536 head and neck cancer Diseases 0.000 claims description 5
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 5
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
• 150000002923 oximes Chemical class 0.000 claims description 5
• 208000001608 teratocarcinoma Diseases 0.000 claims description 5
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 5
• 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims description 4
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 4
• 206010006187 Breast cancer Diseases 0.000 claims description 4
• 208000026310 Breast neoplasm Diseases 0.000 claims description 4
• 208000034578 Multiple myelomas Diseases 0.000 claims description 4
• 206010029260 Neuroblastoma Diseases 0.000 claims description 4
• 208000009905 Neurofibromatoses Diseases 0.000 claims description 4
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 4
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 4
• 206010060862 Prostate cancer Diseases 0.000 claims description 4
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
• 206010039491 Sarcoma Diseases 0.000 claims description 4
• 208000025113 myeloid leukemia Diseases 0.000 claims description 4
• 201000004931 neurofibromatosis Diseases 0.000 claims description 4
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 3
• 208000001446 Anaplastic Thyroid Carcinoma Diseases 0.000 claims description 3
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
• 206010038389 Renal cancer Diseases 0.000 claims description 3
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
• 150000002429 hydrazines Chemical class 0.000 claims description 3
• 201000010982 kidney cancer Diseases 0.000 claims description 3
• 201000007270 liver cancer Diseases 0.000 claims description 3
• 208000014018 liver neoplasm Diseases 0.000 claims description 3
• 208000019179 thyroid gland undifferentiated (anaplastic) carcinoma Diseases 0.000 claims description 3
• 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 claims description 2
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 8
• 206010002240 Anaplastic thyroid cancer Diseases 0.000 claims 2
• OBKRRKAUHSPXPC-QNGWXLTQSA-N (5S)-2-[3-(1-acetylpiperidin-4-yl)-2H-indazol-5-yl]-7-[2-[4-[4-(1-methyl-1,2,4-triazol-3-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-2,7-diazaspiro[4.4]nonan-1-one Chemical compound CN1C=NC(=N1)C1=CC=C(C=C1)C1=CCN(CC1)C(=O)CN1CC[C@]2(CCN(C2=O)C2=CC3=C(NN=C3C3CCN(CC3)C(C)=O)C=C2)C1 OBKRRKAUHSPXPC-QNGWXLTQSA-N 0.000 claims 1
• GTZJXZZYRIMYEL-LHEWISCISA-N (5S)-2-[3-(2-methyl-1,3-benzoxazol-5-yl)-1H-indazol-5-yl]-7-[2-[4-[4-(1-methyl-1,2,4-triazol-3-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-2,7-diazaspiro[4.4]nonan-1-one Chemical compound CN1N=C(N=C1)C1=CC=C(C=C1)C=1CCN(CC=1)C(CN1C[C@@]2(CCN(C2=O)C=2C=C3C(=NNC3=CC=2)C=2C=CC3=C(N=C(O3)C)C=2)CC1)=O GTZJXZZYRIMYEL-LHEWISCISA-N 0.000 claims 1
