ZA200606180B - Chemokine receptor antagonists - Google Patents
Chemokine receptor antagonists Download PDFInfo
- Publication number
- ZA200606180B ZA200606180B ZA200606180A ZA200606180A ZA200606180B ZA 200606180 B ZA200606180 B ZA 200606180B ZA 200606180 A ZA200606180 A ZA 200606180A ZA 200606180 A ZA200606180 A ZA 200606180A ZA 200606180 B ZA200606180 B ZA 200606180B
- Authority
- ZA
- South Africa
- Prior art keywords
- piperidin
- indole
- carboxylic acid
- amide
- ethyl
- Prior art date
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- 229940122444 Chemokine receptor antagonist Drugs 0.000 title description 2
- 239000002559 chemokine receptor antagonist Substances 0.000 title description 2
- -1 amino, carboxy Chemical group 0.000 claims description 79
- 125000003545 alkoxy group Chemical group 0.000 claims description 51
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000003282 alkyl amino group Chemical group 0.000 claims description 19
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 19
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 claims description 19
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000003107 substituted aryl group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- DHBXOVOJDHOGPK-UHFFFAOYSA-N 4-(cyclobutylmethoxy)-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1OCC1CCC1 DHBXOVOJDHOGPK-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- ATJSZTHEQAEHLH-UHFFFAOYSA-N 4-(4-methoxyphenyl)-1h-indole-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=CC2=C1C=C(C(O)=O)N2 ATJSZTHEQAEHLH-UHFFFAOYSA-N 0.000 claims description 6
- KCDNTDCHRUFYIZ-UHFFFAOYSA-N 4-[(5-chloro-1-benzofuran-3-yl)methoxy]-1h-indole-2-carboxylic acid Chemical compound C1=C(Cl)C=C2C(COC3=C4C=C(NC4=CC=C3)C(=O)O)=COC2=C1 KCDNTDCHRUFYIZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- VGFAXKCORNQYFX-UHFFFAOYSA-N 1-[2-(azepan-1-yl)ethyl]piperidin-4-amine Chemical compound C1CC(N)CCN1CCN1CCCCCC1 VGFAXKCORNQYFX-UHFFFAOYSA-N 0.000 claims description 5
- IPCITYBUXQLBOZ-UHFFFAOYSA-N 4-(4-methylphenoxy)-1h-indole-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1OC1=CC=CC2=C1C=C(C(O)=O)N2 IPCITYBUXQLBOZ-UHFFFAOYSA-N 0.000 claims description 5
- RUVKKSCYIJINOW-UHFFFAOYSA-N 4-(furan-3-ylmethoxy)-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1OCC=1C=COC=1 RUVKKSCYIJINOW-UHFFFAOYSA-N 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 239000000651 prodrug Substances 0.000 claims description 5
- 229940002612 prodrug Drugs 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- DAMBXTQUGDTIHT-UHFFFAOYSA-N 4-(3,5-difluorophenoxy)-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1OC1=CC(F)=CC(F)=C1 DAMBXTQUGDTIHT-UHFFFAOYSA-N 0.000 claims description 4
- QCHULMRAPOGNRQ-UHFFFAOYSA-N 4-(3-fluorophenoxy)-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1OC1=CC=CC(F)=C1 QCHULMRAPOGNRQ-UHFFFAOYSA-N 0.000 claims description 4
