CA2846663A1 - Antibacterial compounds and methods for use - Google Patents

Info

Publication number

CA2846663A1

CA2846663A1 CA2846663A CA2846663A CA2846663A1 CA 2846663 A1 CA2846663 A1 CA 2846663A1 CA 2846663 A CA2846663 A CA 2846663A CA 2846663 A CA2846663 A CA 2846663A CA 2846663 A1 CA2846663 A1 CA 2846663A1

Authority

CA

Canada

Prior art keywords

methyl

oxo

dihydropyridine

carboxylic acid

ethyl

Prior art date

2011-08-29

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

• 150000001875 compounds Chemical class 0.000 title claims abstract description 408
• 238000000034 method Methods 0.000 title claims abstract description 282
• 230000000844 anti-bacterial effect Effects 0.000 title description 15
• 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 56
• 208000035143 Bacterial infection Diseases 0.000 claims abstract description 50
• 239000003814 drug Substances 0.000 claims abstract description 28
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
• 229940079593 drug Drugs 0.000 claims abstract description 18
• -1 carboxy, amino Chemical group 0.000 claims description 667
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 251
• 125000003118 aryl group Chemical group 0.000 claims description 133
• 125000000623 heterocyclic group Chemical group 0.000 claims description 96
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 95
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 93
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 70
• 125000001072 heteroaryl group Chemical group 0.000 claims description 63
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
• 125000001424 substituent group Chemical group 0.000 claims description 49
• 125000000217 alkyl group Chemical group 0.000 claims description 48
• 150000003839 salts Chemical class 0.000 claims description 34
• 239000002253 acid Substances 0.000 claims description 31
• 229910052739 hydrogen Inorganic materials 0.000 claims description 31
• 239000003795 chemical substances by application Substances 0.000 claims description 26
• 241000894006 Bacteria Species 0.000 claims description 23
• 239000012453 solvate Substances 0.000 claims description 23
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 239000003242 anti bacterial agent Substances 0.000 claims description 20
• 150000002367 halogens Chemical group 0.000 claims description 20
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 19
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 17
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• 239000001257 hydrogen Substances 0.000 claims description 15
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 15
• 125000001769 aryl amino group Chemical group 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
• 230000001580 bacterial effect Effects 0.000 claims description 13
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
• MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 12
• 125000003386 piperidinyl group Chemical group 0.000 claims description 12
• 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 11
• JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 11
• 125000005960 1,4-diazepanyl group Chemical group 0.000 claims description 11
• 125000003282 alkyl amino group Chemical group 0.000 claims description 11
• 125000002393 azetidinyl group Chemical group 0.000 claims description 11
• 125000002619 bicyclic group Chemical group 0.000 claims description 11
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• 125000002757 morpholinyl group Chemical group 0.000 claims description 11
• 125000004193 piperazinyl group Chemical group 0.000 claims description 11
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 11
• 241000588724 Escherichia coli Species 0.000 claims description 10
• 241000192125 Firmicutes Species 0.000 claims description 10
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 10
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 10
• 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 description 9
• 229940023064 escherichia coli Drugs 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 8
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• 241000425347 Phyla <beetle> Species 0.000 claims description 8
• 230000003115 biocidal effect Effects 0.000 claims description 8
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 8
• 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 8
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 7
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
• 239000012458 free base Substances 0.000 claims description 7
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
• 125000004043 oxo group Chemical group O=* 0.000 claims description 7
• 125000005983 2,5-diazabicyclo[2.2.1]heptan-2-yl group Chemical group 0.000 claims description 6
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 241000194032 Enterococcus faecalis Species 0.000 claims description 6
• 241000191967 Staphylococcus aureus Species 0.000 claims description 6
• 229960003405 ciprofloxacin Drugs 0.000 claims description 6
• 229940032049 enterococcus faecalis Drugs 0.000 claims description 6
• 125000002883 imidazolyl group Chemical group 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
• 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 5
• FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 claims description 5
• 125000005241 heteroarylamino group Chemical group 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 241000588626 Acinetobacter baumannii Species 0.000 claims description 4
• 241001156739 Actinobacteria <phylum> Species 0.000 claims description 4
• 241000193738 Bacillus anthracis Species 0.000 claims description 4
• 241001185363 Chlamydiae Species 0.000 claims description 4
• 241000588747 Klebsiella pneumoniae Species 0.000 claims description 4
• 241000192142 Proteobacteria Species 0.000 claims description 4
• 241001180364 Spirochaetes Species 0.000 claims description 4
• 229940065181 bacillus anthracis Drugs 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 238000002648 combination therapy Methods 0.000 claims description 4
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 229940045505 klebsiella pneumoniae Drugs 0.000 claims description 4
• 229960003702 moxifloxacin Drugs 0.000 claims description 4
• FABPRXSRWADJSP-MEDUHNTESA-N moxifloxacin Chemical compound COC1=C(N2C[C@H]3NCCC[C@H]3C2)C(F)=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 FABPRXSRWADJSP-MEDUHNTESA-N 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 241000894007 species Species 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 3
• 244000063299 Bacillus subtilis Species 0.000 claims description 3
• 235000014469 Bacillus subtilis Nutrition 0.000 claims description 3
• 241000194031 Enterococcus faecium Species 0.000 claims description 3
• 241000589602 Francisella tularensis Species 0.000 claims description 3
• 241000606768 Haemophilus influenzae Species 0.000 claims description 3
• GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 claims description 3
• 241000588655 Moraxella catarrhalis Species 0.000 claims description 3
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 3
• 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 3
• 241000193998 Streptococcus pneumoniae Species 0.000 claims description 3
• 241000607479 Yersinia pestis Species 0.000 claims description 3
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 3
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 3
• 229940118764 francisella tularensis Drugs 0.000 claims description 3
• 229940047650 haemophilus influenzae Drugs 0.000 claims description 3
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 3
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 3
• 125000001041 indolyl group Chemical group 0.000 claims description 3
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 3
• 229960003376 levofloxacin Drugs 0.000 claims description 3
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
• 229940031000 streptococcus pneumoniae Drugs 0.000 claims description 3
• 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 2
• 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims description 2
• 125000005955 1H-indazolyl group Chemical group 0.000 claims description 2
• 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 2
• 241000580482 Acidobacteria Species 0.000 claims description 2
• 241001142141 Aquificae <phylum> Species 0.000 claims description 2
• 241000605059 Bacteroidetes Species 0.000 claims description 2
• 241000949049 Caldiserica Species 0.000 claims description 2
• 241000191368 Chlorobi Species 0.000 claims description 2
• 241001142109 Chloroflexi Species 0.000 claims description 2
• 241001143290 Chrysiogenetes <phylum> Species 0.000 claims description 2
• 241000192700 Cyanobacteria Species 0.000 claims description 2
• 241001143296 Deferribacteres <phylum> Species 0.000 claims description 2
• 241000192095 Deinococcus-Thermus Species 0.000 claims description 2
• 241000970811 Dictyoglomi Species 0.000 claims description 2
• 241001260322 Elusimicrobia <phylum> Species 0.000 claims description 2
• 241000588914 Enterobacter Species 0.000 claims description 2
• 241000923108 Fibrobacteres Species 0.000 claims description 2
