HRP20110180T1 - Spojevi za upotrebu kod upala i upotrebe vezane uz imunitet - Google Patents
Spojevi za upotrebu kod upala i upotrebe vezane uz imunitet Download PDFInfo
- Publication number
- HRP20110180T1 HRP20110180T1 HR20110180T HRP20110180T HRP20110180T1 HR P20110180 T1 HRP20110180 T1 HR P20110180T1 HR 20110180 T HR20110180 T HR 20110180T HR P20110180 T HRP20110180 T HR P20110180T HR P20110180 T1 HRP20110180 T1 HR P20110180T1
- Authority
- HR
- Croatia
- Prior art keywords
- optionally substituted
- trifluoromethyl
- biphenyl
- phenyl
- difluoro
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract 55
- 206010061218 Inflammation Diseases 0.000 title 1
- 230000004054 inflammatory process Effects 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract 41
- 239000012453 solvate Substances 0.000 claims abstract 41
- 239000003018 immunosuppressive agent Substances 0.000 claims abstract 2
- 229940125721 immunosuppressive agent Drugs 0.000 claims abstract 2
- -1 -OR4 Chemical group 0.000 claims 83
- 125000001072 heteroaryl group Chemical group 0.000 claims 77
- 125000000623 heterocyclic group Chemical group 0.000 claims 63
- 125000003107 substituted aryl group Chemical group 0.000 claims 57
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 49
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 49
- 125000003710 aryl alkyl group Chemical group 0.000 claims 47
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 47
- 125000000547 substituted alkyl group Chemical group 0.000 claims 47
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 47
- 125000005843 halogen group Chemical group 0.000 claims 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims 24
- 238000000034 method Methods 0.000 claims 24
- 125000001188 haloalkyl group Chemical group 0.000 claims 23
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 19
- 125000004076 pyridyl group Chemical group 0.000 claims 18
- 229910052757 nitrogen Inorganic materials 0.000 claims 16
- 239000000825 pharmaceutical preparation Substances 0.000 claims 16
- 125000004438 haloalkoxy group Chemical group 0.000 claims 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 14
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 12
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 12
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 8
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 8
- 125000001544 thienyl group Chemical group 0.000 claims 8
- 125000001425 triazolyl group Chemical group 0.000 claims 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 7
- LOKPCLOCVRXPGR-UHFFFAOYSA-N 2,3-difluoro-n-[4-[2-(trifluoromethyl)indolizin-3-yl]phenyl]benzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=CC(=CC=2)C=2N3C=CC=CC3=CC=2C(F)(F)F)=C1F LOKPCLOCVRXPGR-UHFFFAOYSA-N 0.000 claims 6
- HDLANTLODKXVBM-UHFFFAOYSA-N 2,3-difluoro-n-[4-[3-thiophen-3-yl-5-(trifluoromethyl)-1,2,4-triazol-4-yl]phenyl]benzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=CC(=CC=2)N2C(=NN=C2C2=CSC=C2)C(F)(F)F)=C1F HDLANTLODKXVBM-UHFFFAOYSA-N 0.000 claims 6
- 210000004027 cell Anatomy 0.000 claims 6
- 239000003937 drug carrier Substances 0.000 claims 6
- PPSKETUMTSIHFN-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)C=C1 PPSKETUMTSIHFN-UHFFFAOYSA-N 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000002541 furyl group Chemical group 0.000 claims 4
- 238000000338 in vitro Methods 0.000 claims 4
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- RODKSPSXJYTKKC-UHFFFAOYSA-N 2,3-difluoro-n-[2-fluoro-4-[2-(trifluoromethyl)phenyl]phenyl]benzamide Chemical compound FC1=CC=CC(C(=O)NC=2C(=CC(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)F)=C1F RODKSPSXJYTKKC-UHFFFAOYSA-N 0.000 claims 3
