PL194175B1 - Pirydazynony, zawierające je kompozycje farmaceutyczne oraz ich zastosowanie - Google Patents
Pirydazynony, zawierające je kompozycje farmaceutyczne oraz ich zastosowanieInfo
- Publication number
- PL194175B1 PL194175B1 PL98355418A PL35541898A PL194175B1 PL 194175 B1 PL194175 B1 PL 194175B1 PL 98355418 A PL98355418 A PL 98355418A PL 35541898 A PL35541898 A PL 35541898A PL 194175 B1 PL194175 B1 PL 194175B1
- Authority
- PL
- Poland
- Prior art keywords
- pyridazinone
- phenyl
- group
- fluorophenyl
- methylsulfonyl
- Prior art date
Links
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 409
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 62
- 125000003118 aryl group Chemical group 0.000 claims abstract description 41
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 31
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 30
- 150000002367 halogens Chemical class 0.000 claims abstract description 27
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 22
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 21
- 125000005309 thioalkoxy group Chemical group 0.000 claims abstract description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 17
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 17
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims abstract description 16
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 16
- 125000005277 alkyl imino group Chemical group 0.000 claims abstract description 11
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 11
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 11
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 11
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 6
- 125000005080 alkoxycarbonylalkenyl group Chemical group 0.000 claims abstract description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 6
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 4
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims abstract description 3
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims abstract 2
- -1 nitro, carboxyl Chemical group 0.000 claims description 305
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 229910052717 sulfur Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 125000004434 sulfur atom Chemical group 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 108010037462 Cyclooxygenase 2 Proteins 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 150000003180 prostaglandins Chemical class 0.000 claims description 10
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 9
- 229910006069 SO3H Inorganic materials 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 239000011593 sulfur Chemical group 0.000 claims description 9
- 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 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 125000005019 carboxyalkenyl group Chemical group 0.000 claims description 4
- 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 125000005159 cyanoalkoxy group Chemical group 0.000 claims description 3
- 150000001924 cycloalkanes Chemical class 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- QPTNEZSIWLUDPF-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(2-hydroxy-2-methylpropoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCC(C)(O)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 QPTNEZSIWLUDPF-UHFFFAOYSA-N 0.000 claims description 2
- KDJWTTCLGKFONX-CYBMUJFWSA-N 2-(3,4-difluorophenyl)-4-[(2r)-3-hydroxy-2-methylpropoxy]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC[C@@H](CO)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 KDJWTTCLGKFONX-CYBMUJFWSA-N 0.000 claims description 2
- KDJWTTCLGKFONX-ZDUSSCGKSA-N 2-(3,4-difluorophenyl)-4-[(2s)-3-hydroxy-2-methylpropoxy]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC[C@H](CO)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 KDJWTTCLGKFONX-ZDUSSCGKSA-N 0.000 claims description 2
- PORJADFRTDGOOL-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-(3-hydroxy-3-methylbutoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCC(C)(O)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C=C1 PORJADFRTDGOOL-UHFFFAOYSA-N 0.000 claims description 2
- YELGVOXMDKPKTD-UHFFFAOYSA-N 4-[1-(3,4-difluorophenyl)-5-(2-hydroxy-2-methylpropoxy)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound O=C1C(OCC(C)(O)C)=C(C=2C=CC(=CC=2)S(N)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 YELGVOXMDKPKTD-UHFFFAOYSA-N 0.000 claims description 2
- HUHICZNTARYEEM-GFCCVEGCSA-N 4-[1-(3,4-difluorophenyl)-5-[(2r)-3-hydroxy-2-methylpropoxy]-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound O=C1C(OC[C@@H](CO)C)=C(C=2C=CC(=CC=2)S(N)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 HUHICZNTARYEEM-GFCCVEGCSA-N 0.000 claims description 2
- HUHICZNTARYEEM-LBPRGKRZSA-N 4-[1-(3,4-difluorophenyl)-5-[(2s)-3-hydroxy-2-methylpropoxy]-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound O=C1C(OC[C@H](CO)C)=C(C=2C=CC(=CC=2)S(N)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 HUHICZNTARYEEM-LBPRGKRZSA-N 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 208000002193 Pain Diseases 0.000 claims description 2
- 206010037660 Pyrexia Diseases 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 102000010907 Cyclooxygenase 2 Human genes 0.000 claims 1
- 238000006073 displacement reaction Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 508
- 238000000034 method Methods 0.000 description 434
- 238000004458 analytical method Methods 0.000 description 284
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 197
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 186
- 235000019439 ethyl acetate Nutrition 0.000 description 166
- 239000000047 product Substances 0.000 description 159
- 239000000243 solution Substances 0.000 description 158
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 120
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 108
- 239000000203 mixture Substances 0.000 description 96
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
- 238000006243 chemical reaction Methods 0.000 description 78
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 73
- 239000000741 silica gel Substances 0.000 description 69
- 229910002027 silica gel Inorganic materials 0.000 description 69
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
- 239000011541 reaction mixture Substances 0.000 description 62
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 60
- 235000019341 magnesium sulphate Nutrition 0.000 description 60
- 239000007787 solid Substances 0.000 description 59
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 54
- 239000012267 brine Substances 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 51
- 230000002829 reductive effect Effects 0.000 description 51
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 47
- NVNPLEPBDPJYRZ-UHFFFAOYSA-N 1-(bromomethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C=C1 NVNPLEPBDPJYRZ-UHFFFAOYSA-N 0.000 description 46
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 45
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 38
- 239000000706 filtrate Substances 0.000 description 31
- 239000003921 oil Substances 0.000 description 31
- 235000019198 oils Nutrition 0.000 description 31
- 239000012044 organic layer Substances 0.000 description 31
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
- 238000010992 reflux Methods 0.000 description 29
- 239000002253 acid Substances 0.000 description 28
- 239000010410 layer Substances 0.000 description 27
- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical group C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 27
- WMJMABVHDMRMJA-UHFFFAOYSA-M [Cl-].[Mg+]C1CCCCC1 Chemical compound [Cl-].[Mg+]C1CCCCC1 WMJMABVHDMRMJA-UHFFFAOYSA-M 0.000 description 26
- 238000004440 column chromatography Methods 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
- YEUYZNNBXLMFCW-UHFFFAOYSA-N 1-bromo-4-methylsulfanylbenzene Chemical compound CSC1=CC=C(Br)C=C1 YEUYZNNBXLMFCW-UHFFFAOYSA-N 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- KGNQDBQYEBMPFZ-UHFFFAOYSA-N 1-fluoro-4-iodobenzene Chemical compound FC1=CC=C(I)C=C1 KGNQDBQYEBMPFZ-UHFFFAOYSA-N 0.000 description 20
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 20
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 19
- IVUHTLFKBDDICS-UHFFFAOYSA-N (4-methylsulfanylphenyl)boronic acid Chemical compound CSC1=CC=C(B(O)O)C=C1 IVUHTLFKBDDICS-UHFFFAOYSA-N 0.000 description 18
- AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 18
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 17
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 17
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 17
- KNMCZSNDSSMJRZ-UHFFFAOYSA-N 4-chloro-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(Cl)C(=O)N(CC(F)(F)F)N=C1 KNMCZSNDSSMJRZ-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- JJIFTOPVKWDHJI-UHFFFAOYSA-N 4-(bromomethyl)-1,2-difluorobenzene Chemical compound FC1=CC=C(CBr)C=C1F JJIFTOPVKWDHJI-UHFFFAOYSA-N 0.000 description 15
- ZMCKLPPZCCJCBA-UHFFFAOYSA-N 5-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)-1h-pyridazin-6-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)NN=C1 ZMCKLPPZCCJCBA-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 15
- 238000001816 cooling Methods 0.000 description 15
- 229910000027 potassium carbonate Inorganic materials 0.000 description 15
- 238000004809 thin layer chromatography Methods 0.000 description 15
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 230000008878 coupling Effects 0.000 description 14
- 238000010168 coupling process Methods 0.000 description 14
- 238000005859 coupling reaction Methods 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 13
- 125000002947 alkylene group Chemical group 0.000 description 13
- LBUNNMJLXWQQBY-UHFFFAOYSA-N 4-fluorophenylboronic acid Chemical compound OB(O)C1=CC=C(F)C=C1 LBUNNMJLXWQQBY-UHFFFAOYSA-N 0.000 description 12
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 12
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 12
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 11
- BKTKRRPMVDUHJN-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-methoxy-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 BKTKRRPMVDUHJN-UHFFFAOYSA-N 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 238000004587 chromatography analysis Methods 0.000 description 11
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 11
- SJLFASZCKBEVLA-UHFFFAOYSA-N 5-(4-fluorophenoxy)-4-(4-methylsulfonylphenyl)-1h-pyridazin-6-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC(F)=CC=2)C(=O)NN=C1 SJLFASZCKBEVLA-UHFFFAOYSA-N 0.000 description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 150000002148 esters Chemical group 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- 229940124530 sulfonamide Drugs 0.000 description 10
- 150000003456 sulfonamides Chemical class 0.000 description 10
- RKOUFQLNMRAACI-UHFFFAOYSA-N 1,1,1-trifluoro-2-iodoethane Chemical compound FC(F)(F)CI RKOUFQLNMRAACI-UHFFFAOYSA-N 0.000 description 9
- GXAFGGGEYCMXMV-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-methoxy-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound O=C1C(OC)=C(C=2C=CC(SC)=CC=2)C=NN1C1=CC=C(F)C=C1 GXAFGGGEYCMXMV-UHFFFAOYSA-N 0.000 description 9
- HXYBWVBYNJAITG-UHFFFAOYSA-N 2-benzyl-4-(4-fluorophenyl)-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C=CC=CC=2)N=C1 HXYBWVBYNJAITG-UHFFFAOYSA-N 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 239000000651 prodrug Substances 0.000 description 9
- 229940002612 prodrug Drugs 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- 150000003462 sulfoxides Chemical class 0.000 description 9
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 9
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 150000003857 carboxamides Chemical class 0.000 description 8
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 8
- 235000015320 potassium carbonate Nutrition 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- KDVZJKOYSOFXRV-UHFFFAOYSA-N (3,4-dimethylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1C KDVZJKOYSOFXRV-UHFFFAOYSA-N 0.000 description 7
- BOEAXYIGEBSNRU-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-methoxy-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound O=C1C(OC)=C(C=2C=CC(SC)=CC=2)C=NN1C1=CC=C(F)C(F)=C1 BOEAXYIGEBSNRU-UHFFFAOYSA-N 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- WVDYBOADDMMFIY-UHFFFAOYSA-N Cyclopentanethiol Chemical compound SC1CCCC1 WVDYBOADDMMFIY-UHFFFAOYSA-N 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 235000011181 potassium carbonates Nutrition 0.000 description 7
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- NCNYEGJDGNOYJX-NSCUHMNNSA-N (e)-2,3-dibromo-4-oxobut-2-enoic acid Chemical compound OC(=O)C(\Br)=C(/Br)C=O NCNYEGJDGNOYJX-NSCUHMNNSA-N 0.000 description 6
- KMGCKSAIIHOKCX-UHFFFAOYSA-N 2,3-dihydro-1h-inden-2-ol Chemical compound C1=CC=C2CC(O)CC2=C1 KMGCKSAIIHOKCX-UHFFFAOYSA-N 0.000 description 6
- YWFDQBYNCWJPRV-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-methoxy-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound O=C1C(OC)=C(C=2C=CC(SC)=CC=2)C=NN1C1=CC=C(F)C(Cl)=C1 YWFDQBYNCWJPRV-UHFFFAOYSA-N 0.000 description 6
- CTCLYZLWGMZILM-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-methoxy-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound O=C1C(OC)=C(C=2C=CC(SC)=CC=2)C=NN1C1=CC=CC(Cl)=C1 CTCLYZLWGMZILM-UHFFFAOYSA-N 0.000 description 6
- ZQLPPHNIRIEQJN-UHFFFAOYSA-N 2-benzyl-4,5-dibromopyridazin-3-one Chemical compound O=C1C(Br)=C(Br)C=NN1CC1=CC=CC=C1 ZQLPPHNIRIEQJN-UHFFFAOYSA-N 0.000 description 6
- FHNGNRASVGTFOY-UHFFFAOYSA-N 2-benzyl-4-bromo-5-methoxypyridazin-3-one Chemical compound O=C1C(Br)=C(OC)C=NN1CC1=CC=CC=C1 FHNGNRASVGTFOY-UHFFFAOYSA-N 0.000 description 6
- ITLSIRGFHWQRSM-UHFFFAOYSA-N 2-benzyl-4-chloro-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(Cl)C(=O)N(CC=2C=CC=CC=2)N=C1 ITLSIRGFHWQRSM-UHFFFAOYSA-N 0.000 description 6
- KVZQNLPOHROISY-UHFFFAOYSA-N 2-benzyl-4-chloro-5-methoxypyridazin-3-one Chemical compound O=C1C(Cl)=C(OC)C=NN1CC1=CC=CC=C1 KVZQNLPOHROISY-UHFFFAOYSA-N 0.000 description 6
- PFDCBAVRAKFFQZ-UHFFFAOYSA-N 2-benzyl-5-bromo-4-methoxypyridazin-3-one Chemical compound O=C1C(OC)=C(Br)C=NN1CC1=CC=CC=C1 PFDCBAVRAKFFQZ-UHFFFAOYSA-N 0.000 description 6
- JIOQKOOSSQSBLJ-UHFFFAOYSA-N 4,5-dibromo-2-(4-fluorophenyl)pyridazin-3-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C(Br)=C(Br)C=N1 JIOQKOOSSQSBLJ-UHFFFAOYSA-N 0.000 description 6
- YMQPKONILWWJQG-UHFFFAOYSA-N 4-bromo-1,2-difluorobenzene Chemical compound FC1=CC=C(Br)C=C1F YMQPKONILWWJQG-UHFFFAOYSA-N 0.000 description 6
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 6
- WBEWLRPKDVRNOF-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(4-methylsulfonylphenyl)-1h-pyridazin-6-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)C(=O)NN=C1 WBEWLRPKDVRNOF-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- VRIBRBRLSPZWBT-UHFFFAOYSA-N [2-(3-chlorophenyl)-5-(4-methylsulfonylphenyl)-3-oxopyridazin-4-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC(C1=O)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(Cl)=C1 VRIBRBRLSPZWBT-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 6
- 239000004327 boric acid Substances 0.000 description 6
- 239000013058 crude material Substances 0.000 description 6
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 6
- PKDBSOOYVOEUQR-UHFFFAOYSA-N mucobromic acid Natural products OC1OC(=O)C(Br)=C1Br PKDBSOOYVOEUQR-UHFFFAOYSA-N 0.000 description 6
- 230000001590 oxidative effect Effects 0.000 description 6
- 238000012856 packing Methods 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 6
- CNDNUZUKUGDDGL-UHFFFAOYSA-N (3-fluoro-4-methylsulfanylphenyl)boronic acid Chemical compound CSC1=CC=C(B(O)O)C=C1F CNDNUZUKUGDDGL-UHFFFAOYSA-N 0.000 description 5
- FEKUXLUOKFSMRO-UHFFFAOYSA-N (4-fluorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(F)C=C1 FEKUXLUOKFSMRO-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- 108010044467 Isoenzymes Proteins 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 5
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical class CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 5
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 235000017550 sodium carbonate Nutrition 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
- 150000003568 thioethers Chemical class 0.000 description 5
- ZXBMIRYQUFQQNX-UHFFFAOYSA-N (4-fluorophenyl)hydrazine Chemical compound NNC1=CC=C(F)C=C1 ZXBMIRYQUFQQNX-UHFFFAOYSA-N 0.000 description 4
- LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 description 4
- YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 4
- AYTSELVZWGHUEE-UHFFFAOYSA-N 1-fluoro-2-methylsulfanylbenzene Chemical compound CSC1=CC=CC=C1F AYTSELVZWGHUEE-UHFFFAOYSA-N 0.000 description 4
- MXGNZWRLAXCITB-UHFFFAOYSA-N 2-benzyl-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C=CC=CC=2)N=C1 MXGNZWRLAXCITB-UHFFFAOYSA-N 0.000 description 4
- PKUXZQMJKJXUTN-UHFFFAOYSA-N 2-benzyl-4-chloro-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(Cl)C(=O)N(CC=2C=CC=CC=2)N=C1 PKUXZQMJKJXUTN-UHFFFAOYSA-N 0.000 description 4
- JWKOPJXMPIZSCO-UHFFFAOYSA-N 4-(bromomethyl)-2-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CBr)C(=O)N(C=2C=CC(F)=CC=2)N=C1 JWKOPJXMPIZSCO-UHFFFAOYSA-N 0.000 description 4
- RSTBYGMJEKPLBW-UHFFFAOYSA-N 4-chloro-5-methoxy-2-phenylpyridazin-3-one Chemical compound O=C1C(Cl)=C(OC)C=NN1C1=CC=CC=C1 RSTBYGMJEKPLBW-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- QCJFJJDJUAHTMF-UHFFFAOYSA-N 5-(4-fluorophenyl)-4-(4-methylsulfanylphenyl)-1h-pyridazin-6-one Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)NN=C1 QCJFJJDJUAHTMF-UHFFFAOYSA-N 0.000 description 4
- DEHHNGDDBQILRN-UHFFFAOYSA-N 5-bromo-4-propan-2-yloxy-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound CC(C)OC1=C(Br)C=NN(CC(F)(F)F)C1=O DEHHNGDDBQILRN-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 108050003243 Prostaglandin G/H synthase 1 Proteins 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical class [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- 125000001589 carboacyl group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M cesium fluoride Substances [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000010265 fast atom bombardment Methods 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 230000002496 gastric effect Effects 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 125000001786 isothiazolyl group Chemical group 0.000 description 4
- KZGFEBLGGYOPML-UHFFFAOYSA-M magnesium;1-fluoro-3-methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC(F)=C1 KZGFEBLGGYOPML-UHFFFAOYSA-M 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical group COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 3
- LUMLZKVIXLWTCI-NSCUHMNNSA-N (e)-2,3-dichloro-4-oxobut-2-enoic acid Chemical compound OC(=O)C(\Cl)=C(/Cl)C=O LUMLZKVIXLWTCI-NSCUHMNNSA-N 0.000 description 3
- WRHAMNYNYTUFKM-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 WRHAMNYNYTUFKM-UHFFFAOYSA-N 0.000 description 3
- HDQQMCAWIOCJQX-UHFFFAOYSA-N 2-benzyl-4-(4-fluorophenoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC(F)=CC=2)C(=O)N(CC=2C=CC=CC=2)N=C1 HDQQMCAWIOCJQX-UHFFFAOYSA-N 0.000 description 3
- OYFDRNSQHLRVRA-UHFFFAOYSA-N 2-benzyl-4-[(4-fluorophenyl)methyl]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CC=2C=CC(F)=CC=2)C(=O)N(CC=2C=CC=CC=2)N=C1 OYFDRNSQHLRVRA-UHFFFAOYSA-N 0.000 description 3
- BMIGOQGOAGWFMP-UHFFFAOYSA-N 2-benzyl-5-(3-fluoro-4-methylsulfanylphenyl)-4-methoxypyridazin-3-one Chemical compound O=C1C(OC)=C(C=2C=C(F)C(SC)=CC=2)C=NN1CC1=CC=CC=C1 BMIGOQGOAGWFMP-UHFFFAOYSA-N 0.000 description 3
