JP6672176B2 - ボロン酸誘導体およびその治療的使用 - Google Patents
ボロン酸誘導体およびその治療的使用 Download PDFInfo
- Publication number
- JP6672176B2 JP6672176B2 JP2016568679A JP2016568679A JP6672176B2 JP 6672176 B2 JP6672176 B2 JP 6672176B2 JP 2016568679 A JP2016568679 A JP 2016568679A JP 2016568679 A JP2016568679 A JP 2016568679A JP 6672176 B2 JP6672176 B2 JP 6672176B2
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- JP
- Japan
- Prior art keywords
- alkyl
- amino
- group
- hydroxy
- halogen
- 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.)
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- 150000001642 boronic acid derivatives Chemical class 0.000 title description 8
- 230000001225 therapeutic effect Effects 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 359
- -1 hydroxy Chemical group 0.000 claims description 248
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 143
- 125000001424 substituent group Chemical group 0.000 claims description 143
- 229910052736 halogen Chemical group 0.000 claims description 142
- 150000002367 halogens Chemical group 0.000 claims description 140
- 239000000203 mixture Substances 0.000 claims description 112
- 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 108
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 92
- 125000003118 aryl group Chemical group 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 77
- 229910052739 hydrogen Inorganic materials 0.000 claims description 68
- 239000001257 hydrogen Substances 0.000 claims description 68
- 150000001540 azides Chemical group 0.000 claims description 63
- 125000000623 heterocyclic group Chemical group 0.000 claims description 62
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 61
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 50
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
- 239000003795 chemical substances by application Substances 0.000 claims description 40
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical group [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims description 33
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 31
- 239000000651 prodrug Substances 0.000 claims description 30
- 229940002612 prodrug Drugs 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 30
- 239000008194 pharmaceutical composition Substances 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 23
- 229960003644 aztreonam Drugs 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 18
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 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 description 16
- 229960003169 biapenem Drugs 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 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
- 208000035143 Bacterial infection Diseases 0.000 claims description 14
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 13
- 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 11
- 229950010206 tigemonam Drugs 0.000 claims description 11
- 150000003952 β-lactams Chemical group 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 9
- 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 9
- 229960002182 imipenem Drugs 0.000 claims description 9
- 239000003242 anti bacterial agent Substances 0.000 claims description 8
- 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 8
- 229960002260 meropenem Drugs 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 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 description 7
- 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 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 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 7
- 229960000895 doripenem Drugs 0.000 claims description 7
- 229960002770 ertapenem Drugs 0.000 claims description 7
- 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
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 6
- 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 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000004599 antimicrobial Substances 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 229950011346 panipenem Drugs 0.000 claims description 6
- 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
- 230000000844 anti-bacterial effect Effects 0.000 claims description 5
- 230000000845 anti-microbial effect Effects 0.000 claims description 5
- 229940121375 antifungal agent Drugs 0.000 claims description 5
- 239000003429 antifungal agent Substances 0.000 claims description 5
- 229960000484 ceftazidime Drugs 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229960003194 meglumine Drugs 0.000 claims description 5
- 150000003536 tetrazoles Chemical class 0.000 claims description 5
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical group [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 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
- GXXLUDOKHXEFBQ-YJFSRANCSA-N (4r,5s,6s)-3-[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)SC(C1)CN1C1=NCCS1 GXXLUDOKHXEFBQ-YJFSRANCSA-N 0.000 claims description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 4
- 239000000043 antiallergic agent Substances 0.000 claims description 4
