JP2014518267A5 - - Google Patents
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- JP2014518267A5 JP2014518267A5 JP2014518932A JP2014518932A JP2014518267A5 JP 2014518267 A5 JP2014518267 A5 JP 2014518267A5 JP 2014518932 A JP2014518932 A JP 2014518932A JP 2014518932 A JP2014518932 A JP 2014518932A JP 2014518267 A5 JP2014518267 A5 JP 2014518267A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- oxabicyclo
- pyrido
- ethyl
- naphthyridin
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 49
- 125000005843 halogen group Chemical group 0.000 claims 31
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 25
- 229910052717 sulfur Inorganic materials 0.000 claims 24
- -1 NH 2 Chemical group 0.000 claims 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims 22
- 229910052760 oxygen Inorganic materials 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 17
- 229910005965 SO 2 Inorganic materials 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-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
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 claims 4
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 4
- 150000003254 radicals Chemical class 0.000 claims 4
- MZAGXDHQGXUDDX-JSRXJHBZSA-N (e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enamide Chemical group [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/C(N)=O MZAGXDHQGXUDDX-JSRXJHBZSA-N 0.000 claims 3
- VATRZDWMOKJFRC-UHFFFAOYSA-N 2-[[7-fluoro-8-[2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-1,5-naphthyridin-2-yl]oxymethyl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1COC1=CC=C(N=CC(F)=C2CCC34CCC(CC3)(CO4)NCC=3N=C4NC(=O)COC4=CC=3)C2=N1 VATRZDWMOKJFRC-UHFFFAOYSA-N 0.000 claims 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 3
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- PHRMXOZHJPXUJR-UHFFFAOYSA-N 5-[2-hydroxy-2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-6-oxo-1,5-naphthyridine-3-carbonitrile Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)C(CN3C(C=CC4=NC=C(C=C43)C#N)=O)O)=CC=C21 PHRMXOZHJPXUJR-UHFFFAOYSA-N 0.000 claims 2
- YNMAHZUZBRHSMB-UHFFFAOYSA-N 6-[[[1-[(3-chloro-6-methoxy-1,5-naphthyridin-4-yl)oxymethyl]-4-bicyclo[2.2.2]octanyl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(CC4)COC3=C(Cl)C=NC4=CC=C(N=C43)OC)=CC=C21 YNMAHZUZBRHSMB-UHFFFAOYSA-N 0.000 claims 2
- KGBYYYGUVNKMGF-UHFFFAOYSA-N 6-[[[1-[2-(3-chloro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl]-4-bicyclo[2.2.2]octanyl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(CC4)C(O)CC3=C(Cl)C=NC4=CC=C(N=C43)OC)=CC=C21 KGBYYYGUVNKMGF-UHFFFAOYSA-N 0.000 claims 2
- HLRKEWTWMITTSL-UHFFFAOYSA-N 6-[[[4-[1-hydroxy-2-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)C(O)CN3C(=O)C=NC4=CC=C(N=C43)OC)=CC=C21 HLRKEWTWMITTSL-UHFFFAOYSA-N 0.000 claims 2
- RZPMJRMYFYNLEZ-UHFFFAOYSA-N 6-[[[4-[1-hydroxy-2-(7-methoxy-2-oxo-1,8-naphthyridin-1-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)C(O)CN3C(=O)C=CC4=CC=C(N=C43)OC)=CC=C21 RZPMJRMYFYNLEZ-UHFFFAOYSA-N 0.000 claims 2
- ZBAGPAIAXPURHB-UHFFFAOYSA-N 6-[[[4-[2-(3-fluoro-6-methoxy-8-methyl-1,5-naphthyridin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=C(C)C=C(N=C43)OC)=CC=C21 ZBAGPAIAXPURHB-UHFFFAOYSA-N 0.000 claims 2
- XQAFDFNWFSYMIV-UHFFFAOYSA-N 6-[[[4-[2-(7-methoxy-2-oxo-1,8-naphthyridin-1-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCN3C(=O)C=CC4=CC=C(N=C43)OC)=CC=C21 XQAFDFNWFSYMIV-UHFFFAOYSA-N 0.000 claims 2
- HELKSLAMYBXCSD-PSIJGNRBSA-N 6-[[[4-[2-[6-[(3r,4s)-4-aminooxolan-3-yl]oxy-3-fluoro-1,5-naphthyridin-4-yl]ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound N[C@H]1COC[C@@H]1OC1=CC=C(N=CC(F)=C2CCC34CCC(CC3)(CO4)NCC=3N=C4NC(=O)COC4=CC=3)C2=N1 HELKSLAMYBXCSD-PSIJGNRBSA-N 0.000 claims 2
- 208000035143 Bacterial infection Diseases 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 2