- DUXCSEISVMREAX-UHFFFAOYSA-N 3,3-dimethylbutan-1-ol Chemical compound CC(C)(C)CCO DUXCSEISVMREAX-UHFFFAOYSA-N 0.000 description 3
- GZLGTVRDLCJQTO-UHFFFAOYSA-M 3-methylbutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC(C)C)C1=CC=CC=C1 GZLGTVRDLCJQTO-UHFFFAOYSA-M 0.000 description 3
- ZNUFTYAFHHDQKV-UHFFFAOYSA-N 4,5-dibromo-2-(3-chloro-4-fluorophenyl)pyridazin-3-one Chemical compound C1=C(Cl)C(F)=CC=C1N1C(=O)C(Br)=C(Br)C=N1 ZNUFTYAFHHDQKV-UHFFFAOYSA-N 0.000 description 3
- WAWFBWCUUVTFBS-UHFFFAOYSA-N 4-(3-fluoro-4-methylsulfanylphenyl)-5-(3-methylbutyl)-1h-pyridazin-6-one Chemical compound C1=C(F)C(SC)=CC=C1C1=C(CCC(C)C)C(=O)NN=C1 WAWFBWCUUVTFBS-UHFFFAOYSA-N 0.000 description 3
- OTLMOPZOGAUOSL-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-hydroxy-2-phenylpyridazin-3-one Chemical compound O=C1C(C=2C=CC(F)=CC=2)=C(O)C=NN1C1=CC=CC=C1 OTLMOPZOGAUOSL-UHFFFAOYSA-N 0.000 description 3
- CBRTZUPVWSZTBP-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-methoxy-2-phenylpyridazin-3-one Chemical compound O=C1C(C=2C=CC(F)=CC=2)=C(OC)C=NN1C1=CC=CC=C1 CBRTZUPVWSZTBP-UHFFFAOYSA-N 0.000 description 3
- MOWUUYXWEKRASM-UHFFFAOYSA-N 4-(bromomethyl)-2-(3-chlorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CBr)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 MOWUUYXWEKRASM-UHFFFAOYSA-N 0.000 description 3
- YDWMPGYWXSRCGK-UHFFFAOYSA-N 4-[1-benzyl-5-(4-fluorophenyl)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C=CC=CC=2)N=C1 YDWMPGYWXSRCGK-UHFFFAOYSA-N 0.000 description 3
- CJTIWGBQCVYTQE-UHFFFAOYSA-N 4-bromo-2-chloro-1-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1Cl CJTIWGBQCVYTQE-UHFFFAOYSA-N 0.000 description 3
- PUVIIPMVFZISRW-UHFFFAOYSA-N 4-bromo-2-ethenyl-1-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1C=C PUVIIPMVFZISRW-UHFFFAOYSA-N 0.000 description 3
- BGQXFVNKAYFNHF-UHFFFAOYSA-N 5-(3-fluoro-4-methylsulfanylphenyl)-4-(3-methylbutyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=C(F)C(SC)=CC=C1C1=C(CCC(C)C)C(=O)N(CC(F)(F)F)N=C1 BGQXFVNKAYFNHF-UHFFFAOYSA-N 0.000 description 3
- SWYIWTVVIINQHO-UHFFFAOYSA-N 5-(3-fluoro-4-methylsulfinylphenyl)-4-(3-methylbutyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=NN(CC(F)(F)F)C(=O)C(CCC(C)C)=C1C1=CC=C(S(C)=O)C(F)=C1 SWYIWTVVIINQHO-UHFFFAOYSA-N 0.000 description 3
- GCUYTCSEHLQZDV-UHFFFAOYSA-N 5-[(4-fluorophenyl)methyl]-4-(4-methylsulfonylphenyl)-1h-pyridazin-6-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CC=2C=CC(F)=CC=2)C(=O)NN=C1 GCUYTCSEHLQZDV-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- XKNRAADGHJTDFR-UHFFFAOYSA-N C1=CC(S(=O)(=O)C)=CC=C1C1=C(O)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(O)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 XKNRAADGHJTDFR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 229940124639 Selective inhibitor Drugs 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- HDSMHYXPCVVAOS-UHFFFAOYSA-N [5-(4-fluorophenyl)-6-oxo-1-phenylpyridazin-4-yl] trifluoromethanesulfonate Chemical compound C1=CC(F)=CC=C1C(C1=O)=C(OS(=O)(=O)C(F)(F)F)C=NN1C1=CC=CC=C1 HDSMHYXPCVVAOS-UHFFFAOYSA-N 0.000 description 3
- WSOBSOJYZICZQO-UHFFFAOYSA-M [Br-].FC1=CC=CC(C[Mg+])=C1 Chemical compound [Br-].FC1=CC=CC(C[Mg+])=C1 WSOBSOJYZICZQO-UHFFFAOYSA-M 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000005236 alkanoylamino group Chemical group 0.000 description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000005121 aminocarbonylalkoxy group Chemical group 0.000 description 3
- ZIQCCIAIROIHHR-UHFFFAOYSA-N benzene;boric acid Chemical compound OB(O)O.C1=CC=CC=C1 ZIQCCIAIROIHHR-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 235000010418 carrageenan Nutrition 0.000 description 3
- 239000000679 carrageenan Substances 0.000 description 3
- 229920001525 carrageenan Polymers 0.000 description 3
- 229940113118 carrageenan Drugs 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 3
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000005191 hydroxyalkylamino group Chemical group 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical class [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- WJGVYRMMIIWBAU-UHFFFAOYSA-M magnesium;2-methylbutane;bromide Chemical compound [Mg+2].[Br-].CC(C)C[CH2-] WJGVYRMMIIWBAU-UHFFFAOYSA-M 0.000 description 3
- QGEFGPVWRJCFQP-UHFFFAOYSA-M magnesium;methanidylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C1=CC=CC=C1 QGEFGPVWRJCFQP-UHFFFAOYSA-M 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- ZAKLKBFCSHJIRI-UHFFFAOYSA-N mucochloric acid Natural products OC1OC(=O)C(Cl)=C1Cl ZAKLKBFCSHJIRI-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical group 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 3
- QKSQWQOAUQFORH-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C QKSQWQOAUQFORH-UHFFFAOYSA-N 0.000 description 3
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 3
- IILGLPAJXQMKGQ-UHFFFAOYSA-N (3-fluoro-4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1F IILGLPAJXQMKGQ-UHFFFAOYSA-N 0.000 description 2
- MKFDONWOZBIQGF-UHFFFAOYSA-N (3-methyl-4-methylsulfanylphenyl)boronic acid Chemical compound CSC1=CC=C(B(O)O)C=C1C MKFDONWOZBIQGF-UHFFFAOYSA-N 0.000 description 2
- CMJQIHGBUKZEHP-UHFFFAOYSA-N (4-chloro-3-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C(F)=C1 CMJQIHGBUKZEHP-UHFFFAOYSA-N 0.000 description 2
- POPVUKGJWNLYGW-UHFFFAOYSA-N (hydroxyamino) hydrogen sulfate Chemical compound ONOS(O)(=O)=O POPVUKGJWNLYGW-UHFFFAOYSA-N 0.000 description 2
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 2
- JFEVIPGMXQNRRF-UHFFFAOYSA-N 1,1,3-trichloroprop-1-ene Chemical compound ClCC=C(Cl)Cl JFEVIPGMXQNRRF-UHFFFAOYSA-N 0.000 description 2
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 2
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 2
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical class C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ALAQDUSTXPEHMH-UHFFFAOYSA-N 1-bromo-2-methylsulfanylbenzene Chemical compound CSC1=CC=CC=C1Br ALAQDUSTXPEHMH-UHFFFAOYSA-N 0.000 description 2
- JRGGUPZKKTVKOV-UHFFFAOYSA-N 1-bromo-3-chlorobenzene Chemical compound ClC1=CC=CC(Br)=C1 JRGGUPZKKTVKOV-UHFFFAOYSA-N 0.000 description 2
- OPMFFAOEPFATTG-UHFFFAOYSA-N 2,2,2-trifluoroethylhydrazine Chemical compound NNCC(F)(F)F OPMFFAOEPFATTG-UHFFFAOYSA-N 0.000 description 2
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
- PRBCSYHVGZDFRJ-UHFFFAOYSA-N 2,3,3-trifluoroprop-2-en-1-ol Chemical compound OCC(F)=C(F)F PRBCSYHVGZDFRJ-UHFFFAOYSA-N 0.000 description 2
- UNYWPODSYPPUFH-UHFFFAOYSA-N 2,3,3-trifluoroprop-2-enyl methanesulfonate Chemical compound CS(=O)(=O)OCC(F)=C(F)F UNYWPODSYPPUFH-UHFFFAOYSA-N 0.000 description 2
- KIOXUMBWGHXSDJ-UHFFFAOYSA-N 2,4-bis(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=CC(F)=CC=2)N=C1 KIOXUMBWGHXSDJ-UHFFFAOYSA-N 0.000 description 2
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 description 2
- SSDAKJLEKSSAMH-UHFFFAOYSA-N 2,4-dihydro-1h-pyridazin-3-one Chemical compound O=C1CC=CNN1 SSDAKJLEKSSAMH-UHFFFAOYSA-N 0.000 description 2
- OIMFDAYHYFEIPS-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(3-ethenyl-4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(C=C)C(F)=CC=2)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 OIMFDAYHYFEIPS-UHFFFAOYSA-N 0.000 description 2
- KWHHQUCIAKOYTO-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(4-fluorophenyl)-5-(3-methyl-4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=C(C)C(SC)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 KWHHQUCIAKOYTO-UHFFFAOYSA-N 0.000 description 2
- GAYLCBWZYGAIDL-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(4-fluorophenyl)-5-(3-methyl-4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=C(S(C)(=O)=O)C(C)=CC(C2=C(C(=O)N(C=3C=C(F)C(F)=CC=3)N=C2)C=2C=CC(F)=CC=2)=C1 GAYLCBWZYGAIDL-UHFFFAOYSA-N 0.000 description 2
- XRHRMQOSDZHBOA-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-methoxy-5-(3-methyl-4-methylsulfanylphenyl)pyridazin-3-one Chemical compound O=C1C(OC)=C(C=2C=C(C)C(SC)=CC=2)C=NN1C1=CC=C(F)C(F)=C1 XRHRMQOSDZHBOA-UHFFFAOYSA-N 0.000 description 2
- RALITQCPIHBIOW-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-cyclohexyl-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C2CCCCC2)C(=O)N(C=2C=C(Cl)C(F)=CC=2)N=C1 RALITQCPIHBIOW-UHFFFAOYSA-N 0.000 description 2
- QRNOYCCSACTDJS-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(3-methylbutoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCC(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(Cl)=C1 QRNOYCCSACTDJS-UHFFFAOYSA-N 0.000 description 2
- VSWHBTMMQCSFFP-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-[(4-fluorophenoxy)methyl]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(COC=2C=CC(F)=CC=2)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 VSWHBTMMQCSFFP-UHFFFAOYSA-N 0.000 description 2
- KTHOCMVQWOHGOW-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-methyl-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(C)C(=O)N(C=2C=CC(F)=CC=2)N=C1 KTHOCMVQWOHGOW-UHFFFAOYSA-N 0.000 description 2
- OFYWYNUSBLDTBU-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-methyl-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C=C1 OFYWYNUSBLDTBU-UHFFFAOYSA-N 0.000 description 2
- KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- LXUNZSDDXMPKLP-UHFFFAOYSA-N 2-Methylbenzenethiol Chemical compound CC1=CC=CC=C1S LXUNZSDDXMPKLP-UHFFFAOYSA-N 0.000 description 2
- CXVPRKLZTFCIPA-UHFFFAOYSA-N 2-benzyl-4-(4-fluorophenyl)-5-[4-(trifluoromethylsulfanyl)phenyl]pyridazin-3-one Chemical compound C1=CC(F)=CC=C1C(C1=O)=C(C=2C=CC(SC(F)(F)F)=CC=2)C=NN1CC1=CC=CC=C1 CXVPRKLZTFCIPA-UHFFFAOYSA-N 0.000 description 2
- GXTMZHMECBEZEG-UHFFFAOYSA-N 2-benzyl-4-(4-fluorophenyl)-5-[4-(trifluoromethylsulfonyl)phenyl]pyridazin-3-one Chemical compound C1=CC(F)=CC=C1C(C1=O)=C(C=2C=CC(=CC=2)S(=O)(=O)C(F)(F)F)C=NN1CC1=CC=CC=C1 GXTMZHMECBEZEG-UHFFFAOYSA-N 0.000 description 2
- OYPBHRTWZIICMR-UHFFFAOYSA-N 2-benzyl-4-methoxy-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound O=C1C(OC)=C(C=2C=CC(SC)=CC=2)C=NN1CC1=CC=CC=C1 OYPBHRTWZIICMR-UHFFFAOYSA-N 0.000 description 2
- RZKWHNHKVRUTBE-UHFFFAOYSA-N 2-benzyl-5-(3-fluoro-4-methylsulfanylphenyl)-4-(3-methylbutyl)pyridazin-3-one Chemical compound C1=C(F)C(SC)=CC=C1C1=C(CCC(C)C)C(=O)N(CC=2C=CC=CC=2)N=C1 RZKWHNHKVRUTBE-UHFFFAOYSA-N 0.000 description 2
- FSXKVYGFNNIDBZ-UHFFFAOYSA-N 2-benzylpyridazin-3-one Chemical compound O=C1C=CC=NN1CC1=CC=CC=C1 FSXKVYGFNNIDBZ-UHFFFAOYSA-N 0.000 description 2
- WZFSSYQBMILMOU-UHFFFAOYSA-N 2-fluoro-4-[5-(3-methylbutyl)-6-oxo-1-(2,2,2-trifluoroethyl)pyridazin-4-yl]benzenesulfonamide Chemical compound C1=NN(CC(F)(F)F)C(=O)C(CCC(C)C)=C1C1=CC=C(S(N)(=O)=O)C(F)=C1 WZFSSYQBMILMOU-UHFFFAOYSA-N 0.000 description 2
- BDFAOUQQXJIZDG-UHFFFAOYSA-N 2-methylpropane-1-thiol Chemical compound CC(C)CS BDFAOUQQXJIZDG-UHFFFAOYSA-N 0.000 description 2
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical class BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 2
- DSLLLNOSQULGOW-UHFFFAOYSA-N 2-tert-butyl-4-(3-methylbutoxy)-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(OCCC(C)C)C(=O)N(C(C)(C)C)N=C1 DSLLLNOSQULGOW-UHFFFAOYSA-N 0.000 description 2
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical group OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
- AGLQURQNVJVJNB-UHFFFAOYSA-N 4,5-dibromo-1h-pyridazin-6-one Chemical compound BrC=1C=NNC(=O)C=1Br AGLQURQNVJVJNB-UHFFFAOYSA-N 0.000 description 2
- VYDCNWDRQPFXRR-UHFFFAOYSA-N 4,5-dibromo-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound FC(F)(F)CN1N=CC(Br)=C(Br)C1=O VYDCNWDRQPFXRR-UHFFFAOYSA-N 0.000 description 2
- RIDNCXXOUTWXDM-UHFFFAOYSA-N 4,5-dibromo-2-(3,4-difluorophenyl)pyridazin-3-one Chemical compound C1=C(F)C(F)=CC=C1N1C(=O)C(Br)=C(Br)C=N1 RIDNCXXOUTWXDM-UHFFFAOYSA-N 0.000 description 2
- YRUBEFSHXCHAAA-UHFFFAOYSA-N 4,5-dibromo-2-(3-chlorophenyl)pyridazin-3-one Chemical compound ClC1=CC=CC(N2C(C(Br)=C(Br)C=N2)=O)=C1 YRUBEFSHXCHAAA-UHFFFAOYSA-N 0.000 description 2
- WRECSZCHPLHDPH-UHFFFAOYSA-N 4,5-dichloro-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound FC(F)(F)CN1N=CC(Cl)=C(Cl)C1=O WRECSZCHPLHDPH-UHFFFAOYSA-N 0.000 description 2
- DKEOHEKGAYNCQD-UHFFFAOYSA-N 4-(4-fluorophenoxy)-2-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC(F)=CC=2)C(=O)N(C=2C=CC(F)=CC=2)N=C1 DKEOHEKGAYNCQD-UHFFFAOYSA-N 0.000 description 2
- CYCOZFNULYBKRN-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfanylphenyl)-2-(2,3,3-trifluoroprop-2-enyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC(F)=C(F)F)N=C1 CYCOZFNULYBKRN-UHFFFAOYSA-N 0.000 description 2
- GNUFSEZKHMCTAH-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC(F)(F)F)N=C1 GNUFSEZKHMCTAH-UHFFFAOYSA-N 0.000 description 2
- YIBIIXCTHIQWSJ-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(2,3,3-trifluoroprop-2-enyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC(F)=C(F)F)N=C1 YIBIIXCTHIQWSJ-UHFFFAOYSA-N 0.000 description 2
- FCMCBCCRWUAJMW-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-phenylpyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=CC=CC=2)N=C1 FCMCBCCRWUAJMW-UHFFFAOYSA-N 0.000 description 2
- ZHFPZHOBROLGEU-UHFFFAOYSA-N 4-(cyclohexen-1-yl)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2CCCCC=2)C(=O)N(CC(F)(F)F)N=C1 ZHFPZHOBROLGEU-UHFFFAOYSA-N 0.000 description 2
- AIYCHBMSBDEMPL-UHFFFAOYSA-N 4-(cyclopropylmethoxy)-5-(4-methylsulfanylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(OCC2CC2)C(=O)N(CC(F)(F)F)N=C1 AIYCHBMSBDEMPL-UHFFFAOYSA-N 0.000 description 2
- SPKVKCUJVRTWLS-UHFFFAOYSA-N 4-(cyclopropylmethoxy)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OCC2CC2)C(=O)N(CC(F)(F)F)N=C1 SPKVKCUJVRTWLS-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- CKRVONJDBIYRQK-UHFFFAOYSA-N 4-[(3-fluorophenyl)methyl]-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CC=2C=C(F)C=CC=2)C(=O)N(CC(F)(F)F)N=C1 CKRVONJDBIYRQK-UHFFFAOYSA-N 0.000 description 2
- WFXJEEJFWDIZQB-UHFFFAOYSA-N 4-[(4-fluorophenoxy)methyl]-2-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(COC=2C=CC(F)=CC=2)C(=O)N(C=2C=CC(F)=CC=2)N=C1 WFXJEEJFWDIZQB-UHFFFAOYSA-N 0.000 description 2
- DLIQFNPEUJMTIQ-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CC=2C=CC(F)=CC=2)C(=O)N(CC(F)(F)F)N=C1 DLIQFNPEUJMTIQ-UHFFFAOYSA-N 0.000 description 2
- HXVRFWPRKPWXAS-UHFFFAOYSA-N 4-[1,5-bis(4-fluorophenyl)-6-oxopyridazin-4-yl]-2-fluorobenzenesulfonamide Chemical compound C1=C(F)C(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=CC(F)=CC=2)N=C1 HXVRFWPRKPWXAS-UHFFFAOYSA-N 0.000 description 2
- CGONWKDTPMVEPO-UHFFFAOYSA-N 4-[5-(4-chloro-3-fluorophenyl)-6-oxo-1-(2,2,2-trifluoroethyl)pyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=C(F)C(Cl)=CC=2)C(=O)N(CC(F)(F)F)N=C1 CGONWKDTPMVEPO-UHFFFAOYSA-N 0.000 description 2
- QPJNSNUPQMKHBI-UHFFFAOYSA-N 4-[benzyl(methyl)amino]-2-(3-chlorophenyl)-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(N(C)CC=2C=CC=CC=2)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 QPJNSNUPQMKHBI-UHFFFAOYSA-N 0.000 description 2
- VXKYOKPNAXNAFU-UHFFFAOYSA-N 4-bromo-1-fluoro-2-methylbenzene Chemical compound CC1=CC(Br)=CC=C1F VXKYOKPNAXNAFU-UHFFFAOYSA-N 0.000 description 2
- YHOVMTICYSGLFD-UHFFFAOYSA-N 4-bromo-2-fluoro-1-methylsulfanylbenzene Chemical compound CSC1=CC=C(Br)C=C1F YHOVMTICYSGLFD-UHFFFAOYSA-N 0.000 description 2
- BPGGHGJSZLWSHM-UHFFFAOYSA-N 4-chloro-5-(4-methylsulfanylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(Cl)C(=O)N(CC(F)(F)F)N=C1 BPGGHGJSZLWSHM-UHFFFAOYSA-N 0.000 description 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 2
- OTOJGQWOSFQJAH-UHFFFAOYSA-N 4-hydroxy-1h-pyridazin-6-one Chemical compound OC1=CC(=O)C=NN1 OTOJGQWOSFQJAH-UHFFFAOYSA-N 0.000 description 2
- QXSAKPUBHTZHKW-UHFFFAOYSA-N 4-hydroxybenzamide Chemical group NC(=O)C1=CC=C(O)C=C1 QXSAKPUBHTZHKW-UHFFFAOYSA-N 0.000 description 2
- WEYNXCDKWDAFEM-UHFFFAOYSA-N 4-methoxy-5-(4-methylsulfanylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=NN(CC(F)(F)F)C(=O)C(OC)=C1C1=CC=C(SC)C=C1 WEYNXCDKWDAFEM-UHFFFAOYSA-N 0.000 description 2
- KECCFSZFXLAGJS-UHFFFAOYSA-N 4-methylsulfonylphenol Chemical compound CS(=O)(=O)C1=CC=C(O)C=C1 KECCFSZFXLAGJS-UHFFFAOYSA-N 0.000 description 2
- IMKYDIVKXLBEBD-UHFFFAOYSA-N 5-(4-methylsulfanylphenyl)-4-propan-2-yloxy-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(OC(C)C)C(=O)N(CC(F)(F)F)N=C1 IMKYDIVKXLBEBD-UHFFFAOYSA-N 0.000 description 2
- OEZBYVMLSRIOMI-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-4-propan-2-yloxy-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=NN(CC(F)(F)F)C(=O)C(OC(C)C)=C1C1=CC=C(S(C)(=O)=O)C=C1 OEZBYVMLSRIOMI-UHFFFAOYSA-N 0.000 description 2
- BVTCGNRYYSDXJD-UHFFFAOYSA-N 5-bromo-2-(3,4-difluorophenyl)-4-methoxypyridazin-3-one Chemical compound O=C1C(OC)=C(Br)C=NN1C1=CC=C(F)C(F)=C1 BVTCGNRYYSDXJD-UHFFFAOYSA-N 0.000 description 2
- NHGWANWAVJMBGX-UHFFFAOYSA-N 5-bromo-2-(3-chloro-4-fluorophenyl)-4-methoxypyridazin-3-one Chemical compound O=C1C(OC)=C(Br)C=NN1C1=CC=C(F)C(Cl)=C1 NHGWANWAVJMBGX-UHFFFAOYSA-N 0.000 description 2
- SAKIVRJUFHPOHK-UHFFFAOYSA-N 5-bromo-2-(3-chlorophenyl)-4-methoxypyridazin-3-one Chemical compound O=C1C(OC)=C(Br)C=NN1C1=CC=CC(Cl)=C1 SAKIVRJUFHPOHK-UHFFFAOYSA-N 0.000 description 2
- HSIYZTSXBCAHSH-UHFFFAOYSA-N 5-bromo-2-(4-fluorophenyl)-4-methoxypyridazin-3-one Chemical compound O=C1C(OC)=C(Br)C=NN1C1=CC=C(F)C=C1 HSIYZTSXBCAHSH-UHFFFAOYSA-N 0.000 description 2
- IAVYAZXFPIEIQI-UHFFFAOYSA-N 5-bromo-4-(propan-2-ylamino)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound CC(C)NC1=C(Br)C=NN(CC(F)(F)F)C1=O IAVYAZXFPIEIQI-UHFFFAOYSA-N 0.000 description 2
- AOXUEVJNENMLPW-UHFFFAOYSA-N 5-bromo-4-methoxy-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound COC1=C(Br)C=NN(CC(F)(F)F)C1=O AOXUEVJNENMLPW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OVFGHENNGMQIPS-UHFFFAOYSA-N C1=CC(SC)=CC=C1C1=C(O)C(=O)N(CC(F)(F)F)N=C1 Chemical compound C1=CC(SC)=CC=C1C1=C(O)C(=O)N(CC(F)(F)F)N=C1 OVFGHENNGMQIPS-UHFFFAOYSA-N 0.000 description 2
- 108010037464 Cyclooxygenase 1 Proteins 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 2
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 2
- 108010029485 Protein Isoforms Proteins 0.000 description 2
- 102000001708 Protein Isoforms Human genes 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000862969 Stella Species 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical group CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- GAUQFHQUXOMFLJ-UHFFFAOYSA-N [2-[1-benzyl-5-(4-fluorophenyl)-6-oxopyridazin-4-yl]phenyl]sulfonylmethyl acetate Chemical compound CC(=O)OCS(=O)(=O)C1=CC=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C=CC=CC=2)N=C1 GAUQFHQUXOMFLJ-UHFFFAOYSA-N 0.000 description 2
- ALMFIOZYDASRRC-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=C(C(F)(F)F)C=C1 ALMFIOZYDASRRC-UHFFFAOYSA-N 0.000 description 2
- WKPFCYLQSQRCOV-UHFFFAOYSA-N [4-[[5-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)-6-oxopyridazin-1-yl]methyl]phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1CN1C(=O)C(C=2C=CC(F)=CC=2)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=N1 WKPFCYLQSQRCOV-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 description 2
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 125000005018 aryl alkenyl group Chemical group 0.000 description 2
- 125000006213 aryl hydroxyalkyl group Chemical group 0.000 description 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 2
- 125000006212 aryloxy hydroxyalkyl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- WVSCRRLWRRANJY-UHFFFAOYSA-N cyclohexen-1-yl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CCCCC1 WVSCRRLWRRANJY-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 2
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000006264 debenzylation reaction Methods 0.000 description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 2
