JP2016523911A5

JP2016523911A5 -

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Publication number: JP2016523911A5
Authority: JP; Japan
Prior art keywords: carboxamide; indole; methyl; methylphenyl; optionally substituted
Prior art date: 2014-06-26
Legal status : Granted

Application number

JP2016524175A

Other languages

English (en)

Japanese (ja)

Other versions

JP2016523911A (ja

JP6509838B2 (ja

Filing date

2014-06-26

Publication date

2017-08-03

2014-06-26 Application filed filed Critical

2014-06-26 Priority claimed from PCT/US2014/044247 external-priority patent/WO2014210255A1/en

2016-08-12 Publication of JP2016523911A publication Critical patent/JP2016523911A/ja

2017-08-03 Publication of JP2016523911A5 publication Critical patent/JP2016523911A5/ja

2019-05-08 Application granted granted Critical

2019-05-08 Publication of JP6509838B2 publication Critical patent/JP6509838B2/ja

Status Active legal-status Critical Current

2034-06-26 Anticipated expiration legal-status Critical

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-1 substituted Chemical class 0.000 claims 53
150000001875 compounds Chemical class 0.000 claims 37
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 32
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 19
229920006395 saturated elastomer Polymers 0.000 claims 13
125000001072 heteroaryl group Chemical group 0.000 claims 12
125000000623 heterocyclic group Chemical group 0.000 claims 12
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 10
101150065749 Churc1 gene Proteins 0.000 claims 10
102100038239 Protein Churchill Human genes 0.000 claims 10
229910052736 halogen Inorganic materials 0.000 claims 10
150000002367 halogens Chemical class 0.000 claims 10
125000003386 piperidinyl group Chemical group 0.000 claims 10
150000003857 carboxamides Chemical class 0.000 claims 9
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 8
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 8
125000002757 morpholinyl group Chemical group 0.000 claims 8
125000003226 pyrazolyl group Chemical group 0.000 claims 8
229910052757 nitrogen Inorganic materials 0.000 claims 7
150000003839 salts Chemical class 0.000 claims 7
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 6
125000004076 pyridyl group Chemical group 0.000 claims 6
125000001424 substituent group Chemical group 0.000 claims 6
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 5
208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 4
208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 4
125000002393 azetidinyl group Chemical group 0.000 claims 4
229910052805 deuterium Inorganic materials 0.000 claims 4
206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 4
201000010099 disease Diseases 0.000 claims 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
125000003107 substituted aryl group Chemical group 0.000 claims 4
125000000335 thiazolyl group Chemical group 0.000 claims 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 3
QWEWLLNSJDTOKH-UHFFFAOYSA-N 1,3-thiazole-2-carboxamide Chemical compound NC(=O)C1=NC=CS1 QWEWLLNSJDTOKH-UHFFFAOYSA-N 0.000 claims 3
HJNRNIXTGYJMOH-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-4-(1-prop-2-enoylpiperidin-3-yl)-1h-indole-7-carboxamide Chemical compound C1=NN(C)C=C1C1=CC2=C(C3CN(CCC3)C(=O)C=C)C=CC(C(N)=O)=C2N1 HJNRNIXTGYJMOH-UHFFFAOYSA-N 0.000 claims 3
208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
ZVLPFZCGSSCGDH-QWRGUYRKSA-N NC(=O)c1ccc([C@H]2CC[C@@H](C2)NC(=O)C=C)c2cc[nH]c12 Chemical compound NC(=O)c1ccc([C@H]2CC[C@@H](C2)NC(=O)C=C)c2cc[nH]c12 ZVLPFZCGSSCGDH-QWRGUYRKSA-N 0.000 claims 3
230000001684 chronic effect Effects 0.000 claims 3
125000005842 heteroatom Chemical group 0.000 claims 3
125000003566 oxetanyl group Chemical group 0.000 claims 3
125000004193 piperazinyl group Chemical group 0.000 claims 3
125000000714 pyrimidinyl group Chemical group 0.000 claims 3
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 3
125000001412 tetrahydropyranyl group Chemical group 0.000 claims 3
125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
125000005940 1,4-dioxanyl group Chemical group 0.000 claims 2
NXYHVXAWMQRIQZ-UHFFFAOYSA-N 2-(4-methylphenyl)-4-(1h-pyrazol-5-yl)-1h-indole-7-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC2=C(C=3NN=CC=3)C=CC(C(N)=O)=C2N1 NXYHVXAWMQRIQZ-UHFFFAOYSA-N 0.000 claims 2
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 2
AUDNGNGLLRZLDR-UHFFFAOYSA-N 4-(2-aminoethylamino)-2-(4-methylphenyl)-1h-indole-7-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC2=C(NCCN)C=CC(C(N)=O)=C2N1 AUDNGNGLLRZLDR-UHFFFAOYSA-N 0.000 claims 2
NTKHIMDXLAINBM-UHFFFAOYSA-N 4-(2-aminophenyl)-2-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)-1h-indole-7-carboxamide Chemical compound C1N(S(=O)(=O)C)CCC(C=2NC3=C(C(N)=O)C=CC(=C3C=2)C=2C(=CC=CC=2)N)=C1 NTKHIMDXLAINBM-UHFFFAOYSA-N 0.000 claims 2
SEZNBUSTSPNUEM-UHFFFAOYSA-N 4-(3-amino-2-methylphenyl)-2-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)-1h-indole-7-carboxamide Chemical compound CC1=C(N)C=CC=C1C1=CC=C(C(N)=O)C2=C1C=C(C=1CCN(CC=1)S(C)(=O)=O)N2 SEZNBUSTSPNUEM-UHFFFAOYSA-N 0.000 claims 2
YLUGQOCWOPDIMD-UHFFFAOYSA-N 4-(dimethylamino)but-2-enamide Chemical compound CN(C)CC=CC(N)=O YLUGQOCWOPDIMD-UHFFFAOYSA-N 0.000 claims 2
LPBGWJZEPAVKJF-UHFFFAOYSA-N 4-[2-methyl-3-(1-oxo-3,4-dihydroisoquinolin-2-yl)phenyl]-2-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)-1h-indole-7-carboxamide Chemical compound CC1=C(N2C(C3=CC=CC=C3CC2)=O)C=CC=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C1=CCN(S(C)(=O)=O)CC1 LPBGWJZEPAVKJF-UHFFFAOYSA-N 0.000 claims 2
OUTWFGLFYFYILF-UHFFFAOYSA-N 4-[3-(6-fluoro-4-oxoquinazolin-3-yl)-2-methylphenyl]-2-pyridin-3-yl-1h-indole-7-carboxamide Chemical compound C1=CC=C(N2C(C3=CC(F)=CC=C3N=C2)=O)C(C)=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C1=CC=CN=C1 OUTWFGLFYFYILF-UHFFFAOYSA-N 0.000 claims 2
MMGQHMNFRYJGPY-UHFFFAOYSA-N 4-[methyl-(1-prop-2-enoylazetidin-3-yl)amino]-1h-indole-7-carboxamide Chemical compound C=1C=C(C(N)=O)C=2NC=CC=2C=1N(C)C1CN(C(=O)C=C)C1 MMGQHMNFRYJGPY-UHFFFAOYSA-N 0.000 claims 2
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 2
206010002556 Ankylosing Spondylitis Diseases 0.000 claims 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
208000028564 B-cell non-Hodgkin lymphoma Diseases 0.000 claims 2
VOJDSPGXWOOAFB-NWDGAFQWSA-N C(C=C)(=O)N[C@H]1C[C@H](CCC1)C1=C2C=CNC2=C(C=C1)C(=O)N Chemical compound C(C=C)(=O)N[C@H]1C[C@H](CCC1)C1=C2C=CNC2=C(C=C1)C(=O)N VOJDSPGXWOOAFB-NWDGAFQWSA-N 0.000 claims 2
MZSBJBIISWWHIV-UHFFFAOYSA-N CC(C)n1cc(cn1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C Chemical compound CC(C)n1cc(cn1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C MZSBJBIISWWHIV-UHFFFAOYSA-N 0.000 claims 2
UZSXYSMMCLOEHN-UHFFFAOYSA-N CCc1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1 Chemical compound CCc1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1 UZSXYSMMCLOEHN-UHFFFAOYSA-N 0.000 claims 2
WYNJLPVFWIJNOU-UHFFFAOYSA-N CCn1cc(cn1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C Chemical compound CCn1cc(cn1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C WYNJLPVFWIJNOU-UHFFFAOYSA-N 0.000 claims 2
BBIXMNJGTVMMCL-UHFFFAOYSA-N CN1CCC(CC1)C(=O)Nc1cccc(c1C)-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound CN1CCC(CC1)C(=O)Nc1cccc(c1C)-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O BBIXMNJGTVMMCL-UHFFFAOYSA-N 0.000 claims 2
YROFMPHUAZCMHI-UHFFFAOYSA-N CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(CNC(=O)C=C)c1 Chemical compound CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(CNC(=O)C=C)c1 YROFMPHUAZCMHI-UHFFFAOYSA-N 0.000 claims 2
206010009900 Colitis ulcerative Diseases 0.000 claims 2
208000011231 Crohn disease Diseases 0.000 claims 2
208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
208000005615 Interstitial Cystitis Diseases 0.000 claims 2
208000003456 Juvenile Arthritis Diseases 0.000 claims 2
206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 2
208000005777 Lupus Nephritis Diseases 0.000 claims 2
206010052178 Lymphocytic lymphoma Diseases 0.000 claims 2
208000025205 Mantle-Cell Lymphoma Diseases 0.000 claims 2
FRIIAQXQWLDHKH-UHFFFAOYSA-N NC(=O)c1ccc(-c2cccc(NC(=O)C=C)c2)c2cc(CCO)[nH]c12 Chemical compound NC(=O)c1ccc(-c2cccc(NC(=O)C=C)c2)c2cc(CCO)[nH]c12 FRIIAQXQWLDHKH-UHFFFAOYSA-N 0.000 claims 2
UNHZLHSLZZWMNP-NSHDSACASA-N NC(=O)c1ccc([C@H]2CCCN(C2)C(=O)C=C)c2cc[nH]c12 Chemical compound NC(=O)c1ccc([C@H]2CCCN(C2)C(=O)C=C)c2cc[nH]c12 UNHZLHSLZZWMNP-NSHDSACASA-N 0.000 claims 2
VOJDSPGXWOOAFB-RYUDHWBXSA-N NC(=O)c1ccc([C@H]2CCC[C@@H](C2)NC(=O)C=C)c2cc[nH]c12 Chemical compound NC(=O)c1ccc([C@H]2CCC[C@@H](C2)NC(=O)C=C)c2cc[nH]c12 VOJDSPGXWOOAFB-RYUDHWBXSA-N 0.000 claims 2
208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 2
206010035226 Plasma cell myeloma Diseases 0.000 claims 2
208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 2
201000004681 Psoriasis Diseases 0.000 claims 2
201000001263 Psoriatic Arthritis Diseases 0.000 claims 2
208000036824 Psoriatic arthropathy Diseases 0.000 claims 2
