NO332822B1 - Pyridazinderivater, farmasoytiske preparater inneholdende slike, og deres anvendelse som terapeutiske midler - Google Patents
Pyridazinderivater, farmasoytiske preparater inneholdende slike, og deres anvendelse som terapeutiske midler Download PDFInfo
- Publication number
- NO332822B1 NO332822B1 NO20060981A NO20060981A NO332822B1 NO 332822 B1 NO332822 B1 NO 332822B1 NO 20060981 A NO20060981 A NO 20060981A NO 20060981 A NO20060981 A NO 20060981A NO 332822 B1 NO332822 B1 NO 332822B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- optionally substituted
- piperazin
- amide
- halogen
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 3
- 229940124597 therapeutic agent Drugs 0.000 title description 6
- 150000004892 pyridazines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 511
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 69
- 201000010099 disease Diseases 0.000 claims abstract description 53
- 241000124008 Mammalia Species 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 276
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 203
- 150000002367 halogens Chemical group 0.000 claims description 194
- 125000000217 alkyl group Chemical group 0.000 claims description 174
- 229910052739 hydrogen Inorganic materials 0.000 claims description 173
- 239000001257 hydrogen Substances 0.000 claims description 173
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 162
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 157
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 119
- 125000005843 halogen group Chemical group 0.000 claims description 92
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 68
- 125000004076 pyridyl group Chemical group 0.000 claims description 56
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 50
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 50
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 38
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 38
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 37
- 229910052760 oxygen Inorganic materials 0.000 claims description 37
- 239000001301 oxygen Substances 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 31
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 30
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 30
- 238000004519 manufacturing process Methods 0.000 claims description 30
- 150000001408 amides Chemical class 0.000 claims description 27
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 26
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 22
- 125000005605 benzo group Chemical group 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 20
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 20
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 19
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 19
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 17
- 125000002971 oxazolyl group Chemical group 0.000 claims description 17
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 17
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 17
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 17
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 16
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 16
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 16
- 125000002541 furyl group Chemical group 0.000 claims description 15
- 125000004193 piperazinyl group Chemical group 0.000 claims description 15
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 15
- FESRYVBBESMTNR-UHFFFAOYSA-N 3-cyclopropylpropan-1-amine Chemical compound NCCCC1CC1 FESRYVBBESMTNR-UHFFFAOYSA-N 0.000 claims description 14
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 13
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 13
- 208000008589 Obesity Diseases 0.000 claims description 12
- 239000004202 carbamide Substances 0.000 claims description 12
- 235000020824 obesity Nutrition 0.000 claims description 12
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 12
- 125000002883 imidazolyl group Chemical group 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
- 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 description 8
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 8
- 206010019708 Hepatic steatosis Diseases 0.000 claims description 8
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 7
- 208000004930 Fatty Liver Diseases 0.000 claims description 6
- 206010022489 Insulin Resistance Diseases 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 208000010706 fatty liver disease Diseases 0.000 claims description 6
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 6
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 6
- 231100000240 steatosis hepatitis Toxicity 0.000 claims description 6
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 5
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
- MGAPESYORZVKQD-UHFFFAOYSA-N 2-cyclobutylethanamine Chemical compound NCCC1CCC1 MGAPESYORZVKQD-UHFFFAOYSA-N 0.000 claims description 4
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 206010000496 acne Diseases 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 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 description 4
- RUUOPSRRIKJHNH-UHFFFAOYSA-N pyridazine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=N1 RUUOPSRRIKJHNH-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 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 description 2
- 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 description 2
- XMFKLBIJEISLHV-UHFFFAOYSA-N 4-methyl-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]pentanamide Chemical group 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 description 2
- JAWATIRLGNSNCM-UHFFFAOYSA-N 4-phenyl-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]butanamide Chemical group 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- YWOCIALEPJTGBQ-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[5-fluoro-2-(trifluoromethyl)benzoyl]-1,4-diazepan-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC=C(C(F)(F)F)C(C(=O)N2CCN(CCC2)C=2N=NC(=CC=2)C(=O)NCCC2CC2)=C1 YWOCIALEPJTGBQ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- QFQCGXUMMUCOTQ-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[2-[2-(trifluoromethyl)phenyl]acetyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical group 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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 group 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
- 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
- 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
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 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
- 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
- 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
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-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
- 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
- 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
- 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
- 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
- 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
- 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
- 238000000034 method Methods 0.000 abstract description 224
- 102100028897 Stearoyl-CoA desaturase Human genes 0.000 abstract description 60
- 230000001404 mediated effect Effects 0.000 abstract description 16
- 229910052721 tungsten Inorganic materials 0.000 abstract description 2
- 229910052720 vanadium Inorganic materials 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 225
- 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 166
- 238000006243 chemical reaction Methods 0.000 description 160
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 155
- 239000007787 solid Substances 0.000 description 136
- 239000000243 solution Substances 0.000 description 108
- 239000000843 powder Substances 0.000 description 96
- 239000000203 mixture Substances 0.000 description 92
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 87
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
- 239000011541 reaction mixture Substances 0.000 description 69
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 66
- 230000015572 biosynthetic process Effects 0.000 description 63
- 238000003786 synthesis reaction Methods 0.000 description 62
- 125000004432 carbon atom Chemical group C* 0.000 description 61
- 108010087894 Fatty acid desaturases Proteins 0.000 description 59
- 239000002904 solvent Substances 0.000 description 57
- 235000019439 ethyl acetate Nutrition 0.000 description 54
- DCRBBFSMVSLOKM-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-piperazin-1-ylpyridazine-3-carboxamide Chemical compound C=1C=C(N2CCNCC2)N=NC=1C(=O)NCCC1CC1 DCRBBFSMVSLOKM-UHFFFAOYSA-N 0.000 description 53
- 125000003118 aryl group Chemical group 0.000 description 52
- LHEGONYQWRZUFV-UHFFFAOYSA-N [4-(6-aminopyridazin-3-yl)piperazin-1-yl]-[2-(trifluoromethyl)phenyl]methanone Chemical compound N1=NC(N)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 LHEGONYQWRZUFV-UHFFFAOYSA-N 0.000 description 48
- LHISOGUWFQLNLI-UHFFFAOYSA-N 6-chloro-n-(2-cyclopropyl-2-hydroxyethyl)pyridazine-3-carboxamide Chemical compound C1CC1C(O)CNC(=O)C1=CC=C(Cl)N=N1 LHISOGUWFQLNLI-UHFFFAOYSA-N 0.000 description 44
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 42
- 239000000047 product Substances 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 125000001072 heteroaryl group Chemical group 0.000 description 38
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 37
- VDWDAGOWIJYIGH-UHFFFAOYSA-N piperazin-1-yl-[2-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCNCC1 VDWDAGOWIJYIGH-UHFFFAOYSA-N 0.000 description 37
- NASLINFISOTVJJ-UHFFFAOYSA-N 1,2-oxazole-5-carbonyl chloride Chemical compound ClC(=O)C1=CC=NO1 NASLINFISOTVJJ-UHFFFAOYSA-N 0.000 description 36
- 239000011734 sodium Substances 0.000 description 36
- 125000000623 heterocyclic group Chemical group 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
- 125000003710 aryl alkyl group Chemical group 0.000 description 31
- 239000012267 brine Substances 0.000 description 31
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 31
- QVTQYSFCFOGITD-UHFFFAOYSA-N 2,5-dichlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1Cl QVTQYSFCFOGITD-UHFFFAOYSA-N 0.000 description 30
- 238000004440 column chromatography Methods 0.000 description 30
- 230000000694 effects Effects 0.000 description 29
- 101150041968 CDC13 gene Proteins 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 229910052799 carbon Inorganic materials 0.000 description 27
- MUWNXFOPQGBORK-UHFFFAOYSA-N n-(3-methylbutyl)-6-piperazin-1-ylpyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCNCC1 MUWNXFOPQGBORK-UHFFFAOYSA-N 0.000 description 27
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 26
- 238000000746 purification Methods 0.000 description 23
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 22
- 238000010992 reflux Methods 0.000 description 22