- BLLFPHHQELRWKO-UHFFFAOYSA-N 4-(4-fluorophenoxy)-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1OC1=CC=C(F)C=C1 BLLFPHHQELRWKO-UHFFFAOYSA-N 0.000 claims description 4
- OCKZBPJPSOFGCJ-UHFFFAOYSA-N 4-[(4,6-dimethoxy-1-benzofuran-3-yl)methoxy]-1h-indole-2-carboxylic acid Chemical compound C=1OC2=CC(OC)=CC(OC)=C2C=1COC1=CC=CC2=C1C=C(C(O)=O)N2 OCKZBPJPSOFGCJ-UHFFFAOYSA-N 0.000 claims description 4
- IDCLFENUIDJACO-UHFFFAOYSA-N 4-(3-methylphenoxy)-1h-indole-2-carboxylic acid Chemical compound CC1=CC=CC(OC=2C=3C=C(NC=3C=CC=2)C(O)=O)=C1 IDCLFENUIDJACO-UHFFFAOYSA-N 0.000 claims description 3
- XXIRXGQNEUCGCN-UHFFFAOYSA-N 4-(4-ethoxyphenyl)-1h-indole-2-carboxylic acid Chemical compound C1=CC(OCC)=CC=C1C1=CC=CC2=C1C=C(C(O)=O)N2 XXIRXGQNEUCGCN-UHFFFAOYSA-N 0.000 claims description 3
- GYULPARFIRFUOC-UHFFFAOYSA-N 4-[(6-methoxy-1-benzofuran-3-yl)methoxy]-1h-indole-2-carboxylic acid Chemical compound C=1OC2=CC(OC)=CC=C2C=1COC1=CC=CC2=C1C=C(C(O)=O)N2 GYULPARFIRFUOC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 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
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 3
- BLQRZAFDGUVKAC-UHFFFAOYSA-N 1-(2-piperidin-1-ylethyl)piperidin-4-amine Chemical compound C1CC(N)CCN1CCN1CCCCC1 BLQRZAFDGUVKAC-UHFFFAOYSA-N 0.000 claims description 2
- KKMVGFXOQKVBAA-XITMACKWSA-N 1-[[(1S,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]methyl]piperidin-4-amine dihydrochloride Chemical compound Cl.Cl.C1CC(N)CCN1C[C@H]1[C@H]2CCCCN2CCC1 KKMVGFXOQKVBAA-XITMACKWSA-N 0.000 claims description 2
- TYSWNTHAYZCQPF-UHFFFAOYSA-N 4-(2,2-dimethylpropoxy)-1h-indole-2-carboxylic acid Chemical compound CC(C)(C)COC1=CC=CC2=C1C=C(C(O)=O)N2 TYSWNTHAYZCQPF-UHFFFAOYSA-N 0.000 claims description 2
- QZJZMQBDAVXPKB-UHFFFAOYSA-N 4-(3,4-difluorophenoxy)-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1OC1=CC=C(F)C(F)=C1 QZJZMQBDAVXPKB-UHFFFAOYSA-N 0.000 claims description 2
- JRTVOVSPBBKPKI-UHFFFAOYSA-N 4-[(5-chloro-1-benzofuran-3-yl)methoxy]-n-[4-(2-piperidin-1-ylethyl)phenyl]-1h-indole-2-carboxamide Chemical compound C12=CC(Cl)=CC=C2OC=C1COC(C=1C=2)=CC=CC=1NC=2C(=O)NC(C=C1)=CC=C1CCN1CCCCC1 JRTVOVSPBBKPKI-UHFFFAOYSA-N 0.000 claims description 2
- ACAFRCDJOPZHTM-UHFFFAOYSA-N 4-[(5-chloro-1-benzofuran-3-yl)methoxy]-n-[4-[2-(4-hydroxypiperidin-1-yl)ethyl]phenyl]-1h-indole-2-carboxamide Chemical compound C1CC(O)CCN1CCC(C=C1)=CC=C1NC(=O)C(NC1=CC=C2)=CC1=C2OCC1=COC2=CC=C(Cl)C=C12 ACAFRCDJOPZHTM-UHFFFAOYSA-N 0.000 claims description 2
- JFIPUTMNRFWARR-UHFFFAOYSA-N 4-[(5-methoxy-1-benzofuran-3-yl)methoxy]-1h-indole-2-carboxylic acid Chemical compound C12=CC(OC)=CC=C2OC=C1COC1=CC=CC2=C1C=C(C(O)=O)N2 JFIPUTMNRFWARR-UHFFFAOYSA-N 0.000 claims description 2
- OARSMQUCRTVKGP-UHFFFAOYSA-N 4-[2-(azepan-1-yl)ethyl]aniline Chemical compound C1=CC(N)=CC=C1CCN1CCCCCC1 OARSMQUCRTVKGP-UHFFFAOYSA-N 0.000 claims description 2
- BNNKANQMIKLOLT-UHFFFAOYSA-N FC1=CC(=CC2=C1C(=CO2)COC2=C1C=C(NC1=CC=C2)C(=O)O)F.Cl.Cl Chemical compound FC1=CC(=CC2=C1C(=CO2)COC2=C1C=C(NC1=CC=C2)C(=O)O)F.Cl.Cl BNNKANQMIKLOLT-UHFFFAOYSA-N 0.000 claims description 2
- AQXJRHQGKAWNEQ-KYARJDOBSA-N O1C=C(C=C1)COC1=C2C=C(NC2=CC=C1)C(=O)O.[C@H]1(CCCN2CCCC[C@H]12)CN1CCC(CC1)NC(=O)C=1NC2=CC=CC(=C2C1)OCC1=COC=C1 Chemical compound O1C=C(C=C1)COC1=C2C=C(NC2=CC=C1)C(=O)O.[C@H]1(CCCN2CCCC[C@H]12)CN1CCC(CC1)NC(=O)C=1NC2=CC=CC(=C2C1)OCC1=COC=C1 AQXJRHQGKAWNEQ-KYARJDOBSA-N 0.000 claims description 2
- NOZCKVZMBHZJDL-UHFFFAOYSA-N n-[1-[2-(4-hydroxypiperidin-1-yl)ethyl]piperidin-4-yl]-4-(4-methylphenoxy)-1h-indole-2-carboxamide Chemical compound C1=CC(C)=CC=C1OC1=CC=CC2=C1C=C(C(=O)NC1CCN(CCN3CCC(O)CC3)CC1)N2 NOZCKVZMBHZJDL-UHFFFAOYSA-N 0.000 claims description 2
- PFCCKHIOBDLHOD-UHFFFAOYSA-N n-[1-[2-(azepan-1-yl)ethyl]piperidin-4-yl]-4-methoxy-1h-indole-2-carboxamide Chemical compound C=1C=2C(OC)=CC=CC=2NC=1C(=O)NC(CC1)CCN1CCN1CCCCCC1 PFCCKHIOBDLHOD-UHFFFAOYSA-N 0.000 claims description 2
- 208000030507 AIDS Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 208000031886 HIV Infections Diseases 0.000 claims 2
- 208000037357 HIV infectious disease Diseases 0.000 claims 2
- 230000001363 autoimmune Effects 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- QDIMGBUZYHVLAV-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)ethyl]azepan-3-amine Chemical compound C1CC(N)CCN1CCN1CC(N)CCCC1 QDIMGBUZYHVLAV-UHFFFAOYSA-N 0.000 claims 1
- SVURQQFGWMEXHK-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)ethyl]azepan-4-ol Chemical compound C1CC(N)CCN1CCN1CCC(O)CCC1 SVURQQFGWMEXHK-UHFFFAOYSA-N 0.000 claims 1
- JJQKBDUCWXTPFJ-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)ethyl]piperidin-4-ol dihydrochloride Chemical compound Cl.Cl.C1CC(N)CCN1CCN1CCC(O)CC1 JJQKBDUCWXTPFJ-UHFFFAOYSA-N 0.000 claims 1
- URNBAQUZYZACMG-SYZUXVNWSA-N 4-(1-benzofuran-3-ylmethoxy)-n-[1-[(2s)-2-[(3s,4s)-4-hydroxy-3-methylpiperidin-1-yl]propyl]piperidin-4-yl]-1h-indole-2-carboxamide Chemical compound N1([C@H](CN2CCC(CC2)NC(=O)C=2NC3=CC=CC(OCC=4C5=CC=CC=C5OC=4)=C3C=2)C)CC[C@H](O)[C@@H](C)C1 URNBAQUZYZACMG-SYZUXVNWSA-N 0.000 claims 1
- GCCOZSRSXOCMFJ-UHFFFAOYSA-N 4-(2,4-dimethoxyphenyl)-1h-indole-2-carboxylic acid Chemical compound COC1=CC(OC)=CC=C1C1=CC=CC2=C1C=C(C(O)=O)N2 GCCOZSRSXOCMFJ-UHFFFAOYSA-N 0.000 claims 1
- AKVKRXVCIYUQMG-UHFFFAOYSA-N 4-(3,3-dimethylbutoxy)-1h-indole-2-carboxylic acid Chemical compound CC(C)(C)CCOC1=CC=CC2=C1C=C(C(O)=O)N2 AKVKRXVCIYUQMG-UHFFFAOYSA-N 0.000 claims 1
- UPNSURZNBBPMGU-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-1h-indole-2-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=CC2=C1C=C(C(O)=O)N2 UPNSURZNBBPMGU-UHFFFAOYSA-N 0.000 claims 1
