JP2014515041A5 - - Google Patents
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- Publication number
- JP2014515041A5 JP2014515041A5 JP2014510942A JP2014510942A JP2014515041A5 JP 2014515041 A5 JP2014515041 A5 JP 2014515041A5 JP 2014510942 A JP2014510942 A JP 2014510942A JP 2014510942 A JP2014510942 A JP 2014510942A JP 2014515041 A5 JP2014515041 A5 JP 2014515041A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- diaza
- bicyclo
- trans
- hydrazinocarbonyl
- 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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- -1 N ′-[(S) -pyrrolidine-2-carbonyl] -hydrazinocarbonyl Chemical group 0.000 claims 37
- 150000002148 esters Chemical class 0.000 claims 28
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 25
- 239000003242 anti bacterial agent Substances 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 19
- 229910052736 halogen Inorganic materials 0.000 claims 17
- 150000002367 halogens Chemical class 0.000 claims 17
- 125000001424 substituent group Chemical group 0.000 claims 17
- 208000035143 Bacterial infection Diseases 0.000 claims 16
- 208000022362 bacterial infectious disease Diseases 0.000 claims 16
- 239000008194 pharmaceutical composition Substances 0.000 claims 15
- 239000003814 drug Substances 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 11
- FKENQMMABCRJMK-RITPCOANSA-N sulbactam Chemical compound O=S1(=O)C(C)(C)[C@H](C(O)=O)N2C(=O)C[C@H]21 FKENQMMABCRJMK-RITPCOANSA-N 0.000 claims 11
- 229960005256 sulbactam Drugs 0.000 claims 11
- 241000894006 Bacteria Species 0.000 claims 8
- 229930186147 Cephalosporin Natural products 0.000 claims 8
- 108090000204 Dipeptidase 1 Proteins 0.000 claims 8
- 102000006635 beta-lactamase Human genes 0.000 claims 8
- 229940124587 cephalosporin Drugs 0.000 claims 8
- 150000001780 cephalosporins Chemical class 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 208000015181 infectious disease Diseases 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 229930182555 Penicillin Natural products 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 claims 5
- 229960003324 clavulanic acid Drugs 0.000 claims 5
- 159000000000 sodium salts Chemical class 0.000 claims 5
- LPQZKKCYTLCDGQ-WEDXCCLWSA-N tazobactam Chemical compound C([C@]1(C)S([C@H]2N(C(C2)=O)[C@H]1C(O)=O)(=O)=O)N1C=CN=N1 LPQZKKCYTLCDGQ-WEDXCCLWSA-N 0.000 claims 5
- 229960003865 tazobactam Drugs 0.000 claims 5
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 4
- 108010028921 Lipopeptides Proteins 0.000 claims 4
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims 4
- 239000004098 Tetracycline Substances 0.000 claims 4
- 229940126575 aminoglycoside Drugs 0.000 claims 4
- 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 4
- 229960003644 aztreonam Drugs 0.000 claims 4
- 239000003781 beta lactamase inhibitor Substances 0.000 claims 4
- 229940126813 beta-lactamase inhibitor Drugs 0.000 claims 4
