UA73774C2 - A method for the preparation of dihydroxy esters and derivatives thereof - Google Patents
A method for the preparation of dihydroxy esters and derivatives thereof Download PDFInfo
- Publication number
- UA73774C2 UA73774C2 UA2002129795A UA2002129795A UA73774C2 UA 73774 C2 UA73774 C2 UA 73774C2 UA 2002129795 A UA2002129795 A UA 2002129795A UA 2002129795 A UA2002129795 A UA 2002129795A UA 73774 C2 UA73774 C2 UA 73774C2
- Authority
- UA
- Ukraine
- Prior art keywords
- formula
- compound
- group
- optionally substituted
- lipase
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 150000002148 esters Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 8
- 238000005886 esterification reaction Methods 0.000 claims abstract description 7
- 238000011916 stereoselective reduction Methods 0.000 claims abstract description 7
- 230000032050 esterification Effects 0.000 claims abstract description 6
- 102000004882 Lipase Human genes 0.000 claims description 25
- 108090001060 Lipase Proteins 0.000 claims description 25
- 239000004367 Lipase Substances 0.000 claims description 22
- 235000019421 lipase Nutrition 0.000 claims description 22
- 229940040461 lipase Drugs 0.000 claims description 20
- 210000004027 cell Anatomy 0.000 claims description 16
- 102000004190 Enzymes Human genes 0.000 claims description 13
- 108090000790 Enzymes Proteins 0.000 claims description 13
- 229940088598 enzyme Drugs 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- 102000004157 Hydrolases Human genes 0.000 claims description 6
- 108090000604 Hydrolases Proteins 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 230000003993 interaction Effects 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 244000005700 microbiome Species 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 claims description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 3
- 210000002196 fr. b Anatomy 0.000 claims description 3
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 3
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 claims description 2
- 102000019280 Pancreatic lipases Human genes 0.000 claims description 2
- 108050006759 Pancreatic lipases Proteins 0.000 claims description 2
- 229940116369 pancreatic lipase Drugs 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 abstract 4
- 229930194542 Keto Natural products 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000002243 precursor Substances 0.000 abstract 2
- 125000005647 linker group Chemical group 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 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 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000008103 glucose Substances 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- XFNHABJTGIHGPN-UHFFFAOYSA-N tert-butyl 3,5,6-trihydroxyhexanoate Chemical compound CC(C)(C)OC(=O)CC(O)CC(O)CO XFNHABJTGIHGPN-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000010779 crude oil Substances 0.000 description 4
