HRP20110974T1 - Derivati piperazina i njihova uporaba kao terapeutskih sredstava - Google Patents
Derivati piperazina i njihova uporaba kao terapeutskih sredstava Download PDFInfo
- Publication number
- HRP20110974T1 HRP20110974T1 HR20110974T HRP20110974T HRP20110974T1 HR P20110974 T1 HRP20110974 T1 HR P20110974T1 HR 20110974 T HR20110974 T HR 20110974T HR P20110974 T HRP20110974 T HR P20110974T HR P20110974 T1 HRP20110974 T1 HR P20110974T1
- Authority
- HR
- Croatia
- Prior art keywords
- piperazin
- pyridazine
- carboxylic acid
- amide
- trifluoromethylbenzoyl
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims 2
- 150000004885 piperazines Chemical class 0.000 title 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title 1
- 229940124597 therapeutic agent Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 84
- 229910052739 hydrogen Inorganic materials 0.000 claims 145
- 239000001257 hydrogen Substances 0.000 claims 145
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 87
- 125000001424 substituent group Chemical group 0.000 claims 70
- 125000005843 halogen group Chemical group 0.000 claims 65
- 150000002431 hydrogen Chemical class 0.000 claims 58
- -1 chloro, methyl Chemical group 0.000 claims 50
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 31
- 125000003118 aryl group Chemical group 0.000 claims 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 28
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 27
- 125000001153 fluoro group Chemical group F* 0.000 claims 26
- 125000003710 aryl alkyl group Chemical group 0.000 claims 25
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 17
- 201000010099 disease Diseases 0.000 claims 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 13
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 11
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 125000004043 oxo group Chemical group O=* 0.000 claims 11
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims 9
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000003367 polycyclic group Chemical group 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 6
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 5
- 208000004930 Fatty Liver Diseases 0.000 claims 4
- 108010087894 Fatty acid desaturases Proteins 0.000 claims 4
- 206010019708 Hepatic steatosis Diseases 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 4
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 4
- 208000008589 Obesity Diseases 0.000 claims 4
- 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 claims 4
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 4
- 208000010706 fatty liver disease Diseases 0.000 claims 4
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 4
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 4
- 235000020824 obesity Nutrition 0.000 claims 4
- 231100000240 steatosis hepatitis Toxicity 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000004450 alkenylene group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- NHTUUHRKJSDBLX-UHFFFAOYSA-N 1-[1-(4-fluorophenyl)ethyl]-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound C=1C=C(F)C=CC=1C(C)NC(=O)NC(N=N1)=CC=C1N(CC1)CCN1C(=O)C1=CC=CC=C1C(F)(F)F NHTUUHRKJSDBLX-UHFFFAOYSA-N 0.000 claims 2
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- WCGBJDMVMJWYNK-UHFFFAOYSA-N 6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxylic acid Chemical compound N1=NC(C(=O)O)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 WCGBJDMVMJWYNK-UHFFFAOYSA-N 0.000 claims 2
- 208000002874 Acne Vulgaris Diseases 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 208000002705 Glucose Intolerance Diseases 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 206010000496 acne Diseases 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- MPPOAJWOOFSONI-UHFFFAOYSA-N n-(2,5-difluorophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=C(F)C(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 MPPOAJWOOFSONI-UHFFFAOYSA-N 0.000 claims 2
- QFQCGXUMMUCOTQ-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[2-[2-(trifluoromethyl)phenyl]acetyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1CC(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 QFQCGXUMMUCOTQ-UHFFFAOYSA-N 0.000 claims 2
- ZSPRIOXATHSHPO-UHFFFAOYSA-N n-(4-methylpentyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 ZSPRIOXATHSHPO-UHFFFAOYSA-N 0.000 claims 2
- STMZSSSMCXCTIK-UHFFFAOYSA-N n-pyrazin-2-yl-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2N=CC=NC=2)CC1 STMZSSSMCXCTIK-UHFFFAOYSA-N 0.000 claims 2
- 201000009104 prediabetes syndrome Diseases 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 1
- QHSMPJIPQUPYMF-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)NCCCl)=CC=2)CC1 QHSMPJIPQUPYMF-UHFFFAOYSA-N 0.000 claims 1
- AEIWIZFOXARVGN-UHFFFAOYSA-N 1-(2-cyclopropylethyl)-3-[6-[4-(2,6-difluorobenzoyl)piperazin-1-yl]pyridazin-3-yl]urea Chemical compound FC1=CC=CC(F)=C1C(=O)N1CCN(C=2N=NC(NC(=O)NCCC3CC3)=CC=2)CC1 AEIWIZFOXARVGN-UHFFFAOYSA-N 0.000 claims 1
- SUJKQAFERDILBZ-UHFFFAOYSA-N 1-(2-cyclopropylethyl)-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)NCCC3CC3)=CC=2)CC1 SUJKQAFERDILBZ-UHFFFAOYSA-N 0.000 claims 1
- SWOYZPULAJQWBZ-UHFFFAOYSA-N 1-(2-cyclopropylethyl)-3-[6-[4-[2-fluoro-6-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound FC1=CC=CC(C(F)(F)F)=C1C(=O)N1CCN(C=2N=NC(NC(=O)NCCC3CC3)=CC=2)CC1 SWOYZPULAJQWBZ-UHFFFAOYSA-N 0.000 claims 1
- ONVKCEQQNGJCMZ-UHFFFAOYSA-N 1-(2-cyclopropylethyl)-3-[6-[4-[5-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound FC1=CC=C(C(F)(F)F)C(C(=O)N2CCN(CC2)C=2N=NC(NC(=O)NCCC3CC3)=CC=2)=C1 ONVKCEQQNGJCMZ-UHFFFAOYSA-N 0.000 claims 1
- VQALKTICWWQHJV-UHFFFAOYSA-N 1-(2-fluorophenyl)-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound FC1=CC=CC=C1NC(=O)NC1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 VQALKTICWWQHJV-UHFFFAOYSA-N 0.000 claims 1
- GZOURJGSBBBXJT-UHFFFAOYSA-N 1-(2-phenylcyclopropyl)-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)NC3C(C3)C=3C=CC=CC=3)=CC=2)CC1 GZOURJGSBBBXJT-UHFFFAOYSA-N 0.000 claims 1
- JAYIDWBBAOWJEW-UHFFFAOYSA-N 1-(2-phenylethyl)-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)NCCC=3C=CC=CC=3)=CC=2)CC1 JAYIDWBBAOWJEW-UHFFFAOYSA-N 0.000 claims 1
- XKOLIFCVWWWVJP-UHFFFAOYSA-N 1-(2-propan-2-yloxyethyl)-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound N1=NC(NC(=O)NCCOC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 XKOLIFCVWWWVJP-UHFFFAOYSA-N 0.000 claims 1
- NYIHRTLJFFCZNQ-UHFFFAOYSA-N 1-(3,3-dimethylbutyl)-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound N1=NC(NC(=O)NCCC(C)(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 NYIHRTLJFFCZNQ-UHFFFAOYSA-N 0.000 claims 1
- MLHVYKYPIZBTHE-UHFFFAOYSA-N 1-(3-cyclopropylpropyl)-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)NCCCC3CC3)=CC=2)CC1 MLHVYKYPIZBTHE-UHFFFAOYSA-N 0.000 claims 1
- IKIPWXCGCVTDEN-UHFFFAOYSA-N 1-(3-cyclopropylpropyl)-3-[6-[4-[5-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound FC1=CC=C(C(F)(F)F)C(C(=O)N2CCN(CC2)C=2N=NC(NC(=O)NCCCC3CC3)=CC=2)=C1 IKIPWXCGCVTDEN-UHFFFAOYSA-N 0.000 claims 1
- DUQFZGJFMYCKLE-UHFFFAOYSA-N 1-(3-hydroxy-4,4-dimethylpentyl)-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound N1=NC(NC(=O)NCCC(O)C(C)(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 DUQFZGJFMYCKLE-UHFFFAOYSA-N 0.000 claims 1
- WZEGSAHUKHZCEU-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound C1=CC(F)=CC=C1NC(=O)NC1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 WZEGSAHUKHZCEU-UHFFFAOYSA-N 0.000 claims 1
- NBAALUDFISAAJA-UHFFFAOYSA-N 1-(4-methylpentyl)-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound N1=NC(NC(=O)NCCCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 NBAALUDFISAAJA-UHFFFAOYSA-N 0.000 claims 1
- IQBIUUGGLLEKLB-UHFFFAOYSA-N 1-(cyclopropylmethyl)-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)NCC3CC3)=CC=2)CC1 IQBIUUGGLLEKLB-UHFFFAOYSA-N 0.000 claims 1
- AMQRMGHZNCDQDY-UHFFFAOYSA-N 1-(trifluoromethyl)-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]cyclopropane-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)C3(CC3)C(F)(F)F)=CC=2)CC1 AMQRMGHZNCDQDY-UHFFFAOYSA-N 0.000 claims 1
- IHOWRTKMDQEVJH-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)NCC=3C=C(Cl)C(Cl)=CC=3)=CC=2)CC1 IHOWRTKMDQEVJH-UHFFFAOYSA-N 0.000 claims 1
- WIWODNXACLNNFT-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound C1=CC(F)=CC=C1CNC(=O)NC1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 WIWODNXACLNNFT-UHFFFAOYSA-N 0.000 claims 1
- YUSDOTPTQDPADE-UHFFFAOYSA-N 1-[3-(4-fluorophenyl)propyl]-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound C1=CC(F)=CC=C1CCCNC(=O)NC1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 YUSDOTPTQDPADE-UHFFFAOYSA-N 0.000 claims 1
- HHOUJILDLXWSRC-UHFFFAOYSA-N 1-[6-[4-(2,6-difluorobenzoyl)piperazin-1-yl]pyridazin-3-yl]-3-(3-methylbutyl)urea Chemical compound N1=NC(NC(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2F)F)CC1 HHOUJILDLXWSRC-UHFFFAOYSA-N 0.000 claims 1
- FJLHBWDVJRIKHB-UHFFFAOYSA-N 1-benzyl-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)NCC=3C=CC=CC=3)=CC=2)CC1 FJLHBWDVJRIKHB-UHFFFAOYSA-N 0.000 claims 1
- OHFQYUGIKZHXIQ-UHFFFAOYSA-N 1-butyl-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound N1=NC(NC(=O)NCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 OHFQYUGIKZHXIQ-UHFFFAOYSA-N 0.000 claims 1
- PKZCAEWGUUMUON-UHFFFAOYSA-N 1-cyclohexyl-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)NC3CCCCC3)=CC=2)CC1 PKZCAEWGUUMUON-UHFFFAOYSA-N 0.000 claims 1
- MOOYQJSWCLYCCB-UHFFFAOYSA-N 1-cyclopentyl-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)NC3CCCC3)=CC=2)CC1 MOOYQJSWCLYCCB-UHFFFAOYSA-N 0.000 claims 1
- IGTBOEWVXTVNKE-UHFFFAOYSA-N 1-heptyl-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound N1=NC(NC(=O)NCCCCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 IGTBOEWVXTVNKE-UHFFFAOYSA-N 0.000 claims 1
- XFBJWYKEFMWPTF-UHFFFAOYSA-N 1-hexyl-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound N1=NC(NC(=O)NCCCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 XFBJWYKEFMWPTF-UHFFFAOYSA-N 0.000 claims 1
- YTHGKXXSAATIFL-UHFFFAOYSA-N 1-pentyl-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]urea Chemical compound N1=NC(NC(=O)NCCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 YTHGKXXSAATIFL-UHFFFAOYSA-N 0.000 claims 1
- WMGCWISEXXCQQW-UHFFFAOYSA-N 2,2,3,3-tetramethyl-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]cyclopropane-1-carboxamide Chemical compound CC1(C)C(C)(C)C1C(=O)NC1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 WMGCWISEXXCQQW-UHFFFAOYSA-N 0.000 claims 1
- WSDHHYWWADCKJG-UHFFFAOYSA-N 2-(2-cyclopropylethoxy)-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]acetamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)COCCC3CC3)=CC=2)CC1 WSDHHYWWADCKJG-UHFFFAOYSA-N 0.000 claims 1
- INYBUODGPQZYNE-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]acetamide Chemical compound N1=NC(NC(=O)COCCOC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 INYBUODGPQZYNE-UHFFFAOYSA-N 0.000 claims 1