- DSSKDARDNCTZCD-UHFFFAOYSA-N 2,3-difluoro-n-[3-(trifluoromethyl)-4-[2-(trifluoromethyl)phenyl]phenyl]benzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=C(C(C=3C(=CC=CC=3)C(F)(F)F)=CC=2)C(F)(F)F)=C1F DSSKDARDNCTZCD-UHFFFAOYSA-N 0.000 claims 3
- UFZWBTOIQRFNLK-UHFFFAOYSA-N 2,3-difluoro-n-[4-(2,4,5-trimethylphenyl)phenyl]benzamide Chemical compound C1=C(C)C(C)=CC(C)=C1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F UFZWBTOIQRFNLK-UHFFFAOYSA-N 0.000 claims 3
- XUXCFDUQWUWQLT-UHFFFAOYSA-N 2,3-difluoro-n-[4-(2-methoxy-5-methylphenyl)phenyl]benzamide Chemical compound COC1=CC=C(C)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F XUXCFDUQWUWQLT-UHFFFAOYSA-N 0.000 claims 3
- JMICNCFBFBRLIM-UHFFFAOYSA-N 2,3-difluoro-n-[4-(3-methylpent-2-en-2-yl)-3-(trifluoromethyl)phenyl]benzamide Chemical compound C1=C(C(F)(F)F)C(C(C)=C(C)CC)=CC=C1NC(=O)C1=CC=CC(F)=C1F JMICNCFBFBRLIM-UHFFFAOYSA-N 0.000 claims 3
- SASKHUPJTPGMEA-UHFFFAOYSA-N 2,3-difluoro-n-[4-[2-fluoro-5-(trifluoromethyl)phenyl]phenyl]benzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=CC(=CC=2)C=2C(=CC=C(C=2)C(F)(F)F)F)=C1F SASKHUPJTPGMEA-UHFFFAOYSA-N 0.000 claims 3
- HIRKWQUXRHXOJN-UHFFFAOYSA-N 2,3-difluoro-n-[4-[2-fluoro-6-(trifluoromethyl)phenyl]phenyl]benzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=CC(=CC=2)C=2C(=CC=CC=2F)C(F)(F)F)=C1F HIRKWQUXRHXOJN-UHFFFAOYSA-N 0.000 claims 3
- ZADZAOOGRKKHHX-UHFFFAOYSA-N 2,3-difluoro-n-[4-[3-(trifluoromethyl)-2h-indolizin-3-yl]phenyl]benzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=CC(=CC=2)C2(N3C=CC=CC3=CC2)C(F)(F)F)=C1F ZADZAOOGRKKHHX-UHFFFAOYSA-N 0.000 claims 3
- QFGFRYFWZRGBQP-UHFFFAOYSA-N 2,3-difluoro-n-[4-[5-fluoro-2-(trifluoromethyl)indolizin-3-yl]phenyl]benzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=CC(=CC=2)C=2N3C(F)=CC=CC3=CC=2C(F)(F)F)=C1F QFGFRYFWZRGBQP-UHFFFAOYSA-N 0.000 claims 3
- XPIUSJJYZREVOB-UHFFFAOYSA-N 2,3-difluoro-n-[4-[5-methoxy-2-(trifluoromethyl)indolizin-3-yl]phenyl]benzamide Chemical compound N12C(OC)=CC=CC2=CC(C(F)(F)F)=C1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F XPIUSJJYZREVOB-UHFFFAOYSA-N 0.000 claims 3
- VTXPBIAPUCMYJG-UHFFFAOYSA-N 2,3-difluoro-n-[4-[6-methoxy-2-(trifluoromethyl)indolizin-3-yl]phenyl]benzamide Chemical compound N12C=C(OC)C=CC2=CC(C(F)(F)F)=C1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F VTXPBIAPUCMYJG-UHFFFAOYSA-N 0.000 claims 3
- GTVMZYFJPSTISK-UHFFFAOYSA-N 2,3-difluoro-n-[4-[7-methoxy-2-(trifluoromethyl)indolizin-3-yl]phenyl]benzamide Chemical compound FC(F)(F)C=1C=C2C=C(OC)C=CN2C=1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F GTVMZYFJPSTISK-UHFFFAOYSA-N 0.000 claims 3
- RYDKPHTXHUEPFH-UHFFFAOYSA-N 2,3-difluoro-n-[4-[8-methoxy-2-(trifluoromethyl)indolizin-3-yl]phenyl]benzamide Chemical compound FC(F)(F)C=1C=C2C(OC)=CC=CN2C=1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F RYDKPHTXHUEPFH-UHFFFAOYSA-N 0.000 claims 3
- SFQODEMMYULEMB-UHFFFAOYSA-N 2,4,5-trifluoro-n-[4-[5-fluoro-2-(trifluoromethyl)indolizin-3-yl]phenyl]benzamide Chemical compound C1=C(F)C(F)=CC(F)=C1C(=O)NC1=CC=C(C=2N3C(F)=CC=CC3=CC=2C(F)(F)F)C=C1 SFQODEMMYULEMB-UHFFFAOYSA-N 0.000 claims 3
- VVOYIUOZAQJEGS-UHFFFAOYSA-N 2,4,5-trifluoro-n-[4-[5-methoxy-2-(trifluoromethyl)indolizin-3-yl]phenyl]benzamide Chemical compound N12C(OC)=CC=CC2=CC(C(F)(F)F)=C1C(C=C1)=CC=C1NC(=O)C1=CC(F)=C(F)C=C1F VVOYIUOZAQJEGS-UHFFFAOYSA-N 0.000 claims 3
- GQBTWFVTPFDAHC-UHFFFAOYSA-N 2,4,5-trifluoro-n-[4-[6-methoxy-2-(trifluoromethyl)indolizin-3-yl]phenyl]benzamide Chemical compound N12C=C(OC)C=CC2=CC(C(F)(F)F)=C1C(C=C1)=CC=C1NC(=O)C1=CC(F)=C(F)C=C1F GQBTWFVTPFDAHC-UHFFFAOYSA-N 0.000 claims 3
