CA2471458A1 - Dab9 derivatives of lipopeptide antibiotics and methods of making and using the same - Google Patents
Dab9 derivatives of lipopeptide antibiotics and methods of making and using the same Download PDFInfo
- Publication number
- CA2471458A1 CA2471458A1 CA002471458A CA2471458A CA2471458A1 CA 2471458 A1 CA2471458 A1 CA 2471458A1 CA 002471458 A CA002471458 A CA 002471458A CA 2471458 A CA2471458 A CA 2471458A CA 2471458 A1 CA2471458 A1 CA 2471458A1
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- Prior art keywords
- compound
- dab9
- same
- alkyl
- different
- 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
- 238000000034 method Methods 0.000 title claims abstract description 44
- 239000003242 anti bacterial agent Substances 0.000 title abstract description 59
- 229940088710 antibiotic agent Drugs 0.000 title abstract description 58
- 108010028921 Lipopeptides Proteins 0.000 title abstract description 53
- 150000001875 compounds Chemical class 0.000 claims abstract description 117
- 208000015181 infectious disease Diseases 0.000 claims abstract description 21
- 241000192125 Firmicutes Species 0.000 claims abstract description 14
- -1 amidino, carboxy Chemical group 0.000 claims description 101
- 150000001413 amino acids Chemical class 0.000 claims description 36
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 34
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 230000012010 growth Effects 0.000 claims description 9
- 125000003368 amide group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 239000004599 antimicrobial Substances 0.000 claims description 7
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- 241000894006 Bacteria Species 0.000 claims description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 6
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- 239000003814 drug Substances 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 4
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- 125000000172 C5-C10 aryl group Chemical group 0.000 claims 6
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims 4
- 125000003275 alpha amino acid group Chemical group 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
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- 125000003118 aryl group Chemical group 0.000 description 32
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- 125000006850 spacer group Chemical group 0.000 description 18
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- XBNDESPXQUOOBQ-LSMLZNGOSA-N (2r,3s)-4-[[(2s)-1-[[2-[[(2s)-1-[[2-[[(2r,3s)-1-[[(2s)-1-[(2s)-2-[[(1s)-1-[(3s,9ar)-1,4-dioxo-3,6,7,8,9,9a-hexahydro-2h-pyrido[1,2-a]pyrazin-3-yl]ethyl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]amino]-3-amino-1-oxobutan-2-yl]amino]-2-oxoethyl]am Chemical compound CCC(C)CCCCC\C=C\CC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)C(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)NCC(=O)N[C@H]([C@H](C)N)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)[C@H]1C(=O)N2CCCC[C@@H]2C(=O)N1 XBNDESPXQUOOBQ-LSMLZNGOSA-N 0.000 description 16
- 125000001072 heteroaryl group Chemical group 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
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- 125000006239 protecting group Chemical group 0.000 description 13
- 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 11
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- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
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- 238000003786 synthesis reaction Methods 0.000 description 10
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 9
- 125000005418 aryl aryl group Chemical group 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 125000004404 heteroalkyl group Chemical group 0.000 description 9
- 150000003335 secondary amines Chemical class 0.000 description 9
- BYWOWQCRVFUOLF-AQZAFBPESA-N tsushimycin Chemical compound O=C1[C@H](C(C)C)NC(=O)[C@@H](C(C)N)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](C(C)C(O)=O)NC(=O)[C@H]2CCCCN2C(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)C\C=C/CCCCCCCC(C)C)C(C)NC(=O)[C@@H]2CCCN21 BYWOWQCRVFUOLF-AQZAFBPESA-N 0.000 description 9
- 108010038669 tsushimycin Proteins 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 125000004953 trihalomethyl group Chemical group 0.000 description 8