- RUHCATDGSSLXPZ-UHFFFAOYSA-N dicarboxyazaniumylideneazanide Chemical compound OC(=O)[N+](=[N-])C(O)=O RUHCATDGSSLXPZ-UHFFFAOYSA-N 0.000 description 2
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 2
- 229960002986 dinoprostone Drugs 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 125000004476 heterocycloamino group Chemical group 0.000 description 2
- 239000002044 hexane fraction Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 2
- 125000005020 hydroxyalkenyl group Chemical group 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- YIAPLDFPUUJILH-UHFFFAOYSA-N indan-1-ol Chemical compound C1=CC=C2C(O)CCC2=C1 YIAPLDFPUUJILH-UHFFFAOYSA-N 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 150000004694 iodide salts Chemical class 0.000 description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- BRKADVNLTRCLOW-UHFFFAOYSA-M magnesium;fluorobenzene;bromide Chemical compound [Mg+2].[Br-].FC1=CC=[C-]C=C1 BRKADVNLTRCLOW-UHFFFAOYSA-M 0.000 description 2
- BVUQKCCKUOSAEV-UHFFFAOYSA-M magnesium;methylbenzene;bromide Chemical compound [Mg+2].[Br-].CC1=CC=[C-]C=C1 BVUQKCCKUOSAEV-UHFFFAOYSA-M 0.000 description 2
- UZNGRHDUJIVHQT-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].C[C-]=C UZNGRHDUJIVHQT-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- AJPPKGMEHMXPMC-UHFFFAOYSA-N methyl 2-(4-fluorophenyl)acetate Chemical compound COC(=O)CC1=CC=C(F)C=C1 AJPPKGMEHMXPMC-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000005483 neopentyl alcohol group Chemical group 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000004533 oil dispersion Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 2
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 125000004963 sulfonylalkyl group Chemical group 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 125000001984 thiazolidinyl group Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- PIZQWRXTMGASCZ-UHFFFAOYSA-N (1-methylcyclopropyl)methanol Chemical compound OCC1(C)CC1 PIZQWRXTMGASCZ-UHFFFAOYSA-N 0.000 description 1
- IYLGZMTXKJYONK-ACLXAEORSA-N (12s,15r)-15-hydroxy-11,16-dioxo-15,20-dihydrosenecionan-12-yl acetate Chemical compound O1C(=O)[C@](CC)(O)C[C@@H](C)[C@](C)(OC(C)=O)C(=O)OCC2=CCN3[C@H]2[C@H]1CC3 IYLGZMTXKJYONK-ACLXAEORSA-N 0.000 description 1
- LZKLZCSHMDRKJH-UHFFFAOYSA-N (2,5-difluorophenyl)hydrazine;hydrochloride Chemical compound [Cl-].[NH3+]NC1=CC(F)=CC=C1F LZKLZCSHMDRKJH-UHFFFAOYSA-N 0.000 description 1
- NVOLYUXUHWBCRJ-UHFFFAOYSA-N (2-methoxypyridin-3-yl)boronic acid Chemical compound COC1=NC=CC=C1B(O)O NVOLYUXUHWBCRJ-UHFFFAOYSA-N 0.000 description 1
- NSJVYHOPHZMZPN-UHFFFAOYSA-N (2-methylphenyl)boronic acid Chemical compound CC1=CC=CC=C1B(O)O NSJVYHOPHZMZPN-UHFFFAOYSA-N 0.000 description 1
- DOMQFIFVDIAOOT-ROUUACIJSA-N (2S,3R)-N-[4-(2,6-dimethoxyphenyl)-5-(5-methylpyridin-3-yl)-1,2,4-triazol-3-yl]-3-(5-methylpyrimidin-2-yl)butane-2-sulfonamide Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NN=C1C=1C=NC=C(C=1)C)NS(=O)(=O)[C@@H](C)[C@H](C)C1=NC=C(C=N1)C DOMQFIFVDIAOOT-ROUUACIJSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- JKIGHOARKAIPJI-UHFFFAOYSA-N (3,4-dichlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C(Cl)=C1 JKIGHOARKAIPJI-UHFFFAOYSA-N 0.000 description 1
- KBSCNXDDCDSLLP-UHFFFAOYSA-N (3,4-difluorophenyl)hydrazine Chemical compound NNC1=CC=C(F)C(F)=C1 KBSCNXDDCDSLLP-UHFFFAOYSA-N 0.000 description 1
- DJGHSJBYKIQHIK-UHFFFAOYSA-N (3,5-dimethylphenyl)boronic acid Chemical compound CC1=CC(C)=CC(B(O)O)=C1 DJGHSJBYKIQHIK-UHFFFAOYSA-N 0.000 description 1
- RPYIPFXHIKXRKS-UHFFFAOYSA-N (3-bromophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=CC(Br)=C1 RPYIPFXHIKXRKS-UHFFFAOYSA-N 0.000 description 1
- DUORBNTWCCJANU-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)hydrazine Chemical compound NNC1=CC=C(F)C(Cl)=C1 DUORBNTWCCJANU-UHFFFAOYSA-N 0.000 description 1
- GFPJLZASIVURDY-UHFFFAOYSA-N (3-chlorophenyl)hydrazine Chemical compound NNC1=CC=CC(Cl)=C1 GFPJLZASIVURDY-UHFFFAOYSA-N 0.000 description 1
- CRRIAWUJYMLJOE-UHFFFAOYSA-N (3-chlorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=CC(Cl)=C1 CRRIAWUJYMLJOE-UHFFFAOYSA-N 0.000 description 1
- CHCWUTJYLUBETR-UHFFFAOYSA-N (3-ethoxyphenyl)boronic acid Chemical compound CCOC1=CC=CC(B(O)O)=C1 CHCWUTJYLUBETR-UHFFFAOYSA-N 0.000 description 1
- WPVBHUUZDFUIJA-UHFFFAOYSA-N (3-fluoro-4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1F WPVBHUUZDFUIJA-UHFFFAOYSA-N 0.000 description 1
- SKVGLOFWEJFQKU-UHFFFAOYSA-N (3-fluorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=CC(F)=C1 SKVGLOFWEJFQKU-UHFFFAOYSA-N 0.000 description 1
- MOOOGTOEKZWEJA-UHFFFAOYSA-N (3-methylthiophen-2-yl)boronic acid Chemical compound CC=1C=CSC=1B(O)O MOOOGTOEKZWEJA-UHFFFAOYSA-N 0.000 description 1
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- QWMJEUJXWVZSAG-UHFFFAOYSA-N (4-ethenylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=C)C=C1 QWMJEUJXWVZSAG-UHFFFAOYSA-N 0.000 description 1
- WLCGYIWOKVWFLB-UHFFFAOYSA-N (4-propylphenyl)boronic acid Chemical compound CCCC1=CC=C(B(O)O)C=C1 WLCGYIWOKVWFLB-UHFFFAOYSA-N 0.000 description 1
- OTKFCIVOVKCFHR-UHFFFAOYSA-N (Methylsulfinyl)(methylthio)methane Chemical compound CSCS(C)=O OTKFCIVOVKCFHR-UHFFFAOYSA-N 0.000 description 1
- GVNNGJMKAFLSHZ-NSCUHMNNSA-N (e)-1,3-dichlorobut-1-ene Chemical compound CC(Cl)\C=C\Cl GVNNGJMKAFLSHZ-NSCUHMNNSA-N 0.000 description 1
- AFHPVXVEXINDFS-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-4-iodobutane Chemical compound FC(F)(F)C(F)(F)C(F)(F)CI AFHPVXVEXINDFS-UHFFFAOYSA-N 0.000 description 1
- KMGHCDZLSCNMDC-UHFFFAOYSA-N 1,2-bis(methylsulfanyl)benzene Chemical compound CSC1=CC=CC=C1SC KMGHCDZLSCNMDC-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- OFUIFLZWMQEMFY-UHFFFAOYSA-N 1,2-dihydropyridazine-3,4-dione Chemical compound O=C1C=CNNC1=O OFUIFLZWMQEMFY-UHFFFAOYSA-N 0.000 description 1
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 description 1
- PRAYGQDVLDHWHA-UHFFFAOYSA-N 1,3-dibromo-1,1-difluoropropane Chemical compound FC(F)(Br)CCBr PRAYGQDVLDHWHA-UHFFFAOYSA-N 0.000 description 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- 125000005877 1,4-benzodioxanyl group Chemical group 0.000 description 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- OTWORIPHJRKXBR-UHFFFAOYSA-N 1-(1-benzothiophen-3-yl)-2-chloroethanone Chemical compound C1=CC=C2C(C(=O)CCl)=CSC2=C1 OTWORIPHJRKXBR-UHFFFAOYSA-N 0.000 description 1
- PHGMUOJCQCLPBD-UHFFFAOYSA-N 1-(1-bromoethyl)-4-fluorobenzene Chemical compound CC(Br)C1=CC=C(F)C=C1 PHGMUOJCQCLPBD-UHFFFAOYSA-N 0.000 description 1
- JNTWNAKIPDIYJZ-UHFFFAOYSA-N 1-(1-chloroethyl)-2,3,4-trifluorobenzene Chemical compound CC(Cl)C1=CC=C(F)C(F)=C1F JNTWNAKIPDIYJZ-UHFFFAOYSA-N 0.000 description 1
- OHENRIZEXJXOAN-UHFFFAOYSA-N 1-(1-chloroethyl)-3,5-difluorobenzene Chemical compound CC(Cl)C1=CC(F)=CC(F)=C1 OHENRIZEXJXOAN-UHFFFAOYSA-N 0.000 description 1
- MJUVRTYWUMPBTR-MRXNPFEDSA-N 1-(2,2-difluoro-1,3-benzodioxol-5-yl)-n-[1-[(2r)-2,3-dihydroxypropyl]-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)indol-5-yl]cyclopropane-1-carboxamide Chemical compound FC=1C=C2N(C[C@@H](O)CO)C(C(C)(CO)C)=CC2=CC=1NC(=O)C1(C=2C=C3OC(F)(F)OC3=CC=2)CC1 MJUVRTYWUMPBTR-MRXNPFEDSA-N 0.000 description 1
- PSDSORRYQPTKSV-UHFFFAOYSA-N 1-(4-fluorophenyl)ethanol Chemical compound CC(O)C1=CC=C(F)C=C1 PSDSORRYQPTKSV-UHFFFAOYSA-N 0.000 description 1
- FMURNAZHVQDQQN-UHFFFAOYSA-N 1-(4-iodophenyl)pyrrole Chemical compound C1=CC(I)=CC=C1N1C=CC=C1 FMURNAZHVQDQQN-UHFFFAOYSA-N 0.000 description 1
- DGSXDQVPGXFOAN-UHFFFAOYSA-N 1-(bromomethyl)-2,3,4-trifluorobenzene Chemical compound FC1=CC=C(CBr)C(F)=C1F DGSXDQVPGXFOAN-UHFFFAOYSA-N 0.000 description 1
- GAUXEYCSWSMMFZ-UHFFFAOYSA-N 1-(bromomethyl)-2,4,5-trifluorobenzene Chemical compound FC1=CC(F)=C(CBr)C=C1F GAUXEYCSWSMMFZ-UHFFFAOYSA-N 0.000 description 1
- IBLMYGXJKQIGSN-UHFFFAOYSA-N 1-(bromomethyl)-2,4-difluorobenzene Chemical compound FC1=CC=C(CBr)C(F)=C1 IBLMYGXJKQIGSN-UHFFFAOYSA-N 0.000 description 1
- TXVVVEUSVBLDED-UHFFFAOYSA-N 1-(bromomethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1CBr TXVVVEUSVBLDED-UHFFFAOYSA-N 0.000 description 1
- SCBZBMXPJYMXRC-UHFFFAOYSA-N 1-(bromomethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(CBr)=C1 SCBZBMXPJYMXRC-UHFFFAOYSA-N 0.000 description 1
- PDKVWCYJNKLAGE-UHFFFAOYSA-N 1-(bromomethyl)cyclohexene Chemical compound BrCC1=CCCCC1 PDKVWCYJNKLAGE-UHFFFAOYSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- MUVUDWJJCYNODW-UHFFFAOYSA-N 1-adamantyl 5-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)-6-oxopyridazine-1-carboxylate Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C(=O)OC23CC4CC(CC(C4)C2)C3)N=C1 MUVUDWJJCYNODW-UHFFFAOYSA-N 0.000 description 1
- MGHBDQZXPCTTIH-UHFFFAOYSA-N 1-bromo-2,4-difluorobenzene Chemical compound FC1=CC=C(Br)C(F)=C1 MGHBDQZXPCTTIH-UHFFFAOYSA-N 0.000 description 1
- XANVIFOBBVAKCY-UHFFFAOYSA-N 1-bromo-2-fluoro-4-methoxybenzene Chemical compound COC1=CC=C(Br)C(F)=C1 XANVIFOBBVAKCY-UHFFFAOYSA-N 0.000 description 1
- IPWBFGUBXWMIPR-UHFFFAOYSA-N 1-bromo-2-fluorobenzene Chemical compound FC1=CC=CC=C1Br IPWBFGUBXWMIPR-UHFFFAOYSA-N 0.000 description 1
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
- SAIRZMWXVJEBMO-UHFFFAOYSA-N 1-bromo-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)CBr SAIRZMWXVJEBMO-UHFFFAOYSA-N 0.000 description 1
- JHLKSIOJYMGSMB-UHFFFAOYSA-N 1-bromo-3,5-difluorobenzene Chemical compound FC1=CC(F)=CC(Br)=C1 JHLKSIOJYMGSMB-UHFFFAOYSA-N 0.000 description 1
- LMFRTSBQRLSJHC-UHFFFAOYSA-N 1-bromo-3,5-dimethylbenzene Chemical group CC1=CC(C)=CC(Br)=C1 LMFRTSBQRLSJHC-UHFFFAOYSA-N 0.000 description 1
- KQJQPCJDKBKSLV-UHFFFAOYSA-N 1-bromo-3-ethenylbenzene Chemical compound BrC1=CC=CC(C=C)=C1 KQJQPCJDKBKSLV-UHFFFAOYSA-N 0.000 description 1
- WJIFKOVZNJTSGO-UHFFFAOYSA-N 1-bromo-3-methylbenzene Chemical compound CC1=CC=CC(Br)=C1 WJIFKOVZNJTSGO-UHFFFAOYSA-N 0.000 description 1
- NKYFJZAKUPSUSH-UHFFFAOYSA-N 1-bromo-3-methylsulfanylbenzene Chemical compound CSC1=CC=CC(Br)=C1 NKYFJZAKUPSUSH-UHFFFAOYSA-N 0.000 description 1
- USYQKCQEVBFJRP-UHFFFAOYSA-N 1-bromo-3-phenylbenzene Chemical group BrC1=CC=CC(C=2C=CC=CC=2)=C1 USYQKCQEVBFJRP-UHFFFAOYSA-N 0.000 description 1
- XLQSXGGDTHANLN-UHFFFAOYSA-N 1-bromo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Br)C=C1 XLQSXGGDTHANLN-UHFFFAOYSA-N 0.000 description 1
- FPNVMCMDWZNTEU-UHFFFAOYSA-N 1-bromo-4-chloro-2-fluorobenzene Chemical compound FC1=CC(Cl)=CC=C1Br FPNVMCMDWZNTEU-UHFFFAOYSA-N 0.000 description 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 1
- XZKFBZOAIGFZSU-UHFFFAOYSA-N 1-bromo-4-methylpentane Chemical compound CC(C)CCCBr XZKFBZOAIGFZSU-UHFFFAOYSA-N 0.000 description 1
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- XHCAGOVGSDHHNP-UHFFFAOYSA-N 1-bromo-4-tert-butylbenzene Chemical compound CC(C)(C)C1=CC=C(Br)C=C1 XHCAGOVGSDHHNP-UHFFFAOYSA-N 0.000 description 1
- DNLYUDULMRQGPU-UHFFFAOYSA-N 1-bromoprop-2-ynylbenzene Chemical compound C#CC(Br)C1=CC=CC=C1 DNLYUDULMRQGPU-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical class CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- PDOSDJLFIKYYMV-UHFFFAOYSA-N 1-chlorohex-2-yne Chemical compound CCCC#CCCl PDOSDJLFIKYYMV-UHFFFAOYSA-N 0.000 description 1
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical class CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- VSKSBSORLCDRHS-UHFFFAOYSA-N 1-fluoro-3-iodobenzene Chemical compound FC1=CC=CC(I)=C1 VSKSBSORLCDRHS-UHFFFAOYSA-N 0.000 description 1
- SCCCFNJTCDSLCY-UHFFFAOYSA-N 1-iodo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(I)C=C1 SCCCFNJTCDSLCY-UHFFFAOYSA-N 0.000 description 1
- BHWJMPDCCDMCKC-UHFFFAOYSA-N 1-methyl-2-methylsulfanylbenzene Chemical compound CSC1=CC=CC=C1C BHWJMPDCCDMCKC-UHFFFAOYSA-N 0.000 description 1
- CAKWRXVKWGUISE-UHFFFAOYSA-N 1-methylcyclopentan-1-ol Chemical compound CC1(O)CCCC1 CAKWRXVKWGUISE-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 description 1
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
- AMGDNQWQBWPRPR-UHFFFAOYSA-N 2,3,5-trifluoroaniline Chemical compound NC1=CC(F)=CC(F)=C1F AMGDNQWQBWPRPR-UHFFFAOYSA-N 0.000 description 1
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical group C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 description 1
- POBJOHQLAKTHHR-UHFFFAOYSA-N 2,4-bis(4-fluorophenyl)-5-(4-methylsulfinylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=CC(F)=CC=2)N=C1 POBJOHQLAKTHHR-UHFFFAOYSA-N 0.000 description 1
- ZJNPRKCBXLIJBL-UHFFFAOYSA-N 2,4-dichloropyridazin-3-one Chemical compound ClC1=CC=NN(Cl)C1=O ZJNPRKCBXLIJBL-UHFFFAOYSA-N 0.000 description 1
- CEPCPXLLFXPZGW-UHFFFAOYSA-N 2,4-difluoroaniline Chemical compound NC1=CC=C(F)C=C1F CEPCPXLLFXPZGW-UHFFFAOYSA-N 0.000 description 1
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
- MRDPZGANBLPSKR-UHFFFAOYSA-N 2-(1-benzothiophen-3-yl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C3=CC=CC=C3SC=2)N=C1 MRDPZGANBLPSKR-UHFFFAOYSA-N 0.000 description 1
- 125000003870 2-(1-piperidinyl)ethoxy group Chemical group [*]OC([H])([H])C([H])([H])N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- LYVSVJABVNWIRW-UHFFFAOYSA-N 2-(2,3-dihydro-1h-inden-1-yl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C2C3=CC=CC=C3CC2)N=C1 LYVSVJABVNWIRW-UHFFFAOYSA-N 0.000 description 1
- YKZASNVLAVCTIN-UHFFFAOYSA-N 2-(2,3-dihydro-1h-inden-2-yl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C2CC3=CC=CC=C3C2)N=C1 YKZASNVLAVCTIN-UHFFFAOYSA-N 0.000 description 1
- NSJDIGOATHZTAG-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C(=CC(F)=CC=2)F)N=C1 NSJDIGOATHZTAG-UHFFFAOYSA-N 0.000 description 1
- NHLJKDXQQNKUFY-UHFFFAOYSA-N 2-(2,5-difluorophenyl)-5-(4-methylsulfanylphenyl)-4-propan-2-yloxypyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(OC(C)C)C(=O)N(C=2C(=CC=C(F)C=2)F)N=C1 NHLJKDXQQNKUFY-UHFFFAOYSA-N 0.000 description 1
- CLHFSXHNCQVEMX-UHFFFAOYSA-N 2-(2,5-difluorophenyl)-5-(4-methylsulfonylphenyl)-4-propan-2-yloxypyridazin-3-one Chemical compound O=C1C(OC(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC(F)=CC=C1F CLHFSXHNCQVEMX-UHFFFAOYSA-N 0.000 description 1
- XPTYAIQIWGCKSM-UHFFFAOYSA-N 2-(2-adamantyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C2C3CC4CC(C3)CC2C4)N=C1 XPTYAIQIWGCKSM-UHFFFAOYSA-N 0.000 description 1
- WMDHQEHPOVOEOG-UHFFFAOYSA-N 2-(2-bromoethyl)-1,3-dioxane Chemical compound BrCCC1OCCCO1 WMDHQEHPOVOEOG-UHFFFAOYSA-N 0.000 description 1
- AKQTTXNCTAPFQJ-UHFFFAOYSA-N 2-(2-fluorophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C(=CC=CC=2)F)N=C1 AKQTTXNCTAPFQJ-UHFFFAOYSA-N 0.000 description 1
- GSWDFMGVIWOONC-UHFFFAOYSA-N 2-(3,3-dichloroprop-2-enyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=C(Cl)Cl)N=C1 GSWDFMGVIWOONC-UHFFFAOYSA-N 0.000 description 1
- RZZPWPUVOBUSJL-UHFFFAOYSA-N 2-(3,3-dimethyl-2-oxobutyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C=1C=C(F)C=CC=1C=1C(=O)N(CC(=O)C(C)(C)C)N=CC=1C1=CC=C(S(C)(=O)=O)C=C1 RZZPWPUVOBUSJL-UHFFFAOYSA-N 0.000 description 1
- NDMCDTGCUPPGDA-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(2,2-dimethylpropoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCC(C)(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 NDMCDTGCUPPGDA-UHFFFAOYSA-N 0.000 description 1
- PMCGQESQBHKKBB-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(2-methylpropoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCC(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 PMCGQESQBHKKBB-UHFFFAOYSA-N 0.000 description 1
- JLBBZGOWFMLFBR-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(3-ethenyl-4-fluorophenyl)-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(C=C)C(F)=CC=2)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 JLBBZGOWFMLFBR-UHFFFAOYSA-N 0.000 description 1
- YUXGIVLUVDJMOB-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(3-methoxybutoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCC(C)OC)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 YUXGIVLUVDJMOB-UHFFFAOYSA-N 0.000 description 1
- ULCFKXUAWHLZOP-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(3-methylbutoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCC(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 ULCFKXUAWHLZOP-UHFFFAOYSA-N 0.000 description 1
- FMEKYAFTOIRDLB-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(3-methylbutyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(CCC(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 FMEKYAFTOIRDLB-UHFFFAOYSA-N 0.000 description 1
- ZGWLCZVSTHRQOU-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(3-methylpentoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCC(C)CC)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 ZGWLCZVSTHRQOU-UHFFFAOYSA-N 0.000 description 1
- ZNLVJAPQPHHPEU-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(4-fluoro-3-methylphenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=C(F)C(C)=CC(C=2C(N(C=3C=C(F)C(F)=CC=3)N=CC=2C=2C=CC(=CC=2)S(C)(=O)=O)=O)=C1 ZNLVJAPQPHHPEU-UHFFFAOYSA-N 0.000 description 1
- XAAAOJSROIOEPG-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(4-fluorophenoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC(F)=CC=2)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 XAAAOJSROIOEPG-UHFFFAOYSA-N 0.000 description 1
- UJWFGGWCJOFGSU-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(4-methylpent-3-enoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCC=C(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 UJWFGGWCJOFGSU-UHFFFAOYSA-N 0.000 description 1
- AKZDJGRKKBNSQG-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(4-methylphenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(C)=CC=C1C(C1=O)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 AKZDJGRKKBNSQG-UHFFFAOYSA-N 0.000 description 1
- MMUOCNVFSYHWNF-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(5-methylhex-3-enyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(CCC=CC(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 MMUOCNVFSYHWNF-UHFFFAOYSA-N 0.000 description 1
- AWXVHYKAPJPFRV-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(5-methylhexyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(CCCCC(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 AWXVHYKAPJPFRV-UHFFFAOYSA-N 0.000 description 1
- CFPGZIPRPDTWQU-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(6-methylhept-3-enyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(CCC=CCC(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 CFPGZIPRPDTWQU-UHFFFAOYSA-N 0.000 description 1
- UJBRARNXJAMXKU-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-[(3,4-difluorophenyl)methyl]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CC=2C=C(F)C(F)=CC=2)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 UJBRARNXJAMXKU-UHFFFAOYSA-N 0.000 description 1
- OZUXQWOVTKIITR-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-[(3-fluorophenyl)methyl]-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(CC=2C=C(F)C=CC=2)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 OZUXQWOVTKIITR-UHFFFAOYSA-N 0.000 description 1
- HKEGVDKDHCSUOD-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-[(3-fluorophenyl)methyl]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CC=2C=C(F)C=CC=2)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 HKEGVDKDHCSUOD-UHFFFAOYSA-N 0.000 description 1
- OUNRLDMKGPJESX-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-[(4-fluorophenyl)methyl]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CC=2C=CC(F)=CC=2)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 OUNRLDMKGPJESX-UHFFFAOYSA-N 0.000 description 1
- SFFKPYCKUJKOOC-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-ethenyl-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=C)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 SFFKPYCKUJKOOC-UHFFFAOYSA-N 0.000 description 1
