CA2907594A1 - Heteroaryl substituted indazoles - Google Patents

Info

Publication number

CA2907594A1

CA2907594A1 CA2907594A CA2907594A CA2907594A1 CA 2907594 A1 CA2907594 A1 CA 2907594A1 CA 2907594 A CA2907594 A CA 2907594A CA 2907594 A CA2907594 A CA 2907594A CA 2907594 A1 CA2907594 A1 CA 2907594A1

Authority

CA

Canada

Prior art keywords

alkyl

methyl

pyrimidin

hydrogen

indazol

Prior art date

2013-03-21

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 125000001072 heteroaryl group Chemical group 0.000 title claims description 42
• 150000002473 indoazoles Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 285
• -1 1-4C-haloalkoxy Chemical group 0.000 claims description 235
• 229910052739 hydrogen Inorganic materials 0.000 claims description 112
• 239000001257 hydrogen Substances 0.000 claims description 109
• 150000003839 salts Chemical class 0.000 claims description 108
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 96
• 239000000203 mixture Substances 0.000 claims description 70
• 206010028980 Neoplasm Diseases 0.000 claims description 68
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 63
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 54
• 229910052757 nitrogen Inorganic materials 0.000 claims description 50
• 150000002431 hydrogen Chemical class 0.000 claims description 48
• 150000001204 N-oxides Chemical class 0.000 claims description 42
• 229910052736 halogen Inorganic materials 0.000 claims description 42
• 150000002367 halogens Chemical class 0.000 claims description 42
• 238000011282 treatment Methods 0.000 claims description 42
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 35
• 201000010099 disease Diseases 0.000 claims description 28
• 239000004480 active ingredient Substances 0.000 claims description 25
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
• 206010027476 Metastases Diseases 0.000 claims description 21
• 239000000460 chlorine Substances 0.000 claims description 21
• 229910052801 chlorine Inorganic materials 0.000 claims description 20
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• 125000000623 heterocyclic group Chemical group 0.000 claims description 13
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 13
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
• AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
• 230000002489 hematologic effect Effects 0.000 claims description 11
• 125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 claims description 10
• 125000004515 1,2,4-thiadiazol-3-yl group Chemical group S1N=C(N=C1)* 0.000 claims description 10
• JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 10
• 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 10
• 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 10
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
• 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 10
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 10