- 125000005336 allyloxy group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- CXGFHAFDFOMUEC-UHFFFAOYSA-N methyl 2-[[7-fluoro-8-[2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-1,5-naphthyridin-2-yl]oxymethyl]cyclopropane-1-carboxylate Chemical compound COC(=O)C1CC1COC1=CC=C(N=CC(F)=C2CCC34CCC(CC3)(CO4)NCC=3N=C4NC(=O)COC4=CC=3)C2=N1 CXGFHAFDFOMUEC-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- PSBKYMODPYHLAW-UHFFFAOYSA-N octan-4-amine Chemical compound CCCCC(N)CCC PSBKYMODPYHLAW-UHFFFAOYSA-N 0.000 claims 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- VPOVWWOJQLSEFL-UHFFFAOYSA-N (7-ethenyl-8-methyl-3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methyl-[4-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]azanium;chloride Chemical compound [Cl-].N1C(=O)COC(C(C)=C2C=C)=C1N=C2C[NH2+]C(CC1)(CO2)CCC12CCC1=C(F)C=NC2=CC=C(OC)N=C21 VPOVWWOJQLSEFL-UHFFFAOYSA-N 0.000 claims 1
- VBONXIVMCDJCIX-UHFFFAOYSA-N (7-ethyl-8-methyl-3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methyl-[4-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]azanium;chloride Chemical compound [Cl-].C1=C(OC)N=C2C(CCC34CCC(CC4)(CO3)[NH2+]CC3=NC=4NC(=O)COC=4C(C)=C3CC)=C(F)C=NC2=C1 VBONXIVMCDJCIX-UHFFFAOYSA-N 0.000 claims 1
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims 1
- OLOZPSRCROBHRI-UHFFFAOYSA-N 1-[1-(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethylamino)-3-oxabicyclo[2.2.2]octan-4-yl]-2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethanol Chemical compound O1CCOC(C=N2)=C1C=C2CNC(CC1)(CO2)CCC12C(O)CC1=C(F)C=NC2=CC=C(OC)N=C21 OLOZPSRCROBHRI-UHFFFAOYSA-N 0.000 claims 1
- GFQDUKZKOBQWAI-UHFFFAOYSA-N 1-[2-[1-(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethylamino)-3-oxabicyclo[2.2.2]octan-4-yl]-2-hydroxyethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound O1CCOC(C=N2)=C1C=C2CNC(CC1)(CO2)CCC12C(O)CN1C(=O)C=CC2=NC=C(OC)C=C21 GFQDUKZKOBQWAI-UHFFFAOYSA-N 0.000 claims 1
- HGPBSZHFLNTGOF-UHFFFAOYSA-N 1-[[7-fluoro-8-[2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-1,5-naphthyridin-2-yl]oxymethyl]cyclopropane-1-carbonitrile Chemical compound N=1C2=C(CCC34CCC(CC3)(CO4)NCC=3N=C4NC(=O)COC4=CC=3)C(F)=CN=C2C=CC=1OCC1(C#N)CC1 HGPBSZHFLNTGOF-UHFFFAOYSA-N 0.000 claims 1
- LKKIXTRVSFNACN-UHFFFAOYSA-N 1-[[7-fluoro-8-[2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-1,5-naphthyridin-2-yl]oxymethyl]cyclopropane-1-carboxylic acid Chemical compound C=1C=C2N=CC(F)=C(CCC34CCC(CC3)(CO4)NCC=3N=C4NC(=O)COC4=CC=3)C2=NC=1OCC1(C(=O)O)CC1 LKKIXTRVSFNACN-UHFFFAOYSA-N 0.000 claims 1
- CSTGEWWOGMITFK-UHFFFAOYSA-N 2,2-difluoro-4-[[7-fluoro-8-[2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-1,5-naphthyridin-2-yl]oxy]butanoic acid Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)OCCC(F)(F)C(=O)O)=CC=C21 CSTGEWWOGMITFK-UHFFFAOYSA-N 0.000 claims 1
- MTZSHYOEZYDIJD-UHFFFAOYSA-N 2,3-dihydro-1h-pyrido[2,3-b][1,4]oxazin-1-ium-6-ylmethyl-[4-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]azanium;dichloride Chemical compound [Cl-].[Cl-].[NH2+]1CCOC2=NC(C[NH2+]C34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 MTZSHYOEZYDIJD-UHFFFAOYSA-N 0.000 claims 1
- WXIVTWHNZBXIPK-MCUHHSGHSA-N 2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethyl-[1-[(1r)-2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl]-4-bicyclo[2.2.2]octanyl]azanium;chloride Chemical compound [Cl-].O1CCOC(C=N2)=C1C=C2C[NH2+]C(CC1)(CC2)CCC12[C@H](O)CC1=C(F)C=NC2=CC=C(OC)N=C21 WXIVTWHNZBXIPK-MCUHHSGHSA-N 0.000 claims 1
- WXIVTWHNZBXIPK-PVPNGJESSA-N 2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethyl-[1-[(1s)-2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl]-4-bicyclo[2.2.2]octanyl]azanium;chloride Chemical compound [Cl-].O1CCOC(C=N2)=C1C=C2C[NH2+]C(CC1)(CC2)CCC12[C@@H](O)CC1=C(F)C=NC2=CC=C(OC)N=C21 WXIVTWHNZBXIPK-PVPNGJESSA-N 0.000 claims 1
