JP2018510857A5

JP2018510857A5 -

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Publication number: JP2018510857A5
Authority: JP; Japan
Prior art keywords: imidazol; alkyl; fluorophenyl; imidazo; haloalkyl
Prior art date: 2016-02-26
Legal status : Granted

Application number

JP2017546173A

Other languages

English (en)

Japanese (ja)

Other versions

JP6836998B2 (ja

JP2018510857A (ja

Filing date

2016-02-26

Publication date

2019-04-04

2016-02-26 Application filed filed Critical

2016-02-26 Priority claimed from PCT/US2016/019830 external-priority patent/WO2016140884A1/en

2018-04-19 Publication of JP2018510857A publication Critical patent/JP2018510857A/ja

2019-04-04 Publication of JP2018510857A5 publication Critical patent/JP2018510857A5/ja

2021-03-03 Application granted granted Critical

2021-03-03 Publication of JP6836998B2 publication Critical patent/JP6836998B2/ja

Status Expired - Fee Related legal-status Critical Current

2036-02-26 Anticipated expiration legal-status Critical

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125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 153
125000000217 alkyl group Chemical group 0.000 claims 118
229910052736 halogen Inorganic materials 0.000 claims 103
150000002367 halogens Chemical class 0.000 claims 103
125000004093 cyano group Chemical group *C#N 0.000 claims 99
229910052739 hydrogen Inorganic materials 0.000 claims 78
239000001257 hydrogen Substances 0.000 claims 78
125000001188 haloalkyl group Chemical group 0.000 claims 63
150000002431 hydrogen Chemical class 0.000 claims 59
-1 imidazolidin-2-onyl Chemical group 0.000 claims 52
150000001875 compounds Chemical class 0.000 claims 47
229940124597 therapeutic agent Drugs 0.000 claims 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 19
125000003545 alkoxy group Chemical group 0.000 claims 19
239000003814 drug Substances 0.000 claims 19
201000010099 disease Diseases 0.000 claims 16
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 16
150000003839 salts Chemical class 0.000 claims 16
239000012453 solvate Substances 0.000 claims 16
239000003112 inhibitor Substances 0.000 claims 14
125000002619 bicyclic group Chemical group 0.000 claims 13
229940002612 prodrug Drugs 0.000 claims 13
239000000651 prodrug Substances 0.000 claims 13
150000001204 N-oxides Chemical class 0.000 claims 12
206010028980 Neoplasm Diseases 0.000 claims 12
229910052757 nitrogen Inorganic materials 0.000 claims 11
229910052760 oxygen Inorganic materials 0.000 claims 10
229910052717 sulfur Inorganic materials 0.000 claims 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
ULZZPSONFYHMKY-UHFFFAOYSA-N 6-[5-(4-fluoro-3-methylphenyl)-3-methylimidazol-4-yl]-1H-indazole Chemical compound FC1=C(C=C(C=C1)C=1N=CN(C=1C1=CC=C2C=NNC2=C1)C)C ULZZPSONFYHMKY-UHFFFAOYSA-N 0.000 claims 7
125000003342 alkenyl group Chemical group 0.000 claims 7
239000002246 antineoplastic agent Substances 0.000 claims 7
125000004429 atom Chemical group 0.000 claims 7
208000024891 symptom Diseases 0.000 claims 7
102000004887 Transforming Growth Factor beta Human genes 0.000 claims 6
108090001012 Transforming Growth Factor beta Proteins 0.000 claims 6
229940127089 cytotoxic agent Drugs 0.000 claims 6
SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims 6
229960005277 gemcitabine Drugs 0.000 claims 6
229960001756 oxaliplatin Drugs 0.000 claims 6
DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 claims 6
ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 claims 6
201000011510 cancer Diseases 0.000 claims 5
IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 claims 4
NTQODZHOLXYINM-UHFFFAOYSA-N 5-[4-(3-chlorophenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound ClC=1C=C(C=CC=1)C=1N=CNC=1C=1C=C2C=NNC2=CC=1 NTQODZHOLXYINM-UHFFFAOYSA-N 0.000 claims 4
CJNVIIQOYLDXLF-UHFFFAOYSA-N 5-[4-(4-fluoro-3-methylphenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound FC1=C(C=C(C=C1)C=1N=CNC=1C=1C=C2C=NNC2=CC=1)C CJNVIIQOYLDXLF-UHFFFAOYSA-N 0.000 claims 4
AEMRATBUIXJFLD-UHFFFAOYSA-N 6-[4-(3-chlorophenyl)-1H-imidazol-5-yl]-1-methylbenzimidazole Chemical compound ClC=1C=C(C=CC=1)C=1N=CNC=1C=1C=CC2=C(N(C=N2)C)C=1 AEMRATBUIXJFLD-UHFFFAOYSA-N 0.000 claims 4
BFIPITLAVPWQPQ-UHFFFAOYSA-N 6-[4-(3-chlorophenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound ClC=1C=C(C=CC=1)C=1N=CNC=1C1=CC=C2C=NNC2=C1 BFIPITLAVPWQPQ-UHFFFAOYSA-N 0.000 claims 4
ICBOPMCVTUHGHV-UHFFFAOYSA-N 6-[4-(4-fluoro-3-methylphenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound FC1=C(C=C(C=C1)C=1N=CNC=1C1=CC=C2C=NNC2=C1)C ICBOPMCVTUHGHV-UHFFFAOYSA-N 0.000 claims 4
239000012664 BCL-2-inhibitor Substances 0.000 claims 4
229940123711 Bcl2 inhibitor Drugs 0.000 claims 4
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UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims 4
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 4
NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims 4
RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims 4
208000035269 cancer or benign tumor Diseases 0.000 claims 4
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229960001924 melphalan Drugs 0.000 claims 4
SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 claims 4
208000011580 syndromic disease Diseases 0.000 claims 4
RPDOYLXGZVEPIP-UHFFFAOYSA-N 5-[3-methyl-5-(3-methylphenyl)imidazol-4-yl]-1H-indazole Chemical compound CN1C=NC(=C1C=1C=C2C=NNC2=CC=1)C=1C=C(C=CC=1)C RPDOYLXGZVEPIP-UHFFFAOYSA-N 0.000 claims 3
NTTUJGGLUCSPCH-UHFFFAOYSA-N 5-[4-(3,4-difluorophenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound FC=1C=C(C=CC=1F)C=1N=CNC=1C=1C=C2C=NNC2=CC=1 NTTUJGGLUCSPCH-UHFFFAOYSA-N 0.000 claims 3
DLEZDTFBZFAKFN-UHFFFAOYSA-N 5-[4-(3-fluorophenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound FC=1C=C(C=CC=1)C=1N=CNC=1C=1C=C2C=NNC2=CC=1 DLEZDTFBZFAKFN-UHFFFAOYSA-N 0.000 claims 3
HVLQWAFKHOUABL-UHFFFAOYSA-N 5-[4-(3-methylphenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound C1(=CC(=CC=C1)C=1N=CNC=1C=1C=C2C=NNC2=CC=1)C HVLQWAFKHOUABL-UHFFFAOYSA-N 0.000 claims 3
SZNIJWCNFIVOBU-UHFFFAOYSA-N 5-[5-(3-chlorophenyl)-3-methylimidazol-4-yl]-1H-indazole Chemical compound ClC=1C=C(C=CC=1)C=1N=CN(C=1C=1C=C2C=NNC2=CC=1)C SZNIJWCNFIVOBU-UHFFFAOYSA-N 0.000 claims 3
RIHHVSWLZUEDHV-UHFFFAOYSA-N 5-[5-(4-fluorophenyl)-1H-imidazol-4-yl]-1H-indazole Chemical compound FC1=CC=C(C=C1)C=1N=CNC=1C=1C=C2C=NNC2=CC=1 RIHHVSWLZUEDHV-UHFFFAOYSA-N 0.000 claims 3
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LJBLSXZRCXOCHC-UHFFFAOYSA-N 6-[4-(3-chlorophenyl)-1H-imidazol-5-yl]-1,3-benzothiazole Chemical compound ClC=1C=C(C=CC=1)C=1N=CNC=1C1=CC2=C(N=CS2)C=C1 LJBLSXZRCXOCHC-UHFFFAOYSA-N 0.000 claims 3
SCIUZYVNHFPRJI-UHFFFAOYSA-N 6-[4-(3-fluorophenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound FC=1C=C(C=CC=1)C=1N=CNC=1C1=CC=C2C=NNC2=C1 SCIUZYVNHFPRJI-UHFFFAOYSA-N 0.000 claims 3
ANNXUBINVQMBAZ-UHFFFAOYSA-N 6-[4-(3-methylphenyl)-1H-imidazol-5-yl]-1,3-benzothiazole Chemical compound C1(=CC(=CC=C1)C=1N=CNC=1C1=CC2=C(N=CS2)C=C1)C ANNXUBINVQMBAZ-UHFFFAOYSA-N 0.000 claims 3
UBKVNNSPRLRNPY-UHFFFAOYSA-N 6-[5-(3-chlorophenyl)-3-methylimidazol-4-yl]-1H-indazole Chemical compound ClC=1C=C(C=CC=1)C=1N=CN(C=1C1=CC=C2C=NNC2=C1)C UBKVNNSPRLRNPY-UHFFFAOYSA-N 0.000 claims 3
FHZOCUSENXHZON-UHFFFAOYSA-N 6-[5-(4-fluorophenyl)-1H-imidazol-4-yl]-1H-indazole Chemical compound FC1=CC=C(C=C1)C=1N=CNC=1C1=CC=C2C=NNC2=C1 FHZOCUSENXHZON-UHFFFAOYSA-N 0.000 claims 3
210000000481 breast Anatomy 0.000 claims 3
229940079593 drug Drugs 0.000 claims 3
FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims 2
102100025573 1-alkyl-2-acetylglycerophosphocholine esterase Human genes 0.000 claims 2
PHKIAIZZFBUIRE-UHFFFAOYSA-N 1-methyl-6-[4-(3-methylphenyl)-1H-imidazol-5-yl]benzimidazole Chemical compound CN1C=NC2=C1C=C(C=C2)C1=C(N=CN1)C=1C=C(C=CC=1)C PHKIAIZZFBUIRE-UHFFFAOYSA-N 0.000 claims 2
UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 claims 2
CTRPRMNBTVRDFH-UHFFFAOYSA-N 2-n-methyl-1,3,5-triazine-2,4,6-triamine Chemical compound CNC1=NC(N)=NC(N)=N1 CTRPRMNBTVRDFH-UHFFFAOYSA-N 0.000 claims 2
XXJWYDDUDKYVKI-UHFFFAOYSA-N 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-[3-(1-pyrrolidinyl)propoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C(=C4C=C(C)NC4=CC=3)F)N=CN=C2C=C1OCCCN1CCCC1 XXJWYDDUDKYVKI-UHFFFAOYSA-N 0.000 claims 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
OYODQTXFAIKAII-UHFFFAOYSA-N 5-(5-phenyl-1H-imidazol-4-yl)-1H-indazole Chemical compound C1(=CC=CC=C1)C=1N=CNC=1C=1C=C2C=NNC2=CC=1 OYODQTXFAIKAII-UHFFFAOYSA-N 0.000 claims 2
ZVPSOOCJOXYISK-UHFFFAOYSA-N 5-[4-(4-fluoro-3-methylphenyl)-2-methyl-1H-imidazol-5-yl]-1H-indazole Chemical compound FC1=C(C=C(C=C1)C=1N=C(NC=1C=1C=C2C=NNC2=CC=1)C)C ZVPSOOCJOXYISK-UHFFFAOYSA-N 0.000 claims 2
QDHWFEJWFFNZDX-UHFFFAOYSA-N 5-[5-(3,4-difluorophenyl)-3-methylimidazol-4-yl]-1H-indazole Chemical compound FC=1C=C(C=CC=1F)C=1N=CN(C=1C=1C=C2C=NNC2=CC=1)C QDHWFEJWFFNZDX-UHFFFAOYSA-N 0.000 claims 2
NRJVILXDKAQDGZ-UHFFFAOYSA-N 5-[5-(4-chlorophenyl)-1H-imidazol-4-yl]-1H-indazole Chemical compound ClC1=CC=C(C=C1)C=1N=CNC=1C=1C=C2C=NNC2=CC=1 NRJVILXDKAQDGZ-UHFFFAOYSA-N 0.000 claims 2
OZVYHRCDWPPHQS-UHFFFAOYSA-N 6-(5-phenyl-1H-imidazol-4-yl)-1H-indazole Chemical compound C1(=CC=CC=C1)C=1N=CNC=1C1=CC=C2C=NNC2=C1 OZVYHRCDWPPHQS-UHFFFAOYSA-N 0.000 claims 2
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KMKLRSWSFMASCQ-UHFFFAOYSA-N 6-[2-ethyl-5-(4-fluoro-3-methylphenyl)-1H-imidazol-4-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)C=1NC(=C(N=1)C1=CC(=C(C=C1)F)C)C=1C=CC=2N(C=1)N=CN=2 KMKLRSWSFMASCQ-UHFFFAOYSA-N 0.000 claims 2
CUCLVNIPNJPRPH-UHFFFAOYSA-N 6-[2-methyl-5-(2,4,5-trifluorophenyl)-1H-imidazol-4-yl]-1,3-benzothiazole Chemical compound CC=1NC(=C(N=1)C1=C(C=C(C(=C1)F)F)F)C1=CC2=C(N=CS2)C=C1 CUCLVNIPNJPRPH-UHFFFAOYSA-N 0.000 claims 2
VMQYBYYGVIXWET-UHFFFAOYSA-N 6-[4-(3,4-difluorophenyl)-1H-imidazol-5-yl]-1,3-benzothiazole Chemical compound FC=1C=C(C=CC=1F)C=1N=CNC=1C1=CC2=C(N=CS2)C=C1 VMQYBYYGVIXWET-UHFFFAOYSA-N 0.000 claims 2
BZZGSVNUGLYXMO-UHFFFAOYSA-N 6-[4-(3,4-difluorophenyl)-1H-imidazol-5-yl]-1-methylbenzimidazole Chemical compound FC=1C=C(C=CC=1F)C=1N=CNC=1C=1C=CC2=C(N(C=N2)C)C=1 BZZGSVNUGLYXMO-UHFFFAOYSA-N 0.000 claims 2
BZVUIERTZMSASW-UHFFFAOYSA-N 6-[4-(3,4-difluorophenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound FC=1C=C(C=CC=1F)C=1N=CNC=1C1=CC=C2C=NNC2=C1 BZVUIERTZMSASW-UHFFFAOYSA-N 0.000 claims 2
ZEBJYUXUNILVGE-UHFFFAOYSA-N 6-[4-(3-chlorophenyl)-2-ethyl-1H-imidazol-5-yl]-1,3-benzothiazole Chemical compound ClC=1C=C(C=CC=1)C=1N=C(NC=1C1=CC2=C(N=CS2)C=C1)CC ZEBJYUXUNILVGE-UHFFFAOYSA-N 0.000 claims 2
NWZOSSQOJBZGSI-UHFFFAOYSA-N 6-[4-(3-chlorophenyl)-2-methyl-1H-imidazol-5-yl]-1H-indazole Chemical compound ClC=1C=C(C=CC=1)C=1N=C(NC=1C1=CC=C2C=NNC2=C1)C NWZOSSQOJBZGSI-UHFFFAOYSA-N 0.000 claims 2
BVNDRHCGADDHAI-UHFFFAOYSA-N 6-[4-(3-methylphenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound C1(=CC(=CC=C1)C=1N=CNC=1C1=CC=C2C=NNC2=C1)C BVNDRHCGADDHAI-UHFFFAOYSA-N 0.000 claims 2
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SRVKIGXQENKXHA-UHFFFAOYSA-N 5-[2,3-dimethyl-5-(3-methylphenyl)imidazol-4-yl]-1H-indazole Chemical compound CN1C(=NC(=C1C=1C=C2C=NNC2=CC=1)C=1C=C(C=CC=1)C)C SRVKIGXQENKXHA-UHFFFAOYSA-N 0.000 claims 1
SZJXGQDYVIWIGQ-UHFFFAOYSA-N 5-[2-ethyl-4-(3-fluoro-5-methylphenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound C(C)C=1NC(=C(N=1)C1=CC(=CC(=C1)C)F)C=1C=C2C=NNC2=CC=1 SZJXGQDYVIWIGQ-UHFFFAOYSA-N 0.000 claims 1
KJEDFYRIYBTZEU-UHFFFAOYSA-N 5-[2-ethyl-4-(3-methylphenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound C(C)C=1NC(=C(N=1)C=1C=C(C=CC=1)C)C=1C=C2C=NNC2=CC=1 KJEDFYRIYBTZEU-UHFFFAOYSA-N 0.000 claims 1
GXVPBJHVMNRGLS-UHFFFAOYSA-N 5-[2-ethyl-4-(4-fluoro-3-methylphenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound C(C)C=1NC(=C(N=1)C1=CC(=C(C=C1)F)C)C=1C=C2C=NNC2=CC=1 GXVPBJHVMNRGLS-UHFFFAOYSA-N 0.000 claims 1
JUIXZQZFWQBMFQ-UHFFFAOYSA-N 5-[2-ethyl-5-(4-fluorophenyl)-1H-imidazol-4-yl]-1H-indazole Chemical compound C(C)C=1NC(=C(N=1)C1=CC=C(C=C1)F)C=1C=C2C=NNC2=CC=1 JUIXZQZFWQBMFQ-UHFFFAOYSA-N 0.000 claims 1
PKLBMOWTYHIFQU-UHFFFAOYSA-N 5-[2-methyl-4-(3,4,5-trifluorophenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound CC=1NC(=C(N=1)C1=CC(=C(C(=C1)F)F)F)C=1C=C2C=NNC2=CC=1 PKLBMOWTYHIFQU-UHFFFAOYSA-N 0.000 claims 1
UFWJAQOSHUFCAV-UHFFFAOYSA-N 5-[2-methyl-5-(2,4,5-trifluorophenyl)-1H-imidazol-4-yl]-1H-indazole Chemical compound CC=1NC(=C(N=1)C1=C(C=C(C(=C1)F)F)F)C=1C=C2C=NNC2=CC=1 UFWJAQOSHUFCAV-UHFFFAOYSA-N 0.000 claims 1
VMVJVKXRKUIMHJ-UHFFFAOYSA-N 5-[4-(3,4-difluorophenyl)-2-ethyl-1H-imidazol-5-yl]-1H-indazole Chemical compound FC=1C=C(C=CC=1F)C=1N=C(NC=1C=1C=C2C=NNC2=CC=1)CC VMVJVKXRKUIMHJ-UHFFFAOYSA-N 0.000 claims 1
ODLGSIGBWRWNQE-UHFFFAOYSA-N 5-[4-(3,4-difluorophenyl)-2-methyl-1H-imidazol-5-yl]-1H-indazole Chemical compound FC=1C=C(C=CC=1F)C=1N=C(NC=1C=1C=C2C=NNC2=CC=1)C ODLGSIGBWRWNQE-UHFFFAOYSA-N 0.000 claims 1
FJHHRIUKXFGXNF-UHFFFAOYSA-N 5-[4-(3,5-difluorophenyl)-2-methyl-1H-imidazol-5-yl]-1H-indazole Chemical compound FC=1C=C(C=C(C=1)F)C=1N=C(NC=1C=1C=C2C=NNC2=CC=1)C FJHHRIUKXFGXNF-UHFFFAOYSA-N 0.000 claims 1
NLULSMRBQBEKJT-UHFFFAOYSA-N 5-[4-(3-chloro-5-fluorophenyl)-2-ethyl-1H-imidazol-5-yl]-1H-indazole Chemical compound ClC=1C=C(C=C(C=1)F)C=1N=C(NC=1C=1C=C2C=NNC2=CC=1)CC NLULSMRBQBEKJT-UHFFFAOYSA-N 0.000 claims 1
UMKNNASRAKDBQO-UHFFFAOYSA-N 5-[4-(3-chlorophenyl)-2-ethyl-1H-imidazol-5-yl]-1H-indazole Chemical compound ClC=1C=C(C=CC=1)C=1N=C(NC=1C=1C=C2C=NNC2=CC=1)CC UMKNNASRAKDBQO-UHFFFAOYSA-N 0.000 claims 1
NWSNYQSZTHBTDY-UHFFFAOYSA-N 5-[4-(3-chlorophenyl)-2-methyl-1H-imidazol-5-yl]-1H-indazole Chemical compound ClC=1C=C(C=CC=1)C=1N=C(NC=1C=1C=C2C=NNC2=CC=1)C NWSNYQSZTHBTDY-UHFFFAOYSA-N 0.000 claims 1
DYRLKYKREPMBKO-UHFFFAOYSA-N 5-[5-(4-fluoro-3-methylphenyl)-2,3-dimethylimidazol-4-yl]-1H-indazole Chemical compound FC1=C(C=C(C=C1)C=1N=C(N(C=1C=1C=C2C=NNC2=CC=1)C)C)C DYRLKYKREPMBKO-UHFFFAOYSA-N 0.000 claims 1
CORDRCXPMDTNBX-UHFFFAOYSA-N 5-[5-(4-fluorophenyl)-2-methyl-1H-imidazol-4-yl]-1H-indazole Chemical compound FC1=CC=C(C=C1)C=1N=C(NC=1C=1C=C2C=NNC2=CC=1)C CORDRCXPMDTNBX-UHFFFAOYSA-N 0.000 claims 1
ZAJBVEHYCSELCV-UHFFFAOYSA-N 5-[5-(4-fluorophenyl)-3-methylimidazol-4-yl]-1H-indazole Chemical compound FC1=CC=C(C=C1)C=1N=CN(C=1C=1C=C2C=NNC2=CC=1)C ZAJBVEHYCSELCV-UHFFFAOYSA-N 0.000 claims 1
HWSOZSXZHXYROJ-UHFFFAOYSA-N 5-[5-(4-methoxyphenyl)-3-methylimidazol-4-yl]-1H-indazole Chemical compound COC1=CC=C(C=C1)C=1N=CN(C=1C=1C=C2C=NNC2=CC=1)C HWSOZSXZHXYROJ-UHFFFAOYSA-N 0.000 claims 1
FFARGLZRLVWCLR-UHFFFAOYSA-N 5-[6-[3-(2,2-difluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazin-3-yl]-1,3-oxazole Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C1=CN=CO1)C1=CC=C(C=C1)F)F FFARGLZRLVWCLR-UHFFFAOYSA-N 0.000 claims 1
YLPYFINBHMOROE-UHFFFAOYSA-N 5-imidazo[1,2-a]pyridin-6-yl-4-(3-methoxyphenyl)-1,3-thiazol-2-amine Chemical compound N=1C=CN2C=1C=CC(=C2)C1=C(N=C(S1)N)C1=CC(=CC=C1)OC YLPYFINBHMOROE-UHFFFAOYSA-N 0.000 claims 1
MYOBUZFNZHPMCI-UHFFFAOYSA-N 5-imidazo[1,2-a]pyridin-6-yl-4-(4-methoxyphenyl)-1,3-thiazol-2-amine Chemical compound N=1C=CN2C=1C=CC(=C2)C1=C(N=C(S1)N)C1=CC=C(C=C1)OC MYOBUZFNZHPMCI-UHFFFAOYSA-N 0.000 claims 1
NJCSPSNHDMOLMN-UHFFFAOYSA-N 5-imidazo[1,2-a]pyridin-6-yl-4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine Chemical compound N=1C=CN2C=1C=CC(=C2)C1=C(N=C(S1)N)C1=CC(=CC=C1)C(F)(F)F NJCSPSNHDMOLMN-UHFFFAOYSA-N 0.000 claims 1
XQXQMMZOEQAJAX-UHFFFAOYSA-N 5-quinoxalin-6-yl-4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine Chemical compound N1=CC=NC2=CC(=CC=C12)C1=C(N=C(S1)N)C1=CC(=CC=C1)C(F)(F)F XQXQMMZOEQAJAX-UHFFFAOYSA-N 0.000 claims 1
DGWOCDSEKXZKBT-UHFFFAOYSA-N 6-[2,3-dimethyl-5-(3-methylphenyl)imidazol-4-yl]-1,3-benzothiazole Chemical compound CN1C(=NC(=C1C1=CC2=C(N=CS2)C=C1)C=1C=C(C=CC=1)C)C DGWOCDSEKXZKBT-UHFFFAOYSA-N 0.000 claims 1
TWZWVVDYGDEDTC-UHFFFAOYSA-N 6-[2,3-dimethyl-5-(3-methylphenyl)imidazol-4-yl]-1-methylbenzimidazole Chemical compound CN1C(=NC(=C1C=1C=CC2=C(N(C=N2)C)C=1)C=1C=C(C=CC=1)C)C TWZWVVDYGDEDTC-UHFFFAOYSA-N 0.000 claims 1
JJJQNLUGCAPGSZ-UHFFFAOYSA-N 6-[2,3-dimethyl-5-(3-methylphenyl)imidazol-4-yl]-1H-indazole Chemical compound CN1C(=NC(=C1C1=CC=C2C=NNC2=C1)C=1C=C(C=CC=1)C)C JJJQNLUGCAPGSZ-UHFFFAOYSA-N 0.000 claims 1
CAGUYNPICDXDAT-UHFFFAOYSA-N 6-[2-(4-fluorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound FC1=CC=C(C=C1)C=1N=C2N(CCNC2)C=1C=1C=CC=2N(C=1)C(=CN=2)C(=O)N CAGUYNPICDXDAT-UHFFFAOYSA-N 0.000 claims 1
OPHLMHLJLIXRDE-UHFFFAOYSA-N 6-[2-(4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound FC1=CC=C(C=C1)C=1N=C2N(C=1C=1C=CC=3N(C=1)C(=CN=3)C#N)CCC2 OPHLMHLJLIXRDE-UHFFFAOYSA-N 0.000 claims 1
ZCVUZZMCWLHUTN-UHFFFAOYSA-N 6-[2-(4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound FC1=CC=C(C=C1)C=1N=C2N(C=1C=1C=CC=3N(C=1)C(=CN=3)C(=O)N)CCC2 ZCVUZZMCWLHUTN-UHFFFAOYSA-N 0.000 claims 1
WPSPFTKBUPMYAT-UHFFFAOYSA-N 6-[2-(4-fluorophenyl)-7-methyl-6,8-dihydro-5H-imidazo[1,2-a]pyrazin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound FC1=CC=C(C=C1)C=1N=C2N(CCN(C2)C)C=1C=1C=CC=2N(C=1)C(=CN=2)C(=O)N WPSPFTKBUPMYAT-UHFFFAOYSA-N 0.000 claims 1
YGXPXWXYMBIYBJ-UHFFFAOYSA-N 6-[2-amino-3-(2,2-difluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound NC=1N(C(=C(N=1)C1=CC=C(C=C1)F)C=1C=CC=2N(C=1)C(=CN=2)C#N)CC(F)F YGXPXWXYMBIYBJ-UHFFFAOYSA-N 0.000 claims 1
NZYHESAHFRPMAQ-UHFFFAOYSA-N 6-[2-ethyl-4-(3-fluoro-5-methylphenyl)-1H-imidazol-5-yl]-1,3-benzothiazole Chemical compound C(C)C=1NC(=C(N=1)C1=CC(=CC(=C1)C)F)C1=CC2=C(N=CS2)C=C1 NZYHESAHFRPMAQ-UHFFFAOYSA-N 0.000 claims 1
KHCNWTOONOFPQA-UHFFFAOYSA-N 6-[2-ethyl-4-(3-fluoro-5-methylphenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound C(C)C=1NC(=C(N=1)C1=CC(=CC(=C1)C)F)C1=CC=C2C=NNC2=C1 KHCNWTOONOFPQA-UHFFFAOYSA-N 0.000 claims 1
HDRDJZPTUDDSNF-UHFFFAOYSA-N 6-[2-ethyl-4-(3-fluoro-5-methylphenyl)-1H-imidazol-5-yl]imidazo[1,2-a]pyridine Chemical compound C(C)C=1NC(=C(N=1)C1=CC(=CC(=C1)C)F)C=1C=CC=2N(C=1)C=CN=2 HDRDJZPTUDDSNF-UHFFFAOYSA-N 0.000 claims 1
YQPGVGZUDXJINE-UHFFFAOYSA-N 6-[2-ethyl-4-(3-fluoro-5-methylphenyl)-1H-imidazol-5-yl]quinoxaline Chemical compound C(C)C=1NC(=C(N=1)C1=CC(=CC(=C1)C)F)C=1C=C2N=CC=NC2=CC=1 YQPGVGZUDXJINE-UHFFFAOYSA-N 0.000 claims 1
YKKWKVSSIBDNQT-UHFFFAOYSA-N 6-[2-ethyl-4-(3-fluorophenyl)-1H-imidazol-5-yl]-1,3-benzothiazole Chemical compound C(C)C=1NC(=C(N=1)C1=CC(=CC=C1)F)C1=CC2=C(N=CS2)C=C1 YKKWKVSSIBDNQT-UHFFFAOYSA-N 0.000 claims 1
JACDLXPLEQFBQJ-UHFFFAOYSA-N 6-[2-ethyl-4-(3-methylphenyl)-1H-imidazol-5-yl]-1,3-benzothiazole Chemical compound C(C)C=1NC(=C(N=1)C=1C=C(C=CC=1)C)C1=CC2=C(N=CS2)C=C1 JACDLXPLEQFBQJ-UHFFFAOYSA-N 0.000 claims 1
FOJNQQMEEXTXMC-UHFFFAOYSA-N 6-[2-ethyl-4-(3-methylphenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound C(C)C=1NC(=C(N=1)C=1C=C(C=CC=1)C)C1=CC=C2C=NNC2=C1 FOJNQQMEEXTXMC-UHFFFAOYSA-N 0.000 claims 1
ZWTQGYQENJTHQB-UHFFFAOYSA-N 6-[2-ethyl-4-(3-methylphenyl)-1H-imidazol-5-yl]quinoxaline Chemical compound C(C)C=1NC(=C(N=1)C=1C=C(C=CC=1)C)C=1C=C2N=CC=NC2=CC=1 ZWTQGYQENJTHQB-UHFFFAOYSA-N 0.000 claims 1
BTMBSOKJUCONCV-UHFFFAOYSA-N 6-[2-ethyl-4-(4-fluoro-3-methylphenyl)-1H-imidazol-5-yl]-1,3-benzothiazole Chemical compound C(C)C=1NC(=C(N=1)C1=CC(=C(C=C1)F)C)C1=CC2=C(N=CS2)C=C1 BTMBSOKJUCONCV-UHFFFAOYSA-N 0.000 claims 1
DLOUVWMIAXHHQX-UHFFFAOYSA-N 6-[2-ethyl-4-(4-fluoro-3-methylphenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound C(C)C=1NC(=C(N=1)C1=CC(=C(C=C1)F)C)C1=CC=C2C=NNC2=C1 DLOUVWMIAXHHQX-UHFFFAOYSA-N 0.000 claims 1
LIKBZTZESCKFFS-UHFFFAOYSA-N 6-[2-ethyl-4-(4-fluoro-3-methylphenyl)-1H-imidazol-5-yl]quinoline Chemical compound C(C)C=1NC(=C(N=1)C1=CC(=C(C=C1)F)C)C=1C=C2C=CC=NC2=CC=1 LIKBZTZESCKFFS-UHFFFAOYSA-N 0.000 claims 1
PICAYFKWZQCFIF-UHFFFAOYSA-N 6-[2-ethyl-4-(4-fluoro-3-methylphenyl)-1H-imidazol-5-yl]quinoxaline Chemical compound C(C)C=1NC(=C(N=1)C1=CC(=C(C=C1)F)C)C=1C=C2N=CC=NC2=CC=1 PICAYFKWZQCFIF-UHFFFAOYSA-N 0.000 claims 1
LQDTYCGRESGYMP-UHFFFAOYSA-N 6-[2-ethyl-5-(3-fluorophenyl)-1H-imidazol-4-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)C=1NC(=C(N=1)C1=CC(=CC=C1)F)C=1C=CC=2N(C=1)N=CN=2 LQDTYCGRESGYMP-UHFFFAOYSA-N 0.000 claims 1
BWMSLTXVKOEJHM-UHFFFAOYSA-N 6-[2-ethyl-5-(3-fluorophenyl)-1H-imidazol-4-yl]imidazo[1,2-a]pyridine Chemical compound C(C)C=1NC(=C(N=1)C1=CC(=CC=C1)F)C=1C=CC=2N(C=1)C=CN=2 BWMSLTXVKOEJHM-UHFFFAOYSA-N 0.000 claims 1
QRRYAIVGAHXSHB-UHFFFAOYSA-N 6-[2-ethyl-5-(3-methylphenyl)-1H-imidazol-4-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)C=1NC(=C(N=1)C=1C=C(C=CC=1)C)C=1C=CC=2N(C=1)N=CN=2 QRRYAIVGAHXSHB-UHFFFAOYSA-N 0.000 claims 1
WGCXWBRRPBIEHQ-UHFFFAOYSA-N 6-[2-ethyl-5-(3-methylphenyl)-1H-imidazol-4-yl]imidazo[1,2-a]pyridine Chemical compound C(C)C=1NC(=C(N=1)C=1C=C(C=CC=1)C)C=1C=CC=2N(C=1)C=CN=2 WGCXWBRRPBIEHQ-UHFFFAOYSA-N 0.000 claims 1
OOEXUGOKZXYWOU-UHFFFAOYSA-N 6-[2-ethyl-5-(4-fluoro-3-methylphenyl)-1H-imidazol-4-yl]imidazo[1,2-a]pyridine Chemical compound C(C)C=1NC(=C(N=1)C1=CC(=C(C=C1)F)C)C=1C=CC=2N(C=1)C=CN=2 OOEXUGOKZXYWOU-UHFFFAOYSA-N 0.000 claims 1
VJWXAJCEZGEWFX-UHFFFAOYSA-N 6-[2-ethyl-5-(4-fluorophenyl)-1H-imidazol-4-yl]-1,3-benzothiazole Chemical compound C(C)C=1NC(=C(N=1)C1=CC=C(C=C1)F)C1=CC2=C(N=CS2)C=C1 VJWXAJCEZGEWFX-UHFFFAOYSA-N 0.000 claims 1
VJRVZPDUPQHHMR-UHFFFAOYSA-N 6-[2-ethyl-5-(4-fluorophenyl)-1H-imidazol-4-yl]-1H-indazole Chemical compound C(C)C=1NC(=C(N=1)C1=CC=C(C=C1)F)C1=CC=C2C=NNC2=C1 VJRVZPDUPQHHMR-UHFFFAOYSA-N 0.000 claims 1
DBKXPJVDAVYWDR-UHFFFAOYSA-N 6-[2-ethyl-5-(4-fluorophenyl)-1H-imidazol-4-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)C=1NC(=C(N=1)C1=CC=C(C=C1)F)C=1C=CC=2N(C=1)N=CN=2 DBKXPJVDAVYWDR-UHFFFAOYSA-N 0.000 claims 1
SKLWRNIQQOCJMF-UHFFFAOYSA-N 6-[2-ethyl-5-(4-fluorophenyl)-1H-imidazol-4-yl]imidazo[1,2-a]pyridine Chemical compound C(C)C=1NC(=C(N=1)C1=CC=C(C=C1)F)C=1C=CC=2N(C=1)C=CN=2 SKLWRNIQQOCJMF-UHFFFAOYSA-N 0.000 claims 1
WTOAWJPAUILHGA-UHFFFAOYSA-N 6-[2-methyl-4-(3,4,5-trifluorophenyl)-1H-imidazol-5-yl]-1,3-benzothiazole Chemical compound CC=1NC(=C(N=1)C1=CC(=C(C(=C1)F)F)F)C1=CC2=C(N=CS2)C=C1 WTOAWJPAUILHGA-UHFFFAOYSA-N 0.000 claims 1
XAFWIYNOPDLJFD-UHFFFAOYSA-N 6-[2-methyl-4-(3,4,5-trifluorophenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound CC=1NC(=C(N=1)C1=CC(=C(C(=C1)F)F)F)C1=CC=C2C=NNC2=C1 XAFWIYNOPDLJFD-UHFFFAOYSA-N 0.000 claims 1
QURSFSYITQOBRJ-UHFFFAOYSA-N 6-[2-methyl-4-(3,4,5-trifluorophenyl)-1H-imidazol-5-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC=1NC(=C(N=1)C1=CC(=C(C(=C1)F)F)F)C=1C=CC=2N(C=1)N=CN=2 QURSFSYITQOBRJ-UHFFFAOYSA-N 0.000 claims 1
QDFDKUYNPJIJLY-UHFFFAOYSA-N 6-[2-methyl-4-(3,4,5-trifluorophenyl)-1H-imidazol-5-yl]imidazo[1,2-a]pyridine Chemical compound CC=1NC(=C(N=1)C1=CC(=C(C(=C1)F)F)F)C=1C=CC=2N(C=1)C=CN=2 QDFDKUYNPJIJLY-UHFFFAOYSA-N 0.000 claims 1
NSRYFRPHASLGHF-UHFFFAOYSA-N 6-[2-methyl-4-(3,4,5-trifluorophenyl)-1H-imidazol-5-yl]quinoline Chemical compound CC=1NC(=C(N=1)C1=CC(=C(C(=C1)F)F)F)C=1C=C2C=CC=NC2=CC=1 NSRYFRPHASLGHF-UHFFFAOYSA-N 0.000 claims 1
QQNXJRSNSXHWSH-UHFFFAOYSA-N 6-[2-methyl-4-(3,4,5-trifluorophenyl)-1H-imidazol-5-yl]quinoxaline Chemical compound CC=1NC(=C(N=1)C1=CC(=C(C(=C1)F)F)F)C=1C=C2N=CC=NC2=CC=1 QQNXJRSNSXHWSH-UHFFFAOYSA-N 0.000 claims 1
XTUQMFBGWWBBJK-UHFFFAOYSA-N 6-[2-methyl-5-(2,4,5-trifluorophenyl)-1H-imidazol-4-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC=1NC(=C(N=1)C1=C(C=C(C(=C1)F)F)F)C=1C=CC=2N(C=1)N=CN=2 XTUQMFBGWWBBJK-UHFFFAOYSA-N 0.000 claims 1
CNPBZTMRYQNDOU-UHFFFAOYSA-N 6-[2-methyl-5-(2,4,5-trifluorophenyl)-1H-imidazol-4-yl]quinoline Chemical compound CC=1NC(=C(N=1)C1=C(C=C(C(=C1)F)F)F)C=1C=C2C=CC=NC2=CC=1 CNPBZTMRYQNDOU-UHFFFAOYSA-N 0.000 claims 1
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FPQLGUMJFUYAFN-UHFFFAOYSA-N 6-[3-(1,3-dihydroxypropan-2-yl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound OCC(CO)N1C=NC(=C1C=1C=CC=2N(C=1)C(=CN=2)C(=O)N)C1=CC=C(C=C1)F FPQLGUMJFUYAFN-UHFFFAOYSA-N 0.000 claims 1
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OJNNUDOOADABHK-UHFFFAOYSA-N 6-[5-(3-chloro-4-fluorophenyl)-3-(3-hydroxycyclobutyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound OC1CC(C1)n1cnc(c1-c1ccc2ncc(C#N)n2n1)-c1ccc(F)c(Cl)c1 OJNNUDOOADABHK-UHFFFAOYSA-N 0.000 claims 1
LMDNOBRZXKYAJO-UHFFFAOYSA-N 6-[5-(3-chloro-4-fluorophenyl)-3-(3-hydroxycyclobutyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carboxamide Chemical compound NC(=O)C1=CN=C2C=CC(=NN12)C1=C(N=CN1C1CC(O)C1)C1=CC(Cl)=C(F)C=C1 LMDNOBRZXKYAJO-UHFFFAOYSA-N 0.000 claims 1
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CZFFYMSCWHRWSX-UHFFFAOYSA-N 6-[5-(3-chloro-4-fluorophenyl)-3-(3-methylbutyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carboxamide Chemical compound ClC=1C=C(C=CC=1F)C=1N=CN(C=1C=1C=CC=2N(N=1)C(=CN=2)C(=O)N)CCC(C)C CZFFYMSCWHRWSX-UHFFFAOYSA-N 0.000 claims 1
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LUABADMUPNRBMU-CYBMUJFWSA-N 6-[5-(3-chloro-4-fluorophenyl)-3-[(1R)-3,3-difluorocyclopentyl]imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound ClC=1C=C(C=CC=1F)C=1N=CN(C=1C=1C=CC=2N(N=1)C(=CN=2)C#N)[C@H]1CC(CC1)(F)F LUABADMUPNRBMU-CYBMUJFWSA-N 0.000 claims 1
LUABADMUPNRBMU-ZDUSSCGKSA-N 6-[5-(3-chloro-4-fluorophenyl)-3-[(1S)-3,3-difluorocyclopentyl]imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound ClC=1C=C(C=CC=1F)C=1N=CN(C=1C=1C=CC=2N(N=1)C(=CN=2)C#N)[C@@H]1CC(CC1)(F)F LUABADMUPNRBMU-ZDUSSCGKSA-N 0.000 claims 1
NBESPYDHKUMOPU-UHFFFAOYSA-N 6-[5-(3-chloro-4-fluorophenyl)-3-[(3-methyloxetan-3-yl)methyl]imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound ClC=1C=C(C=CC=1F)C=1N=CN(C=1C=1C=CC=2N(N=1)C(=CN=2)C#N)CC1(COC1)C NBESPYDHKUMOPU-UHFFFAOYSA-N 0.000 claims 1
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CMMIZEHBXXNCFI-UHFFFAOYSA-N 6-[5-(3-cyano-4-fluorophenyl)-3-(2,2-difluoroethyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound C(#N)C=1C=C(C=CC=1F)C=1N=CN(C=1C=1C=CC=2N(N=1)C(=CN=2)C#N)CC(F)F CMMIZEHBXXNCFI-UHFFFAOYSA-N 0.000 claims 1
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AHOJTOFZHXDXJV-UHFFFAOYSA-N 6-[5-(4-aminophenyl)-3-(2,2-difluoroethyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound NC1=CC=C(C=C1)C=1N=CN(C=1C=1C=CC=2N(N=1)C(=CN=2)C#N)CC(F)F AHOJTOFZHXDXJV-UHFFFAOYSA-N 0.000 claims 1
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DLDAIECUDPBQEV-UHFFFAOYSA-N N-cyclopropyl-6-[3-(2,2-difluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1(CC1)NC(=O)C1=CN=C2N1C=C(C=C2)C1=C(N=CN1CC(F)F)C1=CC=C(C=C1)F DLDAIECUDPBQEV-UHFFFAOYSA-N 0.000 claims 1
XRWNILSSGPXRRL-UHFFFAOYSA-N N-cyclopropyl-6-[3-(2,2-difluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carboxamide Chemical compound C1(CC1)NC(=O)C1=CN=C2N1N=C(C=C2)C1=C(N=CN1CC(F)F)C1=CC=C(C=C1)F XRWNILSSGPXRRL-UHFFFAOYSA-N 0.000 claims 1
YVLPQHRSYYMYIK-UHFFFAOYSA-N N-tert-butyl-3-[5-(3-cyanoimidazo[1,2-b]pyridazin-6-yl)-4-(4-fluorophenyl)imidazol-1-yl]azetidine-1-carboxamide Chemical compound C(C)(C)(C)NC(=O)N1CC(C1)N1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)C1=CC=C(C=C1)F YVLPQHRSYYMYIK-UHFFFAOYSA-N 0.000 claims 1
239000012270 PD-1 inhibitor Substances 0.000 claims 1
239000012668 PD-1-inhibitor Substances 0.000 claims 1
208000012654 Primary biliary cholangitis Diseases 0.000 claims 1
206010039580 Scar Diseases 0.000 claims 1
XHGJZPUFJXDWQS-UHFFFAOYSA-N [6-[3-(2,2-difluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazin-3-yl]methanol Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)CO)C1=CC=C(C=C1)F)F XHGJZPUFJXDWQS-UHFFFAOYSA-N 0.000 claims 1
239000000427 antigen Substances 0.000 claims 1
102000036639 antigens Human genes 0.000 claims 1
108091007433 antigens Proteins 0.000 claims 1
208000013355 benign neoplasm of brain Diseases 0.000 claims 1
210000004556 brain Anatomy 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
230000007882 cirrhosis Effects 0.000 claims 1
208000019425 cirrhosis of liver Diseases 0.000 claims 1
230000000694 effects Effects 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
150000004677 hydrates Chemical class 0.000 claims 1
YCLUMBJQKREDFM-UHFFFAOYSA-N imidazo[1,2-b]pyridazine-3-carboxamide Chemical compound C1=CC=NN2C(C(=O)N)=CN=C21 YCLUMBJQKREDFM-UHFFFAOYSA-N 0.000 claims 1
238000002347 injection Methods 0.000 claims 1
239000007924 injection Substances 0.000 claims 1
ZRINUMCLUXPCSS-UHFFFAOYSA-N methyl 3-(3-carbamoylimidazo[1,2-a]pyridin-6-yl)-2-(4-fluorophenyl)-6,8-dihydro-5H-imidazo[1,2-a]pyrazine-7-carboxylate Chemical compound C(N)(=O)C1=CN=C2N1C=C(C=C2)C1=C(N=C2N1CCN(C2)C(=O)OC)C1=CC=C(C=C1)F ZRINUMCLUXPCSS-UHFFFAOYSA-N 0.000 claims 1
HRDYKDMFKNHRLI-UHFFFAOYSA-N methyl 3-[5-(3-cyanoimidazo[1,2-b]pyridazin-6-yl)-4-(4-fluorophenyl)imidazol-1-yl]azetidine-1-carboxylate Chemical compound C(#N)C1=CN=C2N1N=C(C=C2)C1=C(N=CN1C1CN(C1)C(=O)OC)C1=CC=C(C=C1)F HRDYKDMFKNHRLI-UHFFFAOYSA-N 0.000 claims 1
QNJMAOVEDIYRQR-UHFFFAOYSA-N methyl N-[6-[3-(2,2-difluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-a]pyridin-3-yl]carbamate Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(C=1)C(=CN=2)NC(OC)=O)C1=CC=C(C=C1)F)F QNJMAOVEDIYRQR-UHFFFAOYSA-N 0.000 claims 1
PETOLPLJUPJGJL-UHFFFAOYSA-N methyl N-[6-[3-(2,2-difluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazin-3-yl]carbamate Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)NC(OC)=O)C1=CC=C(C=C1)F)F PETOLPLJUPJGJL-UHFFFAOYSA-N 0.000 claims 1
GUVLGFQGWDPQJB-UHFFFAOYSA-N methyl N-[[6-[3-(2,2-difluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazin-3-yl]methyl]carbamate Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)CNC(OC)=O)C1=CC=C(C=C1)F)F GUVLGFQGWDPQJB-UHFFFAOYSA-N 0.000 claims 1
229960003301 nivolumab Drugs 0.000 claims 1
229940121655 pd-1 inhibitor Drugs 0.000 claims 1
KIZAYCDMZCYWOZ-UHFFFAOYSA-N propan-2-yl N-[[6-[3-(2,2-difluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazin-3-yl]methyl]carbamate Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)CNC(OC(C)C)=O)C1=CC=C(C=C1)F)F KIZAYCDMZCYWOZ-UHFFFAOYSA-N 0.000 claims 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 1
230000037390 scarring Effects 0.000 claims 1
BQTCCDHKTZZMLE-UHFFFAOYSA-N tert-butyl 3-[5-(3-carbamoylimidazo[1,2-b]pyridazin-6-yl)-4-(4-fluorophenyl)imidazol-1-yl]azetidine-1-carboxylate Chemical compound C(N)(=O)C1=CN=C2N1N=C(C=C2)C1=C(N=CN1C1CN(C1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)F BQTCCDHKTZZMLE-UHFFFAOYSA-N 0.000 claims 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1

JP2017546173A 2015-03-02 2016-02-26 ＴＧＦ−β阻害剤 Expired - Fee Related JP6836998B2 (ja)