JP2013511486A5 - - Google Patents
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- Publication number
- JP2013511486A5 JP2013511486A5 JP2012539312A JP2012539312A JP2013511486A5 JP 2013511486 A5 JP2013511486 A5 JP 2013511486A5 JP 2012539312 A JP2012539312 A JP 2012539312A JP 2012539312 A JP2012539312 A JP 2012539312A JP 2013511486 A5 JP2013511486 A5 JP 2013511486A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- azetidin
- enyl
- oxoprop
- naphthyridine
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 29
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
- -1 3-oxo-3- (3- (2- (thiophen-2-yl) ethoxy) azetidin-1-yl) prop-1-enyl Chemical group 0.000 claims description 10
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 241000191967 Staphylococcus aureus Species 0.000 claims 9
- CQQVSXRUVDVVNO-UBNNNTKFSA-N 6-[(e)-3-[3-[(e)-c-methyl-n-propoxycarbonimidoyl]azetidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C1C(C(/C)=N/OCCC)CN1C(=O)\C=C\C1=CN=C(NC(=O)CC2)C2=C1 CQQVSXRUVDVVNO-UBNNNTKFSA-N 0.000 claims 6
- 208000015181 infectious disease Diseases 0.000 claims 6
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 5
- 230000000813 microbial effect Effects 0.000 claims 5
- IRGSWLRUVQHHTF-VMPITWQZSA-N 6-[(e)-3-[3-(1-benzofuran-2-yl)azetidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C1=CC=C2OC(C3CN(C3)C(\C=C\C=3C=C4CCC(=O)NC4=NC=3)=O)=CC2=C1 IRGSWLRUVQHHTF-VMPITWQZSA-N 0.000 claims 4
- OTHXOQIDEXDBSX-RMKNXTFCSA-N 6-[(e)-3-[3-(3-methyl-1-benzofuran-2-yl)azetidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound N1C(=O)CCC2=CC(/C=C/C(=O)N3CC(C3)C3=C(C4=CC=CC=C4O3)C)=CN=C21 OTHXOQIDEXDBSX-RMKNXTFCSA-N 0.000 claims 4
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 claims 4
- 229960003085 meticillin Drugs 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 108010059993 Vancomycin Proteins 0.000 claims 3
- 229960003165 vancomycin Drugs 0.000 claims 3
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 claims 3
- MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 claims 3
- IEAWJZJDIUZANC-AATRIKPKSA-N (e)-3-[3-[(dimethylamino)methyl]-1h-pyrrolo[2,3-b]pyridin-5-yl]-1-[3-(thiophen-2-ylmethoxy)azetidin-1-yl]prop-2-en-1-one Chemical compound C1=C2C(CN(C)C)=CNC2=NC=C1\C=C\C(=O)N(C1)CC1OCC1=CC=CS1 IEAWJZJDIUZANC-AATRIKPKSA-N 0.000 claims 2
- PPLOEUSGELSLMK-BQYQJAHWSA-N 1'-methyl-6-[(e)-3-[3-(3-methyl-1-benzofuran-2-yl)azetidin-1-yl]-3-oxoprop-1-enyl]spiro[1,4-dihydro-1,8-naphthyridine-3,4'-piperidine]-2-one Chemical compound C1CN(C)CCC21C(=O)NC1=NC=C(\C=C\C(=O)N3CC(C3)C3=C(C4=CC=CC=C4O3)C)C=C1C2 PPLOEUSGELSLMK-BQYQJAHWSA-N 0.000 claims 2
- VFHWQEBTECYEOD-USGQHZDISA-N 1'-methyl-6-[(e)-3-[3-[(e)-c-methyl-n-phenylmethoxycarbonimidoyl]azetidin-1-yl]-3-oxoprop-1-enyl]spiro[1,4-dihydro-1,8-naphthyridine-3,4'-piperidine]-2-one Chemical compound C1CN(C)CCC21C(=O)NC1=NC=C(\C=C\C(=O)N3CC(C3)C(\C)=N\OCC=3C=CC=CC=3)C=C1C2 VFHWQEBTECYEOD-USGQHZDISA-N 0.000 claims 2
