NZ534395A - Substituted pyridinones as modulators of p38 MAP kinase - Google Patents
Substituted pyridinones as modulators of p38 MAP kinaseInfo
- Publication number
- NZ534395A NZ534395A NZ534395A NZ53439503A NZ534395A NZ 534395 A NZ534395 A NZ 534395A NZ 534395 A NZ534395 A NZ 534395A NZ 53439503 A NZ53439503 A NZ 53439503A NZ 534395 A NZ534395 A NZ 534395A
- Authority
- NZ
- New Zealand
- Prior art keywords
- oxy
- methyl
- difluorobenzyl
- pyridin
- bromo
- Prior art date
Links
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 title claims abstract description 19
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 title claims abstract description 19
- 150000005299 pyridinones Chemical class 0.000 title description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 267
- 150000001875 compounds Chemical class 0.000 claims abstract description 244
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 40
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 20
- 102100040247 Tumor necrosis factor Human genes 0.000 claims abstract description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
- 208000035475 disorder Diseases 0.000 claims abstract description 9
- 230000001404 mediated effect Effects 0.000 claims abstract description 8
- 206010061218 Inflammation Diseases 0.000 claims abstract description 6
- 206010003246 arthritis Diseases 0.000 claims abstract description 6
- 230000004054 inflammatory process Effects 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 1695
- 229910052736 halogen Inorganic materials 0.000 claims description 522
- 150000002367 halogens Chemical class 0.000 claims description 522
- 125000003545 alkoxy group Chemical group 0.000 claims description 483
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 255
- -1 hydroxy, hydroxy Chemical group 0.000 claims description 212
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 201
- 125000002252 acyl group Chemical group 0.000 claims description 199
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 196
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 178
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 163
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 148
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 125
- 125000004193 piperazinyl group Chemical group 0.000 claims description 111
- 125000002757 morpholinyl group Chemical group 0.000 claims description 109
- 125000001188 haloalkyl group Chemical group 0.000 claims description 103
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 99
- 125000004076 pyridyl group Chemical group 0.000 claims description 99
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 98
- 125000003386 piperidinyl group Chemical group 0.000 claims description 90
- 229910052739 hydrogen Inorganic materials 0.000 claims description 83
- 229910052757 nitrogen Inorganic materials 0.000 claims description 81
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 81
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 79
- 239000001257 hydrogen Substances 0.000 claims description 74
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 68
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 60
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 60
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 58
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 48
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims description 46
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 46
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 42
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 39
- 125000001041 indolyl group Chemical group 0.000 claims description 37
- 125000001544 thienyl group Chemical group 0.000 claims description 31
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 28
- 150000002431 hydrogen Chemical group 0.000 claims description 25
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 21
- 125000002883 imidazolyl group Chemical group 0.000 claims description 19
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 14
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 14
- 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 230000002917 arthritic effect Effects 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims 367
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 17
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 16
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 14
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 10
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 10
- 125000001589 carboacyl group Chemical group 0.000 claims 10
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 9
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 5
- 241001465754 Metazoa Species 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- BGSKLTFWWOSTJG-UHFFFAOYSA-N 1-benzyl-3-bromo-6-methyl-4-phenylmethoxypyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC=CC=2)C(C)=CC=1OCC1=CC=CC=C1 BGSKLTFWWOSTJG-UHFFFAOYSA-N 0.000 claims 3
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims 3
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- DERJYEZSLHIUKF-UHFFFAOYSA-N procarbazine hydrochloride Chemical compound Cl.CNNCC1=CC=C(C(=O)NC(C)C)C=C1 DERJYEZSLHIUKF-UHFFFAOYSA-N 0.000 claims 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 3
- 230000008961 swelling Effects 0.000 claims 3
- GIUBYHVXUJOTAY-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-3-iodo-4-phenylmethoxypyridin-2-one Chemical compound FC1=CC=CC(CN2C(C(I)=C(OCC=3C=CC=CC=3)C=C2)=O)=C1 GIUBYHVXUJOTAY-UHFFFAOYSA-N 0.000 claims 2
- VWNVEHCYEHSRSA-UHFFFAOYSA-N 1-[(4-bromophenyl)methyl]-4-phenylmethoxypyridin-2-one Chemical compound C1=CC(Br)=CC=C1CN1C(=O)C=C(OCC=2C=CC=CC=2)C=C1 VWNVEHCYEHSRSA-UHFFFAOYSA-N 0.000 claims 2
- YUXODCFVLQIBMF-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-5-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]pyridin-2-one Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)C=CC(C=2ON=C(N=2)C=2C=CC(Cl)=CC=2)=C1 YUXODCFVLQIBMF-UHFFFAOYSA-N 0.000 claims 2
- WTDRKDCEGJTTEL-UHFFFAOYSA-N 1-benzyl-2-oxo-4-phenylmethoxypyridine-3-carbaldehyde Chemical compound C1=CN(CC=2C=CC=CC=2)C(=O)C(C=O)=C1OCC1=CC=CC=C1 WTDRKDCEGJTTEL-UHFFFAOYSA-N 0.000 claims 2
- JPLAXRUZKMVMNY-UHFFFAOYSA-N 1-benzyl-3,5-dibromo-6-methyl-4-phenylmethoxypyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC=CC=2)C(C)=C(Br)C=1OCC1=CC=CC=C1 JPLAXRUZKMVMNY-UHFFFAOYSA-N 0.000 claims 2
- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 2
- PLYAJTJMNHCVCT-UHFFFAOYSA-N 3-bromo-1-(cyclopropylmethyl)-4-[(4-fluorophenyl)methoxy]pyridin-2-one Chemical compound C1=CC(F)=CC=C1COC1=C(Br)C(=O)N(CC2CC2)C=C1 PLYAJTJMNHCVCT-UHFFFAOYSA-N 0.000 claims 2
- IISRJGJCVGIBEC-UHFFFAOYSA-N 3-bromo-1-[(3-fluorophenyl)methyl]-4-[(3-methylphenyl)methoxy]pyridin-2-one Chemical compound CC1=CC=CC(COC2=C(C(=O)N(CC=3C=C(F)C=CC=3)C=C2)Br)=C1 IISRJGJCVGIBEC-UHFFFAOYSA-N 0.000 claims 2
- MOIUAROBUAGUTJ-UHFFFAOYSA-N 3-bromo-1-[(4-bromophenyl)methyl]-4-phenylmethoxypyridin-2-one Chemical compound C1=CC(Br)=CC=C1CN1C(=O)C(Br)=C(OCC=2C=CC=CC=2)C=C1 MOIUAROBUAGUTJ-UHFFFAOYSA-N 0.000 claims 2
- VMWALGUYZTWWIN-UHFFFAOYSA-N 3-bromo-1-[(4-chlorophenyl)methyl]-4-phenylmethoxypyridin-2-one Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)C(Br)=C(OCC=2C=CC=CC=2)C=C1 VMWALGUYZTWWIN-UHFFFAOYSA-N 0.000 claims 2
- CYYUWNLBQDIGQB-UHFFFAOYSA-N 3-bromo-1-[(4-methylsulfanylphenyl)methyl]-4-phenylmethoxypyridin-2-one Chemical compound C1=CC(SC)=CC=C1CN1C(=O)C(Br)=C(OCC=2C=CC=CC=2)C=C1 CYYUWNLBQDIGQB-UHFFFAOYSA-N 0.000 claims 2
- LZQSJJLHDYOERR-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-(2,6-dimethylphenyl)-6-methylpyridin-2-one Chemical compound CC1=CC=CC(C)=C1N1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C LZQSJJLHDYOERR-UHFFFAOYSA-N 0.000 claims 2
- LETRLNNNJTUZTD-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-(2-methoxy-6-methylphenyl)-6-methylpyridin-2-one Chemical compound COC1=CC=CC(C)=C1N1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C LETRLNNNJTUZTD-UHFFFAOYSA-N 0.000 claims 2
- CXEFFYMYFJJZKQ-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-(pyridin-4-ylmethyl)pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CN=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F CXEFFYMYFJJZKQ-UHFFFAOYSA-N 0.000 claims 2
- QTBNYCDGLYVQPT-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[(5-methylpyrazin-2-yl)methyl]pyridin-2-one Chemical compound C1=NC(C)=CN=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C QTBNYCDGLYVQPT-UHFFFAOYSA-N 0.000 claims 2
- ONRGFKNSHXSCRC-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[2-methyl-5-(morpholine-4-carbonyl)phenyl]pyridin-2-one Chemical compound CC1=CC=C(C(=O)N2CCOCC2)C=C1N(C(C=1Br)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F ONRGFKNSHXSCRC-UHFFFAOYSA-N 0.000 claims 2
- FFUZMGQZTNVBKQ-UHFFFAOYSA-N 3-bromo-4-[(4-chlorophenyl)methoxy]-1-(2-phenylsulfanylethyl)pyridin-2-one Chemical compound C1=CC(Cl)=CC=C1COC1=C(Br)C(=O)N(CCSC=2C=CC=CC=2)C=C1 FFUZMGQZTNVBKQ-UHFFFAOYSA-N 0.000 claims 2
- OSHSZXGVTYGWSE-UHFFFAOYSA-N 3-bromo-4-[(4-fluorophenyl)methoxy]-1-[(4-fluorophenyl)methyl]pyridin-2-one Chemical compound C1=CC(F)=CC=C1COC1=C(Br)C(=O)N(CC=2C=CC(F)=CC=2)C=C1 OSHSZXGVTYGWSE-UHFFFAOYSA-N 0.000 claims 2
- SKHNKTSKXVDYLF-UHFFFAOYSA-N 3-bromo-4-[(4-fluorophenyl)methoxy]-1-[(4-methoxyphenyl)methyl]pyridin-2-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C(Br)=C(OCC=2C=CC(F)=CC=2)C=C1 SKHNKTSKXVDYLF-UHFFFAOYSA-N 0.000 claims 2
- QRCBEPKKSSHPMZ-UHFFFAOYSA-N 3-bromo-4-[(4-fluorophenyl)methoxy]-6-methyl-1-(pyridin-4-ylmethyl)pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CN=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1 QRCBEPKKSSHPMZ-UHFFFAOYSA-N 0.000 claims 2
- ZRMQYTPALIALTR-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-(1,2,3,4-tetrahydroisoquinolin-5-ylmethyl)pyridin-2-one Chemical compound FC1=CC(F)=CC=C1COC1=C(Cl)C(=O)N(CC=2C=3CCNCC=3C=CC=2)C=C1 ZRMQYTPALIALTR-UHFFFAOYSA-N 0.000 claims 2
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- SXOQURHLAQXKOT-UHFFFAOYSA-N 4-(benzylamino)-3-bromo-1-[(3-fluorophenyl)methyl]pyridin-2-one Chemical compound FC1=CC=CC(CN2C(C(Br)=C(NCC=3C=CC=CC=3)C=C2)=O)=C1 SXOQURHLAQXKOT-UHFFFAOYSA-N 0.000 claims 2
- LPNHTXFWSVMVCX-UHFFFAOYSA-N 4-[(3-bromo-2-oxo-4-phenylmethoxypyridin-1-yl)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C(=O)C(Br)=C(OCC=2C=CC=CC=2)C=C1 LPNHTXFWSVMVCX-UHFFFAOYSA-N 0.000 claims 2
- ZMQAAYBUCPJPFN-UHFFFAOYSA-N 4-[(3-bromo-2-oxo-4-phenylmethoxypyridin-1-yl)methyl]benzonitrile Chemical compound C1=CN(CC=2C=CC(=CC=2)C#N)C(=O)C(Br)=C1OCC1=CC=CC=C1 ZMQAAYBUCPJPFN-UHFFFAOYSA-N 0.000 claims 2
- HVGIKLCOPMGNEN-UHFFFAOYSA-N 4-[(4-fluorophenyl)methoxy]-1-[(3-fluorophenyl)methyl]-3-iodopyridin-2-one Chemical compound C1=CC(F)=CC=C1COC1=C(I)C(=O)N(CC=2C=C(F)C=CC=2)C=C1 HVGIKLCOPMGNEN-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
- KCAJXIDMCNPGHZ-UHFFFAOYSA-N PH 797804 Chemical compound CNC(=O)C1=CC=C(C)C(N2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 KCAJXIDMCNPGHZ-UHFFFAOYSA-N 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 2
- QNAYBMKLOCPYGJ-UHFFFAOYSA-M alaninate Chemical compound CC(N)C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-M 0.000 claims 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
- GCLLJRULFKBORQ-UHFFFAOYSA-N methyl 4-[(3-bromo-2-oxo-4-phenylmethoxypyridin-1-yl)methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(=O)C(Br)=C(OCC=2C=CC=CC=2)C=C1 GCLLJRULFKBORQ-UHFFFAOYSA-N 0.000 claims 2
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 2
- JWEQRJSCTFBRSI-PCLIKHOPSA-N rboxylate Chemical compound COC(=O)C1C(N2C3=O)C4=CC=CC=C4OC1(C)N=C2S\C3=C\C(C=1)=CC=C(OC)C=1COC1=CC=CC=C1C JWEQRJSCTFBRSI-PCLIKHOPSA-N 0.000 claims 2
- WFWVUJPOXPGYIN-UHFFFAOYSA-N (1-benzyl-2-methyl-6-oxopyridin-4-yl) 4-bromobenzenesulfonate Chemical compound C=1C(=O)N(CC=2C=CC=CC=2)C(C)=CC=1OS(=O)(=O)C1=CC=C(Br)C=C1 WFWVUJPOXPGYIN-UHFFFAOYSA-N 0.000 claims 1
- YFQBAQOBYFEJLA-UHFFFAOYSA-N (1-benzyl-2-methyl-6-oxopyridin-4-yl) methanesulfonate Chemical compound CC1=CC(OS(C)(=O)=O)=CC(=O)N1CC1=CC=CC=C1 YFQBAQOBYFEJLA-UHFFFAOYSA-N 0.000 claims 1
- KJPZZESSMQXXAJ-UHFFFAOYSA-N (1-benzyl-3-bromo-2-oxopyridin-4-yl) n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(=C(C1=O)Br)C=CN1CC1=CC=CC=C1 KJPZZESSMQXXAJ-UHFFFAOYSA-N 0.000 claims 1
- CBLYTKMGUSMUPP-UHFFFAOYSA-N (1-benzyl-3-bromo-6-methyl-2-oxopyridin-4-yl) 4-bromobenzenesulfonate Chemical compound BrC=1C(=O)N(CC=2C=CC=CC=2)C(C)=CC=1OS(=O)(=O)C1=CC=C(Br)C=C1 CBLYTKMGUSMUPP-UHFFFAOYSA-N 0.000 claims 1
- DFDJQBGYKTVVGP-UHFFFAOYSA-N (1-benzyl-3-bromo-6-methyl-2-oxopyridin-4-yl) methanesulfonate Chemical compound CC1=CC(OS(C)(=O)=O)=C(Br)C(=O)N1CC1=CC=CC=C1 DFDJQBGYKTVVGP-UHFFFAOYSA-N 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- GTKFRVNCOAGIOF-UHFFFAOYSA-N 1,3-diacetyl-5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]benzimidazol-2-one Chemical compound C1=C2N(C(C)=O)C(=O)N(C(=O)C)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F GTKFRVNCOAGIOF-UHFFFAOYSA-N 0.000 claims 1
- QBPWCKIRXRNERT-UHFFFAOYSA-N 1,3-dibenzyl-4-hydroxy-6-methylpyridin-2-one Chemical compound O=C1N(CC=2C=CC=CC=2)C(C)=CC(O)=C1CC1=CC=CC=C1 QBPWCKIRXRNERT-UHFFFAOYSA-N 0.000 claims 1
- QLKMKNHZHKGMHV-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-ylmethyl)-3-bromo-4-[(2,4-difluorophenyl)methoxy]pyridin-2-one Chemical compound FC1=CC(F)=CC=C1COC1=C(Br)C(=O)N(CC=2C=C3OCOC3=CC=2)C=C1 QLKMKNHZHKGMHV-UHFFFAOYSA-N 0.000 claims 1
- YQCGCIKXAZIEDJ-UHFFFAOYSA-N 1-(1-acetylimidazol-4-yl)-3-chloro-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound CC(=O)N1C=NC(N2C(C(Cl)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 YQCGCIKXAZIEDJ-UHFFFAOYSA-N 0.000 claims 1
- RFCPVMRBMXDQBE-UHFFFAOYSA-N 1-(2,2-diethoxyethyl)-4-phenylmethoxypyridin-2-one Chemical compound O=C1N(CC(OCC)OCC)C=CC(OCC=2C=CC=CC=2)=C1 RFCPVMRBMXDQBE-UHFFFAOYSA-N 0.000 claims 1
- SKAVMGOTPARDMM-UHFFFAOYSA-N 1-(2,6-difluoro-4-hydroxyphenyl)-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound C=1C(=O)N(C=2C(=CC(O)=CC=2F)F)C(C)=CC=1OCC1=CC=C(F)C=C1F SKAVMGOTPARDMM-UHFFFAOYSA-N 0.000 claims 1
- RLJYOUBKQWCAJQ-UHFFFAOYSA-N 1-(2,6-difluorophenyl)-4-methoxy-6-methyl-5-(2-phenylethyl)pyridin-2-one Chemical compound COC1=CC(=O)N(C=2C(=CC=CC=2F)F)C(C)=C1CCC1=CC=CC=C1 RLJYOUBKQWCAJQ-UHFFFAOYSA-N 0.000 claims 1
- YDTADCOXSIDBHM-UHFFFAOYSA-N 1-(2-chloro-4-hydroxyphenyl)-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound C=1C(=O)N(C=2C(=CC(O)=CC=2)Cl)C(C)=CC=1OCC1=CC=C(F)C=C1F YDTADCOXSIDBHM-UHFFFAOYSA-N 0.000 claims 1
- QHPMIMVJEUGKMN-UHFFFAOYSA-N 1-(4-bromo-2,6-difluorophenyl)-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound C=1C(=O)N(C=2C(=CC(Br)=CC=2F)F)C(C)=CC=1OCC1=CC=C(F)C=C1F QHPMIMVJEUGKMN-UHFFFAOYSA-N 0.000 claims 1
- NPXLKHPUYHEDLX-UHFFFAOYSA-N 1-(difluoromethyl)-4-phenylmethoxypyridin-2-one Chemical compound O=C1N(C(F)F)C=CC(OCC=2C=CC=CC=2)=C1 NPXLKHPUYHEDLX-UHFFFAOYSA-N 0.000 claims 1
- PRGOCMCYLGYLOJ-UHFFFAOYSA-N 1-[(1-acetyl-3-methylsulfonyl-2h-benzimidazol-5-yl)methyl]-3-chloro-4-[(2,4-difluorophenyl)methoxy]pyridin-2-one Chemical compound C=1C=C2N(C(=O)C)CN(S(C)(=O)=O)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F PRGOCMCYLGYLOJ-UHFFFAOYSA-N 0.000 claims 1
- NBKUTWJABLRSTO-UHFFFAOYSA-N 1-[(2,6-dichlorophenyl)methyl]-6-oxo-n-[4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)C1=CN(CC=2C(=CC=CC=2Cl)Cl)C(=O)C=C1 NBKUTWJABLRSTO-UHFFFAOYSA-N 0.000 claims 1
- JPPOJDCLGFQNFH-UHFFFAOYSA-N 1-[(2,6-dichlorophenyl)methyl]-6-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(CNC(=O)C2=CN(CC=3C(=CC=CC=3Cl)Cl)C(=O)C=C2)=C1 JPPOJDCLGFQNFH-UHFFFAOYSA-N 0.000 claims 1
- CVYBEGOWIRNBEY-UHFFFAOYSA-N 1-[(2,6-dichlorophenyl)methyl]-n-(2,4-difluorophenyl)-6-oxopyridine-3-carboxamide Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CN(CC=2C(=CC=CC=2Cl)Cl)C(=O)C=C1 CVYBEGOWIRNBEY-UHFFFAOYSA-N 0.000 claims 1
- RJVMXSXELVJJOP-UHFFFAOYSA-N 1-[(2,6-dichlorophenyl)methyl]-n-(2-morpholin-4-ylethyl)-6-oxopyridine-3-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1CN1C(=O)C=CC(C(=O)NCCN2CCOCC2)=C1 RJVMXSXELVJJOP-UHFFFAOYSA-N 0.000 claims 1
- GANJEJGHTFICKD-UHFFFAOYSA-N 1-[(2,6-dichlorophenyl)methyl]-n-[2-(dimethylamino)ethyl]-6-oxopyridine-3-carboxamide Chemical compound C1=C(C(=O)NCCN(C)C)C=CC(=O)N1CC1=C(Cl)C=CC=C1Cl GANJEJGHTFICKD-UHFFFAOYSA-N 0.000 claims 1
- SZYJBOQAJZUYEE-UHFFFAOYSA-N 1-[(2,6-dichlorophenyl)methyl]-n-[3-(dimethylamino)propyl]-6-oxopyridine-3-carboxamide Chemical compound C1=C(C(=O)NCCCN(C)C)C=CC(=O)N1CC1=C(Cl)C=CC=C1Cl SZYJBOQAJZUYEE-UHFFFAOYSA-N 0.000 claims 1
- QYYSKRXDEFAZEW-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-4-phenylmethoxy-3-(trifluoromethyl)pyridin-2-one Chemical compound FC1=CC=CC(CN2C(C(=C(OCC=3C=CC=CC=3)C=C2)C(F)(F)F)=O)=C1 QYYSKRXDEFAZEW-UHFFFAOYSA-N 0.000 claims 1
- YUWJNMOCZUYMMX-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-4-phenoxypyridin-2-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C=C(OC=2C=CC=CC=2)C=C1 YUWJNMOCZUYMMX-UHFFFAOYSA-N 0.000 claims 1
- NTNHDBNVIAATDY-UHFFFAOYSA-N 1-[(4-methylphenyl)methyl]-4-phenylmethoxypyridin-2-one Chemical compound C1=CC(C)=CC=C1CN1C(=O)C=C(OCC=2C=CC=CC=2)C=C1 NTNHDBNVIAATDY-UHFFFAOYSA-N 0.000 claims 1
