JP2008534540A - 抗菌性アミド−マクロサイクルｖ - Google Patents
抗菌性アミド−マクロサイクルｖ Download PDFInfo
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- JP2008534540A JP2008534540A JP2008503408A JP2008503408A JP2008534540A JP 2008534540 A JP2008534540 A JP 2008534540A JP 2008503408 A JP2008503408 A JP 2008503408A JP 2008503408 A JP2008503408 A JP 2008503408A JP 2008534540 A JP2008534540 A JP 2008534540A
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- Prior art keywords
- amino
- formula
- independently
- represents hydrogen
- methyl
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- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 258
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 258
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 180
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 139
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 121
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 110
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 98
- 150000001721 carbon Chemical group 0.000 claims abstract description 65
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 65
- 201000010099 disease Diseases 0.000 claims abstract description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 12
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 230000006806 disease prevention Effects 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 151
- 238000000034 method Methods 0.000 claims description 126
- 229910052757 nitrogen Inorganic materials 0.000 claims description 103
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 97
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 93
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 62
- 150000003839 salts Chemical class 0.000 claims description 50
- 239000012453 solvate Substances 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000004193 piperazinyl group Chemical group 0.000 claims description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 241001465754 Metazoa Species 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 238000004517 catalytic hydrocracking Methods 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 7
- 150000002678 macrocyclic compounds Chemical class 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 162
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 150
- 239000000203 mixture Substances 0.000 description 109
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 108
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 98
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 46
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 44
- 239000007787 solid Substances 0.000 description 43
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 40
- DKZLUNYIUAQSLG-ROUUACIJSA-N tert-butyl n-[(4s)-4-amino-5-[[(2s)-2,5-bis[(2-methylpropan-2-yl)oxycarbonylamino]pentyl]amino]-5-oxopentyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCC[C@H](NC(=O)OC(C)(C)C)CNC(=O)[C@@H](N)CCCNC(=O)OC(C)(C)C DKZLUNYIUAQSLG-ROUUACIJSA-N 0.000 description 40
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 36
- -1 alkali metal salts Chemical class 0.000 description 34
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
- 0 CC(C)(C)CC(C)(C)C(*)N Chemical compound CC(C)(C)CC(C)(C)C(*)N 0.000 description 31
- 238000000746 purification Methods 0.000 description 31
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 30
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 30
- 239000012043 crude product Substances 0.000 description 28
- 239000012074 organic phase Substances 0.000 description 28
- WORJRXHJTUTINR-UHFFFAOYSA-N 1,4-dioxane;hydron;chloride Chemical compound Cl.C1COCCO1 WORJRXHJTUTINR-UHFFFAOYSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 26
- 238000012360 testing method Methods 0.000 description 26
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 25
- 241000894006 Bacteria Species 0.000 description 25
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
- 235000019341 magnesium sulphate Nutrition 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 239000002585 base Substances 0.000 description 21
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 21
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 20
- 229910052763 palladium Inorganic materials 0.000 description 20
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 19
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 19
- 239000003480 eluent Substances 0.000 description 19
- 239000012071 phase Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- 229910052786 argon Inorganic materials 0.000 description 18
