EA028344B1 - Соединения для лечения спинальной мышечной атрофии - Google Patents

Info

Publication number

EA028344B1

EA028344B1 EA201491412A EA201491412A EA028344B1 EA 028344 B1 EA028344 B1 EA 028344B1 EA 201491412 A EA201491412 A EA 201491412A EA 201491412 A EA201491412 A EA 201491412A EA 028344 B1 EA028344 B1 EA 028344B1

Authority

EA

Eurasian Patent Office

Prior art keywords

isochromen

pyrazin

compound

patient

alkyl

Prior art date

2012-01-26

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 884
• 208000002320 spinal muscular atrophy Diseases 0.000 title claims abstract description 9
• 108090000623 proteins and genes Proteins 0.000 claims description 474
• 108020004999 messenger RNA Proteins 0.000 claims description 426
• -1 1,2,5,6-tetrahydropyridinyl Chemical group 0.000 claims description 378
• 125000000217 alkyl group Chemical group 0.000 claims description 205
• 241000282414 Homo sapiens Species 0.000 claims description 130
• 238000000034 method Methods 0.000 claims description 108
• 102000004169 proteins and genes Human genes 0.000 claims description 82
• 150000003839 salts Chemical class 0.000 claims description 80
• 238000010348 incorporation Methods 0.000 claims description 65
• 239000008194 pharmaceutical composition Substances 0.000 claims description 45
• 239000010802 sludge Substances 0.000 claims description 40
• 238000011282 treatment Methods 0.000 claims description 35
• 210000005260 human cell Anatomy 0.000 claims description 32
• 125000001424 substituent group Chemical group 0.000 claims description 32
• 125000004076 pyridyl group Chemical group 0.000 claims description 29
• 125000003545 alkoxy group Chemical group 0.000 claims description 28
• 230000001965 increasing effect Effects 0.000 claims description 28
• 125000003282 alkyl amino group Chemical group 0.000 claims description 27
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 26
• 125000000623 heterocyclic group Chemical group 0.000 claims description 26
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 22
• 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 22
• 239000003085 diluting agent Substances 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 239000002253 acid Substances 0.000 claims description 14
• 230000002708 enhancing effect Effects 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• IQZZFVDIZRWADY-UHFFFAOYSA-N isocoumarin Chemical compound C1=CC=C2C(=O)OC=CC2=C1 IQZZFVDIZRWADY-UHFFFAOYSA-N 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 239000003937 drug carrier Substances 0.000 claims description 12
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 10
• 150000002367 halogens Chemical class 0.000 claims description 9
• 125000001072 heteroaryl group Chemical group 0.000 claims description 9
• 125000001984 thiazolidinyl group Chemical group 0.000 claims description 9
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
• 239000012458 free base Substances 0.000 claims description 8
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 125000001041 indolyl group Chemical group 0.000 claims description 6
• 125000005310 triazolidinyl group Chemical group N1(NNCC1)* 0.000 claims description 6
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 5
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 125000002393 azetidinyl group Chemical group 0.000 claims description 5