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 21
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 21
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 239000012044 organic layer Substances 0.000 description 20
- 125000001188 haloalkyl group Chemical group 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- 235000014113 dietary fatty acids Nutrition 0.000 description 18
- 229930195729 fatty acid Natural products 0.000 description 18
- 239000000194 fatty acid Substances 0.000 description 18
- GRZHHTYDZVRPIC-UHFFFAOYSA-N (benzyloxy)acetic acid Chemical compound OC(=O)COCC1=CC=CC=C1 GRZHHTYDZVRPIC-UHFFFAOYSA-N 0.000 description 16
- 208000035475 disorder Diseases 0.000 description 16
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 16
- 239000000651 prodrug Substances 0.000 description 16
- 229940002612 prodrug Drugs 0.000 description 16
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 15
- 150000004665 fatty acids Chemical class 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 15
- 229920006395 saturated elastomer Polymers 0.000 description 15
- DYUXVJAFBUZREW-UHFFFAOYSA-N (2-isocyanatocyclopropyl)benzene Chemical compound O=C=NC1CC1C1=CC=CC=C1 DYUXVJAFBUZREW-UHFFFAOYSA-N 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 241000700605 Viruses Species 0.000 description 14
- 150000002632 lipids Chemical class 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- 101710159293 Acyl-CoA desaturase 1 Proteins 0.000 description 13
- 238000003818 flash chromatography Methods 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 12
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- BBXDMCQDLOCXRA-UHFFFAOYSA-N 1-(chloromethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1CCl BBXDMCQDLOCXRA-UHFFFAOYSA-N 0.000 description 11
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- ZNOCYNRWXAYNOU-UHFFFAOYSA-N 6-chloro-n-(2-cyclopropylethyl)pyridazine-3-carboxamide Chemical compound N1=NC(Cl)=CC=C1C(=O)NCCC1CC1 ZNOCYNRWXAYNOU-UHFFFAOYSA-N 0.000 description 10
- HHGZQZULOHYEOH-UHFFFAOYSA-N 6-chloropyridazine-3-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)N=N1 HHGZQZULOHYEOH-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 150000002431 hydrogen Chemical group 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- ZOGZOXRETBBBJI-UHFFFAOYSA-N 2-cyclopropylethanamine Chemical compound NCCC1CC1 ZOGZOXRETBBBJI-UHFFFAOYSA-N 0.000 description 9
- OBUKEMPWKGDRJV-UHFFFAOYSA-N 4,4,4-trifluoro-2-methylbutanoic acid Chemical compound OC(=O)C(C)CC(F)(F)F OBUKEMPWKGDRJV-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 241000699666 Mus <mouse, genus> Species 0.000 description 9
- 239000007832 Na2SO4 Substances 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 9
- KQBDDYSEVSDDMV-UHFFFAOYSA-N 6-chloro-n-(3-methylbutyl)pyridazine-3-carboxamide Chemical compound CC(C)CCNC(=O)C1=CC=C(Cl)N=N1 KQBDDYSEVSDDMV-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 125000004450 alkenylene group Chemical group 0.000 description 8
- 125000000262 haloalkenyl group Chemical group 0.000 description 8
- 238000001727 in vivo Methods 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 150000003254 radicals Chemical group 0.000 description 8
- 125000004385 trihaloalkyl group Chemical group 0.000 description 8
- 241000282412 Homo Species 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 7
- 230000004071 biological effect Effects 0.000 description 7
- 239000003937 drug carrier Substances 0.000 description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 7
- 208000006575 hypertriglyceridemia Diseases 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 150000003626 triacylglycerols Chemical class 0.000 description 7
- MXIUWSYTQJLIKE-UHFFFAOYSA-N 2-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1C(Cl)=O MXIUWSYTQJLIKE-UHFFFAOYSA-N 0.000 description 6
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 206010012601 diabetes mellitus Diseases 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 125000005020 hydroxyalkenyl group Chemical group 0.000 description 6
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 5
- PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 5
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 5
- HSKPEPFDFCWQGY-UHFFFAOYSA-N 5-chloro-2-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1C(Cl)=O HSKPEPFDFCWQGY-UHFFFAOYSA-N 0.000 description 5
- VHTVVTDYYXQDHS-UHFFFAOYSA-N 5-fluoro-2-(trifluoromethyl)benzoyl chloride Chemical compound FC1=CC=C(C(F)(F)F)C(C(Cl)=O)=C1 VHTVVTDYYXQDHS-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 108010062497 VLDL Lipoproteins Proteins 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 235000012000 cholesterol Nutrition 0.000 description 5
- 239000013058 crude material Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 208000006454 hepatitis Diseases 0.000 description 5
- 231100000283 hepatitis Toxicity 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- HPSSZFFAYWBIPY-UHFFFAOYSA-N malvalic acid Chemical compound CCCCCCCCC1=C(CCCCCCC(O)=O)C1 HPSSZFFAYWBIPY-UHFFFAOYSA-N 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IGURRQIIIXYJND-UHFFFAOYSA-N 2-(chloromethyl)-4-fluoro-1-(trifluoromethyl)benzene Chemical compound FC1=CC=C(C(F)(F)F)C(CCl)=C1 IGURRQIIIXYJND-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 4
- FSAFKVORIORDIQ-UHFFFAOYSA-N 6-chloro-n-pentylpyridazine-3-carboxamide Chemical compound CCCCCNC(=O)C1=CC=C(Cl)N=N1 FSAFKVORIORDIQ-UHFFFAOYSA-N 0.000 description 4
- DZCBVXKRERSHAA-UHFFFAOYSA-N 6-oxo-1h-pyridazine-3-carboxylic acid;hydrate Chemical compound O.OC(=O)C=1C=CC(=O)NN=1 DZCBVXKRERSHAA-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- ZKHVSNDPPPJHTM-UHFFFAOYSA-N [5-fluoro-2-(trifluoromethyl)phenyl]-piperazin-1-ylmethanone Chemical compound FC1=CC=C(C(F)(F)F)C(C(=O)N2CCNCC2)=C1 ZKHVSNDPPPJHTM-UHFFFAOYSA-N 0.000 description 4
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 4
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 4
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- QBXNJBGGSWRASI-UHFFFAOYSA-N n-(3-cyclopropylpropyl)-6-piperazin-1-ylpyridazine-3-carboxamide Chemical compound C=1C=C(N2CCNCC2)N=NC=1C(=O)NCCCC1CC1 QBXNJBGGSWRASI-UHFFFAOYSA-N 0.000 description 4
- URJBKUCCCXVRAM-UHFFFAOYSA-N pyridazin-3-ylurea Chemical compound NC(=O)NC1=CC=CN=N1 URJBKUCCCXVRAM-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000012453 solvate Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- JCAJMHONCHYTCA-UHFFFAOYSA-N 2-amino-1-cyclopropylethanol Chemical compound NCC(O)C1CC1 JCAJMHONCHYTCA-UHFFFAOYSA-N 0.000 description 3
- WFHNCBSAQBJTLV-UHFFFAOYSA-N 6-chloro-n-(2-cyclobutylethyl)pyridazine-3-carboxamide Chemical compound N1=NC(Cl)=CC=C1C(=O)NCCC1CCC1 WFHNCBSAQBJTLV-UHFFFAOYSA-N 0.000 description 3
- JBYXPOFIGCOSSB-GOJKSUSPSA-N 9-cis,11-trans-octadecadienoic acid Chemical class CCCCCC\C=C\C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-GOJKSUSPSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 208000024172 Cardiovascular disease Diseases 0.000 description 3
- 241000711573 Coronaviridae Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 108010010234 HDL Lipoproteins Proteins 0.000 description 3
- 241000725303 Human immunodeficiency virus Species 0.000 description 3
- 208000035150 Hypercholesterolemia Diseases 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 230000007812 deficiency Effects 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
- 208000037765 diseases and disorders Diseases 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 230000037356 lipid metabolism Effects 0.000 description 3
- 244000144972 livestock Species 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 230000003228 microsomal effect Effects 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 150000003904 phospholipids Chemical class 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- SIARJEKBADXQJG-LFZQUHGESA-N stearoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCCCCCCCCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 SIARJEKBADXQJG-LFZQUHGESA-N 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- 238000005556 structure-activity relationship Methods 0.000 description 3
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 2
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 2
- SKCBKBCACWDALV-UHFFFAOYSA-N 1-(trifluoromethyl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(C(F)(F)F)CC1 SKCBKBCACWDALV-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 2
- XZRHNAFEYMSXRG-UHFFFAOYSA-N 2,5-dimethylbenzoic acid Chemical compound CC1=CC=C(C)C(C(O)=O)=C1 XZRHNAFEYMSXRG-UHFFFAOYSA-N 0.000 description 2
- NSMWYRLQHIXVAP-UHFFFAOYSA-N 2,5-dimethylpiperazine Chemical compound CC1CNC(C)CN1 NSMWYRLQHIXVAP-UHFFFAOYSA-N 0.000 description 2
- GSNLYQDUCHEFFQ-UHFFFAOYSA-N 2-(trifluoromethyl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C(F)(F)F GSNLYQDUCHEFFQ-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- LUNMJRJMSXZSLC-UHFFFAOYSA-N 2-cyclopropylethanol Chemical compound OCCC1CC1 LUNMJRJMSXZSLC-UHFFFAOYSA-N 0.000 description 2
- JVOCWIRGDNWGKH-UHFFFAOYSA-N 2-cyclopropylethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCC1CC1 JVOCWIRGDNWGKH-UHFFFAOYSA-N 0.000 description 2
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- DTXVKPOKPFWSFF-UHFFFAOYSA-N 3(S)-hydroxy-13-cis-eicosenoyl-CoA Chemical compound NC1=CC=C(Cl)N=N1 DTXVKPOKPFWSFF-UHFFFAOYSA-N 0.000 description 2
- INDZKZONOLGFIL-UHFFFAOYSA-N 3-cyclopropylpropanenitrile Chemical compound N#CCCC1CC1 INDZKZONOLGFIL-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- OEYHURRIOWWRMD-UHFFFAOYSA-N 4-fluoro-2-(trifluoromethyl)benzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C(C(F)(F)F)=C1 OEYHURRIOWWRMD-UHFFFAOYSA-N 0.000 description 2
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- JDUIZNLWCUQOQN-UHFFFAOYSA-N 6-chloro-n-(2-hydroxy-3,3-dimethylbutyl)pyridazine-3-carboxamide Chemical compound CC(C)(C)C(O)CNC(=O)C1=CC=C(Cl)N=N1 JDUIZNLWCUQOQN-UHFFFAOYSA-N 0.000 description 2
- RAEIHVXPNQZPSP-UHFFFAOYSA-N 6-chloro-n-[2-(3-fluorophenyl)ethyl]pyridazine-3-carboxamide Chemical compound FC1=CC=CC(CCNC(=O)C=2N=NC(Cl)=CC=2)=C1 RAEIHVXPNQZPSP-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- 241000710929 Alphavirus Species 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 241000723346 Cinnamomum camphora Species 0.000 description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
- 206010014476 Elevated cholesterol Diseases 0.000 description 2
- 206010014486 Elevated triglycerides Diseases 0.000 description 2
- YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 2
- 241000710781 Flaviviridae Species 0.000 description 2
- 241000711549 Hepacivirus C Species 0.000 description 2
- 101100041816 Homo sapiens SCD gene Proteins 0.000 description 2
- 101000639987 Homo sapiens Stearoyl-CoA desaturase 5 Proteins 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 201000001431 Hyperuricemia Diseases 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 2
- 108010007622 LDL Lipoproteins Proteins 0.000 description 2
- 102000007330 LDL Lipoproteins Human genes 0.000 description 2