- VFDBPMRIAMSUIO-UHFFFAOYSA-N 2-(cyclopropylmethoxy)-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]acetamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)COCC3CC3)=CC=2)CC1 VFDBPMRIAMSUIO-UHFFFAOYSA-N 0.000 claims 1
- TYCBMGDCHIAROX-UHFFFAOYSA-N 2-[4-[6-(2-cyclopropylethylcarbamoyl)pyridazin-3-yl]piperazine-1-carbonyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 TYCBMGDCHIAROX-UHFFFAOYSA-N 0.000 claims 1
- KGXJYWZRANVXTO-UHFFFAOYSA-N 2-[[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carbonyl]amino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 KGXJYWZRANVXTO-UHFFFAOYSA-N 0.000 claims 1
- UYBRIYZPGSHRBZ-UHFFFAOYSA-N 2-amino-3-methyl-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]butanamide Chemical compound N1=NC(NC(=O)C(N)C(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 UYBRIYZPGSHRBZ-UHFFFAOYSA-N 0.000 claims 1
- AWQVLJFNMPFLFN-UHFFFAOYSA-N 2-butoxy-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]acetamide Chemical compound N1=NC(NC(=O)COCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 AWQVLJFNMPFLFN-UHFFFAOYSA-N 0.000 claims 1
- ZOGZOXRETBBBJI-UHFFFAOYSA-N 2-cyclopropylethanamine Chemical compound NCCC1CC1 ZOGZOXRETBBBJI-UHFFFAOYSA-N 0.000 claims 1
- XZUNUWUNUPUTKA-UHFFFAOYSA-N 2-cyclopropylethyl n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]carbamate Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)OCCC3CC3)=CC=2)CC1 XZUNUWUNUPUTKA-UHFFFAOYSA-N 0.000 claims 1
- CFQUWMWZQLULST-UHFFFAOYSA-N 2-ethoxy-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]acetamide Chemical compound N1=NC(NC(=O)COCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 CFQUWMWZQLULST-UHFFFAOYSA-N 0.000 claims 1
- YLEYVHROXXDAGB-UHFFFAOYSA-N 2-methylpropyl n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]carbamate Chemical compound N1=NC(NC(=O)OCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 YLEYVHROXXDAGB-UHFFFAOYSA-N 0.000 claims 1
- VZGFTCAIVPZOJO-UHFFFAOYSA-N 2-phenoxy-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]acetamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)COC=3C=CC=CC=3)=CC=2)CC1 VZGFTCAIVPZOJO-UHFFFAOYSA-N 0.000 claims 1
- PXHTVSMFUBWQOX-UHFFFAOYSA-N 2-phenyl-n-(2-phenylcyclopropanecarbonyl)-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]cyclopropane-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)N(C(=O)C2C(C2)C=2C=CC=CC=2)C(=O)C2C(C2)C=2C=CC=CC=2)CC1 PXHTVSMFUBWQOX-UHFFFAOYSA-N 0.000 claims 1
- HLAROSSQODWMPK-UHFFFAOYSA-N 2-phenyl-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]cyclopropane-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)C3C(C3)C=3C=CC=CC=3)=CC=2)CC1 HLAROSSQODWMPK-UHFFFAOYSA-N 0.000 claims 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 claims 1
- GNWLGTKCHVHIMA-UHFFFAOYSA-N 2-phenylmethoxy-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]acetamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)COCC=3C=CC=CC=3)=CC=2)CC1 GNWLGTKCHVHIMA-UHFFFAOYSA-N 0.000 claims 1
- SZPPBXJCQJTJJE-UHFFFAOYSA-N 3,3-dimethylbutyl n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]carbamate Chemical compound N1=NC(NC(=O)OCCC(C)(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 SZPPBXJCQJTJJE-UHFFFAOYSA-N 0.000 claims 1
- DOHLTIJFXUHVQW-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]propanamide Chemical compound C1=CC(F)=CC=C1CCC(=O)NC1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 DOHLTIJFXUHVQW-UHFFFAOYSA-N 0.000 claims 1
- KQQJLQUTMWNJCO-UHFFFAOYSA-N 3-cyclopentyl-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]propanamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)CCC3CCCC3)=CC=2)CC1 KQQJLQUTMWNJCO-UHFFFAOYSA-N 0.000 claims 1
- MJLVGILSJBLATF-UHFFFAOYSA-N 3-methoxy-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]propanamide Chemical compound N1=NC(NC(=O)CCOC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 MJLVGILSJBLATF-UHFFFAOYSA-N 0.000 claims 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 claims 1
- ZAQCWLFIJDECMO-UHFFFAOYSA-N 3-phenoxy-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]propanamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)CCOC=3C=CC=CC=3)=CC=2)CC1 ZAQCWLFIJDECMO-UHFFFAOYSA-N 0.000 claims 1
- CIROBESLMGPNBE-UHFFFAOYSA-N 4-(4-methoxyphenyl)-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]butanamide Chemical compound C1=CC(OC)=CC=C1CCCC(=O)NC1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 CIROBESLMGPNBE-UHFFFAOYSA-N 0.000 claims 1
- OZLLKCVQEONLNS-UHFFFAOYSA-N 4-[[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carbonyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 OZLLKCVQEONLNS-UHFFFAOYSA-N 0.000 claims 1
- NLRUYFNKLLFTLR-UHFFFAOYSA-N 4-cyclohexyl-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]butanamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)CCCC3CCCCC3)=CC=2)CC1 NLRUYFNKLLFTLR-UHFFFAOYSA-N 0.000 claims 1
- XAAJLLUVJBJPAD-UHFFFAOYSA-N 4-fluoro-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]benzamide Chemical compound C1=CC(F)=CC=C1C(=O)NC1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 XAAJLLUVJBJPAD-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- NLKNHRXAUSSMSF-UHFFFAOYSA-N 4-methyl-2-[[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carbonyl]amino]pentanoic acid Chemical compound N1=NC(C(=O)NC(CC(C)C)C(O)=O)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 NLKNHRXAUSSMSF-UHFFFAOYSA-N 0.000 claims 1
- XMFKLBIJEISLHV-UHFFFAOYSA-N 4-methyl-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]pentanamide Chemical compound N1=NC(NC(=O)CCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 XMFKLBIJEISLHV-UHFFFAOYSA-N 0.000 claims 1
- JAWATIRLGNSNCM-UHFFFAOYSA-N 4-phenyl-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]butanamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)CCCC=3C=CC=CC=3)=CC=2)CC1 JAWATIRLGNSNCM-UHFFFAOYSA-N 0.000 claims 1
- LPZGCZYMJAVHKG-UHFFFAOYSA-N 5-(dithiolan-3-yl)-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]pentanamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)CCCCC3SSCC3)=CC=2)CC1 LPZGCZYMJAVHKG-UHFFFAOYSA-N 0.000 claims 1
- HNMNUBZDSBYGPD-UHFFFAOYSA-N 6-(4-benzoylpiperazin-1-yl)-n-(2-cyclopropylethyl)pyridazine-3-carboxamide Chemical compound C=1C=C(N2CCN(CC2)C(=O)C=2C=CC=CC=2)N=NC=1C(=O)NCCC1CC1 HNMNUBZDSBYGPD-UHFFFAOYSA-N 0.000 claims 1
- MDRKEWFRQPAZPS-UHFFFAOYSA-N 6-[2,5-dimethyl-4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]-n-pentylpyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCCCC)=CC=C1N1C(C)CN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)C(C)C1 MDRKEWFRQPAZPS-UHFFFAOYSA-N 0.000 claims 1
- QCRZNYVQOKBABT-UHFFFAOYSA-N 6-[4-(2,4-dichlorobenzoyl)piperazin-1-yl]-n-(3-methylbutyl)pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC(Cl)=CC=2)Cl)CC1 QCRZNYVQOKBABT-UHFFFAOYSA-N 0.000 claims 1
- PMUDELZALXLCFC-UHFFFAOYSA-N 6-[4-(2,6-difluorobenzoyl)piperazin-1-yl]-n-(3-methylbutyl)pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2F)F)CC1 PMUDELZALXLCFC-UHFFFAOYSA-N 0.000 claims 1
- UFAZONDOQRPAAB-UHFFFAOYSA-N 6-[4-(2-aminobenzoyl)piperazin-1-yl]-n-(3-methylbutyl)pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)N)CC1 UFAZONDOQRPAAB-UHFFFAOYSA-N 0.000 claims 1
- LMLXNRYGWLSELC-UHFFFAOYSA-N 6-[4-(2-chloro-5-fluorobenzoyl)piperazin-1-yl]-n-(2-cyclopropylethyl)pyridazine-3-carboxamide Chemical compound FC1=CC=C(Cl)C(C(=O)N2CCN(CC2)C=2N=NC(=CC=2)C(=O)NCCC2CC2)=C1 LMLXNRYGWLSELC-UHFFFAOYSA-N 0.000 claims 1
- PZMXANYJDOCVDJ-UHFFFAOYSA-N 6-[4-(2-chlorobenzoyl)piperazin-1-yl]-n-(3-methylbutyl)pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)Cl)CC1 PZMXANYJDOCVDJ-UHFFFAOYSA-N 0.000 claims 1
- YDIGAZHGTYRSAG-UHFFFAOYSA-N 6-[4-(2-chloropyridine-3-carbonyl)piperazin-1-yl]-n-(2-cyclopropylethyl)pyridazine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 YDIGAZHGTYRSAG-UHFFFAOYSA-N 0.000 claims 1
- PCDOGMVCJDRQNC-UHFFFAOYSA-N 6-[4-(2-cyanobenzoyl)piperazin-1-yl]-n-(2-cyclopropylethyl)pyridazine-3-carboxamide Chemical compound C=1C=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C#N)N=NC=1C(=O)NCCC1CC1 PCDOGMVCJDRQNC-UHFFFAOYSA-N 0.000 claims 1
- FILCKKXRUNWIRP-UHFFFAOYSA-N 6-[4-(cyclobutanecarbonyl)piperazin-1-yl]-n-(2-cyclopropylethyl)pyridazine-3-carboxamide Chemical compound C=1C=C(N2CCN(CC2)C(=O)C2CCC2)N=NC=1C(=O)NCCC1CC1 FILCKKXRUNWIRP-UHFFFAOYSA-N 0.000 claims 1
- PLIIGGJKZOJZEO-UHFFFAOYSA-N 6-[4-(cyclohexanecarbonyl)piperazin-1-yl]-n-(2-cyclopropylethyl)pyridazine-3-carboxamide Chemical compound C=1C=C(N2CCN(CC2)C(=O)C2CCCCC2)N=NC=1C(=O)NCCC1CC1 PLIIGGJKZOJZEO-UHFFFAOYSA-N 0.000 claims 1
- XMXAMDQTPSEJRG-UHFFFAOYSA-N 6-[4-[(2-chloro-4-fluorophenyl)methyl]piperazin-1-yl]-n-(2-cyclopropylethyl)pyridazine-3-carboxamide Chemical compound ClC1=CC(F)=CC=C1CN1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 XMXAMDQTPSEJRG-UHFFFAOYSA-N 0.000 claims 1
- QGEYOKFFYHBWFA-UHFFFAOYSA-N 6-[4-[2,4-bis(trifluoromethyl)benzoyl]piperazin-1-yl]-n-(2-cyclopropylethyl)pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 QGEYOKFFYHBWFA-UHFFFAOYSA-N 0.000 claims 1
- MLKLPMJRLUEDSF-UHFFFAOYSA-N 6-[4-[2,5-bis(trifluoromethyl)benzoyl]piperazin-1-yl]-n-(2-cyclopropylethyl)pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=C(C(F)(F)F)C(C(=O)N2CCN(CC2)C=2N=NC(=CC=2)C(=O)NCCC2CC2)=C1 MLKLPMJRLUEDSF-UHFFFAOYSA-N 0.000 claims 1
- PKLHLLOKTHYCJK-UHFFFAOYSA-N 6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]-n-[2-(trifluoromethyl)phenyl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 PKLHLLOKTHYCJK-UHFFFAOYSA-N 0.000 claims 1
- HEXMAGZFMZFHGC-UHFFFAOYSA-N 6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]-n-[3-(trifluoromethyl)phenyl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 HEXMAGZFMZFHGC-UHFFFAOYSA-N 0.000 claims 1
- LDKSTMSOLJKZQX-UHFFFAOYSA-N 6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]-n-[4-(trifluoromethyl)phenyl]pyridazine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 LDKSTMSOLJKZQX-UHFFFAOYSA-N 0.000 claims 1
- OMQHEKABFWMTOA-UHFFFAOYSA-N 6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]-n-[5-(trifluoromethyl)pyridin-2-yl]pyridazine-3-carboxamide Chemical compound N1=CC(C(F)(F)F)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 OMQHEKABFWMTOA-UHFFFAOYSA-N 0.000 claims 1
- GKRDSGDSMIVUKZ-UHFFFAOYSA-N 6-[4-[2-chloro-4-(trifluoromethyl)pyrimidine-5-carbonyl]piperazin-1-yl]-n-(2-cyclopropylethyl)pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=NC(Cl)=NC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 GKRDSGDSMIVUKZ-UHFFFAOYSA-N 0.000 claims 1
- GUAHBTVDUIQVBP-UHFFFAOYSA-N 6-[4-[2-chloro-5-(dimethylamino)benzoyl]piperazin-1-yl]-n-(2-cyclopropylethyl)pyridazine-3-carboxamide Chemical compound CN(C)C1=CC=C(Cl)C(C(=O)N2CCN(CC2)C=2N=NC(=CC=2)C(=O)NCCC2CC2)=C1 GUAHBTVDUIQVBP-UHFFFAOYSA-N 0.000 claims 1
- RKOVXDWQQGRLSZ-UHFFFAOYSA-N 6-[4-[2-fluoro-6-(trifluoromethyl)benzoyl]piperazin-1-yl]-n-(3-methylbutyl)pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2F)C(F)(F)F)CC1 RKOVXDWQQGRLSZ-UHFFFAOYSA-N 0.000 claims 1