- XEWAXJQCXCRSSU-JHVREWCZSA-N 1'-methyl-6-[(e)-3-[3-[(e)-c-methyl-n-propoxycarbonimidoyl]azetidin-1-yl]-3-oxoprop-1-enyl]spiro[1,4-dihydro-1,8-naphthyridine-3,4'-piperidine]-2-one Chemical compound C1C(C(/C)=N/OCCC)CN1C(=O)\C=C\C1=CN=C(NC(=O)C2(CCN(C)CC2)C2)C2=C1 XEWAXJQCXCRSSU-JHVREWCZSA-N 0.000 claims 2
- NKNFQSGFCHDMGX-SNAWJCMRSA-N 1'-methyl-6-[(e)-3-oxo-3-[3-(2-thiophen-2-ylethoxy)azetidin-1-yl]prop-1-enyl]spiro[1,4-dihydro-1,8-naphthyridine-3,4'-piperidine]-2-one Chemical compound C1CN(C)CCC21C(=O)NC1=NC=C(\C=C\C(=O)N3CC(C3)OCCC=3SC=CC=3)C=C1C2 NKNFQSGFCHDMGX-SNAWJCMRSA-N 0.000 claims 2
- JEMJJOWUMZGZLV-SNAWJCMRSA-N 1'-methyl-6-[(e)-3-oxo-3-[3-(thiophen-2-ylmethoxy)azetidin-1-yl]prop-1-enyl]spiro[1,4-dihydro-1,8-naphthyridine-3,4'-piperidine]-2-one Chemical compound C1CN(C)CCC21C(=O)NC1=NC=C(\C=C\C(=O)N3CC(C3)OCC=3SC=CC=3)C=C1C2 JEMJJOWUMZGZLV-SNAWJCMRSA-N 0.000 claims 2
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 2
- WUULBUPSYVJOJS-SNAWJCMRSA-N 3-[2-(4-methylpiperazin-1-yl)ethyl]-6-[(e)-3-oxo-3-[3-(thiophen-2-ylmethoxy)azetidin-1-yl]prop-1-enyl]-1,4-dihydropyrido[2,3-d]pyrimidin-2-one Chemical compound C1CN(C)CCN1CCN1C(=O)NC2=NC=C(\C=C\C(=O)N3CC(C3)OCC=3SC=CC=3)C=C2C1 WUULBUPSYVJOJS-SNAWJCMRSA-N 0.000 claims 2
- XSYSYTCUZNKYJG-AATRIKPKSA-N 6-[(e)-3-(3-butoxyazetidin-1-yl)-3-oxoprop-1-enyl]-1'-methylspiro[1,4-dihydro-1,8-naphthyridine-3,4'-piperidine]-2-one Chemical compound C1C(OCCCC)CN1C(=O)\C=C\C1=CN=C(NC(=O)C2(CCN(C)CC2)C2)C2=C1 XSYSYTCUZNKYJG-AATRIKPKSA-N 0.000 claims 2
- FPEKLOOAKYGFFC-RMKNXTFCSA-N 6-[(e)-3-(4-hydroxy-4-phenylpiperidin-1-yl)-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C1CN(C(=O)\C=C\C=2C=C3CCC(=O)NC3=NC=2)CCC1(O)C1=CC=CC=C1 FPEKLOOAKYGFFC-RMKNXTFCSA-N 0.000 claims 2
- KUGSQMJLYWUVGU-GORDUTHDSA-N 6-[(e)-3-(azetidin-1-yl)-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C=1N=C2NC(=O)CCC2=CC=1/C=C/C(=O)N1CCC1 KUGSQMJLYWUVGU-GORDUTHDSA-N 0.000 claims 2
- CXTHEZRFDLOSGG-DHZHZOJOSA-N 6-[(e)-3-[2-(1,3-benzoxazol-2-yl)piperidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C1=CC=C2OC(C3CCCCN3C(\C=C\C=3C=C4CCC(=O)NC4=NC=3)=O)=NC2=C1 CXTHEZRFDLOSGG-DHZHZOJOSA-N 0.000 claims 2
- SYUUXAROKMQQDY-VMPITWQZSA-N 6-[(e)-3-[2-(5-methyl-1,2,4-oxadiazol-3-yl)piperidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound O1C(C)=NC(C2N(CCCC2)C(=O)\C=C\C=2C=C3CCC(=O)NC3=NC=2)=N1 SYUUXAROKMQQDY-VMPITWQZSA-N 0.000 claims 2
- LFCYAMHFEITVFX-ZZXKWVIFSA-N 6-[(e)-3-[3-(2-methylprop-2-enoxy)azetidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C1C(OCC(=C)C)CN1C(=O)\C=C\C1=CN=C(NC(=O)CC2)C2=C1 LFCYAMHFEITVFX-ZZXKWVIFSA-N 0.000 claims 2
