CA2379851A1 - Analogues a base de pseudomycine a chaines laterales n-acyle - Google Patents
Analogues a base de pseudomycine a chaines laterales n-acyle Download PDFInfo
- Publication number
- CA2379851A1 CA2379851A1 CA002379851A CA2379851A CA2379851A1 CA 2379851 A1 CA2379851 A1 CA 2379851A1 CA 002379851 A CA002379851 A CA 002379851A CA 2379851 A CA2379851 A CA 2379851A CA 2379851 A1 CA2379851 A1 CA 2379851A1
- Authority
- CA
- Canada
- Prior art keywords
- pseudomycin
- hydrogen
- compound
- alkyl
- mmol
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- 229940121375 antifungal agent Drugs 0.000 claims abstract description 10
- -1 .alpha.-acetoacetate Chemical group 0.000 claims description 64
- 238000000034 method Methods 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 32
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
- 238000002360 preparation method Methods 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 241001465754 Metazoa Species 0.000 claims description 18
- 125000006239 protecting group Chemical group 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 230000000843 anti-fungal effect Effects 0.000 claims description 12
- XDPWWEOIDYYUDN-HCEIJDMSSA-N 2-[(9z)-18-(4-aminobutyl)-15,24-bis(2-aminoethyl)-21-(carboxymethyl)-3-(2-chloro-1-hydroxyethyl)-27-(3,4-dihydroxytetradecanoylamino)-9-ethylidene-12-(1-hydroxyethyl)-2,5,8,11,14,17,20,23,26-nonaoxo-1-oxa-4,7,10,13,16,19,22,25-octazacyclooctacos-6-yl]-2-h Chemical compound CCCCCCCCCCC(O)C(O)CC(=O)NC1COC(=O)C(C(O)CCl)NC(=O)C(C(O)C(O)=O)NC(=O)\C(=C\C)NC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCCCN)NC(=O)C(CC(O)=O)NC(=O)C(CCN)NC1=O XDPWWEOIDYYUDN-HCEIJDMSSA-N 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
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- 239000012453 solvate Substances 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 6
- 239000003814 drug Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 6
- KZSKIDBMTSZKLE-NDWYDANWSA-N (2s)-2-[(3s,6s,9e,12s,15r,18s,21s,24r,27s)-18-(4-aminobutyl)-15,24-bis(2-aminoethyl)-21-(carboxymethyl)-3-[(1s)-2-chloro-1-hydroxyethyl]-9-ethylidene-12-[(1s)-1-hydroxyethyl]-27-[[(3r)-3-hydroxyhexadecanoyl]amino]-2,5,8,11,14,17,20,23,26-nonaoxo-1-oxa-4,7 Chemical compound CCCCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1COC(=O)[C@H]([C@H](O)CCl)NC(=O)[C@H]([C@H](O)C(O)=O)NC(=O)\C(=C/C)NC(=O)[C@H]([C@H](C)O)NC(=O)[C@@H](CCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](CCN)NC1=O KZSKIDBMTSZKLE-NDWYDANWSA-N 0.000 claims description 5
- 208000015181 infectious disease Diseases 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 206010017533 Fungal infection Diseases 0.000 claims description 4
- 208000031888 Mycoses Diseases 0.000 claims description 4
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 2
- 125000006314 C5-C8 alkoxy group Chemical group 0.000 claims description 2
- 206010017543 Fungal skin infection Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000009885 systemic effect Effects 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 8
- 239000003429 antifungal agent Substances 0.000 abstract description 7
- 238000013461 design Methods 0.000 abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 61
- 238000006243 chemical reaction Methods 0.000 description 57
- 239000000243 solution Substances 0.000 description 56
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 241000589615 Pseudomonas syringae Species 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 31
- 235000019439 ethyl acetate Nutrition 0.000 description 29
- 239000002904 solvent Substances 0.000 description 28
- 238000003756 stirring Methods 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 25
- 239000000047 product Substances 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
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- 239000012044 organic layer Substances 0.000 description 21
- 230000000694 effects Effects 0.000 description 19
- 239000012267 brine Substances 0.000 description 18
- 239000002243 precursor Substances 0.000 description 18
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
- 239000007787 solid Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- 238000004128 high performance liquid chromatography Methods 0.000 description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000002274 desiccant Substances 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
- NYRWZRIVFVWNTD-SGRJACMKSA-N (2s)-2-[(3s,6s,9z,12s,15s,18s,21s,24r,27s)-18-(4-aminobutyl)-15,24-bis(2-aminoethyl)-21-(carboxymethyl)-3-[(1s)-2-chloro-1-hydroxyethyl]-9-ethylidene-12-[(1s)-1-hydroxyethyl]-27-[[(3r)-3-hydroxytetradecanoyl]amino]-2,5,8,11,14,17,20,23,26-nonaoxo-1-oxa-4, Chemical compound CCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1COC(=O)[C@H]([C@H](O)CCl)NC(=O)[C@H]([C@H](O)C(O)=O)NC(=O)\C(=C\C)NC(=O)[C@H]([C@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](CCN)NC1=O NYRWZRIVFVWNTD-SGRJACMKSA-N 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 108010033821 pseudomycin B Proteins 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
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- 101150041968 CDC13 gene Proteins 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 8