• 241001453172 Fusobacteria Species 0.000 claims description 2
• 241001265526 Gemmatimonadetes <phylum> Species 0.000 claims description 2
• 241001387859 Lentisphaerae Species 0.000 claims description 2
• RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 claims description 2
• 241000187479 Mycobacterium tuberculosis Species 0.000 claims description 2
• 241000588653 Neisseria Species 0.000 claims description 2
• 241000192121 Nitrospira <genus> Species 0.000 claims description 2
• 241001180199 Planctomycetes Species 0.000 claims description 2
• 241000607768 Shigella Species 0.000 claims description 2
• 241000193996 Streptococcus pyogenes Species 0.000 claims description 2
• 241000390529 Synergistetes Species 0.000 claims description 2
• 241000131694 Tenericutes Species 0.000 claims description 2
• 239000004098 Tetracycline Substances 0.000 claims description 2
• 241001143138 Thermodesulfobacteria <phylum> Species 0.000 claims description 2
• 241001141092 Thermomicrobia Species 0.000 claims description 2
• 241001143310 Thermotogae <phylum> Species 0.000 claims description 2
• 241001261005 Verrucomicrobia Species 0.000 claims description 2
• 229960003907 linezolid Drugs 0.000 claims description 2
• TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 claims description 2
• 229960003085 meticillin Drugs 0.000 claims description 2
• 229960000210 nalidixic acid Drugs 0.000 claims description 2
• MHWLWQUZZRMNGJ-UHFFFAOYSA-N nalidixic acid Chemical compound C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 claims description 2
• 235000019364 tetracycline Nutrition 0.000 claims description 2
• 150000003522 tetracyclines Chemical class 0.000 claims description 2
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 2
• 229960004089 tigecycline Drugs 0.000 claims description 2
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 107
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
• ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims 2
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 2
• AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 claims 2
• 229960001225 rifampicin Drugs 0.000 claims 2
• JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 claims 2
• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims 2
• VCOPTHOUUNAYKQ-WBTCAYNUSA-N (3s)-3,6-diamino-n-[[(2s,5s,8e,11s,15s)-15-amino-11-[(6r)-2-amino-1,4,5,6-tetrahydropyrimidin-6-yl]-8-[(carbamoylamino)methylidene]-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentazacyclohexadec-5-yl]methyl]hexanamide;(3s)-3,6-diamino-n-[[(2s,5s,8 Chemical compound N1C(=O)\C(=C/NC(N)=O)NC(=O)[C@H](CNC(=O)C[C@@H](N)CCCN)NC(=O)[C@H](C)NC(=O)[C@@H](N)CNC(=O)[C@@H]1[C@@H]1NC(N)=NCC1.N1C(=O)\C(=C/NC(N)=O)NC(=O)[C@H](CNC(=O)C[C@@H](N)CCCN)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CNC(=O)[C@@H]1[C@@H]1NC(N)=NCC1 VCOPTHOUUNAYKQ-WBTCAYNUSA-N 0.000 claims 1
• SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 claims 1
• FFTVPQUHLQBXQZ-KVUCHLLUSA-N (4s,4as,5ar,12ar)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=C(N(C)C)C=CC(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O FFTVPQUHLQBXQZ-KVUCHLLUSA-N 0.000 claims 1
• SOVUOXKZCCAWOJ-HJYUBDRYSA-N (4s,4as,5ar,12ar)-9-[[2-(tert-butylamino)acetyl]amino]-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=C(N(C)C)C=C(NC(=O)CNC(C)(C)C)C(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O SOVUOXKZCCAWOJ-HJYUBDRYSA-N 0.000 claims 1
• WDLWHQDACQUCJR-ZAMMOSSLSA-N (6r,7r)-7-[[(2r)-2-azaniumyl-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(e)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)/C=C/C)C(O)=O)=CC=C(O)C=C1 WDLWHQDACQUCJR-ZAMMOSSLSA-N 0.000 claims 1
• MINDHVHHQZYEEK-UHFFFAOYSA-N (E)-(2S,3R,4R,5S)-5-[(2S,3S,4S,5S)-2,3-epoxy-5-hydroxy-4-methylhexyl]tetrahydro-3,4-dihydroxy-(beta)-methyl-2H-pyran-2-crotonic acid ester with 9-hydroxynonanoic acid Natural products CC(O)C(C)C1OC1CC1C(O)C(O)C(CC(C)=CC(=O)OCCCCCCCCC(O)=O)OC1 MINDHVHHQZYEEK-UHFFFAOYSA-N 0.000 claims 1
• RXZBMPWDPOLZGW-XMRMVWPWSA-N (E)-roxithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N/OCOCCOC)/[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 RXZBMPWDPOLZGW-XMRMVWPWSA-N 0.000 claims 1
• XUBOMFCQGDBHNK-JTQLQIEISA-N (S)-gatifloxacin Chemical compound FC1=CC(C(C(C(O)=O)=CN2C3CC3)=O)=C2C(OC)=C1N1CCN[C@@H](C)C1 XUBOMFCQGDBHNK-JTQLQIEISA-N 0.000 claims 1
• KTCNGKASVZVXHT-UHFFFAOYSA-N 1,2-dihydropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CNC1 KTCNGKASVZVXHT-UHFFFAOYSA-N 0.000 claims 1
• FQDFQKZAUOUNCX-UHFFFAOYSA-N 4-amino-5-ethyl-6-[1-methyl-2-(piperidin-1-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound NC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCCCC4)N(C)C3=CC=2)=C1CC FQDFQKZAUOUNCX-UHFFFAOYSA-N 0.000 claims 1
• SATRPQGGTSUTTN-UHFFFAOYSA-N 4-amino-5-ethyl-6-[1-methyl-2-(pyrrolidin-1-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound NC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCCC4)N(C)C3=CC=2)=C1CC SATRPQGGTSUTTN-UHFFFAOYSA-N 0.000 claims 1
• IPKCJQVTRFILHT-UHFFFAOYSA-N 4-amino-6-[2-[(dimethylamino)methyl]-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound NC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN(C)C)N(C)C3=CC=2)=C1CC IPKCJQVTRFILHT-UHFFFAOYSA-N 0.000 claims 1
• FIVCBTRDINJPOE-UHFFFAOYSA-N 4-amino-6-[2-[[3-(dimethylamino)pyrrolidin-1-yl]methyl]-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound NC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC(CC4)N(C)C)N(C)C3=CC=2)=C1CC FIVCBTRDINJPOE-UHFFFAOYSA-N 0.000 claims 1
• FTGXXRUPIMDVJD-UHFFFAOYSA-N 4-hydroxy-5-methyl-6-[1-methyl-2-(methylaminomethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CNC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1C FTGXXRUPIMDVJD-UHFFFAOYSA-N 0.000 claims 1
• WXVISNMNNXAHQL-UHFFFAOYSA-N 4-hydroxy-5-methyl-6-[1-methyl-2-(propylaminomethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CNCCC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1C WXVISNMNNXAHQL-UHFFFAOYSA-N 0.000 claims 1
• FNFLQJZGEBXICH-UHFFFAOYSA-N 4-hydroxy-5-methyl-6-[1-methyl-2-(pyrrolidin-1-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCCC4)N(C)C3=CC=2)=C1C FNFLQJZGEBXICH-UHFFFAOYSA-N 0.000 claims 1
• SCNGQLHCLOXMTD-UHFFFAOYSA-N 4-hydroxy-5-methyl-6-[1-methyl-2-[(2-methylpropylamino)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CNCC(C)C)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1C SCNGQLHCLOXMTD-UHFFFAOYSA-N 0.000 claims 1
• QUQNGMHROUXRSE-UHFFFAOYSA-N 4-hydroxy-5-methyl-6-[1-methyl-2-[(propan-2-ylamino)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CNC(C)C)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1C QUQNGMHROUXRSE-UHFFFAOYSA-N 0.000 claims 1
• HATXFGAJOZUHQS-UHFFFAOYSA-N 4-hydroxy-5-methyl-6-[1-methyl-2-[[(1-methylcyclopropyl)amino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC4(C)CC4)N(C)C3=CC=2)=C1C HATXFGAJOZUHQS-UHFFFAOYSA-N 0.000 claims 1
• NMWMFAPJNQFETL-UHFFFAOYSA-N 4-hydroxy-5-methyl-6-[1-methyl-2-[[2-(methylamino)ethylamino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CNCCNC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1C NMWMFAPJNQFETL-UHFFFAOYSA-N 0.000 claims 1
• YRWJBALESWCGOH-UHFFFAOYSA-N 4-hydroxy-5-methyl-6-[2-(methylamino)-2,3-dihydro-1h-pyrrolo[1,2-a]indol-6-yl]-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.C=1C=C2N3CC(NC)CC3=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1C YRWJBALESWCGOH-UHFFFAOYSA-N 0.000 claims 1
• BTANIZOGABTGIT-UHFFFAOYSA-N 4-hydroxy-6-[1-methyl-2-(pyrrolidin-1-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C2=CC(C=3NC(=O)C(C(O)=O)=C(O)C=3)=CC=C2N(C)C=1CN1CCCC1 BTANIZOGABTGIT-UHFFFAOYSA-N 0.000 claims 1
• BYYCMAWRMANRBZ-UHFFFAOYSA-N 4-hydroxy-6-[2-[(1-hydroxypropan-2-ylamino)methyl]-1-methylindol-5-yl]-5-methyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CNC(CO)C)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1C BYYCMAWRMANRBZ-UHFFFAOYSA-N 0.000 claims 1
• JTXPUBUZMHWGDQ-UHFFFAOYSA-N 4-hydroxy-6-[2-[(1-methoxypropan-2-ylamino)methyl]-1-methylindol-5-yl]-5-methyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CNC(C)COC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1C JTXPUBUZMHWGDQ-UHFFFAOYSA-N 0.000 claims 1
• JXNQVMYQHQMVGX-UHFFFAOYSA-N 4-hydroxy-6-[2-[(2-hydroxyethylamino)methyl]-1-methylindol-5-yl]-5-methyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCCO)N(C)C3=CC=2)=C1C JXNQVMYQHQMVGX-UHFFFAOYSA-N 0.000 claims 1
• UBZFXIJEEZBMGO-UHFFFAOYSA-N 4-hydroxy-6-[2-[(2-methoxyethylamino)methyl]-1-methylindol-5-yl]-5-methyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CNCCOC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1C UBZFXIJEEZBMGO-UHFFFAOYSA-N 0.000 claims 1
• RHJLYVURYCGACM-UHFFFAOYSA-N 5-(4-fluorophenyl)-4-hydroxy-6-[1-methyl-2-(pyrrolidin-1-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C2=CC(C3=C(C(O)=C(C(O)=O)C(=O)N3)C=3C=CC(F)=CC=3)=CC=C2N(C)C=1CN1CCCC1 RHJLYVURYCGACM-UHFFFAOYSA-N 0.000 claims 1
• RBNAHFFWGQCLNT-UHFFFAOYSA-N 5-cyclopropyl-4-hydroxy-6-[1-methyl-2-(pyrrolidin-1-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C2=CC(C3=C(C(O)=C(C(O)=O)C(=O)N3)C3CC3)=CC=C2N(C)C=1CN1CCCC1 RBNAHFFWGQCLNT-UHFFFAOYSA-N 0.000 claims 1
• OUKZYCNCWPXGSI-UHFFFAOYSA-N 5-cyclopropyl-6-[2-[(cyclopropylmethylamino)methyl]-1-methylindol-5-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C2=CC(C3=C(C(O)=C(C(O)=O)C(=O)N3)C3CC3)=CC=C2N(C)C=1CNCC1CC1 OUKZYCNCWPXGSI-UHFFFAOYSA-N 0.000 claims 1
