JP2009507080A5 - - Google Patents
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- JP2009507080A5 JP2009507080A5 JP2008530213A JP2008530213A JP2009507080A5 JP 2009507080 A5 JP2009507080 A5 JP 2009507080A5 JP 2008530213 A JP2008530213 A JP 2008530213A JP 2008530213 A JP2008530213 A JP 2008530213A JP 2009507080 A5 JP2009507080 A5 JP 2009507080A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- triazole
- carbonyl
- optionally substituted
- phenyl
- Prior art date
- 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.)
- Pending
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- -1 cyano, nitro, oxo, thioxo, trimethylsilanyl Chemical group 0.000 claims 187
- 125000000217 alkyl group Chemical group 0.000 claims 114
- 125000003710 aryl alkyl group Chemical group 0.000 claims 88
- 125000001188 haloalkyl group Chemical group 0.000 claims 80
- 125000005843 halogen group Chemical group 0.000 claims 79
- 229910052739 hydrogen Inorganic materials 0.000 claims 75
- 239000001257 hydrogen Substances 0.000 claims 75
- 125000001072 heteroaryl group Chemical group 0.000 claims 73
- 125000001424 substituent group Chemical group 0.000 claims 71
- 125000003118 aryl group Chemical group 0.000 claims 59
- 125000000623 heterocyclic group Chemical group 0.000 claims 58
- 125000000753 cycloalkyl group Chemical group 0.000 claims 52
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 49
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 46
- 150000002431 hydrogen Chemical class 0.000 claims 46
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 42
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims 34
- 125000004093 cyano group Chemical group *C#N 0.000 claims 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 29
- 125000004450 alkenylene group Chemical group 0.000 claims 28
- 125000002947 alkylene group Chemical group 0.000 claims 28
- 125000003107 substituted aryl group Chemical group 0.000 claims 23
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 22
- 125000003342 alkenyl group Chemical group 0.000 claims 21
- 125000000304 alkynyl group Chemical group 0.000 claims 21
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims 21
- 125000000262 haloalkenyl group Chemical group 0.000 claims 21
- 125000000232 haloalkynyl group Chemical group 0.000 claims 21
- 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 21
- 125000004043 oxo group Chemical group O=* 0.000 claims 19
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 17
- 229910052757 nitrogen Inorganic materials 0.000 claims 15
- 125000004419 alkynylene group Chemical group 0.000 claims 14
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims 14
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 12
- XTMRUJFITBKHKF-UHFFFAOYSA-N O=C=C1NC=NN1 Chemical compound O=C=C1NC=NN1 XTMRUJFITBKHKF-UHFFFAOYSA-N 0.000 claims 8
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 7
- NHAZGSRLKBTDBF-UHFFFAOYSA-N 1,2,4-triazol-1-amine Chemical compound NN1C=NC=N1 NHAZGSRLKBTDBF-UHFFFAOYSA-N 0.000 claims 6
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- ZORDVGLUJGYQHC-UHFFFAOYSA-N (3-amino-1,2,4-triazol-1-yl)-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)N2N=C(N)N=C2)=C1 ZORDVGLUJGYQHC-UHFFFAOYSA-N 0.000 claims 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 3
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
- HPTBXUZCYQBJJP-UHFFFAOYSA-N 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-isocyanato-1,2,4-triazole Chemical compound C(=O)=NN1N=C(N=C1)C1=CC2=C(OCCO2)C=C1 HPTBXUZCYQBJJP-UHFFFAOYSA-N 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- UAJVBJHJSGNUDP-UHFFFAOYSA-N O=C=C1NNC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 Chemical compound O=C=C1NNC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 UAJVBJHJSGNUDP-UHFFFAOYSA-N 0.000 claims 2
- DUNODFUDHXGRMR-UHFFFAOYSA-N O=C=C1NNC(NC=2C=CC(OCCN3CCCCC3)=CC=2)=N1 Chemical compound O=C=C1NNC(NC=2C=CC(OCCN3CCCCC3)=CC=2)=N1 DUNODFUDHXGRMR-UHFFFAOYSA-N 0.000 claims 2
- QTHWVDYFXXHCKO-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 QTHWVDYFXXHCKO-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 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 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 2
- QGIAQCGAUXRCQN-UHFFFAOYSA-N (2-chlorophenyl)-[2,5-diamino-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3H-1,2,4-triazol-1-yl]methanone Chemical compound NC1=NC(N(N1C(=O)C1=C(C=CC=C1)Cl)N)C1=CC2=C(OCCO2)C=C1 QGIAQCGAUXRCQN-UHFFFAOYSA-N 0.000 claims 1
- UMZSCTIOTGRPNG-UHFFFAOYSA-N (3-chlorophenyl)-[2,5-diamino-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3H-1,2,4-triazol-1-yl]methanone Chemical compound NC1=NC(N(N1C(=O)C1=CC(=CC=C1)Cl)N)C1=CC2=C(OCCO2)C=C1 UMZSCTIOTGRPNG-UHFFFAOYSA-N 0.000 claims 1
- PNZPNYODHVFLRC-UHFFFAOYSA-N (4-chlorophenyl)-[2,5-diamino-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3H-1,2,4-triazol-1-yl]methanone Chemical compound NC1=NC(N(N1C(=O)C1=CC=C(C=C1)Cl)N)C1=CC2=C(OCCO2)C=C1 PNZPNYODHVFLRC-UHFFFAOYSA-N 0.000 claims 1
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims 1
- NRFGIUAJIAWVSM-UHFFFAOYSA-N 1-[2-[4-[[5-amino-1-(3-morpholin-4-ylbenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]ethyl]pyrrolidin-2-one Chemical compound N=1N(C(=O)C=2C=C(C=CC=2)N2CCOCC2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1=O NRFGIUAJIAWVSM-UHFFFAOYSA-N 0.000 claims 1
- IHMXXMVGQXHFTN-UHFFFAOYSA-N 1-[2-[4-[[5-amino-1-(4-morpholin-4-ylbenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]ethyl]pyrrolidin-2-one Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)N2CCOCC2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1=O IHMXXMVGQXHFTN-UHFFFAOYSA-N 0.000 claims 1
- XCPODFGJDNBJIR-UHFFFAOYSA-N 1-[2-[4-[[5-amino-1-(4-propan-2-yloxybenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]ethyl]pyrrolidin-2-one Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3C(CCC3)=O)=CC=2)=N1 XCPODFGJDNBJIR-UHFFFAOYSA-N 0.000 claims 1