- 102000016267 Leptin Human genes 0.000 description 2
- 108010092277 Leptin Proteins 0.000 description 2
- 208000021642 Muscular disease Diseases 0.000 description 2
- 201000009623 Myopathy Diseases 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000709664 Picornaviridae Species 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 102000001708 Protein Isoforms Human genes 0.000 description 2
- 108010029485 Protein Isoforms Proteins 0.000 description 2
- 241000315672 SARS coronavirus Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- PQRKPYLNZGDCFH-UHFFFAOYSA-N Sterculic-saeure Natural products CCCCCCCCC1=C(CCCCCCCC(O)=O)C1 PQRKPYLNZGDCFH-UHFFFAOYSA-N 0.000 description 2
- 241000534944 Thia Species 0.000 description 2
- 241000710771 Tick-borne encephalitis virus Species 0.000 description 2
- 241000710772 Yellow fever virus Species 0.000 description 2
- ZJOMYCRHEFBNHK-UHFFFAOYSA-N [4-(6-aminopyridazin-3-yl)piperazin-1-yl]-[5-fluoro-2-(trifluoromethyl)phenyl]methanone Chemical compound N1=NC(N)=CC=C1N1CCN(C(=O)C=2C(=CC=C(F)C=2)C(F)(F)F)CC1 ZJOMYCRHEFBNHK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 229960001948 caffeine Drugs 0.000 description 2
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229960000846 camphor Drugs 0.000 description 2
- 229930008380 camphor Natural products 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000003636 chemical group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000460 chlorine Chemical group 0.000 description 2
- 150000001840 cholesterol esters Chemical class 0.000 description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
- 229960001231 choline Drugs 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229940108924 conjugated linoleic acid Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- WPOPOPFNZYPKAV-UHFFFAOYSA-N cyclobutylmethanol Chemical compound OCC1CCC1 WPOPOPFNZYPKAV-UHFFFAOYSA-N 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical class CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 102000050986 human SCD5 Human genes 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 2
- 229940039781 leptin Drugs 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 2
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 210000004379 membrane Anatomy 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- GEYJRAIMMCYSLF-UHFFFAOYSA-N methyl 6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxylate Chemical compound N1=NC(C(=O)OC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 GEYJRAIMMCYSLF-UHFFFAOYSA-N 0.000 description 2
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- BPUUVKXTQGGXGX-UHFFFAOYSA-N n-(2-cyclobutylethyl)-6-piperazin-1-ylpyridazine-3-carboxamide Chemical compound C=1C=C(N2CCNCC2)N=NC=1C(=O)NCCC1CCC1 BPUUVKXTQGGXGX-UHFFFAOYSA-N 0.000 description 2
- IKOWJKRHWIOSFZ-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-(1,4-diazepan-1-yl)pyridazine-3-carboxamide Chemical compound C=1C=C(N2CCNCCC2)N=NC=1C(=O)NCCC1CC1 IKOWJKRHWIOSFZ-UHFFFAOYSA-N 0.000 description 2
- GTEYIPWLHANVES-UHFFFAOYSA-N n-(3-methylbutyl)-6-[4-(2-methylsulfonylbenzoyl)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(C)(=O)=O)CC1 GTEYIPWLHANVES-UHFFFAOYSA-N 0.000 description 2
- IAAZQDWNODTDSC-UHFFFAOYSA-N n-(3-methylbutyl)-6-[4-[5-(trifluoromethyl)-2h-triazole-4-carbonyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C2=C(N=NN2)C(F)(F)F)CC1 IAAZQDWNODTDSC-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- KNRWRZTXCIZWEE-UHFFFAOYSA-N n-pent-4-enyl-6-piperazin-1-ylpyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCCC=C)=CC=C1N1CCNCC1 KNRWRZTXCIZWEE-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- MNBKLUUYKPBKDU-BBECNAHFSA-N palmitoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCCCCCCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MNBKLUUYKPBKDU-BBECNAHFSA-N 0.000 description 2
- UVBBCQLPTZEDHT-UHFFFAOYSA-N pent-4-en-1-amine Chemical compound NCCCC=C UVBBCQLPTZEDHT-UHFFFAOYSA-N 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- IJNKKLFZNYXODV-UHFFFAOYSA-N tert-butyl 4-[2-(trifluoromethyl)benzenecarbothioyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=S)C1=CC=CC=C1C(F)(F)F IJNKKLFZNYXODV-UHFFFAOYSA-N 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- 238000011287 therapeutic dose Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 2
- 201000005665 thrombophilia Diseases 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- 125000004952 trihaloalkoxy group Chemical group 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
- 208000016261 weight loss Diseases 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 229940051021 yellow-fever virus Drugs 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- WFDYOKBYDJIGLN-UHFFFAOYSA-N (2,6-difluorophenyl)-piperazin-1-ylmethanone Chemical compound FC1=CC=CC(F)=C1C(=O)N1CCNCC1 WFDYOKBYDJIGLN-UHFFFAOYSA-N 0.000 description 1
- DSGKWFGEUBCEIE-UHFFFAOYSA-N (2-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C(Cl)=O DSGKWFGEUBCEIE-UHFFFAOYSA-N 0.000 description 1
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- SMLHLXHCIJUNJT-UHFFFAOYSA-N (2-methylcyclopropyl)-piperazin-1-ylmethanone Chemical compound CC1CC1C(=O)N1CCNCC1 SMLHLXHCIJUNJT-UHFFFAOYSA-N 0.000 description 1
- NPWMTBZSRRLQNJ-VKHMYHEASA-N (3s)-3-aminopiperidine-2,6-dione Chemical compound N[C@H]1CCC(=O)NC1=O NPWMTBZSRRLQNJ-VKHMYHEASA-N 0.000 description 1
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- QZBAYURFHCTXOJ-OWOJBTEDSA-N (e)-4,4,4-trifluorobut-2-enoic acid Chemical compound OC(=O)\C=C\C(F)(F)F QZBAYURFHCTXOJ-OWOJBTEDSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 description 1
- WLNAHQZFPSSVTP-UHFFFAOYSA-N 1,2-dichloro-4-(isocyanatomethyl)benzene Chemical compound ClC1=CC=C(CN=C=O)C=C1Cl WLNAHQZFPSSVTP-UHFFFAOYSA-N 0.000 description 1
- ZILSBZLQGRBMOR-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethanamine Chemical compound NCC1=CC=C2OCOC2=C1 ZILSBZLQGRBMOR-UHFFFAOYSA-N 0.000 description 1
- OMZINLIPPVNUOG-UHFFFAOYSA-N 1,4-dichloro-2-(chloromethyl)benzene Chemical compound ClCC1=CC(Cl)=CC=C1Cl OMZINLIPPVNUOG-UHFFFAOYSA-N 0.000 description 1
- UKESBLFBQANJHH-UHFFFAOYSA-N 1-(Tetrahydro-2-furoyl)piperazine Chemical compound C1CNCCN1C(=O)C1CCCO1 UKESBLFBQANJHH-UHFFFAOYSA-N 0.000 description 1
- FZTZSNPJDFLZOZ-UHFFFAOYSA-N 1-(chloromethyl)-4-fluoro-2-(trifluoromethyl)benzene Chemical compound FC1=CC=C(CCl)C(C(F)(F)F)=C1 FZTZSNPJDFLZOZ-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- IUKICUAZNUHIDR-UHFFFAOYSA-N 1-amino-4,4-dimethylpentan-3-ol Chemical compound CC(C)(C)C(O)CCN IUKICUAZNUHIDR-UHFFFAOYSA-N 0.000 description 1
- LVDUPBPSVVIGNY-UHFFFAOYSA-N 1-benzyl-5-(trifluoromethyl)triazole-4-carboxylic acid Chemical compound FC(F)(F)C1=C(C(=O)O)N=NN1CC1=CC=CC=C1 LVDUPBPSVVIGNY-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- JFLSOKIMYBSASW-UHFFFAOYSA-N 1-chloro-2-[chloro(diphenyl)methyl]benzene Chemical compound ClC1=CC=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 JFLSOKIMYBSASW-UHFFFAOYSA-N 0.000 description 1
- QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
- IWZPNMNTVFKFOH-UHFFFAOYSA-N 1-cyclopropyl-2-nitroethanol Chemical compound [O-][N+](=O)CC(O)C1CC1 IWZPNMNTVFKFOH-UHFFFAOYSA-N 0.000 description 1
- VZNCSZQPNIEEMN-UHFFFAOYSA-N 1-fluoro-2-isocyanatobenzene Chemical compound FC1=CC=CC=C1N=C=O VZNCSZQPNIEEMN-UHFFFAOYSA-N 0.000 description 1
- HHSIWJYERNCLKQ-UHFFFAOYSA-N 1-fluoro-4-(isocyanatomethyl)benzene Chemical compound FC1=CC=C(CN=C=O)C=C1 HHSIWJYERNCLKQ-UHFFFAOYSA-N 0.000 description 1
- DSVGFKBFFICWLZ-UHFFFAOYSA-N 1-fluoro-4-isocyanatobenzene Chemical compound FC1=CC=C(N=C=O)C=C1 DSVGFKBFFICWLZ-UHFFFAOYSA-N 0.000 description 1
- GQXURJDNDYACGE-UHFFFAOYSA-N 1-hydroxycyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(O)CC1 GQXURJDNDYACGE-UHFFFAOYSA-N 0.000 description 1
- RFXBSYPBSRSQDU-UHFFFAOYSA-N 1-isocyanatoheptane Chemical compound CCCCCCCN=C=O RFXBSYPBSRSQDU-UHFFFAOYSA-N 0.000 description 1
- VRVUKQWNRPNACD-UHFFFAOYSA-N 1-isocyanatopentane Chemical compound CCCCCN=C=O VRVUKQWNRPNACD-UHFFFAOYSA-N 0.000 description 1
- BPTGBMUGXIROPX-UHFFFAOYSA-N 1-methyl-5-(trifluoromethyl)pyrazole-4-carbonyl chloride Chemical compound CN1N=CC(C(Cl)=O)=C1C(F)(F)F BPTGBMUGXIROPX-UHFFFAOYSA-N 0.000 description 1
- ILAOVOOZLVGAJF-UHFFFAOYSA-N 1-methylpyrrole-2-carboxylic acid Chemical compound CN1C=CC=C1C(O)=O ILAOVOOZLVGAJF-UHFFFAOYSA-N 0.000 description 1
- 125000005987 1-oxo-thiomorpholinyl group Chemical group 0.000 description 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- SFHVXKNMCGSLAR-UHFFFAOYSA-N 2,2,3,3-tetramethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C(O)=O)C1(C)C SFHVXKNMCGSLAR-UHFFFAOYSA-N 0.000 description 1
- FZUZAXBAUSXGAV-UHFFFAOYSA-N 2,2-difluoro-2-phenylethanamine Chemical compound NCC(F)(F)C1=CC=CC=C1 FZUZAXBAUSXGAV-UHFFFAOYSA-N 0.000 description 1
- TYKNQWWXUIYRSZ-UHFFFAOYSA-N 2,2-difluoro-2-pyridin-2-ylethanamine Chemical compound NCC(F)(F)C1=CC=CC=N1 TYKNQWWXUIYRSZ-UHFFFAOYSA-N 0.000 description 1
- VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical compound CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-UHFFFAOYSA-N 0.000 description 1
- YBZQRYWKYBZZNT-UHFFFAOYSA-N 2,2-dimethylcyclopropane-1-carboxamide Chemical compound CC1(C)CC1C(N)=O YBZQRYWKYBZZNT-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical class O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 description 1
- TZXHEDOCQVTEPT-UHFFFAOYSA-N 2,4-bis(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=C(C(Cl)=O)C(C(F)(F)F)=C1 TZXHEDOCQVTEPT-UHFFFAOYSA-N 0.000 description 1
- IRSVDHPYXFLLDS-UHFFFAOYSA-N 2,4-dichloro-1-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1Cl IRSVDHPYXFLLDS-UHFFFAOYSA-N 0.000 description 1
- CEOCVKWBUWKBKA-UHFFFAOYSA-N 2,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1Cl CEOCVKWBUWKBKA-UHFFFAOYSA-N 0.000 description 1
- LRJNPOCQOZWIGR-UHFFFAOYSA-N 2,5-bis(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=C(C(F)(F)F)C(C(Cl)=O)=C1 LRJNPOCQOZWIGR-UHFFFAOYSA-N 0.000 description 1
- RLRUKKDFNWXXRT-UHFFFAOYSA-N 2,5-difluorobenzoyl chloride Chemical compound FC1=CC=C(F)C(C(Cl)=O)=C1 RLRUKKDFNWXXRT-UHFFFAOYSA-N 0.000 description 1
- AJPKQSSFYHPYMH-UHFFFAOYSA-N 2,6-dichloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)N=C1Cl AJPKQSSFYHPYMH-UHFFFAOYSA-N 0.000 description 1
- QRHUZEVERIHEPT-UHFFFAOYSA-N 2,6-difluorobenzoyl chloride Chemical compound FC1=CC=CC(F)=C1C(Cl)=O QRHUZEVERIHEPT-UHFFFAOYSA-N 0.000 description 1
- OCOCFNMFLNFNIA-ZSCHJXSPSA-N 2-(1-benzylindazol-3-yl)oxyacetic acid;(2s)-2,6-diaminohexanoic acid Chemical compound [NH3+]CCCC[C@H]([NH3+])C([O-])=O.C12=CC=CC=C2C(OCC(=O)[O-])=NN1CC1=CC=CC=C1 OCOCFNMFLNFNIA-ZSCHJXSPSA-N 0.000 description 1
- CLLLODNOQBVIMS-UHFFFAOYSA-N 2-(2-methoxyethoxy)acetic acid Chemical compound COCCOCC(O)=O CLLLODNOQBVIMS-UHFFFAOYSA-N 0.000 description 1
- TYXPXHVKYDUHCS-UHFFFAOYSA-N 2-(3,3,3-trifluoropropoxy)acetic acid Chemical compound OC(=O)COCCC(F)(F)F TYXPXHVKYDUHCS-UHFFFAOYSA-N 0.000 description 1
