AU767956B2 - Formation and anion-exchange of crystalline echinocandin ammonium salts - Google Patents
Formation and anion-exchange of crystalline echinocandin ammonium salts Download PDFInfo
- Publication number
- AU767956B2 AU767956B2 AU37182/00A AU3718200A AU767956B2 AU 767956 B2 AU767956 B2 AU 767956B2 AU 37182/00 A AU37182/00 A AU 37182/00A AU 3718200 A AU3718200 A AU 3718200A AU 767956 B2 AU767956 B2 AU 767956B2
- Authority
- AU
- Australia
- Prior art keywords
- salt
- echinocandin
- nucleus
- crystalline
- hydrogen
- 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.)
- Ceased
Links
- 108010049047 Echinocandins Proteins 0.000 title claims abstract description 26
- 150000003863 ammonium salts Chemical class 0.000 title description 7
- 230000015572 biosynthetic process Effects 0.000 title description 6
- 238000005349 anion exchange Methods 0.000 title description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 51
- 239000012141 concentrate Substances 0.000 claims abstract description 36
- 229910052751 metal Inorganic materials 0.000 claims abstract description 24
- 239000002184 metal Substances 0.000 claims abstract description 24
- 239000012535 impurity Substances 0.000 claims abstract description 23
- 230000008569 process Effects 0.000 claims abstract description 23
- 238000001728 nano-filtration Methods 0.000 claims abstract description 20
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 15
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 238000001816 cooling Methods 0.000 claims abstract description 7
- FAUOJMHVEYMQQG-HVYQDZECSA-N echinocandin B Chemical class C1([C@H](O)[C@@H](O)[C@H]2C(=O)N[C@H](C(=O)N3C[C@H](C)[C@H](O)[C@H]3C(=O)N[C@H](O)[C@H](O)C[C@@H](C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N2)[C@@H](C)O)=O)NC(=O)CCCCCCC\C=C/C\C=C/CCCCC)[C@@H](C)O)=CC=C(O)C=C1 FAUOJMHVEYMQQG-HVYQDZECSA-N 0.000 claims description 27
- 108010069514 Cyclic Peptides Proteins 0.000 claims description 24
- 102000001189 Cyclic Peptides Human genes 0.000 claims description 24
- 238000002425 crystallisation Methods 0.000 claims description 14
- 230000008025 crystallization Effects 0.000 claims description 14
- 239000011734 sodium Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- 239000012453 solvate Substances 0.000 claims description 9
- 239000013078 crystal Substances 0.000 claims description 8
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical group [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 5
- 150000004677 hydrates Chemical class 0.000 claims description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 229940095064 tartrate Drugs 0.000 claims description 5
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 5
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 240000007594 Oryza sativa Species 0.000 claims 1
- 235000007164 Oryza sativa Nutrition 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 235000009566 rice Nutrition 0.000 claims 1
- 150000001450 anions Chemical class 0.000 abstract description 16
- 239000000203 mixture Substances 0.000 abstract description 10
- 239000000243 solution Substances 0.000 description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
- -1 Sporiofungin A Chemical compound 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 235000010633 broth Nutrition 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 238000004821 distillation Methods 0.000 description 12
- 239000011780 sodium chloride Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000000855 fermentation Methods 0.000 description 10
- 230000004151 fermentation Effects 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 8
- 108010062092 echinocandin B Proteins 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000012465 retentate Substances 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 230000020176 deacylation Effects 0.000 description 5
- 238000005947 deacylation reaction Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229930014626 natural product Natural products 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical class N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000002178 crystalline material Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 238000005192 partition Methods 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000003828 vacuum filtration Methods 0.000 description 3
- KPYXMALABCDPGN-HYOZMBHHSA-N (4s)-5-[[(2s)-6-amino-1-[[(2s,3s)-1-[[(2s)-1-[[(2s)-1-[[(2s)-1-[[(2s)-1-[[(2r)-1-[[2-[[2-[[(1s)-3-amino-1-carboxy-3-oxopropyl]amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]a Chemical compound NC(=O)C[C@@H](C(O)=O)NC(=O)CNC(=O)CNC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN)CC1=CC=C(O)C=C1 KPYXMALABCDPGN-HYOZMBHHSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- KAPLTEIQCKDUAT-UHFFFAOYSA-N ac1la431 Chemical compound N1C(=O)C2CC(O)CN2C(=O)C(C(C)O)NC(=O)C(NC(=O)CCCCCCCCCCCCCCC)CC(O)C(O)NC(=O)C2C(O)C(C)CN2C(=O)C(C(O)CC(N)=O)NC(=O)C1C(O)C(O)C1=CC=C(O)C(OS(O)(=O)=O)=C1 KAPLTEIQCKDUAT-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
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- 238000000926 separation method Methods 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
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- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
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- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000002431 aminoalkoxy group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- 239000000356 contaminant Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 108010062096 echinocandin C Proteins 0.000 description 1
- NZZDHXBKVFENNY-YBPCKFEPSA-N echinocandin c Chemical compound C([C@@H](O)[C@H]1C(=O)N[C@H](C(=O)N2C[C@H](C)[C@H](O)[C@H]2C(=O)N[C@H](O)[C@H](O)C[C@@H](C(N[C@H](C(=O)N2C[C@H](O)C[C@H]2C(=O)N1)[C@@H](C)O)=O)NC(=O)CCCCCCC\C=C/C\C=C/CCCCC)[C@@H](C)O)C1=CC=C(O)C=C1 NZZDHXBKVFENNY-YBPCKFEPSA-N 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000005191 hydroxyalkylamino group Chemical group 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 108010084578 mulundocandin Proteins 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- WLGDAKIJYPIYLR-UHFFFAOYSA-N octane-1-sulfonic acid Chemical compound CCCCCCCCS(O)(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 108010016309 pneumocandin B(0) Proteins 0.000 description 1
- DQXPFAADCTZLNL-FXDJFZINSA-N pneumocandin B0 Chemical compound C1([C@H](O)[C@@H](O)[C@H]2C(=O)N[C@H](C(=O)N3CC[C@H](O)[C@H]3C(=O)N[C@H](O)[C@H](O)C[C@@H](C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N2)[C@@H](C)O)=O)NC(=O)CCCCCCCC[C@@H](C)C[C@@H](C)CC)[C@H](O)CC(N)=O)=CC=C(O)C=C1 DQXPFAADCTZLNL-FXDJFZINSA-N 0.000 description 1
- DFQUSLQYURJBIT-KGPSKUFKSA-N pneumocandin ao Chemical compound C1([C@H](O)[C@@H](O)[C@H]2C(=O)N[C@H](C(=O)N3C[C@H](C)[C@H](O)[C@H]3C(=O)N[C@H](O)[C@H](O)C[C@@H](C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N2)[C@@H](C)O)=O)NC(=O)CCCCCCCC[C@@H](C)C[C@@H](C)CC)[C@H](O)CC(N)=O)=CC=C(O)C=C1 DFQUSLQYURJBIT-KGPSKUFKSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011045 prefiltration Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- OGNAOIGAPPSUMG-UHFFFAOYSA-N spiro[2.2]pentane Chemical compound C1CC11CC1 OGNAOIGAPPSUMG-UHFFFAOYSA-N 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
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 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
- 238000011282 treatment Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/14—Extraction; Separation; Purification
- C07K1/36—Extraction; Separation; Purification by a combination of two or more processes of different types
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/84—Manufacture, treatment, or detection of nanostructure
- Y10S977/895—Manufacture, treatment, or detection of nanostructure having step or means utilizing chemical property
- Y10S977/896—Chemical synthesis, e.g. chemical bonding or breaking
- Y10S977/898—Enzymatic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2004200741A AU2004200741A1 (en) | 1999-03-03 | 2004-02-25 | Formation and anion-exchange of crystalline echinocandin ammonium salts |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12307399P | 1999-03-03 | 1999-03-03 | |
| US60/123073 | 1999-03-03 | ||
| PCT/US2000/005494 WO2000052036A1 (en) | 1999-03-03 | 2000-03-02 | Formation and anion-exchange of crystalline echinocandin ammonium salts |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004200741A Division AU2004200741A1 (en) | 1999-03-03 | 2004-02-25 | Formation and anion-exchange of crystalline echinocandin ammonium salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU3718200A AU3718200A (en) | 2000-09-21 |
| AU767956B2 true AU767956B2 (en) | 2003-11-27 |
Family
ID=22406562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU37182/00A Ceased AU767956B2 (en) | 1999-03-03 | 2000-03-02 | Formation and anion-exchange of crystalline echinocandin ammonium salts |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6590073B2 (https=) |
| EP (1) | EP1155034B1 (https=) |
| JP (1) | JP4063497B2 (https=) |
| KR (1) | KR20020002476A (https=) |
| CN (1) | CN1351610A (https=) |
| AT (1) | ATE338060T1 (https=) |
| AU (1) | AU767956B2 (https=) |
| BR (1) | BR0009248A (https=) |
| CA (1) | CA2362826A1 (https=) |
| CY (1) | CY1105777T1 (https=) |
| DE (1) | DE60030415T2 (https=) |
| DK (1) | DK1155034T3 (https=) |
| ES (1) | ES2270819T3 (https=) |
| HK (1) | HK1040087A1 (https=) |
| IL (1) | IL145186A0 (https=) |
| PT (1) | PT1155034E (https=) |
| WO (1) | WO2000052036A1 (https=) |
| ZA (1) | ZA200107999B (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6743777B1 (en) * | 1992-03-19 | 2004-06-01 | Eli Lilly And Company | Cyclic peptide antifungal agents and process for preparation thereof |
| DK1137663T3 (da) | 1998-12-09 | 2007-01-08 | Lilly Co Eli | Oprensning af Echinocandin-cyclopeptidforbindelser |
| HK1040062A1 (zh) * | 1999-03-03 | 2002-05-24 | Eli Lilly And Company | 含有成胶束表面活性剂的棘白菌素药物配方 |
| HK1040369A1 (zh) | 1999-03-03 | 2002-06-07 | Eli Lilly And Company | 制备药物口服ecb配方和组合物的方法 |
| ATE248187T1 (de) | 1999-03-03 | 2003-09-15 | Lilly Co Eli | Echinocandin-kohlenhydrate-komplexe |
| AU767956B2 (en) | 1999-03-03 | 2003-11-27 | Eli Lilly And Company | Formation and anion-exchange of crystalline echinocandin ammonium salts |
| US6991800B2 (en) | 2002-06-13 | 2006-01-31 | Vicuron Pharmaceuticals Inc. | Antifungal parenteral products |
| TW200826957A (en) * | 2006-10-16 | 2008-07-01 | Teva Gyogyszergyar Zartkoruen Mukodo Reszvenytarsasag | Purification processes for echinocandin-type compounds |
| EP2062909A1 (en) * | 2007-11-21 | 2009-05-27 | SOLVAY (Société Anonyme) | Peptide production and purification process |
| US9394340B2 (en) | 2009-03-24 | 2016-07-19 | Cadila Healthcare Limited | Purification process for lipopeptides |
| WO2010108637A1 (en) * | 2009-03-27 | 2010-09-30 | Axellia Pharmaceuticals Aps | Crystalline compound |
| CN102464704B (zh) * | 2010-11-05 | 2013-12-11 | 上海医药工业研究院 | 一种化合物及其制备方法和用途 |
| CN102485879A (zh) * | 2010-12-03 | 2012-06-06 | 上海医药工业研究院 | 一种用于生产wf11899a的发酵培养基 |
| CN102295686A (zh) * | 2011-09-09 | 2011-12-28 | 杭州华东医药集团生物工程研究所有限公司 | 一种纽莫康定b0的提取纯化方法 |
| CN102627689B (zh) * | 2012-03-30 | 2014-08-06 | 上海天伟生物制药有限公司 | 一种环肽类化合物的水合物及其制备方法和用途 |
