CA2907592A1 - 3-heteroaryl substituted indazoles - Google Patents

Info

Publication number

CA2907592A1

CA2907592A1 CA2907592A CA2907592A CA2907592A1 CA 2907592 A1 CA2907592 A1 CA 2907592A1 CA 2907592 A CA2907592 A CA 2907592A CA 2907592 A CA2907592 A CA 2907592A CA 2907592 A1 CA2907592 A1 CA 2907592A1

Authority

CA

Canada

Prior art keywords

alkyl

hydrogen

pyrimidin

indazol

optionally substituted

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

• 150000002473 indoazoles Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 322
• -1 cyano, hydroxy Chemical group 0.000 claims description 308
• 229910052739 hydrogen Inorganic materials 0.000 claims description 166
• 239000001257 hydrogen Substances 0.000 claims description 162
• 150000002431 hydrogen Chemical class 0.000 claims description 110
• 150000003839 salts Chemical class 0.000 claims description 105
• 125000001072 heteroaryl group Chemical group 0.000 claims description 97
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 96
• 229910052757 nitrogen Inorganic materials 0.000 claims description 91
• 206010028980 Neoplasm Diseases 0.000 claims description 72
• 229910052736 halogen Inorganic materials 0.000 claims description 70
• 150000002367 halogens Chemical class 0.000 claims description 70
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 68
• 239000000203 mixture Substances 0.000 claims description 61
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 59
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 54
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 52
• 150000001204 N-oxides Chemical class 0.000 claims description 52
• 229910052731 fluorine Inorganic materials 0.000 claims description 49
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 46
• 239000011737 fluorine Substances 0.000 claims description 46
• 238000011282 treatment Methods 0.000 claims description 42
• 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 claims description 34
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 34
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 32
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 32
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 32
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 28
• 201000010099 disease Diseases 0.000 claims description 28
• 125000004432 carbon atom Chemical group C* 0.000 claims description 27
• 125000005842 heteroatom Chemical group 0.000 claims description 27
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 27
• 239000004480 active ingredient Substances 0.000 claims description 26
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 26
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 23
• 229910052727 yttrium Inorganic materials 0.000 claims description 23
• 206010027476 Metastases Diseases 0.000 claims description 22
• 125000000623 heterocyclic group Chemical group 0.000 claims description 22
• 229910052720 vanadium Inorganic materials 0.000 claims description 22
• 229910052717 sulfur Inorganic materials 0.000 claims description 20
• NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims description 17
• 229960004979 fampridine Drugs 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims description 14
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 230000002489 hematologic effect Effects 0.000 claims description 11
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 11
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
• 230000030833 cell death Effects 0.000 claims description 9
• 238000011321 prophylaxis Methods 0.000 claims description 9
• 230000003463 hyperproliferative effect Effects 0.000 claims description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 239000002246 antineoplastic agent Substances 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 208000024719 uterine cervix neoplasm Diseases 0.000 claims description 5
• 230000006698 induction Effects 0.000 claims description 4
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 3
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
• 230000000973 chemotherapeutic effect Effects 0.000 claims description 3
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
• SSADLTBAUHNWJQ-UHFFFAOYSA-N 2-[1-[(2-fluorophenyl)methyl]indazol-3-yl]-4-(pyrimidin-4-ylamino)pyrimidin-5-ol Chemical compound Oc1cnc(nc1Nc1ccncn1)-c1nn(Cc2ccccc2F)c2ccccc12 SSADLTBAUHNWJQ-UHFFFAOYSA-N 0.000 claims 1