- AUCVZEYHEFAWHO-UHFFFAOYSA-N 2-(3-fluorophenyl)ethanamine Chemical compound NCCC1=CC=CC(F)=C1 AUCVZEYHEFAWHO-UHFFFAOYSA-N 0.000 description 1
- IUWMURBOFGBWBO-UHFFFAOYSA-N 2-(cyclopropylmethoxy)acetic acid Chemical compound OC(=O)COCC1CC1 IUWMURBOFGBWBO-UHFFFAOYSA-N 0.000 description 1
- DVVXXHVHGGWWPE-UHFFFAOYSA-N 2-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=CC=C1C(O)=O DVVXXHVHGGWWPE-UHFFFAOYSA-N 0.000 description 1
- KSHPWYXAJJCUMJ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzoyl chloride Chemical compound FC(F)(F)OC1=CC=CC=C1C(Cl)=O KSHPWYXAJJCUMJ-UHFFFAOYSA-N 0.000 description 1
- ZDVRPKUWYQVVDX-UHFFFAOYSA-N 2-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC=C1C=O ZDVRPKUWYQVVDX-UHFFFAOYSA-N 0.000 description 1
- HYIKIZXFYAKIPK-UHFFFAOYSA-N 2-(trifluoromethyl)furan-3-carboxylic acid Chemical compound OC(=O)C=1C=COC=1C(F)(F)F HYIKIZXFYAKIPK-UHFFFAOYSA-N 0.000 description 1
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 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 description 1
- KLIPUNKCUPNMHM-UHFFFAOYSA-N 2-amino-1-(3-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC(F)=C1 KLIPUNKCUPNMHM-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- HMIAXVWVTBIGON-UHFFFAOYSA-N 2-chloro-1-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCl)C(Cl)=C1 HMIAXVWVTBIGON-UHFFFAOYSA-N 0.000 description 1
- GPIQOFWTZXXOOV-UHFFFAOYSA-N 2-chloro-4,6-dimethoxy-1,3,5-triazine Chemical compound COC1=NC(Cl)=NC(OC)=N1 GPIQOFWTZXXOOV-UHFFFAOYSA-N 0.000 description 1
- WWIMLOPLLNXPLC-UHFFFAOYSA-N 2-chloro-5-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(Cl)C(C(O)=O)=C1 WWIMLOPLLNXPLC-UHFFFAOYSA-N 0.000 description 1
- SGZSJPBASHYOHQ-UHFFFAOYSA-N 2-chloro-5-fluorobenzoyl chloride Chemical compound FC1=CC=C(Cl)C(C(Cl)=O)=C1 SGZSJPBASHYOHQ-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- IBRSSZOHCGUTHI-UHFFFAOYSA-N 2-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1Cl IBRSSZOHCGUTHI-UHFFFAOYSA-N 0.000 description 1
- DTNSDCJFTHMDAK-UHFFFAOYSA-N 2-cyanobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C#N DTNSDCJFTHMDAK-UHFFFAOYSA-N 0.000 description 1
- BWFYLNLITXLIGS-UHFFFAOYSA-N 2-cyclobutylacetonitrile Chemical compound N#CCC1CCC1 BWFYLNLITXLIGS-UHFFFAOYSA-N 0.000 description 1
- HTVFIKCPFOGRIQ-UHFFFAOYSA-N 2-cyclobutylpropan-1-amine Chemical compound NCC(C)C1CCC1 HTVFIKCPFOGRIQ-UHFFFAOYSA-N 0.000 description 1
- NVZWRBQRSDRIGC-UHFFFAOYSA-N 2-cyclobutylpropanenitrile Chemical compound N#CC(C)C1CCC1 NVZWRBQRSDRIGC-UHFFFAOYSA-N 0.000 description 1
- FAUQRRGKJKMEIW-UHFFFAOYSA-N 2-cyclopropylacetonitrile Chemical compound N#CCC1CC1 FAUQRRGKJKMEIW-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 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 description 1
- SMUKODJVMQOSAB-UHFFFAOYSA-N 2-ethylbutanoyl chloride Chemical compound CCC(CC)C(Cl)=O SMUKODJVMQOSAB-UHFFFAOYSA-N 0.000 description 1
- RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical compound FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-UHFFFAOYSA-N 0.000 description 1
- VODKOOOHHCAWFR-UHFFFAOYSA-N 2-iodoacetonitrile Chemical compound ICC#N VODKOOOHHCAWFR-UHFFFAOYSA-N 0.000 description 1
- CPJRDBNLRNFKFI-UHFFFAOYSA-N 2-methyl-5-(trifluoromethyl)-1,3-oxazole-4-carboxylic acid Chemical compound CC1=NC(C(O)=O)=C(C(F)(F)F)O1 CPJRDBNLRNFKFI-UHFFFAOYSA-N 0.000 description 1
- JBCVZJOTIVKNSZ-UHFFFAOYSA-N 2-methyl-5-(trifluoromethyl)triazole-4-carboxylic acid Chemical compound CN1N=C(C(O)=O)C(C(F)(F)F)=N1 JBCVZJOTIVKNSZ-UHFFFAOYSA-N 0.000 description 1
- VSKXJRZPVDLHFY-UHFFFAOYSA-N 2-methylcyclohexane-1-carboxylic acid Chemical compound CC1CCCCC1C(O)=O VSKXJRZPVDLHFY-UHFFFAOYSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 1
- 125000006088 2-oxoazepinyl group Chemical group 0.000 description 1
- 125000004638 2-oxopiperazinyl group Chemical group O=C1N(CCNC1)* 0.000 description 1
- 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 description 1
- SODZBMGDYKEZJG-UHFFFAOYSA-N 2-phenylcyclopropane-1-carbonyl chloride Chemical compound ClC(=O)C1CC1C1=CC=CC=C1 SODZBMGDYKEZJG-UHFFFAOYSA-N 0.000 description 1
- AHDDRJBFJBDEPW-UHFFFAOYSA-N 2-phenylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C1=CC=CC=C1 AHDDRJBFJBDEPW-UHFFFAOYSA-N 0.000 description 1
- HACRKYQRZABURO-UHFFFAOYSA-N 2-phenylethyl isocyanate Chemical compound O=C=NCCC1=CC=CC=C1 HACRKYQRZABURO-UHFFFAOYSA-N 0.000 description 1
- USECIYVEPXUVHT-UHFFFAOYSA-N 2-propan-2-yloxyethanamine Chemical compound CC(C)OCCN USECIYVEPXUVHT-UHFFFAOYSA-N 0.000 description 1
- XPQIPUZPSLAZDV-UHFFFAOYSA-N 2-pyridylethylamine Chemical compound NCCC1=CC=CC=N1 XPQIPUZPSLAZDV-UHFFFAOYSA-N 0.000 description 1
- HVLUYXIJZLDNIS-UHFFFAOYSA-N 2-thiophen-2-ylethanamine Chemical compound NCCC1=CC=CS1 HVLUYXIJZLDNIS-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UHFFFAOYSA-N 2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound OCC1OC(CO)(OC2OC(CO)C(O)C(O)C2O)C(O)C1O CZMRCDWAGMRECN-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- LBWMQVOHFPLVBY-UHFFFAOYSA-N 3,3,3-trifluoro-1-phenylpropan-1-one Chemical compound FC(F)(F)CC(=O)C1=CC=CC=C1 LBWMQVOHFPLVBY-UHFFFAOYSA-N 0.000 description 1
- CTGJACFEVDCYMC-UHFFFAOYSA-N 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid Chemical compound OC(=O)C(O)(C)C(F)(F)F CTGJACFEVDCYMC-UHFFFAOYSA-N 0.000 description 1
- SBPOECSUFWPZFS-UHFFFAOYSA-N 3,3,3-trifluoro-2-methyl-2-(trifluoromethyl)propanoyl chloride Chemical compound ClC(=O)C(C)(C(F)(F)F)C(F)(F)F SBPOECSUFWPZFS-UHFFFAOYSA-N 0.000 description 1
- GPWHFPWZAPOYNO-UHFFFAOYSA-N 3,3-dimethylbutan-1-amine Chemical compound CC(C)(C)CCN GPWHFPWZAPOYNO-UHFFFAOYSA-N 0.000 description 1
- DUXCSEISVMREAX-UHFFFAOYSA-N 3,3-dimethylbutan-1-ol Chemical compound CC(C)(C)CCO DUXCSEISVMREAX-UHFFFAOYSA-N 0.000 description 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 description 1
- ZMKXWDPUXLPHCA-UHFFFAOYSA-N 3-(4-fluorophenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C(F)C=C1 ZMKXWDPUXLPHCA-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- BUSOTUQRURCMCM-UHFFFAOYSA-N 3-Phenoxypropionic acid Chemical compound OC(=O)CCOC1=CC=CC=C1 BUSOTUQRURCMCM-UHFFFAOYSA-N 0.000 description 1
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- PJWDXZJQMUREOZ-UHFFFAOYSA-N 3-benzyl-5-(trifluoromethyl)triazole-4-carboxylic acid Chemical compound OC(=O)C1=C(C(F)(F)F)N=NN1CC1=CC=CC=C1 PJWDXZJQMUREOZ-UHFFFAOYSA-N 0.000 description 1
- PRORLQAJNJMGAR-UHFFFAOYSA-N 3-chloro-6-methylpyridazine Chemical compound CC1=CC=C(Cl)N=N1 PRORLQAJNJMGAR-UHFFFAOYSA-N 0.000 description 1
- SGNOPBAHANXEKY-UHFFFAOYSA-N 3-cyclobutylpropan-1-amine Chemical compound NCCCC1CCC1 SGNOPBAHANXEKY-UHFFFAOYSA-N 0.000 description 1
- FHWMGBNKQOJFOJ-UHFFFAOYSA-N 3-fluoro-2-(trifluoromethyl)benzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1C(F)(F)F FHWMGBNKQOJFOJ-UHFFFAOYSA-N 0.000 description 1
- HTNUUDFQRYBJPH-UHFFFAOYSA-N 3-methoxypropanehydrazide Chemical compound COCCC(=O)NN HTNUUDFQRYBJPH-UHFFFAOYSA-N 0.000 description 1
- CIFSKZDQGRCLBN-UHFFFAOYSA-N 3-methylcyclohexane-1-carboxylic acid Chemical compound CC1CCCC(C(O)=O)C1 CIFSKZDQGRCLBN-UHFFFAOYSA-N 0.000 description 1
- ZSBJCNVMTCMOBW-UHFFFAOYSA-N 4,4,4-trifluoro-3-(trifluoromethyl)but-2-enoic acid Chemical compound OC(=O)C=C(C(F)(F)F)C(F)(F)F ZSBJCNVMTCMOBW-UHFFFAOYSA-N 0.000 description 1
- NOHJBOWARMTILE-UHFFFAOYSA-N 4,4,4-trifluoro-3-hydroxy-3-(trifluoromethyl)butanoic acid Chemical compound OC(=O)CC(O)(C(F)(F)F)C(F)(F)F NOHJBOWARMTILE-UHFFFAOYSA-N 0.000 description 1
- JCJGOWYCFRASTM-UHFFFAOYSA-N 4,4,4-trifluoro-3-hydroxy-3-methylbutanoic acid Chemical compound FC(F)(F)C(O)(C)CC(O)=O JCJGOWYCFRASTM-UHFFFAOYSA-N 0.000 description 1
- QRRCTLYMABZQCS-UHFFFAOYSA-N 4,4,4-trifluoro-3-methylbut-2-enoic acid Chemical compound FC(F)(F)C(C)=CC(O)=O QRRCTLYMABZQCS-UHFFFAOYSA-N 0.000 description 1
- FFZMMBKGTNDVRX-UHFFFAOYSA-N 4,4,4-trifluoro-3-methylbutanoic acid Chemical compound FC(F)(F)C(C)CC(O)=O FFZMMBKGTNDVRX-UHFFFAOYSA-N 0.000 description 1
- WTUCTMYLCMVYEX-UHFFFAOYSA-N 4,4,4-trifluorobutanoic acid Chemical compound OC(=O)CCC(F)(F)F WTUCTMYLCMVYEX-UHFFFAOYSA-N 0.000 description 1
- LZHMNCJMXQKSBY-UHFFFAOYSA-N 4-(4-methoxyphenyl)butanoic acid Chemical compound COC1=CC=C(CCCC(O)=O)C=C1 LZHMNCJMXQKSBY-UHFFFAOYSA-N 0.000 description 1
- NMAKJOWVEDTHOA-UHFFFAOYSA-N 4-(chloromethyl)-1,3-thiazol-2-amine;hydron;chloride Chemical compound Cl.NC1=NC(CCl)=CS1 NMAKJOWVEDTHOA-UHFFFAOYSA-N 0.000 description 1
- LMRJHNFECNKDKH-UHFFFAOYSA-N 4-(trifluoromethyl)nicotinic acid Chemical compound OC(=O)C1=CN=CC=C1C(F)(F)F LMRJHNFECNKDKH-UHFFFAOYSA-N 0.000 description 1
- DDCNZKAQHGFAEH-UHFFFAOYSA-N 4-[2-(trifluoromethyl)benzoyl]piperazine-1-carboxylic acid Chemical compound C1CN(C(=O)O)CCN1C(=O)C1=CC=CC=C1C(F)(F)F DDCNZKAQHGFAEH-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- CVWYAZQAEPRHIQ-UHFFFAOYSA-N 4-chloro-2-(chloromethyl)-1-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1CCl CVWYAZQAEPRHIQ-UHFFFAOYSA-N 0.000 description 1
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
- QTDXSEZXAPHVBI-UHFFFAOYSA-N 4-methylcyclohexane-1-carboxylic acid Chemical compound CC1CCC(C(O)=O)CC1 QTDXSEZXAPHVBI-UHFFFAOYSA-N 0.000 description 1
- QVIAMKXOQGCYCV-UHFFFAOYSA-N 4-methylpentan-1-amine Chemical compound CC(C)CCCN QVIAMKXOQGCYCV-UHFFFAOYSA-N 0.000 description 1
- FBAIGEMWTOSCRU-UHFFFAOYSA-N 4-methylpiperazine-1-carbonyl chloride Chemical compound CN1CCN(C(Cl)=O)CC1 FBAIGEMWTOSCRU-UHFFFAOYSA-N 0.000 description 1
- UNYBSERVIMALSJ-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-imidazole-4-carboxylic acid Chemical compound OC(=O)C=1NC=NC=1C(F)(F)F UNYBSERVIMALSJ-UHFFFAOYSA-N 0.000 description 1
- MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 description 1
- WPXFJBPJUGMYOD-UHFFFAOYSA-N 5-fluoro-2-methoxybenzoic acid Chemical compound COC1=CC=C(F)C=C1C(O)=O WPXFJBPJUGMYOD-UHFFFAOYSA-N 0.000 description 1
- NURNFMNHTHXTDS-UHFFFAOYSA-N 5-methyl-2-(trifluoromethyl)furan-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=C(C(F)(F)F)O1 NURNFMNHTHXTDS-UHFFFAOYSA-N 0.000 description 1
- GHZOZARQZLMNJF-UHFFFAOYSA-N 6-(4-benzylpiperazin-1-yl)-n-(3-methylbutyl)pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(CC=2C=CC=CC=2)CC1 GHZOZARQZLMNJF-UHFFFAOYSA-N 0.000 description 1
- FCKQXWAZMJVJSK-UHFFFAOYSA-N 6-[4-(2,5-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=C(Cl)C=2)Cl)CC1 FCKQXWAZMJVJSK-UHFFFAOYSA-N 0.000 description 1
- VMYALKVAVCTXBK-UHFFFAOYSA-N 6-[4-(6-chloropyridine-2-carbonyl)piperazin-1-yl]-n-(3-methylbutyl)pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C=2N=C(Cl)C=CC=2)CC1 VMYALKVAVCTXBK-UHFFFAOYSA-N 0.000 description 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 description 1
- FDOIWYZGTDRHBD-UHFFFAOYSA-N 6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carbonyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)C(Cl)=O)CC1 FDOIWYZGTDRHBD-UHFFFAOYSA-N 0.000 description 1
- NQXVDIRDXUURGO-UHFFFAOYSA-N 6-[4-[3-benzyl-5-(trifluoromethyl)triazole-4-carbonyl]piperazin-1-yl]-n-(3-methylbutyl)pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C=2N(N=NC=2C(F)(F)F)CC=2C=CC=CC=2)CC1 NQXVDIRDXUURGO-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