| CN102659930B (zh) * | 2012-03-30 | 2014-04-23 | 上海天伟生物制药有限公司 | 一种高纯度环肽类物质的晶体及其制备方法和用途 |
| CN102627688B (zh) * | 2012-03-30 | 2014-12-31 | 上海天伟生物制药有限公司 | 一种高纯度环肽化合物及其制备方法和用途 |
| CN105669839B (zh) * | 2014-12-05 | 2019-08-13 | 重庆乾泰生物医药有限公司 | 一种棘白菌素b母核或其盐的水合物及制备方法和用途 |
| CN105669840B (zh) * | 2014-12-05 | 2019-06-04 | 重庆乾泰生物医药有限公司 | 一种高纯度棘白菌素b母核盐酸盐的晶体及其制备方法 |
| WO2020086931A1 (en) * | 2018-10-25 | 2020-04-30 | Cidara Therapeutics, Inc. | Polymorph of echinocandin antifungal agent |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0031221A1 (en) * | 1979-12-13 | 1981-07-01 | Eli Lilly And Company | Cyclic peptide nuclei |
| EP0744405A2 (en) * | 1995-05-26 | 1996-11-27 | Eli Lilly And Company | Cyclic peptide antifungal agents |
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|---|---|---|---|---|
| US3293482A (en) | 1962-06-21 | 1966-12-20 | Rca Corp | Plural output traveling wave tube |
| JPS5134916B2 (https=) | 1974-03-06 | 1976-09-29 | ||
| US4293489A (en) | 1979-12-13 | 1981-10-06 | Eli Lilly And Company | Derivatives of A-30912A nucleus |
| US4293482A (en) | 1979-12-13 | 1981-10-06 | Eli Lilly And Company | A-30912A Nucleus |
| US4304716A (en) | 1979-12-13 | 1981-12-08 | Eli Lilly And Company | S 31794/F-1 Nucleus |
| US4293483A (en) | 1979-12-13 | 1981-10-06 | Eli Lilly And Company | Derivatives of A-30912A nucleus |
| US4299763A (en) | 1979-12-13 | 1981-11-10 | Eli Lilly And Company | A-30912B Nucleus |
| US4320052A (en) | 1979-12-13 | 1982-03-16 | Eli Lilly And Company | Derivatives of A-30912A nucleus |
| US4876241A (en) | 1987-05-22 | 1989-10-24 | Armour Pharmaceutical Company | Stabilization of biological and pharmaceutical products during thermal inactivation of viral and bacterial contaminants |
| US5166135A (en) | 1988-09-12 | 1992-11-24 | Merck & Company, Inc. | Method for the control of pneumocystis carinii |
| DK173802B1 (da) | 1988-09-12 | 2001-11-05 | Merck & Co Inc | Præparat til behandling af Pneumocystis carinii infeksioner og anvendelse af et cyclohexapeptid til fremstilling af et lægemiddel mod Pneumocystis carinii infektioner |
| CA2037957A1 (en) | 1990-03-12 | 1991-09-13 | Merck & Co., Inc. | N-acylated cyclohexapeptide compounds |
| US5310726A (en) | 1990-03-19 | 1994-05-10 | Merck & Co., Inc. | Lipopeptide compounds |
| IL98349A (en) | 1990-06-07 | 1995-05-26 | Lilly Co Eli | Diphylase lipopeptide |
| IL98506A (en) | 1990-06-18 | 1996-09-12 | Fujisawa Pharmaceutical Co | Cyclic peptide antibiotics processes for the preparation thereof and pharmaceutical compositions containing them |
| US5198421A (en) | 1991-04-26 | 1993-03-30 | Merck & Co., Inc. | Phosphorylated cyclic lipopeptide |
| US5965525A (en) | 1992-03-19 | 1999-10-12 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| MY136593A (en) | 1992-03-19 | 2008-10-31 | Lilly Co Eli | Cyclic peptide antifungal agents and process for preparation thereof |
| US5541160A (en) | 1994-04-04 | 1996-07-30 | Merck & Co., Inc. | Antifungal and anti-pneumocystis compounds, compositions containing such compounds, and methods of use |
| US5646111A (en) | 1995-04-07 | 1997-07-08 | Eli Lilly And Company | Cyclic peptide antifungal Agents |
| US5786325A (en) | 1995-05-26 | 1998-07-28 | Eli Lilly And Company | Cyclic peptide antifungal agents and methods of making and using |
| US5629290A (en) | 1995-05-26 | 1997-05-13 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| US5618787A (en) | 1995-05-26 | 1997-04-08 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| US5629289A (en) | 1995-07-25 | 1997-05-13 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| EP0881907A4 (en) * | 1996-02-01 | 2000-05-10 | Lilly Co Eli | FUNGICIDES IN THE FORM OF CYCLIC PEPTIDES |
| JPH1036284A (ja) * | 1996-07-24 | 1998-02-10 | Sumitomo Pharmaceut Co Ltd | プロテアソーム阻害剤 |