- NWWMVDGHLDWMBV-UHFFFAOYSA-N 4-(3,5-difluorophenoxy)-n-[1-[2-(4-hydroxypiperidin-1-yl)ethyl]piperidin-4-yl]-1h-indole-2-carboxamide Chemical compound C1CC(O)CCN1CCN1CCC(NC(=O)C=2NC3=CC=CC(OC=4C=C(F)C=C(F)C=4)=C3C=2)CC1 NWWMVDGHLDWMBV-UHFFFAOYSA-N 0.000 claims 1
- SATQSNXTQMUKHS-UHFFFAOYSA-N 4-(3-cyanophenyl)-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1C1=CC=CC(C#N)=C1 SATQSNXTQMUKHS-UHFFFAOYSA-N 0.000 claims 1
- NVBRPWXIBLHDQY-UHFFFAOYSA-N 4-(3-methylbutan-2-yloxy)-1h-indole-2-carboxylic acid Chemical compound CC(C)C(C)OC1=CC=CC2=C1C=C(C(O)=O)N2 NVBRPWXIBLHDQY-UHFFFAOYSA-N 0.000 claims 1
- SKUYHVYEULCXMI-UHFFFAOYSA-N 4-(4-methylphenyl)-1h-indole-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=CC=CC2=C1C=C(C(O)=O)N2 SKUYHVYEULCXMI-UHFFFAOYSA-N 0.000 claims 1
- ZKFQLVBQLWTYCF-UHFFFAOYSA-N 4-(6-methoxypyridin-3-yl)-1h-indole-2-carboxylic acid Chemical compound C1=NC(OC)=CC=C1C1=CC=CC2=C1C=C(C(O)=O)N2 ZKFQLVBQLWTYCF-UHFFFAOYSA-N 0.000 claims 1
- YUXHURQFKWPQFY-UHFFFAOYSA-N 4-(cyclobutylmethoxy)-n-[1-[2-(4-hydroxypiperidin-1-yl)ethyl]piperidin-4-yl]-1h-indole-2-carboxamide Chemical compound C1CC(O)CCN1CCN1CCC(NC(=O)C=2NC3=CC=CC(OCC4CCC4)=C3C=2)CC1 YUXHURQFKWPQFY-UHFFFAOYSA-N 0.000 claims 1
- CIBKFDQBZFCVMN-UHFFFAOYSA-N 4-(cyclopentylmethoxy)-n-[1-[2-(4-hydroxypiperidin-1-yl)ethyl]piperidin-4-yl]-1h-indole-2-carboxamide Chemical compound C1CC(O)CCN1CCN1CCC(NC(=O)C=2NC3=CC=CC(OCC4CCCC4)=C3C=2)CC1 CIBKFDQBZFCVMN-UHFFFAOYSA-N 0.000 claims 1
- WLYZZSPYWVBDOR-SFHVURJKSA-N 4-(cyclopropylmethoxy)-n-[1-[(2s)-2-(4-hydroxypiperidin-1-yl)propyl]piperidin-4-yl]-1h-indole-2-carboxamide Chemical compound C([C@H](C)N1CCC(O)CC1)N(CC1)CCC1NC(=O)C(NC1=CC=C2)=CC1=C2OCC1CC1 WLYZZSPYWVBDOR-SFHVURJKSA-N 0.000 claims 1
- USLDRBBIVSNINB-DYLHXGEVSA-N 4-(furan-3-ylmethoxy)-n-[1-[(2s)-2-[(3s,4s)-4-hydroxy-3-methylpiperidin-1-yl]propyl]piperidin-4-yl]-1h-indole-2-carboxamide Chemical compound C([C@H](C)N1C[C@H](C)[C@@H](O)CC1)N(CC1)CCC1NC(=O)C(NC1=CC=C2)=CC1=C2OCC=1C=COC=1 USLDRBBIVSNINB-DYLHXGEVSA-N 0.000 claims 1
- QLQIHCIYQLGEHK-DFBJGRDBSA-N 4-(furan-3-ylmethoxy)-n-[1-[2-[(3s,4s)-4-hydroxy-3-methylpiperidin-1-yl]ethyl]piperidin-4-yl]-1h-indole-2-carboxamide Chemical compound C1C[C@H](O)[C@@H](C)CN1CCN1CCC(NC(=O)C=2NC3=CC=CC(OCC4=COC=C4)=C3C=2)CC1 QLQIHCIYQLGEHK-DFBJGRDBSA-N 0.000 claims 1
- URSHXXPEUJXMRW-UHFFFAOYSA-N 4-[(4-chloro-1-benzofuran-3-yl)methoxy]-1h-indole-2-carboxylic acid Chemical compound C1=CC(Cl)=C2C(COC3=C4C=C(NC4=CC=C3)C(=O)O)=COC2=C1 URSHXXPEUJXMRW-UHFFFAOYSA-N 0.000 claims 1
- BPVVVEHBKAJIAJ-UHFFFAOYSA-N 4-[(5,6-dimethyl-1-benzofuran-3-yl)methoxy]-1h-indole-2-carboxylic acid Chemical compound C1=2C=C(C)C(C)=CC=2OC=C1COC1=CC=CC2=C1C=C(C(O)=O)N2 BPVVVEHBKAJIAJ-UHFFFAOYSA-N 0.000 claims 1
