HRP20110520T1 - Acilaminopirazoli kao inhibitori fgfr - Google Patents
Acilaminopirazoli kao inhibitori fgfr Download PDFInfo
- Publication number
- HRP20110520T1 HRP20110520T1 HR20110520T HRP20110520T HRP20110520T1 HR P20110520 T1 HRP20110520 T1 HR P20110520T1 HR 20110520 T HR20110520 T HR 20110520T HR P20110520 T HRP20110520 T HR P20110520T HR P20110520 T1 HRP20110520 T1 HR P20110520T1
- Authority
- HR
- Croatia
- Prior art keywords
- pyrazol
- ethyl
- dimethoxyphenyl
- benzamide
- hydroxyl
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 claims abstract 87
- 150000002367 halogens Chemical class 0.000 claims abstract 87
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 85
- 125000001424 substituent group Chemical group 0.000 claims abstract 81
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims abstract 59
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 55
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 54
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 34
- 150000001875 compounds Chemical class 0.000 claims abstract 22
- 150000003839 salts Chemical class 0.000 claims abstract 17
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000003118 aryl group Chemical group 0.000 claims abstract 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 6
- 239000001301 oxygen Chemical group 0.000 claims abstract 6
- 229910052717 sulfur Chemical group 0.000 claims abstract 6
- 239000011593 sulfur Chemical group 0.000 claims abstract 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 57
- 229910052739 hydrogen Inorganic materials 0.000 claims 47
- 239000001257 hydrogen Substances 0.000 claims 47
- 150000002431 hydrogen Chemical class 0.000 claims 43
- 125000000623 heterocyclic group Chemical group 0.000 claims 33
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 25
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 15
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 13
- -1 C3-cycloalkyl Chemical group 0.000 claims 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 12
- 125000004429 atom Chemical group 0.000 claims 9
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 8
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 7
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 6
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 6
- 125000002541 furyl group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- BYNNMWGWFIGTIC-LLVKDONJSA-N (2r)-3-naphthalen-1-yloxypropane-1,2-diol Chemical compound C1=CC=C2C(OC[C@H](O)CO)=CC=CC2=C1 BYNNMWGWFIGTIC-LLVKDONJSA-N 0.000 claims 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- VRQMAABPASPXMW-HDICACEKSA-N AZD4547 Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(=CC=3)N3C[C@@H](C)N[C@@H](C)C3)C=2)=C1 VRQMAABPASPXMW-HDICACEKSA-N 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- PFZTXTPVKAGHPW-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(3,4-dimethylpiperazin-1-yl)benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(=CC=3)N3CC(C)N(C)CC3)C=2)=C1 PFZTXTPVKAGHPW-UHFFFAOYSA-N 0.000 claims 2
- BPELTTMGJQPXIY-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-[(3-fluoropiperidin-1-yl)methyl]benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(CN4CC(F)CCC4)=CC=3)C=2)=C1 BPELTTMGJQPXIY-UHFFFAOYSA-N 0.000 claims 2
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims 2
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims 2
- SJSSFUMSAFMFNM-NSHDSACASA-N (2s)-5-(diaminomethylideneamino)-2-(phenylmethoxycarbonylamino)pentanoic acid Chemical compound NC(N)=NCCC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 SJSSFUMSAFMFNM-NSHDSACASA-N 0.000 claims 1
- SOIIHESTBYNJRH-PMPSAXMXSA-N (3r,6r,8as)-6-(benzylsulfonylamino)-n-[3-(diaminomethylideneamino)propyl]-5-oxo-2,3,6,7,8,8a-hexahydro-[1,3]thiazolo[3,2-a]pyridine-3-carboxamide Chemical compound N([C@@H]1CC[C@@H]2SC[C@H](N2C1=O)C(=O)NCCCN=C(N)N)S(=O)(=O)CC1=CC=CC=C1 SOIIHESTBYNJRH-PMPSAXMXSA-N 0.000 claims 1
- RXBMEHOLQJITJI-LEOXJPRUSA-N (4s)-5-amino-4-[[(2s)-2-[[(2s)-2-[[(4-bromophenyl)-hydroxyphosphoryl]methyl]-3-(3-phenyl-1,2-oxazol-5-yl)propanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoic acid Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N)CP(O)(=O)C=1C=CC(Br)=CC=1)C(ON=1)=CC=1C1=CC=CC=C1 RXBMEHOLQJITJI-LEOXJPRUSA-N 0.000 claims 1
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims 1