- JSVCEVCSANKFDY-SFYZADRCSA-N carbacephem Chemical compound C1CC(C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)C)[C@H]21 JSVCEVCSANKFDY-SFYZADRCSA-N 0.000 claims 4
- 229960002100 cefepime Drugs 0.000 claims 4
- HVFLCNVBZFFHBT-ZKDACBOMSA-N cefepime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1C[N+]1(C)CCCC1 HVFLCNVBZFFHBT-ZKDACBOMSA-N 0.000 claims 4
- 229960000484 ceftazidime Drugs 0.000 claims 4
- 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 4
- UCKZMPLVLCKKMO-LHLIQPBNSA-N cephamycin Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](C)[C@]21OC UCKZMPLVLCKKMO-LHLIQPBNSA-N 0.000 claims 4
- 239000003120 macrolide antibiotic agent Substances 0.000 claims 4
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical compound NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 claims 4
- 229960001907 nitrofurazone Drugs 0.000 claims 4
- 229940049954 penicillin Drugs 0.000 claims 4
- 229920001184 polypeptide Polymers 0.000 claims 4
- 108090000765 processed proteins & peptides Proteins 0.000 claims 4
- 102000004196 processed proteins & peptides Human genes 0.000 claims 4
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims 4
- ATEBXHFBFRCZMA-VXTBVIBXSA-N rifabutin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC(=C2N3)C(=O)C=4C(O)=C5C)C)OC)C5=C1C=4C2=NC13CCN(CC(C)C)CC1 ATEBXHFBFRCZMA-VXTBVIBXSA-N 0.000 claims 4
- 229960000885 rifabutin Drugs 0.000 claims 4
- 229940124530 sulfonamide Drugs 0.000 claims 4
- 150000003456 sulfonamides Chemical class 0.000 claims 4
- 229960002180 tetracycline Drugs 0.000 claims 4
- 229930101283 tetracycline Natural products 0.000 claims 4
- 235000019364 tetracycline Nutrition 0.000 claims 4
- 150000003522 tetracyclines Chemical class 0.000 claims 4
- 239000004599 antimicrobial Substances 0.000 claims 3
- 229940036735 ceftaroline Drugs 0.000 claims 3
- ZCCUWMICIWSJIX-NQJJCJBVSA-N ceftaroline fosamil Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OCC)C=2N=C(NP(O)(O)=O)SN=2)CC=1SC(SC=1)=NC=1C1=CC=[N+](C)C=C1 ZCCUWMICIWSJIX-NQJJCJBVSA-N 0.000 claims 3
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 claims 3
- QYQDKDWGWDOFFU-IUODEOHRSA-N Cefotiam Chemical compound CN(C)CCN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CC=3N=C(N)SC=3)[C@H]2SC1 QYQDKDWGWDOFFU-IUODEOHRSA-N 0.000 claims 2
- GNWUOVJNSFPWDD-XMZRARIVSA-M Cefoxitin sodium Chemical compound [Na+].N([C@]1(OC)C(N2C(=C(COC(N)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)CC1=CC=CS1 GNWUOVJNSFPWDD-XMZRARIVSA-M 0.000 claims 2
- KEJCWVGMRLCZQQ-YJBYXUATSA-N Cefuroxime axetil Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(=O)OC(C)OC(C)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 KEJCWVGMRLCZQQ-YJBYXUATSA-N 0.000 claims 2
- JWCSIUVGFCSJCK-CAVRMKNVSA-N Disodium Moxalactam Chemical compound N([C@]1(OC)C(N2C(=C(CSC=3N(N=NN=3)C)CO[C@@H]21)C(O)=O)=O)C(=O)C(C(O)=O)C1=CC=C(O)C=C1 JWCSIUVGFCSJCK-CAVRMKNVSA-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
- 230000000844 anti-bacterial effect Effects 0.000 claims 2
