KR20170007448A - 보론산 유도체 및 그의 치료적 용도 - Google Patents
보론산 유도체 및 그의 치료적 용도 Download PDFInfo
- Publication number
- KR20170007448A KR20170007448A KR1020167035427A KR20167035427A KR20170007448A KR 20170007448 A KR20170007448 A KR 20170007448A KR 1020167035427 A KR1020167035427 A KR 1020167035427A KR 20167035427 A KR20167035427 A KR 20167035427A KR 20170007448 A KR20170007448 A KR 20170007448A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- amino
- group
- hydroxy
- compound
- 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.)
- Withdrawn
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- 150000001642 boronic acid derivatives Chemical class 0.000 title abstract description 8
- 230000001225 therapeutic effect Effects 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 407
- 238000000034 method Methods 0.000 claims abstract description 126
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 38
- 239000003814 drug Substances 0.000 claims abstract description 20
- -1 hydroxy Chemical group 0.000 claims description 227
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 154
- 125000001424 substituent group Chemical group 0.000 claims description 151
- 229910052736 halogen Inorganic materials 0.000 claims description 138
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 136
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 132
- 150000002367 halogens Chemical group 0.000 claims description 99
- 125000003118 aryl group Chemical group 0.000 claims description 90
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 89
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- 239000001257 hydrogen Substances 0.000 claims description 72
- 229910052739 hydrogen Inorganic materials 0.000 claims description 72
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 70
- 125000000623 heterocyclic group Chemical group 0.000 claims description 63
- 206010057190 Respiratory tract infections Diseases 0.000 claims description 62
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 51
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 45
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 44
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 239000000651 prodrug Substances 0.000 claims description 30
- 229940002612 prodrug Drugs 0.000 claims description 30
- 125000002947 alkylene group Chemical group 0.000 claims description 29
- 229930186147 Cephalosporin Natural products 0.000 claims description 28
- 229940124587 cephalosporin Drugs 0.000 claims description 28
- 150000001780 cephalosporins Chemical class 0.000 claims description 28
- 239000003795 chemical substances by application Substances 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 27
- 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 description 26
- WZPBZJONDBGPKJ-VEHQQRBSSA-N aztreonam Chemical group 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 description 25
- 229960003644 aztreonam Drugs 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- BSIMZHVOQZIAOY-SCSAIBSYSA-N 1-carbapenem-3-carboxylic acid Chemical compound OC(=O)C1=CC[C@@H]2CC(=O)N12 BSIMZHVOQZIAOY-SCSAIBSYSA-N 0.000 claims description 22
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 22
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 20
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 18
- 208000035143 Bacterial infection Diseases 0.000 claims description 17
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 17
- 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 description 15
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims description 14
- 229940079593 drug Drugs 0.000 claims description 14
- 206010041925 Staphylococcal infections Diseases 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 208000015688 methicillin-resistant staphylococcus aureus infectious disease Diseases 0.000 claims description 12
- 235000019371 penicillin G benzathine Nutrition 0.000 claims description 12
- 241000606125 Bacteroides Species 0.000 claims description 11
- 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 description 11
- 229960004086 ceftibuten Drugs 0.000 claims description 11
- 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 description 11
- 229960004755 ceftriaxone Drugs 0.000 claims description 11
- 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 description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 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 description 11
- 229960002182 imipenem Drugs 0.000 claims description 11
- 150000002771 monosaccharide derivatives Chemical class 0.000 claims description 11
- 229930182555 Penicillin Natural products 0.000 claims description 10
- 241000589516 Pseudomonas Species 0.000 claims description 10