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 238000009901 transfer hydrogenation reaction Methods 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- -1 C..daloxy Chemical compound 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- IWESSOIVTTYRNX-UHFFFAOYSA-N tert-butyl 5,6-dihydroxy-3-oxohexanoate Chemical compound CC(C)(C)OC(=O)CC(=O)CC(O)CO IWESSOIVTTYRNX-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000011573 trace mineral Substances 0.000 description 3
- 235000013619 trace mineral Nutrition 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 241000256856 Vespidae Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000002906 microbiologic effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000012138 yeast extract Substances 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 1
- ZOWSJJBOQDKOHI-UHFFFAOYSA-N 2,2,2-trifluoroethyl acetate Chemical compound CC(=O)OCC(F)(F)F ZOWSJJBOQDKOHI-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 108010050375 Glucose 1-Dehydrogenase Proteins 0.000 description 1
- 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 1
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 description 1
- XJLXINKUBYWONI-NNYOXOHSSA-N NADP zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-NNYOXOHSSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 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 description 1
- 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 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- JIXOCHSERUXVMW-UHFFFAOYSA-M chlororuthenium Chemical compound [Ru]Cl JIXOCHSERUXVMW-UHFFFAOYSA-M 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 229950006238 nadide Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- PTMFUWGXPRYYMC-UHFFFAOYSA-N triethylazanium;formate Chemical compound OC=O.CCN(CC)CC PTMFUWGXPRYYMC-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
-
- 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
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
-
- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0011120.3A GB0011120D0 (en) | 2000-05-09 | 2000-05-09 | Process |
| PCT/GB2001/001915 WO2001085975A1 (en) | 2000-05-09 | 2001-05-01 | Process for the preparation of dihydroxy esters and derivatives thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA73774C2 true UA73774C2 (en) | 2005-09-15 |
Family
ID=9891211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2002129795A UA73774C2 (en) | 2000-05-09 | 2001-01-05 | A method for the preparation of dihydroxy esters and derivatives thereof |
Country Status (34)
| Country | Link |
|---|---|
| US (4) | US7157255B2 (xx) |
| EP (3) | EP1282719B1 (xx) |
| JP (1) | JP4733901B2 (xx) |
| KR (2) | KR100996977B1 (xx) |
| CN (1) | CN1196793C (xx) |
| AR (2) | AR028074A1 (xx) |
| AT (3) | ATE369437T1 (xx) |
| AU (2) | AU2001252383B2 (xx) |
| BR (1) | BR0110667A (xx) |
| CA (2) | CA2408004C (xx) |
| CY (3) | CY1105376T1 (xx) |
| CZ (3) | CZ302675B6 (xx) |
| DE (3) | DE60120685T2 (xx) |
| DK (3) | DK1657310T3 (xx) |
| EE (1) | EE05062B1 (xx) |
| ES (3) | ES2264981T3 (xx) |
| GB (1) | GB0011120D0 (xx) |
| HK (3) | HK1051708A1 (xx) |
| HU (1) | HUP0302216A3 (xx) |
| IL (4) | IL152608A0 (xx) |
| IS (1) | IS2290B (xx) |