- KFDQLUJBDVXHMN-UHFFFAOYSA-N 2,4,5-trifluoro-n-[4-[7-methoxy-2-(trifluoromethyl)indolizin-3-yl]phenyl]benzamide Chemical compound FC(F)(F)C=1C=C2C=C(OC)C=CN2C=1C(C=C1)=CC=C1NC(=O)C1=CC(F)=C(F)C=C1F KFDQLUJBDVXHMN-UHFFFAOYSA-N 0.000 claims 3
- AUYKGRUXPRZGSH-UHFFFAOYSA-N 2,4,5-trifluoro-n-[4-[8-methoxy-2-(trifluoromethyl)indolizin-3-yl]phenyl]benzamide Chemical compound FC(F)(F)C=1C=C2C(OC)=CC=CN2C=1C(C=C1)=CC=C1NC(=O)C1=CC(F)=C(F)C=C1F AUYKGRUXPRZGSH-UHFFFAOYSA-N 0.000 claims 3
- JXGLLQGTDQCTAM-UHFFFAOYSA-N 2,4-dimethyl-n-[4-[2-(trifluoromethyl)phenyl]phenyl]-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NC(C)=C1C(=O)NC1=CC=C(C=2C(=CC=CC=2)C(F)(F)F)C=C1 JXGLLQGTDQCTAM-UHFFFAOYSA-N 0.000 claims 3
- NQZYZEAOLHZYPW-UHFFFAOYSA-N 2,5-difluoro-n-[4-[2-(trifluoromethyl)indolizin-3-yl]phenyl]benzamide Chemical compound FC1=CC=C(F)C(C(=O)NC=2C=CC(=CC=2)C=2N3C=CC=CC3=CC=2C(F)(F)F)=C1 NQZYZEAOLHZYPW-UHFFFAOYSA-N 0.000 claims 3
- NAQVBBRZJGIBOH-UHFFFAOYSA-N 2,5-difluoro-n-[4-[2-(trifluoromethyl)phenyl]phenyl]benzamide Chemical compound FC1=CC=C(F)C(C(=O)NC=2C=CC(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=C1 NAQVBBRZJGIBOH-UHFFFAOYSA-N 0.000 claims 3
- KNDPPJIUFYWIID-UHFFFAOYSA-N 2,6-difluoro-n-[4-[5-fluoro-2-(trifluoromethyl)indolizin-3-yl]phenyl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2N3C(F)=CC=CC3=CC=2C(F)(F)F)C=C1 KNDPPJIUFYWIID-UHFFFAOYSA-N 0.000 claims 3
- DDWIPMZMXBTQFU-UHFFFAOYSA-N 2,6-difluoro-n-[4-[5-methoxy-2-(trifluoromethyl)indolizin-3-yl]phenyl]benzamide Chemical compound N12C(OC)=CC=CC2=CC(C(F)(F)F)=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F DDWIPMZMXBTQFU-UHFFFAOYSA-N 0.000 claims 3
- RRZSDNHRDXRCFB-UHFFFAOYSA-N 2,6-difluoro-n-[4-[5-methyl-2-(trifluoromethyl)phenyl]phenyl]benzamide Chemical compound CC1=CC=C(C(F)(F)F)C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 RRZSDNHRDXRCFB-UHFFFAOYSA-N 0.000 claims 3
- RTRWBBMWIXDXHU-UHFFFAOYSA-N 2,6-difluoro-n-[4-[6-methoxy-2-(trifluoromethyl)indolizin-3-yl]phenyl]benzamide Chemical compound N12C=C(OC)C=CC2=CC(C(F)(F)F)=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F RTRWBBMWIXDXHU-UHFFFAOYSA-N 0.000 claims 3
- DBYQXPHQVVSMFB-UHFFFAOYSA-N 2,6-difluoro-n-[4-[7-methoxy-2-(trifluoromethyl)indolizin-3-yl]phenyl]benzamide Chemical compound FC(F)(F)C=1C=C2C=C(OC)C=CN2C=1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F DBYQXPHQVVSMFB-UHFFFAOYSA-N 0.000 claims 3
- YAGRGSPLLIWGFE-UHFFFAOYSA-N 2,6-difluoro-n-[4-[8-methoxy-2-(trifluoromethyl)indolizin-3-yl]phenyl]benzamide Chemical compound FC(F)(F)C=1C=C2C(OC)=CC=CN2C=1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F YAGRGSPLLIWGFE-UHFFFAOYSA-N 0.000 claims 3
- AZZPUQMQPKRIJL-UHFFFAOYSA-N 2-ethyl-5-methyl-n-[4-[2-(trifluoromethyl)phenyl]phenyl]pyrazole-3-carboxamide Chemical compound CCN1N=C(C)C=C1C(=O)NC1=CC=C(C=2C(=CC=CC=2)C(F)(F)F)C=C1 AZZPUQMQPKRIJL-UHFFFAOYSA-N 0.000 claims 3
- PAXANZFKHKNUKR-UHFFFAOYSA-N 2-methyl-5-(trifluoromethyl)-n-[4-[2-(trifluoromethyl)phenyl]phenyl]-1,3-oxazole-4-carboxamide Chemical compound O1C(C)=NC(C(=O)NC=2C=CC(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=C1C(F)(F)F PAXANZFKHKNUKR-UHFFFAOYSA-N 0.000 claims 3
- SWYLSLZPJMBYGI-UHFFFAOYSA-N 3,4-dimethoxy-n-[4-[2-(trifluoromethyl)indolizin-3-yl]phenyl]benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NC1=CC=C(C=2N3C=CC=CC3=CC=2C(F)(F)F)C=C1 SWYLSLZPJMBYGI-UHFFFAOYSA-N 0.000 claims 3
- OMERAJJHKZZZEW-UHFFFAOYSA-N 3-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-1,1-diethylurea Chemical compound C1=CC(NC(=O)N(CC)CC)=CC=C1C1=CC(C(F)(F)F)=CC=C1C(F)(F)F OMERAJJHKZZZEW-UHFFFAOYSA-N 0.000 claims 3
- BLUOMGLQBVUWTH-UHFFFAOYSA-N 3-fluoro-n-[4-(2-methylphenyl)phenyl]pyridine-4-carboxamide Chemical compound CC1=CC=CC=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1F BLUOMGLQBVUWTH-UHFFFAOYSA-N 0.000 claims 3
