JP2016509594A5 - - Google Patents

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Publication number

JP2016509594A5

JP2016509594A5 JP2015551761A JP2015551761A JP2016509594A5 JP 2016509594 A5 JP2016509594 A5 JP 2016509594A5 JP 2015551761 A JP2015551761 A JP 2015551761A JP 2015551761 A JP2015551761 A JP 2015551761A JP 2016509594 A5 JP2016509594 A5 JP 2016509594A5

Authority

JP

Japan

Prior art keywords

alkyl

group

compound according

pharmaceutically acceptable

formula

Prior art date

2014-01-02

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

Links

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• 150000001875 compounds Chemical class 0.000 claims 21
• 125000000217 alkyl group Chemical group 0.000 claims 17
• 229910052736 halogen Inorganic materials 0.000 claims 8
• 150000002367 halogens Chemical class 0.000 claims 8
• 150000003839 salts Chemical class 0.000 claims 8
• 239000003795 chemical substances by application Substances 0.000 claims 7
• 239000008194 pharmaceutical composition Substances 0.000 claims 7
• -1 amino, hydroxy Chemical group 0.000 claims 6
• 239000003242 anti bacterial agent Substances 0.000 claims 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
• UUGRTBCTVUNWTN-DLRIENLKSA-N (2s,3s)-3-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1,5-dihydroxy-4-oxopyridin-2-yl)methoxyimino]acetyl]amino]-2-methyl-4-oxoazetidine-1-sulfonic acid Chemical compound O=C1N(S(O)(=O)=O)[C@@H](C)[C@@H]1NC(=O)C(\C=1N=C(N)SC=1)=N/OCC1=CC(=O)C(O)=CN1O UUGRTBCTVUNWTN-DLRIENLKSA-N 0.000 claims 2
• QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 claims 2
• OMAFFHIGWTVZOH-UHFFFAOYSA-N 1-methyltetrazole Chemical compound CN1C=NN=N1 OMAFFHIGWTVZOH-UHFFFAOYSA-N 0.000 claims 2
• WZPBZJONDBGPKJ-UHFFFAOYSA-N Antibiotic SQ 26917 Natural products O=C1N(S(O)(=O)=O)C(C)C1NC(=O)C(=NOC(C)(C)C(O)=O)C1=CSC(N)=N1 WZPBZJONDBGPKJ-UHFFFAOYSA-N 0.000 claims 2
• 208000035143 Bacterial infection Diseases 0.000 claims 2
• TYMABNNERDVXID-DLYFRVTGSA-N Panipenem Chemical compound C([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1S[C@H]1CCN(C(C)=N)C1 TYMABNNERDVXID-DLYFRVTGSA-N 0.000 claims 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
• WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 claims 2
• KLFSEZJCLYBFKQ-WXYNYTDUSA-N [(3s)-3-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1,5-dihydroxy-4-oxopyridin-2-yl)methoxyimino]acetyl]amino]-2,2-dimethyl-4-oxoazetidin-1-yl] hydrogen sulfate Chemical compound O=C1N(OS(O)(=O)=O)C(C)(C)[C@@H]1NC(=O)C(\C=1N=C(N)SC=1)=N/OCC1=CC(=O)C(O)=CN1O KLFSEZJCLYBFKQ-WXYNYTDUSA-N 0.000 claims 2
• 239000000654 additive Substances 0.000 claims 2
• 230000000996 additive effect Effects 0.000 claims 2
• 239000002260 anti-inflammatory agent Substances 0.000 claims 2