• ANGWYKGTWKVXKT-UHFFFAOYSA-N 2-[1-[(2-fluorophenyl)methyl]indazol-3-yl]-5-methoxy-n-pyrimidin-4-ylpyrimidin-4-amine Chemical compound COC1=CN=C(C=2C3=CC=CC=C3N(CC=3C(=CC=CC=3)F)N=2)N=C1NC1=CC=NC=N1 ANGWYKGTWKVXKT-UHFFFAOYSA-N 0.000 claims 1
• KZTYKWLEFVGMCR-UHFFFAOYSA-N 2-[1-[(2-fluorophenyl)methyl]indazol-3-yl]-n-(1-methylpyrazol-4-yl)pyridin-4-amine Chemical compound C1=NN(C)C=C1NC1=CC=NC(C=2C3=CC=CC=C3N(CC=3C(=CC=CC=3)F)N=2)=C1 KZTYKWLEFVGMCR-UHFFFAOYSA-N 0.000 claims 1
• WKNNLMHRHRMFEP-UHFFFAOYSA-N 2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]indazol-3-yl]-5-methoxy-n-(1h-pyrazol-4-yl)pyrimidin-4-amine Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C2=CC=CC=C2C(C=2N=C(NC3=CNN=C3)C(OC)=CN=2)=N1 WKNNLMHRHRMFEP-UHFFFAOYSA-N 0.000 claims 1
• XSSZDCVLKNGLNR-UHFFFAOYSA-N 2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]indazol-3-yl]-5-methoxy-n-phenylpyrimidin-4-amine Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C2=CC=CC=C2C(C=2N=C(NC=3C=CC=CC=3)C(OC)=CN=2)=N1 XSSZDCVLKNGLNR-UHFFFAOYSA-N 0.000 claims 1
• FBUGJGZAAJZBNF-UHFFFAOYSA-N 2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]indazol-3-yl]-5-methoxy-n-pyridazin-4-ylpyrimidin-4-amine Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C2=CC=CC=C2C(C=2N=C(NC=3C=NN=CC=3)C(OC)=CN=2)=N1 FBUGJGZAAJZBNF-UHFFFAOYSA-N 0.000 claims 1
• KPNKTJUDEVNOBG-UHFFFAOYSA-N 2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]indazol-3-yl]-5-methoxy-n-pyrimidin-4-ylpyrimidin-4-amine Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C2=CC=CC=C2C(C=2N=C(NC=3N=CN=CC=3)C(OC)=CN=2)=N1 KPNKTJUDEVNOBG-UHFFFAOYSA-N 0.000 claims 1
• HMOFQRKFXWDHRL-UHFFFAOYSA-N 2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]indazol-3-yl]-n-[1-(ethoxymethyl)pyrazol-4-yl]pyridin-4-amine Chemical compound C1=NN(COCC)C=C1NC1=CC=NC(C=2C3=CC=CC=C3N(CC=3C(=CC(OCC)=CC=3F)F)N=2)=C1 HMOFQRKFXWDHRL-UHFFFAOYSA-N 0.000 claims 1
• DTTFRMIFKNMBND-UHFFFAOYSA-N 2-[[2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]indazol-3-yl]-5-methoxypyrimidin-4-yl]amino]-5-fluoro-n-methylbenzamide Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C2=CC=CC=C2C(C=2N=C(NC=3C(=CC(F)=CC=3)C(=O)NC)C(OC)=CN=2)=N1 DTTFRMIFKNMBND-UHFFFAOYSA-N 0.000 claims 1
• CLDJHHIUPGCXDY-UHFFFAOYSA-N 2-[[2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]indazol-3-yl]-5-methoxypyrimidin-4-yl]amino]-5-fluorobenzamide Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C2=CC=CC=C2C(C=2N=C(NC=3C(=CC(F)=CC=3)C(N)=O)C(OC)=CN=2)=N1 CLDJHHIUPGCXDY-UHFFFAOYSA-N 0.000 claims 1
• RYCORJUCSOULQK-UHFFFAOYSA-N 2-[[2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]indazol-3-yl]-5-methoxypyrimidin-4-yl]amino]-5-fluorobenzoic acid Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C2=CC=CC=C2C(C=2N=C(NC=3C(=CC(F)=CC=3)C(O)=O)C(OC)=CN=2)=N1 RYCORJUCSOULQK-UHFFFAOYSA-N 0.000 claims 1
• ZDHTZSREQCOTBB-UHFFFAOYSA-N 2-[[2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]indazol-3-yl]-5-methoxypyrimidin-4-yl]amino]-n-methylbenzamide Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C2=CC=CC=C2C(C=2N=C(NC=3C(=CC=CC=3)C(=O)NC)C(OC)=CN=2)=N1 ZDHTZSREQCOTBB-UHFFFAOYSA-N 0.000 claims 1
• KZBFKWMXVLVWQX-UHFFFAOYSA-N 2-[[2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]indazol-3-yl]-5-methoxypyrimidin-4-yl]amino]benzamide Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C2=CC=CC=C2C(C=2N=C(NC=3C(=CC=CC=3)C(N)=O)C(OC)=CN=2)=N1 KZBFKWMXVLVWQX-UHFFFAOYSA-N 0.000 claims 1
• FPRKIURXPYNXTA-UHFFFAOYSA-N 2-[[2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]indazol-3-yl]-5-methoxypyrimidin-4-yl]amino]benzoic acid Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C2=CC=CC=C2C(C=2N=C(NC=3C(=CC=CC=3)C(O)=O)C(OC)=CN=2)=N1 FPRKIURXPYNXTA-UHFFFAOYSA-N 0.000 claims 1
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• RYQWBGDYIHWOLN-UHFFFAOYSA-N 5-methoxy-2-[1-[(4-methoxyphenyl)methyl]indazol-3-yl]-n-(2-methylpyrazol-3-yl)pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CN1C2=CC=CC=C2C(C=2N=C(NC=3N(N=CC=3)C)C(OC)=CN=2)=N1 RYQWBGDYIHWOLN-UHFFFAOYSA-N 0.000 claims 1
• SMHQTJFYNKFEBD-UHFFFAOYSA-N 5-methoxy-2-[1-[(4-methoxyphenyl)methyl]indazol-3-yl]-n-phenylpyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CN1C2=CC=CC=C2C(C=2N=C(NC=3C=CC=CC=3)C(OC)=CN=2)=N1 SMHQTJFYNKFEBD-UHFFFAOYSA-N 0.000 claims 1
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