- BXLZNVIERBIUBM-UHFFFAOYSA-N 1-[(4-methylsulfanylphenyl)methyl]-4-phenylmethoxypyridin-2-one Chemical compound C1=CC(SC)=CC=C1CN1C(=O)C=C(OCC=2C=CC=CC=2)C=C1 BXLZNVIERBIUBM-UHFFFAOYSA-N 0.000 claims 1
- AEBRLVPHPAWXPI-UHFFFAOYSA-N 1-[1-acetyl-3-(2-hydroxyacetyl)-2h-benzimidazol-5-yl]-3-chloro-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound C=1C=C2N(C(=O)C)CN(C(=O)CO)C2=CC=1N(C(C=1Cl)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F AEBRLVPHPAWXPI-UHFFFAOYSA-N 0.000 claims 1
- NVNTYLVLHDKJHV-UHFFFAOYSA-N 1-[2,6-difluoro-4-(4-methylpiperazin-1-yl)phenyl]-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound C1CN(C)CCN1C1=CC(F)=C(N2C(C=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)C(F)=C1 NVNTYLVLHDKJHV-UHFFFAOYSA-N 0.000 claims 1
- CTNFYLMGBWVHCE-UHFFFAOYSA-N 1-[2,6-difluoro-4-[2-hydroxyethyl(methyl)amino]phenyl]-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound FC1=CC(N(CCO)C)=CC(F)=C1N1C(=O)C=C(OCC=2C(=CC(F)=CC=2)F)C=C1C CTNFYLMGBWVHCE-UHFFFAOYSA-N 0.000 claims 1
- ZJDZXLBRMUMZNS-UHFFFAOYSA-N 1-[2-chloro-5-(hydroxymethyl)phenyl]-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound C=1C(=O)N(C=2C(=CC=C(CO)C=2)Cl)C(C)=CC=1OCC1=CC=C(F)C=C1F ZJDZXLBRMUMZNS-UHFFFAOYSA-N 0.000 claims 1
- KTPQPAGLITZOAF-UHFFFAOYSA-N 1-[3-(aminomethyl)phenyl]-3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(C=2C=C(CN)C=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F KTPQPAGLITZOAF-UHFFFAOYSA-N 0.000 claims 1
- MZLJHOHEYACBDZ-UHFFFAOYSA-N 1-[3-acetyl-1-(2-hydroxy-2-methylpropanoyl)-2h-benzimidazol-5-yl]-3-chloro-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound C1=C2N(C(=O)C)CN(C(=O)C(C)(C)O)C2=CC=C1N(C(C=1Cl)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F MZLJHOHEYACBDZ-UHFFFAOYSA-N 0.000 claims 1
- ZKRLECUJTKRXPT-UHFFFAOYSA-N 1-[[1,3-bis(2-hydroxyacetyl)-2h-benzimidazol-5-yl]methyl]-3-chloro-4-[(2,4-difluorophenyl)methoxy]pyridin-2-one Chemical compound C=1C=C2N(C(=O)CO)CN(C(=O)CO)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F ZKRLECUJTKRXPT-UHFFFAOYSA-N 0.000 claims 1
- ZAIKSHWJJRTXGF-UHFFFAOYSA-N 1-[[1,3-bis(methylsulfonyl)-2h-benzimidazol-5-yl]methyl]-3-chloro-4-[(2,4-difluorophenyl)methoxy]pyridin-2-one Chemical compound C=1C=C2N(S(=O)(=O)C)CN(S(C)(=O)=O)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F ZAIKSHWJJRTXGF-UHFFFAOYSA-N 0.000 claims 1
- CPDWUIJJXKGWNR-UHFFFAOYSA-N 1-[[1-acetyl-3-(2-hydroxyacetyl)-2h-benzimidazol-5-yl]methyl]-3-chloro-4-[(2,4-difluorophenyl)methoxy]pyridin-2-one Chemical compound C=1C=C2N(C(=O)C)CN(C(=O)CO)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F CPDWUIJJXKGWNR-UHFFFAOYSA-N 0.000 claims 1
- XIAJFWOACHIGML-UHFFFAOYSA-N 1-[[2-(aminomethyl)phenyl]methyl]-3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C(=CC=CC=2)CN)C(C)=CC=1OCC1=CC=C(F)C=C1F XIAJFWOACHIGML-UHFFFAOYSA-N 0.000 claims 1
- BAYKQGHVLAQWKB-UHFFFAOYSA-N 1-[[2-(aminomethyl)phenyl]methyl]-3-bromo-4-[(2,4-difluorophenyl)methoxy]pyridin-2-one Chemical compound NCC1=CC=CC=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1 BAYKQGHVLAQWKB-UHFFFAOYSA-N 0.000 claims 1
- VJXVBBWCFBQNQM-UHFFFAOYSA-N 1-[[3-(aminomethyl)-2-fluorophenyl]methyl]-3-bromo-4-[(2,4-difluorophenyl)methoxy]pyridin-2-one Chemical compound NCC1=CC=CC(CN2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2)=O)=C1F VJXVBBWCFBQNQM-UHFFFAOYSA-N 0.000 claims 1
- AHCOXERXKVTVOT-UHFFFAOYSA-N 1-[[3-(aminomethyl)phenyl]methyl]-3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=C(CN)C=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F AHCOXERXKVTVOT-UHFFFAOYSA-N 0.000 claims 1
- OZOXAZXHCLAXBY-UHFFFAOYSA-N 1-[[3-(aminomethyl)phenyl]methyl]-3-bromo-4-phenylmethoxypyridin-2-one Chemical compound NCC1=CC=CC(CN2C(C(Br)=C(OCC=3C=CC=CC=3)C=C2)=O)=C1 OZOXAZXHCLAXBY-UHFFFAOYSA-N 0.000 claims 1
- NWWGASAIFNYQIF-UHFFFAOYSA-N 1-[[4-(aminomethyl)phenyl]methyl]-3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC(CN)=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F NWWGASAIFNYQIF-UHFFFAOYSA-N 0.000 claims 1
- NAMAXYKTZDVQIQ-UHFFFAOYSA-N 1-[[4-(aminomethyl)phenyl]methyl]-3-bromo-4-phenylmethoxypyridin-2-one Chemical compound C1=CC(CN)=CC=C1CN1C(=O)C(Br)=C(OCC=2C=CC=CC=2)C=C1 NAMAXYKTZDVQIQ-UHFFFAOYSA-N 0.000 claims 1
- ZPORRSFULKXMHC-UHFFFAOYSA-N 1-acetyl-5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-(2-hydroxy-2-methylpropanoyl)benzimidazol-2-one Chemical compound C1=C2N(C(=O)C(C)(C)O)C(=O)N(C(=O)C)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F ZPORRSFULKXMHC-UHFFFAOYSA-N 0.000 claims 1
- OBRZLOYRDILONU-UHFFFAOYSA-N 1-acetyl-5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-(3-hydroxy-3-methylbutanoyl)benzimidazol-2-one Chemical compound C1=C2N(C(=O)CC(C)(C)O)C(=O)N(C(=O)C)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F OBRZLOYRDILONU-UHFFFAOYSA-N 0.000 claims 1
- VBKJSIOMKNTJIX-UHFFFAOYSA-N 1-acetyl-5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-methylsulfonylbenzimidazol-2-one Chemical compound C1=C2N(S(C)(=O)=O)C(=O)N(C(=O)C)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F VBKJSIOMKNTJIX-UHFFFAOYSA-N 0.000 claims 1
- CYDXKVKHWPPFBY-UHFFFAOYSA-N 1-benzyl-2-oxo-4-phenoxypyridine-3-carbaldehyde Chemical compound C1=CN(CC=2C=CC=CC=2)C(=O)C(C=O)=C1OC1=CC=CC=C1 CYDXKVKHWPPFBY-UHFFFAOYSA-N 0.000 claims 1
- HZUVWTPQFBDOFU-UHFFFAOYSA-N 1-benzyl-3,5-dibromo-4-phenylmethoxypyridin-2-one Chemical compound O=C1C(Br)=C(OCC=2C=CC=CC=2)C(Br)=CN1CC1=CC=CC=C1 HZUVWTPQFBDOFU-UHFFFAOYSA-N 0.000 claims 1
- VRRDJQVHIWQNLT-UHFFFAOYSA-N 1-benzyl-3-(hydroxymethyl)-4-phenylmethoxypyridin-2-one Chemical compound C1=CN(CC=2C=CC=CC=2)C(=O)C(CO)=C1OCC1=CC=CC=C1 VRRDJQVHIWQNLT-UHFFFAOYSA-N 0.000 claims 1
- GIPJKWLXPAMYAZ-UHFFFAOYSA-N 1-benzyl-3-bromo-4-(2-phenylethyl)pyridin-2-one Chemical compound C1=CN(CC=2C=CC=CC=2)C(=O)C(Br)=C1CCC1=CC=CC=C1 GIPJKWLXPAMYAZ-UHFFFAOYSA-N 0.000 claims 1
- LUVJHJDVISUMCN-UHFFFAOYSA-N 1-benzyl-3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F LUVJHJDVISUMCN-UHFFFAOYSA-N 0.000 claims 1
- KEGYHOIHAFEQQK-UHFFFAOYSA-N 1-benzyl-3-bromo-4-[(2-chlorophenyl)methoxy]pyridin-2-one Chemical compound ClC1=CC=CC=C1COC1=C(Br)C(=O)N(CC=2C=CC=CC=2)C=C1 KEGYHOIHAFEQQK-UHFFFAOYSA-N 0.000 claims 1
- VBZTXJCTVYBOKW-UHFFFAOYSA-N 1-benzyl-3-bromo-4-phenylmethoxypyridin-2-one Chemical compound C1=CN(CC=2C=CC=CC=2)C(=O)C(Br)=C1OCC1=CC=CC=C1 VBZTXJCTVYBOKW-UHFFFAOYSA-N 0.000 claims 1
- ILUGJQHMRUPEDB-UHFFFAOYSA-N 1-benzyl-3-chloro-4-phenylmethoxypyridin-2-one Chemical compound C1=CN(CC=2C=CC=CC=2)C(=O)C(Cl)=C1OCC1=CC=CC=C1 ILUGJQHMRUPEDB-UHFFFAOYSA-N 0.000 claims 1
- XTYDPQGEIHWUMF-UHFFFAOYSA-N 1-benzyl-3-methyl-4-phenylmethoxypyridin-2-one Chemical compound C1=CN(CC=2C=CC=CC=2)C(=O)C(C)=C1OCC1=CC=CC=C1 XTYDPQGEIHWUMF-UHFFFAOYSA-N 0.000 claims 1
- JXGYXCOBORPGQB-UHFFFAOYSA-N 1-benzyl-4-[(4-methylphenyl)methoxy]pyridin-2-one Chemical compound C1=CC(C)=CC=C1COC1=CC(=O)N(CC=2C=CC=CC=2)C=C1 JXGYXCOBORPGQB-UHFFFAOYSA-N 0.000 claims 1
- DNKCFZIJJBPRKL-UHFFFAOYSA-N 1-benzyl-4-benzylsulfanyl-3-methylpyridin-2-one Chemical compound C1=CN(CC=2C=CC=CC=2)C(=O)C(C)=C1SCC1=CC=CC=C1 DNKCFZIJJBPRKL-UHFFFAOYSA-N 0.000 claims 1
- ZMOBCCHASXMNCZ-UHFFFAOYSA-N 1-benzyl-4-chloro-2-oxopyridine-3-carbaldehyde Chemical compound O=C1C(C=O)=C(Cl)C=CN1CC1=CC=CC=C1 ZMOBCCHASXMNCZ-UHFFFAOYSA-N 0.000 claims 1
- QPAKCDMLIMLCRV-UHFFFAOYSA-N 1-benzyl-4-hydroxy-2-oxopyridine-3-carbaldehyde Chemical compound O=C1C(C=O)=C(O)C=CN1CC1=CC=CC=C1 QPAKCDMLIMLCRV-UHFFFAOYSA-N 0.000 claims 1
- ZGSOHPATWDZJRA-UHFFFAOYSA-N 1-benzyl-4-hydroxy-6-methylpyridin-2-one Chemical compound CC1=CC(O)=CC(=O)N1CC1=CC=CC=C1 ZGSOHPATWDZJRA-UHFFFAOYSA-N 0.000 claims 1
- KKAOSQVDVKSBHR-UHFFFAOYSA-N 1-benzyl-4-phenoxypyridin-2-one Chemical compound C1=CN(CC=2C=CC=CC=2)C(=O)C=C1OC1=CC=CC=C1 KKAOSQVDVKSBHR-UHFFFAOYSA-N 0.000 claims 1
- MPCPIBFZAKSVAX-UHFFFAOYSA-N 1-benzyl-4-phenylmethoxypyridin-2-one Chemical compound C1=CN(CC=2C=CC=CC=2)C(=O)C=C1OCC1=CC=CC=C1 MPCPIBFZAKSVAX-UHFFFAOYSA-N 0.000 claims 1
- VPUSCCRLAWZROK-UHFFFAOYSA-N 1-benzyl-n-(2-morpholin-4-ylethyl)-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC=2C=CC=CC=2)C=C1C(=O)NCCN1CCOCC1 VPUSCCRLAWZROK-UHFFFAOYSA-N 0.000 claims 1
- ITTUOMKUEYHXTL-UHFFFAOYSA-N 1-cyclohexyl-4-[(2,4-difluorophenyl)methoxy]-3,6-dimethylpyridin-2-one Chemical compound CC=1C(=O)N(C2CCCCC2)C(C)=CC=1OCC1=CC=C(F)C=C1F ITTUOMKUEYHXTL-UHFFFAOYSA-N 0.000 claims 1
- CEPCPXLLFXPZGW-UHFFFAOYSA-N 2,4-difluoroaniline Chemical compound NC1=CC=C(F)C=C1F CEPCPXLLFXPZGW-UHFFFAOYSA-N 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- AOOTXMSFTWMODA-UHFFFAOYSA-N 2-(2-oxo-4-phenylmethoxypyridin-1-yl)acetamide Chemical compound O=C1N(CC(=O)N)C=CC(OCC=2C=CC=CC=2)=C1 AOOTXMSFTWMODA-UHFFFAOYSA-N 0.000 claims 1
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 claims 1
- FHIYPHGWPUZJAJ-UHFFFAOYSA-N 2-[3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]phenyl]acetonitrile Chemical compound FC1=CC(F)=CC=C1COC1=C(Br)C(=O)N(CC=2C=C(CC#N)C=CC=2)C=C1 FHIYPHGWPUZJAJ-UHFFFAOYSA-N 0.000 claims 1
- LDBBXHFACYPGFV-UHFFFAOYSA-N 2-[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]-6-methylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C(N2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=N1 LDBBXHFACYPGFV-UHFFFAOYSA-N 0.000 claims 1
- RHDKHHJCIJIPAX-UHFFFAOYSA-N 2-[4-[[3-bromo-2-[[4-(carboxymethyl)phenyl]methoxy]-4-phenylmethoxy-2h-pyridin-1-yl]methyl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1COC1C(Br)=C(OCC=2C=CC=CC=2)C=CN1CC1=CC=C(CC(O)=O)C=C1 RHDKHHJCIJIPAX-UHFFFAOYSA-N 0.000 claims 1
- FGBDUIABQRKWQG-UHFFFAOYSA-N 2-[[1-[(4-amino-2-methylpyrimidin-5-yl)methyl]-3-bromo-6-methyl-2-oxopyridin-4-yl]oxymethyl]-5-fluorobenzonitrile Chemical compound NC1=NC(C)=NC=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)C#N)C=C1C FGBDUIABQRKWQG-UHFFFAOYSA-N 0.000 claims 1
- QQVHCJAJWOEGOF-UHFFFAOYSA-N 2-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]benzonitrile Chemical compound FC1=CC(F)=CC=C1COC1=C(Br)C(=O)N(CC=2C(=CC=CC=2)C#N)C=C1 QQVHCJAJWOEGOF-UHFFFAOYSA-N 0.000 claims 1
- VSXPIAGLILQYTI-UHFFFAOYSA-N 2-chloro-n-[1-[(2,6-dichlorophenyl)methyl]-6-oxo-5-(trifluoromethyl)pyridin-3-yl]-4-fluorobenzamide Chemical compound ClC1=CC(F)=CC=C1C(=O)NC1=CN(CC=2C(=CC=CC=2Cl)Cl)C(=O)C(C(F)(F)F)=C1 VSXPIAGLILQYTI-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- QMRWISYGJVWXBT-UHFFFAOYSA-N 2-oxo-6-(2-phenylethyl)-1h-pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)NC(CCC=2C=CC=CC=2)=C1 QMRWISYGJVWXBT-UHFFFAOYSA-N 0.000 claims 1
- KTUZHAVCKLQHCN-UHFFFAOYSA-N 2-oxo-6-phenyl-1h-pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)NC(C=2C=CC=CC=2)=C1 KTUZHAVCKLQHCN-UHFFFAOYSA-N 0.000 claims 1
- KBBCXEGPUXHNRX-UHFFFAOYSA-N 3-(3-bromo-2-oxo-4-phenylmethoxypyridin-1-yl)propanamide Chemical compound O=C1N(CCC(=O)N)C=CC(OCC=2C=CC=CC=2)=C1Br KBBCXEGPUXHNRX-UHFFFAOYSA-N 0.000 claims 1
- HDQNWVAUYPHXJV-UHFFFAOYSA-N 3-(3-bromo-2-oxo-4-phenylmethoxypyridin-1-yl)propanoic acid Chemical compound O=C1N(CCC(=O)O)C=CC(OCC=2C=CC=CC=2)=C1Br HDQNWVAUYPHXJV-UHFFFAOYSA-N 0.000 claims 1
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 claims 1
- DAWDBPBHXCKLRA-UHFFFAOYSA-N 3-[(3-bromo-2-oxo-4-phenylmethoxypyridin-1-yl)methyl]benzamide Chemical compound NC(=O)C1=CC=CC(CN2C(C(Br)=C(OCC=3C=CC=CC=3)C=C2)=O)=C1 DAWDBPBHXCKLRA-UHFFFAOYSA-N 0.000 claims 1
- PRFCVOGLBVNVOS-UHFFFAOYSA-N 3-[(3-bromo-2-oxo-4-phenylmethoxypyridin-1-yl)methyl]benzonitrile Chemical compound C1=CN(CC=2C=C(C=CC=2)C#N)C(=O)C(Br)=C1OCC1=CC=CC=C1 PRFCVOGLBVNVOS-UHFFFAOYSA-N 0.000 claims 1
- HRYUBBLLQJWVLY-UHFFFAOYSA-N 3-[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]-4-methylbenzaldehyde Chemical compound CC1=CC=C(C=O)C=C1N1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C HRYUBBLLQJWVLY-UHFFFAOYSA-N 0.000 claims 1
- DXZBDVLSWPZSFB-UHFFFAOYSA-N 3-[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]benzoic acid Chemical compound BrC=1C(=O)N(C=2C=C(C=CC=2)C(O)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F DXZBDVLSWPZSFB-UHFFFAOYSA-N 0.000 claims 1
- ZNEJUBUDTXGESD-UHFFFAOYSA-N 3-[3-chloro-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]-4-fluoro-n-methylbenzamide;3-[3-chloro-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(N)=O)C=C1N1C(=O)C(Cl)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C.CNC(=O)C1=CC=C(F)C(N2C(C(Cl)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 ZNEJUBUDTXGESD-UHFFFAOYSA-N 0.000 claims 1
- CUKFFPYJTUEKQA-UHFFFAOYSA-N 3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]benzamide Chemical compound NC(=O)C1=CC=CC(CN2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2)=O)=C1 CUKFFPYJTUEKQA-UHFFFAOYSA-N 0.000 claims 1
- BGIIMEBHVOGZBA-UHFFFAOYSA-N 3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]-n,n-bis(2-hydroxyethyl)benzamide Chemical compound BrC=1C(=O)N(CC=2C=C(C=CC=2)C(=O)N(CCO)CCO)C(C)=CC=1OCC1=CC=C(F)C=C1F BGIIMEBHVOGZBA-UHFFFAOYSA-N 0.000 claims 1
- UKVDBAWTTGZFDV-UHFFFAOYSA-N 3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]-n-(2-hydroxyethyl)benzamide Chemical compound BrC=1C(=O)N(CC=2C=C(C=CC=2)C(=O)NCCO)C(C)=CC=1OCC1=CC=C(F)C=C1F UKVDBAWTTGZFDV-UHFFFAOYSA-N 0.000 claims 1
- XVPBHWKWGYFYLN-UHFFFAOYSA-N 3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]-n-hydroxybenzamide Chemical compound BrC=1C(=O)N(CC=2C=C(C=CC=2)C(=O)NO)C(C)=CC=1OCC1=CC=C(F)C=C1F XVPBHWKWGYFYLN-UHFFFAOYSA-N 0.000 claims 1
- WYGTZMORWGQIPR-UHFFFAOYSA-N 3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(CN2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 WYGTZMORWGQIPR-UHFFFAOYSA-N 0.000 claims 1
- PBOYZQSBWYSLIG-UHFFFAOYSA-N 3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]-n-propan-2-ylbenzamide Chemical compound CC(C)NC(=O)C1=CC=CC(CN2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 PBOYZQSBWYSLIG-UHFFFAOYSA-N 0.000 claims 1
- LWSGIZCOBNMXTH-UHFFFAOYSA-N 3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]benzamide Chemical compound BrC=1C(=O)N(CC=2C=C(C=CC=2)C(N)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F LWSGIZCOBNMXTH-UHFFFAOYSA-N 0.000 claims 1
- VBHZRXWLNOGUCA-UHFFFAOYSA-N 3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]benzoic acid Chemical compound BrC=1C(=O)N(CC=2C=C(C=CC=2)C(O)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F VBHZRXWLNOGUCA-UHFFFAOYSA-N 0.000 claims 1
- BZZUVLCCDXIIPE-UHFFFAOYSA-N 3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]benzonitrile Chemical compound BrC=1C(=O)N(CC=2C=C(C=CC=2)C#N)C(C)=CC=1OCC1=CC=C(F)C=C1F BZZUVLCCDXIIPE-UHFFFAOYSA-N 0.000 claims 1
- VOFOQSWSEVXECN-UHFFFAOYSA-N 3-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-2-fluorobenzamide Chemical compound NC(=O)C1=CC=CC(CN2C(C(Cl)=C(OCC=3C(=CC(F)=CC=3)F)C=C2)=O)=C1F VOFOQSWSEVXECN-UHFFFAOYSA-N 0.000 claims 1
- QTNDSGYMKFLNBE-UHFFFAOYSA-N 3-[[3-chloro-4-[(2,4-difluorophenyl)methylamino]-6-methyl-2-oxopyridin-1-yl]methyl]benzonitrile Chemical compound ClC=1C(=O)N(CC=2C=C(C=CC=2)C#N)C(C)=CC=1NCC1=CC=C(F)C=C1F QTNDSGYMKFLNBE-UHFFFAOYSA-N 0.000 claims 1
- BGCJRJKYYGIUAK-UHFFFAOYSA-N 3-acetyl-5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-1-(2-hydroxy-2-methylpropanoyl)benzimidazol-2-one Chemical compound C=1C=C2N(C(=O)C(C)(C)O)C(=O)N(C(=O)C)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F BGCJRJKYYGIUAK-UHFFFAOYSA-N 0.000 claims 1
- NKLOWPMSCOOUKU-UHFFFAOYSA-N 3-acetyl-5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-1-(2-hydroxyacetyl)benzimidazol-2-one Chemical compound C=1C=C2N(C(=O)CO)C(=O)N(C(=O)C)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F NKLOWPMSCOOUKU-UHFFFAOYSA-N 0.000 claims 1
- ZTIFKJPNTXJZNE-UHFFFAOYSA-N 3-acetyl-5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-1-(3-hydroxy-3-methylbutanoyl)benzimidazol-2-one Chemical compound C=1C=C2N(C(=O)CC(C)(C)O)C(=O)N(C(=O)C)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F ZTIFKJPNTXJZNE-UHFFFAOYSA-N 0.000 claims 1
- ZJDAGNOLYATQJM-UHFFFAOYSA-N 3-acetyl-5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-1-(3-hydroxypropanoyl)benzimidazol-2-one Chemical compound C=1C=C2N(C(=O)CCO)C(=O)N(C(=O)C)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F ZJDAGNOLYATQJM-UHFFFAOYSA-N 0.000 claims 1
- KDBLWWHLEBEWJP-UHFFFAOYSA-N 3-acetyl-5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-1h-benzimidazol-2-one Chemical compound C=1C=C2NC(=O)N(C(=O)C)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F KDBLWWHLEBEWJP-UHFFFAOYSA-N 0.000 claims 1
- WGRDUWCKXAKASJ-UHFFFAOYSA-N 3-acetyl-6-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-1h-benzimidazol-2-one Chemical compound C1=C2NC(=O)N(C(=O)C)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F WGRDUWCKXAKASJ-UHFFFAOYSA-N 0.000 claims 1
- AUACBDRSDSKCDZ-UHFFFAOYSA-N 3-acetyl-6-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-2-oxobenzimidazole-1-carboxamide Chemical compound C1=C2N(C(N)=O)C(=O)N(C(=O)C)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F AUACBDRSDSKCDZ-UHFFFAOYSA-N 0.000 claims 1
- UHDWBUVUVDOEJP-UHFFFAOYSA-N 3-acetyl-6-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-2h-benzimidazole-1-carboxamide Chemical compound C=1C=C2N(C(=O)C)CN(C(N)=O)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F UHDWBUVUVDOEJP-UHFFFAOYSA-N 0.000 claims 1
- PYTYOIVBADCUDS-UHFFFAOYSA-N 3-bromo-1-(2,6-dichlorophenyl)-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(C=2C(=CC=CC=2Cl)Cl)C(C)=CC=1OCC1=CC=C(F)C=C1F PYTYOIVBADCUDS-UHFFFAOYSA-N 0.000 claims 1