| MX (1) | MXPA02010955A (xx) |
| MY (1) | MY127751A (xx) |
| NO (1) | NO20025377L (xx) |
| NZ (1) | NZ522407A (xx) |
| PL (3) | PL208379B1 (xx) |
| PT (3) | PT1657310E (xx) |
| RU (1) | RU2266961C2 (xx) |
| SI (3) | SI1282719T1 (xx) |
| SK (2) | SK287524B6 (xx) |
| TW (1) | TWI240753B (xx) |
| UA (1) | UA73774C2 (xx) |
| WO (1) | WO2001085975A1 (xx) |
| ZA (1) | ZA200208937B (xx) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0011120D0 (en) * | 2000-05-09 | 2000-06-28 | Avecia Ltd | Process |
| CA2380997A1 (en) * | 2000-06-05 | 2001-12-13 | Kaneka Corporation | Process for preparing optically active 2-¬6-(hydroxy-methyl)-1,3-dioxan-4-yl|acetic acid derivatives |
| NL1015744C2 (nl) | 2000-07-19 | 2002-01-22 | Dsm Nv | Werkwijze voor de bereiding van 2-(6-gesubstitueerde-1,3-dioxan-4-yl) azijnzuurderivaten. |
| EP1417180B1 (en) | 2001-07-13 | 2006-12-27 | AstraZeneca UK Limited | Preparation of aminopyrimidine compounds |
| EP1323717A1 (en) | 2001-12-27 | 2003-07-02 | Dsm N.V. | Process for the preparation of 2-(6-Substituted-1,3-Dioxane-4-yL) acetic acid derivatives |
| GB0211751D0 (en) * | 2002-05-22 | 2002-07-03 | Avecia Ltd | Compound and process |
| EP1375493A1 (en) | 2002-06-17 | 2004-01-02 | Dsm N.V. | Process for the preparation of an dioxane acetic acid ester |
| US6951877B2 (en) | 2002-07-19 | 2005-10-04 | Aryx Therapeutics, Inc. | Materials and methods for treating hypercholesterolemia |
| GB0218781D0 (en) | 2002-08-13 | 2002-09-18 | Astrazeneca Ab | Chemical process |
| EP2088142A3 (en) | 2002-12-16 | 2010-04-21 | AstraZeneca UK Limited | Dihydropyrimidines, process for their preparation and use thereof. |
| GB0312896D0 (en) | 2003-06-05 | 2003-07-09 | Astrazeneca Ab | Chemical process |
| UY28501A1 (es) | 2003-09-10 | 2005-04-29 | Astrazeneca Uk Ltd | Compuestos químicos |
| GB0324791D0 (en) | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Chemical process |
| GB0428328D0 (en) | 2004-12-24 | 2005-02-02 | Astrazeneca Uk Ltd | Chemical process |
| GB0514078D0 (en) * | 2005-07-08 | 2005-08-17 | Astrazeneca Uk Ltd | Chemical process |
| AT503017B1 (de) | 2005-12-19 | 2007-07-15 | Iep Gmbh | Verfahren zur enantioselektiven enzymatischen reduktion von hydroxyketoverbindungen |
| US7879585B2 (en) | 2006-10-02 | 2011-02-01 | Codexis, Inc. | Ketoreductase enzymes and uses thereof |
| TW200831469A (en) * | 2006-12-01 | 2008-08-01 | Astrazeneca Uk Ltd | Chemical process |
| CN101624609B (zh) * | 2009-07-31 | 2013-04-17 | 浙江九洲药业股份有限公司 | 酶催化制备(s)-3-取代戊二酸单酯类化合物的方法 |
| US8168686B2 (en) | 2010-12-22 | 2012-05-01 | Rentech, Inc. | Integrated biorefinery for production of liquid fuels |
| US8093306B2 (en) * | 2010-12-22 | 2012-01-10 | Rentech, Inc. | Integrated biorefinery for production of liquid fuels |
| CN102373250B (zh) * | 2011-11-08 | 2012-08-22 | 张家港市信谊化工有限公司 | 阿伐他汀钙侧链中间体的制备方法 |
| CN102618596A (zh) * | 2012-03-20 | 2012-08-01 | 中国药科大学 | 一种非水相体系中生物转化制备关附庚素的方法 |
| WO2014203045A1 (en) | 2013-06-20 | 2014-12-24 | Lupin Limited | A novel, green and cost effective process for synthesis of tert-butyl (3r,5s)-6-oxo-3,5-dihydroxy-3,5-o-isopropylidene-hexanoate |