- 238000009826 distribution Methods 0.000 claims description 10
- 150000002772 monosaccharides Chemical class 0.000 claims description 10
- 229940049954 penicillin Drugs 0.000 claims description 10
- 229960001668 cefuroxime Drugs 0.000 claims description 9
- 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 description 9
- 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 description 9
- 229960002260 meropenem Drugs 0.000 claims description 9
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 8
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 229960003022 amoxicillin Drugs 0.000 claims description 8
- 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 description 8
- 229960000895 doripenem Drugs 0.000 claims description 8
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 claims description 8
- 229940056360 penicillin g Drugs 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 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 description 7
- 239000003242 anti bacterial agent Substances 0.000 claims description 7
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 7
- 229960000484 ceftazidime Drugs 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229950011346 panipenem Drugs 0.000 claims description 7
- JETQIUPBHQNHNZ-NJBDSQKTSA-N (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[[(2r)-2-phenyl-2-sulfoacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound C1([C@H](C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)S(O)(=O)=O)=CC=CC=C1 JETQIUPBHQNHNZ-NJBDSQKTSA-N 0.000 claims description 6
- LZKPUSJSJVEXAW-WDXSGGTDSA-N (4s,5r,6s)-3-[7-[1-(2-amino-2-oxoethyl)pyridin-1-ium-3-carbonyl]imidazo[5,1-b][1,3]thiazol-2-yl]-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C([O-])=O)=O)[C@H](O)C)C(SC1=2)=CN1C=NC=2C(=O)C1=CC=C[N+](CC(N)=O)=C1 LZKPUSJSJVEXAW-WDXSGGTDSA-N 0.000 claims description 6
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 6
- MZAGXDHQGXUDDX-JSRXJHBZSA-N (e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/C(N)=O MZAGXDHQGXUDDX-JSRXJHBZSA-N 0.000 claims description 6
- 241000894006 Bacteria Species 0.000 claims description 6
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 6
- 229930195708 Penicillin V Natural products 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 241000607768 Shigella Species 0.000 claims description 6
- 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 description 6
- 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 description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 229960002699 bacampicillin Drugs 0.000 claims description 6
- PFOLLRNADZZWEX-FFGRCDKISA-N bacampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)[C@H](C(S3)(C)C)C(=O)OC(C)OC(=O)OCC)=CC=CC=C1 PFOLLRNADZZWEX-FFGRCDKISA-N 0.000 claims description 6
- 229960003669 carbenicillin Drugs 0.000 claims description 6
- 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 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 229940056367 penicillin v Drugs 0.000 claims description 6
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 claims description 6
- 229960004932 sulbenicillin Drugs 0.000 claims description 6
- YWKJNRNSJKEFMK-PQFQYKRASA-N (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(5,6,7,8-tetrahydroquinolin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound N([C@@H]1C(N2C(=C(C[N+]=3C=4CCCCC=4C=CC=3)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 YWKJNRNSJKEFMK-PQFQYKRASA-N 0.000 claims description 5
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 5
- QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 claims description 5
- 241000588914 Enterobacter Species 0.000 claims description 5
- 241000588747 Klebsiella pneumoniae Species 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 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 description 5
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims description 5
- 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 description 5
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 5
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 claims description 5
- 241000191940 Staphylococcus Species 0.000 claims description 5
- 229960003866 cefaloridine Drugs 0.000 claims description 5
- 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 description 5
- 229960000603 cefalotin Drugs 0.000 claims description 5
- 229950009592 cefquinome Drugs 0.000 claims description 5
- ZBHXIWJRIFEVQY-IHMPYVIRSA-N ceftiofur 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=1CSC(=O)C1=CC=CO1 ZBHXIWJRIFEVQY-IHMPYVIRSA-N 0.000 claims description 5
- 229960005229 ceftiofur Drugs 0.000 claims description 5
- 229940106164 cephalexin Drugs 0.000 claims description 5
- 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 description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229960003194 meglumine Drugs 0.000 claims description 5
- 229960003085 meticillin Drugs 0.000 claims description 5
- UWYHMGVUTGAWSP-JKIFEVAISA-N oxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1 UWYHMGVUTGAWSP-JKIFEVAISA-N 0.000 claims description 5
- 229960001019 oxacillin Drugs 0.000 claims description 5
- 229960002292 piperacillin Drugs 0.000 claims description 5
- 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 description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
- 229960001114 temocillin Drugs 0.000 claims description 5
- BVCKFLJARNKCSS-DWPRYXJFSA-N temocillin Chemical compound N([C@]1(OC)C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C(C(O)=O)C=1C=CSC=1 BVCKFLJARNKCSS-DWPRYXJFSA-N 0.000 claims description 5
- 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 description 5
- 229950010206 tigemonam Drugs 0.000 claims description 5
- 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 description 4
- 241000589876 Campylobacter Species 0.000 claims description 4
- 241000589877 Campylobacter coli Species 0.000 claims description 4
- 241000194032 Enterococcus faecalis Species 0.000 claims description 4
- 241000588724 Escherichia coli Species 0.000 claims description 4
- 241000606790 Haemophilus Species 0.000 claims description 4
- 241000590002 Helicobacter pylori Species 0.000 claims description 4
- 241000589242 Legionella pneumophila Species 0.000 claims description 4
- 241000186779 Listeria monocytogenes Species 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 241000588767 Proteus vulgaris Species 0.000 claims description 4
- 241000168225 Pseudomonas alcaligenes Species 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- 241000607142 Salmonella Species 0.000 claims description 4
- 229920002684 Sepharose Polymers 0.000 claims description 4
- 241000607720 Serratia Species 0.000 claims description 4
- 241000191967 Staphylococcus aureus Species 0.000 claims description 4
- 241000191963 Staphylococcus epidermidis Species 0.000 claims description 4
- 241000194017 Streptococcus Species 0.000 claims description 4
- 241000607626 Vibrio cholerae Species 0.000 claims description 4
- 229960000723 ampicillin Drugs 0.000 claims description 4
- 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 description 4
- 239000003429 antifungal agent Substances 0.000 claims description 4
- 229940121375 antifungal agent Drugs 0.000 claims description 4
- FUBBGQLTSCSAON-PBFPGSCMSA-N cefaloglycin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 FUBBGQLTSCSAON-PBFPGSCMSA-N 0.000 claims description 4
- 229950004030 cefaloglycin Drugs 0.000 claims description 4
- 229960002129 cefixime Drugs 0.000 claims description 4
- 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 description 4
- 229940032049 enterococcus faecalis Drugs 0.000 claims description 4
- 229940037467 helicobacter pylori Drugs 0.000 claims description 4
- 229940115932 legionella pneumophila Drugs 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 229940007042 proteus vulgaris Drugs 0.000 claims description 4
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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-
2015
- 2015-05-18 KR KR1020167035427A patent/KR20170007448A/ko not_active Withdrawn
- 2015-05-18 JP JP2016568679A patent/JP6672176B2/ja active Active
- 2015-05-18 EP EP15796968.4A patent/EP3145936B1/en active Active
- 2015-05-18 AU AU2015264418A patent/AU2015264418A1/en not_active Abandoned
- 2015-05-18 CA CA2947041A patent/CA2947041A1/en not_active Abandoned
- 2015-05-18 EA EA201691988A patent/EA201691988A1/ru unknown
- 2015-05-18 MX MX2016015093A patent/MX2016015093A/es unknown
- 2015-05-18 WO PCT/US2015/031400 patent/WO2015179308A1/en not_active Ceased
- 2015-05-18 CN CN201580026757.0A patent/CN106459096B/zh active Active
- 2015-05-18 US US15/312,173 patent/US9963467B2/en active Active
- 2015-05-18 BR BR112016026291A patent/BR112016026291A2/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP3145936B1 (en) | 2020-09-30 |
| EA201691988A1 (ru) | 2017-06-30 |
| BR112016026291A2 (pt) | 2017-08-15 |
| WO2015179308A1 (en) | 2015-11-26 |
| CN106459096B (zh) | 2019-03-08 |
| US9963467B2 (en) | 2018-05-08 |
| US20170088561A1 (en) | 2017-03-30 |
| JP2017517508A (ja) | 2017-06-29 |
| EP3145936A1 (en) | 2017-03-29 |
| JP6672176B2 (ja) | 2020-03-25 |
| CN106459096A (zh) | 2017-02-22 |
| EP3145936A4 (en) | 2018-01-17 |
| MX2016015093A (es) | 2017-03-27 |
| CA2947041A1 (en) | 2015-11-26 |
| AU2015264418A1 (en) | 2016-11-10 |
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