IL134566A - Process for the biotransformation of colchicone compounds to the appropriate 3 O-glycosides - Google Patents
Process for the biotransformation of colchicone compounds to the appropriate 3 O-glycosidesInfo
- Publication number
- IL134566A IL134566A IL13456698A IL13456698A IL134566A IL 134566 A IL134566 A IL 134566A IL 13456698 A IL13456698 A IL 13456698A IL 13456698 A IL13456698 A IL 13456698A IL 134566 A IL134566 A IL 134566A
- Authority
- IL
- Israel
- Prior art keywords
- process according
- compounds
- biotransformation
- culture
- carried out
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- 230000036983 biotransformation Effects 0.000 title claims abstract description 26
- 230000008569 process Effects 0.000 title claims abstract description 24
- 150000001875 compounds Chemical class 0.000 title claims abstract description 22
- 230000000694 effects Effects 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
- 241000194107 Bacillus megaterium Species 0.000 claims abstract 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 22
- 239000000758 substrate Substances 0.000 claims description 22
- 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 claims description 9
- 239000008103 glucose Substances 0.000 claims description 9
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 238000005273 aeration Methods 0.000 claims description 6
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 6
- 239000001888 Peptone Substances 0.000 claims description 5
- 108010080698 Peptones Proteins 0.000 claims description 5
- 239000000284 extract Substances 0.000 claims description 5
- 235000013372 meat Nutrition 0.000 claims description 5
- 125000001477 organic nitrogen group Chemical group 0.000 claims description 5
- 235000019319 peptone Nutrition 0.000 claims description 5
- 229930091371 Fructose Natural products 0.000 claims description 4
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 4
- 239000005715 Fructose Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000012137 tryptone Substances 0.000 claims description 4
- 108010009736 Protein Hydrolysates Proteins 0.000 claims description 3
- 239000005018 casein Substances 0.000 claims description 3
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 claims description 3
- 235000021240 caseins Nutrition 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 150000002338 glycosides Chemical group 0.000 claims description 2
- ZXQYGBMAQZUVMI-QQDHXZELSA-N [cyano-(3-phenoxyphenyl)methyl] (1r,3r)-3-[(z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate Chemical class CC1(C)[C@@H](\C=C(/Cl)C(F)(F)F)[C@H]1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-QQDHXZELSA-N 0.000 claims 1
- 230000000259 anti-tumor effect Effects 0.000 abstract description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 1
- 125000003563 glycoside group Chemical group 0.000 abstract 1
- 235000010633 broth Nutrition 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 230000012010 growth Effects 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 244000005700 microbiome Species 0.000 description 11
- 238000000855 fermentation Methods 0.000 description 10
- 230000004151 fermentation Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000001963 growth medium Substances 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 230000009466 transformation Effects 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 7
- 238000011534 incubation Methods 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 239000012138 yeast extract Substances 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 230000000813 microbial effect Effects 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000005457 optimization Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 102000004357 Transferases Human genes 0.000 description 3