• 229940121363 anti-inflammatory agent Drugs 0.000 claims 2
• 239000000043 antiallergic agent Substances 0.000 claims 2
• 239000003443 antiviral agent Substances 0.000 claims 2
• 125000003118 aryl group Chemical group 0.000 claims 2
• WZPBZJONDBGPKJ-VEHQQRBSSA-N aztreonam Chemical compound O=C1N(S([O-])(=O)=O)[C@@H](C)[C@@H]1NC(=O)C(=N/OC(C)(C)C(O)=O)\C1=CSC([NH3+])=N1 WZPBZJONDBGPKJ-VEHQQRBSSA-N 0.000 claims 2
• 229960003644 aztreonam Drugs 0.000 claims 2
• 208000022362 bacterial infectious disease Diseases 0.000 claims 2
• MRMBZHPJVKCOMA-YJFSRANCSA-N biapenem Chemical compound C1N2C=NC=[N+]2CC1SC([C@@H]1C)=C(C([O-])=O)N2[C@H]1[C@@H]([C@H](O)C)C2=O MRMBZHPJVKCOMA-YJFSRANCSA-N 0.000 claims 2
• 229960003169 biapenem Drugs 0.000 claims 2
• ORFOPKXBNMVMKC-DWVKKRMSSA-N ceftazidime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 ORFOPKXBNMVMKC-DWVKKRMSSA-N 0.000 claims 2
• 229960000484 ceftazidime Drugs 0.000 claims 2
• AVAACINZEOAHHE-VFZPANTDSA-N doripenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](CNS(N)(=O)=O)C1 AVAACINZEOAHHE-VFZPANTDSA-N 0.000 claims 2
• 229960000895 doripenem Drugs 0.000 claims 2
• 125000001072 heteroaryl group Chemical group 0.000 claims 2
• 229960002182 imipenem Drugs 0.000 claims 2
• ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 claims 2
• 229960002260 meropenem Drugs 0.000 claims 2
• DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](C(=O)N(C)C)C1 DMJNNHOOLUXYBV-PQTSNVLCSA-N 0.000 claims 2
• 229950011346 panipenem Drugs 0.000 claims 2
• 230000002265 prevention Effects 0.000 claims 2
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 2
• VAMSVIZLXJOLHZ-QWFSEIHXSA-N tigemonam Chemical compound O=C1N(OS(O)(=O)=O)C(C)(C)[C@@H]1NC(=O)C(=N/OCC(O)=O)\C1=CSC(N)=N1 VAMSVIZLXJOLHZ-QWFSEIHXSA-N 0.000 claims 2
• 229950010206 tigemonam Drugs 0.000 claims 2
• 229940124586 β-lactam antibiotics Drugs 0.000 claims 2
• 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims 1
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims 1
• MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 1
• JWAWEQBUZOGIBZ-UHFFFAOYSA-N 1-methyltriazole Chemical compound CN1C=CN=N1 JWAWEQBUZOGIBZ-UHFFFAOYSA-N 0.000 claims 1
• XJLITJHUQRBWPN-UHFFFAOYSA-N 2-acetamidoacetic acid;4-[2-(4-carbamimidoylphenyl)iminohydrazinyl]benzenecarboximidamide Chemical compound CC(=O)NCC(O)=O.C1=CC(C(=N)N)=CC=C1NN=NC1=CC=C(C(N)=N)C=C1 XJLITJHUQRBWPN-UHFFFAOYSA-N 0.000 claims 1
• ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 claims 1
• QRZMXADUXZADTF-UHFFFAOYSA-N 4-aminoimidazole Chemical compound NC1=CNC=N1 QRZMXADUXZADTF-UHFFFAOYSA-N 0.000 claims 1
• KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims 1
• JUZNIMUFDBIJCM-ANEDZVCMSA-N Invanz Chemical compound O=C([C@H]1NC[C@H](C1)SC=1[C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)NC1=CC=CC(C(O)=O)=C1 JUZNIMUFDBIJCM-ANEDZVCMSA-N 0.000 claims 1