201000006704 Ulcerative Colitis Diseases 0.000 claims 2
125000000217 alkyl group Chemical group 0.000 claims 2
208000006673 asthma Diseases 0.000 claims 2
210000003719 b-lymphocyte Anatomy 0.000 claims 2
208000019069 chronic childhood arthritis Diseases 0.000 claims 2
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
201000003444 follicular lymphoma Diseases 0.000 claims 2
201000009277 hairy cell leukemia Diseases 0.000 claims 2
125000000842 isoxazolyl group Chemical group 0.000 claims 2
201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims 2
201000011649 lymphoblastic lymphoma Diseases 0.000 claims 2
125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 2
201000006417 multiple sclerosis Diseases 0.000 claims 2
NATHNSVCDVBPTA-UHFFFAOYSA-N n-[3-[7-carbamoyl-2-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)-1h-indol-4-yl]-2-methylphenyl]-1,3-thiazole-2-carboxamide Chemical compound C1=CC=C(C=2C=3C=C(NC=3C(C(N)=O)=CC=2)C=2CCN(CC=2)S(C)(=O)=O)C(C)=C1NC(=O)C1=NC=CS1 NATHNSVCDVBPTA-UHFFFAOYSA-N 0.000 claims 2
YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 claims 2
201000008482 osteoarthritis Diseases 0.000 claims 2
125000003551 oxepanyl group Chemical group 0.000 claims 2
229910052760 oxygen Inorganic materials 0.000 claims 2
239000008194 pharmaceutical composition Substances 0.000 claims 2
206010039073 rheumatoid arthritis Diseases 0.000 claims 2
229910052717 sulfur Inorganic materials 0.000 claims 2
201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
125000001544 thienyl group Chemical group 0.000 claims 2
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
GDVYZGMAXSNLGM-OWOJBTEDSA-N (e)-3-chloroprop-2-enamide Chemical compound NC(=O)\C=C\Cl GDVYZGMAXSNLGM-OWOJBTEDSA-N 0.000 claims 1
SAUZERSNFCTTSP-ONEGZZNKSA-N (e)-3-pyridin-3-ylprop-2-enamide Chemical compound NC(=O)\C=C\C1=CC=CN=C1 SAUZERSNFCTTSP-ONEGZZNKSA-N 0.000 claims 1
BSSNZUFKXJJCBG-OWOJBTEDSA-N (e)-but-2-enediamide Chemical compound NC(=O)\C=C\C(N)=O BSSNZUFKXJJCBG-OWOJBTEDSA-N 0.000 claims 1
ICJNPIYNARHAEK-UHFFFAOYSA-N 1-methyl-3,6-dihydro-2h-pyridine-5-carboxamide Chemical compound CN1CCC=C(C(N)=O)C1 ICJNPIYNARHAEK-UHFFFAOYSA-N 0.000 claims 1
KJLFFCRGGGXQKE-UHFFFAOYSA-N 1h-indole-6-carboxamide Chemical compound NC(=O)C1=CC=C2C=CNC2=C1 KJLFFCRGGGXQKE-UHFFFAOYSA-N 0.000 claims 1
IICSRUINYZLIGZ-UHFFFAOYSA-N 2-(1-acetyl-2,5-dihydropyrrol-3-yl)-4-[2-methyl-3-(4-oxoquinazolin-3-yl)phenyl]-1h-indole-7-carboxamide Chemical compound C1N(C(=O)C)CC=C1C1=CC2=C(C=3C(=C(C=CC=3)N3C(C4=CC=CC=C4N=C3)=O)C)C=CC(C(N)=O)=C2N1 IICSRUINYZLIGZ-UHFFFAOYSA-N 0.000 claims 1
SKCMEXAMJWCEBX-UHFFFAOYSA-N 2-(1-acetyl-3,6-dihydro-2h-pyridin-4-yl)-4-[2-methyl-3-(4-oxoquinazolin-3-yl)phenyl]-1h-indole-7-carboxamide Chemical compound C1N(C(=O)C)CCC(C=2NC3=C(C(N)=O)C=CC(=C3C=2)C=2C(=C(C=CC=2)N2C(C3=CC=CC=C3N=C2)=O)C)=C1 SKCMEXAMJWCEBX-UHFFFAOYSA-N 0.000 claims 1
RJPBBDLEQSWCJW-UHFFFAOYSA-N 2-(1-acetyl-3,6-dihydro-2h-pyridin-4-yl)-4-[3-(6-fluoro-4-oxoquinazolin-3-yl)-2-methylphenyl]-1h-indole-7-carboxamide Chemical compound C1N(C(=O)C)CCC(C=2NC3=C(C(N)=O)C=CC(=C3C=2)C=2C(=C(C=CC=2)N2C(C3=CC(F)=CC=C3N=C2)=O)C)=C1 RJPBBDLEQSWCJW-UHFFFAOYSA-N 0.000 claims 1
POUHUOHPRFEYLG-UHFFFAOYSA-N 2-(1-acetyl-3,6-dihydro-2h-pyridin-4-yl)-4-[3-[(4-cyclopropylbenzoyl)amino]-2-methylphenyl]-1h-indole-7-carboxamide Chemical compound C1N(C(=O)C)CCC(C=2NC3=C(C(N)=O)C=CC(=C3C=2)C=2C(=C(NC(=O)C=3C=CC(=CC=3)C3CC3)C=CC=2)C)=C1 POUHUOHPRFEYLG-UHFFFAOYSA-N 0.000 claims 1
APLKJSDZPXJSHT-UHFFFAOYSA-N 2-(1-acetyl-3,6-dihydro-2h-pyridin-4-yl)-4-[3-[(4-tert-butylbenzoyl)amino]-2-methylphenyl]-1h-indole-7-carboxamide Chemical compound C1N(C(=O)C)CCC(C=2NC3=C(C(N)=O)C=CC(=C3C=2)C=2C(=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)C)C=CC=2)C)=C1 APLKJSDZPXJSHT-UHFFFAOYSA-N 0.000 claims 1
JRPNURORIBAHHP-UHFFFAOYSA-N 2-(1-acetyl-3,6-dihydro-2h-pyridin-4-yl)-4-[3-[[4-(2-cyanopropan-2-yl)benzoyl]amino]-2-methylphenyl]-1h-indole-7-carboxamide Chemical compound C1N(C(=O)C)CCC(C=2NC3=C(C(N)=O)C=CC(=C3C=2)C=2C(=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)C#N)C=CC=2)C)=C1 JRPNURORIBAHHP-UHFFFAOYSA-N 0.000 claims 1
YWZCROIWSUOWHD-UHFFFAOYSA-N 2-(1-acetylpiperidin-4-yl)-4-(3-amino-2-methylphenyl)-1h-indole-7-carboxamide Chemical compound C1CN(C(=O)C)CCC1C1=CC2=C(C=3C(=C(N)C=CC=3)C)C=CC(C(N)=O)=C2N1 YWZCROIWSUOWHD-UHFFFAOYSA-N 0.000 claims 1
NFRZDNDHJBQTBD-UHFFFAOYSA-N 2-(1-methyl-2,5-dihydropyrrol-3-yl)-4-[2-methyl-3-(4-oxoquinazolin-3-yl)phenyl]-1h-indole-7-carboxamide Chemical compound C1N(C)CC=C1C1=CC2=C(C=3C(=C(C=CC=3)N3C(C4=CC=CC=C4N=C3)=O)C)C=CC(C(N)=O)=C2N1 NFRZDNDHJBQTBD-UHFFFAOYSA-N 0.000 claims 1
TZQAYSKKISJPLV-UHFFFAOYSA-N 2-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)-4-[2-methyl-3-(4-oxoquinazolin-3-yl)phenyl]-1h-indole-7-carboxamide Chemical compound C1N(C)CCC(C=2NC3=C(C(N)=O)C=CC(=C3C=2)C=2C(=C(C=CC=2)N2C(C3=CC=CC=C3N=C2)=O)C)=C1 TZQAYSKKISJPLV-UHFFFAOYSA-N 0.000 claims 1
YUEIHKMWPVHCRD-QGZVFWFLSA-N 2-(1-methylpyrazol-4-yl)-4-[(3r)-3-(4-oxoquinazolin-3-yl)piperidin-1-yl]-1h-indole-7-carboxamide Chemical compound C1=NN(C)C=C1C1=CC2=C(N3C[C@@H](CCC3)N3C(C4=CC=CC=C4N=C3)=O)C=CC(C(N)=O)=C2N1 YUEIHKMWPVHCRD-QGZVFWFLSA-N 0.000 claims 1
CNKOAUCEOSHPNA-QGZVFWFLSA-N 2-(1-methylpyrazol-4-yl)-4-[(3r)-3-[[4-(trifluoromethoxy)benzoyl]amino]piperidin-1-yl]-1h-indole-7-carboxamide Chemical compound C1=NN(C)C=C1C1=CC2=C(N3C[C@@H](CCC3)NC(=O)C=3C=CC(OC(F)(F)F)=CC=3)C=CC(C(N)=O)=C2N1 CNKOAUCEOSHPNA-QGZVFWFLSA-N 0.000 claims 1
LLJRVOOYABPRCT-GOSISDBHSA-N 2-(1-methylpyrazol-4-yl)-4-[(3r)-3-[[4-(trifluoromethyl)benzoyl]amino]piperidin-1-yl]-1h-indole-7-carboxamide Chemical compound C1=NN(C)C=C1C1=CC2=C(N3C[C@@H](CCC3)NC(=O)C=3C=CC(=CC=3)C(F)(F)F)C=CC(C(N)=O)=C2N1 LLJRVOOYABPRCT-GOSISDBHSA-N 0.000 claims 1
SEXZUTLAWKTNBR-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-4-[2-methyl-3-(4,5,6,7-tetrahydro-1-benzothiophene-2-carbonylamino)phenyl]-1h-indole-7-carboxamide Chemical compound CC1=C(NC(=O)C=2SC=3CCCCC=3C=2)C=CC=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C=1C=NN(C)C=1 SEXZUTLAWKTNBR-UHFFFAOYSA-N 0.000 claims 1
COUFPWFCNDXODQ-UHFFFAOYSA-N 2-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)-4-phenyl-1h-indole-7-carboxamide Chemical compound C1N(S(=O)(=O)C)CCC(C=2NC3=C(C(N)=O)C=CC(=C3C=2)C=2C=CC=CC=2)=C1 COUFPWFCNDXODQ-UHFFFAOYSA-N 0.000 claims 1
RVXZOOCMGWQPPY-UHFFFAOYSA-N 2-(2,5-dihydro-1h-pyrrol-3-yl)-4-[2-methyl-3-(4-oxoquinazolin-3-yl)phenyl]-1h-indole-7-carboxamide Chemical compound C1=CC=C(N2C(C3=CC=CC=C3N=C2)=O)C(C)=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C1=CCNC1 RVXZOOCMGWQPPY-UHFFFAOYSA-N 0.000 claims 1
BEZFSGBAWXYAAH-UHFFFAOYSA-N 2-(3,6-dihydro-2h-pyran-4-yl)-4-[2-methyl-3-(4-oxoquinazolin-3-yl)phenyl]-1h-indole-7-carboxamide Chemical compound C1=CC=C(N2C(C3=CC=CC=C3N=C2)=O)C(C)=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C1=CCOCC1 BEZFSGBAWXYAAH-UHFFFAOYSA-N 0.000 claims 1
LSOUGXBIXIHVGE-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-(1h-pyrazol-5-yl)-1h-indole-7-carboxamide Chemical compound C1=2C=C(C=3C=CC(F)=CC=3)NC=2C(C(=O)N)=CC=C1C1=CC=NN1 LSOUGXBIXIHVGE-UHFFFAOYSA-N 0.000 claims 1
AAGBJPBTKJOAMO-LJQANCHMSA-N 2-(4-fluorophenyl)-4-[(3r)-3-(4-oxoquinazolin-3-yl)piperidin-1-yl]-1h-indole-7-carboxamide Chemical compound N1C=2C(C(=O)N)=CC=C(N3C[C@@H](CCC3)N3C(C4=CC=CC=C4N=C3)=O)C=2C=C1C1=CC=C(F)C=C1 AAGBJPBTKJOAMO-LJQANCHMSA-N 0.000 claims 1
CZMVEDKOFQLSSY-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-[2-methyl-3-(4,5,6,7-tetrahydro-1-benzothiophene-2-carbonylamino)phenyl]-1h-indole-7-carboxamide Chemical compound CC1=C(NC(=O)C=2SC=3CCCCC=3C=2)C=CC=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C1=CC=C(F)C=C1 CZMVEDKOFQLSSY-UHFFFAOYSA-N 0.000 claims 1
BJNMCKNVARKVQZ-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-[2-methyl-3-(4-oxoquinazolin-3-yl)phenyl]-1h-indole-7-carboxamide Chemical compound C1=CC=C(N2C(C3=CC=CC=C3N=C2)=O)C(C)=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C1=CC=C(F)C=C1 BJNMCKNVARKVQZ-UHFFFAOYSA-N 0.000 claims 1
RSJQKWCZCABWHH-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-pyridin-3-yl-1h-indole-7-carboxamide Chemical compound C1=2C=C(C=3C=CC(F)=CC=3)NC=2C(C(=O)N)=CC=C1C1=CC=CN=C1 RSJQKWCZCABWHH-UHFFFAOYSA-N 0.000 claims 1
LXTGQEVSAIAAFB-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-pyridin-4-yl-1h-indole-7-carboxamide Chemical compound C1=2C=C(C=3C=CC(F)=CC=3)NC=2C(C(=O)N)=CC=C1C1=CC=NC=C1 LXTGQEVSAIAAFB-UHFFFAOYSA-N 0.000 claims 1
UTOKQUROMRKHQE-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-pyrimidin-5-yl-1h-indole-7-carboxamide Chemical compound C1=2C=C(C=3C=CC(F)=CC=3)NC=2C(C(=O)N)=CC=C1C1=CN=CN=C1 UTOKQUROMRKHQE-UHFFFAOYSA-N 0.000 claims 1
ZTJLNBGLMZRLBJ-UHFFFAOYSA-N 2-(4-methylphenyl)-4-(1,3-thiazol-2-yl)-1h-indole-7-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC2=C(C=3SC=CN=3)C=CC(C(N)=O)=C2N1 ZTJLNBGLMZRLBJ-UHFFFAOYSA-N 0.000 claims 1
YTFAHLYWFVILAO-UHFFFAOYSA-N 2-(4-methylphenyl)-4-(1-methylpyrazol-4-yl)-1h-indole-7-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC2=C(C3=CN(C)N=C3)C=CC(C(N)=O)=C2N1 YTFAHLYWFVILAO-UHFFFAOYSA-N 0.000 claims 1