- ZYBQEOITKRTFMP-UHFFFAOYSA-N 6-[4-[4-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]-n-(3-methylbutyl)pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC(F)=CC=2)C(F)(F)F)CC1 ZYBQEOITKRTFMP-UHFFFAOYSA-N 0.000 claims 1
- XHDJRZIDYSPJIC-UHFFFAOYSA-N 6-[4-[5-chloro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]-n-(2-cyclobutylethyl)pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CCC2)CC1 XHDJRZIDYSPJIC-UHFFFAOYSA-N 0.000 claims 1
- XRUGFRWMDURAFZ-UHFFFAOYSA-N 6-[4-[5-chloro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]-n-(2-cyclopropylethyl)pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 XRUGFRWMDURAFZ-UHFFFAOYSA-N 0.000 claims 1
- LQHQRRJWLFBOBJ-UHFFFAOYSA-N 6-[4-[5-chloro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]-n-(3-cyclopropylpropyl)pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCCC2CC2)CC1 LQHQRRJWLFBOBJ-UHFFFAOYSA-N 0.000 claims 1
- PEYGMVTTXMSMMD-UHFFFAOYSA-N 6-[4-[5-chloro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]-n-hexylpyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=C(Cl)C=2)C(F)(F)F)CC1 PEYGMVTTXMSMMD-UHFFFAOYSA-N 0.000 claims 1
- HYMVANRJYBOZAF-UHFFFAOYSA-N 6-[4-[5-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]-n-(2-hydroxy-3,3-dimethylbutyl)pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCC(O)C(C)(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=C(F)C=2)C(F)(F)F)CC1 HYMVANRJYBOZAF-UHFFFAOYSA-N 0.000 claims 1
- QCLLOYCDSITEOB-UHFFFAOYSA-N 6-[4-[5-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]-n-(3-methylbutyl)pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=C(F)C=2)C(F)(F)F)CC1 QCLLOYCDSITEOB-UHFFFAOYSA-N 0.000 claims 1
- CCPYUAKHQAWVKX-UHFFFAOYSA-N 6-[4-[5-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]-n-(4-methylpentyl)pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=C(F)C=2)C(F)(F)F)CC1 CCPYUAKHQAWVKX-UHFFFAOYSA-N 0.000 claims 1
- HGKLKWZNAYLESQ-UHFFFAOYSA-N 6-[4-[5-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]-n-pentylpyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=C(F)C=2)C(F)(F)F)CC1 HGKLKWZNAYLESQ-UHFFFAOYSA-N 0.000 claims 1
- HNVMNKRBPNWQCQ-UHFFFAOYSA-N 6-[4-[5-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxylic acid Chemical compound N1=NC(C(=O)O)=CC=C1N1CCN(C(=O)C=2C(=CC=C(F)C=2)C(F)(F)F)CC1 HNVMNKRBPNWQCQ-UHFFFAOYSA-N 0.000 claims 1
- YNEHAFRXUAXQFW-UHFFFAOYSA-N 6-[4-[[5-chloro-2-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]-n-(2-cyclopropylethyl)pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1CN1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 YNEHAFRXUAXQFW-UHFFFAOYSA-N 0.000 claims 1
- JCCYFWMYVUSZQE-UHFFFAOYSA-N [1-phenyl-2-[[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carbonyl]amino]ethyl] acetate Chemical compound C=1C=CC=CC=1C(OC(=O)C)CNC(=O)C(N=N1)=CC=C1N(CC1)CCN1C(=O)C1=CC=CC=C1C(F)(F)F JCCYFWMYVUSZQE-UHFFFAOYSA-N 0.000 claims 1
- JRKMAFACFUAQOA-UHFFFAOYSA-N [2-[4-[6-(2-cyclopropylethylcarbamoyl)pyridazin-3-yl]piperazine-1-carbonyl]phenyl] acetate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 JRKMAFACFUAQOA-UHFFFAOYSA-N 0.000 claims 1
- QAFBQYULDBVECY-UHFFFAOYSA-N [2-methyl-4-[[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carbonyl]amino]butan-2-yl] acetate Chemical compound N1=NC(C(=O)NCCC(C)(C)OC(=O)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 QAFBQYULDBVECY-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000005466 alkylenyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- VFLFJFVCZQFPQK-UHFFFAOYSA-N butyl n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]carbamate Chemical compound N1=NC(NC(=O)OCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 VFLFJFVCZQFPQK-UHFFFAOYSA-N 0.000 claims 1
- SRLFFAKOCYHUKL-UHFFFAOYSA-N ethyl 3-[[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]carbamoylamino]propanoate Chemical compound N1=NC(NC(=O)NCCC(=O)OCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 SRLFFAKOCYHUKL-UHFFFAOYSA-N 0.000 claims 1
- WSTCDNHBEXVAAB-UHFFFAOYSA-N ethyl 4-[[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carbonyl]amino]butanoate Chemical compound N1=NC(C(=O)NCCCC(=O)OCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 WSTCDNHBEXVAAB-UHFFFAOYSA-N 0.000 claims 1
- VTZMZPPFWMGTDZ-UHFFFAOYSA-N ethyl n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]carbamate Chemical compound N1=NC(NC(=O)OCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 VTZMZPPFWMGTDZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- GULUMXMVOXARSN-UHFFFAOYSA-N methyl 2-[4-[6-(2-cyclopropylethylcarbamoyl)pyridazin-3-yl]piperazine-1-carbonyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 GULUMXMVOXARSN-UHFFFAOYSA-N 0.000 claims 1
- XQDIFFXCZAACGH-UHFFFAOYSA-N methyl 2-[[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carbonyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 XQDIFFXCZAACGH-UHFFFAOYSA-N 0.000 claims 1
- PAKOYNJYQHCFNU-UHFFFAOYSA-N methyl 4-[[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carbonyl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 PAKOYNJYQHCFNU-UHFFFAOYSA-N 0.000 claims 1
- VAQINPUMKYPWCY-UHFFFAOYSA-N methyl 4-methyl-2-[[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carbonyl]amino]pentanoate Chemical compound N1=NC(C(=O)NC(CC(C)C)C(=O)OC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 VAQINPUMKYPWCY-UHFFFAOYSA-N 0.000 claims 1
- YRWITEQLGAMOAZ-UHFFFAOYSA-N n-(1,3,4-thiadiazol-2-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2SC=NN=2)CC1 YRWITEQLGAMOAZ-UHFFFAOYSA-N 0.000 claims 1
- OBKUHNXYEFUWOV-UHFFFAOYSA-N n-(1,3-thiazol-2-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2SC=CN=2)CC1 OBKUHNXYEFUWOV-UHFFFAOYSA-N 0.000 claims 1
- UQNRSGCHSDLXFC-UHFFFAOYSA-N n-(1h-1,2,4-triazol-5-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2NN=CN=2)CC1 UQNRSGCHSDLXFC-UHFFFAOYSA-N 0.000 claims 1
- SLQTUMVIMBTKIA-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2NC3=CC=CC=C3N=2)CC1 SLQTUMVIMBTKIA-UHFFFAOYSA-N 0.000 claims 1
- RTUJCPJMXIKKPD-UHFFFAOYSA-N n-(1h-indazol-5-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C=C3C=NNC3=CC=2)CC1 RTUJCPJMXIKKPD-UHFFFAOYSA-N 0.000 claims 1
- PGDLXHBDSFVLSR-UHFFFAOYSA-N n-(1h-indazol-6-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C=C3NN=CC3=CC=2)CC1 PGDLXHBDSFVLSR-UHFFFAOYSA-N 0.000 claims 1
- JLQAMRGLJLBFQA-UHFFFAOYSA-N n-(1h-indol-4-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C=3C=CNC=3C=CC=2)CC1 JLQAMRGLJLBFQA-UHFFFAOYSA-N 0.000 claims 1
- MPQPKQGYCFIFIC-UHFFFAOYSA-N n-(1h-indol-6-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C=C3NC=CC3=CC=2)CC1 MPQPKQGYCFIFIC-UHFFFAOYSA-N 0.000 claims 1
- BEHCRTWMTDUKGA-UHFFFAOYSA-N n-(1h-pyrazol-5-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC2=NNC=C2)CC1 BEHCRTWMTDUKGA-UHFFFAOYSA-N 0.000 claims 1
- QBKBJEMUKXOAQM-UHFFFAOYSA-N n-(2,2-difluoro-2-phenylethyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCC(F)(F)C=2C=CC=CC=2)CC1 QBKBJEMUKXOAQM-UHFFFAOYSA-N 0.000 claims 1
- LJIOZNHUZJYFPZ-UHFFFAOYSA-N n-(2,2-difluoro-2-pyridin-2-ylethyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCC(F)(F)C=2N=CC=CC=2)CC1 LJIOZNHUZJYFPZ-UHFFFAOYSA-N 0.000 claims 1
- TZTFMAPBPBRVSJ-UHFFFAOYSA-N n-(2,3-difluorophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=CC(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1F TZTFMAPBPBRVSJ-UHFFFAOYSA-N 0.000 claims 1
- BIKZECVTSDZTKD-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-1-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC2C3=CC=CC=C3CC2)CC1 BIKZECVTSDZTKD-UHFFFAOYSA-N 0.000 claims 1
- PBFWFKLTGRTDCG-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-5-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C=C3CCCC3=CC=2)CC1 PBFWFKLTGRTDCG-UHFFFAOYSA-N 0.000 claims 1
- WUPFGOGYQXTDAF-UHFFFAOYSA-N n-(2,3-dimethylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1C WUPFGOGYQXTDAF-UHFFFAOYSA-N 0.000 claims 1
- BGFCCIMWSIPFMX-UHFFFAOYSA-N n-(2,4-difluorophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 BGFCCIMWSIPFMX-UHFFFAOYSA-N 0.000 claims 1
- QTOZBCGNNZONLT-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=CC(C)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 QTOZBCGNNZONLT-UHFFFAOYSA-N 0.000 claims 1
- HCLXQBFXEGXXNZ-UHFFFAOYSA-N n-(2,5-dichlorophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C(=CC=C(Cl)C=2)Cl)CC1 HCLXQBFXEGXXNZ-UHFFFAOYSA-N 0.000 claims 1
- HJPVDPVCMROXCZ-UHFFFAOYSA-N n-(2,5-dimethoxyphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound COC1=CC=C(OC)C(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 HJPVDPVCMROXCZ-UHFFFAOYSA-N 0.000 claims 1
- RBBXRQNWYUIRKG-UHFFFAOYSA-N n-(2,5-dimethylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=CC=C(C)C(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 RBBXRQNWYUIRKG-UHFFFAOYSA-N 0.000 claims 1
- SVBRSBBHHKLTRC-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C(=CC=CC=2Cl)Cl)CC1 SVBRSBBHHKLTRC-UHFFFAOYSA-N 0.000 claims 1
- FHEOEVILTILROP-UHFFFAOYSA-N n-(2,6-difluorophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=CC(F)=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 FHEOEVILTILROP-UHFFFAOYSA-N 0.000 claims 1
- ACAVNNQICZRPPJ-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 ACAVNNQICZRPPJ-UHFFFAOYSA-N 0.000 claims 1
- HYFCVSJSYXXSNW-UHFFFAOYSA-N n-(2-chloro-3-methylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1Cl HYFCVSJSYXXSNW-UHFFFAOYSA-N 0.000 claims 1
- QKDBESGYTMPSRQ-UHFFFAOYSA-N n-(2-chloro-4-methoxyphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound ClC1=CC(OC)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 QKDBESGYTMPSRQ-UHFFFAOYSA-N 0.000 claims 1
- QMWKKZHEQFMQGK-UHFFFAOYSA-N n-(2-chloro-4-methylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound ClC1=CC(C)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 QMWKKZHEQFMQGK-UHFFFAOYSA-N 0.000 claims 1
- KQYCRSRAHAFKET-UHFFFAOYSA-N n-(2-chloro-5-fluorophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=C(Cl)C(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 KQYCRSRAHAFKET-UHFFFAOYSA-N 0.000 claims 1
- OAKHDJBKBYVJTP-UHFFFAOYSA-N n-(2-chloro-5-methylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=CC=C(Cl)C(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 OAKHDJBKBYVJTP-UHFFFAOYSA-N 0.000 claims 1
- NICRNJWMLNOZNJ-UHFFFAOYSA-N n-(2-chloro-6-methylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=CC=CC(Cl)=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 NICRNJWMLNOZNJ-UHFFFAOYSA-N 0.000 claims 1
- KYHZNPIFHSXMMU-UHFFFAOYSA-N n-(2-chlorophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C(=CC=CC=2)Cl)CC1 KYHZNPIFHSXMMU-UHFFFAOYSA-N 0.000 claims 1
- IQWXNXPBKDQTAW-UHFFFAOYSA-N n-(2-chloropyridin-4-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C=C(Cl)N=CC=2)CC1 IQWXNXPBKDQTAW-UHFFFAOYSA-N 0.000 claims 1
- NLIYVXKSDSDLLY-UHFFFAOYSA-N n-(2-cyano-3-fluorophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=CC(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1C#N NLIYVXKSDSDLLY-UHFFFAOYSA-N 0.000 claims 1