• DXYYDYSKZKOKMB-UHFFFAOYSA-N 5-cyclopropyl-6-[2-[(dimethylamino)methyl]-1-methylindol-5-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CN(C)C)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1C1CC1 DXYYDYSKZKOKMB-UHFFFAOYSA-N 0.000 claims 1
• JABFIMDLCCNBTE-UHFFFAOYSA-N 5-ethyl-2-oxo-6-(3-piperidin-1-yl-2,3-dihydro-1h-pyrrolo[1,2-a]indol-6-yl)-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C4C(N5CCCCC5)CCN4C3=CC=2)=C1CC JABFIMDLCCNBTE-UHFFFAOYSA-N 0.000 claims 1
• RDJGLYWHBFOAOD-UHFFFAOYSA-N 5-ethyl-2-oxo-6-(3-pyrrolidin-1-yl-2,3-dihydro-1h-pyrrolo[1,2-a]indol-6-yl)-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C4C(N5CCCC5)CCN4C3=CC=2)=C1CC RDJGLYWHBFOAOD-UHFFFAOYSA-N 0.000 claims 1
• ZWKFHHKWLLJPAH-UHFFFAOYSA-N 5-ethyl-2-oxo-6-[2-(piperidin-1-ylmethyl)imidazo[1,2-a]pyridin-6-yl]-1h-pyridine-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.C1=C(C(O)=O)C(=O)NC(C2=CN3C=C(CN4CCCCC4)N=C3C=C2)=C1CC ZWKFHHKWLLJPAH-UHFFFAOYSA-N 0.000 claims 1
• UVPZLKUCGQCIEJ-UHFFFAOYSA-N 5-ethyl-2-oxo-6-[2-(pyrrolidin-1-ylmethyl)imidazo[1,2-a]pyridin-6-yl]-1h-pyridine-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.C1=C(C(O)=O)C(=O)NC(C2=CN3C=C(CN4CCCC4)N=C3C=C2)=C1CC UVPZLKUCGQCIEJ-UHFFFAOYSA-N 0.000 claims 1
• QEQPWJGMKDRPTF-UHFFFAOYSA-N 5-ethyl-4-hydroxy-2-oxo-6-(1-phenylindol-5-yl)-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=CN(C3=CC=2)C=2C=CC=CC=2)=C1CC QEQPWJGMKDRPTF-UHFFFAOYSA-N 0.000 claims 1
• QCEPOEQDZQQZOX-UHFFFAOYSA-N 5-ethyl-4-hydroxy-2-oxo-6-(2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indol-7-yl)-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3NC=4CCNCC=4C3=CC=2)=C1CC QCEPOEQDZQQZOX-UHFFFAOYSA-N 0.000 claims 1
• CPQNNOBVQXDKPH-UHFFFAOYSA-N 5-ethyl-4-hydroxy-2-oxo-6-(2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indol-7-yl)-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3NC=4CNCCC=4C3=CC=2)=C1CC CPQNNOBVQXDKPH-UHFFFAOYSA-N 0.000 claims 1
• OABGFPOPKDCDKU-UHFFFAOYSA-N 5-ethyl-4-hydroxy-2-oxo-6-(2-propan-2-yl-1,3,4,9-tetrahydropyrido[3,4-b]indol-7-yl)-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3NC=4CN(CCC=4C3=CC=2)C(C)C)=C1CC OABGFPOPKDCDKU-UHFFFAOYSA-N 0.000 claims 1
• RKAOURQVIDODNF-UHFFFAOYSA-N 5-ethyl-4-hydroxy-2-oxo-6-(2-propyl-1,3,4,9-tetrahydropyrido[3,4-b]indol-7-yl)-1h-pyridine-3-carboxylic acid Chemical compound C1N(CCC)CCC(C2=CC=3)=C1NC2=CC=3C=1NC(=O)C(C(O)=O)=C(O)C=1CC RKAOURQVIDODNF-UHFFFAOYSA-N 0.000 claims 1
• CHJVYKRZLPQBKD-UHFFFAOYSA-N 5-ethyl-4-hydroxy-2-oxo-6-[1-(3-pyrrolidin-1-ylphenyl)indol-5-yl]-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=CN(C3=CC=2)C=2C=C(C=CC=2)N2CCCC2)=C1CC CHJVYKRZLPQBKD-UHFFFAOYSA-N 0.000 claims 1
• IPWFFFYICXHPGN-UHFFFAOYSA-N 5-ethyl-4-hydroxy-2-oxo-6-[1-(4-pyrrolidin-1-ylphenyl)indol-5-yl]-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=CN(C3=CC=2)C=2C=CC(=CC=2)N2CCCC2)=C1CC IPWFFFYICXHPGN-UHFFFAOYSA-N 0.000 claims 1
• QVYDHVXYYGOKAE-UHFFFAOYSA-N 5-ethyl-4-hydroxy-2-oxo-6-[1-[4-(trifluoromethyl)phenyl]indol-5-yl]-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=CN(C3=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1CC QVYDHVXYYGOKAE-UHFFFAOYSA-N 0.000 claims 1
• AWUMODSCMDIQNR-UHFFFAOYSA-N 5-ethyl-4-hydroxy-2-oxo-6-[2-[4-(trifluoromethyl)phenyl]-1h-indol-5-yl]-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(NC3=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1CC AWUMODSCMDIQNR-UHFFFAOYSA-N 0.000 claims 1
• HJZVAQRBEZZCSL-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-(1-methyl-2-pyrrolidin-3-ylindol-5-yl)-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(N(C)C3=CC=2)C2CNCC2)=C1CC HJZVAQRBEZZCSL-UHFFFAOYSA-N 0.000 claims 1
• UXTCMOTXWSRBKR-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-(1-methyl-3,4-dihydro-2h-quinolin-6-yl)-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3CCCN(C)C3=CC=2)=C1CC UXTCMOTXWSRBKR-UHFFFAOYSA-N 0.000 claims 1
• JURMVRXAINHFGD-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-(1-methylindol-3-yl)-2-oxo-1h-pyridine-3-carboxylic acid;5-ethyl-2-oxo-6-(2-phenyl-1,3-benzoxazol-6-yl)-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C3=CC=CC=C3N(C)C=2)=C1CC.C1=C(C(O)=O)C(=O)NC(C=2C=C3OC(=NC3=CC=2)C=2C=CC=CC=2)=C1CC JURMVRXAINHFGD-UHFFFAOYSA-N 0.000 claims 1
• KGSQUUHWTGNDGG-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-(2-methyl-1,3,4,5-tetrahydropyrido[4,3-b]indol-7-yl)-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3NC=4CCN(C)CC=4C3=CC=2)=C1CC KGSQUUHWTGNDGG-UHFFFAOYSA-N 0.000 claims 1
• XSYLFYAHHWQDAR-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-(2-methyl-1,3,4,9-tetrahydropyrido[3,4-b]indol-7-yl)-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3NC=4CN(C)CCC=4C3=CC=2)=C1CC XSYLFYAHHWQDAR-UHFFFAOYSA-N 0.000 claims 1
• WKFFRUOANMRSMS-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-(2-methylindolizin-6-yl)-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C2=CN3C=C(C)C=C3C=C2)=C1CC WKFFRUOANMRSMS-UHFFFAOYSA-N 0.000 claims 1
• YYTFUUODBRRHIG-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-(4-hydroxy-1-methylindol-5-yl)-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C(=C3C=CN(C)C3=CC=2)O)=C1CC YYTFUUODBRRHIG-UHFFFAOYSA-N 0.000 claims 1
• KMSPZSILDNDIPP-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-(6-methyl-4-pyrrolidin-1-ylpyrazolo[1,5-a]pyrazin-2-yl)-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C2=NN3C=C(C)N=C(C3=C2)N2CCCC2)=C1CC KMSPZSILDNDIPP-UHFFFAOYSA-N 0.000 claims 1
• DMGKORHKRCDPLU-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-(2-pyrrolidin-1-ylpropan-2-yl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(N(C)C3=CC=2)C(C)(C)N2CCCC2)=C1CC DMGKORHKRCDPLU-UHFFFAOYSA-N 0.000 claims 1
• RNUUDMJMMZRKQI-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-(methylaminomethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC)N(C)C3=CC=2)=C1CC RNUUDMJMMZRKQI-UHFFFAOYSA-N 0.000 claims 1
• WXBMHVLQQFFGFU-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-(morpholin-4-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCOCC4)N(C)C3=CC=2)=C1CC WXBMHVLQQFFGFU-UHFFFAOYSA-N 0.000 claims 1
• GMLIPPFJJNWKLW-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-(piperazin-1-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCNCC4)N(C)C3=CC=2)=C1CC GMLIPPFJJNWKLW-UHFFFAOYSA-N 0.000 claims 1
• WNYZMDXASVTBNH-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-(piperidin-1-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCCCC4)N(C)C3=CC=2)=C1CC WNYZMDXASVTBNH-UHFFFAOYSA-N 0.000 claims 1
• IQIOLRNYCLEQLD-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-(pyrrolidin-1-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCCC4)N(C)C3=CC=2)=C1CC IQIOLRNYCLEQLD-UHFFFAOYSA-N 0.000 claims 1
• OOWHLWKDGZQMOR-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(1-pyridin-3-ylethylamino)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC(C)C=4C=NC=CC=4)N(C)C3=CC=2)=C1CC OOWHLWKDGZQMOR-UHFFFAOYSA-N 0.000 claims 1
• BFHKKAUTJNEXQV-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(1-pyridin-4-ylethylamino)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC(C)C=4C=CN=CC=4)N(C)C3=CC=2)=C1CC BFHKKAUTJNEXQV-UHFFFAOYSA-N 0.000 claims 1
• BASHUAVPGAQHAN-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(2-methylcyclopropyl)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CC4C(C4)C)N(C)C3=CC=2)=C1CC BASHUAVPGAQHAN-UHFFFAOYSA-N 0.000 claims 1
• YESNNQGPPSPDLX-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(2-methylpyrrolidin-1-yl)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C(CCC4)C)N(C)C3=CC=2)=C1CC YESNNQGPPSPDLX-UHFFFAOYSA-N 0.000 claims 1
• HLFFXZCJSSMVPR-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(2-phenylpropan-2-ylamino)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC(C)(C)C=4C=CC=CC=4)N(C)C3=CC=2)=C1CC HLFFXZCJSSMVPR-UHFFFAOYSA-N 0.000 claims 1
• IEIOUQGMRRWUMU-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(3-pyridin-2-ylpyrrolidin-1-yl)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC(CC4)C=4N=CC=CC=4)N(C)C3=CC=2)=C1CC IEIOUQGMRRWUMU-UHFFFAOYSA-N 0.000 claims 1
• VNAJUOZBRMGWNR-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(3-pyridin-4-ylpyrrolidin-1-yl)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC(CC4)C=4C=CN=CC=4)N(C)C3=CC=2)=C1CC VNAJUOZBRMGWNR-UHFFFAOYSA-N 0.000 claims 1
• CIYOHLWNPURHMX-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(4-methyl-1,4-diazepan-1-yl)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCN(C)CCC4)N(C)C3=CC=2)=C1CC CIYOHLWNPURHMX-UHFFFAOYSA-N 0.000 claims 1
• OAWYWTBCEWYVPM-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(4-methylpiperazin-1-yl)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCN(C)CC4)N(C)C3=CC=2)=C1CC OAWYWTBCEWYVPM-UHFFFAOYSA-N 0.000 claims 1
• YDVBLLCFLRKHTF-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(4-methylpiperidin-1-yl)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCC(C)CC4)N(C)C3=CC=2)=C1CC YDVBLLCFLRKHTF-UHFFFAOYSA-N 0.000 claims 1
• WKOPIMSZUZVLRI-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(4-piperidin-1-ylpiperidin-1-yl)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCC(CC4)N4CCCCC4)N(C)C3=CC=2)=C1CC WKOPIMSZUZVLRI-UHFFFAOYSA-N 0.000 claims 1