- 239000011780 sodium chloride Substances 0.000 description 18
- 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 17
- 235000019253 formic acid Nutrition 0.000 description 17
- 239000007858 starting material Substances 0.000 description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 14
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- IXCAVSIBYPQLGV-NSHDSACASA-N tert-butyl n-[(2s)-1-amino-5-[(2-methylpropan-2-yl)oxycarbonylamino]pentan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NCCC[C@@H](CN)NC(=O)OC(C)(C)C IXCAVSIBYPQLGV-NSHDSACASA-N 0.000 description 14
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
- 208000015181 infectious disease Diseases 0.000 description 13
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 13
- 229960000583 acetic acid Drugs 0.000 description 12
- 238000010790 dilution Methods 0.000 description 12
- 239000012895 dilution Substances 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 238000000825 ultraviolet detection Methods 0.000 description 12
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 11
- 238000002953 preparative HPLC Methods 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 238000013519 translation Methods 0.000 description 11
- XZLRJCSXDLXBSC-UHFFFAOYSA-N 3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl 2-cyanoacetate Chemical group CC(C)(C)OC(=O)NCCCOC(=O)CC#N XZLRJCSXDLXBSC-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 238000000338 in vitro Methods 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000013612 plasmid Substances 0.000 description 9
- 238000010833 quantitative mass spectrometry Methods 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- 229920001817 Agar Polymers 0.000 description 8
- 241000588724 Escherichia coli Species 0.000 description 8
- 235000011054 acetic acid Nutrition 0.000 description 8
- 239000008272 agar Substances 0.000 description 8
- 108010046011 biphenomycin B Proteins 0.000 description 8
- OXLPMCIPYGNLJD-OWSLCNJRSA-N biphenomycin b Chemical compound C=1C2=CC=C(O)C=1C[C@@H](C(O)=O)NC(=O)[C@H](C[C@@H](O)CN)NC(=O)[C@@H](N)CC1=CC2=CC=C1O OXLPMCIPYGNLJD-OWSLCNJRSA-N 0.000 description 8
- 239000000872 buffer Substances 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 description 7
- 239000003242 anti bacterial agent Substances 0.000 description 7
- 229940088710 antibiotic agent Drugs 0.000 description 7
- 230000001580 bacterial effect Effects 0.000 description 7
- 230000012010 growth Effects 0.000 description 7
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000007821 HATU Substances 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- XNRHTMDHGDWBGP-UHFFFAOYSA-N carbamic acid;hydrochloride Chemical compound Cl.NC(O)=O XNRHTMDHGDWBGP-UHFFFAOYSA-N 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 229960003104 ornithine Drugs 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
- RWQCKACYKKSOKK-AWEZNQCLSA-N (2s)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)pentanoic acid Chemical compound CC(C)(C)OC(=O)NCCC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 RWQCKACYKKSOKK-AWEZNQCLSA-N 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
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- 150000001413 amino acids Chemical class 0.000 description 5
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- 229930014626 natural product Natural products 0.000 description 5
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- 238000010898 silica gel chromatography Methods 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
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- 239000003826 tablet Substances 0.000 description 5
- 230000014616 translation Effects 0.000 description 5
- PIEPQKCYPFFYMG-UHFFFAOYSA-N tris acetate Chemical compound CC(O)=O.OCC(N)(CO)CO PIEPQKCYPFFYMG-UHFFFAOYSA-N 0.000 description 5
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- IGXWBGJHJZYPQS-SSDOTTSWSA-N D-Luciferin Chemical compound OC(=O)[C@H]1CSC(C=2SC3=CC=C(O)C=C3N=2)=N1 IGXWBGJHJZYPQS-SSDOTTSWSA-N 0.000 description 4
- CYCGRDQQIOGCKX-UHFFFAOYSA-N Dehydro-luciferin Natural products OC(=O)C1=CSC(C=2SC3=CC(O)=CC=C3N=2)=N1 CYCGRDQQIOGCKX-UHFFFAOYSA-N 0.000 description 4
- BJGNCJDXODQBOB-UHFFFAOYSA-N Fivefly Luciferin Natural products OC(=O)C1CSC(C=2SC3=CC(O)=CC=C3N=2)=N1 BJGNCJDXODQBOB-UHFFFAOYSA-N 0.000 description 4
- DDWFXDSYGUXRAY-UHFFFAOYSA-N Luciferin Natural products CCc1c(C)c(CC2NC(=O)C(=C2C=C)C)[nH]c1Cc3[nH]c4C(=C5/NC(CC(=O)O)C(C)C5CC(=O)O)CC(=O)c4c3C DDWFXDSYGUXRAY-UHFFFAOYSA-N 0.000 description 4