• 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims description 9
• 230000030833 cell death Effects 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 8
• 230000003463 hyperproliferative effect Effects 0.000 claims description 8
• 238000011321 prophylaxis Methods 0.000 claims description 8
• 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 7
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 239000002246 antineoplastic agent Substances 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 208000024719 uterine cervix neoplasm Diseases 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 4
• 230000006698 induction Effects 0.000 claims description 4
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
• 230000000973 chemotherapeutic effect Effects 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
• DIZUXOSYZFWMHT-UHFFFAOYSA-N 2-[1-(imidazo[1,2-a]pyrimidin-2-ylmethyl)indazol-3-yl]-5-methoxy-n-pyridin-4-ylpyrimidin-4-amine Chemical compound COC1=CN=C(C=2C3=CC=CC=C3N(CC=3N=C4N=CC=CN4C=3)N=2)N=C1NC1=CC=NC=C1 DIZUXOSYZFWMHT-UHFFFAOYSA-N 0.000 claims 1
• AOXLMWVSMRTYJC-UHFFFAOYSA-N 2-[1-[(1,5-dimethylpyrazol-4-yl)methyl]indazol-3-yl]-5-methoxy-n-pyridin-4-ylpyrimidin-4-amine Chemical compound COC1=CN=C(C=2C3=CC=CC=C3N(CC3=C(N(C)N=C3)C)N=2)N=C1NC1=CC=NC=C1 AOXLMWVSMRTYJC-UHFFFAOYSA-N 0.000 claims 1
• XCZBIEPAGXBIIL-UHFFFAOYSA-N 2-[1-[(2,4-dichloropyridin-3-yl)methyl]indazol-3-yl]-5-methoxy-n-pyridin-4-ylpyrimidin-4-amine Chemical compound COC1=CN=C(C=2C3=CC=CC=C3N(CC=3C(=NC=CC=3Cl)Cl)N=2)N=C1NC1=CC=NC=C1 XCZBIEPAGXBIIL-UHFFFAOYSA-N 0.000 claims 1
• SQJJJWDHWDOWDM-UHFFFAOYSA-N 2-[1-[(3,5-difluoropyridin-2-yl)methyl]indazol-3-yl]-5-methoxy-n-pyridin-4-ylpyrimidin-4-amine Chemical compound COC1=CN=C(C=2C3=CC=CC=C3N(CC=3C(=CC(F)=CN=3)F)N=2)N=C1NC1=CC=NC=C1 SQJJJWDHWDOWDM-UHFFFAOYSA-N 0.000 claims 1
• MPKGGQJWDWXRBU-UHFFFAOYSA-N 2-[1-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]indazol-3-yl]-4-N-pyrimidin-4-ylpyrimidine-4,6-diamine Chemical compound CC1=NOC(=C1CN1N=C(C2=CC=CC=C12)C1=NC(=CC(=N1)NC1=NC=NC=C1)N)C MPKGGQJWDWXRBU-UHFFFAOYSA-N 0.000 claims 1
• BDFNGLQQVCCDJE-UHFFFAOYSA-N 2-[1-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]indazol-3-yl]-5-methoxy-n-pyridin-4-ylpyrimidin-4-amine Chemical compound COC1=CN=C(C=2C3=CC=CC=C3N(CC3=C(ON=C3C)C)N=2)N=C1NC1=CC=NC=C1 BDFNGLQQVCCDJE-UHFFFAOYSA-N 0.000 claims 1
• CYMIIRZBZSAWTM-UHFFFAOYSA-N 2-[1-[(4-chloro-1-methylpyrazol-3-yl)methyl]indazol-3-yl]-5-methoxy-n-pyridin-4-ylpyrimidin-4-amine Chemical compound COC1=CN=C(C=2C3=CC=CC=C3N(CC=3C(=CN(C)N=3)Cl)N=2)N=C1NC1=CC=NC=C1 CYMIIRZBZSAWTM-UHFFFAOYSA-N 0.000 claims 1
• LZEHKOYSBZCGJC-UHFFFAOYSA-N 2-[1-[(4-chloro-2-methylpyrazol-3-yl)methyl]indazol-3-yl]-5-methoxy-n-pyridin-4-ylpyrimidin-4-amine Chemical compound COC1=CN=C(C=2C3=CC=CC=C3N(CC=3N(N=CC=3Cl)C)N=2)N=C1NC1=CC=NC=C1 LZEHKOYSBZCGJC-UHFFFAOYSA-N 0.000 claims 1