OWZVVQXNOUDXPO-UHFFFAOYSA-N 2-(4-methylphenyl)-4-(1h-pyrazol-4-yl)-1h-indole-7-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC2=C(C3=CNN=C3)C=CC(C(N)=O)=C2N1 OWZVVQXNOUDXPO-UHFFFAOYSA-N 0.000 claims 1
IPJYARINWXFMEN-UHFFFAOYSA-N 2-(4-methylphenyl)-4-[(2-methylpyrazol-3-yl)amino]-1h-indole-7-carboxamide Chemical compound C1=CC(C)=CC=C1C(NC1=C(C(N)=O)C=C2)=CC1=C2NC1=CC=NN1C IPJYARINWXFMEN-UHFFFAOYSA-N 0.000 claims 1
VYONOROZQNIJLE-UHFFFAOYSA-N 2-(4-methylphenyl)-4-pyridin-2-yl-1h-indole-7-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC2=C(C=3N=CC=CC=3)C=CC(C(N)=O)=C2N1 VYONOROZQNIJLE-UHFFFAOYSA-N 0.000 claims 1
CTKLFXRMUYOBSB-UHFFFAOYSA-N 2-(4-methylphenyl)-4-pyridin-3-yl-1h-indole-7-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC2=C(C=3C=NC=CC=3)C=CC(C(N)=O)=C2N1 CTKLFXRMUYOBSB-UHFFFAOYSA-N 0.000 claims 1
PACAOXFQSXXGLD-UHFFFAOYSA-N 2-(4-methylphenyl)-4-pyridin-4-yl-1h-indole-7-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC2=C(C=3C=CN=CC=3)C=CC(C(N)=O)=C2N1 PACAOXFQSXXGLD-UHFFFAOYSA-N 0.000 claims 1
MPVWENZZZCNIJA-UHFFFAOYSA-N 2-(4-methylphenyl)-4-pyrimidin-5-yl-1h-indole-7-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC2=C(C=3C=NC=NC=3)C=CC(C(N)=O)=C2N1 MPVWENZZZCNIJA-UHFFFAOYSA-N 0.000 claims 1
BJXLJSNZGWLSMQ-UHFFFAOYSA-N 2-(4-methylphenyl)-4-thiophen-3-yl-1h-indole-7-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC2=C(C3=CSC=C3)C=CC(C(N)=O)=C2N1 BJXLJSNZGWLSMQ-UHFFFAOYSA-N 0.000 claims 1
BXPAKHVYYLDGKS-ZDUSSCGKSA-N 2-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-yl)-4-[(3R)-1-prop-2-enoylpyrrolidin-3-yl]-1H-indole-7-carboxamide Chemical compound NC(=O)c1ccc([C@H]2CCN(C2)C(=O)C=C)c2cc([nH]c12)-c1cc2COCCn2n1 BXPAKHVYYLDGKS-ZDUSSCGKSA-N 0.000 claims 1
BXPAKHVYYLDGKS-CYBMUJFWSA-N 2-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-yl)-4-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]-1H-indole-7-carboxamide Chemical compound NC(=O)c1ccc([C@@H]2CCN(C2)C(=O)C=C)c2cc([nH]c12)-c1cc2COCCn2n1 BXPAKHVYYLDGKS-CYBMUJFWSA-N 0.000 claims 1
IMMUVOYTVIABAD-UHFFFAOYSA-N 2-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-yl)-4-[methyl-(1-prop-2-enoylazetidin-3-yl)amino]-1H-indole-7-carboxamide Chemical compound CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)-c1cc2COCCn2n1 IMMUVOYTVIABAD-UHFFFAOYSA-N 0.000 claims 1
RXFOFOZOXGURKB-UHFFFAOYSA-N 2-[1-(2-hydroxyethyl)pyrazol-4-yl]-4-[2-methyl-3-(4-oxoquinazolin-3-yl)phenyl]-1h-indole-7-carboxamide Chemical compound C1=CC=C(N2C(C3=CC=CC=C3N=C2)=O)C(C)=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C=1C=NN(CCO)C=1 RXFOFOZOXGURKB-UHFFFAOYSA-N 0.000 claims 1
ZIOMQOCDRBPUQF-LJQANCHMSA-N 2-[1-[(2r)-2,3-dihydroxypropyl]pyrazol-4-yl]-4-[2-methyl-3-(4-oxoquinazolin-3-yl)phenyl]-1h-indole-7-carboxamide Chemical compound C1=CC=C(N2C(C3=CC=CC=C3N=C2)=O)C(C)=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C=1C=NN(C[C@@H](O)CO)C=1 ZIOMQOCDRBPUQF-LJQANCHMSA-N 0.000 claims 1
ZIOMQOCDRBPUQF-IBGZPJMESA-N 2-[1-[(2s)-2,3-dihydroxypropyl]pyrazol-4-yl]-4-[2-methyl-3-(4-oxoquinazolin-3-yl)phenyl]-1h-indole-7-carboxamide Chemical compound C1=CC=C(N2C(C3=CC=CC=C3N=C2)=O)C(C)=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C=1C=NN(C[C@H](O)CO)C=1 ZIOMQOCDRBPUQF-IBGZPJMESA-N 0.000 claims 1
VJIOSCMTZVXQQU-UHFFFAOYSA-N 2-chlorobutanamide Chemical compound CCC(Cl)C(N)=O VJIOSCMTZVXQQU-UHFFFAOYSA-N 0.000 claims 1
IMOLAGKJZFODRK-UHFFFAOYSA-N 2-phenylprop-2-enamide Chemical compound NC(=O)C(=C)C1=CC=CC=C1 IMOLAGKJZFODRK-UHFFFAOYSA-N 0.000 claims 1
QJIIUFLKOQYKMD-UHFFFAOYSA-N 3-cyclopropylprop-2-enamide Chemical compound NC(=O)C=CC1CC1 QJIIUFLKOQYKMD-UHFFFAOYSA-N 0.000 claims 1
MDTDPEHJGYVJHS-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound C1CCCC2=C1C=C(C(=O)N)S2 MDTDPEHJGYVJHS-UHFFFAOYSA-N 0.000 claims 1
UNHZLHSLZZWMNP-UHFFFAOYSA-N 4-(1-prop-2-enoylpiperidin-3-yl)-1h-indole-7-carboxamide Chemical compound C1=2C=CNC=2C(C(=O)N)=CC=C1C1CCCN(C(=O)C=C)C1 UNHZLHSLZZWMNP-UHFFFAOYSA-N 0.000 claims 1
WTMAQOFLKNRMNH-UHFFFAOYSA-N 4-(2-aminoethylamino)-2-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C=1C=2C(NCCN)=CC=C(C(N)=O)C=2NC=1C1=CC=C(F)C=C1 WTMAQOFLKNRMNH-UHFFFAOYSA-N 0.000 claims 1
OESWVKVQBUOVLX-UHFFFAOYSA-N 4-(2-aminophenyl)-1h-indole-7-carboxamide Chemical compound C1=2C=CNC=2C(C(=O)N)=CC=C1C1=CC=CC=C1N OESWVKVQBUOVLX-UHFFFAOYSA-N 0.000 claims 1
YTMJZXHLEPQRKX-UHFFFAOYSA-N 4-(2-aminopyridin-4-yl)-1h-indole-7-carboxamide Chemical compound C1=2C=CNC=2C(C(=O)N)=CC=C1C1=CC=NC(N)=C1 YTMJZXHLEPQRKX-UHFFFAOYSA-N 0.000 claims 1
NICNQYVWCOONIF-UHFFFAOYSA-N 4-(3,5-dimethyl-1,2-oxazol-4-yl)-2-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC=C(C(N)=O)C2=C1C=C(C=1C=CC(F)=CC=1)N2 NICNQYVWCOONIF-UHFFFAOYSA-N 0.000 claims 1
KMFCQSFSMJMZKK-UHFFFAOYSA-N 4-(3,5-dimethyl-1,2-oxazol-4-yl)-2-(4-methylphenyl)-1h-indole-7-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC=C(C(N)=O)C2=C1C=C(C=1C=CC(C)=CC=1)N2 KMFCQSFSMJMZKK-UHFFFAOYSA-N 0.000 claims 1
ASSYCOPBGVLEKT-UHFFFAOYSA-N 4-(3-amino-2-methylphenyl)-1h-indole-7-carboxamide Chemical compound CC1=C(N)C=CC=C1C1=CC=C(C(N)=O)C2=C1C=CN2 ASSYCOPBGVLEKT-UHFFFAOYSA-N 0.000 claims 1
XLFRWPDYBMNRFV-UHFFFAOYSA-N 4-(3-amino-2-methylphenyl)-2-(4,4-difluorocyclohexen-1-yl)-1h-indole-7-carboxamide Chemical compound CC1=C(N)C=CC=C1C1=CC=C(C(N)=O)C2=C1C=C(C=1CCC(F)(F)CC=1)N2 XLFRWPDYBMNRFV-UHFFFAOYSA-N 0.000 claims 1
JTKUYHLGMKSNDK-UHFFFAOYSA-N 4-(5-acetylthiophen-2-yl)-2-(4-methylphenyl)-1h-indole-7-carboxamide Chemical compound S1C(C(=O)C)=CC=C1C1=CC=C(C(N)=O)C2=C1C=C(C=1C=CC(C)=CC=1)N2 JTKUYHLGMKSNDK-UHFFFAOYSA-N 0.000 claims 1
BXMMBMCOQPJIJC-UHFFFAOYSA-N 4-(5-aminopyridin-3-yl)-1h-indole-7-carboxamide Chemical compound C1=2C=CNC=2C(C(=O)N)=CC=C1C1=CN=CC(N)=C1 BXMMBMCOQPJIJC-UHFFFAOYSA-N 0.000 claims 1
RDRVAEKUYYPXMB-LLVKDONJSA-N 4-[(3r)-3-(1,3-thiazol-2-ylcarbamoylamino)piperidin-1-yl]-1h-indole-7-carboxamide Chemical compound N([C@@H]1CCCN(C1)C1=CC=C(C=2NC=CC=21)C(=O)N)C(=O)NC1=NC=CS1 RDRVAEKUYYPXMB-LLVKDONJSA-N 0.000 claims 1
FNZMDGMWCIATRN-CQSZACIVSA-N 4-[(3r)-3-(4-oxoquinazolin-3-yl)piperidin-1-yl]-1h-indole-7-carboxamide Chemical compound C1=NC2=CC=CC=C2C(=O)N1[C@@H](C1)CCCN1C1=CC=C(C(=O)N)C2=C1C=CN2 FNZMDGMWCIATRN-CQSZACIVSA-N 0.000 claims 1
CLDXRPBMZIWVKN-GOSISDBHSA-N 4-[(3r)-3-(4-oxoquinazolin-3-yl)piperidin-1-yl]-2-pyridin-3-yl-1h-indole-7-carboxamide Chemical compound N1C=2C(C(=O)N)=CC=C(N3C[C@@H](CCC3)N3C(C4=CC=CC=C4N=C3)=O)C=2C=C1C1=CC=CN=C1 CLDXRPBMZIWVKN-GOSISDBHSA-N 0.000 claims 1
IBUFPCUVSHSDKT-GOSISDBHSA-N 4-[(3r)-3-(5-fluoro-3-oxo-1h-isoindol-2-yl)piperidin-1-yl]-2-(1-methylpyrazol-4-yl)-1h-indole-7-carboxamide Chemical compound C1=NN(C)C=C1C1=CC2=C(N3C[C@@H](CCC3)N3C(C4=CC(F)=CC=C4C3)=O)C=CC(C(N)=O)=C2N1 IBUFPCUVSHSDKT-GOSISDBHSA-N 0.000 claims 1
JEZAWSITKMVAGA-LJQANCHMSA-N 4-[(3r)-3-(6-fluoro-4-oxoquinazolin-3-yl)piperidin-1-yl]-2-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound N1C=2C(C(=O)N)=CC=C(N3C[C@@H](CCC3)N3C(C4=CC(F)=CC=C4N=C3)=O)C=2C=C1C1=CC=C(F)C=C1 JEZAWSITKMVAGA-LJQANCHMSA-N 0.000 claims 1
IQXTUVDEWDVYQH-OAQYLSRUSA-N 4-[(3r)-3-[(4-cyclopropylbenzoyl)amino]piperidin-1-yl]-2-(1-methylpyrazol-4-yl)-1h-indole-7-carboxamide Chemical compound C1=NN(C)C=C1C1=CC2=C(N3C[C@@H](CCC3)NC(=O)C=3C=CC(=CC=3)C3CC3)C=CC(C(N)=O)=C2N1 IQXTUVDEWDVYQH-OAQYLSRUSA-N 0.000 claims 1
WAQQYMGHSBMFEV-OAHLLOKOSA-N 4-[(3r)-3-[(4-methoxybenzoyl)amino]piperidin-1-yl]-1h-indole-7-carboxamide Chemical compound C1=CC(OC)=CC=C1C(=O)N[C@H]1CN(C=2C=3C=CNC=3C(C(N)=O)=CC=2)CCC1 WAQQYMGHSBMFEV-OAHLLOKOSA-N 0.000 claims 1
WNDONGMTWACYPE-GOSISDBHSA-N 4-[(3r)-3-[(4-methoxybenzoyl)amino]piperidin-1-yl]-2-(1-methylpyrazol-4-yl)-1h-indole-7-carboxamide Chemical compound C1=CC(OC)=CC=C1C(=O)N[C@H]1CN(C=2C=3C=C(NC=3C(C(N)=O)=CC=2)C2=CN(C)N=C2)CCC1 WNDONGMTWACYPE-GOSISDBHSA-N 0.000 claims 1
KOZNEOJILLLALQ-GOSISDBHSA-N 4-[(3r)-3-[(4-tert-butylbenzoyl)amino]piperidin-1-yl]-1h-indole-7-carboxamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)N[C@H]1CN(C=2C=3C=CNC=3C(C(N)=O)=CC=2)CCC1 KOZNEOJILLLALQ-GOSISDBHSA-N 0.000 claims 1
MZNGFMRRLBNNIB-OAQYLSRUSA-N 4-[(3r)-3-[(4-tert-butylbenzoyl)amino]piperidin-1-yl]-2-(1-methylpyrazol-4-yl)-1h-indole-7-carboxamide Chemical compound C1=NN(C)C=C1C1=CC2=C(N3C[C@@H](CCC3)NC(=O)C=3C=CC(=CC=3)C(C)(C)C)C=CC(C(N)=O)=C2N1 MZNGFMRRLBNNIB-OAQYLSRUSA-N 0.000 claims 1
CEFVBCKELLYGKO-JOCHJYFZSA-N 4-[(3r)-3-[(4-tert-butylbenzoyl)amino]piperidin-1-yl]-2-pyridin-3-yl-1h-indole-7-carboxamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)N[C@H]1CN(C=2C=3C=C(NC=3C(C(N)=O)=CC=2)C=2C=NC=CC=2)CCC1 CEFVBCKELLYGKO-JOCHJYFZSA-N 0.000 claims 1
ZCYDQIDCYZMOQG-HXUWFJFHSA-N 4-[(3r)-3-[[4-(1-amino-2-methyl-1-oxopropan-2-yl)benzoyl]amino]piperidin-1-yl]-2-(1-methylpyrazol-4-yl)-1h-indole-7-carboxamide Chemical compound C1=NN(C)C=C1C1=CC2=C(N3C[C@@H](CCC3)NC(=O)C=3C=CC(=CC=3)C(C)(C)C(N)=O)C=CC(C(N)=O)=C2N1 ZCYDQIDCYZMOQG-HXUWFJFHSA-N 0.000 claims 1
ADNBODRQQLNFMC-OAHLLOKOSA-N 4-[(3r)-3-[[4-(trifluoromethyl)benzoyl]amino]piperidin-1-yl]-1h-indole-7-carboxamide Chemical compound N([C@@H]1CCCN(C1)C1=CC=C(C=2NC=CC=21)C(=O)N)C(=O)C1=CC=C(C(F)(F)F)C=C1 ADNBODRQQLNFMC-OAHLLOKOSA-N 0.000 claims 1
