JP2020507564A5 - - Google Patents
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- Publication number
- JP2020507564A5 JP2020507564A5 JP2019542369A JP2019542369A JP2020507564A5 JP 2020507564 A5 JP2020507564 A5 JP 2020507564A5 JP 2019542369 A JP2019542369 A JP 2019542369A JP 2019542369 A JP2019542369 A JP 2019542369A JP 2020507564 A5 JP2020507564 A5 JP 2020507564A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- optionally substituted
- pharmaceutically acceptable
- acceptable salt
- prodrug
- 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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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 35
- 150000001875 compounds Chemical class 0.000 claims 21
- 229940002612 prodrug Drugs 0.000 claims 21
- 239000000651 prodrug Substances 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 21
- 239000012453 solvate Substances 0.000 claims 20
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 10
- -1 Nitro, hydroxyl Chemical group 0.000 claims 8
- 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 5
- 229960001139 cefazolin Drugs 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 229940124597 therapeutic agent Drugs 0.000 claims 4
- 239000002132 β-lactam antibiotic Substances 0.000 claims 4
- 229940124586 β-lactam antibiotics Drugs 0.000 claims 4
- 208000035143 Bacterial infection Diseases 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 2
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 2
- 241000606125 Bacteroides Species 0.000 claims 2
- 241000191940 Staphylococcus Species 0.000 claims 2
- 150000001345 alkine derivatives Chemical class 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
- SRZNHPXWXCNNDU-RHBCBLIFSA-N cefotetan Chemical compound N([C@]1(OC)C(N2C(=C(CSC=3N(N=NN=3)C)CS[C@@H]21)C(O)=O)=O)C(=O)C1SC(=C(C(N)=O)C(O)=O)S1 SRZNHPXWXCNNDU-RHBCBLIFSA-N 0.000 claims 2
- 229960005495 cefotetan Drugs 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 229960003907 linezolid Drugs 0.000 claims 2
- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- LITBAYYWXZOHAW-XDZRHBBOSA-N (2s,5r,6r)-6-[[(2r)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;(2s,3s,5r)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4$l^{6}-thia-1-azabicyclo[3.2.0]hept Chemical compound C([C@]1(C)S([C@H]2N(C(C2)=O)[C@H]1C(O)=O)(=O)=O)N1C=CN=N1.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 LITBAYYWXZOHAW-XDZRHBBOSA-N 0.000 claims 1
- KEDAXBWZURNCHS-GPODMPQUSA-N (4r,5s,6s)-3-[(3s,5s)-5-[(3s)-3-[[2-(diaminomethylideneamino)acetyl]amino]pyrrolidine-1-carbonyl]-1-methylpyrrolidin-3-yl]sulfanyl-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound O=C([C@@H]1C[C@@H](CN1C)SC=1[C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)N1CC[C@H](NC(=O)CN=C(N)N)C1 KEDAXBWZURNCHS-GPODMPQUSA-N 0.000 claims 1
- WDLWHQDACQUCJR-ZAMMOSSLSA-N (6r,7r)-7-[[(2r)-2-azaniumyl-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(e)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)/C=C/C)C(O)=O)=CC=C(O)C=C1 WDLWHQDACQUCJR-ZAMMOSSLSA-N 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- MINDHVHHQZYEEK-UHFFFAOYSA-N (E)-(2S,3R,4R,5S)-5-[(2S,3S,4S,5S)-2,3-epoxy-5-hydroxy-4-methylhexyl]tetrahydro-3,4-dihydroxy-(beta)-methyl-2H-pyran-2-crotonic acid ester with 9-hydroxynonanoic acid Natural products CC(O)C(C)C1OC1CC1C(O)C(O)C(CC(C)=CC(=O)OCCCCCCCCC(O)=O)OC1 MINDHVHHQZYEEK-UHFFFAOYSA-N 0.000 claims 1
- HGGAKXAHAYOLDJ-FHZUQPTBSA-N 6alpha-[(R)-1-hydroxyethyl]-2-[(R)-tetrahydrofuran-2-yl]pen-2-em-3-carboxylic acid Chemical compound S([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1[C@H]1CCCO1 HGGAKXAHAYOLDJ-FHZUQPTBSA-N 0.000 claims 1
- 241000588626 Acinetobacter baumannii Species 0.000 claims 1
- 241000588624 Acinetobacter calcoaceticus Species 0.000 claims 1
- 241001148231 Acinetobacter haemolyticus Species 0.000 claims 1
- 241000607528 Aeromonas hydrophila Species 0.000 claims 1
- 108010001478 Bacitracin Proteins 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- 241001135322 Bacteroides eggerthii Species 0.000 claims 1
- 241000606124 Bacteroides fragilis Species 0.000 claims 1
- 241000606123 Bacteroides thetaiotaomicron Species 0.000 claims 1
- 241000606219 Bacteroides uniformis Species 0.000 claims 1
- 241000606215 Bacteroides vulgatus Species 0.000 claims 1
- 241000588779 Bordetella bronchiseptica Species 0.000 claims 1