- XGTXTWJUWZDYPM-UHFFFAOYSA-N 6-[4-[5-chloro-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(Cl)C=2)C(F)(F)F)CC1 XGTXTWJUWZDYPM-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
- DWDUCTIDCRVQQG-UHFFFAOYSA-N 6-[4-[5-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]-n-pent-4-enylpyridazine-3-carboxamide Chemical compound FC1=CC=C(C(F)(F)F)C(C(=O)N2CCN(CC2)C=2N=NC(=CC=2)C(=O)NCCCC=C)=C1 DWDUCTIDCRVQQG-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
- HBTUCQWZWDNJPV-UHFFFAOYSA-N 6-[4-[[5-fluoro-2-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]-n-(3-methylbutyl)pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(CC=2C(=CC=C(F)C=2)C(F)(F)F)CC1 HBTUCQWZWDNJPV-UHFFFAOYSA-N 0.000 description 1
- PYRFLBYCBZEYGZ-UHFFFAOYSA-N 6-chloro-n-(2-ethoxyethyl)pyridazine-3-carboxamide Chemical compound CCOCCNC(=O)C1=CC=C(Cl)N=N1 PYRFLBYCBZEYGZ-UHFFFAOYSA-N 0.000 description 1
- VJHPSBDBZPHYIO-UHFFFAOYSA-N 6-chloro-n-(2-phenylpropyl)pyridazine-3-carboxamide Chemical compound C=1C=CC=CC=1C(C)CNC(=O)C1=CC=C(Cl)N=N1 VJHPSBDBZPHYIO-UHFFFAOYSA-N 0.000 description 1
- TXVFHPFGRUTLQM-UHFFFAOYSA-N 6-chloro-n-(3,3-dimethylbutyl)pyridazine-3-carboxamide Chemical compound CC(C)(C)CCNC(=O)C1=CC=C(Cl)N=N1 TXVFHPFGRUTLQM-UHFFFAOYSA-N 0.000 description 1
- IUSKNFXEVGOMEG-UHFFFAOYSA-N 6-chloro-n-(3-cyclobutylpropyl)pyridazine-3-carboxamide Chemical compound N1=NC(Cl)=CC=C1C(=O)NCCCC1CCC1 IUSKNFXEVGOMEG-UHFFFAOYSA-N 0.000 description 1
- XDAQNUCKFSITDY-UHFFFAOYSA-N 6-chloro-n-(3-cyclopropylpropyl)pyridazine-3-carboxamide Chemical compound N1=NC(Cl)=CC=C1C(=O)NCCCC1CC1 XDAQNUCKFSITDY-UHFFFAOYSA-N 0.000 description 1
- HFUJMLBBXXQADB-UHFFFAOYSA-N 6-chloro-n-(3-hydroxy-3-methylbutyl)pyridazine-3-carboxamide Chemical compound CC(C)(O)CCNC(=O)C1=CC=C(Cl)N=N1 HFUJMLBBXXQADB-UHFFFAOYSA-N 0.000 description 1
- IBYBKSUBXVRKFF-UHFFFAOYSA-N 6-chloro-n-(3-hydroxy-4,4-dimethylpentyl)pyridazine-3-carboxamide Chemical compound CC(C)(C)C(O)CCNC(=O)C1=CC=C(Cl)N=N1 IBYBKSUBXVRKFF-UHFFFAOYSA-N 0.000 description 1
- HMBXMCMAECQILL-UHFFFAOYSA-N 6-chloro-n-(3-phenylpropyl)pyridazine-3-carboxamide Chemical compound N1=NC(Cl)=CC=C1C(=O)NCCCC1=CC=CC=C1 HMBXMCMAECQILL-UHFFFAOYSA-N 0.000 description 1
- FBDRKYSYZSCAKW-UHFFFAOYSA-N 6-chloro-n-(4-cyclopropylbutyl)pyridazine-3-carboxamide Chemical compound N1=NC(Cl)=CC=C1C(=O)NCCCCC1CC1 FBDRKYSYZSCAKW-UHFFFAOYSA-N 0.000 description 1
- OEFVMOKKOVQFDG-UHFFFAOYSA-N 6-chloro-n-(4-hydroxybutyl)pyridazine-3-carboxamide Chemical compound OCCCCNC(=O)C1=CC=C(Cl)N=N1 OEFVMOKKOVQFDG-UHFFFAOYSA-N 0.000 description 1
- MGJLSLVCUKGBBY-UHFFFAOYSA-N 6-chloro-n-(4-methylpentyl)pyridazine-3-carboxamide Chemical compound CC(C)CCCNC(=O)C1=CC=C(Cl)N=N1 MGJLSLVCUKGBBY-UHFFFAOYSA-N 0.000 description 1
- LAJQRXOXKYKQCS-UHFFFAOYSA-N 6-chloro-n-(cyclopropylmethyl)pyridazine-3-carboxamide Chemical compound N1=NC(Cl)=CC=C1C(=O)NCC1CC1 LAJQRXOXKYKQCS-UHFFFAOYSA-N 0.000 description 1
- AARWOVOQMCDAIE-UHFFFAOYSA-N 6-chloro-n-[(2-methylcyclopropyl)methyl]pyridazine-3-carboxamide Chemical compound CC1CC1CNC(=O)C1=CC=C(Cl)N=N1 AARWOVOQMCDAIE-UHFFFAOYSA-N 0.000 description 1
- WGVFRDLDMXZWCX-UHFFFAOYSA-N 6-chloro-n-[(2-phenylcyclopropyl)methyl]pyridazine-3-carboxamide Chemical compound N1=NC(Cl)=CC=C1C(=O)NCC1C(C=2C=CC=CC=2)C1 WGVFRDLDMXZWCX-UHFFFAOYSA-N 0.000 description 1
- YFTKLBQTAOECJY-NSHDSACASA-N 6-chloro-n-[(2r)-2-hydroxy-2-phenylethyl]pyridazine-3-carboxamide Chemical compound C([C@H](O)C=1C=CC=CC=1)NC(=O)C1=CC=C(Cl)N=N1 YFTKLBQTAOECJY-NSHDSACASA-N 0.000 description 1
- YFTKLBQTAOECJY-LLVKDONJSA-N 6-chloro-n-[(2s)-2-hydroxy-2-phenylethyl]pyridazine-3-carboxamide Chemical compound C([C@@H](O)C=1C=CC=CC=1)NC(=O)C1=CC=C(Cl)N=N1 YFTKLBQTAOECJY-LLVKDONJSA-N 0.000 description 1
- DEZKPZZOAVOSCN-UHFFFAOYSA-N 6-chloro-n-[2-(2,4-difluorophenyl)ethyl]pyridazine-3-carboxamide Chemical compound FC1=CC(F)=CC=C1CCNC(=O)C1=CC=C(Cl)N=N1 DEZKPZZOAVOSCN-UHFFFAOYSA-N 0.000 description 1
- OJKKZYBWJHJOKB-UHFFFAOYSA-N 6-chloro-n-[2-(2-fluorophenyl)ethyl]pyridazine-3-carboxamide Chemical compound FC1=CC=CC=C1CCNC(=O)C1=CC=C(Cl)N=N1 OJKKZYBWJHJOKB-UHFFFAOYSA-N 0.000 description 1
- LPXPEPOKIJDLDG-UHFFFAOYSA-N 6-chloro-n-[2-(3-chlorophenyl)ethyl]pyridazine-3-carboxamide Chemical compound ClC1=CC=CC(CCNC(=O)C=2N=NC(Cl)=CC=2)=C1 LPXPEPOKIJDLDG-UHFFFAOYSA-N 0.000 description 1
- NDTWZTWJFWRZMP-UHFFFAOYSA-N 6-chloro-n-[2-(4-chlorophenoxy)ethyl]pyridazine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1OCCNC(=O)C1=CC=C(Cl)N=N1 NDTWZTWJFWRZMP-UHFFFAOYSA-N 0.000 description 1
- ADDQINXEKVMIGG-UHFFFAOYSA-N 6-chloro-n-[2-(4-chlorophenyl)ethyl]pyridazine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1CCNC(=O)C1=CC=C(Cl)N=N1 ADDQINXEKVMIGG-UHFFFAOYSA-N 0.000 description 1
- OWNTVOXTNLXJHP-UHFFFAOYSA-N 6-chloro-n-[2-(4-fluorophenoxy)ethyl]pyridazine-3-carboxamide Chemical compound C1=CC(F)=CC=C1OCCNC(=O)C1=CC=C(Cl)N=N1 OWNTVOXTNLXJHP-UHFFFAOYSA-N 0.000 description 1
- DVOZOMAUTKUGBG-UHFFFAOYSA-N 6-chloro-n-[2-(4-fluorophenyl)ethyl]pyridazine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCNC(=O)C1=CC=C(Cl)N=N1 DVOZOMAUTKUGBG-UHFFFAOYSA-N 0.000 description 1
- YJMZNOJCCGEMEE-UHFFFAOYSA-N 6-chloro-n-[2-(4-methoxyphenyl)ethyl]pyridazine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1CCNC(=O)C1=CC=C(Cl)N=N1 YJMZNOJCCGEMEE-UHFFFAOYSA-N 0.000 description 1
- FYMJHZDUNORDHZ-UHFFFAOYSA-N 6-chloro-n-[2-(4-phenylphenyl)ethyl]pyridazine-3-carboxamide Chemical compound N1=NC(Cl)=CC=C1C(=O)NCCC1=CC=C(C=2C=CC=CC=2)C=C1 FYMJHZDUNORDHZ-UHFFFAOYSA-N 0.000 description 1
- IHMAMPJVSGDEHL-UHFFFAOYSA-N 6-chloro-n-heptylpyridazine-3-carboxamide Chemical compound CCCCCCCNC(=O)C1=CC=C(Cl)N=N1 IHMAMPJVSGDEHL-UHFFFAOYSA-N 0.000 description 1
- ZEUPFSSRUQUCPS-UHFFFAOYSA-N 6-chloro-n-hexylpyridazine-3-carboxamide Chemical compound CCCCCCNC(=O)C1=CC=C(Cl)N=N1 ZEUPFSSRUQUCPS-UHFFFAOYSA-N 0.000 description 1
- KJKDSZRWVUKCJH-UHFFFAOYSA-N 6-chloro-n-pent-4-enylpyridazine-3-carboxamide Chemical compound ClC1=CC=C(C(=O)NCCCC=C)N=N1 KJKDSZRWVUKCJH-UHFFFAOYSA-N 0.000 description 1
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
- BMXGTJPVXWZTIU-UHFFFAOYSA-N 6-piperazin-1-ylpyridazine-3-carboxylic acid Chemical compound N1=NC(C(=O)O)=CC=C1N1CCNCC1 BMXGTJPVXWZTIU-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- IYDVFMFKIKZKEK-UHFFFAOYSA-N 8-nonylsulfanyloctanoic acid Chemical compound CCCCCCCCCSCCCCCCCC(O)=O IYDVFMFKIKZKEK-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- 108010071619 Apolipoproteins Proteins 0.000 description 1
- 102000007592 Apolipoproteins Human genes 0.000 description 1
- 102000013918 Apolipoproteins E Human genes 0.000 description 1
- 108010025628 Apolipoproteins E Proteins 0.000 description 1
- 101100009092 Arabidopsis thaliana DCD gene Proteins 0.000 description 1
- 101100135607 Arabidopsis thaliana PAO gene Proteins 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 241001533362 Astroviridae Species 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000711515 Berne virus Species 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000711443 Bovine coronavirus Species 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 241000203231 Breda virus Species 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 241001533357 Bymovirus Species 0.000 description 1
- RZYKUPXRYIOEME-UHFFFAOYSA-N CCCCCCCCCCCC[S] Chemical compound CCCCCCCCCCCC[S] RZYKUPXRYIOEME-UHFFFAOYSA-N 0.000 description 1
- 206010006895 Cachexia Diseases 0.000 description 1
- 241000711506 Canine coronavirus Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 208000005623 Carcinogenesis Diseases 0.000 description 1
- 206010050215 Carnitine palmitoyltransferase deficiency Diseases 0.000 description 1
- 208000008964 Chemical and Drug Induced Liver Injury Diseases 0.000 description 1
- 241001502567 Chikungunya virus Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- GAWKMFQFOJCLGN-UHFFFAOYSA-N Cl.C=1C=CC=C(C(F)(F)F)C=1C(C)N(CC1)CCN1C(N=N1)=CC=C1C(=O)NCCC1CC1 Chemical compound Cl.C=1C=CC=C(C(F)(F)F)C=1C(C)N(CC1)CCN1C(N=N1)=CC=C1C(=O)NCCC1CC1 GAWKMFQFOJCLGN-UHFFFAOYSA-N 0.000 description 1
- 241000710777 Classical swine fever virus Species 0.000 description 1
- 208000031288 Combined hyperlipidaemia Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 201000003883 Cystic fibrosis Diseases 0.000 description 1
- 208000001490 Dengue Diseases 0.000 description 1
- 206010012310 Dengue fever Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 238000006646 Dess-Martin oxidation reaction Methods 0.000 description 1
- 208000002249 Diabetes Complications Diseases 0.000 description 1
- 206010012655 Diabetic complications Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 206010072268 Drug-induced liver injury Diseases 0.000 description 1
- 241000710945 Eastern equine encephalitis virus Species 0.000 description 1
- 206010014596 Encephalitis Japanese B Diseases 0.000 description 1
- 241000710188 Encephalomyocarditis virus Species 0.000 description 1
- 241000709661 Enterovirus Species 0.000 description 1
- 206010066919 Epidemic polyarthritis Diseases 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- 102000009114 Fatty acid desaturases Human genes 0.000 description 1
- 241000711475 Feline infectious peritonitis virus Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 241000531123 GB virus C Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010019668 Hepatic fibrosis Diseases 0.000 description 1
- 241000700721 Hepatitis B virus Species 0.000 description 1
- 206010019728 Hepatitis alcoholic Diseases 0.000 description 1
- 241000709721 Hepatovirus A Species 0.000 description 1
- 208000033981 Hereditary haemochromatosis Diseases 0.000 description 1
- 102000003964 Histone deacetylase Human genes 0.000 description 1
- 108090000353 Histone deacetylase Proteins 0.000 description 1
- 101100309604 Homo sapiens SCD5 gene Proteins 0.000 description 1
- 244000309467 Human Coronavirus Species 0.000 description 1
- 241001479210 Human astrovirus Species 0.000 description 1
- 241001428935 Human coronavirus OC43 Species 0.000 description 1
- 241000709701 Human poliovirus 1 Species 0.000 description 1
- 208000001021 Hyperlipoproteinemia Type I Diseases 0.000 description 1
- 241000609530 Ilheus virus Species 0.000 description 1
- 241000711450 Infectious bronchitis virus Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010065973 Iron Overload Diseases 0.000 description 1
- 102000008133 Iron-Binding Proteins Human genes 0.000 description 1
- 108010035210 Iron-Binding Proteins Proteins 0.000 description 1
- 208000032382 Ischaemic stroke Diseases 0.000 description 1
- 201000005807 Japanese encephalitis Diseases 0.000 description 1
- 208000002260 Keloid Diseases 0.000 description 1
- 206010023330 Keloid scar Diseases 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- 241000710770 Langat virus Species 0.000 description 1
- 102000003960 Ligases Human genes 0.000 description 1
- 108090000364 Ligases Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000710769 Louping ill virus Species 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 241000608292 Mayaro virus Species 0.000 description 1
