ES2660210T3 - Derivados de indolcarboxamida y usos de los mismos - Google Patents
Derivados de indolcarboxamida y usos de los mismos Download PDFInfo
- Publication number
- ES2660210T3 ES2660210T3 ES13792084.9T ES13792084T ES2660210T3 ES 2660210 T3 ES2660210 T3 ES 2660210T3 ES 13792084 T ES13792084 T ES 13792084T ES 2660210 T3 ES2660210 T3 ES 2660210T3
- Authority
- ES
- Spain
- Prior art keywords
- indole
- carboxamide
- methylcyclohexyl
- dichloro
- compound
- Prior art date
- 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.)
- Active
Links
- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical class C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 125
- -1 fluoro-substituted methyl Chemical group 0.000 claims abstract description 44
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 239000000460 chlorine Substances 0.000 claims abstract description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 24
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 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 abstract description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 201000008827 tuberculosis Diseases 0.000 claims description 64
- 239000003814 drug Substances 0.000 claims description 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
- 229940079593 drug Drugs 0.000 claims description 27
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 15
- 208000035475 disorder Diseases 0.000 claims description 13
- UATYSFRIVIHVKL-UHFFFAOYSA-N n-(4,4-dimethylcyclohexyl)-4,6-difluoro-1h-indole-2-carboxamide Chemical compound C1CC(C)(C)CCC1NC(=O)C1=CC2=C(F)C=C(F)C=C2N1 UATYSFRIVIHVKL-UHFFFAOYSA-N 0.000 claims description 11
- 206010036790 Productive cough Diseases 0.000 claims description 10
- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 claims description 10
- 208000024794 sputum Diseases 0.000 claims description 10
- 210000003802 sputum Anatomy 0.000 claims description 10
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 claims description 8
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 claims description 8
- 239000008177 pharmaceutical agent Substances 0.000 claims description 8
- 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 description 8
- 101150105572 mmpL3 gene Proteins 0.000 claims description 7
- 208000011580 syndromic disease Diseases 0.000 claims description 7
- TZJDUUVOCXUTRC-UHFFFAOYSA-N 4-chloro-6-fluoro-n-(4-methylcyclohexyl)-1h-indole-2-carboxamide Chemical compound C1CC(C)CCC1NC(=O)C1=CC2=C(Cl)C=C(F)C=C2N1 TZJDUUVOCXUTRC-UHFFFAOYSA-N 0.000 claims description 6
- XLRNTZFYUSYXJI-UHFFFAOYSA-N 6-chloro-4-fluoro-n-(4-methylcyclohexyl)-1h-indole-2-carboxamide Chemical compound C1CC(C)CCC1NC(=O)C1=CC2=C(F)C=C(Cl)C=C2N1 XLRNTZFYUSYXJI-UHFFFAOYSA-N 0.000 claims description 6
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 229960003350 isoniazid Drugs 0.000 claims description 6
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 6
- GOJWKIPRMJQHGL-UHFFFAOYSA-N n-(4-methylcyclohexyl)-4,6-bis(trifluoromethyl)-1h-indole-2-carboxamide Chemical compound C1CC(C)CCC1NC(=O)C1=CC2=C(C(F)(F)F)C=C(C(F)(F)F)C=C2N1 GOJWKIPRMJQHGL-UHFFFAOYSA-N 0.000 claims description 6
- 229960001225 rifampicin Drugs 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 6
- 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 description 5
- MKBJWANFYAYLQQ-MGPUTAFESA-N 6-anilino-4-methyl-n-[(1r,2s)-2-methylcyclohexyl]-1h-indole-2-carboxamide Chemical compound C[C@H]1CCCC[C@H]1NC(=O)C(NC1=C2)=CC1=C(C)C=C2NC1=CC=CC=C1 MKBJWANFYAYLQQ-MGPUTAFESA-N 0.000 claims description 5
- MQYZRHHCNOJKPH-IINYFYTJSA-N 6-bromo-4-methyl-n-[(1r,2s)-2-methylcyclohexyl]-1h-indole-2-carboxamide Chemical compound C[C@H]1CCCC[C@H]1NC(=O)C1=CC2=C(C)C=C(Br)C=C2N1 MQYZRHHCNOJKPH-IINYFYTJSA-N 0.000 claims description 5
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 claims description 5
- 108010065839 Capreomycin Proteins 0.000 claims description 5
- DYDCUQKUCUHJBH-UWTATZPHSA-N D-Cycloserine Chemical compound N[C@@H]1CONC1=O DYDCUQKUCUHJBH-UWTATZPHSA-N 0.000 claims description 5
- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 claims description 5
- 229960004821 amikacin Drugs 0.000 claims description 5
- 229960004602 capreomycin Drugs 0.000 claims description 5
- 229960000285 ethambutol Drugs 0.000 claims description 5
- 208000015181 infectious disease Diseases 0.000 claims description 5
- 229930027917 kanamycin Natural products 0.000 claims description 5
- 229960000318 kanamycin Drugs 0.000 claims description 5
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 claims description 5
- 229930182823 kanamycin A Natural products 0.000 claims description 5
- 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 5
- 229960003702 moxifloxacin Drugs 0.000 claims description 5
- 229960001699 ofloxacin Drugs 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 229960005206 pyrazinamide Drugs 0.000 claims description 5
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims description 5
- SMAJIEHQYVPQNY-UHFFFAOYSA-N 4,6-dimethyl-n-(2-propan-2-ylcyclohexyl)-1h-indole-2-carboxamide Chemical compound CC(C)C1CCCCC1NC(=O)C1=CC2=C(C)C=C(C)C=C2N1 SMAJIEHQYVPQNY-UHFFFAOYSA-N 0.000 claims description 4
- QOICDOWLCQCNEB-GXFFZTMASA-N 4-bromo-n-[(1r,2s)-2-methylcyclohexyl]-1h-indole-2-carboxamide Chemical compound C[C@H]1CCCC[C@H]1NC(=O)C1=CC2=C(Br)C=CC=C2N1 QOICDOWLCQCNEB-GXFFZTMASA-N 0.000 claims description 4
- KZESTTWXIGVGNF-SMDDNHRTSA-N 4-cyano-n-[(1r,2s)-2-methylcyclohexyl]-1h-indole-2-carboxamide Chemical compound C[C@H]1CCCC[C@H]1NC(=O)C1=CC2=C(C#N)C=CC=C2N1 KZESTTWXIGVGNF-SMDDNHRTSA-N 0.000 claims description 4
- VWMMXVYGWBSSHR-GXTWGEPZSA-N 4-methyl-n-[(1r,2s)-2-methylcyclohexyl]-1h-indole-2-carboxamide Chemical compound C[C@H]1CCCC[C@H]1NC(=O)C1=CC2=C(C)C=CC=C2N1 VWMMXVYGWBSSHR-GXTWGEPZSA-N 0.000 claims description 4
- SKSCZARSITZAMO-GXFFZTMASA-N 6-bromo-n-[(1r,2s)-2-methylcyclohexyl]-1h-indole-2-carboxamide Chemical compound C[C@H]1CCCC[C@H]1NC(=O)C1=CC2=CC=C(Br)C=C2N1 SKSCZARSITZAMO-GXFFZTMASA-N 0.000 claims description 4
- VTZOAVRVIGLSDH-UHFFFAOYSA-N 6-chloro-n-(4-methylcyclohexyl)-1h-indole-2-carboxamide Chemical compound C1CC(C)CCC1NC(=O)C1=CC2=CC=C(Cl)C=C2N1 VTZOAVRVIGLSDH-UHFFFAOYSA-N 0.000 claims description 4
- OEZQBGUPOJTHJJ-XHDPSFHLSA-N 6-cyano-4-methyl-n-[(1r,2s)-2-methylcyclohexyl]-1h-indole-2-carboxamide Chemical compound C[C@H]1CCCC[C@H]1NC(=O)C1=CC2=C(C)C=C(C#N)C=C2N1 OEZQBGUPOJTHJJ-XHDPSFHLSA-N 0.000 claims description 4
- WVMIUZBFRMIPHI-SMDDNHRTSA-N 6-cyano-n-[(1r,2s)-2-methylcyclohexyl]-1h-indole-2-carboxamide Chemical compound C[C@H]1CCCC[C@H]1NC(=O)C1=CC2=CC=C(C#N)C=C2N1 WVMIUZBFRMIPHI-SMDDNHRTSA-N 0.000 claims description 4
- OUUAPXVQKFXKRS-GXTWGEPZSA-N 6-methyl-n-[(1r,2s)-2-methylcyclohexyl]-1h-indole-2-carboxamide Chemical compound C[C@H]1CCCC[C@H]1NC(=O)C1=CC2=CC=C(C)C=C2N1 OUUAPXVQKFXKRS-GXTWGEPZSA-N 0.000 claims description 4
- LVPQDFMRAJPWDM-UHFFFAOYSA-N 7-chloro-n-(4-methylcyclohexyl)-1h-indole-2-carboxamide Chemical compound C1CC(C)CCC1NC(=O)C1=CC2=CC=CC(Cl)=C2N1 LVPQDFMRAJPWDM-UHFFFAOYSA-N 0.000 claims description 4
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 claims description 4
- DYDCUQKUCUHJBH-UHFFFAOYSA-N D-Cycloserine Natural products NC1CONC1=O DYDCUQKUCUHJBH-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- VRDIULHPQTYCLN-UHFFFAOYSA-N Prothionamide Chemical compound CCCC1=CC(C(N)=S)=CC=N1 VRDIULHPQTYCLN-UHFFFAOYSA-N 0.000 claims description 4
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 claims description 4
- KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 claims description 4
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 claims description 4
- 229960003022 amoxicillin Drugs 0.000 claims description 4
- 229940121383 antituberculosis agent Drugs 0.000 claims description 4
- MESJKKLEOVJXNZ-HOMQSWHASA-N chembl3086124 Chemical compound C1C[C@@H](C)CC[C@@H]1NC(=O)C1=CC2=C(F)C=C(F)C=C2N1 MESJKKLEOVJXNZ-HOMQSWHASA-N 0.000 claims description 4
- 229940090805 clavulanate Drugs 0.000 claims description 4
- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 claims description 4
- WDQPAMHFFCXSNU-BGABXYSRSA-N clofazimine Chemical compound C12=CC=CC=C2N=C2C=C(NC=3C=CC(Cl)=CC=3)C(=N/C(C)C)/C=C2N1C1=CC=C(Cl)C=C1 WDQPAMHFFCXSNU-BGABXYSRSA-N 0.000 claims description 4
- 229960004287 clofazimine Drugs 0.000 claims description 4
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- 229960002182 imipenem Drugs 0.000 claims description 4
- 229960003376 levofloxacin Drugs 0.000 claims description 4
- 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 4
- 229960003907 linezolid Drugs 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- KLXIQTNTIXYSJA-UHFFFAOYSA-N n-(cyclohexylmethyl)-4,6-dimethyl-1h-indole-2-carboxamide Chemical compound N1C2=CC(C)=CC(C)=C2C=C1C(=O)NCC1CCCCC1 KLXIQTNTIXYSJA-UHFFFAOYSA-N 0.000 claims description 4
- FIMWLESENRVCER-IVMMDQJWSA-N n-[(1r,2s,3r)-2,3-dimethylcyclohexyl]-4,6-dimethyl-1h-indole-2-carboxamide Chemical compound C[C@H]1[C@H](C)CCC[C@H]1NC(=O)C1=CC2=C(C)C=C(C)C=C2N1 FIMWLESENRVCER-IVMMDQJWSA-N 0.000 claims description 4
- FIMWLESENRVCER-XPKDYRNWSA-N n-[(1s,2r,3r)-2,3-dimethylcyclohexyl]-4,6-dimethyl-1h-indole-2-carboxamide Chemical compound C[C@@H]1[C@H](C)CCC[C@@H]1NC(=O)C1=CC2=C(C)C=C(C)C=C2N1 FIMWLESENRVCER-XPKDYRNWSA-N 0.000 claims description 4
- FIMWLESENRVCER-BJJXKVORSA-N n-[(1s,2r,3s)-2,3-dimethylcyclohexyl]-4,6-dimethyl-1h-indole-2-carboxamide Chemical compound C[C@@H]1[C@@H](C)CCC[C@@H]1NC(=O)C1=CC2=C(C)C=C(C)C=C2N1 FIMWLESENRVCER-BJJXKVORSA-N 0.000 claims description 4
- ANRDRZQBFPDAJD-UHFFFAOYSA-N n-cycloheptyl-4,6-dimethyl-1h-indole-2-carboxamide Chemical compound N1C2=CC(C)=CC(C)=C2C=C1C(=O)NC1CCCCCC1 ANRDRZQBFPDAJD-UHFFFAOYSA-N 0.000 claims description 4
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 claims description 4
- 229960000918 protionamide Drugs 0.000 claims description 4
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- 229960003231 thioacetazone Drugs 0.000 claims description 4
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 claims description 4
- 229960002784 thioridazine Drugs 0.000 claims description 4
- 239000000814 tuberculostatic agent Substances 0.000 claims description 4
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims description 3
- USFUDALBHSUWCW-UHFFFAOYSA-N 4-bromo-n-cycloheptyl-6-(trifluoromethyl)-1h-indole-2-carboxamide Chemical compound N1C2=CC(C(F)(F)F)=CC(Br)=C2C=C1C(=O)NC1CCCCCC1 USFUDALBHSUWCW-UHFFFAOYSA-N 0.000 claims description 3
- NYMJRFRRVIFTRU-UHFFFAOYSA-N 4-chloro-n-(4-methylcyclohexyl)-1h-indole-2-carboxamide Chemical compound C1CC(C)CCC1NC(=O)C1=CC2=C(Cl)C=CC=C2N1 NYMJRFRRVIFTRU-UHFFFAOYSA-N 0.000 claims description 3
- ZDNREMVWQAZTFX-SWLSCSKDSA-N 4-cyano-6-methyl-n-[(1r,2s)-2-methylcyclohexyl]-1h-indole-2-carboxamide Chemical compound C[C@H]1CCCC[C@H]1NC(=O)C1=CC2=C(C#N)C=C(C)C=C2N1 ZDNREMVWQAZTFX-SWLSCSKDSA-N 0.000 claims description 3
- HGJLZOCQPVDNDZ-WKILWMFISA-N C(C)(C)[C@@H]1CC[C@H](CC1)NC(=O)C=1NC2=CC(=CC(=C2C1)C)C Chemical compound C(C)(C)[C@@H]1CC[C@H](CC1)NC(=O)C=1NC2=CC(=CC(=C2C1)C)C HGJLZOCQPVDNDZ-WKILWMFISA-N 0.000 claims description 3
- 229960004909 aminosalicylic acid Drugs 0.000 claims description 3
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin 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)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 claims description 3
- 229960002626 clarithromycin Drugs 0.000 claims description 3
- FIMWLESENRVCER-DUVNUKRYSA-N n-[(1r,2s,3s)-2,3-dimethylcyclohexyl]-4,6-dimethyl-1h-indole-2-carboxamide Chemical compound C[C@H]1[C@@H](C)CCC[C@H]1NC(=O)C1=CC2=C(C)C=C(C)C=C2N1 FIMWLESENRVCER-DUVNUKRYSA-N 0.000 claims description 3
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
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- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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Landscapes
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- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261698033P | 2012-09-07 | 2012-09-07 | |
| US201261698033P | 2012-09-07 | ||
| PCT/IB2013/058318 WO2014037900A1 (en) | 2012-09-07 | 2013-09-05 | Indole carboxamide derivatives and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2660210T3 true ES2660210T3 (es) | 2018-03-21 |
Family
ID=49585451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13792084.9T Active ES2660210T3 (es) | 2012-09-07 | 2013-09-05 | Derivados de indolcarboxamida y usos de los mismos |
Country Status (11)
| Country | Link |
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| EA032760B1 (ru) * | 2014-04-04 | 2019-07-31 | Айомет Фарма Лтд | Соединения ингибиторы ido и tdo |
| WO2015164482A1 (en) * | 2014-04-22 | 2015-10-29 | The Johns Hopkins University | Inhibitors of drug-resistant mycobacterium tuberculosis |
| HUE050592T2 (hu) * | 2014-10-24 | 2020-12-28 | Bristol Myers Squibb Co | Indol karboxamid vegyületek, amelyek hasznosak kináz inhibitorokként |
| EP3444031B1 (en) * | 2016-04-15 | 2022-11-30 | CE Pharm Co.,Ltd | Heterocyclic carboxylic acid amide ligand and applications thereof in copper catalyzed coupling reaction of aryl halogeno substitute |
| CN110305798B (zh) * | 2016-06-15 | 2021-11-19 | 中国医学科学院医药生物技术研究所 | 一株曲霉菌的用途及由该曲霉菌制备的化合物及其用途 |
| US10383848B2 (en) * | 2016-08-04 | 2019-08-20 | Creighton University | Indole-based therapeutics |
| US10858319B2 (en) | 2016-10-03 | 2020-12-08 | Iomet Pharma Ltd. | Indole derivatives for use in medicine |
| US11180459B2 (en) | 2017-03-10 | 2021-11-23 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| CA3061238A1 (en) | 2017-03-10 | 2018-09-13 | Rutgers, The State University Of New Jersey | Indole derivatives as efflux pump inhibitors |
| US11938114B2 (en) | 2017-03-10 | 2024-03-26 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| CN111163774A (zh) | 2017-05-26 | 2020-05-15 | 罗格斯新泽西州立大学 | 细菌外排泵抑制剂 |
| US11458121B2 (en) | 2017-06-26 | 2022-10-04 | Rutgers, The State University Of New Jersey | Therapeutic compounds and methods to treat infection |
| US11718633B2 (en) | 2018-05-17 | 2023-08-08 | Council Of Scientific And Industrial Research | Indole compounds, process for the preparation and use thereof |
| KR102219563B1 (ko) * | 2019-02-15 | 2021-02-24 | 에스티팜 주식회사 | 페나진 유도체 제조를 위한 중간체 및 그의 제조방법 |
| CA3151407A1 (en) * | 2019-09-26 | 2021-04-01 | Takushi Kaneko | Indole carboxamide compounds and use thereof for the treatment of mycobacterial infections |
| US20230002372A1 (en) * | 2019-09-26 | 2023-01-05 | The Global Alliance For Tb Drug Development, Inc. | Azaindole carboxamide compounds for the treatment of mycobacterial infections |
| CN110577483B (zh) * | 2019-09-26 | 2020-05-12 | 海南医学院 | 一种3,3-二取代-2-吲哚酮的绿色合成方法 |
| US20220396586A1 (en) * | 2019-09-26 | 2022-12-15 | The Global Alliance For Tb Drug Development, Inc. | Thiazole carboxamide compounds and use thereof for the treatment of mycobacterial infections |
| RU2767542C1 (ru) * | 2021-05-24 | 2022-03-17 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" (ПГНИУ) | Противотуберкулезное средство на основе 4-((гет)ароил)-3- гидрокси-1-(2-гидроксифенил)-5-(фенилтио)-1,5-дигидро-2Н-пиррол-2-онов |
| CN115583908B (zh) * | 2021-07-05 | 2024-08-06 | 西北农林科技大学 | 一种吲哚甲酰胺类化合物及其制备方法和用途 |
| US12012398B2 (en) * | 2021-07-12 | 2024-06-18 | Nido Biosciences, Inc. | Bicyclic compounds as androgen receptor modulators |
| EP4626881A1 (en) * | 2022-12-02 | 2025-10-08 | Merck Sharp & Dohme LLC | Preparation of fused azole derivatives as novel diacylglyceride o-acyltransferase 2 inhibitors |
| CN118724763B (zh) * | 2024-09-02 | 2024-12-06 | 辽宁龙田化工科技有限公司 | 一种4-甲基苯磺酰氯合成方法 |
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| US883049A (en) * | 1907-09-12 | 1908-03-24 | John W Piver | Tongue-and-groove joint for flooring. |
| FR2705095B1 (fr) * | 1993-05-12 | 1995-06-23 | Adir | Nouveaux indoles substitués, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
| HU227197B1 (en) * | 2000-10-24 | 2010-10-28 | Richter Gedeon Nyrt | Nmda receptor antagonist carboxylic acid amide derivatives and pharmaceutical compositions containing them |
| WO2003000657A1 (en) | 2001-06-20 | 2003-01-03 | Daiichi Pharmaceutical Co., Ltd. | Diamine derivatives |
| CA2464214C (en) | 2001-10-22 | 2011-02-08 | The Research Foundation Of State University Of New York | Protein kinase and phosphatase inhibitors, methods for designing them, and methods of using them |
| US6759428B2 (en) | 2001-12-04 | 2004-07-06 | Roche Palo Alto Llc | Indole nitriles |
| AU2002352126A1 (en) | 2001-12-04 | 2003-06-17 | F. Hoffmann-La Roche Ag | Substituted 2-amino-cycloalkanecarboxamides and their use as cysteine protease inhibitors |
| WO2004078163A2 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| AU2003227360A1 (en) * | 2002-04-25 | 2003-11-10 | Yamanouchi Pharmaceutical Co., Ltd. | Novel amide derivatives or salts thereof |
| GB0428173D0 (en) * | 2004-12-23 | 2005-01-26 | Astrazeneca Ab | Compounds |
| CA2617123C (en) * | 2005-08-12 | 2015-05-26 | United States Government As Represented By The Secretary Of The United States Army And The U.S. Army Medical Research & Materiel Command | Broad spectrum antibacterial compounds |
| EP2016078B1 (en) | 2006-04-04 | 2016-06-15 | Fibrogen, Inc. | Pyrrolo- and thiazolo-pyridine compounds as hif modulators |
| WO2009063495A2 (en) | 2007-09-20 | 2009-05-22 | Cadila Healthcare Limited | Substituted indole and its derivatives as cannabinoid modulators |
| AU2009335821A1 (en) * | 2008-12-19 | 2010-07-15 | Bristol-Myers Squibb Company | Carbazole carboxamide compounds useful as kinase inhibitors |
| CN104856991A (zh) | 2009-02-27 | 2015-08-26 | 西佳技术公司 | 用于治疗和预防登革热病毒感染的噻吩并吡啶衍生物 |
| RU2012107101A (ru) | 2009-07-31 | 2013-09-10 | Байокрист Фармасьютикалз, Инк. | Производные пирроло[1,2-в] пиридазина как ингибиторы янус-киназы |
| JP5848712B2 (ja) | 2009-12-11 | 2016-01-27 | ノノ インコーポレイテッド | 虚血性疾患および他の疾患を治療するための薬剤および方法 |
| JP2012107001A (ja) * | 2010-10-22 | 2012-06-07 | Shionogi & Co Ltd | インドールアミド化合物を含有する医薬 |
| US9200046B2 (en) * | 2011-06-29 | 2015-12-01 | Cornell University | Reporter system for high throughput screening of compounds and uses thereof |
-
2013
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- 2013-09-05 CA CA2881351A patent/CA2881351A1/en not_active Abandoned
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- 2013-09-05 EA EA201590504A patent/EA028093B1/ru not_active IP Right Cessation
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- 2013-09-05 US US14/420,074 patent/US9447039B2/en active Active
- 2013-09-05 CN CN201380046508.9A patent/CN104603106B/zh not_active Expired - Fee Related
- 2013-09-05 EP EP13792084.9A patent/EP2892880B1/en not_active Not-in-force
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2020
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| US20160355477A1 (en) | 2016-12-08 |
| BR112015004666A2 (pt) | 2017-07-04 |
| BR112015004666B1 (pt) | 2022-04-26 |
| WO2014037900A1 (en) | 2014-03-13 |
| AU2013311235A1 (en) | 2015-02-26 |
| CN104603106B (zh) | 2017-05-10 |
| CA2881351A1 (en) | 2014-03-13 |
| US20150175539A1 (en) | 2015-06-25 |
| JP2015527388A (ja) | 2015-09-17 |
| EA028093B1 (ru) | 2017-10-31 |
| EP2892880A1 (en) | 2015-07-15 |
| AU2013311235B2 (en) | 2016-03-24 |
| CN104603106A (zh) | 2015-05-06 |
| JP6223452B2 (ja) | 2017-11-01 |
| US9447039B2 (en) | 2016-09-20 |
| IN2015DN01163A (enExample) | 2015-06-26 |
| EA201590504A1 (ru) | 2015-07-30 |
| EP2892880B1 (en) | 2017-11-22 |
| KR20150048759A (ko) | 2015-05-07 |
| US20210032202A1 (en) | 2021-02-04 |
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