PFMWWLJZFVEEBT-UHFFFAOYSA-N 4-[2-methyl-3-(3-oxo-1h-isoindol-2-yl)phenyl]-2-pyridin-3-yl-1h-indole-7-carboxamide Chemical compound CC1=C(N2C(C3=CC=CC=C3C2)=O)C=CC=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C1=CC=CN=C1 PFMWWLJZFVEEBT-UHFFFAOYSA-N 0.000 claims 1
VZZWPPXNRRCJPR-UHFFFAOYSA-N 4-[2-methyl-3-(4,5,6,7-tetrahydro-1-benzothiophene-2-carbonylamino)phenyl]-2-pyridin-3-yl-1h-indole-7-carboxamide Chemical compound CC1=C(NC(=O)C=2SC=3CCCCC=3C=2)C=CC=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C1=CC=CN=C1 VZZWPPXNRRCJPR-UHFFFAOYSA-N 0.000 claims 1
XPZSMQBTPPDJPR-UHFFFAOYSA-N 4-[2-methyl-3-(4-oxoquinazolin-3-yl)phenyl]-1h-indole-7-carboxamide Chemical compound C1=CC=C(N2C(C3=CC=CC=C3N=C2)=O)C(C)=C1C1=CC=C(C(N)=O)C2=C1C=CN2 XPZSMQBTPPDJPR-UHFFFAOYSA-N 0.000 claims 1
WZLBFUJUNHWUAE-UHFFFAOYSA-N 4-[2-methyl-3-(4-oxoquinazolin-3-yl)phenyl]-2-(1,2,3,6-tetrahydropyridin-4-yl)-1h-indole-7-carboxamide Chemical compound C1=CC=C(N2C(C3=CC=CC=C3N=C2)=O)C(C)=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C1=CCNCC1 WZLBFUJUNHWUAE-UHFFFAOYSA-N 0.000 claims 1
KZAIMEBWVUQDIP-UHFFFAOYSA-N 4-[2-methyl-3-(4-oxoquinazolin-3-yl)phenyl]-2-(1-methylpyrazol-4-yl)-1h-indole-7-carboxamide Chemical compound C1=CC=C(N2C(C3=CC=CC=C3N=C2)=O)C(C)=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C=1C=NN(C)C=1 KZAIMEBWVUQDIP-UHFFFAOYSA-N 0.000 claims 1
PXJNRRRHLZQNRR-UHFFFAOYSA-N 4-[2-methyl-3-(4-oxoquinazolin-3-yl)phenyl]-2-pyridin-3-yl-1h-indole-7-carboxamide Chemical compound C1=CC=C(N2C(C3=CC=CC=C3N=C2)=O)C(C)=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C1=CC=CN=C1 PXJNRRRHLZQNRR-UHFFFAOYSA-N 0.000 claims 1
HLLWUYRSVBFCPR-UHFFFAOYSA-N 4-[2-methyl-3-(4-oxoquinazolin-3-yl)phenyl]-2-pyrimidin-5-yl-1h-indole-7-carboxamide Chemical compound C1=CC=C(N2C(C3=CC=CC=C3N=C2)=O)C(C)=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C1=CN=CN=C1 HLLWUYRSVBFCPR-UHFFFAOYSA-N 0.000 claims 1
FRYLRJDJCAOUEZ-UHFFFAOYSA-N 4-[2-methyl-3-(5-methyl-3-oxo-1h-isoindol-2-yl)phenyl]-2-pyridin-3-yl-1h-indole-7-carboxamide Chemical compound O=C1C2=CC(C)=CC=C2CN1C(C=1C)=CC=CC=1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C1=CC=CN=C1 FRYLRJDJCAOUEZ-UHFFFAOYSA-N 0.000 claims 1
DNLNHLRBNUVBAK-UHFFFAOYSA-N 4-[2-methyl-3-(prop-2-enoylamino)phenyl]-2-(2-methylpyrazol-3-yl)-1H-indole-7-carboxamide Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccnn1C DNLNHLRBNUVBAK-UHFFFAOYSA-N 0.000 claims 1
ZXZGHIWUVGGGQY-UHFFFAOYSA-N 4-[2-methyl-3-(prop-2-enoylamino)phenyl]-2-[2-(oxan-2-yl)pyrazol-3-yl]-1H-indole-7-carboxamide Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccnn1C1CCCCO1 ZXZGHIWUVGGGQY-UHFFFAOYSA-N 0.000 claims 1
RFPIWDVTQQTULP-UHFFFAOYSA-N 4-[3-(5-fluoro-3-oxo-1h-isoindol-2-yl)-2-methylphenyl]-2-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound CC1=C(N2C(C3=CC(F)=CC=C3C2)=O)C=CC=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C1=CC=C(F)C=C1 RFPIWDVTQQTULP-UHFFFAOYSA-N 0.000 claims 1
YLFRPFNEZQIRQB-UHFFFAOYSA-N 4-[3-(5-fluoro-3-oxo-1h-isoindol-2-yl)-2-methylphenyl]-2-pyridin-3-yl-1h-indole-7-carboxamide Chemical compound CC1=C(N2C(C3=CC(F)=CC=C3C2)=O)C=CC=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C1=CC=CN=C1 YLFRPFNEZQIRQB-UHFFFAOYSA-N 0.000 claims 1
VYHPGQJSHYLYTR-UHFFFAOYSA-N 4-[3-(6-fluoro-4-oxoquinazolin-3-yl)-2-(hydroxymethyl)phenyl]-2-(1-methylpyrazol-4-yl)-1h-indole-7-carboxamide Chemical compound C1=NN(C)C=C1C1=CC2=C(C=3C(=C(C=CC=3)N3C(C4=CC(F)=CC=C4N=C3)=O)CO)C=CC(C(N)=O)=C2N1 VYHPGQJSHYLYTR-UHFFFAOYSA-N 0.000 claims 1
LYCNFJFIBJJRNC-UHFFFAOYSA-N 4-[3-(6-fluoro-4-oxoquinazolin-3-yl)-2-methylphenyl]-2-pyrimidin-5-yl-1h-indole-7-carboxamide Chemical compound C1=CC=C(N2C(C3=CC(F)=CC=C3N=C2)=O)C(C)=C1C(C=1C=2)=CC=C(C(N)=O)C=1NC=2C1=CN=CN=C1 LYCNFJFIBJJRNC-UHFFFAOYSA-N 0.000 claims 1
PQBUQKZSZHBBNB-UHFFFAOYSA-N 4-[3-(7-cyclopropyl-5-fluoro-4-oxoquinazolin-3-yl)piperidin-1-yl]-1h-indole-7-carboxamide Chemical compound C1=2C=CNC=2C(C(=O)N)=CC=C1N(C1)CCCC1N(C(C1=C(F)C=2)=O)C=NC1=CC=2C1CC1 PQBUQKZSZHBBNB-UHFFFAOYSA-N 0.000 claims 1
AFBFEXSPCHLJDM-UHFFFAOYSA-N 4-[3-[(4-tert-butylbenzoyl)amino]-2-methylphenyl]-1h-indole-7-carboxamide Chemical compound C1=CC=C(C=2C=3C=CNC=3C(C(N)=O)=CC=2)C(C)=C1NC(=O)C1=CC=C(C(C)(C)C)C=C1 AFBFEXSPCHLJDM-UHFFFAOYSA-N 0.000 claims 1
YDAZZTQPSMWJKA-SJLPKXTDSA-N 4-[[(1r,2r)-2-aminocyclohexyl]amino]-2-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound N[C@@H]1CCCC[C@H]1NC1=CC=C(C(N)=O)C2=C1C=C(C=1C=CC(F)=CC=1)N2 YDAZZTQPSMWJKA-SJLPKXTDSA-N 0.000 claims 1
BUZIQDAPQMAGNV-UHFFFAOYSA-N 4-[methyl-(1-prop-2-enoylazetidin-3-yl)amino]-2-(2-methylpyrazol-3-yl)-1H-indole-7-carboxamide Chemical compound CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccnn1C BUZIQDAPQMAGNV-UHFFFAOYSA-N 0.000 claims 1
AQSRRQTWOVJJBA-UHFFFAOYSA-N 4-iodo-2-pyridin-3-yl-1h-indole-7-carboxamide Chemical compound N1C=2C(C(=O)N)=CC=C(I)C=2C=C1C1=CC=CN=C1 AQSRRQTWOVJJBA-UHFFFAOYSA-N 0.000 claims 1
125000001054 5 membered carbocyclic group Chemical group 0.000 claims 1
125000004008 6 membered carbocyclic group Chemical group 0.000 claims 1
208000023275 Autoimmune disease Diseases 0.000 claims 1
YWILRCCCIHSUIF-UHFFFAOYSA-N C(#N)CNC(=O)C=1C=C(C=CC1)C1=C2C=CNC2=C(C=C1)C(=O)N Chemical compound C(#N)CNC(=O)C=1C=C(C=CC1)C1=C2C=CNC2=C(C=C1)C(=O)N YWILRCCCIHSUIF-UHFFFAOYSA-N 0.000 claims 1
MBMHORPRCPVTMF-LLVKDONJSA-N C(C=C)(=O)N1C[C@@H](CC1)C1=C2C=C(NC2=C(C=C1)C(=O)N)C Chemical compound C(C=C)(=O)N1C[C@@H](CC1)C1=C2C=C(NC2=C(C=C1)C(=O)N)C MBMHORPRCPVTMF-LLVKDONJSA-N 0.000 claims 1
MBMHORPRCPVTMF-NSHDSACASA-N C(C=C)(=O)N1C[C@H](CC1)C1=C2C=C(NC2=C(C=C1)C(=O)N)C Chemical compound C(C=C)(=O)N1C[C@H](CC1)C1=C2C=C(NC2=C(C=C1)C(=O)N)C MBMHORPRCPVTMF-NSHDSACASA-N 0.000 claims 1
BSTIGZRODTWMJN-MRXNPFEDSA-N C(C=C)(=O)N[C@H]1CN(CCC1)C1=C2C=C(NC2=C(C=C1)C(=O)N)C=1CCN(CC1)S(=O)(=O)C Chemical compound C(C=C)(=O)N[C@H]1CN(CCC1)C1=C2C=C(NC2=C(C=C1)C(=O)N)C=1CCN(CC1)S(=O)(=O)C BSTIGZRODTWMJN-MRXNPFEDSA-N 0.000 claims 1
ZVLPFZCGSSCGDH-WDEREUQCSA-N C(C=C)(=O)N[C@H]1C[C@H](CC1)C1=C2C=CNC2=C(C=C1)C(=O)N Chemical compound C(C=C)(=O)N[C@H]1C[C@H](CC1)C1=C2C=CNC2=C(C=C1)C(=O)N ZVLPFZCGSSCGDH-WDEREUQCSA-N 0.000 claims 1
ILFXYLXSWQWALV-QGZVFWFLSA-N C(N)(=O)C=1C=CC(=C2C=C(NC12)C=1CCN(CC1)S(=O)(=O)C)N1C[C@@H](CCC1)NC(=O)C=1N=C(OC1)C Chemical compound C(N)(=O)C=1C=CC(=C2C=C(NC12)C=1CCN(CC1)S(=O)(=O)C)N1C[C@@H](CCC1)NC(=O)C=1N=C(OC1)C ILFXYLXSWQWALV-QGZVFWFLSA-N 0.000 claims 1
XCLXZRKRBVJMBQ-QPJJXVBHSA-N C1CN(C)CCN1C\C=C\C(=O)Nc1cccc(-c2ccc(C(N)=O)c3[nH]ccc32)c1C Chemical compound C1CN(C)CCN1C\C=C\C(=O)Nc1cccc(-c2ccc(C(N)=O)c3[nH]ccc32)c1C XCLXZRKRBVJMBQ-QPJJXVBHSA-N 0.000 claims 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
NHFADNOXJFPTKT-UHFFFAOYSA-N CC#CC(=O)Nc1c[nH]c2c(ccc(-c3cccc(NC(=O)c4nccs4)c3C)c12)C(N)=O Chemical compound CC#CC(=O)Nc1c[nH]c2c(ccc(-c3cccc(NC(=O)c4nccs4)c3C)c12)C(N)=O NHFADNOXJFPTKT-UHFFFAOYSA-N 0.000 claims 1
BVPKXRSEESPRSD-UHFFFAOYSA-N CC(=C)C(=O)NCc1ccccc1-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)c2nccs2)c1C Chemical compound CC(=C)C(=O)NCc1ccccc1-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)c2nccs2)c1C BVPKXRSEESPRSD-UHFFFAOYSA-N 0.000 claims 1
MZEFDRLOFVBVEK-UHFFFAOYSA-N CC(=O)C(=O)NCc1cccc(c1)-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound CC(=O)C(=O)NCc1cccc(c1)-c1ccc(C(N)=O)c2[nH]ccc12 MZEFDRLOFVBVEK-UHFFFAOYSA-N 0.000 claims 1
FQYYGTNFJPOIDM-UHFFFAOYSA-N CC(=O)C(=O)Nc1cccc(c1)-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound CC(=O)C(=O)Nc1cccc(c1)-c1ccc(C(N)=O)c2[nH]ccc12 FQYYGTNFJPOIDM-UHFFFAOYSA-N 0.000 claims 1
XHRMCHBCISVRLG-UHFFFAOYSA-N CC(=O)N1CCC(CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)c2ccc(cc2)C2CC2)c1C Chemical compound CC(=O)N1CCC(CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)c2ccc(cc2)C2CC2)c1C XHRMCHBCISVRLG-UHFFFAOYSA-N 0.000 claims 1
FAYZOUVCSVSYLJ-UHFFFAOYSA-N CC(=O)Nc1cccc(c1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C Chemical compound CC(=O)Nc1cccc(c1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C FAYZOUVCSVSYLJ-UHFFFAOYSA-N 0.000 claims 1
LEEBVIAMFSWGHD-UHFFFAOYSA-N CC(=O)Nc1cccc(c1C)-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound CC(=O)Nc1cccc(c1C)-c1ccc(C(N)=O)c2[nH]ccc12 LEEBVIAMFSWGHD-UHFFFAOYSA-N 0.000 claims 1
WOXPAKZBMPAWRO-UHFFFAOYSA-N CC(=O)Nc1ccccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound CC(=O)Nc1ccccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O WOXPAKZBMPAWRO-UHFFFAOYSA-N 0.000 claims 1
ZPZHUJZBGMPJRB-UHFFFAOYSA-N CC(C)Cn1cc(cn1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C Chemical compound CC(C)Cn1cc(cn1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C ZPZHUJZBGMPJRB-UHFFFAOYSA-N 0.000 claims 1
JPRWJTKVYGEBFW-UHFFFAOYSA-N CC(C=CC(S(N1CCCC1)(=O)=O)=C1)=C1N(C=CC1=CC=C2)C1=C2C(N)=O Chemical compound CC(C=CC(S(N1CCCC1)(=O)=O)=C1)=C1N(C=CC1=CC=C2)C1=C2C(N)=O JPRWJTKVYGEBFW-UHFFFAOYSA-N 0.000 claims 1
DRLFORRCLZEVNA-UHFFFAOYSA-N CC(Cl)C(=O)Nc1cccc(c1C)-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound CC(Cl)C(=O)Nc1cccc(c1C)-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O DRLFORRCLZEVNA-UHFFFAOYSA-N 0.000 claims 1
SBATYYHCKAKADI-UHFFFAOYSA-N CC1=C(C=CC=C1NC(C=CCNCC1OCCC1)=O)C1=C2C=CNC2=C(C=C1)C(=O)N Chemical compound CC1=C(C=CC=C1NC(C=CCNCC1OCCC1)=O)C1=C2C=CNC2=C(C=C1)C(=O)N SBATYYHCKAKADI-UHFFFAOYSA-N 0.000 claims 1
DOVIVYKNYGBTAA-UHFFFAOYSA-N CCC(=C)C(=O)Nc1cccc(c1C)-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound CCC(=C)C(=O)Nc1cccc(c1C)-c1ccc(C(N)=O)c2[nH]ccc12 DOVIVYKNYGBTAA-UHFFFAOYSA-N 0.000 claims 1
VQKJOYUZBJMSCO-NSHDSACASA-N CCC(=O)N1CC[C@@H](C1)c1ccc(C(N)=O)c2[nH]c(C)cc12 Chemical compound CCC(=O)N1CC[C@@H](C1)c1ccc(C(N)=O)c2[nH]c(C)cc12 VQKJOYUZBJMSCO-NSHDSACASA-N 0.000 claims 1
VQKJOYUZBJMSCO-LLVKDONJSA-N CCC(=O)N1CC[C@H](C1)c1ccc(C(N)=O)c2[nH]c(C)cc12 Chemical compound CCC(=O)N1CC[C@H](C1)c1ccc(C(N)=O)c2[nH]c(C)cc12 VQKJOYUZBJMSCO-LLVKDONJSA-N 0.000 claims 1
MRRCDSIGELDOLI-UHFFFAOYSA-N CCC(=O)NCc1ccccc1-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)c2nccs2)c1C Chemical compound CCC(=O)NCc1ccccc1-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)c2nccs2)c1C MRRCDSIGELDOLI-UHFFFAOYSA-N 0.000 claims 1
QCJNSKHHYCGJRF-UHFFFAOYSA-N CCC(=O)Nc1cccc(c1C)-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound CCC(=O)Nc1cccc(c1C)-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O QCJNSKHHYCGJRF-UHFFFAOYSA-N 0.000 claims 1
OCQIKWBMHFUMNQ-UHFFFAOYSA-N CCCN1CCC(CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)N(C)C1CN(C1)C(=O)C=C Chemical compound CCCN1CCC(CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)N(C)C1CN(C1)C(=O)C=C OCQIKWBMHFUMNQ-UHFFFAOYSA-N 0.000 claims 1
OUAPHHDAERUUPW-UHFFFAOYSA-N CCN1CCc2cc(ccc2C1)-c1cc2c(ccc(C(N)=O)c2[nH]1)N(C)C1CN(C1)C(=O)C=C Chemical compound CCN1CCc2cc(ccc2C1)-c1cc2c(ccc(C(N)=O)c2[nH]1)N(C)C1CN(C1)C(=O)C=C OUAPHHDAERUUPW-UHFFFAOYSA-N 0.000 claims 1
HOPANDDRHUVWJO-UHFFFAOYSA-N CCOCCc1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1 Chemical compound CCOCCc1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1 HOPANDDRHUVWJO-UHFFFAOYSA-N 0.000 claims 1
GZMCPVDKMCDNQI-UHFFFAOYSA-N CN(C)C(=O)c1ccc(cc1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C Chemical compound CN(C)C(=O)c1ccc(cc1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C GZMCPVDKMCDNQI-UHFFFAOYSA-N 0.000 claims 1
IFBDMPYGCKFJOV-UHFFFAOYSA-N CN(C)CCC(=O)NCc1ccccc1-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)c2nccs2)c1C Chemical compound CN(C)CCC(=O)NCc1ccccc1-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)c2nccs2)c1C IFBDMPYGCKFJOV-UHFFFAOYSA-N 0.000 claims 1
SERFTOGYKLPADE-UHFFFAOYSA-N CN(C)CCC(=O)Nc1cccc(c1C)-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound CN(C)CCC(=O)Nc1cccc(c1C)-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O SERFTOGYKLPADE-UHFFFAOYSA-N 0.000 claims 1
FDNJUGFDOASPKE-UHFFFAOYSA-N CN(C)c1cccc(c1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C Chemical compound CN(C)c1cccc(c1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C FDNJUGFDOASPKE-UHFFFAOYSA-N 0.000 claims 1
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UHFLGIUCXWTDNE-UHFFFAOYSA-N CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(C)cc12 Chemical compound CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(C)cc12 UHFLGIUCXWTDNE-UHFFFAOYSA-N 0.000 claims 1
LVYZYDZHGAKKTJ-UHFFFAOYSA-N CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(CN2CCOCC2)cn1 Chemical compound CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(CN2CCOCC2)cn1 LVYZYDZHGAKKTJ-UHFFFAOYSA-N 0.000 claims 1
JJHRJQYASOPHJA-UHFFFAOYSA-N CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(nc1)N1CCOCC1 Chemical compound CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(nc1)N1CCOCC1 JJHRJQYASOPHJA-UHFFFAOYSA-N 0.000 claims 1
HCVIEQZPXOIWJS-UHFFFAOYSA-N CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc2CCCOc2c1 Chemical compound CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc2CCCOc2c1 HCVIEQZPXOIWJS-UHFFFAOYSA-N 0.000 claims 1
DLNGEJWXYSVUHA-UHFFFAOYSA-N CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc2CCOCc2c1 Chemical compound CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc2CCOCc2c1 DLNGEJWXYSVUHA-UHFFFAOYSA-N 0.000 claims 1
BGVMBEOTJYTJMU-UHFFFAOYSA-N CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc2OCCNc2c1 Chemical compound CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc2OCCNc2c1 BGVMBEOTJYTJMU-UHFFFAOYSA-N 0.000 claims 1
XDCHQGPUHOXPCJ-UHFFFAOYSA-N CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)-c1cn(C)nc1C Chemical compound CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)-c1cn(C)nc1C XDCHQGPUHOXPCJ-UHFFFAOYSA-N 0.000 claims 1
WVGQTQWEXOKROY-UHFFFAOYSA-N CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)-c1cnc2CCOCc2c1 Chemical compound CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)-c1cnc2CCOCc2c1 WVGQTQWEXOKROY-UHFFFAOYSA-N 0.000 claims 1
LQXQJWALGKBICR-UHFFFAOYSA-N CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)-c1cnn(C)c1 Chemical compound CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)-c1cnn(C)c1 LQXQJWALGKBICR-UHFFFAOYSA-N 0.000 claims 1
XONSTIWXPQRMTR-UHFFFAOYSA-N CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)C1(O)COC1 Chemical compound CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)C1(O)COC1 XONSTIWXPQRMTR-UHFFFAOYSA-N 0.000 claims 1
IBKFXXPTIDPEGG-UHFFFAOYSA-N CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCC(CC1)S(C)(=O)=O Chemical compound CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCC(CC1)S(C)(=O)=O IBKFXXPTIDPEGG-UHFFFAOYSA-N 0.000 claims 1
KALUNMAYBYEJSU-UHFFFAOYSA-N CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCC(F)(F)CC1 Chemical compound CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCC(F)(F)CC1 KALUNMAYBYEJSU-UHFFFAOYSA-N 0.000 claims 1
XXDOFUSYHRHOPD-UHFFFAOYSA-N CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)C1CCOC1 Chemical compound CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)C1CCOC1 XXDOFUSYHRHOPD-UHFFFAOYSA-N 0.000 claims 1
XXDOFUSYHRHOPD-GFCCVEGCSA-N CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)[C@@H]1CCOC1 Chemical compound CN(C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]c(cc12)[C@@H]1CCOC1 XXDOFUSYHRHOPD-GFCCVEGCSA-N 0.000 claims 1
DERDSTMMNLJBHE-UHFFFAOYSA-N CN(C1CN(C1)C(=O)C=C)c1cnc(C(N)=O)c2[nH]ccc12 Chemical compound CN(C1CN(C1)C(=O)C=C)c1cnc(C(N)=O)c2[nH]ccc12 DERDSTMMNLJBHE-UHFFFAOYSA-N 0.000 claims 1
RBHDMOYSLMBTKL-UHFFFAOYSA-N CN(c1ccc(C(N)=O)c2[nH]ccc12)C1(C)CN(C1)C(=O)C=C Chemical compound CN(c1ccc(C(N)=O)c2[nH]ccc12)C1(C)CN(C1)C(=O)C=C RBHDMOYSLMBTKL-UHFFFAOYSA-N 0.000 claims 1
ZUYRZLFBTSUYGT-UHFFFAOYSA-N CN1CCCC(C1)C(=O)Nc1cccc(c1C)-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound CN1CCCC(C1)C(=O)Nc1cccc(c1C)-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O ZUYRZLFBTSUYGT-UHFFFAOYSA-N 0.000 claims 1
MGZRPOIKIRIWHI-UHFFFAOYSA-N CN1CCN(CC1)C(=O)c1ccc(cc1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C Chemical compound CN1CCN(CC1)C(=O)c1ccc(cc1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C MGZRPOIKIRIWHI-UHFFFAOYSA-N 0.000 claims 1
SQAUVMGKXFULKX-UHFFFAOYSA-N CN1CCN(CC1)C(=O)c1cccc(c1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C Chemical compound CN1CCN(CC1)C(=O)c1cccc(c1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C SQAUVMGKXFULKX-UHFFFAOYSA-N 0.000 claims 1
LXJPDIZXVSHXQW-UHFFFAOYSA-N CN1CCN(CCC(=O)Nc2cccc(c2C)-c2ccc(C(N)=O)c3[nH]c(cc23)C2=CCN(CC2)S(C)(=O)=O)CC1 Chemical compound CN1CCN(CCC(=O)Nc2cccc(c2C)-c2ccc(C(N)=O)c3[nH]c(cc23)C2=CCN(CC2)S(C)(=O)=O)CC1 LXJPDIZXVSHXQW-UHFFFAOYSA-N 0.000 claims 1
LZXQPEWHMDHTBX-UHFFFAOYSA-N CN1N=CC(C2=CC3=CC=CC(C(N)=O)=C3N2N(CCC2)CC2NC(C2=CC=C(C(F)F)C=C2)=O)=C1 Chemical compound CN1N=CC(C2=CC3=CC=CC(C(N)=O)=C3N2N(CCC2)CC2NC(C2=CC=C(C(F)F)C=C2)=O)=C1 LZXQPEWHMDHTBX-UHFFFAOYSA-N 0.000 claims 1
GGOWFVIOGGPPEA-UHFFFAOYSA-N CNc1cccc(c1)-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound CNc1cccc(c1)-c1ccc(C(N)=O)c2[nH]ccc12 GGOWFVIOGGPPEA-UHFFFAOYSA-N 0.000 claims 1
JHDMIUSVQCALAG-UHFFFAOYSA-N COc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound COc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 JHDMIUSVQCALAG-UHFFFAOYSA-N 0.000 claims 1
WUELFTQBLCPMIU-UHFFFAOYSA-N COc1cc(NC(=O)C=C)cc(c1)-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound COc1cc(NC(=O)C=C)cc(c1)-c1ccc(C(N)=O)c2[nH]ccc12 WUELFTQBLCPMIU-UHFFFAOYSA-N 0.000 claims 1
IOGLQKKXGAKEGJ-UHFFFAOYSA-N COc1cc(ccn1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C Chemical compound COc1cc(ccn1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C IOGLQKKXGAKEGJ-UHFFFAOYSA-N 0.000 claims 1
HKSJHOXOXPVLOO-UHFFFAOYSA-N COc1ccc(Cn2nccc2Nc2ccc(C(N)=O)c3[nH]c(cc23)-c2ccc(C)cc2)cc1 Chemical compound COc1ccc(Cn2nccc2Nc2ccc(C(N)=O)c3[nH]c(cc23)-c2ccc(C)cc2)cc1 HKSJHOXOXPVLOO-UHFFFAOYSA-N 0.000 claims 1
IMAIOVQQLXGNDW-UHFFFAOYSA-N COc1ccc(cc1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C Chemical compound COc1ccc(cc1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C IMAIOVQQLXGNDW-UHFFFAOYSA-N 0.000 claims 1
WOIOGRBVUFUYOF-UHFFFAOYSA-N COc1ccc(cc1NC(=O)C=C)-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound COc1ccc(cc1NC(=O)C=C)-c1ccc(C(N)=O)c2[nH]ccc12 WOIOGRBVUFUYOF-UHFFFAOYSA-N 0.000 claims 1
HWGSPKJTZXGOOP-UHFFFAOYSA-N COc1ccc(cn1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C Chemical compound COc1ccc(cn1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C HWGSPKJTZXGOOP-UHFFFAOYSA-N 0.000 claims 1
FRJRKUYHFNAYQL-UHFFFAOYSA-N COc1cccc(c1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C Chemical compound COc1cccc(c1)-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C FRJRKUYHFNAYQL-UHFFFAOYSA-N 0.000 claims 1
GUUVXYCMUSAQPF-UHFFFAOYSA-N COc1ccccc1-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C Chemical compound COc1ccccc1-c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(NC(=O)C=C)c1C GUUVXYCMUSAQPF-UHFFFAOYSA-N 0.000 claims 1
YFCFRCLLYGGNLJ-GOSISDBHSA-N CS(=O)(=O)N1CCC(=CC1)C1=CC2=C(C=CC(C(N)=O)=C2N1)N1CCC[C@H](C1)N1C=CN2C=CN=C2C1=O Chemical compound CS(=O)(=O)N1CCC(=CC1)C1=CC2=C(C=CC(C(N)=O)=C2N1)N1CCC[C@H](C1)N1C=CN2C=CN=C2C1=O YFCFRCLLYGGNLJ-GOSISDBHSA-N 0.000 claims 1
DDUWWGYASFWLNI-GOSISDBHSA-N CS(=O)(=O)N1CCC(=CC1)C1=CC2=C(C=CC(C(N)=O)=C2N1)N1CCC[C@H](C1)N1CCN2C=CN=C2C1=O Chemical compound CS(=O)(=O)N1CCC(=CC1)C1=CC2=C(C=CC(C(N)=O)=C2N1)N1CCC[C@H](C1)N1CCN2C=CN=C2C1=O DDUWWGYASFWLNI-GOSISDBHSA-N 0.000 claims 1
BIIVKMGRKQLVMK-UHFFFAOYSA-N CS(=O)(=O)N1CCC(=CC1)N1C=CC2=CC=CC(=C12)C(=O)N Chemical compound CS(=O)(=O)N1CCC(=CC1)N1C=CC2=CC=CC(=C12)C(=O)N BIIVKMGRKQLVMK-UHFFFAOYSA-N 0.000 claims 1
WTIXVORYKNPEOO-UHFFFAOYSA-N CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cc(NCc2nccs2)cc(NC(=O)C=C)c1 Chemical compound CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cc(NCc2nccs2)cc(NC(=O)C=C)c1 WTIXVORYKNPEOO-UHFFFAOYSA-N 0.000 claims 1
QLAZORZTICEREP-UHFFFAOYSA-N CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(Nc2ccnc(n2)C#N)c1 Chemical compound CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(Nc2ccnc(n2)C#N)c1 QLAZORZTICEREP-UHFFFAOYSA-N 0.000 claims 1
IFSQTRSCVPTOSJ-UHFFFAOYSA-N CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(OCc2nccs2)c1 Chemical compound CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)-c1cccc(OCc2nccs2)c1 IFSQTRSCVPTOSJ-UHFFFAOYSA-N 0.000 claims 1
HNJODAUPOKHQSE-UHFFFAOYSA-N CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)-c1ccccc1CNC(=O)C=C Chemical compound CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)-c1ccccc1CNC(=O)C=C HNJODAUPOKHQSE-UHFFFAOYSA-N 0.000 claims 1
ZSLLYFIIAGMTTJ-UHFFFAOYSA-N CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)-c1ccccc1NC(=O)C=C Chemical compound CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)-c1ccccc1NC(=O)C=C ZSLLYFIIAGMTTJ-UHFFFAOYSA-N 0.000 claims 1
ONVDQZWHZFZLGI-UHFFFAOYSA-N CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)-c1ccccc1NC(=O)CCl Chemical compound CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)-c1ccccc1NC(=O)CCl ONVDQZWHZFZLGI-UHFFFAOYSA-N 0.000 claims 1
HFKQZFPMNVBLOC-UHFFFAOYSA-N CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)N1CCCC(C1)NC(=O)c1nccs1 Chemical compound CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)N1CCCC(C1)NC(=O)c1nccs1 HFKQZFPMNVBLOC-UHFFFAOYSA-N 0.000 claims 1
HKIXWKQCUXSICT-GOSISDBHSA-N CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)N1CCC[C@H](C1)N1CCCCC1=O Chemical compound CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)N1CCC[C@H](C1)N1CCCCC1=O HKIXWKQCUXSICT-GOSISDBHSA-N 0.000 claims 1
ABFNOPRWVCHWBE-OAQYLSRUSA-N CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)N1CCC[C@H](C1)N1CCc2ccccc2C1=O Chemical compound CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)N1CCC[C@H](C1)N1CCc2ccccc2C1=O ABFNOPRWVCHWBE-OAQYLSRUSA-N 0.000 claims 1
FCUCKTBYENXLAO-UYAOXDASSA-N CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)N1CC[C@@H](O)[C@@H](C1)NC(=O)c1nccs1 Chemical compound CS(=O)(=O)N1CCC(=CC1)c1cc2c(ccc(C(N)=O)c2[nH]1)N1CC[C@@H](O)[C@@H](C1)NC(=O)c1nccs1 FCUCKTBYENXLAO-UYAOXDASSA-N 0.000 claims 1
GMQQEMQOHNQUIU-JTQLQIEISA-N C[C@@H](C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound C[C@@H](C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]ccc12 GMQQEMQOHNQUIU-JTQLQIEISA-N 0.000 claims 1
OSLBDILXKNQAHS-VIFPVBQESA-N C[C@@H](C1CN(C1)C(=O)C=C)c1ncc(C(N)=O)c2[nH]ccc12 Chemical compound C[C@@H](C1CN(C1)C(=O)C=C)c1ncc(C(N)=O)c2[nH]ccc12 OSLBDILXKNQAHS-VIFPVBQESA-N 0.000 claims 1
GMQQEMQOHNQUIU-SNVBAGLBSA-N C[C@H](C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound C[C@H](C1CN(C1)C(=O)C=C)c1ccc(C(N)=O)c2[nH]ccc12 GMQQEMQOHNQUIU-SNVBAGLBSA-N 0.000 claims 1
OSLBDILXKNQAHS-SECBINFHSA-N C[C@H](C1CN(C1)C(=O)C=C)c1ncc(C(N)=O)c2[nH]ccc12 Chemical compound C[C@H](C1CN(C1)C(=O)C=C)c1ncc(C(N)=O)c2[nH]ccc12 OSLBDILXKNQAHS-SECBINFHSA-N 0.000 claims 1
101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 claims 1
PAMCIOFZQONFLP-UHFFFAOYSA-N Cc1c(N)cccc1-c1cnc(C(N)=O)c2[nH]ccc12 Chemical compound Cc1c(N)cccc1-c1cnc(C(N)=O)c2[nH]ccc12 PAMCIOFZQONFLP-UHFFFAOYSA-N 0.000 claims 1
FCHNHFLFJUDERG-MDZDMXLPSA-N Cc1c(NC(=O)/C=C/C(=O)OC)cccc1-c1ccc(C(N)=O)c2[nH]c(C3=CCN(CC3)S(C)(=O)=O)cc12 Chemical compound Cc1c(NC(=O)/C=C/C(=O)OC)cccc1-c1ccc(C(N)=O)c2[nH]c(C3=CCN(CC3)S(C)(=O)=O)cc12 FCHNHFLFJUDERG-MDZDMXLPSA-N 0.000 claims 1
CRZXVCLYCZOPOY-ZHACJKMWSA-N Cc1c(NC(=O)/C=C/C(=O)OCC)cccc1-c1ccc(C(N)=O)c2[nH]c(C3=CCN(CC3)S(C)(=O)=O)cc12 Chemical compound Cc1c(NC(=O)/C=C/C(=O)OCC)cccc1-c1ccc(C(N)=O)c2[nH]c(C3=CCN(CC3)S(C)(=O)=O)cc12 CRZXVCLYCZOPOY-ZHACJKMWSA-N 0.000 claims 1
GYKJDKJHCSQGCR-MDZDMXLPSA-N Cc1c(NC(=O)/C=C/C(=O)OCC)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound Cc1c(NC(=O)/C=C/C(=O)OCC)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 GYKJDKJHCSQGCR-MDZDMXLPSA-N 0.000 claims 1
DAFWMMXCAZXMBH-JXMROGBWSA-N Cc1c(NC(=O)/C=C/C(C)C)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound Cc1c(NC(=O)/C=C/C(C)C)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 DAFWMMXCAZXMBH-JXMROGBWSA-N 0.000 claims 1
LQNFMKLPOIHUAO-GQCTYLIASA-N Cc1c(NC(=O)/C=C/C)cccc1-c1ccc(C(N)=O)c2[nH]c(C3=CCN(CC3)S(C)(=O)=O)cc12 Chemical compound Cc1c(NC(=O)/C=C/C)cccc1-c1ccc(C(N)=O)c2[nH]c(C3=CCN(CC3)S(C)(=O)=O)cc12 LQNFMKLPOIHUAO-GQCTYLIASA-N 0.000 claims 1
SBYKYFXJJBOEKP-HWKANZROSA-N Cc1c(NC(=O)/C=C/C)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound Cc1c(NC(=O)/C=C/C)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 SBYKYFXJJBOEKP-HWKANZROSA-N 0.000 claims 1
LIJAHMFNFPKEKD-VMPITWQZSA-N Cc1c(NC(=O)/C=C/CN(C)C)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound Cc1c(NC(=O)/C=C/CN(C)C)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 LIJAHMFNFPKEKD-VMPITWQZSA-N 0.000 claims 1
LMQNCNNIHKQOFF-QPJJXVBHSA-N Cc1c(NC(=O)/C=C/CNCCOC)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound Cc1c(NC(=O)/C=C/CNCCOC)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 LMQNCNNIHKQOFF-QPJJXVBHSA-N 0.000 claims 1
AZPCXLOTTDMLPE-REZTVBANSA-N Cc1c(NC(=O)C(/C)=C/CC)cccc1-c1ccc(C(N)=O)c2[nH]c(C3=CCN(CC3)S(C)(=O)=O)cc12 Chemical compound Cc1c(NC(=O)C(/C)=C/CC)cccc1-c1ccc(C(N)=O)c2[nH]c(C3=CCN(CC3)S(C)(=O)=O)cc12 AZPCXLOTTDMLPE-REZTVBANSA-N 0.000 claims 1
UQCJBFSAAHTSDT-UHFFFAOYSA-N Cc1c(NC(=O)C(F)(F)Cl)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)C(F)(F)Cl)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O UQCJBFSAAHTSDT-UHFFFAOYSA-N 0.000 claims 1
KUJCWVIEQWSNFO-BNCCVWRVSA-N Cc1c(NC(=O)C(\C)=C/C)cccc1-c1ccc(C(N)=O)c2[nH]c(C3=CCN(CC3)S(C)(=O)=O)cc12 Chemical compound Cc1c(NC(=O)C(\C)=C/C)cccc1-c1ccc(C(N)=O)c2[nH]c(C3=CCN(CC3)S(C)(=O)=O)cc12 KUJCWVIEQWSNFO-BNCCVWRVSA-N 0.000 claims 1
WBLYTXNMIKSUPA-UHFFFAOYSA-N Cc1c(NC(=O)C2=CCCC2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)C2=CCCC2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O WBLYTXNMIKSUPA-UHFFFAOYSA-N 0.000 claims 1
CFFDWPLWKRXSKX-UHFFFAOYSA-N Cc1c(NC(=O)C2=CCCCC2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)C2=CCCCC2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O CFFDWPLWKRXSKX-UHFFFAOYSA-N 0.000 claims 1
NNPFYQRHINSHPR-UHFFFAOYSA-N Cc1c(NC(=O)C2CCCCC2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)C2CCCCC2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O NNPFYQRHINSHPR-UHFFFAOYSA-N 0.000 claims 1
HWUKGKBGKPMXGG-UHFFFAOYSA-N Cc1c(NC(=O)C2CCOCC2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)C2CCOCC2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O HWUKGKBGKPMXGG-UHFFFAOYSA-N 0.000 claims 1
ZQQJATZYERCFPF-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(CN2CCOCC2)cc1 Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(CN2CCOCC2)cc1 ZQQJATZYERCFPF-UHFFFAOYSA-N 0.000 claims 1
HKTJNFJHFNFZDC-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(F)cc1 Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(F)cc1 HKTJNFJHFNFZDC-UHFFFAOYSA-N 0.000 claims 1
WRJNRHPBRBIMCT-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(cc1)C#N Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(cc1)C#N WRJNRHPBRBIMCT-UHFFFAOYSA-N 0.000 claims 1
BVKVWJBHAWKCRS-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(cc1)C(=O)N1CCCC1 Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(cc1)C(=O)N1CCCC1 BVKVWJBHAWKCRS-UHFFFAOYSA-N 0.000 claims 1
IXEINPQFWGGODG-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(cc1)C(=O)N1CCOCC1 Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(cc1)C(=O)N1CCOCC1 IXEINPQFWGGODG-UHFFFAOYSA-N 0.000 claims 1
OEVFVKCGDGRVEB-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(cc1)C(N)=O Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(cc1)C(N)=O OEVFVKCGDGRVEB-UHFFFAOYSA-N 0.000 claims 1
WXZZGTWRPAYESB-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(nc1)N1CCOCC1 Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(nc1)N1CCOCC1 WXZZGTWRPAYESB-UHFFFAOYSA-N 0.000 claims 1
YVPLIJIFPOCTRM-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc2OCCc2c1 Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc2OCCc2c1 YVPLIJIFPOCTRM-UHFFFAOYSA-N 0.000 claims 1
VYWBAOZNJXBKJR-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cccc(F)c1 Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cccc(F)c1 VYWBAOZNJXBKJR-UHFFFAOYSA-N 0.000 claims 1
GYJNMTQJNFJMLH-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cccc(c1)C#N Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cccc(c1)C#N GYJNMTQJNFJMLH-UHFFFAOYSA-N 0.000 claims 1
VHDUKPLNPHRVSN-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cccc(c1)C(N)=O Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cccc(c1)C(N)=O VHDUKPLNPHRVSN-UHFFFAOYSA-N 0.000 claims 1
NNNYJFPVGYYKJO-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccccc1 Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccccc1 NNNYJFPVGYYKJO-UHFFFAOYSA-N 0.000 claims 1
GMIFXZYGXOORIR-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccccc1F Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccccc1F GMIFXZYGXOORIR-UHFFFAOYSA-N 0.000 claims 1
VPYZMMAUEHCYKO-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccccc1S(C)(=O)=O Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccccc1S(C)(=O)=O VPYZMMAUEHCYKO-UHFFFAOYSA-N 0.000 claims 1
NCNWONLJFVNBTJ-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cccnc1 Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cccnc1 NCNWONLJFVNBTJ-UHFFFAOYSA-N 0.000 claims 1
KKTDMBARBZCGTO-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cccnc1F Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cccnc1F KKTDMBARBZCGTO-UHFFFAOYSA-N 0.000 claims 1
HZKIOPURNJHCMO-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccncc1 Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccncc1 HZKIOPURNJHCMO-UHFFFAOYSA-N 0.000 claims 1
SDOUSUDTGZHQIF-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cncnc1 Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cncnc1 SDOUSUDTGZHQIF-UHFFFAOYSA-N 0.000 claims 1
ABISGEILENTRHF-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cnn(CCN2CCOCC2)c1 Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cnn(CCN2CCOCC2)c1 ABISGEILENTRHF-UHFFFAOYSA-N 0.000 claims 1
XNYPZZORGISRKE-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCC(F)(F)CC1 Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCC(F)(F)CC1 XNYPZZORGISRKE-UHFFFAOYSA-N 0.000 claims 1
IDSMWPFVTYNYBE-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O IDSMWPFVTYNYBE-UHFFFAOYSA-N 0.000 claims 1
VCUVORGMNPBWLP-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 VCUVORGMNPBWLP-UHFFFAOYSA-N 0.000 claims 1
KNTQACBDFZPUAI-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1cnc(C(N)=O)c2[nH]ccc12 Chemical compound Cc1c(NC(=O)C=C)cccc1-c1cnc(C(N)=O)c2[nH]ccc12 KNTQACBDFZPUAI-UHFFFAOYSA-N 0.000 claims 1
WPFNZFRAJWFDBQ-UHFFFAOYSA-N Cc1c(NC(=O)C=C)cccc1-c1ncc(C(N)=O)c2[nH]ccc12 Chemical compound Cc1c(NC(=O)C=C)cccc1-c1ncc(C(N)=O)c2[nH]ccc12 WPFNZFRAJWFDBQ-UHFFFAOYSA-N 0.000 claims 1
KRTFWIGPHTZTGK-UHFFFAOYSA-N Cc1c(NC(=O)CC#N)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)CC#N)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O KRTFWIGPHTZTGK-UHFFFAOYSA-N 0.000 claims 1
JXORORQAIWDLFE-UHFFFAOYSA-N Cc1c(NC(=O)CCN2CCCC2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)CCN2CCCC2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O JXORORQAIWDLFE-UHFFFAOYSA-N 0.000 claims 1
DIRNHKSZAKHEQA-UHFFFAOYSA-N Cc1c(NC(=O)CCN2CCCC2)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound Cc1c(NC(=O)CCN2CCCC2)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 DIRNHKSZAKHEQA-UHFFFAOYSA-N 0.000 claims 1
DYANIUIJLWLJBU-UHFFFAOYSA-N Cc1c(NC(=O)CCN2CCCCC2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)CCN2CCCCC2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O DYANIUIJLWLJBU-UHFFFAOYSA-N 0.000 claims 1
OCHVPBKNFYRGKT-UHFFFAOYSA-N Cc1c(NC(=O)CCN2CCOCC2)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound Cc1c(NC(=O)CCN2CCOCC2)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 OCHVPBKNFYRGKT-UHFFFAOYSA-N 0.000 claims 1
NZDAGGSEHOPPBG-UHFFFAOYSA-N Cc1c(NC(=O)CF)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)CF)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O NZDAGGSEHOPPBG-UHFFFAOYSA-N 0.000 claims 1
XXNMXUFOUXMWOW-UHFFFAOYSA-N Cc1c(NC(=O)COc2ccc(F)cc2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)COc2ccc(F)cc2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O XXNMXUFOUXMWOW-UHFFFAOYSA-N 0.000 claims 1
QFTJOBWGFASQPI-UHFFFAOYSA-N Cc1c(NC(=O)COc2ccc(cc2)C#N)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)COc2ccc(cc2)C#N)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O QFTJOBWGFASQPI-UHFFFAOYSA-N 0.000 claims 1
WEZDWRNDISJZEE-UHFFFAOYSA-N Cc1c(NC(=O)COc2ccccc2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)COc2ccccc2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O WEZDWRNDISJZEE-UHFFFAOYSA-N 0.000 claims 1
WXNZZODLMFNGAW-UHFFFAOYSA-N Cc1c(NC(=O)COc2ccccn2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)COc2ccccn2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O WXNZZODLMFNGAW-UHFFFAOYSA-N 0.000 claims 1
NVOMWEQSOKZEGG-UHFFFAOYSA-N Cc1c(NC(=O)COc2cccnc2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)COc2cccnc2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O NVOMWEQSOKZEGG-UHFFFAOYSA-N 0.000 claims 1
RWZLIADCPQKFDV-UHFFFAOYSA-N Cc1c(NC(=O)COc2cccnn2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)COc2cccnn2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O RWZLIADCPQKFDV-UHFFFAOYSA-N 0.000 claims 1
KDNPGULZWGMNFO-KTKRTIGZSA-N Cc1c(NC(=O)\C=C/C(=O)NCC)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound Cc1c(NC(=O)\C=C/C(=O)NCC)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 KDNPGULZWGMNFO-KTKRTIGZSA-N 0.000 claims 1
IZMWRRVTBHSCIP-UHFFFAOYSA-N Cc1c(NC(=O)c2ccc(cc2)C(F)F)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cncnc1 Chemical compound Cc1c(NC(=O)c2ccc(cc2)C(F)F)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cncnc1 IZMWRRVTBHSCIP-UHFFFAOYSA-N 0.000 claims 1
UOLJFIHJIRWYNQ-UHFFFAOYSA-N Cc1c(NC(=O)c2ccc(cc2)C(F)F)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)c2ccc(cc2)C(F)F)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O UOLJFIHJIRWYNQ-UHFFFAOYSA-N 0.000 claims 1
XWFZDPTZWPUQHG-UHFFFAOYSA-N Cc1c(NC(=O)c2ccc(cc2)C(F)F)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound Cc1c(NC(=O)c2ccc(cc2)C(F)F)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 XWFZDPTZWPUQHG-UHFFFAOYSA-N 0.000 claims 1
DMNKXNXZJKNAJD-UHFFFAOYSA-N Cc1c(NC(=O)c2ccc(cc2)C2CC2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cncnc1 Chemical compound Cc1c(NC(=O)c2ccc(cc2)C2CC2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cncnc1 DMNKXNXZJKNAJD-UHFFFAOYSA-N 0.000 claims 1
REPAKHRVIRKAAQ-UHFFFAOYSA-N Cc1c(NC(=O)c2cccnc2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)c2cccnc2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O REPAKHRVIRKAAQ-UHFFFAOYSA-N 0.000 claims 1
QLZMSPIHINMENP-UHFFFAOYSA-N Cc1c(NC(=O)c2cnsc2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NC(=O)c2cnsc2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O QLZMSPIHINMENP-UHFFFAOYSA-N 0.000 claims 1
GYHOMRUVKPOPQG-UHFFFAOYSA-N Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(=O)n(C)c1 Chemical compound Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccc(=O)n(C)c1 GYHOMRUVKPOPQG-UHFFFAOYSA-N 0.000 claims 1
IILZYARQHIQTSF-UHFFFAOYSA-N Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccccc1CNC(=O)C#C Chemical compound Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccccc1CNC(=O)C#C IILZYARQHIQTSF-UHFFFAOYSA-N 0.000 claims 1
WPCKMHXUQFOUKH-UHFFFAOYSA-N Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccccc1CNC(=O)CC#N Chemical compound Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccccc1CNC(=O)CC#N WPCKMHXUQFOUKH-UHFFFAOYSA-N 0.000 claims 1
HWSHQIRKGWPDRF-UHFFFAOYSA-N Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccccc1CNC(=O)CCN1CCCCC1 Chemical compound Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccccc1CNC(=O)CCN1CCCCC1 HWSHQIRKGWPDRF-UHFFFAOYSA-N 0.000 claims 1
DJSLPTIFRSGIHG-UHFFFAOYSA-N Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccccc1CNC(=O)CCl Chemical compound Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccccc1CNC(=O)CCl DJSLPTIFRSGIHG-UHFFFAOYSA-N 0.000 claims 1
ITPDNVDAJJQZKL-UHFFFAOYSA-N Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccccc1CNC(=O)COc1ccc(F)cc1 Chemical compound Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccccc1CNC(=O)COc1ccc(F)cc1 ITPDNVDAJJQZKL-UHFFFAOYSA-N 0.000 claims 1
ZVJZHAYDXXCUQZ-UHFFFAOYSA-N Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccccc1CNC(=O)COc1ccccc1 Chemical compound Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1ccccc1CNC(=O)COc1ccccc1 ZVJZHAYDXXCUQZ-UHFFFAOYSA-N 0.000 claims 1
RVEPFVVEAZFKDW-UHFFFAOYSA-N Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]cc(NC(=O)C=C)c12 Chemical compound Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]cc(NC(=O)C=C)c12 RVEPFVVEAZFKDW-UHFFFAOYSA-N 0.000 claims 1
LHFKQYKLXFGFJW-UHFFFAOYSA-N Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]cc(NC(=O)CC#N)c12 Chemical compound Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]cc(NC(=O)CC#N)c12 LHFKQYKLXFGFJW-UHFFFAOYSA-N 0.000 claims 1
BAUJUCGDWMMZGI-UHFFFAOYSA-N Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]cc(NC(=O)CCl)c12 Chemical compound Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]cc(NC(=O)CCl)c12 BAUJUCGDWMMZGI-UHFFFAOYSA-N 0.000 claims 1
RCYDYQAACYUQKF-UHFFFAOYSA-N Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]cc(NC(=O)COc3ccc(F)cc3)c12 Chemical compound Cc1c(NC(=O)c2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]cc(NC(=O)COc3ccc(F)cc3)c12 RCYDYQAACYUQKF-UHFFFAOYSA-N 0.000 claims 1
VDZGMBDHKREWFJ-UHFFFAOYSA-N Cc1c(NC2COC2)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound Cc1c(NC2COC2)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 VDZGMBDHKREWFJ-UHFFFAOYSA-N 0.000 claims 1
ZTDPSWOWNCOUHW-UHFFFAOYSA-N Cc1c(NCc2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(NCc2nccs2)cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O ZTDPSWOWNCOUHW-UHFFFAOYSA-N 0.000 claims 1
OBTKNHAYGYXZJQ-UHFFFAOYSA-N Cc1c(cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O)N(C1COC1)C(=O)c1ccc(cc1)C(F)F Chemical compound Cc1c(cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O)N(C1COC1)C(=O)c1ccc(cc1)C(F)F OBTKNHAYGYXZJQ-UHFFFAOYSA-N 0.000 claims 1
YFCBQZAUWLZJCR-UHFFFAOYSA-N Cc1c(cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O)N(CCO)C(=O)c1ccc(cc1)C(F)F Chemical compound Cc1c(cccc1-c1ccc(C(N)=O)c2[nH]c(cc12)C1=CCN(CC1)S(C)(=O)=O)N(CCO)C(=O)c1ccc(cc1)C(F)F YFCBQZAUWLZJCR-UHFFFAOYSA-N 0.000 claims 1
MPQURSHQOOFQTH-UHFFFAOYSA-N Cc1c(cccc1-n1cnc2ccc(F)cc2c1=O)-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cnn(CC(C)(C)O)c1 Chemical compound Cc1c(cccc1-n1cnc2ccc(F)cc2c1=O)-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cnn(CC(C)(C)O)c1 MPQURSHQOOFQTH-UHFFFAOYSA-N 0.000 claims 1
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LYKNNXLYWLCCHP-JTQLQIEISA-N NC(=O)c1ncc([C@H]2CCCN(C2)C(=O)C=C)c2cc[nH]c12 Chemical compound NC(=O)c1ncc([C@H]2CCCN(C2)C(=O)C=C)c2cc[nH]c12 LYKNNXLYWLCCHP-JTQLQIEISA-N 0.000 claims 1
OMMLAJVPCFBZEB-MRXNPFEDSA-N O=c1n(cnc2ccccc12)[C@@H]1CCCN(C1)c1ccc(C#N)c2[nH]ccc12 Chemical compound O=c1n(cnc2ccccc12)[C@@H]1CCCN(C1)c1ccc(C#N)c2[nH]ccc12 OMMLAJVPCFBZEB-MRXNPFEDSA-N 0.000 claims 1
SHUSUQPIERAYMB-UHFFFAOYSA-N OC(=O)C(F)(F)F.Cc1ccc(NC(=O)c2nccs2)cc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cccnc1 Chemical compound OC(=O)C(F)(F)F.Cc1ccc(NC(=O)c2nccs2)cc1-c1ccc(C(N)=O)c2[nH]c(cc12)-c1cccnc1 SHUSUQPIERAYMB-UHFFFAOYSA-N 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
125000002947 alkylene group Chemical group 0.000 claims 1
125000003118 aryl group Chemical class 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
AZXVKUOVSDKCDL-HWKANZROSA-N c12c(NC(=O)/C=C/C)c[nH]c2c(C(N)=O)ccc1-c(c1C)cccc1NC(=O)c1nccs1 Chemical compound c12c(NC(=O)/C=C/C)c[nH]c2c(C(N)=O)ccc1-c(c1C)cccc1NC(=O)c1nccs1 AZXVKUOVSDKCDL-HWKANZROSA-N 0.000 claims 1
ZPUYIGVBIQQFEH-CMDGGOBGSA-N c12cc[nH]c2c(C(=O)N)ccc1-c(c1)cccc1NC(=O)\C=C\C(=O)NC1CC1 Chemical compound c12cc[nH]c2c(C(=O)N)ccc1-c(c1)cccc1NC(=O)\C=C\C(=O)NC1CC1 ZPUYIGVBIQQFEH-CMDGGOBGSA-N 0.000 claims 1
CODIZNOXFRTDRA-VOTSOKGWSA-N c12cc[nH]c2c(C(=O)N)ccc1-c1cccc(NC(=O)\C=C\C(O)=O)c1 Chemical compound c12cc[nH]c2c(C(=O)N)ccc1-c1cccc(NC(=O)\C=C\C(O)=O)c1 CODIZNOXFRTDRA-VOTSOKGWSA-N 0.000 claims 1
DOEYZMWJROCHCV-CMDGGOBGSA-N c1c(NC(=O)/C=C/C(=O)N(C)C)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound c1c(NC(=O)/C=C/C(=O)N(C)C)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 DOEYZMWJROCHCV-CMDGGOBGSA-N 0.000 claims 1
KRCUBNJEJLWTCB-BQYQJAHWSA-N c1c(NC(=O)/C=C/C(=O)NC)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound c1c(NC(=O)/C=C/C(=O)NC)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 KRCUBNJEJLWTCB-BQYQJAHWSA-N 0.000 claims 1
WICOVEUSTXTCIO-CMDGGOBGSA-N c1c(NC(=O)/C=C/C(=O)NCC)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound c1c(NC(=O)/C=C/C(=O)NCC)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 WICOVEUSTXTCIO-CMDGGOBGSA-N 0.000 claims 1
OQKNTRVBYNSMLX-BQYQJAHWSA-N c1c(NC(=O)/C=C/C(=O)OC)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound c1c(NC(=O)/C=C/C(=O)OC)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 OQKNTRVBYNSMLX-BQYQJAHWSA-N 0.000 claims 1
CVXUTPCLBCSIBK-GZTJUZNOSA-N c1c(NC(=O)C(\C#N)=C(O)/C)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound c1c(NC(=O)C(\C#N)=C(O)/C)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 CVXUTPCLBCSIBK-GZTJUZNOSA-N 0.000 claims 1
WICOVEUSTXTCIO-HJWRWDBZSA-N c1c(NC(=O)\C=C/C(=O)NCC)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 Chemical compound c1c(NC(=O)\C=C/C(=O)NCC)cccc1-c1ccc(C(N)=O)c2[nH]ccc12 WICOVEUSTXTCIO-HJWRWDBZSA-N 0.000 claims 1
CZYQYHWZNJLRCR-RMKNXTFCSA-N c1ccc(-c2ccc(C(N)=O)c3[nH]ccc32)c(C)c1NC(=O)\C=C\CN1CCCCC1 Chemical compound c1ccc(-c2ccc(C(N)=O)c3[nH]ccc32)c(C)c1NC(=O)\C=C\CN1CCCCC1 CZYQYHWZNJLRCR-RMKNXTFCSA-N 0.000 claims 1
CJJAZCRMLPKAFX-ZZXKWVIFSA-N c1ccc(-c2ccc(C(N)=O)c3[nH]ccc32)c(C)c1NC(=O)\C=C\CN1CCOCC1 Chemical compound c1ccc(-c2ccc(C(N)=O)c3[nH]ccc32)c(C)c1NC(=O)\C=C\CN1CCOCC1 CJJAZCRMLPKAFX-ZZXKWVIFSA-N 0.000 claims 1
SOTXLFILRPVJDX-ZZXKWVIFSA-N c1ccc(-c2ccc(C(N)=O)c3[nH]ccc32)c(C)c1NC(=O)\C=C\CNC1CC1 Chemical compound c1ccc(-c2ccc(C(N)=O)c3[nH]ccc32)c(C)c1NC(=O)\C=C\CNC1CC1 SOTXLFILRPVJDX-ZZXKWVIFSA-N 0.000 claims 1
125000002837 carbocyclic group Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 1
208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 1
125000000392 cycloalkenyl group Chemical group 0.000 claims 1
XRLDSWLMHUQECH-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1CCCC1 XRLDSWLMHUQECH-UHFFFAOYSA-N 0.000 claims 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 1
125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
TZLIBLHVVKQINP-UHFFFAOYSA-N ethyl 3-[7-carbamoyl-4-[2-methyl-3-(4-oxoquinazolin-3-yl)phenyl]-1h-indol-2-yl]-2,5-dihydropyrrole-1-carboxylate Chemical compound C1N(C(=O)OCC)CC=C1C1=CC2=C(C=3C(=C(C=CC=3)N3C(C4=CC=CC=C4N=C3)=O)C)C=CC(C(N)=O)=C2N1 TZLIBLHVVKQINP-UHFFFAOYSA-N 0.000 claims 1
125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
208000032839 leukemia Diseases 0.000 claims 1
210000004698 lymphocyte Anatomy 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
201000000050 myeloid neoplasm Diseases 0.000 claims 1
PBSASXNAZJHOBR-UHFFFAOYSA-N n-(2-methylpropyl)prop-2-enamide Chemical compound CC(C)CNC(=O)C=C PBSASXNAZJHOBR-UHFFFAOYSA-N 0.000 claims 1
PIFXWGQXXICDFZ-UHFFFAOYSA-N n-(cyclopentylmethyl)prop-2-enamide Chemical compound C=CC(=O)NCC1CCCC1 PIFXWGQXXICDFZ-UHFFFAOYSA-N 0.000 claims 1
KLTDYNBFGKZXEA-GFCCVEGCSA-N n-[(3r)-1-(7-carbamoyl-1h-indol-4-yl)piperidin-3-yl]-2-methyl-1,3-oxazole-4-carboxamide Chemical compound O1C(C)=NC(C(=O)N[C@H]2CN(CCC2)C=2C=3C=CNC=3C(C(N)=O)=CC=2)=C1 KLTDYNBFGKZXEA-GFCCVEGCSA-N 0.000 claims 1
ITXNGEZJCOLBOO-UHFFFAOYSA-N n-[3-(7-carbamoyl-2-pyridin-3-yl-1h-indol-4-yl)-2-methylphenyl]-1,3-thiazole-2-carboxamide Chemical compound C1=CC=C(C=2C=3C=C(NC=3C(C(N)=O)=CC=2)C=2C=NC=CC=2)C(C)=C1NC(=O)C1=NC=CS1 ITXNGEZJCOLBOO-UHFFFAOYSA-N 0.000 claims 1
WQKZHQLBYCESRO-UHFFFAOYSA-N n-[3-[7-carbamoyl-2-(1-methylpyrazol-4-yl)-1h-indol-4-yl]-2-(hydroxymethyl)phenyl]-1,3-thiazole-2-carboxamide Chemical compound C1=NN(C)C=C1C1=CC2=C(C=3C(=C(NC(=O)C=4SC=CN=4)C=CC=3)CO)C=CC(C(N)=O)=C2N1 WQKZHQLBYCESRO-UHFFFAOYSA-N 0.000 claims 1
ITIKAAFLZHDMSQ-UHFFFAOYSA-N n-[3-[7-carbamoyl-2-(1-methylpyrazol-4-yl)-1h-indol-4-yl]-2-methylphenyl]-1,3-thiazole-2-carboxamide Chemical compound C1=CC=C(C=2C=3C=C(NC=3C(C(N)=O)=CC=2)C2=CN(C)N=C2)C(C)=C1NC(=O)C1=NC=CS1 ITIKAAFLZHDMSQ-UHFFFAOYSA-N 0.000 claims 1
AASFPRBEMWDUEL-UHFFFAOYSA-N n-[3-[7-carbamoyl-2-(1-methylpyrazol-4-yl)-1h-indol-4-yl]-2-methylphenyl]-n-methyl-1,3-thiazole-2-carboxamide Chemical compound C=1C=CC(C=2C=3C=C(NC=3C(C(N)=O)=CC=2)C2=CN(C)N=C2)=C(C)C=1N(C)C(=O)C1=NC=CS1 AASFPRBEMWDUEL-UHFFFAOYSA-N 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
125000002971 oxazolyl group Chemical group 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
125000002098 pyridazinyl group Chemical group 0.000 claims 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1

JP2016524175A 2013-06-26 2014-06-26 Ｂｔｋ阻害薬としての一級カルボキサミド類 Active JP6509838B2 (ja)