- 230000003115 biocidal effect Effects 0.000 claims 2
- 229940041011 carbapenems Drugs 0.000 claims 2
- RRYMAQUWDLIUPV-BXKDBHETSA-N cefacetrile Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CC#N)[C@@H]12 RRYMAQUWDLIUPV-BXKDBHETSA-N 0.000 claims 2
- 229960003972 cefacetrile Drugs 0.000 claims 2
- 229960005361 cefaclor Drugs 0.000 claims 2
- QYIYFLOTGYLRGG-GPCCPHFNSA-N cefaclor Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CS[C@@H]32)C(O)=O)=O)N)=CC=CC=C1 QYIYFLOTGYLRGG-GPCCPHFNSA-N 0.000 claims 2
- CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 claims 2
- 229960003866 cefaloridine Drugs 0.000 claims 2
- XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 claims 2
- 229960000603 cefalotin Drugs 0.000 claims 2
- 229960003012 cefamandole Drugs 0.000 claims 2
- OLVCFLKTBJRLHI-AXAPSJFSSA-N cefamandole Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)[C@H](O)C=3C=CC=CC=3)[C@H]2SC1 OLVCFLKTBJRLHI-AXAPSJFSSA-N 0.000 claims 2
- 229960001139 cefazolin Drugs 0.000 claims 2
- MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 claims 2
- 229960001817 cefbuperazone Drugs 0.000 claims 2
- SMSRCGPDNDCXFR-CYWZMYCQSA-N cefbuperazone Chemical compound O=C1C(=O)N(CC)CCN1C(=O)N[C@H]([C@H](C)O)C(=O)N[C@]1(OC)C(=O)N2C(C(O)=O)=C(CSC=3N(N=NN=3)C)CS[C@@H]21 SMSRCGPDNDCXFR-CYWZMYCQSA-N 0.000 claims 2
- JUVHVMCKLDZLGN-TVNFHGJBSA-N cefclidin Chemical compound N([C@@H]1C(N2C(=C(C[N+]34CCC(CC3)(CC4)C(N)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=NSC(N)=N1 JUVHVMCKLDZLGN-TVNFHGJBSA-N 0.000 claims 2
- 229960003719 cefdinir Drugs 0.000 claims 2
- RTXOFQZKPXMALH-GHXIOONMSA-N cefdinir Chemical compound S1C(N)=NC(C(=N\O)\C(=O)N[C@@H]2C(N3C(=C(C=C)CS[C@@H]32)C(O)=O)=O)=C1 RTXOFQZKPXMALH-GHXIOONMSA-N 0.000 claims 2
- 229960002142 cefditoren pivoxil Drugs 0.000 claims 2
- AFZFFLVORLEPPO-UVYJNCLZSA-N cefditoren pivoxil Chemical compound S([C@@H]1[C@@H](C(N1C=1C(=O)OCOC(=O)C(C)(C)C)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1\C=C/C=1SC=NC=1C AFZFFLVORLEPPO-UVYJNCLZSA-N 0.000 claims 2
- DASYMCLQENWCJG-XUKDPADISA-N cefetamet pivoxil Chemical compound N([C@@H]1C(N2C(=C(C)CS[C@@H]21)C(=O)OCOC(=O)C(C)(C)C)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 DASYMCLQENWCJG-XUKDPADISA-N 0.000 claims 2
- 229950000726 cefetamet pivoxil Drugs 0.000 claims 2
- 229960002129 cefixime Drugs 0.000 claims 2
- OKBVVJOGVLARMR-QSWIMTSFSA-N cefixime Chemical compound S1C(N)=NC(C(=N\OCC(O)=O)\C(=O)N[C@@H]2C(N3C(=C(C=C)CS[C@@H]32)C(O)=O)=O)=C1 OKBVVJOGVLARMR-QSWIMTSFSA-N 0.000 claims 2
- XAKKNLNAJBNLPC-MAYKBZFQSA-N cefluprenam Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)/C=C/C[N+](C)(CC)CC(N)=O)C([O-])=O)C(=O)C(=N/OCF)\C1=NSC(N)=N1 XAKKNLNAJBNLPC-MAYKBZFQSA-N 0.000 claims 2
- 229950001334 cefluprenam Drugs 0.000 claims 2
- 229960004261 cefotaxime Drugs 0.000 claims 2
- AZZMGZXNTDTSME-JUZDKLSSSA-M cefotaxime sodium Chemical compound [Na+].N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 AZZMGZXNTDTSME-JUZDKLSSSA-M 0.000 claims 2