- FRZNJFWQVYAVCE-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(2-morpholin-4-ylethoxy)phenyl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C=CC(OCCN3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 FRZNJFWQVYAVCE-UHFFFAOYSA-N 0.000 claims 1
- PJAKRMBXANCRRH-UHFFFAOYSA-N 2-(1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl)-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=NC(=NC=3)N3CC4CCCCN4CC3)=C2)=C1 PJAKRMBXANCRRH-UHFFFAOYSA-N 0.000 claims 1
- LZZYDLADMOQZTD-UHFFFAOYSA-N 2-(1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=NC(=NC=3)N3CC4CCCCN4CC3)=C2)=C1 LZZYDLADMOQZTD-UHFFFAOYSA-N 0.000 claims 1
- XIFCRKATKAZDEQ-UHFFFAOYSA-N 2-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl)-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=NC(=NC=3)N3CC4CCCN4CC3)=C2)=C1 XIFCRKATKAZDEQ-UHFFFAOYSA-N 0.000 claims 1
- SAXDDBYCUJXAIQ-UHFFFAOYSA-N 2-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=NC(=NC=3)N3CC4CCCN4CC3)=C2)=C1 SAXDDBYCUJXAIQ-UHFFFAOYSA-N 0.000 claims 1
- GSZMBOOFYZJXIE-UHFFFAOYSA-N 2-(4-cyclopropyl-1,4-diazepan-1-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=NC(=NC=3)N3CCN(CCC3)C3CC3)=C2)=C1 GSZMBOOFYZJXIE-UHFFFAOYSA-N 0.000 claims 1
- YPHOYQVYSBBIRC-UHFFFAOYSA-N 2-(4-cyclopropylpiperazin-1-yl)-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=NC(=NC=3)N3CCN(CC3)C3CC3)=C2)=C1 YPHOYQVYSBBIRC-UHFFFAOYSA-N 0.000 claims 1
- IDPLQWNTAFBGOW-UHFFFAOYSA-N 2-(4-cyclopropylpiperazin-1-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=NC(=NC=3)N3CCN(CC3)C3CC3)=C2)=C1 IDPLQWNTAFBGOW-UHFFFAOYSA-N 0.000 claims 1
- JKKOLPWDKQDVJE-UHFFFAOYSA-N 3-[(3-fluoro-4-methoxyphenyl)methylamino]-6-(trifluoromethyl)quinoxaline-2-carboxylic acid Chemical compound C1=C(F)C(OC)=CC=C1CNC1=NC2=CC(C(F)(F)F)=CC=C2N=C1C(O)=O JKKOLPWDKQDVJE-UHFFFAOYSA-N 0.000 claims 1
- APJAEXGNDLFGPD-AWCRTANDSA-N 3-amino-n-{4-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-hydroxy-1-isobutyl-5-phenyl-pentyl}-benzamide Chemical group C([C@@H]([C@@H](O)C[C@H](CC(C)C)NC(=O)C=1C=CC(N)=CC=1)NC(=O)COC=1C(=CC=CC=1C)C)C1=CC=CC=C1 APJAEXGNDLFGPD-AWCRTANDSA-N 0.000 claims 1
- NHSNMCZCQCZMKT-UHFFFAOYSA-N 4-(1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl)-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CC4NCCCC4C3)=C2)=C1 NHSNMCZCQCZMKT-UHFFFAOYSA-N 0.000 claims 1
- CHSSXTHDKLNKJR-UHFFFAOYSA-N 4-(1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl)-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CC4CCCCN4CC3)=C2)=C1 CHSSXTHDKLNKJR-UHFFFAOYSA-N 0.000 claims 1
- ZYLKUSYOAFZPDW-UHFFFAOYSA-N 4-(1,4-diazepan-1-yl)-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]benzamide Chemical compound COC1=CC(OC)=CC(COC=2NN=C(NC(=O)C=3C=CC(=CC=3)N3CCNCCC3)C=2)=C1 ZYLKUSYOAFZPDW-UHFFFAOYSA-N 0.000 claims 1
- VQZLJZIEDTZTQJ-UHFFFAOYSA-N 4-(1-cyclopropylpiperidin-4-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)C3CCN(CC3)C3CC3)=C2)=C1 VQZLJZIEDTZTQJ-UHFFFAOYSA-N 0.000 claims 1
- NPPNBNZVHZLBMR-UHFFFAOYSA-N 4-(2-aminopropyl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(CC(C)N)=CC=3)C=2)=C1 NPPNBNZVHZLBMR-UHFFFAOYSA-N 0.000 claims 1
- AJRZAIWDKUDXTA-UHFFFAOYSA-N 4-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl)-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CC4CCCN4CC3)=C2)=C1 AJRZAIWDKUDXTA-UHFFFAOYSA-N 0.000 claims 1
- FILOJIFKRJXQCS-UHFFFAOYSA-N 4-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CC4CCCN4CC3)=C2)=C1 FILOJIFKRJXQCS-UHFFFAOYSA-N 0.000 claims 1
- CKNIRFFXNOGDAM-UHFFFAOYSA-N 4-(4-acetylpiperazin-1-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(=CC=3)N3CCN(CC3)C(C)=O)C=2)=C1 CKNIRFFXNOGDAM-UHFFFAOYSA-N 0.000 claims 1
- CPYWICDXAPUQNJ-UHFFFAOYSA-N 4-(4-cyclobutylpiperazin-1-yl)-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CCN(CC3)C3CCC3)=C2)=C1 CPYWICDXAPUQNJ-UHFFFAOYSA-N 0.000 claims 1
- LHCIFVUABPXLJF-UHFFFAOYSA-N 4-(4-cyclobutylpiperazin-1-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(=CC=3)N3CCN(CC3)C3CCC3)C=2)=C1 LHCIFVUABPXLJF-UHFFFAOYSA-N 0.000 claims 1
- REPFWMXEYOBBGF-UHFFFAOYSA-N 4-(4-cyclopropyl-1,4-diazepan-1-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CCN(CCC3)C3CC3)=C2)=C1 REPFWMXEYOBBGF-UHFFFAOYSA-N 0.000 claims 1
- FICSDJQCXTVTCL-UHFFFAOYSA-N 4-(4-cyclopropylpiperazin-1-yl)-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CCN(CC3)C3CC3)=C2)=C1 FICSDJQCXTVTCL-UHFFFAOYSA-N 0.000 claims 1