- 101150046623 Dab2 gene Proteins 0.000 description 7
- 238000003556 assay Methods 0.000 description 7
- 150000005347 biaryls Chemical group 0.000 description 7
- 230000000813 microbial effect Effects 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
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- 238000000855 fermentation Methods 0.000 description 6
- 230000004151 fermentation Effects 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000003755 preservative agent Substances 0.000 description 6
- 229930000044 secondary metabolite Natural products 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- AQZKCOXFXDOYRA-PVASSXKPSA-N (3S)-4-[[2-[[(2R,3S)-1-[[(2S)-1-[(2S)-2-[[(10aR)-3-methyl-1,5-dioxo-2,3,4,7,8,9,10,10a-octahydropyrido[1,2-a][1,4]diazepin-4-yl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]amino]-3-amino-1-oxobutan-2-yl]amino]-2-oxoethyl]amino]-3-[[2-[[(2S)-3-carboxy-2-[[(2S)-3-carboxy-2-[[(2S)-3-carboxy-2-[[(E)-10-methyldodec-3-enoyl]amino]propanoyl]-methylamino]propanoyl]amino]propanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound CCC(C)CCCCC\C=C\CC(=O)N[C@@H](CC(O)=O)C(=O)N(C)[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)NCC(=O)N[C@H]([C@H](C)N)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1C(C)NC(=O)[C@H]2CCCCN2C1=O AQZKCOXFXDOYRA-PVASSXKPSA-N 0.000 description 5
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- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 5
- 125000002015 acyclic group Chemical group 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
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- 125000003277 amino group Chemical group 0.000 description 5
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- 239000000843 powder Substances 0.000 description 5
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical group NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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- 239000011369 resultant mixture Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- FMKFBRKHHLWKDB-UHFFFAOYSA-N rubicene Chemical compound C12=CC=CC=C2C2=CC=CC3=C2C1=C1C=CC=C2C4=CC=CC=C4C3=C21 FMKFBRKHHLWKDB-UHFFFAOYSA-N 0.000 description 1
- WEMQMWWWCBYPOV-UHFFFAOYSA-N s-indacene Chemical compound C=1C2=CC=CC2=CC2=CC=CC2=1 WEMQMWWWCBYPOV-UHFFFAOYSA-N 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000007423 screening assay Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035040 seed growth Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000012289 standard assay Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 231100000057 systemic toxicity Toxicity 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 229960001608 teicoplanin Drugs 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- 230000009105 vegetative growth Effects 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
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
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
-
- 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
-
- 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)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45371002P | 2002-01-03 | 2002-01-03 | |
| US60/453,710 | 2002-01-03 | ||
| PCT/US2003/000158 WO2003057724A1 (en) | 2002-01-03 | 2003-01-02 | Dab9 DERIVATIVES OF LIPOPEPTIDE ANTIBIOTICS AND METHODS OF MAKING AND USING THE SAME |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2471458A1 true CA2471458A1 (en) | 2003-07-17 |
Family
ID=33131662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002471458A Abandoned CA2471458A1 (en) | 2002-01-03 | 2003-01-02 | Dab9 derivatives of lipopeptide antibiotics and methods of making and using the same |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US7125844B2 (enExample) |
| EP (1) | EP1481005A1 (enExample) |
| JP (1) | JP4402463B2 (enExample) |
| AU (1) | AU2003202878B2 (enExample) |
| CA (1) | CA2471458A1 (enExample) |
| WO (1) | WO2003057724A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1481005A1 (en) * | 2002-01-03 | 2004-12-01 | Micrologix Biotech, Inc. | Dab sp 9 /sp DERIVATIVES OF LIPOPEPTIDE ANTIBIOTICS AND METHODS OF MAKING AND USING THE SAME |
| AU2004252174A1 (en) | 2003-06-26 | 2005-01-06 | Migenix Inc. | Compositions of lipopeptide antibiotic derivatives and methods of use thereof |