- 241000710185 Mengo virus Species 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
- FNJSWIPFHMKRAT-UHFFFAOYSA-N Monomethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(O)=O FNJSWIPFHMKRAT-UHFFFAOYSA-N 0.000 description 1
- 241000711466 Murine hepatitis virus Species 0.000 description 1
- 241000710908 Murray Valley encephalitis virus Species 0.000 description 1
- 241000699660 Mus musculus Species 0.000 description 1
- 101000639980 Mus musculus Acyl-CoA desaturase 3 Proteins 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000714209 Norwalk virus Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241000725177 Omsk hemorrhagic fever virus Species 0.000 description 1
- 206010033307 Overweight Diseases 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 208000002606 Paramyxoviridae Infections Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 208000018262 Peripheral vascular disease Diseases 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 241000276498 Pollachius virens Species 0.000 description 1
- 241000156302 Porcine hemagglutinating encephalomyelitis virus Species 0.000 description 1
- 241000710078 Potyvirus Species 0.000 description 1
- 241000710884 Powassan virus Species 0.000 description 1
- 206010036618 Premenstrual syndrome Diseases 0.000 description 1
- 241000220304 Prunus dulcis Species 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 1
- 241000903330 Rabbit coronavirus Species 0.000 description 1
- 241001428933 Rat coronavirus Species 0.000 description 1
- 206010038923 Retinopathy Diseases 0.000 description 1
- 241000538730 Rocio Species 0.000 description 1
- 241000710942 Ross River virus Species 0.000 description 1
- 241000710799 Rubella virus Species 0.000 description 1
- 241001533356 Rymovirus Species 0.000 description 1
- 101150048395 SCD gene Proteins 0.000 description 1
- 101100101423 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) UBI4 gene Proteins 0.000 description 1
- 101150042597 Scd2 gene Proteins 0.000 description 1
- 241000710961 Semliki Forest virus Species 0.000 description 1
- 241000710960 Sindbis virus Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 241000710888 St. Louis encephalitis virus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 101710119798 Stearoyl-CoA desaturase 2 Proteins 0.000 description 1
- 101710119799 Stearoyl-CoA desaturase 4 Proteins 0.000 description 1
- 102100033930 Stearoyl-CoA desaturase 5 Human genes 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000004006 Tick-borne encephalitis Diseases 0.000 description 1
- 102000004357 Transferases Human genes 0.000 description 1
- 108090000992 Transferases Proteins 0.000 description 1
- 208000032109 Transient ischaemic attack Diseases 0.000 description 1
- 241000711484 Transmissible gastroenteritis virus Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 241000711508 Turkey coronavirus Species 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 241000710959 Venezuelan equine encephalitis virus Species 0.000 description 1
- 206010051511 Viral diarrhoea Diseases 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 239000003875 Wang resin Substances 0.000 description 1
- 239000004164 Wax ester Substances 0.000 description 1
- 241000710886 West Nile virus Species 0.000 description 1
- 241000710951 Western equine encephalitis virus Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- RRZUCRYVIGILMG-UHFFFAOYSA-N [2-fluoro-6-(trifluoromethyl)phenyl]-piperazin-1-ylmethanone Chemical compound FC1=CC=CC(C(F)(F)F)=C1C(=O)N1CCNCC1 RRZUCRYVIGILMG-UHFFFAOYSA-N 0.000 description 1
- HWWCAYDJOZHIEM-UHFFFAOYSA-N [3-methyl-1-oxo-1-[[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]amino]butan-2-yl]azanium;chloride Chemical compound [Cl-].N1=NC(NC(=O)C([NH3+])C(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 HWWCAYDJOZHIEM-UHFFFAOYSA-N 0.000 description 1
- PFTVNHVVVKQOAM-UHFFFAOYSA-N [4-(6-aminopyridazin-3-yl)piperazin-1-yl]-(2,5-difluorophenyl)methanone Chemical compound N1=NC(N)=CC=C1N1CCN(C(=O)C=2C(=CC=C(F)C=2)F)CC1 PFTVNHVVVKQOAM-UHFFFAOYSA-N 0.000 description 1
- XXFRUFDFOVZXSX-UHFFFAOYSA-N [4-(6-aminopyridazin-3-yl)piperazin-1-yl]-(2,6-difluorophenyl)methanone Chemical compound N1=NC(N)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2F)F)CC1 XXFRUFDFOVZXSX-UHFFFAOYSA-N 0.000 description 1
- AWQTZTMZMDXIQA-UHFFFAOYSA-N [4-(6-aminopyridazin-3-yl)piperazin-1-yl]-[2-fluoro-6-(trifluoromethyl)phenyl]methanone Chemical compound N1=NC(N)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2F)C(F)(F)F)CC1 AWQTZTMZMDXIQA-UHFFFAOYSA-N 0.000 description 1
- NERFNHBZJXXFGY-UHFFFAOYSA-N [4-[(4-methylphenyl)methoxy]phenyl]methanol Chemical compound C1=CC(C)=CC=C1COC1=CC=C(CO)C=C1 NERFNHBZJXXFGY-UHFFFAOYSA-N 0.000 description 1
- IELIBVHWBDASBD-UHFFFAOYSA-N [4-fluoro-2-(trifluoromethyl)phenyl]-piperazin-1-ylmethanone Chemical compound FC(F)(F)C1=CC(F)=CC=C1C(=O)N1CCNCC1 IELIBVHWBDASBD-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 210000001789 adipocyte Anatomy 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 208000002353 alcoholic hepatitis Diseases 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- ZRYCZAWRXHAAPZ-UHFFFAOYSA-N alpha,alpha-dimethyl valeric acid Chemical compound CCCC(C)(C)C(O)=O ZRYCZAWRXHAAPZ-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000001668 ameliorated effect Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- DQPBABKTKYNPMH-UHFFFAOYSA-N amino hydrogen sulfate Chemical compound NOS(O)(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 244000309743 astrovirus Species 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 125000002785 azepinyl group Chemical group 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005870 benzindolyl group Chemical group 0.000 description 1
- 125000000928 benzodioxinyl group Chemical group O1C(=COC2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000005878 benzonaphthofuranyl group Chemical group 0.000 description 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012069 chiral reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 210000000349 chromosome Anatomy 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 230000007882 cirrhosis Effects 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000006957 competitive inhibition Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- GGIMHJFVOMBCFX-UHFFFAOYSA-M cyanomethyl(trimethyl)phosphanium;iodide Chemical compound [I-].C[P+](C)(C)CC#N GGIMHJFVOMBCFX-UHFFFAOYSA-M 0.000 description 1
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- RNIHFEJHABJCID-UHFFFAOYSA-N cyclobutylmethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1CCC1 RNIHFEJHABJCID-UHFFFAOYSA-N 0.000 description 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 208000025729 dengue disease Diseases 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 229940079920 digestives acid preparations Drugs 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 201000008865 drug-induced hepatitis Diseases 0.000 description 1
- 241001493065 dsRNA viruses Species 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 201000008220 erythropoietic protoporphyria Diseases 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- ZKRJCMKLCDWROR-ONEGZZNKSA-N ethyl (e)-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)\C=C\C(F)(F)F ZKRJCMKLCDWROR-ONEGZZNKSA-N 0.000 description 1
- ALHZYRDSGJMIDK-UHFFFAOYSA-N ethyl 2-[(6-chloropyridazine-3-carbonyl)amino]butanoate Chemical compound CCOC(=O)C(CC)NC(=O)C1=CC=C(Cl)N=N1 ALHZYRDSGJMIDK-UHFFFAOYSA-N 0.000 description 1
- XBSGYVHOINMTIM-UHFFFAOYSA-N ethyl 3-isocyanatopropanoate Chemical compound CCOC(=O)CCN=C=O XBSGYVHOINMTIM-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 208000030533 eye disease Diseases 0.000 description 1
- 230000004129 fatty acid metabolism Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 125000003844 furanonyl group Chemical group 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000000404 glutamine group Chemical group N[C@@H](CCC(N)=O)C(=O)* 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 201000010284 hepatitis E Diseases 0.000 description 1
- 210000003494 hepatocyte Anatomy 0.000 description 1
- TZTFFIFDGZOKCS-UHFFFAOYSA-N heptadecanethioic s-acid Chemical compound CCCCCCCCCCCCCCCCC(O)=S TZTFFIFDGZOKCS-UHFFFAOYSA-N 0.000 description 1
- 125000004447 heteroarylalkenyl group Chemical group 0.000 description 1
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 229960002885 histidine Drugs 0.000 description 1
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 208000020346 hyperlipoproteinemia Diseases 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- CZALJDQHONFVFU-UHFFFAOYSA-N isocyanatocyclopentane Chemical compound O=C=NC1CCCC1 CZALJDQHONFVFU-UHFFFAOYSA-N 0.000 description 1
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
- 210000001117 keloid Anatomy 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 235000020997 lean meat Nutrition 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- AGBQKNBQESQNJD-UHFFFAOYSA-N lipoic acid Chemical compound OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 description 1
- 235000019136 lipoic acid Nutrition 0.000 description 1
- 230000008604 lipoprotein metabolism Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000001853 liver microsome Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 1
- GJWSXJLMFMWHJJ-UHFFFAOYSA-N methyl 2-[(6-chloropyridazine-3-carbonyl)amino]-4-methylpentanoate Chemical compound COC(=O)C(CC(C)C)NC(=O)C1=CC=C(Cl)N=N1 GJWSXJLMFMWHJJ-UHFFFAOYSA-N 0.000 description 1
- FPKXYXKLOWAIOX-UHFFFAOYSA-N methyl 6-chloropyridazine-3-carboxylate Chemical compound COC(=O)C1=CC=C(Cl)N=N1 FPKXYXKLOWAIOX-UHFFFAOYSA-N 0.000 description 1
- REYKVZJYIFOXTI-UHFFFAOYSA-N methyl 6-oxo-1h-pyridazine-3-carboxylate Chemical compound COC(=O)C=1C=CC(=O)NN=1 REYKVZJYIFOXTI-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- RRIRDPSOCUCGBV-UHFFFAOYSA-N methylenedioxyphenethylamine Chemical compound NCCC1=CC=C2OCOC2=C1 RRIRDPSOCUCGBV-UHFFFAOYSA-N 0.000 description 1
- 210000001589 microsome Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- DTJICJPQTIWVPU-UHFFFAOYSA-N n-(1,3-benzodioxol-5-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=2C=C3OCOC3=CC=2)CC1 DTJICJPQTIWVPU-UHFFFAOYSA-N 0.000 description 1
- HIUGAZHBBCYCGZ-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-(3,5-dimethylpiperazin-1-yl)pyridazine-3-carboxamide Chemical compound C1C(C)NC(C)CN1C1=CC=C(C(=O)NCCC2CC2)N=N1 HIUGAZHBBCYCGZ-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 1
- HQXYLBNTDXQOKS-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[2-(trifluoromethyl)cyclopropanecarbonyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC(F)(F)C1CC1C(=O)N1CCN(C=2N=NC(=CC=2)C(=O)NCCC2CC2)CC1 HQXYLBNTDXQOKS-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 1
- KXXQJZDFJCKDLL-UHFFFAOYSA-N n-(3-methylbutyl)-6-[4-(1,2-oxazole-5-carbonyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C=2ON=CC=2)CC1 KXXQJZDFJCKDLL-UHFFFAOYSA-N 0.000 description 1