- LIRNZJCTRSWRJY-UHFFFAOYSA-N 2-[[7-fluoro-8-[2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-1,5-naphthyridin-2-yl]oxy]-n,n-dimethylacetamide Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)OCC(=O)N(C)C)=CC=C21 LIRNZJCTRSWRJY-UHFFFAOYSA-N 0.000 claims 1
- MFNVOCAEZQBGRD-UHFFFAOYSA-N 2-[[7-fluoro-8-[2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-1,5-naphthyridin-2-yl]oxy]-n-methylacetamide Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)OCC(=O)NC)=CC=C21 MFNVOCAEZQBGRD-UHFFFAOYSA-N 0.000 claims 1
- HQAQDKALACBCAU-UHFFFAOYSA-N 2-[[8-[2-[1-(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethylamino)-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-yl]oxy]-n-methylacetamide Chemical compound O1CCOC(C=N2)=C1C=C2CNC(CC1)(CO2)CCC12CCC1=C(F)C=NC2=CC=C(OCC(=O)NC)N=C21 HQAQDKALACBCAU-UHFFFAOYSA-N 0.000 claims 1
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- BOKNGNTXEGPVQY-FIWJQRBSSA-N 3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-4-ium-6-ylmethyl-[4-[(1s)-2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl]-3-oxabicyclo[2.2.2]octan-1-yl]azanium;dichloride Chemical compound [Cl-].[Cl-].O1CC[NH2+]C2=NC(C[NH2+]C34CCC(CC3)(OC4)[C@@H](O)CC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 BOKNGNTXEGPVQY-FIWJQRBSSA-N 0.000 claims 1
- ZHYVUGYKKPCWJA-UHFFFAOYSA-N 3-[[[4-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-1-methyl-1,5-naphthyridin-2-one Chemical compound C1=CC=C2N(C)C(=O)C(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC2=N1 ZHYVUGYKKPCWJA-UHFFFAOYSA-N 0.000 claims 1
- OFJCXPPVVQZWSV-UHFFFAOYSA-N 3-[[[4-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-1-methyl-1,8-naphthyridin-2-one;hydrochloride Chemical compound Cl.C1=CN=C2N(C)C(=O)C(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC2=C1 OFJCXPPVVQZWSV-UHFFFAOYSA-N 0.000 claims 1
- UCYQRYZQZNKFNX-UHFFFAOYSA-N 4-[2-[1-(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethylamino)-3-oxabicyclo[2.2.2]octan-4-yl]-2-hydroxyethyl]-6-methoxypyrido[2,3-b]pyrazin-3-one Chemical compound O1CCOC(C=N2)=C1C=C2CNC(CC1)(CO2)CCC12C(O)CN1C(=O)C=NC2=CC=C(OC)N=C21 UCYQRYZQZNKFNX-UHFFFAOYSA-N 0.000 claims 1
- ABEOYXUXIXFGCT-UHFFFAOYSA-N 4-[2-[1-(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethylamino)-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-6-methoxy-1,5-naphthyridine-3-carbonitrile Chemical compound O1CCOC(C=N2)=C1C=C2CNC(CC1)(CO2)CCC12CCC1=C(C#N)C=NC2=CC=C(OC)N=C21 ABEOYXUXIXFGCT-UHFFFAOYSA-N 0.000 claims 1
- ZIYPNZRTVUGSMH-UHFFFAOYSA-N 4-[2-[1-(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethylamino)-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-6-methoxypyrido[2,3-b]pyrazin-3-one Chemical compound O1CCOC(C=N2)=C1C=C2CNC(CC1)(CO2)CCC12CCN1C(=O)C=NC2=CC=C(OC)N=C21 ZIYPNZRTVUGSMH-UHFFFAOYSA-N 0.000 claims 1
- HOTABTFXYFBILL-UHFFFAOYSA-N 4-[2-hydroxy-2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-6-(3-hydroxypropoxy)-1,5-naphthyridine-3-carbonitrile Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)C(O)CC3=C(C#N)C=NC4=CC=C(N=C43)OCCCO)=CC=C21 HOTABTFXYFBILL-UHFFFAOYSA-N 0.000 claims 1
- HVBWIMUEWVQTIX-UHFFFAOYSA-N 4-[2-hydroxy-2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-6-methoxy-1,5-naphthyridine-3-carbonitrile;hydrochloride Chemical compound Cl.O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)C(O)CC3=C(C#N)C=NC4=CC=C(N=C43)OC)=CC=C21 HVBWIMUEWVQTIX-UHFFFAOYSA-N 0.000 claims 1
- BJRMCASKSDZWPQ-UHFFFAOYSA-N 4-[2-hydroxy-2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-6-oxo-7,8-dihydro-5h-1,5-naphthyridine-3-carbonitrile Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)C(CC=3C(=CN=C4CCC(=O)NC4=3)C#N)O)=CC=C21 BJRMCASKSDZWPQ-UHFFFAOYSA-N 0.000 claims 1
- ZNBXANSHVORBJB-UHFFFAOYSA-N 4-[[7-cyano-8-[2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-1,5-naphthyridin-2-yl]oxy]butanoic acid Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(C#N)C=NC4=CC=C(N=C43)OCCCC(=O)O)=CC=C21 ZNBXANSHVORBJB-UHFFFAOYSA-N 0.000 claims 1
