DE102005014245A1 - Antibakterielle Amid-Makrozyklen V - Google Patents
Antibakterielle Amid-Makrozyklen V Download PDFInfo
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- DE102005014245A1 DE102005014245A1 DE102005014245A DE102005014245A DE102005014245A1 DE 102005014245 A1 DE102005014245 A1 DE 102005014245A1 DE 102005014245 A DE102005014245 A DE 102005014245A DE 102005014245 A DE102005014245 A DE 102005014245A DE 102005014245 A1 DE102005014245 A1 DE 102005014245A1
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- Prior art keywords
- hydrogen
- amino
- independently
- methyl
- formula
- Prior art date
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- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 10
- -1 amide macrocycles Chemical class 0.000 title abstract description 57
- 238000000034 method Methods 0.000 claims abstract description 106
- 201000010099 disease Diseases 0.000 claims abstract description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 238000011282 treatment Methods 0.000 claims abstract description 17
- 238000011321 prophylaxis Methods 0.000 claims abstract description 14
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 11
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims description 203
- 229910052739 hydrogen Inorganic materials 0.000 claims description 203
- 150000001875 compounds Chemical class 0.000 claims description 155
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 123
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 106
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 93
- 150000002431 hydrogen Chemical class 0.000 claims description 93
- 229910052757 nitrogen Inorganic materials 0.000 claims description 85
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 79
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 79
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 76
- 150000001721 carbon Chemical group 0.000 claims description 54
- 229910052799 carbon Inorganic materials 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 53
- 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 50
- 239000012453 solvate Substances 0.000 claims description 44
- 125000004193 piperazinyl group Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 15
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 11
- 238000004587 chromatography analysis Methods 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 159
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 147
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 105
- 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 72
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 70
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 50
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 42
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 42
- 239000007787 solid Substances 0.000 description 42
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 40
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 37
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 32
- 239000003480 eluent Substances 0.000 description 32
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000000746 purification Methods 0.000 description 30
- BXGTVNLGPMZLAZ-UHFFFAOYSA-N n'-ethylmethanediimine;hydrochloride Chemical compound Cl.CCN=C=N BXGTVNLGPMZLAZ-UHFFFAOYSA-N 0.000 description 29
- 239000012074 organic phase Substances 0.000 description 28
- 239000012043 crude product Substances 0.000 description 27
- WORJRXHJTUTINR-UHFFFAOYSA-N 1,4-dioxane;hydron;chloride Chemical compound Cl.C1COCCO1 WORJRXHJTUTINR-UHFFFAOYSA-N 0.000 description 26
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 25
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 25
- 235000019341 magnesium sulphate Nutrition 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 239000002585 base Substances 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- 238000005160 1H NMR spectroscopy Methods 0.000 description 23
- 239000000706 filtrate Substances 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 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 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 235000019253 formic acid Nutrition 0.000 description 20
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 19
- 238000004128 high performance liquid chromatography Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- 239000011780 sodium chloride Substances 0.000 description 19
- 0 CC(C)(C)CC(C)(C)C(*)N Chemical compound CC(C)(C)CC(C)(C)C(*)N 0.000 description 18
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
- 229910052786 argon Inorganic materials 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- 229910052763 palladium Inorganic materials 0.000 description 16
- 208000015181 infectious disease Diseases 0.000 description 13
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 13
- 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 13
- 229960000583 acetic acid Drugs 0.000 description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 238000000825 ultraviolet detection Methods 0.000 description 12
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 10
- 238000010790 dilution Methods 0.000 description 10