- 108090000992 Transferases Proteins 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 235000010419 agar Nutrition 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 229940041514 candida albicans extract Drugs 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000002054 inoculum Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000001131 transforming effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LMBIHYWAZRMYEM-UHFFFAOYSA-N 1,2,3-trimethoxy-10-methylsulfanyl-5,6-dihydrobenzo[a]heptalene-7,9-dione Chemical compound C1CC(=O)C2=CC(=O)C(SC)=CC=C2C2=C1C=C(OC)C(OC)=C2OC LMBIHYWAZRMYEM-UHFFFAOYSA-N 0.000 description 2
- VVPWAFWXRZAOAI-UHFFFAOYSA-N 1-chloroprop-1-en-2-ol Chemical compound CC(O)=CCl VVPWAFWXRZAOAI-UHFFFAOYSA-N 0.000 description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 238000009631 Broth culture Methods 0.000 description 2
- 102000051366 Glycosyltransferases Human genes 0.000 description 2
- 108700023372 Glycosyltransferases Proteins 0.000 description 2
- 239000006142 Luria-Bertani Agar Substances 0.000 description 2
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 2
- 229960001338 colchicine Drugs 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 235000013681 dietary sucrose Nutrition 0.000 description 2
- AIUDWMLXCFRVDR-UHFFFAOYSA-N dimethyl 2-(3-ethyl-3-methylpentyl)propanedioate Chemical class CCC(C)(CC)CCC(C(=O)OC)C(=O)OC AIUDWMLXCFRVDR-UHFFFAOYSA-N 0.000 description 2
- 238000011143 downstream manufacturing Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000012737 fresh medium Substances 0.000 description 2
- 229930182478 glucoside Natural products 0.000 description 2
- 150000008131 glucosides Chemical class 0.000 description 2
- 230000036512 infertility Effects 0.000 description 2
- 238000009630 liquid culture Methods 0.000 description 2
- 230000002906 microbiologic effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229940066779 peptones Drugs 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229960004793 sucrose Drugs 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000010257 thawing Methods 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000004382 Amylase Substances 0.000 description 1
- 241000193755 Bacillus cereus Species 0.000 description 1
- 241000051622 Bacillus meqaterium Species 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 102100034523 Histone H4 Human genes 0.000 description 1
- 101001067880 Homo sapiens Histone H4 Proteins 0.000 description 1
- LEQAKWQJCITZNK-AXHKHJLKSA-N N-[(7S)-1,2-dimethoxy-10-(methylthio)-9-oxo-3-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide Chemical compound C1([C@@H](NC(C)=O)CCC2=C3)=CC(=O)C(SC)=CC=C1C2=C(OC)C(OC)=C3O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O LEQAKWQJCITZNK-AXHKHJLKSA-N 0.000 description 1
- 206010029719 Nonspecific reaction Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 238000011138 biotechnological process Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000002031 ethanolic fraction Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 229940087061 glucosyl steviol Drugs 0.000 description 1
- 238000005858 glycosidation reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010829 isocratic elution Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 238000011206 morphological examination Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- CMEGANPVAXDBPL-INIZCTEOSA-N n-[(7s)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-6,7-dihydro-5h-benzo[a]heptalen-7-yl]acetamide Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(SC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC CMEGANPVAXDBPL-INIZCTEOSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 239000006152 selective media Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229960000287 thiocolchicoside Drugs 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 238000005820 transferase reaction Methods 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/56—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical directly bound to a condensed ring system having three or more carbocyclic rings, e.g. daunomycin, adriamycin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT97MI002255A IT1295272B1 (it) | 1997-10-03 | 1997-10-03 | Biotrasformazione di composti colchiconici nei corrispondenti 3- glicosilderivati |