- FNAYJRCXTHWBOH-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-5-(3-fluoro-4-methylsulfonylphenyl)-4-(3-methylbutyl)pyridazin-3-one Chemical compound O=C1C(CCC(C)C)=C(C=2C=C(F)C(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 FNAYJRCXTHWBOH-UHFFFAOYSA-N 0.000 description 1
- CYKCVECVSRTMFA-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-5-(3-fluoro-4-methylsulfonylphenyl)-4-(4-fluorophenoxy)pyridazin-3-one Chemical compound C1=C(F)C(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC(F)=CC=2)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 CYKCVECVSRTMFA-UHFFFAOYSA-N 0.000 description 1
- UVWBUKFJDUFZHW-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-5-(4-methylsulfonylphenyl)-4-(2-phenylethynyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C#CC=2C=CC=CC=2)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 UVWBUKFJDUFZHW-UHFFFAOYSA-N 0.000 description 1
- DHLMAUADSWPOQX-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-5-(4-methylsulfonylphenyl)-4-(2-propan-2-yloxyethoxy)pyridazin-3-one Chemical compound O=C1C(OCCOC(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 DHLMAUADSWPOQX-UHFFFAOYSA-N 0.000 description 1
- CBPZHDYTBFOGBV-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-5-(4-methylsulfonylphenyl)-4-prop-1-ynylpyridazin-3-one Chemical compound O=C1C(C#CC)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 CBPZHDYTBFOGBV-UHFFFAOYSA-N 0.000 description 1
- PCMUGLNIDIAFRH-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-5-(4-methylsulfonylphenyl)-4-thiophen-2-ylpyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2SC=CC=2)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 PCMUGLNIDIAFRH-UHFFFAOYSA-N 0.000 description 1
- SRQAJMUHZROVHW-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)ethanol Chemical compound COC1=CC=C(CCO)C=C1OC SRQAJMUHZROVHW-UHFFFAOYSA-N 0.000 description 1
- MGJQRGNUVTXXII-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=C(Cl)C=C(Cl)C=2)N=C1 MGJQRGNUVTXXII-UHFFFAOYSA-N 0.000 description 1
- XCMNHYQQSPVCPZ-UHFFFAOYSA-N 2-(3,5-difluorophenyl)-4-(4-fluorophenoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC(F)=CC=2)C(=O)N(C=2C=C(F)C=C(F)C=2)N=C1 XCMNHYQQSPVCPZ-UHFFFAOYSA-N 0.000 description 1
- RFXFKYSABZPBCU-UHFFFAOYSA-N 2-(3,5-difluorophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=C(F)C=C(F)C=2)N=C1 RFXFKYSABZPBCU-UHFFFAOYSA-N 0.000 description 1
- JFYNULTUBVPGCZ-UHFFFAOYSA-N 2-(3,5-dimethylphenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound CC1=CC(C)=CC(N2C(C(C=3C=CC(F)=CC=3)=C(C=3C=CC(=CC=3)S(C)(=O)=O)C=N2)=O)=C1 JFYNULTUBVPGCZ-UHFFFAOYSA-N 0.000 description 1
- UEEFOBJFXIQIDQ-UHFFFAOYSA-N 2-(3-bromophenyl)-4-(4-fluorophenoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC(F)=CC=2)C(=O)N(C=2C=C(Br)C=CC=2)N=C1 UEEFOBJFXIQIDQ-UHFFFAOYSA-N 0.000 description 1
- JNSJDAPMIUMRDS-UHFFFAOYSA-N 2-(3-bromophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=C(Br)C=CC=2)N=C1 JNSJDAPMIUMRDS-UHFFFAOYSA-N 0.000 description 1
- MGVXEONFYAMBLD-UHFFFAOYSA-N 2-(3-bromophenyl)-5-(4-methylsulfonylphenyl)-4-propan-2-yloxypyridazin-3-one Chemical compound O=C1C(OC(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(Br)=C1 MGVXEONFYAMBLD-UHFFFAOYSA-N 0.000 description 1
- GAGRAEISSQCIOC-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-(3,5-difluoro-4-methoxyphenyl)-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=C(F)C=C1C(C1=O)=C(C=2C=CC(SC)=CC=2)C=NN1C1=CC=C(F)C(Cl)=C1 GAGRAEISSQCIOC-UHFFFAOYSA-N 0.000 description 1
- VWKNOFUTLUBLSR-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-(3,5-difluoro-4-methoxyphenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=C(F)C=C1C(C1=O)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(Cl)=C1 VWKNOFUTLUBLSR-UHFFFAOYSA-N 0.000 description 1
- PYOWMEYFYLXMLM-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-(3-methylbutyl)-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(CCC(C)C)C(=O)N(C=2C=C(Cl)C(F)=CC=2)N=C1 PYOWMEYFYLXMLM-UHFFFAOYSA-N 0.000 description 1
- RHZYUFMHFDVPAH-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-(3-methylbutyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(CCC(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(Cl)=C1 RHZYUFMHFDVPAH-UHFFFAOYSA-N 0.000 description 1
- QXDXUGXRAFDKKV-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-(4-chlorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)C(=O)N(C=2C=C(Cl)C(F)=CC=2)N=C1 QXDXUGXRAFDKKV-UHFFFAOYSA-N 0.000 description 1
- YVTOWWUMHYNIIE-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-(4-fluoro-3-methylphenyl)-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(C)C(F)=CC=2)C(=O)N(C=2C=C(Cl)C(F)=CC=2)N=C1 YVTOWWUMHYNIIE-UHFFFAOYSA-N 0.000 description 1
- ZDVJZYQNOUCEIP-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-(4-fluoro-3-methylphenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=C(F)C(C)=CC(C=2C(N(C=3C=C(Cl)C(F)=CC=3)N=CC=2C=2C=CC(=CC=2)S(C)(=O)=O)=O)=C1 ZDVJZYQNOUCEIP-UHFFFAOYSA-N 0.000 description 1
- TXBDEQGNPLKVCW-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=C(Cl)C(F)=CC=2)N=C1 TXBDEQGNPLKVCW-UHFFFAOYSA-N 0.000 description 1
- FQIVTBQXZLSLOC-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-[(3-fluorophenyl)methyl]-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(CC=2C=C(F)C=CC=2)C(=O)N(C=2C=C(Cl)C(F)=CC=2)N=C1 FQIVTBQXZLSLOC-UHFFFAOYSA-N 0.000 description 1
- MTOWLIXDMZMDNW-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-[(3-fluorophenyl)methyl]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CC=2C=C(F)C=CC=2)C(=O)N(C=2C=C(Cl)C(F)=CC=2)N=C1 MTOWLIXDMZMDNW-UHFFFAOYSA-N 0.000 description 1
- PNUKEHLLDXICOE-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-[(4-fluorophenyl)methyl]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CC=2C=CC(F)=CC=2)C(=O)N(C=2C=C(Cl)C(F)=CC=2)N=C1 PNUKEHLLDXICOE-UHFFFAOYSA-N 0.000 description 1
- LYHKHMCDCKULQD-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-cyclohexyl-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(C2CCCCC2)C(=O)N(C=2C=C(Cl)C(F)=CC=2)N=C1 LYHKHMCDCKULQD-UHFFFAOYSA-N 0.000 description 1
- NBIXDBGGOMFFEZ-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-5-(3-fluoro-4-methylsulfonylphenyl)-4-(2-methylpropoxy)pyridazin-3-one Chemical compound O=C1C(OCC(C)C)=C(C=2C=C(F)C(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(Cl)=C1 NBIXDBGGOMFFEZ-UHFFFAOYSA-N 0.000 description 1
- TVVKLWAHEIFDOI-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-5-(3-fluoro-4-methylsulfonylphenyl)-4-(3-methylbutyl)pyridazin-3-one Chemical compound O=C1C(CCC(C)C)=C(C=2C=C(F)C(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(Cl)=C1 TVVKLWAHEIFDOI-UHFFFAOYSA-N 0.000 description 1
- PKRXRGFJHNLRAF-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(2,2-dimethylpropoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCC(C)(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(Cl)=C1 PKRXRGFJHNLRAF-UHFFFAOYSA-N 0.000 description 1
- PKBIXTOJELJDIA-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(2,4-dimethylpentan-3-yloxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC(C(C)C)C(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(Cl)=C1 PKBIXTOJELJDIA-UHFFFAOYSA-N 0.000 description 1
- HAFBIFLPDHICKN-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(2-methylpropoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCC(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(Cl)=C1 HAFBIFLPDHICKN-UHFFFAOYSA-N 0.000 description 1
- MADQSQJNCCGLAO-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(4-fluoro-3-methylphenyl)-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(C)C(F)=CC=2)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 MADQSQJNCCGLAO-UHFFFAOYSA-N 0.000 description 1
- ASECOZKANKXLHP-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(4-fluoro-3-methylphenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=C(F)C(C)=CC(C=2C(N(C=3C=C(Cl)C=CC=3)N=CC=2C=2C=CC(=CC=2)S(C)(=O)=O)=O)=C1 ASECOZKANKXLHP-UHFFFAOYSA-N 0.000 description 1
- QQQYXEQTAATFNG-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(4-fluorophenoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC(F)=CC=2)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 QQQYXEQTAATFNG-UHFFFAOYSA-N 0.000 description 1
- MSHFSGMAQYGNSR-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(4-fluorophenyl)-5-(3-methyl-4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=C(C)C(SC)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 MSHFSGMAQYGNSR-UHFFFAOYSA-N 0.000 description 1
- MEUNOXFZDGSFEM-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 MEUNOXFZDGSFEM-UHFFFAOYSA-N 0.000 description 1
- GICWTNFSAPWCRX-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(4-methoxyphenoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(OC)=CC=C1OC(C1=O)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(Cl)=C1 GICWTNFSAPWCRX-UHFFFAOYSA-N 0.000 description 1
- MPOYPUTXUUGZAM-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(4-methylphenyl)sulfanyl-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(C)=CC=C1SC(C1=O)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(Cl)=C1 MPOYPUTXUUGZAM-UHFFFAOYSA-N 0.000 description 1
- MMTXJJSTFKNADK-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(furan-2-ylmethylsulfanyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(SCC=2OC=CC=2)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 MMTXJJSTFKNADK-UHFFFAOYSA-N 0.000 description 1
- JXFYKPGAAYLKFR-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-[(2-methylpropan-2-yl)oxy]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC(C)(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(Cl)=C1 JXFYKPGAAYLKFR-UHFFFAOYSA-N 0.000 description 1
- BLMRSACSUBIHKU-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-[(3-fluorophenyl)methyl]-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(CC=2C=C(F)C=CC=2)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 BLMRSACSUBIHKU-UHFFFAOYSA-N 0.000 description 1
- TXLUSHFAYHSCDJ-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-[(3-fluorophenyl)methyl]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CC=2C=C(F)C=CC=2)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 TXLUSHFAYHSCDJ-UHFFFAOYSA-N 0.000 description 1
- VLOKVGIGLHQVDM-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-[2-(dimethylamino)ethoxy]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCN(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(Cl)=C1 VLOKVGIGLHQVDM-UHFFFAOYSA-N 0.000 description 1
- CVURQOAKBNUVEJ-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-[3-(dimethylamino)phenyl]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound CN(C)C1=CC=CC(C=2C(N(C=3C=C(Cl)C=CC=3)N=CC=2C=2C=CC(=CC=2)S(C)(=O)=O)=O)=C1 CVURQOAKBNUVEJ-UHFFFAOYSA-N 0.000 description 1
- UNDNIEAJYRMIFL-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-cyclohexyloxy-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC2CCCCC2)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 UNDNIEAJYRMIFL-UHFFFAOYSA-N 0.000 description 1
- DUEFBCZGFCCQII-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-cyclopentyl-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C2CCCC2)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 DUEFBCZGFCCQII-UHFFFAOYSA-N 0.000 description 1
- ZWZXEIVSKMVDHV-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-methoxy-5-(3-methyl-4-methylsulfanylphenyl)pyridazin-3-one Chemical compound O=C1C(OC)=C(C=2C=C(C)C(SC)=CC=2)C=NN1C1=CC=CC(Cl)=C1 ZWZXEIVSKMVDHV-UHFFFAOYSA-N 0.000 description 1
- JWEKVIVDJDVMEW-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-methoxy-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(Cl)=C1 JWEKVIVDJDVMEW-UHFFFAOYSA-N 0.000 description 1
- KIRMRGBGXMZXBU-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-methyl-5-(3-methyl-4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=C(C)C(SC)=CC=C1C1=C(C)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 KIRMRGBGXMZXBU-UHFFFAOYSA-N 0.000 description 1
- QYYUHONWBQBXTG-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-methyl-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(C)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 QYYUHONWBQBXTG-UHFFFAOYSA-N 0.000 description 1
- ZECDSMNYFWKAOY-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-methyl-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(Cl)=C1 ZECDSMNYFWKAOY-UHFFFAOYSA-N 0.000 description 1
- JDABXFAFLXSJOU-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-(4-methylsulfanylphenyl)-4-propan-2-yloxypyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(OC(C)C)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 JDABXFAFLXSJOU-UHFFFAOYSA-N 0.000 description 1
- AFNKKAWQKJKDKX-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-(4-methylsulfonylphenyl)-4-(phenylmethoxymethyl)pyridazin-3-one Chemical compound ClC=1C=C(C=CC=1)N1N=CC(=C(C1=O)COCC1=CC=CC=C1)C1=CC=C(C=C1)S(=O)(=O)C AFNKKAWQKJKDKX-UHFFFAOYSA-N 0.000 description 1
- RSNDACDBYBEAQL-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-(4-methylsulfonylphenyl)-4-phenoxypyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC=CC=2)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 RSNDACDBYBEAQL-UHFFFAOYSA-N 0.000 description 1
- VSVSJJCOXBXNNE-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-(4-methylsulfonylphenyl)-4-propan-2-yloxypyridazin-3-one Chemical compound O=C1C(OC(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(Cl)=C1 VSVSJJCOXBXNNE-UHFFFAOYSA-N 0.000 description 1
- HVMIJDZIDSDTEI-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-(4-methylsulfonylphenyl)-4-pyridin-2-ylsulfanylpyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(SC=2N=CC=CC=2)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 HVMIJDZIDSDTEI-UHFFFAOYSA-N 0.000 description 1
- ULCQZXKKAWZJOW-UHFFFAOYSA-N 2-(3-ethenylphenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=C(C=C)C=CC=2)N=C1 ULCQZXKKAWZJOW-UHFFFAOYSA-N 0.000 description 1
- FBOUWMGKVIQINZ-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1N1C(=O)C(C=2C=CC(F)=CC=2)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=N1 FBOUWMGKVIQINZ-UHFFFAOYSA-N 0.000 description 1
- MEHJMXDESBHSPV-UHFFFAOYSA-N 2-(3-fluorophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=C(F)C=CC=2)N=C1 MEHJMXDESBHSPV-UHFFFAOYSA-N 0.000 description 1
- XUNVAEZUPWYCRV-UHFFFAOYSA-N 2-(3-fluorophenyl)-5-(4-methylsulfonylphenyl)-4-propan-2-yloxypyridazin-3-one Chemical compound O=C1C(OC(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(F)=C1 XUNVAEZUPWYCRV-UHFFFAOYSA-N 0.000 description 1
- CFFAPLZGSUNYMC-UHFFFAOYSA-N 2-(4-bromophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=CC(Br)=CC=2)N=C1 CFFAPLZGSUNYMC-UHFFFAOYSA-N 0.000 description 1
- ZNGPSRWLKXBYRU-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C(=CC(Cl)=CC=2)F)N=C1 ZNGPSRWLKXBYRU-UHFFFAOYSA-N 0.000 description 1
- IANWEGXVOYEDEB-UHFFFAOYSA-N 2-(4-chloro-3-fluorophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=C(F)C(Cl)=CC=2)N=C1 IANWEGXVOYEDEB-UHFFFAOYSA-N 0.000 description 1
- ZXPIYBVODWBCTP-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=CC(Cl)=CC=2)N=C1 ZXPIYBVODWBCTP-UHFFFAOYSA-N 0.000 description 1
- DNCZVIMOQRINLF-UHFFFAOYSA-N 2-(4-fluoro-3-methylphenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=C(F)C(C)=CC(N2C(C(C=3C=CC(F)=CC=3)=C(C=3C=CC(=CC=3)S(C)(=O)=O)C=N2)=O)=C1 DNCZVIMOQRINLF-UHFFFAOYSA-N 0.000 description 1
- FBSDABSAFURJDP-UHFFFAOYSA-N 2-(4-fluoro-3-methylsulfanylphenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=C(F)C(SC)=CC(N2C(C(C=3C=CC(F)=CC=3)=C(C=3C=CC(=CC=3)S(C)(=O)=O)C=N2)=O)=C1 FBSDABSAFURJDP-UHFFFAOYSA-N 0.000 description 1
- CENBXGGVWUCBFH-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-(2-methylpropylsulfanylmethyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(CSCC(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C=C1 CENBXGGVWUCBFH-UHFFFAOYSA-N 0.000 description 1
- ICDNHBBYEUQTRX-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-(4-methylphenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(C)=CC=C1C(C1=O)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C=C1 ICDNHBBYEUQTRX-UHFFFAOYSA-N 0.000 description 1
- AAKLXHDNVHZTED-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-(iodomethyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CI)C(=O)N(C=2C=CC(F)=CC=2)N=C1 AAKLXHDNVHZTED-UHFFFAOYSA-N 0.000 description 1
- KTDOILHDQRWXIH-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-[(3-fluorophenyl)methyl]-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(CC=2C=C(F)C=CC=2)C(=O)N(C=2C=CC(F)=CC=2)N=C1 KTDOILHDQRWXIH-UHFFFAOYSA-N 0.000 description 1
- ZTQJWCKFSAVCBO-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-[(3-fluorophenyl)methyl]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CC=2C=C(F)C=CC=2)C(=O)N(C=2C=CC(F)=CC=2)N=C1 ZTQJWCKFSAVCBO-UHFFFAOYSA-N 0.000 description 1
- GAYYLSIKYIFCPK-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-(4-methylsulfanylphenyl)-4-propan-2-yloxypyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(OC(C)C)C(=O)N(C=2C=CC(F)=CC=2)N=C1 GAYYLSIKYIFCPK-UHFFFAOYSA-N 0.000 description 1
- XKCFQZNRABQLBB-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-4-(2-phenylethynyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C#CC=2C=CC=CC=2)C(=O)N(C=2C=CC(F)=CC=2)N=C1 XKCFQZNRABQLBB-UHFFFAOYSA-N 0.000 description 1
- XMXDUCGHRGFLAJ-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-4-(phenoxymethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(COC=2C=CC=CC=2)C(=O)N(C=2C=CC(F)=CC=2)N=C1 XMXDUCGHRGFLAJ-UHFFFAOYSA-N 0.000 description 1
- VVRGUOVHFONAEO-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-4-piperidin-1-ylpyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(N2CCCCC2)C(=O)N(C=2C=CC(F)=CC=2)N=C1 VVRGUOVHFONAEO-UHFFFAOYSA-N 0.000 description 1
- VJDSLKDWJCVONB-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-4-propan-2-yloxypyridazin-3-one Chemical compound O=C1C(OC(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C=C1 VJDSLKDWJCVONB-UHFFFAOYSA-N 0.000 description 1
- JXFLEQQEJKCLIP-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-4-pyrrolidin-1-ylpyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(N2CCCC2)C(=O)N(C=2C=CC(F)=CC=2)N=C1 JXFLEQQEJKCLIP-UHFFFAOYSA-N 0.000 description 1
- MGKPFALCNDRSQD-UHFFFAOYSA-N 2-(4-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(F)C=C1 MGKPFALCNDRSQD-UHFFFAOYSA-N 0.000 description 1
- FOUPVWYVSXKUSG-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C(C=2C=CC(F)=CC=2)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=N1 FOUPVWYVSXKUSG-UHFFFAOYSA-N 0.000 description 1
- MEOWEODZGJYKGZ-UHFFFAOYSA-N 2-(5-chlorothiophen-2-yl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2SC(Cl)=CC=2)N=C1 MEOWEODZGJYKGZ-UHFFFAOYSA-N 0.000 description 1
- SPPLWANVCVTGEQ-UHFFFAOYSA-N 2-(bromomethyl)-1,3,5-trifluorobenzene Chemical compound FC1=CC(F)=C(CBr)C(F)=C1 SPPLWANVCVTGEQ-UHFFFAOYSA-N 0.000 description 1
- YMQQUUAZCBTKCG-UHFFFAOYSA-N 2-(bromomethyl)-5-chloro-1,3-thiazole Chemical compound ClC1=CN=C(CBr)S1 YMQQUUAZCBTKCG-UHFFFAOYSA-N 0.000 description 1
- NFNNZPYIRODXQL-UHFFFAOYSA-N 2-(bromomethyl)-5-chlorothiophene Chemical compound ClC1=CC=C(CBr)S1 NFNNZPYIRODXQL-UHFFFAOYSA-N 0.000 description 1
- ZQQLDLLYNATGDU-UHFFFAOYSA-N 2-(bromomethyl)-5-methyl-1,3-thiazole Chemical compound CC1=CN=C(CBr)S1 ZQQLDLLYNATGDU-UHFFFAOYSA-N 0.000 description 1
- WRVNJUJFUXXZJU-UHFFFAOYSA-N 2-(bromomethyl)-5-methylthiophene Chemical compound CC1=CC=C(CBr)S1 WRVNJUJFUXXZJU-UHFFFAOYSA-N 0.000 description 1
- OFPWMRMIFDHXFE-UHFFFAOYSA-N 2-(bromomethyl)pyridine Chemical compound BrCC1=CC=CC=N1 OFPWMRMIFDHXFE-UHFFFAOYSA-N 0.000 description 1
- JHDSVVPTMIYVGV-UHFFFAOYSA-N 2-(chloromethyl)-1-benzothiophene Chemical compound C1=CC=C2SC(CCl)=CC2=C1 JHDSVVPTMIYVGV-UHFFFAOYSA-N 0.000 description 1
- TYLAXVCCIGSMHK-UHFFFAOYSA-N 2-(chloromethyl)-6-fluoroquinoline Chemical compound N1=C(CCl)C=CC2=CC(F)=CC=C21 TYLAXVCCIGSMHK-UHFFFAOYSA-N 0.000 description 1
- DDEAEWMDOSXKBX-UHFFFAOYSA-N 2-(chloromethyl)quinoline Chemical compound C1=CC=CC2=NC(CCl)=CC=C21 DDEAEWMDOSXKBX-UHFFFAOYSA-N 0.000 description 1
- NRXNITPRTPIEKU-UHFFFAOYSA-N 2-(cyclopropylmethyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC2CC2)N=C1 NRXNITPRTPIEKU-UHFFFAOYSA-N 0.000 description 1
- KKFDCBRMNNSAAW-UHFFFAOYSA-N 2-(morpholin-4-yl)ethanol Chemical group OCCN1CCOCC1 KKFDCBRMNNSAAW-UHFFFAOYSA-N 0.000 description 1
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 1
- ZFFTZDQKIXPDAF-UHFFFAOYSA-N 2-Furanmethanethiol Chemical compound SCC1=CC=CO1 ZFFTZDQKIXPDAF-UHFFFAOYSA-N 0.000 description 1
- HRCYYPDMCGVKCY-UHFFFAOYSA-N 2-[(2,4-difluorophenyl)methyl]-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C(=CC(F)=CC=2)F)N=C1 HRCYYPDMCGVKCY-UHFFFAOYSA-N 0.000 description 1
- DAHAUWDJTVTSHD-UHFFFAOYSA-N 2-[(5-chloro-1,3-thiazol-2-yl)methyl]-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2SC(Cl)=CN=2)N=C1 DAHAUWDJTVTSHD-UHFFFAOYSA-N 0.000 description 1
- DMXSQLSERPGIGW-UHFFFAOYSA-N 2-[(5-chlorothiophen-2-yl)methyl]-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2SC(Cl)=CC=2)N=C1 DMXSQLSERPGIGW-UHFFFAOYSA-N 0.000 description 1
- UFMUDBKCLZFOBE-UHFFFAOYSA-N 2-[2-(1-benzothiophen-3-yl)-2-oxoethyl]-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC(=O)C=2C3=CC=CC=C3SC=2)N=C1 UFMUDBKCLZFOBE-UHFFFAOYSA-N 0.000 description 1
- OEIFKFCLEWNULG-UHFFFAOYSA-N 2-[2-(2,4-difluorophenyl)-2-oxoethyl]-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC(=O)C=2C(=CC(F)=CC=2)F)N=C1 OEIFKFCLEWNULG-UHFFFAOYSA-N 0.000 description 1
- WKDAFSHHDWMMNC-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-2-oxoethyl]-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC(=O)C=2C=CC(Cl)=CC=2)N=C1 WKDAFSHHDWMMNC-UHFFFAOYSA-N 0.000 description 1
- CYUJGVHTOCQSMB-UHFFFAOYSA-N 2-[2-[4-(diethylamino)phenyl]-2-oxoethyl]-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)CN1C(=O)C(C=2C=CC(F)=CC=2)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=N1 CYUJGVHTOCQSMB-UHFFFAOYSA-N 0.000 description 1
- XOTYHJHAEAFDAR-UHFFFAOYSA-N 2-[5-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)-6-oxopyridazin-1-yl]benzaldehyde Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C(=CC=CC=2)C=O)N=C1 XOTYHJHAEAFDAR-UHFFFAOYSA-N 0.000 description 1
- AJHBQZQCDCTOFD-UHFFFAOYSA-N 2-benzyl-4,5-dichloropyridazin-3-one Chemical compound O=C1C(Cl)=C(Cl)C=NN1CC1=CC=CC=C1 AJHBQZQCDCTOFD-UHFFFAOYSA-N 0.000 description 1
- SCFDQNAREOMPJI-UHFFFAOYSA-N 2-benzyl-4-(2-methoxyphenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound COC1=CC=CC=C1C(C1=O)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1CC1=CC=CC=C1 SCFDQNAREOMPJI-UHFFFAOYSA-N 0.000 description 1
- LIAIRLWQVDXKLU-UHFFFAOYSA-N 2-benzyl-4-(3,4-dimethylphenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=C(C)C(C)=CC=C1C(C1=O)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1CC1=CC=CC=C1 LIAIRLWQVDXKLU-UHFFFAOYSA-N 0.000 description 1
- YMGOWAMJUPASGL-UHFFFAOYSA-N 2-benzyl-4-(3-chloro-4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(Cl)C(F)=CC=2)C(=O)N(CC=2C=CC=CC=2)N=C1 YMGOWAMJUPASGL-UHFFFAOYSA-N 0.000 description 1
- GVPNBCPEKPUUFJ-UHFFFAOYSA-N 2-benzyl-4-(3-ethoxyphenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound CCOC1=CC=CC(C=2C(N(CC=3C=CC=CC=3)N=CC=2C=2C=CC(=CC=2)S(C)(=O)=O)=O)=C1 GVPNBCPEKPUUFJ-UHFFFAOYSA-N 0.000 description 1
- CDFHHUPBJIQWBL-UHFFFAOYSA-N 2-benzyl-4-(3-fluoro-4-methoxyphenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C(C1=O)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1CC1=CC=CC=C1 CDFHHUPBJIQWBL-UHFFFAOYSA-N 0.000 description 1
- HSZCWVUQSHYFPP-UHFFFAOYSA-N 2-benzyl-4-(4-chlorophenoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC(Cl)=CC=2)C(=O)N(CC=2C=CC=CC=2)N=C1 HSZCWVUQSHYFPP-UHFFFAOYSA-N 0.000 description 1
- IWRFCSDZPOVQGA-UHFFFAOYSA-N 2-benzyl-4-(4-chlorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)C(=O)N(CC=2C=CC=CC=2)N=C1 IWRFCSDZPOVQGA-UHFFFAOYSA-N 0.000 description 1
- GWZITMRSDYVGTO-UHFFFAOYSA-N 2-benzyl-4-(4-ethenylphenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(C=C)=CC=2)C(=O)N(CC=2C=CC=CC=2)N=C1 GWZITMRSDYVGTO-UHFFFAOYSA-N 0.000 description 1
- LFKRGMPYBJNFSP-UHFFFAOYSA-N 2-benzyl-4-(4-fluorophenyl)-5-(4-methylsulfinylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C=CC=CC=2)N=C1 LFKRGMPYBJNFSP-UHFFFAOYSA-N 0.000 description 1
- ANARSYFBGMQWHT-UHFFFAOYSA-N 2-benzyl-4-(4-fluorophenyl)-5-hydroxypyridazin-3-one Chemical compound O=C1C(C=2C=CC(F)=CC=2)=C(O)C=NN1CC1=CC=CC=C1 ANARSYFBGMQWHT-UHFFFAOYSA-N 0.000 description 1
- MDCXGPBSVZGDTH-UHFFFAOYSA-N 2-benzyl-4-(4-fluorophenyl)-5-methoxypyridazin-3-one Chemical compound O=C1C(C=2C=CC(F)=CC=2)=C(OC)C=NN1CC1=CC=CC=C1 MDCXGPBSVZGDTH-UHFFFAOYSA-N 0.000 description 1
- XSXPPZLNIUHGFT-UHFFFAOYSA-N 2-benzyl-4-(5-chlorothiophen-2-yl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2SC(Cl)=CC=2)C(=O)N(CC=2C=CC=CC=2)N=C1 XSXPPZLNIUHGFT-UHFFFAOYSA-N 0.000 description 1
- JCDIBZWZLPWSFF-UHFFFAOYSA-N 2-benzyl-4-bromo-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(Br)C(=O)N(CC=2C=CC=CC=2)N=C1 JCDIBZWZLPWSFF-UHFFFAOYSA-N 0.000 description 1
- ZYDULQDIVQUJDV-UHFFFAOYSA-N 2-benzyl-4-chloro-5-(3-fluoro-4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=C(F)C(SC)=CC=C1C1=C(Cl)C(=O)N(CC=2C=CC=CC=2)N=C1 ZYDULQDIVQUJDV-UHFFFAOYSA-N 0.000 description 1
- UAYOKPPGWGHMEU-UHFFFAOYSA-N 2-benzyl-4-chloro-5-(4-methylsulfinylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)C)=CC=C1C1=C(Cl)C(=O)N(CC=2C=CC=CC=2)N=C1 UAYOKPPGWGHMEU-UHFFFAOYSA-N 0.000 description 1
- RUNVTBUDUQJDPQ-UHFFFAOYSA-N 2-benzyl-4-methoxy-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1CC1=CC=CC=C1 RUNVTBUDUQJDPQ-UHFFFAOYSA-N 0.000 description 1
- CCOUBNQRBMFQEZ-UHFFFAOYSA-N 2-benzyl-5-(4-methylsulfanylpentyl)-4-propan-2-yloxypyridazin-3-one Chemical compound O=C1C(OC(C)C)=C(CCCC(C)SC)C=NN1CC1=CC=CC=C1 CCOUBNQRBMFQEZ-UHFFFAOYSA-N 0.000 description 1
- QJULOHVROUJPEN-UHFFFAOYSA-N 2-benzyl-5-(4-methylsulfonylphenyl)-4-(1-oxo-3h-2-benzofuran-5-yl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C3COC(=O)C3=CC=2)C(=O)N(CC=2C=CC=CC=2)N=C1 QJULOHVROUJPEN-UHFFFAOYSA-N 0.000 description 1
- MOIYILFWUQBJIB-UHFFFAOYSA-N 2-benzyl-5-(4-methylsulfonylphenyl)-4-(3-nitrophenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(C=CC=2)[N+]([O-])=O)C(=O)N(CC=2C=CC=CC=2)N=C1 MOIYILFWUQBJIB-UHFFFAOYSA-N 0.000 description 1
- BIISQWTWJRFLBW-UHFFFAOYSA-N 2-benzyl-5-(4-methylsulfonylphenyl)-4-(propan-2-ylamino)pyridazin-3-one Chemical compound O=C1C(NC(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1CC1=CC=CC=C1 BIISQWTWJRFLBW-UHFFFAOYSA-N 0.000 description 1
- SGFXDAKGCBEGCS-UHFFFAOYSA-N 2-benzyl-5-(4-methylsulfonylphenyl)-4-[4-(trifluoromethyl)phenyl]pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(=CC=2)C(F)(F)F)C(=O)N(CC=2C=CC=CC=2)N=C1 SGFXDAKGCBEGCS-UHFFFAOYSA-N 0.000 description 1
- CMCUIBJDJUGWQY-UHFFFAOYSA-N 2-benzyl-5-(4-methylsulfonylphenyl)-4-propan-2-yloxypyridazin-3-one Chemical compound O=C1C(OC(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1CC1=CC=CC=C1 CMCUIBJDJUGWQY-UHFFFAOYSA-N 0.000 description 1
- BLLVUEYSKPPNAT-UHFFFAOYSA-N 2-benzyl-5-(4-methylsulfonylphenyl)-4-thiophen-3-ylpyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C2=CSC=C2)C(=O)N(CC=2C=CC=CC=2)N=C1 BLLVUEYSKPPNAT-UHFFFAOYSA-N 0.000 description 1
- FLAYZKKEOIAALB-UHFFFAOYSA-N 2-bromo-1-(4-chlorophenyl)ethanone Chemical compound ClC1=CC=C(C(=O)CBr)C=C1 FLAYZKKEOIAALB-UHFFFAOYSA-N 0.000 description 1
- AOAGGWLQIILIIV-UHFFFAOYSA-N 2-bromo-1-[4-(trifluoromethoxy)phenyl]ethanone Chemical compound FC(F)(F)OC1=CC=C(C(=O)CBr)C=C1 AOAGGWLQIILIIV-UHFFFAOYSA-N 0.000 description 1
- HEMROKPXTCOASZ-UHFFFAOYSA-N 2-bromo-1-[4-(trifluoromethyl)phenyl]ethanone Chemical compound FC(F)(F)C1=CC=C(C(=O)CBr)C=C1 HEMROKPXTCOASZ-UHFFFAOYSA-N 0.000 description 1
- YYJBWYBULYUKMR-UHFFFAOYSA-N 2-bromo-3-methylthiophene Chemical compound CC=1C=CSC=1Br YYJBWYBULYUKMR-UHFFFAOYSA-N 0.000 description 1
- ZFAJPWYXLYGUJU-UHFFFAOYSA-N 2-bromo-5-chlorothiophene Chemical compound ClC1=CC=C(Br)S1 ZFAJPWYXLYGUJU-UHFFFAOYSA-N 0.000 description 1
- ACDLOOGOFKSUPO-UHFFFAOYSA-N 2-bromo-5-methylthiophene Chemical compound CC1=CC=C(Br)S1 ACDLOOGOFKSUPO-UHFFFAOYSA-N 0.000 description 1
- ZPNFMDYBAQDFDY-UHFFFAOYSA-N 2-bromo-5-nitrothiophene Chemical compound [O-][N+](=O)C1=CC=C(Br)S1 ZPNFMDYBAQDFDY-UHFFFAOYSA-N 0.000 description 1
- NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 description 1
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 1
- VMLBUKDIZHJJHV-UHFFFAOYSA-N 2-but-3-en-2-yl-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C=1C=C(F)C=CC=1C=1C(=O)N(C(C=C)C)N=CC=1C1=CC=C(S(C)(=O)=O)C=C1 VMLBUKDIZHJJHV-UHFFFAOYSA-N 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
- XHGKAZUMLWXZTQ-UHFFFAOYSA-N 2-chloro-1-[4-(diethylamino)phenyl]ethanone Chemical compound CCN(CC)C1=CC=C(C(=O)CCl)C=C1 XHGKAZUMLWXZTQ-UHFFFAOYSA-N 0.000 description 1
- DBKWFYJNNDUPDV-UHFFFAOYSA-N 2-cyclobutyl-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C2CCC2)N=C1 DBKWFYJNNDUPDV-UHFFFAOYSA-N 0.000 description 1
- WSUUNWCFCJZKBR-UHFFFAOYSA-N 2-cyclohexyl-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C2CCCCC2)N=C1 WSUUNWCFCJZKBR-UHFFFAOYSA-N 0.000 description 1
- GYUUUDNYDSXXNE-UHFFFAOYSA-N 2-cyclopentyl-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C2CCCC2)N=C1 GYUUUDNYDSXXNE-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- XNCYLNQITSCLRH-UHFFFAOYSA-N 2-fluoro-4-[5-(4-fluorophenyl)-1-(3-methylbut-2-enyl)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound C=1C=C(F)C=CC=1C=1C(=O)N(CC=C(C)C)N=CC=1C1=CC=C(S(N)(=O)=O)C(F)=C1 XNCYLNQITSCLRH-UHFFFAOYSA-N 0.000 description 1
- MKRRYWGEQVWJCA-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethoxy)phenol Chemical compound OC1=CC(OC(F)(F)F)=CC=C1F MKRRYWGEQVWJCA-UHFFFAOYSA-N 0.000 description 1
- WJTZZPVVTSDNJJ-UHFFFAOYSA-N 2-fluorobenzenethiol Chemical compound FC1=CC=CC=C1S WJTZZPVVTSDNJJ-UHFFFAOYSA-N 0.000 description 1
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 1
- BVIJQMCYYASIFP-UHFFFAOYSA-N 2-methylcyclopentan-1-ol Chemical group CC1CCCC1O BVIJQMCYYASIFP-UHFFFAOYSA-N 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- QDXIYJIGKOVDHS-UHFFFAOYSA-N 2-methylprop-1-ene-1-thione Chemical compound CC(C)=C=S QDXIYJIGKOVDHS-UHFFFAOYSA-N 0.000 description 1
- VIKPDPHNYHUZQW-UHFFFAOYSA-M 2-methylpropyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC(C)C)C1=CC=CC=C1 VIKPDPHNYHUZQW-UHFFFAOYSA-M 0.000 description 1
- WBBPRCNXBQTYLF-UHFFFAOYSA-N 2-methylthioethanol Chemical compound CSCCO WBBPRCNXBQTYLF-UHFFFAOYSA-N 0.000 description 1
- 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
- 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 1
- HCGFUIQPSOCUHI-UHFFFAOYSA-N 2-propan-2-yloxyethanol Chemical compound CC(C)OCCO HCGFUIQPSOCUHI-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ANFVZRTXGLHTNI-UHFFFAOYSA-N 2-tert-butyl-4,5-dichloropyridazin-3-one Chemical compound CC(C)(C)N1N=CC(Cl)=C(Cl)C1=O ANFVZRTXGLHTNI-UHFFFAOYSA-N 0.000 description 1
- PMFRMZIFSRAMGH-UHFFFAOYSA-N 2-tert-butyl-4-(3-methylbutoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=NN(C(C)(C)C)C(=O)C(OCCC(C)C)=C1C1=CC=C(S(C)(=O)=O)C=C1 PMFRMZIFSRAMGH-UHFFFAOYSA-N 0.000 description 1
- FDHCVVFPAHVJQL-UHFFFAOYSA-N 2-tert-butyl-5-chloro-4-(3-methylbutoxy)pyridazin-3-one Chemical compound CC(C)CCOC1=C(Cl)C=NN(C(C)(C)C)C1=O FDHCVVFPAHVJQL-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- HQNOODJDSFSURF-UHFFFAOYSA-N 3-(1h-imidazol-2-yl)propan-1-amine Chemical compound NCCCC1=NC=CN1 HQNOODJDSFSURF-UHFFFAOYSA-N 0.000 description 1
- KHCXGFNZZRXOND-UHFFFAOYSA-N 3-(bromomethyl)pyridine Chemical compound BrCC1=CC=CN=C1 KHCXGFNZZRXOND-UHFFFAOYSA-N 0.000 description 1
- KKWWFYAKOFXBEY-UHFFFAOYSA-N 3-(chloromethyl)thiophene Chemical compound ClCC=1C=CSC=1 KKWWFYAKOFXBEY-UHFFFAOYSA-N 0.000 description 1
- MESJRHHDBDCQTH-UHFFFAOYSA-N 3-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC(O)=C1 MESJRHHDBDCQTH-UHFFFAOYSA-N 0.000 description 1
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 description 1
- NTGFDTPBDFXLNF-UHFFFAOYSA-N 3-[2-(3,4-difluorophenyl)-5-(4-methylsulfonylphenyl)-3-oxopyridazin-4-yl]propanal Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CCC=O)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 NTGFDTPBDFXLNF-UHFFFAOYSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
- RDFYIXTVXGJTSZ-UHFFFAOYSA-N 3-[[5-(4-methylsulfonylphenyl)-3-oxo-2-(2,2,2-trifluoroethyl)pyridazin-4-yl]amino]propanenitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(NCCC#N)C(=O)N(CC(F)(F)F)N=C1 RDFYIXTVXGJTSZ-UHFFFAOYSA-N 0.000 description 1
- SRWDQSRTOOMPMO-UHFFFAOYSA-N 3-bromo-1-benzothiophene Chemical compound C1=CC=C2C(Br)=CSC2=C1 SRWDQSRTOOMPMO-UHFFFAOYSA-N 0.000 description 1
- AJKDUJRRWLQXHM-UHFFFAOYSA-N 3-bromocyclohexene Chemical compound BrC1CCCC=C1 AJKDUJRRWLQXHM-UHFFFAOYSA-N 0.000 description 1
- LXWLEQZDXOQZGW-UHFFFAOYSA-N 3-bromofuran Chemical compound BrC=1C=COC=1 LXWLEQZDXOQZGW-UHFFFAOYSA-N 0.000 description 1
- RUROFEVDCUGKHD-UHFFFAOYSA-N 3-bromoprop-1-enylbenzene Chemical compound BrCC=CC1=CC=CC=C1 RUROFEVDCUGKHD-UHFFFAOYSA-N 0.000 description 1
- XCMISAPCWHTVNG-UHFFFAOYSA-N 3-bromothiophene Chemical compound BrC=1C=CSC=1 XCMISAPCWHTVNG-UHFFFAOYSA-N 0.000 description 1
- SFSHSIFYTWIGSF-UHFFFAOYSA-N 3-chloro-4-fluorobenzenethiol Chemical compound FC1=CC=C(S)C=C1Cl SFSHSIFYTWIGSF-UHFFFAOYSA-N 0.000 description 1
- ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
- QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 1
- SJTBRFHBXDZMPS-UHFFFAOYSA-N 3-fluorophenol Chemical compound OC1=CC=CC(F)=C1 SJTBRFHBXDZMPS-UHFFFAOYSA-N 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- VTFGJEYZCUWSAM-UHFFFAOYSA-N 3-methoxy-5-(trifluoromethyl)aniline Chemical compound COC1=CC(N)=CC(C(F)(F)F)=C1 VTFGJEYZCUWSAM-UHFFFAOYSA-N 0.000 description 1
- VEALHWXMCIRWGC-UHFFFAOYSA-N 3-methylcyclopentan-1-ol Chemical compound CC1CCC(O)C1 VEALHWXMCIRWGC-UHFFFAOYSA-N 0.000 description 1
- ZNRGSYUVFVNSAW-UHFFFAOYSA-N 3-nitrophenylboronic acid Chemical compound OB(O)C1=CC=CC([N+]([O-])=O)=C1 ZNRGSYUVFVNSAW-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- MTBWVKXRTWAYSV-UHFFFAOYSA-N 4,5-dichloro-2-phenyl-1,5-dihydropyridazin-6-one Chemical compound N1C(=O)C(Cl)C(Cl)=CN1C1=CC=CC=C1 MTBWVKXRTWAYSV-UHFFFAOYSA-N 0.000 description 1
- VKWCOHVAHQOJGU-UHFFFAOYSA-N 4,5-dichloro-2-phenylpyridazin-3-one Chemical compound O=C1C(Cl)=C(Cl)C=NN1C1=CC=CC=C1 VKWCOHVAHQOJGU-UHFFFAOYSA-N 0.000 description 1
- BPFQWHPWGMLYJG-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-2-benzyl-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2OC3=CC=CC=C3C=2)C(=O)N(CC=2C=CC=CC=2)N=C1 BPFQWHPWGMLYJG-UHFFFAOYSA-N 0.000 description 1
- JROOYCGCPLLVMQ-UHFFFAOYSA-N 4-(1-chloroethyl)-1,2-difluorobenzene Chemical compound CC(Cl)C1=CC=C(F)C(F)=C1 JROOYCGCPLLVMQ-UHFFFAOYSA-N 0.000 description 1
- KWEYKNXAIGKUDP-UHFFFAOYSA-N 4-(2,2-dimethylpropoxy)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=NN(CC(F)(F)F)C(=O)C(OCC(C)(C)C)=C1C1=CC=C(S(C)(=O)=O)C=C1 KWEYKNXAIGKUDP-UHFFFAOYSA-N 0.000 description 1
- GHZTVSJIOQOVMI-UHFFFAOYSA-N 4-(2,3-dihydro-1h-inden-1-ylamino)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(NC2C3=CC=CC=C3CC2)C(=O)N(CC(F)(F)F)N=C1 GHZTVSJIOQOVMI-UHFFFAOYSA-N 0.000 description 1
- PMFJRKWCAUQCMI-UHFFFAOYSA-N 4-(2,3-dihydro-1h-inden-1-yloxy)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC2C3=CC=CC=C3CC2)C(=O)N(CC(F)(F)F)N=C1 PMFJRKWCAUQCMI-UHFFFAOYSA-N 0.000 description 1
- QXXZORRJFWBBKJ-UHFFFAOYSA-N 4-(2,4-difluoroanilino)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(NC=2C(=CC(F)=CC=2)F)C(=O)N(CC(F)(F)F)N=C1 QXXZORRJFWBBKJ-UHFFFAOYSA-N 0.000 description 1
- QISIMXZXEZXIDN-UHFFFAOYSA-N 4-(2,5-dimethoxyanilino)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound COC1=CC=C(OC)C(NC=2C(N(CC(F)(F)F)N=CC=2C=2C=CC(=CC=2)S(C)(=O)=O)=O)=C1 QISIMXZXEZXIDN-UHFFFAOYSA-N 0.000 description 1
- LJANCPRIUMHGJE-UHFFFAOYSA-N 4-(2-bromoacetyl)benzonitrile Chemical compound BrCC(=O)C1=CC=C(C#N)C=C1 LJANCPRIUMHGJE-UHFFFAOYSA-N 0.000 description 1
- XNKHQJNQFKXQGI-UHFFFAOYSA-N 4-(2-ethylhexoxy)-2-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCC(CC)CCCC)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C=C1 XNKHQJNQFKXQGI-UHFFFAOYSA-N 0.000 description 1
- JCIXCYVNSAQYGO-UHFFFAOYSA-N 4-(2-methylphenyl)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound CC1=CC=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN(CC(F)(F)F)C1=O JCIXCYVNSAQYGO-UHFFFAOYSA-N 0.000 description 1
- WSWJNNVWVOLFRQ-UHFFFAOYSA-N 4-(2-methylpropylsulfanyl)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=NN(CC(F)(F)F)C(=O)C(SCC(C)C)=C1C1=CC=C(S(C)(=O)=O)C=C1 WSWJNNVWVOLFRQ-UHFFFAOYSA-N 0.000 description 1
- LCQOHNYKMYAZGF-UHFFFAOYSA-N 4-(2-methylsulfanylethoxy)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=NN(CC(F)(F)F)C(=O)C(OCCSC)=C1C1=CC=C(S(C)(=O)=O)C=C1 LCQOHNYKMYAZGF-UHFFFAOYSA-N 0.000 description 1
- UYQMXYRAGLBDKD-UHFFFAOYSA-N 4-(3,3-dimethylbutoxy)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=NN(CC(F)(F)F)C(=O)C(OCCC(C)(C)C)=C1C1=CC=C(S(C)(=O)=O)C=C1 UYQMXYRAGLBDKD-UHFFFAOYSA-N 0.000 description 1
- GAORKELXTLORHP-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(Cl)C(Cl)=CC=2)C(=O)N(CC(F)(F)F)N=C1 GAORKELXTLORHP-UHFFFAOYSA-N 0.000 description 1
- NKZSZZXYUGAAQP-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(Cl)C=C(Cl)C=2)C(=O)N(CC(F)(F)F)N=C1 NKZSZZXYUGAAQP-UHFFFAOYSA-N 0.000 description 1
- NRISOYZRNMJFHR-UHFFFAOYSA-N 4-(3,5-difluoro-4-methoxyphenyl)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=C(F)C=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN(CC(F)(F)F)C1=O NRISOYZRNMJFHR-UHFFFAOYSA-N 0.000 description 1
- HHKMXDFEMWUVCF-UHFFFAOYSA-N 4-(3-chloro-4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(Cl)C(F)=CC=2)C(=O)N(CC(F)(F)F)N=C1 HHKMXDFEMWUVCF-UHFFFAOYSA-N 0.000 description 1
- VVOHRFBWQOLNBB-UHFFFAOYSA-N 4-(3-chloro-4-fluorophenyl)sulfanyl-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(SC=2C=C(Cl)C(F)=CC=2)C(=O)N(CC(F)(F)F)N=C1 VVOHRFBWQOLNBB-UHFFFAOYSA-N 0.000 description 1
- IEYXTHLCAFXKHQ-UHFFFAOYSA-N 4-(3-cyclopropylidenepropyl)-2-(3,4-difluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CCC=C2CC2)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 IEYXTHLCAFXKHQ-UHFFFAOYSA-N 0.000 description 1
- IKTPZMXGBWZGPG-UHFFFAOYSA-N 4-(3-ethoxyphenyl)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound CCOC1=CC=CC(C=2C(N(CC(F)(F)F)N=CC=2C=2C=CC(=CC=2)S(C)(=O)=O)=O)=C1 IKTPZMXGBWZGPG-UHFFFAOYSA-N 0.000 description 1
- ZLRHRSRATWVCOH-UHFFFAOYSA-N 4-(3-fluoro-4-methoxyphenyl)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN(CC(F)(F)F)C1=O ZLRHRSRATWVCOH-UHFFFAOYSA-N 0.000 description 1
- ZTPOXKCNZVJDRB-UHFFFAOYSA-N 4-(3-fluoro-4-methylphenyl)-2-(4-fluorophenyl)-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(F)C(C)=CC=2)C(=O)N(C=2C=CC(F)=CC=2)N=C1 ZTPOXKCNZVJDRB-UHFFFAOYSA-N 0.000 description 1
- GXCCDSNIWOXJEF-UHFFFAOYSA-N 4-(3-fluoro-4-methylphenyl)-2-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=C(F)C(C)=CC=C1C(C1=O)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C=C1 GXCCDSNIWOXJEF-UHFFFAOYSA-N 0.000 description 1
- OSBWTPJAKCQPBI-UHFFFAOYSA-N 4-(3-fluoro-4-methylphenyl)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=C(F)C(C)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN(CC(F)(F)F)C1=O OSBWTPJAKCQPBI-UHFFFAOYSA-N 0.000 description 1
- PBKFOFXFQRXNIH-UHFFFAOYSA-N 4-(3-fluoroanilino)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(NC=2C=C(F)C=CC=2)C(=O)N(CC(F)(F)F)N=C1 PBKFOFXFQRXNIH-UHFFFAOYSA-N 0.000 description 1