- 239000012895 dilution Substances 0.000 description 10
- 238000000338 in vitro Methods 0.000 description 10
- 238000002953 preparative HPLC Methods 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 9
- 108010046011 biphenomycin B Proteins 0.000 description 9
- 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 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- 239000013612 plasmid Substances 0.000 description 9
- 239000007821 HATU Substances 0.000 description 8
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 8
- 235000011054 acetic acid Nutrition 0.000 description 8
- 239000000284 extract Substances 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
- 229920001817 Agar Polymers 0.000 description 7
- 241000588724 Escherichia coli Species 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
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- 230000003115 biocidal effect Effects 0.000 description 7
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 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 6
- 241000894006 Bacteria Species 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
- 108090000331 Firefly luciferases Proteins 0.000 description 5
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- 238000005481 NMR spectroscopy Methods 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
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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 5
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- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 5
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- 238000003786 synthesis reaction Methods 0.000 description 5
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 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
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- 235000011178 triphosphate Nutrition 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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)
Priority Applications (17)
| 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 |
| EP06723614A EP1869068A1 (de) | 2005-03-30 | 2006-03-22 | Antibakterielle amid-makrozyklen v |
| RU2007139760/04A RU2409588C2 (ru) | 2005-03-30 | 2006-03-22 | Бактерицидные содержащие амидные группы макроциклы v |
| AU2006228751A AU2006228751A1 (en) | 2005-03-30 | 2006-03-22 | Antibacterial amide-macrocycles V |
| NZ562003A NZ562003A (en) | 2005-03-30 | 2006-03-22 | Macrocyclic biphenyl-peptide compounds |
| CNA2006800188391A CN101228182A (zh) | 2005-03-30 | 2006-03-22 | 抗菌酰胺-大环类ⅴ |
| ZA200709336A ZA200709336B (en) | 2005-03-30 | 2006-03-22 | Antibacterial amide-macrocycles V |
| JP2008503408A JP2008534540A (ja) | 2005-03-30 | 2006-03-22 | 抗菌性アミド−マクロサイクルｖ |
| UAA200711765A UA91541C2 (ru) | 2005-03-30 | 2006-03-22 | Бактерицидные макроциклы v, которые содержат амидные группы |
| MX2007012146A MX2007012146A (es) | 2005-03-30 | 2006-03-22 | Amida-macrociclos v antibacterianos. |
| CA002602755A CA2602755A1 (en) | 2005-03-30 | 2006-03-22 | Antibacterial amide-macrocycles v |
| BRPI0612219-1A BRPI0612219A2 (pt) | 2005-03-30 | 2006-03-22 | macrociclos amida v antibacterianos |
| KR1020077025008A KR20070116169A (ko) | 2005-03-30 | 2006-03-22 | 항박테리아성 아미드-마크로사이클 ｖ |
| IL185899A IL185899A0 (en) | 2005-03-30 | 2007-09-11 | Antibacterial amide-macrocycles v |
| US11/906,088 US20080275018A1 (en) | 2005-03-30 | 2007-09-28 | Antibacterial amide-macrocycles v |
| NO20075270A NO20075270L (no) | 2005-03-30 | 2007-10-15 | Antibakterielle amid-makrocykler V |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005014245A DE102005014245A1 (de) | 2005-03-30 | 2005-03-30 | Antibakterielle Amid-Makrozyklen V |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102005014245A1 true DE102005014245A1 (de) | 2006-10-05 |
Family
ID=36572224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102005014245A Withdrawn DE102005014245A1 (de) | 2005-03-30 | 2005-03-30 | Antibakterielle Amid-Makrozyklen V |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20080275018A1 (enExample) |
| 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) |
| NZ (1) | NZ562003A (enExample) |
| RU (1) | RU2409588C2 (enExample) |
| UA (1) | UA91541C2 (enExample) |
| WO (1) | WO2006103015A1 (enExample) |
| ZA (1) | ZA200709336B (enExample) |
Families Citing this family (15)
| 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 |
| EP3388444A1 (en) * | 2017-04-10 | 2018-10-17 | F. Hoffmann-La Roche AG | Anti-bacterial peptide macrocycles and use thereof |
| 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 |
| 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 |
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
- 2005-03-30 DE DE102005014245A patent/DE102005014245A1/de not_active Withdrawn
-
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
-
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
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 |
| JP2008534540A (ja) | 2008-08-28 |
| WO2006103015A1 (de) | 2006-10-05 |
| UA91541C2 (ru) | 2010-08-10 |
| AU2006228751A1 (en) | 2006-10-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R120 | Application withdrawn or ip right abandoned | ||
| R120 | Application withdrawn or ip right abandoned |
Effective date: 20110628 |