- WVKINTDHLSSGLX-UHFFFAOYSA-N 3-fluoro-n-[4-[2-(trifluoromethyl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound FC1=CN=CC=C1C(=O)NC1=CC=C(C=2C(=CC=CC=2)C(F)(F)F)C=C1 WVKINTDHLSSGLX-UHFFFAOYSA-N 0.000 claims 3
- FDFQGFZSSOZOPH-UHFFFAOYSA-N 3-fluoro-n-[4-[3-(trifluoromethyl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound FC1=CN=CC=C1C(=O)NC1=CC=C(C=2C=C(C=CC=2)C(F)(F)F)C=C1 FDFQGFZSSOZOPH-UHFFFAOYSA-N 0.000 claims 3
- OBOQPEBXELZASA-UHFFFAOYSA-N 3-methyl-n-[4-(2-methylsulfanylphenyl)phenyl]pyridine-4-carboxamide Chemical compound CSC1=CC=CC=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C OBOQPEBXELZASA-UHFFFAOYSA-N 0.000 claims 3
- BBYVGUCKNFNBHG-UHFFFAOYSA-N 3-methyl-n-[4-(2-propan-2-ylphenyl)phenyl]pyridine-4-carboxamide Chemical compound CC(C)C1=CC=CC=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C BBYVGUCKNFNBHG-UHFFFAOYSA-N 0.000 claims 3
- OSMAGAVKVRGYGR-UHFFFAOYSA-N 3-methylpyridine-4-carboxylic acid Chemical compound CC1=CN=CC=C1C(O)=O OSMAGAVKVRGYGR-UHFFFAOYSA-N 0.000 claims 3
- VRYAOEYBOOCTDR-UHFFFAOYSA-N 4-(trifluoromethyl)-n-[4-[2-(trifluoromethyl)phenyl]phenyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=NC=C1C(=O)NC1=CC=C(C=2C(=CC=CC=2)C(F)(F)F)C=C1 VRYAOEYBOOCTDR-UHFFFAOYSA-N 0.000 claims 3
- GXNXKZCFHUUEFU-UHFFFAOYSA-N 4-fluoro-n-[4-[2-(trifluoromethyl)phenyl]phenyl]benzamide Chemical compound C1=CC(F)=CC=C1C(=O)NC1=CC=C(C=2C(=CC=CC=2)C(F)(F)F)C=C1 GXNXKZCFHUUEFU-UHFFFAOYSA-N 0.000 claims 3
- SVBUQWXXBPEXNY-UHFFFAOYSA-N 4-methyl-n-[4-(2-methylindolizin-3-yl)phenyl]thiadiazole-5-carboxamide Chemical compound CC=1C=C2C=CC=CN2C=1C(C=C1)=CC=C1NC(=O)C=1SN=NC=1C SVBUQWXXBPEXNY-UHFFFAOYSA-N 0.000 claims 3
- 102000004310 Ion Channels Human genes 0.000 claims 3
- 108090000862 Ion Channels Proteins 0.000 claims 3
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- DIIFIXDKOOPCAR-UHFFFAOYSA-N methyl 3-[4-[(2,3-difluorobenzoyl)amino]phenyl]-2-(trifluoromethyl)indolizine-6-carboxylate Chemical compound N12C=C(C(=O)OC)C=CC2=CC(C(F)(F)F)=C1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F DIIFIXDKOOPCAR-UHFFFAOYSA-N 0.000 claims 3
- AYJXHVVXQGQMAD-UHFFFAOYSA-N methyl 3-[4-[(2,3-difluorobenzoyl)amino]phenyl]-5-methoxy-2-(trifluoromethyl)indolizine-6-carboxylate Chemical compound N12C(OC)=C(C(=O)OC)C=CC2=CC(C(F)(F)F)=C1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F AYJXHVVXQGQMAD-UHFFFAOYSA-N 0.000 claims 3
- ZHCZWORURPKSCB-UHFFFAOYSA-N methyl 3-[4-[(2,4,5-trifluorobenzoyl)amino]phenyl]-2-(trifluoromethyl)indolizine-6-carboxylate Chemical compound N12C=C(C(=O)OC)C=CC2=CC(C(F)(F)F)=C1C(C=C1)=CC=C1NC(=O)C1=CC(F)=C(F)C=C1F ZHCZWORURPKSCB-UHFFFAOYSA-N 0.000 claims 3
- UQZZNFPVJIJKIT-UHFFFAOYSA-N methyl 3-[4-[(2,6-difluorobenzoyl)amino]phenyl]-2-(trifluoromethyl)indolizine-6-carboxylate Chemical compound N12C=C(C(=O)OC)C=CC2=CC(C(F)(F)F)=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F UQZZNFPVJIJKIT-UHFFFAOYSA-N 0.000 claims 3
- IJXIARDLYSGWSL-UHFFFAOYSA-N methyl 3-[4-[(2,6-difluorobenzoyl)amino]phenyl]-5-methoxy-2-(trifluoromethyl)indolizine-6-carboxylate Chemical compound N12C(OC)=C(C(=O)OC)C=CC2=CC(C(F)(F)F)=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F IJXIARDLYSGWSL-UHFFFAOYSA-N 0.000 claims 3
- VLZKOGFREJDPGT-UHFFFAOYSA-N methyl 5-chloro-3-[4-[(2,3-difluorobenzoyl)amino]phenyl]-2-(trifluoromethyl)indolizine-6-carboxylate Chemical compound N12C(Cl)=C(C(=O)OC)C=CC2=CC(C(F)(F)F)=C1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F VLZKOGFREJDPGT-UHFFFAOYSA-N 0.000 claims 3