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- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 4
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- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 4
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- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
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- 238000003786 synthesis reaction Methods 0.000 description 4
- RPGNYNNWBVBFEJ-NRFANRHFSA-N tert-butyl n-[(3s)-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethylamino]-1-oxo-7-(phenylmethoxycarbonylamino)heptan-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NCCNC(=O)C[C@@H](NC(=O)OC(C)(C)C)CCCCNC(=O)OCC1=CC=CC=C1 RPGNYNNWBVBFEJ-NRFANRHFSA-N 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 3
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- 201000004813 Bronchopneumonia Diseases 0.000 description 3
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
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- RRNCSVKXILDLTN-PMACEKPBSA-N tert-butyl n-[(4s)-4-amino-5-[[(4s)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-6-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethylamino]-6-oxohexyl]amino]-5-oxopentyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCC[C@H](N)C(=O)NCCC[C@H](NC(=O)OC(C)(C)C)CC(=O)NCCNC(=O)OC(C)(C)C RRNCSVKXILDLTN-PMACEKPBSA-N 0.000 description 1
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- OKARKEXHWPAJDT-OALUTQOASA-N tert-butyl n-[(4s)-4-amino-6-[[(2s)-2,5-bis[(2-methylpropan-2-yl)oxycarbonylamino]pentyl]amino]-6-oxohexyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCC[C@H](N)CC(=O)NC[C@@H](NC(=O)OC(C)(C)C)CCCNC(=O)OC(C)(C)C OKARKEXHWPAJDT-OALUTQOASA-N 0.000 description 1
- VGJJHPRLNBPIBP-SVBPBHIXSA-N tert-butyl n-[(4s)-6-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethylamino]-4-[[(2s)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)pentanoyl]amino]-6-oxohexyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCNC(=O)C[C@H](CCCNC(=O)OC(C)(C)C)NC(=O)[C@H](CCCNC(=O)OC(C)(C)C)NC(=O)OCC1=CC=CC=C1 VGJJHPRLNBPIBP-SVBPBHIXSA-N 0.000 description 1
- GNLGWZUKBYEZGD-ZVAWYAOSSA-N tert-butyl n-[3-amino-5-[[(2s)-2,5-bis[(2-methylpropan-2-yl)oxycarbonylamino]pentyl]amino]-5-oxopentyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCC[C@H](NC(=O)OC(C)(C)C)CNC(=O)CC(N)CCNC(=O)OC(C)(C)C GNLGWZUKBYEZGD-ZVAWYAOSSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0812—Tripeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/07—Tetrapeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1016—Tetrapeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/02—Linear peptides containing at least one abnormal peptide link
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005014245A DE102005014245A1 (de) | 2005-03-30 | 2005-03-30 | Antibakterielle Amid-Makrozyklen V |
| PCT/EP2006/002617 WO2006103015A1 (de) | 2005-03-30 | 2006-03-22 | Antibakterielle amid-makrozyklen v |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008534540A true JP2008534540A (ja) | 2008-08-28 |
| JP2008534540A5 JP2008534540A5 (enExample) | 2009-05-21 |
Family
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Family Applications (1)
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| JP2008503408A Withdrawn JP2008534540A (ja) | 2005-03-30 | 2006-03-22 | 抗菌性アミド−マクロサイクルｖ |
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| EP (1) | EP1869068A1 (enExample) |
| JP (1) | JP2008534540A (enExample) |
| KR (1) | KR20070116169A (enExample) |
| CN (1) | CN101228182A (enExample) |
| AU (1) | AU2006228751A1 (enExample) |
| BR (1) | BRPI0612219A2 (enExample) |
| CA (1) | CA2602755A1 (enExample) |
| DE (1) | DE102005014245A1 (enExample) |
| IL (1) | IL185899A0 (enExample) |
| MX (1) | MX2007012146A (enExample) |
| NO (1) | NO20075270L (enExample) |
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| UA (1) | UA91541C2 (enExample) |
| WO (1) | WO2006103015A1 (enExample) |
| ZA (1) | ZA200709336B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020516580A (ja) * | 2017-04-10 | 2020-06-11 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 抗菌ペプチドマクロ環とその使用 |
| WO2024262518A1 (ja) * | 2023-06-20 | 2024-12-26 | 国立大学法人北海道大学 | スキャニング用アミノ酸化合物、スキャニング用改変ペプチド、スキャニング用キット及びペプチドの活性部位のスキャニング方法 |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10358824A1 (de) | 2003-12-16 | 2005-07-21 | Bayer Healthcare Ag | Antibakterielle Makrozyklen mit substituiertem Biphenyl |