• RORJPNLIANQEIZ-UHFFFAOYSA-N 2-[1-[[3-(difluoromethyl)-1-methyl-5-(2,2,2-trifluoroethoxy)pyrazol-4-yl]methyl]indazol-3-yl]-5-methoxy-n-pyridin-4-ylpyrimidin-4-amine Chemical compound COC1=CN=C(C=2C3=CC=CC=C3N(CC3=C(N(C)N=C3C(F)F)OCC(F)(F)F)N=2)N=C1NC1=CC=NC=C1 RORJPNLIANQEIZ-UHFFFAOYSA-N 0.000 claims 1
• YVWQPIUXEZPUAH-UHFFFAOYSA-N 2-[1-[[3-(difluoromethyl)-5-methyltriazol-4-yl]methyl]indazol-3-yl]-5-methoxy-N-pyridin-4-ylpyrimidin-4-amine Chemical compound FC(N1N=NC(=C1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=CC=NC=C1)OC)C)F YVWQPIUXEZPUAH-UHFFFAOYSA-N 0.000 claims 1
• XJBKFQYLEVZLTB-UHFFFAOYSA-N 2-[1-[[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methyl]indazol-3-yl]-5-methoxy-n-pyridin-4-ylpyrimidin-4-amine Chemical compound COC1=CN=C(C=2C3=CC=CC=C3N(CC3=C(N(C)N=C3C(F)(F)F)C(F)F)N=2)N=C1NC1=CC=NC=C1 XJBKFQYLEVZLTB-UHFFFAOYSA-N 0.000 claims 1
• NLOYTXBYYLEGRV-UHFFFAOYSA-N 3-[[3-[5-methoxy-4-(pyridin-4-ylamino)pyrimidin-2-yl]indazol-1-yl]methyl]-1,2,4-thiadiazol-5-amine Chemical compound COC1=CN=C(C=2C3=CC=CC=C3N(CC=3N=C(N)SN=3)N=2)N=C1NC1=CC=NC=C1 NLOYTXBYYLEGRV-UHFFFAOYSA-N 0.000 claims 1
• KVCLBAKRZREQPO-UHFFFAOYSA-N 3-[[3-[5-methoxy-4-(pyridin-4-ylamino)pyrimidin-2-yl]indazol-1-yl]methyl]-n-methyl-1,2,4-oxadiazole-5-carboxamide Chemical compound O1C(C(=O)NC)=NC(CN2C3=CC=CC=C3C(C=3N=C(NC=4C=CN=CC=4)C(OC)=CN=3)=N2)=N1 KVCLBAKRZREQPO-UHFFFAOYSA-N 0.000 claims 1
• GBEZMDABCHMJCA-UHFFFAOYSA-N 4-[[5-methoxy-2-[1-(1,3-thiazol-4-ylmethyl)indazol-3-yl]pyrimidin-4-yl]amino]pyridine-3-carboxamide Chemical compound COC1=CN=C(C=2C3=CC=CC=C3N(CC=3N=CSC=3)N=2)N=C1NC1=CC=NC=C1C(N)=O GBEZMDABCHMJCA-UHFFFAOYSA-N 0.000 claims 1
• VTBCSKMGLIJKBL-UHFFFAOYSA-N 4-[[5-methoxy-2-[1-[(3-propan-2-yl-1,2-oxazol-5-yl)methyl]indazol-3-yl]pyrimidin-4-yl]amino]-n-methylpyridine-3-carboxamide Chemical compound CNC(=O)C1=CN=CC=C1NC1=NC(C=2C3=CC=CC=C3N(CC=3ON=C(C=3)C(C)C)N=2)=NC=C1OC VTBCSKMGLIJKBL-UHFFFAOYSA-N 0.000 claims 1
• POMVBCACGIIYNX-UHFFFAOYSA-N 4-[[5-methoxy-2-[1-[(3-propan-2-yl-1,2-oxazol-5-yl)methyl]indazol-3-yl]pyrimidin-4-yl]amino]pyridine-3-carboxamide Chemical compound COC1=CN=C(C=2C3=CC=CC=C3N(CC=3ON=C(C=3)C(C)C)N=2)N=C1NC1=CC=NC=C1C(N)=O POMVBCACGIIYNX-UHFFFAOYSA-N 0.000 claims 1
• BAHPORRCUIQCLD-UHFFFAOYSA-N 4-[[5-methoxy-2-[1-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]indazol-3-yl]pyrimidin-4-yl]amino]-n-methylpyridine-3-carboxamide Chemical compound CNC(=O)C1=CN=CC=C1NC1=NC(C=2C3=CC=CC=C3N(CC=3OC(C)=NN=3)N=2)=NC=C1OC BAHPORRCUIQCLD-UHFFFAOYSA-N 0.000 claims 1
• HWXGOTUJGINOKR-UHFFFAOYSA-N 4-[[5-methoxy-2-[1-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]indazol-3-yl]pyrimidin-4-yl]amino]pyridine-3-carboxamide Chemical compound COC1=CN=C(C=2C3=CC=CC=C3N(CC=3OC(C)=NN=3)N=2)N=C1NC1=CC=NC=C1C(N)=O HWXGOTUJGINOKR-UHFFFAOYSA-N 0.000 claims 1