| CN105503816B (zh) * | 2016-02-17 | 2018-02-13 | 中节能万润股份有限公司 | 一种固体(4R‑cis)‑6‑甲酰基‑2,2‑二甲基‑1,3‑二氧己环‑4‑乙酸叔丁酯的制备方法 |
| CN108530416B (zh) * | 2017-11-02 | 2020-05-12 | 江苏阿尔法药业有限公司 | 一种瑞舒伐他汀中间体的制备方法 |
| CN109574830B (zh) * | 2019-01-04 | 2021-04-13 | 浙江宏元药业股份有限公司 | 一种瑞舒伐他汀钙中间体及其制备方法和应用 |
| KR102384854B1 (ko) | 2021-06-15 | 2022-04-11 | 한대성 | 풀빅산 및 일라이트를 이용한 침대 |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB885516A (en) | 1958-01-16 | 1961-12-28 | Arthur Henry Clarkson | Higher fatty acid esters of dextran |
| US3325466A (en) | 1961-01-11 | 1967-06-13 | American Cyanamid Co | Tertiary butyl group as a carboxyl protecting group in the synthesis of peptides |
| GB1078709A (en) * | 1965-10-14 | 1967-08-09 | Lockspike Ltd | Fastening members for securing railway rails and railway rail and fastening arrangements employing the fastening members |
| US3992432A (en) * | 1967-04-05 | 1976-11-16 | Continental Oil Company | Phase transfer catalysis of heterogeneous reactions by quaternary salts |
| JPS5559140A (en) * | 1978-10-30 | 1980-05-02 | Sankyo Co Ltd | 3,5-dihydroxypentanoic alkyl ester derivative, its preparation and remedy for hyperlipemia containing the same as the effective component |
| GB9005966D0 (en) | 1990-03-16 | 1990-05-09 | May & Baker Ltd | New compositions of matter |
| JP3097143B2 (ja) | 1991-02-21 | 2000-10-10 | チッソ株式会社 | 生理活性物質合成用光学活性化合物の製造法および光学活性中間体化合物 |
| EP0604483A1 (en) | 1991-09-20 | 1994-07-06 | Zeneca Limited | Process for the preparation of enantiomerically pure 4-hydroxytetrahydro-2-pyranone derivatives |
| WO1993008823A1 (en) | 1991-11-06 | 1993-05-13 | Tanabe Seiyaku Co., Ltd. | Guanidinyl and related cell adhesion modulation compounds |
| US5278313A (en) * | 1992-03-27 | 1994-01-11 | E. R. Squibb & Sons, Inc. | Process for the preparation of 1,3-dioxane derivatives useful in the preparation of HMG-COA reductase inhibitors |
| US5324662A (en) * | 1992-05-15 | 1994-06-28 | E. R. Squibb & Sons, Inc. | Stereoselective microbial or enzymatic reduction of 3,5-dioxo esters to 3-hydroxy-5-oxo, 3-oxo-5-hydroxy, and 3,5-dihydroxy esters |
| EP0579370B1 (en) * | 1992-06-10 | 2000-08-16 | Chisso Corporation | An optically active 1,5-disubstituted-2,4-0-isoproylidene-2,4-dihydroxypentane and a process for producing the same |
| JP3491296B2 (ja) * | 1992-06-10 | 2004-01-26 | チッソ株式会社 | 光学活性１、５−ジ置換−２、４−ｏ−イソプロピリデン−２、４−ジヒドロキシペンタンおよびその製造法 |
| JP3076154B2 (ja) | 1992-08-13 | 2000-08-14 | 高砂香料工業株式会社 | （３ｒ，５ｓ）−３，５，６−トリヒドロキシヘキサン酸誘導体及びその製造方法 |
| JP3155107B2 (ja) * | 1993-01-12 | 2001-04-09 | ダイセル化学工業株式会社 | 光学活性４−ハロ−３−ヒドロキシ酪酸エステルの製造方法 |
| US5795749A (en) | 1995-04-05 | 1998-08-18 | The Scripps Research Institution | Use of 2-deoxyribose-5-phosphate aldolase to prepare 2-deoxyfucose, analogues and derivatives |
| JPH08336393A (ja) * | 1995-04-13 | 1996-12-24 | Mitsubishi Chem Corp | 光学活性なγ−置換−β−ヒドロキシ酪酸エステルの製造法 |
| GB9512837D0 (en) * | 1995-06-23 | 1995-08-23 | Zeneca Ltd | reduction of ketone groups |
| GB9523924D0 (en) | 1995-11-23 | 1996-01-24 | Zeneca Ltd | Production of optically active 2-substituted tetrahydropyran-4-ones |