- LJRWEWAERUZBPM-UHFFFAOYSA-N 3-bromo-1-(2,6-dichlorophenyl)-6-methyl-4-phenylmethoxypyridin-2-one Chemical compound BrC=1C(=O)N(C=2C(=CC=CC=2Cl)Cl)C(C)=CC=1OCC1=CC=CC=C1 LJRWEWAERUZBPM-UHFFFAOYSA-N 0.000 claims 1
- IKPVTJPSVJQTJW-UHFFFAOYSA-N 3-bromo-1-(2,6-difluorophenyl)-4-[(2,4-difluorophenyl)methoxy]-5-(1,2-dihydroxy-2-phenylethyl)-6-methylpyridin-2-one Chemical compound C=1C=C(F)C=C(F)C=1COC1=C(Br)C(=O)N(C=2C(=CC=CC=2F)F)C(C)=C1C(O)C(O)C1=CC=CC=C1 IKPVTJPSVJQTJW-UHFFFAOYSA-N 0.000 claims 1
- OYRUVUXLRCJBQR-UHFFFAOYSA-N 3-bromo-1-(2,6-difluorophenyl)-4-[(2,4-difluorophenyl)methoxy]-5-(hydroxyiminomethyl)-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(C=2C(=CC=CC=2F)F)C(C)=C(C=NO)C=1OCC1=CC=C(F)C=C1F OYRUVUXLRCJBQR-UHFFFAOYSA-N 0.000 claims 1
- PAIFGIKSRFQHQW-UHFFFAOYSA-N 3-bromo-1-(2,6-difluorophenyl)-4-[(2,4-difluorophenyl)methoxy]-5-ethenyl-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(C=2C(=CC=CC=2F)F)C(C)=C(C=C)C=1OCC1=CC=C(F)C=C1F PAIFGIKSRFQHQW-UHFFFAOYSA-N 0.000 claims 1
- DGKNVUBVVYMFQC-UHFFFAOYSA-N 3-bromo-1-(2,6-difluorophenyl)-4-[(2,4-difluorophenyl)methoxy]-6-(hydroxymethyl)pyridin-2-one Chemical compound BrC=1C(=O)N(C=2C(=CC=CC=2F)F)C(CO)=CC=1OCC1=CC=C(F)C=C1F DGKNVUBVVYMFQC-UHFFFAOYSA-N 0.000 claims 1
- CDUZXXAHLSHGLY-UHFFFAOYSA-N 3-bromo-1-(2,6-difluorophenyl)-4-[(2,4-difluorophenyl)methoxy]-6-[(dimethylamino)methyl]pyridin-2-one Chemical compound BrC=1C(=O)N(C=2C(=CC=CC=2F)F)C(CN(C)C)=CC=1OCC1=CC=C(F)C=C1F CDUZXXAHLSHGLY-UHFFFAOYSA-N 0.000 claims 1
- GHTHHULGSSWQOH-UHFFFAOYSA-N 3-bromo-1-(2,6-difluorophenyl)-4-[(2,4-difluorophenyl)methoxy]-6-methyl-5-(oxiran-2-yl)pyridin-2-one Chemical compound C=1C=C(F)C=C(F)C=1COC1=C(Br)C(=O)N(C=2C(=CC=CC=2F)F)C(C)=C1C1CO1 GHTHHULGSSWQOH-UHFFFAOYSA-N 0.000 claims 1
- GOZUPPYBSRVJCV-UHFFFAOYSA-N 3-bromo-1-(2,6-difluorophenyl)-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(C=2C(=CC=CC=2F)F)C(C)=CC=1OCC1=CC=C(F)C=C1F GOZUPPYBSRVJCV-UHFFFAOYSA-N 0.000 claims 1
- FTNCRJMWVSRKLQ-UHFFFAOYSA-N 3-bromo-1-(2,6-difluorophenyl)-4-[(2,4-difluorophenyl)methylamino]-6-methylpyridin-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.BrC=1C(=O)N(C=2C(=CC=CC=2F)F)C(C)=CC=1NCC1=CC=C(F)C=C1F FTNCRJMWVSRKLQ-UHFFFAOYSA-N 0.000 claims 1
- MNZLNMOQSBBSFB-UHFFFAOYSA-N 3-bromo-1-(2,6-difluorophenyl)-4-methoxy-6-methyl-5-(2-phenylethenyl)pyridin-2-one Chemical compound COC1=C(Br)C(=O)N(C=2C(=CC=CC=2F)F)C(C)=C1C=CC1=CC=CC=C1 MNZLNMOQSBBSFB-UHFFFAOYSA-N 0.000 claims 1
- MDJRCEQYPKSHCR-UHFFFAOYSA-N 3-bromo-1-(2,6-difluorophenyl)-4-methoxy-6-methyl-5-(2-phenylethyl)pyridin-2-one Chemical compound CC=1N(C=2C(=CC=CC=2F)F)C(=O)C(Br)=C(OC)C=1CCC1=CC=CC=C1 MDJRCEQYPKSHCR-UHFFFAOYSA-N 0.000 claims 1
- HWWJESWTDDBSKP-UHFFFAOYSA-N 3-bromo-1-(2,6-difluorophenyl)-4-methoxy-6-methyl-5-[(4-methylphenyl)methyl]pyridin-2-one Chemical compound CC=1N(C=2C(=CC=CC=2F)F)C(=O)C(Br)=C(OC)C=1CC1=CC=C(C)C=C1 HWWJESWTDDBSKP-UHFFFAOYSA-N 0.000 claims 1
- FOFZYUDEWXSUHS-UHFFFAOYSA-N 3-bromo-1-(2,6-difluorophenyl)-5-ethenyl-4-methoxy-6-methylpyridin-2-one Chemical compound CC1=C(C=C)C(OC)=C(Br)C(=O)N1C1=C(F)C=CC=C1F FOFZYUDEWXSUHS-UHFFFAOYSA-N 0.000 claims 1
- KBFGSUTZQQUJCZ-UHFFFAOYSA-N 3-bromo-1-(2,6-dimethylphenyl)-4-[(4-fluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound CC1=CC=CC(C)=C1N1C(=O)C(Br)=C(OCC=2C=CC(F)=CC=2)C=C1C KBFGSUTZQQUJCZ-UHFFFAOYSA-N 0.000 claims 1
- WWKDYZXSYNVDLC-UHFFFAOYSA-N 3-bromo-1-(2,6-dimethylphenyl)-6-methyl-4-[(2,4,6-trifluorophenyl)methoxy]pyridin-2-one Chemical compound CC1=CC=CC(C)=C1N1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2F)F)C=C1C WWKDYZXSYNVDLC-UHFFFAOYSA-N 0.000 claims 1
- SYKOHFFWDWSILL-UHFFFAOYSA-N 3-bromo-1-(2-chlorophenyl)-6-methyl-4-phenylmethoxypyridin-2-one Chemical compound BrC=1C(=O)N(C=2C(=CC=CC=2)Cl)C(C)=CC=1OCC1=CC=CC=C1 SYKOHFFWDWSILL-UHFFFAOYSA-N 0.000 claims 1
- ZDQKATDQQRFJSG-UHFFFAOYSA-N 3-bromo-1-(4-bromo-2,6-difluorophenyl)-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(C=2C(=CC(Br)=CC=2F)F)C(C)=CC=1OCC1=CC=C(F)C=C1F ZDQKATDQQRFJSG-UHFFFAOYSA-N 0.000 claims 1
- HPZZTJRXAGMYDR-UHFFFAOYSA-N 3-bromo-1-(cyclohexylmethyl)-4-[(4-fluorophenyl)methoxy]pyridin-2-one Chemical compound C1=CC(F)=CC=C1COC1=C(Br)C(=O)N(CC2CCCCC2)C=C1 HPZZTJRXAGMYDR-UHFFFAOYSA-N 0.000 claims 1
- XXFGDXRZXGVUKN-UHFFFAOYSA-N 3-bromo-1-(cyclopropylmethyl)-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC2CC2)C(C)=CC=1OCC1=CC=C(F)C=C1F XXFGDXRZXGVUKN-UHFFFAOYSA-N 0.000 claims 1
- YCCHEVWNNOVBCC-UHFFFAOYSA-N 3-bromo-1-[(3-chlorophenyl)methyl]-4-[(4-fluorophenyl)methoxy]pyridin-2-one Chemical compound C1=CC(F)=CC=C1COC1=C(Br)C(=O)N(CC=2C=C(Cl)C=CC=2)C=C1 YCCHEVWNNOVBCC-UHFFFAOYSA-N 0.000 claims 1
- DJRDPFQHCYHPEI-UHFFFAOYSA-N 3-bromo-1-[(3-fluorophenyl)methyl]-4-(3,4,5-trimethoxyanilino)pyridin-2-one Chemical compound COC1=C(OC)C(OC)=CC(NC2=C(C(=O)N(CC=3C=C(F)C=CC=3)C=C2)Br)=C1 DJRDPFQHCYHPEI-UHFFFAOYSA-N 0.000 claims 1
- MGZMKZCEJDMPSG-UHFFFAOYSA-N 3-bromo-1-[(3-fluorophenyl)methyl]-4-(3-methoxyphenyl)pyridin-2-one Chemical compound COC1=CC=CC(C2=C(C(=O)N(CC=3C=C(F)C=CC=3)C=C2)Br)=C1 MGZMKZCEJDMPSG-UHFFFAOYSA-N 0.000 claims 1
- CYUUYASHPVYPDC-UHFFFAOYSA-N 3-bromo-1-[(3-fluorophenyl)methyl]-4-(3-propan-2-ylphenyl)pyridin-2-one Chemical compound CC(C)C1=CC=CC(C2=C(C(=O)N(CC=3C=C(F)C=CC=3)C=C2)Br)=C1 CYUUYASHPVYPDC-UHFFFAOYSA-N 0.000 claims 1
- KWCYFVAUNPVYIU-UHFFFAOYSA-N 3-bromo-1-[(3-fluorophenyl)methyl]-4-[(2,3,4-trifluorophenyl)methoxy]pyridin-2-one Chemical compound FC1=CC=CC(CN2C(C(Br)=C(OCC=3C(=C(F)C(F)=CC=3)F)C=C2)=O)=C1 KWCYFVAUNPVYIU-UHFFFAOYSA-N 0.000 claims 1
- ISPBEKCONPBDHT-UHFFFAOYSA-N 3-bromo-1-[(3-fluorophenyl)methyl]-4-[(3-methoxyphenyl)methoxy]pyridin-2-one Chemical compound COC1=CC=CC(COC2=C(C(=O)N(CC=3C=C(F)C=CC=3)C=C2)Br)=C1 ISPBEKCONPBDHT-UHFFFAOYSA-N 0.000 claims 1
- AJHRIIBTIBSXRZ-UHFFFAOYSA-N 3-bromo-1-[(3-fluorophenyl)methyl]-4-[3-(trifluoromethyl)phenyl]pyridin-2-one Chemical compound FC1=CC=CC(CN2C(C(Br)=C(C=C2)C=2C=C(C=CC=2)C(F)(F)F)=O)=C1 AJHRIIBTIBSXRZ-UHFFFAOYSA-N 0.000 claims 1
- MKAUKQOTOSOSRD-UHFFFAOYSA-N 3-bromo-1-[(3-fluorophenyl)methyl]-4-[4-(4-fluorophenyl)piperazin-1-yl]pyridin-2-one Chemical compound C1=CC(F)=CC=C1N1CCN(C2=C(C(=O)N(CC=3C=C(F)C=CC=3)C=C2)Br)CC1 MKAUKQOTOSOSRD-UHFFFAOYSA-N 0.000 claims 1
- XONCIDSPNJZMLA-UHFFFAOYSA-N 3-bromo-1-[(3-fluorophenyl)methyl]-4-[[3-(trifluoromethyl)phenyl]methylamino]pyridin-2-one Chemical compound FC1=CC=CC(CN2C(C(Br)=C(NCC=3C=C(C=CC=3)C(F)(F)F)C=C2)=O)=C1 XONCIDSPNJZMLA-UHFFFAOYSA-N 0.000 claims 1
- JKDVZJBTDZNXJT-UHFFFAOYSA-N 3-bromo-1-[(3-fluorophenyl)methyl]-4-[[4-fluoro-2-(trifluoromethyl)phenyl]methylamino]pyridin-2-one Chemical compound FC1=CC=CC(CN2C(C(Br)=C(NCC=3C(=CC(F)=CC=3)C(F)(F)F)C=C2)=O)=C1 JKDVZJBTDZNXJT-UHFFFAOYSA-N 0.000 claims 1
- URTSKRRLLJOBMM-UHFFFAOYSA-N 3-bromo-1-[(3-fluorophenyl)methyl]-4-naphthalen-2-ylpyridin-2-one Chemical compound FC1=CC=CC(CN2C(C(Br)=C(C=3C=C4C=CC=CC4=CC=3)C=C2)=O)=C1 URTSKRRLLJOBMM-UHFFFAOYSA-N 0.000 claims 1
- XDRGITSMHZBTQM-UHFFFAOYSA-N 3-bromo-1-[(3-fluorophenyl)methyl]-4-phenylmethoxypyridin-2-one Chemical compound FC1=CC=CC(CN2C(C(Br)=C(OCC=3C=CC=CC=3)C=C2)=O)=C1 XDRGITSMHZBTQM-UHFFFAOYSA-N 0.000 claims 1
- PLWXNASPXHHLCW-UHFFFAOYSA-N 3-bromo-1-[(3-fluorophenyl)methyl]-4-thiophen-3-ylpyridin-2-one Chemical compound FC1=CC=CC(CN2C(C(Br)=C(C3=CSC=C3)C=C2)=O)=C1 PLWXNASPXHHLCW-UHFFFAOYSA-N 0.000 claims 1
- HIAKFPKSNDCJIG-UHFFFAOYSA-N 3-bromo-1-[(3-fluorophenyl)methyl]-6-methyl-4-(2-phenylethyl)pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=C(F)C=CC=2)C(C)=CC=1CCC1=CC=CC=C1 HIAKFPKSNDCJIG-UHFFFAOYSA-N 0.000 claims 1
- ZOLVFOOYAUHMCG-UHFFFAOYSA-N 3-bromo-1-[(4-fluorophenyl)methyl]-4-[(4-fluorophenyl)methylamino]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC(F)=CC=2)C(C)=CC=1NCC1=CC=C(F)C=C1 ZOLVFOOYAUHMCG-UHFFFAOYSA-N 0.000 claims 1
- WDQFELYCHMWETR-UHFFFAOYSA-N 3-bromo-1-[(4-fluorophenyl)methyl]-4-phenylmethoxypyridin-2-one Chemical compound C1=CC(F)=CC=C1CN1C(=O)C(Br)=C(OCC=2C=CC=CC=2)C=C1 WDQFELYCHMWETR-UHFFFAOYSA-N 0.000 claims 1
- ODBDXLLHQAWGMD-UHFFFAOYSA-N 3-bromo-1-[(4-methoxyphenyl)methyl]-4-phenoxypyridin-2-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C(Br)=C(OC=2C=CC=CC=2)C=C1 ODBDXLLHQAWGMD-UHFFFAOYSA-N 0.000 claims 1
- YYWRKEQKRIJDBF-UHFFFAOYSA-N 3-bromo-1-[[5-(chloromethyl)pyrazin-2-yl]methyl]-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2N=CC(CCl)=NC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F YYWRKEQKRIJDBF-UHFFFAOYSA-N 0.000 claims 1
- AXDKIGXWRRZING-UHFFFAOYSA-N 3-bromo-1-ethyl-4-phenylmethoxypyridin-2-one Chemical compound O=C1N(CC)C=CC(OCC=2C=CC=CC=2)=C1Br AXDKIGXWRRZING-UHFFFAOYSA-N 0.000 claims 1
- CZJKPXYWNNZADO-UHFFFAOYSA-N 3-bromo-1-methylsulfonyl-4-phenylmethoxypyridin-2-one Chemical compound O=C1N(S(=O)(=O)C)C=CC(OCC=2C=CC=CC=2)=C1Br CZJKPXYWNNZADO-UHFFFAOYSA-N 0.000 claims 1
- PYYOXZVAAIOWFD-UHFFFAOYSA-N 3-bromo-4-(4-fluorophenyl)-1-[(3-fluorophenyl)methyl]pyridin-2-one Chemical compound C1=CC(F)=CC=C1C1=C(Br)C(=O)N(CC=2C=C(F)C=CC=2)C=C1 PYYOXZVAAIOWFD-UHFFFAOYSA-N 0.000 claims 1
- UBCPORPPYBHIGX-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-(pyridin-3-ylmethyl)pyridin-2-one Chemical compound FC1=CC(F)=CC=C1COC1=C(Br)C(=O)N(CC=2C=NC=CC=2)C=C1 UBCPORPPYBHIGX-UHFFFAOYSA-N 0.000 claims 1
- CKJWOZQKDKHLTO-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[(2,4-difluorophenyl)methyl]pyridin-2-one Chemical compound FC1=CC(F)=CC=C1COC1=C(Br)C(=O)N(CC=2C(=CC(F)=CC=2)F)C=C1 CKJWOZQKDKHLTO-UHFFFAOYSA-N 0.000 claims 1
- WHQZLCGMEMTORY-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[(2-fluorophenyl)methyl]pyridin-2-one Chemical compound FC1=CC(F)=CC=C1COC1=C(Br)C(=O)N(CC=2C(=CC=CC=2)F)C=C1 WHQZLCGMEMTORY-UHFFFAOYSA-N 0.000 claims 1
- JURCTYDNVUPMHW-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[(3-fluorophenyl)methyl]pyridin-2-one Chemical compound FC1=CC(F)=CC=C1COC1=C(Br)C(=O)N(CC=2C=C(F)C=CC=2)C=C1 JURCTYDNVUPMHW-UHFFFAOYSA-N 0.000 claims 1
- HHMPIYKOEZVBLI-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[(3-methoxyphenyl)methyl]pyridin-2-one Chemical compound COC1=CC=CC(CN2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2)=O)=C1 HHMPIYKOEZVBLI-UHFFFAOYSA-N 0.000 claims 1
- CFCCLYABTGQRRK-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[(4-hydroxyphenyl)methyl]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC(O)=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F CFCCLYABTGQRRK-UHFFFAOYSA-N 0.000 claims 1
- IKRHZQGQOXJQTE-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[(4-methoxyphenyl)methyl]-6-methylpyridin-2-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C IKRHZQGQOXJQTE-UHFFFAOYSA-N 0.000 claims 1
- FCRPSBNBZCFXJE-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[2-fluoro-6-(4-methylpiperazin-1-yl)phenyl]-6-methylpyridin-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CN(C)CCN1C1=CC=CC(F)=C1N1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C FCRPSBNBZCFXJE-UHFFFAOYSA-N 0.000 claims 1
- RMUXSXNNEYSTSF-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[3-(hydroxymethyl)phenyl]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(C=2C=C(CO)C=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F RMUXSXNNEYSTSF-UHFFFAOYSA-N 0.000 claims 1
- DZVQDZGSPICOEQ-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[4-(dimethylamino)-2,6-difluorophenyl]-6-methylpyridin-2-one Chemical compound FC1=CC(N(C)C)=CC(F)=C1N1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C DZVQDZGSPICOEQ-UHFFFAOYSA-N 0.000 claims 1
- MZYXKDNQIOYGCR-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[4-(hydroxymethyl)-2-methoxyphenyl]-6-methylpyridin-2-one Chemical compound COC1=CC(CO)=CC=C1N1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C MZYXKDNQIOYGCR-UHFFFAOYSA-N 0.000 claims 1
- OOXYFLNSDWHTMI-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[5-(2-hydroxypropan-2-yl)pyridin-2-yl]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(C=2N=CC(=CC=2)C(C)(C)O)C(C)=CC=1OCC1=CC=C(F)C=C1F OOXYFLNSDWHTMI-UHFFFAOYSA-N 0.000 claims 1
- GJCVZCYDXHUBND-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[5-[(dimethylamino)methyl]-2-methylphenyl]-6-methylpyridin-2-one;hydrochloride Chemical compound Cl.CN(C)CC1=CC=C(C)C(N2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 GJCVZCYDXHUBND-UHFFFAOYSA-N 0.000 claims 1
- VKGYUOOFLDCUKP-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[[1-(2-hydroxyacetyl)-2,3-dihydroindol-5-yl]methyl]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=C3CCN(C3=CC=2)C(=O)CO)C(C)=CC=1OCC1=CC=C(F)C=C1F VKGYUOOFLDCUKP-UHFFFAOYSA-N 0.000 claims 1
- SYSSICAQHOQMHH-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[[2-methyl-4-(methylamino)pyrimidin-5-yl]methyl]pyridin-2-one Chemical compound CNC1=NC(C)=NC=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1 SYSSICAQHOQMHH-UHFFFAOYSA-N 0.000 claims 1
- BMMCSJCFURIBLB-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[[3-(hydroxymethyl)phenyl]methyl]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=C(CO)C=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F BMMCSJCFURIBLB-UHFFFAOYSA-N 0.000 claims 1
- IDCZHNCTHXXGQT-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[[3-(methylaminomethyl)phenyl]methyl]pyridin-2-one Chemical compound CNCC1=CC=CC(CN2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2)=O)=C1 IDCZHNCTHXXGQT-UHFFFAOYSA-N 0.000 claims 1
- RHIYYOQCRBLTAF-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[[3-[(2-hydroxyethylamino)methyl]phenyl]methyl]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=C(CNCCO)C=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F RHIYYOQCRBLTAF-UHFFFAOYSA-N 0.000 claims 1
- YKKDTWCJTMOIQU-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[[3-[(dimethylamino)methyl]phenyl]methyl]-6-methylpyridin-2-one Chemical compound CN(C)CC1=CC=CC(CN2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 YKKDTWCJTMOIQU-UHFFFAOYSA-N 0.000 claims 1
- JEYVELKUHKYRAN-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[[3-[(dimethylamino)methyl]phenyl]methyl]pyridin-2-one Chemical compound CN(C)CC1=CC=CC(CN2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2)=O)=C1 JEYVELKUHKYRAN-UHFFFAOYSA-N 0.000 claims 1
- GHFIWNGCIMBPCL-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[[3-[(propan-2-ylamino)methyl]phenyl]methyl]pyridin-2-one Chemical compound CC(C)NCC1=CC=CC(CN2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2)=O)=C1 GHFIWNGCIMBPCL-UHFFFAOYSA-N 0.000 claims 1
- RFNPFHVTUALNRU-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[[4-(hydroxymethyl)phenyl]methyl]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC(CO)=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F RFNPFHVTUALNRU-UHFFFAOYSA-N 0.000 claims 1
- JUVJYTZFOIDBCF-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[[4-[(2-hydroxyethylamino)methyl]phenyl]methyl]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC(CNCCO)=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F JUVJYTZFOIDBCF-UHFFFAOYSA-N 0.000 claims 1
- DHXKHAXDIKGJKS-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[[4-[(dimethylamino)methyl]phenyl]methyl]-6-methylpyridin-2-one Chemical compound C1=CC(CN(C)C)=CC=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C DHXKHAXDIKGJKS-UHFFFAOYSA-N 0.000 claims 1
- QRDITZSOTLKYIO-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[[4-[(dimethylamino)methyl]phenyl]methyl]pyridin-2-one Chemical compound C1=CC(CN(C)C)=CC=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1 QRDITZSOTLKYIO-UHFFFAOYSA-N 0.000 claims 1
- QXQSOVBZGVKXFF-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[[5-(2-hydroxypropan-2-yl)pyrazin-2-yl]methyl]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2N=CC(=NC=2)C(C)(C)O)C(C)=CC=1OCC1=CC=C(F)C=C1F QXQSOVBZGVKXFF-UHFFFAOYSA-N 0.000 claims 1
- VRUMKXUXAUOMFG-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[[5-[(dimethylamino)methyl]pyrazin-2-yl]methyl]-6-methylpyridin-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=NC(CN(C)C)=CN=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C VRUMKXUXAUOMFG-UHFFFAOYSA-N 0.000 claims 1
- BHNCKTRMRCYGCM-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[[5-[[2-hydroxyethyl(methyl)amino]methyl]pyrazin-2-yl]methyl]-6-methylpyridin-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=NC(CN(CCO)C)=CN=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C BHNCKTRMRCYGCM-UHFFFAOYSA-N 0.000 claims 1
- RFVZVMFSQNGNBV-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-(2-methylsulfanylpyrimidin-4-yl)pyridin-2-one Chemical compound CSC1=NC=CC(N2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=N1 RFVZVMFSQNGNBV-UHFFFAOYSA-N 0.000 claims 1
- GRVCRQOYOUROBE-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-(pyridin-3-ylmethyl)pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=NC=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F GRVCRQOYOUROBE-UHFFFAOYSA-N 0.000 claims 1
- KVULQBZQKJHUPR-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[2-methyl-5-[(propan-2-ylamino)methyl]phenyl]pyridin-2-one;hydrochloride Chemical compound Cl.CC(C)NCC1=CC=C(C)C(N2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 KVULQBZQKJHUPR-UHFFFAOYSA-N 0.000 claims 1
- WZEXEBLOKGSXSY-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[3-(4-methylpiperazine-1-carbonyl)phenyl]pyridin-2-one Chemical compound C1CN(C)CCN1C(=O)C1=CC=CC(N2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 WZEXEBLOKGSXSY-UHFFFAOYSA-N 0.000 claims 1