- RGHWQSMOWWEXGJ-UHFFFAOYSA-N 4-[[7-fluoro-8-[2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-1,5-naphthyridin-2-yl]oxy]butanenitrile Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C4N=C(OCCCC#N)C=CC4=NC=C3F)=CC=C21 RGHWQSMOWWEXGJ-UHFFFAOYSA-N 0.000 claims 1
- IUHQCBLXDNGGHW-UHFFFAOYSA-N 4-[[7-fluoro-8-[2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-1,5-naphthyridin-2-yl]oxy]butanoic acid Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)OCCCC(=O)O)=CC=C21 IUHQCBLXDNGGHW-UHFFFAOYSA-N 0.000 claims 1
- FBXGQDUVJBKEAJ-UHFFFAOYSA-N 4h-oxazin-3-one Chemical compound O=C1CC=CON1 FBXGQDUVJBKEAJ-UHFFFAOYSA-N 0.000 claims 1
- GHEUSQFNMVKILT-UHFFFAOYSA-N 5,8-difluoro-3-[[[4-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-1-methylquinolin-2-one Chemical compound C1=CC(F)=C2N(C)C(=O)C(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC2=C1F GHEUSQFNMVKILT-UHFFFAOYSA-N 0.000 claims 1
- OJPYTUYOJDWPJQ-UHFFFAOYSA-N 5-[2-[1-(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethylamino)-3-oxabicyclo[2.2.2]octan-4-yl]-2-hydroxyethyl]-6-oxo-1,5-naphthyridine-3-carbonitrile Chemical compound O1CCOC(C=N2)=C1C=C2CNC(CC1)(CO2)CCC12C(O)CN1C(=O)C=CC2=NC=C(C#N)C=C21 OJPYTUYOJDWPJQ-UHFFFAOYSA-N 0.000 claims 1
- LLQTWPUPOTXGPN-UHFFFAOYSA-N 5-[[7-fluoro-8-[2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-1,5-naphthyridin-2-yl]oxy]pentanoic acid Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)OCCCCC(=O)O)=CC=C21 LLQTWPUPOTXGPN-UHFFFAOYSA-N 0.000 claims 1
- KPCUSHHKTYZSMW-UHFFFAOYSA-N 6-(2-hydroxyethoxy)-4-[2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-1,5-naphthyridine-3-carbonitrile Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(C#N)C=NC4=CC=C(N=C43)OCCO)=CC=C21 KPCUSHHKTYZSMW-UHFFFAOYSA-N 0.000 claims 1
- WRPRYKXQAHOHAS-UHFFFAOYSA-N 6-(2-hydroxyethoxy)-4-[2-hydroxy-2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-1,5-naphthyridine-3-carbonitrile Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)C(O)CC3=C(C#N)C=NC4=CC=C(N=C43)OCCO)=CC=C21 WRPRYKXQAHOHAS-UHFFFAOYSA-N 0.000 claims 1
- MURXRTWXVGTFOZ-UHFFFAOYSA-N 6-(3-hydroxypropoxy)-4-[2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-1,5-naphthyridine-3-carbonitrile Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(C#N)C=NC4=CC=C(N=C43)OCCCO)=CC=C21 MURXRTWXVGTFOZ-UHFFFAOYSA-N 0.000 claims 1
- RRINSAUUXYCEQD-VOTSOKGWSA-N 6-[[[1-[(e)-2-(3-chloro-6-methoxy-1,5-naphthyridin-4-yl)ethenyl]-4-bicyclo[2.2.2]octanyl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(CC4)/C=C/C3=C(Cl)C=NC4=CC=C(N=C43)OC)=CC=C21 RRINSAUUXYCEQD-VOTSOKGWSA-N 0.000 claims 1
- FAQUJVPRWNZYRS-UHFFFAOYSA-N 6-[[[1-[2-(3-chloro-6-methoxy-1,5-naphthyridin-4-yl)-2-hydroxyethyl]-4-bicyclo[2.2.2]octanyl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(CC4)CC(O)C3=C(Cl)C=NC4=CC=C(N=C43)OC)=CC=C21 FAQUJVPRWNZYRS-UHFFFAOYSA-N 0.000 claims 1
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- KYWQVGWCOMVMOB-UHFFFAOYSA-N 6-[[[1-[2-(3-chloro-6-methoxy-1,5-naphthyridin-4-yl)ethynyl]-4-bicyclo[2.2.2]octanyl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(CC4)C#CC3=C(Cl)C=NC4=CC=C(N=C43)OC)=CC=C21 KYWQVGWCOMVMOB-UHFFFAOYSA-N 0.000 claims 1
- LGHDBJZNOAKLSA-UHFFFAOYSA-N 6-[[[1-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-4-bicyclo[2.2.2]octanyl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(CC4)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 LGHDBJZNOAKLSA-UHFFFAOYSA-N 0.000 claims 1
- IJHGKXUQHWKCCE-UHFFFAOYSA-N 6-[[[1-[2-(3-hydroxy-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-2-oxabicyclo[2.2.2]octan-4-yl]amino]methyl]-4H-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(O)C=NC4=CC=C(N=C43)OC)=CC=C21 IJHGKXUQHWKCCE-UHFFFAOYSA-N 0.000 claims 1