- VMCAIVHSLYANJU-UHFFFAOYSA-N methyl 5-chloro-3-[4-[(2,3-difluorobenzoyl)amino]phenyl]-2-(trifluoromethyl)indolizine-7-carboxylate Chemical compound FC(F)(F)C=1C=C2C=C(C(=O)OC)C=C(Cl)N2C=1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F VMCAIVHSLYANJU-UHFFFAOYSA-N 0.000 claims 3
- CZOWQOJYJWMBGP-UHFFFAOYSA-N methyl 5-chloro-3-[4-[(2,4,5-trifluorobenzoyl)amino]phenyl]-2-(trifluoromethyl)indolizine-6-carboxylate Chemical compound N12C(Cl)=C(C(=O)OC)C=CC2=CC(C(F)(F)F)=C1C(C=C1)=CC=C1NC(=O)C1=CC(F)=C(F)C=C1F CZOWQOJYJWMBGP-UHFFFAOYSA-N 0.000 claims 3
- VICUSRNZVKWVEZ-UHFFFAOYSA-N methyl 5-chloro-3-[4-[(2,4,5-trifluorobenzoyl)amino]phenyl]-2-(trifluoromethyl)indolizine-7-carboxylate Chemical compound FC(F)(F)C=1C=C2C=C(C(=O)OC)C=C(Cl)N2C=1C(C=C1)=CC=C1NC(=O)C1=CC(F)=C(F)C=C1F VICUSRNZVKWVEZ-UHFFFAOYSA-N 0.000 claims 3
- JWQUQOHUTYGXTC-UHFFFAOYSA-N methyl 5-chloro-3-[4-[(2,6-difluorobenzoyl)amino]phenyl]-2-(trifluoromethyl)indolizine-6-carboxylate Chemical compound N12C(Cl)=C(C(=O)OC)C=CC2=CC(C(F)(F)F)=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F JWQUQOHUTYGXTC-UHFFFAOYSA-N 0.000 claims 3
- UCGATTXUVRZMDQ-UHFFFAOYSA-N methyl 5-chloro-3-[4-[(2,6-difluorobenzoyl)amino]phenyl]-2-(trifluoromethyl)indolizine-7-carboxylate Chemical compound FC(F)(F)C=1C=C2C=C(C(=O)OC)C=C(Cl)N2C=1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F UCGATTXUVRZMDQ-UHFFFAOYSA-N 0.000 claims 3
- MILUUJCYYCFTDC-UHFFFAOYSA-N methyl 5-methoxy-3-[4-[(2,4,5-trifluorobenzoyl)amino]phenyl]-2-(trifluoromethyl)indolizine-6-carboxylate Chemical compound N12C(OC)=C(C(=O)OC)C=CC2=CC(C(F)(F)F)=C1C(C=C1)=CC=C1NC(=O)C1=CC(F)=C(F)C=C1F MILUUJCYYCFTDC-UHFFFAOYSA-N 0.000 claims 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 3
- AWSLHGOLWFEELK-UHFFFAOYSA-N n-[4-(2,5-dichlorophenyl)phenyl]-2,3-difluorobenzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=CC(=CC=2)C=2C(=CC=C(Cl)C=2)Cl)=C1F AWSLHGOLWFEELK-UHFFFAOYSA-N 0.000 claims 3
- JDRVPORPMVPGLD-UHFFFAOYSA-N n-[4-(2,5-dichlorophenyl)phenyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2C(=CC=C(Cl)C=2)Cl)C=C1 JDRVPORPMVPGLD-UHFFFAOYSA-N 0.000 claims 3
- AIWPFUYDXBUFGY-UHFFFAOYSA-N n-[4-(2,5-diethylphenyl)phenyl]-3-methylpyridine-4-carboxamide Chemical compound CCC1=CC=C(CC)C(C=2C=CC(NC(=O)C=3C(=CN=CC=3)C)=CC=2)=C1 AIWPFUYDXBUFGY-UHFFFAOYSA-N 0.000 claims 3
- FCEZDQJVOFOLSE-UHFFFAOYSA-N n-[4-(2,5-dimethoxyphenyl)phenyl]-2,3-difluorobenzamide Chemical compound COC1=CC=C(OC)C(C=2C=CC(NC(=O)C=3C(=C(F)C=CC=3)F)=CC=2)=C1 FCEZDQJVOFOLSE-UHFFFAOYSA-N 0.000 claims 3
- SYCDGKRZAAXWDM-UHFFFAOYSA-N n-[4-(2,5-dimethoxyphenyl)phenyl]-2,6-difluorobenzamide Chemical compound COC1=CC=C(OC)C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 SYCDGKRZAAXWDM-UHFFFAOYSA-N 0.000 claims 3
- QFRHSVYOONQQDG-UHFFFAOYSA-N n-[4-(2,5-dimethoxyphenyl)phenyl]-2-methylbenzamide Chemical compound COC1=CC=C(OC)C(C=2C=CC(NC(=O)C=3C(=CC=CC=3)C)=CC=2)=C1 QFRHSVYOONQQDG-UHFFFAOYSA-N 0.000 claims 3
- GFEIWXNLDKUWIK-UHFFFAOYSA-N n-[4-(2,5-dimethoxyphenyl)phenyl]-3-fluoropyridine-4-carboxamide Chemical compound COC1=CC=C(OC)C(C=2C=CC(NC(=O)C=3C(=CN=CC=3)F)=CC=2)=C1 GFEIWXNLDKUWIK-UHFFFAOYSA-N 0.000 claims 3
- WJFCPKXXHNSABN-UHFFFAOYSA-N n-[4-(2,5-dimethoxyphenyl)phenyl]-3-methylpyridine-4-carboxamide Chemical compound COC1=CC=C(OC)C(C=2C=CC(NC(=O)C=3C(=CN=CC=3)C)=CC=2)=C1 WJFCPKXXHNSABN-UHFFFAOYSA-N 0.000 claims 3
- LYQZSCWNQRGLGX-UHFFFAOYSA-N n-[4-(2,5-dimethoxyphenyl)phenyl]-4-methylthiadiazole-5-carboxamide Chemical compound COC1=CC=C(OC)C(C=2C=CC(NC(=O)C3=C(N=NS3)C)=CC=2)=C1 LYQZSCWNQRGLGX-UHFFFAOYSA-N 0.000 claims 3
- QARVELYUQXUXPD-UHFFFAOYSA-N n-[4-(2,5-dimethylphenyl)phenyl]-2,3-difluorobenzamide Chemical compound CC1=CC=C(C)C(C=2C=CC(NC(=O)C=3C(=C(F)C=CC=3)F)=CC=2)=C1 QARVELYUQXUXPD-UHFFFAOYSA-N 0.000 claims 3
