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
Abstract
Spoj, naznačen time, da ima formulu (I): gdje: x i y su svaki neovisno 1; W je -C(O)N(R1)-; -C(O)N[C(O)R1a]-, -N(R1)C(O)N(R1)- ili -N(R1)C(O)-; V je -C(O)-, -C(S)- ili -C(R10)H;
Claims (90)
1. Spoj, naznačen time, da ima formulu (I):
[image]
gdje:
x i y su svaki neovisno 1;
W je -C(O)N(R1)-; -C(O)N[C(O)R1a]-, -N(R1)C(O)N(R1)- ili -N(R1)C(O)-;
V je -C(O)-, -C(S)- ili -C(R10)H;svaki R1 je neovisno odabran iz skupine koju čine vodik; C1-C6alkil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, metil ili trifluorometil; i C2-C6alkil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine metoksi i hidroksi;
R1a je odabran iz skupine koju čine vodik, C1-C6alkil i C3-C15cikloalkil;
R2 je odabran iz skupine koju čine C1-C12alkil, C2-C12alkenil, C2-C12hidroksialkil, C2-C12hidroksialkenil, C1-C12alkoksi, C2-C12alkoksialkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril i C3-C12heteroarilalkil; ili
R2 je višeprstenasta struktura koja ima 2 do 4 prstena, gdje su prsteni neovisno odabrani iz skupine koju čine C3-C12cikloalkil, C3-C12heterociklil, C6-C19aril i C1-C12heteroaril, pri čemu neki ili svi prsteni mogu biti stopljeni jedan s drugim;
R3 je odabran iz skupine koju čine C1-C12alkil, C2-C12alkenil, C2-C12hidroksialkil, C2-C12hidroksialkenil, C1-C12alkoksi, C2-C12alkoksialkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril i C3-C12heteroarilalkil; ili
R3 je višeprstenasta struktura koja ima 2 do 4 prstena, gdje su prsteni neovisno odabrani iz skupine koju čine C3-C12cikloalkil, C3-C12heterociklil, C6-C19aril i C1-C12heteroaril, pri čemu neki ili svi prsteni mogu biti stopljeni jedan s drugim;
R4 i R5 su svaki neovisno odabrani od sljedećih: vodik, fluoro, kloro, metil, metoksi, trifluorometil, cijano, nitro ili -N(R12)2;
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila;
ili R6 i R6a zajedno, ili R7 i R7a zajedno, ili R8 i R8a zajedno, ili R9 i R9a zajedno su okso skupina, uz uvjet da kada V je -C(O)-, R7 i R7a zajedno ili R8 i R8a zajedno ne tvore okso skupinu, dok preostali R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila; ili
jedan od R6, R6a, R7 i R7a zajedno s jednim od R8, R8a, R9 i R9a tvore alkilenski most, dok preostali R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila;
R10 je vodik ili C1-C3alkil;
svaki R12 je neovisno odabran od vodika ili C1-C6alkila; i gdje svaki C1-C3alkil, C1-C6alkil, C1-C12alkil, i svaki alkilni dio svakog od sljedećih: C2-C12hidroksialkil, C1-C12alkoksi, C2-C12alkoksialkil, C4-C12cikloalkilalkil, C7-C12aralkil, C3-C12heterociklilalkil i C3-C12heteroarilalkil, su nesupstituirani ili supstituirani jednom ili više od sljedećih skupina: C1-C12alkil, C2-C12alkenil, halo, C2-C12haloalkenil, cijano, nitro, C6-C19aril, C3-C12cikloalkil, C3-C12heterociklil, C1-C12heteroaril, -OR14, -OC(O)-R14, -N(R14)2, -C(O)R14, -C(O)OR14, -C(O)N(R14)2, -N(R14)C(O)OR16, -N (R14)C(O)R16, -N(R14)(S(O)tR16) (gdje t je 1 do 2), -S(O)tOR16 (gdje t je 1 do 2), -S(O)tR16 (gdje t je 0 do 2), i -S(O)tN(R14)2 (gdje t je 1 do 2), pri čemu svaki R14 je neovisno vodik, C1-C12alkil, haloC1-C12alkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril (nesupstituiran ili supstituiran jednim ili više halo skupina), C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril ili C3-C12heteroarilalkil; i
svaki R16 je C1-C12alkil, haloC1-C12alkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril ili C3-C12heteroarilalkil, i gdje svaki od gornjih supstituenata je nesupstituiran; pri čemu svaki C2-C12alkenil i svaki alkenilni dio od svakog od C2-C12hidroksialkenila su nesupstituirani ili supstituirani jednom od sljedećih skupina: C1-C12alkil, C2-C12alkenil, halo, C1-C12haloalkil, C2-C12haloalkenil, cijano, nitro, C6-C19aril, C7-C12aralkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril, C3-C12heteroarilalkil, -OR14, -OC(O)-R14, -N(R14)2, -C(O)R14, -C (O)OR14, -C(O)N(R14)2, -N(R14)C(O)OR16, -N(R14)C(O)R16, -N(R14)(S(O)tR16) (gdje t je 1 do 2), -S(O)tOR16 (gdje t je 1 do 2), -S(O)tR16 (gdje t je 0 do 2) i -S(O)tN(R14)2 (gdje t je 1 do 2), gdje svaki R14 je neovisno vodik, C1-C12alkil, haloC1-C12alkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril ili C3-C12heteroarilalkil; i
svaki R16 je C1-C12alkil, haloC1-C12alkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril ili C3-C12heteroarilalkil, i gdje svaki od gornjih supstituenata je nesupstituiran; pri čemu svaki C3-C12cikloalkil, svaki cikloalkilni dio od svakog C4-C12cikloalkilalkila, svaki C6-C19aril i svaki arilni dio od svakog C7-C12aralkila su nesupstituirani ili supstituirani jednim ili više supstituenata odabranih iz skupine koju čine C1-C12alkil, C2-C12alkenil, halo, C1-C12haloalkil, C2-C12haloalkenil, cijano, nitro, C6-C19aril, C7-C12aralkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril, C3-C12heteroarilalkil, -R15-OR14, -R15-OC(O)-R14, -R15-N(R14)2, -R15-C(O)R14, -R15-C(O)OR14, -R15-C(O)N(R14)2, -R15-N(R14)C(O)OR16, -R15-N(R14)C(O)R16, -R15-N(R14)(S (O)tR16) (gdje t je 1 do 2), -R15-S(O)tOR16 (gdje t je 1 do 2), -R15-S(O)tR16 (gdje t je 0 do 2) i -R15-S(O)tN (R14)2 (gdje t je 1 do 2) gdje svaki R14 je neovisno vodik, C1-C12alkil, C1-C12haloalkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril ili C3-C12heteroarilalkil;
svaki R15 je neovisno izravna veza, ili ravnolančani ili razgranati prsten C1-C12alkilenila i C2-C12alkenilena; i
svaki R16je C1-C12alkil, C1-C12haloalkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril ili C3-C12heteroarilalkil, i gdje svaki od gornjih supstituenata je nesupstituiran;
pri čemu svaki C3-C12heterociklil, svaki heterociklilni dio svakog C3-C12heterociklilalkila, svaki C1-C12heteroaril i svaki heteroarilni dio C3-C12heteroarilalkila su nesupstituirani ili supstituirani jednim ili više supstituenata odabranih iz skupine koju čine C1-C12alkil, C2-C12alkenil, halo, C1-C12haloalkil, C2-C12haloalkenil, cijano, okso, tiokso, nitro, C6-C19aril, C7-C12aralkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril, C3-C12heteroarilalkil, -R15-OR14, -R15-OC(O)-R14, -R15-N(R14)2, -R15-C(O)R14, -R15-C(O)OR14, -R15-C(O)N(R14)2, -R15-N(R14)C(O)OR16, -R15-N(R14) C(O)R16, -R15-N(R14)(S(O)tR16) (gdje t je 1 do 2), -R15-S(O)tOR16 (gdje t je 1 do 2), -R15-S(O)tR16 (gdje t je 0 do 2) i -R15-S(O)tN(R14)2 (gdje t je 1 do 2), gdje svaki R14 je neovisno vodik, C1-C12alkil, C2-C12alkenil, C1-C12haloalkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril ili C3-C12heteroarilalkil;
svaki R15 je neovisno izravna veza ili ravnolančani ili razgranati prsten C1-C12alkilena ili C2-C12alkenilena; i
svaki R16 je C1-C12alkil, C2-C12alkenil, C1-C12haloalkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril ili C3-C12heteroarilalkil, i gdje svaki od gornjih supstituenata je nesupstituiran; i
njegov stereoizomer, enantiomer ili tautomer, njegova farmaceutski prihvatljiva sol, ili njegov farmaceutski sastav.