- CUTQBIQQHQAYKS-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[3-(morpholine-4-carbonyl)phenyl]pyridin-2-one Chemical compound BrC=1C(=O)N(C=2C=C(C=CC=2)C(=O)N2CCOCC2)C(C)=CC=1OCC1=CC=C(F)C=C1F CUTQBIQQHQAYKS-UHFFFAOYSA-N 0.000 claims 1
- MUHMYVVWGAAZIU-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[3-(piperidine-1-carbonyl)phenyl]pyridin-2-one Chemical compound BrC=1C(=O)N(C=2C=C(C=CC=2)C(=O)N2CCCCC2)C(C)=CC=1OCC1=CC=C(F)C=C1F MUHMYVVWGAAZIU-UHFFFAOYSA-N 0.000 claims 1
- SZTTWIFQLGRJNL-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[3-(pyrrolidine-1-carbonyl)phenyl]pyridin-2-one Chemical compound BrC=1C(=O)N(C=2C=C(C=CC=2)C(=O)N2CCCC2)C(C)=CC=1OCC1=CC=C(F)C=C1F SZTTWIFQLGRJNL-UHFFFAOYSA-N 0.000 claims 1
- CWRTUCLGTMHNGV-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[4-(morpholine-4-carbonyl)phenyl]pyridin-2-one Chemical compound BrC=1C(=O)N(C=2C=CC(=CC=2)C(=O)N2CCOCC2)C(C)=CC=1OCC1=CC=C(F)C=C1F CWRTUCLGTMHNGV-UHFFFAOYSA-N 0.000 claims 1
- KNYSZNVJNGUJIK-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[4-(piperazine-1-carbonyl)phenyl]pyridin-2-one;hydrochloride Chemical compound Cl.BrC=1C(=O)N(C=2C=CC(=CC=2)C(=O)N2CCNCC2)C(C)=CC=1OCC1=CC=C(F)C=C1F KNYSZNVJNGUJIK-UHFFFAOYSA-N 0.000 claims 1
- VDFLWTMGBUSJOQ-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[3-(morpholin-4-ylmethyl)phenyl]methyl]pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=C(CN3CCOCC3)C=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F VDFLWTMGBUSJOQ-UHFFFAOYSA-N 0.000 claims 1
- IAKOYOLDLXNUDA-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[3-(morpholine-4-carbonyl)phenyl]methyl]pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=C(C=CC=2)C(=O)N2CCOCC2)C(C)=CC=1OCC1=CC=C(F)C=C1F IAKOYOLDLXNUDA-UHFFFAOYSA-N 0.000 claims 1
- STDRUJNTLJXCBL-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[3-(piperazin-1-ylmethyl)phenyl]methyl]pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=C(CN3CCNCC3)C=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F STDRUJNTLJXCBL-UHFFFAOYSA-N 0.000 claims 1
- YDOBOFSWXAHGDU-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[3-(piperazine-1-carbonyl)phenyl]methyl]pyridin-2-one;hydrochloride Chemical compound Cl.BrC=1C(=O)N(CC=2C=C(C=CC=2)C(=O)N2CCNCC2)C(C)=CC=1OCC1=CC=C(F)C=C1F YDOBOFSWXAHGDU-UHFFFAOYSA-N 0.000 claims 1
- WIMSUHIRKPCMIK-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[3-(piperidin-1-ylmethyl)phenyl]methyl]pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=C(CN3CCCCC3)C=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F WIMSUHIRKPCMIK-UHFFFAOYSA-N 0.000 claims 1
- LFTMVIZEAYWSBK-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[3-(piperidine-1-carbonyl)phenyl]methyl]pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=C(C=CC=2)C(=O)N2CCCCC2)C(C)=CC=1OCC1=CC=C(F)C=C1F LFTMVIZEAYWSBK-UHFFFAOYSA-N 0.000 claims 1
- KSOATGNRJBFBRN-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[3-(pyrrolidine-1-carbonyl)phenyl]methyl]pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=C(C=CC=2)C(=O)N2CCCC2)C(C)=CC=1OCC1=CC=C(F)C=C1F KSOATGNRJBFBRN-UHFFFAOYSA-N 0.000 claims 1
- KFCMYVRZOANEQN-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[3-[(propan-2-ylamino)methyl]phenyl]methyl]pyridin-2-one Chemical compound CC(C)NCC1=CC=CC(CN2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 KFCMYVRZOANEQN-UHFFFAOYSA-N 0.000 claims 1
- BIPSOOCSFJZMPJ-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[4-(4-methylpiperazine-1-carbonyl)phenyl]methyl]pyridin-2-one Chemical compound C1CN(C)CCN1C(=O)C(C=C1)=CC=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C BIPSOOCSFJZMPJ-UHFFFAOYSA-N 0.000 claims 1
- NNRZDPMJVSZIGC-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[4-(methylaminomethyl)phenyl]methyl]pyridin-2-one Chemical compound C1=CC(CNC)=CC=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C NNRZDPMJVSZIGC-UHFFFAOYSA-N 0.000 claims 1
- HGUGUFBQOOYLIG-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[4-(morpholin-4-ylmethyl)phenyl]methyl]pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC(CN3CCOCC3)=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F HGUGUFBQOOYLIG-UHFFFAOYSA-N 0.000 claims 1
- AZLNZHPAZDPBFP-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[4-(morpholine-4-carbonyl)phenyl]methyl]pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC(=CC=2)C(=O)N2CCOCC2)C(C)=CC=1OCC1=CC=C(F)C=C1F AZLNZHPAZDPBFP-UHFFFAOYSA-N 0.000 claims 1
- NUZGHPNAXRJEBI-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[4-(piperazin-1-ylmethyl)phenyl]methyl]pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC(CN3CCNCC3)=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F NUZGHPNAXRJEBI-UHFFFAOYSA-N 0.000 claims 1
- BLJJRXQRIHIWBB-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[4-(piperidin-1-ylmethyl)phenyl]methyl]pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC(CN3CCCCC3)=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F BLJJRXQRIHIWBB-UHFFFAOYSA-N 0.000 claims 1
- BUBJGYIZDJDHFJ-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[4-(piperidine-1-carbonyl)phenyl]methyl]pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC(=CC=2)C(=O)N2CCCCC2)C(C)=CC=1OCC1=CC=C(F)C=C1F BUBJGYIZDJDHFJ-UHFFFAOYSA-N 0.000 claims 1
- GXLFHDJNLABUGA-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[4-(pyrrolidine-1-carbonyl)phenyl]methyl]pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC(=CC=2)C(=O)N2CCCC2)C(C)=CC=1OCC1=CC=C(F)C=C1F GXLFHDJNLABUGA-UHFFFAOYSA-N 0.000 claims 1
- FVRNNZLBRRHPPE-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[4-[(propan-2-ylamino)methyl]phenyl]methyl]pyridin-2-one Chemical compound C1=CC(CNC(C)C)=CC=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C FVRNNZLBRRHPPE-UHFFFAOYSA-N 0.000 claims 1
- YKPFXMCWRDFLFD-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[5-(methylaminomethyl)pyrazin-2-yl]methyl]pyridin-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=NC(CNC)=CN=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C YKPFXMCWRDFLFD-UHFFFAOYSA-N 0.000 claims 1
- KWMLVJCBRJIQNB-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1h-pyridin-2-one Chemical compound O=C1NC(C)=CC(OCC=2C(=CC(F)=CC=2)F)=C1Br KWMLVJCBRJIQNB-UHFFFAOYSA-N 0.000 claims 1
- NXEMXHJBILEEQI-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methylamino]-1-[(3-fluorophenyl)methyl]pyridin-2-one Chemical compound FC1=CC(F)=CC=C1CNC1=C(Br)C(=O)N(CC=2C=C(F)C=CC=2)C=C1 NXEMXHJBILEEQI-UHFFFAOYSA-N 0.000 claims 1
- CPIIZOXPHSIVJV-UHFFFAOYSA-N 3-bromo-4-[(3,4-difluorophenyl)methoxy]-1-[(3-fluorophenyl)methyl]pyridin-2-one Chemical compound FC1=CC=CC(CN2C(C(Br)=C(OCC=3C=C(F)C(F)=CC=3)C=C2)=O)=C1 CPIIZOXPHSIVJV-UHFFFAOYSA-N 0.000 claims 1
- ODFACWUQGHQAIZ-UHFFFAOYSA-N 3-bromo-4-[(3-chlorophenyl)methoxy]-1-[(3-fluorophenyl)methyl]pyridin-2-one Chemical compound FC1=CC=CC(CN2C(C(Br)=C(OCC=3C=C(Cl)C=CC=3)C=C2)=O)=C1 ODFACWUQGHQAIZ-UHFFFAOYSA-N 0.000 claims 1
- CKOUMHBUHJOLLC-UHFFFAOYSA-N 3-bromo-4-[(4-chloro-2-fluorophenyl)methylamino]-1-[(3-fluorophenyl)methyl]pyridin-2-one Chemical compound FC1=CC=CC(CN2C(C(Br)=C(NCC=3C(=CC(Cl)=CC=3)F)C=C2)=O)=C1 CKOUMHBUHJOLLC-UHFFFAOYSA-N 0.000 claims 1
- RQNLLSTUKKZSQA-UHFFFAOYSA-N 3-bromo-4-[(4-chlorophenyl)methoxy]-1-(2-phenylethyl)pyridin-2-one Chemical compound C1=CC(Cl)=CC=C1COC1=C(Br)C(=O)N(CCC=2C=CC=CC=2)C=C1 RQNLLSTUKKZSQA-UHFFFAOYSA-N 0.000 claims 1
- DHACVKCSQJYQLT-UHFFFAOYSA-N 3-bromo-4-[(4-chlorophenyl)methoxy]-1-[(4-methoxyphenyl)methyl]pyridin-2-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C(Br)=C(OCC=2C=CC(Cl)=CC=2)C=C1 DHACVKCSQJYQLT-UHFFFAOYSA-N 0.000 claims 1
- LPIYWNIAXNOXHM-UHFFFAOYSA-N 3-bromo-4-[(4-fluorophenyl)methoxy]-1-(3-phenylpropyl)pyridin-2-one Chemical compound C1=CC(F)=CC=C1COC1=C(Br)C(=O)N(CCCC=2C=CC=CC=2)C=C1 LPIYWNIAXNOXHM-UHFFFAOYSA-N 0.000 claims 1
- UZJFRXCJUVIVMW-UHFFFAOYSA-N 3-bromo-4-[(4-fluorophenyl)methoxy]-1-(pyridin-3-ylmethyl)pyridin-2-one Chemical compound C1=CC(F)=CC=C1COC1=C(Br)C(=O)N(CC=2C=NC=CC=2)C=C1 UZJFRXCJUVIVMW-UHFFFAOYSA-N 0.000 claims 1
- PYJZBBGMYAYLMC-UHFFFAOYSA-N 3-bromo-4-[(4-fluorophenyl)methoxy]-1-[(3-fluorophenyl)methyl]pyridin-2-one Chemical compound C1=CC(F)=CC=C1COC1=C(Br)C(=O)N(CC=2C=C(F)C=CC=2)C=C1 PYJZBBGMYAYLMC-UHFFFAOYSA-N 0.000 claims 1
- BISRNVADLDRNLO-UHFFFAOYSA-N 3-bromo-4-[(4-fluorophenyl)methoxy]-1-[[2-(hydroxymethyl)phenyl]methyl]pyridin-2-one Chemical compound OCC1=CC=CC=C1CN1C(=O)C(Br)=C(OCC=2C=CC(F)=CC=2)C=C1 BISRNVADLDRNLO-UHFFFAOYSA-N 0.000 claims 1
- WNDFWYAGSNZSPE-UHFFFAOYSA-N 3-bromo-4-[(4-fluorophenyl)methoxy]-1-[[4-(trifluoromethyl)phenyl]methyl]pyridin-2-one Chemical compound C1=CC(F)=CC=C1COC1=C(Br)C(=O)N(CC=2C=CC(=CC=2)C(F)(F)F)C=C1 WNDFWYAGSNZSPE-UHFFFAOYSA-N 0.000 claims 1
- OFGYTNBQKUHLKP-UHFFFAOYSA-N 3-bromo-4-[(4-fluorophenyl)methoxy]-6-methyl-1-(pyridin-2-ylmethyl)pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2N=CC=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1 OFGYTNBQKUHLKP-UHFFFAOYSA-N 0.000 claims 1
- IGRZUDHUUQCAQG-UHFFFAOYSA-N 3-bromo-4-[(4-fluorophenyl)methoxy]-6-methyl-1-(pyridin-3-ylmethyl)pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=NC=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1 IGRZUDHUUQCAQG-UHFFFAOYSA-N 0.000 claims 1
- UMDIOJBZAHPYJK-UHFFFAOYSA-N 3-bromo-4-phenylmethoxy-1-(2-thiophen-3-ylethyl)pyridin-2-one Chemical compound C1=CN(CCC2=CSC=C2)C(=O)C(Br)=C1OCC1=CC=CC=C1 UMDIOJBZAHPYJK-UHFFFAOYSA-N 0.000 claims 1
- SLVBVJHGSQRBPU-UHFFFAOYSA-N 3-bromo-4-phenylmethoxy-1-(piperidin-3-ylmethyl)pyridin-2-one Chemical compound C1=CN(CC2CNCCC2)C(=O)C(Br)=C1OCC1=CC=CC=C1 SLVBVJHGSQRBPU-UHFFFAOYSA-N 0.000 claims 1
- BGOOIDYLWWWXQA-UHFFFAOYSA-N 3-bromo-4-phenylmethoxy-1-(piperidin-4-ylmethyl)pyridin-2-one;hydrochloride Chemical compound Cl.C1=CN(CC2CCNCC2)C(=O)C(Br)=C1OCC1=CC=CC=C1 BGOOIDYLWWWXQA-UHFFFAOYSA-N 0.000 claims 1
- DEAFHBHPKIDTKB-UHFFFAOYSA-N 3-bromo-4-phenylmethoxy-1-[[4-(trifluoromethoxy)phenyl]methyl]pyridin-2-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1CN1C(=O)C(Br)=C(OCC=2C=CC=CC=2)C=C1 DEAFHBHPKIDTKB-UHFFFAOYSA-N 0.000 claims 1
- VERMHXLZMHMKBH-UHFFFAOYSA-N 3-bromo-4-phenylmethoxy-1-[[4-(trifluoromethyl)phenyl]methyl]pyridin-2-one Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1C(=O)C(Br)=C(OCC=2C=CC=CC=2)C=C1 VERMHXLZMHMKBH-UHFFFAOYSA-N 0.000 claims 1
- DIWZMLPXCBIWCZ-UHFFFAOYSA-N 3-bromo-6-methyl-1-(pyridin-3-ylmethyl)-4-(pyridin-3-ylmethylamino)pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=NC=CC=2)C(C)=CC=1NCC1=CC=CN=C1 DIWZMLPXCBIWCZ-UHFFFAOYSA-N 0.000 claims 1
- AJVLNNWCBOKTQK-UHFFFAOYSA-N 3-chloro-1-(1,3-diacetyl-2h-benzimidazol-5-yl)-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound C=1C=C2N(C(=O)C)CN(C(C)=O)C2=CC=1N(C(C=1Cl)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F AJVLNNWCBOKTQK-UHFFFAOYSA-N 0.000 claims 1
- FLFQSJTVQZCKBB-UHFFFAOYSA-N 3-chloro-1-(2,6-difluorophenyl)-4-[(2,4-difluorophenyl)methoxy]-6-(hydroxymethyl)pyridin-2-one Chemical compound ClC=1C(=O)N(C=2C(=CC=CC=2F)F)C(CO)=CC=1OCC1=CC=C(F)C=C1F FLFQSJTVQZCKBB-UHFFFAOYSA-N 0.000 claims 1
- NUCMFOMVSQZVCI-UHFFFAOYSA-N 3-chloro-1-(2,6-difluorophenyl)-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound ClC=1C(=O)N(C=2C(=CC=CC=2F)F)C(C)=CC=1OCC1=CC=C(F)C=C1F NUCMFOMVSQZVCI-UHFFFAOYSA-N 0.000 claims 1
- KDNRKGYAOFHCRR-UHFFFAOYSA-N 3-chloro-1-(2,6-difluorophenyl)-4-[(2,4-difluorophenyl)methylamino]-6-methylpyridin-2-one Chemical compound ClC=1C(=O)N(C=2C(=CC=CC=2F)F)C(C)=CC=1NCC1=CC=C(F)C=C1F KDNRKGYAOFHCRR-UHFFFAOYSA-N 0.000 claims 1
- OMEJIWUXGNIFAW-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-(1,2,3,4-tetrahydroisoquinolin-6-ylmethyl)pyridin-2-one Chemical compound FC1=CC(F)=CC=C1COC1=C(Cl)C(=O)N(CC=2C=C3CCNCC3=CC=2)C=C1 OMEJIWUXGNIFAW-UHFFFAOYSA-N 0.000 claims 1
- SKMQHUSWXIUNBZ-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-(isoquinolin-6-ylmethyl)pyridin-2-one Chemical compound FC1=CC(F)=CC=C1COC1=C(Cl)C(=O)N(CC=2C=C3C=CN=CC3=CC=2)C=C1 SKMQHUSWXIUNBZ-UHFFFAOYSA-N 0.000 claims 1
- RUIPRJDRHUEYPK-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[(1-methylsulfonyl-2,3-dihydrobenzimidazol-5-yl)methyl]pyridin-2-one Chemical compound C=1C=C2N(S(=O)(=O)C)CNC2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F RUIPRJDRHUEYPK-UHFFFAOYSA-N 0.000 claims 1
- QPBXINNKFMNRMD-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[(2-methylsulfonyl-3,4-dihydro-1h-isoquinolin-6-yl)methyl]pyridin-2-one Chemical compound C=1C=C2CN(S(=O)(=O)C)CCC2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F QPBXINNKFMNRMD-UHFFFAOYSA-N 0.000 claims 1
- ORFLNKSGORMXJT-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[(3-fluorophenyl)methyl]pyridin-2-one Chemical compound FC1=CC(F)=CC=C1COC1=C(Cl)C(=O)N(CC=2C=C(F)C=CC=2)C=C1 ORFLNKSGORMXJT-UHFFFAOYSA-N 0.000 claims 1
- ZRUONFYXOYGUIB-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[(3-methylsulfonyl-1,2-dihydrobenzimidazol-5-yl)methyl]pyridin-2-one Chemical compound C1=C2N(S(=O)(=O)C)CNC2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F ZRUONFYXOYGUIB-UHFFFAOYSA-N 0.000 claims 1
- OLEWEELJNYYORF-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[(3-methylsulfonylphenyl)methyl]pyridin-2-one Chemical compound CS(=O)(=O)C1=CC=CC(CN2C(C(Cl)=C(OCC=3C(=CC(F)=CC=3)F)C=C2)=O)=C1 OLEWEELJNYYORF-UHFFFAOYSA-N 0.000 claims 1
- HVYNTQVTSGSKHZ-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[1-(2-hydroxy-2-methylpropanoyl)benzimidazol-5-yl]-6-methylpyridin-2-one Chemical compound ClC=1C(=O)N(C=2C=C3N=CN(C3=CC=2)C(=O)C(C)(C)O)C(C)=CC=1OCC1=CC=C(F)C=C1F HVYNTQVTSGSKHZ-UHFFFAOYSA-N 0.000 claims 1
- SOWQJKBIMJISCY-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[1-(2-hydroxyacetyl)-3-methylsulfonyl-2h-benzimidazol-5-yl]-6-methylpyridin-2-one Chemical compound ClC=1C(=O)N(C=2C=C3N(CN(C3=CC=2)C(=O)CO)S(C)(=O)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F SOWQJKBIMJISCY-UHFFFAOYSA-N 0.000 claims 1
- CIBCIPYLGDICRU-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[1-(2-hydroxyacetyl)benzimidazol-5-yl]-6-methylpyridin-2-one Chemical compound ClC=1C(=O)N(C=2C=C3N=CN(C3=CC=2)C(=O)CO)C(C)=CC=1OCC1=CC=C(F)C=C1F CIBCIPYLGDICRU-UHFFFAOYSA-N 0.000 claims 1
- MSMALMFGLYASNH-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[1-(2-hydroxyacetyl)indol-5-yl]-6-methylpyridin-2-one Chemical compound ClC=1C(=O)N(C=2C=C3C=CN(C3=CC=2)C(=O)CO)C(C)=CC=1OCC1=CC=C(F)C=C1F MSMALMFGLYASNH-UHFFFAOYSA-N 0.000 claims 1
- PFHOSYOZZIUHFX-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[1-(3-hydroxy-3-methylbutanoyl)pyrazol-4-yl]-6-methylpyridin-2-one Chemical compound ClC=1C(=O)N(C2=CN(N=C2)C(=O)CC(C)(C)O)C(C)=CC=1OCC1=CC=C(F)C=C1F PFHOSYOZZIUHFX-UHFFFAOYSA-N 0.000 claims 1
- MUKXOYUNHGKZML-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[1-(3-hydroxy-3-methylbutanoyl)pyrrol-3-yl]-6-methylpyridin-2-one Chemical compound ClC=1C(=O)N(C2=CN(C=C2)C(=O)CC(C)(C)O)C(C)=CC=1OCC1=CC=C(F)C=C1F MUKXOYUNHGKZML-UHFFFAOYSA-N 0.000 claims 1
- SWBSXBQNENLBSL-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[1-(3-hydroxypropanoyl)benzimidazol-5-yl]-6-methylpyridin-2-one Chemical compound ClC=1C(=O)N(C=2C=C3N=CN(C3=CC=2)C(=O)CCO)C(C)=CC=1OCC1=CC=C(F)C=C1F SWBSXBQNENLBSL-UHFFFAOYSA-N 0.000 claims 1
- MOZWEOVJEUWMBB-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[1-(3-hydroxypropanoyl)pyrazol-4-yl]-6-methylpyridin-2-one Chemical compound ClC=1C(=O)N(C2=CN(N=C2)C(=O)CCO)C(C)=CC=1OCC1=CC=C(F)C=C1F MOZWEOVJEUWMBB-UHFFFAOYSA-N 0.000 claims 1
- PEOSJTNOLJTLFT-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[2-(2-hydroxy-2-methylpropanoyl)-3,4-dihydro-1h-isoquinolin-6-yl]-6-methylpyridin-2-one Chemical compound ClC=1C(=O)N(C=2C=C3CCN(CC3=CC=2)C(=O)C(C)(C)O)C(C)=CC=1OCC1=CC=C(F)C=C1F PEOSJTNOLJTLFT-UHFFFAOYSA-N 0.000 claims 1
- VQUQGWUSUCGFGQ-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[2-(3-hydroxy-3-methylbutanoyl)-3,4-dihydro-1h-isoquinolin-7-yl]-6-methylpyridin-2-one Chemical compound ClC=1C(=O)N(C=2C=C3CN(CCC3=CC=2)C(=O)CC(C)(C)O)C(C)=CC=1OCC1=CC=C(F)C=C1F VQUQGWUSUCGFGQ-UHFFFAOYSA-N 0.000 claims 1
- MEBQGBOWJHPUIR-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[3-(2-hydroxyacetyl)-1-(2-hydroxy-2-methylpropanoyl)-2h-benzimidazol-5-yl]-6-methylpyridin-2-one Chemical compound ClC=1C(=O)N(C=2C=C3N(C(=O)CO)CN(C3=CC=2)C(=O)C(C)(C)O)C(C)=CC=1OCC1=CC=C(F)C=C1F MEBQGBOWJHPUIR-UHFFFAOYSA-N 0.000 claims 1
- SPOQSWJOEKDCFO-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[3-(3-hydroxy-3-methylbutanoyl)-1-methylsulfonyl-2h-benzimidazol-5-yl]-6-methylpyridin-2-one Chemical compound ClC=1C(=O)N(C=2C=C3N(C(=O)CC(C)(C)O)CN(C3=CC=2)S(C)(=O)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F SPOQSWJOEKDCFO-UHFFFAOYSA-N 0.000 claims 1
- PUDJOBIRRYTVMG-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[3-(3-hydroxypropanoyl)-1-methylsulfonyl-2h-benzimidazol-5-yl]-6-methylpyridin-2-one Chemical compound ClC=1C(=O)N(C=2C=C3N(C(=O)CCO)CN(C3=CC=2)S(C)(=O)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F PUDJOBIRRYTVMG-UHFFFAOYSA-N 0.000 claims 1
- XBYMYXPIISEPBE-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[[1-(2-hydroxy-2-methylpropanoyl)-2,3-dihydrobenzimidazol-5-yl]methyl]pyridin-2-one Chemical compound C=1C=C2N(C(=O)C(C)(O)C)CNC2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F XBYMYXPIISEPBE-UHFFFAOYSA-N 0.000 claims 1