- LQBVKHFEGCXMHL-UHFFFAOYSA-N 4-(3-hydroxypropylamino)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(NCCCO)C(=O)N(CC(F)(F)F)N=C1 LQBVKHFEGCXMHL-UHFFFAOYSA-N 0.000 description 1
- QVZRNLSJIOHKQJ-UHFFFAOYSA-N 4-(3-imidazol-1-ylpropylamino)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(NCCCN2C=NC=C2)C(=O)N(CC(F)(F)F)N=C1 QVZRNLSJIOHKQJ-UHFFFAOYSA-N 0.000 description 1
- MWOPAMDTCACHRB-UHFFFAOYSA-N 4-(3-methoxypropylamino)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=NN(CC(F)(F)F)C(=O)C(NCCCOC)=C1C1=CC=C(S(C)(=O)=O)C=C1 MWOPAMDTCACHRB-UHFFFAOYSA-N 0.000 description 1
- PYROKHVFPQCNCQ-UHFFFAOYSA-N 4-(4-bromophenoxy)-2-(3,4-difluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC(Br)=CC=2)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 PYROKHVFPQCNCQ-UHFFFAOYSA-N 0.000 description 1
- WIYHCXBVNBWRDA-UHFFFAOYSA-N 4-(4-chloro-3-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(F)C(Cl)=CC=2)C(=O)N(CC(F)(F)F)N=C1 WIYHCXBVNBWRDA-UHFFFAOYSA-N 0.000 description 1
- WBVDHQAMFTULTI-UHFFFAOYSA-N 4-(4-chlorophenoxy)-2-(3,4-difluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC(Cl)=CC=2)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 WBVDHQAMFTULTI-UHFFFAOYSA-N 0.000 description 1
- HFJCWIUBIVTUCP-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(3,4-difluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 HFJCWIUBIVTUCP-UHFFFAOYSA-N 0.000 description 1
- LUOHZTKOTDYTLZ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)C(=O)N(C=2C=CC(F)=CC=2)N=C1 LUOHZTKOTDYTLZ-UHFFFAOYSA-N 0.000 description 1
- MSKZXMARLZMONE-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(5-chlorothiophen-2-yl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)C(=O)N(C=2SC(Cl)=CC=2)N=C1 MSKZXMARLZMONE-UHFFFAOYSA-N 0.000 description 1
- HJPJJVWLGFNQST-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(4-methylsulfinylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)C(=O)N(CC(F)(F)F)N=C1 HJPJJVWLGFNQST-UHFFFAOYSA-N 0.000 description 1
- ILCIYNLLJFVIEP-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)C(=O)N(CC(F)(F)F)N=C1 ILCIYNLLJFVIEP-UHFFFAOYSA-N 0.000 description 1
- HBBYCCVZJOYFCQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(4-methylsulfonylphenyl)-2-[3-(trifluoromethyl)phenyl]pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)C(=O)N(C=2C=C(C=CC=2)C(F)(F)F)N=C1 HBBYCCVZJOYFCQ-UHFFFAOYSA-N 0.000 description 1
- OPBROOMIRRATQN-UHFFFAOYSA-N 4-(4-ethenylphenyl)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(C=C)=CC=2)C(=O)N(CC(F)(F)F)N=C1 OPBROOMIRRATQN-UHFFFAOYSA-N 0.000 description 1
- MCHNSYCCEBZIDY-UHFFFAOYSA-N 4-(4-fluoro-3-methylphenyl)-2-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=C(F)C(C)=CC(C=2C(N(C=3C=CC(F)=CC=3)N=CC=2C=2C=CC(=CC=2)S(C)(=O)=O)=O)=C1 MCHNSYCCEBZIDY-UHFFFAOYSA-N 0.000 description 1
- NLNSPCOZLHDQLH-UHFFFAOYSA-N 4-(4-fluoroanilino)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(NC=2C=CC(F)=CC=2)C(=O)N(CC(F)(F)F)N=C1 NLNSPCOZLHDQLH-UHFFFAOYSA-N 0.000 description 1
- DGVBFAVCXUVTPK-UHFFFAOYSA-N 4-(4-fluorophenoxy)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC(F)=CC=2)C(=O)N(CC(F)(F)F)N=C1 DGVBFAVCXUVTPK-UHFFFAOYSA-N 0.000 description 1
- PBHUMZQCBGQCCD-UHFFFAOYSA-N 4-(4-fluorophenyl)-2,5-bis(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=CC(=CC=2)S(C)(=O)=O)N=C1 PBHUMZQCBGQCCD-UHFFFAOYSA-N 0.000 description 1
- MWNUZQYQYSIBLS-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(1-methylcyclopentyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound N1=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=C(C=2C=CC(F)=CC=2)C(=O)N1C1(C)CCCC1 MWNUZQYQYSIBLS-UHFFFAOYSA-N 0.000 description 1
- YBJUJWSEZDHNCM-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(2,3,3,4,4,4-hexafluorobut-1-enyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=C(F)C(F)(F)C(F)(F)F)N=C1 YBJUJWSEZDHNCM-UHFFFAOYSA-N 0.000 description 1
- NITJKKMAMNMNCV-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(2-methylcyclopentyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound CC1CCCC1N1C(=O)C(C=2C=CC(F)=CC=2)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=N1 NITJKKMAMNMNCV-UHFFFAOYSA-N 0.000 description 1
- RONARLCTDGRRLY-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(2-methylsulfanylphenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound CSC1=CC=CC=C1N1C(=O)C(C=2C=CC(F)=CC=2)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=N1 RONARLCTDGRRLY-UHFFFAOYSA-N 0.000 description 1
- BTVCUBHJRIGKQW-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(3-methylbut-2-enyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C=1C=C(F)C=CC=1C=1C(=O)N(CC=C(C)C)N=CC=1C1=CC=C(S(C)(=O)=O)C=C1 BTVCUBHJRIGKQW-UHFFFAOYSA-N 0.000 description 1
- OWIFSQITKUBZAG-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(3-methylcyclopentyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1C(C)CCC1N1C(=O)C(C=2C=CC(F)=CC=2)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=N1 OWIFSQITKUBZAG-UHFFFAOYSA-N 0.000 description 1
- QCBOFMYNMKFLKG-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(3-methylphenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound CC1=CC=CC(N2C(C(C=3C=CC(F)=CC=3)=C(C=3C=CC(=CC=3)S(C)(=O)=O)C=N2)=O)=C1 QCBOFMYNMKFLKG-UHFFFAOYSA-N 0.000 description 1
- RDVGYWMZPJOGLE-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(3-methylsulfanylphenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound CSC1=CC=CC(N2C(C(C=3C=CC(F)=CC=3)=C(C=3C=CC(=CC=3)S(C)(=O)=O)C=N2)=O)=C1 RDVGYWMZPJOGLE-UHFFFAOYSA-N 0.000 description 1
- ZOPZLCFCLPQBQE-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(3-methylsulfonylphenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=C(C=CC=2)S(C)(=O)=O)N=C1 ZOPZLCFCLPQBQE-UHFFFAOYSA-N 0.000 description 1
- BHFHQQGZBNNEDH-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(4-methylphenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(C)=CC=C1N1C(=O)C(C=2C=CC(F)=CC=2)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=N1 BHFHQQGZBNNEDH-UHFFFAOYSA-N 0.000 description 1
- ZIQJTDRSNQQVIY-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(4-methylsulfanylphenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1N1C(=O)C(C=2C=CC(F)=CC=2)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=N1 ZIQJTDRSNQQVIY-UHFFFAOYSA-N 0.000 description 1
- MNHBPEHKGPEZRA-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(furan-3-yl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C2=COC=C2)N=C1 MNHBPEHKGPEZRA-UHFFFAOYSA-N 0.000 description 1
- PEJBFCCTYARZRI-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-[(4-fluorophenyl)methyl]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C=CC(F)=CC=2)N=C1 PEJBFCCTYARZRI-UHFFFAOYSA-N 0.000 description 1
- JAHCDEDAMGLMKC-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-[(4-hydroxyphenyl)methyl]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C=CC(O)=CC=2)N=C1 JAHCDEDAMGLMKC-UHFFFAOYSA-N 0.000 description 1
- MMULWYGDMKYDQU-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-[(6-fluoroquinolin-2-yl)methyl]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2N=C3C=CC(F)=CC3=CC=2)N=C1 MMULWYGDMKYDQU-UHFFFAOYSA-N 0.000 description 1
- AMVIOLHDUJZPJP-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-[1-(4-fluorophenyl)ethyl]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound N1=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=C(C=2C=CC(F)=CC=2)C(=O)N1C(C)C1=CC=C(F)C=C1 AMVIOLHDUJZPJP-UHFFFAOYSA-N 0.000 description 1
- AGLMMKDKVQRDNU-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-hex-2-ynyl-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C=1C=C(F)C=CC=1C=1C(=O)N(CC#CCCC)N=CC=1C1=CC=C(S(C)(=O)=O)C=C1 AGLMMKDKVQRDNU-UHFFFAOYSA-N 0.000 description 1
- COKCHMNJSVAMQI-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfanylphenyl)-2-phenylpyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=CC=CC=2)N=C1 COKCHMNJSVAMQI-UHFFFAOYSA-N 0.000 description 1
- SMKWHXLAVQILQQ-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfinylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC(F)(F)F)N=C1 SMKWHXLAVQILQQ-UHFFFAOYSA-N 0.000 description 1
- UCVBGLXRXZWUNI-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(1-phenylprop-2-ynyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C(C#C)C=2C=CC=CC=2)N=C1 UCVBGLXRXZWUNI-UHFFFAOYSA-N 0.000 description 1
- RPNZXOBNBMTHIJ-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(2-nitrophenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C(=CC=CC=2)[N+]([O-])=O)N=C1 RPNZXOBNBMTHIJ-UHFFFAOYSA-N 0.000 description 1
- PQAJKUNRYBPAOX-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(2-phenylethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CCC=2C=CC=CC=2)N=C1 PQAJKUNRYBPAOX-UHFFFAOYSA-N 0.000 description 1
- LHYINZDBFBFMRT-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(3,4,4-trifluorobut-3-enyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CCC(F)=C(F)F)N=C1 LHYINZDBFBFMRT-UHFFFAOYSA-N 0.000 description 1
- GUHBBGPXLZOYSE-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(3-methylthiophen-2-yl)pyridazin-3-one Chemical compound C1=CSC(N2C(C(C=3C=CC(F)=CC=3)=C(C=3C=CC(=CC=3)S(C)(=O)=O)C=N2)=O)=C1C GUHBBGPXLZOYSE-UHFFFAOYSA-N 0.000 description 1
- KEXMGDVGSAPGAG-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(3-phenylprop-2-enyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=CC=2C=CC=CC=2)N=C1 KEXMGDVGSAPGAG-UHFFFAOYSA-N 0.000 description 1
- BJTQJWWAPJOQRV-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(4-nitrophenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=CC(=CC=2)[N+]([O-])=O)N=C1 BJTQJWWAPJOQRV-UHFFFAOYSA-N 0.000 description 1
- PCKSLQDDRWSHPA-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(4-phenoxyphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=CC(OC=3C=CC=CC=3)=CC=2)N=C1 PCKSLQDDRWSHPA-UHFFFAOYSA-N 0.000 description 1
- PXMNUPZTBPKWAN-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(5-methylthiophen-2-yl)pyridazin-3-one Chemical compound S1C(C)=CC=C1N1C(=O)C(C=2C=CC(F)=CC=2)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=N1 PXMNUPZTBPKWAN-UHFFFAOYSA-N 0.000 description 1
- WJVDNFKEOFBNMX-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(5-nitrothiophen-2-yl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2SC(=CC=2)[N+]([O-])=O)N=C1 WJVDNFKEOFBNMX-UHFFFAOYSA-N 0.000 description 1
- AQPYLLMKFQYDKV-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(pyridin-2-ylmethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2N=CC=CC=2)N=C1 AQPYLLMKFQYDKV-UHFFFAOYSA-N 0.000 description 1
- JNABHUZYKNWFOC-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(pyridin-3-ylmethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C=NC=CC=2)N=C1 JNABHUZYKNWFOC-UHFFFAOYSA-N 0.000 description 1
- YBNJUBBNDVOUOR-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(pyridin-4-ylmethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C=CN=CC=2)N=C1 YBNJUBBNDVOUOR-UHFFFAOYSA-N 0.000 description 1
- WMEJIUYUGQHTGB-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(quinolin-2-ylmethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2N=C3C=CC=CC3=CC=2)N=C1 WMEJIUYUGQHTGB-UHFFFAOYSA-N 0.000 description 1
- FVZCGBJEIMRHLJ-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(thiophen-3-ylmethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC2=CSC=C2)N=C1 FVZCGBJEIMRHLJ-UHFFFAOYSA-N 0.000 description 1
- YVANPYBPMVCVRI-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-[(2,3,4,5,6-pentafluorophenyl)methyl]pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C(=C(F)C(F)=C(F)C=2F)F)N=C1 YVANPYBPMVCVRI-UHFFFAOYSA-N 0.000 description 1
- QKPDEESNBWPEKQ-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-[(3-nitrophenyl)methyl]pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C=C(C=CC=2)[N+]([O-])=O)N=C1 QKPDEESNBWPEKQ-UHFFFAOYSA-N 0.000 description 1
- LEFVQZJUZZZQAK-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-[(4-nitrophenyl)methyl]pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C=CC(=CC=2)[N+]([O-])=O)N=C1 LEFVQZJUZZZQAK-UHFFFAOYSA-N 0.000 description 1
- LIIPTFMIBJKHFA-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-[(5-methyl-1,3-thiazol-2-yl)methyl]pyridazin-3-one Chemical compound S1C(C)=CN=C1CN1C(=O)C(C=2C=CC(F)=CC=2)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=N1 LIIPTFMIBJKHFA-UHFFFAOYSA-N 0.000 description 1
- GEQXTMIAUVKXRF-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-[(5-methylthiophen-2-yl)methyl]pyridazin-3-one Chemical compound S1C(C)=CC=C1CN1C(=O)C(C=2C=CC(F)=CC=2)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=N1 GEQXTMIAUVKXRF-UHFFFAOYSA-N 0.000 description 1
- ALKZOXFMFBFUHA-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-[2-oxo-2-[4-(trifluoromethoxy)phenyl]ethyl]pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC(=O)C=2C=CC(OC(F)(F)F)=CC=2)N=C1 ALKZOXFMFBFUHA-UHFFFAOYSA-N 0.000 description 1
- MAPAWHXDWIILSY-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-[2-oxo-2-[4-(trifluoromethyl)phenyl]ethyl]pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC(=O)C=2C=CC(=CC=2)C(F)(F)F)N=C1 MAPAWHXDWIILSY-UHFFFAOYSA-N 0.000 description 1
- VDDKUEQDADHMTM-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-[4-(trifluoromethyl)phenyl]pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=CC(=CC=2)C(F)(F)F)N=C1 VDDKUEQDADHMTM-UHFFFAOYSA-N 0.000 description 1
- DEEDNENXBRWRAU-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-[[2-(trifluoromethyl)phenyl]methyl]pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C(=CC=CC=2)C(F)(F)F)N=C1 DEEDNENXBRWRAU-UHFFFAOYSA-N 0.000 description 1
- AWLJHDDAQHMKMI-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-phenacylpyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC(=O)C=2C=CC=CC=2)N=C1 AWLJHDDAQHMKMI-UHFFFAOYSA-N 0.000 description 1
- WKDJJTSGQQEAFR-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-prop-2-ynylpyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC#C)N=C1 WKDJJTSGQQEAFR-UHFFFAOYSA-N 0.000 description 1
- DMKJARWAPLHQGD-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-thiophen-2-ylpyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2SC=CC=2)N=C1 DMKJARWAPLHQGD-UHFFFAOYSA-N 0.000 description 1
- LZLSQXAFUYIWMD-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-thiophen-3-ylpyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C2=CSC=C2)N=C1 LZLSQXAFUYIWMD-UHFFFAOYSA-N 0.000 description 1
- ACXZYFJDQHIFBC-UHFFFAOYSA-N 4-(4-fluorophenyl)-6-methyl-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1C(C)=NN(CC(F)(F)F)C(=O)C=1C1=CC=C(F)C=C1 ACXZYFJDQHIFBC-UHFFFAOYSA-N 0.000 description 1
- JIUUWBMHUNMYGK-UHFFFAOYSA-N 4-(4-fluorophenyl)sulfanyl-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(SC=2C=CC(F)=CC=2)C(=O)N(CC(F)(F)F)N=C1 JIUUWBMHUNMYGK-UHFFFAOYSA-N 0.000 description 1
- XUPINJZETUSRRV-UHFFFAOYSA-N 4-(4-methoxyphenoxy)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(OC)=CC=C1OC1=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN(CC(F)(F)F)C1=O XUPINJZETUSRRV-UHFFFAOYSA-N 0.000 description 1
- QDRQZQCAXQXGIT-UHFFFAOYSA-N 4-(4-methylphenyl)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN(CC(F)(F)F)C1=O QDRQZQCAXQXGIT-UHFFFAOYSA-N 0.000 description 1
- PGSLNGQLGFAGAV-UHFFFAOYSA-N 4-(4-methylsulfonylphenoxy)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC1=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN(CC(F)(F)F)C1=O PGSLNGQLGFAGAV-UHFFFAOYSA-N 0.000 description 1
- KRLKXOLFFQWKPZ-UHFFFAOYSA-N 4-(bromomethyl)pyridine Chemical compound BrCC1=CC=NC=C1 KRLKXOLFFQWKPZ-UHFFFAOYSA-N 0.000 description 1
- JJWHSQWPDPJKTF-UHFFFAOYSA-N 4-(cyclobutylamino)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(NC2CCC2)C(=O)N(CC(F)(F)F)N=C1 JJWHSQWPDPJKTF-UHFFFAOYSA-N 0.000 description 1
- MFHRVTIBDYVWPE-UHFFFAOYSA-N 4-(cyclohexylamino)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(NC2CCCCC2)C(=O)N(CC(F)(F)F)N=C1 MFHRVTIBDYVWPE-UHFFFAOYSA-N 0.000 description 1
- NMKJROYNSDYGHE-UHFFFAOYSA-N 4-(cyclopentylamino)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(NC2CCCC2)C(=O)N(CC(F)(F)F)N=C1 NMKJROYNSDYGHE-UHFFFAOYSA-N 0.000 description 1
- STASBJQXIYRCKU-UHFFFAOYSA-N 4-(cyclopropylamino)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(NC2CC2)C(=O)N(CC(F)(F)F)N=C1 STASBJQXIYRCKU-UHFFFAOYSA-N 0.000 description 1
- NPTPMALREQBTHA-UHFFFAOYSA-N 4-(furan-2-ylmethoxy)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OCC=2OC=CC=2)C(=O)N(CC(F)(F)F)N=C1 NPTPMALREQBTHA-UHFFFAOYSA-N 0.000 description 1
- HRNNNYZRMMSALR-UHFFFAOYSA-N 4-(sulfanylmethyl)benzaldehyde Chemical compound SCC1=CC=C(C=O)C=C1 HRNNNYZRMMSALR-UHFFFAOYSA-N 0.000 description 1
- FDPVDEHVNAIKIJ-UHFFFAOYSA-N 4-(tert-butylsulfanylmethyl)-2-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(CSC(C)(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C=C1 FDPVDEHVNAIKIJ-UHFFFAOYSA-N 0.000 description 1
- LOLKAJARZKDJTD-UHFFFAOYSA-N 4-Ethoxy-4-oxobutanoic acid Chemical class CCOC(=O)CCC(O)=O LOLKAJARZKDJTD-UHFFFAOYSA-N 0.000 description 1
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
- WYDJPZRGAKOVCG-UHFFFAOYSA-N 4-[(1-methylcyclopropyl)methoxy]-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1C=NN(CC(F)(F)F)C(=O)C=1OCC1(C)CC1 WYDJPZRGAKOVCG-UHFFFAOYSA-N 0.000 description 1
- MEPWDQMOMUAYGU-UHFFFAOYSA-N 4-[(3-fluorophenoxy)methyl]-2-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(COC=2C=C(F)C=CC=2)C(=O)N(C=2C=CC(F)=CC=2)N=C1 MEPWDQMOMUAYGU-UHFFFAOYSA-N 0.000 description 1
- MPCPULVQGKLAOO-UHFFFAOYSA-N 4-[1-(3,3-dichloroprop-2-enyl)-5-(4-fluorophenyl)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=C(Cl)Cl)N=C1 MPCPULVQGKLAOO-UHFFFAOYSA-N 0.000 description 1
- BBQOSODABMDILL-UHFFFAOYSA-N 4-[1-(3,3-difluoroprop-2-enyl)-5-(4-fluorophenyl)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=C(F)F)N=C1 BBQOSODABMDILL-UHFFFAOYSA-N 0.000 description 1
- NGFXOPNZCHXLMH-UHFFFAOYSA-N 4-[1-(4-fluorophenyl)-5-[(3-fluorophenyl)methyl]-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(CC=2C=C(F)C=CC=2)C(=O)N(C=2C=CC(F)=CC=2)N=C1 NGFXOPNZCHXLMH-UHFFFAOYSA-N 0.000 description 1
- KKDYOABTKOYEDP-UHFFFAOYSA-N 4-[1-(4-fluorophenyl)ethoxy]-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C=1C=C(F)C=CC=1C(C)OC(C(N(CC(F)(F)F)N=C1)=O)=C1C1=CC=C(S(C)(=O)=O)C=C1 KKDYOABTKOYEDP-UHFFFAOYSA-N 0.000 description 1
- JOFGHXIYZSAORW-UHFFFAOYSA-N 4-[1-(cyclohexen-1-ylmethyl)-5-(4-fluorophenyl)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2CCCCC=2)N=C1 JOFGHXIYZSAORW-UHFFFAOYSA-N 0.000 description 1
- QMDJCGCOCRSOHK-UHFFFAOYSA-N 4-[1-[(2,4-difluorophenyl)methyl]-5-(4-fluorophenyl)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C(=CC(F)=CC=2)F)N=C1 QMDJCGCOCRSOHK-UHFFFAOYSA-N 0.000 description 1
- MUERPSUSPDVSPW-UHFFFAOYSA-N 4-[1-[(3,4-difluorophenyl)methyl]-5-(4-fluorophenyl)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C=C(F)C(F)=CC=2)N=C1 MUERPSUSPDVSPW-UHFFFAOYSA-N 0.000 description 1
- PIZUVFYDUHYGTA-JLHYYAGUSA-N 4-[1-[(e)-4-chlorobut-2-en-2-yl]-5-(4-fluorophenyl)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound C=1C=C(F)C=CC=1C=1C(=O)N(C(=C/CCl)/C)N=CC=1C1=CC=C(S(N)(=O)=O)C=C1 PIZUVFYDUHYGTA-JLHYYAGUSA-N 0.000 description 1
- FBMCFYFIHIDBKF-UHFFFAOYSA-N 4-[1-[1-(3,4-difluorophenyl)ethyl]-5-(4-fluorophenyl)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound N1=CC(C=2C=CC(=CC=2)S(N)(=O)=O)=C(C=2C=CC(F)=CC=2)C(=O)N1C(C)C1=CC=C(F)C(F)=C1 FBMCFYFIHIDBKF-UHFFFAOYSA-N 0.000 description 1
- ITCVOXHEJLTCEK-UHFFFAOYSA-N 4-[1-[1-(3,5-difluorophenyl)ethyl]-5-(4-fluorophenyl)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound N1=CC(C=2C=CC(=CC=2)S(N)(=O)=O)=C(C=2C=CC(F)=CC=2)C(=O)N1C(C)C1=CC(F)=CC(F)=C1 ITCVOXHEJLTCEK-UHFFFAOYSA-N 0.000 description 1