| FR2741620B1 (fr) | 1995-11-28 | 1997-12-26 | Oreal | Procede de preparation de composes a groupement beta-hydroxy -delta-lactone analogues de la (+) compactine et de la (+) mevinoline |
| US6278001B1 (en) * | 1995-11-28 | 2001-08-21 | L'oréal | Method for preparing (+) compactin and (+) mevinolin analog compounds having a β-hydroxy-δ-lactone grouping |
| DE19610984A1 (de) * | 1996-03-21 | 1997-09-25 | Boehringer Mannheim Gmbh | Alkohol-Dehydrogenase und deren Verwendung zur enzymatischen Herstellung chiraler Hydroxyverbindungen |
| JPH11187869A (ja) * | 1997-12-25 | 1999-07-13 | Daicel Chem Ind Ltd | 新規な４−ハロアセト酢酸エステル還元酵素、該酵素の製造方法、及び該酵素を利用したアルコールの製造方法 |
| EP1077212B1 (en) * | 1998-04-30 | 2003-08-20 | Kaneka Corporation | Process for producing 6-cyanomethyl-1,3-dioxane-4-acetic acid derivatives |
| US6472544B1 (en) * | 1998-08-05 | 2002-10-29 | Kaneka Corporation | Process for the preparation of optically active 2-[6-hydroxymethyl)-1,3-dioxan-4yl]acetic acid derivatives |
| HUP0103021A3 (en) | 1998-12-10 | 2002-04-29 | Kaneka Corp | Process for producing simvastatin derivatives |
| DE19857302C2 (de) * | 1998-12-14 | 2000-10-26 | Forschungszentrum Juelich Gmbh | Verfahren zur enantioselektiven Reduktion von 3,5-Dioxocarbonsäuren, deren Salze und Ester |
| GB9903472D0 (en) * | 1999-02-17 | 1999-04-07 | Zeneca Ltd | Chemical process |
| HU227840B1 (en) | 1999-05-06 | 2012-05-02 | Egis Gyogyszergyar Nyilvanosan M Kod Ruszvunytarsasag | Intermediates of atorvastatin synthesis and process for producing them |
| ES2219345T3 (es) * | 1999-06-04 | 2004-12-01 | Kaneka Corporation | Procedimiento para la preparacion de derivados del acido 5-hidroxi-3-oxopentanoico. |
| JP2003504070A (ja) * | 1999-07-09 | 2003-02-04 | フォルシュングスツェントルム ユーリッヒ ゲゼルシャフト ミット ベシュレンクテル ハフツング | ケトカルボン酸及びそのエステルの還元のための方法 |
| AU2000254249A1 (en) | 2000-03-28 | 2001-10-08 | Biocon India Limited | Synthesis of (r-(r*,r*))-2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1- |
| GB0011120D0 (en) | 2000-05-09 | 2000-06-28 | Avecia Ltd | Process |
| CA2380997A1 (en) * | 2000-06-05 | 2001-12-13 | Kaneka Corporation | Process for preparing optically active 2-¬6-(hydroxy-methyl)-1,3-dioxan-4-yl|acetic acid derivatives |
| NL1015744C2 (nl) * | 2000-07-19 | 2002-01-22 | Dsm Nv | Werkwijze voor de bereiding van 2-(6-gesubstitueerde-1,3-dioxan-4-yl) azijnzuurderivaten. |
| EP1417180B1 (en) | 2001-07-13 | 2006-12-27 | AstraZeneca UK Limited | Preparation of aminopyrimidine compounds |
| EP1323717A1 (en) | 2001-12-27 | 2003-07-02 | Dsm N.V. | Process for the preparation of 2-(6-Substituted-1,3-Dioxane-4-yL) acetic acid derivatives |
| NZ534688A (en) * | 2002-02-25 | 2005-04-29 | Biocon Ltd | Novel boronate esters |
| KR100511533B1 (ko) | 2002-04-09 | 2005-08-31 | 임광민 | 키랄 중간체, 그의 제조방법 및 그를 이용한 HMG-CoA환원저해제의 제조방법 |
| EP1375493A1 (en) | 2002-06-17 | 2004-01-02 | Dsm N.V. | Process for the preparation of an dioxane acetic acid ester |
| GB0218781D0 (en) | 2002-08-13 | 2002-09-18 | Astrazeneca Ab | Chemical process |
| EP2088142A3 (en) | 2002-12-16 | 2010-04-21 | AstraZeneca UK Limited | Dihydropyrimidines, process for their preparation and use thereof. |
