KR20040104613A - 인터루킨-4 유전자 발현 억제제로서의 3-치환된아미노-1η-인돌-2-카복실산 및 3-치환된아미노-벤조티오펜-2-카복실산 유도체 - Google Patents
인터루킨-4 유전자 발현 억제제로서의 3-치환된아미노-1η-인돌-2-카복실산 및 3-치환된아미노-벤조티오펜-2-카복실산 유도체 Download PDFInfo
- Publication number
- KR20040104613A KR20040104613A KR10-2004-7017097A KR20047017097A KR20040104613A KR 20040104613 A KR20040104613 A KR 20040104613A KR 20047017097 A KR20047017097 A KR 20047017097A KR 20040104613 A KR20040104613 A KR 20040104613A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- carboxylic acid
- indole
- ester
- phenyl
- 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.)
- Ceased
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- -1 3-substituted amino-benzothiophene-2-carboxylic acid Chemical class 0.000 title claims abstract description 163
- 108090000978 Interleukin-4 Proteins 0.000 title abstract description 65
- 102000004388 Interleukin-4 Human genes 0.000 title abstract description 64
- 229940028885 interleukin-4 Drugs 0.000 title abstract description 58
- 230000014509 gene expression Effects 0.000 title description 29
- 239000003112 inhibitor Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 276
- 125000000217 alkyl group Chemical group 0.000 claims description 350
- 238000000034 method Methods 0.000 claims description 118
- 238000006243 chemical reaction Methods 0.000 claims description 103
- QPZYGDVYAXCTLM-UHFFFAOYSA-N 3-(pyridin-4-ylamino)-1h-indole-2-carboxylic acid Chemical compound OC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 QPZYGDVYAXCTLM-UHFFFAOYSA-N 0.000 claims description 95
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 94
- 229910052739 hydrogen Inorganic materials 0.000 claims description 88
- 239000001257 hydrogen Substances 0.000 claims description 79
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 78
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 77
- 229910052736 halogen Inorganic materials 0.000 claims description 57
- 150000002367 halogens Chemical class 0.000 claims description 57
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 56
- 229920001774 Perfluoroether Polymers 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 30
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 27
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 19
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 19
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 17
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 12
- 125000005504 styryl group Chemical group 0.000 claims description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000003944 tolyl group Chemical group 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 5
- JZGZKRJVTIRPOK-UHFFFAOYSA-N ethyl thiophene-2-carboxylate Chemical compound CCOC(=O)C1=CC=CS1 JZGZKRJVTIRPOK-UHFFFAOYSA-N 0.000 claims description 5
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 5
- AETKQAJQFJIMNR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl) 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OC(=O)C1=C(NC=2C=CN=CC=2)C2=CC=CC=C2N1 AETKQAJQFJIMNR-UHFFFAOYSA-N 0.000 claims description 4
- VEDSFPLPICCHGF-UHFFFAOYSA-N (2-morpholin-4-yl-2-oxoethyl) 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound C1COCCN1C(=O)COC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 VEDSFPLPICCHGF-UHFFFAOYSA-N 0.000 claims description 4
- SDEOJHFQBUZEDT-UHFFFAOYSA-N (2-oxopiperidin-1-yl)methyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound N1C2=CC=CC=C2C(NC=2C=CN=CC=2)=C1C(=O)OCN1CCCCC1=O SDEOJHFQBUZEDT-UHFFFAOYSA-N 0.000 claims description 4