- VLXUGBNCLUOOQR-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[[1-(2-hydroxy-2-methylpropanoyl)-3-methylsulfonyl-2h-benzimidazol-5-yl]methyl]pyridin-2-one Chemical compound C=1C=C2N(C(=O)C(C)(O)C)CN(S(C)(=O)=O)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F VLXUGBNCLUOOQR-UHFFFAOYSA-N 0.000 claims 1
- XZSXBDMOPPGNKT-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[[1-(2-hydroxyacetyl)-3-methylsulfonyl-2h-benzimidazol-5-yl]methyl]pyridin-2-one Chemical compound C1=C2N(S(=O)(=O)C)CN(C(=O)CO)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F XZSXBDMOPPGNKT-UHFFFAOYSA-N 0.000 claims 1
- PBFFOCGEPBFKPG-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[[1-(3-hydroxy-3-methylbutanoyl)-3-methylsulfonyl-2h-benzimidazol-5-yl]methyl]pyridin-2-one Chemical compound C=1C=C2N(C(=O)CC(C)(O)C)CN(S(C)(=O)=O)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F PBFFOCGEPBFKPG-UHFFFAOYSA-N 0.000 claims 1
- NBFUQEBHSRHQMH-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[[1-(3-hydroxypropanoyl)-3-methylsulfonyl-2h-benzimidazol-5-yl]methyl]pyridin-2-one Chemical compound C1=C2N(S(=O)(=O)C)CN(C(=O)CCO)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F NBFUQEBHSRHQMH-UHFFFAOYSA-N 0.000 claims 1
- SVYXWSNETFAZFN-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[[2-(2-hydroxy-2-methylpropanoyl)-3,4-dihydro-1h-isoquinolin-6-yl]methyl]pyridin-2-one Chemical compound C=1C=C2CN(C(=O)C(C)(O)C)CCC2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F SVYXWSNETFAZFN-UHFFFAOYSA-N 0.000 claims 1
- ZFDLVVJOMMDKAN-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[[2-(3-hydroxy-3-methylbutanoyl)-3,4-dihydro-1h-isoquinolin-6-yl]methyl]pyridin-2-one Chemical compound C=1C=C2CN(C(=O)CC(C)(O)C)CCC2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F ZFDLVVJOMMDKAN-UHFFFAOYSA-N 0.000 claims 1
- BDIOSYCLYXARIO-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[[2-(3-hydroxypropanoyl)-3,4-dihydro-1h-isoquinolin-5-yl]methyl]pyridin-2-one Chemical compound C1=CC=C2CN(C(=O)CCO)CCC2=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F BDIOSYCLYXARIO-UHFFFAOYSA-N 0.000 claims 1
- UQLZALOXKUVYDS-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[[2-(3-hydroxypropanoyl)-3,4-dihydro-1h-isoquinolin-6-yl]methyl]pyridin-2-one Chemical compound C=1C=C2CN(C(=O)CCO)CCC2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F UQLZALOXKUVYDS-UHFFFAOYSA-N 0.000 claims 1
- ALIDOSNJZCVAHE-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[[3-(3-hydroxy-3-methylbutanoyl)-1-(2-hydroxy-2-methylpropanoyl)-2h-benzimidazol-5-yl]methyl]pyridin-2-one Chemical compound C1=C2N(C(=O)CC(C)(O)C)CN(C(=O)C(C)(C)O)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F ALIDOSNJZCVAHE-UHFFFAOYSA-N 0.000 claims 1
- BOLABAFDRSTQKC-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[[3-(3-hydroxy-3-methylbutanoyl)-1-(3-hydroxypropanoyl)-2h-benzimidazol-5-yl]methyl]pyridin-2-one Chemical compound C1=C2N(C(=O)CC(C)(O)C)CN(C(=O)CCO)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F BOLABAFDRSTQKC-UHFFFAOYSA-N 0.000 claims 1
- KPIQUZSWYPVHLD-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[[4-[(propan-2-ylamino)methyl]phenyl]methyl]pyridin-2-one Chemical compound C1=CC(CNC(C)C)=CC=C1CN1C(=O)C(Cl)=C(OCC=2C(=CC(F)=CC=2)F)C=C1 KPIQUZSWYPVHLD-UHFFFAOYSA-N 0.000 claims 1
- ZPCPVLQTRFRVPM-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[[5-(hydroxymethyl)pyrazin-2-yl]methyl]-6-methylpyridin-2-one Chemical compound ClC=1C(=O)N(CC=2N=CC(CO)=NC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F ZPCPVLQTRFRVPM-UHFFFAOYSA-N 0.000 claims 1
- CBKWTULSSMLSLR-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-6-(hydroxymethyl)-1-(2,4,6-trifluorophenyl)pyridin-2-one Chemical compound ClC=1C(=O)N(C=2C(=CC(F)=CC=2F)F)C(CO)=CC=1OCC1=CC=C(F)C=C1F CBKWTULSSMLSLR-UHFFFAOYSA-N 0.000 claims 1
- SXTHUFBQBPCVLS-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-(2-methylsulfonyl-1,3-dihydroisoindol-5-yl)pyridin-2-one Chemical compound ClC=1C(=O)N(C=2C=C3CN(CC3=CC=2)S(C)(=O)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F SXTHUFBQBPCVLS-UHFFFAOYSA-N 0.000 claims 1
- PZYZPNXSBWNPBB-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[(5-methylpyrazin-2-yl)methyl]pyridin-2-one Chemical compound C1=NC(C)=CN=C1CN1C(=O)C(Cl)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C PZYZPNXSBWNPBB-UHFFFAOYSA-N 0.000 claims 1
- KDLWNYZRJLQAKM-UHFFFAOYSA-N 3-ethynyl-1-[(3-fluorophenyl)methyl]-4-phenylmethoxypyridin-2-one Chemical compound FC1=CC=CC(CN2C(C(C#C)=C(OCC=3C=CC=CC=3)C=C2)=O)=C1 KDLWNYZRJLQAKM-UHFFFAOYSA-N 0.000 claims 1
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims 1
- ZCIPCHJTWHQTQK-UHFFFAOYSA-N 3-methyl-4-phenylmethoxy-1h-pyridin-2-one Chemical compound C1=CNC(=O)C(C)=C1OCC1=CC=CC=C1 ZCIPCHJTWHQTQK-UHFFFAOYSA-N 0.000 claims 1
- ALZCZOWYDIAIML-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-3-bromo-1-[(3-fluorophenyl)methyl]pyridin-2-one Chemical compound FC1=CC=CC(CN2C(C(Br)=C(C=C2)C=2C=C3OCOC3=CC=2)=O)=C1 ALZCZOWYDIAIML-UHFFFAOYSA-N 0.000 claims 1
- DDCPGFSLXJOUMP-UHFFFAOYSA-N 4-(benzylamino)-3-bromo-1-(2,6-difluorophenyl)-5-iodo-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(C=2C(=CC=CC=2F)F)C(C)=C(I)C=1NCC1=CC=CC=C1 DDCPGFSLXJOUMP-UHFFFAOYSA-N 0.000 claims 1
- JPKOUXZOOCGXJI-UHFFFAOYSA-N 4-[(2,4-difluorophenyl)methoxy]-1-[(3-fluorophenyl)methyl]-2-oxopyridine-3-carbonitrile Chemical compound FC1=CC(F)=CC=C1COC1=C(C#N)C(=O)N(CC=2C=C(F)C=CC=2)C=C1 JPKOUXZOOCGXJI-UHFFFAOYSA-N 0.000 claims 1
- IPYOKKYLHBAIJM-UHFFFAOYSA-N 4-[(2,4-difluorophenyl)methoxy]-1-[(3-fluorophenyl)methyl]-3-iodopyridin-2-one Chemical compound FC1=CC(F)=CC=C1COC1=C(I)C(=O)N(CC=2C=C(F)C=CC=2)C=C1 IPYOKKYLHBAIJM-UHFFFAOYSA-N 0.000 claims 1
- WJQHVDALFUOTDG-UHFFFAOYSA-N 4-[(2,4-difluorophenyl)methoxy]-6-(hydroxymethyl)-1-(pyridin-3-ylmethyl)pyridin-2-one Chemical compound C=1C(=O)N(CC=2C=NC=CC=2)C(CO)=CC=1OCC1=CC=C(F)C=C1F WJQHVDALFUOTDG-UHFFFAOYSA-N 0.000 claims 1
- IHUBCGSHNPNUAT-UHFFFAOYSA-N 4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-(2,4,6-trifluorophenyl)pyridin-2-one Chemical compound C=1C(=O)N(C=2C(=CC(F)=CC=2F)F)C(C)=CC=1OCC1=CC=C(F)C=C1F IHUBCGSHNPNUAT-UHFFFAOYSA-N 0.000 claims 1
- BJEBDXLHEYRRAC-UHFFFAOYSA-N 4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-prop-2-ynylpyridin-2-one Chemical compound O=C1N(CC#C)C(C)=CC(OCC=2C(=CC(F)=CC=2)F)=C1 BJEBDXLHEYRRAC-UHFFFAOYSA-N 0.000 claims 1
- FUVNFEODLQDYGC-UHFFFAOYSA-N 4-[(3-bromo-2-oxo-4-phenylmethoxypyridin-1-yl)methyl]-n'-hydroxybenzenecarboximidamide Chemical compound C1=CC(C(=N)NO)=CC=C1CN1C(=O)C(Br)=C(OCC=2C=CC=CC=2)C=C1 FUVNFEODLQDYGC-UHFFFAOYSA-N 0.000 claims 1
- XUSWSJKJBCFERE-UHFFFAOYSA-N 4-[(3-bromo-2-oxo-4-phenylmethoxypyridin-1-yl)methyl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1CN1C(=O)C(Br)=C(OCC=2C=CC=CC=2)C=C1 XUSWSJKJBCFERE-UHFFFAOYSA-N 0.000 claims 1
- YSCLHNVWEJBYIL-UHFFFAOYSA-N 4-[(4-fluorophenyl)methoxy]-1-[(3-fluorophenyl)methyl]-3-methylpyridin-2-one Chemical compound C1=CN(CC=2C=C(F)C=CC=2)C(=O)C(C)=C1OCC1=CC=C(F)C=C1 YSCLHNVWEJBYIL-UHFFFAOYSA-N 0.000 claims 1
- ZOIWWTMGMDUHIB-UHFFFAOYSA-N 4-[(4-fluorophenyl)methoxy]-1-[(4-fluorophenyl)methyl]pyridin-2-one Chemical compound C1=CC(F)=CC=C1COC1=CC(=O)N(CC=2C=CC(F)=CC=2)C=C1 ZOIWWTMGMDUHIB-UHFFFAOYSA-N 0.000 claims 1
- UGNGRMLPJRLXSZ-UHFFFAOYSA-N 4-[3-amino-1-(2,4-difluorophenyl)propoxy]-3-bromo-6-methyl-1-(pyridin-3-ylmethyl)pyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=NC=CC=2)C(C)=CC=1OC(CCN)C1=CC=C(F)C=C1F UGNGRMLPJRLXSZ-UHFFFAOYSA-N 0.000 claims 1
- RDZHPBXLNCQMMD-UHFFFAOYSA-N 4-[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]benzoic acid Chemical compound BrC=1C(=O)N(C=2C=CC(=CC=2)C(O)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F RDZHPBXLNCQMMD-UHFFFAOYSA-N 0.000 claims 1
- YQQQPHHFMSPUAW-UHFFFAOYSA-N 4-[4-[(2,4-difluorophenyl)methoxy]-2-methyl-6-oxopyridin-1-yl]-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1N1C(=O)C=C(OCC=2C(=CC(F)=CC=2)F)C=C1C YQQQPHHFMSPUAW-UHFFFAOYSA-N 0.000 claims 1
- LNRJPUUZXMLUGR-UHFFFAOYSA-N 4-[[2-(aminomethyl)-4-fluorophenyl]methoxy]-3-bromo-1-(2,6-difluorophenyl)-6-methylpyridin-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.BrC=1C(=O)N(C=2C(=CC=CC=2F)F)C(C)=CC=1OCC1=CC=C(F)C=C1CN LNRJPUUZXMLUGR-UHFFFAOYSA-N 0.000 claims 1
- UVDFQEJCBXJWMA-UHFFFAOYSA-N 4-[[3-bromo-1-[(3-fluorophenyl)methyl]-2-oxopyridin-4-yl]oxymethyl]benzonitrile Chemical compound FC1=CC=CC(CN2C(C(Br)=C(OCC=3C=CC(=CC=3)C#N)C=C2)=O)=C1 UVDFQEJCBXJWMA-UHFFFAOYSA-N 0.000 claims 1
- RFOHLLROMHBLCG-UHFFFAOYSA-N 4-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1 RFOHLLROMHBLCG-UHFFFAOYSA-N 0.000 claims 1
- CCYTWXVZAMGVTG-UHFFFAOYSA-N 4-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]-n,n-bis(2-hydroxyethyl)benzamide Chemical compound BrC=1C(=O)N(CC=2C=CC(=CC=2)C(=O)N(CCO)CCO)C(C)=CC=1OCC1=CC=C(F)C=C1F CCYTWXVZAMGVTG-UHFFFAOYSA-N 0.000 claims 1
- KEPLONZHLUBUHL-UHFFFAOYSA-N 4-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C KEPLONZHLUBUHL-UHFFFAOYSA-N 0.000 claims 1
- GQPCOGSNBSWCDX-UHFFFAOYSA-N 4-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]-n-(2-hydroxyethyl)-n-methylbenzamide Chemical compound C1=CC(C(=O)N(CCO)C)=CC=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C GQPCOGSNBSWCDX-UHFFFAOYSA-N 0.000 claims 1
- HVUPCGDITCGWTG-UHFFFAOYSA-N 4-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]-n-(2-hydroxyethyl)benzamide Chemical compound BrC=1C(=O)N(CC=2C=CC(=CC=2)C(=O)NCCO)C(C)=CC=1OCC1=CC=C(F)C=C1F HVUPCGDITCGWTG-UHFFFAOYSA-N 0.000 claims 1
- YRUFBXUWPCXWPD-UHFFFAOYSA-N 4-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]-n-(2-methoxyethyl)benzamide Chemical compound C1=CC(C(=O)NCCOC)=CC=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C YRUFBXUWPCXWPD-UHFFFAOYSA-N 0.000 claims 1
- KUMQZNRIVRBPOU-UHFFFAOYSA-N 4-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]-n-hydroxybenzamide Chemical compound BrC=1C(=O)N(CC=2C=CC(=CC=2)C(=O)NO)C(C)=CC=1OCC1=CC=C(F)C=C1F KUMQZNRIVRBPOU-UHFFFAOYSA-N 0.000 claims 1
- JIWODETXTHEHSL-UHFFFAOYSA-N 4-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]-n-propan-2-ylbenzamide Chemical compound C1=CC(C(=O)NC(C)C)=CC=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C JIWODETXTHEHSL-UHFFFAOYSA-N 0.000 claims 1
- PHGFIDCHPGXZAU-UHFFFAOYSA-N 4-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]benzamide Chemical compound BrC=1C(=O)N(CC=2C=CC(=CC=2)C(N)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F PHGFIDCHPGXZAU-UHFFFAOYSA-N 0.000 claims 1
- SOAHDRVTQWAHKR-UHFFFAOYSA-N 4-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]benzoic acid Chemical compound BrC=1C(=O)N(CC=2C=CC(=CC=2)C(O)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F SOAHDRVTQWAHKR-UHFFFAOYSA-N 0.000 claims 1
- IJXNDQYOHDEKFE-UHFFFAOYSA-N 4-[[3-bromo-4-[(4-fluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]benzonitrile Chemical compound C1=CC(F)=CC=C1COC1=C(Br)C(=O)N(CC=2C=CC(=CC=2)C#N)C=C1 IJXNDQYOHDEKFE-UHFFFAOYSA-N 0.000 claims 1
- LZQQXWGNGILECB-UHFFFAOYSA-N 4-chloro-3-[3-chloro-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]-N-methylbenzamide 3-[3-chloro-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]-4-fluorobenzamide Chemical compound Cc1cc(OCc2ccc(F)cc2F)c(Cl)c(=O)n1-c1cc(ccc1F)C(N)=O.CNC(=O)c1ccc(Cl)c(c1)-n1c(C)cc(OCc2ccc(F)cc2F)c(Cl)c1=O LZQQXWGNGILECB-UHFFFAOYSA-N 0.000 claims 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- ZVABDPNQEHMTGA-UHFFFAOYSA-N 4-phenoxy-1h-pyridin-2-one Chemical compound C1=CNC(=O)C=C1OC1=CC=CC=C1 ZVABDPNQEHMTGA-UHFFFAOYSA-N 0.000 claims 1
- QYWHWHBNZILDDP-UHFFFAOYSA-N 4-phenylmethoxy-1-[[4-(trifluoromethyl)phenyl]methyl]pyridin-2-one Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1C(=O)C=C(OCC=2C=CC=CC=2)C=C1 QYWHWHBNZILDDP-UHFFFAOYSA-N 0.000 claims 1
- DOVNUEPFPBWTSV-UHFFFAOYSA-N 4-phenylmethoxy-1h-pyridin-2-one Chemical compound C1=CNC(=O)C=C1OCC1=CC=CC=C1 DOVNUEPFPBWTSV-UHFFFAOYSA-N 0.000 claims 1
- NEDODNWPAUBXFZ-UHFFFAOYSA-N 5-[3-chloro-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]-2,3-dihydroindole-1-carboxamide Chemical compound ClC=1C(=O)N(C=2C=C3CCN(C3=CC=2)C(N)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F NEDODNWPAUBXFZ-UHFFFAOYSA-N 0.000 claims 1
- JAXCVAHZECOKSS-UHFFFAOYSA-N 5-[3-chloro-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]-2h-benzimidazole-1,3-dicarboxamide Chemical compound ClC=1C(=O)N(C=2C=C3N(C(N)=O)CN(C3=CC=2)C(N)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F JAXCVAHZECOKSS-UHFFFAOYSA-N 0.000 claims 1
- MSHANTMGWWINOE-UHFFFAOYSA-N 5-[4-(3-chlorophenyl)piperazine-1-carbonyl]-1-[(3,4-dichlorophenyl)methyl]pyridin-2-one Chemical compound ClC1=CC=CC(N2CCN(CC2)C(=O)C2=CN(CC=3C=C(Cl)C(Cl)=CC=3)C(=O)C=C2)=C1 MSHANTMGWWINOE-UHFFFAOYSA-N 0.000 claims 1
- VJQHCICDPQRLQX-UHFFFAOYSA-N 5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC(F)=CC=C1COC1=C(Cl)C(=O)N(CC=2C=C3NC(=O)NC3=CC=2)C=C1 VJQHCICDPQRLQX-UHFFFAOYSA-N 0.000 claims 1
- QWIDSENEVMTGPE-UHFFFAOYSA-N 5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-1,3-dihydroindol-2-one Chemical compound FC1=CC(F)=CC=C1COC1=C(Cl)C(=O)N(CC=2C=C3CC(=O)NC3=CC=2)C=C1 QWIDSENEVMTGPE-UHFFFAOYSA-N 0.000 claims 1
- YSWYCRFQHVRODE-UHFFFAOYSA-N 5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-2-oxobenzimidazole-1,3-dicarboxamide Chemical compound C1=C2N(C(N)=O)C(=O)N(C(=O)N)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F YSWYCRFQHVRODE-UHFFFAOYSA-N 0.000 claims 1
- LFOSXZHPFHUPOS-UHFFFAOYSA-N 5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-2h-benzimidazole-1,3-dicarboxamide Chemical compound C=1C=C2N(C(=O)N)CN(C(N)=O)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F LFOSXZHPFHUPOS-UHFFFAOYSA-N 0.000 claims 1
- YTYOWNWVMCDEHQ-UHFFFAOYSA-N 5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-(3-hydroxy-3-methylbutanoyl)-1-(2-hydroxy-2-methylpropanoyl)benzimidazol-2-one Chemical compound C=1C=C2N(C(=O)C(C)(C)O)C(=O)N(C(=O)CC(C)(O)C)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F YTYOWNWVMCDEHQ-UHFFFAOYSA-N 0.000 claims 1
- KERNJHABIVROAM-UHFFFAOYSA-N 5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-(3-hydroxy-3-methylbutanoyl)-1-(3-hydroxypropanoyl)benzimidazol-2-one Chemical compound C=1C=C2N(C(=O)CCO)C(=O)N(C(=O)CC(C)(O)C)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F KERNJHABIVROAM-UHFFFAOYSA-N 0.000 claims 1
- JNQCDIQZBGYVEM-UHFFFAOYSA-N 5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-(3-hydroxy-3-methylbutanoyl)-1-methylsulfonylbenzimidazol-2-one Chemical compound C=1C=C2N(S(C)(=O)=O)C(=O)N(C(=O)CC(C)(O)C)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F JNQCDIQZBGYVEM-UHFFFAOYSA-N 0.000 claims 1
- AKRXQEFZYCXAGL-UHFFFAOYSA-N 5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-(3-hydroxy-3-methylbutanoyl)-1h-benzimidazol-2-one Chemical compound C=1C=C2NC(=O)N(C(=O)CC(C)(O)C)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F AKRXQEFZYCXAGL-UHFFFAOYSA-N 0.000 claims 1
- JLBRQWBDTKOIIV-UHFFFAOYSA-N 5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-(3-hydroxy-3-methylbutanoyl)-2-oxobenzimidazole-1-carboxamide Chemical compound C=1C=C2N(C(N)=O)C(=O)N(C(=O)CC(C)(O)C)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F JLBRQWBDTKOIIV-UHFFFAOYSA-N 0.000 claims 1
- AEGHAPRRSUEIQU-UHFFFAOYSA-N 5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-(3-hydroxypropanoyl)-2h-benzimidazole-1-carboxamide Chemical compound C=1C=C2N(C(=O)N)CN(C(=O)CCO)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F AEGHAPRRSUEIQU-UHFFFAOYSA-N 0.000 claims 1
- BDXQAFBGNSNARV-UHFFFAOYSA-N 5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-methylsulfonyl-1h-benzimidazol-2-one Chemical compound C=1C=C2NC(=O)N(S(=O)(=O)C)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F BDXQAFBGNSNARV-UHFFFAOYSA-N 0.000 claims 1
- YDRVOXILPORTAK-UHFFFAOYSA-N 5-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-methylsulfonyl-2h-benzimidazole-1-carboxamide Chemical compound C1=C2N(S(=O)(=O)C)CN(C(N)=O)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F YDRVOXILPORTAK-UHFFFAOYSA-N 0.000 claims 1
- WBEPWFNEOJBNJX-UHFFFAOYSA-N 5-bromo-1-(2,6-difluorophenyl)-2-[2-(2,4-difluorophenyl)ethyl]-4-[(2,4-difluorophenyl)methoxy]-6-oxopyridine-3-carbaldehyde Chemical compound FC1=CC(F)=CC=C1CCC1=C(C=O)C(OCC=2C(=CC(F)=CC=2)F)=C(Br)C(=O)N1C1=C(F)C=CC=C1F WBEPWFNEOJBNJX-UHFFFAOYSA-N 0.000 claims 1
- FTJSPMAXTZOMIY-UHFFFAOYSA-N 5-bromo-1-(2,6-difluorophenyl)-4-[(2,4-difluorophenyl)methoxy]-6-oxopyridine-2-carbaldehyde Chemical compound FC1=CC(F)=CC=C1COC1=C(Br)C(=O)N(C=2C(=CC=CC=2F)F)C(C=O)=C1 FTJSPMAXTZOMIY-UHFFFAOYSA-N 0.000 claims 1
- SXWDWSQMOZDMFF-UHFFFAOYSA-N 5-bromo-1-(2,6-difluorophenyl)-4-[(2,4-difluorophenyl)methoxy]-6-oxopyridine-2-carboxylic acid Chemical compound BrC=1C(=O)N(C=2C(=CC=CC=2F)F)C(C(=O)O)=CC=1OCC1=CC=C(F)C=C1F SXWDWSQMOZDMFF-UHFFFAOYSA-N 0.000 claims 1
- NIBXLYZABNCOHJ-UHFFFAOYSA-N 5-chloro-1-[(2,6-dichlorophenyl)methyl]-6-oxo-n-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)C2=CN(CC=3C(=CC=CC=3Cl)Cl)C(=O)C(Cl)=C2)=C1 NIBXLYZABNCOHJ-UHFFFAOYSA-N 0.000 claims 1
- HXMOZYJVVBFMGP-UHFFFAOYSA-N 5-chloro-1-[(2,6-dichlorophenyl)methyl]-n-(2,4-difluorophenyl)-6-oxopyridine-3-carboxamide Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CN(CC=2C(=CC=CC=2Cl)Cl)C(=O)C(Cl)=C1 HXMOZYJVVBFMGP-UHFFFAOYSA-N 0.000 claims 1