- XLGAVYAFMODNHY-UHFFFAOYSA-N n-(3-methylbutyl)-6-[4-(4,4,4-trifluoro-2-methylbutanoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C(C)CC(F)(F)F)CC1 XLGAVYAFMODNHY-UHFFFAOYSA-N 0.000 description 1
- MCELPMSKGYBMJK-UHFFFAOYSA-N n-(3-methylbutyl)-6-[4-(4,4,4-trifluoro-3-methylbut-2-enoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C=C(C)C(F)(F)F)CC1 MCELPMSKGYBMJK-UHFFFAOYSA-N 0.000 description 1
- BYVZCUGJYXPQFA-UHFFFAOYSA-N n-(3-methylbutyl)-6-[4-(4,4,4-trifluoro-3-methylbutanoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)CC(C)C(F)(F)F)CC1 BYVZCUGJYXPQFA-UHFFFAOYSA-N 0.000 description 1
- WJCQKXJQFBAQIF-UHFFFAOYSA-N n-(3-methylbutyl)-6-[4-(4,4,4-trifluorobutanoyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)CCC(F)(F)F)CC1 WJCQKXJQFBAQIF-UHFFFAOYSA-N 0.000 description 1
- OEOJLGQPPAIHLI-UHFFFAOYSA-N n-(3-methylbutyl)-6-[4-(4-methylpiperazine-1-carbonyl)piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)N2CCN(C)CC2)CC1 OEOJLGQPPAIHLI-UHFFFAOYSA-N 0.000 description 1
- ZBUZEZRPZOMTMK-UHFFFAOYSA-N n-(3-methylbutyl)-6-[4-[1-(trifluoromethyl)cyclopropanecarbonyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C2(CC2)C(F)(F)F)CC1 ZBUZEZRPZOMTMK-UHFFFAOYSA-N 0.000 description 1
- TWAYMXUZSDMPKF-UHFFFAOYSA-N n-(3-methylbutyl)-6-[4-[1-methyl-5-(trifluoromethyl)pyrazole-4-carbonyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C2=C(N(C)N=C2)C(F)(F)F)CC1 TWAYMXUZSDMPKF-UHFFFAOYSA-N 0.000 description 1
- BXZAGFWMFJNEDZ-UHFFFAOYSA-N n-(3-methylbutyl)-6-[4-[2-(trifluoromethoxy)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)OC(F)(F)F)CC1 BXZAGFWMFJNEDZ-UHFFFAOYSA-N 0.000 description 1
- BPJWSCOTFJMAJE-UHFFFAOYSA-N n-(3-methylbutyl)-6-[4-[2-methyl-5-(trifluoromethyl)triazole-4-carbonyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=NN(C)N=2)C(F)(F)F)CC1 BPJWSCOTFJMAJE-UHFFFAOYSA-N 0.000 description 1
- MPSGPOWYGAFZIJ-UHFFFAOYSA-N n-(3-methylbutyl)-6-[4-[4-(trifluoromethyl)pyridine-3-carbonyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=NC=2)C(F)(F)F)CC1 MPSGPOWYGAFZIJ-UHFFFAOYSA-N 0.000 description 1
- GATFEPZZBAGMCQ-UHFFFAOYSA-N n-(3-methylbutyl)-6-[4-[[2-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCC(C)C)=CC=C1N1CCN(CC=2C(=CC=CC=2)C(F)(F)F)CC1 GATFEPZZBAGMCQ-UHFFFAOYSA-N 0.000 description 1
- YBEGCFFHJCQYKN-UHFFFAOYSA-N n-(4-methylpentyl)-6-piperazin-1-ylpyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCCC(C)C)=CC=C1N1CCNCC1 YBEGCFFHJCQYKN-UHFFFAOYSA-N 0.000 description 1
- LEYAZDIVGBMRHE-UHFFFAOYSA-N n-(cyclobutylmethyl)-6-piperazin-1-ylpyridazine-3-carboxamide Chemical compound C=1C=C(N2CCNCC2)N=NC=1C(=O)NCC1CCC1 LEYAZDIVGBMRHE-UHFFFAOYSA-N 0.000 description 1
- WRKZKTLKOYZIAX-UHFFFAOYSA-N n-[2-(2,4-difluorophenyl)ethyl]-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC(F)=CC=C1CCNC(=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=N1 WRKZKTLKOYZIAX-UHFFFAOYSA-N 0.000 description 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 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- QUBQVORXQDFOIX-UHFFFAOYSA-N n-hexyl-6-piperazin-1-ylpyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NCCCCCC)=CC=C1N1CCNCC1 QUBQVORXQDFOIX-UHFFFAOYSA-N 0.000 description 1
- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 230000009826 neoplastic cell growth Effects 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 229940074355 nitric acid Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 235000021590 normal diet Nutrition 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000005060 octahydroindolyl group Chemical group N1(CCC2CCCCC12)* 0.000 description 1
- 125000005061 octahydroisoindolyl group Chemical group C1(NCC2CCCCC12)* 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- XDUHQPOXLUAVEE-BPMMELMSSA-N oleoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCC\C=C/CCCCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 XDUHQPOXLUAVEE-BPMMELMSSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- QBYOCCWNZAOZTL-MDMKAECGSA-N palmitoleoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCC\C=C/CCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 QBYOCCWNZAOZTL-MDMKAECGSA-N 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- LQAVWYMTUMSFBE-UHFFFAOYSA-N pent-4-en-1-ol Chemical compound OCCCC=C LQAVWYMTUMSFBE-UHFFFAOYSA-N 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229950009215 phenylbutanoic acid Drugs 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
- DFOXKPDFWGNLJU-UHFFFAOYSA-N pinacolyl alcohol Chemical compound CC(O)C(C)(C)C DFOXKPDFWGNLJU-UHFFFAOYSA-N 0.000 description 1
- GMPXEUQDMLJCQG-UHFFFAOYSA-N piperazin-1-yl-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)N1CCNCC1 GMPXEUQDMLJCQG-UHFFFAOYSA-N 0.000 description 1
- XCUUPNXLEWJEKY-UHFFFAOYSA-N piperazin-1-yl-[2-(trifluoromethyl)phenyl]methanethione Chemical compound FC(F)(F)C1=CC=CC=C1C(=S)N1CCNCC1 XCUUPNXLEWJEKY-UHFFFAOYSA-N 0.000 description 1
- UKBZYQYTGZWCSF-UHFFFAOYSA-N piperazin-1-yl-[2-(trifluoromethyl)phenyl]methanone;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC=CC=C1C(=O)N1CCNCC1 UKBZYQYTGZWCSF-UHFFFAOYSA-N 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- LETVJWLLIMJADE-UHFFFAOYSA-N pyridazin-3-amine Chemical compound NC1=CC=CN=N1 LETVJWLLIMJADE-UHFFFAOYSA-N 0.000 description 1
- XACWJIQLDLUFSR-UHFFFAOYSA-N pyrrolidine-1-carbonyl chloride Chemical compound ClC(=O)N1CCCC1 XACWJIQLDLUFSR-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000003362 replicative effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004141 reverse cholesterol transport Effects 0.000 description 1
- 230000006965 reversible inhibition Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical group 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000003462 sulfoxides Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- WDPWEXWMQDRXAL-UHFFFAOYSA-N tert-butyl 1,4-diazepane-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCNCC1 WDPWEXWMQDRXAL-UHFFFAOYSA-N 0.000 description 1
- WEZYFYMYMKUAHY-UHFFFAOYSA-N tert-butyl 2,4-dibenzylpiperazine-1-carboxylate Chemical compound C1C(CC=2C=CC=CC=2)N(C(=O)OC(C)(C)C)CCN1CC1=CC=CC=C1 WEZYFYMYMKUAHY-UHFFFAOYSA-N 0.000 description 1
- LXOFYXAMQPVFHC-UHFFFAOYSA-N tert-butyl 4-[2-(trifluoromethyl)benzoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)C1=CC=CC=C1C(F)(F)F LXOFYXAMQPVFHC-UHFFFAOYSA-N 0.000 description 1
- YZUAOVCUGSBIPP-UHFFFAOYSA-N tert-butyl N-[1-([1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl]carbamate Chemical compound C1=CC=CN2C(C(NC(=O)OC(C)(C)C)C)=NN=C21 YZUAOVCUGSBIPP-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
- 201000010875 transient cerebral ischemia Diseases 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000005455 trithianyl group Chemical group 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 235000019386 wax ester Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 238000011684 zucker rat (obese) Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Gastroenterology & Hepatology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US49109503P | 2003-07-30 | 2003-07-30 | |
US54689804P | 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 | |
US54678604P | 2004-02-23 | 2004-02-23 | |
US55344604P | 2004-03-16 | 2004-03-16 | |
US55349104P | 2004-03-16 | 2004-03-16 | |
US55341604P | 2004-03-16 | 2004-03-16 | |
US55340404P | 2004-03-16 | 2004-03-16 | |
US55340304P | 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 (2)
Publication Number | Publication Date |
---|---|
NO20060981L NO20060981L (no) | 2006-05-02 |
NO332822B1 true NO332822B1 (no) | 2013-01-21 |
Family
ID=34120234
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20060981A NO332822B1 (no) | 2003-07-30 | 2006-02-28 | Pyridazinderivater, farmasoytiske preparater inneholdende slike, og deres anvendelse som terapeutiske midler |
Country Status (23)
Country | Link |
---|---|
US (1) | US7335658B2 (es) |
EP (3) | EP3042895A1 (es) |
JP (1) | JP4808616B2 (es) |
KR (1) | KR100934554B1 (es) |
AR (1) | AR047557A1 (es) |
AT (1) | ATE527242T1 (es) |
AU (2) | AU2004261252C1 (es) |
CA (1) | CA2533899C (es) |
CY (1) | CY1112178T1 (es) |
DK (1) | DK1648874T3 (es) |
EC (1) | ECSP066313A (es) |
ES (2) | ES2375134T3 (es) |
HK (2) | HK1097256A1 (es) |
HR (1) | HRP20110974T1 (es) |
IL (1) | IL173395A (es) |
MA (1) | MA28011A1 (es) |
NO (1) | NO332822B1 (es) |
NZ (1) | NZ545265A (es) |
PL (1) | PL1648874T3 (es) |
PT (1) | PT1648874E (es) |
TN (1) | TNSN06034A1 (es) |
TW (2) | TWI345974B (es) |
WO (1) | WO2005011655A2 (es) |
Families Citing this family (67)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040226056A1 (en) * | 1998-12-22 | 2004-11-11 | Myriad Genetics, Incorporated | Compositions and methods for treating neurological disorders and diseases |
US7390813B1 (en) * | 2001-12-21 | 2008-06-24 | Xenon Pharmaceuticals Inc. | Pyridylpiperazines and aminonicotinamides and their use as therapeutic agents |
US20050119251A1 (en) * | 2001-12-21 | 2005-06-02 | Jian-Min Fu | Nicotinamide derivatives and their use as therapeutic agents |
US7754711B2 (en) * | 2003-07-30 | 2010-07-13 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
US7759348B2 (en) * | 2003-07-30 | 2010-07-20 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
ATE532772T1 (de) * | 2003-07-30 | 2011-11-15 | Xenon Pharmaceuticals Inc | Piperazinderivate und deren verwendung als therapeutische mittel |
WO2005011655A2 (en) | 2003-07-30 | 2005-02-10 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
KR20060037410A (ko) * | 2003-07-30 | 2006-05-03 | 제논 파마슈티칼스 인크. | 피리다진 유도체 및 그의 치료제로서의 용도 |
WO2005072681A2 (en) * | 2004-01-23 | 2005-08-11 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments of inflammatory and neurotic pain. |
US8071603B2 (en) | 2004-09-20 | 2011-12-06 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
US7592343B2 (en) * | 2004-09-20 | 2009-09-22 | Xenon Pharmaceuticals Inc. | Pyridazine-piperazine compounds and their use as stearoyl-CoA desaturase inhibitors |
AR051294A1 (es) * | 2004-09-20 | 2007-01-03 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa |
CA2580787A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes |
WO2006034341A2 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-coa-desaturase |
US20080167321A1 (en) * | 2004-09-20 | 2008-07-10 | Xenon Pharmaceuticals Inc. | Pyridine Derivatives For Inhibiting Human Stearoyl-Coa-Desaturase |
EP1799668A1 (en) * | 2004-09-20 | 2007-06-27 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-coa desaturase |
JP4958786B2 (ja) * | 2004-09-20 | 2012-06-20 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 複素環誘導体および治療薬としてのそれらの使用 |
BRPI0515488A (pt) | 2004-09-20 | 2008-07-29 | Xenon Pharmaceuticals Inc | derivados de heterocìclicos e seu uso como agentes terapêuticos |
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 |
BRPI0611187A2 (pt) | 2005-06-03 | 2010-08-24 | Xenon Pharmaceuticals Inc | derivados aminotiazàis como inibidores da estearoil-coa desaturase humana |
CN101203244A (zh) * | 2005-07-01 | 2008-06-18 | 诺瓦提斯公司 | 肾素抑制剂和胰岛素分泌促进剂或胰岛素敏化剂的组合产品 |
JO2769B1 (en) | 2005-10-26 | 2014-03-15 | جانسين فارماسوتيكا ان. في | Rapid decomposition of physiologically antagonistic agents of the 2-dopamine receptor |
