JP2008502689A5 - - Google Patents
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- JP2008502689A5 JP2008502689A5 JP2007516640A JP2007516640A JP2008502689A5 JP 2008502689 A5 JP2008502689 A5 JP 2008502689A5 JP 2007516640 A JP2007516640 A JP 2007516640A JP 2007516640 A JP2007516640 A JP 2007516640A JP 2008502689 A5 JP2008502689 A5 JP 2008502689A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- methyloxy
- ethyl
- pyrrolidinyl
- amino
- 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.)
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 38
- -1 hydroxy, amino, piperidyl Chemical group 0.000 claims 32
- 125000000217 alkyl group Chemical group 0.000 claims 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 8
- 125000004423 acyloxy group Chemical group 0.000 claims 8
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 6
- 125000002252 acyl group Chemical group 0.000 claims 6
- 125000004414 alkyl thio group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 4
- 125000005035 acylthio group Chemical group 0.000 claims 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 4
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 4
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 4
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 125000005110 aryl thio group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 3
- 125000004468 heterocyclylthio group Chemical group 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 238000006467 substitution reaction Methods 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- OTAKZEXNJOXEJV-UHFFFAOYSA-N 6-[[[1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-4-hydroxy-3-methylpyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CNCC3(C(O)CN(C3)CCC3=C(F)C=NC4=CC=C(N=C43)OC)C)=CC=C21 OTAKZEXNJOXEJV-UHFFFAOYSA-N 0.000 claims 2
- QMGXSNRJPLUSFZ-UHFFFAOYSA-N 6-[[[1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-4-hydroxy-4-methylpyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CNCC3CN(CC3(O)C)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 QMGXSNRJPLUSFZ-UHFFFAOYSA-N 0.000 claims 2
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000005647 linker group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- JJRSUAHARRNFCE-QRWLVFNGSA-N (3r,4r)-4-[(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethylamino)methyl]-1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-ol Chemical compound O1CCOC(C=N2)=C1C=C2CNC[C@H](C1)[C@@H](O)CN1CCC1=C(F)C=NC2=CC=C(OC)N=C21 JJRSUAHARRNFCE-QRWLVFNGSA-N 0.000 claims 1
- MIOBHLQDCGKYKZ-MGPUTAFESA-N (3s,4s)-1-[2-(3-chloro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-4-[(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethylamino)methyl]pyrrolidin-3-ol Chemical compound O1CCOC(C=N2)=C1C=C2CNC[C@@H](C1)[C@H](O)CN1CCC1=C(Cl)C=NC2=CC=C(OC)N=C21 MIOBHLQDCGKYKZ-MGPUTAFESA-N 0.000 claims 1
- JBAGRTYXJAZXTN-QFBILLFUSA-N (3s,4s)-1-[2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]-4-[([1,3]oxathiolo[5,4-c]pyridin-6-ylmethylamino)methyl]pyrrolidin-3-ol Chemical compound C([C@@H]1[C@H](O)CN(C1)CCC1=CC=NC2=CC=C(N=C21)OC)NCC(N=C1)=CC2=C1OCS2 JBAGRTYXJAZXTN-QFBILLFUSA-N 0.000 claims 1