• NKTGFOYXRPAKCD-UHFFFAOYSA-N 4-[[5-methoxy-2-[1-[[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]methyl]indazol-3-yl]pyrimidin-4-yl]amino]-n-methylpyridine-3-carboxamide Chemical compound CNC(=O)C1=CN=CC=C1NC1=NC(C=2C3=CC=CC=C3N(CC=3ON=C(COC)N=3)N=2)=NC=C1OC NKTGFOYXRPAKCD-UHFFFAOYSA-N 0.000 claims 1
• SGBADWSIRDQPMK-UHFFFAOYSA-N 4-[[5-methoxy-2-[1-[[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]methyl]indazol-3-yl]pyrimidin-4-yl]amino]pyridine-3-carboxamide Chemical compound COCC1=NOC(CN2C3=CC=CC=C3C(C=3N=C(NC=4C(=CN=CC=4)C(N)=O)C(OC)=CN=3)=N2)=N1 SGBADWSIRDQPMK-UHFFFAOYSA-N 0.000 claims 1
• XSCYHWKSVSMIHP-UHFFFAOYSA-N 4-[[6-amino-2-[1-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]indazol-3-yl]pyrimidin-4-yl]amino]-n-(2-hydroxyethyl)pyridine-3-carboxamide Chemical compound CC1=NOC(C)=C1CN1C2=CC=CC=C2C(C=2N=C(NC=3C(=CN=CC=3)C(=O)NCCO)C=C(N)N=2)=N1 XSCYHWKSVSMIHP-UHFFFAOYSA-N 0.000 claims 1
• ZBGMMTUEKRPYEM-UHFFFAOYSA-N 5-methoxy-2-[1-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]indazol-3-yl]-n-pyridin-4-ylpyrimidin-4-amine Chemical compound COC1=CN=C(C=2C3=CC=CC=C3N(CC=3OC(C)=NN=3)N=2)N=C1NC1=CC=NC=C1 ZBGMMTUEKRPYEM-UHFFFAOYSA-N 0.000 claims 1
• UVRFYQGDKBEWJJ-UHFFFAOYSA-N 5-methoxy-2-[1-[[2-methyl-6-(trifluoromethyl)pyridin-3-yl]methyl]indazol-3-yl]-N-pyridin-4-ylpyrimidin-4-amine Chemical compound COC=1C(=NC(=NC=1)C1=NN(C2=CC=CC=C12)CC=1C(=NC(=CC=1)C(F)(F)F)C)NC1=CC=NC=C1 UVRFYQGDKBEWJJ-UHFFFAOYSA-N 0.000 claims 1
• OYVAYKZZPAIENB-UHFFFAOYSA-N 5-methoxy-2-[1-[[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]methyl]indazol-3-yl]-n-pyridin-4-ylpyrimidin-4-amine Chemical compound COCC1=NOC(CN2C3=CC=CC=C3C(C=3N=C(NC=4C=CN=CC=4)C(OC)=CN=3)=N2)=N1 OYVAYKZZPAIENB-UHFFFAOYSA-N 0.000 claims 1
• IRIYNGNWDHTUPQ-UHFFFAOYSA-N 5-methoxy-2-[1-[[3-methyl-5-(trifluoromethyl)triazol-4-yl]methyl]indazol-3-yl]-n-pyridin-4-ylpyrimidin-4-amine Chemical compound COC1=CN=C(C=2C3=CC=CC=C3N(CC=3N(N=NC=3C(F)(F)F)C)N=2)N=C1NC1=CC=NC=C1 IRIYNGNWDHTUPQ-UHFFFAOYSA-N 0.000 claims 1
• XABJQAGEXHGUBR-UHFFFAOYSA-N 6-[[3-[5-methoxy-4-(pyridin-4-ylamino)pyrimidin-2-yl]indazol-1-yl]methyl]-1h-pyrimidine-2,4-dione Chemical compound COC1=CN=C(C=2C3=CC=CC=C3N(CC=3NC(=O)NC(=O)C=3)N=2)N=C1NC1=CC=NC=C1 XABJQAGEXHGUBR-UHFFFAOYSA-N 0.000 claims 1
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• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
• DFVCMYFGPPGVHB-UHFFFAOYSA-N ethyl 4-[[6-amino-2-[1-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]indazol-3-yl]pyrimidin-4-yl]amino]pyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=CC=C1NC1=CC(N)=NC(C=2C3=CC=CC=C3N(CC3=C(ON=C3C)C)N=2)=N1 DFVCMYFGPPGVHB-UHFFFAOYSA-N 0.000 claims 1
• KLSPSGLWKJATAO-UHFFFAOYSA-N n-[[3-(difluoromethyl)-5-methyltriazol-4-yl]methyl]-2-[1-[[3-(difluoromethyl)-5-methyltriazol-4-yl]methyl]indazol-3-yl]-5-methoxy-n-pyridin-4-ylpyrimidin-4-amine Chemical compound COC1=CN=C(C=2C3=CC=CC=C3N(CC=3N(N=NC=3C)C(F)F)N=2)N=C1N(C=1C=CN=CC=1)CC1=C(C)N=NN1C(F)F KLSPSGLWKJATAO-UHFFFAOYSA-N 0.000 claims 1
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