- 229960001242 cefotiam Drugs 0.000 claims 2
- 229960002682 cefoxitin Drugs 0.000 claims 2
- QDUIJCOKQCCXQY-WHJQOFBOSA-N cefozopran Chemical compound N([C@@H]1C(N2C(=C(CN3C4=CC=CN=[N+]4C=C3)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=NSC(N)=N1 QDUIJCOKQCCXQY-WHJQOFBOSA-N 0.000 claims 2
- 229960002642 cefozopran Drugs 0.000 claims 2
- LNZMRLHZGOBKAN-KAWPREARSA-N cefpimizole Chemical compound N1=CNC(C(=O)N[C@@H](C(=O)N[C@@H]2C(N3C(=C(C[N+]=4C=CC(CCS(O)(=O)=O)=CC=4)CS[C@@H]32)C([O-])=O)=O)C=2C=CC=CC=2)=C1C(=O)O LNZMRLHZGOBKAN-KAWPREARSA-N 0.000 claims 2
- 229950004036 cefpimizole Drugs 0.000 claims 2
- 229960003202 cefsulodin Drugs 0.000 claims 2
- SYLKGLMBLAAGSC-QLVMHMETSA-N cefsulodin Chemical compound C1=CC(C(=O)N)=CC=[N+]1CC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)[C@@H](C=3C=CC=CC=3)S(O)(=O)=O)[C@H]2SC1 SYLKGLMBLAAGSC-QLVMHMETSA-N 0.000 claims 2
- UNJFKXSSGBWRBZ-BJCIPQKHSA-N ceftibuten Chemical compound S1C(N)=NC(C(=C\CC(O)=O)\C(=O)N[C@@H]2C(N3C(=CCS[C@@H]32)C(O)=O)=O)=C1 UNJFKXSSGBWRBZ-BJCIPQKHSA-N 0.000 claims 2
- 229960001991 ceftizoxime Drugs 0.000 claims 2
- NNULBSISHYWZJU-LLKWHZGFSA-N ceftizoxime Chemical compound N([C@@H]1C(N2C(=CCS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 NNULBSISHYWZJU-LLKWHZGFSA-N 0.000 claims 2
- 229960004755 ceftriaxone Drugs 0.000 claims 2
- VAAUVRVFOQPIGI-SPQHTLEESA-N ceftriaxone Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(=O)C(=O)NN1C VAAUVRVFOQPIGI-SPQHTLEESA-N 0.000 claims 2
- 229960001668 cefuroxime Drugs 0.000 claims 2
- JFPVXVDWJQMJEE-IZRZKJBUSA-N cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-IZRZKJBUSA-N 0.000 claims 2
- 229960002620 cefuroxime axetil Drugs 0.000 claims 2
- 229940106164 cephalexin Drugs 0.000 claims 2
- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 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
- 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
- 229960002182 imipenem Drugs 0.000 claims 2
- 229960000433 latamoxef Drugs 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
- 229940041009 monobactams Drugs 0.000 claims 2
- 150000002961 penems Chemical class 0.000 claims 2
- 150000002960 penicillins Chemical class 0.000 claims 2
- 229960002292 piperacillin Drugs 0.000 claims 2
- WCMIIGXFCMNQDS-IDYPWDAWSA-M piperacillin sodium Chemical compound [Na+].O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC=CC=1)C(=O)N[C@@H]1C(=O)N2[C@@H](C([O-])=O)C(C)(C)S[C@@H]21 WCMIIGXFCMNQDS-IDYPWDAWSA-M 0.000 claims 2
- 229940124586 β-lactam antibiotics Drugs 0.000 claims 2
- HYDTWJWCBMFIQL-GMTAPVOTSA-N 2-[[(2r,5r)-7-oxo-2-[[[(3r)-piperidine-3-carbonyl]amino]carbamoyl]-1,6-diazabicyclo[3.2.1]octan-6-yl]oxy]acetic acid Chemical compound O=C([C@@H]1N2C[C@@](CC1)(N(C2=O)OCC(O)=O)[H])NNC(=O)[C@@H]1CCCNC1 HYDTWJWCBMFIQL-GMTAPVOTSA-N 0.000 claims 1
- MBMIFCNAWJUXOY-HBNTYKKESA-N C1C[C@H](NC1)CCC(=O)NNC(=O)[C@H]2CC[C@@H]3CN2C(=O)N3OS(=O)(=O)O Chemical compound C1C[C@H](NC1)CCC(=O)NNC(=O)[C@H]2CC[C@@H]3CN2C(=O)N3OS(=O)(=O)O MBMIFCNAWJUXOY-HBNTYKKESA-N 0.000 claims 1
