JP2011507959A5 - - Google Patents
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- JP2011507959A5 JP2011507959A5 JP2010540728A JP2010540728A JP2011507959A5 JP 2011507959 A5 JP2011507959 A5 JP 2011507959A5 JP 2010540728 A JP2010540728 A JP 2010540728A JP 2010540728 A JP2010540728 A JP 2010540728A JP 2011507959 A5 JP2011507959 A5 JP 2011507959A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- alkoxy
- group
- aryl
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 48
- 125000001072 heteroaryl group Chemical group 0.000 claims 43
- 229910052739 hydrogen Inorganic materials 0.000 claims 41
- 239000001257 hydrogen Substances 0.000 claims 41
- 229910052736 halogen Inorganic materials 0.000 claims 38
- 150000002367 halogens Chemical class 0.000 claims 38
- 150000001875 compounds Chemical class 0.000 claims 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 31
- 125000003118 aryl group Chemical group 0.000 claims 30
- 125000001424 substituent group Chemical group 0.000 claims 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 28
- 125000003107 substituted aryl group Chemical group 0.000 claims 24
- 150000002431 hydrogen Chemical class 0.000 claims 23
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims 20
- 229910052799 carbon Inorganic materials 0.000 claims 18
- 125000004429 atom Chemical group 0.000 claims 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 15
- 125000003342 alkenyl group Chemical group 0.000 claims 14
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 13
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 12
- 125000000304 alkynyl group Chemical group 0.000 claims 11
- 229940024606 amino acid Drugs 0.000 claims 11
- 235000001014 amino acid Nutrition 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 150000001413 amino acids Chemical class 0.000 claims 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 9
- 125000003277 amino group Chemical group 0.000 claims 8
- 150000003138 primary alcohols Chemical class 0.000 claims 8
- 230000010933 acylation Effects 0.000 claims 7
- 238000005917 acylation reaction Methods 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000002252 acyl group Chemical group 0.000 claims 6
- 125000003282 alkyl amino group Chemical group 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 150000002772 monosaccharides Chemical class 0.000 claims 6
- 150000003141 primary amines Chemical class 0.000 claims 6
- -1 Boc-amino Chemical group 0.000 claims 5
- 125000004104 aryloxy group Chemical group 0.000 claims 5
- 208000015181 infectious disease Diseases 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 229930186147 Cephalosporin Natural products 0.000 claims 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 4
- 229940124587 cephalosporin Drugs 0.000 claims 4
- 150000001780 cephalosporins Chemical class 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000001350 alkyl halides Chemical class 0.000 claims 3
- 125000005418 aryl aryl group Chemical group 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 2
- 241000894006 Bacteria Species 0.000 claims 2
- 201000001178 Bacterial Pneumonia Diseases 0.000 claims 2
- 208000035143 Bacterial infection Diseases 0.000 claims 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 2
- NUAQIRUAZSJTAI-YRPZDAAMSA-N O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@H](N)CC(C)C)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@H](N)CC(C)C)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 NUAQIRUAZSJTAI-YRPZDAAMSA-N 0.000 claims 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 108010053950 Teicoplanin Proteins 0.000 claims 2
- 108010059993 Vancomycin Proteins 0.000 claims 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 2
- 150000001299 aldehydes Chemical class 0.000 claims 2
- 230000029936 alkylation Effects 0.000 claims 2
- 238000005804 alkylation reaction Methods 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 229960001230 asparagine Drugs 0.000 claims 2
- 235000009582 asparagine Nutrition 0.000 claims 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- DDTDNCYHLGRFBM-YZEKDTGTSA-N chembl2367892 Chemical compound CC(=O)N[C@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1O[C@@H]([C@H]1C(N[C@@H](C2=CC(O)=CC(O[C@@H]3[C@H]([C@H](O)[C@H](O)[C@@H](CO)O3)O)=C2C=2C(O)=CC=C(C=2)[C@@H](NC(=O)[C@@H]2NC(=O)[C@@H]3C=4C=C(O)C=C(C=4)OC=4C(O)=CC=C(C=4)[C@@H](N)C(=O)N[C@H](CC=4C=C(Cl)C(O5)=CC=4)C(=O)N3)C(=O)N1)C(O)=O)=O)C(C=C1Cl)=CC=C1OC1=C(O[C@H]3[C@H]([C@@H](O)[C@H](O)[C@H](CO)O3)NC(C)=O)C5=CC2=C1 DDTDNCYHLGRFBM-YZEKDTGTSA-N 0.000 claims 2
- 229960002488 dalbavancin Drugs 0.000 claims 2
- 108700009376 dalbavancin Proteins 0.000 claims 2
- 150000002466 imines Chemical class 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims 2
- VHFGEBVPHAGQPI-MYYQHNLBSA-N oritavancin Chemical compound O([C@@H]1C2=CC=C(C(=C2)Cl)OC=2C=C3C=C(C=2O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O[C@@H]2O[C@@H](C)[C@H](O)[C@@](C)(NCC=4C=CC(=CC=4)C=4C=CC(Cl)=CC=4)C2)OC2=CC=C(C=C2Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]2C(=O)N[C@@H]1C(N[C@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@@H](O)[C@H](C)O1 VHFGEBVPHAGQPI-MYYQHNLBSA-N 0.000 claims 2
- 229960001607 oritavancin Drugs 0.000 claims 2
- 108010006945 oritavancin Proteins 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 125000001749 primary amide group Chemical group 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 238000006268 reductive amination reaction Methods 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 229960001608 teicoplanin Drugs 0.000 claims 2
- ONUMZHGUFYIKPM-MXNFEBESSA-N telavancin Chemical compound O1[C@@H](C)[C@@H](O)[C@](NCCNCCCCCCCCCC)(C)C[C@@H]1O[C@H]1[C@H](OC=2C3=CC=4[C@H](C(N[C@H]5C(=O)N[C@H](C(N[C@@H](C6=CC(O)=C(CNCP(O)(O)=O)C(O)=C6C=6C(O)=CC=C5C=6)C(O)=O)=O)[C@H](O)C5=CC=C(C(=C5)Cl)O3)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](NC(=O)[C@@H](CC(C)C)NC)[C@H](O)C3=CC=C(C(=C3)Cl)OC=2C=4)O[C@H](CO)[C@@H](O)[C@@H]1O ONUMZHGUFYIKPM-MXNFEBESSA-N 0.000 claims 2
- 229960005240 telavancin Drugs 0.000 claims 2
- 108010089019 telavancin Proteins 0.000 claims 2
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 claims 2
- 229960003165 vancomycin Drugs 0.000 claims 2
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 claims 2
- KGPGQDLTDHGEGT-JCIKCJKQSA-N zeven Chemical compound C=1C([C@@H]2C(=O)N[C@H](C(N[C@H](C3=CC(O)=C4)C(=O)NCCCN(C)C)=O)[C@H](O)C5=CC=C(C(=C5)Cl)OC=5C=C6C=C(C=5O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@H](O5)C(O)=O)NC(=O)CCCCCCCCC(C)C)OC5=CC=C(C=C5)C[C@@H]5C(=O)N[C@H](C(N[C@H]6C(=O)N2)=O)C=2C(Cl)=C(O)C=C(C=2)OC=2C(O)=CC=C(C=2)[C@H](C(N5)=O)NC)=CC=C(O)C=1C3=C4O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O KGPGQDLTDHGEGT-JCIKCJKQSA-N 0.000 claims 2
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
- 208000031729 Bacteremia Diseases 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin 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=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 claims 1
- JUZNIMUFDBIJCM-ANEDZVCMSA-N Invanz Chemical compound O=C([C@H]1NC[C@H](C1)SC=1[C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)NC1=CC=CC(C(O)=O)=C1 JUZNIMUFDBIJCM-ANEDZVCMSA-N 0.000 claims 1
- 241000124008 Mammalia 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
- FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 claims 1
- 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 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
- 150000001345 alkine derivatives Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 239000003782 beta lactam antibiotic agent Substances 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000006352 cycloaddition reaction Methods 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- YFAGHNZHGGCZAX-JKIFEVAISA-N dicloxacillin 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=C(Cl)C=CC=C1Cl YFAGHNZHGGCZAX-JKIFEVAISA-N 0.000 claims 1
- 229960001585 dicloxacillin Drugs 0.000 claims 1
- 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 1
- 229960000895 doripenem Drugs 0.000 claims 1
- UECIPBUIMXSXEI-BNSVOVDNSA-N eremomycin Chemical compound O([C@@H]1C2=CC=C(C=C2)OC=2C=C3C=C(C=2O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O[C@@H]2O[C@@H](C)[C@H](O)[C@@](C)(N)C2)OC2=CC=C(C=C2Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]2C(=O)N[C@@H]1C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@@H](O)[C@H](C)O1 UECIPBUIMXSXEI-BNSVOVDNSA-N 0.000 claims 1
- 108010013356 eremomycin Proteins 0.000 claims 1
- UECIPBUIMXSXEI-UHFFFAOYSA-N eremomycin Natural products C=1C2=CC=C(O)C=1C1=C(O)C=C(O)C=C1C(C(O)=O)NC(=O)C1NC(=O)C2NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC(C=3OC4C(C(O)C(O)C(CO)O4)OC4OC(C)C(O)C(C)(N)C4)=CC2=CC=3OC(C=C2)=CC=C2C1OC1CC(C)(N)C(O)C(C)O1 UECIPBUIMXSXEI-UHFFFAOYSA-N 0.000 claims 1
- 229960002770 ertapenem Drugs 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
- 229960000379 faropenem Drugs 0.000 claims 1
- 229960004273 floxacillin Drugs 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 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
- 229960002182 imipenem Drugs 0.000 claims 1
- 238000007912 intraperitoneal administration Methods 0.000 claims 1
- DQDCGTUHSVXZIS-UHFFFAOYSA-N iodobenzene;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.IC1=CC=CC=C1 DQDCGTUHSVXZIS-UHFFFAOYSA-N 0.000 claims 1
- 239000012948 isocyanate Substances 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
- 229960002260 meropenem Drugs 0.000 claims 1
- 229960003085 meticillin Drugs 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 229950011346 panipenem Drugs 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 239000002132 β-lactam antibiotic Substances 0.000 claims 1
- 229940124586 β-lactam antibiotics Drugs 0.000 claims 1
- 0 C*(*)CCNC=* Chemical compound C*(*)CCNC=* 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1678307P | 2007-12-26 | 2007-12-26 | |
| PCT/US2008/085716 WO2009085562A1 (en) | 2007-12-26 | 2008-12-05 | Novel semi-synthetic glycopeptides as antibacterial agents |
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| JP2011507959A JP2011507959A (ja) | 2011-03-10 |
| JP2011507959A5 true JP2011507959A5 (https=) | 2013-01-24 |
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| US (1) | US20120129763A1 (https=) |
| EP (1) | EP2238102A4 (https=) |
| JP (1) | JP2011507959A (https=) |
| KR (1) | KR20100109936A (https=) |
| CN (1) | CN101959849A (https=) |
| AR (1) | AR071552A1 (https=) |
| AU (1) | AU2008343502A1 (https=) |
| CA (1) | CA2710602A1 (https=) |
| GB (1) | GB2457549B (https=) |
| IL (1) | IL206622A0 (https=) |
| TW (1) | TW200940083A (https=) |
| WO (1) | WO2009085562A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100105607A1 (en) * | 2008-10-24 | 2010-04-29 | Lead Therapeutics, Inc. | Novel semi-synthetic glycopeptides as antibacterial agents |
| GB2465863A (en) * | 2008-12-05 | 2010-06-09 | Lead Therapeutics Inc | Semi-synthetic heptapeptidic glycopeptides for the treatment of bacterial infections |
| WO2011140009A1 (en) * | 2010-05-04 | 2011-11-10 | Biomarin Pharmaceutical Inc. | Methods of using semi-synthetic glycopeptides as antibacterial agents |
| CN103897040B (zh) * | 2012-12-27 | 2018-05-22 | 浙江医药股份有限公司新昌制药厂 | 新型糖肽类化合物或其药用盐及其制备方法、以及药物组合物和用途 |
| CN105585617A (zh) * | 2016-03-24 | 2016-05-18 | 中国医学科学院医药生物技术研究所 | 去甲万古霉素衍生物及其制备纯化方法 |
| CN107619433B (zh) * | 2016-07-15 | 2023-03-17 | 上海来益生物药物研究开发中心有限责任公司 | 糖肽类衍生物及其药学可接受的盐、制备方法和应用 |
| GB2577420B (en) * | 2017-05-22 | 2022-07-06 | Insmed Inc | Glycopeptide derivative compounds and uses thereof |
| CN109422800A (zh) * | 2017-08-22 | 2019-03-05 | 复旦大学 | 抗革兰氏阳性菌季铵盐糖肽类化合物及其药用用途 |
| CN108948157B (zh) * | 2018-07-31 | 2021-08-03 | 丽珠集团新北江制药股份有限公司 | 一种制备特拉万星的方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0662674B2 (ja) * | 1985-01-11 | 1994-08-17 | 三共株式会社 | 抗生物質クロロポリスポリンｂまたはｃ |
| US4643987A (en) * | 1985-08-14 | 1987-02-17 | Eli Lilly And Company | Modified glycopeptides |
| DE69908819T2 (de) * | 1998-12-23 | 2004-05-06 | Theravance, Inc., South San Francisco | Glycopeptid-derivate und pharmazeutische zusammensetzungen, die sie enthalten |
| US6699836B2 (en) * | 1999-04-02 | 2004-03-02 | The Trustees Of Princeton University | Vancomycin analogs |
| JP4381531B2 (ja) * | 1999-12-08 | 2009-12-09 | 塩野義製薬株式会社 | グリコペプチド誘導体 |
| MXPA02006029A (es) * | 1999-12-15 | 2004-08-23 | Cubist Pharm Inc | Lipopeptidos novedosos como agentes antibacterianos. |
| US6770621B2 (en) * | 2000-05-02 | 2004-08-03 | Theravance, Inc. | Polyacid glycopeptide derivatives |
| UA75083C2 (uk) * | 2000-06-22 | 2006-03-15 | Тераванс, Інк. | Похідні глікопептидфосфонатів |
| US20030008812A1 (en) * | 2001-02-02 | 2003-01-09 | Christensen Burton G. | Glycopeptide derivatives |
| TWI233932B (en) * | 2001-08-24 | 2005-06-11 | Theravance Inc | Process for purifying glycopeptide phosphonate derivatives |
| US7521418B2 (en) * | 2003-05-27 | 2009-04-21 | Theravance, Inc. | Use of a polyene macrolide antifungal agent in combination with a glycopeptide antibacterial agent |
| WO2005007162A1 (en) * | 2003-07-10 | 2005-01-27 | Vertex Pharmaceuticals Incorporated | Compounds augmenting the activity of antibacterial agents |
| ATE381957T1 (de) * | 2003-07-22 | 2008-01-15 | Theravance Inc | Verwendung eines antimykotischen echinocandin- mittels in kombination mit einem antibakteriellen glycopeptid-mittel |
| US20070185015A1 (en) * | 2005-02-28 | 2007-08-09 | Chiron Corporation and North China Pharmaceutical Corporation | Semi-synthetic desmethyl-vancomycin-based glycopeptides with antibiotic activity |
| US7632918B2 (en) * | 2005-02-28 | 2009-12-15 | Novartis Vaccines And Diagnostics, Inc. | Semi-synthetic glycopeptides with antibiotic activity |
| US7368422B2 (en) * | 2005-02-28 | 2008-05-06 | Novartis Vaccines And Diagnostics Inc. | Semi-synthetic rearranged vancomycin/desmethyl-vancomycin-based glycopeptides with antibiotic activity |
| CN1883706A (zh) * | 2006-05-22 | 2006-12-27 | 济南康泉医药科技有限公司 | 一种局部应用的抗生素缓释剂 |
| US8236926B2 (en) * | 2006-09-06 | 2012-08-07 | Wisconsin Alumni Research Foundation | Rapid glycopeptide optimization via neoglycosylation |
-
2008
- 2008-12-05 CN CN2008801275540A patent/CN101959849A/zh active Pending
- 2008-12-05 EP EP08868184A patent/EP2238102A4/en not_active Withdrawn
- 2008-12-05 CA CA2710602A patent/CA2710602A1/en not_active Abandoned
- 2008-12-05 WO PCT/US2008/085716 patent/WO2009085562A1/en not_active Ceased
- 2008-12-05 KR KR1020107016605A patent/KR20100109936A/ko not_active Withdrawn
- 2008-12-05 AU AU2008343502A patent/AU2008343502A1/en not_active Abandoned
- 2008-12-05 JP JP2010540728A patent/JP2011507959A/ja active Pending
- 2008-12-18 TW TW097149455A patent/TW200940083A/zh unknown
- 2008-12-23 GB GB0823463A patent/GB2457549B/en not_active Expired - Fee Related
- 2008-12-23 AR ARP080105718A patent/AR071552A1/es not_active Application Discontinuation
-
2010
- 2010-06-24 IL IL206622A patent/IL206622A0/en unknown
-
2012
- 2012-01-25 US US13/358,374 patent/US20120129763A1/en not_active Abandoned
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