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical group CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims 1
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
• 229950003476 aminothiazole Drugs 0.000 claims 1
• 239000003429 antifungal agent Substances 0.000 claims 1
• 229940121375 antifungal agent Drugs 0.000 claims 1
• 150000001540 azides Chemical class 0.000 claims 1
• 125000004093 cyano group Chemical group *C#N 0.000 claims 1
• 229960002770 ertapenem Drugs 0.000 claims 1
• 230000002538 fungal effect Effects 0.000 claims 1
• 125000000623 heterocyclic group Chemical group 0.000 claims 1
• 229960003194 meglumine Drugs 0.000 claims 1
• 239000000203 mixture Substances 0.000 claims 1
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
• 150000003536 tetrazoles Chemical class 0.000 claims 1
• 150000003852 triazoles Chemical class 0.000 claims 1
• 0 CCOC(OC(C)OC(c1c2OB3*=C(CSC)N[C@]3Cc2ccc1)=O)=O Chemical compound CCOC(OC(C)OC(c1c2OB3*=C(CSC)N[C@]3Cc2ccc1)=O)=O 0.000 description 2
• VELHQRMGDOGMPM-UHFFFAOYSA-N CC(C)(C)C(OCOC(c(cccc1CC2NC(CSC)=O)c1OB2O)=O)=O Chemical compound CC(C)(C)C(OCOC(c(cccc1CC2NC(CSC)=O)c1OB2O)=O)=O VELHQRMGDOGMPM-UHFFFAOYSA-N 0.000 description 1
• WUQGISQYFIRBLU-ZDUSSCGKSA-N CC(C)OC(OCOC(c(cccc1C[C@@H]2NC(CSC)=O)c1OB2O)=O)=O Chemical compound CC(C)OC(OCOC(c(cccc1C[C@@H]2NC(CSC)=O)c1OB2O)=O)=O WUQGISQYFIRBLU-ZDUSSCGKSA-N 0.000 description 1
• IEYYFPPOBKZHPG-HNNXBMFYSA-N CCC(CC)C(OCOC(c(cccc1C[C@@H]2NC(CSC)=O)c1OB2O)=O)=O Chemical compound CCC(CC)C(OCOC(c(cccc1C[C@@H]2NC(CSC)=O)c1OB2O)=O)=O IEYYFPPOBKZHPG-HNNXBMFYSA-N 0.000 description 1
• JLXAZUMNJODWBO-ZDUSSCGKSA-N CCCC(OCOC(c(cccc1C[C@@H]2NC(CSC)=O)c1OB2O)=O)=O Chemical compound CCCC(OCOC(c(cccc1C[C@@H]2NC(CSC)=O)c1OB2O)=O)=O JLXAZUMNJODWBO-ZDUSSCGKSA-N 0.000 description 1
• GNWXQXUVACQZAY-VIFPVBQESA-N COB([C@H](Cc1ccc2)N/C(/c3nnc(N)[o]3)=[O]\C)Oc1c2C(O)=O Chemical compound COB([C@H](Cc1ccc2)N/C(/c3nnc(N)[o]3)=[O]\C)Oc1c2C(O)=O GNWXQXUVACQZAY-VIFPVBQESA-N 0.000 description 1
• QTNJTYOSJMJPKB-ZETCQYMHSA-N Nc1nnc(C(N[C@H]2Cc3cccc(C(O)=O)c3OB2O)=O)[s]1 Chemical compound Nc1nnc(C(N[C@H]2Cc3cccc(C(O)=O)c3OB2O)=O)[s]1 QTNJTYOSJMJPKB-ZETCQYMHSA-N 0.000 description 1
• ZZZBWSAVQFPOLP-LBPRGKRZSA-N OB([C@H](Cc1ccc2)NC(c3cc(F)cnc3)=O)Oc1c2C(O)=O Chemical compound OB([C@H](Cc1ccc2)NC(c3cc(F)cnc3)=O)Oc1c2C(O)=O ZZZBWSAVQFPOLP-LBPRGKRZSA-N 0.000 description 1
• OMCMDOYTIDGOJK-LBPRGKRZSA-N OB([C@H](Cc1ccc2)NC(c3cccnc3)=O)Oc1c2C(O)=O Chemical compound OB([C@H](Cc1ccc2)NC(c3cccnc3)=O)Oc1c2C(O)=O OMCMDOYTIDGOJK-LBPRGKRZSA-N 0.000 description 1
• OQGUPXPWULVSPM-NSHDSACASA-N OB([C@H](Cc1ccc2)NC(c3cncnc3)=O)Oc1c2C(O)=O Chemical compound OB([C@H](Cc1ccc2)NC(c3cncnc3)=O)Oc1c2C(O)=O OQGUPXPWULVSPM-NSHDSACASA-N 0.000 description 1