CA2632936A1 (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 |
WO2007143597A2 (en) | 2006-06-05 | 2007-12-13 | Novartis Ag | Organic compounds |
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 |
WO2008096746A1 (ja) | 2007-02-06 | 2008-08-14 | Takeda Pharmaceutical Company Limited | スピロ化合物およびその用途 |
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 |
CN101663292A (zh) * | 2007-04-23 | 2010-03-03 | 詹森药业有限公司 | 作为快速解离的多巴胺2受体拮抗剂的4-烷氧基哒嗪衍生物 |
CA2682671C (en) | 2007-04-23 | 2015-11-17 | Janssen Pharmaceutica N.V. | Thia(dia)zoles as fast dissociating dopamine 2 receptor antagonists |
PT2142529E (pt) | 2007-04-27 | 2014-03-20 | Purdue Pharma Lp | Antagonistas de trpv1 e as respectivas utilizações |
CN101820757A (zh) | 2007-06-01 | 2010-09-01 | 普林斯顿大学托管委员会 | 通过调节宿主细胞代谢途径治疗病毒感染 |
WO2008157844A1 (en) | 2007-06-21 | 2008-12-24 | Forest Laboratories Holdings Limited | Novel piperazine derivatives as inhibitors of stearoyl-coa desaturase |
KR101189189B1 (ko) | 2007-08-08 | 2012-10-10 | 그레이스웨이 파머수티컬스, 엘엘씨 | 페녹시-피롤리딘 유도체 및 이의 용도 및 조성물 |
WO2009038974A1 (en) | 2007-09-20 | 2009-03-26 | Irm Llc | Compounds and compositions as modulators of gpr119 activity |
WO2009037542A2 (en) | 2007-09-20 | 2009-03-26 | Glenmark Pharmaceuticals, S.A. | Spirocyclic compounds as stearoyl coa desaturase inhibitors |
KR101198582B1 (ko) * | 2007-12-11 | 2012-11-06 | 에프. 호프만-라 로슈 아게 | 스테아로일-coa 불포화화 효소의 억제제 |
LT2307374T (lt) | 2008-07-31 | 2017-04-25 | Janssen Pharmaceutica Nv | Piperazin-1-il-trifluormetil-pakeistieji piridinai kaip greitai disocijuojantys dopamino 2 receptoriaus antagonistai |
WO2010094120A1 (en) | 2009-02-17 | 2010-08-26 | Merck Frosst Canada Ltd. | 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 |
MX2012004078A (es) | 2009-10-09 | 2012-07-25 | Irm Llc | Compuestos y composiciones como moduladores de la actividad de gpr119. |
US8394858B2 (en) | 2009-12-03 | 2013-03-12 | Novartis Ag | Cyclohexane derivatives and uses thereof |
US8697739B2 (en) | 2010-07-29 | 2014-04-15 | Novartis Ag | Bicyclic acetyl-CoA carboxylase inhibitors and uses thereof |
SG195136A1 (en) | 2011-06-22 | 2013-12-30 | Purdue Pharma Lp | Trpv1 antagonists including dihydroxy substituent and uses thereof |
MX2014004426A (es) | 2011-10-15 | 2014-07-09 | Genentech Inc | Metodos de uso de antagonistas de scd1. |
US9260441B2 (en) | 2012-03-28 | 2016-02-16 | Intervet Inc. | Heteroaryl compounds with cyclic bridging unit |
MX2014014174A (es) | 2012-05-22 | 2015-07-06 | Hoffmann La Roche | Inhibidores selectivos de celulas no diferenciadas. |
WO2014052619A1 (en) | 2012-09-27 | 2014-04-03 | Irm Llc | Piperidine derivatives and compositions as modulators of gpr119 activity |
DK3350165T3 (da) | 2015-09-16 | 2023-09-25 | Organovo Inc | Farnesoid-X-receptoragonister og anvendelser deraf |
CN110099898B (zh) | 2016-10-24 | 2023-07-25 | 优曼尼蒂治疗公司 | 化合物及其用途 |
IL304017A (en) | 2017-01-06 | 2023-08-01 | Yumanity Therapeutics Inc | Methods for treating neurological disorders |
WO2018170166A1 (en) | 2017-03-15 | 2018-09-20 | Metacrine, Inc. | Farnesoid x receptor agonists and uses thereof |
MX2019010907A (es) | 2017-03-15 | 2019-11-07 | Metacrine Inc | Agonistas del receptor x farnesoide, y usos de los mismos. |
EP3700934A4 (en) | 2017-10-24 | 2021-10-27 | Yumanity Therapeutics, Inc. | COMPOUNDS AND USES OF THESE COMPOUNDS |
BR112020022790A2 (pt) * | 2018-05-09 | 2021-02-02 | Lg Chem, Ltd | novo composto que exibe atividade inibitória de enteropeptidase |
BR112021004919A2 (pt) | 2018-09-18 | 2021-06-01 | Metacrine, Inc. | agonistas de receptor farnesoide x e usos dos mesmos |
CA3127791A1 (en) | 2019-01-24 | 2020-07-30 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
Family Cites Families (57)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US667452A (en) * | 1900-09-08 | 1901-02-05 | John A Hendrickson | Computing attachment for pumps. |
US2985657A (en) * | 1959-10-12 | 1961-05-23 | Paul A J Janssen | 1-(aroylalkyl)-4-heterocyclylpiperazines |
DE2341925A1 (de) | 1973-08-20 | 1975-03-06 | Thomae Gmbh Dr K | Neue pyrimidinderivate und verfahren zu ihrer herstellung |
AT340933B (de) * | 1973-08-20 | 1978-01-10 | Thomae Gmbh Dr K | Verfahren zur herstellung neuer pyrimidinderivate und ihrer saureadditionssalze |
US5001125A (en) | 1984-03-26 | 1991-03-19 | Janssen Pharmaceutica N.V. | Anti-virally active pyridazinamines |
ES8802151A1 (es) | 1985-07-31 | 1988-04-01 | Janssen Pharmaceutica Nv | Un procedimiento para la preparacion de nuevos piridazinaminas. |
JPH02502824A (ja) | 1987-04-03 | 1990-09-06 | ジ・アップジョン・カンパニー | アミノ‐9,10‐セコステロイド類 |
CA1338012C (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 |
DE69705819T2 (de) * | 1996-01-15 | 2002-04-11 | Janssen Pharmaceutica N.V., Beerse | Angiogenesis hemmende pyridazinamine |
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 |
AU8096798A (en) | 1997-06-27 | 1999-01-19 | Resolution Pharmaceuticals Inc. | Dopamine d4 receptor ligands |
ATE229945T1 (de) | 1998-03-19 | 2003-01-15 | Upjohn Co | Zur behandlung von cmv infektionen geeignete 1,3, 4-thiadiazole |
WO2000023450A1 (fr) * | 1998-10-21 | 2000-04-27 | Takeda Chemical Industries, Ltd. | Derives fusionnes de pyridazine, procede de preparation correspondant et utilisation de ces derives |
WO2000025768A1 (en) | 1998-10-29 | 2000-05-11 | Trega Biosciences, Inc. | Oxadiazole, thiadiazole and triazole derivatives and combinatorial libraries thereof |
WO2000044743A1 (fr) | 1999-01-28 | 2000-08-03 | Nippon Shinyaku Co., Ltd. | Derives d'amides et compositions de medicaments |
EP1147112B1 (en) | 1999-01-29 | 2003-10-29 | Abbott Laboratories | Diazabicyclic derivatives as nicotinic acetylcholine receptor ligands |
EP1035115B1 (en) | 1999-02-24 | 2004-09-29 | F. Hoffmann-La Roche Ag | 4-Phenylpyridine derivatives and their use as NK-1 receptor antagonists |
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 |
EP1243268A4 (en) | 1999-12-14 | 2003-05-21 | Nippon Shinyaku Co Ltd | MEDICINAL COMPOSITION |
US6987001B2 (en) | 2000-02-24 | 2006-01-17 | Xenon Pharmaceuticals Inc. | Methods and compositions using stearoyl-CoA desaturase to identify triglyceride reducing therapeutic agents |
AU2001247372A1 (en) | 2000-03-15 | 2001-09-24 | 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 |
US7232662B2 (en) | 2000-09-26 | 2007-06-19 | Xenon Pharmaceuticals 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 |
IL158941A0 (en) * | 2001-05-22 | 2004-05-12 | Neurogen Corp | Melanin concentrating hormone receptor ligands: substituted 1-benzyl-4-aryl piperazine analogues |
WO2002102778A1 (fr) | 2001-06-15 | 2002-12-27 | Yamanouchi Pharmaceutical Co., Ltd. | Derive de phenylpyridinecarbonylpiperazine |
JP4186518B2 (ja) * | 2001-06-15 | 2008-11-26 | アステラス製薬株式会社 | フェニルピリジン誘導体 |
EP1452525A4 (en) | 2001-10-30 | 2005-01-26 | Nippon Shinyaku Co Ltd | AMIDE DERIVATIVES AND CORRESPONDING MEDICAMENTS |
US6620811B2 (en) | 2001-11-19 | 2003-09-16 | Hoffmann-La Roche Inc. | Isonicotin- and nicotinamide derivatives of benzothiazoles |
CA2468716A1 (en) | 2001-11-28 | 2003-06-05 | Fujisawa Pharmaceutical Co., Ltd. | Heterocyclic amide compounds as apolipoprotein b inhibitors |
AU2002350172A1 (en) | 2001-12-07 | 2003-06-23 | Eli Lilly And Company | Substituted heterocyclic carboxamides with antithrombotic activity |
EP1474401A2 (en) | 2002-02-05 | 2004-11-10 | Novo Nordisk A/S | Novel aryl- and heteroarylpiperazines |
CA2476586C (en) * | 2002-03-13 | 2011-11-01 | Janssen Pharmaceutica N.V. | Sulfonyl-derivatives as novel inhibitors of histone deacetylase |
JP4725945B2 (ja) | 2002-03-13 | 2011-07-13 | 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 | ヒストンデアセチラーゼの新規な阻害剤としてのスルホニルアミノ誘導体 |
PL212089B1 (pl) | 2002-03-13 | 2012-08-31 | Janssen Pharmaceutica Nv | Związki heterocykliczne jako inhibitory deacetylazy histonowej, kompozycja farmaceutyczna je zawierająca, ich zastosowanie, sposób wytwarzania, sposób wykrywania lub identyfikacji HDAC oraz kompozycja |
WO2003091247A2 (en) | 2002-04-25 | 2003-11-06 | Pharmacia Corporation | Piperidinyl-and piperazinyl-sulfonylmethyl hydroxamic acids and their use as protease inhibitors |
US20040072877A1 (en) | 2002-07-25 | 2004-04-15 | Ntambi James M. | Method for increasing insulin sensitivity and for treating and preventing type 2 diabetes |
WO2004035549A1 (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 |
BRPI0406809A (pt) | 2003-01-17 | 2005-12-27 | Warner Lambert Co | Heterociclos substituìdos de 2-aminopiridina como inibidores da proliferação celular |
ATE532772T1 (de) | 2003-07-30 | 2011-11-15 | Xenon Pharmaceuticals Inc | Piperazinderivate und deren verwendung als therapeutische mittel |
WO2005011655A2 (en) | 2003-07-30 | 2005-02-10 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
KR20060037410A (ko) * | 2003-07-30 | 2006-05-03 | 제논 파마슈티칼스 인크. | 피리다진 유도체 및 그의 치료제로서의 용도 |
-
2004
- 2004-07-29 WO PCT/US2004/024548 patent/WO2005011655A2/en active Application Filing
- 2004-07-29 AR ARP040102690A patent/AR047557A1/es not_active Application Discontinuation
- 2004-07-29 PL PL04779562T patent/PL1648874T3/pl unknown
- 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 EP EP16000190.5A patent/EP3042895A1/en not_active Withdrawn
- 2004-07-29 ES ES04779562T patent/ES2375134T3/es not_active Expired - Lifetime
- 2004-07-29 TW TW093122736A patent/TWI345974B/zh not_active IP Right Cessation
- 2004-07-29 EP EP10184939.6A patent/EP2316827B1/en not_active Expired - Lifetime
- 2004-07-29 TW TW099123172A patent/TW201038270A/zh unknown
- 2004-07-29 US US10/901,563 patent/US7335658B2/en not_active Expired - Fee Related
- 2004-07-29 NZ NZ545265A patent/NZ545265A/en not_active IP Right Cessation
- 2004-07-29 EP EP04779562A patent/EP1648874B1/en not_active Expired - Lifetime
- 2004-07-29 DK DK04779562.0T patent/DK1648874T3/da active
- 2004-07-29 ES ES10184939.6T patent/ES2568769T3/es not_active Expired - Lifetime
- 2004-07-29 JP JP2006522075A patent/JP4808616B2/ja not_active Expired - Fee Related
- 2004-07-29 CA CA2533899A patent/CA2533899C/en not_active Expired - Lifetime
- 2004-07-29 AU AU2004261252A patent/AU2004261252C1/en not_active Ceased
- 2004-07-29 PT PT04779562T patent/PT1648874E/pt unknown
-
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 |
---|---|---|
NO332822B1 (no) | Pyridazinderivater, farmasoytiske preparater inneholdende slike, og deres anvendelse som terapeutiske midler | |
CA2597069C (en) | Pyridazine derivatives and their use as therapeutic agents | |
US7919496B2 (en) | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-CoA desaturase enzymes | |
EP1651616B1 (en) | Pyridazine derivatives and their use as therapeutic agents | |
AU2004261268A1 (en) | Piperazine derivatives and their use as therapeutic agents | |
MXPA06001205A (es) | Derivados de piridazina y su uso como agentes terapeuticos | |
MXPA06001206A (es) | Derivados de piperazina y su uso como agentes terapeuticos | |
MXPA06001204A (es) | Derivados de piridazinay su uso como agentes terapeuticos |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM1K | Lapsed by not paying the annual fees |