- ARGQRQILNLOQOL-UHFFFAOYSA-N 5-chloro-1-[(2,6-dichlorophenyl)methyl]-n-methyl-6-oxo-n-phenylpyridine-3-carboxamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C(=C1)C=C(Cl)C(=O)N1CC1=C(Cl)C=CC=C1Cl ARGQRQILNLOQOL-UHFFFAOYSA-N 0.000 claims 1
- NXBRNUAFTAXPTO-UHFFFAOYSA-N 6-[3-bromo-4-(5-carboxypyridin-2-yl)oxy-6-methyl-2-oxopyridin-1-yl]pyridine-3-carboxylic acid Chemical compound BrC=1C(=O)N(C=2N=CC(=CC=2)C(O)=O)C(C)=CC=1OC1=CC=C(C(O)=O)C=N1 NXBRNUAFTAXPTO-UHFFFAOYSA-N 0.000 claims 1
- NAJLWJHVAWSHDO-UHFFFAOYSA-N 6-[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]-n-(2-hydroxyethyl)pyridine-3-carboxamide Chemical compound BrC=1C(=O)N(C=2N=CC(=CC=2)C(=O)NCCO)C(C)=CC=1OCC1=CC=C(F)C=C1F NAJLWJHVAWSHDO-UHFFFAOYSA-N 0.000 claims 1
- KHCQLJLTTFFVTP-UHFFFAOYSA-N 6-[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]-n-(2-methoxyethyl)pyridine-3-carboxamide Chemical compound N1=CC(C(=O)NCCOC)=CC=C1N1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C KHCQLJLTTFFVTP-UHFFFAOYSA-N 0.000 claims 1
- PPPARADQKVWOOR-UHFFFAOYSA-N 6-[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]pyridine-3-carboxylic acid Chemical compound BrC=1C(=O)N(C=2N=CC(=CC=2)C(O)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F PPPARADQKVWOOR-UHFFFAOYSA-N 0.000 claims 1
- IHTPDZPGRWZDGO-UHFFFAOYSA-N 6-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-2,3-dihydrobenzimidazole-1-carboxamide Chemical compound C1=C2N(C(=O)N)CNC2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F IHTPDZPGRWZDGO-UHFFFAOYSA-N 0.000 claims 1
- ATXKEXVPLDSUSS-UHFFFAOYSA-N 6-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-(2-hydroxy-2-methylpropanoyl)-1h-benzimidazol-2-one Chemical compound C1=C2NC(=O)N(C(=O)C(C)(O)C)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F ATXKEXVPLDSUSS-UHFFFAOYSA-N 0.000 claims 1
- FZNBMXQBNPJZOB-UHFFFAOYSA-N 6-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-(2-hydroxy-2-methylpropanoyl)-2-oxobenzimidazole-1-carboxamide Chemical compound C1=C2N(C(N)=O)C(=O)N(C(=O)C(C)(O)C)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F FZNBMXQBNPJZOB-UHFFFAOYSA-N 0.000 claims 1
- NSEQBICQNCRMDI-UHFFFAOYSA-N 6-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-(2-hydroxyacetyl)-1h-benzimidazol-2-one Chemical compound C1=C2NC(=O)N(C(=O)CO)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F NSEQBICQNCRMDI-UHFFFAOYSA-N 0.000 claims 1
- PWZXIXRCCLAFEU-UHFFFAOYSA-N 6-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-(2-hydroxyacetyl)-2-oxobenzimidazole-1-carboxamide Chemical compound C=1C=C2N(C(=O)CO)C(=O)N(C(=O)N)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F PWZXIXRCCLAFEU-UHFFFAOYSA-N 0.000 claims 1
- FKWLNTCWNWXTPZ-UHFFFAOYSA-N 6-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-(2-hydroxyacetyl)-2h-benzimidazole-1-carboxamide Chemical compound C1=C2N(C(=O)N)CN(C(=O)CO)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F FKWLNTCWNWXTPZ-UHFFFAOYSA-N 0.000 claims 1
- DQLRPVNEEFPFFF-UHFFFAOYSA-N 6-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-(3-hydroxy-3-methylbutanoyl)-2-oxobenzimidazole-1-carboxamide Chemical compound C1=C2N(C(N)=O)C(=O)N(C(=O)CC(C)(O)C)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F DQLRPVNEEFPFFF-UHFFFAOYSA-N 0.000 claims 1
- KDFFPEGKNJSUHJ-UHFFFAOYSA-N 6-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-(3-hydroxy-3-methylbutanoyl)-2h-benzimidazole-1-carboxamide Chemical compound C=1C=C2N(C(=O)CC(C)(O)C)CN(C(N)=O)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F KDFFPEGKNJSUHJ-UHFFFAOYSA-N 0.000 claims 1
- GEKSGAOTKPZVMU-UHFFFAOYSA-N 6-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-(3-hydroxypropanoyl)-2-oxobenzimidazole-1-carboxamide Chemical compound C=1C=C2N(C(=O)CCO)C(=O)N(C(=O)N)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F GEKSGAOTKPZVMU-UHFFFAOYSA-N 0.000 claims 1
- JFPREYGAMMLIQP-UHFFFAOYSA-N 6-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-(3-hydroxypropanoyl)-2h-benzimidazole-1-carboxamide Chemical compound C1=C2N(C(=O)N)CN(C(=O)CCO)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F JFPREYGAMMLIQP-UHFFFAOYSA-N 0.000 claims 1
- NYJQOWMRHVVTQB-UHFFFAOYSA-N 6-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-methylsulfonyl-1h-benzimidazol-2-one Chemical compound C1=C2NC(=O)N(S(=O)(=O)C)C2=CC=C1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F NYJQOWMRHVVTQB-UHFFFAOYSA-N 0.000 claims 1
- MWYDBBAXHQIQHU-UHFFFAOYSA-N 6-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-3-methylsulfonyl-2h-benzimidazole-1-carboxamide Chemical compound C=1C=C2N(S(=O)(=O)C)CN(C(N)=O)C2=CC=1CN(C(C=1Cl)=O)C=CC=1OCC1=CC=C(F)C=C1F MWYDBBAXHQIQHU-UHFFFAOYSA-N 0.000 claims 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims 1
- XMIHBKAXOKZUMD-UHFFFAOYSA-N BrC=1C(N(C=CC1OCC1=C(C=C(C=C1)F)F)CC=1C=C2CCNC2=CC1)=O.ClC=1C(N(C(=CC1OCC1=C(C=C(C=C1)F)F)C)CC1=NC=C(N=C1)CO)=O Chemical compound BrC=1C(N(C=CC1OCC1=C(C=C(C=C1)F)F)CC=1C=C2CCNC2=CC1)=O.ClC=1C(N(C(=CC1OCC1=C(C=C(C=C1)F)F)C)CC1=NC=C(N=C1)CO)=O XMIHBKAXOKZUMD-UHFFFAOYSA-N 0.000 claims 1
- PDKBMTGXJNKXPO-UHFFFAOYSA-N ClC=1C(N(C(=CC1OCC1=C(C=C(C=C1)F)F)C)C1=C(C=C(C=C1)C(CO)O)C)=O.ClC=1C(N(C(=CC1OCC1=C(C=C(C=C1)F)F)C)C1=C(C=C(C(=O)NC)C=C1)C)=O Chemical compound ClC=1C(N(C(=CC1OCC1=C(C=C(C=C1)F)F)C)C1=C(C=C(C=C1)C(CO)O)C)=O.ClC=1C(N(C(=CC1OCC1=C(C=C(C=C1)F)F)C)C1=C(C=C(C(=O)NC)C=C1)C)=O PDKBMTGXJNKXPO-UHFFFAOYSA-N 0.000 claims 1
- ARYCPHXSMFACLY-UHFFFAOYSA-N ClC=1C(N(C(=CC1OCC1=C(C=C(C=C1)F)F)C)C=1C=C(C(=O)NC)C=CC1C)=O.BrC=1C(N(C(=CC1OCC1=C(C=C(C=C1)F)F)C)CC1=NNC=C1)=O Chemical compound ClC=1C(N(C(=CC1OCC1=C(C=C(C=C1)F)F)C)C=1C=C(C(=O)NC)C=CC1C)=O.BrC=1C(N(C(=CC1OCC1=C(C=C(C=C1)F)F)C)CC1=NNC=C1)=O ARYCPHXSMFACLY-UHFFFAOYSA-N 0.000 claims 1
- 102000000503 Collagen Type II Human genes 0.000 claims 1
- 108010041390 Collagen Type II Proteins 0.000 claims 1
- 208000009386 Experimental Arthritis Diseases 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- 206010023198 Joint ankylosis Diseases 0.000 claims 1
- 241000699666 Mus <mouse, genus> Species 0.000 claims 1
- 241000699670 Mus sp. Species 0.000 claims 1
- DJUBBMOIHKWZCE-UHFFFAOYSA-N [5-bromo-1-(2,6-difluorophenyl)-4-[(2,4-difluorophenyl)methoxy]-2-methyl-6-oxopyridin-3-yl]methyl carbamate Chemical compound BrC=1C(=O)N(C=2C(=CC=CC=2F)F)C(C)=C(COC(N)=O)C=1OCC1=CC=C(F)C=C1F DJUBBMOIHKWZCE-UHFFFAOYSA-N 0.000 claims 1
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 claims 1
- INGJGMLGVYESBF-UHFFFAOYSA-N benzyl 2-(5-nitro-2,4-dioxo-1h-pyrimidin-3-yl)acetate Chemical compound O=C1C([N+](=O)[O-])=CNC(=O)N1CC(=O)OCC1=CC=CC=C1 INGJGMLGVYESBF-UHFFFAOYSA-N 0.000 claims 1
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 claims 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-M crotonate Chemical compound C\C=C\C([O-])=O LDHQCZJRKDOVOX-NSCUHMNNSA-M 0.000 claims 1
- 125000006287 difluorobenzyl group Chemical group 0.000 claims 1
- NQBNFFMGTBCCSQ-UHFFFAOYSA-N ethyl 2-(3-bromo-2-oxo-4-phenylmethoxypyridin-1-yl)acetate Chemical compound O=C1N(CC(=O)OCC)C=CC(OCC=2C=CC=CC=2)=C1Br NQBNFFMGTBCCSQ-UHFFFAOYSA-N 0.000 claims 1
- LYJNGYVQVFIIOC-UHFFFAOYSA-N ethyl 2-[3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]phenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC(CN2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2)=O)=C1 LYJNGYVQVFIIOC-UHFFFAOYSA-N 0.000 claims 1
- GXCCVVXOUZMSLF-UHFFFAOYSA-N ethyl n-[[2-[[3-bromo-1-(2,6-difluorophenyl)-6-methyl-2-oxopyridin-4-yl]oxymethyl]-5-fluorophenyl]methyl]carbamate Chemical compound CCOC(=O)NCC1=CC(F)=CC=C1COC1=C(Br)C(=O)N(C=2C(=CC=CC=2F)F)C(C)=C1 GXCCVVXOUZMSLF-UHFFFAOYSA-N 0.000 claims 1
- 230000002068 genetic effect Effects 0.000 claims 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims 1
- ZCILFMOQBYTARB-UHFFFAOYSA-N methyl 3-[(3-bromo-2-oxo-4-phenylmethoxypyridin-1-yl)methyl]benzoate Chemical compound COC(=O)C1=CC=CC(CN2C(C(Br)=C(OCC=3C=CC=CC=3)C=C2)=O)=C1 ZCILFMOQBYTARB-UHFFFAOYSA-N 0.000 claims 1
- XELNYLBCIGPEDD-UHFFFAOYSA-N methyl 3-[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]benzoate Chemical compound COC(=O)C1=CC=CC(N2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 XELNYLBCIGPEDD-UHFFFAOYSA-N 0.000 claims 1
- RLKOUSNTHXWJRJ-UHFFFAOYSA-N methyl 3-[4-[(2,4-difluorophenyl)methoxy]-2-methyl-6-oxopyridin-1-yl]benzoate Chemical compound COC(=O)C1=CC=CC(N2C(C=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 RLKOUSNTHXWJRJ-UHFFFAOYSA-N 0.000 claims 1
- NWISOJWOWODBPX-UHFFFAOYSA-N methyl 3-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]-2-fluorobenzoate Chemical compound COC(=O)C1=CC=CC(CN2C(C(Cl)=C(OCC=3C(=CC(F)=CC=3)F)C=C2)=O)=C1F NWISOJWOWODBPX-UHFFFAOYSA-N 0.000 claims 1
- ULKLCFUAMMUPIA-UHFFFAOYSA-N methyl 3-chloro-4-[4-[(2,4-difluorophenyl)methoxy]-2-methyl-6-oxopyridin-1-yl]benzoate Chemical compound ClC1=CC(C(=O)OC)=CC=C1N1C(=O)C=C(OCC=2C(=CC(F)=CC=2)F)C=C1C ULKLCFUAMMUPIA-UHFFFAOYSA-N 0.000 claims 1
- VAFPWSDXIBPWPS-UHFFFAOYSA-N methyl 4-[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]-3-chlorobenzoate Chemical compound ClC1=CC(C(=O)OC)=CC=C1N1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C VAFPWSDXIBPWPS-UHFFFAOYSA-N 0.000 claims 1
- LFYZFOPGUIUPOK-UHFFFAOYSA-N methyl 4-[[3-bromo-1-[(3-fluorophenyl)methyl]-2-oxopyridin-4-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=C(Br)C(=O)N(CC=2C=C(F)C=CC=2)C=C1 LFYZFOPGUIUPOK-UHFFFAOYSA-N 0.000 claims 1
- LNANAACEAOTYPW-UHFFFAOYSA-N methyl 4-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1 LNANAACEAOTYPW-UHFFFAOYSA-N 0.000 claims 1
- AXODGVODIJPRIV-UHFFFAOYSA-N methyl 5-chloro-1-[(4-chlorophenyl)methyl]-6-oxopyridine-3-carboxylate Chemical compound C1=C(C(=O)OC)C=C(Cl)C(=O)N1CC1=CC=C(Cl)C=C1 AXODGVODIJPRIV-UHFFFAOYSA-N 0.000 claims 1
- QXJAFDTXHPTKFK-UHFFFAOYSA-N methyl n-[[2-[[3-bromo-1-(2,6-difluorophenyl)-6-methyl-2-oxopyridin-4-yl]oxymethyl]-3,5-difluorophenyl]methyl]carbamate Chemical compound COC(=O)NCC1=CC(F)=CC(F)=C1COC1=C(Br)C(=O)N(C=2C(=CC=CC=2F)F)C(C)=C1 QXJAFDTXHPTKFK-UHFFFAOYSA-N 0.000 claims 1
- JRCZENCXYLNJMX-UHFFFAOYSA-N methyl n-[[3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]phenyl]methyl]carbamate Chemical compound COC(=O)NCC1=CC=CC(CN2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 JRCZENCXYLNJMX-UHFFFAOYSA-N 0.000 claims 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- MEWDEAFKDHADBR-UHFFFAOYSA-N n'-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-1-[(2,6-dichlorophenyl)methyl]-6-oxopyridine-3-carbohydrazide Chemical compound ClC1=CC(C(F)(F)F)=CN=C1NNC(=O)C1=CN(CC=2C(=CC=CC=2Cl)Cl)C(=O)C=C1 MEWDEAFKDHADBR-UHFFFAOYSA-N 0.000 claims 1
- FYQOZNKJMOVJMW-UHFFFAOYSA-N n-(4-chlorophenyl)-1-[(2,6-dichlorophenyl)methyl]-6-oxopyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=CN(CC=2C(=CC=CC=2Cl)Cl)C(=O)C=C1 FYQOZNKJMOVJMW-UHFFFAOYSA-N 0.000 claims 1
- DPWQLEZVMSMJGF-UHFFFAOYSA-N n-[4-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CN1C(=O)C(Cl)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C DPWQLEZVMSMJGF-UHFFFAOYSA-N 0.000 claims 1
- UIIVHABJXIQXPN-UHFFFAOYSA-N n-[[3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]phenyl]methyl]-2-hydroxyacetamide Chemical compound BrC=1C(=O)N(CC=2C=C(CNC(=O)CO)C=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F UIIVHABJXIQXPN-UHFFFAOYSA-N 0.000 claims 1
- OHZMHESVEUJRLX-UHFFFAOYSA-N n-[[3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]phenyl]methyl]acetamide Chemical compound CC(=O)NCC1=CC=CC(CN2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 OHZMHESVEUJRLX-UHFFFAOYSA-N 0.000 claims 1
- IMRYITDYAFPLIV-UHFFFAOYSA-N n-[[3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]phenyl]methyl]methanesulfonamide Chemical compound BrC=1C(=O)N(CC=2C=C(CNS(C)(=O)=O)C=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F IMRYITDYAFPLIV-UHFFFAOYSA-N 0.000 claims 1
- DSRHLGUMLACDFJ-UHFFFAOYSA-N n-[[4-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]phenyl]methyl]-1-hydroxycyclopropane-1-carboxamide Chemical compound ClC=1C(=O)N(CC=2C=CC(CNC(=O)C3(O)CC3)=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F DSRHLGUMLACDFJ-UHFFFAOYSA-N 0.000 claims 1
- MZXAVKHTGQDLOY-UHFFFAOYSA-N n-[[4-[[3-chloro-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]phenyl]methyl]-2-hydroxyacetamide Chemical compound ClC=1C(=O)N(CC=2C=CC(CNC(=O)CO)=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F MZXAVKHTGQDLOY-UHFFFAOYSA-N 0.000 claims 1
- WXAHZYBJENKAKI-UHFFFAOYSA-N n-benzyl-5-chloro-1-[(2,6-dichlorophenyl)methyl]-6-oxopyridine-3-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1CN1C(=O)C(Cl)=CC(C(=O)NCC=2C=CC=CC=2)=C1 WXAHZYBJENKAKI-UHFFFAOYSA-N 0.000 claims 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 1
- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 claims 1
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims 1
- 125000006488 t-butyl benzyl group Chemical group 0.000 claims 1
- DZBFOPVLIKGEJH-UHFFFAOYSA-N tert-butyl 4-[3-bromo-1-[(3-fluorophenyl)methyl]-2-oxopyridin-4-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=C(Br)C(=O)N(CC=2C=C(F)C=CC=2)C=C1 DZBFOPVLIKGEJH-UHFFFAOYSA-N 0.000 claims 1
- HJTNRRCOSMEXPJ-UHFFFAOYSA-N tert-butyl n-[[3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]phenyl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC(CN2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2)=O)=C1 HJTNRRCOSMEXPJ-UHFFFAOYSA-N 0.000 claims 1
- KNDWZTLUGLBFGU-UHFFFAOYSA-N tert-butyl n-[[3-[[3-bromo-4-[(4-fluorophenyl)methoxy]-2-oxopyridin-1-yl]methyl]phenyl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC(CN2C(C(Br)=C(OCC=3C=CC(F)=CC=3)C=C2)=O)=C1 KNDWZTLUGLBFGU-UHFFFAOYSA-N 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 59
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 56
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 53
- 125000003710 aryl alkyl group Chemical group 0.000 description 51
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 46
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 35
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 34
- 125000003118 aryl group Chemical group 0.000 description 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 31
- 125000004663 dialkyl amino group Chemical group 0.000 description 30
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 24
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 21
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 21
- 125000002071 phenylalkoxy group Chemical group 0.000 description 20
- 125000003282 alkyl amino group Chemical group 0.000 description 19
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 18
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 17
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 16
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 16
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 15
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 14
- 125000004103 aminoalkyl group Chemical group 0.000 description 13
- 125000005495 pyridazyl group Chemical group 0.000 description 13
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 12
- 125000003884 phenylalkyl group Chemical group 0.000 description 12
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 11
- 125000004104 aryloxy group Chemical group 0.000 description 11
- 125000001624 naphthyl group Chemical group 0.000 description 11
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 10
- 102000000589 Interleukin-1 Human genes 0.000 description 10
- 108010002352 Interleukin-1 Proteins 0.000 description 10
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- 125000001153 fluoro group Chemical group F* 0.000 description 9
- 125000002632 imidazolidinyl group Chemical group 0.000 description 9
- 102000004127 Cytokines Human genes 0.000 description 8
- 108090000695 Cytokines Proteins 0.000 description 8
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 8
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 7
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 7
- 125000001246 bromo group Chemical group Br* 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 description 7
- 102000043136 MAP kinase family Human genes 0.000 description 6
- 108091054455 MAP kinase family Proteins 0.000 description 6
- 206010040070 Septic Shock Diseases 0.000 description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 5
- 108091000080 Phosphotransferase Proteins 0.000 description 5
- 125000005110 aryl thio group Chemical group 0.000 description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 5
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 5
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 102000020233 phosphotransferase Human genes 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 125000005015 aryl alkynyl group Chemical group 0.000 description 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 4
- 125000003831 tetrazolyl group Chemical group 0.000 description 4
- 125000000335 thiazolyl group Chemical group 0.000 description 4
- 125000004306 triazinyl group Chemical group 0.000 description 4
- 208000030507 AIDS Diseases 0.000 description 3
- 206010006895 Cachexia Diseases 0.000 description 3
- 102000004889 Interleukin-6 Human genes 0.000 description 3
- 108090001005 Interleukin-6 Proteins 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 206010040047 Sepsis Diseases 0.000 description 3
- 125000005164 aryl thioalkyl group Chemical group 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000000770 proinflammatory effect Effects 0.000 description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 description 3