- PPQGXVXPGBVZLX-FJSYBICCSA-N 4-[(5-chloro-1-benzofuran-3-yl)methoxy]-n-[1-[(2s)-2-(4-hydroxypiperidin-1-yl)propyl]piperidin-4-yl]-1h-indole-2-carboxamide;dihydrochloride Chemical compound Cl.Cl.N1([C@H](CN2CCC(CC2)NC(=O)C=2NC3=CC=CC(OCC=4C5=CC(Cl)=CC=C5OC=4)=C3C=2)C)CCC(O)CC1 PPQGXVXPGBVZLX-FJSYBICCSA-N 0.000 claims 1
- MPECPRUPLTYGFK-UHFFFAOYSA-N 4-[(5-chloro-1-benzofuran-3-yl)methoxy]-n-[1-[2-(4-hydroxypiperidin-1-yl)ethyl]piperidin-4-yl]-1h-indole-2-carboxamide Chemical compound C1CC(O)CCN1CCN1CCC(NC(=O)C=2NC3=CC=CC(OCC=4C5=CC(Cl)=CC=C5OC=4)=C3C=2)CC1 MPECPRUPLTYGFK-UHFFFAOYSA-N 0.000 claims 1
- DPSGRAGJFCWUGA-FJSYBICCSA-N 4-[(6-chloro-1-benzofuran-3-yl)methoxy]-n-[1-[(2s)-2-(4-hydroxypiperidin-1-yl)propyl]piperidin-4-yl]-1h-indole-2-carboxamide;dihydrochloride Chemical compound Cl.Cl.N1([C@H](CN2CCC(CC2)NC(=O)C=2NC3=CC=CC(OCC=4C5=CC=C(Cl)C=C5OC=4)=C3C=2)C)CCC(O)CC1 DPSGRAGJFCWUGA-FJSYBICCSA-N 0.000 claims 1
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- HTIMGXCDQHAORQ-UHFFFAOYSA-N 4-[3-(3-methoxypropoxy)phenyl]-1h-indole-2-carboxylic acid Chemical compound COCCCOC1=CC=CC(C=2C=3C=C(NC=3C=CC=2)C(O)=O)=C1 HTIMGXCDQHAORQ-UHFFFAOYSA-N 0.000 claims 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
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- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- VKESIMXYEVBFLH-UHFFFAOYSA-N n-[1-[2-(azepan-1-yl)ethyl]piperidin-4-yl]-4-(cyclobutylmethoxy)-1h-indole-2-carboxamide Chemical compound C=1C2=C(OCC3CCC3)C=CC=C2NC=1C(=O)NC(CC1)CCN1CCN1CCCCCC1 VKESIMXYEVBFLH-UHFFFAOYSA-N 0.000 description 1
- CGRWVBBYCZIADS-UHFFFAOYSA-N n-[1-[2-(azepan-1-yl)ethyl]piperidin-4-yl]-4-(furan-3-ylmethoxy)-1h-indole-2-carboxamide Chemical compound C=1C2=C(OCC3=COC=C3)C=CC=C2NC=1C(=O)NC(CC1)CCN1CCN1CCCCCC1 CGRWVBBYCZIADS-UHFFFAOYSA-N 0.000 description 1
- MSOVDNCCJWINIX-MUAVYFROSA-N n-[1-[[(1s,9ar)-2,3,4,6,7,8,9,9a-octahydro-1h-quinolizin-1-yl]methyl]piperidin-4-yl]-4-[(4-methoxy-1-benzofuran-3-yl)methoxy]-1h-indole-2-carboxamide Chemical compound C1CCN2CCCC[C@@H]2[C@@H]1CN(CC1)CCC1NC(=O)C(N1)=CC2=C1C=CC=C2OCC1=COC2=C1C(OC)=CC=C2 MSOVDNCCJWINIX-MUAVYFROSA-N 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 239000001301 oxygen Substances 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
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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
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AR065369A1 (es) * | 2007-02-19 | 2009-06-03 | Novartis Ag | Derivados de ciclohexil - amida del acido aril- carboxilico |
US20100035862A1 (en) * | 2008-06-25 | 2010-02-11 | Abbott Laboratories | Novel aza-cyclic indole-2-carboxamides and methods of use thereof |
US8273900B2 (en) * | 2008-08-07 | 2012-09-25 | Novartis Ag | Organic compounds |
SI2513115T1 (sl) | 2009-12-18 | 2014-02-28 | Basilea Pharmaceutica Ag | Triciklični antibiotiki |
ES2594409T3 (es) | 2011-02-23 | 2016-12-20 | Lupin Limited | Derivados de heteroarilo como moduladores del nAChR á7 |