2. Spoj, naznačen time, da ima formulu (II):
[image]
gdje:
x i y su svaki neovisno 1;
W je odabran od -C(O)N(R1)- i -N(R1)C(O)-;
svaki R1je neovisno odabran iz skupine koju čine vodik; C1-C6alkil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, metil ili trifluorometil; i C2-C6alkil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine metoksi i hidroksi;
R2 je odabran iz skupine koju čine C7-C12alkil, C3-C12alkenil, C7-C12hidroksialkil, C2-C12alkoksialkil, C3-C12hidroksialkenil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C13-C19aralkil, C3-C12heterociklilalkil i C3-C12heteroarilalkil; ili
R2 je višeprstenasta struktura koja ima 2 do 4 prstena, gdje su prsteni neovisno odabrani iz skupine koju čine C3-C12cikloalkil, C3-C12heterociklil, C6-C19aril i C1-C12heteroaril, pri čemu neki ili svi prsteni mogu biti stopljeni jedan s drugim;
R3 je odabran iz skupine koju čine C3-C12alkil, C3-C12alkenil, C3-C12hidroksialkil, C3-C12hidroksialkenil, C3-C12alkoksi, C3-C12alkoksialkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C5-C12heteroaril i C3-C12heteroarilalkil; ili
R3 je višeprstenasta struktura koja ima 2 do 4 prstena, gdje su prsteni neovisno odabrani iz skupine koju čine C3-C12cikloalkil, C3-C12heterociklil, C6-C19aril i C1-C12heteroaril, pri čemu neki ili svi prsteni mogu biti stopljeni jedan s drugim;
R4i R5su svaki neovisno odabrani od sljedećih: vodik, fluoro, kloro, metil, metoksi ili trifluorometil; i
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila; ili R6 i R6a zajedno, ili R9 i R9a zajedno su okso skupina, dok su preostali R6, R6a, R7, R7a, R8, R8a, R9 i R9a svaki neovisno odabrani od vodika ili C1-C3alkila; ili
jedan od R6, R6a, R7 i R7a zajedno s jednim od R8, R8a, R9 i R9atvore alkilenski most, dok su preostali R6, R6a, R7, R7a, R8, R8a, R9 i R9asvaki neovisno odabrani od vodika ili C1-C3alkila; gdje svaki od sljedećih: C1-C3alkil, C1-C6alkil, C1-C12alkil, i svaki alkilni dio svakog od sljedećih: C1-C12hidroksialkil, C1-C12alkoksi, C2-C12alkoksialkil, C4-C12cikloalkilalkil, C13-C19aralkil, C3-C12heterociklilalkil i C3-C12heteroarilalkil, su nesupstituirani ili supstituirani jednom ili više od sljedećih skupina: C1-C12alkil, C2-C12alkenil, halo, C2-C12haloalkenil, cijano, nitro, C6-C19aril, C3-C12cikloalkil, C3-C12heterociklil, C1-C12heteroaril, -OR14, -OC(O)-R14, -N(R14)2, -C(O)R14, -C(O)OR14, -C(O)N(R14)2, -N(R14)C(O)OR16, -N (R14)C(O)R16, -N(R14)(S(O)tR16) (gdje t je 1 do 2), -S(O)tOR16 (gdje t je 1 do 2), -S(O)tR16 (gdje t je 0 do 2) i -S(O)tN(R14)2 (gdje t je 1 do 2), gdje svaki R14 je neovisno vodik, C1-C12alkil, haloC1-C12alkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril (nesupstituiran ili supstituiran jednom ili više halo skupina), C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril ili C3-C12heteroarilalkil; i
svaki R16 je C1-C12alkil, haloC1-C12alkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril ili C3-C12heteroarilalkil, pri čemu svaki od gornjih supstituenata je nesupstituiran;
gdje svaki C2-C12alkenil i svaki alkenilni dio svakog od C2-C12hidroksialkenila su nesupstituirani ili supstituirani jednom od sljedećih skupina: C1-C12alkil, C2-C12alkenil, halo, C1-C12haloalkil, C2-C12haloalkenil, cijano, nitro, C6-C19aril, C7-C12aralkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril, C3-C12heteroarilalkil, -OR14, -OC(O)-R14, -N(R14)2, -C(O)R14, -C (O)OR14, -C(O)N(R14)2, -N(R14)C(O)OR16, -N(R14)C(O)R16, -N(R14)(S(O)tR16) (gdje t je 1 do 2), -S(O)tOR16 (gdje t je 1 do 2), -S(O)tR16 (gdje t je 0 do 2) i -S(O)tN(R14)2 (gdje t je 1 do 2), gdje svaki R14 je neovisno vodik, C1-C12alkil, haloC1-C12alkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril ili C3-C12heteroarilalkil: i
svaki R16 je C1-C12alkil, haloC1-C12alkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril ili C3-C12heteroarilalkil, pri čemu svaki od gornjih supstituenata je nesupstituiran;
gdje svaki C3-C12heterociklil, svaki heterociklilni dio od svakog C3-C12hetrociklilalkila, svaki C1-C12heteroaril i svaki heteroarilni dio od svakog C3-C12heteroarilalkila su nesupstituirani ili supstituirani jednim ili više supstituenata odabranih iz skupine koju čine C1-C12alkil, C2-C12alkenil, halo, C1-C12haloalkil, C2-C12haloalkenil, cijano, okso, tiokso, nitro, C6-C19aril, C7-C12aralkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril, C3-C12heteroarilalkil, -R15-OR14, -R15-OC(O)-R14, -R15-N(R14)2, -R15-C(O)R14, -R15-C(O)OR14, -R15-C(O)N(R14)2, -R15-N(R14)C(O)OR16, -R15-N(R14)C(O)R16, -R15-N(R14)(S(O)tR16) (gdje t je 1 do 2), -R15-S(O)tOR16 (gdje t je 1 do 2), -R15-S(O)tR16 (gdje t je 0 do 2) i -R15-S(O)tN(R14)2 (gdje t je 1 do 2), gdje svaki R14 je neovisno vodik, C1-C12alkil, C2-C12alkenil, C1-C12haloalkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril ili C3-C12heteroarilalkil;
svaki R15 je neovisno izravna veza ili ravnolančani ili razgranati prsten C1-C12alkilena ili C2-C12alkenilena; i
svaki R16 je C1-C12alkil, C2-C12alkenil, C1-C12haloalkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril ili C3-C12heteroarilalkil, pri čemu svaki od gornjih supstituenata je nesupstituiran; i
njegov stereoizomer, enantiomer ili tautomer, njegova farmaceutski prihvatljiva sol, ili njegov farmaceutski sastav.
3. Spoj prema zahtjevu 2, naznačen time, da:
x i y su svaki 1;
W je odabran od -C(O)N(R1)- i -N(R1)C(O)-;
svaki R1 je neovisno odabran od vodika ili C1-C6alkila;
R2 je odabran iz skupine koju čine C7-C12alkil, C3-C12alkenil, C7-C12hidroksialkil, C2-C12alkoksialkil, C3-C12hidroksialkenil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C13-C19aralkil, C3-C12heterociklilalkil i C3-C12heteroarilalkil;
svaki R2 je nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, C1-C3alkil, -OR11, -C(O)OR11, C1-C6trihaloalkil, C3-C12cikloalkil, C3-C12heterociklil, C6-C19aril, C1-C12heteroaril i C1-C12heteroarilC3-C12cikloalkil;
R3 je odabran iz skupine koju čine C3-C12alkil, C3-C12alkenil, C3-C12hidroksialkil, C3-C12hidroksialkenil, C3-C12alkoksi, C3-C12alkoksialkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C5-C12heteroaril i C3-C12heteroarilalkil;
svaki R3 je nesupstituiran ili supstituiran jednim ili više supsituenata odabranih iz skupine koju čine C1-C6alkil, C1-C6trihaloalkil, C1-C6trihaloalkoksi, C1-C6alkoksi, C1-C6alkilsulfonil, halo, cijano, nitro, hidroksi, -N(R12)2, -C(O)OR11, -S(O)2N(R12)2, C3-C12cikloalkil, C3-C12heterociklil, C6-C19aril, C7-C12aralkil, C1-C12heteroaril i C1-C12heteroarilC3-C12cikloalkil;
R4i R5 su svaki neovisno odabrani od sljedećih: vodik, fluoro, kloro, metil, metoksi ili trifluorometil;
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila; svaki R11je neovisno odabran od vodika, C1-C6alkila, C6-C19arila ili C7-C12aralkila; i
svaki R12 je neovisno odabran od vodika ili C1-C6alkila.
4. Spoj prema zahtjevu 3, naznačen time, da:
W je -N(R1)C(O)-;
R1 je vodik;
R2 je C4-C12cikloalkilalkil;
R3 je C3-C12alkil ili C3-C12alkenil, svaki nesupstituiran ili supstituiran jednom ili više halo skupina;
R4 i R5 su svaki vodik; i
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki vodik.
5. Spoj prema zahtjevu 4, naznačen time, da je odabran iz skupine koju čine sljedeći:
6-[4-(2-etilbutiril)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(3,3,3-trifluoro-2-metil-2-trifluorometilpropionil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklo-propiletil)amid;
6-[4-(2,2-dimetilpropionil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2,2-dimetilbutiril)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2,2-dimetilpentanoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(4,4,4-trifluorobut-2-enoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid; i
6-[4-(4,4,4-trifluoro-3-trifluorometilbut-2-enoil)-piperazin-1-il]piridazin-3-karboksilna kiselina
(2-ciklopropiletil)amid.
6. Spoj prema zahtjevu 3, naznačen time, da:
W je -N(R1)C(O)-;
R1 je vodik;
R2 je C4-C12cikloalkilalkil;
R3 je C3-C12cikloalkil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih od hidroksi, C1-C6trihaloalkila ili C1-C6alkila;
R4 i R5 su svaki vodik; i
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki vodik.
7. Spoj prema zahtjevu 6, naznačen time, da je odabran iz skupine koju čine sljedeći:
6-[4-(1-hidroksiciklopropankarbonil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-(4-ciklobutankarbonilpiperazin-1-il)piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2-rifluorometilciklopropankarbonil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil) amid;
6-(4-cikloheksankarbonilpiperazin-1-il)piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2-metilcikloheksankarbonil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(3-metilcikloheksankarbonil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(4-metilcikloheksankarbonil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2-metilciklopropankarbonil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid; i
6-[4-(2,2,3,3-tetrametilciklopropankarbonil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid.
8. Spoj prema zahtjevu 3, naznačen time, da:
W je -N(R1)C(O)-;
R2 je C4-C12cikloalkilalkil;
R3 je C3-C12hidroksialkil nesupstituiran ili supstituiran jednom ili više halo skupina;
R4 i R5 su svaki vodik; i
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki vodik.
9. Spoj prema zahtjevu 8, naznačen time, da je odabran iz skupine koju čine sljedeći:
6-[4-(4,4,4-trifluoro-3-hidroksi-3-trifluorometilbutiril)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(4,4,4-trifluoro-3-hidroksi-3-metilbutiril)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid; i
6-[4-(3,3,3-trifluoro-2-hidroksi-2-metilpropionil)piperazin-1-il]piridazin-3-karboksilna kiselina
(2-ciklopropiletil)amid.
10. Spoj prema zahtjevu 3, naznačen time, da:
W je -N(R1)C(O)-;
R1 je vodik;
R2 je C4-C12cikloalkilalkil;
R3 je C3-C12alkoksi;
R4 i R5 su svaki vodik; i
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki vodik.
11. Spoj prema zahtjevu 10, naznačen time, da je odabran iz skupine koju čine sljedeći:
4-[6-(3-metilbutilkarbamoil)piridazin-3-il]piperazin-1-karboksilna kiselina t-butil ester; i
4-[6-(2-ciklopropiletilkarbamoil)piridazin-3-il]piperazin-1-karboksilna kiselina t-butil ester.
12. Spoj prema zahtjevu 3, naznačen time, da:
W je -N(R1)C(O)-;
R1 je vodik;
R2 je C4-C12cikloalkilalkil;
R3 je C7-C12aralkil nesupstituiran ili supstituiran jednim ili više supstituenata neovisno odabranih od halo ili C1-C6trihaloalkila;
R4 i R5 su svaki vodik; i
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki vodik.
13. Spoj prema zahtjevu 12, naznačen time, da je to
6-{4-[2-(2-trifluorometilfenil)acetil]piperazin-1-il}piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid.
14. Spoj prema zahtjevu 3, naznačen time, da:
W je -N(R1)C(O)-;
R1 je vodik;
R2 je C4-C12cikloalkilalkil;
R3 je C3-C12heterociklil ili C5-C12heteroaril, svaki nesupstituiran ili supstituiran jednim ili više supstituenata neovisno odabranih od halo, C1-C6alkila, C1-C6trihaloalkila ili C7-C12aralkila;
R4 i R5 su svaki vodik; i
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki vodik.
15. Spoj prema zahtjevu 14, naznačen time, da je odabran iz skupine od sljedećih:
6-[4-(piridin-2-karbonil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2-trifluorometilfuran-3-karbonil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2-kloro-4-trifluorometilpirimidin-5-karbonil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(5-metil-2-trifluorometilfuran-3-karbonil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2-kloropiridin-3-karbonil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2-metil-5-trifluorometiloksazol-4-karbonil)piperazin-1-il]-piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2,6-dikloropiridin-3-karbonil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(pirolidin-1-karbonil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(1-metil-1H-pirol-2-karbonil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid; i
6-[4-(tetrahidrofuran-2-karbonil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid.
16. Spoj prema zahtjevu 1, naznačen time, da:
x i y su svaki neovisno 1;
W je odabran od -C(O)N(R1)- i -N(R1)C(O)-;
V je -C(O)- ili -C(S)-;
svaki R1 je neovisno odabran iz skupine koju čine vodik;
C1-C6alkil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, metil ili trifluorometil; i
C2-C6alkil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine metoksi i hidroksi;
R2 je odabran iz skupine koju čine C1-C12alkil, C2-C12alkenil, C2-C12hidroksialkil, C2-C12hidroksialkenil, C1-C6alkoksi, C3-C12alkoksialkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril i C3-C12heteroarilalkil; ili
R2 je višeprstenasta struktura koja ima 2 do 4 prstena, gdje su prsteni neovisno odabrani iz skupine koju čine C3-C12cikloalkil, C3-C12heterociklil, C6-C19aril i C1-C12heteroaril, pri čemu neki ili svi prsteni mogu biti stopljeni jedan s drugim;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, cijano, nitro, hidroksi, C1-C6alkil, C1-C6trihaloalkil, C1-C6trihaloalkoksi, C1-C6alkilsulfonil, -N (R11)2, -OC(O)R11, -C(O)OR11, -S(O)2N(R11)2, C3-C12cikloalkil, C3-C12heterociklil, C1-C12heteroaril i C1-C12heteroarilC3-C12cikloalkil, uz uvjet da R3nije fenil supstituiran sa nesupstituiranim ili supstituiranim tienilom;
R4i R5su svaki neovisno odabrani od sljedećih: vodik, fluoro, kloro, metil, metoksi ili trifluorometil;
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila;
ili R6 i R6a zajedno, ili R7 i R7a zajedno, ili R8 i R8a zajedno, ili R9 i R9a zajedno su okso skupina, uz uvjet da kada V je -C(O)-, tada R7 i R7a zajedno ili R8 i R8a zajedno ne tvore okso skupinu, dok preostali R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila; ili
jedan od R6, R6a, R7 i R7a zajedno s jednim od R8, R8a, R9 i R9atvore alkilenski most, dok preostali R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila; i
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C12cikloalkil, C6-C19aril ili C7-C12aralkil;
njegov stereoizomer, enantiomer ili tautomer, njegova farmaceutski prihvaljiva sol, ili njegov farmaceutski sastav.
17. Spoj prema zahtjevu 16, naznačen time, da:
x i y su svaki 1;
V je -C(O)- ili -C(S)-;
W je odabran od -C(O)N(R1)- i -N(R1)C(O)-;
svaki R1 je neovisno odabran od vodika ili C1-C6alkila;
R2 je odabran iz skupine koju čine C1-C12alkil, C2-C12alkenil, C2-C12hidroksialkil, C2-C12hidroksialkenil, C1-C6alkoksi, C3-C12alkoksialkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril i C3-C12heteroarilalkil;
svaki R2 je nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, cijano, okso, tiokso, C1-C3alkil, -OR11, -C(O)R11, -OC(O)R11, -C(O)OR11, -C(O)N(R12)2, -N(R12)2, C1-C6trihaloalkil, C3-C12cikloalkil, C3-C12heterociklil, C6-C19aril, C1-C12heteroaril i C1-C12heteroarilC3-C12cikloalkil;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, cijano, nitro, hidroksi, C1-C6alkil, C1-C6trihaloalkil, C1-C6trihaloalkoksi, C1-C6alkilsulfonil, -N(R12)2, -OC(O)R11, -C(O)OR11, -S(O)2N(R12)2, C3-C12cikloalkil, C3-C12heterociklil i C1-C12heteroarilC3-C12cikloalkil;
R4 i R5 su svaki neovisno odabrani od sljedećih: vodik, fluoro, kloro, metil, metoksi ili trifluorometil;
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila; ili
R6 i R6a zajedno ili R9 i R9a zajedno su okso skupina, dok preostali R6, R6a, R7, R7a, R8, R8a,
R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila;
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C12cikloalkil, C6-C19aril ili C7-C12aralkil; i
svaki R12 je neovisno odabran od vodika ili C1-C6alkila.
18. Spoj prema zahtjevu 17, naznačen time, da:
x i y su svaki 1;
V je -C(O)-ili -C(S)-;
W je -N(R1)C(O)-;
R1 je vodik, metil ili etil;
R4i R5su svaki neovisno odabrani od sljedećih: vodik, fluoro, kloro, metil, metoksi ili trifluorometil; i
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila.
19. Spoj prema zahtjevu 18, naznačen time, da:
R2 je C4-C12cikloalkilalkil nesupstituiran ili supstituiran jednim ili više supstituenata odabrabnih iz skupine koju čine -OR11, C1-C3alkil ili C6-C19aril;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, cijano, nitro, hidroksi, C1-C6alkil, C1-C6trihaloalkil, C1-C6trihaloalkoksi, C1-C6alkilsulfonil, -N(R12)2, -OC(O)R11, -C(O)OR11, -S(O)2N(R12)2 i C3-C12cikloalkil;
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C12cikloalkil, C6-C19aril ili C7-C12aralkil;
svaki R12 je neovisno odabran od vodika ili C1-C6alkila.
20. Spoj prema zahtjevu 19, naznačen time, da je odabran iz skupine koju čine sljedeći:
6-(4-benzoilpiperazin-1-il)piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2-kloro-5-fluorobenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(5-kloro-2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2,6-difluorobenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2,5-bis-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2,4-bis-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2,5-difluorobenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(5-fluoro-2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-ciklopropilpropil)amid;
6-[4-(2-fluorobenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(3-fluoro-2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(4-fluoro-2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-ciklopropilpropil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-metilciklopropilmetil)amid;
6-[4-(5-fluoro-2-metoksibenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2-dimetilaminobenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2-kloro-5-dimetilaminobenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2,5-dimetilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2,5-diklorobenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina ciklobutilmetilamid;
octena kiselina 2-{4-[6-(2-ciklopropiletilkarbamoil)-piridazin-3-il]piperazin-1-karbonil}fenil ester;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropil-2-hidroksietil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-fenilciklopropilmetil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-ciklopropilpropil)amid;
6-[4-(2-cijanobenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-{4-[2-(2-trifluorometilfenil)acetil]piperazin-1-il}piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(4-fluoro-2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(5-kloro-2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-ciklopropilpropil)amid;
6-[3,5-dimetil-4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
2-{4-[6-(2-ciklopropiletilkarbamoil)piridazin-3-il]piperazin-1-karbonil}benzoična kiselina metil ester;
6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (2-ciklobutil-etil)-amid;
2-{4-[6-(2-ciklopropil-etilkarbamoil)-piridazin-3-il]-piperazin-1-karbonil}-benzoična kiselina;
6-[4-(5-kloro-2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (2-ciklobutil-etil)-amid;
6-[4-(5-fluoro-2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (2-ciklobutil-etil)-amid;
6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (3-ciklobutil-propil)-amid;
6-[4-(2-trifluorometil-tiobenzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (2-ciklopropil-etil)-amid;
6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (4-ciklopropil-butil)-amid; i
6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (2,2-dimetil-ciklopropilmetil)-amid.
21. Spoj prema zahtjevu 18, naznačen time, da:
V je -C(O)-;
R2 je C1-C12alkil ili C2-C12alkenil, svaki nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, ariloksi, -C(O)R11, -OC(O)R11 ili -C(O)OR11;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, cijano, nitro, hidroksi, C1-C6alkil, C1-C6trihaloalkil, C1-C6trihaloalkoksi, C1-C6alkilsulfonil, -N(R12)2, -OC (O)R11, -C(O)OR11, -S(O)2N(R12)2 i C3-C12cikloalkil;
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C6cikloalkil, C7-C12aralkil, ili C6-C19aril (nesupstituiran ili supstituiran jednom ili više halo skupina);
i svaki R12 je neovisno odabran od vodika ili C1-C6alkila.
22. Spoj prema zahtjevu 21, naznačen time, da je odabran iz skupine koju čine sljedeći:
6-[4-(2-nitrobenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-metilbutil)amid;
6-[4-(2-klorobenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-metilbutil)amid;
6-[4-(2,4-diklorobenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-metilbutil)amid;
6-[4-(2-aminobenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-metilbutil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina [2-(4-klorofenoksi)etil]amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina [2-(4-fluorofenoksi)etil]amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3,3-dimetilbutil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina pentilamid;
4-({6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karbonil}amino)butirinska kiselina etil ester;
6-[4-(5-fluoro-2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina pentilamid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (4-metilpentil)amid;
6-[4-(2-fluoro-6-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-metilbutil)amid;
6-[4-(2,6-difluorobenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-metilbutil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-okso-2-feniletil)amid;
octena kiselina 1,1-dimetil-3-({6-[4-(2-trifluorometil-benzoil)piperazin-1-il]piridazin-3-karbonil}amino)propil ester;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-fenoksietil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina heksilamid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (4-metilpentil)amid;
6-[4-(5-fluoro-2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (4-metilpentil)amid;
6-[2,5-dimetil-4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina pentilamid;
6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina heptilamid;
6-[4-(2-sulfamoil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (3-metilbutil)-amid;
6-[4-(5-kloro-2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina heksilamid;
6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (2-ciklopropil-2-oksoetil)-amid;
4-trifluorometil-6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (3-metilbutil)-amid; i
6-[4-(5-fluoro-2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina pentil-4-enilamid.
23. Spoj prema zahtjevu 18, naznačen time, da:
V je -C(O)-;
R2je C2-C12hidroksialkil ili C2-C12hidroksialkenil, svaki nesupstituiran ili supstituiran jednom ili više halo skupina;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, cijano, nitro, hidroksi, C1-C6alkil, C1-C6trihaloalkil, C1-C6trihaloalkoksi, C1-C6alkilsulfonil, -N(R12)2, -OC(O)R11, -C(O)OR11, -S(O)2N(R12)2 i C3-C12cikloalkil;
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C6cikloalkil, C7-C12aralkil ili C6-C19aril (nesupstituiran ili supstituiran jednom ili više halo skupina); i
svaki R12 je neovisno odabran od vodika ili C1-C6alkila.
24. Spoj prema zahtjevu 23, naznačen time, da je odabran iz skupine koju čine sljedeći:
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (4-hidroksibutil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-hidroksi-4,4-dimetilpentil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-hidroksi-3-metilbutil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-hidroksi-3,3-dimetilbutil)amid; i
6-[4-(5-fluoro-2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-hidroksi-3,3-dimetil-butil)amid.
25. Spoj prema zahtjevu 18, naznačen time, da:
V je -C(O)-;
R2 je C7-C12aralkil, gdje je arilni dio od C7-C12aralkil skupine nesupstituiran ili supstituiran jednim ili više supstituenata neovisno odabranih od sljedećih: halo, C1-C3alkil, -OR11, -C(O)OR11, C1-C6trihaloalkil, C3-C12cikloalkil i C6-C19aril, i alkilni dio od C7-C12aralkil skupine je nesupstituiran ili supstituiran jednim ili više supstituenata neovisno odabranih od halo, -OR11 i -OC(O)R11;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, cijano, nitro, hidroksi, C1-C6alkil, C1-C6trihaloalkil, C1-C6trihaloalkoksi, C1-C6alkilsulfonil, -N(R12)2, -OC (O)R11, -C(O)OR11, -S(O)2N(R12)2 i C3-C12cikloalkil;
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C6cikloalkil, C7-C12aralkil, ili C6-C19aril (nesupstituiran ili supstituiran jednom ili više halo skupina); i
svaki R12 je neovisno odabran od vodika ili C1-C6alkila.
26. Spoj prema zahtjevu 25, naznačen time, da je odabran iz skupine koju čine sljedeći:
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina [2-(2,4-fluorofenil)etil]amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina [2-(2-fluorofenil)etil]amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina [2-(4-klorofenil)etil]amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina [2-(3-klorofenil)etil]amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-fenilpropil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-bifenil-4-iletil)amid;
(R)-6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-hidroksi-2-feniletil)-amid;
(S)-6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-hidroksi-2-feniletil)-amid;
octena kiselina 1-fenil-2-({6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]piridazin-3-karbonil} amino)etil ester;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina [3-(4-fluorofenil)propil]amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2,2-difluoro-2-feniletil)amid; i
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina [2-(3-fluorofenil)-2-hidroksietil]amid.