- FBNMSHRTMOBKFF-UHFFFAOYSA-N (2-oxopyrrolidin-1-yl)methyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound N1C2=CC=CC=C2C(NC=2C=CN=CC=2)=C1C(=O)OCN1CCCC1=O FBNMSHRTMOBKFF-UHFFFAOYSA-N 0.000 claims description 4
- MUEXUQOKWIFGKS-UHFFFAOYSA-N (n-(4-methylphenyl)sulfonylanilino)methyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N(C=1C=CC=CC=1)COC(=O)C1=C(NC=2C=CN=CC=2)C2=CC=CC=C2N1 MUEXUQOKWIFGKS-UHFFFAOYSA-N 0.000 claims description 4
- LKXXFDBDQXSVEX-UHFFFAOYSA-N 2,3-dimethylbutan-2-yloxycarbonyloxymethyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound CC(C)C(C)(C)OC(=O)OCOC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 LKXXFDBDQXSVEX-UHFFFAOYSA-N 0.000 claims description 4
- WEWDORJUJHXQRY-UHFFFAOYSA-N [2-(azetidin-1-yl)-2-oxoethyl] 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound C1CCN1C(=O)COC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 WEWDORJUJHXQRY-UHFFFAOYSA-N 0.000 claims description 4
- YVOPHWLKGPJKEY-UHFFFAOYSA-N [3-(pyridin-4-ylamino)-1h-indole-2-carbonyl]oxymethyl morpholine-4-carboxylate Chemical compound C1COCCN1C(=O)OCOC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 YVOPHWLKGPJKEY-UHFFFAOYSA-N 0.000 claims description 4
- UUMZYHNMONWXOI-UHFFFAOYSA-N [benzenesulfonyl(methyl)amino]methyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound C=1C=CC=CC=1S(=O)(=O)N(C)COC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 UUMZYHNMONWXOI-UHFFFAOYSA-N 0.000 claims description 4
- ADRLVASWJZCENK-UHFFFAOYSA-N [methyl-(4-methylphenyl)sulfonylamino]methyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)N(C)COC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 ADRLVASWJZCENK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000005042 acyloxymethyl group Chemical group 0.000 claims description 4
- RJICFSNQKOFTBZ-UHFFFAOYSA-N cyclohexyloxycarbonyloxymethyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound C1CCCCC1OC(=O)OCOC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 RJICFSNQKOFTBZ-UHFFFAOYSA-N 0.000 claims description 4
- RATQANZPQWXPRO-UHFFFAOYSA-N diethylcarbamoyloxymethyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound CCN(CC)C(=O)OCOC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 RATQANZPQWXPRO-UHFFFAOYSA-N 0.000 claims description 4
- REAPVJGXQMYICO-UHFFFAOYSA-N piperidine-1-carbonyloxymethyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound C1CCCCN1C(=O)OCOC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 REAPVJGXQMYICO-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- VCQURUZYYSOUHP-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl) 2,2,2-trifluoroacetate Chemical compound FC1=C(F)C(F)=C(OC(=O)C(F)(F)F)C(F)=C1F VCQURUZYYSOUHP-UHFFFAOYSA-N 0.000 claims description 3
- PYSSHAMICMLSIJ-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound CCOC(=O)COC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 PYSSHAMICMLSIJ-UHFFFAOYSA-N 0.000 claims description 3
- BWRGAIQARMNAPH-UHFFFAOYSA-N (2-methylpropan-2-yl)oxycarbonyloxymethyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound CC(C)(C)OC(=O)OCOC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 BWRGAIQARMNAPH-UHFFFAOYSA-N 0.000 claims description 3
- BRMASUJOYZZBJM-UHFFFAOYSA-N (2-oxo-2-pyrrolidin-1-ylethyl) 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound C1CCCN1C(=O)COC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 BRMASUJOYZZBJM-UHFFFAOYSA-N 0.000 claims description 3
- FJALKCZHZODKGP-UHFFFAOYSA-N 2,2-dimethylpropanoyloxymethyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound CC(C)(C)C(=O)OCOC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 FJALKCZHZODKGP-UHFFFAOYSA-N 0.000 claims description 3
- FBMNYSXUWJPSOU-UHFFFAOYSA-N 2,3-dihydro-1h-inden-5-yl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound C=1C=C2CCCC2=CC=1OC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 FBMNYSXUWJPSOU-UHFFFAOYSA-N 0.000 claims description 3
- AFNDYDOXMMANFI-UHFFFAOYSA-N 2-(diethylamino)ethyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound CCN(CC)CCOC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 AFNDYDOXMMANFI-UHFFFAOYSA-N 0.000 claims description 3
- RYCDZBIWZBHTFS-UHFFFAOYSA-N 2-(dimethylamino)ethyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound CN(C)CCOC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 RYCDZBIWZBHTFS-UHFFFAOYSA-N 0.000 claims description 3
- KTFSEMVJMBRAPC-UHFFFAOYSA-N 2-methoxyethyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound COCCOC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 KTFSEMVJMBRAPC-UHFFFAOYSA-N 0.000 claims description 3
- BSPIIAWBOGGPKD-UHFFFAOYSA-N 2-piperidin-1-ylethyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound N1C2=CC=CC=C2C(NC=2C=CN=CC=2)=C1C(=O)OCCN1CCCCC1 BSPIIAWBOGGPKD-UHFFFAOYSA-N 0.000 claims description 3
- ZSLORZDXSGORKT-UHFFFAOYSA-N 3-(pyridin-4-ylamino)-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 ZSLORZDXSGORKT-UHFFFAOYSA-N 0.000 claims description 3
- IGUPPZUAMSEYQC-UHFFFAOYSA-N 3-ethoxypropyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound CCOCCCOC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 IGUPPZUAMSEYQC-UHFFFAOYSA-N 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- XBFDYEHIYFGBLH-NSHDSACASA-N [(2s)-1-methoxy-1-oxopropan-2-yl] 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound COC(=O)[C@H](C)OC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 XBFDYEHIYFGBLH-NSHDSACASA-N 0.000 claims description 3
- CKAAQTRNSDOHRP-UHFFFAOYSA-N [2-(diethylamino)-2-oxoethyl] 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound CCN(CC)C(=O)COC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 CKAAQTRNSDOHRP-UHFFFAOYSA-N 0.000 claims description 3
- QVRPGCXQCRQTDD-UHFFFAOYSA-N [2-[benzyl(ethyl)amino]-2-oxoethyl] 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound N1C2=CC=CC=C2C(NC=2C=CN=CC=2)=C1C(=O)OCC(=O)N(CC)CC1=CC=CC=C1 QVRPGCXQCRQTDD-UHFFFAOYSA-N 0.000 claims description 3
- ARXIVQWPBASQNA-UHFFFAOYSA-N [benzoyl-(2-ethoxy-2-oxoethyl)amino]methyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound C=1C=CC=CC=1C(=O)N(CC(=O)OCC)COC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 ARXIVQWPBASQNA-UHFFFAOYSA-N 0.000 claims description 3
- FUCZGFDMJIVSKU-UHFFFAOYSA-N acetyloxymethyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound CC(=O)OCOC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 FUCZGFDMJIVSKU-UHFFFAOYSA-N 0.000 claims description 3
- 239000012190 activator Substances 0.000 claims description 3
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
- RROBIDXNTUAHFW-UHFFFAOYSA-N benzotriazol-1-yloxy-tris(dimethylamino)phosphanium Chemical compound C1=CC=C2N(O[P+](N(C)C)(N(C)C)N(C)C)N=NC2=C1 RROBIDXNTUAHFW-UHFFFAOYSA-N 0.000 claims description 3
- CVNITGVWCLWWAF-UHFFFAOYSA-N benzylcarbamoyloxymethyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound N1C2=CC=CC=C2C(NC=2C=CN=CC=2)=C1C(=O)OCOC(=O)NCC1=CC=CC=C1 CVNITGVWCLWWAF-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- MTHIEIPUAMHCGE-UHFFFAOYSA-N n-methoxy-n-methyl-3-(pyridin-4-ylamino)-1h-indole-2-carboxamide Chemical compound CON(C)C(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 MTHIEIPUAMHCGE-UHFFFAOYSA-N 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- KVXSMMGUTQEMLL-UHFFFAOYSA-N 2-(aminomethyl)-n-pyridin-4-yl-1h-indol-3-amine Chemical compound NCC=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 KVXSMMGUTQEMLL-UHFFFAOYSA-N 0.000 claims description 2
- HODVDYFYUUTVBQ-UHFFFAOYSA-N 3-(2-phenylethenylsulfonylamino)-3h-indole-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=CC=C2C1NS(=O)(=O)C=CC1=CC=CC=C1 HODVDYFYUUTVBQ-UHFFFAOYSA-N 0.000 claims description 2
- FYCXRQLQDNGQKN-UHFFFAOYSA-N 3-(naphthalen-1-ylsulfonylamino)-3h-indole-2-carboxylic acid Chemical compound C1=CC=C2C(S(=O)(=O)NC3C4=CC=CC=C4N=C3C(=O)O)=CC=CC2=C1 FYCXRQLQDNGQKN-UHFFFAOYSA-N 0.000 claims description 2
- KVHBKOZGUKOJDY-UHFFFAOYSA-N 3-(pyridin-4-ylamino)-1h-indole-2-carbaldehyde Chemical compound O=CC=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 KVHBKOZGUKOJDY-UHFFFAOYSA-N 0.000 claims description 2
- XHKKHCAQPHRULC-UHFFFAOYSA-N 3-(pyrimidin-2-ylamino)-1h-indole-2-carboxylic acid Chemical compound OC(=O)C=1NC2=CC=CC=C2C=1NC1=NC=CC=N1 XHKKHCAQPHRULC-UHFFFAOYSA-N 0.000 claims description 2
- AZQYHNYXKUQQIW-UHFFFAOYSA-N 3-[(2-acetamido-1,3-thiazol-5-yl)sulfonylamino]-3h-indole-2-carboxylic acid Chemical compound S1C(NC(=O)C)=NC=C1S(=O)(=O)NC1C2=CC=CC=C2N=C1C(O)=O AZQYHNYXKUQQIW-UHFFFAOYSA-N 0.000 claims description 2
- PBAFTYPCPHZXTG-UHFFFAOYSA-N 3-[(7,7-dimethyl-3-oxo-2-bicyclo[2.2.1]heptanyl)methylsulfonylamino]-3h-indole-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=CC=C2C1NS(=O)(=O)CC1C(=O)C2CCC1C2(C)C PBAFTYPCPHZXTG-UHFFFAOYSA-N 0.000 claims description 2
- UMDFTHOQHLYQGK-UHFFFAOYSA-N 3-[[4-[[4-(dimethylamino)phenyl]diazenyl]phenyl]sulfonylamino]-3h-indole-2-carboxylic acid Chemical compound C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S(=O)(=O)NC2C3=CC=CC=C3N=C2C(O)=O)C=C1 UMDFTHOQHLYQGK-UHFFFAOYSA-N 0.000 claims description 2
- ASRILBMIHNCTQB-UHFFFAOYSA-N 3-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]-3h-indole-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=CC=C2C1NS(=O)(=O)C1=C2C=CC=C(N(C)C)C2=CC=C1 ASRILBMIHNCTQB-UHFFFAOYSA-N 0.000 claims description 2
- CRZKYZFCONVASA-UHFFFAOYSA-N 5,6-dimethoxy-3-(pyridin-4-ylamino)-1h-indole-2-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(C(O)=O)=C1NC1=CC=NC=C1 CRZKYZFCONVASA-UHFFFAOYSA-N 0.000 claims description 2
- JWSPZOUFDPNSCD-UHFFFAOYSA-N 6-phenyl-3-(pyridin-4-ylamino)-1h-indole-2-carboxylic acid Chemical compound OC(=O)C=1NC2=CC(C=3C=CC=CC=3)=CC=C2C=1NC1=CC=NC=C1 JWSPZOUFDPNSCD-UHFFFAOYSA-N 0.000 claims description 2
- DEBJGFOUTRHSJF-UHFFFAOYSA-N CS(=O)(=O)O.S1C(=CC=C1)C(=O)O Chemical compound CS(=O)(=O)O.S1C(=CC=C1)C(=O)O DEBJGFOUTRHSJF-UHFFFAOYSA-N 0.000 claims description 2
- OCPOAZASPYBOGJ-UHFFFAOYSA-N [3-(pyridin-4-ylamino)-1h-indol-2-yl]methanol Chemical compound OCC=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 OCPOAZASPYBOGJ-UHFFFAOYSA-N 0.000 claims description 2
- KGEYLRTZZBNBLR-UHFFFAOYSA-N ethyl 3-[[6-(morpholine-4-carbonyl)pyridine-3-carbonyl]amino]-3h-indole-2-carboxylate Chemical compound CCOC(=O)C1=NC2=CC=CC=C2C1NC(=O)C(C=N1)=CC=C1C(=O)N1CCOCC1 KGEYLRTZZBNBLR-UHFFFAOYSA-N 0.000 claims description 2
- CCCPSFQKYIJVCA-UHFFFAOYSA-N ethyl 3-amino-3-(2,6-dichloropyridine-4-carbonyl)indole-2-carboxylate Chemical compound CCOC(=O)C1=NC2=CC=CC=C2C1(N)C(=O)C1=CC(Cl)=NC(Cl)=C1 CCCPSFQKYIJVCA-UHFFFAOYSA-N 0.000 claims description 2
- VRWQOBWWFTVTEZ-UHFFFAOYSA-N ethyl 3-amino-3-(2-chloro-6-methoxypyridine-4-carbonyl)indole-2-carboxylate Chemical compound CCOC(=O)C1=NC2=CC=CC=C2C1(N)C(=O)C1=CC(Cl)=NC(OC)=C1 VRWQOBWWFTVTEZ-UHFFFAOYSA-N 0.000 claims description 2
- HEXFTKUKGIOPMV-UHFFFAOYSA-N ethyl 3-amino-3-(2-chloro-6-methylpyridine-4-carbonyl)indole-2-carboxylate Chemical compound CCOC(=O)C1=NC2=CC=CC=C2C1(N)C(=O)C1=CC(C)=NC(Cl)=C1 HEXFTKUKGIOPMV-UHFFFAOYSA-N 0.000 claims description 2
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- 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
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- 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
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- 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
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Public Health (AREA)
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- Animal Behavior & Ethology (AREA)
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- Orthopedic Medicine & Surgery (AREA)
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- Otolaryngology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (5)
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| US37530402P | 2002-04-23 | 2002-04-23 | |
| US60/375,304 | 2002-04-23 | ||
| GBGB0217920.8A GB0217920D0 (en) | 2002-04-23 | 2002-08-02 | Interleukin-4 Gene Expression inhibitors |
| GB0217920.8 | 2002-08-02 | ||
| PCT/US2003/012661 WO2003091215A1 (en) | 2002-04-23 | 2003-04-23 | 3-substituted amino-1h-indole-2-carboxylic acid and 3-substituted amino-benzo’ b! thiophene-2-carboxylic acid derivatives as interieukin-4 gene expression inhibitors |
Publications (1)
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| KR20040104613A true KR20040104613A (ko) | 2004-12-10 |
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| KR1020047017098A Expired - Fee Related KR100972304B1 (ko) | 2002-04-23 | 2003-04-23 | 3-치환된 아미노-1H-인돌-2-카복실산 및 3-치환된 아미노-벤조(b)티오펜-2-카복실산 |
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| GB (1) | GB0217920D0 (https=) |
| TW (1) | TWI296926B (https=) |
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| SE0302035D0 (sv) * | 2003-07-09 | 2003-07-09 | Biolipox Ab | New compound |
| WO2005023246A1 (en) * | 2003-09-04 | 2005-03-17 | Aventis Pharmaceuticals Inc. | Substituted indoles as inhibitors of poly (adp-ribose) polymerase (parp) |
| US7417063B2 (en) * | 2004-04-13 | 2008-08-26 | Bristol-Myers Squibb Company | Bicyclic heterocycles useful as serine protease inhibitors |
| RU2256451C1 (ru) * | 2004-04-21 | 2005-07-20 | Закрытое акционерное общество "Мастерлек" | Лекарственное средство для лечения атипичной пневмонии |
| JP2008527030A (ja) * | 2005-01-19 | 2008-07-24 | バイオリポックス エービー | 炎症の治療に有用なインドール類 |
| CN101142185A (zh) * | 2005-01-19 | 2008-03-12 | 比奥里波克斯公司 | 用于炎症治疗的吲哚 |
| JP5275236B2 (ja) * | 2006-09-29 | 2013-08-28 | スミスクライン ビーチャム コーポレーション | 置換されたインドール化合物 |
| WO2008098096A1 (en) * | 2007-02-08 | 2008-08-14 | Boehringer Ingelheim International Gmbh | Anti-cytokine heterocyclic compounds |
| US8786873B2 (en) * | 2009-07-20 | 2014-07-22 | General Electric Company | Application server for use with a modular imaging system |
| CN101628842A (zh) * | 2009-08-27 | 2010-01-20 | 中国人民解放军防化指挥工程学院 | 烷氧羰基甲氧基作为羧基保护基 |
| US8243882B2 (en) | 2010-05-07 | 2012-08-14 | General Electric Company | System and method for indicating association between autonomous detector and imaging subsystem |
| KR101292836B1 (ko) * | 2011-03-28 | 2013-08-05 | 한국화학연구원 | 벤조퓨란 또는 벤조싸이오펜 유도체 및 이의 약학적으로 허용가능한 염을 유효성분으로 함유하는 척수손상 관련 질환의 예방 또는 치료용 약학적 조성물 |
| CN105708834A (zh) * | 2011-10-18 | 2016-06-29 | 株式会社爱茉莉太平洋 | 包含丁香脂素的sirt1活化剂 |
| US9962251B2 (en) | 2013-10-17 | 2018-05-08 | Boston Scientific Scimed, Inc. | Devices and methods for delivering implants |
| AU2017220184B2 (en) * | 2016-02-19 | 2024-04-18 | Regeneron Pharmaceuticals, Inc. | Methods for enhancing efficacy of a vaccine by administering an IL-4R antagonist |
| KR101833460B1 (ko) | 2016-07-05 | 2018-04-13 | 충남대학교산학협력단 | 대식세포(macrophage)의 극성(polarization)조절에 의하여 결핵균 생존 및 증식을 억제하기 위한 조성물. |
| EP3655961A4 (en) * | 2017-07-17 | 2021-09-01 | Massachusetts Institute of Technology | HEALTHY AND SICK BARRIER TISSUE CELL ATLAS |
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| US499355A (en) * | 1893-06-13 | Machine for making beam-stirrups | ||
| US4675332A (en) * | 1984-12-10 | 1987-06-23 | Warner-Lambert Company | Acidic tetrazolyl substituted indole compounds and their use as antiallergy agents |
| HU895334D0 (en) * | 1986-07-30 | 1990-01-28 | Sandoz Ag | Process for the preparation of nasal pharmaceutical compositions |
| FR2628425B1 (fr) * | 1988-03-08 | 1992-04-03 | Rhone Poulenc Sante | Derives d'isoindolinone, leurs procedes de preparation et les medicaments les contenant |
| US5189054A (en) * | 1990-11-02 | 1993-02-23 | Merrell Dow Pharmaceuticals Inc. | 3-amidoindolyl derivatives and pharmaceutical compositions thereof |
| AU641052B2 (en) * | 1990-11-02 | 1993-09-09 | Aventisub Ii Inc. | 3-amidoindolyl derivatives |
| US5328920A (en) * | 1991-04-17 | 1994-07-12 | Hoechst-Roussel Pharmaceuticals Incorporated | Substituted (pyridinylamino)-indoles |
| US5177088A (en) * | 1991-04-17 | 1993-01-05 | Hoechst-Roussel Pharmaceuticals Incorporated | Substituted 3-(pyridinylamino)-indoles |
| GB9219472D0 (en) * | 1992-09-15 | 1992-10-28 | Leo Pharm Prod Ltd | Chemical compounds |
| US5489586A (en) * | 1994-03-07 | 1996-02-06 | Warner-Lambert Company | Method for treating inflammatory disease in humans |
| US5969146A (en) | 1995-10-11 | 1999-10-19 | Synthelabo | Oxazolidin-2-one derivatives, preparation method therefor and therapeutical use thereof |
| US6313151B1 (en) * | 1997-06-26 | 2001-11-06 | Eli Lilly And Company | Antithrombotic agents |
| GB9902455D0 (en) | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| US6365370B1 (en) * | 1999-09-01 | 2002-04-02 | Ortho-Mcneil Pharmaceutical, Inc. | DNA encoding a human subunit 5-HT3-C of the 5-HT3 serotonin receptor |
-
2002
- 2002-08-02 GB GBGB0217920.8A patent/GB0217920D0/en not_active Ceased
-
2003
- 2003-04-22 TW TW092109279A patent/TWI296926B/zh not_active IP Right Cessation
- 2003-04-23 AR ARP030101394A patent/AR039345A1/es unknown
- 2003-04-23 US US10/421,511 patent/US7169925B2/en not_active Expired - Fee Related
- 2003-04-23 JP JP2003587779A patent/JP4746271B2/ja not_active Expired - Fee Related
- 2003-04-23 KR KR10-2004-7017097A patent/KR20040104613A/ko not_active Ceased
- 2003-04-23 US US10/421,597 patent/US20040006123A1/en not_active Abandoned
- 2003-04-23 KR KR1020047017098A patent/KR100972304B1/ko not_active Expired - Fee Related
-
2007
- 2007-11-30 US US11/947,922 patent/US20080132481A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20040006123A1 (en) | 2004-01-08 |
| TW200408389A (en) | 2004-06-01 |
| KR20040106382A (ko) | 2004-12-17 |
| US20080132481A1 (en) | 2008-06-05 |
| US7169925B2 (en) | 2007-01-30 |
| US20040010029A1 (en) | 2004-01-15 |
| AR039345A1 (es) | 2005-02-16 |
| KR100972304B1 (ko) | 2010-07-26 |
| JP2005529134A (ja) | 2005-09-29 |
| JP4746271B2 (ja) | 2011-08-10 |
| GB0217920D0 (en) | 2002-09-11 |
| TWI296926B (en) | 2008-05-21 |
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