- 230000036303 septic shock Effects 0.000 description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 2
- 206010001513 AIDS related complex Diseases 0.000 description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 2
- 229910014585 C2-Ce Inorganic materials 0.000 description 2
- 206010009900 Colitis ulcerative Diseases 0.000 description 2
- 102000029816 Collagenase Human genes 0.000 description 2
- 108060005980 Collagenase Proteins 0.000 description 2
- 208000011231 Crohn disease Diseases 0.000 description 2
- 241000701022 Cytomegalovirus Species 0.000 description 2
- 201000005569 Gout Diseases 0.000 description 2
- 206010018634 Gouty Arthritis Diseases 0.000 description 2
- 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 2
- 102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 2
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 2
- 241000701085 Human alphaherpesvirus 3 Species 0.000 description 2
- 241000701041 Human betaherpesvirus 7 Species 0.000 description 2
- 241001502974 Human gammaherpesvirus 8 Species 0.000 description 2
- 241000701027 Human herpesvirus 6 Species 0.000 description 2
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 2
- 206010063837 Reperfusion injury Diseases 0.000 description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 2
- 229910006074 SO2NH2 Inorganic materials 0.000 description 2
- 206010044248 Toxic shock syndrome Diseases 0.000 description 2
- 231100000650 Toxic shock syndrome Toxicity 0.000 description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 2
- 125000005018 aryl alkenyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 208000019664 bone resorption disease Diseases 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229960002424 collagenase Drugs 0.000 description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- 201000008482 osteoarthritis Diseases 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 230000026731 phosphorylation Effects 0.000 description 2
- 238000006366 phosphorylation reaction Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 230000002685 pulmonary effect Effects 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000004001 thioalkyl group Chemical group 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 230000006433 tumor necrosis factor production Effects 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- 108010005254 Activating Transcription Factors Proteins 0.000 description 1
- 102000005869 Activating Transcription Factors Human genes 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 101100027896 Arabidopsis thaliana OCP3 gene Proteins 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 1
- 108091008038 CHOP Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000000844 Cell Surface Receptors Human genes 0.000 description 1
- 108010001857 Cell Surface Receptors Proteins 0.000 description 1
- 206010063094 Cerebral malaria Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102100023033 Cyclic AMP-dependent transcription factor ATF-2 Human genes 0.000 description 1
- 108010037462 Cyclooxygenase 2 Proteins 0.000 description 1
- 102100029145 DNA damage-inducible transcript 3 protein Human genes 0.000 description 1
- 206010014824 Endotoxic shock Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 206010020164 HIV infection CDC Group III Diseases 0.000 description 1
- 101000974934 Homo sapiens Cyclic AMP-dependent transcription factor ATF-2 Proteins 0.000 description 1
- 101000997829 Homo sapiens Glial cell line-derived neurotrophic factor Proteins 0.000 description 1
- 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 1
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 1
- 241000701044 Human gammaherpesvirus 4 Species 0.000 description 1
- 241000713340 Human immunodeficiency virus 2 Species 0.000 description 1
- 108010044467 Isoenzymes Proteins 0.000 description 1
- 102000055120 MEF2 Transcription Factors Human genes 0.000 description 1
- 108010018650 MEF2 Transcription Factors Proteins 0.000 description 1
- 206010028289 Muscle atrophy Diseases 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 208000033464 Reiter syndrome Diseases 0.000 description 1
- 206010051497 Rhinotracheitis Diseases 0.000 description 1
- 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 1
- 201000010001 Silicosis Diseases 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 208000030886 Traumatic Brain injury Diseases 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 210000004413 cardiac myocyte Anatomy 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 230000009429 distress Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 230000006353 environmental stress Effects 0.000 description 1
- 230000003090 exacerbative effect Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 208000024908 graft versus host disease Diseases 0.000 description 1
- 210000002443 helper t lymphocyte Anatomy 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000018276 interleukin-1 production Effects 0.000 description 1
- 229940100601 interleukin-6 Drugs 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 208000012947 ischemia reperfusion injury Diseases 0.000 description 1
- 208000011379 keloid formation Diseases 0.000 description 1
- 229920006008 lipopolysaccharide Polymers 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 230000011242 neutrophil chemotaxis Effects 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000865 phosphorylative effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 208000009305 pseudorabies Diseases 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 208000002574 reactive arthritis Diseases 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000009772 tissue formation Effects 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D401/10—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 aromatic rings
-
- 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
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- 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
- C07D405/14—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 three or more hetero rings
-
- 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
- C07D409/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D413/10—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 carbon chain containing aromatic rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pulmonology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Molecular Biology (AREA)
- Hematology (AREA)
- Ophthalmology & Optometry (AREA)
- Psychology (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35702902P | 2002-02-14 | 2002-02-14 | |
| US43691502P | 2002-12-30 | 2002-12-30 | |
| PCT/US2003/004634 WO2003068230A1 (en) | 2002-02-14 | 2003-02-14 | Substituted pyridinones as modulators of p38 map kinase |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ534395A true NZ534395A (en) | 2006-10-27 |
Family
ID=27737560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ534395A NZ534395A (en) | 2002-02-14 | 2003-02-14 | Substituted pyridinones as modulators of p38 MAP kinase |
Country Status (32)
| Country | Link |
|---|---|
| US (3) | US7067540B2 (enExample) |
| EP (1) | EP1490064B1 (enExample) |
| JP (2) | JP4164031B2 (enExample) |
| KR (1) | KR100705519B1 (enExample) |
| CN (1) | CN100486576C (enExample) |
| AP (1) | AP1822A (enExample) |
| AT (1) | ATE448784T1 (enExample) |
| BR (1) | BR0307631A (enExample) |
| CA (1) | CA2476012C (enExample) |
| CO (1) | CO5640132A2 (enExample) |
| CY (1) | CY1109680T1 (enExample) |
| DE (1) | DE60330126D1 (enExample) |
| DK (1) | DK1490064T3 (enExample) |
| EA (1) | EA008008B1 (enExample) |
| EC (1) | ECSP045229A (enExample) |
| ES (1) | ES2334990T3 (enExample) |
| GE (1) | GEP20063937B (enExample) |
| HR (1) | HRP20040707B1 (enExample) |
| IL (1) | IL163162A (enExample) |
| IS (1) | IS2735B (enExample) |
| MA (1) | MA27268A1 (enExample) |
| MX (1) | MXPA04007470A (enExample) |
| NO (1) | NO327984B1 (enExample) |
| NZ (1) | NZ534395A (enExample) |
| OA (1) | OA12771A (enExample) |
| PL (1) | PL218749B1 (enExample) |
| PT (1) | PT1490064E (enExample) |
| RS (1) | RS52392B (enExample) |
| SI (1) | SI1490064T1 (enExample) |
| TN (1) | TNSN04156A1 (enExample) |
| WO (1) | WO2003068230A1 (enExample) |
| ZA (1) | ZA200406275B (enExample) |
Families Citing this family (128)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL218749B1 (pl) * | 2002-02-14 | 2015-01-30 | Pharmacia Corp | Pochodna pirydynonu oraz jej zastosowanie do wytwarzania leku |
| CN101404986B (zh) * | 2002-05-17 | 2011-09-28 | 赛奎拉公司 | 用于诊断和治疗感染性疾病的组合物和制药方法 |
| US7456222B2 (en) * | 2002-05-17 | 2008-11-25 | Sequella, Inc. | Anti tubercular drug: compositions and methods |
| US20040033986A1 (en) * | 2002-05-17 | 2004-02-19 | Protopopova Marina Nikolaevna | Anti tubercular drug: compositions and methods |
| EP1405849A1 (en) * | 2002-10-04 | 2004-04-07 | Corning Incorporated | Halogenated styrene compounds and low-absorption-loss polymers obtainable therefrom |
| CL2004002050A1 (es) * | 2003-08-13 | 2005-06-03 | Pharmacia Corp Sa Organizada B | Compuestos derivados de piridinonas sustituidas; su uso en el tratamiento de afecciones causadas o exacerbadas por actividad p38 map kinasa y/o tnf no regulada, tales como inflamaciones, tumores, sida y otros. |
| US7884097B2 (en) * | 2003-09-05 | 2011-02-08 | Sequella, Inc. | Methods and compositions comprising diamines as new anti-tubercular therapeutics |
| JP4614884B2 (ja) * | 2003-11-14 | 2011-01-19 | シャンハイ ゲノミックス インク | ピリドンの誘導体とその使用 |
| JP4869075B2 (ja) * | 2003-11-19 | 2012-02-01 | アレイ バイオファーマ、インコーポレイテッド | Mekの複素環阻害剤及びその使用方法 |
| HRP20100675T1 (hr) | 2003-12-23 | 2011-01-31 | Astex Therapeutics Limited | Derivati pirazola kao modulatori protein kinaze |
| JPWO2005085200A1 (ja) * | 2004-03-05 | 2008-01-17 | 萬有製薬株式会社 | ピリドン誘導体 |
| JPWO2005105743A1 (ja) * | 2004-04-28 | 2008-03-13 | 小野薬品工業株式会社 | 含窒素複素環化合物およびその医薬用途 |
| TWI355380B (en) * | 2004-05-27 | 2012-01-01 | Nihon Nohyaku Co Ltd | Substituted pyrazinecarboxanilide derivatives or s |
| JP4853759B2 (ja) * | 2004-05-27 | 2012-01-11 | 日本農薬株式会社 | 置換ピラジンカルボン酸アニリド誘導体又はその塩類、その中間体及び農園芸用薬剤並びにその使用方法 |
| PL1778686T3 (pl) | 2004-08-12 | 2009-04-30 | Pfizer | Pochodne triazolopirydynylosulfanylowe jako inhibitory kinazy MAP P38 |
| GB0420722D0 (en) * | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
| EP1802590A1 (en) * | 2004-10-13 | 2007-07-04 | Pharmacia & Upjohn Company LLC | Substituted n-alkylpyrimidinones |
| JP4973191B2 (ja) * | 2004-11-10 | 2012-07-11 | 小野薬品工業株式会社 | 含窒素複素環化合物およびその医薬用途 |
| US20070293544A1 (en) * | 2004-11-24 | 2007-12-20 | Ulrich Abel | Novel 4-Arylamino Pyridone Derivatives as Mek Inhibitors for the Treatment of Hyper-Proliferative Disorders |
| BRPI0516383A (pt) | 2004-12-21 | 2008-09-02 | Serono Lab | derivados cìclicos de sulfonil amino e o uso dos mesmos |
| UA86862C2 (en) | 2005-01-31 | 2009-05-25 | Лаборатуар Сероно С.А. | N-hydroxyamide derivatives and use thereof |
| PT1928454E (pt) * | 2005-05-10 | 2014-12-04 | Intermune Inc | Derivativos da piridona para modulação do sistema de proteína quinase ativada pelo stress |
| EP1902032A1 (en) | 2005-06-22 | 2008-03-26 | Astex Therapeutics Limited | Pharmaceutical compounds |
| US8541461B2 (en) | 2005-06-23 | 2013-09-24 | Astex Therapeutics Limited | Pharmaceutical combinations comprising pyrazole derivatives as protein kinase modulators |
| TW200740755A (en) * | 2005-07-13 | 2007-11-01 | Bayer Cropscience Sa | Dihalogenation of N,O-disubstituted hydroxypyridones and their uses |
| EP1916239A4 (en) | 2005-08-10 | 2009-10-21 | Banyu Pharma Co Ltd | PYRIDOLVERBINDUNG |
| JPWO2007024004A1 (ja) | 2005-08-24 | 2009-03-05 | 萬有製薬株式会社 | フェニルピリドン誘導体 |
| ATE528302T1 (de) | 2005-08-29 | 2011-10-15 | Vertex Pharma | 3,5-disubstituierte pyrid-2-one, die als hemmer der tec-familie von nicht-rezeptor tyrosin- kinasen nützlich sind |
| AU2006285145A1 (en) * | 2005-08-29 | 2007-03-08 | Vertex Pharmaceuticals Incorporated | 3,5-disubstituted pyrid-2-ones useful as inhibitors of Tec family of non-.receptor tyrosine kinases |
| WO2007027594A1 (en) | 2005-08-29 | 2007-03-08 | Vertex Pharmaceuticals Incorporated | 3,5-disubstituted pyrid-2-ones useful as inhibitors of tec family of non-receptor tyrosine kinases |
| WO2007025991A2 (en) | 2005-09-01 | 2007-03-08 | Ares Trading S.A. | Treatment of optic neuritis |
| EP1939194A4 (en) | 2005-09-07 | 2010-12-08 | Banyu Pharma Co Ltd | BICYCLIC AROMATIC SUBSTITUTED PYRIDONE DERIVATIVE |
| US7973060B2 (en) * | 2005-10-13 | 2011-07-05 | Crystalgenomics, Inc. | Fab I inhibitor and process for preparing same |
| TWI417095B (zh) | 2006-03-15 | 2013-12-01 | Janssen Pharmaceuticals Inc | 1,4-二取代之3-氰基-吡啶酮衍生物及其作為mGluR2-受體之正向異位性調節劑之用途 |
| US7718830B2 (en) | 2006-04-24 | 2010-05-18 | Allergan, Inc. | Abnormal cannabidiols as agents for lowering intraocular pressure |
| US7618966B2 (en) | 2006-04-24 | 2009-11-17 | Allergan, Inc. | Abnormal Cannabidiols as agents for lowering intraocular pressure |
| AU2007244978B2 (en) * | 2006-04-24 | 2013-05-30 | Allergan, Inc. | Abnormal Cannabidiols as agents for lowering intraocular pressure |
| UY30378A1 (es) * | 2006-06-02 | 2008-01-02 | Janssen Pharmaceutica Nv | Nuevos derivados de piridinona n-aril y n-heteroaril sustituidos para usar en enfermedades mediadas por mch-1 |
| PT2029572E (pt) * | 2006-06-05 | 2011-02-09 | Novartis Ag | Compostos orgânicos |
| CA2656535C (en) * | 2006-07-14 | 2011-08-23 | Amgen Inc. | Alkyne-substituted pyridone compounds and methods of use |
| RU2453543C2 (ru) | 2006-08-25 | 2012-06-20 | Бёрингер Ингельхайм Интернациональ Гмбх | Новые производные пиридона, обладающие антагонистической активностью в отношении mch, и лекарственные средства, включающие такие соединения |
| WO2008041090A1 (en) * | 2006-10-06 | 2008-04-10 | Pfizer Limited | Malanin concentrating hormone receptor-1 antagonist pyridinones |
| WO2008071646A1 (en) | 2006-12-11 | 2008-06-19 | Boehringer Ingelheim International Gmbh | New pyridazine derivatives with mch antagonistic activity and medicaments comprising these compounds |
| WO2008072079A2 (en) * | 2006-12-13 | 2008-06-19 | Pfizer Products Inc. | Processes for the preparation of 3-(4-(2,4-difluorobenzyloxy)-3-bromo-6-methyl-2-oxopyridin-1(2h)-yl)-n,4-dimethylbenzamide |
| US9562019B2 (en) * | 2006-12-21 | 2017-02-07 | Sloan-Kettering Institute For Cancer Research | Substituted pyridazines as EGFR and/or KRAS inhibitors |
| JP2010515745A (ja) * | 2007-01-10 | 2010-05-13 | アルバニー モレキュラー リサーチ, インコーポレイテッド | 5−フロピリジノン置換インダゾール |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| GB0704932D0 (en) | 2007-03-14 | 2007-04-25 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| KR101767849B1 (ko) | 2007-06-20 | 2017-08-11 | 오스펙스 파마슈티칼스, 인코포레이티드 | 섬유증 저해제로서의 치환된 n-아릴 피리디논 |
| US7928230B2 (en) * | 2007-07-17 | 2011-04-19 | Bristol-Myers Squibb Company | Method for modulating GPR119 G protein-coupled receptor and selected compounds |
| AU2008297877C1 (en) | 2007-09-14 | 2013-11-07 | Addex Pharma S.A. | 1,3-disubstituted-4-phenyl-1 H-pyridin-2-ones |
| CN101848893B (zh) | 2007-09-14 | 2012-06-06 | 奥梅-杨森制药有限公司 | 1,3-二取代的4-(芳基-x-苯基)-1h-吡啶-2-酮 |
| EP2203439B1 (en) | 2007-09-14 | 2011-01-26 | Ortho-McNeil-Janssen Pharmaceuticals, Inc. | 1',3'-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2h, 1'h-ý1, 4'¨bipyridinyl-2'-ones |
| JP5592265B2 (ja) | 2007-11-01 | 2014-09-17 | アキュセラ インコーポレイテッド | 眼の疾患及び障害治療用のアミン誘導体化合物 |
| CN101861316B (zh) | 2007-11-14 | 2013-08-21 | 奥梅-杨森制药有限公司 | 咪唑并[1,2-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途 |
| EP2222661B1 (en) * | 2007-11-20 | 2016-04-20 | Merck Sharp & Dohme Corp. | Non-nucleoside reverse transcriptase inhibitors |
| WO2009136965A1 (en) * | 2008-05-06 | 2009-11-12 | Sequella, Inc. | Compositions and methods comprising capuramycin analogues |
| US8304413B2 (en) | 2008-06-03 | 2012-11-06 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
| MX2011002042A (es) | 2008-09-02 | 2011-06-20 | Ortho Mcneil Janssen Pharm | Derivados de 3-azabiciclo[3.1.o]hexilo como moduladores de los receptores del glutamato metabotropico. |
| EA201100311A1 (ru) | 2008-09-11 | 2011-10-31 | Пфайзер Инк. | Амидные производные гетероарилов и их применение в качестве активаторов глюкокиназы |
| ES2466341T3 (es) | 2008-10-16 | 2014-06-10 | Janssen Pharmaceuticals, Inc. | Derivados de indol y benzomorfolina como moduladores de receptores de glutamato metabotrópicos |
| WO2010060589A1 (en) | 2008-11-28 | 2010-06-03 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors |
| CA2748587A1 (en) | 2009-01-20 | 2010-07-29 | Pfizer Inc. | Substituted pyrazinone amides |
| AU2010222589B2 (en) | 2009-03-11 | 2012-08-16 | Pfizer Inc. | Benzofuranyl derivatives used as glucokinase inhibitors |
| EP2430022B1 (en) | 2009-05-12 | 2013-11-20 | Janssen Pharmaceuticals, Inc. | 1,2,4-Triazolo[4,3-a]pyridine derivatives and their use for the treatment or prevention of neurological and psychiatric disorders |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| JP5707390B2 (ja) | 2009-05-12 | 2015-04-30 | ジャンセン ファーマシューティカルズ, インコーポレイテッド | 1,2,4−トリアゾロ[4,3−a]ピリジン誘導体およびmGluR2受容体の正のアロステリック調節因子としてのその使用 |