- OLCMYEGONUCTMG-UHFFFAOYSA-N n-(2-cyanophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C(=CC=CC=2)C#N)CC1 OLCMYEGONUCTMG-UHFFFAOYSA-N 0.000 claims 1
- SMBUWWFDFXOIJB-UHFFFAOYSA-N n-(2-cyclobutylethyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CCC2)CC1 SMBUWWFDFXOIJB-UHFFFAOYSA-N 0.000 claims 1
- ZYSNCJVDWYIMTL-UHFFFAOYSA-N n-(2-cyclobutylethyl)-6-[4-[5-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=C(C(F)(F)F)C(C(=O)N2CCN(CC2)C=2N=NC(=CC=2)C(=O)NCCC2CCC2)=C1 ZYSNCJVDWYIMTL-UHFFFAOYSA-N 0.000 claims 1
- ISZBFPJCHSOENQ-UHFFFAOYSA-N n-(2-cyclopropyl-2-hydroxyethyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1CC1C(O)CNC(=O)C(N=N1)=CC=C1N(CC1)CCN1C(=O)C1=CC=CC=C1C(F)(F)F ISZBFPJCHSOENQ-UHFFFAOYSA-N 0.000 claims 1
- IIBJDJXZGQMEIJ-UHFFFAOYSA-N n-(2-cyclopropyl-2-oxoethyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCC(=O)C2CC2)CC1 IIBJDJXZGQMEIJ-UHFFFAOYSA-N 0.000 claims 1
- AKUOTROCUSJZIK-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[3,5-dimethyl-4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1CN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC(C)N1C(=O)C1=CC=CC=C1C(F)(F)F AKUOTROCUSJZIK-UHFFFAOYSA-N 0.000 claims 1
- BDLYEEDNAPRFQU-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(1-hydroxycyclopropanecarbonyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1CN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CCN1C(=O)C1(O)CC1 BDLYEEDNAPRFQU-UHFFFAOYSA-N 0.000 claims 1
- FBNDZYRZDNNAFS-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(1-methylpyrrole-2-carbonyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CN1C=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 FBNDZYRZDNNAFS-UHFFFAOYSA-N 0.000 claims 1
- QSGGYPPXORFBOQ-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(2,2,3,3-tetramethylcyclopropanecarbonyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1(C)C(C)(C)C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 QSGGYPPXORFBOQ-UHFFFAOYSA-N 0.000 claims 1
- RENYYZLLNXEOMQ-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(2,2-dimethylbutanoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1CN(C(=O)C(C)(C)CC)CCN1C1=CC=C(C(=O)NCCC2CC2)N=N1 RENYYZLLNXEOMQ-UHFFFAOYSA-N 0.000 claims 1
- QQVRTWNIEGALDY-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(2,2-dimethylpentanoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1CN(C(=O)C(C)(C)CCC)CCN1C1=CC=C(C(=O)NCCC2CC2)N=N1 QQVRTWNIEGALDY-UHFFFAOYSA-N 0.000 claims 1
- YOHKXELWQRPSBM-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(2,2-dimethylpropanoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1CN(C(=O)C(C)(C)C)CCN1C1=CC=C(C(=O)NCCC2CC2)N=N1 YOHKXELWQRPSBM-UHFFFAOYSA-N 0.000 claims 1
- UPRHRDVCISBLNY-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(2,5-dichlorobenzoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound ClC1=CC=C(Cl)C(C(=O)N2CCN(CC2)C=2N=NC(=CC=2)C(=O)NCCC2CC2)=C1 UPRHRDVCISBLNY-UHFFFAOYSA-N 0.000 claims 1
- JTBDXEGRUZRAST-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(2,5-difluorobenzoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=C(F)C(C(=O)N2CCN(CC2)C=2N=NC(=CC=2)C(=O)NCCC2CC2)=C1 JTBDXEGRUZRAST-UHFFFAOYSA-N 0.000 claims 1
- KOCLPXHENKOLAS-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(2,5-dimethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=CC=C(C)C(C(=O)N2CCN(CC2)C=2N=NC(=CC=2)C(=O)NCCC2CC2)=C1 KOCLPXHENKOLAS-UHFFFAOYSA-N 0.000 claims 1
- GVYKUVLDUWWRTD-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(2,6-dichloropyridine-3-carbonyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound ClC1=NC(Cl)=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 GVYKUVLDUWWRTD-UHFFFAOYSA-N 0.000 claims 1
- QOWSHFRWLKCYFK-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(2,6-difluorobenzoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=CC(F)=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 QOWSHFRWLKCYFK-UHFFFAOYSA-N 0.000 claims 1
- YCYQQVNYEDXJQM-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(2-ethylbutanoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1CN(C(=O)C(CC)CC)CCN1C1=CC=C(C(=O)NCCC2CC2)N=N1 YCYQQVNYEDXJQM-UHFFFAOYSA-N 0.000 claims 1
- DZESEDNMYNFEEI-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(2-fluorobenzoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 DZESEDNMYNFEEI-UHFFFAOYSA-N 0.000 claims 1
- RIKHYRIMBJOBEB-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(2-methylcyclohexanecarbonyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1CCCCC1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 RIKHYRIMBJOBEB-UHFFFAOYSA-N 0.000 claims 1
- CKBZAFHZWNZSNQ-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(2-methylcyclopropanecarbonyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1CC1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 CKBZAFHZWNZSNQ-UHFFFAOYSA-N 0.000 claims 1
- BHNZOKFYIKXNFL-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1CN(C(=O)C(O)(C)C(F)(F)F)CCN1C1=CC=C(C(=O)NCCC2CC2)N=N1 BHNZOKFYIKXNFL-UHFFFAOYSA-N 0.000 claims 1
- HBNZOEKUZWRTRC-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(3-methylcyclohexanecarbonyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1C(C)CCCC1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 HBNZOEKUZWRTRC-UHFFFAOYSA-N 0.000 claims 1
- IZYGMDAVQFBXAX-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(4,4,4-trifluoro-3-hydroxy-3-methylbutanoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1CN(C(=O)CC(O)(C)C(F)(F)F)CCN1C1=CC=C(C(=O)NCCC2CC2)N=N1 IZYGMDAVQFBXAX-UHFFFAOYSA-N 0.000 claims 1
- XCQKWERVUSCEGP-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(4,4,4-trifluorobut-2-enoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1CN(C(=O)C=CC(F)(F)F)CCN1C1=CC=C(C(=O)NCCC2CC2)N=N1 XCQKWERVUSCEGP-UHFFFAOYSA-N 0.000 claims 1
- GZFVOLOWFRKFIW-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(4-methylcyclohexanecarbonyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1CC(C)CCC1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 GZFVOLOWFRKFIW-UHFFFAOYSA-N 0.000 claims 1
- AHZBLQTUNBWBJD-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(5-fluoro-2-methoxybenzoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound COC1=CC=C(F)C=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 AHZBLQTUNBWBJD-UHFFFAOYSA-N 0.000 claims 1
- FLFDMQAYBUNSQM-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(oxolane-2-carbonyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C=1C=C(N2CCN(CC2)C(=O)C2OCCC2)N=NC=1C(=O)NCCC1CC1 FLFDMQAYBUNSQM-UHFFFAOYSA-N 0.000 claims 1
- CNOOCRLQUQJUST-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(pyridine-2-carbonyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C=1C=C(N2CCN(CC2)C(=O)C=2N=CC=CC=2)N=NC=1C(=O)NCCC1CC1 CNOOCRLQUQJUST-UHFFFAOYSA-N 0.000 claims 1
- IOVJCCOJHCRLJN-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-(pyrrolidine-1-carbonyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C=1C=C(N2CCN(CC2)C(=O)N2CCCC2)N=NC=1C(=O)NCCC1CC1 IOVJCCOJHCRLJN-UHFFFAOYSA-N 0.000 claims 1
- ANFCTEHHNKCDGM-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[(2,4-dichlorophenyl)methyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1CN1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 ANFCTEHHNKCDGM-UHFFFAOYSA-N 0.000 claims 1
- YDGQDNDCPFNAQZ-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[(2,5-dichlorophenyl)methyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound ClC1=CC=C(Cl)C(CN2CCN(CC2)C=2N=NC(=CC=2)C(=O)NCCC2CC2)=C1 YDGQDNDCPFNAQZ-UHFFFAOYSA-N 0.000 claims 1
- COMNYBABLUFJDK-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[1-[2-(trifluoromethyl)phenyl]ethyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C=1C=CC=C(C(F)(F)F)C=1C(C)N(CC1)CCN1C(N=N1)=CC=C1C(=O)NCCC1CC1 COMNYBABLUFJDK-UHFFFAOYSA-N 0.000 claims 1
- YIOLCQFUHDXWJC-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[2-(dimethylamino)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CN(C)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 YIOLCQFUHDXWJC-UHFFFAOYSA-N 0.000 claims 1
- QKVGXDPQQGMVEC-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[2-(trifluoromethyl)benzenecarbothioyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=S)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 QKVGXDPQQGMVEC-UHFFFAOYSA-N 0.000 claims 1
- OCXBYYNZEUUCEO-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 OCXBYYNZEUUCEO-UHFFFAOYSA-N 0.000 claims 1
- RCVPUPWQGZXUEJ-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[2-(trifluoromethyl)furan-3-carbonyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound O1C=CC(C(=O)N2CCN(CC2)C=2N=NC(=CC=2)C(=O)NCCC2CC2)=C1C(F)(F)F RCVPUPWQGZXUEJ-UHFFFAOYSA-N 0.000 claims 1
- VNDASIKFZXLPIW-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[2-methyl-5-(trifluoromethyl)-1,3-oxazole-4-carbonyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound O1C(C)=NC(C(=O)N2CCN(CC2)C=2N=NC(=CC=2)C(=O)NCCC2CC2)=C1C(F)(F)F VNDASIKFZXLPIW-UHFFFAOYSA-N 0.000 claims 1
- OXYOAVSPJRYTSY-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[3,3,3-trifluoro-2-methyl-2-(trifluoromethyl)propanoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1CN(C(=O)C(C)(C(F)(F)F)C(F)(F)F)CCN1C1=CC=C(C(=O)NCCC2CC2)N=N1 OXYOAVSPJRYTSY-UHFFFAOYSA-N 0.000 claims 1
- AHPITNKHMUCYLX-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[3-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=CC(C(=O)N2CCN(CC2)C=2N=NC(=CC=2)C(=O)NCCC2CC2)=C1C(F)(F)F AHPITNKHMUCYLX-UHFFFAOYSA-N 0.000 claims 1
- WDPZGLXWKPXODH-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[4,4,4-trifluoro-3-(trifluoromethyl)but-2-enoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1CN(C(=O)C=C(C(F)(F)F)C(F)(F)F)CCN1C1=CC=C(C(=O)NCCC2CC2)N=N1 WDPZGLXWKPXODH-UHFFFAOYSA-N 0.000 claims 1
- ZDGTXHQFUXCXRO-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[4,4,4-trifluoro-3-hydroxy-3-(trifluoromethyl)butanoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1CN(C(=O)CC(O)(C(F)(F)F)C(F)(F)F)CCN1C1=CC=C(C(=O)NCCC2CC2)N=N1 ZDGTXHQFUXCXRO-UHFFFAOYSA-N 0.000 claims 1
- RXBOSKCKGPDBKY-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[4-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC(F)=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 RXBOSKCKGPDBKY-UHFFFAOYSA-N 0.000 claims 1
- QMZSSLLJQUFMHM-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[5-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=C(C(F)(F)F)C(C(=O)N2CCN(CC2)C=2N=NC(=CC=2)C(=O)NCCC2CC2)=C1 QMZSSLLJQUFMHM-UHFFFAOYSA-N 0.000 claims 1
- KJMXCRFBUNSWBZ-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[5-methyl-2-(trifluoromethyl)furan-3-carbonyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound O1C(C)=CC(C(=O)N2CCN(CC2)C=2N=NC(=CC=2)C(=O)NCCC2CC2)=C1C(F)(F)F KJMXCRFBUNSWBZ-UHFFFAOYSA-N 0.000 claims 1
- LHOYXBTVVSCEJI-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[[2-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1CN1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 LHOYXBTVVSCEJI-UHFFFAOYSA-N 0.000 claims 1