- 241000588780 Bordetella parapertussis Species 0.000 claims 1
- 241000588832 Bordetella pertussis Species 0.000 claims 1
- 241000589969 Borreliella burgdorferi Species 0.000 claims 1
- 241000589513 Burkholderia cepacia Species 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- 241000589877 Campylobacter coli Species 0.000 claims 1
- 241000589874 Campylobacter fetus Species 0.000 claims 1
- 241000589875 Campylobacter jejuni Species 0.000 claims 1
- 229930186147 Cephalosporin Natural products 0.000 claims 1
- 241000588919 Citrobacter freundii Species 0.000 claims 1
- 241000193163 Clostridioides difficile Species 0.000 claims 1
- 108010078777 Colistin Proteins 0.000 claims 1
- 241000186227 Corynebacterium diphtheriae Species 0.000 claims 1
- 241000918600 Corynebacterium ulcerans Species 0.000 claims 1
- 108010013198 Daptomycin Proteins 0.000 claims 1
- 241001600125 Delftia acidovorans Species 0.000 claims 1
- 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 1
- NTUBEBXBDGKBTJ-WGLOMNHJSA-N Doripenem hydrate Chemical compound O.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 NTUBEBXBDGKBTJ-WGLOMNHJSA-N 0.000 claims 1
- 241000588697 Enterobacter cloacae Species 0.000 claims 1
- 241000194032 Enterococcus faecalis Species 0.000 claims 1
- 241000194031 Enterococcus faecium Species 0.000 claims 1
- 241000588724 Escherichia coli Species 0.000 claims 1
- 241000589602 Francisella tularensis Species 0.000 claims 1
- 241000207201 Gardnerella vaginalis Species 0.000 claims 1
- 241000606788 Haemophilus haemolyticus Species 0.000 claims 1
- 241000606768 Haemophilus influenzae Species 0.000 claims 1
- 241000606822 Haemophilus parahaemolyticus Species 0.000 claims 1
- 241000606766 Haemophilus parainfluenzae Species 0.000 claims 1
- 241000590002 Helicobacter pylori Species 0.000 claims 1
- 241001454354 Kingella Species 0.000 claims 1
- 241000588915 Klebsiella aerogenes Species 0.000 claims 1
- 241000588749 Klebsiella oxytoca Species 0.000 claims 1
- 241000588747 Klebsiella pneumoniae Species 0.000 claims 1
- 241000589242 Legionella pneumophila Species 0.000 claims 1
- 241000186779 Listeria monocytogenes Species 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 241001293418 Mannheimia haemolytica Species 0.000 claims 1
- 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 1
- 241000588621 Moraxella Species 0.000 claims 1
- 241000588655 Moraxella catarrhalis Species 0.000 claims 1
- 241000588772 Morganella morganii Species 0.000 claims 1
- 241000186367 Mycobacterium avium Species 0.000 claims 1
- 241000186364 Mycobacterium intracellulare Species 0.000 claims 1
- 241000186362 Mycobacterium leprae Species 0.000 claims 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims 1
- 241000588652 Neisseria gonorrhoeae Species 0.000 claims 1
- 241000588650 Neisseria meningitidis Species 0.000 claims 1
- 241001135232 Odoribacter splanchnicus Species 0.000 claims 1
- 241000606210 Parabacteroides distasonis Species 0.000 claims 1
- 241000606856 Pasteurella multocida Species 0.000 claims 1
- 229930182555 Penicillin Natural products 0.000 claims 1
- 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 1
- 241000588770 Proteus mirabilis Species 0.000 claims 1
- 241000588767 Proteus vulgaris Species 0.000 claims 1
- 241000576783 Providencia alcalifaciens Species 0.000 claims 1
- 241000588777 Providencia rettgeri Species 0.000 claims 1
- 241000588778 Providencia stuartii Species 0.000 claims 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims 1
- 241000168225 Pseudomonas alcaligenes Species 0.000 claims 1
- 241000589540 Pseudomonas fluorescens Species 0.000 claims 1
- 241000589776 Pseudomonas putida Species 0.000 claims 1
- 241001354013 Salmonella enterica subsp. enterica serovar Enteritidis Species 0.000 claims 1
- 241000531795 Salmonella enterica subsp. enterica serovar Paratyphi A Species 0.000 claims 1
- 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 claims 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 claims 1
- 241000607715 Serratia marcescens Species 0.000 claims 1
- 241000607764 Shigella dysenteriae Species 0.000 claims 1
- 241000607762 Shigella flexneri Species 0.000 claims 1
- 241000607760 Shigella sonnei Species 0.000 claims 1
- 241000191967 Staphylococcus aureus Species 0.000 claims 1
- 241000191963 Staphylococcus epidermidis Species 0.000 claims 1