- STPJYJRCCBVRDB-UHFFFAOYSA-N 1-[2-[4-[[5-amino-1-[4-(thiadiazol-4-yl)benzoyl]-1,2,4-triazol-3-yl]amino]phenoxy]ethyl]pyrrolidin-2-one Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)C=2N=NSC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1=O STPJYJRCCBVRDB-UHFFFAOYSA-N 0.000 claims 1
- QCLROQCLVYUOBI-UHFFFAOYSA-N 1-[2-[4-[[5-amino-1-[4-[(2-methylpropan-2-yl)oxy]benzoyl]-1,2,4-triazol-3-yl]amino]phenoxy]ethyl]pyrrolidin-2-one Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3C(CCC3)=O)=CC=2)=N1 QCLROQCLVYUOBI-UHFFFAOYSA-N 0.000 claims 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- DXMODMWMLNYQAH-UHFFFAOYSA-N 2-[3-[[5-amino-1-(2-methylbenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]acetonitrile Chemical compound CC1=CC=CC=C1C(=O)N1C(N)=NC(NC=2C=C(OCC#N)C=CC=2)=N1 DXMODMWMLNYQAH-UHFFFAOYSA-N 0.000 claims 1
- RIXUNLLOBWWNHG-UHFFFAOYSA-N 2-[3-[[5-amino-1-(3-methylbenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]-n-cyclohexylacetamide Chemical compound CC1=CC=CC(C(=O)N2C(=NC(NC=3C=C(OCC(=O)NC4CCCCC4)C=CC=3)=N2)N)=C1 RIXUNLLOBWWNHG-UHFFFAOYSA-N 0.000 claims 1
- XJRWFNSWOOWKFM-UHFFFAOYSA-N 2-[3-[[5-amino-1-(3-methylbenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]-n-methylacetamide Chemical compound CNC(=O)COC1=CC=CC(NC2=NN(C(N)=N2)C(=O)C=2C=C(C)C=CC=2)=C1 XJRWFNSWOOWKFM-UHFFFAOYSA-N 0.000 claims 1
- VSUSEMIMJXCYLF-UHFFFAOYSA-N 2-[3-[[5-amino-1-(3-methylbenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]acetonitrile Chemical compound CC1=CC=CC(C(=O)N2C(=NC(NC=3C=C(OCC#N)C=CC=3)=N2)N)=C1 VSUSEMIMJXCYLF-UHFFFAOYSA-N 0.000 claims 1
- GIADVRXJCAKMTN-UHFFFAOYSA-N 2-[3-[[5-amino-1-(4-methylbenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]acetonitrile Chemical compound C1=CC(C)=CC=C1C(=O)N1C(N)=NC(NC=2C=C(OCC#N)C=CC=2)=N1 GIADVRXJCAKMTN-UHFFFAOYSA-N 0.000 claims 1
- HRDAREHLSSSHBT-UHFFFAOYSA-N 2-[3-[[5-amino-1-(4-propan-2-yloxybenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]acetonitrile Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=C(OCC#N)C=CC=2)=N1 HRDAREHLSSSHBT-UHFFFAOYSA-N 0.000 claims 1
- KTQVEJGFDVZXDD-UHFFFAOYSA-N 2-[3-[[5-amino-2-(3-methylbenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]-n-cyclohexylacetamide Chemical compound CC1=CC=CC(C(=O)N2C(=NC(N)=N2)NC=2C=C(OCC(=O)NC3CCCCC3)C=CC=2)=C1 KTQVEJGFDVZXDD-UHFFFAOYSA-N 0.000 claims 1
- NCJZUMFNIHRNPJ-UHFFFAOYSA-N 2-[4-[[5-amino-1-(4-propan-2-yloxybenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]acetonitrile Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCC#N)=CC=2)=N1 NCJZUMFNIHRNPJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- VZOUJKBRNNSEGL-UHFFFAOYSA-N 3-[[5-amino-1-(1h-indole-6-carbonyl)-1,2,4-triazol-3-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound C1=C2C=CNC2=CC(C(=O)N2C(N)=NC(=N2)NC2C3CC(C=C3)C2C(=O)N)=C1 VZOUJKBRNNSEGL-UHFFFAOYSA-N 0.000 claims 1
- SZCMEIUZIVDZKU-UHFFFAOYSA-N 3-[[5-amino-1-(4-propan-2-yloxybenzoyl)-1,2,4-triazol-3-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC2C(C3CC2C=C3)C(N)=O)=N1 SZCMEIUZIVDZKU-UHFFFAOYSA-N 0.000 claims 1