- XMOXGTRKFABWCI-UHFFFAOYSA-N n-[4-(2,5-dimethylphenyl)phenyl]-2,6-difluorobenzamide Chemical compound CC1=CC=C(C)C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 XMOXGTRKFABWCI-UHFFFAOYSA-N 0.000 claims 3
- LTOLCFSKQADMSS-UHFFFAOYSA-N n-[4-(2,5-dimethylphenyl)phenyl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CC=C(C)C(C=2C=CC(NC(=O)C=3C(=CN=CC=3)C)=CC=2)=C1 LTOLCFSKQADMSS-UHFFFAOYSA-N 0.000 claims 3
- KHFIUDNMDXTWNI-UHFFFAOYSA-N n-[4-(2-ethylphenyl)phenyl]-3-methylpyridine-4-carboxamide Chemical compound CCC1=CC=CC=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C KHFIUDNMDXTWNI-UHFFFAOYSA-N 0.000 claims 3
- QATQHJQOLQPIRZ-UHFFFAOYSA-N n-[4-(2-methoxy-5-methylphenyl)phenyl]-3-methylpyridine-4-carboxamide Chemical compound COC1=CC=C(C)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C QATQHJQOLQPIRZ-UHFFFAOYSA-N 0.000 claims 3
- AWWXCSDSZCUWJM-UHFFFAOYSA-N n-[4-(5-acetyl-2-methoxyphenyl)phenyl]-2,3-difluorobenzamide Chemical compound COC1=CC=C(C(C)=O)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F AWWXCSDSZCUWJM-UHFFFAOYSA-N 0.000 claims 3
- CMRMTMIMVCKYRY-UHFFFAOYSA-N n-[4-(5-acetyl-2-methoxyphenyl)phenyl]-4-methylthiadiazole-5-carboxamide Chemical compound COC1=CC=C(C(C)=O)C=C1C(C=C1)=CC=C1NC(=O)C1=C(C)N=NS1 CMRMTMIMVCKYRY-UHFFFAOYSA-N 0.000 claims 3
- IPLAIQHWYPFYGK-UHFFFAOYSA-N n-[4-(5-chloro-2-ethoxyphenyl)phenyl]-3-methylpyridine-4-carboxamide Chemical compound CCOC1=CC=C(Cl)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C IPLAIQHWYPFYGK-UHFFFAOYSA-N 0.000 claims 3
- VFPMSRIISKWJAQ-UHFFFAOYSA-N n-[4-(5-chloro-2-methoxyphenyl)phenyl]-2,3-difluorobenzamide Chemical compound COC1=CC=C(Cl)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F VFPMSRIISKWJAQ-UHFFFAOYSA-N 0.000 claims 3
- OBUCADJIHSQDOH-UHFFFAOYSA-N n-[4-(5-chloro-2-methoxyphenyl)phenyl]-2,4,5-trifluorobenzamide Chemical compound COC1=CC=C(Cl)C=C1C(C=C1)=CC=C1NC(=O)C1=CC(F)=C(F)C=C1F OBUCADJIHSQDOH-UHFFFAOYSA-N 0.000 claims 3
- YMWMWBUCWBLRRE-UHFFFAOYSA-N n-[4-(5-chloro-2-methoxyphenyl)phenyl]-3-fluoropyridine-4-carboxamide Chemical compound COC1=CC=C(Cl)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1F YMWMWBUCWBLRRE-UHFFFAOYSA-N 0.000 claims 3
- CZODDPCOZRPILV-UHFFFAOYSA-N n-[4-(5-chloro-2-methoxyphenyl)phenyl]-3-methylpyridine-4-carboxamide Chemical compound COC1=CC=C(Cl)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C CZODDPCOZRPILV-UHFFFAOYSA-N 0.000 claims 3
- XWDSDPOAPWWTRU-UHFFFAOYSA-N n-[4-(5-cyano-2-methoxyphenyl)phenyl]-2,3-difluorobenzamide Chemical compound COC1=CC=C(C#N)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F XWDSDPOAPWWTRU-UHFFFAOYSA-N 0.000 claims 3
- ZXLMCFOMRMQXLZ-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-1,2-oxazole-5-carboxamide Chemical compound FC(F)(F)C1=CC=C(C(F)(F)F)C(C=2C=CC(NC(=O)C=3ON=CC=3)=CC=2)=C1 ZXLMCFOMRMQXLZ-UHFFFAOYSA-N 0.000 claims 3
- AZIBAKRFJNYNEO-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-2,3-difluorobenzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=CC(=CC=2)C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)=C1F AZIBAKRFJNYNEO-UHFFFAOYSA-N 0.000 claims 3
- OOYPXXUSPRQVFT-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound FC(F)(F)C1=CC=C(C(F)(F)F)C(C=2C=CC(NC(=O)C=3C=4OCCOC=4C=CC=3)=CC=2)=C1 OOYPXXUSPRQVFT-UHFFFAOYSA-N 0.000 claims 3
- STNNMCWOBNDNKA-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-2,3-dimethylbenzamide Chemical compound CC1=CC=CC(C(=O)NC=2C=CC(=CC=2)C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)=C1C STNNMCWOBNDNKA-UHFFFAOYSA-N 0.000 claims 3
- GRZSAMOBNGCJOZ-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-2,5-difluorobenzamide Chemical compound FC1=CC=C(F)C(C(=O)NC=2C=CC(=CC=2)C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)=C1 GRZSAMOBNGCJOZ-UHFFFAOYSA-N 0.000 claims 3
