TW201326153A - 磷酸二酯酶第１０ａ型之新穎抑制劑化合物 - Google Patents

Info

Publication number

TW201326153A

TW201326153A TW101141932A TW101141932A TW201326153A TW 201326153 A TW201326153 A TW 201326153A TW 101141932 A TW101141932 A TW 101141932A TW 101141932 A TW101141932 A TW 101141932A TW 201326153 A TW201326153 A TW 201326153A

Authority

TW

Taiwan

Prior art keywords

ethyl

quinolin

pyridin

group

pyridazine

Prior art date

2011-11-09

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 379
• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 title claims abstract description 17
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 title claims abstract description 17
• 239000003112 inhibitor Substances 0.000 title abstract description 5
• -1 trimethyldecyl Chemical group 0.000 claims abstract description 997
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 372
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 203
• 239000001257 hydrogen Substances 0.000 claims abstract description 180
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 110
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 107
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 107
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 99
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 79
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 55
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 50
• 150000002367 halogens Chemical class 0.000 claims abstract description 49
• 239000003814 drug Substances 0.000 claims abstract description 36
• 238000011282 treatment Methods 0.000 claims abstract description 32
• 208000020016 psychiatric disease Diseases 0.000 claims abstract description 14
• 230000000926 neurological effect Effects 0.000 claims abstract description 13
• 208000012902 Nervous system disease Diseases 0.000 claims abstract description 8
• 208000025966 Neurological disease Diseases 0.000 claims abstract description 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 6
• 238000004519 manufacturing process Methods 0.000 claims abstract description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 424
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 131
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 119
• 125000005842 heteroatom Chemical group 0.000 claims description 107
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 99
• 229910052731 fluorine Inorganic materials 0.000 claims description 90
• 150000003839 salts Chemical class 0.000 claims description 89
• 239000011737 fluorine Substances 0.000 claims description 88
• 229940002612 prodrug Drugs 0.000 claims description 83
• 239000000651 prodrug Substances 0.000 claims description 83
• 125000001072 heteroaryl group Chemical group 0.000 claims description 77
• 150000001204 N-oxides Chemical class 0.000 claims description 69
• 229920006395 saturated elastomer Polymers 0.000 claims description 65
• 150000004677 hydrates Chemical class 0.000 claims description 61
• 239000000126 substance Substances 0.000 claims description 59
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 46
• 125000001424 substituent group Chemical group 0.000 claims description 45
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 44
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 44
• 125000004432 carbon atom Chemical group C* 0.000 claims description 43
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 42
• 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 42
• 239000000460 chlorine Chemical group 0.000 claims description 38
• VOIKXRQSXFJVMT-UHFFFAOYSA-N 5h-thieno[2,3-d]pyridazin-4-one Chemical compound O=C1NN=CC2=C1C=CS2 VOIKXRQSXFJVMT-UHFFFAOYSA-N 0.000 claims description 36
• 125000000623 heterocyclic group Chemical group 0.000 claims description 36
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 35
• 229910052801 chlorine Inorganic materials 0.000 claims description 35
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 34
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 34
• 125000002950 monocyclic group Chemical group 0.000 claims description 27
• 125000004076 pyridyl group Chemical group 0.000 claims description 27
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
• 125000002619 bicyclic group Chemical group 0.000 claims description 25
• 125000002541 furyl group Chemical group 0.000 claims description 25
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 25
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 24
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 23
• 125000002883 imidazolyl group Chemical group 0.000 claims description 23
• 125000002971 oxazolyl group Chemical group 0.000 claims description 23
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 23
• 125000000335 thiazolyl group Chemical group 0.000 claims description 23
• 125000001544 thienyl group Chemical group 0.000 claims description 23
• 241000124008 Mammalia Species 0.000 claims description 22
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 22
• 125000000217 alkyl group Chemical group 0.000 claims description 20
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 20
• 201000010099 disease Diseases 0.000 claims description 19
• 201000000980 schizophrenia Diseases 0.000 claims description 19
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 18
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
• 125000002837 carbocyclic group Chemical group 0.000 claims description 17
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 17
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 16
• 239000001301 oxygen Substances 0.000 claims description 16
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 15
• SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
• 208000019901 Anxiety disease Diseases 0.000 claims description 14
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• 125000004429 atom Chemical group 0.000 claims description 13
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 13
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 11
• 125000001153 fluoro group Chemical group F* 0.000 claims description 11
• VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 claims description 11
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 11
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
• 208000010877 cognitive disease Diseases 0.000 claims description 9
• 230000002401 inhibitory effect Effects 0.000 claims description 9
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 9
• 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 9
• 229930192474 thiophene Natural products 0.000 claims description 9