| GB0312896D0 (en) | 2003-06-05 | 2003-07-09 | Astrazeneca Ab | Chemical process |
| WO2004113314A1 (en) | 2003-06-23 | 2004-12-29 | Biocon Limited | Novel boronate esters |
| UY28501A1 (es) | 2003-09-10 | 2005-04-29 | Astrazeneca Uk Ltd | Compuestos químicos |
| GB0321827D0 (en) | 2003-09-18 | 2003-10-15 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0324791D0 (en) | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Chemical process |
| JP4266879B2 (ja) | 2004-05-12 | 2009-05-20 | 大阪瓦斯株式会社 | ガス化炉及び複合リサイクル装置 |
| US7161004B2 (en) * | 2004-06-21 | 2007-01-09 | Dr. Reddy's Laboratories Limited | Processes to produce intermediates for rosuvastatin |
| GB0428328D0 (en) | 2004-12-24 | 2005-02-02 | Astrazeneca Uk Ltd | Chemical process |
| GB0514078D0 (en) | 2005-07-08 | 2005-08-17 | Astrazeneca Uk Ltd | Chemical process |
| TW200831469A (en) | 2006-12-01 | 2008-08-01 | Astrazeneca Uk Ltd | Chemical process |
-
2000
- 2000-05-09 GB GBGB0011120.3A patent/GB0011120D0/en not_active Ceased
-
2001
- 2001-01-05 UA UA2002129795A patent/UA73774C2/uk unknown
- 2001-05-01 NZ NZ522407A patent/NZ522407A/en not_active IP Right Cessation
- 2001-05-01 JP JP2001582563A patent/JP4733901B2/ja not_active Expired - Lifetime
- 2001-05-01 EE EEP200200628A patent/EE05062B1/xx not_active IP Right Cessation
- 2001-05-01 CN CNB018124895A patent/CN1196793C/zh not_active Expired - Lifetime
- 2001-05-01 IL IL15260801A patent/IL152608A0/xx unknown
- 2001-05-01 AT AT06002032T patent/ATE369437T1/de active
- 2001-05-01 AU AU2001252383A patent/AU2001252383B2/en not_active Ceased
- 2001-05-01 PT PT06002032T patent/PT1657310E/pt unknown
- 2001-05-01 WO PCT/GB2001/001915 patent/WO2001085975A1/en active Application Filing
- 2001-05-01 ES ES01925699T patent/ES2264981T3/es not_active Expired - Lifetime
- 2001-05-01 DK DK06002032T patent/DK1657310T3/da active
- 2001-05-01 CZ CZ20110205A patent/CZ302675B6/cs not_active IP Right Cessation
- 2001-05-01 SI SI200130591T patent/SI1282719T1/sl unknown
- 2001-05-01 SK SK5088-2008A patent/SK287524B6/sk not_active IP Right Cessation
- 2001-05-01 US US10/275,092 patent/US7157255B2/en not_active Expired - Lifetime
- 2001-05-01 SI SI200130963T patent/SI1726658T1/sl unknown
- 2001-05-01 DE DE60120685T patent/DE60120685T2/de not_active Expired - Lifetime
- 2001-05-01 CA CA2408004A patent/CA2408004C/en not_active Expired - Fee Related
- 2001-05-01 SI SI200130758T patent/SI1657310T1/sl unknown
- 2001-05-01 HU HU0302216A patent/HUP0302216A3/hu unknown
- 2001-05-01 EP EP01925699A patent/EP1282719B1/en not_active Expired - Lifetime
- 2001-05-01 PL PL387244A patent/PL208379B1/pl not_active IP Right Cessation
- 2001-05-01 DE DE60129865T patent/DE60129865T2/de not_active Expired - Lifetime
- 2001-05-01 KR KR1020087005996A patent/KR100996977B1/ko not_active IP Right Cessation
- 2001-05-01 EP EP06019415A patent/EP1726658B1/en not_active Expired - Lifetime
- 2001-05-01 MX MXPA02010955A patent/MXPA02010955A/es active IP Right Grant
- 2001-05-01 SK SK1589-2002A patent/SK286746B6/sk not_active IP Right Cessation