- ACPCHWSBLRIFQH-UHFFFAOYSA-N 4-[1-benzyl-5-(4-fluorophenyl)-6-oxopyridazin-4-yl]-2-fluorobenzenesulfonamide Chemical compound C1=C(F)C(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C=CC=CC=2)N=C1 ACPCHWSBLRIFQH-UHFFFAOYSA-N 0.000 description 1
- TUKWLBJIITZYBH-UHFFFAOYSA-N 4-[1-benzyl-5-(4-fluorophenyl)-6-oxopyridazin-4-yl]benzenesulfonyl chloride Chemical compound C1=CC(F)=CC=C1C(C1=O)=C(C=2C=CC(=CC=2)S(Cl)(=O)=O)C=NN1CC1=CC=CC=C1 TUKWLBJIITZYBH-UHFFFAOYSA-N 0.000 description 1
- HRGWZCQIBCMDKL-UHFFFAOYSA-N 4-[1-cyclohex-3-en-1-yl-5-(4-fluorophenyl)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C2CC=CCC2)N=C1 HRGWZCQIBCMDKL-UHFFFAOYSA-N 0.000 description 1
- LPYXKSIZHACWOD-UHFFFAOYSA-N 4-[2-(3,4-dimethoxyphenyl)ethylamino]-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1CCNC1=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN(CC(F)(F)F)C1=O LPYXKSIZHACWOD-UHFFFAOYSA-N 0.000 description 1
- YBWAAXUWCXOLDI-UHFFFAOYSA-N 4-[2-[5-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)-6-oxopyridazin-1-yl]acetyl]benzonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC(=O)C=2C=CC(=CC=2)C#N)N=C1 YBWAAXUWCXOLDI-UHFFFAOYSA-N 0.000 description 1
- YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
- WIRDRWAILZRLHB-UHFFFAOYSA-N 4-[3-methoxy-5-(trifluoromethyl)anilino]-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound FC(F)(F)C1=CC(OC)=CC(NC=2C(N(CC(F)(F)F)N=CC=2C=2C=CC(=CC=2)S(C)(=O)=O)=O)=C1 WIRDRWAILZRLHB-UHFFFAOYSA-N 0.000 description 1
- FNCOMNQXHUPYBS-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-6-oxo-1-(2,2,2-trifluoroethyl)pyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)C(=O)N(CC(F)(F)F)N=C1 FNCOMNQXHUPYBS-UHFFFAOYSA-N 0.000 description 1
- QSHLSGYSUAQNCU-UHFFFAOYSA-N 4-[5-(4-fluorophenoxy)-6-oxo-1-(2,2,2-trifluoroethyl)pyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(OC=2C=CC(F)=CC=2)C(=O)N(CC(F)(F)F)N=C1 QSHLSGYSUAQNCU-UHFFFAOYSA-N 0.000 description 1
- BAFLYVGRIPBNPJ-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-1-[(3-fluorophenyl)methyl]-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C=C(F)C=CC=2)N=C1 BAFLYVGRIPBNPJ-UHFFFAOYSA-N 0.000 description 1
- UNSUCZRMEMHMFL-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-1-[(4-fluorophenyl)methyl]-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C=CC(F)=CC=2)N=C1 UNSUCZRMEMHMFL-UHFFFAOYSA-N 0.000 description 1
- XAGNVQUCCBLCQS-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-1-[1-(3-fluorophenyl)ethyl]-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound N1=CC(C=2C=CC(=CC=2)S(N)(=O)=O)=C(C=2C=CC(F)=CC=2)C(=O)N1C(C)C1=CC=CC(F)=C1 XAGNVQUCCBLCQS-UHFFFAOYSA-N 0.000 description 1
- JLRGLJBKMBMJFT-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)-6-oxopyridazin-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C1 JLRGLJBKMBMJFT-UHFFFAOYSA-N 0.000 description 1
- ODPWITAOYPIUIV-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)-6-oxopyridazin-1-yl]benzonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(C=2C=CC(=CC=2)C#N)N=C1 ODPWITAOYPIUIV-UHFFFAOYSA-N 0.000 description 1
- YZRFYMBQGCOXAY-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-6-oxo-1-(2,2,2-trifluoroethyl)pyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC(F)(F)F)N=C1 YZRFYMBQGCOXAY-UHFFFAOYSA-N 0.000 description 1
- RJVXRQKJQXBUAX-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-6-oxo-1-(2,3,3-trifluoroprop-2-enyl)pyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC(F)=C(F)F)N=C1 RJVXRQKJQXBUAX-UHFFFAOYSA-N 0.000 description 1
- KBHPPNZQHIKYII-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-6-oxo-1-[(2,3,4,5,6-pentafluorophenyl)methyl]pyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C(=C(F)C(F)=C(F)C=2F)F)N=C1 KBHPPNZQHIKYII-UHFFFAOYSA-N 0.000 description 1
- DWDQVOIEKHHGBC-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-6-oxo-1-[(2,3,4-trifluorophenyl)methyl]pyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C(=C(F)C(F)=CC=2)F)N=C1 DWDQVOIEKHHGBC-UHFFFAOYSA-N 0.000 description 1
- MYCGGJZNPDJHMA-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-6-oxo-1-[(2,4,5-trifluorophenyl)methyl]pyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C(=CC(F)=C(F)C=2)F)N=C1 MYCGGJZNPDJHMA-UHFFFAOYSA-N 0.000 description 1
- NSABLBMEVNEEOF-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-6-oxo-1-[(2,4,6-trifluorophenyl)methyl]pyridazin-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)N(CC=2C(=CC(F)=CC=2F)F)N=C1 NSABLBMEVNEEOF-UHFFFAOYSA-N 0.000 description 1
- ZIHJZFFAKQTKQK-ZHACJKMWSA-N 4-[5-(4-fluorophenyl)-6-oxo-1-[(e)-4,4,4-trifluoro-3-methylbut-1-enyl]pyridazin-4-yl]benzenesulfonamide Chemical compound C=1C=C(F)C=CC=1C=1C(=O)N(/C=C/C(C)C(F)(F)F)N=CC=1C1=CC=C(S(N)(=O)=O)C=C1 ZIHJZFFAKQTKQK-ZHACJKMWSA-N 0.000 description 1
- UHJUBRVSTNJENG-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-6-oxo-1-[1-(2,3,4-trifluorophenyl)ethyl]pyridazin-4-yl]benzenesulfonamide Chemical compound N1=CC(C=2C=CC(=CC=2)S(N)(=O)=O)=C(C=2C=CC(F)=CC=2)C(=O)N1C(C)C1=CC=C(F)C(F)=C1F UHJUBRVSTNJENG-UHFFFAOYSA-N 0.000 description 1
- QBCRYZSYHPPFOY-UHFFFAOYSA-N 4-[5-(4-methylsulfonylphenyl)-3-oxo-2-(2,2,2-trifluoroethyl)pyridazin-4-yl]oxybenzonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC(=CC=2)C#N)C(=O)N(CC(F)(F)F)N=C1 QBCRYZSYHPPFOY-UHFFFAOYSA-N 0.000 description 1
- SLOIQVSWCHKGEH-UHFFFAOYSA-N 4-[6-oxo-5-propan-2-yloxy-1-(2,2,2-trifluoroethyl)pyridazin-4-yl]benzenesulfonamide Chemical compound C1=NN(CC(F)(F)F)C(=O)C(OC(C)C)=C1C1=CC=C(S(N)(=O)=O)C=C1 SLOIQVSWCHKGEH-UHFFFAOYSA-N 0.000 description 1
- XYWIPYBIIRTJMM-IBGZPJMESA-N 4-[[(2S)-2-[4-[5-chloro-2-[4-(trifluoromethyl)triazol-1-yl]phenyl]-5-methoxy-2-oxopyridin-1-yl]butanoyl]amino]-2-fluorobenzamide Chemical compound CC[C@H](N1C=C(OC)C(=CC1=O)C1=C(C=CC(Cl)=C1)N1C=C(N=N1)C(F)(F)F)C(=O)NC1=CC(F)=C(C=C1)C(N)=O XYWIPYBIIRTJMM-IBGZPJMESA-N 0.000 description 1
- UVUSABCBHGBAHH-SNVBAGLBSA-N 4-[[(2r)-2-hydroxypropyl]amino]-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=NN(CC(F)(F)F)C(=O)C(NC[C@H](O)C)=C1C1=CC=C(S(C)(=O)=O)C=C1 UVUSABCBHGBAHH-SNVBAGLBSA-N 0.000 description 1
- DODIHWBMINJCSJ-UHFFFAOYSA-N 4-[[5-(4-methylsulfonylphenyl)-3-oxo-2-(2,2,2-trifluoroethyl)pyridazin-4-yl]amino]benzonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(NC=2C=CC(=CC=2)C#N)C(=O)N(CC(F)(F)F)N=C1 DODIHWBMINJCSJ-UHFFFAOYSA-N 0.000 description 1
- ARRCKCLXJHDDMI-UHFFFAOYSA-N 4-[benzyl(methyl)amino]-2-(3-chlorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1C=NN(C=2C=C(Cl)C=CC=2)C(=O)C=1N(C)CC1=CC=CC=C1 ARRCKCLXJHDDMI-UHFFFAOYSA-N 0.000 description 1
- UBPKBVRLHVVULG-UHFFFAOYSA-N 4-amino-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(N)C(=O)N(CC(F)(F)F)N=C1 UBPKBVRLHVVULG-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- MOKVXZNIKKNAFE-UHFFFAOYSA-N 4-anilino-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(NC=2C=CC=CC=2)C(=O)N(CC(F)(F)F)N=C1 MOKVXZNIKKNAFE-UHFFFAOYSA-N 0.000 description 1
- VQUAISDTJYCVSA-UHFFFAOYSA-N 4-benzyl-2-(3,4-difluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CC=2C=CC=CC=2)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 VQUAISDTJYCVSA-UHFFFAOYSA-N 0.000 description 1
- DNWURFRAEBOVJO-UHFFFAOYSA-N 4-benzyl-2-(3-chloro-4-fluorophenyl)-5-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(CC=2C=CC=CC=2)C(=O)N(C=2C=C(Cl)C(F)=CC=2)N=C1 DNWURFRAEBOVJO-UHFFFAOYSA-N 0.000 description 1
- IJGVSURRCSHTBB-UHFFFAOYSA-N 4-benzyl-2-(3-chloro-4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CC=2C=CC=CC=2)C(=O)N(C=2C=C(Cl)C(F)=CC=2)N=C1 IJGVSURRCSHTBB-UHFFFAOYSA-N 0.000 description 1
- PQMMUFSSUASWKD-UHFFFAOYSA-N 4-benzyl-2-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CC=2C=CC=CC=2)C(=O)N(C=2C=CC(F)=CC=2)N=C1 PQMMUFSSUASWKD-UHFFFAOYSA-N 0.000 description 1
- YRYBTORHBHKNDI-UHFFFAOYSA-N 4-benzyl-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CC=2C=CC=CC=2)C(=O)N(CC(F)(F)F)N=C1 YRYBTORHBHKNDI-UHFFFAOYSA-N 0.000 description 1
- HDPAREFHZNNWJH-UHFFFAOYSA-N 4-benzylsulfanyl-2-(3-chlorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(SCC=2C=CC=CC=2)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 HDPAREFHZNNWJH-UHFFFAOYSA-N 0.000 description 1
- KXHZMZOUMKKFJC-UHFFFAOYSA-N 4-benzylsulfanyl-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(SCC=2C=CC=CC=2)C(=O)N(CC(F)(F)F)N=C1 KXHZMZOUMKKFJC-UHFFFAOYSA-N 0.000 description 1
- ZDGXQRYZNUCOEP-UHFFFAOYSA-N 4-bromo-1,1,1-trifluoro-2-methylbut-2-ene Chemical compound FC(F)(F)C(C)=CCBr ZDGXQRYZNUCOEP-UHFFFAOYSA-N 0.000 description 1
- GQCQMFYIFUDARF-UHFFFAOYSA-N 4-bromo-1,1,2-trifluorobut-1-ene Chemical group FC(F)=C(F)CCBr GQCQMFYIFUDARF-UHFFFAOYSA-N 0.000 description 1
- AGYWDGVTLKNTBS-UHFFFAOYSA-N 4-bromo-1-chloro-2-fluorobenzene Chemical compound FC1=CC(Br)=CC=C1Cl AGYWDGVTLKNTBS-UHFFFAOYSA-N 0.000 description 1
- ADJYZINEAMDEFL-UHFFFAOYSA-N 4-bromo-1-methoxy-2-methylsulfanylbenzene Chemical compound COC1=CC=C(Br)C=C1SC ADJYZINEAMDEFL-UHFFFAOYSA-N 0.000 description 1
- DWNXGZBXFDNKOR-UHFFFAOYSA-N 4-bromo-2-fluoro-1-methoxybenzene Chemical compound COC1=CC=C(Br)C=C1F DWNXGZBXFDNKOR-UHFFFAOYSA-N 0.000 description 1
- RLVDBGSMCSDUST-UHFFFAOYSA-N 4-bromo-2-methyl-1-methylsulfanylbenzene Chemical compound CSC1=CC=C(Br)C=C1C RLVDBGSMCSDUST-UHFFFAOYSA-N 0.000 description 1
- STYQHICBPYRHQK-UHFFFAOYSA-N 4-bromobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Br)C=C1 STYQHICBPYRHQK-UHFFFAOYSA-N 0.000 description 1
- HQSCPPCMBMFJJN-UHFFFAOYSA-N 4-bromobenzonitrile Chemical compound BrC1=CC=C(C#N)C=C1 HQSCPPCMBMFJJN-UHFFFAOYSA-N 0.000 description 1
- 125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- JDUYPUMQALQRCN-UHFFFAOYSA-N 4-bromophenyl phenyl ether Chemical compound C1=CC(Br)=CC=C1OC1=CC=CC=C1 JDUYPUMQALQRCN-UHFFFAOYSA-N 0.000 description 1
- LTCDDUZNHKJLBA-UHFFFAOYSA-N 4-but-2-en-2-yl-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=NN(CC(F)(F)F)C(=O)C(C(C)=CC)=C1C1=CC=C(S(C)(=O)=O)C=C1 LTCDDUZNHKJLBA-UHFFFAOYSA-N 0.000 description 1
- GLSDPSDPWPLTEV-UHFFFAOYSA-N 4-chloro-5-hydroxy-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound OC=1C=NN(CC(F)(F)F)C(=O)C=1Cl GLSDPSDPWPLTEV-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical group OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
- SXOLOMITTITKRE-UHFFFAOYSA-N 4-cyclohexyl-2-(3,4-difluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C2CCCCC2)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 SXOLOMITTITKRE-UHFFFAOYSA-N 0.000 description 1
- FIAFIHWYZYPMME-UHFFFAOYSA-N 4-cyclohexyl-2-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C2CCCCC2)C(=O)N(C=2C=CC(F)=CC=2)N=C1 FIAFIHWYZYPMME-UHFFFAOYSA-N 0.000 description 1
- OGBZCJUQRGBBLH-UHFFFAOYSA-N 4-cyclohexyl-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C2CCCCC2)C(=O)N(CC(F)(F)F)N=C1 OGBZCJUQRGBBLH-UHFFFAOYSA-N 0.000 description 1
- IIHDJEOWVUUEDS-UHFFFAOYSA-N 4-cyclohexyloxy-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC2CCCCC2)C(=O)N(CC(F)(F)F)N=C1 IIHDJEOWVUUEDS-UHFFFAOYSA-N 0.000 description 1
- LXKAPPJHMDQZSO-UHFFFAOYSA-N 4-cyclohexylsulfanyl-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(SC2CCCCC2)C(=O)N(CC(F)(F)F)N=C1 LXKAPPJHMDQZSO-UHFFFAOYSA-N 0.000 description 1
- CYYXZIRYGFSHLX-UHFFFAOYSA-N 4-cyclopentyloxy-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC2CCCC2)C(=O)N(CC(F)(F)F)N=C1 CYYXZIRYGFSHLX-UHFFFAOYSA-N 0.000 description 1
- LGBQYTSYUNXMAF-UHFFFAOYSA-N 4-cyclopentylsulfanyl-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(SC2CCCC2)C(=O)N(CC(F)(F)F)N=C1 LGBQYTSYUNXMAF-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical group NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- FKKLUOCEIANSFL-UHFFFAOYSA-N 4-methylpent-3-en-1-ol Chemical compound CC(C)=CCCO FKKLUOCEIANSFL-UHFFFAOYSA-N 0.000 description 1
- QRVYABWJVXXOTN-UHFFFAOYSA-N 4-methylsulfanylbenzaldehyde Chemical compound CSC1=CC=C(C=O)C=C1 QRVYABWJVXXOTN-UHFFFAOYSA-N 0.000 description 1
- VOLRSQPSJGXRNJ-UHFFFAOYSA-N 4-nitrobenzyl bromide Chemical compound [O-][N+](=O)C1=CC=C(CBr)C=C1 VOLRSQPSJGXRNJ-UHFFFAOYSA-N 0.000 description 1
- GVYKTJXEQRUDMX-UHFFFAOYSA-N 4-sulfonyl-1,2-dihydropyridazin-3-one Chemical compound O=C1NNC=CC1=S(=O)=O GVYKTJXEQRUDMX-UHFFFAOYSA-N 0.000 description 1
- UUAVJCDYOHIIQW-UHFFFAOYSA-N 4-sulfonylpyridazin-3-one Chemical compound O=C1N=NC=CC1=S(=O)=O UUAVJCDYOHIIQW-UHFFFAOYSA-N 0.000 description 1
- CUCARHVTCNILLV-UHFFFAOYSA-N 4-tert-butyl-2-(3,4-difluorophenyl)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(C(C)(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 CUCARHVTCNILLV-UHFFFAOYSA-N 0.000 description 1
- KNYKQYBYIWWHQQ-UHFFFAOYSA-N 4-tert-butylsulfanyl-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=NN(CC(F)(F)F)C(=O)C(SC(C)(C)C)=C1C1=CC=C(S(C)(=O)=O)C=C1 KNYKQYBYIWWHQQ-UHFFFAOYSA-N 0.000 description 1
- 125000004864 4-thiomethylphenyl group Chemical group 0.000 description 1
- BTQRRILXQPDFQO-UHFFFAOYSA-N 5-(4-fluorophenyl)-3-methyl-4-(4-methylsulfonylphenyl)-1h-pyridazin-6-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1C(C)=NNC(=O)C=1C1=CC=C(F)C=C1 BTQRRILXQPDFQO-UHFFFAOYSA-N 0.000 description 1
- ORCFQIZNXZRUGJ-UHFFFAOYSA-N 5-(4-fluorophenyl)-4-(4-methylsulfanylphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(SC)=CC=C1C1C(C=2C=CC(F)=CC=2)C(=O)NN=C1 ORCFQIZNXZRUGJ-UHFFFAOYSA-N 0.000 description 1
- RVEWBSLUJVMCOJ-UHFFFAOYSA-N 5-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1C(C=2C=CC(F)=CC=2)C(=O)NN=C1 RVEWBSLUJVMCOJ-UHFFFAOYSA-N 0.000 description 1
- SKOPTUAIRLFZGH-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)-4-(2,2,2-trifluoroethylsulfanyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(SCC(F)(F)F)C(=O)N(CC(F)(F)F)N=C1 SKOPTUAIRLFZGH-UHFFFAOYSA-N 0.000 description 1
- XBDYFGSCLZSSNX-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)-4-[3-(trifluoromethyl)phenyl]pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(C=CC=2)C(F)(F)F)C(=O)N(CC(F)(F)F)N=C1 XBDYFGSCLZSSNX-UHFFFAOYSA-N 0.000 description 1
- FXIUAWJHIHRDFL-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)-4-[4-(trifluoromethyl)phenyl]pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(=CC=2)C(F)(F)F)C(=O)N(CC(F)(F)F)N=C1 FXIUAWJHIHRDFL-UHFFFAOYSA-N 0.000 description 1
- TVDIYPPHWHUGLJ-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-4-(1-oxo-3h-2-benzofuran-5-yl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C3COC(=O)C3=CC=2)C(=O)N(CC(F)(F)F)N=C1 TVDIYPPHWHUGLJ-UHFFFAOYSA-N 0.000 description 1
- FESHIQBIYHNNKB-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-4-(1h-1,2,4-triazol-5-ylsulfanyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(SC2=NNC=N2)C(=O)N(CC(F)(F)F)N=C1 FESHIQBIYHNNKB-UHFFFAOYSA-N 0.000 description 1
- KJBJFSTYBPCPBM-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-4-(2,3,5-trifluoroanilino)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(NC=2C(=C(F)C=C(F)C=2)F)C(=O)N(CC(F)(F)F)N=C1 KJBJFSTYBPCPBM-UHFFFAOYSA-N 0.000 description 1
- VCKJESNFOSTZHG-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-4-(2-piperidin-1-ylethylamino)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(NCCN2CCCCC2)C(=O)N(CC(F)(F)F)N=C1 VCKJESNFOSTZHG-UHFFFAOYSA-N 0.000 description 1
- BDHNOJWTZWMGQQ-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-4-(3-nitrophenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(C=CC=2)[N+]([O-])=O)C(=O)N(CC(F)(F)F)N=C1 BDHNOJWTZWMGQQ-UHFFFAOYSA-N 0.000 description 1
- WGBKBZQZQRRSRH-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-4-(4-phenylphenoxy)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC(=CC=2)C=2C=CC=CC=2)C(=O)N(CC(F)(F)F)N=C1 WGBKBZQZQRRSRH-UHFFFAOYSA-N 0.000 description 1
- PWBYMGKKMQVMJB-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-4-(4-propylphenoxy)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(CCC)=CC=C1OC1=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN(CC(F)(F)F)C1=O PWBYMGKKMQVMJB-UHFFFAOYSA-N 0.000 description 1
- UYMGEMAFTUQADA-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-4-(4-propylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(CCC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN(CC(F)(F)F)C1=O UYMGEMAFTUQADA-UHFFFAOYSA-N 0.000 description 1
- CSYSLXRBRFBFQZ-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-4-(propan-2-ylamino)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=NN(CC(F)(F)F)C(=O)C(NC(C)C)=C1C1=CC=C(S(C)(=O)=O)C=C1 CSYSLXRBRFBFQZ-UHFFFAOYSA-N 0.000 description 1
- DBDFGUIJKFTAEM-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-4-phenylmethoxy-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OCC=2C=CC=CC=2)C(=O)N(CC(F)(F)F)N=C1 DBDFGUIJKFTAEM-UHFFFAOYSA-N 0.000 description 1
- WPFQDTGJUFRWDQ-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-4-piperidin-1-yl-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(N2CCCCC2)C(=O)N(CC(F)(F)F)N=C1 WPFQDTGJUFRWDQ-UHFFFAOYSA-N 0.000 description 1
- PADDMNIMZJIGGS-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-4-prop-2-enyl-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(CC=C)C(=O)N(CC(F)(F)F)N=C1 PADDMNIMZJIGGS-UHFFFAOYSA-N 0.000 description 1
- JBNPDONMDIEQOW-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-4-propan-2-ylsulfanyl-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=NN(CC(F)(F)F)C(=O)C(SC(C)C)=C1C1=CC=C(S(C)(=O)=O)C=C1 JBNPDONMDIEQOW-UHFFFAOYSA-N 0.000 description 1
- NICPALOBHSRDCA-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-4-pyridin-3-yloxy-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=NC=CC=2)C(=O)N(CC(F)(F)F)N=C1 NICPALOBHSRDCA-UHFFFAOYSA-N 0.000 description 1
- GBRSPKXOFRTAHS-UHFFFAOYSA-N 5-(4-nitrophenyl)-1,2-oxazole-3-carboxylic acid Chemical compound O1N=C(C(=O)O)C=C1C1=CC=C([N+]([O-])=O)C=C1 GBRSPKXOFRTAHS-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- WCBPTWDNLIFCRH-UHFFFAOYSA-N 5-bromo-2-(4-fluorophenyl)-4-propan-2-yloxypyridazin-3-one Chemical compound O=C1C(OC(C)C)=C(Br)C=NN1C1=CC=C(F)C=C1 WCBPTWDNLIFCRH-UHFFFAOYSA-N 0.000 description 1
- MMFGGDVQLQQQRX-UHFFFAOYSA-N 5-bromo-2-fluorobenzaldehyde Chemical compound FC1=CC=C(Br)C=C1C=O MMFGGDVQLQQQRX-UHFFFAOYSA-N 0.000 description 1
- DUAZKLYNTLDKQK-UHFFFAOYSA-N 5-hydroxy-2(5h)-furanone Chemical class OC1OC(=O)C=C1 DUAZKLYNTLDKQK-UHFFFAOYSA-N 0.000 description 1
- PXNZRPJFJIKDKT-UHFFFAOYSA-N 5-hydroxy-5-methylfuran-2-one Chemical compound CC1(O)OC(=O)C=C1 PXNZRPJFJIKDKT-UHFFFAOYSA-N 0.000 description 1
- LLPOBYGXVLYIJR-UHFFFAOYSA-N 5-methylidene-1,4,2,3-dioxadithiolane Chemical compound C=C1OSSO1 LLPOBYGXVLYIJR-UHFFFAOYSA-N 0.000 description 1
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical group CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- VBJXQFMXZXUSGP-UHFFFAOYSA-N CSC1=CC=C(C=C1)CC(=C=S)C Chemical compound CSC1=CC=C(C=C1)CC(=C=S)C VBJXQFMXZXUSGP-UHFFFAOYSA-N 0.000 description 1
- 101100496968 Caenorhabditis elegans ctc-1 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- HDBYUCSVKZBWDH-UHFFFAOYSA-N ClC1=CC=C[S+]1Br Chemical compound ClC1=CC=C[S+]1Br HDBYUCSVKZBWDH-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 102220501443 Cytosolic iron-sulfur assembly component 3_C27N_mutation Human genes 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- NLLWMDYGRUZWHR-UHFFFAOYSA-N FC(C1=C(C=C(C=C1)[N+](=O)[O-])N1N=CC(=C(C1=O)C1=CC=C(C=C1)F)C1=CC=C(C=C1)S(=O)(=O)C)(F)F Chemical compound FC(C1=C(C=C(C=C1)[N+](=O)[O-])N1N=CC(=C(C1=O)C1=CC=C(C=C1)F)C1=CC=C(C=C1)S(=O)(=O)C)(F)F NLLWMDYGRUZWHR-UHFFFAOYSA-N 0.000 description 1
- PTGAOHULGRCGGG-UHFFFAOYSA-N FC(CN1N=CC(=C(C1=O)N=[N+]=[N-])C1=CC=C(C=C1)SC)(F)F Chemical compound FC(CN1N=CC(=C(C1=O)N=[N+]=[N-])C1=CC=C(C=C1)SC)(F)F PTGAOHULGRCGGG-UHFFFAOYSA-N 0.000 description 1
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 101000605122 Homo sapiens Prostaglandin G/H synthase 1 Proteins 0.000 description 1