- OQQWRMVCEJFSBE-UHFFFAOYSA-N 3-[[5-amino-1-[3-(dimethylamino)benzoyl]-1,2,4-triazol-3-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CN(C)C1=CC=CC(C(=O)N2C(=NC(NC3C(C4CC3C=C4)C(N)=O)=N2)N)=C1 OQQWRMVCEJFSBE-UHFFFAOYSA-N 0.000 claims 1
- GRZCEOUYNCPZJG-UHFFFAOYSA-N 3-[[5-amino-1-[4-(dimethylamino)benzoyl]-1,2,4-triazol-3-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C(N)=NC(NC2C(C3CC2C=C3)C(N)=O)=N1 GRZCEOUYNCPZJG-UHFFFAOYSA-N 0.000 claims 1
- CYXNUEGTPOTDHD-UHFFFAOYSA-N 3-[[5-amino-2-(1h-indole-6-carbonyl)-1,2,4-triazol-3-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound C1=C2C=CNC2=CC(C(=O)N2N=C(N)N=C2NC2C3CC(C=C3)C2C(=O)N)=C1 CYXNUEGTPOTDHD-UHFFFAOYSA-N 0.000 claims 1
- NOHPLIRXGAGHEQ-UHFFFAOYSA-N 3-[[5-amino-2-(4-propan-2-yloxybenzoyl)-1,2,4-triazol-3-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(NC2C(C3CC2C=C3)C(N)=O)=NC(N)=N1 NOHPLIRXGAGHEQ-UHFFFAOYSA-N 0.000 claims 1
- BTNRXORWAUSFNH-UHFFFAOYSA-N 3-[[5-amino-2-[3-(dimethylamino)benzoyl]-1,2,4-triazol-3-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CN(C)C1=CC=CC(C(=O)N2C(=NC(N)=N2)NC2C(C3CC2C=C3)C(N)=O)=C1 BTNRXORWAUSFNH-UHFFFAOYSA-N 0.000 claims 1
- MKKKMNSNNKBPNA-UHFFFAOYSA-N 3-[[5-amino-2-[4-(dimethylamino)benzoyl]-1,2,4-triazol-3-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C(NC2C(C3CC2C=C3)C(N)=O)=NC(N)=N1 MKKKMNSNNKBPNA-UHFFFAOYSA-N 0.000 claims 1
- FHHQLWMLTNNLPW-UHFFFAOYSA-N 3-amino-n-(1,3-benzodioxol-5-yl)-5-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound C=1C=C2OCOC2=CC=1NC(=O)N1N=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCCCC1 FHHQLWMLTNNLPW-UHFFFAOYSA-N 0.000 claims 1
- XPWWFEIYDZXDGX-UHFFFAOYSA-N 3-amino-n-(3,5-dimethoxyphenyl)-5-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound COC1=CC(OC)=CC(NC(=O)N2C(=NC(N)=N2)NC=2C=CC(OCCN3CCCCC3)=CC=2)=C1 XPWWFEIYDZXDGX-UHFFFAOYSA-N 0.000 claims 1
- PAKVXTXEMKZLGR-UHFFFAOYSA-N 3-amino-n-(3-methylphenyl)-5-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound CC1=CC=CC(NC(=O)N2C(=NC(N)=N2)NC=2C=CC(OCCN3CCCCC3)=CC=2)=C1 PAKVXTXEMKZLGR-UHFFFAOYSA-N 0.000 claims 1
- QEOMQUZNUXBEDX-UHFFFAOYSA-N 3-amino-n-(4-butoxyphenyl)-5-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1NC(=O)N1C(NC=2C=CC(OCCN3CCCCC3)=CC=2)=NC(N)=N1 QEOMQUZNUXBEDX-UHFFFAOYSA-N 0.000 claims 1
- RZUJWQSMYGJDRX-UHFFFAOYSA-N 3-amino-n-(4-methoxyphenyl)-5-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)N1C(NC=2C=CC(OCCN3CCCCC3)=CC=2)=NC(N)=N1 RZUJWQSMYGJDRX-UHFFFAOYSA-N 0.000 claims 1
- PNBMCFSJJPCLTP-UHFFFAOYSA-N 3-amino-n-(4-methylphenyl)-5-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound C1=CC(C)=CC=C1NC(=O)N1C(NC=2C=CC(OCCN3CCCCC3)=CC=2)=NC(N)=N1 PNBMCFSJJPCLTP-UHFFFAOYSA-N 0.000 claims 1
- NBXVLSOIHGPLCB-UHFFFAOYSA-N 3-amino-n-cyclohexyl-5-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound C1CCCCC1NC(=O)N1N=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCCCC1 NBXVLSOIHGPLCB-UHFFFAOYSA-N 0.000 claims 1