- 2001-05-01 RU RU2002132884/13A patent/RU2266961C2/ru not_active IP Right Cessation
- 2001-05-01 AU AU5238301A patent/AU5238301A/xx active Pending
- 2001-05-01 PL PL359336A patent/PL208359B1/pl not_active IP Right Cessation
- 2001-05-01 CA CA002677945A patent/CA2677945A1/en not_active Abandoned
- 2001-05-01 CZ CZ20110204A patent/CZ302674B6/cs not_active IP Right Cessation
- 2001-05-01 EP EP06002032A patent/EP1657310B1/en not_active Expired - Lifetime
- 2001-05-01 BR BR0110667-8A patent/BR0110667A/pt not_active IP Right Cessation
- 2001-05-01 DK DK06019415.6T patent/DK1726658T3/da active
- 2001-05-01 ES ES06019415T patent/ES2340190T3/es not_active Expired - Lifetime
- 2001-05-01 AT AT06019415T patent/ATE458823T1/de active
- 2001-05-01 DK DK01925699T patent/DK1282719T3/da active
- 2001-05-01 DE DE60141424T patent/DE60141424D1/de not_active Expired - Lifetime
- 2001-05-01 PL PL387243A patent/PL208377B1/pl not_active IP Right Cessation
- 2001-05-01 ES ES06002032T patent/ES2289722T3/es not_active Expired - Lifetime
- 2001-05-01 PT PT06019415T patent/PT1726658E/pt unknown
- 2001-05-01 CZ CZ20023675A patent/CZ302632B6/cs not_active IP Right Cessation
- 2001-05-01 AT AT01925699T patent/ATE330020T1/de active
- 2001-05-01 PT PT01925699T patent/PT1282719E/pt unknown
- 2001-05-01 KR KR1020027014987A patent/KR100914675B1/ko not_active IP Right Cessation
- 2001-05-03 AR ARP010102091A patent/AR028074A1/es active IP Right Grant
- 2001-05-04 TW TW090110741A patent/TWI240753B/zh not_active IP Right Cessation
- 2001-05-08 MY MYPI20012105A patent/MY127751A/en unknown
-
2002
- 2002-11-03 IL IL152608A patent/IL152608A/en not_active IP Right Cessation
- 2002-11-04 ZA ZA200208937A patent/ZA200208937B/en unknown
- 2002-11-07 IS IS6609A patent/IS2290B/is unknown
- 2002-11-08 NO NO20025377A patent/NO20025377L/no not_active Application Discontinuation
-
2003
- 2003-06-05 HK HK03103991A patent/HK1051708A1/xx not_active IP Right Cessation
-
2006
- 2006-04-27 US US11/412,047 patent/US7416865B2/en not_active Expired - Lifetime
- 2006-09-12 CY CY20061101301T patent/CY1105376T1/el unknown
- 2006-09-22 HK HK06110633A patent/HK1090090A1/xx not_active IP Right Cessation
-
2007
- 2007-02-09 HK HK07101586.1A patent/HK1096998A1/xx not_active IP Right Cessation
- 2007-10-05 CY CY20071101270T patent/CY1106910T1/el unknown
-
2008
- 2008-07-23 US US12/178,424 patent/US7732171B2/en not_active Expired - Fee Related
- 2008-08-12 IL IL193404A patent/IL193404A/en not_active IP Right Cessation
- 2008-08-12 IL IL193405A patent/IL193405A/en not_active IP Right Cessation
- 2008-09-15 AR ARP080104001A patent/AR070946A2/es not_active Application Discontinuation
-
2010
- 2010-04-27 CY CY20101100376T patent/CY1109991T1/el unknown
- 2010-04-27 US US12/768,459 patent/US7888083B2/en not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| UA73774C2 (en) | A method for the preparation of dihydroxy esters and derivatives thereof | |
| AU2001252383A1 (en) | Process for the preparation of dihydroxy esters and derivatives thereof | |
| JPH06228053A (ja) | ２−メチレングルタール酸１−モノエステルとその製造法 |