EA020715B1 - ПРОИЗВОДНЫЕ 1H-ИМИДАЗО[4,5-c]ХИНОЛИНОНА - Google Patents

Info

Publication number

EA020715B1

EA020715B1 EA201101704A EA201101704A EA020715B1 EA 020715 B1 EA020715 B1 EA 020715B1 EA 201101704 A EA201101704 A EA 201101704A EA 201101704 A EA201101704 A EA 201101704A EA 020715 B1 EA020715 B1 EA 020715B1

Authority

EA

Eurasian Patent Office

Prior art keywords

methyl

pyrazol

dihydroimidazo

quinolin

dimethyl

Prior art date

2009-06-04

Links

• Espacenet
• Global Dossier
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• IQYPSFAWXDKDBA-UHFFFAOYSA-N 1,3-dihydroimidazo[4,5-c]quinolin-2-one Chemical class C1=CC=CC2=C(NC(=O)N3)C3=CN=C21 IQYPSFAWXDKDBA-UHFFFAOYSA-N 0.000 title abstract 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 92
• 201000010099 disease Diseases 0.000 claims abstract description 89
• 150000003839 salts Chemical class 0.000 claims abstract description 65
• 230000001419 dependent effect Effects 0.000 claims abstract description 53
• 238000011282 treatment Methods 0.000 claims abstract description 51
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 50
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 49
• 238000000034 method Methods 0.000 claims abstract description 45
• 150000002632 lipids Chemical class 0.000 claims abstract description 44
• 238000002360 preparation method Methods 0.000 claims abstract description 18
• 241001465754 Metazoa Species 0.000 claims abstract description 11
• -1 methoxyethyl Chemical group 0.000 claims description 2499
• 125000004076 pyridyl group Chemical group 0.000 claims description 254
• 150000001875 compounds Chemical class 0.000 claims description 244
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 52
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 48
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 47
• 229910052739 hydrogen Inorganic materials 0.000 claims description 47
• 239000001257 hydrogen Substances 0.000 claims description 47
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
• 102000001253 Protein Kinase Human genes 0.000 claims description 39
• 108060006633 protein kinase Proteins 0.000 claims description 39
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 30
• 206010028980 Neoplasm Diseases 0.000 claims description 27
• 150000002431 hydrogen Chemical class 0.000 claims description 25
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 24
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims description 16
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 15
• 125000004429 atom Chemical group 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 230000002062 proliferating effect Effects 0.000 claims description 12
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
• 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 10
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
• 201000004681 Psoriasis Diseases 0.000 claims description 10
• 201000011510 cancer Diseases 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 239000000460 chlorine Substances 0.000 claims description 10
• 125000001041 indolyl group Chemical group 0.000 claims description 10
• UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 claims description 9
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 9
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 9
• 230000005764 inhibitory process Effects 0.000 claims description 9
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 230000008482 dysregulation Effects 0.000 claims description 8
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical group CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 8
• 230000009826 neoplastic cell growth Effects 0.000 claims description 8
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
• 208000026310 Breast neoplasm Diseases 0.000 claims description 7
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 7
• 239000003795 chemical substances by application Substances 0.000 claims description 7
• 208000032839 leukemia Diseases 0.000 claims description 7
• 208000011580 syndromic disease Diseases 0.000 claims description 7
• DGCOGZQDAXUUBY-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole Chemical group C1=CC=C2OC(F)(F)OC2=C1 DGCOGZQDAXUUBY-UHFFFAOYSA-N 0.000 claims description 6
• 206010004146 Basal cell carcinoma Diseases 0.000 claims description 6
• 206010039710 Scleroderma Diseases 0.000 claims description 6
• 230000001028 anti-proliverative effect Effects 0.000 claims description 6
• KHBQMWCZKVMBLN-IDEBNGHGSA-N benzenesulfonamide Chemical group NS(=O)(=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 KHBQMWCZKVMBLN-IDEBNGHGSA-N 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 6
• 206010061218 Inflammation Diseases 0.000 claims description 5
• 208000002260 Keloid Diseases 0.000 claims description 5
• 206010050207 Skin fibrosis Diseases 0.000 claims description 5
• 210000002950 fibroblast Anatomy 0.000 claims description 5
• 230000003463 hyperproliferative effect Effects 0.000 claims description 5