• NWPDFALVYJWUJA-DHUJRADRSA-N (5S)-2-[3-(3,6-dihydro-2H-pyran-4-yl)-1H-indazol-5-yl]-7-[2-[4-[4-(1-methyl-1,2,4-triazol-3-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-2,7-diazaspiro[4.4]nonan-1-one Chemical compound CN1C=NC(=N1)C1=CC=C(C=C1)C1=CCN(CC1)C(=O)CN1CC[C@]2(CCN(C2=O)C2=CC3=C(NN=C3C3=CCOCC3)C=C2)C1 NWPDFALVYJWUJA-DHUJRADRSA-N 0.000 claims 1
• RSOAEEGYFGFBCE-QNGWXLTQSA-N (5S)-2-[3-(4-methoxyphenyl)-1H-indazol-5-yl]-7-[2-[4-[4-(1-methyl-1,2,4-triazol-3-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-2,7-diazaspiro[4.4]nonan-1-one Chemical compound COC1=CC=C(C=C1)C1=NNC2=C1C=C(C=C2)N1CC[C@]2(CCN(CC(=O)N3CCC(=CC3)C3=CC=C(C=C3)C3=NN(C)C=N3)C2)C1=O RSOAEEGYFGFBCE-QNGWXLTQSA-N 0.000 claims 1
• KJEOBKKNJGKUMR-BHVANESWSA-N (5S)-2-[3-(4-methoxypiperidin-1-yl)-1H-indazol-5-yl]-7-[2-[4-[4-(1-methyl-1,2,4-triazol-3-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-2,7-diazaspiro[4.4]nonan-1-one Chemical compound COC1CCN(CC1)C1=NNC2=C1C=C(C=C2)N1CC[C@]2(CCN(CC(=O)N3CCC(=CC3)C3=CC=C(C=C3)C3=NN(C)C=N3)C2)C1=O KJEOBKKNJGKUMR-BHVANESWSA-N 0.000 claims 1
• GEORDXNJIBHRFW-DHUJRADRSA-N (5S)-2-[3-[2-(difluoromethyl)pyrimidin-5-yl]-1H-indazol-5-yl]-7-[2-[4-[4-(1-methyl-1,2,4-triazol-3-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-2,7-diazaspiro[4.4]nonan-1-one Chemical compound CN1C=NC(=N1)C1=CC=C(C=C1)C1=CCN(CC1)C(=O)CN1CC[C@]2(CCN(C2=O)C2=CC3=C(NN=C3C3=CN=C(N=C3)C(F)F)C=C2)C1 GEORDXNJIBHRFW-DHUJRADRSA-N 0.000 claims 1
• HNVBYPHCKMNORJ-DNUYPZOSSA-N (5S)-2-[3-[6-(1-hydroxypropan-2-yl)pyridin-3-yl]-1H-indazol-5-yl]-7-[2-[4-[4-(1-methyl-1,2,4-triazol-3-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-2,7-diazaspiro[4.4]nonan-1-one Chemical compound CC(CO)C1=CC=C(C=N1)C1=NNC2=C1C=C(C=C2)N1CC[C@]2(CCN(CC(=O)N3CCC(=CC3)C3=CC=C(C=C3)C3=NN(C)C=N3)C2)C1=O HNVBYPHCKMNORJ-DNUYPZOSSA-N 0.000 claims 1
• YNIJUTINJJMWKK-BHVANESWSA-N (5S)-2-[3-[6-(difluoromethyl)pyridin-3-yl]-1H-indazol-5-yl]-7-[2-[4-[4-(1-methyl-1,2,4-triazol-3-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-2,7-diazaspiro[4.4]nonan-1-one Chemical compound CN1C=NC(=N1)C1=CC=C(C=C1)C1=CCN(CC1)C(=O)CN1CC[C@]2(CCN(C2=O)C2=CC3=C(NN=C3C3=CC=C(N=C3)C(F)F)C=C2)C1 YNIJUTINJJMWKK-BHVANESWSA-N 0.000 claims 1
• DFLXRQAIQUAIFJ-KDXMTYKHSA-N (5S)-7-[2-[4-[4-(1-cyclopropyl-1,2,4-triazol-3-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-2-[3-(6-propan-2-yloxypyridin-3-yl)-1H-pyrazolo[4,3-b]pyridin-5-yl]-2,7-diazaspiro[4.4]nonan-1-one Chemical compound CC(C)OC1=CC=C(C=N1)C1=NNC2=C1N=C(C=C2)N1CC[C@]2(CCN(CC(=O)N3CCC(=CC3)C3=CC=C(C=C3)C3=NN(C=N3)C3CC3)C2)C1=O DFLXRQAIQUAIFJ-KDXMTYKHSA-N 0.000 claims 1