• FDRQPOIJYVAPHV-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(4-propan-2-ylpiperazin-1-yl)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCN(CC4)C(C)C)N(C)C3=CC=2)=C1CC FDRQPOIJYVAPHV-UHFFFAOYSA-N 0.000 claims 1
• IELVAUAJPGIILG-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(nonylamino)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CNCCCCCCCCC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1CC IELVAUAJPGIILG-UHFFFAOYSA-N 0.000 claims 1
• LKTDBYFGLDZBCG-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(octylamino)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CNCCCCCCCC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1CC LKTDBYFGLDZBCG-UHFFFAOYSA-N 0.000 claims 1
• QCEOVBDPCWMZHI-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(oxan-4-ylmethylamino)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC4CCOCC4)N(C)C3=CC=2)=C1CC QCEOVBDPCWMZHI-UHFFFAOYSA-N 0.000 claims 1
• IYMOINHEWACRQY-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(pentylamino)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CNCCCCC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1CC IYMOINHEWACRQY-UHFFFAOYSA-N 0.000 claims 1
• RFMRFVMQAHZJHN-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(piperidin-4-ylamino)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC4CCNCC4)N(C)C3=CC=2)=C1CC RFMRFVMQAHZJHN-UHFFFAOYSA-N 0.000 claims 1
• CYBYEULWLQHMEX-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(prop-2-ynylamino)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC#C)N(C)C3=CC=2)=C1CC CYBYEULWLQHMEX-UHFFFAOYSA-N 0.000 claims 1
• DITYGYSTJDSCMY-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(pyridin-2-ylmethylamino)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC=4N=CC=CC=4)N(C)C3=CC=2)=C1CC DITYGYSTJDSCMY-UHFFFAOYSA-N 0.000 claims 1
• LSCOCBQAVATKCF-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(pyridin-3-ylmethylamino)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC=4C=NC=CC=4)N(C)C3=CC=2)=C1CC LSCOCBQAVATKCF-UHFFFAOYSA-N 0.000 claims 1
• QHCJPTYPPATXAT-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[(pyridin-4-ylmethylamino)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC=4C=CN=CC=4)N(C)C3=CC=2)=C1CC QHCJPTYPPATXAT-UHFFFAOYSA-N 0.000 claims 1
• JMYMTGXAEBUGEX-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[(1-methylazetidin-3-yl)amino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC4CN(C)C4)N(C)C3=CC=2)=C1CC JMYMTGXAEBUGEX-UHFFFAOYSA-N 0.000 claims 1
• PSAJGMYPKHWYTE-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[(1-methylcyclobutyl)amino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC4(C)CCC4)N(C)C3=CC=2)=C1CC PSAJGMYPKHWYTE-UHFFFAOYSA-N 0.000 claims 1
• MZMFLLSKNZLMHJ-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[(1-methylcyclopropyl)amino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC4(C)CC4)N(C)C3=CC=2)=C1CC MZMFLLSKNZLMHJ-UHFFFAOYSA-N 0.000 claims 1
• CJAKNEBMZYDZLC-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[(1-methylpiperidin-2-yl)methylamino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC4N(CCCC4)C)N(C)C3=CC=2)=C1CC CJAKNEBMZYDZLC-UHFFFAOYSA-N 0.000 claims 1
• VAAHXTXUBCRGDP-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[(1-methylpiperidin-3-yl)methylamino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC4CN(C)CCC4)N(C)C3=CC=2)=C1CC VAAHXTXUBCRGDP-UHFFFAOYSA-N 0.000 claims 1
• CBBUCXGQOFEYPO-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[(1-methylpiperidin-4-yl)methylamino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC4CCN(C)CC4)N(C)C3=CC=2)=C1CC CBBUCXGQOFEYPO-UHFFFAOYSA-N 0.000 claims 1
• XYSDIFFJVWAJBI-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[(3-methylphenyl)methylamino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC=4C=C(C)C=CC=4)N(C)C3=CC=2)=C1CC XYSDIFFJVWAJBI-UHFFFAOYSA-N 0.000 claims 1
• FOLYMZQCIRLQCM-GASCZTMLSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[(3r,5s)-3,4,5-trimethylpiperazin-1-yl]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C[C@@H](C)N(C)[C@@H](C)C4)N(C)C3=CC=2)=C1CC FOLYMZQCIRLQCM-GASCZTMLSA-N 0.000 claims 1
• FRCGVMMXNHREMT-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[(4-methylphenyl)methylamino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC=4C=CC(C)=CC=4)N(C)C3=CC=2)=C1CC FRCGVMMXNHREMT-UHFFFAOYSA-N 0.000 claims 1
• OZVHZOCWLUQDIU-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[2-(methylamino)ethylamino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCCNC)N(C)C3=CC=2)=C1CC OZVHZOCWLUQDIU-UHFFFAOYSA-N 0.000 claims 1
• VNGUSCJNWLXARA-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[2-(trifluoromethyl)piperidin-1-yl]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C(CCCC4)C(F)(F)F)N(C)C3=CC=2)=C1CC VNGUSCJNWLXARA-UHFFFAOYSA-N 0.000 claims 1
• ORKHQYXVKVKEPR-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[3-(methylamino)pyrrolidin-1-yl]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC(CC4)NC)N(C)C3=CC=2)=C1CC ORKHQYXVKVKEPR-UHFFFAOYSA-N 0.000 claims 1
• BELLWEPYOLYMCC-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[4-(methylamino)piperidin-1-yl]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCC(CC4)NC)N(C)C3=CC=2)=C1CC BELLWEPYOLYMCC-UHFFFAOYSA-N 0.000 claims 1
• YJCRUDCCOQBPGG-RSAXXLAASA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[[(1s)-1-phenylethyl]amino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN[C@@H](C)C=4C=CC=CC=4)N(C)C3=CC=2)=C1CC YJCRUDCCOQBPGG-RSAXXLAASA-N 0.000 claims 1
• IFZILXOFRSUSEL-SNVBAGLBSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[[(2r)-1,1,1-trifluoropropan-2-yl]amino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN[C@H](C)C(F)(F)F)N(C)C3=CC=2)=C1CC IFZILXOFRSUSEL-SNVBAGLBSA-N 0.000 claims 1
• BFFKXPKTGLHYFV-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[methyl(piperidin-3-yl)amino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN(C)C4CNCCC4)N(C)C3=CC=2)=C1CC BFFKXPKTGLHYFV-UHFFFAOYSA-N 0.000 claims 1
• LOFSUIQSUKQLHV-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[methyl(piperidin-4-yl)amino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN(C)C4CCNCC4)N(C)C3=CC=2)=C1CC LOFSUIQSUKQLHV-UHFFFAOYSA-N 0.000 claims 1
• QHBMDAPXGOHSEL-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[methyl(pyridin-3-ylmethyl)amino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN(C)CC=4C=NC=CC=4)N(C)C3=CC=2)=C1CC QHBMDAPXGOHSEL-UHFFFAOYSA-N 0.000 claims 1
• PTSQIWZGZSBDQT-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[1-methyl-2-[[methyl(pyridin-4-ylmethyl)amino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN(C)CC=4C=CN=CC=4)N(C)C3=CC=2)=C1CC PTSQIWZGZSBDQT-UHFFFAOYSA-N 0.000 claims 1
• YFQVPTIWQCNZSE-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[2-(methylamino)-2,3-dihydro-1h-pyrrolo[1,2-a]indol-6-yl]-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C4CC(CN4C3=CC=2)NC)=C1CC YFQVPTIWQCNZSE-UHFFFAOYSA-N 0.000 claims 1
• LBLVQKNGKKCIAN-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[2-[(3-hydroxyazetidin-1-yl)methyl]-1-methylindol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC(O)C4)N(C)C3=CC=2)=C1CC LBLVQKNGKKCIAN-UHFFFAOYSA-N 0.000 claims 1
• KMNHBLQCZYWLFQ-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[2-[(3-hydroxypiperidin-1-yl)methyl]-1-methylindol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC(O)CCC4)N(C)C3=CC=2)=C1CC KMNHBLQCZYWLFQ-UHFFFAOYSA-N 0.000 claims 1
• ZTUWRACZPKQYER-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[2-[(3-hydroxypyrrolidin-1-yl)methyl]-1-methylindol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC(O)CC4)N(C)C3=CC=2)=C1CC ZTUWRACZPKQYER-UHFFFAOYSA-N 0.000 claims 1
• JRRITRYNAFQDOB-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[2-[(3-methoxypyrrolidin-1-yl)methyl]-1-methylindol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC(CC4)OC)N(C)C3=CC=2)=C1CC JRRITRYNAFQDOB-UHFFFAOYSA-N 0.000 claims 1
• OWLVKVUWAMFOBB-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[2-[(4-hydroxypiperidin-1-yl)methyl]-1-methylindol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCC(O)CC4)N(C)C3=CC=2)=C1CC OWLVKVUWAMFOBB-UHFFFAOYSA-N 0.000 claims 1
• KXWVNSUDDREEAN-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[2-[[(2-methoxyphenyl)methylamino]methyl]-1-methylindol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC=4C(=CC=CC=4)OC)N(C)C3=CC=2)=C1CC KXWVNSUDDREEAN-UHFFFAOYSA-N 0.000 claims 1
• CVPINQGGCUHGHF-SFHVURJKSA-N 5-ethyl-4-hydroxy-6-[2-[[(2s)-2-methoxycarbonylpyrrolidin-1-yl]methyl]-1-methylindol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4[C@@H](CCC4)C(=O)OC)N(C)C3=CC=2)=C1CC CVPINQGGCUHGHF-SFHVURJKSA-N 0.000 claims 1
• QPCZUMGRXQQJAW-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[2-[[(3-methoxyphenyl)methylamino]methyl]-1-methylindol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC=4C=C(OC)C=CC=4)N(C)C3=CC=2)=C1CC QPCZUMGRXQQJAW-UHFFFAOYSA-N 0.000 claims 1
• FSVHWVLZRPVOIF-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[2-[[(4-methoxyphenyl)methylamino]methyl]-1-methylindol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC=4C=CC(OC)=CC=4)N(C)C3=CC=2)=C1CC FSVHWVLZRPVOIF-UHFFFAOYSA-N 0.000 claims 1
• XWKYBHLFOWIWIU-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[2-[[2-(2-methoxyethyl)piperidin-1-yl]methyl]-1-methylindol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C(CCCC4)CCOC)N(C)C3=CC=2)=C1CC XWKYBHLFOWIWIU-UHFFFAOYSA-N 0.000 claims 1
• FGAQQEVLAJPPLB-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[2-[[2-(3-methoxypropyl)piperidin-1-yl]methyl]-1-methylindol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C(CCCC4)CCCOC)N(C)C3=CC=2)=C1CC FGAQQEVLAJPPLB-UHFFFAOYSA-N 0.000 claims 1
• GTJQRWVXLSJFMS-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[2-[[2-methoxyethyl(methyl)amino]methyl]-1-methylindol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN(C)CCOC)N(C)C3=CC=2)=C1CC GTJQRWVXLSJFMS-UHFFFAOYSA-N 0.000 claims 1
• TXJLJHWDWOUFKF-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[2-[[3-(hydroxymethyl)azetidin-1-yl]methyl]-1-methylindol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC(CO)C4)N(C)C3=CC=2)=C1CC TXJLJHWDWOUFKF-UHFFFAOYSA-N 0.000 claims 1
• SVQWLCIXUQEPCM-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[2-[methyl(propyl)amino]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-6-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N3CC(N(C)CCC)CC3=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1CC SVQWLCIXUQEPCM-UHFFFAOYSA-N 0.000 claims 1
• DRTDMIAESSEXIR-UHFFFAOYSA-N 5-ethyl-4-hydroxy-6-[7-(methylamino)-6,7,8,9-tetrahydropyrido[1,2-a]indol-2-yl]-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C4CCC(CN4C3=CC=2)NC)=C1CC DRTDMIAESSEXIR-UHFFFAOYSA-N 0.000 claims 1
• BGKBGHOXDAOVCV-UHFFFAOYSA-N 5-ethyl-6-(1-methyl-2-piperazin-2-ylindol-5-yl)-2-oxo-1h-pyridine-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(N(C)C3=CC=2)C2NCCNC2)=C1CC BGKBGHOXDAOVCV-UHFFFAOYSA-N 0.000 claims 1
• MCCXNCVKEVXWEE-UHFFFAOYSA-N 5-ethyl-6-(1-methyl-2-pyrrolidin-3-ylindol-5-yl)-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(N(C)C3=CC=2)C2CNCC2)=C1CC MCCXNCVKEVXWEE-UHFFFAOYSA-N 0.000 claims 1
• BYKWHHVALWMKBV-UHFFFAOYSA-N 5-ethyl-6-(1-methyl-3,4-dihydro-2h-quinolin-6-yl)-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3CCCN(C)C3=CC=2)=C1CC BYKWHHVALWMKBV-UHFFFAOYSA-N 0.000 claims 1
• MHBXOQLNUOAQHR-UHFFFAOYSA-N 5-ethyl-6-(1-methylpyrrolo[2,3-b]pyridin-5-yl)-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=CN(C)C3=NC=2)=C1CC MHBXOQLNUOAQHR-UHFFFAOYSA-N 0.000 claims 1
• MJTUFYYNWWDGJK-UHFFFAOYSA-N 5-ethyl-6-(2-ethyl-1,3,4,5-tetrahydropyrido[4,3-b]indol-7-yl)-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2C=3CN(CC)CCC=3NC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1CC MJTUFYYNWWDGJK-UHFFFAOYSA-N 0.000 claims 1
• GKLMOTZYFYNMMU-UHFFFAOYSA-N 5-ethyl-6-(2-ethyl-1,3,4,9-tetrahydropyrido[3,4-b]indol-7-yl)-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1N(CC)CCC(C2=CC=3)=C1NC2=CC=3C=1NC(=O)C(C(O)=O)=C(O)C=1CC GKLMOTZYFYNMMU-UHFFFAOYSA-N 0.000 claims 1
• MYHLDJMDUBAURV-UHFFFAOYSA-N 5-ethyl-6-(3-morpholin-4-yl-2,3-dihydro-1h-pyrrolo[1,2-a]indol-6-yl)-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C4C(N5CCOCC5)CCN4C3=CC=2)=C1CC MYHLDJMDUBAURV-UHFFFAOYSA-N 0.000 claims 1
• YTWFYFPFCGDFFG-UHFFFAOYSA-N 5-ethyl-6-(4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3OCCN(C)C3=CC=2)=C1CC YTWFYFPFCGDFFG-UHFFFAOYSA-N 0.000 claims 1
• DRIBKIDKQQARBR-UHFFFAOYSA-N 5-ethyl-6-(5-fluoro-1,6-dimethylindol-2-yl)-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2N(C3=CC(C)=C(F)C=C3C=2)C)=C1CC DRIBKIDKQQARBR-UHFFFAOYSA-N 0.000 claims 1
• YWZOAICAKHJLBP-UHFFFAOYSA-N 5-ethyl-6-(6-ethyl-1h-indol-2-yl)-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound N1C2=CC(CC)=CC=C2C=C1C=1NC(=O)C(C(O)=O)=C(O)C=1CC YWZOAICAKHJLBP-UHFFFAOYSA-N 0.000 claims 1
• IYGUZEGLNXFOPO-UHFFFAOYSA-N 5-ethyl-6-(9-methyl-5,6,7,8-tetrahydrocarbazol-3-yl)-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=4CCCCC=4N(C)C3=CC=2)=C1CC IYGUZEGLNXFOPO-UHFFFAOYSA-N 0.000 claims 1
• DOUUXBMZKHWQBB-UHFFFAOYSA-N 5-ethyl-6-[1-(2-hydroxyethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;5-ethyl-4-hydroxy-6-(1-methylindol-5-yl)-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=CN(C)C3=CC=2)=C1CC.C1=C(C(O)=O)C(=O)NC(C=2C=C3C=CN(CCO)C3=CC=2)=C1CC DOUUXBMZKHWQBB-UHFFFAOYSA-N 0.000 claims 1
• SHXMIMXEMDYOFP-UHFFFAOYSA-N 5-ethyl-6-[1-(4-fluorophenyl)indol-5-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=CN(C3=CC=2)C=2C=CC(F)=CC=2)=C1CC SHXMIMXEMDYOFP-UHFFFAOYSA-N 0.000 claims 1
• OVKWTHMCZPOWJX-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-(1,4,5,6-tetrahydropyrimidin-2-yl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(N(C)C3=CC=2)C=2NCCCN=2)=C1CC OVKWTHMCZPOWJX-UHFFFAOYSA-N 0.000 claims 1
• OPCGIEGIYORNKO-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-(1-methylpiperazin-2-yl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(N(C)C3=CC=2)C2N(CCNC2)C)=C1CC OPCGIEGIYORNKO-UHFFFAOYSA-N 0.000 claims 1
• ZUARQHVYINQDJZ-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-(1-pyrrolidin-1-ylethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(N(C)C3=CC=2)C(C)N2CCCC2)=C1CC ZUARQHVYINQDJZ-UHFFFAOYSA-N 0.000 claims 1
• KNZBVFUEFLYNRF-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-(2-morpholin-4-ylethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CCN4CCOCC4)N(C)C3=CC=2)=C1CC KNZBVFUEFLYNRF-UHFFFAOYSA-N 0.000 claims 1
• NNWKXVWKQQSDGU-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-(2-piperidin-1-ylethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CCN4CCCCC4)N(C)C3=CC=2)=C1CC NNWKXVWKQQSDGU-UHFFFAOYSA-N 0.000 claims 1
• OXDLEUOABDPWOQ-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-(2-pyrrolidin-1-ylethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CCN4CCCC4)N(C)C3=CC=2)=C1CC OXDLEUOABDPWOQ-UHFFFAOYSA-N 0.000 claims 1
• WPDXGQIJXZTTJZ-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-(2-pyrrolidin-1-ylpropan-2-yl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(N(C)C3=CC=2)C(C)(C)N2CCCC2)=C1CC WPDXGQIJXZTTJZ-UHFFFAOYSA-N 0.000 claims 1
• IUZJYUAZGFFUFC-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-(methylaminomethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC)N(C)C3=CC=2)=C1CC IUZJYUAZGFFUFC-UHFFFAOYSA-N 0.000 claims 1
• WOODZSRTDYHECQ-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-(morpholin-4-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCOCC4)N(C)C3=CC=2)=C1CC WOODZSRTDYHECQ-UHFFFAOYSA-N 0.000 claims 1
• VNWLBWRSGDHMBQ-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-(piperazin-1-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCNCC4)N(C)C3=CC=2)=C1CC VNWLBWRSGDHMBQ-UHFFFAOYSA-N 0.000 claims 1
• HWLOFCCUXFPILT-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-(piperidin-1-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCCCC4)N(C)C3=CC=2)=C1CC HWLOFCCUXFPILT-UHFFFAOYSA-N 0.000 claims 1
• AOXPJGSASFUBCM-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-(pyrrolidin-1-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3,4-dicarboxylic acid Chemical compound N1C(=O)C(C(O)=O)=C(C(O)=O)C(CC)=C1C1=CC=C(N(C)C(CN2CCCC2)=C2)C2=C1 AOXPJGSASFUBCM-UHFFFAOYSA-N 0.000 claims 1
• WCYAWIJRODWSFY-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-(pyrrolidin-1-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCCC4)N(C)C3=CC=2)=C1CC WCYAWIJRODWSFY-UHFFFAOYSA-N 0.000 claims 1
• QNFLUILBVOLTNT-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-(pyrrolidin-1-ylmethyl)pyrrolo[3,2-b]pyridin-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2N=C3C=C(CN4CCCC4)N(C)C3=CC=2)=C1CC QNFLUILBVOLTNT-UHFFFAOYSA-N 0.000 claims 1
• GNCYKZPEISJPSI-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-[(2-methylpyrrolidin-1-yl)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C(CCC4)C)N(C)C3=CC=2)=C1CC GNCYKZPEISJPSI-UHFFFAOYSA-N 0.000 claims 1
• QADVHQIFYWAKMA-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-[(2-phenylpyrrolidin-1-yl)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C(CCC4)C=4C=CC=CC=4)N(C)C3=CC=2)=C1CC QADVHQIFYWAKMA-UHFFFAOYSA-N 0.000 claims 1
• HDWJONVAVFCZDV-PKLMIRHRSA-N 5-ethyl-6-[1-methyl-2-[(2r)-pyrrolidin-2-yl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(N(C)C3=CC=2)[C@@H]2NCCC2)=C1CC HDWJONVAVFCZDV-PKLMIRHRSA-N 0.000 claims 1
• HDWJONVAVFCZDV-NTISSMGPSA-N 5-ethyl-6-[1-methyl-2-[(2s)-pyrrolidin-2-yl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(N(C)C3=CC=2)[C@H]2NCCC2)=C1CC HDWJONVAVFCZDV-NTISSMGPSA-N 0.000 claims 1
• YOZDNDJCJBYAKL-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-[(4-methylpiperazin-1-yl)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCN(C)CC4)N(C)C3=CC=2)=C1CC YOZDNDJCJBYAKL-UHFFFAOYSA-N 0.000 claims 1
• CQRFOAGGFAFFRZ-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-[(4-propan-2-ylpiperazin-1-yl)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCN(CC4)C(C)C)N(C)C3=CC=2)=C1CC CQRFOAGGFAFFRZ-UHFFFAOYSA-N 0.000 claims 1
• IOHZRWZGNNQUHA-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-[(pyridin-2-ylmethylamino)methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC=4N=CC=CC=4)N(C)C3=CC=2)=C1CC IOHZRWZGNNQUHA-UHFFFAOYSA-N 0.000 claims 1
• VHNRPEIJPAMIOE-UHFFFAOYSA-N 5-ethyl-6-[1-methyl-2-[[3-(methylamino)pyrrolidin-1-yl]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC(CC4)NC)N(C)C3=CC=2)=C1CC VHNRPEIJPAMIOE-UHFFFAOYSA-N 0.000 claims 1
• IMSJEXYOLSPFDU-MRXNPFEDSA-N 5-ethyl-6-[1-methyl-2-[[[(1r)-1-phenylethyl]amino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN[C@H](C)C=4C=CC=CC=4)N(C)C3=CC=2)=C1CC IMSJEXYOLSPFDU-MRXNPFEDSA-N 0.000 claims 1
• UQUOXIMOPOBIPY-HSZRJFAPSA-N 5-ethyl-6-[1-methyl-2-[[[(1r)-1-phenylpropyl]amino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=CC=CC=1)CC(N(C1=CC=2)C)=CC1=CC=2C=1NC(=O)C(C(O)=O)=CC=1CC UQUOXIMOPOBIPY-HSZRJFAPSA-N 0.000 claims 1
• IMSJEXYOLSPFDU-INIZCTEOSA-N 5-ethyl-6-[1-methyl-2-[[[(1s)-1-phenylethyl]amino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN[C@@H](C)C=4C=CC=CC=4)N(C)C3=CC=2)=C1CC IMSJEXYOLSPFDU-INIZCTEOSA-N 0.000 claims 1
• UQUOXIMOPOBIPY-QHCPKHFHSA-N 5-ethyl-6-[1-methyl-2-[[[(1s)-1-phenylpropyl]amino]methyl]indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound N([C@@H](CC)C=1C=CC=CC=1)CC(N(C1=CC=2)C)=CC1=CC=2C=1NC(=O)C(C(O)=O)=CC=1CC UQUOXIMOPOBIPY-QHCPKHFHSA-N 0.000 claims 1
• BHGWAYPKDAJJSK-UHFFFAOYSA-N 5-ethyl-6-[2-(ethylaminomethyl)-1-methylindol-5-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CNCC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1CC BHGWAYPKDAJJSK-UHFFFAOYSA-N 0.000 claims 1
• IIGSQAXCZKPEBM-UHFFFAOYSA-N 5-ethyl-6-[2-(ethylaminomethyl)-1h-indol-6-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.C1=C2NC(CNCC)=CC2=CC=C1C=1NC(=O)C(C(O)=O)=C(O)C=1CC IIGSQAXCZKPEBM-UHFFFAOYSA-N 0.000 claims 1
• GJQAGWPODSLOFE-UHFFFAOYSA-N 5-ethyl-6-[2-(ethylaminomethyl)-3-fluoro-1-methylindol-5-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CNCC)=C(F)C2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1CC GJQAGWPODSLOFE-UHFFFAOYSA-N 0.000 claims 1
• XSIVOEACITYVMC-UHFFFAOYSA-N 5-ethyl-6-[2-[(2-fluoroethylamino)methyl]-1-methylindol-5-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCCF)N(C)C3=CC=2)=C1CC XSIVOEACITYVMC-UHFFFAOYSA-N 0.000 claims 1
• CADWETNNTUCVEH-UHFFFAOYSA-N 5-ethyl-6-[2-[(3-fluoroazetidin-1-yl)methyl]-1-methylindol-5-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC(F)C4)N(C)C3=CC=2)=C1CC CADWETNNTUCVEH-UHFFFAOYSA-N 0.000 claims 1
• AFBPHIVJAMBAPM-UHFFFAOYSA-N 5-ethyl-6-[2-[(3-hydroxypyrrolidin-1-yl)methyl]-1-methylindol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC(O)CC4)N(C)C3=CC=2)=C1CC AFBPHIVJAMBAPM-UHFFFAOYSA-N 0.000 claims 1
• LKXZBUZJHNHGHR-UHFFFAOYSA-N 5-ethyl-6-[2-[(heptylamino)methyl]-1-methylindol-5-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CNCCCCCCC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1CC LKXZBUZJHNHGHR-UHFFFAOYSA-N 0.000 claims 1
• KNONDCOPQQOFRJ-UHFFFAOYSA-N 5-ethyl-6-[2-[(hexylamino)methyl]-1-methylindol-5-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CNCCCCCC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1CC KNONDCOPQQOFRJ-UHFFFAOYSA-N 0.000 claims 1
• UKLORIZRZPOCKT-UHFFFAOYSA-N 5-ethyl-6-[2-[[(2-fluorophenyl)methylamino]methyl]-1-methylindol-5-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC=4C(=CC=CC=4)F)N(C)C3=CC=2)=C1CC UKLORIZRZPOCKT-UHFFFAOYSA-N 0.000 claims 1
• ZBDZMILOWTVUFQ-QGZVFWFLSA-N 5-ethyl-6-[2-[[(2r)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]-1-methylindol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4[C@H](CCC4)CO)N(C)C3=CC=2)=C1CC ZBDZMILOWTVUFQ-QGZVFWFLSA-N 0.000 claims 1
• AUIYJKHXXDXKOF-UHFFFAOYSA-N 5-ethyl-6-[2-[[(3-fluorophenyl)methylamino]methyl]-1-methylindol-5-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC=4C=C(F)C=CC=4)N(C)C3=CC=2)=C1CC AUIYJKHXXDXKOF-UHFFFAOYSA-N 0.000 claims 1
• XLQZGLIOZQHLGI-MRXNPFEDSA-N 5-ethyl-6-[2-[[(3r)-3-fluoropyrrolidin-1-yl]methyl]-1-methylindol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C[C@H](F)CC4)N(C)C3=CC=2)=C1CC XLQZGLIOZQHLGI-MRXNPFEDSA-N 0.000 claims 1
• SJQPTGIZVISUTF-CQSZACIVSA-N 5-ethyl-6-[2-[[(3r)-3-fluoropyrrolidin-1-yl]methyl]-1-methylindol-5-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C[C@H](F)CC4)N(C)C3=CC=2)=C1CC SJQPTGIZVISUTF-CQSZACIVSA-N 0.000 claims 1
• PNGNKMZOAXZKNN-UHFFFAOYSA-N 5-ethyl-6-[2-[[(4-fluorophenyl)methylamino]methyl]-1-methylindol-5-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC=4C=CC(F)=CC=4)N(C)C3=CC=2)=C1CC PNGNKMZOAXZKNN-UHFFFAOYSA-N 0.000 claims 1
• XONZGCCSTACTJY-UHFFFAOYSA-N 5-ethyl-6-[2-[ethyl(methyl)amino]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-6-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N3CC(N(C)CC)CC3=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1CC XONZGCCSTACTJY-UHFFFAOYSA-N 0.000 claims 1
• UJXVMQBTJNPPFC-UHFFFAOYSA-N 5-ethyl-6-[3-fluoro-1-methyl-2-(methylaminomethyl)indol-5-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C(F)=C(CNC)N(C)C3=CC=2)=C1CC UJXVMQBTJNPPFC-UHFFFAOYSA-N 0.000 claims 1
• JKIVQEMFQXQASX-UHFFFAOYSA-N 5-ethyl-6-[3-fluoro-1-methyl-2-[(propan-2-ylamino)methyl]indol-5-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C(F)=C(CNC(C)C)N(C)C3=CC=2)=C1CC JKIVQEMFQXQASX-UHFFFAOYSA-N 0.000 claims 1
• XYKIDPUHCMFHOY-UHFFFAOYSA-N 5-ethyl-6-[4-fluoro-1-methyl-2-(pyrrolidin-1-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C(=C3C=C(CN4CCCC4)N(C)C3=CC=2)F)=C1CC XYKIDPUHCMFHOY-UHFFFAOYSA-N 0.000 claims 1
• IOXVLZIQZNPIQQ-UHFFFAOYSA-N 5-ethyl-6-[6-methoxy-1-methyl-2-(morpholin-4-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C(=CC=3N(C)C(CN4CCOCC4)=CC=3C=2)OC)=C1CC IOXVLZIQZNPIQQ-UHFFFAOYSA-N 0.000 claims 1
• AJLHRKIDJFHKHQ-UHFFFAOYSA-N 5-ethyl-6-[6-methoxy-1-methyl-2-(pyrrolidin-1-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C(=CC=3N(C)C(CN4CCCC4)=CC=3C=2)OC)=C1CC AJLHRKIDJFHKHQ-UHFFFAOYSA-N 0.000 claims 1
• BIZLCOUCUDHQKZ-UHFFFAOYSA-N 5-ethyl-6-[6-methyl-5-(pyrrolidin-1-ylmethyl)thieno[2,3-b]pyrrol-2-yl]-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(=O)NC(C=2SC=3N(C)C(CN4CCCC4)=CC=3C=2)=C1CC BIZLCOUCUDHQKZ-UHFFFAOYSA-N 0.000 claims 1
• QWXRBGANZTVJGY-UHFFFAOYSA-N 5-ethyl-6-[7-fluoro-1-methyl-2-(morpholin-4-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCOCC4)N(C)C3=C(F)C=2)=C1CC QWXRBGANZTVJGY-UHFFFAOYSA-N 0.000 claims 1
• SBGCBSCKJJFYAF-UHFFFAOYSA-N 5-ethyl-6-[7-fluoro-1-methyl-2-(piperidin-1-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCCCC4)N(C)C3=C(F)C=2)=C1CC SBGCBSCKJJFYAF-UHFFFAOYSA-N 0.000 claims 1
• WAVUQHPUOONKGP-UHFFFAOYSA-N 5-ethyl-6-[7-fluoro-1-methyl-2-(pyrrolidin-1-ylmethyl)indol-5-yl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCCC4)N(C)C3=C(F)C=2)=C1CC WAVUQHPUOONKGP-UHFFFAOYSA-N 0.000 claims 1
• QAFRZMGNSYNKHP-UHFFFAOYSA-N 6-(2-amino-2,3-dihydro-1h-pyrrolo[1,2-a]indol-6-yl)-4-hydroxy-5-methyl-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C4CC(N)CN4C3=CC=2)=C1C QAFRZMGNSYNKHP-UHFFFAOYSA-N 0.000 claims 1
• QYUDRUHPUBHJAY-UHFFFAOYSA-N 6-(2-amino-2,3-dihydro-1h-pyrrolo[1,2-a]indol-6-yl)-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C4CC(N)CN4C3=CC=2)=C1CC QYUDRUHPUBHJAY-UHFFFAOYSA-N 0.000 claims 1
• WIHAZWOOHUSAHH-UHFFFAOYSA-N 6-(3-cyano-1-methyl-2-pyrrolidin-1-ylindol-5-yl)-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C(C#N)=C(N4CCCC4)N(C)C3=CC=2)=C1CC WIHAZWOOHUSAHH-UHFFFAOYSA-N 0.000 claims 1
• ZQQPQAWLQHGPLP-UHFFFAOYSA-N 6-(9h-carbazol-2-yl)-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1CC ZQQPQAWLQHGPLP-UHFFFAOYSA-N 0.000 claims 1
• FRWUNWTULJBGIK-NHYQQRJDSA-N 6-[(2s,3s)-2-(aminomethyl)-3-(methylamino)-2,3-dihydro-1h-pyrrolo[1,2-a]indol-6-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C4[C@@H](NC)[C@@H](CN)CN4C3=CC=2)=C1CC FRWUNWTULJBGIK-NHYQQRJDSA-N 0.000 claims 1
• AAYHOCDDAPGACC-OJNIYTAOSA-N 6-[(7r,9r)-7-amino-9-(methylamino)-6,7,8,9-tetrahydropyrido[1,2-a]indol-2-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C4[C@H](NC)C[C@@H](N)CN4C3=CC=2)=C1CC AAYHOCDDAPGACC-OJNIYTAOSA-N 0.000 claims 1
• JJEJAVNDYROVAB-UHFFFAOYSA-N 6-[1,6-dimethyl-2-(morpholin-4-ylmethyl)indol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C(=CC=3N(C)C(CN4CCOCC4)=CC=3C=2)C)=C1CC JJEJAVNDYROVAB-UHFFFAOYSA-N 0.000 claims 1
• LXXUHRLHKWLRPP-UHFFFAOYSA-N 6-[1,6-dimethyl-2-(piperidin-1-ylmethyl)indol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C(=CC=3N(C)C(CN4CCCCC4)=CC=3C=2)C)=C1CC LXXUHRLHKWLRPP-UHFFFAOYSA-N 0.000 claims 1
• BEVSEFWRMQELAG-UHFFFAOYSA-N 6-[1,6-dimethyl-2-(pyrrolidin-1-ylmethyl)indol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C(=CC=3N(C)C(CN4CCCC4)=CC=3C=2)C)=C1CC BEVSEFWRMQELAG-UHFFFAOYSA-N 0.000 claims 1
• FAPBBEPVBFTMNJ-UHFFFAOYSA-N 6-[1,7-dimethyl-2-(morpholin-4-ylmethyl)indol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCOCC4)N(C)C3=C(C)C=2)=C1CC FAPBBEPVBFTMNJ-UHFFFAOYSA-N 0.000 claims 1
• YHKKTUMWJUUZHN-UHFFFAOYSA-N 6-[1,7-dimethyl-2-(piperidin-1-ylmethyl)indol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCCCC4)N(C)C3=C(C)C=2)=C1CC YHKKTUMWJUUZHN-UHFFFAOYSA-N 0.000 claims 1
• RLWSVNJULNNUJS-UHFFFAOYSA-N 6-[1,7-dimethyl-2-(pyrrolidin-1-ylmethyl)indol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCCC4)N(C)C3=C(C)C=2)=C1CC RLWSVNJULNNUJS-UHFFFAOYSA-N 0.000 claims 1
• YPQCGLUCTHZRHT-UHFFFAOYSA-N 6-[1-(1,3-dioxolan-2-ylmethyl)indol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=CN(CC4OCCO4)C3=CC=2)=C1CC YPQCGLUCTHZRHT-UHFFFAOYSA-N 0.000 claims 1
• YAUJJJRAYZABGE-UHFFFAOYSA-N 6-[2-(1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-ylmethyl)-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC5NCCCC5C4)N(C)C3=CC=2)=C1CC YAUJJJRAYZABGE-UHFFFAOYSA-N 0.000 claims 1
• MKTMZTXHYKIOSY-UHFFFAOYSA-N 6-[2-(1,4-diazepan-1-ylmethyl)-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCNCCC4)N(C)C3=CC=2)=C1CC MKTMZTXHYKIOSY-UHFFFAOYSA-N 0.000 claims 1
• WDZLNOCKIHYERO-UHFFFAOYSA-N 6-[2-(2,5-diazabicyclo[2.2.1]heptan-2-ylmethyl)-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C5CC(NC5)C4)N(C)C3=CC=2)=C1CC WDZLNOCKIHYERO-UHFFFAOYSA-N 0.000 claims 1
• GRPCKLSSQAGQLB-UHFFFAOYSA-N 6-[2-(2,5-diazabicyclo[2.2.1]heptan-2-ylmethyl)-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C5CC(NC5)C4)N(C)C3=CC=2)=C1CC GRPCKLSSQAGQLB-UHFFFAOYSA-N 0.000 claims 1
• ALIMRMUTCSJGRR-UHFFFAOYSA-N 6-[2-(3,4-dihydro-1h-isoquinolin-2-ylmethyl)-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC5=CC=CC=C5CC4)N(C)C3=CC=2)=C1CC ALIMRMUTCSJGRR-UHFFFAOYSA-N 0.000 claims 1
• PBFACCARCNHVOX-UHFFFAOYSA-N 6-[2-(4,5-dihydro-1h-imidazol-2-yl)-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(N(C)C3=CC=2)C=2NCCN=2)=C1CC PBFACCARCNHVOX-UHFFFAOYSA-N 0.000 claims 1
• JXBBHGVFHGQRNB-UHFFFAOYSA-N 6-[2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-ylmethyl)-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC5=NC=CC=C5C4)N(C)C3=CC=2)=C1CC JXBBHGVFHGQRNB-UHFFFAOYSA-N 0.000 claims 1
• XMQGBGSYKPEPOW-UHFFFAOYSA-N 6-[2-(aminomethyl)-1-methylindol-5-yl]-4-hydroxy-5-methyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN)N(C)C3=CC=2)=C1C XMQGBGSYKPEPOW-UHFFFAOYSA-N 0.000 claims 1
• HOLMKESJZBBACI-UHFFFAOYSA-N 6-[2-(aminomethyl)-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN)N(C)C3=CC=2)=C1CC HOLMKESJZBBACI-UHFFFAOYSA-N 0.000 claims 1
• DRUKFIBTJWIECT-UHFFFAOYSA-N 6-[2-(aminomethyl)-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN)N(C)C3=CC=2)=C1CC DRUKFIBTJWIECT-UHFFFAOYSA-N 0.000 claims 1
• KHQWONZPBOJALU-UHFFFAOYSA-N 6-[2-(anilinomethyl)-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC=4C=CC=CC=4)N(C)C3=CC=2)=C1CC KHQWONZPBOJALU-UHFFFAOYSA-N 0.000 claims 1
• IJZGMZMTOYYKKC-UHFFFAOYSA-N 6-[2-(azetidin-1-ylmethyl)-1-methylindol-5-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C2=CC(C=3NC(=O)C(C(O)=O)=C(O)C=3)=CC=C2N(C)C=1CN1CCC1 IJZGMZMTOYYKKC-UHFFFAOYSA-N 0.000 claims 1
• IYBBCVUQYMKWFC-UHFFFAOYSA-N 6-[2-(azetidin-1-ylmethyl)-1-methylindol-5-yl]-4-hydroxy-5-methyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCC4)N(C)C3=CC=2)=C1C IYBBCVUQYMKWFC-UHFFFAOYSA-N 0.000 claims 1
• YGPDNAJGPRXDSQ-UHFFFAOYSA-N 6-[2-(azetidin-1-ylmethyl)-1-methylindol-5-yl]-5-(4-fluorophenyl)-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C2=CC(C3=C(C(O)=C(C(O)=O)C(=O)N3)C=3C=CC(F)=CC=3)=CC=C2N(C)C=1CN1CCC1 YGPDNAJGPRXDSQ-UHFFFAOYSA-N 0.000 claims 1
• XYUBWAJKIJGBAU-UHFFFAOYSA-N 6-[2-(azetidin-1-ylmethyl)-1-methylindol-5-yl]-5-cyclopropyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C2=CC(C3=C(C(O)=C(C(O)=O)C(=O)N3)C3CC3)=CC=C2N(C)C=1CN1CCC1 XYUBWAJKIJGBAU-UHFFFAOYSA-N 0.000 claims 1
• MWBIEZFKXNMFNE-UHFFFAOYSA-N 6-[2-(azetidin-1-ylmethyl)-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3,4-dicarboxylic acid Chemical compound N1C(=O)C(C(O)=O)=C(C(O)=O)C(CC)=C1C1=CC=C(N(C)C(CN2CCC2)=C2)C2=C1 MWBIEZFKXNMFNE-UHFFFAOYSA-N 0.000 claims 1
• GPCOFPLGNMOVRO-UHFFFAOYSA-N 6-[2-(azetidin-1-ylmethyl)-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCC4)N(C)C3=CC=2)=C1CC GPCOFPLGNMOVRO-UHFFFAOYSA-N 0.000 claims 1
• VAWPXAIHTYKFRX-UHFFFAOYSA-N 6-[2-(butylaminomethyl)-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CNCCCC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1CC VAWPXAIHTYKFRX-UHFFFAOYSA-N 0.000 claims 1
• VLFSAHXESFKOSQ-UHFFFAOYSA-N 6-[2-(diethylaminomethyl)-1,6-dimethylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound CC=1C=C2N(C)C(CN(CC)CC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=CC=1CC VLFSAHXESFKOSQ-UHFFFAOYSA-N 0.000 claims 1
• PJEIONLNUFJWQR-UHFFFAOYSA-N 6-[2-(diethylaminomethyl)-1,7-dimethylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C(C)=C2N(C)C(CN(CC)CC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=CC=1CC PJEIONLNUFJWQR-UHFFFAOYSA-N 0.000 claims 1
• HGMZJNYIZQLHHG-UHFFFAOYSA-N 6-[2-(diethylaminomethyl)-1-methylindol-5-yl]-4-hydroxy-5-methyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CN(CC)CC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1C HGMZJNYIZQLHHG-UHFFFAOYSA-N 0.000 claims 1
• JTGMVFBPENUBNZ-UHFFFAOYSA-N 6-[2-(diethylaminomethyl)-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CN(CC)CC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=CC=1CC JTGMVFBPENUBNZ-UHFFFAOYSA-N 0.000 claims 1
• YYNYZOYDXWDZNE-UHFFFAOYSA-N 6-[2-(diethylaminomethyl)-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CN(CC)CC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1CC YYNYZOYDXWDZNE-UHFFFAOYSA-N 0.000 claims 1
• ZDJYTQQWQNFJHI-UHFFFAOYSA-N 6-[2-(diethylaminomethyl)-7-fluoro-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C(F)=C2N(C)C(CN(CC)CC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=CC=1CC ZDJYTQQWQNFJHI-UHFFFAOYSA-N 0.000 claims 1
• XOVROGHSOXVODX-UHFFFAOYSA-N 6-[2-(diethylaminomethyl)imidazo[1,2-a]pyridin-6-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.C1=CC2=NC(CN(CC)CC)=CN2C=C1C=1NC(=O)C(C(O)=O)=CC=1CC XOVROGHSOXVODX-UHFFFAOYSA-N 0.000 claims 1
• UYWBRNZKJOEUSX-UHFFFAOYSA-N 6-[2-(dimethylamino)-2,3-dihydro-1h-pyrrolo[1,2-a]indol-6-yl]-4-hydroxy-5-methyl-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.C=1C=C2N3CC(N(C)C)CC3=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1C UYWBRNZKJOEUSX-UHFFFAOYSA-N 0.000 claims 1
• XOCQVEXMBBORQR-UHFFFAOYSA-N 6-[2-(dimethylamino)-2,3-dihydro-1h-pyrrolo[1,2-a]indol-6-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C4CC(CN4C3=CC=2)N(C)C)=C1CC XOCQVEXMBBORQR-UHFFFAOYSA-N 0.000 claims 1
• BBNFIABVLQSTGR-UHFFFAOYSA-N 6-[2-(ethylaminomethyl)-1-methylindol-5-yl]-4-hydroxy-5-methyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CNCC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1C BBNFIABVLQSTGR-UHFFFAOYSA-N 0.000 claims 1
• MCRWVQXONOSJGZ-UHFFFAOYSA-N 6-[2-(ethylaminomethyl)-1h-indol-6-yl]-4-hydroxy-5-methyl-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.C1=C2NC(CNCC)=CC2=CC=C1C=1NC(=O)C(C(O)=O)=C(O)C=1C MCRWVQXONOSJGZ-UHFFFAOYSA-N 0.000 claims 1
• PPRXBICYFJGPCX-UHFFFAOYSA-N 6-[2-[(1,3-difluoropropan-2-ylamino)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC(CF)CF)N(C)C3=CC=2)=C1CC PPRXBICYFJGPCX-UHFFFAOYSA-N 0.000 claims 1
• MJEPXXGJQKNIHN-UHFFFAOYSA-N 6-[2-[(2,2-dimethylpropylamino)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC(C)(C)C)N(C)C3=CC=2)=C1CC MJEPXXGJQKNIHN-UHFFFAOYSA-N 0.000 claims 1
• WBRQMAZPOHIYDP-UHFFFAOYSA-N 6-[2-[(2-aminoethylamino)methyl]-1-methylindol-5-yl]-4-hydroxy-5-methyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCCN)N(C)C3=CC=2)=C1C WBRQMAZPOHIYDP-UHFFFAOYSA-N 0.000 claims 1
• GCIKPSHTNCBGIN-UHFFFAOYSA-N 6-[2-[(2-aminoethylamino)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCCN)N(C)C3=CC=2)=C1CC GCIKPSHTNCBGIN-UHFFFAOYSA-N 0.000 claims 1
• TWJCGVZGZKPNFH-UHFFFAOYSA-N 6-[2-[(3,3-difluoroazetidin-1-yl)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC(F)(F)C4)N(C)C3=CC=2)=C1CC TWJCGVZGZKPNFH-UHFFFAOYSA-N 0.000 claims 1
• YNGXABFKXGPQCN-UHFFFAOYSA-N 6-[2-[(3,3-difluoropyrrolidin-1-yl)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC(F)(F)CC4)N(C)C3=CC=2)=C1CC YNGXABFKXGPQCN-UHFFFAOYSA-N 0.000 claims 1
• LCZQGNXIPFUJFA-UHFFFAOYSA-N 6-[2-[(3-aminoazetidin-1-yl)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC(N)C4)N(C)C3=CC=2)=C1CC LCZQGNXIPFUJFA-UHFFFAOYSA-N 0.000 claims 1
• VPIHVILVLIBUBS-UHFFFAOYSA-N 6-[2-[(3-carboxyazetidin-1-yl)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CC(C4)C(O)=O)N(C)C3=CC=2)=C1CC VPIHVILVLIBUBS-UHFFFAOYSA-N 0.000 claims 1
• BMLCBKFOZZIDIN-UHFFFAOYSA-N 6-[2-[(4,4-difluoropiperidin-1-yl)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCC(F)(F)CC4)N(C)C3=CC=2)=C1CC BMLCBKFOZZIDIN-UHFFFAOYSA-N 0.000 claims 1
• QZLLCNZQYUDCPM-UHFFFAOYSA-N 6-[2-[(4-acetylpiperazin-1-yl)methyl]-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCN(CC4)C(C)=O)N(C)C3=CC=2)=C1CC QZLLCNZQYUDCPM-UHFFFAOYSA-N 0.000 claims 1
• SQWNOKVKVLFKIA-UHFFFAOYSA-N 6-[2-[(4-acetylpiperazin-1-yl)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCN(CC4)C(C)=O)N(C)C3=CC=2)=C1CC SQWNOKVKVLFKIA-UHFFFAOYSA-N 0.000 claims 1
• WJBQGYNMQUWCGU-UHFFFAOYSA-N 6-[2-[(4-aminopiperidin-1-yl)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4CCC(N)CC4)N(C)C3=CC=2)=C1CC WJBQGYNMQUWCGU-UHFFFAOYSA-N 0.000 claims 1
• AKHUUOZAFXGRBL-UHFFFAOYSA-N 6-[2-[(benzylamino)methyl]-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC=4C=CC=CC=4)N(C)C3=CC=2)=C1CC AKHUUOZAFXGRBL-UHFFFAOYSA-N 0.000 claims 1
• IGJXWDVFDBULRA-UHFFFAOYSA-N 6-[2-[(benzylamino)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC=4C=CC=CC=4)N(C)C3=CC=2)=C1CC IGJXWDVFDBULRA-UHFFFAOYSA-N 0.000 claims 1
• ABAABTPBJGOTNM-UHFFFAOYSA-N 6-[2-[(butan-2-ylamino)methyl]-1-methylindol-5-yl]-4-hydroxy-5-methyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CNC(C)CC)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1C ABAABTPBJGOTNM-UHFFFAOYSA-N 0.000 claims 1
• CGXCSYLSICCARF-UHFFFAOYSA-N 6-[2-[(butan-2-ylamino)methyl]-1h-indol-6-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.C1=C2NC(CNC(C)CC)=CC2=CC=C1C=1NC(=O)C(C(O)=O)=C(O)C=1CC CGXCSYLSICCARF-UHFFFAOYSA-N 0.000 claims 1
• UVIDTOPVXZJKKJ-UHFFFAOYSA-N 6-[2-[(cyclobutylamino)methyl]-1-methylindol-5-yl]-4-hydroxy-5-methyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC4CCC4)N(C)C3=CC=2)=C1C UVIDTOPVXZJKKJ-UHFFFAOYSA-N 0.000 claims 1
• IARYTKMIUPFOTR-UHFFFAOYSA-N 6-[2-[(cyclobutylamino)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC4CCC4)N(C)C3=CC=2)=C1CC IARYTKMIUPFOTR-UHFFFAOYSA-N 0.000 claims 1
• NAQOSNLTMCBPRD-UHFFFAOYSA-N 6-[2-[(cyclobutylmethylamino)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC4CCC4)N(C)C3=CC=2)=C1CC NAQOSNLTMCBPRD-UHFFFAOYSA-N 0.000 claims 1
• HYWMXDHXFGTCLU-UHFFFAOYSA-N 6-[2-[(cycloheptylmethylamino)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC4CCCCCC4)N(C)C3=CC=2)=C1CC HYWMXDHXFGTCLU-UHFFFAOYSA-N 0.000 claims 1
• KMCCINGOAAQXKA-UHFFFAOYSA-N 6-[2-[(cyclohexylamino)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC4CCCCC4)N(C)C3=CC=2)=C1CC KMCCINGOAAQXKA-UHFFFAOYSA-N 0.000 claims 1
• YKHCMFKZEFNVSB-UHFFFAOYSA-N 6-[2-[(cyclopentylamino)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC4CCCC4)N(C)C3=CC=2)=C1CC YKHCMFKZEFNVSB-UHFFFAOYSA-N 0.000 claims 1
• IQYOXDHDEPALSQ-UHFFFAOYSA-N 6-[2-[(cyclopentylmethylamino)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC4CCCC4)N(C)C3=CC=2)=C1CC IQYOXDHDEPALSQ-UHFFFAOYSA-N 0.000 claims 1
• GHODNTJWPGBGHV-UHFFFAOYSA-N 6-[2-[(cyclopropylamino)methyl]-1-methylindol-5-yl]-4-hydroxy-5-methyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC4CC4)N(C)C3=CC=2)=C1C GHODNTJWPGBGHV-UHFFFAOYSA-N 0.000 claims 1
• AHFYVLYANFOYCO-UHFFFAOYSA-N 6-[2-[(cyclopropylamino)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC4CC4)N(C)C3=CC=2)=C1CC AHFYVLYANFOYCO-UHFFFAOYSA-N 0.000 claims 1
• FHCZPVNXSBHGOA-UHFFFAOYSA-N 6-[2-[(cyclopropylmethylamino)methyl]-1-methylindol-5-yl]-4-hydroxy-5-methyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC4CC4)N(C)C3=CC=2)=C1C FHCZPVNXSBHGOA-UHFFFAOYSA-N 0.000 claims 1
• SFSQOALOZVTRGL-UHFFFAOYSA-N 6-[2-[(cyclopropylmethylamino)methyl]-1-methylindol-5-yl]-5-(4-fluorophenyl)-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C2=CC(C3=C(C(O)=C(C(O)=O)C(=O)N3)C=3C=CC(F)=CC=3)=CC=C2N(C)C=1CNCC1CC1 SFSQOALOZVTRGL-UHFFFAOYSA-N 0.000 claims 1
• DGGHAGJJNSNUFP-UHFFFAOYSA-N 6-[2-[(cyclopropylmethylamino)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNCC4CC4)N(C)C3=CC=2)=C1CC DGGHAGJJNSNUFP-UHFFFAOYSA-N 0.000 claims 1
• FHGKMEMSQRYNKC-UHFFFAOYSA-N 6-[2-[(dimethylamino)methyl]-1,6-dimethylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C(=CC=3N(C)C(CN(C)C)=CC=3C=2)C)=C1CC FHGKMEMSQRYNKC-UHFFFAOYSA-N 0.000 claims 1
• SQWRNXDPONMLMC-UHFFFAOYSA-N 6-[2-[(dimethylamino)methyl]-1,7-dimethylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN(C)C)N(C)C3=C(C)C=2)=C1CC SQWRNXDPONMLMC-UHFFFAOYSA-N 0.000 claims 1
• WLZDNAUKVWZXTE-UHFFFAOYSA-N 6-[2-[(dimethylamino)methyl]-1-methylindol-5-yl]-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CN(C)C)=CC2=CC=1C1=CC(O)=C(C(O)=O)C(=O)N1 WLZDNAUKVWZXTE-UHFFFAOYSA-N 0.000 claims 1
• JLMCDZYAWSTZMJ-UHFFFAOYSA-N 6-[2-[(dimethylamino)methyl]-1-methylindol-5-yl]-4-hydroxy-2-oxo-5-propan-2-yl-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN(C)C)N(C)C3=CC=2)=C1C(C)C JLMCDZYAWSTZMJ-UHFFFAOYSA-N 0.000 claims 1
• QNFNVBHSHTUNKN-UHFFFAOYSA-N 6-[2-[(dimethylamino)methyl]-1-methylindol-5-yl]-4-hydroxy-2-oxo-5-propyl-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN(C)C)N(C)C3=CC=2)=C1CCC QNFNVBHSHTUNKN-UHFFFAOYSA-N 0.000 claims 1
• LDOGXIAANRXUJF-UHFFFAOYSA-N 6-[2-[(dimethylamino)methyl]-1-methylindol-5-yl]-4-hydroxy-5-methyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CN(C)C)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1C LDOGXIAANRXUJF-UHFFFAOYSA-N 0.000 claims 1
• WWNRQAWTHYDLFX-UHFFFAOYSA-N 6-[2-[(dimethylamino)methyl]-1-methylindol-5-yl]-5-(4-fluorophenyl)-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C=1C=C2N(C)C(CN(C)C)=CC2=CC=1C=1NC(=O)C(C(O)=O)=C(O)C=1C1=CC=C(F)C=C1 WWNRQAWTHYDLFX-UHFFFAOYSA-N 0.000 claims 1
• DZAPFMQAECCELO-UHFFFAOYSA-N 6-[2-[(dimethylamino)methyl]-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3,4-dicarboxylic acid Chemical compound N1C(=O)C(C(O)=O)=C(C(O)=O)C(CC)=C1C1=CC=C(N(C)C(CN(C)C)=C2)C2=C1 DZAPFMQAECCELO-UHFFFAOYSA-N 0.000 claims 1
• MVKRBLJIVXVOBO-UHFFFAOYSA-N 6-[2-[(dimethylamino)methyl]-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN(C)C)N(C)C3=CC=2)=C1CC MVKRBLJIVXVOBO-UHFFFAOYSA-N 0.000 claims 1
• XBUYXFOWZZAWON-UHFFFAOYSA-N 6-[2-[(dimethylamino)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN(C)C)N(C)C3=CC=2)=C1CC XBUYXFOWZZAWON-UHFFFAOYSA-N 0.000 claims 1
• GBMYWWRVRPBUIR-UHFFFAOYSA-N 6-[2-[(dimethylamino)methyl]-1h-indol-6-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC1=C(C(O)=O)C(=O)NC(C=2C=C3NC(CN(C)C)=CC3=CC=2)=C1CC GBMYWWRVRPBUIR-UHFFFAOYSA-N 0.000 claims 1
• FAEISHWDXHIBKQ-UHFFFAOYSA-N 6-[2-[(dimethylamino)methyl]-7-fluoro-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN(C)C)N(C)C3=C(F)C=2)=C1CC FAEISHWDXHIBKQ-UHFFFAOYSA-N 0.000 claims 1
• XQGPMCJFYVUBJO-UHFFFAOYSA-N 6-[2-[(dimethylamino)methyl]imidazo[1,2-a]pyridin-6-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.C1=C(C(O)=O)C(=O)NC(C2=CN3C=C(CN(C)C)N=C3C=C2)=C1CC XQGPMCJFYVUBJO-UHFFFAOYSA-N 0.000 claims 1
• ZJCGSQWYVASKPQ-UHFFFAOYSA-N 6-[2-[(tert-butylamino)methyl]-1-methylindol-5-yl]-4-hydroxy-5-methyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC(C)(C)C)N(C)C3=CC=2)=C1C ZJCGSQWYVASKPQ-UHFFFAOYSA-N 0.000 claims 1
• CWLMGUGZWPZLFX-UHFFFAOYSA-N 6-[2-[(tert-butylamino)methyl]-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC(C)(C)C)N(C)C3=CC=2)=C1CC CWLMGUGZWPZLFX-UHFFFAOYSA-N 0.000 claims 1
• FUTKEHOEWOLASX-UHFFFAOYSA-N 6-[2-[(tert-butylamino)methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CNC(C)(C)C)N(C)C3=CC=2)=C1CC FUTKEHOEWOLASX-UHFFFAOYSA-N 0.000 claims 1
• IUDNOIUPAIYRRU-UHFFFAOYSA-N 6-[2-[(tert-butylamino)methyl]-3-fluoro-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C(F)=C(CNC(C)(C)C)N(C)C3=CC=2)=C1CC IUDNOIUPAIYRRU-UHFFFAOYSA-N 0.000 claims 1
• NPDQRSLAXWJHHA-UHFFFAOYSA-N 6-[2-[2-(dimethylamino)ethyl]-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CCN(C)C)N(C)C3=CC=2)=C1CC NPDQRSLAXWJHHA-UHFFFAOYSA-N 0.000 claims 1
• GZKQPCOOMQLNPK-UHFFFAOYSA-N 6-[2-[2-(dimethylamino)propan-2-yl]-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(N(C)C3=CC=2)C(C)(C)N(C)C)=C1CC GZKQPCOOMQLNPK-UHFFFAOYSA-N 0.000 claims 1
• UHCOJFLMPFLLAV-UHFFFAOYSA-N 6-[2-[2-(dimethylamino)propan-2-yl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(N(C)C3=CC=2)C(C)(C)N(C)C)=C1CC UHCOJFLMPFLLAV-UHFFFAOYSA-N 0.000 claims 1
• DSCXFTAMRUYCOT-GASCZTMLSA-N 6-[2-[[(2r,6s)-2,6-dimethylmorpholin-4-yl]methyl]-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C[C@@H](C)O[C@@H](C)C4)N(C)C3=CC=2)=C1CC DSCXFTAMRUYCOT-GASCZTMLSA-N 0.000 claims 1
• XEMNAIFZUFSELF-NRFANRHFSA-N 6-[2-[[(2s)-2-(anilinomethyl)pyrrolidin-1-yl]methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4[C@@H](CCC4)CNC=4C=CC=CC=4)N(C)C3=CC=2)=C1CC XEMNAIFZUFSELF-NRFANRHFSA-N 0.000 claims 1
• ZHSKCYJHJBEUAO-FXPIJTFKSA-N 6-[2-[[(3ar,4r,6as)-4-(dibenzylamino)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C[C@@H]5[C@@H](CC[C@@H]5C4)N(CC=4C=CC=CC=4)CC=4C=CC=CC=4)N(C)C3=CC=2)=C1CC ZHSKCYJHJBEUAO-FXPIJTFKSA-N 0.000 claims 1
• HIOZAHZHKCCWPK-RVSNTGDXSA-N 6-[2-[[(3ar,4r,6as)-4-(dimethylamino)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]methyl]-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C[C@@H]5[C@@H](CC[C@@H]5C4)N(C)C)N(C)C3=CC=2)=C1CC HIOZAHZHKCCWPK-RVSNTGDXSA-N 0.000 claims 1
• DREFIDLQNSJLMC-QGCDCVKKSA-N 6-[2-[[(3ar,4r,6as)-4-(dimethylamino)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C[C@@H]5[C@@H](CC[C@@H]5C4)N(C)C)N(C)C3=CC=2)=C1CC DREFIDLQNSJLMC-QGCDCVKKSA-N 0.000 claims 1
• VRYOARSOUYLXJZ-MDASCCDHSA-N 6-[2-[[(3ar,4r,6as)-4-amino-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C[C@@H]5[C@H](N)CC[C@@H]5C4)N(C)C3=CC=2)=C1CC VRYOARSOUYLXJZ-MDASCCDHSA-N 0.000 claims 1
• XZERUVJBFSAAAU-JWNONTMASA-N 6-[2-[[(3ar,4r,7as)-4-(dibenzylamino)-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl]methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C[C@@H]5[C@@H](CCC[C@@H]5C4)N(CC=4C=CC=CC=4)CC=4C=CC=CC=4)N(C)C3=CC=2)=C1CC XZERUVJBFSAAAU-JWNONTMASA-N 0.000 claims 1
• GCSBTXIUHJXGMP-HFRGRHLUSA-N 6-[2-[[(3ar,4r,7as)-4-(dimethylamino)-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl]methyl]-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C[C@@H]5[C@@H](CCC[C@@H]5C4)N(C)C)N(C)C3=CC=2)=C1CC GCSBTXIUHJXGMP-HFRGRHLUSA-N 0.000 claims 1
• WZRMNXLMPHKJJP-JEVIFJNESA-N 6-[2-[[(3ar,4r,7as)-4-[benzyl(methyl)amino]-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl]methyl]-1-methylindol-5-yl]-5-ethyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C[C@@H]5[C@@H](CCC[C@@H]5C4)N(C)CC=4C=CC=CC=4)N(C)C3=CC=2)=C1CC WZRMNXLMPHKJJP-JEVIFJNESA-N 0.000 claims 1
• VSUXUXXIIFORGR-UIAACRFSSA-N 6-[2-[[(3ar,4r,7as)-4-amino-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl]methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C[C@@H]5[C@H](N)CCC[C@@H]5C4)N(C)C3=CC=2)=C1CC VSUXUXXIIFORGR-UIAACRFSSA-N 0.000 claims 1
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• BBZHVPUGDNAPLH-AWEZNQCLSA-N 6-[2-[[(3s)-3-aminopyrrolidin-1-yl]methyl]-1-methylindol-5-yl]-5-ethyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC1=C(C(O)=O)C(=O)NC(C=2C=C3C=C(CN4C[C@@H](N)CC4)N(C)C3=CC=2)=C1CC BBZHVPUGDNAPLH-AWEZNQCLSA-N 0.000 claims 1
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