• 230000004054 inflammatory process Effects 0.000 claims description 5
• 210000001117 keloid Anatomy 0.000 claims description 5
• 210000003734 kidney Anatomy 0.000 claims description 5
• 210000004185 liver Anatomy 0.000 claims description 5
• 210000004072 lung Anatomy 0.000 claims description 5
• 210000000496 pancreas Anatomy 0.000 claims description 5
• 210000002307 prostate Anatomy 0.000 claims description 5
• 208000017520 skin disease Diseases 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• LFEXGBPVZBXATF-UHFFFAOYSA-N 2,3-dimethylbenzenesulfonamide Chemical group CC1=CC=CC(S(N)(=O)=O)=C1C LFEXGBPVZBXATF-UHFFFAOYSA-N 0.000 claims description 4
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 4
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 4
• 206010006187 Breast cancer Diseases 0.000 claims description 4
• 201000009030 Carcinoma Diseases 0.000 claims description 4
• 206010009944 Colon cancer Diseases 0.000 claims description 4
• 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims description 4
• 206010020649 Hyperkeratosis Diseases 0.000 claims description 4
• 208000001126 Keratosis Diseases 0.000 claims description 4
• 208000008770 Multiple Hamartoma Syndrome Diseases 0.000 claims description 4
• 208000034578 Multiple myelomas Diseases 0.000 claims description 4
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 4
• 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 4
• 206010039491 Sarcoma Diseases 0.000 claims description 4
• 210000004100 adrenal gland Anatomy 0.000 claims description 4
• 210000004556 brain Anatomy 0.000 claims description 4
• 210000000481 breast Anatomy 0.000 claims description 4
• 201000008275 breast carcinoma Diseases 0.000 claims description 4
• 210000001072 colon Anatomy 0.000 claims description 4
• 201000002758 colorectal adenoma Diseases 0.000 claims description 4
• 210000001035 gastrointestinal tract Anatomy 0.000 claims description 4
• 208000005017 glioblastoma Diseases 0.000 claims description 4
• 210000001672 ovary Anatomy 0.000 claims description 4
• 210000000664 rectum Anatomy 0.000 claims description 4
• 210000002784 stomach Anatomy 0.000 claims description 4
• 229940124597 therapeutic agent Drugs 0.000 claims description 4
• 210000001685 thyroid gland Anatomy 0.000 claims description 4
• 238000011200 topical administration Methods 0.000 claims description 4
• 210000003932 urinary bladder Anatomy 0.000 claims description 4
• 210000001215 vagina Anatomy 0.000 claims description 4
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 206010025323 Lymphomas Diseases 0.000 claims description 3
• 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 claims description 3
• 230000001225 therapeutic effect Effects 0.000 claims description 3
• 208000012609 Cowden disease Diseases 0.000 claims description 2
• 150000001408 amides Chemical class 0.000 claims description 2
• 210000002615 epidermis Anatomy 0.000 claims description 2
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 2
• 239000010802 sludge Substances 0.000 claims description 2
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims 196
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 46
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 15
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 8
• SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 5
• IRFHMTUHTBSEBK-QGZVFWFLSA-N tert-butyl n-[(2s)-2-(2,5-difluorophenyl)-3-quinolin-3-ylpropyl]carbamate Chemical compound C1([C@H](CC=2C=C3C=CC=CC3=NC=2)CNC(=O)OC(C)(C)C)=CC(F)=CC=C1F IRFHMTUHTBSEBK-QGZVFWFLSA-N 0.000 claims 5
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
• 206010041823 squamous cell carcinoma Diseases 0.000 claims 3
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
• MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 claims 1
• ZUIQWGFHNGSMEL-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(1,3,3-trimethyl-2-oxopyrrolo[2,3-b]pyridin-5-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C=1N=C2N(C)C(=O)C(C)(C)C2=CC=1C(C=C1C=23)=CC=C1N=CC=2N(C)C(=O)N3C1=CN(C)N=C1C ZUIQWGFHNGSMEL-UHFFFAOYSA-N 0.000 claims 1
• IELISPRQTNVBEH-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(1-methyl-2,3-dihydroindol-5-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C=1C=C2N(C)CCC2=CC=1C(C=C1C=23)=CC=C1N=CC=2N(C)C(=O)N3C1=CN(C)N=C1C IELISPRQTNVBEH-UHFFFAOYSA-N 0.000 claims 1
• KKYACOIQQGSTKA-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(2-propan-2-yloxypyridin-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OC(C)C)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 KKYACOIQQGSTKA-UHFFFAOYSA-N 0.000 claims 1
• UXAMIEHBQJBNJR-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(2-pyrrolidin-1-ylpyrimidin-5-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(=NC=3)N3CCCC3)=CC=C1N=C2 UXAMIEHBQJBNJR-UHFFFAOYSA-N 0.000 claims 1
• OTXNLGMPEHAPSP-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(3-propan-2-yloxyphenyl)imidazo[4,5-c]quinolin-2-one Chemical compound CC(C)OC1=CC=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 OTXNLGMPEHAPSP-UHFFFAOYSA-N 0.000 claims 1
• LQRRFDPNMZOYBL-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(5-methylpyridin-3-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(C)C=NC=3)=CC=C1N=C2 LQRRFDPNMZOYBL-UHFFFAOYSA-N 0.000 claims 1
• TXPSDQNYXFUVPQ-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(5-methylsulfonylpyridin-3-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(C=NC=3)S(C)(=O)=O)=CC=C1N=C2 TXPSDQNYXFUVPQ-UHFFFAOYSA-N 0.000 claims 1
• JKMWINSPNJPJSO-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(5-propan-2-yloxypyridin-3-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC(C)OC1=CN=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 JKMWINSPNJPJSO-UHFFFAOYSA-N 0.000 claims 1
• RZMOAAYESUOZLU-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(6-methylpyridin-3-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(C)=CC=3)=CC=C1N=C2 RZMOAAYESUOZLU-UHFFFAOYSA-N 0.000 claims 1
• SJGLDFUMCMBQSF-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(6-propoxypyridin-3-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OCCC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 SJGLDFUMCMBQSF-UHFFFAOYSA-N 0.000 claims 1
• IANGAVAGXRAWID-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(6-pyrazol-1-ylpyridin-3-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(=CC=3)N3N=CC=C3)=CC=C1N=C2 IANGAVAGXRAWID-UHFFFAOYSA-N 0.000 claims 1
• RGPCFKPSYWVOHF-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(6-pyrrolidin-1-ylpyridin-3-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(=CC=3)N3CCCC3)=CC=C1N=C2 RGPCFKPSYWVOHF-UHFFFAOYSA-N 0.000 claims 1
• UHQHUHUQGCTYTC-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-[2-(methylamino)pyrimidin-5-yl]imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(NC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 UHQHUHUQGCTYTC-UHFFFAOYSA-N 0.000 claims 1
• HCTQTNVJYFAZJY-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]imidazo[4,5-c]quinolin-2-one Chemical compound C1CN(C)CCN1C1=CC=C(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)C=N1 HCTQTNVJYFAZJY-UHFFFAOYSA-N 0.000 claims 1
• OYCORHHCBVOODP-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-phenylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=CC=CC=3)=CC=C1N=C2 OYCORHHCBVOODP-UHFFFAOYSA-N 0.000 claims 1
• VEEDCROLERMEEG-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-pyrazin-2-ylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3N=CC=NC=3)=CC=C1N=C2 VEEDCROLERMEEG-UHFFFAOYSA-N 0.000 claims 1
• KKKNBQIQRWHAHB-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-pyridin-3-ylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC=CC=3)=CC=C1N=C2 KKKNBQIQRWHAHB-UHFFFAOYSA-N 0.000 claims 1
• BMANKENEKFXXPT-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-pyridin-3-ylimidazo[4,5-c]quinoline-2-thione Chemical compound CC1=NN(C)C=C1N1C(=S)N(C)C2=C1C1=CC(C=3C=NC=CC=3)=CC=C1N=C2 BMANKENEKFXXPT-UHFFFAOYSA-N 0.000 claims 1
• RVODCJRTHUSBKW-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-pyrimidin-5-ylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC=NC=3)=CC=C1N=C2 RVODCJRTHUSBKW-UHFFFAOYSA-N 0.000 claims 1
• OSWIYXISAICTFC-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-quinolin-3-ylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C4C=CC=CC4=NC=3)=CC=C1N=C2 OSWIYXISAICTFC-UHFFFAOYSA-N 0.000 claims 1
• DYTBHABOPBCRCF-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(2-ethoxypyrimidin-5-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OCC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 DYTBHABOPBCRCF-UHFFFAOYSA-N 0.000 claims 1
• IECRRPARKHRVLZ-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(2-fluoro-3-propan-2-yloxyphenyl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC(C)OC1=CC=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1F IECRRPARKHRVLZ-UHFFFAOYSA-N 0.000 claims 1
• QWMFQYKHLSPVLB-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(2-methoxypyrimidin-5-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 QWMFQYKHLSPVLB-UHFFFAOYSA-N 0.000 claims 1
• FHOKPXCNQYOFLG-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(3-ethoxy-4-methoxyphenyl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OC)C(OCC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 FHOKPXCNQYOFLG-UHFFFAOYSA-N 0.000 claims 1
• MGVKXFBPFCSAIQ-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(3-ethoxyphenyl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CCOC1=CC=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 MGVKXFBPFCSAIQ-UHFFFAOYSA-N 0.000 claims 1
• NQAMUCRSNZFHLZ-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(3-fluoro-5-hydroxyphenyl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(F)C=C(O)C=3)=CC=C1N=C2 NQAMUCRSNZFHLZ-UHFFFAOYSA-N 0.000 claims 1
• ZQWAUUQVNVSJDR-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(3-hydroxyphenyl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(O)C=CC=3)=CC=C1N=C2 ZQWAUUQVNVSJDR-UHFFFAOYSA-N 0.000 claims 1
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