- JCULLUDCSGOFBT-GORDUTHDSA-N 6-[(e)-3-[3-(5-methyl-1,2,4-oxadiazol-3-yl)azetidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound O1C(C)=NC(C2CN(C2)C(=O)\C=C\C=2C=C3CCC(=O)NC3=NC=2)=N1 JCULLUDCSGOFBT-GORDUTHDSA-N 0.000 claims 2
- KMUUZBAIAHTLTC-GORDUTHDSA-N 6-[(e)-3-[3-[(1-methylpyrazol-3-yl)methoxy]azetidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound CN1C=CC(COC2CN(C2)C(=O)\C=C\C=2C=C3CCC(=O)NC3=NC=2)=N1 KMUUZBAIAHTLTC-GORDUTHDSA-N 0.000 claims 2
- MHQJJKSHMWQUPO-GORDUTHDSA-N 6-[(e)-3-[3-[(3-methylthiophen-2-yl)methoxy]azetidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C1=CSC(COC2CN(C2)C(=O)\C=C\C=2C=C3CCC(=O)NC3=NC=2)=C1C MHQJJKSHMWQUPO-GORDUTHDSA-N 0.000 claims 2
- ZIRROQDMKBOMQJ-DAFODLJHSA-N 6-[(e)-3-[3-[(4-bromothiophen-2-yl)methoxy]azetidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound BrC1=CSC(COC2CN(C2)C(=O)\C=C\C=2C=C3CCC(=O)NC3=NC=2)=C1 ZIRROQDMKBOMQJ-DAFODLJHSA-N 0.000 claims 2
- ZZARNBFLZRFGDW-DAFODLJHSA-N 6-[(e)-3-[3-[(4-chlorothiophen-2-yl)methoxy]azetidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound ClC1=CSC(COC2CN(C2)C(=O)\C=C\C=2C=C3CCC(=O)NC3=NC=2)=C1 ZZARNBFLZRFGDW-DAFODLJHSA-N 0.000 claims 2
- DYQOBDOAKVJDIV-XVNBXDOJSA-N 6-[(e)-3-[3-[(5-methylthiophen-2-yl)methoxy]azetidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound S1C(C)=CC=C1COC1CN(C(=O)\C=C\C=2C=C3CCC(=O)NC3=NC=2)C1 DYQOBDOAKVJDIV-XVNBXDOJSA-N 0.000 claims 2
- VGRSOAVDMJUWIS-LHPQVSFSSA-N 6-[(e)-3-[3-[(e)-2-methylbut-2-enoxy]azetidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C1C(OCC(/C)=C/C)CN1C(=O)\C=C\C1=CN=C(NC(=O)CC2)C2=C1 VGRSOAVDMJUWIS-LHPQVSFSSA-N 0.000 claims 2
- QAKGQHANERWTJB-AOGGBPEJSA-N 6-[(e)-3-[3-[(e)-but-2-enoxy]azetidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C1C(OC/C=C/C)CN1C(=O)\C=C\C1=CN=C(NC(=O)CC2)C2=C1 QAKGQHANERWTJB-AOGGBPEJSA-N 0.000 claims 2
- QAKGQHANERWTJB-UDJLOATDSA-N 6-[(e)-3-[3-[(z)-but-2-enoxy]azetidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C1C(OC\C=C/C)CN1C(=O)\C=C\C1=CN=C(NC(=O)CC2)C2=C1 QAKGQHANERWTJB-UDJLOATDSA-N 0.000 claims 2
- NVPQSHFBQKIUEH-LGCJVJRSSA-N 6-[(e)-3-[3-[(z)-n-ethoxy-c-methylcarbonimidoyl]azetidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C1C(C(\C)=N/OCC)CN1C(=O)\C=C\C1=CN=C(NC(=O)CC2)C2=C1 NVPQSHFBQKIUEH-LGCJVJRSSA-N 0.000 claims 2
- WYKRWRKJVRDEPC-DAFODLJHSA-N 6-[(e)-3-[4-(2-hydroxyethyl)piperidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C1CC(CCO)CCN1C(=O)\C=C\C1=CN=C(NC(=O)CC2)C2=C1 WYKRWRKJVRDEPC-DAFODLJHSA-N 0.000 claims 2
- PJZDJQFKDJPICJ-LZCJLJQNSA-N 6-[(e)-3-[4-[(4-fluorophenoxy)methyl]piperidin-1-yl]-3-oxoprop-1-enyl]-2-oxo-1h-1,8-naphthyridine-3-carboxamide Chemical compound C=1N=C2NC(=O)C(C(=O)N)=CC2=CC=1\C=C\C(=O)N(CC1)CCC1COC1=CC=C(F)C=C1 PJZDJQFKDJPICJ-LZCJLJQNSA-N 0.000 claims 2