| WO2007092633A2 (en) * | 2006-02-09 | 2007-08-16 | Elevance Renewable Sciences, Inc. | Antimicrobial compositions, methods and systems |
| US7951232B2 (en) * | 2006-02-09 | 2011-05-31 | Elevance Renewable Sciences, Inc. | Surface coating compositions and methods |
| GB0821540D0 (en) | 2008-11-25 | 2008-12-31 | Merlion Pharmaceuticals Pte Ltd | Lipopeptide compounds and their use |
| US9504756B2 (en) * | 2012-05-15 | 2016-11-29 | Seattle Genetics, Inc. | Self-stabilizing linker conjugates |
| BR112019001945A2 (pt) | 2016-08-09 | 2019-05-07 | Seattle Genetics, Inc. | composição de conjugado de fármaco aglutinante, formulação farmaceuticamente aceitável, métodos para tratar uma doença ou afecção hiperproliferativa, para inibir a multiplicação de uma célula tumoral ou célula cancerígena e para preparar uma composição de conjugado de fármaco aglutinado, e, composto |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB923544A (en) | 1959-07-21 | 1963-04-10 | Takeda Pharmaceutical | A new antibiotic-glumamycin |
| US3057779A (en) | 1960-03-14 | 1962-10-09 | American Cyanamid Co | Antibiotic and production thereof |
| US3639582A (en) | 1967-04-14 | 1972-02-01 | Zaidan Hojin Biseibutsu | Antibiotic laspartomycin |
| DE1800363A1 (de) | 1967-10-04 | 1969-07-03 | Shionogi & Co | Tsushimycin und seine Herstellung |
| FR2124060B1 (enExample) | 1971-02-02 | 1974-04-12 | Rhone Poulenc Sa | |
| US4524135A (en) | 1982-05-21 | 1985-06-18 | Eli Lilly And Company | A-21978C cyclic peptides |
| ZA883887B (en) | 1987-06-10 | 1990-02-28 | Lilly Co Eli | Chromatographic purification process |
| US5039789A (en) | 1988-04-11 | 1991-08-13 | Eli Lilly And Company | A54145 cyclic peptides |
| US4994270A (en) | 1988-04-11 | 1991-02-19 | Eli Lilly And Company | A54145 antibiotics and process for their production |
| US5028590A (en) | 1988-04-11 | 1991-07-02 | Eli Lilly And Company | Derivatives of A54145 cyclic peptides |
| US4977083A (en) | 1988-04-11 | 1990-12-11 | Eli Lilly And Company | Processes for preparing A54145 compounds |
| TW455591B (en) * | 1993-06-08 | 2001-09-21 | Hoechst Ag | Lipopeptides from actinoplanes sp. with pharmacological action, process for their production and the use thereof |
| DE4411025A1 (de) | 1994-03-30 | 1995-10-05 | Hoechst Ag | Lipopeptid-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung |
| WO1997047738A1 (en) | 1996-06-13 | 1997-12-18 | Fujisawa Pharmaceutical Co., Ltd. | Cyclic lipopeptide acylase |
| DE19807972A1 (de) | 1998-02-25 | 1999-08-26 | Hoechst Marion Roussel De Gmbh | Lipopeptidantibiotika-Calciumsalze, Verfahren zu ihrer Herstellung und Verwendung |
| US6716962B2 (en) | 2000-07-17 | 2004-04-06 | Micrologix Biotech Inc. | Extractive purification of lipopeptide antibiotics |
| US6750199B2 (en) * | 2000-07-17 | 2004-06-15 | Micrologix Biotech Inc. | Antimicrobial sulfonamide derivatives of lipopeptide antibiotics |
| AU7893301A (en) | 2000-07-17 | 2002-01-30 | Intrabiotics Pharmaceuticals | Antimicrobial sulfonamide derivatives of lipopeptide antibiotics |
| EP1481005A1 (en) * | 2002-01-03 | 2004-12-01 | Micrologix Biotech, Inc. | Dab sp 9 /sp DERIVATIVES OF LIPOPEPTIDE ANTIBIOTICS AND METHODS OF MAKING AND USING THE SAME |
-
2003
- 2003-01-02 EP EP03701990A patent/EP1481005A1/en not_active Withdrawn
- 2003-01-02 AU AU2003202878A patent/AU2003202878B2/en not_active Ceased
- 2003-01-02 JP JP2003558038A patent/JP4402463B2/ja not_active Expired - Fee Related
- 2003-01-02 CA CA002471458A patent/CA2471458A1/en not_active Abandoned
- 2003-01-02 WO PCT/US2003/000158 patent/WO2003057724A1/en not_active Ceased
- 2003-01-02 US US10/336,641 patent/US7125844B2/en not_active Expired - Fee Related
-
2006
- 2006-10-05 US US11/539,139 patent/US7655623B2/en not_active Expired - Fee Related
-
2010
- 2010-02-01 US US12/697,937 patent/US20100137199A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003202878B2 (en) | 2008-07-31 |
| US7655623B2 (en) | 2010-02-02 |
| JP4402463B2 (ja) | 2010-01-20 |
| WO2003057724A1 (en) | 2003-07-17 |
| US20100137199A1 (en) | 2010-06-03 |
| EP1481005A1 (en) | 2004-12-01 |
| JP2005524622A (ja) | 2005-08-18 |
| US20070167357A1 (en) | 2007-07-19 |
| AU2003202878A1 (en) | 2003-07-24 |
| US20040138107A1 (en) | 2004-07-15 |
| US7125844B2 (en) | 2006-10-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |