AU2014249050B2 - Histone dementhylase inhibitors - Google Patents

Info

Publication number

AU2014249050B2

AU2014249050B2 AU2014249050A AU2014249050A AU2014249050B2 AU 2014249050 B2 AU2014249050 B2 AU 2014249050B2 AU 2014249050 A AU2014249050 A AU 2014249050A AU 2014249050 A AU2014249050 A AU 2014249050A AU 2014249050 B2 AU2014249050 B2 AU 2014249050B2

Authority

AU

Australia

Prior art keywords

compound

pyridine

pyrrolo

formula

methyl

Prior art date

2013-03-12

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.)

Ceased

Links

• Espacenet
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• 108010033040 Histones Proteins 0.000 title description 25
• 239000003112 inhibitor Substances 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 495
• 238000000034 method Methods 0.000 claims abstract description 169
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 27
• 108010074870 Histone Demethylases Proteins 0.000 claims abstract description 26
• 102000008157 Histone Demethylases Human genes 0.000 claims abstract description 26
• 201000011510 cancer Diseases 0.000 claims abstract description 19
• 230000005764 inhibitory process Effects 0.000 claims abstract description 14
• 239000008194 pharmaceutical composition Chemical class 0.000 claims abstract description 14
• 238000011282 treatment Methods 0.000 claims abstract description 10
• 206010006187 Breast cancer Diseases 0.000 claims abstract description 8
• 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 107
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 95
• 125000000217 alkyl group Chemical group 0.000 claims description 87
• 125000001072 heteroaryl group Chemical group 0.000 claims description 65
• 125000000623 heterocyclic group Chemical group 0.000 claims description 65
• 125000003118 aryl group Chemical group 0.000 claims description 60
• 150000003839 salts Chemical class 0.000 claims description 50
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
• 239000001257 hydrogen Substances 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 27
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 125000003282 alkyl amino group Chemical group 0.000 claims description 15
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 15
• 230000002401 inhibitory effect Effects 0.000 claims description 10
• 150000001204 N-oxides Chemical class 0.000 claims description 8
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• 150000002367 halogens Chemical group 0.000 claims description 7
• FLSRYTNCCBDWES-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-1H-pyrrolo[3,2-b]pyridine-7-carboxylic acid Chemical compound OC(=O)c1ccnc2cc(Cc3ccccc3Cl)[nH]c12 FLSRYTNCCBDWES-UHFFFAOYSA-N 0.000 claims description 5
• LYHNEWHXQFZJRR-UHFFFAOYSA-N methyl 2-[hydroxy(phenyl)methyl]-1h-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound N1C=2C(C(=O)OC)=CC=NC=2C=C1C(O)C1=CC=CC=C1 LYHNEWHXQFZJRR-UHFFFAOYSA-N 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• GAVWFVROXVJBIK-UHFFFAOYSA-N 2-(1-hydroxycyclopentyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylic acid Chemical compound OC(=O)c1ccnc2cc([nH]c12)C1(O)CCCC1 GAVWFVROXVJBIK-UHFFFAOYSA-N 0.000 claims description 3
• VFNSKTHFPJWUKV-UHFFFAOYSA-N 2-(1-phenoxyethyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylic acid Chemical compound CC(Oc1ccccc1)c1cc2nccc(C(O)=O)c2[nH]1 VFNSKTHFPJWUKV-UHFFFAOYSA-N 0.000 claims description 3
• YYVQUZIWKZVUOA-UHFFFAOYSA-N 2-(4,4-dimethylpiperidine-1-carbonyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylic acid Chemical compound CC1(CCN(CC1)C(=O)C1=CC2=NC=CC(=C2N1)C(=O)O)C YYVQUZIWKZVUOA-UHFFFAOYSA-N 0.000 claims description 3
• FFZURRPWJDSXFU-UHFFFAOYSA-N 2-(phenoxymethyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylic acid Chemical compound OC(=O)c1ccnc2cc(COc3ccccc3)[nH]c12 FFZURRPWJDSXFU-UHFFFAOYSA-N 0.000 claims description 3