• DWHIRSWNWDXFMQ-UHFFFAOYSA-N 4h-pyridazin-5-one Chemical compound O=C1CC=NN=C1 DWHIRSWNWDXFMQ-UHFFFAOYSA-N 0.000 claims description 8
• SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims description 7
• 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 7
• 208000020925 Bipolar disease Diseases 0.000 claims description 7
• 230000036506 anxiety Effects 0.000 claims description 7
• WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 6
• QGFYFOHMBDMGBZ-UHFFFAOYSA-N 5-[(7-chloroquinolin-4-yl)amino]-2-(diethylaminomethyl)phenol Chemical compound C1=C(O)C(CN(CC)CC)=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 QGFYFOHMBDMGBZ-UHFFFAOYSA-N 0.000 claims description 6
• 239000002253 acid Substances 0.000 claims description 6
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 6
• RROZJMWKQNSJOL-OXJNMPFZSA-N 3-pyrimidin-5-yl-5-[(1R,2R)-2-quinolin-2-ylcyclopropyl]thieno[3,2-c]pyridin-4-one Chemical compound N1=CN=CC(=C1)C1=CSC2=C1C(N(C=C2)[C@H]2[C@@H](C2)C2=NC1=CC=CC=C1C=C2)=O RROZJMWKQNSJOL-OXJNMPFZSA-N 0.000 claims description 5
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
• DHLCTHXZKHGREA-UHFFFAOYSA-N 6h-pyrido[2,3-d]pyridazin-5-one Chemical compound C1=CC=C2C(=O)NN=CC2=N1 DHLCTHXZKHGREA-UHFFFAOYSA-N 0.000 claims description 5
• LCSGWIUZBNBGDL-UHFFFAOYSA-N 8-(2-fluoropyridin-4-yl)-2-(2-quinolin-2-ylcyclopropyl)isoquinolin-1-one Chemical compound C1=NC(F)=CC(C=2C=3C(=O)N(C4C(C4)C=4N=C5C=CC=CC5=CC=4)C=CC=3C=CC=2)=C1 LCSGWIUZBNBGDL-UHFFFAOYSA-N 0.000 claims description 5
• 208000023105 Huntington disease Diseases 0.000 claims description 5
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• ASNUDELVENWRMB-LAUBAEHRSA-N 3-pyridin-4-yl-5-[(1R,2R)-2-quinolin-2-ylcyclopropyl]thieno[3,2-c]pyridin-4-one Chemical compound C1[C@H]([C@@H]1N2C=CC3=C(C2=O)C(=CS3)C4=CC=NC=C4)C5=NC6=CC=CC=C6C=C5 ASNUDELVENWRMB-LAUBAEHRSA-N 0.000 claims description 4
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 4
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
• 208000008589 Obesity Diseases 0.000 claims description 4
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 4
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
• 235000005911 diet Nutrition 0.000 claims description 4
• 150000002148 esters Chemical class 0.000 claims description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 235000020824 obesity Nutrition 0.000 claims description 4
• OELZFJUWWFRWLC-UHFFFAOYSA-N oxazine-1 Chemical compound C1=CC(N(CC)CC)=CC2=[O+]C3=CC(N(CC)CC)=CC=C3N=C21 OELZFJUWWFRWLC-UHFFFAOYSA-N 0.000 claims description 4
• 230000036961 partial effect Effects 0.000 claims description 4
• FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 claims description 4
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
• 150000003254 radicals Chemical class 0.000 claims description 4
• 125000003003 spiro group Chemical group 0.000 claims description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
• ASNUDELVENWRMB-UHFFFAOYSA-N 3-pyridin-4-yl-5-(2-quinolin-2-ylcyclopropyl)thieno[3,2-c]pyridin-4-one Chemical compound C1=2C(=O)N(C3C(C3)C=3N=C4C=CC=CC4=CC=3)C=CC=2SC=C1C1=CC=NC=C1 ASNUDELVENWRMB-UHFFFAOYSA-N 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• RROZJMWKQNSJOL-UHFFFAOYSA-N 3-pyrimidin-5-yl-5-(2-quinolin-2-ylcyclopropyl)thieno[3,2-c]pyridin-4-one Chemical compound C1=2C(=O)N(C3C(C3)C=3N=C4C=CC=CC4=CC=3)C=CC=2SC=C1C1=CN=CN=C1 RROZJMWKQNSJOL-UHFFFAOYSA-N 0.000 claims description 3