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- 238000004108 freeze drying Methods 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 241000222122 Candida albicans Species 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 238000002953 preparative HPLC Methods 0.000 description 7
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 239000003054 catalyst Substances 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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- 125000001424 substituent group Chemical group 0.000 description 5
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 5
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
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- IHYNKGRWCDKNEG-UHFFFAOYSA-N n-(4-bromophenyl)-2,6-dihydroxybenzamide Chemical compound OC1=CC=CC(O)=C1C(=O)NC1=CC=C(Br)C=C1 IHYNKGRWCDKNEG-UHFFFAOYSA-N 0.000 description 1
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- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
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- 239000007790 solid phase Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
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- OGNAOIGAPPSUMG-UHFFFAOYSA-N spiro[2.2]pentane Chemical compound C1CC11CC1 OGNAOIGAPPSUMG-UHFFFAOYSA-N 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008227 sterile water for injection Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZEFNRWGWQDGTR-UHFFFAOYSA-N tetradec-1-yne Chemical compound CCCCCCCCCCCCC#C DZEFNRWGWQDGTR-UHFFFAOYSA-N 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Substances C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 1
- JQSHBVHOMNKWFT-DTORHVGOSA-N varenicline Chemical compound C12=CC3=NC=CN=C3C=C2[C@H]2C[C@@H]1CNC2 JQSHBVHOMNKWFT-DTORHVGOSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- 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
-
- 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
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Communicable Diseases (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Epoxy Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Abstract
L'invention concerne des composés semi-synthétiques à base de pseudomycine représentés par la structure (I), qui peuvent être utiles comme agents antifongiques ou comme intermédiaires dans l'élaboration d'agents antifongiques.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14398999P | 1999-07-15 | 1999-07-15 | |
| US60/143,989 | 1999-07-15 | ||
| PCT/US2000/015017 WO2001005814A1 (fr) | 1999-07-15 | 2000-06-08 | Analogues a base de pseudomycine a chaines laterales n-acyle |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2379851A1 true CA2379851A1 (fr) | 2001-01-25 |
Family
ID=22506582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002379851A Abandoned CA2379851A1 (fr) | 1999-07-15 | 2000-06-08 | Analogues a base de pseudomycine a chaines laterales n-acyle |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP1200460A1 (fr) |
| JP (1) | JP2003505397A (fr) |
| CN (1) | CN1360593A (fr) |
| AU (1) | AU5724900A (fr) |
| BR (1) | BR0012447A (fr) |
| CA (1) | CA2379851A1 (fr) |
| EA (1) | EA200200160A1 (fr) |
| HU (1) | HUP0202347A2 (fr) |
| MX (1) | MXPA02000321A (fr) |
| NO (1) | NO20020193L (fr) |
| WO (1) | WO2001005814A1 (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004051025A1 (de) | 2004-10-20 | 2006-04-27 | Bayer Healthcare Ag | Substituierte Nonadepsipeptide |
| DE102004051023A1 (de) | 2004-10-20 | 2006-05-04 | Bayer Healthcare Ag | Desoxo-Nonadepsipeptide |
| DE102004053410A1 (de) | 2004-11-05 | 2006-05-11 | Bayer Healthcare Ag | Cyclische Nonadepsipeptidamide |
| DE102006018080A1 (de) | 2006-04-13 | 2007-10-18 | Aicuris Gmbh & Co. Kg | Lysobactinamide |
| AU2010244930B2 (en) * | 2009-05-04 | 2016-07-28 | Liminal Biosciences Limited | Substituted aromatic compounds and pharmaceutical uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5576298A (en) * | 1992-11-30 | 1996-11-19 | Research And Development Institute, Inc. At Montana State University | Peptides from pseudomonas syringae possessing broad-spectrum antibiotic activity |
-
2000
- 2000-06-08 CA CA002379851A patent/CA2379851A1/fr not_active Abandoned
- 2000-06-08 AU AU57249/00A patent/AU5724900A/en not_active Abandoned
- 2000-06-08 BR BR0012447-8A patent/BR0012447A/pt not_active Application Discontinuation
- 2000-06-08 MX MXPA02000321A patent/MXPA02000321A/es unknown
- 2000-06-08 EP EP00942655A patent/EP1200460A1/fr not_active Withdrawn
- 2000-06-08 HU HU0202347A patent/HUP0202347A2/hu unknown
- 2000-06-08 JP JP2001511471A patent/JP2003505397A/ja not_active Withdrawn
- 2000-06-08 EA EA200200160A patent/EA200200160A1/ru unknown
- 2000-06-08 WO PCT/US2000/015017 patent/WO2001005814A1/fr not_active Application Discontinuation
- 2000-06-08 CN CN00810291A patent/CN1360593A/zh active Pending
-
2002
- 2002-01-14 NO NO20020193A patent/NO20020193L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BR0012447A (pt) | 2002-04-02 |
| JP2003505397A (ja) | 2003-02-12 |
| NO20020193D0 (no) | 2002-01-14 |
| WO2001005814A1 (fr) | 2001-01-25 |
| EA200200160A1 (ru) | 2002-08-29 |
| NO20020193L (no) | 2002-03-14 |
| EP1200460A1 (fr) | 2002-05-02 |
| AU5724900A (en) | 2001-02-05 |
| HUP0202347A2 (en) | 2002-10-28 |
| CN1360593A (zh) | 2002-07-24 |
| MXPA02000321A (es) | 2002-06-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |