KR20140097318A - 포스포디에스테라제 타입 １０ａ의 억제제 - Google Patents

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Publication number

KR20140097318A

KR20140097318A KR1020147015427A KR20147015427A KR20140097318A KR 20140097318 A KR20140097318 A KR 20140097318A KR 1020147015427 A KR1020147015427 A KR 1020147015427A KR 20147015427 A KR20147015427 A KR 20147015427A KR 20140097318 A KR20140097318 A KR 20140097318A

Authority

KR

South Korea

Prior art keywords

quinolin

ethyl

pyridin

cyclopropyl

thieno

Prior art date

2011-11-09

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

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• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 title claims abstract description 18
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 title claims abstract description 18
• 239000003112 inhibitor Substances 0.000 title abstract description 10
• 150000001875 compounds Chemical class 0.000 claims abstract description 396
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 317
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 191
• 239000001257 hydrogen Substances 0.000 claims abstract description 170
• 229910052717 sulfur 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 100
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 98
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 94
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 80
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 62
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 49
• 150000002367 halogens Chemical class 0.000 claims abstract description 48
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 39
• 238000011282 treatment Methods 0.000 claims abstract description 36
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
• -1 1,2-ethene-diyl Chemical group 0.000 claims description 720
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 132
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 128
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 110
• 125000005842 heteroatom Chemical group 0.000 claims description 110
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 88
• 150000003839 salts Chemical class 0.000 claims description 87
• 229910052731 fluorine Inorganic materials 0.000 claims description 84
• 239000000651 prodrug Substances 0.000 claims description 84
• 229940002612 prodrug Drugs 0.000 claims description 84
• 229920006395 saturated elastomer Polymers 0.000 claims description 82
• 239000011737 fluorine Substances 0.000 claims description 79
• 150000001204 N-oxides Chemical class 0.000 claims description 71
• 150000004677 hydrates Chemical class 0.000 claims description 66
• 125000001424 substituent group Chemical group 0.000 claims description 57
• 239000000126 substance Substances 0.000 claims description 56
• 125000004432 carbon atom Chemical group C* 0.000 claims description 49
• 238000000034 method Methods 0.000 claims description 49
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
• IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 claims description 39
• 239000000460 chlorine Chemical group 0.000 claims description 37
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 37
• 229910052801 chlorine Inorganic materials 0.000 claims description 34
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 34
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 33
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 32
• 230000005764 inhibitory process Effects 0.000 claims description 30
• 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 30
• 125000001153 fluoro group Chemical group F* 0.000 claims description 29
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 26
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 26
• 125000001544 thienyl group Chemical group 0.000 claims description 26
• 125000001072 heteroaryl group Chemical group 0.000 claims description 25
• 125000000623 heterocyclic group Chemical group 0.000 claims description 25
• 125000004076 pyridyl group Chemical group 0.000 claims description 25
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 25
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 24
• 241000124008 Mammalia Species 0.000 claims description 23
• 125000002541 furyl group Chemical group 0.000 claims description 23
• 125000002883 imidazolyl group Chemical group 0.000 claims description 22
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 21
• 125000000335 thiazolyl group Chemical group 0.000 claims description 21
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 20
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 20
• 125000002971 oxazolyl group Chemical group 0.000 claims description 20
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
• DUPNPBCUJHMSFZ-UHFFFAOYSA-N 5h-thieno[3,2-c]pyridin-4-one Chemical compound O=C1NC=CC2=C1C=CS2 DUPNPBCUJHMSFZ-UHFFFAOYSA-N 0.000 claims description 18
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 18
• 201000000980 schizophrenia Diseases 0.000 claims description 18
• 201000010099 disease Diseases 0.000 claims description 17
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 15
• 125000000217 alkyl group Chemical group 0.000 claims description 14
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 14
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 14
• VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 claims description 14
• 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 13
• 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 12
• 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 12
• 229910052740 iodine Inorganic materials 0.000 claims description 12
• 238000003786 synthesis reaction Methods 0.000 claims description 12
• 208000019901 Anxiety disease Diseases 0.000 claims description 11
• 125000004429 atom Chemical group 0.000 claims description 11
• 230000015572 biosynthetic process Effects 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 11
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 10
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
• 208000010877 cognitive disease Diseases 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 claims description 9
• 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 9
• 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 8
• XPPXUDVPZXZMHC-UHFFFAOYSA-N 8-morpholin-4-yl-2-(2-quinolin-2-ylcyclopropyl)isoquinolin-1-one Chemical compound C=12C(=O)N(C3C(C3)C=3N=C4C=CC=CC4=CC=3)C=CC2=CC=CC=1N1CCOCC1 XPPXUDVPZXZMHC-UHFFFAOYSA-N 0.000 claims description 8
• CYQLXLAJVANNIE-UHFFFAOYSA-N 8-pyridin-4-yl-2-(2-quinolin-2-ylcyclopropyl)isoquinolin-1-one Chemical compound C=12C(=O)N(C3C(C3)C=3N=C4C=CC=CC4=CC=3)C=CC2=CC=CC=1C1=CC=NC=C1 CYQLXLAJVANNIE-UHFFFAOYSA-N 0.000 claims description 8
• 230000036506 anxiety Effects 0.000 claims description 8
• 208000020925 Bipolar disease Diseases 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
• 239000001301 oxygen Substances 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
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 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 claims description 6
• MQKXIURELWPBHC-UHFFFAOYSA-N 8-pyridin-4-yl-2-(2-quinolin-2-ylcyclopropyl)phthalazin-1-one Chemical compound C=12C(=O)N(C3C(C3)C=3N=C4C=CC=CC4=CC=3)N=CC2=CC=CC=1C1=CC=NC=C1 MQKXIURELWPBHC-UHFFFAOYSA-N 0.000 claims description 6
• NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical compound N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 claims description 6
• 238000007429 general method Methods 0.000 claims description 6
• 125000002950 monocyclic group Chemical group 0.000 claims description 6
• 208000020401 Depressive disease Diseases 0.000 claims description 5
• 208000023105 Huntington disease Diseases 0.000 claims description 5
• 125000003118 aryl group Chemical group 0.000 claims description 5
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
• 125000001041 indolyl group Chemical group 0.000 claims description 5
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 5
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
• 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 4
• AVTACHRNMUXQIN-UHFFFAOYSA-N 2-[2-(6-fluoroquinolin-2-yl)cyclopropyl]-8-pyridin-3-ylisoquinolin-1-one Chemical compound C1=CC2=CC(F)=CC=C2N=C1C1CC1N(C(C1=2)=O)C=CC1=CC=CC=2C1=CC=CN=C1 AVTACHRNMUXQIN-UHFFFAOYSA-N 0.000 claims description 4
• OEZPXSYTAGOBNS-UHFFFAOYSA-N 2-[2-(6-fluoroquinolin-2-yl)cyclopropyl]-8-pyridin-4-ylisoquinolin-1-one Chemical compound C1=CC2=CC(F)=CC=C2N=C1C1CC1N(C(C1=2)=O)C=CC1=CC=CC=2C1=CC=NC=C1 OEZPXSYTAGOBNS-UHFFFAOYSA-N 0.000 claims description 4
• NZGNEUSBEOWIEE-UHFFFAOYSA-N 2-[2-(6-fluoroquinolin-2-yl)cyclopropyl]-8-pyridin-4-ylphthalazin-1-one Chemical compound C1=CC2=CC(F)=CC=C2N=C1C1CC1N(C(C1=2)=O)N=CC1=CC=CC=2C1=CC=NC=C1 NZGNEUSBEOWIEE-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 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 4
• FKKFWPZJMQQYAB-UHFFFAOYSA-N 3-pyridazin-4-yl-5-(2-quinolin-2-ylcyclopropyl)furo[3,2-c]pyridin-4-one Chemical compound C1=2C(=O)N(C3C(C3)C=3N=C4C=CC=CC4=CC=3)C=CC=2OC=C1C1=CC=NN=C1 FKKFWPZJMQQYAB-UHFFFAOYSA-N 0.000 claims description 4
• PZSUHIDQNAZRJU-UHFFFAOYSA-N 3-pyridazin-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=NN=C1 PZSUHIDQNAZRJU-UHFFFAOYSA-N 0.000 claims description 4
• AOKVZGMQMSKCEQ-UHFFFAOYSA-N 3-pyridin-3-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=CN=C1 AOKVZGMQMSKCEQ-UHFFFAOYSA-N 0.000 claims description 4
• YFDQPCLLOLSBMJ-UHFFFAOYSA-N 3-pyridin-4-yl-5-(2-quinolin-2-ylcyclopropyl)furo[3,2-c]pyridin-4-one Chemical compound C1=2C(=O)N(C3C(C3)C=3N=C4C=CC=CC4=CC=3)C=CC=2OC=C1C1=CC=NC=C1 YFDQPCLLOLSBMJ-UHFFFAOYSA-N 0.000 claims description 4
• MGRMNBJBPWQARR-UHFFFAOYSA-N 3-pyridin-4-yl-5-(2-quinolin-2-ylcyclopropyl)thieno[2,3-d]pyridazin-4-one Chemical compound C1=2C(=O)N(C3C(C3)C=3N=C4C=CC=CC4=CC=3)N=CC=2SC=C1C1=CC=NC=C1 MGRMNBJBPWQARR-UHFFFAOYSA-N 0.000 claims description 4
• FVKSBWFXOSEBOR-UHFFFAOYSA-N 3-pyrimidin-5-yl-5-(2-quinolin-2-ylcyclopropyl)thieno[2,3-d]pyridazin-4-one Chemical compound C1=2C(=O)N(C3C(C3)C=3N=C4C=CC=CC4=CC=3)N=CC=2SC=C1C1=CN=CN=C1 FVKSBWFXOSEBOR-UHFFFAOYSA-N 0.000 claims description 4