- QCZBMHLGOAYDBY-FXAWDEMLSA-N (3s,4s)-4-[(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethylamino)methyl]-1-[2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-ol Chemical compound O1CCOC(C=N2)=C1C=C2CNC[C@@H](C1)[C@H](O)CN1CCC1=CC=NC2=CC=C(OC)N=C21 QCZBMHLGOAYDBY-FXAWDEMLSA-N 0.000 claims 1
- QELFYMZXFIYEMT-FDDCHVKYSA-N (3s,4s)-4-[(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethylamino)methyl]-1-[2-(6-methoxyquinolin-4-yl)ethyl]pyrrolidin-3-ol Chemical compound O1CCOC(C=N2)=C1C=C2CNC[C@@H](C1)[C@H](O)CN1CCC1=CC=NC2=CC=C(OC)C=C21 QELFYMZXFIYEMT-FDDCHVKYSA-N 0.000 claims 1
- NJRYQMQXELIPEV-HRAATJIYSA-N (3s,4s)-4-[[(6-fluoro-2,3-dihydro-1,4-benzodioxin-7-yl)methylamino]methyl]-1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-ol Chemical compound O1CCOC(C=C2F)=C1C=C2CNC[C@@H](C1)[C@H](O)CN1CCC1=C(F)C=NC2=CC=C(OC)N=C21 NJRYQMQXELIPEV-HRAATJIYSA-N 0.000 claims 1
- MYXOEAOZEKNPRT-GHTZIAJQSA-N (3s,4s)-4-[[(6-fluoro-2,3-dihydro-1,4-benzodioxin-7-yl)methylamino]methyl]-1-[2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-ol Chemical compound O1CCOC(C=C2F)=C1C=C2CNC[C@@H](C1)[C@H](O)CN1CCC1=CC=NC2=CC=C(OC)N=C21 MYXOEAOZEKNPRT-GHTZIAJQSA-N 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- VMDJJFHEGITTME-VAXTVUGKSA-N (nz)-n-[(4r)-4-[(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethylamino)methyl]-1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-ylidene]hydroxylamine Chemical compound O1CCOC(C=N2)=C1C=C2CNC[C@@H](\C(C1)=N\O)CN1CCC1=C(F)C=NC2=CC=C(OC)N=C21 VMDJJFHEGITTME-VAXTVUGKSA-N 0.000 claims 1
- JWLXHUMOWOLHDD-SFHVURJKSA-N 1-[(3s)-1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-yl]-n-[(5-methyl-2,3-dihydro-1,4-benzodioxin-7-yl)methyl]methanamine Chemical compound O1CCOC2=CC(CNC[C@@H]3CCN(C3)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC(C)=C21 JWLXHUMOWOLHDD-SFHVURJKSA-N 0.000 claims 1
- NXWNIBCILBABGX-LAUBAEHRSA-N 4-[2-[(3s,4s)-3-[(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethylamino)methyl]-4-hydroxypyrrolidin-1-yl]ethyl]-6-methoxy-1,5-naphthyridine-3-carbonitrile Chemical compound O1CCOC(C=N2)=C1C=C2CNC[C@@H](C1)[C@H](O)CN1CCC1=C(C#N)C=NC2=CC=C(OC)N=C21 NXWNIBCILBABGX-LAUBAEHRSA-N 0.000 claims 1
- AQTGJUAYRROZMJ-OXJNMPFZSA-N 4-[2-[(3s,4s)-3-hydroxy-4-[[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]methyl]pyrrolidin-1-yl]ethyl]-6-methoxy-1,5-naphthyridine-3-carbonitrile Chemical compound O1CC(=O)NC2=NC(CNC[C@@H]3[C@H](O)CN(C3)CCC3=C(C#N)C=NC4=CC=C(N=C43)OC)=CC=C21 AQTGJUAYRROZMJ-OXJNMPFZSA-N 0.000 claims 1
- MXAJIJQIHDVTKE-OXJNMPFZSA-N 4-[2-[(3s,4s)-3-hydroxy-4-[[(3-oxo-4h-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino]methyl]pyrrolidin-1-yl]ethyl]-6-methoxy-1,5-naphthyridine-3-carbonitrile Chemical compound S1CC(=O)NC2=NC(CNC[C@@H]3[C@H](O)CN(C3)CCC3=C(C#N)C=NC4=CC=C(N=C43)OC)=CC=C21 MXAJIJQIHDVTKE-OXJNMPFZSA-N 0.000 claims 1
- FXLONCJBIWCVAE-MRXNPFEDSA-N 6-[[2-[(3r)-1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-yl]propan-2-ylamino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CNC(C)(C)[C@@H]3CCN(C3)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 FXLONCJBIWCVAE-MRXNPFEDSA-N 0.000 claims 1