- XRTUEMFKRZPEGQ-LZCJLJQNSA-N 6-[(e)-3-[4-[(4-fluorophenoxy)methyl]piperidin-1-yl]-3-oxoprop-1-enyl]-2-oxo-3,4-dihydro-1h-1,8-naphthyridine-3-carboxamide Chemical compound C=1N=C2NC(=O)C(C(=O)N)CC2=CC=1\C=C\C(=O)N(CC1)CCC1COC1=CC=C(F)C=C1 XRTUEMFKRZPEGQ-LZCJLJQNSA-N 0.000 claims 2
- FHLCDKAROOLURZ-LZCJLJQNSA-N 6-[(e)-3-[4-[(4-fluorophenoxy)methyl]piperidin-1-yl]-3-oxoprop-1-enyl]-3-(hydroxymethyl)-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C=1N=C2NC(=O)C(CO)CC2=CC=1\C=C\C(=O)N(CC1)CCC1COC1=CC=C(F)C=C1 FHLCDKAROOLURZ-LZCJLJQNSA-N 0.000 claims 2
- ZGGLXSGTNJGICQ-DHZHZOJOSA-N 6-[(e)-3-oxo-3-(2-phenylpyrrolidin-1-yl)prop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C=1N=C2NC(=O)CCC2=CC=1/C=C/C(=O)N1CCCC1C1=CC=CC=C1 ZGGLXSGTNJGICQ-DHZHZOJOSA-N 0.000 claims 2
- JGWYJIPGJZUQTP-VMPITWQZSA-N 6-[(e)-3-oxo-3-(3-pentoxyazetidin-1-yl)prop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C1C(OCCCCC)CN1C(=O)\C=C\C1=CN=C(NC(=O)CC2)C2=C1 JGWYJIPGJZUQTP-VMPITWQZSA-N 0.000 claims 2
- XLPKMGVYSWAPAJ-RMKNXTFCSA-N 6-[(e)-3-oxo-3-(3-phenoxyazetidin-1-yl)prop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C=1N=C2NC(=O)CCC2=CC=1/C=C/C(=O)N(C1)CC1OC1=CC=CC=C1 XLPKMGVYSWAPAJ-RMKNXTFCSA-N 0.000 claims 2
- MIUDHBYEEHQKIE-RMKNXTFCSA-N 6-[(e)-3-oxo-3-(3-phenoxypyrrolidin-1-yl)prop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C=1N=C2NC(=O)CCC2=CC=1/C=C/C(=O)N(C1)CCC1OC1=CC=CC=C1 MIUDHBYEEHQKIE-RMKNXTFCSA-N 0.000 claims 2
- IUDCXSXORCOVKT-ZZXKWVIFSA-N 6-[(e)-3-oxo-3-(3-pyridin-3-yloxypyrrolidin-1-yl)prop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C=1N=C2NC(=O)CCC2=CC=1/C=C/C(=O)N(C1)CCC1OC1=CC=CN=C1 IUDCXSXORCOVKT-ZZXKWVIFSA-N 0.000 claims 2
- SNXFJGDLNWCNJI-QPJJXVBHSA-N 6-[(e)-3-oxo-3-(4-propylpiperidin-1-yl)prop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C1CC(CCC)CCN1C(=O)\C=C\C1=CN=C(NC(=O)CC2)C2=C1 SNXFJGDLNWCNJI-QPJJXVBHSA-N 0.000 claims 2
- KISSQSDZTGAZSH-DAFODLJHSA-N 6-[(e)-3-oxo-3-[3-(1,3-thiazol-2-ylmethoxy)azetidin-1-yl]prop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C=1N=C2NC(=O)CCC2=CC=1/C=C/C(=O)N(C1)CC1OCC1=NC=CS1 KISSQSDZTGAZSH-DAFODLJHSA-N 0.000 claims 2
- WMRHMMUTJPJVQF-DAFODLJHSA-N 6-[(e)-3-oxo-3-[3-(3,3,3-trifluoropropoxy)azetidin-1-yl]prop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C1C(OCCC(F)(F)F)CN1C(=O)\C=C\C1=CN=C(NC(=O)CC2)C2=C1 WMRHMMUTJPJVQF-DAFODLJHSA-N 0.000 claims 2
- GPCLMQRZYYYQLI-VMPITWQZSA-N 6-[(e)-3-oxo-3-[3-(3-thiophen-2-ylpropoxy)azetidin-1-yl]prop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C=1N=C2NC(=O)CCC2=CC=1/C=C/C(=O)N(C1)CC1OCCCC1=CC=CS1 GPCLMQRZYYYQLI-VMPITWQZSA-N 0.000 claims 2
- HMQPTXWWOPSKRZ-GORDUTHDSA-N 6-[(e)-3-oxo-3-[3-(4,4,4-trifluorobutoxy)azetidin-1-yl]prop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C1C(OCCCC(F)(F)F)CN1C(=O)\C=C\C1=CN=C(NC(=O)CC2)C2=C1 HMQPTXWWOPSKRZ-GORDUTHDSA-N 0.000 claims 2