- YPQKZFJFBDPWCW-UHFFFAOYSA-N 3-amino-n-cyclopentyl-5-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound C1CCCC1NC(=O)N1N=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCCCC1 YPQKZFJFBDPWCW-UHFFFAOYSA-N 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- IQSMMJOQMRCYDT-UHFFFAOYSA-N 4-[5-amino-3-(4-morpholin-4-ylanilino)-1,2,4-triazole-1-carbonyl]benzenesulfonamide Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)S(N)(=O)=O)C(N)=NC=1NC(C=C1)=CC=C1N1CCOCC1 IQSMMJOQMRCYDT-UHFFFAOYSA-N 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- 125000006189 4-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- QUSPJWAWDJCOCQ-UHFFFAOYSA-N 5-amino-3-[4-(2-piperidin-1-ylethoxy)anilino]-n-(4-propan-2-ylphenyl)-1,2,4-triazole-1-carboxamide Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCCC3)=CC=2)=N1 QUSPJWAWDJCOCQ-UHFFFAOYSA-N 0.000 claims 1
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- BQUBZOLEDXRCRX-UHFFFAOYSA-N [5-amino-3-[4-(2-imidazol-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1-benzothiophen-5-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3C=CSC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1C=CN=C1 BQUBZOLEDXRCRX-UHFFFAOYSA-N 0.000 claims 1
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- JPPJJTBLJIPAPV-UHFFFAOYSA-N [5-amino-3-[4-(2-morpholin-4-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(5-propan-2-yloxypyridin-3-yl)methanone Chemical compound CC(C)OC1=CN=CC(C(=O)N2C(=NC(NC=3C=CC(OCCN4CCOCC4)=CC=3)=N2)N)=C1 JPPJJTBLJIPAPV-UHFFFAOYSA-N 0.000 claims 1
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- IQVMMLHCIWFEMX-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1-benzothiophen-2-yl)methanone Chemical compound N=1N(C(=O)C=2SC3=CC=CC=C3C=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 IQVMMLHCIWFEMX-UHFFFAOYSA-N 0.000 claims 1
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- ONIFBTFCFMFNLG-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1h-indol-2-yl)methanone Chemical compound N=1N(C(=O)C=2NC3=CC=CC=C3C=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 ONIFBTFCFMFNLG-UHFFFAOYSA-N 0.000 claims 1
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- PQKHESAPHRHJGE-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(2,6-difluorophenyl)methanone Chemical compound N=1N(C(=O)C=2C(=CC=CC=2F)F)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 PQKHESAPHRHJGE-UHFFFAOYSA-N 0.000 claims 1
- CORYDBAMRNVLSN-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(2h-benzotriazol-5-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3N=NNC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 CORYDBAMRNVLSN-UHFFFAOYSA-N 0.000 claims 1
- JFPTZTHNFDZNSH-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(3,5-difluoro-4-methoxyphenyl)methanone Chemical compound C1=C(F)C(OC)=C(F)C=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 JFPTZTHNFDZNSH-UHFFFAOYSA-N 0.000 claims 1
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- PMJKSODWBZVCKQ-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(3-thiophen-2-ylphenyl)methanone Chemical compound N=1N(C(=O)C=2C=C(C=CC=2)C=2SC=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 PMJKSODWBZVCKQ-UHFFFAOYSA-N 0.000 claims 1