• BPGVSQWUBDBBAJ-DHUJRADRSA-N (5S)-7-[2-[4-[4-(1-methyl-1,2,4-triazol-3-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-2-[3-(oxan-4-yl)-2H-indazol-5-yl]-2,7-diazaspiro[4.4]nonan-1-one Chemical compound CN1C=NC(=N1)C1=CC=C(C=C1)C1=CCN(CC1)C(=O)CN1CC[C@]2(CCN(C2=O)C2=CC3=C(NN=C3C3CCOCC3)C=C2)C1 BPGVSQWUBDBBAJ-DHUJRADRSA-N 0.000 claims 1
• AQZWQCDSFJRAEJ-DHUJRADRSA-N (5S)-7-[2-[4-[4-(1-methyl-1,2,4-triazol-3-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-2-[3-[6-(trifluoromethyl)pyridin-3-yl]-1H-indazol-5-yl]-2,7-diazaspiro[4.4]nonan-1-one Chemical compound CN1C=NC(=N1)C1=CC=C(C=C1)C1=CCN(CC1)C(=O)CN1CC[C@]2(CCN(C2=O)C2=CC3=C(NN=C3C3=CC=C(N=C3)C(F)(F)F)C=C2)C1 AQZWQCDSFJRAEJ-DHUJRADRSA-N 0.000 claims 1
• XHFIEJBGBYWSDA-DHUJRADRSA-N (5S)-7-[2-[4-[5-(1-methyl-1,2,4-triazol-3-yl)-1,3-thiazol-2-yl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-2-[3-(6-propan-2-yloxypyridin-3-yl)-1H-indazol-5-yl]-2,7-diazaspiro[4.4]nonan-1-one Chemical compound CC(C)OC1=CC=C(C=N1)C1=NNC2=C1C=C(C=C2)N1CC[C@]2(CCN(CC(=O)N3CCC(=CC3)C3=NC=C(S3)C3=NN(C)C=N3)C2)C1=O XHFIEJBGBYWSDA-DHUJRADRSA-N 0.000 claims 1
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
• GAXAFTQHTHBBPG-LHEWISCISA-N 2-methoxy-4-[5-[(5S)-7-[2-[4-[4-(1-methyl-1,2,4-triazol-3-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-1-oxo-2,7-diazaspiro[4.4]nonan-2-yl]-1H-indazol-3-yl]benzonitrile Chemical compound COC1=C(C=CC(=C1)C1=NNC2=C1C=C(C=C2)N1CC[C@]2(CCN(CC(=O)N3CCC(=CC3)C3=CC=C(C=C3)C3=NN(C)C=N3)C2)C1=O)C#N GAXAFTQHTHBBPG-LHEWISCISA-N 0.000 claims 1
• VGKFRMVABBXTKV-LHEWISCISA-N 2-methoxy-4-[5-[(5S)-7-[2-[4-[4-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-1-oxo-2,7-diazaspiro[4.4]nonan-2-yl]-1H-indazol-3-yl]benzonitrile Chemical compound COC1=C(C=CC(=C1)C1=NNC2=C1C=C(C=C2)N1CC[C@]2(CCN(CC(=O)N3CCC(=CC3)C3=CC=C(C=C3)C3=NN(C)C(=O)O3)C2)C1=O)C#N VGKFRMVABBXTKV-LHEWISCISA-N 0.000 claims 1
• QUTCNADPXCXUDU-LHEWISCISA-N 2-methoxy-5-[5-[(5S)-7-[2-[4-[4-(1-methyl-1,2,4-triazol-3-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-1-oxo-2,7-diazaspiro[4.4]nonan-2-yl]-1H-indazol-3-yl]benzonitrile Chemical compound COC1=C(C=C(C=C1)C1=NNC2=C1C=C(C=C2)N1CC[C@]2(CCN(CC(=O)N3CCC(=CC3)C3=CC=C(C=C3)C3=NN(C)C=N3)C2)C1=O)C#N QUTCNADPXCXUDU-LHEWISCISA-N 0.000 claims 1
• IYSICUHAZQBAHA-LHEWISCISA-N 2-methoxy-5-[5-[(5S)-7-[2-[4-[4-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-1-oxo-2,7-diazaspiro[4.4]nonan-2-yl]-1H-indazol-3-yl]benzonitrile Chemical compound COC1=C(C=C(C=C1)C1=NNC2=C1C=C(C=C2)N1CC[C@]2(CCN(CC(=O)N3CCC(=CC3)C3=CC=C(C=C3)C3=NN(C)C(=O)O3)C2)C1=O)C#N IYSICUHAZQBAHA-LHEWISCISA-N 0.000 claims 1