27. Spoj prema zahtjevu 18, naznačen time, da:
V je -C(O)-;
R2 je C1-C6alkoksi ili C3-C12alkoksialkil, svaki nesupstituiran ili supstituiran jednim ili više supstituenata neovisno odabranih od halo ili C3-C12cikloalkila;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, cijano, nitro, hidroksi, C1-C6alkil, C1-C6trihaloalkil, C1-C6trihaloalkoksi, C1-C6alkilsulfonil, -N(R12)2, -OC (O)R11, -C(O)OR11, -S(O)2N(R12)2 i C3-C12cikloalkil; svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C6cikloalkil, C7-C12aralkil, ili C6-C19aril (nesupstituiran ili supstituiran s jednom ili više halo skupina); i
svaki R12 je neovisno odabran od vodika ili C1-C6alkila.
28. Spoj prema zahtjevu 27, naznačen time, da je odabran iz skupine koju čine sljedeći:
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-etoksietil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-metoksi-3,3-dimetilbutil)amid; i
2-(2-ciklopropil-etoksi)-N-{6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-il}-acetamid.
29. Spoj prema zahtjevu 18, naznačen time, da:
V je -C(O)-;
R2 je C6-C19aril nesupstituiran ili supstituiran s jednim ili više supstituenata neovisno odabranih od sljedećih: halo, cijano, C1-C3alkil, -OR11, -C(O)R11, -OC(O)R11, -C(O)OR11, -C(O)N(R12)2, C1-C6trihaloalkil, C3-C12cikloalkil, C3-C12heterociklil, C6-C19aril, C1-C12heteroaril i C1-C12heteroarilC3-C12cikloalkil;
R3 je fenil nesupstituiran ili supstituiran sa C1-C6trihaloalkil ili C1-C6trihaloalkoksi;
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C6cikloalkil, C7-C12aralkil, ili C6-C19aril (nesupstituiran ili supstituiran s jednom ili više halo skupina); i
svaki R12 je neovisno odabran od vodika ili C1-C6alkila.
30. Spoj prema zahtjevu 29, naznačen time, da je odabran iz skupine koju čine sljedeći:
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (4-klorofenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (4-karbamoil-fenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-karbamoil-fenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina m-tolilamid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina p-tolilamid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina o-tolilamid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-propilfenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina (4-propilfenil)amid;
6-[4-(2-trifluorometil-benzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (4-izopropilfenil)amid;
6-[4-(2-trifluorometil-benzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-izopropilfenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-klorofenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-cijano-3-fluorofenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2,4-dimetil-fenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2,5-dimetil-fenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2,6-dimetil-fenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2,3-dimetil-fenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3,5-dimetil-fenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3,4-dimetil-fenil)amid;
6-[4-(2-trifluorometil-benzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (4-etilfenil)amid;
6-[4-(2-trifluorometil-benzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-etilfenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-fluoro-2-metilfenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-fluoro-4-metilfenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (4-fluoro-2-metilfenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-fluoro-5-metilfenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina (3-fluoro-5-metilfenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina (3-fluorofenil)-amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina (2-fluorofenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (4-fluorofenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2,4-difluoro-fenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2,5-difluoro-fenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina (3,4-difluoro-fenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina (2,3-difluoro-fenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2,6-difluoro-fenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (4-cijanofenil)-amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-cijanofenil)-amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-cijanofenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-klorofenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-kloro-2-metilfenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-kloro-3-metilfenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2,5-diklorofenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-kloro-5-metilfenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-kloro-6-metilfenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (4-kloro-2-metilfenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (4-kloro-3-metilfenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-kloro-4-metilfenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-kloro-4-metilfenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-kloro-5-fluorofenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (5-kloro-2-fluorofenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2,5-difluorofenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2,6-diklorofenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-trifluorometilfenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (4-trifluorometilfenil)amid;
6-[4-(2-trifluorometilbenzoil)-piperazin-1-il]piridazin-3-karboksilna kiselina (3-trifluorometilfenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina fenilamid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (5-kloro-2-metoksifenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2,5-dimetoksifenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-kloro-4-metoksifenil)amid;
6-[4-(2-trifluorometilbenzoil)-piperazin-1-il]piridazin-3-karboksilna kiselina (4-metoksi-fenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-metoksifenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-metoksifenil)amid;
4-({6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karbonil}amino)-benzoična kiselina metil ester;
4-({6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karbonil}amino)-benzoična kiselina;
2-({6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karbonil}amino)-benzoična kiselina metil ester;
2-({6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karbonil}amino)-benzoična kiselina;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3,4-diklorofenil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina indan-1-ilamid; i
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina indan-5-ilamid;
31. Spoj prema zahtjevu 18, naznačen time, da:
V je -C(O)-;
R2 je C1-C12heteroaril nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, cijano, okso, tiokso, C1-C3alkil, -OR11, -C(O)R11, -OC(O)R11, -C(O)OR11, -C(O)N(R12)2 i C1-C6trihaloalkil;
R3 je fenil nesupstituiran ili supstituiran C1-C6trihaloalkilom ili C1-C6trihaloalkoksi;
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C6cikloalkil, C7-C12aralkil ili C6-C19aril (nesupstituiran ili supstituiran jednom ili više halo skupina); i
svaki R12 je neovisno odabran od vodika ili C1-C6alkila.
32. Spoj prema zahtjevu 31, naznačen time, da je C1-C12heteroaril odabran iz skupine koju čine piridinil, purinil, pirazinil, indolil, indazolil, benzoimidazolil, imidazolil, tetrazolil, triazolil, izoksazolil, pirazolil, pirimidinil, tiadiazolil, tiazolil i piridazinil.
33. Spoj prema zahtjevu 32, naznačen time, da je odabran iz skupine koju čine sljedeći:
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (5-kloropiridin-2-il)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (5-trifluorometilpiridin-2-il)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (7H-purin-6-il)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina pirazin-2-ilamid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina (1H-tetrazol-5-il)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2H-[1,2,4]triazol-3-il)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-metil-izoksazol-5-il)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina (5-metil-izoksazol-3-il)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina (1H-pirazol-3-il)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina (5-metil-1H-pirazol-3-il)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina pirimidin-2-ilamid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina pirazin-2-ilamid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina (4-metil-pirimidin-2-il)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina (2-okso-2,3-dihidro-pirimidin-4-il)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina (6-okso-1,6-dihidro-pirimidin-2-il)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina [1,3,4]tiadiazol-2-ilamid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina tiazol-2-ilamid;
6-[4-(2-trifluorometil-benzoil)piperazin-1-il]piridazin-3-karboksilna kiselina piridin-2-ilamid;
6-[4-(2-trifluorometil-benzoil)piperazin-1-il]piridazin-3-karboksilna kiselina piridazin-3-ilamid;
6-[4-(2-trifluorometil-benzoil)piperazin-1-il]piridazin-3-karboksilna kiselina piridin-3-ilamid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina piridin-4-ilamid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (6-okso-1,6-dihidro-[1,3,5]triazin-2-il)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (5-fluoro-piridin-2-il)-amid;
6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (5-cijano-piridin-2-il)-amid;
6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (4,6-dimetil-pirimidin-2-il)-amid;
6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (2-kloro-piridin-4-il)-amid;
6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (1H-indol-6-il)-amid;
6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (1H-indol-4-il)-amid;
6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (1H-indazol-5-il)-amid;
6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (1H-indazol-6-il)-amid;
6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (4-metil-tiazol-2-il)-amid;
6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (5-metil-tiazol-2-il)-amid;
6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (5-tiokso-4,5-dihidro-1H-[1,2,4]triazol-3-il)-amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina (1H-benzoimidazol-2-il)-amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (6-metilpiridazin-3-il)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (6-metoksipiridazin-3-il)amid; i
6-[4-(2-trifluorometilbenzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (6-kloro-piridazin-3-il)-amid.
34. Spoj prema zahtjevu 18, naznačen time, da:
V is -C(O)-;
R2 je C3-C12heterociklil, C3-C12heterociklilalkil ili C3-C12heteroarilalkil, svaki nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, cijano, okso, tiokso, C1-C3alkil, -OR11, -C(O)R11, -OC(O)R11, -C(O)OR11, -C(O)N(R12)2 i C1-C6trihaloalkil;
R3 je fenil nesupstituiran ili supstituiran sljedećima: halo, C1-C6trihaloalkil ili C1C6trihaloalkoksi;
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C6cikloalkil, C7-C12aralkil, ili C6-C19aril (nesupstituiran ili supstituiran jednom ili više halo skupina); i
svaki R12 je neovisno odabran od vodika ili C1-C6alkila.
35. Spoj prema zahtjevu 34, naznačen time, da je odabran iz skupine koju čine sljedeći:
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina (2-okso-1,3-diaza-biciklo[3.1.0]heks-3-en-4-il)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karboksilna kiselina (5-okso-4,5-dihidro-1H-pirazol-3-il)amid;
5-[1,2]ditiolan-3-il-pentanoinska kiselina {6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-il}-amid;
6-[4-(2-trifluorometil-benzoil)-piperazin-1-il]-piridazin-3-karboksilna kiselina (2-tiofen-2-il-etil)-amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-benzo[1,3]dioksol-5-il-etil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2,2-difluoro-2-piridin-2-iletil)amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-piridin-2-iletil)amid; i
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (piridin-2-il-metil)amid.
36. Spoj prema zahtjevu 17, naznačen time, da:
x i y su svaki 1;
V je -C(O)-;
W je -C(O)N(R1)-;
R1 je vodik, metil ili etil;
R4i R5su svaki neovisno odabrani od sljedećih: vodik, fluoro, kloro, metil, metoksi ili trifluorometil; i
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila.
37. Spoj prema zahtjevu 36, naznačen time, da:
R2 je C3-C12cikloalkil ili C4-C12cikloalkilalkil, svaki nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine -OR11, C1-C3alkil, C1-C6trihaloalkil ili C6-C19aril;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, C1-C6trihaloalkil i C1-C6trihaloalkoksi; i
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C6cikloalkil, C6-C19aril ili C7-C12aralkil.
38. Spoj prema zahtjevu 37, naznačen time, da je odabran iz skupine koju čine sljedeći:
4-cikloheksil-N-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}butiramid;
2,2,3,3-tetrametilciklopropankarboksilna kiselina {6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}amid;
ciklopropankarboksilna kiselina {6-[4-(2-trifluorometil-benzoil)piperazin-1-il]piridazin-3-il}amid;
1-trifluorometilciklopropankarboksilna kiselina {6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}amid;
2-fenilciklopropankarboksilna kiselina (2-fenilciklopropankarbonil) {6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}amid; i
2-fenilciklopropankarboksilna kiselina {6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il} amid.
39. Spoj prema zahtjevu 36, naznačen time, da:
R2 je C1-C12alkil, C2-C12alkenil, C1-C6alkoksi ili C3-C12alkoksialkil, od kojih je svaki nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, cijano, okso, tiokso, C1-C3alkil, -OR11, -C(O)R11, -OC(O)R11, -C(O)OR11, -C(O)N(R12)2, -N(R12)2, C1-C6trihaloalkil,C3-C12cikloalkil i C6-C19aril;
R3 je fenil nesupstituiran ili supstituiran sa halo, C1-C6trihaloalkil ili C1-C6trihaloalkoksi;
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C6cikloalkil, C7-C12aralkil, ili C6-C19aril (nesupstituiran ili supstituiran jednom ili više halo skupina); i
svaki R12 je neovisno odabran od vodika ili C1-C6alkila.