- DCCBGJMDDKTXFR-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-2,5-dimethylpyrazole-3-carboxamide Chemical compound CN1N=C(C)C=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)C=C1 DCCBGJMDDKTXFR-UHFFFAOYSA-N 0.000 claims 3
- DIPKRDUMYXHGED-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)C=C1 DIPKRDUMYXHGED-UHFFFAOYSA-N 0.000 claims 3
- ITDRLFXSUNQUCT-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-2-hydroxybenzamide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)C=C1 ITDRLFXSUNQUCT-UHFFFAOYSA-N 0.000 claims 3
- NWKXLNMUKDLVNL-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-2-methylpyridine-3-carboxamide Chemical compound CC1=NC=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)C=C1 NWKXLNMUKDLVNL-UHFFFAOYSA-N 0.000 claims 3
- CBXVBEVNTQIZJG-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-3,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)C=C1 CBXVBEVNTQIZJG-UHFFFAOYSA-N 0.000 claims 3
- ARBSTFMOMBBEPA-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-3-chloro-2-methylbenzamide Chemical compound CC1=C(Cl)C=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)C=C1 ARBSTFMOMBBEPA-UHFFFAOYSA-N 0.000 claims 3
- GUFNCESSHKLNFB-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-3-fluoro-2-methylbenzamide Chemical compound CC1=C(F)C=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)C=C1 GUFNCESSHKLNFB-UHFFFAOYSA-N 0.000 claims 3
- YIGKCCOEDOTGOC-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-3-fluoropyridine-4-carboxamide Chemical compound FC1=CN=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)C=C1 YIGKCCOEDOTGOC-UHFFFAOYSA-N 0.000 claims 3
- YJSSRKJNFIABEH-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-3-methoxy-2-methylbenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=CC(=CC=2)C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)=C1C YJSSRKJNFIABEH-UHFFFAOYSA-N 0.000 claims 3
- PSMOZGNRGSEFCS-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-3-methyl-1,2-oxazole-4-carboxamide Chemical compound CC1=NOC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)C=C1 PSMOZGNRGSEFCS-UHFFFAOYSA-N 0.000 claims 3
- GWFQDZLHSGIQQR-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-3-methylimidazole-4-carboxamide Chemical compound CN1C=NC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)C=C1 GWFQDZLHSGIQQR-UHFFFAOYSA-N 0.000 claims 3
- XHSDIRNUHNMNNA-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)C=C1 XHSDIRNUHNMNNA-UHFFFAOYSA-N 0.000 claims 3
- MVXUADGWVCMXHZ-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2C=CC(=CC=2)C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)=C1C MVXUADGWVCMXHZ-UHFFFAOYSA-N 0.000 claims 3
- AWWJEAXMFGXWPH-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-5-methyl-1,2-oxazole-3-carboxamide Chemical compound O1C(C)=CC(C(=O)NC=2C=CC(=CC=2)C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)=N1 AWWJEAXMFGXWPH-UHFFFAOYSA-N 0.000 claims 3
- VKDISYKBFFETTH-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)=C1C VKDISYKBFFETTH-UHFFFAOYSA-N 0.000 claims 3
- NZNGKOPYISEFEG-UHFFFAOYSA-N n-[4-[2,5-bis(trifluoromethyl)phenyl]phenyl]thiadiazole-4-carboxamide Chemical compound FC(F)(F)C1=CC=C(C(F)(F)F)C(C=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 NZNGKOPYISEFEG-UHFFFAOYSA-N 0.000 claims 3
- XJWAMOYSDNAJBB-UHFFFAOYSA-N n-[4-[2-(dimethylamino)-5-(trifluoromethoxy)phenyl]phenyl]-4-methylthiadiazole-5-carboxamide Chemical compound CN(C)C1=CC=C(OC(F)(F)F)C=C1C(C=C1)=CC=C1NC(=O)C1=C(C)N=NS1 XJWAMOYSDNAJBB-UHFFFAOYSA-N 0.000 claims 3
