CA2763821A1 - 1h-imidazo[4,5-c]quinolinone derivatives - Google Patents

Info

Publication number

CA2763821A1

CA2763821A1 CA2763821A CA2763821A CA2763821A1 CA 2763821 A1 CA2763821 A1 CA 2763821A1 CA 2763821 A CA2763821 A CA 2763821A CA 2763821 A CA2763821 A CA 2763821A CA 2763821 A1 CA2763821 A1 CA 2763821A1

Authority

CA

Canada

Prior art keywords

methyl

dihydro

pyrazol

imidazo

quinolin

Prior art date

2009-06-04

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 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
• 238000000034 method Methods 0.000 claims abstract description 129
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 85
• 201000010099 disease Diseases 0.000 claims abstract description 82
• 150000003839 salts Chemical class 0.000 claims abstract description 68
• 238000011282 treatment Methods 0.000 claims abstract description 59
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 47
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 47
• 230000001419 dependent effect Effects 0.000 claims abstract description 40
• 150000002632 lipids Chemical class 0.000 claims abstract description 39
• 238000002360 preparation method Methods 0.000 claims abstract description 13
• 241001465754 Metazoa Species 0.000 claims abstract description 11
• -1 di-substituted amino Chemical group 0.000 claims description 1228
• 150000001875 compounds Chemical class 0.000 claims description 412
• 125000004076 pyridyl group Chemical group 0.000 claims description 390
• 125000000217 alkyl group Chemical group 0.000 claims description 341
• 125000003545 alkoxy group Chemical group 0.000 claims description 153
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 114
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 110
• 125000001424 substituent group Chemical group 0.000 claims description 75
• 125000005843 halogen group Chemical group 0.000 claims description 70
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 60
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 57
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 54
• 125000000623 heterocyclic group Chemical group 0.000 claims description 52
• 229910052739 hydrogen Inorganic materials 0.000 claims description 51
• 239000001257 hydrogen Substances 0.000 claims description 51
• 125000003282 alkyl amino group Chemical group 0.000 claims description 48
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
• 125000001072 heteroaryl group Chemical group 0.000 claims description 34
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 28
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 27
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 26
• 206010028980 Neoplasm Diseases 0.000 claims description 25
• 229910052757 nitrogen Inorganic materials 0.000 claims description 24
• 125000006413 ring segment Chemical group 0.000 claims description 24
• 239000012453 solvate Substances 0.000 claims description 24
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 23
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
• 229940002612 prodrug Drugs 0.000 claims description 21
• 239000000651 prodrug Substances 0.000 claims description 21
• 125000003118 aryl group Chemical group 0.000 claims description 20
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 19
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 19
• 102000001253 Protein Kinase Human genes 0.000 claims description 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
• 108060006633 protein kinase Proteins 0.000 claims description 18
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims description 17
• 125000002393 azetidinyl group Chemical group 0.000 claims description 16
• 125000003342 alkenyl group Chemical group 0.000 claims description 15
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 15
• 229940124530 sulfonamide Drugs 0.000 claims description 15
• 150000003456 sulfonamides Chemical class 0.000 claims description 15
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 14
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 13
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 230000002062 proliferating effect Effects 0.000 claims description 12
• 150000003254 radicals Chemical class 0.000 claims description 12
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 11
• 125000004193 piperazinyl group Chemical group 0.000 claims description 11
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 10
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 10
• 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 10
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 10
• 230000005764 inhibitory process Effects 0.000 claims description 10
• 239000001301 oxygen Substances 0.000 claims description 10
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 9
• 201000011510 cancer Diseases 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 125000005493 quinolyl group Chemical group 0.000 claims description 9
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 9
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 8
• 108091007960 PI3Ks Proteins 0.000 claims description 8
• 201000004681 Psoriasis Diseases 0.000 claims description 8
• 125000000304 alkynyl group Chemical group 0.000 claims description 8
• 125000004122 cyclic group Chemical group 0.000 claims description 8
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 229930185107 quinolinone Natural products 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 238000011200 topical administration Methods 0.000 claims description 8
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 7
• 125000002883 imidazolyl group Chemical group 0.000 claims description 7
• 125000001041 indolyl group Chemical group 0.000 claims description 7
• 208000032839 leukemia Diseases 0.000 claims description 7
• 210000002307 prostate Anatomy 0.000 claims description 7
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 6
• 208000008770 Multiple Hamartoma Syndrome Diseases 0.000 claims description 6
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 6
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 6
• 125000006383 alkylpyridyl group Chemical group 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000002541 furyl group Chemical group 0.000 claims description 6
• 125000006377 halopyridyl group Chemical group 0.000 claims description 6
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 6
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 6
• 230000009826 neoplastic cell growth Effects 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 6
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 6
• 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
• 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 5
• 206010004146 Basal cell carcinoma Diseases 0.000 claims description 5
• 206010039710 Scleroderma Diseases 0.000 claims description 5
• 208000009621 actinic keratosis Diseases 0.000 claims description 5
• 125000004442 acylamino group Chemical group 0.000 claims description 5
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
• 208000017520 skin disease Diseases 0.000 claims description 5
• 125000004434 sulfur atom Chemical group 0.000 claims description 5
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• 125000001425 triazolyl group Chemical group 0.000 claims description 5
• 201000002847 Cowden syndrome Diseases 0.000 claims description 4
• 206010061218 Inflammation Diseases 0.000 claims description 4
• 208000002260 Keloid Diseases 0.000 claims description 4
• 206010050207 Skin fibrosis Diseases 0.000 claims description 4
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 201000008275 breast carcinoma Diseases 0.000 claims description 4
• 125000001589 carboacyl group Chemical group 0.000 claims description 4
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
• 230000008482 dysregulation Effects 0.000 claims description 4
• 210000002950 fibroblast Anatomy 0.000 claims description 4
• 206010020718 hyperplasia Diseases 0.000 claims description 4
• 230000003463 hyperproliferative effect Effects 0.000 claims description 4
• 230000004054 inflammatory process Effects 0.000 claims description 4
• 210000001117 keloid Anatomy 0.000 claims description 4
• 210000003734 kidney Anatomy 0.000 claims description 4
• 210000004185 liver Anatomy 0.000 claims description 4
• 210000004072 lung Anatomy 0.000 claims description 4
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 229940124597 therapeutic agent Drugs 0.000 claims description 4
• 150000003852 triazoles Chemical class 0.000 claims description 4
• 201000009030 Carcinoma Diseases 0.000 claims description 3
• 206010009944 Colon cancer Diseases 0.000 claims description 3
• 208000012609 Cowden disease Diseases 0.000 claims description 3
• 206010061968 Gastric neoplasm Diseases 0.000 claims description 3
• 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims description 3
• 208000034578 Multiple myelomas Diseases 0.000 claims description 3
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
• 206010039491 Sarcoma Diseases 0.000 claims description 3
• 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 claims description 3
• 125000005354 acylalkyl group Chemical group 0.000 claims description 3
• 210000004100 adrenal gland Anatomy 0.000 claims description 3
• 125000000033 alkoxyamino group Chemical group 0.000 claims description 3
• 125000005094 alkyl carbonyl amino alkyl group Chemical group 0.000 claims description 3
• 210000004556 brain Anatomy 0.000 claims description 3
• 210000000481 breast Anatomy 0.000 claims description 3
• 210000001072 colon Anatomy 0.000 claims description 3
• 201000002758 colorectal adenoma Diseases 0.000 claims description 3
• 208000025440 neoplasm of neck Diseases 0.000 claims description 3
• 210000001672 ovary Anatomy 0.000 claims description 3
• 210000000496 pancreas Anatomy 0.000 claims description 3
• 210000000664 rectum Anatomy 0.000 claims description 3
• 206010041823 squamous cell carcinoma Diseases 0.000 claims description 3
• 210000002784 stomach Anatomy 0.000 claims description 3
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
• 210000001685 thyroid gland Anatomy 0.000 claims description 3
• 210000003932 urinary bladder Anatomy 0.000 claims description 3
• 210000001215 vagina Anatomy 0.000 claims description 3
• 201000007815 Bannayan-Riley-Ruvalcaba syndrome Diseases 0.000 claims description 2
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
• 206010025323 Lymphomas Diseases 0.000 claims description 2