40. Spoj prema zahtjevu 39, naznačen time, da je odabran iz skupine koju čine sljedeći:
2-benziloksi-N-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}acetamid;
2-etoksi-N-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}acetamid;
2-ciklopropilmetoksi-N-{6-[4-(2-trifluorometilbenzoil)-piperazin-1-il]piridazin-3-il}acetamid;
2-(2-metoksietoksi)-N-{6-[4-(2-trifluorometilbenzoil)-piperazin-1-il]piridazin-3-il}acetamid;
N-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}-2-(3,3,3-trifluoropropoksi)acetamid;
3-metoksi-N-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}propionamid;
3-fenoksi-N-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-il}propionamid;
2-butoksi-N-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}acetamid;
2-metil-1-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-ilkarbamoil}propilamin;
2-fenoksi-N-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}acetamid;
{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}karbaminska kiselina butil ester;
{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}karbaminska kiselina propil ester;
{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}karbaminska kiselina izobutil ester;
{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}karbaminska kiselina etil ester;
heksanoična kiselina {6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-il}amid;
4-fluoro-N-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-il}benzamid;
{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}karbaminska kiselina 3,3-dimetilbutil ester; i
{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}karbaminska kiselina 2-ciklopropiletil ester.
41. Spoj prema zahtjevu 36, naznačen time, da:
R2 je C7-C12aralkil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, cijano, okso, tiokso, C1-C3alkil, -OR11, -C(O)R11, -OC(O)R11, -C(O)OR11, -C(O)N(R12)2, -N(R12)2, C1-C6trihaloalkil, C3-C12cikloalkil i C6-C19aril;
R3 je fenil nesupstituiran ili supstituiran sa halo, C1-C6trihaloalkil ili C1-C6trihaloalkoksi;
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C6cikloalkil, C7-C12aralkil ili C6-C19aril (nesupstituiran ili supstituiran jednom ili više halo skupina); i
svaki R12 je neovisno odabran od vodika ili C1-C6alkila.
42. Spoj prema zahtjevu 41, naznačen time, da je odabran iz skupine koju čine sljedeći:
4-(4-metoksifenil)-N-{6-[4-(2-trifluorometilbenzoil)-piperazin-1-il]piridazin-3-il}butiramid; i
3-(4-fluorofenil)-N-{6-[4-(2-trifluorometilbenzoil)-piperazin-1-il]-piridazin-3-il}propionamid.
43. Spoj prema zahtjevu 19, naznačen time, da:
x i y su svaki 1;
V je -C(O)-;
W je -N(R1)C(O)-;
R1 je vodik, metil ili etil;
R2 je ciklopropiletil ili ciklopropilmetil;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine fluoro, kloro i trifluorometil;
R4 i R5 su svaki vodik; i
R6, R6a, R7, R7a, R8, R8a, R9, i R9a su svaki vodik.
44. Spoj prema zahtjevu 43, naznačen time, da je odabran iz skupine koju čine sljedeći:
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(5-fluoro-2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid; i
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina ciklopropilmetilamid.
45. Spoj prema zahtjevu 21, naznačen time, da:
x i y su svaki 1;
V je -C(O)-;
W je -N(R1)C(O)-;
R1 je vodik, metil ili etil;
R2je C1-C6alkil nesupstituiran ili supstituiran sa -C(O)OR11;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine fluoro, kloro i trifluorometil;
R4 i R5 su svaki vodik;
R6, R6a, R7, R7a, R8, R8a, R9, i R9a su svaki vodik; i
R11 je vodik, metil, etil ili 1,1-dimetiletil.
46. Spoj prema zahtjevu 45, naznačen time, da je odabran iz skupine koju čine sljedeći:
4-metil-2-({6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-karbonil}amino)pentanoinska kiselina metilester;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-metilbutil)amid;
6-[4-(5-fluoro-2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-metilbutil)amid;
6-[4-(4-fluoro-2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-metilbutil)amid; i
4-metil-2-({6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karbonil}amino)pentanoinska kiselina.
47. Spoj prema zahtjevu 25, naznačen time, da:
x i y su svaki 1;
V je -C(O)-;
W je -N(R1)C(O)-;
R1 je vodik, metil ili etil;
R2 je 2-feniletil ili 3-fenilpropil gdje je fenilna skupina nesupstituirana ili supstituirana jednim ili više supstituenata neovisno odabranih od kloro, fluoro ili -OR11;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine fluoro, kloro i trifluorometil;
R4 i R5 su svaki vodik;
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki vodik; i
R11 je vodik, metil, etil ili 1,1-dimetiletil.
48. Spoj prema zahtjevu 47, naznačen time, da je odabran iz skupine koju čine sljedeći:
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina fenetilamid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina [2-(4-metoksifenil)etil]amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina [2-(3-fluorofenil)etil]amid;
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-fenilpropil)amid; i
6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-karboksilna kiselina [2-(4-fluorofenil)etil]amid.
49. Spoj prema zahtjevu 37, naznačen time, da:
x i y su svaki 1;
V je -C(O)-;
W je -C(O)N(R1)-;
R1 je vodik, metil ili etil;
R2 je ciklopropiletil, ciklopropilmetil ili ciklopentiletil;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine fluoro, kloro i trifluorometil;
R4i R5su svaki neovisno odabrani od sljedećih: vodik, fluoro, kloro, metil, metoksi ili trifluorometil; i
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki vodik.
50. Spoj prema zahtjevu 49, naznačen time, da je to
3-ciklopentil-N-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il} propionamid.
51. Spoj prema zahtjevu 39, naznačen time, da:
x i y su svaki 1;
V je -C(O)-;
W je -C(O)N(R1)-;
R1 je vodik, metil ili etil;
R2 je C1-C6alkil;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine fluoro, kloro i trifluorometil;
R4i R5su svaki neovisno odabrani od sljedećih: vodik, fluoro, kloro, metil, metoksi ili trifluorometil; i
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki vodik.
52. Spoj prema zahtjevu 51, naznačen time, da je to
4-metilpentanoinska kiselina {6-[4-(2-trifluorometilbenzoil)-piperazin-1-il]piridazin-3-il}amid.
53. Spoj prema zahtjevu 41, naznačen time, da:
x i y su svaki 1;
V je -C(O)-;
W je -C(O)N(R1)-;
R1 je vodik, metil ili etil;
R2 je 3-fenilpropil;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine fluoro, kloro i trifluorometil;
R4i R5su svaki neovisno odabrani od sljedećih: vodik, fluoro, kloro, metil, metoksi ili trifluorometil; i
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki vodik.
54. Spoj prema zahtjevu 53, naznačen time, da je to
4-fenil-N-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}butiramid.
55. Spoj prema zahtjevu 1, naznačen time, da:
x i y su svaki neovisno 1;
W je -N(R1)C(O)N(R1)-;
V je -C(O)-;
svaki R1 je neovisno odabran iz skupine koju čine vodik; C1-C6alkil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, metil ili trifluorometil; i C2-C6alkil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine metoksi i hidroksi;
R2 je odabran iz skupine koju čine C1-C12alkil, C2-C12alkenil, C2-C12hidroksialkil, C2-C12hidroksialkenil, C2-C12alkoksialkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C3-C12heterociklil, C3-C12heterociklilalkil, C6-C19aril, C7-C12aralkil, C1-C12heteroaril i C3-C12heteroarilalkil; ili
R2 je višeprstenasta struktura koja ima 2 do 4 prstena, gdje su prsteni neovisno odabrani iz skupine koju čine C3-C12cikloalkil, C3-C12heterociklil, C6-C19aril i C1-C12heteroaril, pri čemu neki ili svi prsteni mogu biti stopljeni jedan s drugim;
R3 je odabran iz skupine koju čine C1-C12alkil, C2-C12alkenil, C2-C12hidroksialkil, C2-C12 hidroksialkenil, C1-C12alkoksi, C2-C12alkoksialkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril i C3-C12heteroarilalkil; ili
R3 je višeprstenasta struktura koja ima 2 do 4 prstena, gdje su prsteni neovisno odabrani iz skupine koju čine C3-C12cikloalkil, C3-C12heterociklil, C6-C19aril i C1-C12heteroaril, pri čemu neki ili svi prsteni mogu biti stopljeni jedan s drugim;
R4i R5su svaki neovisno odabrani od sljedećih: vodik, fluoro, kloro, metil, metoksi ili trifluorometil;
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila; ili R6 i R6a zajedno, ili R9 i R9a zajedno su okso skupina, dok preostali R6, R6a, R7, R7a, R8,
R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila; ili
jedan od R6, R6a, R7 i R7a zajedno s jednim od R8, R8a, R9 i R9atvore alkilenski most, dok preostali R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila;
njegov stereoizomer, enantiomer ili tautomer, njegova farmaceutski prihvatljiva sol, ili njegov farmaceutski sastav.
56. Spoj prema zahtjevu 55, naznačen time, da:
x i y su svaki 1;
svaki R1 je vodik ili C1-C6alkil;
R2 je odabran iz skupine koju čine C3-C12alkil, C3-C12alkenil, C3-C12hidroksialkil, C3-C12hidroksialkenil, C3-C12alkoksialkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C3-C12heterociklil, C3-C12heterociklilalkil, C6-C19aril, C7-C12aralkil, C1-C12heteroaril i C3-C12heteroarilalkil;
svaki R2 je nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, okso, tiokso, C1-C3alkil, -OR11, -C(O)OR11, C1-C6trihaloalkil, C3-C12cikloalkil,C3-C12heterociklil, C6-C19aril, C1-C12heteroaril i C1-C12heteroarilC3-C12cikloalkil;
R3 je odabran iz skupine koju čine C3-C12alkil, C3-12alkenil, C3-C12hidroksialkil, C3-C12 hidroksialkenil, C3-C12alkoksi, C3-C12alkoksialkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril i C3-C12heteroarilalkil;
gdje svaka od gornjih R3 skupina je nesupstituirana ili supstituirana jednim ili više supstituenata odabranih iz skupine koju čine C1-C6alkil, C1-C6trihaloalkil, C1-C6trihaloalkoksi, C1-C6alkoksi, C1-C6alkilsulfonil, halo, cijano, nitro, hidroksi, -N(R12)2, -C(O)OR11, -S(O)2N(R12)2, C3-C12cikloalkil, C3-C12heterociklil, C6-C19aril, C1C12heteroaril i C1-C12heteroarilC1-C12cikloalkil;
R4 i R5 su svaki neovisno odabrani od sljedećih: vodik, fluoro, kloro, metil, metoksi ili trifluorometil;
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila; ili
R6 i R6a zajedno ili R7 i R7a zajedno su okso skupina, dok preostali R6, R6a, R7, R7a, R8, R8a,
R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila; ili
jedan od R6, R6a, R7 i R7a zajedno s jednim od R8, R8a, R9 i R9a tvore alkilenski most, dok preostali R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila;
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C6cikloalkil, C6-C19aril ili C7-C12aralkil; i
svaki R12 je neovisno odabran od vodika ili C1-C6alkila.