• 239000001257 hydrogen Substances 0.000 claims description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 125000003965 isoxazolidinyl group Chemical group 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• 125000002755 pyrazolinyl group Chemical group 0.000 claims description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
• 125000001422 pyrrolinyl group Chemical group 0.000 claims description 5
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 4
• 125000004414 alkyl thio group Chemical group 0.000 claims description 4
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 4
• 125000002636 imidazolinyl group Chemical group 0.000 claims description 4
• 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 4
• 125000003971 isoxazolinyl group Chemical group 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000000160 oxazolidinyl group Chemical group 0.000 claims description 4
• 125000005968 oxazolinyl group Chemical group 0.000 claims description 4
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
• 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 4
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
• 125000002769 thiazolinyl group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 3
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 3
• IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 claims description 3
• 125000005960 1,4-diazepanyl group Chemical group 0.000 claims description 3
• 125000005955 1H-indazolyl group Chemical group 0.000 claims description 3
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 3
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000004613 furo[2,3-c]pyridinyl group Chemical group O1C(=CC=2C1=CN=CC2)* 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
• 125000002971 oxazolyl group Chemical group 0.000 claims description 3
• 125000003566 oxetanyl group Chemical group 0.000 claims description 3
• 125000000466 oxiranyl group Chemical group 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
• 125000004306 triazinyl group Chemical group 0.000 claims description 3
• FTUSZJTUFHXUPG-UHFFFAOYSA-N 1,2,3,3a,4,5-hexahydropyrrolo[2,3-c]pyrrole Chemical compound C1NC=C2NCCC21 FTUSZJTUFHXUPG-UHFFFAOYSA-N 0.000 claims description 2
• FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 claims description 2
• UUZJJNBYJDFQHL-UHFFFAOYSA-N 1,2,3-triazolidine Chemical compound C1CNNN1 UUZJJNBYJDFQHL-UHFFFAOYSA-N 0.000 claims description 2
• CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims description 2
• RZQQXRVPPOOCQR-UHFFFAOYSA-N 2,3-dihydro-1,3,4-oxadiazole Chemical compound C1NN=CO1 RZQQXRVPPOOCQR-UHFFFAOYSA-N 0.000 claims description 2
• XGGJEBZNLNGURJ-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-7-piperazin-1-ylisochromen-1-one Chemical compound C1=C2C(=O)OC(C=3C=C4OCOC4=CC=3)=CC2=CC=C1N1CCNCC1 XGGJEBZNLNGURJ-UHFFFAOYSA-N 0.000 claims description 2
• RMMBPLGUTLDIOV-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-7-(1,4-diazepan-1-yl)isochromen-1-one Chemical compound C1=C2C(=O)OC(C=3SC4=CC=CC=C4N=3)=CC2=CC=C1N1CCCNCC1 RMMBPLGUTLDIOV-UHFFFAOYSA-N 0.000 claims description 2
• DIDYFUQMYQIJOM-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-7-piperazin-1-ylisochromen-1-one Chemical compound C1=C2C(=O)OC(C=3SC4=CC=CC=C4N=3)=CC2=CC=C1N1CCNCC1 DIDYFUQMYQIJOM-UHFFFAOYSA-N 0.000 claims description 2
• VWOLTIFBOYOVQN-UHFFFAOYSA-N 3-(1,3-dimethylpyrrolo[1,2-a]pyrazin-7-yl)-7-[4-(2-hydroxyethyl)piperazin-1-yl]isochromen-1-one Chemical compound C1=C2C(C)=NC(C)=CN2C=C1C(OC(=O)C1=C2)=CC1=CC=C2N1CCN(CCO)CC1 VWOLTIFBOYOVQN-UHFFFAOYSA-N 0.000 claims description 2
• AFKHSHXNKQEFCE-UHFFFAOYSA-N 3-(2-methyl-1,3-benzothiazol-5-yl)-7-piperazin-1-ylisochromen-1-one Chemical compound C=1C=C2SC(C)=NC2=CC=1C(OC(=O)C1=C2)=CC1=CC=C2N1CCNCC1 AFKHSHXNKQEFCE-UHFFFAOYSA-N 0.000 claims description 2
• HVDQRLLJJQHVCY-UHFFFAOYSA-N 3-(2-methyl-1,3-benzothiazol-6-yl)-7-[4-(oxetan-3-yl)piperazin-1-yl]isochromen-1-one Chemical compound C1=C2SC(C)=NC2=CC=C1C(OC(=O)C1=C2)=CC1=CC=C2N(CC1)CCN1C1COC1 HVDQRLLJJQHVCY-UHFFFAOYSA-N 0.000 claims description 2
• VJHJOFDYLVZNCO-UHFFFAOYSA-N 3-(2-methylindazol-5-yl)-7-piperazin-1-ylisochromen-1-one Chemical compound C1=CC2=NN(C)C=C2C=C1C(OC(=O)C1=C2)=CC1=CC=C2N1CCNCC1 VJHJOFDYLVZNCO-UHFFFAOYSA-N 0.000 claims description 2
• YLMGJLMUAAUMNC-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-7-piperazin-1-ylisochromen-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC2=CC=C(N3CCNCC3)C=C2C(=O)O1 YLMGJLMUAAUMNC-UHFFFAOYSA-N 0.000 claims description 2
• QCZRHNHWJXCHCP-UHFFFAOYSA-N 3-(4-ethoxyphenyl)-7-piperazin-1-ylisochromen-1-one Chemical compound C1=CC(OCC)=CC=C1C1=CC2=CC=C(N3CCNCC3)C=C2C(=O)O1 QCZRHNHWJXCHCP-UHFFFAOYSA-N 0.000 claims description 2
• AQQCUSSDYYCHML-UHFFFAOYSA-N 3-(4-methoxyphenyl)-7-piperazin-1-ylisochromen-1-one Chemical compound C1=CC(OC)=CC=C1C1=CC2=CC=C(N3CCNCC3)C=C2C(=O)O1 AQQCUSSDYYCHML-UHFFFAOYSA-N 0.000 claims description 2
• XXQSIQIKTMDLDE-UHFFFAOYSA-N 3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-(1,2,3,6-tetrahydropyridin-4-yl)isochromen-1-one Chemical compound N1=C2C(C)=NC(C)=CN2C=C1C(OC(=O)C1=C2)=CC1=CC=C2C1=CCNCC1 XXQSIQIKTMDLDE-UHFFFAOYSA-N 0.000 claims description 2
• IFFFIGBSTGOFBF-UHFFFAOYSA-N 3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-(1-ethylpiperidin-4-yl)isochromen-1-one Chemical compound C1CN(CC)CCC1C1=CC=C(C=C(OC2=O)C=3N=C4C(C)=NC(C)=CN4C=3)C2=C1 IFFFIGBSTGOFBF-UHFFFAOYSA-N 0.000 claims description 2
• ZVSGJGATQDYOQK-UHFFFAOYSA-N 3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-(1-methylpiperidin-4-yl)isochromen-1-one Chemical compound C1CN(C)CCC1C1=CC=C(C=C(OC2=O)C=3N=C4C(C)=NC(C)=CN4C=3)C2=C1 ZVSGJGATQDYOQK-UHFFFAOYSA-N 0.000 claims description 2
• XYRFITNWPNSDGK-UHFFFAOYSA-N 3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-(4-hydroxypiperidin-1-yl)isochromen-1-one Chemical compound N1=C2C(C)=NC(C)=CN2C=C1C(OC(=O)C1=C2)=CC1=CC=C2N1CCC(O)CC1 XYRFITNWPNSDGK-UHFFFAOYSA-N 0.000 claims description 2
• ZWBHLGVOQDQGQA-UHFFFAOYSA-N 3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-[1-(2-methoxyethyl)-3,6-dihydro-2h-pyridin-4-yl]isochromen-1-one Chemical compound C1N(CCOC)CCC(C=2C=C3C(=O)OC(=CC3=CC=2)C=2N=C3C(C)=NC(C)=CN3C=2)=C1 ZWBHLGVOQDQGQA-UHFFFAOYSA-N 0.000 claims description 2
• YWGBAYRIEZOWAJ-UHFFFAOYSA-N 3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-[4-(2-hydroxyethyl)piperazin-1-yl]isochromen-1-one Chemical compound N1=C2C(C)=NC(C)=CN2C=C1C(OC(=O)C1=C2)=CC1=CC=C2N1CCN(CCO)CC1 YWGBAYRIEZOWAJ-UHFFFAOYSA-N 0.000 claims description 2
• MDCCGEZNAMVHIF-UHFFFAOYSA-N 3-(6-chloro-8-methylimidazo[1,2-a]pyrazin-2-yl)-7-(4-ethylpiperazin-1-yl)isochromen-1-one Chemical compound C1CN(CC)CCN1C1=CC=C(C=C(OC2=O)C=3N=C4C(C)=NC(Cl)=CN4C=3)C2=C1 MDCCGEZNAMVHIF-UHFFFAOYSA-N 0.000 claims description 2
• YUIHGIDMTNXZJU-UHFFFAOYSA-N 3-(6-chloro-8-methylimidazo[1,2-a]pyrazin-2-yl)-7-(4-methylpiperazin-1-yl)isochromen-1-one Chemical compound C1CN(C)CCN1C1=CC=C(C=C(OC2=O)C=3N=C4C(C)=NC(Cl)=CN4C=3)C2=C1 YUIHGIDMTNXZJU-UHFFFAOYSA-N 0.000 claims description 2
• KWSJOLNZNNPCAX-UHFFFAOYSA-N 3-(6-chloro-8-methylimidazo[1,2-a]pyrazin-2-yl)-7-(4-propan-2-ylpiperazin-1-yl)isochromen-1-one Chemical compound C1CN(C(C)C)CCN1C1=CC=C(C=C(OC2=O)C=3N=C4C(C)=NC(Cl)=CN4C=3)C2=C1 KWSJOLNZNNPCAX-UHFFFAOYSA-N 0.000 claims description 2
• ZUBXCOBCOQCRBD-UHFFFAOYSA-N 3-(8-chloroimidazo[1,2-a]pyridin-2-yl)-7-(4-methylpiperazin-1-yl)isochromen-1-one Chemical compound C1CN(C)CCN1C1=CC=C(C=C(OC2=O)C=3N=C4C(Cl)=CC=CN4C=3)C2=C1 ZUBXCOBCOQCRBD-UHFFFAOYSA-N 0.000 claims description 2
• PHCLTSBGAGKKHH-UHFFFAOYSA-N 3-(8-ethyl-6-methylimidazo[1,2-a]pyrazin-2-yl)-7-piperazin-1-ylisochromen-1-one Chemical compound C(C)C=1C=2N(C=C(N1)C)C=C(N2)C=2OC(C1=CC(=CC=C1C2)N2CCNCC2)=O PHCLTSBGAGKKHH-UHFFFAOYSA-N 0.000 claims description 2
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
• GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 claims description 2
• WEDKTMOIKOKBSH-UHFFFAOYSA-N 4,5-dihydrothiadiazole Chemical compound C1CN=NS1 WEDKTMOIKOKBSH-UHFFFAOYSA-N 0.000 claims description 2
• UCCPBFKKTGXNNZ-UHFFFAOYSA-N 7-(1-cyclobutylpiperidin-4-yl)-3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)isochromen-1-one Chemical compound N1=C2C(C)=NC(C)=CN2C=C1C(OC(=O)C1=C2)=CC1=CC=C2C(CC1)CCN1C1CCC1 UCCPBFKKTGXNNZ-UHFFFAOYSA-N 0.000 claims description 2
• YHZCLFQUTMKJQF-UHFFFAOYSA-N 7-(4-cyclobutylpiperazin-1-yl)-3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)isochromen-1-one Chemical compound N1=C2C(C)=NC(C)=CN2C=C1C(OC(=O)C1=C2)=CC1=CC=C2N(CC1)CCN1C1CCC1 YHZCLFQUTMKJQF-UHFFFAOYSA-N 0.000 claims description 2
• SZSRSHSBPSVCQJ-UHFFFAOYSA-N 7-(4-cyclopropylpiperazin-1-yl)-3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)isochromen-1-one Chemical compound N1=C2C(C)=NC(C)=CN2C=C1C(OC(=O)C1=C2)=CC1=CC=C2N(CC1)CCN1C1CC1 SZSRSHSBPSVCQJ-UHFFFAOYSA-N 0.000 claims description 2
• AQQLCAIKLCHXRF-UHFFFAOYSA-N 7-(4-methylpiperazin-1-yl)-3-pyridin-2-ylisochromen-1-one Chemical compound C1CN(C)CCN1C1=CC=C(C=C(OC2=O)C=3N=CC=CC=3)C2=C1 AQQLCAIKLCHXRF-UHFFFAOYSA-N 0.000 claims description 2
• DODIFWVGHVVVDW-UHFFFAOYSA-N 7-(4-tert-butylpiperazin-1-yl)-3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)isochromen-1-one Chemical compound N1=C2C(C)=NC(C)=CN2C=C1C(OC(=O)C1=C2)=CC1=CC=C2N1CCN(C(C)(C)C)CC1 DODIFWVGHVVVDW-UHFFFAOYSA-N 0.000 claims description 2
• MVQCAJCURNVZAM-UHFFFAOYSA-N 7-piperazin-1-yl-3-pyridin-2-ylisochromen-1-one Chemical compound C1=C2C(=O)OC(C=3N=CC=CC=3)=CC2=CC=C1N1CCNCC1 MVQCAJCURNVZAM-UHFFFAOYSA-N 0.000 claims description 2
• XWQYRLYOWZXQJK-UHFFFAOYSA-N 7-piperazin-1-yl-3-thiophen-3-ylisochromen-1-one Chemical compound C1=C2C(=O)OC(C3=CSC=C3)=CC2=CC=C1N1CCNCC1 XWQYRLYOWZXQJK-UHFFFAOYSA-N 0.000 claims description 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 2
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
• DTHHUAXKOMWYBI-UHFFFAOYSA-N oxadiazolidine Chemical compound C1CONN1 DTHHUAXKOMWYBI-UHFFFAOYSA-N 0.000 claims description 2
• 125000004043 oxo group Chemical group O=* 0.000 claims description 2
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
• RLTPJVKHGBFGQA-UHFFFAOYSA-N thiadiazolidine Chemical compound C1CSNN1 RLTPJVKHGBFGQA-UHFFFAOYSA-N 0.000 claims description 2
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