- UIGLITXJJBGYOH-DNVCBOLYSA-N 6-[[[(3r)-1-[(2s)-2-hydroxy-2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC[C@H]3CCN(C3)C[C@@H](O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 UIGLITXJJBGYOH-DNVCBOLYSA-N 0.000 claims 1
- HEXIHVLAGMRYGG-DNVCBOLYSA-N 6-[[[(3r)-1-[(2s)-2-hydroxy-2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CNC[C@H]3CCN(C3)C[C@@H](O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 HEXIHVLAGMRYGG-DNVCBOLYSA-N 0.000 claims 1
- AXXZHMOPGYOROT-OAHLLOKOSA-N 6-[[[(3r)-1-[2-(3,8-difluoro-6-methoxyquinolin-4-yl)ethyl]pyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CNC[C@H]3CCN(C3)CCC3=C(F)C=NC4=C(F)C=C(C=C43)OC)=CC=C21 AXXZHMOPGYOROT-OAHLLOKOSA-N 0.000 claims 1
- NKMDSVLWUMHSFB-OAHLLOKOSA-N 6-[[[(3r)-1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CNC[C@H]3CCN(C3)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 NKMDSVLWUMHSFB-OAHLLOKOSA-N 0.000 claims 1
- FIVKBBWDRIEIOO-KUHUBIRLSA-N 6-[[[(3r,4r)-1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-4-hydroxypyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC[C@H]3[C@@H](O)CN(C3)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 FIVKBBWDRIEIOO-KUHUBIRLSA-N 0.000 claims 1
- WMGIRTOMZPNXRB-KUHUBIRLSA-N 6-[[[(3r,4r)-1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-4-hydroxypyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CNC[C@H]3[C@@H](O)CN(C3)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 WMGIRTOMZPNXRB-KUHUBIRLSA-N 0.000 claims 1
- KDBOONFUDZSGRQ-CVEARBPZSA-N 6-[[[(3r,4s)-1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-4-(hydroxymethyl)pyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CNC[C@H]3[C@H](CO)CN(C3)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 KDBOONFUDZSGRQ-CVEARBPZSA-N 0.000 claims 1
- LQAZCEZBWLJKGB-KITJZVIWSA-N 6-[[[(3r,4z)-1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-4-hydroxyiminopyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC[C@@H]\3CN(CC/3=N\O)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 LQAZCEZBWLJKGB-KITJZVIWSA-N 0.000 claims 1
- DRNPWHSMRJRDNK-KITJZVIWSA-N 6-[[[(3r,4z)-1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-4-hydroxyiminopyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CNC[C@@H]\3CN(CC/3=N\O)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 DRNPWHSMRJRDNK-KITJZVIWSA-N 0.000 claims 1
- CYSVUKAIZDXTKR-KSSFIOAISA-N 6-[[[(3s)-1-[(2r)-2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-2-hydroxyethyl]pyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CNC[C@@H]3CCN(C3)C[C@H](O)C3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 CYSVUKAIZDXTKR-KSSFIOAISA-N 0.000 claims 1
- UIGLITXJJBGYOH-HNAYVOBHSA-N 6-[[[(3s)-1-[(2s)-2-hydroxy-2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC[C@@H]3CCN(C3)C[C@@H](O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 UIGLITXJJBGYOH-HNAYVOBHSA-N 0.000 claims 1
- HEXIHVLAGMRYGG-HNAYVOBHSA-N 6-[[[(3s)-1-[(2s)-2-hydroxy-2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CNC[C@@H]3CCN(C3)C[C@@H](O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 HEXIHVLAGMRYGG-HNAYVOBHSA-N 0.000 claims 1