57. Spoj prema zahtjevu 56, naznačen time, da:
R2 je C3-C12cikloalkil ili C4-C12cikloalkilalkil, svaki nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine -OR11, C1-C3alkil ili C6-C19aril;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, C1-C6trihaloalkil i C1-C6trihaloalkoksi; i
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C6cikloalkil, C6-C19aril ili C7-C12aralkil.
58. Spoj prema zahtjevu 57, naznačen time, da je odabran iz skupine koju čine sljedeći:
1-(2-fenilciklopropil)-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea;
1-ciklopentil-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-il}urea;
1-(3-ciklopropilpropil)-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea;
1-ciklopropilmetil-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea;
1-(2-ciklopropiletil)-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea;
1-(2-ciklopropiletil)-3-{6-[4-(2-fluoro-6-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea;
1-(2-ciklopropiletil)-3-{6-[4-(5-fluoro-2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea;
1-cikloheksil-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea;
1-(2-ciklopropiletil)-3-{6-[4-(2,6-difluorobenzoil)piperazin-1-il]piridazin-3-il}urea; i
1-(3-ciklopropilpropil)-3-{6-[4-(5-fluoro-2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea.
59. Spoj prema zahtjevu 56, naznačen time, da:
R2 je C7-C12aralkil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, -OR11 ili C1-C3alkil;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, C1-C6trihaloalkil i C1-C6trihaloalkoksi; i
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C6cikloalkil, C6-C19aril ili C7-C12aralkil.
60. Spoj prema zahtjevu 59, naznačen time, da je odabran iz skupine koju čine sljedeći:
1-[1-(4-fluorofenil)etil]-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il)urea;
1-[1-(4-fluorofenil)etil]-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea;
1-[3-(4-fluorofenil)propil]-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea;
1-fenetil-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-il}urea;
1-(4-fluorobenzil)-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea; i
1-(3,4-diklorobenzil)-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea.
61. Spoj prema zahtjevu 56, naznačen time, da:
R2 je C6-C19aril nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, -OR11 ili C1-C3alkil;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, C1-C6trihaloalkil i C1-C6trihaloalkoksi; i
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C6cikloalkil, C6-C19aril ili C7-C12aralkil.
62. Spoj prema zahtjevu 61, naznačen time, da je odabran iz skupine koju čine sljedeći:
1-(4-fluorofenil)-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-il}urea; i
1-(2-fluorofenil)-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea.
63. Spoj prema zahtjevu 56, naznačen time, da:
R2 je C3-C12alkil, C3-C12hidroksialkil ili C3-C12alkoksialkil, svaki nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, -OR11 ili -C(O)OR11;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, C1-C6trihaloalkil i C1-C6trihaloalkoksi; i
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C6cikloalkil, C6-C19aril ili C7-C12aralkil.
64. Spoj prema zahtjevu 63, naznačen time, da je odabran iz skupine koju čine sljedeći:
3-(3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]-piridazin-3-il}ureido)propionska kiselina etil ester;
1-butil-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea;
1-(2-kloroetil)-3-{6-[4-(2-trifluorometilbenzoil)-piperazin-1-il]piridazin-3-il}urea;
1-{6-[4-(2,6-difluorobenzoil)piperazin-1-il]piridazin-3-il}-3-(3-metilbutil)urea;
1-(3,3-dimetilbutil)-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea;
1-(2-izopropoksietil)-3-{6-[4-(2-trifluorometilbenzoil)-piperazin-1-il]piridazin-3-il}urea;
1-(3-hidroksi-4,4-dimetilpentil)-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea; 1-heksil-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea;
1-heptil-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea; i
1-(4-metilpentil)-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea.
65. Spoj prema zahtjevu 59, naznačen time, da:
x i y su svaki 1;
svaki R1 je vodik, metil ili etil;
R2 je benzil;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine fluoro, kloro i trifluorometil;
R4i R5su svaki neovisno odabrani od sljedećih: vodik, fluoro, kloro, metil, metoksi ili trifluorometil; i
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki vodik.
66. Spoj prema zahtjevu 65, naznačen time, da je to
1-benzil-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea.
67. Spoj prema zahtjevu 63, naznačen time, da:
x i y su svaki 1;
svaki R1 je vodik, metil ili etil;
R2 je pentil;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine fluoro, kloro i trifluorometil;
R4i R5su svaki neovisno odabrani od sljedećih: vodik, fluoro, kloro, metil, metoksi ili trifluorometil; i
R6, R6a , R7, R7a , R8, R8a, R9 i R9a su svaki vodik.
68. Spoj prema zahtjevu 67, naznačen time, da je to
1-pentil-3-{6-[4-(2-trifluorometilbenzoil)piperazin-1-il]piridazin-3-il}urea.
69. Spoj prema zahtjevu 1, naznačen time, da:
x i y su svaki neovisno 1;
W je -C(O)N(R1)-, -N(R1)C(O)N(R1)- ili -N(R1)C(O)-;
V je -C(R10)H;
svaki R1 je neovisno odabran iz skupine koju čine vodik; C1-C6alkil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, metil ili trifluorometil; i C2-C6alkil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine metoksi i hidroksi;
R2 je odabran iz skupine koju čine C7-C12alkil, C2-C12alkenil, C7-C12hidroksialkil, C2-C12hidroksialkenil, C1-C12alkoksi, C2-C12alkoksialkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C13-C19aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril i C3-C12heteroarilalkil;
R3 je odabran iz skupine koju čine C1-C12alkil, C2-C12alkenil, C2-C12hidroksialkil, C2-C12hidroksialkenil, C1-C12alkoksi, C2-C12alkoksialkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril i C3-C12heteroarilalkil;
R4 i R5 su svaki neovisno odabrani od sljedećih: vodik, fluoro, kloro, metil, metoksi, trifluorometil, cijano, nitro ili -N(R12)2;
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila;
ili R6 i R6a zajedno, ili R7 i R7a zajedno, ili R8 i R8a zajedno, ili R9 i R9a zajedno su okso skupina, dok preostali R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila; ili
jedan od R6, R6a, R7 i R7a zajedno s jednim od R8, R8a, R9 i R9a tvore alkilenski most, dok preostali R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila;
R10 je vodik ili C1-C3alkil; i
svaki R12 je neovisno odabran od vodika ili C1-C6alkila; međutim uz uvjet da R2ne može biti pirazinil, piridinonil, pirolidinonil ili imidazolil;
njegov stereoizomer, enantiomer ili tautomer, njegova farmaceutski prihvatljiva sol, ili njegov farmaceutski sastav.
70. Spoj prema zahtjevu 69, naznačen time, da:
x i y su svaki neovisno 1;
W je -N(R1)C(O)-;
svaki R1 je vodik ili C1-C6alkil;
R2 je odabran iz skupine koju čine C7-C12alkil, C2-C12alkenil, C7-C12hidroksialkil, C2-C12hidroksialkenil, C1-C12alkoksi, C2-C12alkoksialkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C13-C19aralkil, C1-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril i C3-C12heteroarilalkil;
svaki R2 je nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, cijano, okso, tiokso, C1-C3alkil, -OR11, -C(O)R11, -OC(O)R11, -C(O)OR11, -C(O)N(R12)2, -N(R12)2, C1-C6trihaloalkil, C3-C12cikloalkil, C3-C12heterociklil, C6-C19aril, C1-C12heteroaril i C1-C12heteroarilC3-C12cikloalkil;
R3 je odabran iz skupine koju čine C1-C12alkil, C2-C12alkenil, C2-C12hidroksialkil, C2-C12hidroksialkenil, C1-C12alkoksi, C2-C12alkoksialkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril i C3-C12heteroarilalkil;
svaki R3 je nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, cijano, nitro, hidroksi, C1-C6alkil, C1-C6trihaloalkil, C1-C6trihaloalkoksi, C1-C6alkilsulfonil, -N(R12)2, -OC(O)R11, -C(O)OR11, -S(O)2N(R12)2, C3-C12cikloalkil, C3-C12heterociklil i C1-C12heteroarilC3-C12cikloalkil;
R4 i R5 su svaki neovisno odabrani od sljedećih: vodik, fluoro, kloro, metil, metoksi, trifluorometil, cijano, nitro ili -N(R12)2;
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila;
R10 je vodik ili C1-C3alkil;
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C6cikloalkil, C6-C19aril ili C7-C12aralkil; i
svaki R12 je neovisno odabran od vodika ili C1-C6alkila.
71. Spoj prema zahtjevu 70, naznačen time, da:
R2 je C3-C12cikloalkil ili C4-C12cikloalkilalkil, svaki nesupstituiran ili supstituiran jednim ili
više supstituenata odabranih iz skupine koju čine halo, C1-C6trihaloalkil, -OR11, C1-C3alkil ili C6-C19aril;
R3 je fenil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, cijano, nitro, hidroksi, C1-C6alkil, C1-C6trihaloalkil, C1-C6trihaloalkoksi, C1-C6alkilsulfonil, -N(R12)2, -OC(O)R11, -C(O)OR11, -S(O)2N(R12)2 i C3-C12cikloalkil;
svaki R11 je neovisno odabran od sljedećih: vodik, C1-C6alkil, C3-C6cikloalkil, C6-C19aril ili C7-C12aralkil; i
svaki R12 je neovisno odabran od vodika ili C1-C6alkila.
72. Spoj prema zahtjevu 71, naznačen time, da je odabran iz skupine koju čine sljedeći:
6-[4-(2-trifluorometilbenzil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(5-fluoro-2-trifluorometilbenzil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(4-fluoro-2-trifluorometilbenzil)-piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(5-kloro-2-trifluorometilbenzil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2-kloro-4-fluorobenzil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2,5-diklorobenzil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(2,4-diklorobenzil)piperazin-1-il]piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid;
6-[4-(5-fluoro-2-trifluorometilbenzil)piperazin-1-il]piridazin-3-karboksilna kiselina (3-ciklopropilpropil)amid; i
6-{4-[1-(2-trifluorometilfenil)etil]piperazin-1-il}-piridazin-3-karboksilna kiselina (2-ciklopropiletil)amid.
73. Spoj prema zahtjevu 1, naznačen time, da:
x i y su svaki neovisno 1;
W je -C(O)N(R1)-, -N(R1)C(O)N(R1)- ili -N(R1)C(O)-;
V je -C(R10)H;
svaki R1 je neovisno odabran iz skupine koju čine vodik; C1-C6alkil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine halo, metil ili trifluorometil; i C2-C6alkil nesupstituiran ili supstituiran jednim ili više supstituenata odabranih iz skupine koju čine metoksi i hidroksi;
R2 je odabran iz skupine koju čine C1-C12alkil, C2-C12alkenil, C2-C12hidroksialkil, C2-C12hidroksialkenil, C1-C12alkoksi, C2-C12alkoksialkil, C3-C12cikloalkil, C4-C12cikloalkilalkil, C6-C19aril, C7-C12aralkil, C3-C12heterociklil, C3-C12heterociklilalkil, C1-C12heteroaril i C3-C12heteroarilalkil;
R3 je odabran iz skupine koju čine C1-C12alkil, C2-C12alkenil, C2-C12hidroksialkil, C2-C12hidroksialkenil, C1-C12alkoksi ili C2-C12alkoksialkil;R4 i R5 su svaki neovisno odabrani od sljedećih: vodik, fluoro, kloro, metil, metoksi, trifluorometil, cijano, nitro ili -N(R12)2;
R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila;
ili R6 i R6a zajedno, ili R7 i R7a zajedno, ili R8 i R8a zajedno, ili R9 i R9a zajedno su okso skupina, dok preostali R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila; ili
jedan od R6, R6a, R7 i R7a zajedno s jednim od R8, R8a, R9 i R9a tvore alkilenski most, dok preostali R6, R6a, R7, R7a, R8, R8a, R9 i R9a su svaki neovisno odabrani od vodika ili C1-C3alkila;
R10 je vodik ili C1-C3alkil; i
svaki R12 je neovisno odabran od vodika ili C1-C6alkila;
njegov stereoizomer, enantiomer ili tautomer, njegova farmaceutski prihvatljiva sol, ili njegov farmaceutski sastav.
74. Farmaceutski sastav, naznačen time, da obuhvaća farmaceutski prihvatljivo pomoćno sredstvo i terapeutski učinkovitu količinu spoja prema bilo kojem od zahtjeva 1 do 73.
75. Spoj prema bilo kojem od zahtjeva 1 do 73, naznačen time, da se koristi za liječenje bolesti ili stanja posredovanih stearoil-CoA desaturazom (SCD) kod sisavaca.
76. Spoj prema zahtjevu 75, naznačen time, da sisavac je čovjek.
77. Spoj prema zahtjevu 76, naznačen time, da bolest ili stanje je odabrana/odabrano iz skupine koju čine dijabetes tipa II, smanjena tolerancija glukoze, rezistentnost inzulina, pretilost, masna jetra, ne-alkoholični steatohepatitis, dislipidemija, akne i metabolički sindrom te bilo koja kombinacija navedenih.
78. Spoj prema zahtjevu 77, naznačen time, da bolest ili stanje je dijabetes tipa II.
79. Spoj prema zahtjevu 77, naznačen time, da bolest ili stanje je pretilost.
80. Spoj prema zahtjevu 77, naznačen time, da bolest ili stanje je metabolički sindrom.
81. Spoj prema zahtjevu 77, naznačen time, da bolest ili stanje je masna jetra.
82. Spoj prema zahtjevu 77, naznačen time, da bolest ili stanje je ne-alkoholični steatohepatitis.
83. Uporaba spoja prema bilo kojem od zahtjeva 1 do 73, naznačena time, da je za proizvodnju lijeka za liječenje bolesti ili stanja posredovanih stearoil-CoA desaturazom (SCD) kod sisavaca.
84. Uporaba prema zahtjevu 83, naznačena time, da sisavac je čovjek.
85. Uporaba prema zahtjevu 84, naznačena time, da bolest ili stanje je odabrana/odabrano iz skupine koju čine dijabetes tipa II, smanjena tolerancija glukoze, rezistentnost inzulina, pretilost, masna jetra, ne-alkoholični steatohepatitis, dislipidemija, akne i metabolički sindrom te bilo koja kombinacija navedenih.
86. Uporaba prema zahtjevu 85, naznačena time, da bolest ili stanje je dijabetes tipa II.
87. Uporaba prema zahtjevu 85, naznačena time, da bolest ili stanje je pretilost.
88. Uporaba prema zahtjevu 85, naznačena time, da bolest ili stanje je metabolički sindrom.
89. Uporaba prema zahtjevu 85, naznačena time, da bolest ili stanje je masna jetra.
90. Uporaba prema zahtjevu 85, naznačena time, da bolest ili stanje je ne-alkoholični steatohepatitis.
Applications Claiming Priority (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US49109503P | 2003-07-30 | 2003-07-30 | |
US54689804P | 2004-02-23 | 2004-02-23 | |
US54678604P | 2004-02-23 | 2004-02-23 | |
US54681504P | 2004-02-23 | 2004-02-23 | |
US54682004P | 2004-02-23 | 2004-02-23 | |
US54693404P | 2004-02-23 | 2004-02-23 | |
US55340304P | 2004-03-16 | 2004-03-16 | |
US55349104P | 2004-03-16 | 2004-03-16 | |
US55341604P | 2004-03-16 | 2004-03-16 | |
US55344604P | 2004-03-16 | 2004-03-16 | |
US55340404P | 2004-03-16 | 2004-03-16 | |
PCT/US2004/024548 WO2005011655A2 (en) | 2003-07-30 | 2004-07-29 | Pyridazine derivatives and their use as therapeutic agents |
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 (hr) |
EP (3) | EP1648874B1 (hr) |
JP (1) | JP4808616B2 (hr) |
KR (1) | KR100934554B1 (hr) |
AR (1) | AR047557A1 (hr) |
AT (1) | ATE527242T1 (hr) |
AU (2) | AU2004261252C1 (hr) |
CA (1) | CA2533899C (hr) |
CY (1) | CY1112178T1 (hr) |
DK (1) | DK1648874T3 (hr) |
EC (1) | ECSP066313A (hr) |
ES (2) | ES2568769T3 (hr) |
HK (2) | HK1097256A1 (hr) |
HR (1) | HRP20110974T1 (hr) |
IL (1) | IL173395A (hr) |
MA (1) | MA28011A1 (hr) |
NO (1) | NO332822B1 (hr) |
NZ (1) | NZ545265A (hr) |
PL (1) | PL1648874T3 (hr) |
PT (1) | PT1648874E (hr) |
TN (1) | TNSN06034A1 (hr) |
TW (2) | TW201038270A (hr) |
WO (1) | WO2005011655A2 (hr) |
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 |
US20050119251A1 (en) * | 2001-12-21 | 2005-06-02 | Jian-Min Fu | Nicotinamide derivatives and their use as therapeutic agents |
US7390813B1 (en) * | 2001-12-21 | 2008-06-24 | Xenon Pharmaceuticals Inc. | Pyridylpiperazines and aminonicotinamides and their use as therapeutic agents |
EP2316826A1 (en) * | 2003-07-30 | 2011-05-04 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutics agents |
NZ545265A (en) | 2003-07-30 | 2009-11-27 | Xenon Pharmaceuticals Inc | Pyridazine derivatives and their use for treating diseases mediated by stearoyl-CoA desaturase (SCD) enzymes |
US7759348B2 (en) * | 2003-07-30 | 2010-07-20 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
SG145701A1 (en) * | 2003-07-30 | 2008-09-29 | Xenon Pharmaceuticals Inc | Piperazine derivatives and their use as therapeutic agents |
US7754711B2 (en) | 2003-07-30 | 2010-07-13 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
JP2007518816A (ja) * | 2004-01-23 | 2007-07-12 | アムジエン・インコーポレーテツド | バニロイド受容体リガンド及び炎症性及び神経因性疼痛の治療におけるこれらの使用 |
US7592343B2 (en) * | 2004-09-20 | 2009-09-22 | Xenon Pharmaceuticals Inc. | Pyridazine-piperazine compounds and their use as stearoyl-CoA desaturase inhibitors |
CN101084212A (zh) * | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为硬脂酰CoA去饱和酶介导剂的用途 |
MX2007003321A (es) * | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como agentes terapeuticos. |
EP2316458A1 (en) * | 2004-09-20 | 2011-05-04 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-coa-desaturase |
EP2289510A1 (en) | 2004-09-20 | 2011-03-02 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes |
WO2006034440A2 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
US20080167321A1 (en) * | 2004-09-20 | 2008-07-10 | Xenon Pharmaceuticals Inc. | Pyridine Derivatives For Inhibiting Human Stearoyl-Coa-Desaturase |
CN101084207A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为硬脂酰CoA去饱和酶抑制剂的用途 |
BRPI0515477A (pt) * | 2004-09-20 | 2008-07-22 | Xenon Pharmaceuticals Inc | derivados heterocìclicos bicìclicos e o uso dos mesmos como inibidores de estaroil-coa-desaturase (scd) |
GT200600046A (es) * | 2005-02-09 | 2006-09-25 | Terapia de combinacion | |
WO2007044085A2 (en) * | 2005-05-19 | 2007-04-19 | Xenon Pharmaceuticals Inc. | Heteroaryl compounds and their uses as therapeutic agents |
WO2006125180A1 (en) * | 2005-05-19 | 2006-11-23 | Xenon Pharmaceuticals Inc. | Piperazine derivatives and their uses as therapeutic agents |
WO2006125179A1 (en) * | 2005-05-19 | 2006-11-23 | Xenon Pharmaceuticals Inc. | Tricyclic compounds and their uses as therapeutic agents |
CN101208089A (zh) * | 2005-06-03 | 2008-06-25 | 泽农医药公司 | 氨基噻唑衍生物作为人硬酯酰-CoA去饱和酶抑制剂 |
WO2007005763A2 (en) * | 2005-07-01 | 2007-01-11 | Novartis Ag | Combination of a renin inhibitor and an insulin secretion enhancer or an insulin sensitizer |
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 (en) * | 2006-05-19 | 2007-11-29 | Xenon Pharmaceuticals Inc. | Macrocyclic compounds and their uses as stearoyl-coa desaturase |
CN101460476B (zh) | 2006-06-05 | 2013-12-04 | 诺瓦提斯公司 | 有机化合物 |
US8314138B2 (en) | 2006-08-24 | 2012-11-20 | Novartis Ag | Pyrazole derivative as SCD1 inhibitors for the treatment of diabetes |
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 |
EP2099755A2 (en) * | 2006-11-20 | 2009-09-16 | Glenmark Pharmaceuticals S.A. | Acetylene derivatives as stearoyl coa desaturase inhibitors |
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 |
WO2008104524A1 (en) * | 2007-02-28 | 2008-09-04 | Smithkline Beecham Corporation | Thiadiazole derivatives, inhibitors of stearoyl-coa desaturase |
JP5431305B2 (ja) | 2007-04-23 | 2014-03-05 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 高速解離性ドパミン2受容体アンタゴニストとしての4−アルコキシピリダジン誘導体 |
AU2008240729B2 (en) | 2007-04-23 | 2012-08-23 | Janssen Pharmaceutica N.V. | Thia(dia)zoles as fast dissociating dopamine 2 receptor antagonists |
CA2833209C (en) * | 2007-04-27 | 2016-06-28 | Purdue Pharma L.P. | Piperidine and piperazine compounds as trpv1 antagonists |
EP2581081A3 (en) | 2007-06-01 | 2013-07-31 | The Trustees Of Princeton University | Treatment of viral infections by modulation of host cell metabolic pathways |
WO2008157844A1 (en) | 2007-06-21 | 2008-12-24 | Forest Laboratories Holdings Limited | Novel piperazine derivatives as inhibitors of stearoyl-coa desaturase |
CN101821234B (zh) | 2007-08-08 | 2014-06-25 | 格里斯威医药有限责任公司 | 苯氧基吡咯烷衍生物及其应用和组合物 |
WO2009037542A2 (en) | 2007-09-20 | 2009-03-26 | Glenmark Pharmaceuticals, S.A. | Spirocyclic compounds as stearoyl coa desaturase inhibitors |
BRPI0817211A2 (pt) | 2007-09-20 | 2017-05-16 | Irm Llc | composto composições como moduladores da atividade de gpr119 |
BRPI0820972A2 (pt) * | 2007-12-11 | 2018-08-14 | Hoffmann La Roche | compostos inibidores de estearoil-coa dessaturase 1, processo para a sua preparação, composição farmacêutica que compreende, uso dos mesmos e método para o tratamento e profilaxia de obesidade. |
DK2307374T3 (en) | 2008-07-31 | 2017-05-01 | Janssen Pharmaceutica Nv | PIPERAZIN-1-YLTRIFLUORMETHYL-SUBSTITUTED PYRIDINES AS QUICK DISSOCATING DOPAMIN-2 RECEPTOR ANTAGONISTS |
EP2398809B1 (en) | 2009-02-17 | 2015-07-08 | Merck Canada Inc. | Novel spiro compounds useful as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
EP2459568A4 (en) | 2009-07-28 | 2013-02-27 | Merck Frosst Canada Ltd | NOVEL SPIRO COMPOUNDS USEFUL AS DELTA-9 DEATURASE STEAROYL COENZYME INHIBITORS |
WO2011014520A2 (en) | 2009-07-29 | 2011-02-03 | Irm Llc | Compounds and compositions as modulators of gpr119 activity |
US20130012709A1 (en) | 2009-09-10 | 2013-01-10 | Centre National De La Recherche Scientifique | NOVEL INHIBITORS OF STEAROYL-CoA-DESATURASE-1 AND THEIR USES |
KR20120092629A (ko) | 2009-10-09 | 2012-08-21 | 아이알엠 엘엘씨 | Gpr119 활성의 조절제로서의 화합물 및 조성물 |
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 |
UA113288C2 (xx) | 2011-06-22 | 2017-01-10 | Trpv1 антагоністи, що містять дигідроксизамісник, і їх застосування | |
CA2850836A1 (en) | 2011-10-15 | 2013-04-18 | Genentech, Inc. | Methods of using scd1 antagonists |
US9260441B2 (en) | 2012-03-28 | 2016-02-16 | Intervet Inc. | Heteroaryl compounds with cyclic bridging unit |
RU2014149559A (ru) | 2012-05-22 | 2016-06-27 | Ийсум Рисёч Девелопмент Кампани Оф Зэ Хибру Юниверсити Оф Иерусалим Лтд. | Селективные ингибиторы недифференцированных клеток |
WO2014052619A1 (en) | 2012-09-27 | 2014-04-03 | Irm Llc | Piperidine derivatives and compositions as modulators of gpr119 activity |
EP3350165B1 (en) | 2015-09-16 | 2023-07-26 | Organovo, Inc. | Farnesoid x receptor agonists and uses thereof |
US11970486B2 (en) | 2016-10-24 | 2024-04-30 | Janssen Pharmaceutica Nv | Compounds and uses thereof |
AU2018205275B2 (en) | 2017-01-06 | 2024-05-02 | Janssen Pharmaceutica Nv | Methods for the treatment of neurological disorders |
US10961198B2 (en) | 2017-03-15 | 2021-03-30 | Metacrine, Inc. | Farnesoid X receptor agonists and uses thereof |
IL269065B (en) | 2017-03-15 | 2022-09-01 | Metacrine Inc | Paranoid x receptor agonists and uses thereof |
WO2019084157A1 (en) | 2017-10-24 | 2019-05-02 | Yumanity Therapeutics, Inc. | COMPOUNDS AND USES THEREOF |
PE20211496A1 (es) * | 2018-05-09 | 2021-08-11 | Lg Chemical Ltd | Nuevo compuesto que presenta actividad inhibidora de enteropeptidasa |
MA53665A (fr) | 2018-09-18 | 2021-07-28 | Metacrine Inc | Agonistes du récepteur farnésoïde x et leurs utilisations |
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. |
KR890700581A (ko) | 1987-04-03 | 1989-04-25 | 로버어트 에이 아미테이지 | 아미노 -9,10-세코스테로이드 |
CA1338012C (en) | 1987-04-27 | 1996-01-30 | John Michael Mccall | Pharmaceutically active amines |
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 (de) | 1991-06-19 | 1992-12-30 | Hoechst Aktiengesellschaft | Chirale Azetidinon-Derivate und ihre Verwendung als Dotierstoffe in Flüssigkristallmischungen |
DE4302051A1 (de) | 1993-01-26 | 1994-07-28 | Thomae Gmbh Dr K | 5-gliedrige Heterocyclen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
AU717744B2 (en) * | 1996-01-15 | 2000-03-30 | Janssen Pharmaceutica N.V. | 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 (en) | 1997-06-27 | 1999-01-07 | Resolution Pharmaceuticals Inc. | Dopamine d4 receptor ligands |
DK1064273T3 (da) | 1998-03-19 | 2003-03-31 | Upjohn Co | 1,3,4-Thiadiazoler, som er nyttige til behandling af CMV-infektioner |
CA2348022A1 (en) * | 1998-10-21 | 2000-04-27 | Takeda Chemical Industries, Ltd. | Condensed pyridazine derivatives, their production and use |
EP1126833A4 (en) | 1998-10-29 | 2004-09-08 | Trega Biosciences Inc | OXADIAZOLE, THIADIAZOLE AND TRIAZOLE DERIVATIVES AND COMBINATORIAL LIBRARIES CONTAINING THESE DERIVATIVES |
WO2000044743A1 (fr) | 1999-01-28 | 2000-08-03 | Nippon Shinyaku Co., Ltd. | Derives d'amides et compositions de medicaments |
JP4676062B2 (ja) | 1999-01-29 | 2011-04-27 | アボット・ラボラトリーズ | ニコチン性アセチルコリン受容体リガンドとしてのジアザ2環式誘導体 |
DK1394150T3 (da) | 1999-02-24 | 2011-03-21 | Hoffmann La Roche | 4-phenylpyridinderivater og deres anvendelse som NK-1-receptorantagonister |
KR20020005662A (ko) | 1999-04-09 | 2002-01-17 | 기따자또 이찌로 | 질소함유 복소환화합물 및 벤즈아미드화합물 및 그 것을함유해서 되는 의약 |
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 |
AU1887401A (en) | 1999-12-14 | 2001-06-25 | Nippon Shinyaku Co. Ltd. | Medicinal composition |
EP2172560A3 (en) * | 2000-02-24 | 2010-09-29 | Xenon Pharmaceuticals Inc. | stearoyl-coa desaturase to identify triglyceride reducing therapeutic agents |
CA2403017A1 (en) | 2000-03-15 | 2001-09-20 | Warner-Lambert Company | 5-amide substituted diarylamines as mex inhibitors |
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 |
ATE374765T1 (de) * | 2000-07-27 | 2007-10-15 | Lilly Co Eli | Substituierte heterocyclische amide |
WO2002026944A2 (en) | 2000-09-26 | 2002-04-04 | Xenon Genetics, Inc. | METHODS AND COMPOSITIONS EMPLOYING A NOVEL STEAROYL-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 |
MXPA03010612A (es) * | 2001-05-22 | 2004-04-02 | Neurogen Corp | Ligandos receptores de la hormona concentradora de melanina: analogos de 1-bencil-4-aril piperazina substiruidos. |
KR20040010713A (ko) * | 2001-06-15 | 2004-01-31 | 야마노우치세이야쿠 가부시키가이샤 | 페닐피리딘 카보닐 피페라진 유도체 |
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 |
JPWO2003037862A1 (ja) | 2001-10-30 | 2005-02-17 | 日本新薬株式会社 | アミド誘導体及び医薬 |
US6620811B2 (en) | 2001-11-19 | 2003-09-16 | Hoffmann-La Roche Inc. | Isonicotin- and nicotinamide derivatives of benzothiazoles |
JP2005510564A (ja) | 2001-11-28 | 2005-04-21 | 藤沢薬品工業株式会社 | アポリポタンパク質b阻害剤としての複素環式アミド化合物 |
WO2003050088A1 (en) | 2001-12-07 | 2003-06-19 | Eli Lilly And Company | Substituted heterocyclic carboxamides with antithrombotic activity |
IL162859A0 (en) | 2002-02-05 | 2005-11-20 | Novo Nordisk As | Novel aryl-and heteroarylpiperazines |
CN101450934B (zh) | 2002-03-13 | 2012-10-10 | 詹森药业有限公司 | 用作组蛋白去乙酰酶抑制剂的磺酰基衍生物 |
OA12790A (en) | 2002-03-13 | 2006-07-10 | Janssen Pharmaceutica Nv | New inhibitors of histone deacetylase. |
MXPA04007776A (es) | 2002-03-13 | 2004-10-15 | Janssen Pharmaceutica Nv | Derivados de sulfonilamino como nuevos inhibidores de histona deacetilasa. |
US7119203B2 (en) | 2002-04-25 | 2006-10-10 | Pharmacia Corporation | Piperidinyl- and piperazinyl-sulfonylmethyl hydroxamic acids and their use as protease inhibitors |
CA2493584A1 (en) | 2002-07-25 | 2004-02-05 | Wisconsin Alumni Research Foundation | Inhibition of stearoyl-coa desaturase 1 (scd1) increases insulin sensitivity and treats diabetes |
CA2501539A1 (en) | 2002-10-17 | 2004-04-29 | Amgen Inc. | Benzimidazole derivatives and their use as vanilloid receptor ligands |
JP2004203871A (ja) | 2002-12-13 | 2004-07-22 | Yamanouchi Pharmaceut Co Ltd | 医薬組成物 |
JP2006516561A (ja) | 2003-01-17 | 2006-07-06 | 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 | 細胞増殖の阻害剤としての2−アミノピリジン置換ヘテロ環類 |
SG145701A1 (en) | 2003-07-30 | 2008-09-29 | Xenon Pharmaceuticals Inc | Piperazine derivatives and their use as therapeutic agents |
EP2316826A1 (en) | 2003-07-30 | 2011-05-04 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutics agents |
NZ545265A (en) | 2003-07-30 | 2009-11-27 | Xenon Pharmaceuticals Inc | Pyridazine derivatives and their use for treating diseases mediated by stearoyl-CoA desaturase (SCD) enzymes |
-
2004
- 2004-07-29 NZ NZ545265A patent/NZ545265A/en not_active IP Right Cessation
- 2004-07-29 AT AT04779562T patent/ATE527242T1/de active
- 2004-07-29 KR KR1020067002017A patent/KR100934554B1/ko not_active IP Right Cessation
- 2004-07-29 PT PT04779562T patent/PT1648874E/pt unknown
- 2004-07-29 AU AU2004261252A patent/AU2004261252C1/en not_active Ceased
- 2004-07-29 US US10/901,563 patent/US7335658B2/en not_active Expired - Fee Related
- 2004-07-29 CA CA2533899A patent/CA2533899C/en active Active
- 2004-07-29 TW TW099123172A patent/TW201038270A/zh unknown
- 2004-07-29 ES ES10184939.6T patent/ES2568769T3/es active Active
- 2004-07-29 EP EP04779562A patent/EP1648874B1/en active Active
- 2004-07-29 TW TW093122736A patent/TWI345974B/zh not_active IP Right Cessation
- 2004-07-29 JP JP2006522075A patent/JP4808616B2/ja not_active Expired - Fee Related
- 2004-07-29 ES ES04779562T patent/ES2375134T3/es active Active
- 2004-07-29 AR ARP040102690A patent/AR047557A1/es not_active Application Discontinuation
- 2004-07-29 EP EP16000190.5A patent/EP3042895A1/en not_active Withdrawn
- 2004-07-29 PL PL04779562T patent/PL1648874T3/pl unknown
- 2004-07-29 EP EP10184939.6A patent/EP2316827B1/en active Active
- 2004-07-29 DK DK04779562.0T patent/DK1648874T3/da active
- 2004-07-29 WO PCT/US2004/024548 patent/WO2005011655A2/en active Application Filing
-
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 (hr) | ||
ZA200600125B (en) | Pyridazine derivatives and their use as therapeutic agents | |
CA2597069C (en) | Pyridazine derivatives and their use as therapeutic agents | |
MX2007009592A (es) | Terapia de combinacion. | |
US7759348B2 (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 |