- GPJKIUMNZAQZFH-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-n-[5-(2-phenylethyl)-1h-pyrazol-3-yl]benzamide Chemical compound C1CN(C)CCN1C1=CC=C(C(=O)NC=2NN=C(CCC=3C=CC=CC=3)C=2)C=C1 GPJKIUMNZAQZFH-UHFFFAOYSA-N 0.000 claims 1
- GEMFRLOKPQVJLT-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-n-[5-(2-pyridin-3-ylethyl)-1h-pyrazol-3-yl]benzamide Chemical compound C1CN(C)CCN1C1=CC=C(C(=O)NC=2NN=C(CCC=3C=NC=CC=3)C=2)C=C1 GEMFRLOKPQVJLT-UHFFFAOYSA-N 0.000 claims 1
- DPRSWOBINUHRTN-UHFFFAOYSA-N 4-(hydroxymethyl)-n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=CC(CO)=CC=3)=C2)=C1 DPRSWOBINUHRTN-UHFFFAOYSA-N 0.000 claims 1
- MMYHYVFABXWZGF-UHFFFAOYSA-N 4-(methanesulfonamido)-n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=CC(NS(C)(=O)=O)=CC=3)=C2)=C1 MMYHYVFABXWZGF-UHFFFAOYSA-N 0.000 claims 1
- KWECWVXCPHIAFO-UHFFFAOYSA-N 4-[(7-cyano-3,4-dihydro-1h-isoquinolin-2-yl)methyl]-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(CN4CC5=CC(=CC=C5CC4)C#N)=CC=3)C=2)=C1 KWECWVXCPHIAFO-UHFFFAOYSA-N 0.000 claims 1
- VVBRWELWMMRIGM-UHFFFAOYSA-N 4-[2-(4,4-difluoropiperidin-1-yl)ethoxy]-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=CC(OCCN4CCC(F)(F)CC4)=CC=3)C=2)=C1 VVBRWELWMMRIGM-UHFFFAOYSA-N 0.000 claims 1
- BUYUFJZVMVFQLQ-UHFFFAOYSA-N 4-[2-(5,5,8,8-tetramethyl-6,7-dihydroquinoxalin-2-yl)ethynyl]benzoic acid Chemical compound CC1(C=2N=CC(=NC=2C(CC1)(C)C)C#CC1=CC=C(C(=O)O)C=C1)C BUYUFJZVMVFQLQ-UHFFFAOYSA-N 0.000 claims 1
- JCNUWWFTYZKKMO-UHFFFAOYSA-N 4-acetamido-n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=CC(NC(C)=O)=CC=3)=C2)=C1 JCNUWWFTYZKKMO-UHFFFAOYSA-N 0.000 claims 1
- WQUBEIMCFHCJCO-AWCRTANDSA-N 4-amino-n-{4-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-hydroxy-1-isobutyl-5-phenyl-pentyl}-benzamide Chemical group C([C@@H]([C@@H](O)C[C@H](CC(C)C)NC(=O)C=1C=C(N)C=CC=1)NC(=O)COC=1C(=CC=CC=1C)C)C1=CC=CC=C1 WQUBEIMCFHCJCO-AWCRTANDSA-N 0.000 claims 1
- UXVZRJOTGSEMKR-UHFFFAOYSA-N 4-benzamido-n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=CC(NC(=O)C=4C=CC=CC=4)=CC=3)=C2)=C1 UXVZRJOTGSEMKR-UHFFFAOYSA-N 0.000 claims 1
- KNJZJTPWIMKMLS-UHFFFAOYSA-N 4-cyano-n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)C#N)=C2)=C1 KNJZJTPWIMKMLS-UHFFFAOYSA-N 0.000 claims 1
- RSLUCSKUCDYSQI-UHFFFAOYSA-N 4-n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzene-1,4-dicarboxamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)C(N)=O)=C2)=C1 RSLUCSKUCDYSQI-UHFFFAOYSA-N 0.000 claims 1
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- ZAFKNYDURSJKQP-UHFFFAOYSA-N 5-(1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl)-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3N=CC(=NC=3)N3CC4CCCCN4CC3)=C2)=C1 ZAFKNYDURSJKQP-UHFFFAOYSA-N 0.000 claims 1
- DTNXPDAEHCDVIB-UHFFFAOYSA-N 5-(1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3N=CC(=NC=3)N3CC4CCCCN4CC3)=C2)=C1 DTNXPDAEHCDVIB-UHFFFAOYSA-N 0.000 claims 1
- WHUJVYOGWOQXJA-UHFFFAOYSA-N 5-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl)-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3N=CC(=NC=3)N3CC4CCCN4CC3)=C2)=C1 WHUJVYOGWOQXJA-UHFFFAOYSA-N 0.000 claims 1
- DMVGEABLDWSSRT-UHFFFAOYSA-N 5-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl)-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]thiophene-2-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3SC(=CC=3)N3CC4CCCN4CC3)=C2)=C1 DMVGEABLDWSSRT-UHFFFAOYSA-N 0.000 claims 1
- AABBJGRKPVKZBZ-UHFFFAOYSA-N 5-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3N=CC(=NC=3)N3CC4CCCN4CC3)=C2)=C1 AABBJGRKPVKZBZ-UHFFFAOYSA-N 0.000 claims 1
- WIYZJAWGAMJTGS-UHFFFAOYSA-N 5-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]thiophene-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3SC(=CC=3)N3CC4CCCN4CC3)=C2)=C1 WIYZJAWGAMJTGS-UHFFFAOYSA-N 0.000 claims 1
- DKMXLWLZNWCMCI-UHFFFAOYSA-N 5-(4-cyclopropyl-1,4-diazepan-1-yl)-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3N=CC(=NC=3)N3CCN(CCC3)C3CC3)=C2)=C1 DKMXLWLZNWCMCI-UHFFFAOYSA-N 0.000 claims 1
- NMMYWKWTRBUURS-UHFFFAOYSA-N 5-(4-cyclopropylpiperazin-1-yl)-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3N=CC(=NC=3)N3CCN(CC3)C3CC3)=C2)=C1 NMMYWKWTRBUURS-UHFFFAOYSA-N 0.000 claims 1
- PKXJQHUMHSTQSA-CALCHBBNSA-N 5-[(3s,5r)-4-(cyanomethyl)-3,5-dimethylpiperazin-1-yl]-n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3N=CC(=NC=3)N3C[C@@H](C)N(CC#N)[C@@H](C)C3)=C2)=C1 PKXJQHUMHSTQSA-CALCHBBNSA-N 0.000 claims 1