- NUSJTKGZIBQZGQ-SCLLHFNJSA-M CC(C)(C(NNC([C@@H](CC[C@H](C1)N2OS([O-])(=O)=O)N1C2=O)=O)=O)C#N.[Na+] Chemical compound CC(C)(C(NNC([C@@H](CC[C@H](C1)N2OS([O-])(=O)=O)N1C2=O)=O)=O)C#N.[Na+] NUSJTKGZIBQZGQ-SCLLHFNJSA-M 0.000 claims 1
- 229940123930 Lactamase inhibitor Drugs 0.000 claims 1
- UYLDIIWDUDIANL-RFZPGFLSSA-N [(2R,5R)-2-(hydrazinecarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound N(N)C(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O UYLDIIWDUDIANL-RFZPGFLSSA-N 0.000 claims 1
- XBQYSOJNZSCBNF-RNFRBKRXSA-N [(2R,5R)-2-[(3-aminopropanoylamino)carbamoyl]-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound NCCC(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O XBQYSOJNZSCBNF-RNFRBKRXSA-N 0.000 claims 1
- DKQYIDUFCOSIGB-HTQZYQBOSA-N [(2R,5R)-2-[(4-aminobutanoylamino)carbamoyl]-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound NCCCC(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O DKQYIDUFCOSIGB-HTQZYQBOSA-N 0.000 claims 1
- OGLYOHMUJKXRIO-RKDXNWHRSA-N [(2R,5R)-2-[(5-aminopentanoylamino)carbamoyl]-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound NCCCCC(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O OGLYOHMUJKXRIO-RKDXNWHRSA-N 0.000 claims 1
- XYTWGTZSUPIYFZ-HTQZYQBOSA-N [(2R,5R)-2-[(azetidine-3-carbonylamino)carbamoyl]-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound N1CC(C1)C(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O XYTWGTZSUPIYFZ-HTQZYQBOSA-N 0.000 claims 1
- APBHTOUFSZXYCV-PHDIDXHHSA-N [(2R,5R)-2-[[(2-aminoacetyl)amino]carbamoyl]-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound NCC(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O APBHTOUFSZXYCV-PHDIDXHHSA-N 0.000 claims 1
- QEJZBLVKSRUUKM-DSYKOEDSSA-N [(2R,5R)-2-[[[(2S)-2-amino-3-hydroxypropanoyl]amino]carbamoyl]-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound N[C@H](C(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O)CO QEJZBLVKSRUUKM-DSYKOEDSSA-N 0.000 claims 1
- HGDFYIWSKIRGEH-LURQLKTLSA-N [(2R,5R)-2-[[[(2S,4R)-4-hydroxypyrrolidine-2-carbonyl]amino]carbamoyl]-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound O[C@@H]1C[C@H](NC1)C(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O HGDFYIWSKIRGEH-LURQLKTLSA-N 0.000 claims 1
- BSIPLMLCLGSFOX-DOLQZWNJSA-N [(2R,5R)-2-[[[(2S,4R)-4-methoxypyrrolidine-2-carbonyl]amino]carbamoyl]-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound CO[C@@H]1C[C@H](NC1)C(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O BSIPLMLCLGSFOX-DOLQZWNJSA-N 0.000 claims 1
- UDWBQLXRVRBWLL-UYXSQOIJSA-N [(2R,5R)-2-[[[(2S,4S)-4-(diaminomethylideneamino)pyrrolidine-2-carbonyl]amino]carbamoyl]-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound N(C(=N)N)[C@H]1C[C@H](NC1)C(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O UDWBQLXRVRBWLL-UYXSQOIJSA-N 0.000 claims 1