- QDUWFNDIZVGQSU-HNNXBMFYSA-N 6-[[[(3s)-1-[2-(3,8-difluoro-6-methoxyquinolin-4-yl)ethyl]pyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC[C@@H]3CCN(C3)CCC3=C(F)C=NC4=C(F)C=C(C=C43)OC)=CC=C21 QDUWFNDIZVGQSU-HNNXBMFYSA-N 0.000 claims 1
- AXXZHMOPGYOROT-HNNXBMFYSA-N 6-[[[(3s)-1-[2-(3,8-difluoro-6-methoxyquinolin-4-yl)ethyl]pyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CNC[C@@H]3CCN(C3)CCC3=C(F)C=NC4=C(F)C=C(C=C43)OC)=CC=C21 AXXZHMOPGYOROT-HNNXBMFYSA-N 0.000 claims 1
- VXHBLDXAEZGAIY-HNNXBMFYSA-N 6-[[[(3s)-1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC[C@@H]3CCN(C3)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 VXHBLDXAEZGAIY-HNNXBMFYSA-N 0.000 claims 1
- NKMDSVLWUMHSFB-HNNXBMFYSA-N 6-[[[(3s)-1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CNC[C@@H]3CCN(C3)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 NKMDSVLWUMHSFB-HNNXBMFYSA-N 0.000 claims 1
- MLAGDUZKYKHYGP-INIZCTEOSA-N 6-[[[(3s)-1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-yl]methylamino]methyl]-7-methyl-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound N1C(=O)CSC(C=C2C)=C1N=C2CNC[C@@H](C1)CCN1CCC1=C(F)C=NC2=CC=C(OC)N=C21 MLAGDUZKYKHYGP-INIZCTEOSA-N 0.000 claims 1
- XWBVGODIKXTXCZ-INIZCTEOSA-N 6-[[[(3s)-1-[2-(3-fluoro-6-methoxyquinolin-4-yl)ethyl]pyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC[C@@H]3CCN(C3)CCC3=C(F)C=NC4=CC=C(C=C43)OC)=CC=C21 XWBVGODIKXTXCZ-INIZCTEOSA-N 0.000 claims 1
- ISEASKLKYNBYQW-INIZCTEOSA-N 6-[[[(3s)-1-[2-(3-fluoro-6-methoxyquinolin-4-yl)ethyl]pyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CNC[C@@H]3CCN(C3)CCC3=C(F)C=NC4=CC=C(C=C43)OC)=CC=C21 ISEASKLKYNBYQW-INIZCTEOSA-N 0.000 claims 1
- CZALNXCRGLFYHR-INIZCTEOSA-N 6-[[[(3s)-1-[2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-yl]methylamino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CNC[C@@H]3CCN(C3)CCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 CZALNXCRGLFYHR-INIZCTEOSA-N 0.000 claims 1
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- HTKGTXYWJIZZLQ-OAHLLOKOSA-N n-[[(3s)-1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-yl]methyl]-3-oxo-4h-1,4-benzothiazine-6-sulfonamide Chemical compound S1CC(=O)NC2=CC(S(=O)(=O)NC[C@H]3CCN(C3)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 HTKGTXYWJIZZLQ-OAHLLOKOSA-N 0.000 claims 1
- PQEFLKRWGRTJFY-AWEZNQCLSA-N n-[[(3s)-1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-yl]methyl]-3-oxo-4h-pyrido[3,2-b][1,4]thiazine-6-carboxamide Chemical compound S1CC(=O)NC2=NC(C(=O)NC[C@@H]3CCN(C3)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 PQEFLKRWGRTJFY-AWEZNQCLSA-N 0.000 claims 1
- LXNSGMKWFGLKPB-HNNXBMFYSA-N n-[[(3s)-1-[2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-yl]methyl]-3-oxo-4h-pyrido[3,2-b][1,4]thiazine-6-carboxamide Chemical compound S1CC(=O)NC2=NC(C(=O)NC[C@@H]3CCN(C3)CCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 LXNSGMKWFGLKPB-HNNXBMFYSA-N 0.000 claims 1
- PHBJPXOVFMFBMC-SCLBCKFNSA-N n-[[(3s,4s)-1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-4-hydroxypyrrolidin-3-yl]methyl]-3-oxo-4h-pyrido[3,2-b][1,4]oxazine-6-carboxamide Chemical compound O1CC(=O)NC2=NC(C(=O)NC[C@@H]3[C@H](O)CN(C3)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 PHBJPXOVFMFBMC-SCLBCKFNSA-N 0.000 claims 1
- RTDOBIOUVJNREA-SCLBCKFNSA-N n-[[(3s,4s)-1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-4-hydroxypyrrolidin-3-yl]methyl]-3-oxo-4h-pyrido[3,2-b][1,4]thiazine-6-carboxamide Chemical compound S1CC(=O)NC2=NC(C(=O)NC[C@@H]3[C@H](O)CN(C3)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 RTDOBIOUVJNREA-SCLBCKFNSA-N 0.000 claims 1
- YXGFDPHTQBNTFS-UHFFFAOYSA-N n-[[1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]pyrrolidin-3-yl]methyl]-n-methyl-3-oxo-4h-pyrido[3,2-b][1,4]thiazine-6-carboxamide Chemical compound S1CC(=O)NC2=NC(C(=O)N(C)CC3CCN(C3)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 YXGFDPHTQBNTFS-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
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| US57987304P | 2004-06-15 | 2004-06-15 | |
| PCT/US2005/020950 WO2006002047A2 (en) | 2004-06-15 | 2005-06-15 | Antibacterial agents |
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| JP2008502689A JP2008502689A (ja) | 2008-01-31 |
| JP2008502689A5 true JP2008502689A5 (https=) | 2008-08-14 |
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| EP (1) | EP1796466A4 (https=) |
| JP (1) | JP2008502689A (https=) |
| WO (1) | WO2006002047A2 (https=) |
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| US7655648B2 (en) | 2004-08-02 | 2010-02-02 | Glaxo Group Limited | Antibacterial agents |
| US7709472B2 (en) | 2005-01-25 | 2010-05-04 | Glaxo Group Limited | Antibacterial agents |
| MY150958A (en) | 2005-06-16 | 2014-03-31 | Astrazeneca Ab | Compounds for the treatment of multi-drug resistant bacterial infections |
| KR20080064173A (ko) * | 2005-10-21 | 2008-07-08 | 글락소 그룹 리미티드 | 항균제로서 유용한 페리 축합 트리시클릭 화합물 |
| EP1790342A1 (de) | 2005-11-11 | 2007-05-30 | Zentaris GmbH | Pyridopyrazin-Derivate und deren Verwendung als Modulatoren der Signaltransduktionswege |
| US8217042B2 (en) | 2005-11-11 | 2012-07-10 | Zentaris Gmbh | Pyridopyrazines and their use as modulators of kinases |
| EP2007377A4 (en) | 2006-04-06 | 2011-08-17 | Glaxo Group Ltd | ANTIBACTERIAL ACTIVE SUBSTANCES |
| WO2007115947A1 (en) | 2006-04-06 | 2007-10-18 | Glaxo Group Limited | Pyrrolo-quinoxalinone derivatives as antibacterials |
| EP1992628A1 (en) | 2007-05-18 | 2008-11-19 | Glaxo Group Limited | Derivatives and analogs of N-ethylquinolones and N-ethylazaquinolones |
| CL2008001003A1 (es) | 2007-04-11 | 2008-10-17 | Actelion Pharmaceuticals Ltd | Compuestos derivados de oxazolidinona; composicion farmaceutica que comprende a dichos compuestos; y su uso para preparar un medicamento para tratar una infeccion bacteriana. |
| EA015821B1 (ru) * | 2007-04-20 | 2011-12-30 | Глэксо Груп Лимитед | Трициклические азотсодержащие соединения в качестве антибактериальных агентов |
| EP2080761A1 (en) | 2008-01-18 | 2009-07-22 | Glaxo Group Limited | Compounds |
| EP2276766A1 (en) | 2008-04-15 | 2011-01-26 | Actelion Pharmaceuticals Ltd. | Tricyclic antibiotics |
| WO2010043714A1 (en) | 2008-10-17 | 2010-04-22 | Glaxo Group Limited | Tricyclic nitrogen compounds used as antibacterials |