- XYCPGWBYOGDHGU-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(3h-benzimidazol-5-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3N=CNC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 XYCPGWBYOGDHGU-UHFFFAOYSA-N 0.000 claims 1
- JRTMMKHRRJVMIA-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-imidazol-1-ylphenyl)methanone Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)N2C=NC=C2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 JRTMMKHRRJVMIA-UHFFFAOYSA-N 0.000 claims 1
- YPDRFTHPKGCNKC-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 YPDRFTHPKGCNKC-UHFFFAOYSA-N 0.000 claims 1
- XCNPORZRTBGECV-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-methylsulfanylphenyl)methanone Chemical compound C1=CC(SC)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 XCNPORZRTBGECV-UHFFFAOYSA-N 0.000 claims 1
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- WWKVOBHYPQZZRF-UHFFFAOYSA-N [5-amino-3-[4-(3-pyrrolidin-1-ylpropoxy)anilino]-1,2,4-triazol-1-yl]-[4-(dimethylamino)phenyl]methanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCCN3CCCC3)=CC=2)=N1 WWKVOBHYPQZZRF-UHFFFAOYSA-N 0.000 claims 1
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- WOSXALFTTCGOIZ-UHFFFAOYSA-N [5-amino-3-[4-[2-(azepan-1-yl)ethoxy]anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCCCC3)=CC=2)=N1 WOSXALFTTCGOIZ-UHFFFAOYSA-N 0.000 claims 1
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- RTLULVTVVBDSDM-UHFFFAOYSA-N [5-amino-3-[4-[2-(dimethylamino)ethoxy]anilino]-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN(C)C)=CC=2)=N1 RTLULVTVVBDSDM-UHFFFAOYSA-N 0.000 claims 1
- LBBHRIGBOUDBRS-UHFFFAOYSA-N [5-amino-3-[4-[2-(dimethylamino)ethoxy]anilino]-1,2,4-triazol-1-yl]-[4-(dimethylamino)phenyl]methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NN(C(=O)C=2C=CC(=CC=2)N(C)C)C(N)=N1 LBBHRIGBOUDBRS-UHFFFAOYSA-N 0.000 claims 1
- SBYOFFSKGSUHND-UHFFFAOYSA-N [5-amino-3-[4-[2-(dimethylamino)ethoxy]anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NN(C(=O)C=2C=CC(OC(C)(C)C)=CC=2)C(N)=N1 SBYOFFSKGSUHND-UHFFFAOYSA-N 0.000 claims 1
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- SWKQJEHGFYCCML-UHFFFAOYSA-N [5-amino-3-[4-[2-(dimethylamino)propoxy]anilino]-1,2,4-triazol-1-yl]-[4-(dimethylamino)phenyl]methanone Chemical compound C1=CC(OCC(C)N(C)C)=CC=C1NC1=NN(C(=O)C=2C=CC(=CC=2)N(C)C)C(N)=N1 SWKQJEHGFYCCML-UHFFFAOYSA-N 0.000 claims 1
- MUQZHQIPUVMVNR-UHFFFAOYSA-N [5-amino-3-[4-[2-(dimethylamino)propoxy]anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OCC(C)N(C)C)=CC=C1NC1=NN(C(=O)C=2C=CC(OC(C)(C)C)=CC=2)C(N)=N1 MUQZHQIPUVMVNR-UHFFFAOYSA-N 0.000 claims 1
- XULOGEQBAXOQEB-KRWDZBQOSA-N [5-amino-3-[4-[2-[(3s)-3-fluoropyrrolidin-1-yl]ethoxy]anilino]-1,2,4-triazol-1-yl]-(1h-indol-6-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3NC=CC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CC[C@H](F)C1 XULOGEQBAXOQEB-KRWDZBQOSA-N 0.000 claims 1
- CGGDXBVNKUMGTM-INIZCTEOSA-N [5-amino-3-[4-[2-[(3s)-3-fluoropyrrolidin-1-yl]ethoxy]anilino]-1,2,4-triazol-1-yl]-(2,3-dihydro-1,4-benzodioxin-6-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3OCCOC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CC[C@H](F)C1 CGGDXBVNKUMGTM-INIZCTEOSA-N 0.000 claims 1