• AVPCTOPEWYDAOF-QNGWXLTQSA-N 3-[5-[(5S)-7-[2-[4-[4-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-1-oxo-2,7-diazaspiro[4.4]nonan-2-yl]-1H-indazol-3-yl]benzonitrile Chemical compound CN1N=C(OC1=O)C1=CC=C(C=C1)C1=CCN(CC1)C(=O)CN1CC[C@]2(CCN(C2=O)C2=CC3=C(NN=C3C3=CC=CC(=C3)C#N)C=C2)C1 AVPCTOPEWYDAOF-QNGWXLTQSA-N 0.000 claims 1
• UBIWVURAOAWIKD-LHEWISCISA-N 3-methyl-5-[4-[1-[2-[(5S)-1-oxo-2-[3-(6-propan-2-yloxypyridin-3-yl)-1H-indazol-5-yl]-2,7-diazaspiro[4.4]nonan-7-yl]acetyl]-3,6-dihydro-2H-pyridin-4-yl]phenyl]-1,3,4-oxadiazol-2-one Chemical compound CC(C)OC1=CC=C(C=N1)C1=NNC2=C1C=C(C=C2)N1CC[C@]2(CCN(CC(=O)N3CCC(=CC3)C3=CC=C(C=C3)C3=NN(C)C(=O)O3)C2)C1=O UBIWVURAOAWIKD-LHEWISCISA-N 0.000 claims 1
• SDGQMSQBXNJHJM-LHEWISCISA-N 3-methyl-5-[4-[1-[2-[(5S)-2-[3-(2-methyl-1,3-benzoxazol-5-yl)-1H-indazol-5-yl]-1-oxo-2,7-diazaspiro[4.4]nonan-7-yl]acetyl]-3,6-dihydro-2H-pyridin-4-yl]phenyl]-1,3,4-oxadiazol-2-one Chemical compound CN1N=C(OC1=O)C1=CC=C(C=C1)C1=CCN(CC1)C(=O)CN1CC[C@]2(CCN(C2=O)C2=CC3=C(NN=C3C3=CC=C4OC(C)=NC4=C3)C=C2)C1 SDGQMSQBXNJHJM-LHEWISCISA-N 0.000 claims 1
• VOQRHOCHBNQSDK-DHUJRADRSA-N 3-methyl-5-[4-[1-[2-[(5S)-2-[3-(oxan-4-yl)-2H-indazol-5-yl]-1-oxo-2,7-diazaspiro[4.4]nonan-7-yl]acetyl]-3,6-dihydro-2H-pyridin-4-yl]phenyl]-1,3,4-oxadiazol-2-one Chemical compound CN1N=C(OC1=O)C1=CC=C(C=C1)C1=CCN(CC1)C(=O)CN1CC[C@]2(CCN(C2=O)C2=CC3=C(NN=C3C3CCOCC3)C=C2)C1 VOQRHOCHBNQSDK-DHUJRADRSA-N 0.000 claims 1
• AZRIIERYKDENHS-QNGWXLTQSA-N 4-[5-[(5S)-7-[2-[4-[4-(1-methyl-1,2,4-triazol-3-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-1-oxo-2,7-diazaspiro[4.4]nonan-2-yl]-1H-indazol-3-yl]benzonitrile Chemical compound CN1C=NC(=N1)C1=CC=C(C=C1)C1=CCN(CC1)C(=O)CN1CC[C@]2(CCN(C2=O)C2=CC3=C(NN=C3C3=CC=C(C=C3)C#N)C=C2)C1 AZRIIERYKDENHS-QNGWXLTQSA-N 0.000 claims 1
• CFIIXPSJXDHGHV-QNGWXLTQSA-N 4-[5-[(5S)-7-[2-[4-[4-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-1-oxo-2,7-diazaspiro[4.4]nonan-2-yl]-1H-indazol-3-yl]benzonitrile Chemical compound CN1N=C(OC1=O)C1=CC=C(C=C1)C1=CCN(CC1)C(=O)CN1CC[C@]2(CCN(C2=O)C2=CC3=C(NN=C3C3=CC=C(C=C3)C#N)C=C2)C1 CFIIXPSJXDHGHV-QNGWXLTQSA-N 0.000 claims 1
• PGOSFFMPLHMFDQ-QNGWXLTQSA-N 5-[4-[1-[2-[(5S)-2-[3-(1-acetylpiperidin-4-yl)-2H-indazol-5-yl]-1-oxo-2,7-diazaspiro[4.4]nonan-7-yl]acetyl]-3,6-dihydro-2H-pyridin-4-yl]phenyl]-3-methyl-1,3,4-oxadiazol-2-one Chemical compound CN1N=C(OC1=O)C1=CC=C(C=C1)C1=CCN(CC1)C(=O)CN1CC[C@]2(CCN(C2=O)C2=CC3=C(NN=C3C3CCN(CC3)C(C)=O)C=C2)C1 PGOSFFMPLHMFDQ-QNGWXLTQSA-N 0.000 claims 1
• JQOOTZJBZLSXKF-BHVANESWSA-N 5-[4-[1-[2-[(5S)-2-[3-(4-methoxypiperidin-1-yl)-1H-indazol-5-yl]-1-oxo-2,7-diazaspiro[4.4]nonan-7-yl]acetyl]-3,6-dihydro-2H-pyridin-4-yl]phenyl]-3-methyl-1,3,4-oxadiazol-2-one Chemical compound COC1CCN(CC1)C1=NNC2=C1C=C(C=C2)N1CC[C@]2(CCN(CC(=O)N3CCC(=CC3)C3=CC=C(C=C3)C3=NN(C)C(=O)O3)C2)C1=O JQOOTZJBZLSXKF-BHVANESWSA-N 0.000 claims 1
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