- KPGBKFUZHIMGAB-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[[4-fluoro-2-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC(F)=CC=C1CN1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 KPGBKFUZHIMGAB-UHFFFAOYSA-N 0.000 claims 1
- FVOBAZRDCGHGKJ-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[[5-fluoro-2-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=C(C(F)(F)F)C(CN2CCN(CC2)C=2N=NC(=CC=2)C(=O)NCCC2CC2)=C1 FVOBAZRDCGHGKJ-UHFFFAOYSA-N 0.000 claims 1
- ZDVGDFZUSDPVMQ-UHFFFAOYSA-N n-(2-ethoxyethyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCOCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 ZDVGDFZUSDPVMQ-UHFFFAOYSA-N 0.000 claims 1
- JAWJVODNQZUXBQ-UHFFFAOYSA-N n-(2-ethylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CCC1=CC=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 JAWJVODNQZUXBQ-UHFFFAOYSA-N 0.000 claims 1
- CZIASDJVAMADSF-UHFFFAOYSA-N n-(2-fluoro-4-methylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC(C)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 CZIASDJVAMADSF-UHFFFAOYSA-N 0.000 claims 1
- AFYBOWSWYRSJMA-UHFFFAOYSA-N n-(2-fluoro-5-methylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=CC=C(F)C(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 AFYBOWSWYRSJMA-UHFFFAOYSA-N 0.000 claims 1
- FUWHAOFCKAYDEC-UHFFFAOYSA-N n-(2-fluorophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 FUWHAOFCKAYDEC-UHFFFAOYSA-N 0.000 claims 1
- JOTQJOVHIMGILT-UHFFFAOYSA-N n-(2-hydroxy-3,3-dimethylbutyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCC(O)C(C)(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 JOTQJOVHIMGILT-UHFFFAOYSA-N 0.000 claims 1
- KPOSGYPSFNOMQY-UHFFFAOYSA-N n-(2-methoxy-3,3-dimethylbutyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCC(OC)C(C)(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 KPOSGYPSFNOMQY-UHFFFAOYSA-N 0.000 claims 1
- WKDRZUAWZNBSEP-UHFFFAOYSA-N n-(2-methoxyphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound COC1=CC=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 WKDRZUAWZNBSEP-UHFFFAOYSA-N 0.000 claims 1
- YJXQRSURIDXOFV-UHFFFAOYSA-N n-(2-methylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=CC=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 YJXQRSURIDXOFV-UHFFFAOYSA-N 0.000 claims 1
- KLFGVOKTQFHRQM-UHFFFAOYSA-N n-(2-oxo-1h-pyrimidin-6-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2NC(=O)N=CC=2)CC1 KLFGVOKTQFHRQM-UHFFFAOYSA-N 0.000 claims 1
- VXMFCSPSOUUUSS-UHFFFAOYSA-N n-(2-phenoxyethyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCOC=2C=CC=CC=2)CC1 VXMFCSPSOUUUSS-UHFFFAOYSA-N 0.000 claims 1
- TVSDBYTZFAQONZ-UHFFFAOYSA-N n-(2-phenylethyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC=2C=CC=CC=2)CC1 TVSDBYTZFAQONZ-UHFFFAOYSA-N 0.000 claims 1
- AXJYGGLVVOCLNI-UHFFFAOYSA-N n-(2-phenylpropyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C=1C=CC=CC=1C(C)CNC(=O)C(N=N1)=CC=C1N(CC1)CCN1C(=O)C1=CC=CC=C1C(F)(F)F AXJYGGLVVOCLNI-UHFFFAOYSA-N 0.000 claims 1
- SOGBLUWTWAALRN-UHFFFAOYSA-N n-(2-propan-2-ylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC(C)C1=CC=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 SOGBLUWTWAALRN-UHFFFAOYSA-N 0.000 claims 1
- IKMUGYWQHPADTI-UHFFFAOYSA-N n-(2-propylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CCCC1=CC=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 IKMUGYWQHPADTI-UHFFFAOYSA-N 0.000 claims 1
- ATJBTUXOEIYAIL-UHFFFAOYSA-N n-(2-pyridin-2-ylethyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC=2N=CC=CC=2)CC1 ATJBTUXOEIYAIL-UHFFFAOYSA-N 0.000 claims 1
- UEHMNCLJIXURAH-UHFFFAOYSA-N n-(2-thiophen-2-ylethyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC=2SC=CC=2)CC1 UEHMNCLJIXURAH-UHFFFAOYSA-N 0.000 claims 1
- PRTJJARBKFELPF-UHFFFAOYSA-N n-(2h-tetrazol-5-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2NN=NN=2)CC1 PRTJJARBKFELPF-UHFFFAOYSA-N 0.000 claims 1
- MXCXLYWZNSPKOF-UHFFFAOYSA-N n-(3,3-dimethylbutyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 MXCXLYWZNSPKOF-UHFFFAOYSA-N 0.000 claims 1
- VXAULYAGNZLQKQ-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C=C(Cl)C(Cl)=CC=2)CC1 VXAULYAGNZLQKQ-UHFFFAOYSA-N 0.000 claims 1
- IWGPLILGJXSWKZ-UHFFFAOYSA-N n-(3,4-difluorophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1=C(F)C(F)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 IWGPLILGJXSWKZ-UHFFFAOYSA-N 0.000 claims 1
- HTGRCPXYVJSLIQ-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1=C(C)C(C)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 HTGRCPXYVJSLIQ-UHFFFAOYSA-N 0.000 claims 1
- RSZZKUCIKNLWKC-UHFFFAOYSA-N n-(3,5-dimethylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=CC(C)=CC(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 RSZZKUCIKNLWKC-UHFFFAOYSA-N 0.000 claims 1
- YMLINECUCKULTA-UHFFFAOYSA-N n-(3-carbamoylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound NC(=O)C1=CC=CC(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 YMLINECUCKULTA-UHFFFAOYSA-N 0.000 claims 1
- JMNKFSLYJWMTOW-UHFFFAOYSA-N n-(3-chloro-2-methylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=C(Cl)C=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 JMNKFSLYJWMTOW-UHFFFAOYSA-N 0.000 claims 1
- PECWFBAJZSQZEQ-UHFFFAOYSA-N n-(3-chloro-4-methylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1=C(Cl)C(C)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 PECWFBAJZSQZEQ-UHFFFAOYSA-N 0.000 claims 1
- GIHOXHHGOSFJAT-UHFFFAOYSA-N n-(3-chlorophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C=C(Cl)C=CC=2)CC1 GIHOXHHGOSFJAT-UHFFFAOYSA-N 0.000 claims 1
- HTPWDJCBOSWOOS-UHFFFAOYSA-N n-(3-cyanophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C=C(C=CC=2)C#N)CC1 HTPWDJCBOSWOOS-UHFFFAOYSA-N 0.000 claims 1
- PRINUHCMXYLNKR-UHFFFAOYSA-N n-(3-cyclobutylpropyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCCC2CCC2)CC1 PRINUHCMXYLNKR-UHFFFAOYSA-N 0.000 claims 1
- ALNBEEWFQUYNMP-UHFFFAOYSA-N n-(3-cyclopropylpropyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCCC2CC2)CC1 ALNBEEWFQUYNMP-UHFFFAOYSA-N 0.000 claims 1
- QFZKDKVMPKIZHT-UHFFFAOYSA-N n-(3-cyclopropylpropyl)-6-[4-[4-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC(F)=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCCC2CC2)CC1 QFZKDKVMPKIZHT-UHFFFAOYSA-N 0.000 claims 1
- WWEQKPHXLQZYMO-UHFFFAOYSA-N n-(3-cyclopropylpropyl)-6-[4-[5-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=C(C(F)(F)F)C(C(=O)N2CCN(CC2)C=2N=NC(=CC=2)C(=O)NCCCC2CC2)=C1 WWEQKPHXLQZYMO-UHFFFAOYSA-N 0.000 claims 1
- QMROEJLVGZHHGX-UHFFFAOYSA-N n-(3-cyclopropylpropyl)-6-[4-[[5-fluoro-2-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=C(C(F)(F)F)C(CN2CCN(CC2)C=2N=NC(=CC=2)C(=O)NCCCC2CC2)=C1 QMROEJLVGZHHGX-UHFFFAOYSA-N 0.000 claims 1
- IKDKQTYWXPTBOE-UHFFFAOYSA-N n-(3-fluoro-2-methylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=C(F)C=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 IKDKQTYWXPTBOE-UHFFFAOYSA-N 0.000 claims 1
- SLHUFPXKJIQWNY-UHFFFAOYSA-N n-(3-fluoro-5-methylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=CC(F)=CC(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 SLHUFPXKJIQWNY-UHFFFAOYSA-N 0.000 claims 1
- DDGINPNRFYFVFW-UHFFFAOYSA-N n-(3-fluorophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=CC(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 DDGINPNRFYFVFW-UHFFFAOYSA-N 0.000 claims 1
- ASQKCXTVHBOYJJ-UHFFFAOYSA-N n-(3-hydroxy-3-methylbutyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)(O)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 ASQKCXTVHBOYJJ-UHFFFAOYSA-N 0.000 claims 1
- PGNYKMPHEJXWLF-UHFFFAOYSA-N n-(3-hydroxy-4,4-dimethylpentyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(O)C(C)(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 PGNYKMPHEJXWLF-UHFFFAOYSA-N 0.000 claims 1
- DQERSMQGVKIECT-UHFFFAOYSA-N n-(3-methoxyphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound COC1=CC=CC(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 DQERSMQGVKIECT-UHFFFAOYSA-N 0.000 claims 1
- FXQAREWCOXZJKT-UHFFFAOYSA-N n-(3-methyl-1,2-oxazol-5-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound O1N=C(C)C=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 FXQAREWCOXZJKT-UHFFFAOYSA-N 0.000 claims 1
- QSEQCDMSNVRPEC-UHFFFAOYSA-N n-(3-methylbutyl)-4-(trifluoromethyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1=C(C(F)(F)F)C(C(=O)NCCC(C)C)=NN=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 QSEQCDMSNVRPEC-UHFFFAOYSA-N 0.000 claims 1
- MBPQWXISAKUWRS-UHFFFAOYSA-N n-(3-methylbutyl)-6-[4-(2-nitrobenzoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)[N+]([O-])=O)CC1 MBPQWXISAKUWRS-UHFFFAOYSA-N 0.000 claims 1
- SMGVEGODOURNKT-UHFFFAOYSA-N n-(3-methylbutyl)-6-[4-(2-sulfamoylbenzoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)S(N)(=O)=O)CC1 SMGVEGODOURNKT-UHFFFAOYSA-N 0.000 claims 1
- NGGBGFKKADSXPM-UHFFFAOYSA-N n-(3-methylbutyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 NGGBGFKKADSXPM-UHFFFAOYSA-N 0.000 claims 1
- AWSWGFLZVRYNMI-UHFFFAOYSA-N n-(3-phenylpropyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCCC=2C=CC=CC=2)CC1 AWSWGFLZVRYNMI-UHFFFAOYSA-N 0.000 claims 1
- ZUVOCOFMLBUQDP-UHFFFAOYSA-N n-(4,6-dimethylpyrimidin-2-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=CC(C)=NC(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 ZUVOCOFMLBUQDP-UHFFFAOYSA-N 0.000 claims 1
- NLVBHCMJNDMKDY-UHFFFAOYSA-N n-(4-carbamoylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 NLVBHCMJNDMKDY-UHFFFAOYSA-N 0.000 claims 1
- NCNJSXZJGMBRBG-UHFFFAOYSA-N n-(4-chloro-2-methylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=CC(Cl)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 NCNJSXZJGMBRBG-UHFFFAOYSA-N 0.000 claims 1
- LGOPGPWXZOZAPV-UHFFFAOYSA-N n-(4-chloro-3-methylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1=C(Cl)C(C)=CC(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 LGOPGPWXZOZAPV-UHFFFAOYSA-N 0.000 claims 1
- ROYPFGQMSMXLRB-UHFFFAOYSA-N n-(4-chlorophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)CC1 ROYPFGQMSMXLRB-UHFFFAOYSA-N 0.000 claims 1
- GXUNZVASJNAWGF-UHFFFAOYSA-N n-(4-cyanophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C=CC(=CC=2)C#N)CC1 GXUNZVASJNAWGF-UHFFFAOYSA-N 0.000 claims 1
- ZSWOIVIXCCZNJP-UHFFFAOYSA-N n-(4-cyclopropylbutyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCCCC2CC2)CC1 ZSWOIVIXCCZNJP-UHFFFAOYSA-N 0.000 claims 1
- LQDYBIZOEVNNTE-UHFFFAOYSA-N n-(4-ethylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1=CC(CC)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 LQDYBIZOEVNNTE-UHFFFAOYSA-N 0.000 claims 1
- CSHKQIOZGCJLAE-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=CC(F)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 CSHKQIOZGCJLAE-UHFFFAOYSA-N 0.000 claims 1
- KLOHKVLHDFKDRJ-UHFFFAOYSA-N n-(4-fluorophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 KLOHKVLHDFKDRJ-UHFFFAOYSA-N 0.000 claims 1
- YEIDPMLPZBBHGB-UHFFFAOYSA-N n-(4-hydroxybutyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCCCO)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 YEIDPMLPZBBHGB-UHFFFAOYSA-N 0.000 claims 1
- DSSMFWLSJLEISE-UHFFFAOYSA-N n-(4-methoxyphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 DSSMFWLSJLEISE-UHFFFAOYSA-N 0.000 claims 1
- OHGNJGDOBAZXFZ-UHFFFAOYSA-N n-(4-methyl-1,3-thiazol-2-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=CSC(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 OHGNJGDOBAZXFZ-UHFFFAOYSA-N 0.000 claims 1
- VWIAOXLSRYZUSF-UHFFFAOYSA-N n-(4-methylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1=CC(C)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 VWIAOXLSRYZUSF-UHFFFAOYSA-N 0.000 claims 1
- ZKZFQQWOGWEQPG-UHFFFAOYSA-N n-(4-methylpyrimidin-2-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1=CC=NC(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 ZKZFQQWOGWEQPG-UHFFFAOYSA-N 0.000 claims 1
- YXZNAAYHGXXOPI-UHFFFAOYSA-N n-(4-oxo-3,5-diazabicyclo[3.1.0]hex-2-en-2-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C3CN3C(=O)N=2)CC1 YXZNAAYHGXXOPI-UHFFFAOYSA-N 0.000 claims 1
- LAZRCMHUWQNAST-UHFFFAOYSA-N n-(4-propan-2-ylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 LAZRCMHUWQNAST-UHFFFAOYSA-N 0.000 claims 1
- YFHVBTGLXSGYCN-UHFFFAOYSA-N n-(4-propylphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1=CC(CCC)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 YFHVBTGLXSGYCN-UHFFFAOYSA-N 0.000 claims 1
- VWLUHFQCHNUBPL-UHFFFAOYSA-N n-(5-chloro-2-fluorophenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=C(Cl)C=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 VWLUHFQCHNUBPL-UHFFFAOYSA-N 0.000 claims 1
- JGUZFTUMRWMMNH-UHFFFAOYSA-N n-(5-chloro-2-methoxyphenyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound COC1=CC=C(Cl)C=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 JGUZFTUMRWMMNH-UHFFFAOYSA-N 0.000 claims 1
- DSNMWDLSJLVXIR-UHFFFAOYSA-N n-(5-chloropyridin-2-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2N=CC(Cl)=CC=2)CC1 DSNMWDLSJLVXIR-UHFFFAOYSA-N 0.000 claims 1
- IXQUZMNYKNNNDL-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2N=CC(=CC=2)C#N)CC1 IXQUZMNYKNNNDL-UHFFFAOYSA-N 0.000 claims 1
- ZUMCDWMUICAMQT-UHFFFAOYSA-N n-(5-fluoropyridin-2-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=CC(F)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 ZUMCDWMUICAMQT-UHFFFAOYSA-N 0.000 claims 1
- UBVXZJPMPUKULC-UHFFFAOYSA-N n-(5-methyl-1,2-oxazol-3-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound O1C(C)=CC(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 UBVXZJPMPUKULC-UHFFFAOYSA-N 0.000 claims 1
- PNFBXKKLZXUIND-UHFFFAOYSA-N n-(5-methyl-1,3-thiazol-2-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound S1C(C)=CN=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 PNFBXKKLZXUIND-UHFFFAOYSA-N 0.000 claims 1
- QOCSFKDTJZABAG-UHFFFAOYSA-N n-(5-methyl-1h-pyrazol-3-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1C(C)=CC(NC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 QOCSFKDTJZABAG-UHFFFAOYSA-N 0.000 claims 1
- IMTHTNUJWSAZNK-UHFFFAOYSA-N n-(5-oxo-1,4-dihydropyrazol-3-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2CC(=O)NN=2)CC1 IMTHTNUJWSAZNK-UHFFFAOYSA-N 0.000 claims 1
- JYBTYFRAPQRDMC-UHFFFAOYSA-N n-(5-sulfanylidene-1,2-dihydro-1,2,4-triazol-3-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2NC(=S)NN=2)CC1 JYBTYFRAPQRDMC-UHFFFAOYSA-N 0.000 claims 1
- GLBHSDGTCOEJDA-UHFFFAOYSA-N n-(6-chloropyridazin-3-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2N=NC(Cl)=CC=2)CC1 GLBHSDGTCOEJDA-UHFFFAOYSA-N 0.000 claims 1
- XMAZSXXJVYEMGD-UHFFFAOYSA-N n-(6-methoxypyridazin-3-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(OC)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 XMAZSXXJVYEMGD-UHFFFAOYSA-N 0.000 claims 1
- IGJBJBFPMLBRHX-UHFFFAOYSA-N n-(6-methylpyridazin-3-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C)=CC=C1NC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 IGJBJBFPMLBRHX-UHFFFAOYSA-N 0.000 claims 1
- AXQDZGOAKUJYKA-UHFFFAOYSA-N n-(6-oxo-1h-1,3,5-triazin-2-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2NC(=O)N=CN=2)CC1 AXQDZGOAKUJYKA-UHFFFAOYSA-N 0.000 claims 1
- GVFUXQZTYLDSCH-UHFFFAOYSA-N n-(6-oxo-1h-pyrimidin-2-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2NC(=O)C=CN=2)CC1 GVFUXQZTYLDSCH-UHFFFAOYSA-N 0.000 claims 1
- DQEHCQJMEFCQCQ-UHFFFAOYSA-N n-(7h-purin-6-yl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C=3NC=NC=3N=CN=2)CC1 DQEHCQJMEFCQCQ-UHFFFAOYSA-N 0.000 claims 1
- NZOIMDGOELMWNX-UHFFFAOYSA-N n-(cyclobutylmethyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCC2CCC2)CC1 NZOIMDGOELMWNX-UHFFFAOYSA-N 0.000 claims 1
- URPZPSJDBIORSO-UHFFFAOYSA-N n-(cyclopropylmethyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCC2CC2)CC1 URPZPSJDBIORSO-UHFFFAOYSA-N 0.000 claims 1
- FCEGHVPVYLQHLP-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCC=2N=CC=CC=2)CC1 FCEGHVPVYLQHLP-UHFFFAOYSA-N 0.000 claims 1
- HLASEFFCSOFDIQ-UHFFFAOYSA-N n-[(2,2-dimethylcyclopropyl)methyl]-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1(C)CC1CNC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 HLASEFFCSOFDIQ-UHFFFAOYSA-N 0.000 claims 1
- LLIPAVSLRGJIBP-UHFFFAOYSA-N n-[(2-methylcyclopropyl)methyl]-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound CC1CC1CNC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 LLIPAVSLRGJIBP-UHFFFAOYSA-N 0.000 claims 1
- FNQOCOGXHLMBKB-UHFFFAOYSA-N n-[(2-phenylcyclopropyl)methyl]-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCC2C(C2)C=2C=CC=CC=2)CC1 FNQOCOGXHLMBKB-UHFFFAOYSA-N 0.000 claims 1
- COTQFOUJZXUUCG-NRFANRHFSA-N n-[(2r)-2-hydroxy-2-phenylethyl]-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C([C@H](O)C=1C=CC=CC=1)NC(=O)C(N=N1)=CC=C1N(CC1)CCN1C(=O)C1=CC=CC=C1C(F)(F)F COTQFOUJZXUUCG-NRFANRHFSA-N 0.000 claims 1
- COTQFOUJZXUUCG-OAQYLSRUSA-N n-[(2s)-2-hydroxy-2-phenylethyl]-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C([C@@H](O)C=1C=CC=CC=1)NC(=O)C(N=N1)=CC=C1N(CC1)CCN1C(=O)C1=CC=CC=C1C(F)(F)F COTQFOUJZXUUCG-OAQYLSRUSA-N 0.000 claims 1
- LMBHUUVILRXSIM-UHFFFAOYSA-N n-[2-(1,3-benzodioxol-5-yl)ethyl]-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC=2C=C3OCOC3=CC=2)CC1 LMBHUUVILRXSIM-UHFFFAOYSA-N 0.000 claims 1
- RXSTUVONHTURFI-UHFFFAOYSA-N n-[2-(2-fluorophenyl)ethyl]-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=CC=C1CCNC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 RXSTUVONHTURFI-UHFFFAOYSA-N 0.000 claims 1
- GMIYLKVUTOIYTN-UHFFFAOYSA-N n-[2-(3-chlorophenyl)ethyl]-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC=2C=C(Cl)C=CC=2)CC1 GMIYLKVUTOIYTN-UHFFFAOYSA-N 0.000 claims 1
- ZGPHZIHDGZBXEE-UHFFFAOYSA-N n-[2-(3-fluorophenyl)-2-hydroxyethyl]-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C=1C=CC(F)=CC=1C(O)CNC(=O)C(N=N1)=CC=C1N(CC1)CCN1C(=O)C1=CC=CC=C1C(F)(F)F ZGPHZIHDGZBXEE-UHFFFAOYSA-N 0.000 claims 1
- LECLQOKASFRFCY-UHFFFAOYSA-N n-[2-(3-fluorophenyl)ethyl]-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=CC(CCNC(=O)C=2N=NC(=CC=2)N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 LECLQOKASFRFCY-UHFFFAOYSA-N 0.000 claims 1
- MUORGZWDLMUFBM-UHFFFAOYSA-N n-[2-(4-chlorophenoxy)ethyl]-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCOC=2C=CC(Cl)=CC=2)CC1 MUORGZWDLMUFBM-UHFFFAOYSA-N 0.000 claims 1
- UGKDREJPNQYAJM-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC=2C=CC(Cl)=CC=2)CC1 UGKDREJPNQYAJM-UHFFFAOYSA-N 0.000 claims 1
- BXPXZJDSRUFNKN-UHFFFAOYSA-N n-[2-(4-fluorophenoxy)ethyl]-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1=CC(F)=CC=C1OCCNC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 BXPXZJDSRUFNKN-UHFFFAOYSA-N 0.000 claims 1
- JANKIHNSSUTOOG-UHFFFAOYSA-N n-[2-(4-fluorophenyl)ethyl]-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCNC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 JANKIHNSSUTOOG-UHFFFAOYSA-N 0.000 claims 1
- UPUANEQSUFKGBB-UHFFFAOYSA-N n-[2-(4-methoxyphenyl)ethyl]-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1CCNC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 UPUANEQSUFKGBB-UHFFFAOYSA-N 0.000 claims 1
- XNZFGEAAZTUXCD-UHFFFAOYSA-N n-[2-(4-phenylphenyl)ethyl]-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 XNZFGEAAZTUXCD-UHFFFAOYSA-N 0.000 claims 1
- CLBFWBCILNLSNH-UHFFFAOYSA-N n-[3-(4-fluorophenyl)propyl]-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCNC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 CLBFWBCILNLSNH-UHFFFAOYSA-N 0.000 claims 1
- JIBXIBUQTSMNSW-UHFFFAOYSA-N n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]-2-(3,3,3-trifluoropropoxy)acetamide Chemical compound N1=NC(NC(=O)COCCC(F)(F)F)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 JIBXIBUQTSMNSW-UHFFFAOYSA-N 0.000 claims 1
- LNUASDFUAFXQRC-UHFFFAOYSA-N n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NC(=O)C3CC3)=CC=2)CC1 LNUASDFUAFXQRC-UHFFFAOYSA-N 0.000 claims 1
- QMECANJPJYNFFI-UHFFFAOYSA-N n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]hexanamide Chemical compound N1=NC(NC(=O)CCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 QMECANJPJYNFFI-UHFFFAOYSA-N 0.000 claims 1
- KHZYPVIQTUBFJE-UHFFFAOYSA-N n-heptyl-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCCCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 KHZYPVIQTUBFJE-UHFFFAOYSA-N 0.000 claims 1
- BMWFXJOQYUAESO-UHFFFAOYSA-N n-hexyl-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 BMWFXJOQYUAESO-UHFFFAOYSA-N 0.000 claims 1
- NCJMWOVOUKBBEF-UHFFFAOYSA-N n-pentyl-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 NCJMWOVOUKBBEF-UHFFFAOYSA-N 0.000 claims 1
- IJDYQKWQIBEHBO-UHFFFAOYSA-N n-phenacyl-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCC(=O)C=2C=CC=CC=2)CC1 IJDYQKWQIBEHBO-UHFFFAOYSA-N 0.000 claims 1
- XILJDMHVCGVOES-UHFFFAOYSA-N n-phenyl-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C=CC=CC=2)CC1 XILJDMHVCGVOES-UHFFFAOYSA-N 0.000 claims 1
- LKNHNSABBWIULS-UHFFFAOYSA-N n-pyridazin-3-yl-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2N=NC=CC=2)CC1 LKNHNSABBWIULS-UHFFFAOYSA-N 0.000 claims 1
- XTANQZHSXMDLMO-UHFFFAOYSA-N n-pyridin-2-yl-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2N=CC=CC=2)CC1 XTANQZHSXMDLMO-UHFFFAOYSA-N 0.000 claims 1
- TVWUPMFFLXBHEX-UHFFFAOYSA-N n-pyridin-3-yl-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C=NC=CC=2)CC1 TVWUPMFFLXBHEX-UHFFFAOYSA-N 0.000 claims 1
- IUBCCQVCKFCVCP-UHFFFAOYSA-N n-pyridin-4-yl-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2C=CN=CC=2)CC1 IUBCCQVCKFCVCP-UHFFFAOYSA-N 0.000 claims 1
- DPLQPKAIGFGBSE-UHFFFAOYSA-N n-pyrimidin-2-yl-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NC=2N=CC=CN=2)CC1 DPLQPKAIGFGBSE-UHFFFAOYSA-N 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- GEKAUYCAUDEOII-UHFFFAOYSA-N propyl n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]carbamate Chemical compound N1=NC(NC(=O)OCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 GEKAUYCAUDEOII-UHFFFAOYSA-N 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- RUUOPSRRIKJHNH-UHFFFAOYSA-N pyridazine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=N1 RUUOPSRRIKJHNH-UHFFFAOYSA-N 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- OTTOHCHPIQGDAD-UHFFFAOYSA-N tert-butyl 4-[6-(2-cyclopropylethylcarbamoyl)pyridazin-3-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(C(=O)NCCC2CC2)N=N1 OTTOHCHPIQGDAD-UHFFFAOYSA-N 0.000 claims 1