| ES2536200T3 (es) * | 2009-05-25 | 2015-05-21 | Central South University | Preparación de compuestos de tipo 1-(bencilo sustituido)-5-trifluorometil-2-(1H)piridona, sales de estos y sus aplicaciones |
| US8426407B2 (en) | 2009-05-25 | 2013-04-23 | Central South University | Preparation of 1-(substituted aryl)-5-trifluoromethyl-2-(1H)pyridone compounds and salts thereof and their applications |
| US20110021570A1 (en) | 2009-07-23 | 2011-01-27 | Nancy-Ellen Haynes | Pyridone glucokinase activators |
| CN101973936B (zh) * | 2010-09-28 | 2012-02-08 | 太原理工大学 | 一种吡啶酮衍生物的制备方法 |
| EP2661435B1 (en) | 2010-11-08 | 2015-08-19 | Janssen Pharmaceuticals, Inc. | 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
| WO2012062750A1 (en) | 2010-11-08 | 2012-05-18 | Janssen Pharmaceuticals, Inc. | 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
| CA2814998C (en) | 2010-11-08 | 2019-10-29 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| US9359300B2 (en) | 2010-12-06 | 2016-06-07 | Confluence Life Sciences, Inc. | Methyl/difluorophenyl-methoxy substituted pyridinone-pyridinyl compounds, methyl-pyridinyl-methoxy substituted pyridinone-pyridinyl compounds, and methyl-pyrimidinyl-methoxy substituted pyridinone-pyridinyl compounds |
| ES2873029T3 (es) * | 2010-12-06 | 2021-11-03 | Aclaris Therapeutics Inc | Compuestos de piridinona-piridinilo sustituidos |
| WO2012078674A1 (en) | 2010-12-06 | 2012-06-14 | Confluence Life Sciences, Inc. | Substituted indole/indazole-pyrimidinyl compounds |
| US8563558B2 (en) | 2010-12-06 | 2013-10-22 | Confluence Life Sciences, Inc. | Substituted pyridine urea compounds |
| AP3336A (en) * | 2011-03-07 | 2015-07-31 | Pfizer | Fluoro-pyridinone derivatives useful as antibacterial agents |
| AU2012225611B2 (en) | 2011-03-08 | 2016-09-15 | Auspex Pharmaceuticals, Inc. | Substituted N-Aryl pyridinones |
| MX2014002298A (es) * | 2011-08-29 | 2014-07-22 | Ptc Therapeutics Inc | Compuestos antibacterianos y metodos para su uso. |
| JP2014525452A (ja) * | 2011-08-29 | 2014-09-29 | ピーティーシー セラピューティクス, インコーポレイテッド | 抗菌化合物および使用方法 |
| EP2768826A1 (de) * | 2011-10-17 | 2014-08-27 | Bayer Intellectual Property GmbH | Substituierte oxadiazolylpyridinone und - pyridazinone als hif - hemmer |
| BR112014012288A2 (pt) | 2011-11-22 | 2017-05-23 | Intermune Inc | métodos para diagnosticar e tratar fibrose pulmonar idiopática |
| WO2013086208A1 (en) * | 2011-12-06 | 2013-06-13 | Confluence Life Sciences, Inc. | Substituted pyrimidinone-phenyl-pyrimidinyl compounds |
| JP6137193B2 (ja) | 2011-12-21 | 2017-05-31 | 小野薬品工業株式会社 | 第XIa因子阻害剤としての新規ピリジノンおよびピリミジノン誘導体 |
| EP2802571A1 (en) * | 2012-01-12 | 2014-11-19 | Takeda Pharmaceutical Company Limited | Benzimidazole derivatives as mch receptor antagonists |
| PL2820009T3 (pl) * | 2012-03-01 | 2018-09-28 | Array Biopharma, Inc. | Inhibitory kinaz serynowo/treoninowych |
| CN103288719A (zh) * | 2012-03-05 | 2013-09-11 | 苏州欧凯医药技术有限公司 | 非核甘艾滋病毒抑制物-吡啶酮类先导体的合成 |
| JP5924984B2 (ja) * | 2012-03-06 | 2016-05-25 | 国立大学法人東京農工大学 | トリフルオロメチルピリジノン化合物およびその製造方法 |
| MX2015000830A (es) | 2012-07-18 | 2015-10-26 | Sunshine Lake Pharma Co Ltd | Derivados heterociclicos nitrogenosos y su aplicacion en farmacos. |
| US9018380B2 (en) | 2012-08-24 | 2015-04-28 | Boar of Regents, The University of Texas System | Heterocyclic modulators of HIF activity for treatment of disease |
| EP2888256A4 (en) * | 2012-08-24 | 2016-02-17 | Univ Texas | HETEROCYCLIC HIF ACTIVITY MODULATORS FOR THE TREATMENT OF DISEASES |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| ES2614281T3 (es) | 2012-12-13 | 2017-05-30 | Novartis Ag | Derivados de piridona y derivados de los mismos en el tratamiento de tuberculosis |
| PL2953931T3 (pl) * | 2013-01-31 | 2017-09-29 | Vertex Pharmaceuticals Incorporated | Pirydonoamidy jako modulatory kanałów sodowych |
| WO2014181213A1 (en) | 2013-05-10 | 2014-11-13 | Pfizer Inc. | Crystalline form of (sa)-(-)-3-(3-bromo-4-((2,4-difluorobenzyl)oxy)-6-methyl-2-oxopyridin-1 (2h)-yl)-n,4-dimethylbenzamide |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| US9115089B2 (en) | 2013-06-07 | 2015-08-25 | Confluence Life Sciences, Inc. | Methyl/fluoro-pyridinyl-methoxy substituted pyridinone-pyridinyl compounds and fluoro-pyrimidinyl-methoxy substituted pyridinone-pyridinyl compounds |
| CA2917490A1 (en) | 2013-07-09 | 2015-01-15 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| SMT201800521T1 (it) | 2013-12-13 | 2018-11-09 | Vertex Pharma | Profarmaci di piridonammidi utili come modulatori di canali del sodio |
| AU2015208233B2 (en) | 2014-01-21 | 2019-08-29 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
| ME03518B (me) | 2014-01-21 | 2020-04-20 | Janssen Pharmaceutica Nv | Kombinacije koje obuhvataju pozitivne alosterične modulatore ili ortosterične agoniste metabotropnog glutamatergičnog receptora podtipa 2 i njihova primjena |
| DK3110420T3 (da) | 2014-02-25 | 2019-05-13 | Board Of Regents Univ Of Texas System | Salte af heterocykliske modulatorer af hif-aktivitet til behandling af sygdomme |
| KR102373700B1 (ko) | 2014-04-02 | 2022-03-11 | 인터뮨, 인크. | 항섬유성 피리디논 |
| PL3174852T3 (pl) * | 2014-07-30 | 2018-11-30 | ABAC Therapeutics, S.L. | Arylohydrazydy zawierające ugrupowanie 2-pirydonu jako selektywne środki przeciwbakteryjne |
| JP6610562B2 (ja) | 2014-12-10 | 2019-11-27 | 小野薬品工業株式会社 | ジヒドロインドリジノン誘導体 |
| EA034912B1 (ru) * | 2015-06-03 | 2020-04-06 | Бристол-Маерс Сквибб Компани | 4-гидрокси-3-(гетероарил)пиридин-2-оновые агонисты apj для применения в лечении сердечно-сосудистых заболеваний |
| CN105153027A (zh) * | 2015-07-21 | 2015-12-16 | 东华大学 | 一种3-氰基-4-羟基-2-吡啶酮类化合物及其制备和应用 |
| CN106466318B (zh) * | 2015-08-21 | 2019-01-01 | 中南大学 | 1-杂环取代苄基吡啶酮类化合物在制备治疗糖尿病肾病药物中的应用 |
| WO2017151409A1 (en) | 2016-02-29 | 2017-09-08 | University Of Florida Research Foundation, Incorporated | Chemotherapeutic methods |
| WO2018213426A1 (en) | 2017-05-16 | 2018-11-22 | Vertex Pharmaceuticals Incorporated | Deuterated pyridone amides and prodrugs thereof as modulators of sodium channels |
| KR102236356B1 (ko) | 2017-11-24 | 2021-04-05 | 주식회사 종근당 | 루푸스의 예방 또는 치료를 위한 조성물 |
| JP2021512935A (ja) | 2018-02-12 | 2021-05-20 | バーテックス ファーマシューティカルズ インコーポレイテッドVertex Pharmaceuticals Incorporated | 疼痛を処置する方法 |
| KR20190099952A (ko) * | 2018-02-20 | 2019-08-28 | 주식회사 종근당 | 포도막염의 예방 또는 치료를 위한 조성물 |
| US12351556B2 (en) * | 2019-10-04 | 2025-07-08 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Pyridin-2(1H)one derivatives, their preparation and their use for the treatment of pain |
| PH12022551379A1 (en) | 2019-12-06 | 2023-05-03 | Vertex Pharma | Substituted tetrahydrofurans as modulators of sodium channels |
| GB201918413D0 (en) * | 2019-12-13 | 2020-01-29 | Z Factor Ltd | Compounds and their use for the treatment of alpha1-antitrypsin deficiency |
| MX2022011755A (es) | 2020-03-27 | 2022-11-16 | Aclaris Therapeutics Inc | Proceso, composiciones y formas cristalinas de compuestos de piridinona-piridinilo sustituidos. |
| CN112552232B (zh) * | 2020-12-16 | 2022-11-25 | 浙江工业大学 | 一种吡啶酮六位炔胺修饰衍生物及其制备方法与应用 |
| KR20230152692A (ko) | 2021-02-02 | 2023-11-03 | 리미널 바이오사이언시스 리미티드 | Gpr84 길항제 및 이의 용도 |
| PE20240144A1 (es) * | 2021-03-31 | 2024-02-01 | Xinthera Inc | Inhibidores de mk2 y usos de estos |
| DK4347031T3 (da) | 2021-06-04 | 2025-12-01 | Vertex Pharma | N-(hydroxyalkyl-(hetero)aryl)-tetrahydrofuran-carboxamider som modulatorer af natriumkanaler |
| US11685719B2 (en) | 2021-07-09 | 2023-06-27 | Xinthera, Inc. | Pyridinone MK2 inhibitors and uses thereof |
| WO2023134765A1 (zh) * | 2022-01-14 | 2023-07-20 | 上海翰森生物医药科技有限公司 | 含五元环类衍生物、其制备方法和应用 |
| WO2024022412A1 (zh) * | 2022-07-28 | 2024-02-01 | 深圳信立泰药业股份有限公司 | 一种式(i)所示的三联吡啶二酮化合物晶型及其制备方法与应用 |
Family Cites Families (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE267045C (enExample) | ||||
| NL6816241A (enExample) * | 1967-12-01 | 1969-06-03 | ||
| BE758759A (fr) * | 1969-11-12 | 1971-05-10 | Merck & Co Inc | Pyridones anti-inflammatoires |
| US3644626A (en) * | 1969-11-25 | 1972-02-22 | Merck & Co Inc | Novel pyridones in compositions and methods for treating inflammation pain and fever |
| NL7016899A (enExample) * | 1969-12-03 | 1971-06-07 | ||
| DE3434921A1 (de) | 1984-09-22 | 1986-05-07 | Sandoz-Patent-GmbH, 7850 Lörrach | Heterocyclische monoazoverbindungen |
| JPH01305081A (ja) | 1988-04-04 | 1989-12-08 | E R Squibb & Sons Inc | 3―アシルアミノ―1―[[[(置換スルホニル)アミノ〕カルボニル〕アミノ〕―2―アゼチジノン類 |
| US5164506A (en) | 1988-12-14 | 1992-11-17 | Bayer Aktiengesellschaft | Substituted 2-pyridones and pyrid-2-thiones compounds |
| US5032602A (en) | 1988-12-14 | 1991-07-16 | Bayer Aktiengesellschaft | Inhibiting HMG-CoA reductase with novel substituted 2-pyridones and pyrid-2-thiones |
| US5308854A (en) | 1990-06-18 | 1994-05-03 | Merck & Co., Inc. | Inhibitors of HIV reverse transcriptase |
| IL100917A0 (en) | 1991-02-16 | 1992-11-15 | Fisons Plc | Pyridinone and pyrimidinone derivatives,their preparation and pharmaceutical compositions containing them |
| DE4221583A1 (de) | 1991-11-12 | 1993-05-13 | Bayer Ag | Substituierte biphenylpyridone |
| DE4141788A1 (de) | 1991-12-18 | 1993-06-24 | Merck Patent Gmbh | Imidazopyridine |
| US5378720A (en) | 1991-12-19 | 1995-01-03 | Sterling Winthrop Inc. | Saccharin derivative proteolytic enzyme inhibitors |
| AU668694B2 (en) | 1991-12-19 | 1996-05-16 | Sanofi-Synthelabo | Saccharin derivative proteolytic enzyme inhibitors |
| DE4206045A1 (de) | 1992-02-27 | 1993-09-02 | Bayer Ag | Sulfonylbenzyl substituierte pyridone |
| GB9406144D0 (en) | 1993-03-29 | 1994-05-18 | Zeneca Ltd | Heterocyclic compounds |
| DE4314964A1 (de) | 1993-05-06 | 1994-11-10 | Bayer Ag | Pyridinylmethyl-substiutierte Pyridine und Pyridone |
| DE4316077A1 (de) | 1993-05-13 | 1994-11-17 | Bayer Ag | Substituierte Mono- und Bihydridylmethylpyridone |
| US5744605A (en) | 1993-06-30 | 1998-04-28 | University Of Pittsburgh | Intermediates in the synthesis of (+) camptothecin and related compounds and synthesis thereof |
| DE4341453A1 (de) | 1993-12-06 | 1995-06-08 | Merck Patent Gmbh | Imidazopyridine |
| US5789426A (en) | 1995-01-20 | 1998-08-04 | Cornell Research Foundation, Inc. | Method for the treatment of fibroproliferative disorders by application of inhibitors of protein hydroxylation |
| US5869428A (en) | 1995-03-13 | 1999-02-09 | Ishihara Sangyo Kaisha Ltd. | Pyridonesulfonylurea compounds, process for their production and herbicides containing them |
| US5849587A (en) | 1995-06-09 | 1998-12-15 | Cornell Research Foundation, Inc. | Method of inhibiting viral replication in eukaryotic cells and of inducing apoptosis of virally-infected cells |
| WO1997010712A1 (en) * | 1995-09-19 | 1997-03-27 | Margolin Solomon B | Inhibition of tumor necrosis factor alpha |
| AU720616B2 (en) | 1996-02-22 | 2000-06-08 | Merck & Co., Inc. | Pyridinone thrombin inhibitors |
| DE19619950A1 (de) * | 1996-04-17 | 1997-10-23 | Bayer Ag | Heterocyclisch-substituierte Phenylglycinolamide |
| PL329441A1 (en) | 1996-04-23 | 1999-03-29 | Merck & Co Inc | Pyrasinone-type thrombin inhibitors |
| JPH09315008A (ja) | 1996-05-31 | 1997-12-09 | Fuji Photo Film Co Ltd | 感熱記録材料 |
| EP0944382A1 (en) * | 1996-09-30 | 1999-09-29 | Brigham & Women's Hospital | Methods and compounds for treatment of abnormal uterine bleeding |
| JP2001508796A (ja) | 1997-01-22 | 2001-07-03 | メルク エンド カンパニー インコーポレーテッド | トロンビン阻害薬 |
| AR012117A1 (es) | 1997-03-21 | 2000-09-27 | Novartis Ag | Compuestos herbicidas, proceso para su preparacion, compuestos intermediarios para su exclusivo uso en dicho proceso, composicion herbicidae inhibidora del crecimiento de las plantas, metodo para controlar el crecimiento indeseado de plantas y uso de dicha composicion en el control de |
| US6514977B1 (en) * | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
| CN1295570A (zh) | 1998-04-08 | 2001-05-16 | 诺瓦提斯公司 | N-吡啶酮基除草剂 |
| DE19826671A1 (de) | 1998-06-16 | 1999-12-23 | Hoechst Schering Agrevo Gmbh | 1,3-Oxazolin- und 1,3-Thiazolin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
| US6344323B1 (en) | 1998-09-16 | 2002-02-05 | Vitagenix, Inc. | Compositions and methods for inhibiting cox-2 expression and treating cox-2 associated disorders by using cox-2 antisense oligonucleotides |
| HK1041876B (en) | 1998-10-27 | 2006-06-23 | Abbott Laboratories | Prostaglandin endoperoxide h synthase biosynthesis inhibitors |
| JP2000128878A (ja) | 1998-10-28 | 2000-05-09 | Teijin Ltd | ベンゾフリル−α−ピリドン誘導体 |
| EP1058549A4 (en) | 1998-12-23 | 2003-11-12 | Bristol Myers Squibb Pharma Co | FACTOR Xa OR THROMBIN INHIBITORS |
| MXPA01011340A (es) * | 1999-05-07 | 2003-08-01 | Texas Biotechnology Corp | Derivados de acido carboxilico que inhiben la union de las integrinas a sus receptores. |
| GEP20063915B (en) | 2000-11-17 | 2006-09-11 | Bristol Myers Squibb Co | PYRROLOTRIAZINE COMPOUNDS USEFUL AS KINASE INHIBITORS AND USE THEREOF FOR TREATING p38 KINASE-ASSOCIATED CONDITIONS |
| PL218749B1 (pl) * | 2002-02-14 | 2015-01-30 | Pharmacia Corp | Pochodna pirydynonu oraz jej zastosowanie do wytwarzania leku |
| BR0309053A (pt) | 2002-04-19 | 2005-02-22 | Smithkline Beecham Corp | Compostos |
| CL2004002050A1 (es) * | 2003-08-13 | 2005-06-03 | Pharmacia Corp Sa Organizada B | Compuestos derivados de piridinonas sustituidas; su uso en el tratamiento de afecciones causadas o exacerbadas por actividad p38 map kinasa y/o tnf no regulada, tales como inflamaciones, tumores, sida y otros. |
| CA2640665A1 (en) * | 2006-02-10 | 2007-08-16 | Pfizer Products Inc. | Pyridinone pyrazole urea and pyrimidinone pyrazole urea derivatives |
-
2003
- 2003-02-14 PL PL371943A patent/PL218749B1/pl unknown
- 2003-02-14 DK DK03713478T patent/DK1490064T3/da active
- 2003-02-14 JP JP2003567412A patent/JP4164031B2/ja not_active Expired - Fee Related
- 2003-02-14 NZ NZ534395A patent/NZ534395A/en not_active IP Right Cessation
- 2003-02-14 SI SI200331709T patent/SI1490064T1/sl unknown
- 2003-02-14 PT PT03713478T patent/PT1490064E/pt unknown
- 2003-02-14 AT AT03713478T patent/ATE448784T1/de active
- 2003-02-14 MX MXPA04007470A patent/MXPA04007470A/es active IP Right Grant
- 2003-02-14 HR HRP20040707AA patent/HRP20040707B1/hr not_active IP Right Cessation
- 2003-02-14 RS YU74904A patent/RS52392B/sr unknown
- 2003-02-14 EA EA200400953A patent/EA008008B1/ru not_active IP Right Cessation
- 2003-02-14 BR BR0307631-8A patent/BR0307631A/pt not_active IP Right Cessation
- 2003-02-14 CN CNB038080427A patent/CN100486576C/zh not_active Expired - Fee Related
- 2003-02-14 OA OA1200400210A patent/OA12771A/en unknown
- 2003-02-14 DE DE60330126T patent/DE60330126D1/de not_active Expired - Lifetime
- 2003-02-14 CA CA2476012A patent/CA2476012C/en not_active Expired - Fee Related
- 2003-02-14 ES ES03713478T patent/ES2334990T3/es not_active Expired - Lifetime
- 2003-02-14 EP EP03713478A patent/EP1490064B1/en not_active Expired - Lifetime
- 2003-02-14 WO PCT/US2003/004634 patent/WO2003068230A1/en not_active Ceased
- 2003-02-14 AP APAP/P/2004/003105A patent/AP1822A/en active
- 2003-02-14 KR KR1020047012622A patent/KR100705519B1/ko not_active Expired - Fee Related
- 2003-02-14 US US10/367,987 patent/US7067540B2/en not_active Expired - Lifetime
- 2003-02-14 GE GEAP8358A patent/GEP20063937B/en unknown
-
2004
- 2004-07-22 IL IL163162A patent/IL163162A/en not_active IP Right Cessation
- 2004-07-26 IS IS7374A patent/IS2735B/is unknown
- 2004-08-05 ZA ZA2004/06275A patent/ZA200406275B/en unknown
- 2004-08-06 CO CO04076760A patent/CO5640132A2/es active IP Right Grant
- 2004-08-09 MA MA27818A patent/MA27268A1/fr unknown
- 2004-08-12 EC EC2004005229A patent/ECSP045229A/es unknown
- 2004-08-12 TN TNP2004000156A patent/TNSN04156A1/fr unknown
- 2004-09-13 NO NO20043820A patent/NO327984B1/no not_active IP Right Cessation
-
2005
- 2005-09-14 US US11/226,556 patent/US7629363B2/en not_active Expired - Fee Related
-
2006
- 2006-09-13 US US11/531,492 patent/US20070088033A1/en not_active Abandoned
- 2006-09-28 JP JP2006263778A patent/JP5325380B2/ja not_active Expired - Fee Related
-
2009
- 2009-12-30 CY CY20091101348T patent/CY1109680T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5325380B2 (ja) | P38mapキナーゼのモジュレータとしての置換されたピリジノン | |
| US20050176775A1 (en) | Substituted pyridinones | |
| CA2521081C (en) | Pyrimidin-4-one derivatives and their use as p38 kinase modulators | |
| US7888374B2 (en) | Inhibitors of c-jun N-terminal kinases | |
| US8227613B2 (en) | Heteroaryl carboxamide derivatives | |
| US7795271B2 (en) | Substituted pyrimidinones | |
| NZ532511A (en) | Heterocyclic compounds for use in the treatment of disorders of the urinary tract | |
| AU2002346979A1 (en) | Heterocyclic compounds for use in the treatment of disorders of the urinary tract | |
| AU2003217433B2 (en) | Substituted pyridinones as modulators of p38 MAP Kinase | |
| KR100901931B1 (ko) | P38 map 키나제의 조절제로서의 치환된 피리디논 | |
| AU2007202607B2 (en) | Substituted Pyridinones as Modulators of p38 MAP Kinase | |
| JP7789662B2 (ja) | Mta協働prmt5阻害剤 | |
| HK1074992B (en) | Substituted pyridinones as modulators of p38 map kinase | |
| HK1135382B (en) | Substituted pyridinones as modulators of p38 map kinase |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RENW | Renewal (renewal fees accepted) | ||
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 3 YEARS UNTIL 14 FEB 2016 BY THOMSON REUTERS Effective date: 20130305 |
|
| LAPS | Patent lapsed |