| ES2561631T3 (es) | 2009-01-15 | 2016-02-29 | Glaxo Group Limited | Compuestos de naftiridin-2(1H)-ona útiles como agentes antibacterianos |
| WO2010084152A1 (en) | 2009-01-21 | 2010-07-29 | Basilea Pharmaceutica Ag | Novel bicyclic antibiotics |
| AR076222A1 (es) | 2009-04-09 | 2011-05-26 | Actelion Pharmaceuticals Ltd | Derivados 2-hidroxietil-1h-quinolin-ona y sus analogos azaisotericos con actividad antibacteriana y composiciones farmaceuticas que los contienen |
| BR112012016733A2 (pt) | 2010-01-07 | 2015-09-01 | Du Pont | "composto, composição fungicida e método" |
| NZ601080A (en) * | 2010-01-08 | 2014-03-28 | Kyorin Seiyaku Kk | Method for producing 3,4-disubstituted pyrrolidine derivative and production intermediate thereof |
| US20140080810A1 (en) | 2010-11-15 | 2014-03-20 | Exelixis, Inc. | Benzoxazepines as Inhibitors of PI3K/mTOR and Methods of Their Use and Manufacture |
| CA2854266A1 (en) | 2011-11-30 | 2013-06-06 | Actelion Pharmaceuticals Ltd | 3,7-disubstituted octahydro-2h-pyrido[4,3-e][1,3]oxazin-2-one antibiotics |
| DE102012006884A1 (de) * | 2012-04-04 | 2013-10-10 | Merck Patent Gmbh | Cyclische Amide als MetAP-2 Inhibitoren |
| CN102702098A (zh) * | 2012-05-24 | 2012-10-03 | 盛世泰科生物医药技术(苏州)有限公司 | 6-甲氧基-1,2,3,4四氢喹啉-5羧酸甲酯的合成 |
| WO2014057415A2 (en) * | 2012-10-10 | 2014-04-17 | Vitas Pharma Research Pvt Ltd | Inhibitors of dna gyrase for the treatment of bacterial infections |
| JP6546654B2 (ja) | 2014-08-22 | 2019-07-17 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | 淋菌感染を治療するための三環式含窒素化合物 |
| GB201509006D0 (en) | 2015-05-26 | 2015-07-08 | Redx Pharma Plc | Antibacterial compounds |
| UY36851A (es) | 2015-08-16 | 2017-03-31 | Glaxosmithkline Ip Dev Ltd | Compuestos para uso en aplicaciones antibacterianas |
| US9957233B1 (en) | 2016-08-05 | 2018-05-01 | Calitor Sciences, Llc | Process for preparing substituted quinolin-4-ol compounds |
| JP2021515767A (ja) | 2018-03-07 | 2021-06-24 | バイエル・アクチエンゲゼルシヤフト | Ｅｒｋ５阻害剤の同定及び使用 |
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| FR2679906B1 (fr) | 1991-07-31 | 1995-01-20 | Adir | Nouvelles (isoquinolein-5 yl) sulfonamides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| WO1997017973A1 (en) | 1995-11-13 | 1997-05-22 | Smithkline Beecham Corporation | Hemoregulatory compounds |
| US6489354B1 (en) | 1999-03-02 | 2002-12-03 | Merck & Co., Inc. | 3-alkyl substituted pyrrolidine modulators of chemokine receptor activity |
| GB9917408D0 (en) | 1999-07-23 | 1999-09-22 | Smithkline Beecham Plc | Compounds |
| US6410566B1 (en) | 2000-05-16 | 2002-06-25 | Teijin Limited | Cyclic amine derivatives and their use as drugs |
| JP2002047272A (ja) | 2000-07-26 | 2002-02-12 | Dai Ichi Seiyaku Co Ltd | ポリアミンアミド誘導体 |
| CZ2003243A3 (cs) | 2000-07-26 | 2003-09-17 | Smithkline Beecham P. L. C. | Aminopiperidinové chinoliny a jejich azaisosterické analogy s antibakteriální aktivitou |
| GB0101577D0 (en) | 2001-01-22 | 2001-03-07 | Smithkline Beecham Plc | Compounds |
| WO2003064431A2 (en) | 2002-01-29 | 2003-08-07 | Glaxo Group Limited | Aminopiperidine compounds, process for their preparation, and pharmaceutical compositions containing them |