- KLMDXGXUEQSEQU-UHFFFAOYSA-N tert-butyl 4-[6-(3-methylbutylcarbamoyl)pyridazin-3-yl]piperazine-1-carboxylate Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)OC(C)(C)C)CC1 KLMDXGXUEQSEQU-UHFFFAOYSA-N 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000000464 thioxo group Chemical group S=* 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
Classifications
-
- 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
-
- 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
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D237/20—Nitrogen 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
- C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Gastroenterology & Hepatology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US49109503P | 2003-07-30 | 2003-07-30 | |
US54693404P | 2004-02-23 | 2004-02-23 | |
US54681504P | 2004-02-23 | 2004-02-23 | |
US54682004P | 2004-02-23 | 2004-02-23 | |
US54678604P | 2004-02-23 | 2004-02-23 | |
US54689804P | 2004-02-23 | 2004-02-23 | |
US55341604P | 2004-03-16 | 2004-03-16 | |
US55349104P | 2004-03-16 | 2004-03-16 | |
US55340404P | 2004-03-16 | 2004-03-16 | |
US55340304P | 2004-03-16 | 2004-03-16 | |
US55344604P | 2004-03-16 | 2004-03-16 | |
PCT/US2004/024548 WO2005011655A2 (fr) | 2003-07-30 | 2004-07-29 | Derives de pyridazine et leur utilisation en tant qu'agents therapeutiques |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20110974T1 true HRP20110974T1 (hr) | 2012-01-31 |
Family
ID=34120234
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20110974T HRP20110974T1 (hr) | 2003-07-30 | 2011-12-28 | Derivati piperazina i njihova uporaba kao terapeutskih sredstava |
Country Status (23)
Country | Link |
---|---|
US (1) | US7335658B2 (fr) |
EP (3) | EP3042895A1 (fr) |
JP (1) | JP4808616B2 (fr) |
KR (1) | KR100934554B1 (fr) |
AR (1) | AR047557A1 (fr) |
AT (1) | ATE527242T1 (fr) |
AU (2) | AU2004261252C1 (fr) |
CA (1) | CA2533899C (fr) |
CY (1) | CY1112178T1 (fr) |
DK (1) | DK1648874T3 (fr) |
EC (1) | ECSP066313A (fr) |
ES (2) | ES2568769T3 (fr) |
HK (2) | HK1097256A1 (fr) |
HR (1) | HRP20110974T1 (fr) |
IL (1) | IL173395A (fr) |
MA (1) | MA28011A1 (fr) |
NO (1) | NO332822B1 (fr) |
NZ (1) | NZ545265A (fr) |
PL (1) | PL1648874T3 (fr) |
PT (1) | PT1648874E (fr) |
TN (1) | TNSN06034A1 (fr) |
TW (2) | TWI345974B (fr) |
WO (1) | WO2005011655A2 (fr) |
Families Citing this family (66)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040226056A1 (en) * | 1998-12-22 | 2004-11-11 | Myriad Genetics, Incorporated | Compositions and methods for treating neurological disorders and diseases |
US7390813B1 (en) * | 2001-12-21 | 2008-06-24 | Xenon Pharmaceuticals Inc. | Pyridylpiperazines and aminonicotinamides and their use as therapeutic agents |
US20050119251A1 (en) * | 2001-12-21 | 2005-06-02 | Jian-Min Fu | Nicotinamide derivatives and their use as therapeutic agents |
US7335658B2 (en) | 2003-07-30 | 2008-02-26 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
CN101712653A (zh) * | 2003-07-30 | 2010-05-26 | 泽农医药公司 | 哒嗪衍生物和它们作为治疗剂的用途 |
US7754711B2 (en) * | 2003-07-30 | 2010-07-13 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
ATE532772T1 (de) * | 2003-07-30 | 2011-11-15 | Xenon Pharmaceuticals Inc | Piperazinderivate und deren verwendung als therapeutische mittel |
US7759348B2 (en) * | 2003-07-30 | 2010-07-20 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
US20050165028A1 (en) * | 2004-01-23 | 2005-07-28 | Norman Mark H. | Vanilloid receptor ligands and their use in treatments |
TW200626138A (en) | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
AU2005286648A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
TW200626148A (en) * | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
EP2269610A3 (fr) * | 2004-09-20 | 2011-03-09 | Xenon Pharmaceuticals Inc. | Dérivés hétérocycliques et leur utilisation en tant qu'inhibiteurs de la stearoyl-coa desaturase |
CA2580787A1 (fr) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Derives heterocycliques et utilisation de ceux-ci comme agents therapeutiques |
AR051095A1 (es) * | 2004-09-20 | 2006-12-20 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso comoinhibidores de la estearoil-coa desaturasa |
CN101083992A (zh) * | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 抑制人硬脂酰CoA去饱和酶的哒嗪衍生物 |
MX2007003327A (es) * | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos, y su uso como mediadores de estearoil-coa desaturasa. |
AR051092A1 (es) * | 2004-09-20 | 2006-12-20 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa |
GT200600046A (es) * | 2005-02-09 | 2006-09-25 | Terapia de combinacion | |
WO2006125179A1 (fr) * | 2005-05-19 | 2006-11-23 | Xenon Pharmaceuticals Inc. | Composes tricycliques: utilisation comme agents therapeutiques |
WO2007044085A2 (fr) * | 2005-05-19 | 2007-04-19 | Xenon Pharmaceuticals Inc. | Composes heteroaryle et leurs utilisations en tant qu'agents therapeutiques |
WO2006125180A1 (fr) * | 2005-05-19 | 2006-11-23 | Xenon Pharmaceuticals Inc. | Derives de piperazine: utilisation comme agents therapeutiques |
CA2618646A1 (fr) * | 2005-06-03 | 2007-11-15 | Xenon Pharmaceuticals Inc. | Derives aminothiazole utilises en tant qu'inhibiteurs de la stearoyle-coa desaturase humaine |
EP1907004A2 (fr) * | 2005-07-01 | 2008-04-09 | Novartis AG | Combinaison d'un inhibiteur de rénine et d'un promoteur de sécretion d'insulin ou un sensibilisateur d'insulin organiques |
JO2769B1 (en) | 2005-10-26 | 2014-03-15 | جانسين فارماسوتيكا ان. في | Rapid decomposition of physiologically antagonistic agents of the 2-dopamine receptor |
AU2006326815A1 (en) * | 2005-12-20 | 2007-06-28 | Merck Frosst Canada Ltd. | Heteroaromatic compounds as inhibitors of stearoyl-coenzyme A delta-9 desaturase |
US7989461B2 (en) * | 2005-12-23 | 2011-08-02 | Amgen Inc. | Substituted quinazolinamine compounds for the treatment of cancer |
WO2007136746A2 (fr) * | 2006-05-19 | 2007-11-29 | Xenon Pharmaceuticals Inc. | Composés macrocycliques et leurs utilisations en tant qu'agents thérapeutiques |
CN101460476B (zh) | 2006-06-05 | 2013-12-04 | 诺瓦提斯公司 | 有机化合物 |
MX2009002019A (es) | 2006-08-24 | 2009-03-09 | Novartis Ag | Derivados de 2-(pirazin-2-il)-tiazol y 2-(1h-pirazol-3-il)-tiazol asi como compuestos relacionados como inhibidores de la estearoil-coa-desaturasa (scd) para el tratamiento de trastornos metabolicos, cardiovasculares, y otros. |
US8246433B2 (en) * | 2006-08-25 | 2012-08-21 | Alma Mater Sports, Llc | Team based fantasy sport contest |
WO2008056687A1 (fr) * | 2006-11-09 | 2008-05-15 | Daiichi Sankyo Company, Limited | Nouveau dérivé de spiropipéridine |
JP2010510201A (ja) * | 2006-11-20 | 2010-04-02 | グレンマーク・ファーマシューティカルズ・エスエー | ステアリン酸CoA脱飽和酵素阻害剤としてのアセチレン誘導体 |
US8575167B2 (en) | 2007-02-06 | 2013-11-05 | Takeda Pharmaceutical Company Limited | Spiro compounds having stearoyl-CoA desaturase action |
JO2849B1 (en) | 2007-02-13 | 2015-03-15 | جانسين فارماسوتيكا ان. في | Dopamine 2 receptor antagonists are rapidly hydrolyzed |
US20100120669A1 (en) * | 2007-02-28 | 2010-05-13 | Anne Marie Jeanne Bouillot | Thiadiazole derivatives, inhibitors of stearoyl-coa desaturase |
CN101663292A (zh) | 2007-04-23 | 2010-03-03 | 詹森药业有限公司 | 作为快速解离的多巴胺2受体拮抗剂的4-烷氧基哒嗪衍生物 |
KR101506156B1 (ko) | 2007-04-23 | 2015-03-26 | 얀센 파마슈티카 엔.브이. | 속해리성 도파민 2 수용체 길항제로서의 티아(디아)졸 |
PL2142529T3 (pl) * | 2007-04-27 | 2014-06-30 | Purdue Pharma Lp | Antagoniści trpv1 i ich zastosowania |
CA2687964A1 (fr) | 2007-06-01 | 2009-02-19 | The Trustees Of Princeton University | Traitement d'infections virales par modulation de voies metaboliques de cellules hotes |
WO2008157844A1 (fr) | 2007-06-21 | 2008-12-24 | Forest Laboratories Holdings Limited | Nouveaux dérivés de pipérazine en tant qu'inhibiteurs de stéaroyl-coa désaturase |
MX2010001485A (es) | 2007-08-08 | 2010-06-01 | Graceway Pharmaceuticals Llc | Derivado de fenoxi-pirrolidina y su uso, y composiciones. |
CA2697551C (fr) | 2007-09-20 | 2013-03-12 | Irm Llc | Composes et compositions en tant que modulateurs de l'activite de gpr119 |
WO2009037542A2 (fr) | 2007-09-20 | 2009-03-26 | Glenmark Pharmaceuticals, S.A. | Composés spirocycliques en tant qu'inhibiteurs de stéaroyle coa désaturase |
MX2010006108A (es) * | 2007-12-11 | 2010-06-25 | Hoffmann La Roche | Inhibidores de estearoil-coa-desaturasa. |
EA019048B1 (ru) * | 2008-07-31 | 2013-12-30 | Янссен Фармацевтика Нв | Пиперазин-1-илтрифторметилзамещенные пиридины в качестве быстро диссоциирующихся антагонистов d-рецепторов дофамина |
WO2010094120A1 (fr) | 2009-02-17 | 2010-08-26 | Merck Frosst Canada Ltd. | Nouveaux composés spiro utiles comme inhibiteurs de la stéaroyl-coenzyme a delta-9 désaturase |
WO2011011872A1 (fr) | 2009-07-28 | 2011-02-03 | Merck Frosst Canada Ltd. | Nouveaux composés spiro utiles en tant qu'inhibiteurs de la stéaroyl-coenzyme a delta-9 désaturase |
WO2011014520A2 (fr) | 2009-07-29 | 2011-02-03 | Irm Llc | Composés et compositions pouvant servir de modulateurs de l'activité du gpr119 |
EP2475367A1 (fr) | 2009-09-10 | 2012-07-18 | Centre National De La Recherche Scientifique | Nouveaux inhibiteurs de stearoyl-coa-desaturase-1 et leurs utilisations |
MX2012004078A (es) | 2009-10-09 | 2012-07-25 | Irm Llc | Compuestos y composiciones como moduladores de la actividad de gpr119. |
US8394858B2 (en) | 2009-12-03 | 2013-03-12 | Novartis Ag | Cyclohexane derivatives and uses thereof |
US8697739B2 (en) | 2010-07-29 | 2014-04-15 | Novartis Ag | Bicyclic acetyl-CoA carboxylase inhibitors and uses thereof |
RU2621708C2 (ru) | 2011-06-22 | 2017-06-07 | ПУРДЬЮ ФАРМА Эл. Пи. | Антагонисты trpv1, включающие дигидроксигруппу в качестве заместителя, и их применение |
US9358250B2 (en) | 2011-10-15 | 2016-06-07 | Genentech, Inc. | Methods of using SCD1 antagonists |
US9260441B2 (en) | 2012-03-28 | 2016-02-16 | Intervet Inc. | Heteroaryl compounds with cyclic bridging unit |
WO2013175474A2 (fr) | 2012-05-22 | 2013-11-28 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Inhibiteurs sélectifs de cellules indifférenciées |
WO2014052619A1 (fr) | 2012-09-27 | 2014-04-03 | Irm Llc | Dérivés et compositions de pipéridine comme modulateurs de l'activité de gpr119 |
WO2017049173A1 (fr) | 2015-09-16 | 2017-03-23 | Metacrine, Inc. | Agonistes du récepteur x farnésoïde et leurs utilisations |
WO2018081167A1 (fr) | 2016-10-24 | 2018-05-03 | Yumanity Therapeutics | Composés et utilisations de ces derniers |
EP3566055A4 (fr) | 2017-01-06 | 2020-12-02 | Yumanity Therapeutics, Inc. | Méthodes de traitement de troubles neurologiques |
JP7258763B2 (ja) | 2017-03-15 | 2023-04-17 | メタクリン,インク. | ファルネソイドx受容体アゴニストおよびその使用 |
JP7174709B2 (ja) | 2017-03-15 | 2022-11-17 | メタクリン,インク. | ファルネソイドx受容体アゴニストおよびその使用 |
