DE102005014247A1 - Antibakterielle Amid-Makrozyklen VI - Google Patents
Antibakterielle Amid-Makrozyklen VI Download PDFInfo
- Publication number
- DE102005014247A1 DE102005014247A1 DE102005014247A DE102005014247A DE102005014247A1 DE 102005014247 A1 DE102005014247 A1 DE 102005014247A1 DE 102005014247 A DE102005014247 A DE 102005014247A DE 102005014247 A DE102005014247 A DE 102005014247A DE 102005014247 A1 DE102005014247 A1 DE 102005014247A1
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- Prior art keywords
- hydrogen
- formula
- hydroxy
- amino
- salts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 10
- -1 Amide Macrocycles Chemical class 0.000 title abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 63
- 238000002360 preparation method Methods 0.000 claims abstract description 18
- 201000010099 disease Diseases 0.000 claims abstract description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 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
- 150000001875 compounds Chemical class 0.000 claims description 108
- 239000001257 hydrogen Substances 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 60
- 150000003839 salts Chemical class 0.000 claims description 45
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 150000002431 hydrogen Chemical class 0.000 claims description 36
- 239000012453 solvate Substances 0.000 claims description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
- 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 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- 150000001721 carbon Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 241001465754 Metazoa Species 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 6
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 238000004587 chromatography analysis Methods 0.000 claims description 4
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 52
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 30
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 24
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- 239000002585 base Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 239000003480 eluent Substances 0.000 description 14
- 208000015181 infectious disease Diseases 0.000 description 13
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- 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 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- 235000019253 formic acid Nutrition 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000011780 sodium chloride Substances 0.000 description 11
- 238000013519 translation Methods 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 10
- FSUJQLPVNJKXBI-UHFFFAOYSA-N benzyl n-[2-(2-hydroxyethylamino)ethyl]carbamate Chemical compound OCCNCCNC(=O)OCC1=CC=CC=C1 FSUJQLPVNJKXBI-UHFFFAOYSA-N 0.000 description 10
- 238000010790 dilution Methods 0.000 description 10
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- 238000000338 in vitro Methods 0.000 description 10
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 235000011181 potassium carbonates Nutrition 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 7
- XPBHPXODAUHISM-UHFFFAOYSA-N 2-(phenylmethoxycarbonylamino)ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCNC(=O)OCC1=CC=CC=C1 XPBHPXODAUHISM-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 229920001817 Agar Polymers 0.000 description 7
- 241000894006 Bacteria Species 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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- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
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- WORJRXHJTUTINR-UHFFFAOYSA-N 1,4-dioxane;hydron;chloride Chemical compound Cl.C1COCCO1 WORJRXHJTUTINR-UHFFFAOYSA-N 0.000 description 6
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 6
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- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000011975 tartaric acid Chemical class 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 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 1
- PTVRCUVHYMGECC-UHFFFAOYSA-N tert-butyl 2-(aminomethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CN PTVRCUVHYMGECC-UHFFFAOYSA-N 0.000 description 1
- GQUWCDIBOGGCKZ-UHFFFAOYSA-N tert-butyl 2-[[2-(phenylmethoxycarbonylamino)ethylamino]methyl]piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CNCCNC(=O)OCC1=CC=CC=C1 GQUWCDIBOGGCKZ-UHFFFAOYSA-N 0.000 description 1
- CDWCFJWEDQWEPN-UHFFFAOYSA-N tert-butyl N-methyl-N-[2-[2-(phenylmethoxycarbonylamino)ethylamino]ethyl]carbamate Chemical compound C(C1=CC=CC=C1)OC(NCCNCCN(C)C(=O)OC(C)(C)C)=O CDWCFJWEDQWEPN-UHFFFAOYSA-N 0.000 description 1
- QYJVBVKFXDHFPQ-UHFFFAOYSA-N tert-butyl n-(2-aminoethyl)-n-methylcarbamate Chemical compound NCCN(C)C(=O)OC(C)(C)C QYJVBVKFXDHFPQ-UHFFFAOYSA-N 0.000 description 1