| EP1470125A1 (en) | 2002-01-29 | 2004-10-27 | Glaxo Group Limited | Aminopiperidine derivatives |
| TW200406413A (en) | 2002-06-26 | 2004-05-01 | Glaxo Group Ltd | Compounds |
| AR040336A1 (es) * | 2002-06-26 | 2005-03-30 | Glaxo Group Ltd | Compuesto de piperidina, uso del mismo para la fabricacion de un medicamento, composicion farmaceutica que lo comprende y procedimiento para preparar dicho compuesto |
| GB0217294D0 (en) | 2002-07-25 | 2002-09-04 | Glaxo Group Ltd | Medicaments |
| WO2004035569A2 (de) | 2002-10-10 | 2004-04-29 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Neue verbindungen mit antibakterieller aktivität |
| ATE479683T1 (de) | 2002-11-05 | 2010-09-15 | Glaxo Group Ltd | Antibakterielle mittel |
| DE60331849D1 (de) | 2002-11-05 | 2010-05-06 | Glaxosmithkline Llc | Antibakterielle wirkstoffe |
| AU2003294565A1 (en) | 2002-12-04 | 2004-06-23 | Glaxo Group Limited | Quinolines and nitrogenated derivatives thereof and their use as antibacterial agents |
| TW200427688A (en) | 2002-12-18 | 2004-12-16 | Glaxo Group Ltd | Antibacterial agents |
| TW200507841A (en) | 2003-03-27 | 2005-03-01 | Glaxo Group Ltd | Antibacterial agents |
| US7232833B2 (en) | 2003-03-28 | 2007-06-19 | Novexel | 4-substituted quinoline derivatives, method and intermediates for their preparation and pharmaceutical compositions containing them |
| FR2852954B1 (fr) | 2003-03-28 | 2006-07-14 | Aventis Pharma Sa | Derives de quinoleines-4-substituees, leurs procede et intermediaires de preparation et les compositions pharmaceutiques qui les contiennent |
| DE10316081A1 (de) | 2003-04-08 | 2004-10-21 | Morphochem AG Aktiengesellschaft für kombinatorische Chemie | Neue Verbindungen mit antibakterieller Aktivität |
| FR2858619B1 (fr) | 2003-08-08 | 2006-12-22 | Aventis Pharma Sa | Derives de quinoleines-4-substituees, leurs procede et intermediaires de preparation et les compositions pharmaceutiques qui les contiennent |
| US7348434B2 (en) | 2003-08-08 | 2008-03-25 | Antony Bigot | 4-substituted quinoline derivatives, method and intermediates for their preparation and pharmaceutical compositions containing them |
| FR2872164B1 (fr) | 2004-06-29 | 2006-11-17 | Aventis Pharma Sa | Derives de quinoleines-4-substituees, leur procede et intermediaires de preparation et les compositions pharmaceutiques qui les contiennent |
| US20070254872A1 (en) * | 2004-07-08 | 2007-11-01 | Glaxo Group Limited | Antibacterial Agents |
| DE102004041163A1 (de) | 2004-08-25 | 2006-03-02 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Neue Verbindungen mit antibakterieller Aktivität |
| JP5314244B2 (ja) | 2004-10-27 | 2013-10-16 | 富山化学工業株式会社 | 新規な含窒素複素環化合物およびその塩 |
| NZ562034A (en) | 2005-03-31 | 2009-10-30 | Janssen Pharmaceutica Nv | Bicyclic pyrazole compounds as antibacterial agents |
-
2005
- 2005-06-15 US US11/628,705 patent/US7691850B2/en not_active Expired - Fee Related
- 2005-06-15 EP EP05785327A patent/EP1796466A4/en not_active Withdrawn
- 2005-06-15 WO PCT/US2005/020950 patent/WO2006002047A2/en not_active Ceased
- 2005-06-15 JP JP2007516640A patent/JP2008502689A/ja active Pending
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