CA3083000A1 (fr) | 2017-10-24 | 2019-05-02 | Yumanity Therapeutics, Inc. | Composes et utilisations de ces composes |
AU2019265268C1 (en) * | 2018-05-09 | 2022-08-04 | Lg Chem, Ltd. | Novel compound exhibiting enteropeptidase inhibitory activity |
JP2022500392A (ja) | 2018-09-18 | 2022-01-04 | メタクリン,インク. | ファルネソイドx受容体アゴニストおよびその使用 |
Family Cites Families (57)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US667452A (en) * | 1900-09-08 | 1901-02-05 | John A Hendrickson | Computing attachment for pumps. |
US2985657A (en) | 1959-10-12 | 1961-05-23 | Paul A J Janssen | 1-(aroylalkyl)-4-heterocyclylpiperazines |
DE2341925A1 (de) | 1973-08-20 | 1975-03-06 | Thomae Gmbh Dr K | Neue pyrimidinderivate und verfahren zu ihrer herstellung |
AT340933B (de) | 1973-08-20 | 1978-01-10 | Thomae Gmbh Dr K | Verfahren zur herstellung neuer pyrimidinderivate und ihrer saureadditionssalze |
US5001125A (en) | 1984-03-26 | 1991-03-19 | Janssen Pharmaceutica N.V. | Anti-virally active pyridazinamines |
ES8802151A1 (es) | 1985-07-31 | 1988-04-01 | Janssen Pharmaceutica Nv | Un procedimiento para la preparacion de nuevos piridazinaminas. |
JPH02502824A (ja) | 1987-04-03 | 1990-09-06 | ジ・アップジョン・カンパニー | アミノ‐9,10‐セコステロイド類 |
CA1338012C (fr) | 1987-04-27 | 1996-01-30 | John Michael Mccall | Amines possedant des proprietes pharmaceutiques |
MY104343A (en) | 1987-11-23 | 1994-03-31 | Janssen Pharmaceutica Nv | Novel pyridizinamine deravatives |
US4994456A (en) | 1989-03-01 | 1991-02-19 | Nisshin Flour Milling Co., Ltd. | Pyridinecarboxylic acid amide derivatives and pharmaceutical compositions comprising same |
IL96891A0 (en) | 1990-01-17 | 1992-03-29 | Merck Sharp & Dohme | Indole-substituted five-membered heteroaromatic compounds,their preparation and pharmaceutical compositions containing them |
US5166147A (en) | 1990-07-09 | 1992-11-24 | The Du Pont Merck Pharmaceutical Company | 4-heteroaryl-and 4-aryl-1,4-dihydropyridine, derivatives with calcium agonist and alpha1 -antagonist activity |
GB9019143D0 (en) * | 1990-09-01 | 1990-10-17 | Bp Chem Int Ltd | Thixotropic compositions |
EP0520292A1 (fr) | 1991-06-19 | 1992-12-30 | Hoechst Aktiengesellschaft | Dérivés d'azétidinones chirales et leur utilisation comme agents de dopage dans des mélanges de cristaux liquides |
DE4302051A1 (de) | 1993-01-26 | 1994-07-28 | Thomae Gmbh Dr K | 5-gliedrige Heterocyclen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
ZA97288B (en) * | 1996-01-15 | 1998-07-14 | Janssen Pharmaceutica Nv | Angiogenesis inhibiting pyridazinamines |
DE19614204A1 (de) * | 1996-04-10 | 1997-10-16 | Thomae Gmbh Dr K | Carbonsäurederivate, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
JPH107572A (ja) | 1996-06-17 | 1998-01-13 | Sumitomo Pharmaceut Co Ltd | 腫瘍壊死因子産生阻害剤 |
WO1999000386A1 (fr) | 1997-06-27 | 1999-01-07 | Resolution Pharmaceuticals Inc. | Ligands du recepteur d4 de la dopamine |
NZ507032A (en) | 1998-03-19 | 2003-06-30 | Pharmacia & Upjohn | 1,3,4-thiadiazoles useful for the treatment of herpes and cytomegalovirus infections |
US6627630B1 (en) | 1998-10-21 | 2003-09-30 | Takeda Chemical Industries, Ltd. | Condensed pyridazine derivatives, their production and use |
AU1455500A (en) | 1998-10-29 | 2000-05-22 | Trega Biosciences, Inc. | Oxadiazole, thiadiazole and triazole derivatives and combinatorial libraries thereof |
AU2319100A (en) | 1999-01-28 | 2000-08-18 | Nippon Shinyaku Co. Ltd. | Amide derivatives and drug compositions |
DE60038823D1 (de) | 1999-01-29 | 2008-06-19 | Abbott Lab | Diazabicycloderivate als Nikotin-Acetylcholin-Rezeptorliganden |
EP1035115B1 (fr) | 1999-02-24 | 2004-09-29 | F. Hoffmann-La Roche Ag | Dérivés de 4-phenylpyridine et leur utilisation comme antagonistes du recepteur NK-1 |
BR0009650A (pt) | 1999-04-09 | 2002-01-02 | Meiji Seika Kaisha | Composto, composição farmacêutica, processos para inibir a secreção de uma lipoproteìna contendo apolipoproteìna b, para inibir a biossìntese de triglicerìdeos e para prevenir ou tratar hiperlipidemia, doenças arterioscleróticas e pancreatite, e, uso do composto |
JP3637961B2 (ja) * | 1999-09-16 | 2005-04-13 | 田辺製薬株式会社 | 芳香族含窒素六員環化合物 |
US6677452B1 (en) | 1999-09-30 | 2004-01-13 | Lion Bioscience Ag | Pyridine carboxamide or sulfonamide derivatives and combinatorial libraries thereof |
WO2001043746A1 (fr) | 1999-12-14 | 2001-06-21 | Nippon Shinyaku Co., Ltd. | Composition medicinale |
AU2001247228B2 (en) | 2000-02-24 | 2007-01-18 | Wisconsin Alumni Research Foundation | Stearoyl-CoA desaturase to identify triglyceride reducing therapeutic agents |
JP2003527379A (ja) | 2000-03-15 | 2003-09-16 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | Mex阻害物質としての5−アミド置換ジアリールアミン類 |
US20020045613A1 (en) | 2000-04-27 | 2002-04-18 | Heinz Pauls | 1-aroyl-piperidinyl benzamidines |
GB0013383D0 (en) | 2000-06-01 | 2000-07-26 | Glaxo Group Ltd | Therapeutic benzamide derivatives |
AU2001280438A1 (en) | 2000-07-27 | 2002-02-13 | Eli Lilly And Company | Substituted heterocyclic amides |
EP1322767B1 (fr) | 2000-09-26 | 2008-07-23 | Xenon Pharmaceuticals Inc. | Techniques et compositions utilisant une nouvelle stearyle-coa desaturase hscd5 |
DE10060412A1 (de) | 2000-12-05 | 2002-06-06 | Bayer Ag | DELTA1-Pyrroline |
US20020169166A1 (en) | 2001-03-09 | 2002-11-14 | Cowart Marlon D. | Benzimidazoles that are useful in treating sexual dysfunction |
FR2823209B1 (fr) | 2001-04-04 | 2003-12-12 | Fournier Lab Sa | Nouvelles thiohydantoines et leur utilisation en therapeutique |
IL158941A0 (en) * | 2001-05-22 | 2004-05-12 | Neurogen Corp | Melanin concentrating hormone receptor ligands: substituted 1-benzyl-4-aryl piperazine analogues |
EP1396487B1 (fr) | 2001-06-15 | 2008-12-10 | Astellas Pharma Inc. | Derive de phenylpyridinecarbonylpiperazine |
JP4186518B2 (ja) * | 2001-06-15 | 2008-11-26 | アステラス製薬株式会社 | フェニルピリジン誘導体 |
US20050014942A1 (en) | 2001-10-30 | 2005-01-20 | Yasufumi Maruyama | Amide derivatives and drugs |
US6620811B2 (en) | 2001-11-19 | 2003-09-16 | Hoffmann-La Roche Inc. | Isonicotin- and nicotinamide derivatives of benzothiazoles |
WO2003045921A1 (fr) | 2001-11-28 | 2003-06-05 | Fujisawa Pharmaceutical Co., Ltd. | Composes d'amide heterocycliques en tant qu'inhibiteurs de l'apolipoproteine b |
WO2003050088A1 (fr) | 2001-12-07 | 2003-06-19 | Eli Lilly And Company | Carboxamides heterocycliques substitues a action antithrombotique |
MXPA04007612A (es) | 2002-02-05 | 2004-11-10 | Novo Nordisk As | Aril- y heteroarilpiperazinas novedosas. |
AU2003212335B8 (en) | 2002-03-13 | 2009-04-23 | Janssen Pharmaceutica N.V. | Aminocarbonyl-derivatives as novel inhibitors of histone deacetylase |
OA12792A (en) * | 2002-03-13 | 2006-07-10 | Janssen Pharmaceutica Nv | Sulfonyl-derivatives as novel inhibitors of histone deacetylase. |
DK1485354T3 (da) | 2002-03-13 | 2008-09-01 | Janssen Pharmaceutica Nv | Sulfonylamino-derivater som nye inhibitorer af histandeacetylase |
AU2003221786A1 (en) | 2002-04-25 | 2003-11-10 | Pharmacia Corporation | Piperidinyl-and piperazinyl-sulfonylmethyl hydroxamic acids and their use as protease inhibitors |
WO2004010927A2 (fr) | 2002-07-25 | 2004-02-05 | Wisconsin Alumni Research Foundation | Methode d'accroissement de la sensibilite a l'insuline, de traitement et de prevention de diabetes de type 2 |
MXPA05003948A (es) | 2002-10-17 | 2005-06-17 | Amgen Inc | Derivados de bencimidazol y su uso como ligandos de receptor vaniloide. |
JP2004203871A (ja) | 2002-12-13 | 2004-07-22 | Yamanouchi Pharmaceut Co Ltd | 医薬組成物 |
BRPI0406809A (pt) | 2003-01-17 | 2005-12-27 | Warner Lambert Co | Heterociclos substituìdos de 2-aminopiridina como inibidores da proliferação celular |
ATE532772T1 (de) | 2003-07-30 | 2011-11-15 | Xenon Pharmaceuticals Inc | Piperazinderivate und deren verwendung als therapeutische mittel |
CN101712653A (zh) | 2003-07-30 | 2010-05-26 | 泽农医药公司 | 哒嗪衍生物和它们作为治疗剂的用途 |
US7335658B2 (en) | 2003-07-30 | 2008-02-26 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
-
2004
- 2004-07-29 US US10/901,563 patent/US7335658B2/en not_active Expired - Fee Related
- 2004-07-29 AU AU2004261252A patent/AU2004261252C1/en not_active Ceased
- 2004-07-29 EP EP16000190.5A patent/EP3042895A1/fr not_active Withdrawn
- 2004-07-29 ES ES10184939.6T patent/ES2568769T3/es active Active
- 2004-07-29 EP EP04779562A patent/EP1648874B1/fr active Active
- 2004-07-29 CA CA2533899A patent/CA2533899C/fr active Active
- 2004-07-29 WO PCT/US2004/024548 patent/WO2005011655A2/fr active Application Filing
- 2004-07-29 TW TW093122736A patent/TWI345974B/zh not_active IP Right Cessation
- 2004-07-29 KR KR1020067002017A patent/KR100934554B1/ko not_active IP Right Cessation
- 2004-07-29 AT AT04779562T patent/ATE527242T1/de active
- 2004-07-29 TW TW099123172A patent/TW201038270A/zh unknown
- 2004-07-29 NZ NZ545265A patent/NZ545265A/en not_active IP Right Cessation
- 2004-07-29 EP EP10184939.6A patent/EP2316827B1/fr active Active
- 2004-07-29 ES ES04779562T patent/ES2375134T3/es active Active
- 2004-07-29 PT PT04779562T patent/PT1648874E/pt unknown
- 2004-07-29 PL PL04779562T patent/PL1648874T3/pl unknown
- 2004-07-29 DK DK04779562.0T patent/DK1648874T3/da active
- 2004-07-29 JP JP2006522075A patent/JP4808616B2/ja not_active Expired - Fee Related
- 2004-07-29 AR ARP040102690A patent/AR047557A1/es not_active Application Discontinuation
-
2006
- 2006-01-25 EC EC2006006313A patent/ECSP066313A/es unknown
- 2006-01-26 IL IL173395A patent/IL173395A/en not_active IP Right Cessation
- 2006-01-27 TN TNP2006000034A patent/TNSN06034A1/en unknown
- 2006-02-27 MA MA28839A patent/MA28011A1/fr unknown
- 2006-02-28 NO NO20060981A patent/NO332822B1/no not_active IP Right Cessation
-
2007
- 2007-02-01 HK HK07101166.9A patent/HK1097256A1/xx not_active IP Right Cessation
-
2009
- 2009-05-05 AU AU2009201788A patent/AU2009201788B2/en not_active Ceased
-
2011
- 2011-12-28 HR HR20110974T patent/HRP20110974T1/hr unknown
- 2011-12-29 CY CY20111101290T patent/CY1112178T1/el unknown
-
2016
- 2016-12-23 HK HK16114675A patent/HK1226399A1/zh unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
HRP20110974T1 (hr) | Derivati piperazina i njihova uporaba kao terapeutskih sredstava | |
JP2007500717A5 (fr) | ||
ZA200600125B (en) | Pyridazine derivatives and their use as therapeutic agents | |
CA2597069C (fr) | Derives de pyridazine et leur utilisation en tant qu'agents therapeutiques | |
MX2007009592A (es) | Terapia de combinacion. | |
US20080280916A1 (en) | Pyridazine derivatives and their use as therapeutic agents | |
RU2006105716A (ru) | Производные пиридазина и их применение в качестве терапевтических средств | |
AU2007333234A1 (en) | Method of preventing or treating myocardial ischemia | |
CN102245574A (zh) | 用于治疗代谢疾病的化合物、药物组合物以及方法 | |
RU2326118C2 (ru) | Производные пиридазина и их применение в качестве терапевтических агентов | |
RU2008103142A (ru) | Комбинация органических соединений | |
MXPA06001205A (en) | Pyridazine derivatives and their use as therapeutic agents |