• MIUMGHXOBSQBOU-UHFFFAOYSA-N 2-[(3,5-difluorophenoxy)methyl]-1H-pyrrolo[3,2-b]pyridine-7-carboxylic acid Chemical compound OC(=O)c1ccnc2cc(COc3cc(F)cc(F)c3)[nH]c12 MIUMGHXOBSQBOU-UHFFFAOYSA-N 0.000 claims description 3
• SKIADERQBBOJPL-UHFFFAOYSA-N 2-[(3-methylphenoxy)methyl]-1H-pyrrolo[3,2-b]pyridine-7-carboxylic acid Chemical compound Cc1cccc(OCc2cc3nccc(C(O)=O)c3[nH]2)c1 SKIADERQBBOJPL-UHFFFAOYSA-N 0.000 claims description 3
• PTTDMGLUDKSVEN-UHFFFAOYSA-N 2-[(4-chlorophenoxy)methyl]-1H-pyrrolo[3,2-b]pyridine-7-carboxylic acid Chemical compound OC(=O)c1ccnc2cc(COc3ccc(Cl)cc3)[nH]c12 PTTDMGLUDKSVEN-UHFFFAOYSA-N 0.000 claims description 3
• CEIHDMRTHCSEQL-UHFFFAOYSA-N 2-[(4-fluorophenyl)methyl]-1H-pyrrolo[3,2-b]pyridine-7-carboxylic acid Chemical compound OC(=O)c1ccnc2cc(Cc3ccc(F)cc3)[nH]c12 CEIHDMRTHCSEQL-UHFFFAOYSA-N 0.000 claims description 3
• YXMPZMPYIOJEEH-UHFFFAOYSA-N 2-[cyclopropyl(hydroxy)methyl]-1H-pyrrolo[3,2-b]pyridine-7-carboxylic acid Chemical compound OC(C1CC1)c1cc2nccc(C(O)=O)c2[nH]1 YXMPZMPYIOJEEH-UHFFFAOYSA-N 0.000 claims description 3
• GKUPKODNWZNZJU-UHFFFAOYSA-N 2-[hydroxy-(2-methylpyrazol-3-yl)methyl]-1H-pyrrolo[3,2-b]pyridine-7-carboxylic acid Chemical compound Cn1nccc1C(O)c1cc2nccc(C(O)=O)c2[nH]1 GKUPKODNWZNZJU-UHFFFAOYSA-N 0.000 claims description 3
• DNMHSZMGJQXBPR-UHFFFAOYSA-N 2-[hydroxy-(3-methylphenyl)methyl]-1h-pyrrolo[3,2-b]pyridine-7-carboxylic acid Chemical compound CC1=CC=CC(C(O)C=2NC3=C(C(O)=O)C=CN=C3C=2)=C1 DNMHSZMGJQXBPR-UHFFFAOYSA-N 0.000 claims description 3
• 239000003814 drug Substances 0.000 claims description 3
• SVTALYNTRBNTBC-UHFFFAOYSA-N 2-(2-cyclopropyl-1-hydroxyethyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylic acid Chemical compound OC(CC1CC1)c1cc2nccc(C(O)=O)c2[nH]1 SVTALYNTRBNTBC-UHFFFAOYSA-N 0.000 claims description 2
• 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• YVSBFLGSNJSZJQ-UHFFFAOYSA-N 2-(pyrrolidine-1-carbonyl)-1h-pyrrolo[3,2-b]pyridine-7-carboxylic acid Chemical compound N1C=2C(C(=O)O)=CC=NC=2C=C1C(=O)N1CCCC1 YVSBFLGSNJSZJQ-UHFFFAOYSA-N 0.000 claims 1
• 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
• 201000004101 esophageal cancer Diseases 0.000 claims 1
• -1 pyrrolopyridine derivative compounds Chemical class 0.000 abstract description 126
• 239000000203 mixture Substances 0.000 abstract description 34
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 14
• 201000010099 disease Diseases 0.000 abstract description 11
• 206010005003 Bladder cancer Diseases 0.000 abstract description 5
• 206010058467 Lung neoplasm malignant Diseases 0.000 abstract description 5
• 208000000236 Prostatic Neoplasms Diseases 0.000 abstract description 5
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 abstract description 5
• 201000005202 lung cancer Diseases 0.000 abstract description 5
• 208000020816 lung neoplasm Diseases 0.000 abstract description 5
• 201000005112 urinary bladder cancer Diseases 0.000 abstract description 5
• 206010060862 Prostate cancer Diseases 0.000 abstract description 4
• 201000001441 melanoma Diseases 0.000 abstract description 4
• 230000001613 neoplastic effect Effects 0.000 abstract description 3
• 238000002360 preparation method Methods 0.000 description 144
• 238000005481 NMR spectroscopy Methods 0.000 description 129
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 64
• 238000006243 chemical reaction Methods 0.000 description 46
• 125000004432 carbon atom Chemical group C* 0.000 description 32
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 32
• 150000003254 radicals Chemical class 0.000 description 30
• 210000004027 cell Anatomy 0.000 description 28
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 26
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 24
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 22
• 239000000126 substance Substances 0.000 description 22
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
• 238000003556 assay Methods 0.000 description 21
• KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 18
• 101150041968 CDC13 gene Proteins 0.000 description 18
• 238000005160 1H NMR spectroscopy Methods 0.000 description 16
• 101001088893 Homo sapiens Lysine-specific demethylase 4C Proteins 0.000 description 16
• 108090000623 proteins and genes Proteins 0.000 description 16
• 125000001424 substituent group Chemical group 0.000 description 16
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
• 101000615488 Homo sapiens Methyl-CpG-binding domain protein 2 Proteins 0.000 description 15
• 102100033230 Lysine-specific demethylase 4C Human genes 0.000 description 15
• 102100021299 Methyl-CpG-binding domain protein 2 Human genes 0.000 description 15
• 125000004415 heterocyclylalkyl group Chemical group 0.000 description 15
• 102000006947 Histones Human genes 0.000 description 14
• 101000613625 Homo sapiens Lysine-specific demethylase 4A Proteins 0.000 description 14
• 102100040863 Lysine-specific demethylase 4A Human genes 0.000 description 14
• 125000003710 aryl alkyl group Chemical group 0.000 description 14
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
• 239000002253 acid Substances 0.000 description 13
• 238000001514 detection method Methods 0.000 description 13
• 235000019439 ethyl acetate Nutrition 0.000 description 13
• 125000003709 fluoroalkyl group Chemical group 0.000 description 13
• 125000004446 heteroarylalkyl group Chemical group 0.000 description 13
• 229910052757 nitrogen Inorganic materials 0.000 description 13
• 229910052799 carbon Inorganic materials 0.000 description 12
• 235000018102 proteins Nutrition 0.000 description 12
• 102000004169 proteins and genes Human genes 0.000 description 12
• 238000012360 testing method Methods 0.000 description 12
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
• 125000004450 alkenylene group Chemical group 0.000 description 11
• 125000005884 carbocyclylalkyl group Chemical group 0.000 description 11
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 10
• 102100033247 Lysine-specific demethylase 5B Human genes 0.000 description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
• 238000004440 column chromatography Methods 0.000 description 10
• 125000004122 cyclic group Chemical group 0.000 description 10
• 125000005843 halogen group Chemical group 0.000 description 10
• 235000018977 lysine Nutrition 0.000 description 10
• 238000007069 methylation reaction Methods 0.000 description 10
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
• 239000000651 prodrug Substances 0.000 description 10
• 229940002612 prodrug Drugs 0.000 description 10
• 238000003756 stirring Methods 0.000 description 10
• 238000002877 time resolved fluorescence resonance energy transfer Methods 0.000 description 10
• 101001088883 Homo sapiens Lysine-specific demethylase 5B Proteins 0.000 description 9
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 9
• 239000004472 Lysine Substances 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 125000003342 alkenyl group Chemical group 0.000 description 9
• 125000000304 alkynyl group Chemical group 0.000 description 9
• 239000002585 base Substances 0.000 description 9
• 108090000765 processed proteins & peptides Proteins 0.000 description 9
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
• 101100477411 Dictyostelium discoideum set1 gene Proteins 0.000 description 8
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
• HWXBTNAVRSUOJR-UHFFFAOYSA-N alpha-hydroxyglutaric acid Natural products OC(=O)C(O)CCC(O)=O HWXBTNAVRSUOJR-UHFFFAOYSA-N 0.000 description 8
• 229940009533 alpha-ketoglutaric acid Drugs 0.000 description 8
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• 125000004433 nitrogen atom Chemical group N* 0.000 description 8
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• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
• 239000003153 chemical reaction reagent Substances 0.000 description 7
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• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• 101001088892 Homo sapiens Lysine-specific demethylase 5A Proteins 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• 239000012267 brine Substances 0.000 description 6
• 239000003921 oil Substances 0.000 description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
• 239000011541 reaction mixture Substances 0.000 description 6
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
• 239000002904 solvent Substances 0.000 description 6
• 125000003107 substituted aryl group Chemical group 0.000 description 6
• 125000003831 tetrazolyl group Chemical group 0.000 description 6
• WOVKYSAHUYNSMH-RRKCRQDMSA-N 5-bromodeoxyuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Br)=C1 WOVKYSAHUYNSMH-RRKCRQDMSA-N 0.000 description 5
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• 125000001841 imino group Chemical group [H]N=* 0.000 description 5
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• 229920006395 saturated elastomer Polymers 0.000 description 5
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
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• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
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• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
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• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
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• DIEUGINJYISDCB-UHFFFAOYSA-N ethyl 6-amino-5-methoxy-1h-indole-2-carboxylate Chemical compound COC1=C(N)C=C2NC(C(=O)OCC)=CC2=C1 DIEUGINJYISDCB-UHFFFAOYSA-N 0.000 description 4
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• 230000005284 excitation Effects 0.000 description 4
• IMBKASBLAKCLEM-UHFFFAOYSA-L ferrous ammonium sulfate (anhydrous) Chemical compound [NH4+].[NH4+].[Fe+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O IMBKASBLAKCLEM-UHFFFAOYSA-L 0.000 description 4
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• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• KSZMBXHYSQDICN-UHFFFAOYSA-N methyl 3-amino-2-chloropyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC(Cl)=C1N KSZMBXHYSQDICN-UHFFFAOYSA-N 0.000 description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
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• PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 4
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• 102000016624 JmjC domains Human genes 0.000 description 3
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• CBHYEKXZUJKIFP-UHFFFAOYSA-N methyl 2-(1-hydroxypropyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound CCC(O)c1cc2nccc(C(=O)OC)c2[nH]1 CBHYEKXZUJKIFP-UHFFFAOYSA-N 0.000 description 2
• AZPANMQXTFKPAS-UHFFFAOYSA-N methyl 2-(2,2-dimethylpyrrolidine-1-carbonyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc([nH]c12)C(=O)N1CCCC1(C)C AZPANMQXTFKPAS-UHFFFAOYSA-N 0.000 description 2
• ILHWOVQUFIOJCF-UHFFFAOYSA-N methyl 2-(2,3-dihydro-1-benzofuran-5-yloxymethyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc(COc3ccc4OCCc4c3)[nH]c12 ILHWOVQUFIOJCF-UHFFFAOYSA-N 0.000 description 2
• KQTRKXVPRHGMMK-UHFFFAOYSA-N methyl 2-(2,3-dihydroindole-1-carbonyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc([nH]c12)C(=O)N1CCc2ccccc12 KQTRKXVPRHGMMK-UHFFFAOYSA-N 0.000 description 2
• KKKRNYIFNPXOHS-UHFFFAOYSA-N methyl 2-(2-cyanoethyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc(CCC#N)[nH]c12 KKKRNYIFNPXOHS-UHFFFAOYSA-N 0.000 description 2
• SORGNBCIASSAMH-UHFFFAOYSA-N methyl 2-(2-cyclopropyl-1-hydroxyethyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc([nH]c12)C(O)CC1CC1 SORGNBCIASSAMH-UHFFFAOYSA-N 0.000 description 2
• NTMWRTATHXGDLP-UHFFFAOYSA-N methyl 2-(2-hydroxypropan-2-yl)-1h-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)C1=CC=NC2=C1NC(C(C)(C)O)=C2 NTMWRTATHXGDLP-UHFFFAOYSA-N 0.000 description 2
• FJXLPPZIUHDDNM-UHFFFAOYSA-N methyl 2-(3,4-dihydro-2H-quinoline-1-carbonyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound N1(CCCC2=CC=CC=C12)C(=O)C1=CC2=NC=CC(=C2N1)C(=O)OC FJXLPPZIUHDDNM-UHFFFAOYSA-N 0.000 description 2
• LOTMOAVJJPAAHQ-UHFFFAOYSA-N methyl 2-(3-phenylpiperidine-1-carbonyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc([nH]c12)C(=O)N1CCCC(C1)c1ccccc1 LOTMOAVJJPAAHQ-UHFFFAOYSA-N 0.000 description 2
• UXZDAQNEYNJZBT-UHFFFAOYSA-N methyl 2-(3-phenylpyrrolidine-1-carbonyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc([nH]c12)C(=O)N1CCC(C1)c1ccccc1 UXZDAQNEYNJZBT-UHFFFAOYSA-N 0.000 description 2
• DXODFNCCDMPWIP-UHFFFAOYSA-N methyl 2-(4,4-dimethylpiperidine-1-carbonyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc([nH]c12)C(=O)N1CCC(C)(C)CC1 DXODFNCCDMPWIP-UHFFFAOYSA-N 0.000 description 2
• DDAUBHYKYBXPQN-UHFFFAOYSA-N methyl 2-(4-methoxy-2-methylphenyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc([nH]c12)-c1ccc(OC)cc1C DDAUBHYKYBXPQN-UHFFFAOYSA-N 0.000 description 2
• YROWUSARYSGPIU-UHFFFAOYSA-N methyl 2-(cyclohexylmethyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc(CC3CCCCC3)[nH]c12 YROWUSARYSGPIU-UHFFFAOYSA-N 0.000 description 2
• BWUQYUDHNYIGTF-UHFFFAOYSA-N methyl 2-(cyclopentylmethyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc(CC3CCCC3)[nH]c12 BWUQYUDHNYIGTF-UHFFFAOYSA-N 0.000 description 2
• DTQHKSVJUFHWRN-UHFFFAOYSA-N methyl 2-(methoxymethyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COCc1cc2nccc(C(=O)OC)c2[nH]1 DTQHKSVJUFHWRN-UHFFFAOYSA-N 0.000 description 2
• JSXIVOWOFDZPPT-UHFFFAOYSA-N methyl 2-(piperidine-1-carbonyl)-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc([nH]c12)C(=O)N1CCCCC1 JSXIVOWOFDZPPT-UHFFFAOYSA-N 0.000 description 2
• WDONAPBKHGJDQD-UHFFFAOYSA-N methyl 2-[(2-chlorophenyl)methyl]-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc(Cc3ccccc3Cl)[nH]c12 WDONAPBKHGJDQD-UHFFFAOYSA-N 0.000 description 2
• SDEFQXCZIBRRNB-UHFFFAOYSA-N methyl 2-[(2-methylphenoxy)methyl]-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc(COc3ccccc3C)[nH]c12 SDEFQXCZIBRRNB-UHFFFAOYSA-N 0.000 description 2
• JLODWJOBETWRKG-UHFFFAOYSA-N methyl 2-[(3-methylphenoxy)methyl]-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc(COc3cccc(C)c3)[nH]c12 JLODWJOBETWRKG-UHFFFAOYSA-N 0.000 description 2
• IGLHMENSXNDITI-UHFFFAOYSA-N methyl 2-[(3-methylphenyl)methyl]-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc(Cc3cccc(C)c3)[nH]c12 IGLHMENSXNDITI-UHFFFAOYSA-N 0.000 description 2
• CRRBKSPYDVFVMH-UHFFFAOYSA-N methyl 2-[(4-chlorophenoxy)methyl]-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc(COc3ccc(Cl)cc3)[nH]c12 CRRBKSPYDVFVMH-UHFFFAOYSA-N 0.000 description 2
• JKNAGLOINBWOBG-UHFFFAOYSA-N methyl 2-[(4-methylphenoxy)methyl]-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc(COc3ccc(C)cc3)[nH]c12 JKNAGLOINBWOBG-UHFFFAOYSA-N 0.000 description 2
• XYKLRHZOPNWXRD-UHFFFAOYSA-N methyl 2-[[4-(trifluoromethyl)phenoxy]methyl]-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc(COc3ccc(cc3)C(F)(F)F)[nH]c12 XYKLRHZOPNWXRD-UHFFFAOYSA-N 0.000 description 2
• MPKCMJQIYMSSTD-UHFFFAOYSA-N methyl 2-[cyclopropyl(hydroxy)methyl]-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc([nH]c12)C(O)C1CC1 MPKCMJQIYMSSTD-UHFFFAOYSA-N 0.000 description 2
• JDBGFXLUVCJGRQ-UHFFFAOYSA-N methyl 2-[hydroxy(oxan-4-yl)methyl]-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc([nH]c12)C(O)C1CCOCC1 JDBGFXLUVCJGRQ-UHFFFAOYSA-N 0.000 description 2
• FQEMSHRKUOJNBC-UHFFFAOYSA-N methyl 2-[hydroxy-(1-methylpyrazol-4-yl)methyl]-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc([nH]c12)C(O)c1cnn(C)c1 FQEMSHRKUOJNBC-UHFFFAOYSA-N 0.000 description 2
• CAZSDITUVPNQBH-UHFFFAOYSA-N methyl 2-[hydroxy-(2-methylpyrazol-3-yl)methyl]-1H-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound COC(=O)c1ccnc2cc([nH]c12)C(O)c1ccnn1C CAZSDITUVPNQBH-UHFFFAOYSA-N 0.000 description 2
• GGDVOVFHOWTHRR-UHFFFAOYSA-N methyl 2-benzyl-1h-pyrrolo[3,2-b]pyridine-7-carboxylate Chemical compound N1C=2C(C(=O)OC)=CC=NC=2C=C1CC1=CC=CC=C1 GGDVOVFHOWTHRR-UHFFFAOYSA-N 0.000 description 2
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