- XFZIFHKGOFRWQM-UHFFFAOYSA-N n-[4-[2-(dimethylamino)-5-methoxyphenyl]phenyl]-3-methylpyridine-4-carboxamide Chemical compound COC1=CC=C(N(C)C)C(C=2C=CC(NC(=O)C=3C(=CN=CC=3)C)=CC=2)=C1 XFZIFHKGOFRWQM-UHFFFAOYSA-N 0.000 claims 3
- RXWIVLAWCPUVIM-UHFFFAOYSA-N n-[4-[2-(dimethylcarbamoyl)phenyl]phenyl]-2,3-difluorobenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F RXWIVLAWCPUVIM-UHFFFAOYSA-N 0.000 claims 3
- IRCBDIAWUVTZQS-UHFFFAOYSA-N n-[4-[2-(trifluoromethyl)phenyl]phenyl]pyrazine-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(C=C1)=CC=C1NC(=O)C1=CN=CC=N1 IRCBDIAWUVTZQS-UHFFFAOYSA-N 0.000 claims 3
- ULHIUBLDSQPXNI-UHFFFAOYSA-N n-[4-[2-(trifluoromethyl)phenyl]phenyl]pyridine-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(C=C1)=CC=C1NC(=O)C1=CC=CC=N1 ULHIUBLDSQPXNI-UHFFFAOYSA-N 0.000 claims 3
- DGXGZABVIDHAGT-UHFFFAOYSA-N n-[4-[2-(trifluoromethyl)phenyl]phenyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(C=C1)=CC=C1NC(=O)C1=CC=CN=C1 DGXGZABVIDHAGT-UHFFFAOYSA-N 0.000 claims 3
- OMVYQTCZIGVSOI-UHFFFAOYSA-N n-[4-[2-(trifluoromethyl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1 OMVYQTCZIGVSOI-UHFFFAOYSA-N 0.000 claims 3
- BUFCMFZEYHEEDY-UHFFFAOYSA-N n-[4-[2-(trifluoromethyl)phenyl]phenyl]thiophene-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(C=C1)=CC=C1NC(=O)C1=CC=CS1 BUFCMFZEYHEEDY-UHFFFAOYSA-N 0.000 claims 3
- OHHIGBIGGBDEJY-UHFFFAOYSA-N n-[4-[2-chloro-5-(trifluoromethyl)phenyl]phenyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)C=C1 OHHIGBIGGBDEJY-UHFFFAOYSA-N 0.000 claims 3
- GOLKVSXQONDNNF-UHFFFAOYSA-N n-[4-[2-chloro-5-(trifluoromethyl)phenyl]phenyl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)C=C1 GOLKVSXQONDNNF-UHFFFAOYSA-N 0.000 claims 3
- NWYZKPUWWPUBFA-UHFFFAOYSA-N n-[4-[2-chloro-5-(trifluoromethyl)phenyl]phenyl]-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2C=CC(=CC=2)C=2C(=CC=C(C=2)C(F)(F)F)Cl)=C1C NWYZKPUWWPUBFA-UHFFFAOYSA-N 0.000 claims 3
- BYDKKUFSIJOVFC-UHFFFAOYSA-N n-[4-[3,5-bis(trifluoromethyl)-1,2,4-triazol-4-yl]phenyl]-2,3-difluorobenzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=CC(=CC=2)N2C(=NN=C2C(F)(F)F)C(F)(F)F)=C1F BYDKKUFSIJOVFC-UHFFFAOYSA-N 0.000 claims 3
- NBGBCUVPHXLEQI-UHFFFAOYSA-N n-[4-[3,5-bis(trifluoromethyl)-1,2,4-triazol-4-yl]phenyl]-3-methylthiophene-2-carboxamide Chemical compound C1=CSC(C(=O)NC=2C=CC(=CC=2)N2C(=NN=C2C(F)(F)F)C(F)(F)F)=C1C NBGBCUVPHXLEQI-UHFFFAOYSA-N 0.000 claims 3
- YKIPGTVZUNPXDG-UHFFFAOYSA-N n-[4-[3-cyano-5-(trifluoromethyl)pyridin-2-yl]phenyl]-2,3-difluorobenzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=CC(=CC=2)C=2C(=CC(=CN=2)C(F)(F)F)C#N)=C1F YKIPGTVZUNPXDG-UHFFFAOYSA-N 0.000 claims 3
- PPBFLKBIPGUOBK-UHFFFAOYSA-N n-[4-[5-chloro-2,7-bis(trifluoromethyl)indolizin-3-yl]phenyl]-2,3-difluorobenzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=CC(=CC=2)C=2N3C(Cl)=CC(=CC3=CC=2C(F)(F)F)C(F)(F)F)=C1F PPBFLKBIPGUOBK-UHFFFAOYSA-N 0.000 claims 3
- AZAZERJRGZRUSK-UHFFFAOYSA-N n-[4-[5-chloro-2,7-bis(trifluoromethyl)indolizin-3-yl]phenyl]-2,4,5-trifluorobenzamide Chemical compound C1=C(F)C(F)=CC(F)=C1C(=O)NC1=CC=C(C=2N3C(Cl)=CC(=CC3=CC=2C(F)(F)F)C(F)(F)F)C=C1 AZAZERJRGZRUSK-UHFFFAOYSA-N 0.000 claims 3
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Classifications
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- 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
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- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
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- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
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- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
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