- 239000003443 antiviral agent Substances 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 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
- OMAFFHIGWTVZOH-UHFFFAOYSA-N 1-methyltetrazole Chemical compound CN1C=NN=N1 OMAFFHIGWTVZOH-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 230000000843 anti-fungal effect Effects 0.000 claims description 3
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 3
- 230000000840 anti-viral effect Effects 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 claims description 2
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 2
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 2
- JWAWEQBUZOGIBZ-UHFFFAOYSA-N 1-methyltriazole Chemical compound CN1C=CN=N1 JWAWEQBUZOGIBZ-UHFFFAOYSA-N 0.000 claims description 2
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 claims description 2
- QRZMXADUXZADTF-UHFFFAOYSA-N 4-aminoimidazole Chemical compound NC1=CNC=N1 QRZMXADUXZADTF-UHFFFAOYSA-N 0.000 claims description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 2
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims description 2
- 241000257303 Hymenoptera Species 0.000 claims description 2
- 241001024304 Mino Species 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- 102000013566 Plasminogen Human genes 0.000 claims description 2
- 108010051456 Plasminogen Proteins 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims description 2
- 229950003476 aminothiazole Drugs 0.000 claims description 2
- 230000001548 androgenic effect Effects 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 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 3
- 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 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 139
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
- 239000000243 solution Substances 0.000 description 102
- 238000000034 method Methods 0.000 description 60
- 230000015572 biosynthetic process Effects 0.000 description 59
- 238000003786 synthesis reaction Methods 0.000 description 55
- 238000005481 NMR spectroscopy Methods 0.000 description 50
- 235000019439 ethyl acetate Nutrition 0.000 description 42
- 125000004432 carbon atom Chemical group C* 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 125000002947 alkylene group Chemical group 0.000 description 27
- 239000007787 solid Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 22
- 238000004440 column chromatography Methods 0.000 description 22
- 239000003921 oil Substances 0.000 description 22
- 235000019198 oils Nutrition 0.000 description 22
- 125000004122 cyclic group Chemical group 0.000 description 20
- 102000006635 beta-lactamase Human genes 0.000 description 19
- 238000011282 treatment Methods 0.000 description 19
- HGTBAIVLETUVCG-UHFFFAOYSA-N (methylthio)acetic acid Chemical compound CSCC(O)=O HGTBAIVLETUVCG-UHFFFAOYSA-N 0.000 description 18
- 125000006239 protecting group Chemical group 0.000 description 18
- WZPBZJONDBGPKJ-VEHQQRBSSA-L 2-[(z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(2s,3s)-2-methyl-4-oxo-1-sulfonatoazetidin-3-yl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoate 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(N)=N1 WZPBZJONDBGPKJ-VEHQQRBSSA-L 0.000 description 17
- 0 *[n]1nnnc1S Chemical compound *[n]1nnnc1S 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 125000000304 alkynyl group Chemical group 0.000 description 15
- 125000004429 atom Chemical group 0.000 description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 108020004256 Beta-lactamase Proteins 0.000 description 13
- 125000004450 alkenylene group Chemical group 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000003814 drug Substances 0.000 description 12
- 125000005843 halogen group Chemical group 0.000 description 12
- 125000004404 heteroalkyl group Chemical group 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- 239000002552 dosage form Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- BSIMZHVOQZIAOY-SCSAIBSYSA-N 1-carbapenem-3-carboxylic acid Chemical compound OC(=O)C1=CC[C@@H]2CC(=O)N12 BSIMZHVOQZIAOY-SCSAIBSYSA-N 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000003937 drug carrier Substances 0.000 description 9
- 238000001990 intravenous administration Methods 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- 150000002771 monosaccharide derivatives Chemical class 0.000 description 9
- 150000002772 monosaccharides Chemical class 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 238000006467 substitution reaction Methods 0.000 description 9
- JVVRCYWZTJLJSG-UHFFFAOYSA-N 4-dimethylaminophenol Chemical compound CN(C)C1=CC=C(O)C=C1 JVVRCYWZTJLJSG-UHFFFAOYSA-N 0.000 description 8
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-dimethylaminopyridine Substances CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- 241000606125 Bacteroides Species 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- 239000003781 beta lactamase inhibitor Substances 0.000 description 8
- 229940126813 beta-lactamase inhibitor Drugs 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 230000000670 limiting effect Effects 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