US20140005174A1 (en) * | 2011-03-17 | 2014-01-02 | Anilkumar G. Nair | Indole derivatives useful as ccr2 antagonists |
ES2596369T3 (es) | 2011-06-17 | 2017-01-09 | Basilea Pharmaceutica Ag | Antibióticos N-heterotricíclicos |
US8846656B2 (en) | 2011-07-22 | 2014-09-30 | Novartis Ag | Tetrahydropyrido-pyridine and tetrahydropyrido-pyrimidine compounds and use thereof as C5a receptor modulators |
CN102952062B (zh) * | 2011-08-12 | 2016-06-08 | 中国医学科学院医药生物技术研究所 | 取代苯并杂环类化合物及其制备方法和应用 |
LT2797416T (lt) | 2011-12-28 | 2017-10-25 | Global Blood Therapeutics, Inc. | Pakeistieji benzaldehido junginiai ir jų panaudojimo būdai, didinant audinių aprūpinimą deguonimi |
ES2790358T3 (es) | 2011-12-28 | 2020-10-27 | Global Blood Therapeutics Inc | Compuestos de heteroaril aldehído sustituido y métodos para su uso en el aumento de la oxigenación tisular |
IN2014MN01756A (fr) | 2012-03-06 | 2015-07-03 | Lupin Ltd | |
US9802900B2 (en) | 2013-03-15 | 2017-10-31 | Global Blood Therapeutics, Inc. | Bicyclic heteroaryl compounds and uses thereof for the modulation of hemoglobin |
KR20150132146A (ko) | 2013-03-15 | 2015-11-25 | 글로벌 블러드 테라퓨틱스, 인크. | 헤모글로빈 조정을 위한 화합물 및 이의 용도 |
US9458139B2 (en) | 2013-03-15 | 2016-10-04 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
US10266551B2 (en) | 2013-03-15 | 2019-04-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
WO2014145040A1 (fr) | 2013-03-15 | 2014-09-18 | Global Blood Therapeutics, Inc. | Composés aldéhydes substitués et leurs procédés d'utilisation pour accroître l'oxygénation tissulaire |
MX2015011445A (es) | 2013-03-15 | 2016-04-20 | Global Blood Therapeutics Inc | Compuestos y usos de estos para la modulacion de la hemoglobina. |
US9604999B2 (en) | 2013-03-15 | 2017-03-28 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
US9422279B2 (en) | 2013-03-15 | 2016-08-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
AU2014237348C1 (en) | 2013-03-15 | 2019-02-07 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
US20140274961A1 (en) | 2013-03-15 | 2014-09-18 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
US8952171B2 (en) | 2013-03-15 | 2015-02-10 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
EA201992707A1 (ru) | 2013-11-18 | 2020-06-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
BR112015032160B1 (pt) | 2014-02-07 | 2021-11-30 | Global Blood Therapeutics, Inc | Ansolvato cristalino de composto, composição e composição farmacêutica |
CN104710347B (zh) * | 2015-01-14 | 2018-01-16 | 杭州澳赛诺生物科技有限公司 | (r)‑1‑苄基‑3‑甲基‑1,2,3,6‑四氢哌啶的合成方法 |
MA41841A (fr) | 2015-03-30 | 2018-02-06 | Global Blood Therapeutics Inc | Composés aldéhyde pour le traitement de la fibrose pulmonaire, de l'hypoxie, et de maladies auto-immunes et des tissus conjonctifs |
WO2017066705A1 (fr) * | 2015-10-14 | 2017-04-20 | Aquinnah Pharmaceuticals, Inc. | Composés, compositions et méthodes d'utilisation contre des granules de stress |
MA43373A (fr) | 2015-12-04 | 2018-10-10 | Global Blood Therapeutics Inc | Régimes posologiques pour 2-hydroxy-6-((2- (1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)méthoxy)benzaldéhyde |
CN105820104B (zh) * | 2016-03-10 | 2018-12-11 | 温州医科大学 | 一种具有抗炎作用的吲哚-2-酰胺类化合物及其在制备抗炎药物中的应用 |
TWI663160B (zh) | 2016-05-12 | 2019-06-21 | 全球血液治療公司 | 用於合成2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)-吡啶-3-基)甲氧基)苯甲醛之方法 |
TW202332423A (zh) | 2016-10-12 | 2023-08-16 | 美商全球血液治療公司 | 包含2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)吡啶-3-基)甲氧基)-苯甲醛之片劑 |
AU2018231120B2 (en) * | 2017-03-10 | 2022-06-23 | Rutgers, The State University Of New Jersey | Indole derivatives as efflux pump inhibitors |
WO2020072377A1 (fr) | 2018-10-01 | 2020-04-09 | Global Blood Therapeutics, Inc. | Modulateurs de l'hémoglobine pour le traitement de la drépanocytose |
US20240059688A1 (en) * | 2020-12-22 | 2024-02-22 | Luxembourg Institute Of Health (Lih) | Conolidine analogues as selective ackr3 modulators for the treatment of cancer |
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IE903196A1 (en) | 1989-09-05 | 1991-03-13 | Searle & Co | Substituted n-benzylpiperidine amides |
JP3514490B2 (ja) | 1992-08-21 | 2004-03-31 | 杏林製薬株式会社 | トリフルオロメチルピロロインドールカルボン酸エステル誘導体及びその製造方法 |
AR008331A1 (es) | 1997-01-23 | 1999-12-29 | Smithkline Beecham Corp | Compuestos antagonistas de un receptor de il-8, uso de los mismos para la fabricacion de medicamentos, procedimiento para su obtencion, composicionesfarmaceuticas que los contienen |
EP0991406A4 (fr) | 1997-01-23 | 2000-12-13 | Smithkline Beecham Corp | Antagonistes du recepteur de l'il-8 |
WO1998050364A1 (fr) * | 1997-05-03 | 1998-11-12 | Smithkline Beecham Plc | Derives de tetrahydroisoquinoline comme modulateurs des recepteurs d3 de la dopamine |
US20040043995A1 (en) * | 1997-05-13 | 2004-03-04 | Eric Bignon | Novel triazole derivatives, process for their preparation and pharmaceutical compositions containing them |
FR2763337B1 (fr) * | 1997-05-13 | 1999-08-20 | Sanofi Sa | Nouveaux derives du triazole, un procede pour leur preparation et compositions pharmaceutiques les contenant |
US6172061B1 (en) | 1997-12-19 | 2001-01-09 | Takeda Chemical Industries, Ltd. | Pharmaceutical composition for antagonizing CCR5 comprising anilide derivative |
ZA9811576B (en) * | 1997-12-19 | 2000-06-19 | Takeda Chemical Industries Ltd | Anilide derivative, production and use thereof. |
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- 2005-02-10 EP EP05707321A patent/EP1720859B1/fr active Active
- 2005-02-10 WO PCT/EP2005/001362 patent/WO2005077932A2/fr active Application Filing
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2007
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2010
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