- PPHUZVJANIVFJQ-HDICACEKSA-N 5-[(3s,5r)-4-(cyanomethyl)-3,5-dimethylpiperazin-1-yl]-n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3N=CC(=NC=3)N3C[C@@H](C)N(CC#N)[C@@H](C)C3)=C2)=C1 PPHUZVJANIVFJQ-HDICACEKSA-N 0.000 claims 1
- HRCNSDLFNYOODP-UHFFFAOYSA-N 5-[[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]carbamoyl]pyridine-2-carboxylic acid Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=NC(=CC=3)C(O)=O)=C2)=C1 HRCNSDLFNYOODP-UHFFFAOYSA-N 0.000 claims 1
- JMSZVABYDKIGIA-UHFFFAOYSA-N 5-formamido-n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyridine-2-carboxamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3N=CC(NC=O)=CC=3)=C2)=C1 JMSZVABYDKIGIA-UHFFFAOYSA-N 0.000 claims 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- NCTHHJRIJGFPTG-UHFFFAOYSA-N 6,7-bis(aziridin-1-yl)-4-[7-[[6,7-bis(aziridin-1-yl)-5,8-dioxoquinazolin-4-yl]amino]heptylamino]quinazoline-5,8-dione Chemical compound C1CN1C=1C(=O)C2=C(NCCCCCCCNC=3C=4C(=O)C(N5CC5)=C(N5CC5)C(=O)C=4N=CN=3)N=CN=C2C(=O)C=1N1CC1 NCTHHJRIJGFPTG-UHFFFAOYSA-N 0.000 claims 1
- YZUNCEWXBIYTFT-UHFFFAOYSA-N 6-(2-methoxyethoxy)-n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyridine-3-carboxamide Chemical compound C1=NC(OCCOC)=CC=C1C(=O)NC1=CC(CCC=2C=C(OC)C=CC=2)=NN1 YZUNCEWXBIYTFT-UHFFFAOYSA-N 0.000 claims 1
- ZSKOTTDPJUEZJX-UHFFFAOYSA-N 6-(ethylamino)-n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyridine-3-carboxamide Chemical compound C1=NC(NCC)=CC=C1C(=O)NC1=CC(CCC=2C=C(OC)C=CC=2)=NN1 ZSKOTTDPJUEZJX-UHFFFAOYSA-N 0.000 claims 1
- ZHDHSBKTLRLUCQ-UHFFFAOYSA-N 6-[4-(6-bromo-1,2-benzothiazol-3-yl)phenoxy]-n-methyl-n-prop-2-enylhexan-1-amine Chemical compound C1=CC(OCCCCCCN(C)CC=C)=CC=C1C1=NSC2=CC(Br)=CC=C12 ZHDHSBKTLRLUCQ-UHFFFAOYSA-N 0.000 claims 1
- KETBCMTYHZNGEV-UHFFFAOYSA-N 6-anilino-n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyridine-3-carboxamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=NC(NC=4C=CC=CC=4)=CC=3)=C2)=C1 KETBCMTYHZNGEV-UHFFFAOYSA-N 0.000 claims 1
- DOVOTUJDSHELKJ-UHFFFAOYSA-N 6-chloro-n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyridine-3-carboxamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=NC(Cl)=CC=3)=C2)=C1 DOVOTUJDSHELKJ-UHFFFAOYSA-N 0.000 claims 1
- PTEJDKGWDNPCNH-UHFFFAOYSA-N 6-cyano-n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyridine-3-carboxamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=NC(=CC=3)C#N)=C2)=C1 PTEJDKGWDNPCNH-UHFFFAOYSA-N 0.000 claims 1
- WCYYXYDRJSKZOD-UHFFFAOYSA-N 6-methoxy-n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]pyridine-3-carboxamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=NC(OC)=CC=3)=C2)=C1 WCYYXYDRJSKZOD-UHFFFAOYSA-N 0.000 claims 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- ZOUTYVWHWSUKPL-RNCFNFMXSA-N C[C@H](CS)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(O)=O Chemical compound C[C@H](CS)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(O)=O ZOUTYVWHWSUKPL-RNCFNFMXSA-N 0.000 claims 1
- DSODRWWHAUGSGD-UHFFFAOYSA-N [5-(carbamimidoylsulfanylmethyl)thiophen-2-yl]methyl carbamimidothioate;dihydrochloride Chemical compound Cl.Cl.NC(=N)SCC1=CC=C(CSC(N)=N)S1 DSODRWWHAUGSGD-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical compound C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- LBDQPXFVZSAJPM-UHFFFAOYSA-N ethyl 5-[[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]carbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC=C1C(=O)NC1=CC(CCC=2C=C(OC)C=CC=2)=NN1 LBDQPXFVZSAJPM-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- NJMBQRNWBHNVOZ-UHFFFAOYSA-N methyl 5-[[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]carbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NC1=CC(CCC=2C=C(OC)C=CC=2)=NN1 NJMBQRNWBHNVOZ-UHFFFAOYSA-N 0.000 claims 1
- YUVSEEWMRSXTRL-UHFFFAOYSA-N methyl 6-[[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]carbamoyl]pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OC)=CC=C1C(=O)NC1=CC(CCC=2C=C(OC)C=CC=2)=NN1 YUVSEEWMRSXTRL-UHFFFAOYSA-N 0.000 claims 1
- HTBHTRYNRHGOML-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-2-(3,4-dimethylpiperazin-1-yl)pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=NC(=NC=3)N3CC(C)N(C)CC3)=C2)=C1 HTBHTRYNRHGOML-UHFFFAOYSA-N 0.000 claims 1
- KABBUICSDDSZHY-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-2-(4-methylpiperazin-1-yl)pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(COC=2NN=C(NC(=O)C=3C=NC(=NC=3)N3CCN(C)CC3)C=2)=C1 KABBUICSDDSZHY-UHFFFAOYSA-N 0.000 claims 1
- BXUCLDIBYXBAKH-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-3-piperazin-1-ylbenzamide Chemical compound COC1=CC(OC)=CC(COC=2NN=C(NC(=O)C=3C=C(C=CC=3)N3CCNCC3)C=2)=C1 BXUCLDIBYXBAKH-UHFFFAOYSA-N 0.000 claims 1
- APPRGXHIUOWFLJ-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-4-(1-methylpiperidin-4-yl)benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(=CC=3)C3CCN(C)CC3)=C2)=C1 APPRGXHIUOWFLJ-UHFFFAOYSA-N 0.000 claims 1
- KZTLOKUXUKISRM-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-4-(3,3-dimethylpiperazin-1-yl)benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CC(C)(C)NCC3)=C2)=C1 KZTLOKUXUKISRM-UHFFFAOYSA-N 0.000 claims 1
- DFDRSTKZIRHZJZ-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-4-(3,4-dimethylpiperazin-1-yl)benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CC(C)N(C)CC3)=C2)=C1 DFDRSTKZIRHZJZ-UHFFFAOYSA-N 0.000 claims 1
- VTKDZLYDUNFECD-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-4-(4-ethylpiperazin-1-yl)benzamide Chemical compound C1CN(CC)CCN1C1=CC=C(C(=O)NC=2NN=C(OCC=3C=C(OC)C=C(OC)C=3)C=2)C=C1 VTKDZLYDUNFECD-UHFFFAOYSA-N 0.000 claims 1
- LYZMEFMTACWOAW-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-4-(4-methylpiperazin-1-yl)benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CCN(C)CC3)=C2)=C1 LYZMEFMTACWOAW-UHFFFAOYSA-N 0.000 claims 1
- ADTZRSTUJXIHGE-HDICACEKSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-4-[(3r,5s)-3,4,5-trimethylpiperazin-1-yl]benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(=CC=3)N3C[C@@H](C)N(C)[C@@H](C)C3)=C2)=C1 ADTZRSTUJXIHGE-HDICACEKSA-N 0.000 claims 1
- AKOUAKDGWAGIOY-CALCHBBNSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(=CC=3)N3C[C@@H](C)N[C@@H](C)C3)=C2)=C1 AKOUAKDGWAGIOY-CALCHBBNSA-N 0.000 claims 1
- PQPZBQHFOADSEF-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-4-[2-(dimethylamino)ethylamino]benzamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=CC(NCCN(C)C)=CC=3)=C2)=C1 PQPZBQHFOADSEF-UHFFFAOYSA-N 0.000 claims 1
- RCMFWEPHBXSEJD-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC(OCC=2C=C(OC)C=C(OC)C=2)=NN1 RCMFWEPHBXSEJD-UHFFFAOYSA-N 0.000 claims 1
- VGRSGFKGDIBBDY-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-5-(3,3-dimethylpiperazin-1-yl)thiophene-2-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3SC(=CC=3)N3CC(C)(C)NCC3)=C2)=C1 VGRSGFKGDIBBDY-UHFFFAOYSA-N 0.000 claims 1
- IKEAYQIGDUZGRU-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-5-(3,4-dimethylpiperazin-1-yl)pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3N=CC(=NC=3)N3CC(C)N(C)CC3)=C2)=C1 IKEAYQIGDUZGRU-UHFFFAOYSA-N 0.000 claims 1
- IHTGUNPCPCXBLL-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-5-(3,4-dimethylpiperazin-1-yl)thiophene-2-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3SC(=CC=3)N3CC(C)N(C)CC3)=C2)=C1 IHTGUNPCPCXBLL-UHFFFAOYSA-N 0.000 claims 1
- VOXIVECESPVFBW-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-5-(4-ethylpiperazin-1-yl)thiophene-2-carboxamide Chemical compound C1CN(CC)CCN1C1=CC=C(C(=O)NC=2NN=C(OCC=3C=C(OC)C=C(OC)C=3)C=2)S1 VOXIVECESPVFBW-UHFFFAOYSA-N 0.000 claims 1
- ZALAXLCSSNUIBI-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-5-(4-methylpiperazin-1-yl)pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3N=CC(=NC=3)N3CCN(C)CC3)=C2)=C1 ZALAXLCSSNUIBI-UHFFFAOYSA-N 0.000 claims 1
- BLYXFMYJELIOBF-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-5-(4-methylpiperazin-1-yl)pyridine-2-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3N=CC(=CC=3)N3CCN(C)CC3)=C2)=C1 BLYXFMYJELIOBF-UHFFFAOYSA-N 0.000 claims 1
- PQOAVCZIWSDZRF-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-5-(4-methylpiperazin-1-yl)thiophene-2-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3SC(=CC=3)N3CCN(C)CC3)=C2)=C1 PQOAVCZIWSDZRF-UHFFFAOYSA-N 0.000 claims 1
- BZYIETPSKLUOBV-IYBDPMFKSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-5-[(3r,5s)-3,4,5-trimethylpiperazin-1-yl]pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3N=CC(=NC=3)N3C[C@@H](C)N(C)[C@@H](C)C3)=C2)=C1 BZYIETPSKLUOBV-IYBDPMFKSA-N 0.000 claims 1
- ZXQKDGVRECCNPW-GASCZTMLSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-5-[(3r,5s)-3,5-dimethylpiperazin-1-yl]thiophene-2-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3SC(=CC=3)N3C[C@@H](C)N[C@@H](C)C3)=C2)=C1 ZXQKDGVRECCNPW-GASCZTMLSA-N 0.000 claims 1
- BJKOXNCTKHXBQB-UHFFFAOYSA-N n-[3-[(3,5-dimethoxyphenyl)methoxy]-1h-pyrazol-5-yl]-6-piperazin-1-ylpyridine-3-carboxamide Chemical compound COC1=CC(OC)=CC(COC2=NNC(NC(=O)C=3C=NC(=CC=3)N3CCNCC3)=C2)=C1 BJKOXNCTKHXBQB-UHFFFAOYSA-N 0.000 claims 1
- NZSWVTUNTOOPSX-UHFFFAOYSA-N n-[5-[2-(1,3-benzodioxol-5-yl)ethyl]-1h-pyrazol-3-yl]-4-(4-methylpiperazin-1-yl)benzamide Chemical compound C1CN(C)CCN1C1=CC=C(C(=O)NC=2NN=C(CCC=3C=C4OCOC4=CC=3)C=2)C=C1 NZSWVTUNTOOPSX-UHFFFAOYSA-N 0.000 claims 1
- CHHAULSRBCMTEH-UHFFFAOYSA-N n-[5-[2-(2,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(4-methylpiperazin-1-yl)benzamide Chemical compound COC1=CC=C(OC)C(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CCN(C)CC3)=C2)=C1 CHHAULSRBCMTEH-UHFFFAOYSA-N 0.000 claims 1
- XQOCOFYGTCSAOM-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-2-(1-methylpiperidin-4-yl)pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=NC(=NC=3)C3CCN(C)CC3)=C2)=C1 XQOCOFYGTCSAOM-UHFFFAOYSA-N 0.000 claims 1
- FVNRGESZWOWIOE-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-2-(3,4-dimethylpiperazin-1-yl)pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=NC(=NC=3)N3CC(C)N(C)CC3)=C2)=C1 FVNRGESZWOWIOE-UHFFFAOYSA-N 0.000 claims 1
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- MJXRPIUNMFYPIO-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-2-(4-methyl-3-oxopiperazin-1-yl)pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=NC(=NC=3)N3CC(=O)N(C)CC3)=C2)=C1 MJXRPIUNMFYPIO-UHFFFAOYSA-N 0.000 claims 1
- SBOMLRJHYLXHOT-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-2-(4-methylpiperazin-1-yl)pyrimidine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=NC(=NC=3)N3CCN(C)CC3)=C2)=C1 SBOMLRJHYLXHOT-UHFFFAOYSA-N 0.000 claims 1
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- WTLALQRLHBXTHM-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(4-methyl-1,4-diazepan-1-yl)benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CCN(C)CCC3)=C2)=C1 WTLALQRLHBXTHM-UHFFFAOYSA-N 0.000 claims 1
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- SAXJUWBPYDYASN-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-5-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3N=CC(=NC=3)C=3CCN(C)CC=3)=C2)=C1 SAXJUWBPYDYASN-UHFFFAOYSA-N 0.000 claims 1
- ZIPLHWXKFUXUNN-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-5-(1-methylpiperidin-4-yl)pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3N=CC(=NC=3)C3CCN(C)CC3)=C2)=C1 ZIPLHWXKFUXUNN-UHFFFAOYSA-N 0.000 claims 1
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- JFUSILMVWGCWLX-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-5-(3,4-dimethylpiperazin-1-yl)pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3N=CC(=NC=3)N3CC(C)N(C)CC3)=C2)=C1 JFUSILMVWGCWLX-UHFFFAOYSA-N 0.000 claims 1
- ZNGRBVZIZAFWNU-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-5-(4-ethyl-1,4-diazepan-1-yl)pyrazine-2-carboxamide Chemical compound C1CN(CC)CCCN1C1=CN=C(C(=O)NC=2NN=C(CCC=3C=C(OC)C=C(OC)C=3)C=2)C=N1 ZNGRBVZIZAFWNU-UHFFFAOYSA-N 0.000 claims 1
- IYRCAAUUYKMAKQ-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-5-(4-methyl-1,4-diazepan-1-yl)pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3N=CC(=NC=3)N3CCN(C)CCC3)=C2)=C1 IYRCAAUUYKMAKQ-UHFFFAOYSA-N 0.000 claims 1
- OVNWQCURJHAVGY-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-5-(4-methylpiperazin-1-yl)thiophene-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3SC(=CC=3)N3CCN(C)CC3)=C2)=C1 OVNWQCURJHAVGY-UHFFFAOYSA-N 0.000 claims 1
- GMKZWTWCMBSCGK-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-5-(4-prop-2-enyl-1,4-diazepan-1-yl)pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3N=CC(=NC=3)N3CCN(CC=C)CCC3)=C2)=C1 GMKZWTWCMBSCGK-UHFFFAOYSA-N 0.000 claims 1
- LUHURQHAFYBLBY-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-5-(4-propan-2-yl-1,4-diazepan-1-yl)pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3N=CC(=NC=3)N3CCN(CCC3)C(C)C)=C2)=C1 LUHURQHAFYBLBY-UHFFFAOYSA-N 0.000 claims 1
- OCWXAVNWIGGMBR-CALCHBBNSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-5-[(3r,5s)-3,4,5-trimethylpiperazin-1-yl]pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3N=CC(=NC=3)N3C[C@@H](C)N(C)[C@@H](C)C3)=C2)=C1 OCWXAVNWIGGMBR-CALCHBBNSA-N 0.000 claims 1
- WNKZQUJCJALKIX-IYBDPMFKSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-5-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3N=CC(=NC=3)N3C[C@@H](C)N[C@@H](C)C3)=C2)=C1 WNKZQUJCJALKIX-IYBDPMFKSA-N 0.000 claims 1
- CDLCIPZEXTYNPH-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-5-[3-(dimethylamino)pyrrolidin-1-yl]pyrazine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3N=CC(=NC=3)N3CC(CC3)N(C)C)=C2)=C1 CDLCIPZEXTYNPH-UHFFFAOYSA-N 0.000 claims 1
- NCZOJGDOHRHOQD-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-5-[3-(methylamino)pyrrolidin-1-yl]pyrazine-2-carboxamide Chemical compound C1C(NC)CCN1C1=CN=C(C(=O)NC=2NN=C(CCC=3C=C(OC)C=C(OC)C=3)C=2)C=N1 NCZOJGDOHRHOQD-UHFFFAOYSA-N 0.000 claims 1
- XVRPCVLXVGHVAA-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-5-piperazin-1-ylthiophene-2-carboxamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3SC(=CC=3)N3CCNCC3)C=2)=C1 XVRPCVLXVGHVAA-UHFFFAOYSA-N 0.000 claims 1
- UCUOXLSNCCLZBK-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-6-piperazin-1-ylpyridine-3-carboxamide Chemical compound COC1=CC(OC)=CC(CCC=2NN=C(NC(=O)C=3C=NC(=CC=3)N3CCNCC3)C=2)=C1 UCUOXLSNCCLZBK-UHFFFAOYSA-N 0.000 claims 1
- YVHYCABINBWMSD-UHFFFAOYSA-N n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]benzamide Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3C=CC=CC=3)=C2)=C1 YVHYCABINBWMSD-UHFFFAOYSA-N 0.000 claims 1
- NERSYEVEMXIENO-UHFFFAOYSA-N n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(1,2,4-triazol-1-yl)benzamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3N=CN=C3)=C2)=C1 NERSYEVEMXIENO-UHFFFAOYSA-N 0.000 claims 1
- MXFBGPIFXVDVTK-UHFFFAOYSA-N n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(1,3-oxazol-5-yl)benzamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)C=3OC=NC=3)=C2)=C1 MXFBGPIFXVDVTK-UHFFFAOYSA-N 0.000 claims 1
- LOVODCJIKKDXSM-UHFFFAOYSA-N n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(4-methylpiperazin-1-yl)benzamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CCN(C)CC3)=C2)=C1 LOVODCJIKKDXSM-UHFFFAOYSA-N 0.000 claims 1
- JNHJFIWNWXVPHO-UHFFFAOYSA-N n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(4-methylsulfonylpiperazin-1-yl)benzamide Chemical compound COC1=CC=CC(CCC=2NN=C(NC(=O)C=3C=CC(=CC=3)N3CCN(CC3)S(C)(=O)=O)C=2)=C1 JNHJFIWNWXVPHO-UHFFFAOYSA-N 0.000 claims 1
- WCGDVAQMLCCSHF-UHFFFAOYSA-N n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(tetrazol-1-yl)benzamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3N=NN=C3)=C2)=C1 WCGDVAQMLCCSHF-UHFFFAOYSA-N 0.000 claims 1
- QXIBHSZJCFGLSW-UHFFFAOYSA-N n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-methylsulfonylbenzamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)S(C)(=O)=O)=C2)=C1 QXIBHSZJCFGLSW-UHFFFAOYSA-N 0.000 claims 1
- IPDAVNIQTDGVHJ-UHFFFAOYSA-N n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-oxo-1h-pyridine-2-carboxamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3N=CC=C(O)C=3)=C2)=C1 IPDAVNIQTDGVHJ-UHFFFAOYSA-N 0.000 claims 1
- DWNMLVLUEUYNEV-UHFFFAOYSA-N n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-pyrazol-1-ylbenzamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3N=CC=C3)=C2)=C1 DWNMLVLUEUYNEV-UHFFFAOYSA-N 0.000 claims 1
- MKWKYJBXOMZCGN-UHFFFAOYSA-N n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]-5-(prop-2-ynylamino)pyridine-2-carboxamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3N=CC(NCC#C)=CC=3)=C2)=C1 MKWKYJBXOMZCGN-UHFFFAOYSA-N 0.000 claims 1
- HHHMAWQHXWYEMS-UHFFFAOYSA-N n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]-5-methylpyrazine-2-carboxamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3N=CC(C)=NC=3)=C2)=C1 HHHMAWQHXWYEMS-UHFFFAOYSA-N 0.000 claims 1
- RYIUGXUIDYOLFJ-UHFFFAOYSA-N n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]-6-(2-pyrrolidin-1-ylethyl)pyridine-3-carboxamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=NC(CCN4CCCC4)=CC=3)=C2)=C1 RYIUGXUIDYOLFJ-UHFFFAOYSA-N 0.000 claims 1
- BUYXVORXGIUHMH-UHFFFAOYSA-N n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]-6-methylpyridine-3-carboxamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=NC(C)=CC=3)=C2)=C1 BUYXVORXGIUHMH-UHFFFAOYSA-N 0.000 claims 1
- IHCHQEBYCOBAGV-UHFFFAOYSA-N n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]-6-morpholin-4-ylpyridine-3-carboxamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=NC(=CC=3)N3CCOCC3)=C2)=C1 IHCHQEBYCOBAGV-UHFFFAOYSA-N 0.000 claims 1
- KCSJEJZNVGZZHO-UHFFFAOYSA-N n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=NC(O)=CC=3)=C2)=C1 KCSJEJZNVGZZHO-UHFFFAOYSA-N 0.000 claims 1
- BZWUWVKEJZYNEK-UHFFFAOYSA-N n-[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]-6-pyrazol-1-ylpyridine-3-carboxamide Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=NC(=CC=3)N3N=CC=C3)=C2)=C1 BZWUWVKEJZYNEK-UHFFFAOYSA-N 0.000 claims 1
- KDBSSIATPVEZQM-UHFFFAOYSA-N n-[5-[2-(furan-2-yl)ethyl]-1h-pyrazol-3-yl]-4-(4-methylpiperazin-1-yl)benzamide Chemical compound C1CN(C)CCN1C1=CC=C(C(=O)NC=2NN=C(CCC=3OC=CC=3)C=2)C=C1 KDBSSIATPVEZQM-UHFFFAOYSA-N 0.000 claims 1
- BOADZWPFOWQIRX-UHFFFAOYSA-N n-[5-[2-(furan-3-yl)ethyl]-1h-pyrazol-3-yl]-4-(4-methylpiperazin-1-yl)benzamide Chemical compound C1CN(C)CCN1C1=CC=C(C(=O)NC=2NN=C(CCC3=COC=C3)C=2)C=C1 BOADZWPFOWQIRX-UHFFFAOYSA-N 0.000 claims 1
- IQNLCUHYNOFIIG-UHFFFAOYSA-N n-[5-[2-[3-(2-methoxyethoxy)phenyl]ethyl]-1h-pyrazol-3-yl]-4-(4-methylpiperazin-1-yl)benzamide Chemical compound COCCOC1=CC=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CCN(C)CC3)=C2)=C1 IQNLCUHYNOFIIG-UHFFFAOYSA-N 0.000 claims 1
- IKCJWUFUEGARTD-UHFFFAOYSA-N n-[5-[2-[5-[(dimethylamino)methyl]furan-2-yl]ethyl]-1h-pyrazol-3-yl]-4-(4-methylpiperazin-1-yl)benzamide Chemical compound O1C(CN(C)C)=CC=C1CCC1=CC(NC(=O)C=2C=CC(=CC=2)N2CCN(C)CC2)=NN1 IKCJWUFUEGARTD-UHFFFAOYSA-N 0.000 claims 1
- DRBFMRQQSOQEMH-UHFFFAOYSA-N n-methyl-3-[2-[3-[[4-(4-methylpiperazin-1-yl)benzoyl]amino]-1h-pyrazol-5-yl]ethyl]benzamide Chemical compound CNC(=O)C1=CC=CC(CCC2=NNC(NC(=O)C=3C=CC(=CC=3)N3CCN(C)CC3)=C2)=C1 DRBFMRQQSOQEMH-UHFFFAOYSA-N 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- GFSSREOCZPVSRP-UHFFFAOYSA-N prop-2-enyl n-[5-[[5-[2-(3-methoxyphenyl)ethyl]-1h-pyrazol-3-yl]carbamoyl]pyridin-2-yl]carbamate Chemical compound COC1=CC=CC(CCC2=NNC(NC(=O)C=3C=NC(NC(=O)OCC=C)=CC=3)=C2)=C1 GFSSREOCZPVSRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 1
- DMYLUKNFEYWGCH-UHFFFAOYSA-N pyridazine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=N1 DMYLUKNFEYWGCH-UHFFFAOYSA-N 0.000 claims 1
- KWVGLKZINKFZDB-UHFFFAOYSA-N tert-butyl 4-[5-[[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]carbamoyl]thiophen-2-yl]piperazine-1-carboxylate Chemical compound COC1=CC(OC)=CC(CCC2=NNC(NC(=O)C=3SC(=CC=3)N3CCN(CC3)C(=O)OC(C)(C)C)=C2)=C1 KWVGLKZINKFZDB-UHFFFAOYSA-N 0.000 claims 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US87119006P | 2006-12-21 | 2006-12-21 | |
US98554207P | 2007-11-05 | 2007-11-05 | |
PCT/GB2007/004917 WO2008075068A2 (en) | 2006-12-21 | 2007-12-20 | Acylaminopyrazoles as fgfr inhibitors |
Publications (1)
Publication Number | Publication Date |
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HRP20110520T1 true HRP20110520T1 (hr) | 2011-08-31 |
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ID=39536793
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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HR20110520T HRP20110520T1 (hr) | 2006-12-21 | 2011-07-11 | Acilaminopirazoli kao inhibitori fgfr |
Country Status (29)
Country | Link |
---|---|
US (6) | US7737149B2 (ko) |
EP (1) | EP2125748B1 (ko) |
JP (1) | JP5000726B2 (ko) |
KR (1) | KR101467593B1 (ko) |
AR (1) | AR064454A1 (ko) |
AT (1) | ATE510825T1 (ko) |
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- 2007-12-20 JP JP2009542220A patent/JP5000726B2/ja not_active Expired - Fee Related
- 2007-12-20 AU AU2007336011A patent/AU2007336011B2/en active Active
- 2007-12-20 KR KR1020097014263A patent/KR101467593B1/ko active IP Right Grant
- 2007-12-20 PL PL07848646T patent/PL2125748T3/pl unknown
- 2007-12-29 SA SA07280734A patent/SA07280734B1/ar unknown
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2008
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2009
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- 2009-05-27 IL IL199019A patent/IL199019A/en active IP Right Grant
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2010
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- 2010-05-20 HK HK10104975.9A patent/HK1139137A1/xx unknown
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2011
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2012
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2013
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2017
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