• MPOYBFYHRQBZPM-UHFFFAOYSA-N 3h-pyridin-4-one Chemical compound O=C1CC=NC=C1 MPOYBFYHRQBZPM-UHFFFAOYSA-N 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 3
• 230000000378 dietary effect Effects 0.000 claims description 3
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
• OJEOJUQOECNDND-UHFFFAOYSA-N oxetan-3-amine Chemical compound NC1COC1 OJEOJUQOECNDND-UHFFFAOYSA-N 0.000 claims description 3
• VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 claims description 3
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
• 125000005493 quinolyl group Chemical group 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 238000002560 therapeutic procedure Methods 0.000 claims description 3
• PCVUPNNIMVDXTJ-UHFFFAOYSA-N 2-[2-(1,3-benzothiazol-2-yl)ethyl]-8-pyridin-4-ylisoquinolin-1-one Chemical compound C=12C(=O)N(CCC=3SC4=CC=CC=C4N=3)C=CC2=CC=CC=1C1=CC=NC=C1 PCVUPNNIMVDXTJ-UHFFFAOYSA-N 0.000 claims description 2
• RNZOPJWJVAXPFR-UHFFFAOYSA-N 2-[2-(3-methylquinolin-2-yl)ethyl]-8-pyridin-4-ylisoquinolin-1-one Chemical compound CC1=CC2=CC=CC=C2N=C1CCN(C(C1=2)=O)C=CC1=CC=CC=2C1=CC=NC=C1 RNZOPJWJVAXPFR-UHFFFAOYSA-N 0.000 claims description 2
• GUSZZCFDFJEHQY-UHFFFAOYSA-N 2-[2-(5-methylpyridin-2-yl)ethyl]-8-pyridin-4-ylisoquinolin-1-one Chemical compound N1=CC(C)=CC=C1CCN1C(=O)C2=C(C=3C=CN=CC=3)C=CC=C2C=C1 GUSZZCFDFJEHQY-UHFFFAOYSA-N 0.000 claims description 2
• SIXKYHRABSUILN-UHFFFAOYSA-N 2-[2-(6-fluoroquinolin-2-yl)cyclopropyl]-8-morpholin-4-ylisoquinolin-1-one Chemical compound C1=CC2=CC(F)=CC=C2N=C1C1CC1N(C(C1=2)=O)C=CC1=CC=CC=2N1CCOCC1 SIXKYHRABSUILN-UHFFFAOYSA-N 0.000 claims description 2
• YYKZVHXBOVKANS-UHFFFAOYSA-N 2-[2-(6-fluoroquinolin-2-yl)cyclopropyl]-8-pyrimidin-5-ylisoquinolin-1-one Chemical compound C1=CC2=CC(F)=CC=C2N=C1C1CC1N(C(C1=2)=O)C=CC1=CC=CC=2C1=CN=CN=C1 YYKZVHXBOVKANS-UHFFFAOYSA-N 0.000 claims description 2
• GBLUIIINCIVDDD-UHFFFAOYSA-N 2-[2-(8-fluoroquinolin-2-yl)ethyl]-8-pyridin-4-ylisoquinolin-1-one Chemical compound N1=C2C(F)=CC=CC2=CC=C1CCN(C(C1=2)=O)C=CC1=CC=CC=2C1=CC=NC=C1 GBLUIIINCIVDDD-UHFFFAOYSA-N 0.000 claims description 2
• ULMDVRBWINKKKT-UHFFFAOYSA-N 3-(1-benzofuran-2-yl)-5-(2-quinolin-2-ylethyl)thieno[2,3-d]pyridazin-4-one Chemical compound C1=CC=C2OC(C3=CSC=4C=NN(CCC=5N=C6C=CC=CC6=CC=5)C(C3=4)=O)=CC2=C1 ULMDVRBWINKKKT-UHFFFAOYSA-N 0.000 claims description 2
• HRAMAKGPDRKFFD-UHFFFAOYSA-N 3-(1h-pyrazol-5-yl)-5-(2-quinolin-2-ylethyl)thieno[2,3-d]pyridazin-4-one Chemical compound C1=2C(=O)N(CCC=3N=C4C=CC=CC4=CC=3)N=CC=2SC=C1C=1C=CNN=1 HRAMAKGPDRKFFD-UHFFFAOYSA-N 0.000 claims description 2
• FVDXMNXFJQEXSP-UHFFFAOYSA-N 3-(2,3-dihydro-1-benzofuran-5-yl)-5-(2-quinolin-2-ylethyl)thieno[2,3-d]pyridazin-4-one Chemical compound C1=C2OCCC2=CC(C2=CSC=3C=NN(CCC=4N=C5C=CC=CC5=CC=4)C(C2=3)=O)=C1 FVDXMNXFJQEXSP-UHFFFAOYSA-N 0.000 claims description 2
• PUCCFQQFKJXEIK-UHFFFAOYSA-N 3-(2,5-dichlorophenyl)-5-(2-quinolin-2-ylethyl)thieno[2,3-d]pyridazin-4-one Chemical compound ClC1=CC=C(Cl)C(C=2C=3C(=O)N(CCC=4N=C5C=CC=CC5=CC=4)N=CC=3SC=2)=C1 PUCCFQQFKJXEIK-UHFFFAOYSA-N 0.000 claims description 2