- 101000605127 Homo sapiens Prostaglandin G/H synthase 2 Proteins 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- FEYNFHSRETUBEM-UHFFFAOYSA-N N-[3-(1,1-difluoroethyl)phenyl]-1-(4-methoxyphenyl)-3-methyl-5-oxo-4H-pyrazole-4-carboxamide Chemical compound COc1ccc(cc1)N1N=C(C)C(C(=O)Nc2cccc(c2)C(C)(F)F)C1=O FEYNFHSRETUBEM-UHFFFAOYSA-N 0.000 description 1
- GANVVEVENXLPOL-UHFFFAOYSA-N N1(C=CC=C1)C1=CC=C(C=C1)N1N=CC(=C(C1=O)C1=CC=C(C=C1)F)C1=CC=C(C=C1)S(=O)(=O)C Chemical compound N1(C=CC=C1)C1=CC=C(C=C1)N1N=CC(=C(C1=O)C1=CC=C(C=C1)F)C1=CC=C(C=C1)S(=O)(=O)C GANVVEVENXLPOL-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
- 101100221647 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cox-1 gene Proteins 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- AEQWOQQHLOPWCA-UHFFFAOYSA-N OBO.CSC1=CC=CC=C1 Chemical compound OBO.CSC1=CC=CC=C1 AEQWOQQHLOPWCA-UHFFFAOYSA-N 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 229910019213 POCl3 Inorganic materials 0.000 description 1
- 101150062589 PTGS1 gene Proteins 0.000 description 1
- 229920002230 Pectic acid Polymers 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical group NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 description 1
- 229910006124 SOCl2 Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 description 1
- OICKXBLUSSLLHO-UHFFFAOYSA-N [1-benzyl-5-(4-fluorophenyl)-6-oxopyridazin-4-yl] trifluoromethanesulfonate Chemical compound C1=CC(F)=CC=C1C(C1=O)=C(OS(=O)(=O)C(F)(F)F)C=NN1CC1=CC=CC=C1 OICKXBLUSSLLHO-UHFFFAOYSA-N 0.000 description 1
- HMQYWSYDKFJLJS-UHFFFAOYSA-N [2-(3,4-difluorophenyl)-5-(3-fluoro-4-methylsulfonylphenyl)-3-oxopyridazin-4-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC(C1=O)=C(C=2C=C(F)C(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 HMQYWSYDKFJLJS-UHFFFAOYSA-N 0.000 description 1
- KPBUQEUKGVSXFS-UHFFFAOYSA-N [2-(3,4-difluorophenyl)-5-(4-methylsulfonylphenyl)-3-oxopyridazin-4-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC(C1=O)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 KPBUQEUKGVSXFS-UHFFFAOYSA-N 0.000 description 1
- BRPJTYKNOSLFHD-UHFFFAOYSA-N [2-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-3-oxopyridazin-4-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC(C1=O)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C=C1 BRPJTYKNOSLFHD-UHFFFAOYSA-N 0.000 description 1
- IIGYWPIOFPWSRY-UHFFFAOYSA-N [3-amino-6-pyridin-4-yl-4-(trifluoromethyl)thieno[2,3-b]pyridin-2-yl]-(2,3-dihydro-1,4-benzodioxin-6-yl)methanone Chemical compound C=1C(C(F)(F)F)=C2C(N)=C(C(=O)C=3C=C4OCCOC4=CC=3)SC2=NC=1C1=CC=NC=C1 IIGYWPIOFPWSRY-UHFFFAOYSA-N 0.000 description 1
- SMBSEUSQDBBAIH-UHFFFAOYSA-N [5-chloro-6-oxo-1-(2,2,2-trifluoroethyl)pyridazin-4-yl] trifluoromethanesulfonate Chemical compound FC(F)(F)CN1N=CC(OS(=O)(=O)C(F)(F)F)=C(Cl)C1=O SMBSEUSQDBBAIH-UHFFFAOYSA-N 0.000 description 1
- OBUYHLRHYXFFBC-UHFFFAOYSA-M [Br-].CC(C)CCCC[Mg+] Chemical compound [Br-].CC(C)CCCC[Mg+] OBUYHLRHYXFFBC-UHFFFAOYSA-M 0.000 description 1
- YGGBUBJZSWZIDG-UHFFFAOYSA-M [Br-].FC1=CC([Mg+])=CC=C1C=C Chemical compound [Br-].FC1=CC([Mg+])=CC=C1C=C YGGBUBJZSWZIDG-UHFFFAOYSA-M 0.000 description 1
- SJQMIXOMFZKLGS-UHFFFAOYSA-L [Br-].[Mg+2].FC1=C(C=CC=C1)C.[Br-] Chemical compound [Br-].[Mg+2].FC1=C(C=CC=C1)C.[Br-] SJQMIXOMFZKLGS-UHFFFAOYSA-L 0.000 description 1
- DXMAARCZJITWJZ-UHFFFAOYSA-L [Mg+2].[Br-].[Br-].CC#C Chemical compound [Mg+2].[Br-].[Br-].CC#C DXMAARCZJITWJZ-UHFFFAOYSA-L 0.000 description 1
- AVPMRIWGOGRNBF-UHFFFAOYSA-N [bromo(fluoro)methyl]benzene Chemical compound FC(Br)C1=CC=CC=C1 AVPMRIWGOGRNBF-UHFFFAOYSA-N 0.000 description 1
- QQIRAVWVGBTHMJ-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;lithium Chemical compound [Li].C[Si](C)(C)N[Si](C)(C)C QQIRAVWVGBTHMJ-UHFFFAOYSA-N 0.000 description 1
- LRIUKPUCKCECPT-UHFFFAOYSA-N [hydroxy(phenyl)-$l^{3}-iodanyl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OI(O)C1=CC=CC=C1 LRIUKPUCKCECPT-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- UFSKCTMESWSZJP-UHFFFAOYSA-N acetyloxymethylsulfonylmethyl acetate Chemical compound CC(=O)OCS(=O)(=O)COC(C)=O UFSKCTMESWSZJP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 1
- FOWDOWQYRZXQDP-UHFFFAOYSA-N adamantan-2-ol Chemical compound C1C(C2)CC3CC1C(O)C2C3 FOWDOWQYRZXQDP-UHFFFAOYSA-N 0.000 description 1
- 125000005076 adamantyloxycarbonyl group Chemical group C12(CC3CC(CC(C1)C3)C2)OC(=O)* 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000006307 alkoxy benzyl group Chemical group 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 125000005205 alkoxycarbonyloxyalkyl group Chemical group 0.000 description 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
- 208000030961 allergic reaction Diseases 0.000 description 1
- AEMOLEFTQBMNLQ-BKBMJHBISA-N alpha-D-galacturonic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-BKBMJHBISA-N 0.000 description 1
- UAMZETBJZRERCQ-UHFFFAOYSA-N alpha-aminopropionitrile Chemical group CC(N)C#N UAMZETBJZRERCQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000002431 aminoalkoxy group Chemical group 0.000 description 1
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 238000011861 anti-inflammatory therapy Methods 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 229940111136 antiinflammatory and antirheumatic drug fenamates Drugs 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 1
- 125000005015 aryl alkynyl group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- PRBLRLQZOKOQCQ-UHFFFAOYSA-N benzylhydrazine;hydron;chloride Chemical compound Cl.NNCC1=CC=CC=C1 PRBLRLQZOKOQCQ-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000006696 biosynthetic metabolic pathway Effects 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- KXVUSQIDCZRUKF-UHFFFAOYSA-N bromocyclobutane Chemical compound BrC1CCC1 KXVUSQIDCZRUKF-UHFFFAOYSA-N 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 description 1
- AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical class CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- WIKQEUJFZPCFNJ-UHFFFAOYSA-N carbonic acid;silver Chemical compound [Ag].[Ag].OC(O)=O WIKQEUJFZPCFNJ-UHFFFAOYSA-N 0.000 description 1
- 125000005518 carboxamido group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- BJDCWCLMFKKGEE-CMDXXVQNSA-N chembl252518 Chemical compound C([C@@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2O[C@H](O)[C@@H]4C BJDCWCLMFKKGEE-CMDXXVQNSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000011260 co-administration Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 description 1
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 1
- CMKBCTPCXZNQKX-UHFFFAOYSA-N cyclohexanethiol Chemical compound SC1CCCCC1 CMKBCTPCXZNQKX-UHFFFAOYSA-N 0.000 description 1
- 125000000062 cyclohexylmethoxy group Chemical group [H]C([H])(O*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- XMPWFKHMCNRJCL-UHFFFAOYSA-M cyclopropyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C1CC1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XMPWFKHMCNRJCL-UHFFFAOYSA-M 0.000 description 1
- IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical group NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000004986 diarylamino group Chemical group 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 1
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- UZZWBUYVTBPQIV-UHFFFAOYSA-N dme dimethoxyethane Chemical compound COCCOC.COCCOC UZZWBUYVTBPQIV-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000002662 enteric coated tablet Substances 0.000 description 1
- 238000007824 enzymatic assay Methods 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- LXCHKJVKUPIUAL-UHFFFAOYSA-N ethyl 3,3,3-trifluoro-2-[(6-fluoro-1,3-benzothiazol-2-yl)amino]-2-(pentanoylamino)propanoate Chemical compound C1=C(F)C=C2SC(NC(NC(=O)CCCC)(C(=O)OCC)C(F)(F)F)=NC2=C1 LXCHKJVKUPIUAL-UHFFFAOYSA-N 0.000 description 1
- BBWMASBANDIFMV-UHFFFAOYSA-N ethyl 4-phenylpiperidine-4-carboxylate;hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C1(C(=O)OCC)CC[NH2+]CC1 BBWMASBANDIFMV-UHFFFAOYSA-N 0.000 description 1
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- BPQPBEVHMFRECG-UHFFFAOYSA-N fluoro formate Chemical compound FOC=O BPQPBEVHMFRECG-UHFFFAOYSA-N 0.000 description 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 description 1
- 125000005291 haloalkenyloxy group Chemical group 0.000 description 1
- 125000000232 haloalkynyl group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical class CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
- WQFXFJBXDHKAKY-UHFFFAOYSA-L magnesium ethynylbenzene dibromide Chemical compound [Mg+2].[Br-].[Br-].C#CC1=CC=CC=C1 WQFXFJBXDHKAKY-UHFFFAOYSA-L 0.000 description 1
- QLGSDGDHUROFKU-UHFFFAOYSA-M magnesium;1-fluoro-2-methylbenzene-5-ide;bromide Chemical compound [Mg+2].[Br-].CC1=CC=[C-]C=C1F QLGSDGDHUROFKU-UHFFFAOYSA-M 0.000 description 1
- JHMNJUQVLPODJN-UHFFFAOYSA-M magnesium;1-fluoro-4-methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=C(F)C=C1 JHMNJUQVLPODJN-UHFFFAOYSA-M 0.000 description 1
- UKZCGMDMXDLAGZ-UHFFFAOYSA-M magnesium;2-methylpropane;bromide Chemical compound [Mg+2].[Br-].C[C-](C)C UKZCGMDMXDLAGZ-UHFFFAOYSA-M 0.000 description 1
- HTJPDOPKPWUNBX-UHFFFAOYSA-M magnesium;2h-thiophen-2-ide;bromide Chemical compound [Mg+2].[Br-].C=1C=[C-]SC=1 HTJPDOPKPWUNBX-UHFFFAOYSA-M 0.000 description 1
- FGYXQBPXHQHYNU-UHFFFAOYSA-M magnesium;but-2-ene;bromide Chemical compound [Mg+2].[Br-].CC=[C-]C FGYXQBPXHQHYNU-UHFFFAOYSA-M 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 description 1
- JGPDOURHDDKDEZ-UHFFFAOYSA-M magnesium;ethynylbenzene;bromide Chemical compound [Mg+2].[Br-].[C-]#CC1=CC=CC=C1 JGPDOURHDDKDEZ-UHFFFAOYSA-M 0.000 description 1
- SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- GFBWODZPLVOXSH-UHFFFAOYSA-N methyl 2-(4-fluorophenyl)-4-methylsulfanyl-3-(4-methylsulfanylphenyl)-4-methylsulfinylbutanoate Chemical compound C=1C=C(F)C=CC=1C(C(=O)OC)C(C(SC)S(C)=O)C1=CC=C(SC)C=C1 GFBWODZPLVOXSH-UHFFFAOYSA-N 0.000 description 1
- NLWBJPPMPLPZIE-UHFFFAOYSA-N methyl 4-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=C(CBr)C=C1 NLWBJPPMPLPZIE-UHFFFAOYSA-N 0.000 description 1
- OJLOPKGSLYJEMD-URPKTTJQSA-N methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(1e)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate Chemical compound CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC OJLOPKGSLYJEMD-URPKTTJQSA-N 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
- MPHBIACXKTZAFW-UHFFFAOYSA-N methylsulfanyl(methylsulfonyl)methane Chemical compound CSCS(C)(=O)=O MPHBIACXKTZAFW-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229960005249 misoprostol Drugs 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- PEECTLLHENGOKU-UHFFFAOYSA-N n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC=C1.CN(C)C1=CC=NC=C1 PEECTLLHENGOKU-UHFFFAOYSA-N 0.000 description 1
- UVRQSUHQNDJDMJ-UHFFFAOYSA-N n-(4-chlorophenyl)-2-[1-(4-hexoxyphenyl)-2,5-dioxopyrrolidin-3-yl]sulfanylacetamide Chemical compound C1=CC(OCCCCCC)=CC=C1N1C(=O)C(SCC(=O)NC=2C=CC(Cl)=CC=2)CC1=O UVRQSUHQNDJDMJ-UHFFFAOYSA-N 0.000 description 1
- FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 1
- AYEQJLOHMLYKAV-UHFFFAOYSA-N n-(4-sulfanylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S)C=C1 AYEQJLOHMLYKAV-UHFFFAOYSA-N 0.000 description 1
- UVXAAFITSHYVSI-UHFFFAOYSA-N n-[2-chloro-5-(trifluoromethyl)phenyl]-2-[[5-(phenoxymethyl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide Chemical compound FC(F)(F)C1=CC=C(Cl)C(NC(=O)CSC=2OC(COC=3C=CC=CC=3)=NN=2)=C1 UVXAAFITSHYVSI-UHFFFAOYSA-N 0.000 description 1
- QROYZARICDCRJK-UHFFFAOYSA-N n-[4-[5-(4-methylsulfonylphenyl)-3-oxo-2-(2,2,2-trifluoroethyl)pyridazin-4-yl]sulfanylphenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1SC1=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN(CC(F)(F)F)C1=O QROYZARICDCRJK-UHFFFAOYSA-N 0.000 description 1
- VFBILHPIHUPBPZ-UHFFFAOYSA-N n-[[2-[4-(difluoromethoxy)-3-propan-2-yloxyphenyl]-1,3-oxazol-4-yl]methyl]-2-ethoxybenzamide Chemical compound CCOC1=CC=CC=C1C(=O)NCC1=COC(C=2C=C(OC(C)C)C(OC(F)F)=CC=2)=N1 VFBILHPIHUPBPZ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DOWVMJFBDGWVML-UHFFFAOYSA-N n-cyclohexyl-n-methyl-4-(1-oxidopyridin-1-ium-3-yl)imidazole-1-carboxamide Chemical compound C1=NC(C=2C=[N+]([O-])C=CC=2)=CN1C(=O)N(C)C1CCCCC1 DOWVMJFBDGWVML-UHFFFAOYSA-N 0.000 description 1
- NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000016087 ovulation Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 description 1
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000007310 pathophysiology Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- XDEPVFFKOVDUNO-UHFFFAOYSA-N pentafluorobenzyl bromide Chemical compound FC1=C(F)C(F)=C(CBr)C(F)=C1F XDEPVFFKOVDUNO-UHFFFAOYSA-N 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 208000008423 pleurisy Diseases 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- CUNPJFGIODEJLQ-UHFFFAOYSA-M potassium;2,2,2-trifluoroacetate Chemical compound [K+].[O-]C(=O)C(F)(F)F CUNPJFGIODEJLQ-UHFFFAOYSA-M 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002089 prostaglandin antagonist Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 102200145454 rs121908575 Human genes 0.000 description 1
- IYLGZMTXKJYONK-UHFFFAOYSA-N ruwenine Natural products O1C(=O)C(CC)(O)CC(C)C(C)(OC(C)=O)C(=O)OCC2=CCN3C2C1CC3 IYLGZMTXKJYONK-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- KQTXIZHBFFWWFW-UHFFFAOYSA-L silver(I) carbonate Inorganic materials [Ag]OC(=O)O[Ag] KQTXIZHBFFWWFW-UHFFFAOYSA-L 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000004206 stomach function Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- DDPWVABNMBRBFI-UHFFFAOYSA-N tert-butylhydrazine;hydron;chloride Chemical compound Cl.CC(C)(C)NN DDPWVABNMBRBFI-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/18—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US91702397A | 1997-08-22 | 1997-08-22 | |
US12957098A | 1998-08-05 | 1998-08-05 | |
PCT/US1998/016479 WO1999010331A1 (en) | 1997-08-22 | 1998-08-10 | Arylpyridazinones as prostaglandin endoperoxide h synthase biosynthesis inhibitors |
Publications (2)
Publication Number | Publication Date |
---|---|
PL355418A1 PL355418A1 (en) | 2004-04-19 |
PL194175B1 true PL194175B1 (pl) | 2007-05-31 |
Family
ID=26827711
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PL98355418A PL194175B1 (pl) | 1997-08-22 | 1998-08-10 | Pirydazynony, zawierające je kompozycje farmaceutyczne oraz ich zastosowanie |
Country Status (14)
Country | Link |
---|---|
JP (1) | JP2003516925A (cs) |
KR (1) | KR100675028B1 (cs) |
CN (1) | CN1167687C (cs) |
AR (1) | AR015422A1 (cs) |
AU (1) | AU741317B2 (cs) |
BG (1) | BG64675B1 (cs) |
CZ (1) | CZ300847B6 (cs) |
HU (1) | HUP0400909A3 (cs) |
IL (1) | IL133552A (cs) |
NO (1) | NO315423B1 (cs) |
NZ (1) | NZ501808A (cs) |
PL (1) | PL194175B1 (cs) |
SK (1) | SK286972B6 (cs) |
TR (1) | TR200000478T2 (cs) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HK1041876B (en) * | 1998-10-27 | 2006-06-23 | Abbott Laboratories | Prostaglandin endoperoxide h synthase biosynthesis inhibitors |
FR2969606B1 (fr) * | 2010-12-22 | 2013-01-11 | Pf Medicament | Derives de diarylpyridazinones, leur preparation et leur application en therapeutique humaine |
CN107334767B (zh) * | 2017-06-08 | 2019-03-05 | 中国医学科学院医药生物技术研究所 | 一种哒嗪酮类化合物在肿瘤治疗中的应用 |
JP7147444B2 (ja) * | 2018-10-03 | 2022-10-05 | 株式会社島津製作所 | 試料注入装置および試料注入システム |
CN114560814B (zh) * | 2022-03-02 | 2023-10-20 | 天津理工大学 | 一种取代2,3-二氮杂萘酮类化合物的合成方法 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4238490A (en) * | 1979-02-12 | 1980-12-09 | Diamond Shamrock Corporation | Antihypertensive pyridazin(2H)-3-ones |
BR8108745A (pt) * | 1980-08-07 | 1982-07-06 | Diamond Shamrock Corp | Difenilpiridazinonas herbicidas e reguladores do crescimento da planta |
US4404203A (en) * | 1981-05-14 | 1983-09-13 | Warner-Lambert Company | Substituted 6-phenyl-3(2H)-pyridazinones useful as cardiotonic agents |
WO1988009675A1 (en) * | 1987-06-05 | 1988-12-15 | Medicis Corporation | Inhibition of arachidonic acid metabolism |
IL115889A0 (en) * | 1994-11-14 | 1996-01-31 | Rohm & Haas | Pyridazinones and their use as fungicides |
US5622948A (en) * | 1994-12-01 | 1997-04-22 | Syntex (U.S.A.) Inc. | Pyrrole pyridazine and pyridazinone anti-inflammatory agents |
CA2224563A1 (en) * | 1995-06-12 | 1996-12-27 | G.D. Searle & Co. | Combination of a cyclooxygenase-2 inhibitor and a leukotriene b4 receptor antagonist for the treatment of inflammations |
ES2224366T3 (es) * | 1997-03-14 | 2005-03-01 | MERCK FROSST CANADA & CO. | Piridazinonas como inhibidores de ciclooxigenasa-2. |
-
1998
- 1998-08-10 HU HU0400909A patent/HUP0400909A3/hu unknown
- 1998-08-10 JP JP2000507660A patent/JP2003516925A/ja active Pending
- 1998-08-10 SK SK231-2000A patent/SK286972B6/sk not_active IP Right Cessation
- 1998-08-10 CN CNB988083221A patent/CN1167687C/zh not_active Expired - Fee Related
- 1998-08-10 CZ CZ20000446A patent/CZ300847B6/cs not_active IP Right Cessation
- 1998-08-10 AU AU86976/98A patent/AU741317B2/en not_active Ceased
- 1998-08-10 NZ NZ501808A patent/NZ501808A/xx unknown
- 1998-08-10 KR KR1020007001824A patent/KR100675028B1/ko not_active Expired - Fee Related
- 1998-08-10 PL PL98355418A patent/PL194175B1/pl not_active IP Right Cessation
- 1998-08-10 IL IL13355298A patent/IL133552A/xx not_active IP Right Cessation
- 1998-08-10 TR TR2000/00478T patent/TR200000478T2/xx unknown
- 1998-08-24 AR ARP980104193A patent/AR015422A1/es active IP Right Grant
-
2000
- 2000-02-22 NO NO20000863A patent/NO315423B1/no not_active IP Right Cessation
- 2000-03-15 BG BG104241A patent/BG64675B1/bg unknown
Also Published As
Publication number | Publication date |
---|---|
AR015422A1 (es) | 2001-05-02 |
CN1167687C (zh) | 2004-09-22 |
IL133552A0 (en) | 2001-04-30 |
SK2312000A3 (en) | 2001-02-12 |
CZ300847B6 (cs) | 2009-08-26 |
AU8697698A (en) | 1999-03-16 |
BG64675B1 (bg) | 2005-11-30 |
NO315423B1 (no) | 2003-09-01 |
JP2003516925A (ja) | 2003-05-20 |
HUP0400909A3 (en) | 2004-10-28 |
IL133552A (en) | 2005-12-18 |
KR100675028B1 (ko) | 2007-01-29 |
NO20000863D0 (no) | 2000-02-22 |
SK286972B6 (sk) | 2009-08-06 |
BG104241A (en) | 2000-10-31 |
KR20010023196A (ko) | 2001-03-26 |
CZ2000446A3 (cs) | 2000-05-17 |
NO20000863L (no) | 2000-02-22 |
PL355418A1 (en) | 2004-04-19 |
NZ501808A (en) | 2002-12-20 |
TR200000478T2 (tr) | 2002-04-22 |
AU741317B2 (en) | 2001-11-29 |
CN1277605A (zh) | 2000-12-20 |
HUP0400909A2 (hu) | 2004-07-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2299300C (en) | Arylpyridazinones as prostaglandin endoperoxide h synthase bisoynthesis inhibitors | |
US6307047B1 (en) | Prostaglandin endoperoxide H synthase biosynthesis inhibitors | |
KR100666838B1 (ko) | 프로스타글란딘 엔도퍼옥사이드 h 신타제 생합성 억제제 및 이를 포함하는 약제학적 조성물 | |
AU2008206441B2 (en) | N-substituted glycine derivatives: hydroxylase inhibitors | |
JP5237799B2 (ja) | ピラゾールベースのlxrモジュレーター | |
AU2005280487A1 (en) | Modulators of nuclear receptors | |
CA2305413A1 (en) | Aryl furan derivatives as pde iv inhibitors | |
CA2460942A1 (en) | Substituted pyrazolyl compounds for the treatment of inflammation | |
CA2305414A1 (en) | Aryl thiophene derivatives as pde iv inhibitors | |
KR100675028B1 (ko) | 프로스타글란딘 엔도퍼옥사이드 h 신타제 생합성 억제제로서의 아릴피리다지논, 이를 포함하는 약제학적 조성물 및 이의 제조방법 | |
CA2485298C (en) | Substituted pyrazolyl compounds for the treatment of inflammation | |
AU773237B2 (en) | Prostaglandin endoperoxide H synthase biosynthesis inhibitors | |
CA2578858A1 (en) | Arylpyridazinones as prostaglandin endoperoxide h synthase biosynthesis inhibitors | |
MXPA01004247A (en) | Prostaglandin endoperoxide h synthase biosynthesis inhibitors |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
VDSO | Invalidation of derivated patent or utility model |
Ref document number: 375838 Country of ref document: PL |
|
LAPS | Decisions on the lapse of the protection rights |
Effective date: 20110810 |