- LZNOKWJGNPKUSE-UHFFFAOYSA-N tert-butyl n-(3-amino-2-hydroxypropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC(O)CN LZNOKWJGNPKUSE-UHFFFAOYSA-N 0.000 description 1
- NXSMDBGXTHXEBZ-LBPRGKRZSA-N tert-butyl n-[(2s)-1-amino-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCC[C@@H](CN)NC(=O)OC(C)(C)C NXSMDBGXTHXEBZ-LBPRGKRZSA-N 0.000 description 1
- KSRBRHJOHVOAPM-LBPRGKRZSA-N tert-butyl n-[(2s)-1-azido-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCC[C@@H](CN=[N+]=[N-])NC(=O)OC(C)(C)C KSRBRHJOHVOAPM-LBPRGKRZSA-N 0.000 description 1
- JPXPKCDMMNBHHS-LBPRGKRZSA-N tert-butyl n-[(2s)-1-hydroxy-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCC[C@@H](CO)NC(=O)OC(C)(C)C JPXPKCDMMNBHHS-LBPRGKRZSA-N 0.000 description 1
- 125000003142 tertiary amide group Chemical group 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 206010044008 tonsillitis Diseases 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 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
- 238000010626 work up procedure Methods 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
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
-
- 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
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D245/00—Heterocyclic compounds containing rings of more than seven members having two nitrogen atoms as the only ring hetero atoms
- C07D245/04—Heterocyclic compounds containing rings of more than seven members having two nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005014247A DE102005014247A1 (de) | 2005-03-30 | 2005-03-30 | Antibakterielle Amid-Makrozyklen VI |
| ES06723578T ES2327444T3 (es) | 2005-03-30 | 2006-03-21 | Macrociclos de amida vi antibacterianos. |
| EP06723578A EP1866291B1 (de) | 2005-03-30 | 2006-03-21 | Antibakterielle amid-makrozyklen vi |
| DE502006004234T DE502006004234D1 (de) | 2005-03-30 | 2006-03-21 | Antibakterielle amid-makrozyklen vi |
| CA002602743A CA2602743A1 (en) | 2005-03-30 | 2006-03-21 | Antibacterial amide macrocycles vi |
| JP2008503404A JP2008534537A (ja) | 2005-03-30 | 2006-03-21 | 抗菌性アミドマクロサイクルｖｉ |
| PCT/EP2006/002564 WO2006103009A1 (de) | 2005-03-30 | 2006-03-21 | Antibakterielle amid-makrozyklen vi |
| US11/904,550 US20080300231A1 (en) | 2005-03-30 | 2007-09-26 | Antibacterial amide macrocycles VI |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005014247A DE102005014247A1 (de) | 2005-03-30 | 2005-03-30 | Antibakterielle Amid-Makrozyklen VI |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102005014247A1 true DE102005014247A1 (de) | 2006-10-05 |
Family
ID=36228560
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102005014247A Withdrawn DE102005014247A1 (de) | 2005-03-30 | 2005-03-30 | Antibakterielle Amid-Makrozyklen VI |
| DE502006004234T Active DE502006004234D1 (de) | 2005-03-30 | 2006-03-21 | Antibakterielle amid-makrozyklen vi |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE502006004234T Active DE502006004234D1 (de) | 2005-03-30 | 2006-03-21 | Antibakterielle amid-makrozyklen vi |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20080300231A1 (enExample) |
| EP (1) | EP1866291B1 (enExample) |
| JP (1) | JP2008534537A (enExample) |
| CA (1) | CA2602743A1 (enExample) |
| DE (2) | DE102005014247A1 (enExample) |
| ES (1) | ES2327444T3 (enExample) |
| WO (1) | WO2006103009A1 (enExample) |
Families Citing this family (7)
| 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 |
| US10501493B2 (en) | 2011-05-27 | 2019-12-10 | Rqx Pharmaceuticals, Inc. | Broad spectrum antibiotics |
| CN104903302B (zh) * | 2012-11-21 | 2019-03-29 | 阿奇克斯制药公司 | 大环广谱抗生素 |
| MX2016015218A (es) | 2014-05-20 | 2017-07-04 | Genentech Inc | Antibioticos macrociclicos de amplio espectro. |
| MX387476B (es) | 2015-11-20 | 2025-03-18 | Rqx Pharmaceuticals Inc | Antibióticos de amplio espectro macrocíclico. |
| CA3141853A1 (en) | 2019-05-28 | 2020-12-03 | F. Hoffmann-La Roche Ag | Macrocyclic broad spectrum antibiotics |
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 DE102005014247A patent/DE102005014247A1/de not_active Withdrawn
-
2006
- 2006-03-21 WO PCT/EP2006/002564 patent/WO2006103009A1/de not_active Ceased
- 2006-03-21 EP EP06723578A patent/EP1866291B1/de not_active Not-in-force
- 2006-03-21 JP JP2008503404A patent/JP2008534537A/ja not_active Withdrawn
- 2006-03-21 CA CA002602743A patent/CA2602743A1/en not_active Abandoned
- 2006-03-21 ES ES06723578T patent/ES2327444T3/es active Active
- 2006-03-21 DE DE502006004234T patent/DE502006004234D1/de active Active
-
2007
- 2007-09-26 US US11/904,550 patent/US20080300231A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1866291A1 (de) | 2007-12-19 |
| JP2008534537A (ja) | 2008-08-28 |
| DE502006004234D1 (de) | 2009-08-27 |
| CA2602743A1 (en) | 2006-10-05 |
| EP1866291B1 (de) | 2009-07-15 |
| US20080300231A1 (en) | 2008-12-04 |
| ES2327444T3 (es) | 2009-10-29 |
| WO2006103009A1 (de) | 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 |