- 229930186147 Cephalosporin Natural products 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 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 description 7
- 239000002253 acid Substances 0.000 description 7
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 7
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Classifications
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
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- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
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| EP2941246A4 (en) | 2013-01-04 | 2016-12-21 | Rempex Pharmaceuticals Inc | BORONIC ACID DERIVATIVES AND THEIR THERAPEUTIC USES |
| CN105101970B (zh) * | 2013-01-10 | 2018-11-20 | 维纳拓尔斯制药公司 | β-内酰胺酶抑制剂 |
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| ES2985626T3 (es) | 2014-05-05 | 2024-11-06 | Melinta Therapeutics Inc | Sales y polimorfos de derivados cíclicos de éster de ácido borónico y usos terapéuticos de los mismos |
| SMT201900611T1 (it) | 2014-05-05 | 2020-01-14 | Rempex Pharmaceuticals Inc | Sintesi di sali boronati e usi degli stessi |
| US9511142B2 (en) | 2014-06-11 | 2016-12-06 | VenatoRx Pharmaceuticals, Inc. | Beta-lactamase inhibitors |
| ES2874579T3 (es) | 2014-06-11 | 2021-11-05 | Venatorx Pharmaceuticals Inc | Inhibidores de betalactamasa |
| US20150361108A1 (en) * | 2014-06-11 | 2015-12-17 | VenatoRx Pharmaceuticals, Inc. | Orally bioavailable beta-lactamase inhibitors |
| MX2016016666A (es) * | 2014-07-01 | 2017-08-08 | Rempex Pharmaceuticals Inc | Derivados de acido boronico y usos terapeuticos de los mismos. |
| US10662205B2 (en) | 2014-11-18 | 2020-05-26 | Qpex Biopharma, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| WO2016149393A1 (en) | 2015-03-17 | 2016-09-22 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| BR112017028448A2 (pt) | 2015-07-02 | 2018-08-28 | Horizon Orphan Llc | análogos de cisteamina resistentes a ado e usos dos mesmos |
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| WO2017100537A1 (en) | 2015-12-10 | 2017-06-15 | VenatoRx Pharmaceuticals, Inc. | Beta-lactamase inhibitors |
| DK3478693T3 (da) | 2016-06-30 | 2021-09-20 | Qpex Biopharma Inc | Boronsyrederivater og terapeutiske anvendelser deraf |
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| JOP20190188A1 (ar) | 2017-02-01 | 2019-08-01 | Rempex Pharmaceuticals Inc | جهاز وعملية تدفق مستمرة لإنتاج مشتق حمض بورونيك |
| WO2018199291A1 (ja) * | 2017-04-28 | 2018-11-01 | 大日本住友製薬株式会社 | ヘテロ環誘導体 |
| EP3630782A4 (en) | 2017-05-26 | 2021-03-03 | Venatorx Pharmaceuticals, Inc. | Penicillin-binding protein inhibitors |
| WO2018218154A1 (en) | 2017-05-26 | 2018-11-29 | VenatoRx Pharmaceuticals, Inc. | Penicillin-binding protein inhibitors |
| WO2019009369A1 (ja) * | 2017-07-06 | 2019-01-10 | 大日本住友製薬株式会社 | イミン誘導体 |
| TW201906616A (zh) * | 2017-07-06 | 2019-02-16 | 日商大日本住友製藥股份有限公司 | 醯胺衍生物 |
| JP7377545B2 (ja) | 2017-10-11 | 2023-11-10 | キューペックス バイオファーマ， インコーポレイテッド | ボロン酸誘導体およびその合成 |
| AU2019256351B2 (en) | 2018-04-20 | 2024-02-29 | Qpex Biopharma, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| CN118638140A (zh) * | 2018-04-27 | 2024-09-13 | 住友制药株式会社 | 氧代取代化合物 |
| EP3802551A4 (en) | 2018-05-25 | 2022-03-02 | Venatorx Pharmaceuticals, Inc. | Penicillin-binding protein inhibitors |
| KR20210097758A (ko) * | 2018-11-29 | 2021-08-09 | 베나토알엑스 파마슈티컬스, 인크. | 베타-락타마제 억제제를 포함하는 조합 조성물 및 이의 용도 |
| WO2020138499A1 (ja) * | 2018-12-28 | 2020-07-02 | 大日本住友製薬株式会社 | アルキル置換化合物 |
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| JP7550421B2 (ja) * | 2019-10-25 | 2024-09-13 | 住友ファーマ株式会社 | オキソ置換化合物からなる医薬 |
| EP4049680A4 (en) * | 2019-10-25 | 2024-01-10 | Sumitomo Pharma Co., Ltd. | NEW SUBSTITUTED CONDENSED RING CONNECTION |
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| US4194047A (en) | 1975-11-21 | 1980-03-18 | Merck & Co., Inc. | Substituted N-methylene derivatives of thienamycin |
| US4260543A (en) | 1978-07-03 | 1981-04-07 | Merck & Co., Inc. | Crystalline N-formimidoyl thienamycin |
| US4409214A (en) | 1979-11-19 | 1983-10-11 | Fujisawa Pharmaceutical, Co., Ltd. | 7-Acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof |
| FR2573070B1 (fr) | 1984-11-13 | 1987-01-30 | Rhone Poulenc Sante | Procede de preparation de composes carbonyles |
| US4783443A (en) | 1986-03-03 | 1988-11-08 | The University Of Chicago | Amino acyl cephalosporin derivatives |
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2015
- 2015-05-18 CN CN201580026757.0A patent/CN106459096B/zh active Active
- 2015-05-18 AU AU2015264418A patent/AU2015264418A1/en not_active Abandoned
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| EP3145936B1 (en) | 2020-09-30 |
| CN106459096A (zh) | 2017-02-22 |
| AU2015264418A1 (en) | 2016-11-10 |
| BR112016026291A2 (pt) | 2017-08-15 |
| EA201691988A1 (ru) | 2017-06-30 |
| CA2947041A1 (en) | 2015-11-26 |
| US20170088561A1 (en) | 2017-03-30 |
| JP2017517508A (ja) | 2017-06-29 |
| EP3145936A1 (en) | 2017-03-29 |
| CN106459096B (zh) | 2019-03-08 |
| WO2015179308A1 (en) | 2015-11-26 |
| KR20170007448A (ko) | 2017-01-18 |
| MX2016015093A (es) | 2017-03-27 |
| US9963467B2 (en) | 2018-05-08 |
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