| WO1999006062A1 (en) | 1997-08-04 | 1999-02-11 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| CN1240713C (zh) * | 1998-02-09 | 2006-02-08 | 藤泽药品工业株式会社 | 化合物 |
| US6323176B1 (en) | 1998-02-25 | 2001-11-27 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| ATE287899T1 (de) | 1998-08-20 | 2005-02-15 | Lilly Co Eli | Verfahren zur herstellung von ring-modifizierten zyklischen peptidanalogen |
| CA2340647A1 (en) | 1998-08-28 | 2000-03-09 | Eli Lilly And Company | Reversible boronate complexes of 1,2-cis-diol cyclic-peptides |
| DK1137663T3 (da) | 1998-12-09 | 2007-01-08 | Lilly Co Eli | Oprensning af Echinocandin-cyclopeptidforbindelser |
| AU767357B2 (en) | 1998-12-16 | 2003-11-06 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| AU2189500A (en) | 1998-12-16 | 2000-07-03 | Eli Lilly And Company | Cyclic peptide antifungal agents having a sugar substituent |
| AU767956B2 (en) | 1999-03-03 | 2003-11-27 | Eli Lilly And Company | Formation and anion-exchange of crystalline echinocandin ammonium salts |
| HK1040369A1 (zh) | 1999-03-03 | 2002-06-07 | Eli Lilly And Company | 制备药物口服ecb配方和组合物的方法 |
| HK1040062A1 (zh) | 1999-03-03 | 2002-05-24 | Eli Lilly And Company | 含有成胶束表面活性剂的棘白菌素药物配方 |
| ATE248187T1 (de) | 1999-03-03 | 2003-09-15 | Lilly Co Eli | Echinocandin-kohlenhydrate-komplexe |
-
2000
- 2000-03-02 AU AU37182/00A patent/AU767956B2/en not_active Ceased
- 2000-03-02 WO PCT/US2000/005494 patent/WO2000052036A1/en not_active Ceased
- 2000-03-02 JP JP2000602260A patent/JP4063497B2/ja not_active Expired - Lifetime
- 2000-03-02 ES ES00916011T patent/ES2270819T3/es not_active Expired - Lifetime
- 2000-03-02 EP EP00916011A patent/EP1155034B1/en not_active Expired - Lifetime
- 2000-03-02 BR BR0009248-7A patent/BR0009248A/pt not_active IP Right Cessation
- 2000-03-02 IL IL14518600A patent/IL145186A0/xx unknown
- 2000-03-02 DK DK00916011T patent/DK1155034T3/da active
- 2000-03-02 DE DE60030415T patent/DE60030415T2/de not_active Expired - Lifetime
- 2000-03-02 PT PT00916011T patent/PT1155034E/pt unknown
- 2000-03-02 KR KR1020017011233A patent/KR20020002476A/ko not_active Withdrawn
- 2000-03-02 CA CA002362826A patent/CA2362826A1/en not_active Abandoned
- 2000-03-02 HK HK02101825.7A patent/HK1040087A1/zh unknown
- 2000-03-02 CN CN00804419A patent/CN1351610A/zh active Pending
- 2000-03-02 AT AT00916011T patent/ATE338060T1/de active
-
2001
- 2001-08-30 US US09/944,309 patent/US6590073B2/en not_active Expired - Lifetime
- 2001-09-28 ZA ZA200107999A patent/ZA200107999B/xx unknown
-
2006
- 2006-11-13 CY CY20061101646T patent/CY1105777T1/el unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0031221A1 (en) * | 1979-12-13 | 1981-07-01 | Eli Lilly And Company | Cyclic peptide nuclei |
| EP0744405A2 (en) * | 1995-05-26 | 1996-11-27 | Eli Lilly And Company | Cyclic peptide antifungal agents |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60030415T2 (de) | 2007-08-30 |
| CY1105777T1 (el) | 2011-02-02 |
| WO2000052036A1 (en) | 2000-09-08 |
| EP1155034B1 (en) | 2006-08-30 |
| US20020161176A1 (en) | 2002-10-31 |
| HK1040087A1 (zh) | 2002-05-24 |
| DK1155034T3 (da) | 2007-01-08 |
| BR0009248A (pt) | 2001-11-20 |
| WO2000052036A8 (en) | 2001-06-21 |
| AU3718200A (en) | 2000-09-21 |
| CN1351610A (zh) | 2002-05-29 |
| KR20020002476A (ko) | 2002-01-09 |
| PT1155034E (pt) | 2007-01-31 |
| JP2002538165A (ja) | 2002-11-12 |
| ATE338060T1 (de) | 2006-09-15 |
| IL145186A0 (en) | 2002-06-30 |
| ES2270819T3 (es) | 2007-04-16 |
| EP1155034A1 (en) | 2001-11-21 |
| ZA200107999B (en) | 2003-06-25 |
| DE60030415D1 (de) | 2006-10-12 |
| US6590073B2 (en) | 2003-07-08 |
| CA2362826A1 (en) | 2000-09-08 |
| JP4063497B2 (ja) | 2008-03-19 |
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