JP2013539751A5 - - Google Patents
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- JP2013539751A5 JP2013539751A5 JP2013529181A JP2013529181A JP2013539751A5 JP 2013539751 A5 JP2013539751 A5 JP 2013539751A5 JP 2013529181 A JP2013529181 A JP 2013529181A JP 2013529181 A JP2013529181 A JP 2013529181A JP 2013539751 A5 JP2013539751 A5 JP 2013539751A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hydrogen
- aryl
- alkoxy
- nitro
- 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.)
- Ceased
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 124
- 229910052739 hydrogen Inorganic materials 0.000 claims description 108
- 239000001257 hydrogen Substances 0.000 claims description 100
- 125000000623 heterocyclic group Chemical group 0.000 claims description 84
- 125000001072 heteroaryl group Chemical group 0.000 claims description 80
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 68
- -1 amino, hydroxyl Chemical group 0.000 claims description 66
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 64
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 56
- 229910052736 halogen Inorganic materials 0.000 claims description 56
- 150000002367 halogens Chemical group 0.000 claims description 56
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 53
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 52
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 52
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 48
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 48
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 150000002431 hydrogen Chemical group 0.000 claims description 43
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 36
- 229910052799 carbon Inorganic materials 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000004429 atom Chemical group 0.000 claims description 25
- 125000002950 monocyclic group Chemical group 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 20
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 20
- 125000002619 bicyclic group Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 241000894006 Bacteria Species 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 208000035143 Bacterial infection Diseases 0.000 claims description 17
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 17
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 241000194017 Streptococcus Species 0.000 claims description 11
- 241000194035 Lactococcus lactis Species 0.000 claims description 10
- 241000191940 Staphylococcus Species 0.000 claims description 10
- 235000014897 Streptococcus lactis Nutrition 0.000 claims description 10
- 208000015181 infectious disease Diseases 0.000 claims description 9
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 8
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims description 8
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 241000589875 Campylobacter jejuni Species 0.000 claims description 6
- 241000186226 Corynebacterium glutamicum Species 0.000 claims description 6
- 241000590002 Helicobacter pylori Species 0.000 claims description 6
- 241001134658 Streptococcus mitis Species 0.000 claims description 6
- 241000193998 Streptococcus pneumoniae Species 0.000 claims description 6
- 241000193996 Streptococcus pyogenes Species 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000003051 glycosyloxy group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229940037467 helicobacter pylori Drugs 0.000 claims description 6
- 230000001717 pathogenic effect Effects 0.000 claims description 6
- 241000191984 Staphylococcus haemolyticus Species 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229940037649 staphylococcus haemolyticus Drugs 0.000 claims description 5
- 125000004001 thioalkyl group Chemical group 0.000 claims description 5
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 4
- 125000006373 (C2-C10) alkyl group Chemical group 0.000 claims description 4
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003147 glycosyl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 4
- 230000004962 physiological condition Effects 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- 241000158504 Rhodococcus hoagii Species 0.000 claims description 3
- 241001147736 Staphylococcus capitis Species 0.000 claims description 3
- 241001147695 Staphylococcus caprae Species 0.000 claims description 3
- 241000191965 Staphylococcus carnosus Species 0.000 claims description 3
- 241000191963 Staphylococcus epidermidis Species 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 2
- 241001524101 Rhodococcus opacus Species 0.000 claims description 2
- 241000607479 Yersinia pestis Species 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000002207 metabolite Substances 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000000651 prodrug Substances 0.000 claims description 2
- 229940002612 prodrug Drugs 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 241000606161 Chlamydia Species 0.000 claims 3
- 241000606153 Chlamydia trachomatis Species 0.000 claims 1
- 241000186227 Corynebacterium diphtheriae Species 0.000 claims 1
- 241000186427 Cutibacterium acnes Species 0.000 claims 1
- 241001147698 Staphylococcus cohnii Species 0.000 claims 1
- 241001301565 Staphylococcus hominis subsp. novobiosepticus Species 0.000 claims 1
- 241001134656 Staphylococcus lugdunensis Species 0.000 claims 1
- 241000194025 Streptococcus oralis Species 0.000 claims 1
- 201000005010 Streptococcus pneumonia Diseases 0.000 claims 1
- 229940038705 chlamydia trachomatis Drugs 0.000 claims 1
- 230000002538 fungal effect Effects 0.000 claims 1
- 229940055019 propionibacterium acne Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 description 45
- 108010087967 type I signal peptidase Proteins 0.000 description 33
- 230000001580 bacterial effect Effects 0.000 description 22
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 21
- 150000001413 amino acids Chemical class 0.000 description 21
- 230000003197 catalytic effect Effects 0.000 description 15
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 14
- 241000192087 Staphylococcus hominis Species 0.000 description 14
- 239000000523 sample Substances 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 9
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 6
- 241001647372 Chlamydia pneumoniae Species 0.000 description 5
- 108010019589 Staphylococcus aureus glutamic acid-specific endopeptidase Proteins 0.000 description 5
- 239000003242 anti bacterial agent Substances 0.000 description 5
- 206010013023 diphtheria Diseases 0.000 description 5
- 201000001371 inclusion conjunctivitis Diseases 0.000 description 5
- 244000052769 pathogen Species 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 5
- 206010044325 trachoma Diseases 0.000 description 5
- 0 C[C@](C(NCC(N(C)[C@@](c(cc1-c(cc(C[C@@](C(O)=O)NC([C@](C)N2)=O)cc3)c3O)ccc1O)C2=O)=O)=O)NC([C@](CO)N(C)C(*)=O)=O Chemical compound C[C@](C(NCC(N(C)[C@@](c(cc1-c(cc(C[C@@](C(O)=O)NC([C@](C)N2)=O)cc3)c3O)ccc1O)C2=O)=O)=O)NC([C@](CO)N(C)C(*)=O)=O 0.000 description 4
- 125000003275 alpha amino acid group Chemical group 0.000 description 4
- 229940088710 antibiotic agent Drugs 0.000 description 4
- 102000039446 nucleic acids Human genes 0.000 description 4
- 108020004707 nucleic acids Proteins 0.000 description 4
- 150000007523 nucleic acids Chemical class 0.000 description 4
- 108091005804 Peptidases Proteins 0.000 description 3
- 102000035195 Peptidases Human genes 0.000 description 3
- 241000607142 Salmonella Species 0.000 description 3
- 241000194042 Streptococcus dysgalactiae Species 0.000 description 3
- 241000282898 Sus scrofa Species 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 235000019833 protease Nutrition 0.000 description 3
- 229940115920 streptococcus dysgalactiae Drugs 0.000 description 3
- 241000588626 Acinetobacter baumannii Species 0.000 description 2
- 241000193738 Bacillus anthracis Species 0.000 description 2
- 241000588832 Bordetella pertussis Species 0.000 description 2
- 241000193163 Clostridioides difficile Species 0.000 description 2
- 241000194032 Enterococcus faecalis Species 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 241000606768 Haemophilus influenzae Species 0.000 description 2
- 241000588747 Klebsiella pneumoniae Species 0.000 description 2
- 241000224016 Plasmodium Species 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 241000193985 Streptococcus agalactiae Species 0.000 description 2
- 241000194019 Streptococcus mutans Species 0.000 description 2
- 241000607626 Vibrio cholerae Species 0.000 description 2
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 description 2
- 229940032049 enterococcus faecalis Drugs 0.000 description 2
- 229940047650 haemophilus influenzae Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- 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 description 1
- 108010001478 Bacitracin Proteins 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 241000588923 Citrobacter Species 0.000 description 1
- 241000588917 Citrobacter koseri Species 0.000 description 1
- 241001478240 Coccus Species 0.000 description 1
- 108010078777 Colistin Proteins 0.000 description 1
- 108010013198 Daptomycin Proteins 0.000 description 1
- 241000186781 Listeria Species 0.000 description 1
- 241000186779 Listeria monocytogenes Species 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- 241000588650 Neisseria meningitidis Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 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 description 1
- 241000607762 Shigella flexneri Species 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940065181 bacillus anthracis Drugs 0.000 description 1
- 229960003071 bacitracin Drugs 0.000 description 1
- 229930184125 bacitracin Natural products 0.000 description 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 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 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 description 1
- 229960005091 chloramphenicol Drugs 0.000 description 1
- 229960003346 colistin Drugs 0.000 description 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 description 1
- 229960005484 daptomycin Drugs 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229940124307 fluoroquinolone Drugs 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 229960003907 linezolid Drugs 0.000 description 1
- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 description 1
- 229940115931 listeria monocytogenes Drugs 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229960003128 mupirocin Drugs 0.000 description 1
- 229930187697 mupirocin Natural products 0.000 description 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 description 1
- 230000035772 mutation Effects 0.000 description 1
- JORAUNFTUVJTNG-BSTBCYLQSA-N n-[(2s)-4-amino-1-[[(2s,3r)-1-[[(2s)-4-amino-1-oxo-1-[[(3s,6s,9s,12s,15r,18s,21s)-6,9,18-tris(2-aminoethyl)-3-[(1r)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-h Chemical compound CC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O.CCC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O JORAUNFTUVJTNG-BSTBCYLQSA-N 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- XDJYMJULXQKGMM-UHFFFAOYSA-N polymyxin E1 Natural products CCC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O XDJYMJULXQKGMM-UHFFFAOYSA-N 0.000 description 1
- KNIWPHSUTGNZST-UHFFFAOYSA-N polymyxin E2 Natural products CC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O KNIWPHSUTGNZST-UHFFFAOYSA-N 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000003910 polypeptide antibiotic agent Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 229960001225 rifampicin Drugs 0.000 description 1
- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38298810P | 2010-09-15 | 2010-09-15 | |
| US61/382,988 | 2010-09-15 | ||
| PCT/US2011/049967 WO2012036907A2 (en) | 2010-09-15 | 2011-08-31 | Broad spectrum antibiotic arylomycin analogs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013539751A JP2013539751A (ja) | 2013-10-28 |
| JP2013539751A5 true JP2013539751A5 (OSRAM) | 2014-10-16 |
Family
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Family Applications (1)
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| JP2013529181A Ceased JP2013539751A (ja) | 2010-09-15 | 2011-08-31 | 広域抗生物質アリロマイシン類縁体 |
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| Country | Link |
|---|---|
| US (1) | US9187524B2 (OSRAM) |
| EP (1) | EP2616093A4 (OSRAM) |
| JP (1) | JP2013539751A (OSRAM) |
| KR (1) | KR20130105659A (OSRAM) |
| CN (1) | CN103209700A (OSRAM) |
| BR (1) | BR112013006265A2 (OSRAM) |
| CA (1) | CA2811295A1 (OSRAM) |
| MX (1) | MX2013003035A (OSRAM) |
| RU (1) | RU2013112483A (OSRAM) |
| WO (1) | WO2012036907A2 (OSRAM) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20130105659A (ko) | 2010-09-15 | 2013-09-25 | 더 스크립스 리서치 인스티튜트 | 광범위 스펙트럼 항생제 아릴로마이신 유사체 |
| US10501493B2 (en) | 2011-05-27 | 2019-12-10 | Rqx Pharmaceuticals, Inc. | Broad spectrum antibiotics |
| 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 |
| CA2892027A1 (en) * | 2012-11-21 | 2014-05-30 | Rqx Pharmaceuticals, Inc. | Macrocyclic broad spectrum antibiotics |
| CN103103261A (zh) * | 2013-01-05 | 2013-05-15 | 张国新 | 检测幽门螺杆菌对克拉霉素耐药性试剂盒及制备方法 |
| RU2016146581A (ru) * | 2014-05-20 | 2018-06-21 | АрКьюЭкс ФАРМАСЪЮТИКЛС, ИНК. | Макроциклические антибиотики широкого спектра действия |
| CN107106533B (zh) | 2014-10-31 | 2020-11-06 | 罗切斯特大学 | 用于治疗微生物感染的增效组合物 |
| EP3377474B1 (en) | 2015-11-20 | 2023-08-16 | RQX Pharmaceuticals, Inc. | Macrocyclic broad spectrum antibiotics |
| WO2017214534A1 (en) | 2016-06-10 | 2017-12-14 | The Scripps Research Institute | Synthesis of the arylomycin macrocyclic core |
| IL268483B2 (en) * | 2017-02-15 | 2024-02-01 | Rqx Pharmaceuticals Inc | Macrocyclic broad spectrum antibiotics |
| EP3388445A1 (en) * | 2017-04-10 | 2018-10-17 | F. Hoffmann-La Roche AG | Peptide macrocycles and use thereof in the treatment of bacterial infections |
| IL295889B2 (en) | 2019-05-28 | 2025-01-01 | Hoffmann La Roche | Broad-spectrum macrocyclic antibiotic |
| CN116023430B (zh) * | 2022-12-20 | 2025-11-25 | 中国药科大学 | 2-(2-(2-苯甲酰氨基)乙酰胺)苯甲酸类衍生物及其制备方法和用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2234876C (en) | 1995-11-03 | 2002-09-10 | Vasantha Nagarajan | Positive selection vector for bacillus sp. |
| US6951840B2 (en) * | 2001-08-31 | 2005-10-04 | Eli Lilly And Company | Lipoglycopeptide antibiotics |
| DE102005014245A1 (de) | 2005-03-30 | 2006-10-05 | Aicuris Gmbh & Co. Kg | Antibakterielle Amid-Makrozyklen V |
| 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 |
-
2011
- 2011-08-31 KR KR1020137009510A patent/KR20130105659A/ko not_active Withdrawn
- 2011-08-31 JP JP2013529181A patent/JP2013539751A/ja not_active Ceased
- 2011-08-31 CN CN2011800550186A patent/CN103209700A/zh active Pending
- 2011-08-31 BR BR112013006265A patent/BR112013006265A2/pt not_active IP Right Cessation
- 2011-08-31 MX MX2013003035A patent/MX2013003035A/es not_active Application Discontinuation
- 2011-08-31 EP EP11825668.4A patent/EP2616093A4/en not_active Withdrawn
- 2011-08-31 CA CA2811295A patent/CA2811295A1/en not_active Abandoned
- 2011-08-31 RU RU2013112483/04A patent/RU2013112483A/ru not_active Application Discontinuation
- 2011-08-31 WO PCT/US2011/049967 patent/WO2012036907A2/en not_active Ceased
- 2011-08-31 US US13/821,195 patent/US9187524B2/en not_active Expired - Fee Related
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