- CCPAGMQABLBLNT-UHFFFAOYSA-N 6-[[[1-[2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]-4-bicyclo[2.2.2]octanyl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(CC4)CCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 CCPAGMQABLBLNT-UHFFFAOYSA-N 0.000 claims 1
- KECDBAMABNMCOQ-UHFFFAOYSA-N 6-[[[4-[(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)oxymethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)COC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 KECDBAMABNMCOQ-UHFFFAOYSA-N 0.000 claims 1
- NXGYRTWZYXLOEB-VOTSOKGWSA-N 6-[[[4-[(e)-2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethenyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)/C=C/C3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 NXGYRTWZYXLOEB-VOTSOKGWSA-N 0.000 claims 1
- RWWVMZZZRSGQDJ-UHFFFAOYSA-N 6-[[[4-[1-hydroxy-2-(7-methoxy-2-oxo-1,5-naphthyridin-1-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)C(O)CN3C(=O)C=CC4=NC=C(C=C43)OC)=CC=C21 RWWVMZZZRSGQDJ-UHFFFAOYSA-N 0.000 claims 1
- RPGAJANDUNUCGD-UHFFFAOYSA-N 6-[[[4-[1-hydroxy-2-(7-methoxy-2-oxo-1,5-naphthyridin-1-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one;hydrochloride Chemical compound Cl.O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)C(O)CN3C(=O)C=CC4=NC=C(C=C43)OC)=CC=C21 RPGAJANDUNUCGD-UHFFFAOYSA-N 0.000 claims 1
- VGXLTSCPVFVTRF-UHFFFAOYSA-N 6-[[[4-[2-(3,8-difluoro-6-methoxyquinolin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=C(F)C=C(C=C43)OC)=CC=C21 VGXLTSCPVFVTRF-UHFFFAOYSA-N 0.000 claims 1
- KORWOFIKLKGGQH-UHFFFAOYSA-N 6-[[[4-[2-(3-chloro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(Cl)C=NC4=CC=C(N=C43)OC)=CC=C21 KORWOFIKLKGGQH-UHFFFAOYSA-N 0.000 claims 1
- RXTPXDFPFGCINK-UHFFFAOYSA-N 6-[[[4-[2-(3-fluoro-1,5-naphthyridin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C4N=CC=CC4=NC=C3F)=CC=C21 RXTPXDFPFGCINK-UHFFFAOYSA-N 0.000 claims 1
- JWCUKLIKGBNEKA-UHFFFAOYSA-N 6-[[[4-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)C(O)CC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 JWCUKLIKGBNEKA-UHFFFAOYSA-N 0.000 claims 1
- SJBZAZZMIZEOHC-UHFFFAOYSA-N 6-[[[4-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)C(O)CC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 SJBZAZZMIZEOHC-UHFFFAOYSA-N 0.000 claims 1
- HPPWFRFBBQNSJX-UHFFFAOYSA-N 6-[[[4-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-2-hydroxyethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CC(O)C3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 HPPWFRFBBQNSJX-UHFFFAOYSA-N 0.000 claims 1
- CJLSFOJNRRNGPL-UHFFFAOYSA-N 6-[[[4-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-2-hydroxyethyl]-3-thiabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(SC4)CC(O)C3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 CJLSFOJNRRNGPL-UHFFFAOYSA-N 0.000 claims 1
- BCOYDHFZZXSZFA-UHFFFAOYSA-N 6-[[[4-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 BCOYDHFZZXSZFA-UHFFFAOYSA-N 0.000 claims 1
- VHUJFZUVWWPLDS-UHFFFAOYSA-N 6-[[[4-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 VHUJFZUVWWPLDS-UHFFFAOYSA-N 0.000 claims 1
- YZQJLUCGCYHYSE-UHFFFAOYSA-N 6-[[[4-[2-(3-fluoro-6-methoxyquinolin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(C=C43)OC)=CC=C21 YZQJLUCGCYHYSE-UHFFFAOYSA-N 0.000 claims 1
- HMKRKNIGUHIIBQ-UHFFFAOYSA-N 6-[[[4-[2-(3-fluoro-6-methyl-1,5-naphthyridin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)C)=CC=C21 HMKRKNIGUHIIBQ-UHFFFAOYSA-N 0.000 claims 1
- MBHXCYHYWQPDMS-UHFFFAOYSA-N 6-[[[4-[2-(3-fluoro-6-oxo-5h-1,5-naphthyridin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)O)=CC=C21 MBHXCYHYWQPDMS-UHFFFAOYSA-N 0.000 claims 1
- VGLLCLTVTFPDBG-UHFFFAOYSA-N 6-[[[4-[2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 VGLLCLTVTFPDBG-UHFFFAOYSA-N 0.000 claims 1
- CRSFUKCKGCUYKZ-UHFFFAOYSA-N 6-[[[4-[2-(6-methoxypyrido[3,2-d]pyrimidin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one;hydrochloride Chemical compound Cl.O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=NC=NC4=CC=C(N=C43)OC)=CC=C21 CRSFUKCKGCUYKZ-UHFFFAOYSA-N 0.000 claims 1
- AWNYNJVFJWAKMB-UHFFFAOYSA-N 6-[[[4-[2-(7-fluoro-2-oxo-1,5-naphthyridin-1-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCN3C(=O)C=CC4=NC=C(C=C43)F)=CC=C21 AWNYNJVFJWAKMB-UHFFFAOYSA-N 0.000 claims 1
- XBAMQMPZBSSJLC-UHFFFAOYSA-N 6-[[[4-[2-(7-methoxy-2-oxo-1,5-naphthyridin-1-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCN3C(=O)C=CC4=NC=C(C=C43)OC)=CC=C21 XBAMQMPZBSSJLC-UHFFFAOYSA-N 0.000 claims 1
- RFCBQFWVBIQVBT-UHFFFAOYSA-N 6-[[[4-[2-(7-methoxy-2-oxopyrido[2,3-b]pyrazin-1-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCN3C(=O)C=NC4=NC=C(C=C43)OC)=CC=C21 RFCBQFWVBIQVBT-UHFFFAOYSA-N 0.000 claims 1
- SCVXXLXKCCHPRP-UHFFFAOYSA-N 6-[[[4-[2-(7-methoxy-4-oxoquinolin-1-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCN3C=4C(C(C=C3)=O)=CC=C(C=4)OC)=CC=C21 SCVXXLXKCCHPRP-UHFFFAOYSA-N 0.000 claims 1
- ZYKOAEGHWUIGAW-UHFFFAOYSA-N 6-[[[4-[2-(7-methyl-2-oxo-1,8-naphthyridin-1-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCN3C(=O)C=CC4=CC=C(N=C43)C)=CC=C21 ZYKOAEGHWUIGAW-UHFFFAOYSA-N 0.000 claims 1
- GQFNJEBVWJQHSF-UHFFFAOYSA-N 6-[[[4-[2-[3-fluoro-6-(2-hydroxyethoxy)-1,5-naphthyridin-4-yl]-1-hydroxyethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one;hydrochloride Chemical compound Cl.O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)C(O)CC3=C(F)C=NC4=CC=C(N=C43)OCCO)=CC=C21 GQFNJEBVWJQHSF-UHFFFAOYSA-N 0.000 claims 1
- HBISBEJOUCABCD-UHFFFAOYSA-N 6-[[[4-[2-[3-fluoro-6-(2-hydroxyethoxy)-1,5-naphthyridin-4-yl]ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)OCCO)=CC=C21 HBISBEJOUCABCD-UHFFFAOYSA-N 0.000 claims 1
- KEYFYLOJJBRLQT-UHFFFAOYSA-N 6-[[[4-[2-[3-fluoro-6-(2-hydroxyethylamino)-1,5-naphthyridin-4-yl]ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)NCCO)=CC=C21 KEYFYLOJJBRLQT-UHFFFAOYSA-N 0.000 claims 1
- IAMAZFIIXDZFEZ-UHFFFAOYSA-N 6-[[[4-[2-[3-fluoro-6-(2-oxo-1,3-oxazolidin-3-yl)-1,5-naphthyridin-4-yl]ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound N=1C2=C(CCC34CCC(CC3)(CO4)NCC=3N=C4NC(=O)COC4=CC=3)C(F)=CN=C2C=CC=1N1CCOC1=O IAMAZFIIXDZFEZ-UHFFFAOYSA-N 0.000 claims 1
- VELGCXBRGSZRJU-UHFFFAOYSA-N 6-[[[4-[2-[3-fluoro-6-(3-hydroxyazetidin-1-yl)-1,5-naphthyridin-4-yl]ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound C1C(O)CN1C1=CC=C(N=CC(F)=C2CCC34CCC(CC3)(CO4)NCC=3N=C4NC(=O)COC4=CC=3)C2=N1 VELGCXBRGSZRJU-UHFFFAOYSA-N 0.000 claims 1
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- SSAGDEQLRRHDJL-UHFFFAOYSA-N [4-[2-(6-bromo-3-oxo-1,4-benzoxazin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]azanium;chloride Chemical compound [Cl-].O1CC(=O)NC2=NC(C[NH2+]C34CCC(CC3)(OC4)CCN3C(=O)COC4=CC=C(C=C43)Br)=CC=C21 SSAGDEQLRRHDJL-UHFFFAOYSA-N 0.000 claims 1
- JSCHJWGRDCSHPY-UHFFFAOYSA-N [4-[2-(6-cyano-3-oxo-1,4-benzoxazin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-yl]-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]azanium;chloride Chemical compound [Cl-].O=C1COC2=CC=C(C#N)C=C2N1CCC(OC1)(CC2)CCC21[NH2+]CC1=CC=C2OCC(=O)NC2=N1 JSCHJWGRDCSHPY-UHFFFAOYSA-N 0.000 claims 1
- YCHMAJMWLOWACG-UHFFFAOYSA-N [4-[2-[3-fluoro-6-(2-hydroxyethoxy)-1,5-naphthyridin-4-yl]-2-hydroxypropyl]-3-oxabicyclo[2.2.2]octan-1-yl]-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]azanium;chloride Chemical compound [Cl-].C1=C(OCCO)N=C2C(C(O)(CC34CCC(CC3)(CO4)[NH2+]CC=3N=C4NC(=O)COC4=CC=3)C)=C(F)C=NC2=C1 YCHMAJMWLOWACG-UHFFFAOYSA-N 0.000 claims 1
- WWDIQIDHXIWKSE-UHFFFAOYSA-N [4-[2-[3-fluoro-6-(3-hydroxypropoxy)-1,5-naphthyridin-4-yl]-2-hydroxyethyl]-3-oxabicyclo[2.2.2]octan-1-yl]-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]azanium;chloride Chemical compound [Cl-].O1CC(=O)NC2=NC(C[NH2+]C34CCC(CC3)(OC4)CC(O)C3=C(F)C=NC4=CC=C(N=C43)OCCCO)=CC=C21 WWDIQIDHXIWKSE-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical compound C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 claims 1