- NKMYMZZVJYWLMK-KRWDZBQOSA-N [5-amino-3-[4-[2-[(3s)-3-fluoropyrrolidin-1-yl]ethoxy]anilino]-1,2,4-triazol-1-yl]-[4-(dimethylamino)phenyl]methanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3C[C@@H](F)CC3)=CC=2)=N1 NKMYMZZVJYWLMK-KRWDZBQOSA-N 0.000 claims 1
- XLEJTDFDSNDDOA-SFHVURJKSA-N [5-amino-3-[4-[2-[(3s)-3-fluoropyrrolidin-1-yl]ethoxy]anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3C[C@@H](F)CC3)=CC=2)=N1 XLEJTDFDSNDDOA-SFHVURJKSA-N 0.000 claims 1
- DGSVYYMCDPETKA-UHFFFAOYSA-N [5-amino-3-[4-[3-(dimethylamino)propoxy]anilino]-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(OCCCN(C)C)=CC=C1NC1=NN(C(=O)C=2C=CC(C)=CC=2)C(N)=N1 DGSVYYMCDPETKA-UHFFFAOYSA-N 0.000 claims 1
- BYJZHXOTFQRQKF-UHFFFAOYSA-N [5-amino-3-[[2-(oxan-2-yloxymethyl)-1-benzofuran-5-yl]amino]-1,2,4-triazol-1-yl]-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)N2C(=NC(NC=3C=C4C=C(COC5OCCCC5)OC4=CC=3)=N2)N)=C1 BYJZHXOTFQRQKF-UHFFFAOYSA-N 0.000 claims 1
- OHLSVDKURRPCMA-UHFFFAOYSA-N [5-amino-3-[n-(2-hydroxyethoxy)anilino]-1,2,4-triazol-1-yl]-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)N2C(=NC(=N2)N(OCCO)C=2C=CC=CC=2)N)=C1 OHLSVDKURRPCMA-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- RPSYDJLGXZBKTR-UHFFFAOYSA-N methyl 2-[3-[[5-amino-1-(3-methylbenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]acetate Chemical compound COC(=O)COC1=CC=CC(NC2=NN(C(N)=N2)C(=O)C=2C=C(C)C=CC=2)=C1 RPSYDJLGXZBKTR-UHFFFAOYSA-N 0.000 claims 1
- RZELWGOKESWMKX-UHFFFAOYSA-N methyl 2-[3-[[5-amino-1-(4-propan-2-yloxybenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]acetate Chemical compound COC(=O)COC1=CC=CC(NC2=NN(C(N)=N2)C(=O)C=2C=CC(OC(C)C)=CC=2)=C1 RZELWGOKESWMKX-UHFFFAOYSA-N 0.000 claims 1
- HRHUEZYMNYVRKZ-UHFFFAOYSA-N methyl 2-[4-[[5-amino-1-(4-propan-2-yloxybenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]acetate Chemical compound C1=CC(OCC(=O)OC)=CC=C1NC1=NN(C(=O)C=2C=CC(OC(C)C)=CC=2)C(N)=N1 HRHUEZYMNYVRKZ-UHFFFAOYSA-N 0.000 claims 1
- MWKVKSICXMIXCE-UHFFFAOYSA-N methyl 3-[5-amino-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carbonyl]benzoate Chemical compound COC(=O)C1=CC=CC(C(=O)N2C(=NC(NC=3C=CC(OCCN4CCCCC4)=CC=3)=N2)N)=C1 MWKVKSICXMIXCE-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- WFEVFIDXUMSSRB-UHFFFAOYSA-N n-[4-[5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carbonyl]phenyl]-2,2-dimethylpropanamide Chemical compound C1=CC(NC(=O)C(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 WFEVFIDXUMSSRB-UHFFFAOYSA-N 0.000 claims 1
- MEXNIACOWQTXMF-UHFFFAOYSA-N n-[5-amino-1-(3-methylbenzoyl)-1,2,4-triazol-3-yl]-n-[3-[4-(2-chloro-6-fluorophenyl)piperazin-1-yl]propyl]-3-methylbenzamide Chemical compound CC1=CC=CC(C(=O)N(CCCN2CCN(CC2)C=2C(=CC=CC=2F)Cl)C2=NN(C(N)=N2)C(=O)C=2C=C(C)C=CC=2)=C1 MEXNIACOWQTXMF-UHFFFAOYSA-N 0.000 claims 1
- JGNUEHAWRGWWMP-UHFFFAOYSA-N n-phenyl-1,2,4-triazol-1-amine Chemical compound C1=NC=NN1NC1=CC=CC=C1 JGNUEHAWRGWWMP-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims 1
- JFNLZVQOOSMTJK-UHFFFAOYSA-N norbornene Chemical compound C1C2CCC1C=C2 JFNLZVQOOSMTJK-UHFFFAOYSA-N 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- AFNNIHIBTGXLNY-UHFFFAOYSA-N tert-butyl 5-amino-3-(4-piperidin-1-ylanilino)-1,2,4-triazole-1-carboxylate Chemical compound N1=C(N)N(C(=O)OC(C)(C)C)N=C1NC1=CC=C(N2CCCCC2)C=C1 AFNNIHIBTGXLNY-UHFFFAOYSA-N 0.000 claims 1
- FIVTXGSTVPHMFT-UHFFFAOYSA-N tert-butyl n-[4-[5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carbonyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 FIVTXGSTVPHMFT-UHFFFAOYSA-N 0.000 claims 1
- DHGXKEQQMGHMBH-UHFFFAOYSA-N tert-butyl n-[[4-[5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carbonyl]phenyl]methyl]carbamate Chemical compound C1=CC(CNC(=O)OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 DHGXKEQQMGHMBH-UHFFFAOYSA-N 0.000 claims 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 0 *CC(*)*C(N**)=N Chemical compound *CC(*)*C(N**)=N 0.000 description 2
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| EP2074115B1 (en) | 2006-12-29 | 2018-03-07 | Rigel Pharmaceuticals, Inc. | N3-heteroaryl substituted triazoles and n5-heteroaryl substituted triazoles useful as axl inhibitors |
| WO2008083353A1 (en) | 2006-12-29 | 2008-07-10 | Rigel Pharmaceuticals, Inc. | Bicyclic aryl and bicyclic heteroaryl substituted triazoles useful as axl inhibitors |
| AU2007342007A1 (en) | 2006-12-29 | 2008-07-10 | Rigel Pharmaceuticals, Inc. | Substituted triazoles useful as Axl inhibitors |
| US8012965B2 (en) | 2006-12-29 | 2011-09-06 | Rigel Pharmaceuticals, Inc. | Bridged bicyclic aryl and bridged bicyclic heteroaryl substituted triazoles useful as axl inhibitors |
| CA2690653A1 (en) | 2007-06-15 | 2008-12-24 | Irm Llc | Protein kinase inhibitors and methods for using thereof |
| ES2424259T3 (es) | 2007-10-26 | 2013-09-30 | Rigel Pharmaceuticals, Inc. | Triazoles sustituidos con arilo policíclico y heteroarilo policíclico, útiles como agentes inhibidores del Axl |
| JP5592884B2 (ja) | 2008-07-09 | 2014-09-17 | ライジェル ファーマシューティカルズ， インコーポレイテッド | Ａｘｌ阻害剤として有用な多環式ヘテロアリール置換トリアゾール |
| WO2010005879A1 (en) | 2008-07-09 | 2010-01-14 | Rigel Pharmaceuticals, Inc. | Bridged bicyclic heteroaryl substituted triazoles useful as axl inhibitors |
| CA2749843C (en) | 2009-01-16 | 2017-09-05 | Rigel Pharmaceuticals, Inc. | Axl inhibitors for use in combination therapy for preventing, treating or managing metastatic cancer |
-
2006
- 2006-09-07 US US11/518,550 patent/US7884119B2/en active Active
- 2006-09-07 JP JP2008530213A patent/JP2009507080A/ja active Pending
- 2006-09-07 WO PCT/US2006/034970 patent/WO2007030680A2/en not_active Ceased
- 2006-09-07 CA CA2621503A patent/CA2621503C/en not_active Expired - Fee Related
- 2006-09-07 EP EP20060814315 patent/EP1922310A2/en not_active Withdrawn
-
2010
- 2010-12-10 US US12/965,545 patent/US8389557B2/en not_active Expired - Fee Related
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