| PCT/EP1998/006226 WO1999018229A1 (en) | 1997-10-03 | 1998-09-30 | A process for the biotransformation of colchicone compounds into the corresponding 3-glycosyl derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL134566A0 IL134566A0 (en) | 2001-04-30 |
| IL134566A true IL134566A (en) | 2004-06-20 |
Family
ID=11377985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL13456698A IL134566A (en) | 1997-10-03 | 1998-09-30 | Process for the biotransformation of colchicone compounds to the appropriate 3 O-glycosides |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6372458B1 (pl) |
| EP (1) | EP1019521B1 (pl) |
| KR (1) | KR100536676B1 (pl) |
| CN (1) | CN1188527C (pl) |
| AT (1) | ATE328106T1 (pl) |
| AU (1) | AU745222B2 (pl) |
| CA (1) | CA2305046C (pl) |
| CZ (1) | CZ295749B6 (pl) |
| DE (1) | DE69834736T2 (pl) |
| DK (1) | DK1019521T3 (pl) |
| ES (1) | ES2264214T3 (pl) |
| HU (1) | HU225686B1 (pl) |
| IL (1) | IL134566A (pl) |
| IT (1) | IT1295272B1 (pl) |
| NO (1) | NO320096B1 (pl) |
| PL (1) | PL190865B1 (pl) |
| PT (1) | PT1019521E (pl) |
| RU (1) | RU2218409C2 (pl) |
| SK (1) | SK285923B6 (pl) |
| WO (1) | WO1999018229A1 (pl) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040175782A1 (en) * | 2003-03-06 | 2004-09-09 | Tethys Research Llc | Biotransformation of compounds using non-prokaryotic microalgae |
| US7910334B2 (en) * | 2004-05-12 | 2011-03-22 | Indena S.P.A. | Biotransformation of colchicinoid compounds |
| US8795986B2 (en) * | 2010-09-22 | 2014-08-05 | Sequent Scientific Ltd. | Microbial method for the biotransformation of colchicinoid compounds |
| WO2015097567A1 (en) | 2013-12-23 | 2015-07-02 | Alkaloids Corporation | Process for the conversion of colchicinoids to their 3-glycosylated derivatives via their respective 3-demethyl analogues |
| CN105861601B (zh) * | 2016-04-29 | 2019-05-24 | 中国药科大学 | 一种生物转化制备二氢去氢双松柏醇葡萄糖单糖苷(hmzg)的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1344157A (fr) * | 1959-05-22 | 1963-11-29 | Roussel Uclaf | Nouvelles colchicines et leur procédé d'obtention |
| US3442953A (en) * | 1963-06-19 | 1969-05-06 | Roussel Uclaf | Novel 7-oxo-7-desacetylaminocolchicine compounds |
| JPS5233195B2 (pl) * | 1971-09-30 | 1977-08-26 | ||
| IT1285777B1 (it) * | 1996-10-07 | 1998-06-18 | Indena Spa | Processo di biotrasformazione di composti colchicinoidi nei corrispondenti 3-glicosilderivati |
-
1997
- 1997-10-03 IT IT97MI002255A patent/IT1295272B1/it active IP Right Grant
-
1998
- 1998-09-30 AT AT98952675T patent/ATE328106T1/de active
- 1998-09-30 CN CNB988098180A patent/CN1188527C/zh not_active Expired - Fee Related
- 1998-09-30 RU RU2000111512/13A patent/RU2218409C2/ru not_active IP Right Cessation
- 1998-09-30 DK DK98952675T patent/DK1019521T3/da active
- 1998-09-30 WO PCT/EP1998/006226 patent/WO1999018229A1/en not_active Ceased
- 1998-09-30 PL PL339620A patent/PL190865B1/pl unknown
- 1998-09-30 HU HU0004840A patent/HU225686B1/hu not_active IP Right Cessation
- 1998-09-30 PT PT98952675T patent/PT1019521E/pt unknown
- 1998-09-30 CZ CZ20001196A patent/CZ295749B6/cs not_active IP Right Cessation
- 1998-09-30 ES ES98952675T patent/ES2264214T3/es not_active Expired - Lifetime
- 1998-09-30 AU AU10283/99A patent/AU745222B2/en not_active Ceased
- 1998-09-30 EP EP98952675A patent/EP1019521B1/en not_active Expired - Lifetime
- 1998-09-30 CA CA002305046A patent/CA2305046C/en not_active Expired - Fee Related
- 1998-09-30 KR KR10-2000-7003216A patent/KR100536676B1/ko not_active Expired - Fee Related
- 1998-09-30 DE DE69834736T patent/DE69834736T2/de not_active Expired - Lifetime
- 1998-09-30 SK SK483-2000A patent/SK285923B6/sk not_active IP Right Cessation
- 1998-09-30 IL IL13456698A patent/IL134566A/en not_active IP Right Cessation
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2000
- 2000-03-31 US US09/539,867 patent/US6372458B1/en not_active Expired - Lifetime
- 2000-04-03 NO NO20001706A patent/NO320096B1/no not_active IP Right Cessation
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