- QATPMNXCDSKNPZ-ZZXKWVIFSA-N 6-[(e)-3-oxo-3-[3-(thiophen-2-ylmethoxy)azetidin-1-yl]prop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C=1N=C2NC(=O)CCC2=CC=1/C=C/C(=O)N(C1)CC1OCC1=CC=CS1 QATPMNXCDSKNPZ-ZZXKWVIFSA-N 0.000 claims 2
- GQMLYNXCQKUYTD-MFZKSGLQSA-N 6-[(e)-3-oxo-3-[3-[(e)-1-pyrimidin-2-ylpropan-2-ylideneamino]oxyazetidin-1-yl]prop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C1N(C(=O)\C=C\C=2C=C3CCC(=O)NC3=NC=2)CC1O\N=C(/C)CC1=NC=CC=N1 GQMLYNXCQKUYTD-MFZKSGLQSA-N 0.000 claims 2
- WGWUWXYHWXPSCP-QPJJXVBHSA-N 6-[(e)-3-oxo-3-piperidin-1-ylprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C=1N=C2NC(=O)CCC2=CC=1/C=C/C(=O)N1CCCCC1 WGWUWXYHWXPSCP-QPJJXVBHSA-N 0.000 claims 2
- WZFFTNBBSJVUDW-ZZXKWVIFSA-N 6-[(e)-3-oxo-3-pyrrolidin-1-ylprop-1-enyl]-3,4-dihydro-1h-1,8-naphthyridin-2-one Chemical compound C=1N=C2NC(=O)CCC2=CC=1/C=C/C(=O)N1CCCC1 WZFFTNBBSJVUDW-ZZXKWVIFSA-N 0.000 claims 2
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- SIIWVGRQAAYYBW-ONEGZZNKSA-N 7-[(e)-3-oxo-3-[3-(thiophen-2-ylmethoxy)azetidin-1-yl]prop-1-enyl]-1,3,4,5-tetrahydropyrido[2,3-e][1,4]diazepin-2-one Chemical compound C=1N=C2NC(=O)CNCC2=CC=1/C=C/C(=O)N(C1)CC1OCC1=CC=CS1 SIIWVGRQAAYYBW-ONEGZZNKSA-N 0.000 claims 2
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- AJLRYGIHUNUBKA-UHFFFAOYSA-N O=C(C=CC(CC1=CC=CN=C1N1)C1=O)N(C1)CC1OC1=CC=CC2=C1OC=C2 Chemical compound O=C(C=CC(CC1=CC=CN=C1N1)C1=O)N(C1)CC1OC1=CC=CC2=C1OC=C2 AJLRYGIHUNUBKA-UHFFFAOYSA-N 0.000 claims 2
- YIQJRDZMPFDCCI-UHFFFAOYSA-N O=C(C=CC(CC1=CC=CN=C1N1)C1=O)N(C1)CC1OCC1=CC=CO1 Chemical compound O=C(C=CC(CC1=CC=CN=C1N1)C1=O)N(C1)CC1OCC1=CC=CO1 YIQJRDZMPFDCCI-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
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- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 2
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- 241000191980 Staphylococcus intermedius Species 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
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- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229940047650 haemophilus influenzae Drugs 0.000 claims 1
- 229940045505 klebsiella pneumoniae Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 244000000010 microbial pathogen Species 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 0 CC(C)(*)*N(C)C(C=C*)=O Chemical compound CC(C)(*)*N(C)C(C=C*)=O 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
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| WO2008009122A1 (en) | 2006-07-20 | 2008-01-24 | Affinium Pharmaceuticals, Inc. | Acrylamide derivatives as fab i inhibitors |
| MX2012005759A (es) | 2009-11-18 | 2012-10-03 | Fab Pharma S A S | Acrilamidas heterociclicas novedosas y su uso como farmacos. |
| JO3611B1 (ar) | 2011-08-10 | 2020-08-27 | Janssen Sciences Ireland Uc | سايكلو بنتا (سي (بيرول 4,3 ثاني هيدرو 1 hمستبدله [8,1] نافثيريدينونات مضادة للجراثيم |
| EP2742044B1 (en) * | 2011-08-10 | 2019-12-04 | Janssen Sciences Ireland Unlimited Company | Antibacterial homopiperidinyl substituted 3,4-dihydro-1h-[1,8]naphthyridinones |
| CA2842531C (en) * | 2011-08-10 | 2019-07-16 | Janssen R&D Ireland | Antibacterial piperidinyl substituted 3,4-dihydro-1h-[1,8]naphthyridinones |
| EP2758376A4 (en) | 2011-09-19 | 2015-04-29 | Vitas Pharma Res Private Ltd | HETEROCYCLIC COMPOUNDS AS INHIBITORS OF FATTY ACID BIOSYNTHESIS FOR BACTERIAL INFECTIONS |
| US9062075B2 (en) | 2011-12-02 | 2015-06-23 | Aurigene Discovery Technologies Limited | Tetrahydropyridine derivatives as FabI inhibitors |
| MY165902A (en) | 2011-12-02 | 2018-05-18 | Aurigene Discovery Tech Ltd | Substituted pyridine derivatives as fabi inhibitors |
| AR090880A1 (es) | 2012-04-30 | 2014-12-10 | Janssen R & D Ireland | Derivados de pirimidina |
| NZ702695A (en) * | 2012-06-19 | 2015-10-30 | Debiopharm Int Sa | Prodrug derivatives of (e)-n-methyl-n-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide |
| CA2879623C (en) * | 2012-08-10 | 2021-11-02 | Janssen Sciences Ireland Uc | Fused bicyclic azole heterocycle as inhibitors of the enzyme fabi |
| EA201590331A1 (ru) * | 2012-08-10 | 2016-05-31 | Янссен Сайенсиз Айрлэнд Юси | Новые антибактериальные соединения |
| WO2014072930A2 (en) * | 2012-11-09 | 2014-05-15 | Aurigene Discovery Technologies Limited | Fused pyridine derivatives as antibacterial agents |
| WO2014195844A1 (en) * | 2013-06-04 | 2014-12-11 | Aurigene Discovery Technologies Limited | TETRAHYDROPYRIDINE DERIVATIVES AS FabI INHIBITORS |
| CN104292142B (zh) * | 2013-07-17 | 2019-05-14 | 天津大地康和医药技术有限公司 | 一种n-芳基杂环丁烷脱芳基方法 |
| WO2015071780A1 (en) * | 2013-11-12 | 2015-05-21 | Aurigene Discovery Technologies Limited | Alkylidine substituted heterocyclyl derivatives as anti-bacterial agents |
| CN104529854B (zh) * | 2015-01-14 | 2016-10-05 | 武汉金联药业有限公司 | 一种取代氮杂环丁烷类医药中间体化合物的合成方法 |
| TW202247838A (zh) | 2015-07-02 | 2022-12-16 | 美商地平線罕見醫學製藥有限責任公司 | Ado抗性半胱胺類似物及其用途 |
| ES2842443T3 (es) | 2016-02-26 | 2021-07-14 | Debiopharm Int Sa | Medicamento para el tratamiento de infecciones del pie diabético |
| CN108440523A (zh) * | 2018-04-23 | 2018-08-24 | 爱斯特（成都）生物制药股份有限公司 | 一种合成6-溴-3,4-二氢-1h-[1,8]萘啶-2-酮的新方法 |
| IL285204B2 (en) | 2019-02-14 | 2025-02-01 | Debiopharm Int Sa | Formulation of apavicin, method for its preparation |
| EP3982975A1 (en) | 2019-06-14 | 2022-04-20 | Debiopharm International SA | Afabicin for use for treating bacterial infections involving biofilm |
| CN114351128B (zh) * | 2021-12-10 | 2022-12-13 | 江阴纳力新材料科技有限公司 | 镀铜液添加剂、镀铜液、镀铜薄膜及其制备方法、负极集流体、锂电池 |
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| CN1020864C (zh) * | 1988-09-14 | 1993-05-26 | 中国科学院上海有机化学研究所 | 醛的烯基化反应的催化剂及其应用 |
| TW224042B (OSRAM) * | 1992-04-04 | 1994-05-21 | Basf Ag | |
| WO1997033870A1 (en) * | 1996-03-15 | 1997-09-18 | Ss Pharmaceutical Co., Ltd. | Novel pyridine derivatives and medicines containing the same as active ingredient |
| CN1286684A (zh) | 1996-05-01 | 2001-03-07 | 奥索·麦克尼尔药品公司 | 治疗血栓形成疾病的吡咯烷、哌啶和六氢吖庚因的甲酰胺衍生物 |
| PE20010635A1 (es) | 1999-10-08 | 2001-08-15 | Smithkline Beecham Corp | Inhibidores de fab i utiles para el tratamiento de infecciones bacterianas |
| DK1560584T3 (da) | 2001-04-06 | 2009-05-18 | Affinium Pharm Inc | Fab I inhibitorer |
| JP2004099499A (ja) * | 2002-09-09 | 2004-04-02 | Sanei Gen Ffi Inc | 抗微生物剤 |
| AU2003298937A1 (en) | 2002-12-06 | 2004-06-30 | Affinium Pharmaceuticals, Inc. | Heterocyclic compounds, methods of making them and their use in therapy |
| DK1828167T3 (da) | 2004-06-04 | 2014-10-20 | Debiopharm Int Sa | Acrylamidderivater som antibiotiske midler |
| WO2006081273A1 (en) * | 2005-01-26 | 2006-08-03 | Allergan, Inc. | 3-aryl-3-hydroxy-2-amino-propionic acid amides, 3-heteroayryl-3-hydroxy-2-amino-propionic acid amides and related compounds having analgesic and/or immunostimulant activity |
| CA2632476A1 (en) | 2005-12-05 | 2007-06-14 | Affinium Pharmaceuticals, Inc. | Heterocyclylacrylamide compounds as fabi inhibitors and antibacterial agents |
| WO2007086584A1 (ja) * | 2006-01-30 | 2007-08-02 | Meiji Seika Kaisha, Ltd. | 新規ＦａｂＫおよびＦａｂＩ／Ｋ阻害剤 |
| EP1845087A1 (en) | 2006-04-14 | 2007-10-17 | Mutabilis SA | Hydroxyphenyl derivatives and biological applications thereof |
| WO2008009122A1 (en) | 2006-07-20 | 2008-01-24 | Affinium Pharmaceuticals, Inc. | Acrylamide derivatives as fab i inhibitors |
| EP1942104A1 (en) | 2006-12-20 | 2008-07-09 | sanofi-aventis | Heteroarylcyclopropanecarboxamides and their use as pharmaceuticals |
| EP1939180A1 (en) | 2006-12-20 | 2008-07-02 | sanofi-aventis | Heteroarylacrylamides and their use as pharmaceuticals for the stimulation of the expression of endothelial NO synthase |
| WO2008098374A1 (en) | 2007-02-16 | 2008-08-21 | Affinium Pharmaceuticals, Inc. | Salts, prodrugs and polymorphs of fab i inhibitors |
| WO2009110002A1 (en) * | 2008-03-05 | 2009-09-11 | Council Of Scientific & Industrial Research | Novel efflux pump inhibitors |
| JP2012102018A (ja) * | 2009-03-03 | 2012-05-31 | Astellas Pharma Inc | アミド化合物 |
| MX2012005759A (es) | 2009-11-18 | 2012-10-03 | Fab Pharma S A S | Acrilamidas heterociclicas novedosas y su uso como farmacos. |
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- 2010-11-17 CA CA2776849A patent/CA2776849A1/en not_active Abandoned
- 2010-11-17 BR BR112012011793A patent/BR112012011793A2/pt not_active IP Right Cessation
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2012
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