• MYOKVRYNQIVFJX-UHFFFAOYSA-N 4-chloro-8-pyrimidin-5-yl-2-(2-quinolin-2-ylcyclopropyl)isoquinolin-1-one Chemical compound C1=CC=C2C(Cl)=CN(C3C(C3)C=3N=C4C=CC=CC4=CC=3)C(=O)C2=C1C1=CN=CN=C1 MYOKVRYNQIVFJX-UHFFFAOYSA-N 0.000 claims description 4
• PPQAGFQZBYYBPQ-UHFFFAOYSA-N 4-fluoro-8-pyridin-4-yl-2-(2-quinolin-2-ylcyclopropyl)isoquinolin-1-one Chemical compound C1=CC=C2C(F)=CN(C3C(C3)C=3N=C4C=CC=CC4=CC=3)C(=O)C2=C1C1=CC=NC=C1 PPQAGFQZBYYBPQ-UHFFFAOYSA-N 0.000 claims description 4
• ZEHYTCXDQFTMRW-UHFFFAOYSA-N 4-fluoro-8-pyrimidin-5-yl-2-(2-quinolin-2-ylcyclopropyl)isoquinolin-1-one Chemical compound C1=CC=C2C(F)=CN(C3C(C3)C=3N=C4C=CC=CC4=CC=3)C(=O)C2=C1C1=CN=CN=C1 ZEHYTCXDQFTMRW-UHFFFAOYSA-N 0.000 claims description 4
• JMHFKEWHJJGYTP-UHFFFAOYSA-N 4-pyridin-4-yl-6-(2-quinolin-2-ylcyclopropyl)pyrido[2,3-d]pyridazin-5-one Chemical compound C=12C(=O)N(C3C(C3)C=3N=C4C=CC=CC4=CC=3)N=CC2=NC=CC=1C1=CC=NC=C1 JMHFKEWHJJGYTP-UHFFFAOYSA-N 0.000 claims description 4
• RQDUVXXBTYJKIN-UHFFFAOYSA-N 5-[2-(6-fluoroquinolin-2-yl)cyclopropyl]-3-pyridin-4-ylthieno[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=C1 RQDUVXXBTYJKIN-UHFFFAOYSA-N 0.000 claims description 4
• XDCLDCDNXHQJEI-UHFFFAOYSA-N 5-pyridin-3-yl-2-(2-quinolin-2-ylcyclopropyl)isoquinolin-1-one Chemical compound C1=CC=C2C(=O)N(C3C(C3)C=3N=C4C=CC=CC4=CC=3)C=CC2=C1C1=CC=CN=C1 XDCLDCDNXHQJEI-UHFFFAOYSA-N 0.000 claims description 4
• XHCLSIRVDUTRAS-UHFFFAOYSA-N 5-pyridin-4-yl-2-(2-quinolin-2-ylcyclopropyl)isoquinolin-1-one Chemical compound C1=CC=C2C(=O)N(C3C(C3)C=3N=C4C=CC=CC4=CC=3)C=CC2=C1C1=CC=NC=C1 XHCLSIRVDUTRAS-UHFFFAOYSA-N 0.000 claims description 4
• QEUNFNUYYKEICD-UHFFFAOYSA-N 5-pyrimidin-5-yl-2-(2-quinolin-2-ylcyclopropyl)isoquinolin-1-one Chemical compound C1=CC=C2C(=O)N(C3C(C3)C=3N=C4C=CC=CC4=CC=3)C=CC2=C1C1=CN=CN=C1 QEUNFNUYYKEICD-UHFFFAOYSA-N 0.000 claims description 4
• PJBHVFBLRDATND-UHFFFAOYSA-N 8-(1-methylpyrazol-4-yl)-2-(2-quinolin-2-ylcyclopropyl)isoquinolin-1-one Chemical compound C1=NN(C)C=C1C1=CC=CC2=C1C(=O)N(C1C(C1)C=1N=C3C=CC=CC3=CC=1)C=C2 PJBHVFBLRDATND-UHFFFAOYSA-N 0.000 claims description 4
• INBIIFXPBZMYKQ-UHFFFAOYSA-N 8-(2,3-dihydrofuran-4-yl)-2-(2-quinolin-2-ylcyclopropyl)isoquinolin-1-one Chemical compound C=12C(=O)N(C3C(C3)C=3N=C4C=CC=CC4=CC=3)C=CC2=CC=CC=1C1=COCC1 INBIIFXPBZMYKQ-UHFFFAOYSA-N 0.000 claims description 4
• HMEUYKQNWQWISF-UHFFFAOYSA-N 8-(2-oxa-7-azaspiro[3.4]octan-7-yl)-2-(2-quinolin-2-ylcyclopropyl)isoquinolin-1-one Chemical compound C=12C(=O)N(C3C(C3)C=3N=C4C=CC=CC4=CC=3)C=CC2=CC=CC=1N(C1)CCC21COC2 HMEUYKQNWQWISF-UHFFFAOYSA-N 0.000 claims description 4
• HXFHTFGZTNXCET-UHFFFAOYSA-N 8-(3-fluoropyridin-4-yl)-2-(2-quinolin-2-ylcyclopropyl)isoquinolin-1-one Chemical compound FC1=CN=CC=C1C1=CC=CC2=C1C(=O)N(C1C(C1)C=1N=C3C=CC=CC3=CC=1)C=C2 HXFHTFGZTNXCET-UHFFFAOYSA-N 0.000 claims description 4
• PWCXNISNHONFFV-UHFFFAOYSA-N 8-(3-methoxypiperidin-1-yl)-2-(2-quinolin-2-ylcyclopropyl)isoquinolin-1-one Chemical compound C1C(OC)CCCN1C1=CC=CC2=C1C(=O)N(C1C(C1)C=1N=C3C=CC=CC3=CC=1)C=C2 PWCXNISNHONFFV-UHFFFAOYSA-N 0.000 claims description 4
• OKKDTIKQKNZBFH-UHFFFAOYSA-N 8-(4,4-difluoropiperidin-1-yl)-2-(2-quinolin-2-ylcyclopropyl)isoquinolin-1-one Chemical compound C1CC(F)(F)CCN1C1=CC=CC2=C1C(=O)N(C1C(C1)C=1N=C3C=CC=CC3=CC=1)C=C2 OKKDTIKQKNZBFH-UHFFFAOYSA-N 0.000 claims description 4
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