- 229940124587 cephalosporin Drugs 0.000 claims 1
- 150000001780 cephalosporins Chemical class 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- SGBIPKSFOQACNA-UHFFFAOYSA-N cyclopropanecarboxylic acid;hydrochloride Chemical compound Cl.OC(=O)C1CC1 SGBIPKSFOQACNA-UHFFFAOYSA-N 0.000 claims 1
- AUMKIRNMXZPPIG-UHFFFAOYSA-N ethyl 4-[[7-fluoro-8-[2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-1,5-naphthyridin-2-yl]oxy]butanoate Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)OCCCC(=O)OCC)=CC=C21 AUMKIRNMXZPPIG-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- SDQZRJQWIQHIKN-UHFFFAOYSA-N methyl 1-[[7-fluoro-8-[2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-1,5-naphthyridin-2-yl]oxymethyl]cyclopropane-1-carboxylate Chemical compound C=1C=C2N=CC(F)=C(CCC34CCC(CC3)(CO4)NCC=3N=C4NC(=O)COC4=CC=3)C2=NC=1OCC1(C(=O)OC)CC1 SDQZRJQWIQHIKN-UHFFFAOYSA-N 0.000 claims 1
- FBXMQLGXPQSALD-UHFFFAOYSA-N methyl 5-[[7-fluoro-8-[2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-1,5-naphthyridin-2-yl]oxy]pentanoate Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)OCCCCC(=O)OC)=CC=C21 FBXMQLGXPQSALD-UHFFFAOYSA-N 0.000 claims 1
- GUTOCTQLMMUUBN-UHFFFAOYSA-N methyl 7-fluoro-8-[2-[1-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]-3-oxabicyclo[2.2.2]octan-4-yl]ethyl]-1,5-naphthyridine-2-carboxylate Chemical compound O1CC(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)C(=O)OC)=CC=C21 GUTOCTQLMMUUBN-UHFFFAOYSA-N 0.000 claims 1
- BMPYUKPQAZFIGL-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-amine Chemical compound O1CCOC2=CC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 BMPYUKPQAZFIGL-UHFFFAOYSA-N 0.000 claims 1
- UNKZSMSMKBLWLQ-UHFFFAOYSA-N n-[(2,2-dioxo-1h-pyrido[2,3-e][1,3,4]oxathiazin-7-yl)methyl]-4-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-amine Chemical compound O1CS(=O)(=O)NC2=NC(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC=C21 UNKZSMSMKBLWLQ-UHFFFAOYSA-N 0.000 claims 1
- IYOXETKIHBRUHA-UHFFFAOYSA-N n-[(5,8-difluoro-2-methoxyquinolin-3-yl)methyl]-4-[2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl]-3-oxabicyclo[2.2.2]octan-1-amine Chemical compound C1=CC(F)=C2N=C(OC)C(CNC34CCC(CC3)(OC4)CCC3=C(F)C=NC4=CC=C(N=C43)OC)=CC2=C1F IYOXETKIHBRUHA-UHFFFAOYSA-N 0.000 claims 1
- CRXYSJGFRUZNAY-UHFFFAOYSA-N octan-4-amine;hydrochloride Chemical compound Cl.CCCCC(N)CCC CRXYSJGFRUZNAY-UHFFFAOYSA-N 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 229940049954 penicillin Drugs 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 0 CC(C(C)O1)O*1=O Chemical compound CC(C(C)O1)O*1=O 0.000 description 1
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| US201161501692P | 2011-06-27 | 2011-06-27 | |
| US61/501,692 | 2011-06-27 | ||
| PCT/US2012/044267 WO2013003383A1 (en) | 2011-06-27 | 2012-06-26 | Bridged bicyclic compounds for the treatment of bacterial infections |
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| JP2014518267A JP2014518267A (ja) | 2014-07-28 |
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| EP (1) | EP2723737A1 (https=) |
| JP (1) | JP2014518267A (https=) |
| AU (1) | AU2012275499A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB201111705D0 (en) * | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Compounds and their use |
| JO3115B1 (ar) | 2011-08-22 | 2017-09-20 | Takeda Pharmaceuticals Co | مركبات بيريدازينون واستخدامها كمثبطات daao |
| UA111861C2 (uk) | 2011-11-15 | 2016-06-24 | Такеда Фармасьютікал Компані Лімітед | Ароматична гетероциклічна сполука дигідрокси |
| AR089929A1 (es) * | 2012-02-10 | 2014-10-01 | Actelion Pharmaceuticals Ltd | Proceso para manufacturar un derivado de naftiridina |