| DE102005032781A1 (de) * | 2005-07-14 | 2007-01-18 | Aicuris Gmbh & Co. Kg | Antibakterielle Amid-Markozyklen VII |
| MX2013003035A (es) | 2010-09-15 | 2013-12-16 | Scripps Research Inst | Analogos de arilomicina como antibióticos de amplio espectro. |
| WO2012166665A2 (en) * | 2011-05-27 | 2012-12-06 | Rqx Pharmaceuticals, Inc. | Broad spectrum antibiotics |
| US10501493B2 (en) | 2011-05-27 | 2019-12-10 | Rqx Pharmaceuticals, Inc. | Broad spectrum antibiotics |
| CA2892027A1 (en) | 2012-11-21 | 2014-05-30 | Rqx Pharmaceuticals, Inc. | Macrocyclic broad spectrum antibiotics |
| KR20170027721A (ko) | 2014-05-20 | 2017-03-10 | 알큐엑스 파마슈티컬스, 인크. | 마크로시클릭 광범위 항생제 |
| AU2016347456B2 (en) | 2015-10-27 | 2018-12-13 | F. Hoffmann-La Roche Ag | Peptide macrocycles against acinetobacter baumannii |
| KR20180109858A (ko) | 2015-11-20 | 2018-10-08 | 알큐엑스 파마슈티컬스, 인크. | 마크로시클릭 광범위 항생제 |
| MX2020002010A (es) | 2017-08-21 | 2020-07-13 | Celgene Corp | Procesos para la preparacion de 4,5-diamino-5-oxopentanoato de (s)-terc-butilo. |
| US11505573B2 (en) | 2018-03-28 | 2022-11-22 | Hoffmann-La Roche Inc. | Peptide macrocycles against Acinetobacter baumannii |
| US11819532B2 (en) | 2018-04-23 | 2023-11-21 | Hoffmann-La Roche Inc. | Peptide macrocycles against Acinetobacter baumannii |
| IL288294B (en) | 2019-05-28 | 2022-09-01 | Hoffmann La Roche | A broad-spectrum macrocyclic antibiotic |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3452136A (en) * | 1968-04-17 | 1969-06-24 | American Cyanamid Co | Antibiotic af283 and production thereof |
| FR2720066B1 (fr) * | 1994-05-20 | 1996-06-28 | Rhone Poulenc Rorer Sa | Peptides antagonistes de la neurotensine. |
| DE10226921A1 (de) * | 2002-06-17 | 2003-12-24 | Bayer Ag | Antibakterielle Amid-Makrozyklen |
| DE10234422A1 (de) * | 2002-07-29 | 2004-02-12 | Bayer Ag | Antibakterielle Ester-Makrozyklen |
| CA2540646A1 (en) * | 2003-10-01 | 2005-04-14 | Bayer Healthcare Ag | Antibacterial amide macrocycles |
| DE10358824A1 (de) * | 2003-12-16 | 2005-07-21 | Bayer Healthcare Ag | Antibakterielle Makrozyklen mit substituiertem Biphenyl |
| DE102005014240A1 (de) * | 2004-09-24 | 2006-03-30 | Bayer Healthcare Ag | Antibakterielle Amid-Makrozyklen IV |
-
2005
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2006
- 2006-03-22 MX MX2007012146A patent/MX2007012146A/es not_active Application Discontinuation
- 2006-03-22 EP EP06723614A patent/EP1869068A1/de not_active Withdrawn
- 2006-03-22 NZ NZ562003A patent/NZ562003A/en unknown
- 2006-03-22 CN CNA2006800188391A patent/CN101228182A/zh active Pending
- 2006-03-22 ZA ZA200709336A patent/ZA200709336B/xx unknown
- 2006-03-22 WO PCT/EP2006/002617 patent/WO2006103015A1/de not_active Ceased
- 2006-03-22 JP JP2008503408A patent/JP2008534540A/ja not_active Withdrawn
- 2006-03-22 RU RU2007139760/04A patent/RU2409588C2/ru not_active IP Right Cessation
- 2006-03-22 CA CA002602755A patent/CA2602755A1/en not_active Abandoned
- 2006-03-22 KR KR1020077025008A patent/KR20070116169A/ko not_active Ceased
- 2006-03-22 BR BRPI0612219-1A patent/BRPI0612219A2/pt not_active IP Right Cessation
- 2006-03-22 UA UAA200711765A patent/UA91541C2/ru unknown
- 2006-03-22 AU AU2006228751A patent/AU2006228751A1/en not_active Abandoned
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2007
- 2007-09-11 IL IL185899A patent/IL185899A0/en unknown
- 2007-09-28 US US11/906,088 patent/US20080275018A1/en not_active Abandoned
- 2007-10-15 NO NO20075270A patent/NO20075270L/no not_active Application Discontinuation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020516580A (ja) * | 2017-04-10 | 2020-06-11 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 抗菌ペプチドマクロ環とその使用 |
| JP7330887B2 (ja) | 2017-04-10 | 2023-08-22 | エフ． ホフマン－ラ ロシュ アーゲー | 抗菌ペプチドマクロ環とその使用 |
| WO2024262518A1 (ja) * | 2023-06-20 | 2024-12-26 | 国立大学法人北海道大学 | スキャニング用アミノ酸化合物、スキャニング用改変ペプチド、スキャニング用キット及びペプチドの活性部位のスキャニング方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| IL185899A0 (en) | 2008-12-29 |
| RU2007139760A (ru) | 2009-05-10 |
| MX2007012146A (es) | 2007-12-10 |
| KR20070116169A (ko) | 2007-12-06 |
| NZ562003A (en) | 2010-11-26 |
| US20080275018A1 (en) | 2008-11-06 |
| CA2602755A1 (en) | 2006-10-05 |
| ZA200709336B (en) | 2009-09-30 |
| EP1869068A1 (de) | 2007-12-26 |
| BRPI0612219A2 (pt) | 2009-01-13 |
| NO20075270L (no) | 2007-12-18 |
| RU2409588C2 (ru) | 2011-01-20 |
| CN101228182A (zh) | 2008-07-23 |
| WO2006103015A1 (de) | 2006-10-05 |
| UA91541C2 (ru) | 2010-08-10 |
| DE102005014245A1 (de) | 2006-10-05 |
| AU2006228751A1 (en) | 2006-10-05 |
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