- CIIXHNAIHMNPNA-UYXSQOIJSA-N [(2R,5R)-2-[[[(2S,4S)-4-aminopyrrolidine-2-carbonyl]amino]carbamoyl]-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound N[C@H]1C[C@H](NC1)C(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O CIIXHNAIHMNPNA-UYXSQOIJSA-N 0.000 claims 1
- HHIXMUSUBFKSRV-UYXSQOIJSA-N [(2R,5R)-2-[[[(2S,4S)-4-fluoropyrrolidine-2-carbonyl]amino]carbamoyl]-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound F[C@H]1C[C@H](NC1)C(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O HHIXMUSUBFKSRV-UYXSQOIJSA-N 0.000 claims 1
- CJDXSFPMLHXKPP-PQDIPPBSSA-N [(2R,5R)-7-oxo-2-[(3-piperidin-2-ylpropanoylamino)carbamoyl]-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound N1C(CCCC1)CCC(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O CJDXSFPMLHXKPP-PQDIPPBSSA-N 0.000 claims 1
- KXTJXSAKJFXLEI-RCAUJQPQSA-N [(2R,5R)-7-oxo-2-[(piperidine-2-carbonylamino)carbamoyl]-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound N1C(CCCC1)C(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O KXTJXSAKJFXLEI-RCAUJQPQSA-N 0.000 claims 1
- GYXFEMGIRUYDEP-NXEZZACHSA-N [(2R,5R)-7-oxo-2-[(piperidine-4-carbonylamino)carbamoyl]-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound N1CCC(CC1)C(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O GYXFEMGIRUYDEP-NXEZZACHSA-N 0.000 claims 1
- GSHJUFCGOVFWMM-RKDXNWHRSA-N [(2R,5R)-7-oxo-2-[(pyrrolidine-1-carbonylamino)carbamoyl]-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound N1(CCCC1)C(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O GSHJUFCGOVFWMM-RKDXNWHRSA-N 0.000 claims 1
- NRZLXMVYLARNKK-NXEZZACHSA-N [(2R,5R)-7-oxo-2-[[(2-piperazin-1-ylacetyl)amino]carbamoyl]-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound N1CCN(CC1)CC(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O NRZLXMVYLARNKK-NXEZZACHSA-N 0.000 claims 1
- WXSCNWNDBSBAIG-NXEZZACHSA-N [(2R,5R)-7-oxo-2-[[(3-oxo-3-piperazin-1-ylpropanoyl)amino]carbamoyl]-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound O=C(CC(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O)N1CCNCC1 WXSCNWNDBSBAIG-NXEZZACHSA-N 0.000 claims 1
- KXTJXSAKJFXLEI-OPRDCNLKSA-N [(2R,5R)-7-oxo-2-[[[(2R)-piperidine-2-carbonyl]amino]carbamoyl]-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound N1[C@H](CCCC1)C(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O KXTJXSAKJFXLEI-OPRDCNLKSA-N 0.000 claims 1
- KXTJXSAKJFXLEI-KXUCPTDWSA-N [(2R,5R)-7-oxo-2-[[[(2S)-piperidine-2-carbonyl]amino]carbamoyl]-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound N1[C@@H](CCCC1)C(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O KXTJXSAKJFXLEI-KXUCPTDWSA-N 0.000 claims 1
- YCZPXRQPDCXTIO-OPRDCNLKSA-N [(2R,5R)-7-oxo-2-[[[(3R)-piperidine-3-carbonyl]amino]carbamoyl]-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound N1C[C@@H](CCC1)C(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O YCZPXRQPDCXTIO-OPRDCNLKSA-N 0.000 claims 1
- NAURQUDBIPQVFZ-IWSPIJDZSA-N [(2R,5R)-7-oxo-2-[[[(3R)-pyrrolidine-3-carbonyl]amino]carbamoyl]-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound N1C[C@@H](CC1)C(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O NAURQUDBIPQVFZ-IWSPIJDZSA-N 0.000 claims 1
- NAURQUDBIPQVFZ-DJLDLDEBSA-N [(2R,5R)-7-oxo-2-[[[(3S)-pyrrolidine-3-carbonyl]amino]carbamoyl]-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound N1C[C@H](CC1)C(=O)NNC(=O)[C@@H]1N2C(N([C@H](CC1)C2)OS(O)(=O)=O)=O NAURQUDBIPQVFZ-DJLDLDEBSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
- 230000000845 anti-microbial effect Effects 0.000 claims 1
- 150000001768 cations Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 1
- 0 CNNC(C(CCC(C1)N2O*)N1C2=O)=O Chemical compound CNNC(C(CCC(C1)N2O*)N1C2=O)=O 0.000 description 1
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| FR2937034B1 (fr) * | 2008-10-10 | 2012-11-23 | Novexel | Nouveaux composes heterocycliques azotes, leur preparation et leur utilisation comme medicaments antibacteriens |
| FR2951171A1 (fr) * | 2009-10-09 | 2011-04-15 | Novexel | Nouveau sel de sodium d'un compose azabicyclique sous forme enantiomere cristallisee et nouvelles formes polymorphes et pseudopolymorphes ainsi que leur preparation |
| DK2748165T3 (en) * | 2011-08-27 | 2016-12-19 | Wockhardt Ltd | 1,6-diazabicyclo [3,2,1] octane-7-ON DERIVATIVES AND THEIR USE IN THE TREATMENT OF BACTERIAL INFECTIONS |
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2012
- 2012-08-24 DK DK12772808.7T patent/DK2748165T3/en active
- 2012-08-24 JP JP2014510942A patent/JP5666743B2/ja active Active
- 2012-08-24 BR BR112013028813-2A patent/BR112013028813B1/pt active IP Right Grant
- 2012-08-24 CA CA2833241A patent/CA2833241C/en active Active
- 2012-08-24 MX MX2013013887A patent/MX348974B/es active IP Right Grant
- 2012-08-24 HU HUE12772808A patent/HUE030311T2/en unknown
- 2012-08-24 CN CN201280025141.8A patent/CN103619843B/zh active Active
- 2012-08-24 RU RU2013155902/04A patent/RU2578370C2/ru active
- 2012-08-24 WO PCT/IB2012/054290 patent/WO2013030733A1/en not_active Ceased
- 2012-08-24 ES ES12772808.7T patent/ES2603198T3/es active Active
- 2012-08-24 US US14/111,592 patent/US8822450B2/en active Active
- 2012-08-24 RU RU2016106633A patent/RU2636147C1/ru active
- 2012-08-24 KR KR1020137034052A patent/KR101512738B1/ko active Active
- 2012-08-24 AU AU2012303691A patent/AU2012303691B2/en active Active
- 2012-08-24 PT PT127728087T patent/PT2748165T/pt unknown
- 2012-08-24 EP EP12772808.7A patent/EP2748165B1/en active Active
- 2012-08-24 PL PL12772808T patent/PL2748165T3/pl unknown
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2013
- 2013-10-14 ZA ZA2013/07631A patent/ZA201307631B/en unknown
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2014
- 2014-06-03 US US14/294,364 patent/US8853197B1/en active Active
- 2014-08-06 US US14/452,652 patent/US8987297B2/en active Active
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2015
- 2015-01-30 US US14/609,704 patent/US9132133B2/en active Active
- 2015-07-09 US US14/795,048 patent/US9381200B2/en active Active
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