| GB201222711D0 (en) | 2012-12-17 | 2013-01-30 | Takeda Pharmaceutical | Novel compounds |
| JP6112724B2 (ja) * | 2013-10-31 | 2017-04-12 | 日本化薬株式会社 | １，５−ナフチリジン誘導体およびそれを有効成分として含んでなる殺虫剤 |
| WO2015103509A1 (en) | 2014-01-06 | 2015-07-09 | Bristol-Myers Squibb Company | Pyrrolidinyl sulfone derivatives and their use as ror gamma modulators |
| EP3050888A1 (en) | 2015-01-27 | 2016-08-03 | Merck Sharp & Dohme Corp. | Compounds for the treatment of bacterial infections |
| UY36851A (es) * | 2015-08-16 | 2017-03-31 | Glaxosmithkline Ip Dev Ltd | Compuestos para uso en aplicaciones antibacterianas |
| WO2017153235A1 (de) | 2016-03-09 | 2017-09-14 | Bayer Pharma Aktiengesellschaft | Substituierte n-cyclo-3-aryl-1-naphthamide und ihre verwendung |
| BR112018075297A2 (pt) * | 2016-06-08 | 2019-03-19 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A | composto, composição farmacêutica, e, método para tratar uma infecção bacteriana |
| HRP20220144T1 (hr) | 2016-09-09 | 2022-04-15 | Novartis Ag | Spojevi i pripravci kao inhibitori endosomskih toll-u sličnih receptora |
| WO2019090074A1 (en) * | 2017-11-02 | 2019-05-09 | Calico Life Sciences Llc | Modulators of the integrated stress pathway |
| JP7190513B2 (ja) | 2018-06-15 | 2022-12-15 | ブリストル－マイヤーズ スクイブ カンパニー | ガレクチン－３抑制剤を模したテトラヒドロピラン系チオ二糖類 |
| CN108947940A (zh) * | 2018-06-20 | 2018-12-07 | 天津全和诚科技有限责任公司 | 一种2-氧杂环丁烷衍生物的合成方法 |
| CA3125900A1 (en) | 2019-01-08 | 2020-07-16 | Kyorin Pharmaceutical Co., Ltd. | 15-pgdh inhibitor |
| EP3911641A1 (en) | 2019-01-14 | 2021-11-24 | Innate Tumor Immunity, Inc. | Nlrp3 modulators |
| US12304897B2 (en) | 2019-01-31 | 2025-05-20 | Kyorin Pharmaceutical Co., Ltd. | 15-PGDH inhibitors |
| WO2021252775A1 (en) | 2020-06-11 | 2021-12-16 | Chdi Foundation, Inc. | Heterocyclic compounds and imaging agents for imaging huntingtin protein |
| AU2021385752A1 (en) | 2020-11-26 | 2023-06-29 | Jiangsu Hengrui Pharmaceuticals Co., Ltd. | Fused tricyclic compound, preparation method therefor and application thereof in medicine |
| CN114957056A (zh) * | 2021-02-20 | 2022-08-30 | 帕潘纳(北京)科技有限公司 | 制备3-甲基-2-氯-4-甲基磺酰基苯甲酸甲酯及其中间体的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR244550A1 (es) | 1978-07-24 | 1993-11-30 | Merck & Co Inc | Procedimiento para obtener una composicion de antibioticos del tipo de la tienamicina con inhibidores de la dipeptidasa |
| CN100390178C (zh) | 1999-11-12 | 2008-05-28 | 拜奥根Idec马萨诸塞公司 | 作为腺苷受体拮抗剂的多环烷基嘌呤 |
| CA2580621A1 (en) * | 2004-09-24 | 2006-03-30 | Actelion Pharmaceuticals Ltd | New bicyclic antibiotics |
| DE102007026341A1 (de) | 2007-06-06 | 2008-12-11 | Merck Patent Gmbh | Benzoxazolonderivate |
| ATE520687T1 (de) * | 2007-06-15 | 2011-09-15 | Actelion Pharmaceuticals Ltd | 3-amino-6-(1-amino-ethyl)-tetrahydropyranderiva e |
| MX2010012855A (es) * | 2008-06-03 | 2010-12-21 | Actelion Pharmaceuticals Ltd | Derivados de [4-(1-amino-etil)-ciclohexil]-metil-amina y [6-(1-amino-etil)-tetrahidro-piran-3-il]-metil-amina como antibacterianos. |
| WO2010043714A1 (en) * | 2008-10-17 | 2010-04-22 | Glaxo Group Limited | Tricyclic nitrogen compounds used as antibacterials |
| TW201022279A (en) * | 2008-11-14 | 2010-06-16 | Astrazeneca Ab | Chemical compounds |
| CN102232078B (zh) * | 2008-12-12 | 2014-07-16 | 埃科特莱茵药品有限公司 | 5-氨基-2-(1-羟基-乙基)-四氢吡喃衍生物 |
| 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 |
-
2012
- 2012-06-26 US US14/126,225 patent/US20140243302A1/en not_active Abandoned
- 2012-06-26 WO PCT/US2012/044267 patent/WO2013003383A1/en not_active Ceased
- 2012-06-26 JP JP2014518932A patent/JP2014518267A/ja active Pending
- 2012-06-26 CA CA2840060A patent/CA2840060A1/en not_active Abandoned
- 2012-06-26 AU AU2012275499A patent/AU2012275499A1/en not_active Abandoned
- 2012-06-26 EP EP12735698.8A patent/EP2723737A1/en not_active Withdrawn
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