• DNGAPPWFPQYXHZ-UHFFFAOYSA-N 3-(2-chloro-4-fluorophenyl)-5-(2-quinolin-2-ylethyl)thieno[2,3-d]pyridazin-4-one Chemical compound ClC1=CC(F)=CC=C1C1=CSC2=C1C(=O)N(CCC=1N=C3C=CC=CC3=CC=1)N=C2 DNGAPPWFPQYXHZ-UHFFFAOYSA-N 0.000 claims description 2
• XUPANYHEJOSCDA-UHFFFAOYSA-N 3-(2-ethylphenyl)-5-(2-quinolin-2-ylethyl)thieno[2,3-d]pyridazin-4-one Chemical compound CCC1=CC=CC=C1C1=CSC2=C1C(=O)N(CCC=1N=C3C=CC=CC3=CC=1)N=C2 XUPANYHEJOSCDA-UHFFFAOYSA-N 0.000 claims description 2
• RYORFSMHEDEJPU-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenyl)-5-(2-quinolin-2-ylethyl)thieno[2,3-d]pyridazin-4-one Chemical compound FC1=CC(C)=CC=C1C1=CSC2=C1C(=O)N(CCC=1N=C3C=CC=CC3=CC=1)N=C2 RYORFSMHEDEJPU-UHFFFAOYSA-N 0.000 claims description 2
• FVHHUOKOJFNQHF-UHFFFAOYSA-N 3-(2-fluoro-5-methoxyphenyl)-5-(2-quinolin-2-ylethyl)thieno[2,3-d]pyridazin-4-one Chemical compound COC1=CC=C(F)C(C=2C=3C(=O)N(CCC=4N=C5C=CC=CC5=CC=4)N=CC=3SC=2)=C1 FVHHUOKOJFNQHF-UHFFFAOYSA-N 0.000 claims description 2
• IJVFXZRAODURBL-UHFFFAOYSA-N 3-(2-fluoropyridin-4-yl)-5-[2-(6-fluoroquinolin-2-yl)cyclopropyl]thieno[3,2-c]pyridin-4-one Chemical compound C1=CC2=CC(F)=CC=C2N=C1C1CC1N(C(C=12)=O)C=CC=1SC=C2C1=CC=NC(F)=C1 IJVFXZRAODURBL-UHFFFAOYSA-N 0.000 claims description 2
• ZYXIVTZVKLFZKM-UHFFFAOYSA-N 3-(2-methylphenyl)-5-(2-quinolin-2-ylethyl)thieno[2,3-d]pyridazin-4-one Chemical compound CC1=CC=CC=C1C1=CSC2=C1C(=O)N(CCC=1N=C3C=CC=CC3=CC=1)N=C2 ZYXIVTZVKLFZKM-UHFFFAOYSA-N 0.000 claims description 2
• ZGDQKGYAOYVOIH-UHFFFAOYSA-N 3-(2-methylpyrimidin-5-yl)-5-(2-quinolin-2-ylcyclopropyl)thieno[3,2-c]pyridin-4-one Chemical compound C1=NC(C)=NC=C1C1=CSC2=C1C(=O)N(C1C(C1)C=1N=C3C=CC=CC3=CC=1)C=C2 ZGDQKGYAOYVOIH-UHFFFAOYSA-N 0.000 claims description 2
• YGBCPOLEDWOMSR-UHFFFAOYSA-N 3-(2-pyridin-3-ylethynyl)-5-(2-quinolin-2-ylethyl)thieno[2,3-d]pyridazin-4-one Chemical compound C1=2C(=O)N(CCC=3N=C4C=CC=CC4=CC=3)N=CC=2SC=C1C#CC1=CC=CN=C1 YGBCPOLEDWOMSR-UHFFFAOYSA-N 0.000 claims description 2
• UIZJAMSZHCRPFY-UHFFFAOYSA-N 3-(2-pyridin-4-ylethynyl)-5-(2-quinolin-2-ylethyl)thieno[2,3-d]pyridazin-4-one Chemical compound C1=2C(=O)N(CCC=3N=C4C=CC=CC4=CC=3)N=CC=2SC=C1C#CC1=CC=NC=C1 UIZJAMSZHCRPFY-UHFFFAOYSA-N 0.000 claims description 2
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• YDMWKMJIKYUHRE-UHFFFAOYSA-N 3-(3-chloro-4-fluorophenyl)-5-(2-quinolin-2-ylethyl)thieno[2,3-d]pyridazin-4-one Chemical compound C1=C(Cl)C(F)=CC=C1C1=CSC2=C1C(=O)N(CCC=1N=C3C=CC=CC3=CC=1)N=C2 YDMWKMJIKYUHRE-UHFFFAOYSA-N 0.000 claims description 2
• WVFAYBUSNQRFQL-UHFFFAOYSA-N 3-(3-hydroxyphenyl)-5-(2-quinolin-2-ylethyl)thieno[2,3-d]pyridazin-4-one Chemical compound OC1=CC=CC(C=2C=3C(=O)N(CCC=4N=C5C=CC=CC5=CC=4)N=CC=3SC=2)=C1 WVFAYBUSNQRFQL-UHFFFAOYSA-N 0.000 claims description 2
• YLUAVPASONNKNY-UHFFFAOYSA-N 3-(3-hydroxyphenyl)-5-(2-quinolin-2-ylethyl)thieno[3,2-c]pyridin-4-one Chemical compound OC1=CC=CC(C=2C=3C(=O)N(CCC=4N=C5C=CC=CC5=CC=4)C=CC=3SC=2)=C1 YLUAVPASONNKNY-UHFFFAOYSA-N 0.000 claims description 2
• VLQOEPZOKPQTHP-UHFFFAOYSA-N 3-(3-hydroxypyridin-4-yl)-5-(2-quinolin-2-ylethyl)thieno[3,2-c]pyridin-4-one Chemical compound OC1=CN=CC=C1C1=CSC2=C1C(=O)N(CCC=1N=C3C=CC=CC3=CC=1)C=C2 VLQOEPZOKPQTHP-UHFFFAOYSA-N 0.000 claims description 2
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• 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
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