• 102100038332 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform Human genes 0.000 claims description 2
• 102100036056 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform Human genes 0.000 claims description 2
• 101710204747 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform Proteins 0.000 claims description 2
• 102100036052 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform Human genes 0.000 claims description 2
• 101710096503 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform Proteins 0.000 claims description 2
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 2
• 125000004423 acyloxy group Chemical group 0.000 claims description 2
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
• 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims description 2
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 208000005017 glioblastoma Diseases 0.000 claims description 2
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 2
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
• 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 2
• NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 2
• 230000000699 topical effect Effects 0.000 claims description 2
• 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims 4
• HPTLKFZXEFDOAY-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[5-(ethylamino)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CCNC1=CN=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 HPTLKFZXEFDOAY-UHFFFAOYSA-N 0.000 claims 2
• 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
• MXMGPTDEHDYXAT-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(1-methylpyrrolo[2,3-b]pyridin-5-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C4C=CN(C)C4=NC=3)=CC=C1N=C2 MXMGPTDEHDYXAT-UHFFFAOYSA-N 0.000 claims 1
• SFZKNCLTLOKJOI-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(1-methylpyrrolo[3,2-b]pyridin-6-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C4N(C)C=CC4=NC=3)=CC=C1N=C2 SFZKNCLTLOKJOI-UHFFFAOYSA-N 0.000 claims 1
• BHDWCVVWJLIEKA-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C4NC=CC4=NC=3)=CC=C1N=C2 BHDWCVVWJLIEKA-UHFFFAOYSA-N 0.000 claims 1
• JYMCDBHFLWTIPU-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(2-oxo-1,3-dihydroindol-5-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C4CC(=O)NC4=CC=3)=CC=C1N=C2 JYMCDBHFLWTIPU-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
• DCUYLKAFZCNOIG-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(3-methylsulfonylphenyl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(C=CC=3)S(C)(=O)=O)=CC=C1N=C2 DCUYLKAFZCNOIG-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
• PRVQPOABMQMJMQ-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(3-pyrrolidin-1-ylsulfonylphenyl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(C=CC=3)S(=O)(=O)N3CCCC3)=CC=C1N=C2 PRVQPOABMQMJMQ-UHFFFAOYSA-N 0.000 claims 1
• FROZIHADXIQWOU-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(4-methyl-2,3-dihydropyrido[3,2-b][1,4]oxazin-7-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C=1N=C2N(C)CCOC2=CC=1C(C=C1C=23)=CC=C1N=CC=2N(C)C(=O)N3C1=CN(C)N=C1C FROZIHADXIQWOU-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
• YWDAJLXJSLKKPA-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(6-methyl-5-propan-2-yloxypyridin-3-yl)imidazo[4,5-c]quinolin-2-one Chemical compound N1=C(C)C(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 YWDAJLXJSLKKPA-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
• RUPJVEKBCXESLQ-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-(6-piperazin-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)N3CCNCC3)=CC=C1N=C2 RUPJVEKBCXESLQ-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
• BIUCQTOPTKWGGS-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-[5-(propan-2-ylamino)pyridin-3-yl]imidazo[4,5-c]quinolin-2-one Chemical compound CC(C)NC1=CN=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 BIUCQTOPTKWGGS-UHFFFAOYSA-N 0.000 claims 1
• VGLOTZOSBKONTN-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-[5-[methyl(propan-2-yl)amino]pyridin-3-yl]imidazo[4,5-c]quinolin-2-one Chemical compound CC(C)N(C)C1=CN=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 VGLOTZOSBKONTN-UHFFFAOYSA-N 0.000 claims 1
• XIYMWNHFLNULAA-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-[6-(2-methylimidazol-1-yl)pyridin-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)N3C(=NC=C3)C)=CC=C1N=C2 XIYMWNHFLNULAA-UHFFFAOYSA-N 0.000 claims 1
• MBLKKVJZDGISTH-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-[6-(2h-tetrazol-5-yl)pyridin-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)C3=NNN=N3)=CC=C1N=C2 MBLKKVJZDGISTH-UHFFFAOYSA-N 0.000 claims 1
• LVHSOVZBRRPSPB-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-[6-(3-phenylmethoxypropoxy)pyridin-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(OCCCOCC=4C=CC=CC=4)=CC=3)=CC=C1N=C2 LVHSOVZBRRPSPB-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
• DNJLZVASPOPYKC-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-[6-(methylamino)-5-(trifluoromethyl)pyridin-3-yl]imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(C(F)(F)F)C(NC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 DNJLZVASPOPYKC-UHFFFAOYSA-N 0.000 claims 1
• MGEMSFMTHGPAJZ-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-[6-(oxan-4-ylamino)pyridin-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(NC4CCOCC4)=CC=3)=CC=C1N=C2 MGEMSFMTHGPAJZ-UHFFFAOYSA-N 0.000 claims 1
• DKPLYWZHXGGMEJ-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-[6-methyl-5-(methylamino)pyridin-3-yl]imidazo[4,5-c]quinolin-2-one Chemical compound N1=C(C)C(NC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 DKPLYWZHXGGMEJ-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
• ZDWNVZVPHKACMG-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-3-methyl-8-pyridin-2-ylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3N=CC=CC=3)=CC=C1N=C2 ZDWNVZVPHKACMG-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
• OBXQUDQRYXPVER-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(1-ethyl-3-methyl-2-oxoimidazo[4,5-b]pyridin-6-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C=1N=C2N(C)C(=O)N(CC)C2=CC=1C(C=C1C=23)=CC=C1N=CC=2N(C)C(=O)N3C1=CN(C)N=C1C OBXQUDQRYXPVER-UHFFFAOYSA-N 0.000 claims 1
• HMYPSMZYEFVHKV-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(2-ethoxypyridin-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OCC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 HMYPSMZYEFVHKV-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
• SSVNASCAPYZITK-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(2-methoxy-3-methylimidazo[4,5-b]pyridin-6-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C=1N=C2N(C)C(OC)=NC2=CC=1C(C=C1C=23)=CC=C1N=CC=2N(C)C(=O)N3C1=CN(C)N=C1C SSVNASCAPYZITK-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
• YASIQRFBBRCCOY-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(4-ethoxy-3-methoxyphenyl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OC)C(OCC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 YASIQRFBBRCCOY-UHFFFAOYSA-N 0.000 claims 1
• KLDUDOYFBKCYMP-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(5-ethoxy-6-ethylpyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(CC)C(OCC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 KLDUDOYFBKCYMP-UHFFFAOYSA-N 0.000 claims 1
• OKCIYJAJRUQWMH-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(5-ethoxy-6-methoxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=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 OKCIYJAJRUQWMH-UHFFFAOYSA-N 0.000 claims 1
• FLLHYJRGDOAUQB-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(5-ethoxy-6-methylpyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(C)C(OCC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 FLLHYJRGDOAUQB-UHFFFAOYSA-N 0.000 claims 1
• IZAJYAFKAMMMBH-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(5-ethoxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CCOC1=CN=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 IZAJYAFKAMMMBH-UHFFFAOYSA-N 0.000 claims 1
• GEHNDGQTLWGWPB-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(5-fluoro-6-methoxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(F)C(OC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 GEHNDGQTLWGWPB-UHFFFAOYSA-N 0.000 claims 1
• VKFIYZMAHMYPCV-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(5-hydroxy-6-methylpyridin-3-yl)-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(C)=NC=3)=CC=C1N=C2 VKFIYZMAHMYPCV-UHFFFAOYSA-N 0.000 claims 1
• GCOVLEVLHOSHAN-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(5-methoxy-6-methylpyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(C)C(OC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 GCOVLEVLHOSHAN-UHFFFAOYSA-N 0.000 claims 1
• QBDDZTLLQQBVOK-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(5-methoxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound COC1=CN=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 QBDDZTLLQQBVOK-UHFFFAOYSA-N 0.000 claims 1
• AYYWYSOXTNBQMO-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(6-ethoxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OCC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 AYYWYSOXTNBQMO-UHFFFAOYSA-N 0.000 claims 1
• YFXCBAMIYIOKDX-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(6-ethoxypyridin-3-yl)-3h-imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OCC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2)C3=C1 YFXCBAMIYIOKDX-UHFFFAOYSA-N 0.000 claims 1
• UFJZVWGRIXJLRG-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(6-ethyl-5-hydroxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(O)C(CC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 UFJZVWGRIXJLRG-UHFFFAOYSA-N 0.000 claims 1
• UMUIMFZVVDMSAS-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(6-ethyl-5-propan-2-yloxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OC(C)C)C(CC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 UMUIMFZVVDMSAS-UHFFFAOYSA-N 0.000 claims 1
• HRXIJNSPULLJIN-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(6-methoxy-5-nitropyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C([N+]([O-])=O)C(OC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 HRXIJNSPULLJIN-UHFFFAOYSA-N 0.000 claims 1
• YQHUGIMCEWYJIA-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(6-methoxy-5-propan-2-yloxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OC(C)C)C(OC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 YQHUGIMCEWYJIA-UHFFFAOYSA-N 0.000 claims 1
• OUBRJQOQTYPGFM-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(6-methoxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 OUBRJQOQTYPGFM-UHFFFAOYSA-N 0.000 claims 1
• HWPIMRFVTKPCAI-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-(6-methoxypyridin-3-yl)-3h-imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2)C3=C1 HWPIMRFVTKPCAI-UHFFFAOYSA-N 0.000 claims 1
• GYEHLJRDOXWRNB-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[1-(2-hydroxyethyl)pyrazol-4-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C3=CN(CCO)N=C3)=CC=C1N=C2 GYEHLJRDOXWRNB-UHFFFAOYSA-N 0.000 claims 1
• XVVJCUQIOHIFQB-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[1-(2-methoxyethyl)-3-methyl-2-oxoimidazo[4,5-b]pyridin-6-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C=1N=C2N(C)C(=O)N(CCOC)C2=CC=1C(C=C1C=23)=CC=C1N=CC=2N(C)C(=O)N3C1=CN(C)N=C1C XVVJCUQIOHIFQB-UHFFFAOYSA-N 0.000 claims 1
• BTXKTXRPLWVRMV-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[3-hydroxy-5-(trifluoromethyl)phenyl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(C=C(O)C=3)C(F)(F)F)=CC=C1N=C2 BTXKTXRPLWVRMV-UHFFFAOYSA-N 0.000 claims 1
• IWORQMGTINOTTO-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[3-methoxy-4-(2-methoxyethoxy)phenyl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OC)C(OCCOC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 IWORQMGTINOTTO-UHFFFAOYSA-N 0.000 claims 1
• WQBSNDLGFILBFL-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[4-(1h-imidazol-2-yl)phenyl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=CC(=CC=3)C=3NC=CN=3)=CC=C1N=C2 WQBSNDLGFILBFL-UHFFFAOYSA-N 0.000 claims 1
• SWFCYNYDAJGYJG-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[5-(1-hydroxy-2-methylpropan-2-yl)pyridin-3-yl]-3-methylimidazo[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)C(C)(C)CO)=CC=C1N=C2 SWFCYNYDAJGYJG-UHFFFAOYSA-N 0.000 claims 1
• CQKLRZZPSLVYTQ-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[5-(1-hydroxycyclopentyl)pyridin-3-yl]-3-methylimidazo[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)C3(O)CCCC3)=CC=C1N=C2 CQKLRZZPSLVYTQ-UHFFFAOYSA-N 0.000 claims 1
• SCOLKFZBUMDLEI-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[5-(2-ethoxypropan-2-yl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CCOC(C)(C)C1=CN=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 SCOLKFZBUMDLEI-UHFFFAOYSA-N 0.000 claims 1
• BYGUAZWKRLEAIB-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[5-(2-fluoroethoxy)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(OCCF)C=NC=3)=CC=C1N=C2 BYGUAZWKRLEAIB-UHFFFAOYSA-N 0.000 claims 1
• ZJYUDWFYVVEQLZ-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[5-(2-hydroxypropan-2-yl)pyridin-3-yl]-3-methylimidazo[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)C(C)(C)O)=CC=C1N=C2 ZJYUDWFYVVEQLZ-UHFFFAOYSA-N 0.000 claims 1
• YTOKPYJWIRXATK-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[5-(2-methoxyethoxy)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound COCCOC1=CN=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 YTOKPYJWIRXATK-UHFFFAOYSA-N 0.000 claims 1
• FUQGMMCVVHXUDL-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[5-(2-methoxypropan-2-yl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound COC(C)(C)C1=CN=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 FUQGMMCVVHXUDL-UHFFFAOYSA-N 0.000 claims 1
• QTCFZKSPYAXFBC-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[5-(ethoxymethyl)-6-(ethylamino)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(COCC)C(NCC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 QTCFZKSPYAXFBC-UHFFFAOYSA-N 0.000 claims 1
• FANIDXJTSOJKST-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[5-(ethylamino)-6-methylpyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(C)C(NCC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 FANIDXJTSOJKST-UHFFFAOYSA-N 0.000 claims 1
• FNCCXQQJKNAQGF-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[5-(methoxymethyl)-6-(methylamino)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(COC)C(NC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 FNCCXQQJKNAQGF-UHFFFAOYSA-N 0.000 claims 1
• SDZSUZVZSMTDIR-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[5-[ethyl(methyl)amino]-6-methylpyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(C)C(N(C)CC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 SDZSUZVZSMTDIR-UHFFFAOYSA-N 0.000 claims 1
• SMTUAZLWXNWYDS-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[5-[ethyl(methyl)amino]pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CCN(C)C1=CN=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 SMTUAZLWXNWYDS-UHFFFAOYSA-N 0.000 claims 1
• QLAHGENDIDSGRC-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[5-ethoxy-6-(hydroxymethyl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(CO)C(OCC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 QLAHGENDIDSGRC-UHFFFAOYSA-N 0.000 claims 1
• GGTOONFAOXLMQI-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[5-ethoxy-6-(methoxymethyl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(COC)C(OCC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 GGTOONFAOXLMQI-UHFFFAOYSA-N 0.000 claims 1
• GGTOONFAOXLMQI-VPYROQPTSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[5-ethoxy-6-(trideuteriomethoxymethyl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OCC)C(COC([2H])([2H])[2H])=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 GGTOONFAOXLMQI-VPYROQPTSA-N 0.000 claims 1
• BRWRQUUJXRHZFU-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[5-fluoro-6-(methylamino)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(F)C(NC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 BRWRQUUJXRHZFU-UHFFFAOYSA-N 0.000 claims 1
• DNXBDIOCYSMLRY-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[5-methoxy-6-(methoxymethyl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OC)C(COC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 DNXBDIOCYSMLRY-UHFFFAOYSA-N 0.000 claims 1
• RDAQGSYECOVCOX-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-(2-hydroxyethoxy)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(OCCO)=CC=3)=CC=C1N=C2 RDAQGSYECOVCOX-UHFFFAOYSA-N 0.000 claims 1
• ZMFBZHLHXHMBOD-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-(2-hydroxyethylamino)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(NCCO)=CC=3)=CC=C1N=C2 ZMFBZHLHXHMBOD-UHFFFAOYSA-N 0.000 claims 1
• YWXDGIUABOYJSM-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-(2-methoxyethoxy)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OCCOC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 YWXDGIUABOYJSM-UHFFFAOYSA-N 0.000 claims 1
• UHTHATQRMBOXCK-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-(ethylamino)-5-(methoxymethyl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(COC)C(NCC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 UHTHATQRMBOXCK-UHFFFAOYSA-N 0.000 claims 1
• SFKRWDGCAHAHFV-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-(ethylamino)-5-(trifluoromethyl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(C(F)(F)F)C(NCC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 SFKRWDGCAHAHFV-UHFFFAOYSA-N 0.000 claims 1
• BNPSUNJBNOJNCD-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-(hydroxymethyl)-5-(2-methoxyethoxy)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(CO)C(OCCOC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 BNPSUNJBNOJNCD-UHFFFAOYSA-N 0.000 claims 1
• FQDYSETYERVIQT-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-(hydroxymethyl)-5-(methylamino)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(CO)C(NC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 FQDYSETYERVIQT-UHFFFAOYSA-N 0.000 claims 1
• LCJJDUCYSHCJLK-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-(hydroxymethyl)-5-propan-2-yloxypyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(CO)C(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 LCJJDUCYSHCJLK-UHFFFAOYSA-N 0.000 claims 1
• QPOPFQOYVUWLGO-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-(hydroxymethyl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(CO)=CC=3)=CC=C1N=C2 QPOPFQOYVUWLGO-UHFFFAOYSA-N 0.000 claims 1
• XHNOXJZUOTVGFJ-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-(methoxymethyl)-5-(methylamino)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(COC)C(NC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 XHNOXJZUOTVGFJ-UHFFFAOYSA-N 0.000 claims 1
• RFDSBXXJAQPOGG-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-(methoxymethyl)-5-propan-2-yloxypyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OC(C)C)C(COC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 RFDSBXXJAQPOGG-UHFFFAOYSA-N 0.000 claims 1
• XRYARIJYFLNCRO-GOSISDBHSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-[(3r)-3-hydroxypyrrolidin-1-yl]pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(=CC=3)N3C[C@H](O)CC3)=CC=C1N=C2 XRYARIJYFLNCRO-GOSISDBHSA-N 0.000 claims 1
• NGQXAQGOFDIITH-LJQANCHMSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-[(3r)-3-methoxypyrrolidin-1-yl]pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1[C@H](OC)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 NGQXAQGOFDIITH-LJQANCHMSA-N 0.000 claims 1
• XRYARIJYFLNCRO-SFHVURJKSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-[(3s)-3-hydroxypyrrolidin-1-yl]pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(=CC=3)N3C[C@@H](O)CC3)=CC=C1N=C2 XRYARIJYFLNCRO-SFHVURJKSA-N 0.000 claims 1
• NGQXAQGOFDIITH-IBGZPJMESA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-[(3s)-3-methoxypyrrolidin-1-yl]pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1[C@@H](OC)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 NGQXAQGOFDIITH-IBGZPJMESA-N 0.000 claims 1
• JBSQKSWXFLWVIN-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-[ethyl(methyl)amino]pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(N(C)CC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 JBSQKSWXFLWVIN-UHFFFAOYSA-N 0.000 claims 1
• YXOMEXTVNYMLRM-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-ethyl-5-(ethylamino)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(CC)C(NCC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 YXOMEXTVNYMLRM-UHFFFAOYSA-N 0.000 claims 1
• PLTLCVGXXHNNDX-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-ethyl-5-(propan-2-ylamino)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(NC(C)C)C(CC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 PLTLCVGXXHNNDX-UHFFFAOYSA-N 0.000 claims 1
• PYIYHQJHHZFUFP-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-fluoro-5-(methylamino)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(F)C(NC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 PYIYHQJHHZFUFP-UHFFFAOYSA-N 0.000 claims 1
• VRPDYWGRNLIOBW-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-8-[6-methoxy-5-(methoxymethyl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(OC)C(COC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 VRPDYWGRNLIOBW-UHFFFAOYSA-N 0.000 claims 1
• UNHJPRWRSGKYSH-UHFFFAOYSA-N 1-(1,5-dimethylpyrazol-4-yl)-8-(6-methoxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OC)=CC=C1C1=CC=C(N=CC2=C3N(C4=C(N(C)N=C4)C)C(=O)N2C)C3=C1 UNHJPRWRSGKYSH-UHFFFAOYSA-N 0.000 claims 1
• QDKISVBPRUQQJX-UHFFFAOYSA-N 1-(1-ethyl-3-methylpyrazol-4-yl)-3-methyl-8-(4-pyrazol-1-ylphenyl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=CC(=CC=3)N3N=CC=C3)=CC=C1N=C2 QDKISVBPRUQQJX-UHFFFAOYSA-N 0.000 claims 1
• AGKJHSRPJCEWSR-UHFFFAOYSA-N 1-(1-ethyl-3-methylpyrazol-4-yl)-3-methyl-8-(5-propan-2-yloxypyridin-3-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(OC(C)C)C=NC=3)=CC=C1N=C2 AGKJHSRPJCEWSR-UHFFFAOYSA-N 0.000 claims 1
• QKPMMMOAUFMASE-UHFFFAOYSA-N 1-(1-ethyl-3-methylpyrazol-4-yl)-3-methyl-8-(6-methyl-5-propan-2-yloxypyridin-3-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(OC(C)C)C(C)=NC=3)=CC=C1N=C2 QKPMMMOAUFMASE-UHFFFAOYSA-N 0.000 claims 1
• CSBCHXIPCLUCIB-UHFFFAOYSA-N 1-(1-ethyl-3-methylpyrazol-4-yl)-3-methyl-8-[6-(methylamino)pyridin-3-yl]imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(NC)=CC=3)=CC=C1N=C2 CSBCHXIPCLUCIB-UHFFFAOYSA-N 0.000 claims 1
• XNFDHISXGYHXDW-UHFFFAOYSA-N 1-(1-ethyl-3-methylpyrazol-4-yl)-8-(2-methoxypyrimidin-5-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(OC)=NC=3)=CC=C1N=C2 XNFDHISXGYHXDW-UHFFFAOYSA-N 0.000 claims 1
• HWZDYNRHFLRZHN-UHFFFAOYSA-N 1-(1-ethyl-3-methylpyrazol-4-yl)-8-(6-methoxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(OC)=CC=3)=CC=C1N=C2 HWZDYNRHFLRZHN-UHFFFAOYSA-N 0.000 claims 1
• SHYUPAWGCULQMV-UHFFFAOYSA-N 1-(1-ethyl-3-methylpyrazol-4-yl)-8-[3-methoxy-4-(2-methoxyethoxy)phenyl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(OC)C(OCCOC)=CC=3)=CC=C1N=C2 SHYUPAWGCULQMV-UHFFFAOYSA-N 0.000 claims 1
• GMMNMXBGQFHQPY-UHFFFAOYSA-N 1-(1-ethyl-3-methylpyrazol-4-yl)-8-[5-(methoxymethyl)-6-(methylamino)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(COC)C(NC)=NC=3)=CC=C1N=C2 GMMNMXBGQFHQPY-UHFFFAOYSA-N 0.000 claims 1
• BWYIBUBMLOUGAV-UHFFFAOYSA-N 1-(1-ethyl-3-methylpyrazol-4-yl)-8-[5-methoxy-6-(methoxymethyl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(OC)C(COC)=NC=3)=CC=C1N=C2 BWYIBUBMLOUGAV-UHFFFAOYSA-N 0.000 claims 1
• OADJZUAJBWJPIE-UHFFFAOYSA-N 1-(1-ethyl-3-methylpyrazol-4-yl)-8-[6-(hydroxymethyl)-5-(methylamino)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(NC)C(CO)=NC=3)=CC=C1N=C2 OADJZUAJBWJPIE-UHFFFAOYSA-N 0.000 claims 1
• VGCWHUUHLIBYFK-UHFFFAOYSA-N 1-(1-ethyl-3-methylpyrazol-4-yl)-8-[6-(methoxymethyl)-5-(methylamino)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(NC)C(COC)=NC=3)=CC=C1N=C2 VGCWHUUHLIBYFK-UHFFFAOYSA-N 0.000 claims 1
• GOOBWHSOXSHCLE-UHFFFAOYSA-N 1-(1-ethyl-3-methylpyrazol-4-yl)-8-[6-(methoxymethyl)-5-propan-2-yloxypyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(OC(C)C)C(COC)=NC=3)=CC=C1N=C2 GOOBWHSOXSHCLE-UHFFFAOYSA-N 0.000 claims 1
• VVMHQLUWFUNUHX-UHFFFAOYSA-N 1-(1-ethyl-3-methylpyrazol-4-yl)-8-[6-(methoxymethyl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(COC)=CC=3)=CC=C1N=C2 VVMHQLUWFUNUHX-UHFFFAOYSA-N 0.000 claims 1
• CLYHJXQYUJLUAR-UHFFFAOYSA-N 1-(1-ethyl-3-methylpyrazol-4-yl)-8-[6-fluoro-5-(methylamino)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(NC)C(F)=NC=3)=CC=C1N=C2 CLYHJXQYUJLUAR-UHFFFAOYSA-N 0.000 claims 1
• HOGBXHRFKFJITA-UHFFFAOYSA-N 1-(2,4-dimethylpyrazol-3-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=5N(N=CC=5C)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 HOGBXHRFKFJITA-UHFFFAOYSA-N 0.000 claims 1
• RAGGZQWFTJXTQJ-UHFFFAOYSA-N 1-(2,4-dimethylpyrazol-3-yl)-8-(5-ethoxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CCOC1=CN=CC(C=2C=C3C=4N(C=5N(N=CC=5C)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 RAGGZQWFTJXTQJ-UHFFFAOYSA-N 0.000 claims 1
• AHKUXPTXLIMGNH-UHFFFAOYSA-N 1-(2,4-dimethylpyrazol-3-yl)-8-(6-methoxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4N(N=CC=4C)C)C(=O)N2C)C3=C1 AHKUXPTXLIMGNH-UHFFFAOYSA-N 0.000 claims 1
• MXZDEWJTLPXYGZ-UHFFFAOYSA-N 1-(2,5-dimethylpyrazol-3-yl)-3-methyl-8-(5-morpholin-4-ylpyridin-3-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CN1N=C(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(C=NC=3)N3CCOCC3)=CC=C1N=C2 MXZDEWJTLPXYGZ-UHFFFAOYSA-N 0.000 claims 1
• GUAQFVOAGOUQJD-UHFFFAOYSA-N 1-(2,5-dimethylpyrazol-3-yl)-8-(2-fluoropyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CN1N=C(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C(=NC=CC=3)F)=CC=C1N=C2 GUAQFVOAGOUQJD-UHFFFAOYSA-N 0.000 claims 1
• ZEUNTERTAXRBNO-UHFFFAOYSA-N 1-(2,5-dimethylpyrazol-3-yl)-8-(5-hydroxy-6-methylpyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CN1N=C(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(O)C(C)=NC=3)=CC=C1N=C2 ZEUNTERTAXRBNO-UHFFFAOYSA-N 0.000 claims 1
• OXQQUSIDGMPITK-UHFFFAOYSA-N 1-(2,5-dimethylpyrazol-3-yl)-8-(6-methoxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4N(N=C(C)C=4)C)C(=O)N2C)C3=C1 OXQQUSIDGMPITK-UHFFFAOYSA-N 0.000 claims 1
• JGFVJFWCAHXRHC-UHFFFAOYSA-N 1-(2-ethylpyrazol-3-yl)-8-(6-methoxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CCN1N=CC=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(OC)=CC=3)=CC=C1N=C2 JGFVJFWCAHXRHC-UHFFFAOYSA-N 0.000 claims 1
• SQPOTWUTDQGLKJ-UHFFFAOYSA-N 1-(3,5-dimethyl-1,2-oxazol-4-yl)-8-[5-(ethylamino)-6-fluoropyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(F)C(NCC)=CC(C=2C=C3C=4N(C5=C(ON=C5C)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 SQPOTWUTDQGLKJ-UHFFFAOYSA-N 0.000 claims 1
• GSHPNOIWKBBFMI-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-3-methyl-8-[5-methyl-6-(methylamino)pyridin-3-yl]imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(C)C(NC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)Cl)C(=O)N2C)C3=C1 GSHPNOIWKBBFMI-UHFFFAOYSA-N 0.000 claims 1
• SGPIFLKFYHGTCO-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-3-methyl-8-[6-(methylamino)pyridin-3-yl]imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(NC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)Cl)C(=O)N2C)C3=C1 SGPIFLKFYHGTCO-UHFFFAOYSA-N 0.000 claims 1
• XCWWSQSYCWCFIO-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-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)Cl)C(=O)N2C)C3=C1 XCWWSQSYCWCFIO-UHFFFAOYSA-N 0.000 claims 1
• DNPWWYOGHVHZRY-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-(3,4-dimethoxyphenyl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)Cl)C(=O)N2C)C3=C1 DNPWWYOGHVHZRY-UHFFFAOYSA-N 0.000 claims 1
• YRIYNNZITVCEQP-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-(5-ethoxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CCOC1=CN=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)Cl)C(=O)N(C)C=4C=NC3=CC=2)=C1 YRIYNNZITVCEQP-UHFFFAOYSA-N 0.000 claims 1
• KEFFNESMSOAVGU-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-(6-ethoxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OCC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)Cl)C(=O)N2C)C3=C1 KEFFNESMSOAVGU-UHFFFAOYSA-N 0.000 claims 1
• CQDMELBNUHGQQC-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-[5-(2-hydroxypropan-2-yl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound ClC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(C=NC=3)C(C)(C)O)=CC=C1N=C2 CQDMELBNUHGQQC-UHFFFAOYSA-N 0.000 claims 1
• JVVGDUUMIOMCBL-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-[5-(2-methoxyethoxy)-6-methylpyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(C)C(OCCOC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)Cl)C(=O)N(C)C=4C=NC3=CC=2)=C1 JVVGDUUMIOMCBL-UHFFFAOYSA-N 0.000 claims 1
• FYLJVVLAUMLETL-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-[5-(2-methoxyethoxy)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound COCCOC1=CN=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)Cl)C(=O)N(C)C=4C=NC3=CC=2)=C1 FYLJVVLAUMLETL-UHFFFAOYSA-N 0.000 claims 1
• LYWVUAHREBMRBE-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-[5-(ethylamino)-6-methoxypyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(OC)C(NCC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)Cl)C(=O)N(C)C=4C=NC3=CC=2)=C1 LYWVUAHREBMRBE-UHFFFAOYSA-N 0.000 claims 1
• KIHMPIBJBBMOIZ-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-[5-(ethylamino)-6-methylpyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(C)C(NCC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)Cl)C(=O)N(C)C=4C=NC3=CC=2)=C1 KIHMPIBJBBMOIZ-UHFFFAOYSA-N 0.000 claims 1
• AODRZGHQZRKHMI-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-[5-(hydroxymethyl)-6-methoxypyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(CO)C(OC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)Cl)C(=O)N2C)C3=C1 AODRZGHQZRKHMI-UHFFFAOYSA-N 0.000 claims 1
• RVTGCGPKUYHKFN-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-[5-(methoxymethyl)-6-(methylamino)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(COC)C(NC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)Cl)C(=O)N2C)C3=C1 RVTGCGPKUYHKFN-UHFFFAOYSA-N 0.000 claims 1
• ZGCDLHOYEAXHDR-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-[5-(methoxymethyl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound COCC1=CN=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)Cl)C(=O)N(C)C=4C=NC3=CC=2)=C1 ZGCDLHOYEAXHDR-UHFFFAOYSA-N 0.000 claims 1
• JDLCZFOQSRNJDQ-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-[5-methoxy-6-(methoxymethyl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OC)C(COC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)Cl)C(=O)N2C)C3=C1 JDLCZFOQSRNJDQ-UHFFFAOYSA-N 0.000 claims 1
• JDLCZFOQSRNJDQ-HPRDVNIFSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-[5-methoxy-6-(trideuteriomethoxymethyl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OC)C(COC([2H])([2H])[2H])=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)Cl)C(=O)N2C)C3=C1 JDLCZFOQSRNJDQ-HPRDVNIFSA-N 0.000 claims 1
• VXRLOZCKABUJKG-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-[6-(dimethylamino)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(N(C)C)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)Cl)C(=O)N2C)C3=C1 VXRLOZCKABUJKG-UHFFFAOYSA-N 0.000 claims 1
• AQAZUOXGUWNPLP-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-[6-(hydroxymethyl)-5-(methylamino)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(CO)C(NC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)Cl)C(=O)N(C)C=4C=NC3=CC=2)=C1 AQAZUOXGUWNPLP-UHFFFAOYSA-N 0.000 claims 1
• QGDNPYNAEWWDRI-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-[6-(hydroxymethyl)-5-methoxypyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(CO)C(OC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)Cl)C(=O)N(C)C=4C=NC3=CC=2)=C1 QGDNPYNAEWWDRI-UHFFFAOYSA-N 0.000 claims 1
• RRHWMNZGEAQQEI-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-[6-(hydroxymethyl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound ClC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(CO)=CC=3)=CC=C1N=C2 RRHWMNZGEAQQEI-UHFFFAOYSA-N 0.000 claims 1
• VKCSHXCRJZCRLM-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-[6-(methoxymethyl)-5-(methylamino)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(COC)C(NC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)Cl)C(=O)N(C)C=4C=NC3=CC=2)=C1 VKCSHXCRJZCRLM-UHFFFAOYSA-N 0.000 claims 1
• OAUCULMCQPSJNW-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-[6-(methoxymethyl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(COC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)Cl)C(=O)N2C)C3=C1 OAUCULMCQPSJNW-UHFFFAOYSA-N 0.000 claims 1
• LNBGPXXEIRLIEZ-UHFFFAOYSA-N 1-(3-chloro-1-methylpyrazol-4-yl)-8-[6-methoxy-5-(methoxymethyl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(OC)C(COC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)Cl)C(=O)N(C)C=4C=NC3=CC=2)=C1 LNBGPXXEIRLIEZ-UHFFFAOYSA-N 0.000 claims 1
• BJVGMJBYLIMWMU-UHFFFAOYSA-N 1-[1-(2-hydroxyethyl)-3-methylpyrazol-4-yl]-3-methyl-8-(5-morpholin-4-ylpyridin-3-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CCO)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(C=NC=3)N3CCOCC3)=CC=C1N=C2 BJVGMJBYLIMWMU-UHFFFAOYSA-N 0.000 claims 1
• RNRVQURGTUVOPD-UHFFFAOYSA-N 1-[1-(2-hydroxyethyl)-3-methylpyrazol-4-yl]-8-(5-methoxy-6-methylpyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(C)C(OC)=CC(C=2C=C3C=4N(C=5C(=NN(CCO)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 RNRVQURGTUVOPD-UHFFFAOYSA-N 0.000 claims 1
• UCNNOZOIPMTELY-UHFFFAOYSA-N 1-[1-(2-hydroxyethyl)-3-methylpyrazol-4-yl]-8-(6-methoxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(CCO)C=4)C)C(=O)N2C)C3=C1 UCNNOZOIPMTELY-UHFFFAOYSA-N 0.000 claims 1
• LKGNAVBQEVHRLV-UHFFFAOYSA-N 1-[1-[2-(azetidin-1-yl)-2-oxoethyl]-3-methylpyrazol-4-yl]-3-methyl-8-(2-pyrrolidin-1-ylpyrimidin-5-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(N2C(N(C)C3=C2C2=CC(=CC=C2N=C3)C=2C=NC(=NC=2)N2CCCC2)=O)C(C)=NN1CC(=O)N1CCC1 LKGNAVBQEVHRLV-UHFFFAOYSA-N 0.000 claims 1
• MXHNRTGFIJLZKL-UHFFFAOYSA-N 1-[1-[2-(azetidin-1-yl)-2-oxoethyl]-3-methylpyrazol-4-yl]-8-(6-ethoxypyridin-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OCC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(CC(=O)N5CCC5)C=4)C)C(=O)N2C)C3=C1 MXHNRTGFIJLZKL-UHFFFAOYSA-N 0.000 claims 1
• WOORDBFVUABCNR-UHFFFAOYSA-N 1-[5-[1-(1,3-dimethylpyrazol-4-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-8-yl]pyridin-3-yl]cyclobutane-1-carbonitrile Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(C=NC=3)C3(CCC3)C#N)=CC=C1N=C2 WOORDBFVUABCNR-UHFFFAOYSA-N 0.000 claims 1
• VPRWOVZFYZGQHD-UHFFFAOYSA-N 1-[5-[1-(1-ethyl-3-methylpyrazol-4-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-8-yl]pyridin-3-yl]cyclobutane-1-carbonitrile Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(C=NC=3)C3(CCC3)C#N)=CC=C1N=C2 VPRWOVZFYZGQHD-UHFFFAOYSA-N 0.000 claims 1
• YPAOBAWVBOKKGF-UHFFFAOYSA-N 1-methyl-6-[3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)-2-oxoimidazo[4,5-c]quinolin-8-yl]-4h-pyrido[2,3-d][1,3]oxazin-2-one Chemical compound CC1=NN(C(C)C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C4COC(=O)N(C)C4=NC=3)=CC=C1N=C2 YPAOBAWVBOKKGF-UHFFFAOYSA-N 0.000 claims 1
• PKLFKZOZWDTWGI-UHFFFAOYSA-N 2-[3,5-dimethyl-4-[3-methyl-2-oxo-8-(4-pyrazol-1-ylphenyl)imidazo[4,5-c]quinolin-1-yl]pyrazol-1-yl]-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CN1N=C(C)C(N2C(N(C)C3=C2C2=CC(=CC=C2N=C3)C=2C=CC(=CC=2)N2N=CC=C2)=O)=C1C PKLFKZOZWDTWGI-UHFFFAOYSA-N 0.000 claims 1
• OKDMKFLTPBOOCN-UHFFFAOYSA-N 2-[4-[8-(5-ethoxy-6-methylpyridin-3-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-1-yl]-3,5-dimethylpyrazol-1-yl]-n,n-dimethylacetamide Chemical compound N1=C(C)C(OCC)=CC(C=2C=C3C=4N(C5=C(N(CC(=O)N(C)C)N=C5C)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 OKDMKFLTPBOOCN-UHFFFAOYSA-N 0.000 claims 1
• LQWVQBUTKZMQIO-UHFFFAOYSA-N 2-[4-[8-(5-ethoxypyridin-3-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-1-yl]-3-methylpyrazol-1-yl]-n,n-dimethylacetamide Chemical compound CCOC1=CN=CC(C=2C=C3C=4N(C=5C(=NN(CC(=O)N(C)C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 LQWVQBUTKZMQIO-UHFFFAOYSA-N 0.000 claims 1
• URWLNMGORNCENB-UHFFFAOYSA-N 2-[4-[8-(6-ethoxypyridin-3-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-1-yl]-3,5-dimethylpyrazol-1-yl]-n,n-dimethylacetamide Chemical compound C1=NC(OCC)=CC=C1C1=CC=C(N=CC2=C3N(C4=C(N(CC(=O)N(C)C)N=C4C)C)C(=O)N2C)C3=C1 URWLNMGORNCENB-UHFFFAOYSA-N 0.000 claims 1
• WDAKZIDBUZLDSR-UHFFFAOYSA-N 2-[4-[8-(6-ethoxypyridin-3-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-1-yl]-3-methylpyrazol-1-yl]-n-ethyl-n-methylacetamide Chemical compound C1=NC(OCC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(CC(=O)N(C)CC)C=4)C)C(=O)N2C)C3=C1 WDAKZIDBUZLDSR-UHFFFAOYSA-N 0.000 claims 1
• LKDMJTWWXWHUDA-UHFFFAOYSA-N 2-[4-[8-(6-methoxypyridin-3-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-1-yl]-3-methylpyrazol-1-yl]-n,n-dimethylacetamide Chemical compound C1=NC(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(CC(=O)N(C)C)C=4)C)C(=O)N2C)C3=C1 LKDMJTWWXWHUDA-UHFFFAOYSA-N 0.000 claims 1
• SAJFWULVLGKWHI-UHFFFAOYSA-N 2-[4-[8-(6-methoxypyridin-3-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-1-yl]-3-methylpyrazol-1-yl]acetic acid Chemical compound C1=NC(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(CC(O)=O)C=4)C)C(=O)N2C)C3=C1 SAJFWULVLGKWHI-UHFFFAOYSA-N 0.000 claims 1
• CGXZEKGHSKWPES-UHFFFAOYSA-N 2-[4-[8-[5-(ethylamino)-6-methylpyridin-3-yl]-3-methyl-2-oxoimidazo[4,5-c]quinolin-1-yl]-3,5-dimethylpyrazol-1-yl]-n,n-dimethylacetamide Chemical compound N1=C(C)C(NCC)=CC(C=2C=C3C=4N(C5=C(N(CC(=O)N(C)C)N=C5C)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 CGXZEKGHSKWPES-UHFFFAOYSA-N 0.000 claims 1
• FUTLJGVRPWZGDS-UHFFFAOYSA-N 2-[5-[1-(1,3-dimethylpyrazol-4-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-8-yl]pyridin-3-yl]-2-methylpropanenitrile Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(C=NC=3)C(C)(C)C#N)=CC=C1N=C2 FUTLJGVRPWZGDS-UHFFFAOYSA-N 0.000 claims 1
• XPBRQEUWPVRANF-UHFFFAOYSA-N 2-[5-[1-(1,3-dimethylpyrazol-4-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-8-yl]pyridin-3-yl]-n-methylacetamide Chemical compound CNC(=O)CC1=CN=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 XPBRQEUWPVRANF-UHFFFAOYSA-N 0.000 claims 1
• NTWWWZQUKOMMJE-UHFFFAOYSA-N 2-amino-5-[1-(1,3-dimethylpyrazol-4-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-8-yl]-n-(2-methoxyethyl)pyridine-3-carboxamide Chemical compound N1=C(N)C(C(=O)NCCOC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 NTWWWZQUKOMMJE-UHFFFAOYSA-N 0.000 claims 1
• PAJJTVWGVZDYMA-UHFFFAOYSA-N 2-amino-5-[1-(1,3-dimethylpyrazol-4-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-8-yl]-n-propan-2-ylpyridine-3-carboxamide Chemical compound N1=C(N)C(C(=O)NC(C)C)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 PAJJTVWGVZDYMA-UHFFFAOYSA-N 0.000 claims 1
• BDEXYHKOOMBBFO-UHFFFAOYSA-N 2-amino-n-methyl-5-[3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)-2-oxoimidazo[4,5-c]quinolin-8-yl]pyridine-3-carboxamide Chemical compound N1=C(N)C(C(=O)NC)=CC(C=2C=C3C=4N(C=5C(=NN(C=5)C(C)C)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 BDEXYHKOOMBBFO-UHFFFAOYSA-N 0.000 claims 1
• AFHYOSBGPJORNH-UHFFFAOYSA-N 3-[1-(1,3-dimethylpyrazol-4-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-8-yl]-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 AFHYOSBGPJORNH-UHFFFAOYSA-N 0.000 claims 1
• VQZOQOVLXOHWFD-UHFFFAOYSA-N 3-[1-(1,3-dimethylpyrazol-4-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-8-yl]benzamide Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(C=CC=3)C(N)=O)=CC=C1N=C2 VQZOQOVLXOHWFD-UHFFFAOYSA-N 0.000 claims 1
• OECJWQXKGGWOMR-UHFFFAOYSA-N 3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)-8-pyridin-2-ylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C(C)C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3N=CC=CC=3)=CC=C1N=C2 OECJWQXKGGWOMR-UHFFFAOYSA-N 0.000 claims 1
• GGLVXGKAUVVBCZ-UHFFFAOYSA-N 3-methyl-1-[3-methyl-1-(2-oxo-2-pyrrolidin-1-ylethyl)pyrazol-4-yl]-8-(2-pyrrolidin-1-ylpyrimidin-5-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(N2C(N(C)C3=C2C2=CC(=CC=C2N=C3)C=2C=NC(=NC=2)N2CCCC2)=O)C(C)=NN1CC(=O)N1CCCC1 GGLVXGKAUVVBCZ-UHFFFAOYSA-N 0.000 claims 1
• OUKUPAUMEUARNN-UHFFFAOYSA-N 3-methyl-1-[3-methyl-1-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]pyrazol-4-yl]-8-phenylimidazo[4,5-c]quinolin-2-one Chemical compound C1CN(C)CCN1C(=O)CN1N=C(C)C(N2C(N(C)C3=C2C2=CC(=CC=C2N=C3)C=2C=CC=CC=2)=O)=C1 OUKUPAUMEUARNN-UHFFFAOYSA-N 0.000 claims 1
• OEBSQOVYSVDMOQ-UHFFFAOYSA-N 3-methyl-8-[2-(methylamino)pyrimidin-5-yl]-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(NC)=NC=C1C1=CC=C(N=CC2=C3N(C4=C(N(C)N=C4C)C)C(=O)N2C)C3=C1 OEBSQOVYSVDMOQ-UHFFFAOYSA-N 0.000 claims 1
• MSKXZARYQBURSQ-UHFFFAOYSA-N 3-methyl-8-[5-(methylamino)pyridin-3-yl]-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CNC1=CN=CC(C=2C=C3C=4N(C=5C(=NN(C=5)C(C)C)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 MSKXZARYQBURSQ-UHFFFAOYSA-N 0.000 claims 1
• VTWSTNRQQNQEOA-UHFFFAOYSA-N 3-methyl-8-[6-(methylamino)-5-(trifluoromethyl)pyridin-3-yl]-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(C(F)(F)F)C(NC)=NC=C1C1=CC=C(N=CC2=C3N(C4=C(N(C)N=C4C)C)C(=O)N2C)C3=C1 VTWSTNRQQNQEOA-UHFFFAOYSA-N 0.000 claims 1
• VVNDAFCZUYDHDC-UHFFFAOYSA-N 3-methyl-8-[6-(methylamino)-5-(trifluoromethyl)pyridin-3-yl]-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(C(F)(F)F)C(NC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C=4)C(C)C)C)C(=O)N2C)C3=C1 VVNDAFCZUYDHDC-UHFFFAOYSA-N 0.000 claims 1
• PVMGJISOZCUTMV-UHFFFAOYSA-N 3-methyl-8-[6-(methylamino)pyridin-3-yl]-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(NC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C=4)C(C)C)C)C(=O)N2C)C3=C1 PVMGJISOZCUTMV-UHFFFAOYSA-N 0.000 claims 1
• CHHWKHGRXKPULB-UHFFFAOYSA-N 3-methyl-8-[6-(methylamino)pyridin-3-yl]-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinoline-2-thione Chemical compound C1=NC(NC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C=4)C(C)C)C)C(=S)N2C)C3=C1 CHHWKHGRXKPULB-UHFFFAOYSA-N 0.000 claims 1
• VTWSTNRQQNQEOA-HPRDVNIFSA-N 3-methyl-8-[6-(trideuteriomethylamino)-5-(trifluoromethyl)pyridin-3-yl]-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(C(F)(F)F)C(NC([2H])([2H])[2H])=NC=C1C1=CC=C(N=CC2=C3N(C4=C(N(C)N=C4C)C)C(=O)N2C)C3=C1 VTWSTNRQQNQEOA-HPRDVNIFSA-N 0.000 claims 1
• DEYVYCTTXGRVBG-UHFFFAOYSA-N 4-[1-(1,3-dimethylpyrazol-4-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-8-yl]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 DEYVYCTTXGRVBG-UHFFFAOYSA-N 0.000 claims 1
• LEOIKBCGRYIEBD-UHFFFAOYSA-N 4-[1-(3-chloro-1-methylpyrazol-4-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-8-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)Cl)C(=O)N2C)C3=C1 LEOIKBCGRYIEBD-UHFFFAOYSA-N 0.000 claims 1
• WZLPWCAUGOYTFK-UHFFFAOYSA-N 5-[1-(1,3-dimethylpyrazol-4-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-8-yl]-2-methoxy-n-methylpyridine-3-carboxamide Chemical compound N1=C(OC)C(C(=O)NC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 WZLPWCAUGOYTFK-UHFFFAOYSA-N 0.000 claims 1
• OVPFKQNXJFYGIB-UHFFFAOYSA-N 5-[1-(1,3-dimethylpyrazol-4-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-8-yl]-2-methoxypyridine-3-carbonitrile Chemical compound C1=C(C#N)C(OC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 OVPFKQNXJFYGIB-UHFFFAOYSA-N 0.000 claims 1
• XKPMINJSZKKMHO-UHFFFAOYSA-N 5-[1-(1,3-dimethylpyrazol-4-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-8-yl]-2-methoxypyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(OC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 XKPMINJSZKKMHO-UHFFFAOYSA-N 0.000 claims 1
• KDWLZSBJHYKTOH-UHFFFAOYSA-N 5-[1-(1,3-dimethylpyrazol-4-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-8-yl]-n-ethyl-2-(methylamino)pyridine-3-carboxamide Chemical compound N1=C(NC)C(C(=O)NCC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 KDWLZSBJHYKTOH-UHFFFAOYSA-N 0.000 claims 1
• HZTQVKYKQJWGJL-UHFFFAOYSA-N 5-[1-(1,3-dimethylpyrazol-4-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-8-yl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 HZTQVKYKQJWGJL-UHFFFAOYSA-N 0.000 claims 1
• YWAFHGGJFKWLBI-UHFFFAOYSA-N 5-[1-(1,3-dimethylpyrazol-4-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-8-yl]pyridine-2-carbonitrile Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(=CC=3)C#N)=CC=C1N=C2 YWAFHGGJFKWLBI-UHFFFAOYSA-N 0.000 claims 1
• DENBVUSAUKUMAN-UHFFFAOYSA-N 5-[1-(1,3-dimethylpyrazol-4-yl)-3-methyl-2-oxoimidazo[4,5-c]quinolin-8-yl]pyridine-2-carboxamide Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(=CC=3)C(N)=O)=CC=C1N=C2 DENBVUSAUKUMAN-UHFFFAOYSA-N 0.000 claims 1
• SKKFHPTXRKEZFI-UHFFFAOYSA-N 5-[3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)-2-oxoimidazo[4,5-c]quinolin-8-yl]pyridine-2-carboxamide Chemical compound CC1=NN(C(C)C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(=CC=3)C(N)=O)=CC=C1N=C2 SKKFHPTXRKEZFI-UHFFFAOYSA-N 0.000 claims 1
• HVDORYFRVKUDLZ-UHFFFAOYSA-N 8-(1,3-dimethyl-2-oxoimidazo[4,5-b]pyridin-6-yl)-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C4N(C)C(=O)N(C)C4=NC=3)=CC=C1N=C2 HVDORYFRVKUDLZ-UHFFFAOYSA-N 0.000 claims 1
• JRJYHVNUEJGSCL-UHFFFAOYSA-N 8-(2,4-dimethoxypyrimidin-5-yl)-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound COC1=NC(OC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 JRJYHVNUEJGSCL-UHFFFAOYSA-N 0.000 claims 1
• OCQPKQVXUZWWQU-UHFFFAOYSA-N 8-(2,4-dimethoxypyrimidin-5-yl)-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound COC1=NC(OC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C=4)C(C)C)C)C(=O)N2C)C3=C1 OCQPKQVXUZWWQU-UHFFFAOYSA-N 0.000 claims 1
• XUBXRDIZOWYLLY-UHFFFAOYSA-N 8-(2-aminopyrimidin-5-yl)-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(N)=NC=3)=CC=C1N=C2 XUBXRDIZOWYLLY-UHFFFAOYSA-N 0.000 claims 1
• HAMRSVJTSJFITJ-UHFFFAOYSA-N 8-(2-aminopyrimidin-5-yl)-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C(C)=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(N)=NC=3)=CC=C1N=C2 HAMRSVJTSJFITJ-UHFFFAOYSA-N 0.000 claims 1
• CLFLMSNFSZTXHT-UHFFFAOYSA-N 8-(2-fluoropyridin-4-yl)-3-methyl-1-(2-methylpyrazol-3-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CN1N=CC=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(F)N=CC=3)=CC=C1N=C2 CLFLMSNFSZTXHT-UHFFFAOYSA-N 0.000 claims 1
• VXMYXIOZMYNGFV-UHFFFAOYSA-N 8-(3,4-diethoxyphenyl)-1-(1-ethyl-3-methylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OCC)C(OCC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(CC)C=4)C)C(=O)N2C)C3=C1 VXMYXIOZMYNGFV-UHFFFAOYSA-N 0.000 claims 1
• GOQVEQWVOCJJMO-UHFFFAOYSA-N 8-(3,4-dimethoxyphenyl)-1-(1,3-dimethylpyrazol-4-yl)-3-ethylimidazo[4,5-c][1,5]naphthyridin-2-one Chemical compound O=C1N(CC)C2=CN=C3C=CC(C=4C=C(OC)C(OC)=CC=4)=NC3=C2N1C1=CN(C)N=C1C GOQVEQWVOCJJMO-UHFFFAOYSA-N 0.000 claims 1
• RQAAYOSCBTUKFO-UHFFFAOYSA-N 8-(3,4-dimethoxyphenyl)-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c][1,5]naphthyridin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=N1 RQAAYOSCBTUKFO-UHFFFAOYSA-N 0.000 claims 1
• MIICZQUCWZHLIZ-UHFFFAOYSA-N 8-(3,4-dimethoxyphenyl)-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 MIICZQUCWZHLIZ-UHFFFAOYSA-N 0.000 claims 1
• FBNMCZWHJCXITM-UHFFFAOYSA-N 8-(3,4-dimethoxyphenyl)-1-(1,3-dimethylpyrazol-4-yl)-3h-imidazo[4,5-c][1,5]naphthyridin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2)C3=N1 FBNMCZWHJCXITM-UHFFFAOYSA-N 0.000 claims 1
• SMIPWYASWWBPSN-UHFFFAOYSA-N 8-(3,4-dimethoxyphenyl)-1-(1,3-dimethylpyrazol-4-yl)-3h-imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2)C3=C1 SMIPWYASWWBPSN-UHFFFAOYSA-N 0.000 claims 1
• YAQZXPWLBRYMBW-UHFFFAOYSA-N 8-(3,4-dimethoxyphenyl)-1-(1,5-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(N=CC2=C3N(C4=C(N(C)N=C4)C)C(=O)N2C)C3=C1 YAQZXPWLBRYMBW-UHFFFAOYSA-N 0.000 claims 1
• YPYUQFWYDOIWNT-UHFFFAOYSA-N 8-(3,4-dimethoxyphenyl)-1-(1-ethyl-3-methylpyrazol-4-yl)-3-methylimidazo[4,5-c][1,5]naphthyridin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=NC(C=3C=C(OC)C(OC)=CC=3)=CC=C1N=C2 YPYUQFWYDOIWNT-UHFFFAOYSA-N 0.000 claims 1
• BBQBWESMTXHESY-UHFFFAOYSA-N 8-(3,4-dimethoxyphenyl)-1-(2,5-dimethylpyrazol-3-yl)-3-methylimidazo[4,5-c][1,5]naphthyridin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4N(N=C(C)C=4)C)C(=O)N2C)C3=N1 BBQBWESMTXHESY-UHFFFAOYSA-N 0.000 claims 1
• SFBUMIGAPABTEI-UHFFFAOYSA-N 8-(3,4-dimethoxyphenyl)-1-(2,5-dimethylpyrazol-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4N(N=C(C)C=4)C)C(=O)N2C)C3=C1 SFBUMIGAPABTEI-UHFFFAOYSA-N 0.000 claims 1
• BMKDSICKFMGLCH-UHFFFAOYSA-N 8-(3,4-dimethoxyphenyl)-1-(2-ethylpyrazol-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CCN1N=CC=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(OC)C(OC)=CC=3)=CC=C1N=C2 BMKDSICKFMGLCH-UHFFFAOYSA-N 0.000 claims 1
• PRFURPBEMCTXLS-UHFFFAOYSA-N 8-(3,4-dimethoxyphenyl)-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(N=CC2=C3N(C4=C(N(C)N=C4C)C)C(=O)N2C)C3=C1 PRFURPBEMCTXLS-UHFFFAOYSA-N 0.000 claims 1
• BJPFGKLZKXNSAY-UHFFFAOYSA-N 8-(3,4-dimethoxyphenyl)-3-methyl-1-(2-methylpyrazol-3-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4N(N=CC=4)C)C(=O)N2C)C3=C1 BJPFGKLZKXNSAY-UHFFFAOYSA-N 0.000 claims 1
• DUIOOTVMCFOUCG-UHFFFAOYSA-N 8-(3,4-dimethoxyphenyl)-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C=4)C(C)C)C)C(=O)N2C)C3=C1 DUIOOTVMCFOUCG-UHFFFAOYSA-N 0.000 claims 1
• DNAIZUFINPUCDQ-UHFFFAOYSA-N 8-(3-ethoxy-4-methoxyphenyl)-1-(1-ethyl-3-methylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(OC)C(OCC)=CC(C=2C=C3C=4N(C=5C(=NN(CC)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 DNAIZUFINPUCDQ-UHFFFAOYSA-N 0.000 claims 1
• XPXDXAMDCOKUKB-UHFFFAOYSA-N 8-(3-hydroxyphenyl)-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C(C)=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(O)C=CC=3)=CC=C1N=C2 XPXDXAMDCOKUKB-UHFFFAOYSA-N 0.000 claims 1
• BYDSFNZRAXZQAW-UHFFFAOYSA-N 8-(4-hydroxy-3-methoxyphenyl)-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(O)C(OC)=CC(C=2C=C3C=4N(C5=C(N(C)N=C5C)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 BYDSFNZRAXZQAW-UHFFFAOYSA-N 0.000 claims 1
• VSIRXYSPIHDQNK-UHFFFAOYSA-N 8-(5,6-dimethoxypyridin-3-yl)-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(OC)C(OC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 VSIRXYSPIHDQNK-UHFFFAOYSA-N 0.000 claims 1
• MOGRFFGQUFURNQ-UHFFFAOYSA-N 8-(5-amino-6-chloropyridin-3-yl)-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(N)C(Cl)=NC=3)=CC=C1N=C2 MOGRFFGQUFURNQ-UHFFFAOYSA-N 0.000 claims 1
• VXDKZUWESIQQLO-UHFFFAOYSA-N 8-(5-amino-6-chloropyridin-3-yl)-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C(C)C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(N)C(Cl)=NC=3)=CC=C1N=C2 VXDKZUWESIQQLO-UHFFFAOYSA-N 0.000 claims 1
• FKNCRAPPNYNGEJ-UHFFFAOYSA-N 8-(5-amino-6-fluoropyridin-3-yl)-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(N)C(F)=NC=3)=CC=C1N=C2 FKNCRAPPNYNGEJ-UHFFFAOYSA-N 0.000 claims 1
• SRFUFXUJXYYYNO-UHFFFAOYSA-N 8-(5-amino-6-fluoropyridin-3-yl)-1-(2,5-dimethylpyrazol-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CN1N=C(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(N)C(F)=NC=3)=CC=C1N=C2 SRFUFXUJXYYYNO-UHFFFAOYSA-N 0.000 claims 1
• SLOMYVIPZCMQRX-UHFFFAOYSA-N 8-(5-amino-6-fluoropyridin-3-yl)-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C(C)C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(N)C(F)=NC=3)=CC=C1N=C2 SLOMYVIPZCMQRX-UHFFFAOYSA-N 0.000 claims 1
• MUJODELDYUKCJH-UHFFFAOYSA-N 8-(5-amino-6-methoxypyridin-3-yl)-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(N)C(OC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2C)C3=C1 MUJODELDYUKCJH-UHFFFAOYSA-N 0.000 claims 1
• XGJOSTVRNOGEFS-UHFFFAOYSA-N 8-(5-amino-6-methoxypyridin-3-yl)-1-(3-chloro-1-methylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(N)C(OC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)Cl)C(=O)N2C)C3=C1 XGJOSTVRNOGEFS-UHFFFAOYSA-N 0.000 claims 1
• FDKSPPHJRSPQBS-UHFFFAOYSA-N 8-(5-amino-6-methylpyridin-3-yl)-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(N)C(C)=NC=3)=CC=C1N=C2 FDKSPPHJRSPQBS-UHFFFAOYSA-N 0.000 claims 1
• CHNSONXVTVTEJF-UHFFFAOYSA-N 8-(5-amino-6-methylpyridin-3-yl)-1-(3-chloro-1-methylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(N)C(C)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)Cl)C(=O)N2C)C3=C1 CHNSONXVTVTEJF-UHFFFAOYSA-N 0.000 claims 1
• AXUARBNISUDUFA-UHFFFAOYSA-N 8-(5-aminopyridin-3-yl)-1-(1,3-dimethylpyrazol-4-yl)-3-ethylimidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(CC)C2=CN=C3C=CC(C=4C=C(N)C=NC=4)=CC3=C2N1C1=CN(C)N=C1C AXUARBNISUDUFA-UHFFFAOYSA-N 0.000 claims 1
• KBMSYCUGRPHXAV-UHFFFAOYSA-N 8-(5-aminopyridin-3-yl)-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(N)C=NC=3)=CC=C1N=C2 KBMSYCUGRPHXAV-UHFFFAOYSA-N 0.000 claims 1
• XWEAMTQONZXUFB-UHFFFAOYSA-N 8-(5-aminopyridin-3-yl)-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C(C)C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(N)C=NC=3)=CC=C1N=C2 XWEAMTQONZXUFB-UHFFFAOYSA-N 0.000 claims 1
• JRUMWTQOHPOLOE-UHFFFAOYSA-N 8-(5-cyclobutyloxypyridin-3-yl)-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(OC4CCC4)C=NC=3)=CC=C1N=C2 JRUMWTQOHPOLOE-UHFFFAOYSA-N 0.000 claims 1
• YEJGUNRDHCURNS-UHFFFAOYSA-N 8-(5-ethoxypyridin-3-yl)-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CCOC1=CN=CC(C=2C=C3C=4N(C5=C(N(C)N=C5C)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 YEJGUNRDHCURNS-UHFFFAOYSA-N 0.000 claims 1
• RDHJKPXOFUGAST-UHFFFAOYSA-N 8-(6-amino-5-chloropyridin-3-yl)-1-(1-ethyl-3-methylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(Cl)C(N)=NC=3)=CC=C1N=C2 RDHJKPXOFUGAST-UHFFFAOYSA-N 0.000 claims 1
• CUPNAZPMKRWSBE-UHFFFAOYSA-N 8-(6-amino-5-chloropyridin-3-yl)-1-(3,5-dimethyl-1,2-oxazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NOC(C)=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(Cl)C(N)=NC=3)=CC=C1N=C2 CUPNAZPMKRWSBE-UHFFFAOYSA-N 0.000 claims 1
• MSDPWZVNKFWIOL-UHFFFAOYSA-N 8-(6-amino-5-chloropyridin-3-yl)-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C(C)=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(Cl)C(N)=NC=3)=CC=C1N=C2 MSDPWZVNKFWIOL-UHFFFAOYSA-N 0.000 claims 1
• ZINTZCNFUCFFQT-UHFFFAOYSA-N 8-(6-amino-5-fluoropyridin-3-yl)-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C(C)=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(F)C(N)=NC=3)=CC=C1N=C2 ZINTZCNFUCFFQT-UHFFFAOYSA-N 0.000 claims 1
• ARAKPOMZXRDXAC-UHFFFAOYSA-N 8-(6-amino-5-fluoropyridin-3-yl)-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C(C)C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(F)C(N)=NC=3)=CC=C1N=C2 ARAKPOMZXRDXAC-UHFFFAOYSA-N 0.000 claims 1
• GENUIYLCNHBEFJ-UHFFFAOYSA-N 8-(6-aminopyridin-3-yl)-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(N)=CC=3)=CC=C1N=C2 GENUIYLCNHBEFJ-UHFFFAOYSA-N 0.000 claims 1
• AFOKUHJLMHXZOT-UHFFFAOYSA-N 8-(6-aminopyridin-3-yl)-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C(C)C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(N)=CC=3)=CC=C1N=C2 AFOKUHJLMHXZOT-UHFFFAOYSA-N 0.000 claims 1
• ZNPDJDIALHQSNL-UHFFFAOYSA-N 8-(6-ethoxypyridin-3-yl)-1-(2-ethylpyrazol-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OCC)=CC=C1C1=CC=C(N=CC2=C3N(C=4N(N=CC=4)CC)C(=O)N2C)C3=C1 ZNPDJDIALHQSNL-UHFFFAOYSA-N 0.000 claims 1
• PKOUDGGGKKCLDO-UHFFFAOYSA-N 8-(6-ethoxypyridin-3-yl)-1-[1-(2-hydroxyethyl)-3-methylpyrazol-4-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OCC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(CCO)C=4)C)C(=O)N2C)C3=C1 PKOUDGGGKKCLDO-UHFFFAOYSA-N 0.000 claims 1
• WNSOTAOUAICYHQ-UHFFFAOYSA-N 8-(6-ethoxypyridin-3-yl)-1-[1-(2-methoxyethyl)-3,5-dimethylpyrazol-4-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OCC)=CC=C1C1=CC=C(N=CC2=C3N(C4=C(N(CCOC)N=C4C)C)C(=O)N2C)C3=C1 WNSOTAOUAICYHQ-UHFFFAOYSA-N 0.000 claims 1
• MSMIBRUSSZKBPI-UHFFFAOYSA-N 8-(6-ethoxypyridin-3-yl)-1-[1-(2-methoxyethyl)-3-methylpyrazol-4-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OCC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(CCOC)C=4)C)C(=O)N2C)C3=C1 MSMIBRUSSZKBPI-UHFFFAOYSA-N 0.000 claims 1
• NPYRUPLOELXVRW-UHFFFAOYSA-N 8-(6-ethoxypyridin-3-yl)-1-[3-methyl-1-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]pyrazol-4-yl]-3h-imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OCC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(CC(=O)N5CCN(C)CC5)C=4)C)C(=O)N2)C3=C1 NPYRUPLOELXVRW-UHFFFAOYSA-N 0.000 claims 1
• ZJQSTBLQSZVVIP-UHFFFAOYSA-N 8-(6-ethoxypyridin-3-yl)-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OCC)=CC=C1C1=CC=C(N=CC2=C3N(C4=C(N(C)N=C4C)C)C(=O)N2C)C3=C1 ZJQSTBLQSZVVIP-UHFFFAOYSA-N 0.000 claims 1
• QTHNHOVBOFPDMJ-UHFFFAOYSA-N 8-(6-ethoxypyridin-3-yl)-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OCC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C=4)C(C)C)C)C(=O)N2C)C3=C1 QTHNHOVBOFPDMJ-UHFFFAOYSA-N 0.000 claims 1
• SGVTZOJAAAGOAP-UHFFFAOYSA-N 8-(6-methoxypyridin-3-yl)-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OC)=CC=C1C1=CC=C(N=CC2=C3N(C4=C(N(C)N=C4C)C)C(=O)N2C)C3=C1 SGVTZOJAAAGOAP-UHFFFAOYSA-N 0.000 claims 1
• HQGNUSGLZMDKRX-UHFFFAOYSA-N 8-(6-methoxypyridin-3-yl)-3-methyl-1-(2-methylpyrazol-3-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4N(N=CC=4)C)C(=O)N2C)C3=C1 HQGNUSGLZMDKRX-UHFFFAOYSA-N 0.000 claims 1
• ATGQQXJOJVPHPE-UHFFFAOYSA-N 8-(6-methoxypyridin-3-yl)-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C=4)C(C)C)C)C(=O)N2C)C3=C1 ATGQQXJOJVPHPE-UHFFFAOYSA-N 0.000 claims 1
• AURCYJANPOULGD-UHFFFAOYSA-N 8-[2-(dimethylamino)-3-methylimidazo[4,5-b]pyridin-6-yl]-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C=1N=C2N(C)C(N(C)C)=NC2=CC=1C(C=C1C=23)=CC=C1N=CC=2N(C)C(=O)N3C1=CN(C)N=C1C AURCYJANPOULGD-UHFFFAOYSA-N 0.000 claims 1
• DOLYBIRZDRGWHG-UHFFFAOYSA-N 8-[2-(dimethylamino)pyrimidin-5-yl]-1-(1,3-dimethylpyrazol-4-yl)-3h-imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(N(C)C)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C)C=4)C)C(=O)N2)C3=C1 DOLYBIRZDRGWHG-UHFFFAOYSA-N 0.000 claims 1
• LXAJENLOHBEUQO-UHFFFAOYSA-N 8-[2-(dimethylamino)pyrimidin-5-yl]-1-(1-ethyl-3-methylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(=NC=3)N(C)C)=CC=C1N=C2 LXAJENLOHBEUQO-UHFFFAOYSA-N 0.000 claims 1
• LURHWXCTLPXLAD-UHFFFAOYSA-N 8-[2-(dimethylamino)pyrimidin-5-yl]-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C(C)C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(=NC=3)N(C)C)=CC=C1N=C2 LURHWXCTLPXLAD-UHFFFAOYSA-N 0.000 claims 1
• HOLPSVCMGJBJQK-UHFFFAOYSA-N 8-[5-(1,3-difluoro-2-hydroxypropan-2-yl)pyridin-3-yl]-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C(C)C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(C=NC=3)C(O)(CF)CF)=CC=C1N=C2 HOLPSVCMGJBJQK-UHFFFAOYSA-N 0.000 claims 1
• OCVPUECEYLYKRS-UHFFFAOYSA-N 8-[5-(1,3-difluoropropan-2-yloxy)pyridin-3-yl]-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(OC(CF)CF)C=NC=3)=CC=C1N=C2 OCVPUECEYLYKRS-UHFFFAOYSA-N 0.000 claims 1
• MOTJEYLREFISDT-UHFFFAOYSA-N 8-[5-(2-hydroxypropan-2-yl)pyridin-3-yl]-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C(C)C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(C=NC=3)C(C)(C)O)=CC=C1N=C2 MOTJEYLREFISDT-UHFFFAOYSA-N 0.000 claims 1
• GXWNJJAYMFXLMU-UHFFFAOYSA-N 8-[5-(cyclobutylamino)pyridin-3-yl]-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(NC4CCC4)C=NC=3)=CC=C1N=C2 GXWNJJAYMFXLMU-UHFFFAOYSA-N 0.000 claims 1
• DHXAWVOKVCZGQW-UHFFFAOYSA-N 8-[5-(diethylamino)pyridin-3-yl]-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CCN(CC)C1=CN=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 DHXAWVOKVCZGQW-UHFFFAOYSA-N 0.000 claims 1
• LLEZSVCWXAWYSI-UHFFFAOYSA-N 8-[5-(dimethylamino)-6-fluoropyridin-3-yl]-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(F)C(N(C)C)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 LLEZSVCWXAWYSI-UHFFFAOYSA-N 0.000 claims 1
• XKWKNKCMKPCRAX-UHFFFAOYSA-N 8-[5-(dimethylamino)-6-methylpyridin-3-yl]-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(C)C(N(C)C)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 XKWKNKCMKPCRAX-UHFFFAOYSA-N 0.000 claims 1
• XAMXMHVPWPPLBF-UHFFFAOYSA-N 8-[5-(dimethylamino)pyridin-3-yl]-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CN(C)C1=CN=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 XAMXMHVPWPPLBF-UHFFFAOYSA-N 0.000 claims 1
• AGKABLJZRGNLHJ-UHFFFAOYSA-N 8-[5-(ethylamino)-6-(hydroxymethyl)pyridin-3-yl]-1-(1-ethyl-3-methylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(CO)C(NCC)=CC(C=2C=C3C=4N(C=5C(=NN(CC)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 AGKABLJZRGNLHJ-UHFFFAOYSA-N 0.000 claims 1
• ZMGITWHPASMJTG-UHFFFAOYSA-N 8-[5-(ethylamino)-6-(hydroxymethyl)pyridin-3-yl]-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound N1=C(CO)C(NCC)=CC(C=2C=C3C=4N(C5=C(N(C)N=C5C)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 ZMGITWHPASMJTG-UHFFFAOYSA-N 0.000 claims 1
• UHJIURVMAZPSFS-UHFFFAOYSA-N 8-[5-(ethylamino)-6-(hydroxymethyl)pyridin-3-yl]-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound N1=C(CO)C(NCC)=CC(C=2C=C3C=4N(C=5C(=NN(C=5)C(C)C)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 UHJIURVMAZPSFS-UHFFFAOYSA-N 0.000 claims 1
• XTDZQFNXZCQIIJ-UHFFFAOYSA-N 8-[5-(ethylamino)-6-(methoxymethyl)pyridin-3-yl]-1-(1-ethyl-3-methylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(COC)C(NCC)=CC(C=2C=C3C=4N(C=5C(=NN(CC)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 XTDZQFNXZCQIIJ-UHFFFAOYSA-N 0.000 claims 1
• QIQICPOYTXNSGR-UHFFFAOYSA-N 8-[5-(ethylamino)-6-fluoropyridin-3-yl]-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound N1=C(F)C(NCC)=CC(C=2C=C3C=4N(C5=C(N(C)N=C5C)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 QIQICPOYTXNSGR-UHFFFAOYSA-N 0.000 claims 1
• UKOLEGXAFCNVRI-UHFFFAOYSA-N 8-[5-(ethylamino)-6-methoxypyridin-3-yl]-1-[1-(2-methoxyethyl)-3,5-dimethylpyrazol-4-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(OC)C(NCC)=CC(C=2C=C3C=4N(C5=C(N(CCOC)N=C5C)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 UKOLEGXAFCNVRI-UHFFFAOYSA-N 0.000 claims 1
• JNAZSHWAIGJAOZ-UHFFFAOYSA-N 8-[5-(ethylamino)-6-methylpyridin-3-yl]-1-(1-ethyl-3-methylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(C)C(NCC)=CC(C=2C=C3C=4N(C=5C(=NN(CC)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 JNAZSHWAIGJAOZ-UHFFFAOYSA-N 0.000 claims 1
• IMMCOQHSEADKGM-UHFFFAOYSA-N 8-[5-(ethylamino)-6-methylpyridin-3-yl]-1-[1-(2-hydroxyethyl)-3,5-dimethylpyrazol-4-yl]-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(C)C(NCC)=CC(C=2C=C3C=4N(C5=C(N(CCO)N=C5C)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 IMMCOQHSEADKGM-UHFFFAOYSA-N 0.000 claims 1
• CYHAKXRBSOPECR-UHFFFAOYSA-N 8-[5-(hydroxymethyl)-6-(methylamino)pyridin-3-yl]-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(CO)C(NC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C=4)C(C)C)C)C(=O)N2C)C3=C1 CYHAKXRBSOPECR-UHFFFAOYSA-N 0.000 claims 1
• ARPMQRGUWQIWFR-UHFFFAOYSA-N 8-[5-(methoxymethyl)-6-(methylamino)pyridin-3-yl]-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(COC)C(NC)=NC=C1C1=CC=C(N=CC2=C3N(C4=C(N(C)N=C4C)C)C(=O)N2C)C3=C1 ARPMQRGUWQIWFR-UHFFFAOYSA-N 0.000 claims 1
• MOGXISLJAFIMPL-UHFFFAOYSA-N 8-[5-(methoxymethyl)-6-(methylamino)pyridin-3-yl]-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(COC)C(NC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C=4)C(C)C)C)C(=O)N2C)C3=C1 MOGXISLJAFIMPL-UHFFFAOYSA-N 0.000 claims 1
• PPFPFQANCDAIDO-UHFFFAOYSA-N 8-[5-[cyclobutyl(methyl)amino]pyridin-3-yl]-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C=1N=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=CC=1N(C)C1CCC1 PPFPFQANCDAIDO-UHFFFAOYSA-N 0.000 claims 1
• GDWVJKCWBIHLSK-UHFFFAOYSA-N 8-[5-chloro-6-(hydroxymethyl)pyridin-3-yl]-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(Cl)C(CO)=NC=3)=CC=C1N=C2 GDWVJKCWBIHLSK-UHFFFAOYSA-N 0.000 claims 1
• UVJVPOCJGFOOBE-UHFFFAOYSA-N 8-[5-chloro-6-(methylamino)pyridin-3-yl]-1-(1-ethyl-3-methylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(Cl)C(NC)=NC=3)=CC=C1N=C2 UVJVPOCJGFOOBE-UHFFFAOYSA-N 0.000 claims 1
• POKPXPOBYBDYEC-UHFFFAOYSA-N 8-[5-chloro-6-(methylamino)pyridin-3-yl]-1-(2,5-dimethylpyrazol-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(Cl)C(NC)=NC=C1C1=CC=C(N=CC2=C3N(C=4N(N=C(C)C=4)C)C(=O)N2C)C3=C1 POKPXPOBYBDYEC-UHFFFAOYSA-N 0.000 claims 1
• SCGNQHDDQOTFQT-UHFFFAOYSA-N 8-[5-chloro-6-(methylamino)pyridin-3-yl]-1-(3,5-dimethyl-1,2-oxazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=C(Cl)C(NC)=NC=C1C1=CC=C(N=CC2=C3N(C4=C(ON=C4C)C)C(=O)N2C)C3=C1 SCGNQHDDQOTFQT-UHFFFAOYSA-N 0.000 claims 1
• FEBYLEBGVFTTDM-UHFFFAOYSA-N 8-[5-chloro-6-(methylamino)pyridin-3-yl]-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(Cl)C(NC)=NC=C1C1=CC=C(N=CC2=C3N(C4=C(N(C)N=C4C)C)C(=O)N2C)C3=C1 FEBYLEBGVFTTDM-UHFFFAOYSA-N 0.000 claims 1
• ANSDEQGGKDYPTF-UHFFFAOYSA-N 8-[5-chloro-6-(methylamino)pyridin-3-yl]-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(Cl)C(NC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C=4)C(C)C)C)C(=O)N2C)C3=C1 ANSDEQGGKDYPTF-UHFFFAOYSA-N 0.000 claims 1
• WDGRFXLTEJLYIV-UHFFFAOYSA-N 8-[5-fluoro-6-(methylamino)pyridin-3-yl]-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(F)C(NC)=NC=C1C1=CC=C(N=CC2=C3N(C4=C(N(C)N=C4C)C)C(=O)N2C)C3=C1 WDGRFXLTEJLYIV-UHFFFAOYSA-N 0.000 claims 1
• NMHSTFOUOYZVCA-UHFFFAOYSA-N 8-[5-fluoro-6-(methylamino)pyridin-3-yl]-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(F)C(NC)=NC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C=4)C(C)C)C)C(=O)N2C)C3=C1 NMHSTFOUOYZVCA-UHFFFAOYSA-N 0.000 claims 1
• PAZJHPLHBXUGOH-UHFFFAOYSA-N 8-[6-(2-hydroxyethylamino)pyridin-3-yl]-3-methyl-1-(2-methylpyrazol-3-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CN1N=CC=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(NCCO)=CC=3)=CC=C1N=C2 PAZJHPLHBXUGOH-UHFFFAOYSA-N 0.000 claims 1
• WXFTVMQXPSQOJZ-UHFFFAOYSA-N 8-[6-(azetidin-1-yl)pyridin-3-yl]-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(=CC=3)N3CCC3)=CC=C1N=C2 WXFTVMQXPSQOJZ-UHFFFAOYSA-N 0.000 claims 1
• JBQOSLVQLYMGBZ-UHFFFAOYSA-N 8-[6-(cyclopropylmethoxy)pyridin-3-yl]-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(OCC4CC4)=CC=3)=CC=C1N=C2 JBQOSLVQLYMGBZ-UHFFFAOYSA-N 0.000 claims 1
• KHXHEBVREJYLKC-UHFFFAOYSA-N 8-[6-(dimethylamino)pyridin-3-yl]-1-(1,5-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(N(C)C)=CC=C1C1=CC=C(N=CC2=C3N(C4=C(N(C)N=C4)C)C(=O)N2C)C3=C1 KHXHEBVREJYLKC-UHFFFAOYSA-N 0.000 claims 1
• IIGUGJJTUAEDGU-UHFFFAOYSA-N 8-[6-(dimethylamino)pyridin-3-yl]-1-(2,5-dimethylpyrazol-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(N(C)C)=CC=C1C1=CC=C(N=CC2=C3N(C=4N(N=C(C)C=4)C)C(=O)N2C)C3=C1 IIGUGJJTUAEDGU-UHFFFAOYSA-N 0.000 claims 1
• DHOVLBVIKZPMCG-UHFFFAOYSA-N 8-[6-(dimethylamino)pyridin-3-yl]-1-(2-ethylpyrazol-3-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CCN1N=CC=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(=CC=3)N(C)C)=CC=C1N=C2 DHOVLBVIKZPMCG-UHFFFAOYSA-N 0.000 claims 1
• FPVLLTOWRGTQRA-UHFFFAOYSA-N 8-[6-(dimethylamino)pyridin-3-yl]-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(N(C)C)=CC=C1C1=CC=C(N=CC2=C3N(C4=C(N(C)N=C4C)C)C(=O)N2C)C3=C1 FPVLLTOWRGTQRA-UHFFFAOYSA-N 0.000 claims 1
• BZRHOIHWJDDLSV-UHFFFAOYSA-N 8-[6-(dimethylamino)pyridin-3-yl]-3-methyl-1-(2-methylpyrazol-3-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(N(C)C)=CC=C1C1=CC=C(N=CC2=C3N(C=4N(N=CC=4)C)C(=O)N2C)C3=C1 BZRHOIHWJDDLSV-UHFFFAOYSA-N 0.000 claims 1
• DTGIMSRCAHUWOT-UHFFFAOYSA-N 8-[6-(dimethylamino)pyridin-3-yl]-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C(C)C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(=CC=3)N(C)C)=CC=C1N=C2 DTGIMSRCAHUWOT-UHFFFAOYSA-N 0.000 claims 1
• KYSBCBBMRLWOBJ-UHFFFAOYSA-N 8-[6-(ethylamino)-5-(methoxymethyl)pyridin-3-yl]-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(COC)C(NCC)=NC=C1C1=CC=C(N=CC2=C3N(C4=C(N(C)N=C4C)C)C(=O)N2C)C3=C1 KYSBCBBMRLWOBJ-UHFFFAOYSA-N 0.000 claims 1
• ULRXENZPBYCHTI-UHFFFAOYSA-N 8-[6-(ethylamino)-5-(trifluoromethyl)pyridin-3-yl]-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=C(C(F)(F)F)C(NCC)=NC=C1C1=CC=C(N=CC2=C3N(C4=C(N(C)N=C4C)C)C(=O)N2C)C3=C1 ULRXENZPBYCHTI-UHFFFAOYSA-N 0.000 claims 1
• ZFVUBHVYGUDESC-UHFFFAOYSA-N 8-[6-(hydroxymethyl)-5-(methylamino)pyridin-3-yl]-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound N1=C(CO)C(NC)=CC(C=2C=C3C=4N(C5=C(N(C)N=C5C)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 ZFVUBHVYGUDESC-UHFFFAOYSA-N 0.000 claims 1
• SEOOEPZQVOLXIF-UHFFFAOYSA-N 8-[6-(hydroxymethyl)-5-(methylamino)pyridin-3-yl]-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound N1=C(CO)C(NC)=CC(C=2C=C3C=4N(C=5C(=NN(C=5)C(C)C)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 SEOOEPZQVOLXIF-UHFFFAOYSA-N 0.000 claims 1
• RYFQSONNYIIDGM-UHFFFAOYSA-N 8-[6-(hydroxymethyl)pyridin-3-yl]-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C(C)=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(CO)=CC=3)=CC=C1N=C2 RYFQSONNYIIDGM-UHFFFAOYSA-N 0.000 claims 1
• DQMQBHHQHQZUIV-UHFFFAOYSA-N 8-[6-(hydroxymethyl)pyridin-3-yl]-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C(C)C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=NC(CO)=CC=3)=CC=C1N=C2 DQMQBHHQHQZUIV-UHFFFAOYSA-N 0.000 claims 1
• ZEEPKGXFQYBBBT-UHFFFAOYSA-N 8-[6-(methoxymethyl)pyridin-3-yl]-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(COC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C=4)C(C)C)C)C(=O)N2C)C3=C1 ZEEPKGXFQYBBBT-UHFFFAOYSA-N 0.000 claims 1
• MKNUNVSHIBQXQH-UHFFFAOYSA-N 8-[6-[ethyl(methyl)amino]pyridin-3-yl]-1-(1-ethyl-3-methylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(N(C)CC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(CC)C=4)C)C(=O)N2C)C3=C1 MKNUNVSHIBQXQH-UHFFFAOYSA-N 0.000 claims 1
• ZWOGZGLKWJNMFN-UHFFFAOYSA-N 8-[6-[ethyl(methyl)amino]pyridin-3-yl]-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=NC(N(C)CC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C(=NN(C=4)C(C)C)C)C(=O)N2C)C3=C1 ZWOGZGLKWJNMFN-UHFFFAOYSA-N 0.000 claims 1
• XWQCLHUSQNHJRB-UHFFFAOYSA-N 8-[6-amino-5-(ethoxymethyl)pyridin-3-yl]-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(N)C(COCC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 XWQCLHUSQNHJRB-UHFFFAOYSA-N 0.000 claims 1
• ZHJBJOVKJWLQSY-UHFFFAOYSA-N 8-[6-amino-5-(ethoxymethyl)pyridin-3-yl]-1-(1-ethyl-3-methylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(N)C(COCC)=CC(C=2C=C3C=4N(C=5C(=NN(CC)C=5)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 ZHJBJOVKJWLQSY-UHFFFAOYSA-N 0.000 claims 1
• OQTJUMAVIXCFNC-UHFFFAOYSA-N 8-[6-amino-5-(ethoxymethyl)pyridin-3-yl]-1-(3-chloro-1-methylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound N1=C(N)C(COCC)=CC(C=2C=C3C=4N(C=5C(=NN(C)C=5)Cl)C(=O)N(C)C=4C=NC3=CC=2)=C1 OQTJUMAVIXCFNC-UHFFFAOYSA-N 0.000 claims 1
• UGVKSBNXYMHXQQ-UHFFFAOYSA-N 8-[6-amino-5-(ethoxymethyl)pyridin-3-yl]-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound N1=C(N)C(COCC)=CC(C=2C=C3C=4N(C5=C(N(C)N=C5C)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 UGVKSBNXYMHXQQ-UHFFFAOYSA-N 0.000 claims 1
• IBDDMBBVRAHWCV-UHFFFAOYSA-N 8-[6-amino-5-(hydroxymethyl)pyridin-3-yl]-1-(3-chloro-1-methylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound ClC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(CO)C(N)=NC=3)=CC=C1N=C2 IBDDMBBVRAHWCV-UHFFFAOYSA-N 0.000 claims 1
• JLLSNDQSOOOOQL-UHFFFAOYSA-N 8-[6-amino-5-(hydroxymethyl)pyridin-3-yl]-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C(C)=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(CO)C(N)=NC=3)=CC=C1N=C2 JLLSNDQSOOOOQL-UHFFFAOYSA-N 0.000 claims 1
• QKAZISREMQLINJ-UHFFFAOYSA-N 8-[6-amino-5-(hydroxymethyl)pyridin-3-yl]-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C(C)C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(CO)C(N)=NC=3)=CC=C1N=C2 QKAZISREMQLINJ-UHFFFAOYSA-N 0.000 claims 1
• BTZIVIQJBCIWHO-UHFFFAOYSA-N 8-[6-amino-5-(methoxymethyl)pyridin-3-yl]-1-(1-ethyl-3-methylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(CC)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(COC)C(N)=NC=3)=CC=C1N=C2 BTZIVIQJBCIWHO-UHFFFAOYSA-N 0.000 claims 1
• HWOFZKHEHJIPNA-UHFFFAOYSA-N 8-[6-amino-5-(methoxymethyl)pyridin-3-yl]-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound N1=C(N)C(COC)=CC(C=2C=C3C=4N(C=5C(=NN(C=5)C(C)C)C)C(=O)N(C)C=4C=NC3=CC=2)=C1 HWOFZKHEHJIPNA-UHFFFAOYSA-N 0.000 claims 1
• OUIUXFDXDCIGFJ-UHFFFAOYSA-N 8-[6-amino-5-(trifluoromethyl)pyridin-3-yl]-1-(1,3-dimethylpyrazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(C(N)=NC=3)C(F)(F)F)=CC=C1N=C2 OUIUXFDXDCIGFJ-UHFFFAOYSA-N 0.000 claims 1
• DNXFZSBXLRYTAM-UHFFFAOYSA-N 8-[6-amino-5-(trifluoromethyl)pyridin-3-yl]-1-(3,5-dimethyl-1,2-oxazol-4-yl)-3-methylimidazo[4,5-c]quinolin-2-one Chemical compound CC1=NOC(C)=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(C(N)=NC=3)C(F)(F)F)=CC=C1N=C2 DNXFZSBXLRYTAM-UHFFFAOYSA-N 0.000 claims 1
• TZEXCFPOPNIIHX-UHFFFAOYSA-N 8-[6-amino-5-(trifluoromethyl)pyridin-3-yl]-3-methyl-1-(1,3,5-trimethylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C)C(C)=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(C(N)=NC=3)C(F)(F)F)=CC=C1N=C2 TZEXCFPOPNIIHX-UHFFFAOYSA-N 0.000 claims 1
• FGBVGLAPYPTTIS-UHFFFAOYSA-N 8-[6-amino-5-(trifluoromethyl)pyridin-3-yl]-3-methyl-1-(3-methyl-1-propan-2-ylpyrazol-4-yl)imidazo[4,5-c]quinolin-2-one Chemical compound CC1=NN(C(C)C)C=C1N1C(=O)N(C)C2=C1C1=CC(C=3C=C(C(N)=NC=3)C(F)(F)F)=CC=C1N=C2 FGBVGLAPYPTTIS-UHFFFAOYSA-N 0.000 claims 1
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