- 241000191984 Staphylococcus haemolyticus Species 0.000 claims 1
- 241000192087 Staphylococcus hominis Species 0.000 claims 1
- 241000191982 Staphylococcus hyicus Species 0.000 claims 1
- 241001147691 Staphylococcus saprophyticus Species 0.000 claims 1
- 241000122973 Stenotrophomonas maltophilia Species 0.000 claims 1
- 241000193985 Streptococcus agalactiae Species 0.000 claims 1
- 241000193998 Streptococcus pneumoniae Species 0.000 claims 1
- 241000193996 Streptococcus pyogenes Species 0.000 claims 1
- 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 1
- 241000607626 Vibrio cholerae Species 0.000 claims 1
- 241000607272 Vibrio parahaemolyticus Species 0.000 claims 1
- 241000607447 Yersinia enterocolitica Species 0.000 claims 1
- 241000607481 Yersinia intermedia Species 0.000 claims 1
- 241000607479 Yersinia pestis Species 0.000 claims 1
- 241000607477 Yersinia pseudotuberculosis Species 0.000 claims 1
- 241000606834 [Haemophilus] ducreyi Species 0.000 claims 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 claims 1
- 229960003022 amoxicillin Drugs 0.000 claims 1
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 claims 1
- 229960000723 ampicillin Drugs 0.000 claims 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 229940088710 antibiotic agent Drugs 0.000 claims 1
- 229960003644 aztreonam Drugs 0.000 claims 1
- 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 1
- 229960003071 bacitracin Drugs 0.000 claims 1
- 229930184125 bacitracin Natural products 0.000 claims 1
- CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 claims 1
- 239000003781 beta lactamase inhibitor Substances 0.000 claims 1
- 229940126813 beta-lactamase inhibitor Drugs 0.000 claims 1
- 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 1
- 229960003169 biapenem Drugs 0.000 claims 1
- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical compound C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 claims 1
- 229960003669 carbenicillin Drugs 0.000 claims 1
- FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 claims 1
- 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 1
- 229960003012 cefamandole Drugs 0.000 claims 1
- 229960005090 cefpodoxime Drugs 0.000 claims 1
- WYUSVOMTXWRGEK-HBWVYFAYSA-N cefpodoxime Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC)C(O)=O)C(=O)C(=N/OC)\C1=CSC(N)=N1 WYUSVOMTXWRGEK-HBWVYFAYSA-N 0.000 claims 1
- 229960002580 cefprozil Drugs 0.000 claims 1
- 229960000484 ceftazidime Drugs 0.000 claims 1
- 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 1
- 229960001991 ceftizoxime Drugs 0.000 claims 1
- 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 1
- 229960004755 ceftriaxone Drugs 0.000 claims 1
- 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 1
- 229940124587 cephalosporin Drugs 0.000 claims 1
- 150000001780 cephalosporins Chemical class 0.000 claims 1
- 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 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229960005091 chloramphenicol Drugs 0.000 claims 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 claims 1
- 229960003346 colistin Drugs 0.000 claims 1
- 229960005484 daptomycin Drugs 0.000 claims 1
- DOAKLVKFURWEDJ-QCMAZARJSA-N daptomycin Chemical compound C([C@H]1C(=O)O[C@H](C)[C@@H](C(NCC(=O)N[C@@H](CCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C)C(=O)N[C@@H](CC(O)=O)C(=O)NCC(=O)N[C@H](CO)C(=O)N[C@H](C(=O)N1)[C@H](C)CC(O)=O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](CC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)CCCCCCCCC)C(=O)C1=CC=CC=C1N DOAKLVKFURWEDJ-QCMAZARJSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 229940092559 enterobacter aerogenes Drugs 0.000 claims 1
- 229940032049 enterococcus faecalis Drugs 0.000 claims 1
- 229960000379 faropenem Drugs 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229940124307 fluoroquinolone Drugs 0.000 claims 1
- 229940118764 francisella tularensis Drugs 0.000 claims 1
- 229940047650 haemophilus influenzae Drugs 0.000 claims 1
- 229940037467 helicobacter pylori Drugs 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229960002182 imipenem Drugs 0.000 claims 1
- 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 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 229960000433 latamoxef Drugs 0.000 claims 1
- 229940115932 legionella pneumophila Drugs 0.000 claims 1
- 239000003120 macrolide antibiotic agent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229960002260 meropenem Drugs 0.000 claims 1
- 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 1
- 229960003085 meticillin Drugs 0.000 claims 1
- 229960000198 mezlocillin Drugs 0.000 claims 1
- YPBATNHYBCGSSN-VWPFQQQWSA-N mezlocillin Chemical compound N([C@@H](C(=O)N[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C=1C=CC=CC=1)C(=O)N1CCN(S(C)(=O)=O)C1=O YPBATNHYBCGSSN-VWPFQQQWSA-N 0.000 claims 1
- 229940076266 morganella morganii Drugs 0.000 claims 1
- 229960003128 mupirocin Drugs 0.000 claims 1
- 229930187697 mupirocin Natural products 0.000 claims 1
- DDHVILIIHBIMQU-YJGQQKNPSA-L mupirocin calcium hydrate Chemical compound O.O.[Ca+2].C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@@H]1[C@@H](O)[C@@H](O)[C@H](C\C(C)=C\C(=O)OCCCCCCCCC([O-])=O)OC1.C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@@H]1[C@@H](O)[C@@H](O)[C@H](C\C(C)=C\C(=O)OCCCCCCCCC([O-])=O)OC1 DDHVILIIHBIMQU-YJGQQKNPSA-L 0.000 claims 1
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- 229960001019 oxacillin Drugs 0.000 claims 1
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- 229940051027 pasteurella multocida Drugs 0.000 claims 1
- 229940049954 penicillin Drugs 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
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- 229940104641 piperacillin / tazobactam Drugs 0.000 claims 1
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- 239000003910 polypeptide antibiotic agent Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229940007042 proteus vulgaris Drugs 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 229940007046 shigella dysenteriae Drugs 0.000 claims 1
- 229940115939 shigella sonnei Drugs 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 229940037649 staphylococcus haemolyticus Drugs 0.000 claims 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 229960004659 ticarcillin Drugs 0.000 claims 1
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 claims 1
- 229950003816 tomopenem Drugs 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- 229940118696 vibrio cholerae Drugs 0.000 claims 1
- 229940098232 yersinia enterocolitica Drugs 0.000 claims 1
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 claims 1
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| EP3377474B1 (en) | 2015-11-20 | 2023-08-16 | RQX Pharmaceuticals, Inc. | Macrocyclic broad spectrum antibiotics |
| MX2019003087A (es) | 2016-09-16 | 2019-08-12 | Cortexyme Inc | Inhibidores cetónicos de gingipain de lisina. |
| IL295889B2 (en) | 2019-05-28 | 2025-01-01 | Hoffmann La Roche | Broad-spectrum macrocyclic antibiotic |
| CN112480007B (zh) * | 2020-12-08 | 2022-11-18 | 宿迁市科莱博生物化学有限公司 | 一种1，3-二甲基-1h-吡唑-4-羧酸的合成方法 |
| CN116284026B (zh) * | 2023-03-16 | 2024-05-14 | 天津师范大学 | 一种水溶性阳离子分子笼及其合成方法与应用 |
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| BR112012021931A2 (pt) * | 2010-03-09 | 2016-05-31 | Merck Canada Inc | composto, composição farmacêutica, método para tratar uma infecção bacteriana, e, uso de composto |
| KR20130105659A (ko) * | 2010-09-15 | 2013-09-25 | 더 스크립스 리서치 인스티튜트 | 광범위 스펙트럼 항생제 아릴로마이신 유사체 |
| WO2012166665A2 (en) * | 2011-05-27 | 2012-12-06 | Rqx Pharmaceuticals, Inc. | Broad spectrum antibiotics |
| CA2867448A1 (en) | 2012-03-14 | 2013-09-19 | Floyd E. Romesberg | Broad spectrum antibiotic arylomycin analogs |
| EP2913854B1 (en) * | 2012-10-23 | 2020-05-27 | Fuji Electric Co., Ltd. | Semiconductor device and method for manufacturing same |
| CN103788176A (zh) * | 2012-10-31 | 2014-05-14 | 上海来益生物药物研究开发中心有限责任公司 | 一种arylomycin类化合物及其制备方法和应用 |
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| US20190067498A1 (en) * | 2017-08-28 | 2019-02-28 | Meng Tao | Light-induced aluminum plating on silicon for solar cell metallization |
| RU2016146581A (ru) * | 2014-05-20 | 2018-06-21 | АрКьюЭкс ФАРМАСЪЮТИКЛС, ИНК. | Макроциклические антибиотики широкого спектра действия |
| EP3377474B1 (en) | 2015-11-20 | 2023-08-16 | RQX Pharmaceuticals, Inc. | Macrocyclic broad spectrum antibiotics |
| TWI725075B (zh) * | 2015-11-20 | 2021-04-21 | 美商Ｒｑｘ製藥公司 | 巨環廣效抗生素 |
| CA3057997A1 (en) | 2017-03-27 | 2018-10-04 | F. Hoffmann-La Roche Ag | Process for making arylomyin ring analogs |
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