FI93741B - Förfarande för framställning av optiskt rena (2S,3S)- och (2R,3R)-threo-alkyl-2-hydroxi-3-(4-metoxifenyl)-3-(2-X-fenyltio)propionater eller motsvarande acylerade föreningar - Google Patents
Förfarande för framställning av optiskt rena (2S,3S)- och (2R,3R)-threo-alkyl-2-hydroxi-3-(4-metoxifenyl)-3-(2-X-fenyltio)propionater eller motsvarande acylerade föreningar Download PDFInfo
- Publication number
- FI93741B FI93741B FI931298A FI931298A FI93741B FI 93741 B FI93741 B FI 93741B FI 931298 A FI931298 A FI 931298A FI 931298 A FI931298 A FI 931298A FI 93741 B FI93741 B FI 93741B
- Authority
- FI
- Finland
- Prior art keywords
- methoxyphenyl
- phenylthio
- compound
- enzyme
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 26
- 150000001875 compounds Chemical class 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 12
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 title claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 title claims description 6
- 102000004190 Enzymes Human genes 0.000 claims description 32
- 108090000790 Enzymes Proteins 0.000 claims description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 25
- 102000004882 Lipase Human genes 0.000 claims description 19
- 108090001060 Lipase Proteins 0.000 claims description 19
- 239000004367 Lipase Substances 0.000 claims description 19
- 235000019421 lipase Nutrition 0.000 claims description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- 238000005917 acylation reaction Methods 0.000 claims description 10
- 230000010933 acylation Effects 0.000 claims description 9
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- -1 CH 3 Chemical group 0.000 claims description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005909 Kieselgur Substances 0.000 claims description 3
- IKGQWEZMFQRDMA-UHFFFAOYSA-N acetic acid;n-propan-2-ylidenehydroxylamine Chemical compound CC(O)=O.CC(C)=NO IKGQWEZMFQRDMA-UHFFFAOYSA-N 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 238000001640 fractional crystallisation Methods 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 229920001567 vinyl ester resin Polymers 0.000 claims description 3
- 241000589513 Burkholderia cepacia Species 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 12
- 239000003480 eluent Substances 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
- 229960004166 diltiazem Drugs 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 6
- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 244000309464 bull Species 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000019766 L-Lysine Nutrition 0.000 description 3
- 239000004472 Lysine Substances 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
- 239000011942 biocatalyst Substances 0.000 description 3
- 230000002210 biocatalytic effect Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229940125890 compound Ia Drugs 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 108010093096 Immobilized Enzymes Proteins 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000179532 [Candida] cylindracea Species 0.000 description 2
- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 238000007281 aminoalkylation reaction Methods 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- VGLKHVQPWGFXEG-NCJHBDPTSA-K europium(3+);(1z)-2,2,3,3,4,4,4-heptafluoro-1-(4,7,7-trimethyl-3-oxo-2-bicyclo[2.2.1]heptanylidene)butan-1-olate Chemical compound [Eu+3].C1CC2(C)C(=O)\C(=C(/[O-])C(F)(F)C(F)(F)C(F)(F)F)C1C2(C)C.C1CC2(C)C(=O)\C(=C(/[O-])C(F)(F)C(F)(F)C(F)(F)F)C1C2(C)C.C1CC2(C)C(=O)\C(=C(/[O-])C(F)(F)C(F)(F)C(F)(F)F)C1C2(C)C VGLKHVQPWGFXEG-NCJHBDPTSA-K 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical group SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JNPGUXGVLNJQSQ-BGGMYYEUSA-M (e,3r,5s)-7-[4-(4-fluorophenyl)-1,2-di(propan-2-yl)pyrrol-3-yl]-3,5-dihydroxyhept-6-enoate Chemical compound CC(C)N1C(C(C)C)=C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)C(C=2C=CC(F)=CC=2)=C1 JNPGUXGVLNJQSQ-BGGMYYEUSA-M 0.000 description 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZLGALPUSFOPSBM-UHFFFAOYSA-N 2-(2-nitrophenyl)sulfanylpropanoic acid Chemical compound OC(=O)C(C)SC1=CC=CC=C1[N+]([O-])=O ZLGALPUSFOPSBM-UHFFFAOYSA-N 0.000 description 1
- CXSYMIMVXMVRMC-UHFFFAOYSA-N 3-(2-aminophenyl)sulfanyl-2-methoxy-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(OC)(C(O)=O)CSC1=CC=CC=C1N CXSYMIMVXMVRMC-UHFFFAOYSA-N 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 108090000312 Calcium Channels Proteins 0.000 description 1
- 102000003922 Calcium Channels Human genes 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 238000010268 HPLC based assay Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000235403 Rhizomucor miehei Species 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
- 229930006000 Sucrose Natural products 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
-
- 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
- C12P11/00—Preparation of sulfur-containing organic compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Analytical Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Claims (6)
1. Förfarande för framställning av (2S,3S)-i/»reo-alkyl-2-hydroxi-3-(4-metoxifenyl)-3-(2-X-fenyltio)propionater och (2R,3R)-/Areo-alkyl-2-acyloxi-3-(4-metoxifenyl)-3-(2-X- 5 fenyltio)propionater med formel 1 och 2 CH,0 CH,0 CH,0 Öo„ Lipas>^_^0H + ;co» COjR, S COjR, s ¢0,8, α α σ' racemisk 11 2 (2S.3S) (2R.3R) kännetecknat därav, att den rasemiska föreningens, med formeln 1, (2R.3R) -enantiomer där X är N02, NH2, NHCOCH3, NHCOCF3, NHC02CH3, NHC02(CH3)3 15 eller NHCHO och R, är en alkyl grupp, acyleras i vattenfritt organiskt lösningsmedel, katalyserad med en lipas, och efter acylering föreningen med formeln 1 separeras frän föreningen med formeln 2.
2. Förfarande enligt patentkrav 1, kännetecknat därav, att lipasen är lipasen av
20 Pseudomonas cepacia.
3. Förfarande enligt nägot av patentkraven 1-2, kännetecknat därav, att enzymet är använt som isolerat pulver eller det är immobiliserat pä ett kiselguhr baserat bärmedel. 25
4. Förfarande enligt nägot av patentkraven 1-3, kännetecknat därav, att syraanhydrider, vinylestrar eller acetonoximacetat används som acyleringsreagens. ,5 93741
5. Förfarande enligt nägot av patentkraven 1-4, kännetecknat därav att dietyleter, toluen, tetrahydrofuran, di-isopropyleter eller vinylacetat används som lösningsmedel.
6. Förfarande enligt nägot av patentkraven 1-5, kännetecknat därav att, föreningen 5 (2S,3S)-fAreo-alkyl-2-hydroxi-3-(4-metoxifenyl)-3-(2-X-fenyltio)propionat separeras frän föreningen (2R,3R)-iAreo-alkyl-2-acyIoxi-3-(4-metoxifenyl)-3-(2-X-fenyltio)propionat med tillhjälp av fraktioneringskristallisation eller kromatografi.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI931298A FI93741C (sv) | 1993-03-24 | 1993-03-24 | Förfarande för framställning av optiskt rena (2S,3S)- och (2R,3R)-threo-alkyl-2-hydroxi-3-(4-metoxifenyl)-3-(2-X-fenyltio)propionater eller motsvarande acylerade föreningar |
| HU9400762A HU216797B (hu) | 1993-03-24 | 1994-03-12 | Eljárás a (2S, 3S)-treo-2-hidroxi-3-(4-metoxi-fenil)-3-(fenil-tio)- és (2R, 3R)-treo-2-alkanoil-oxi-3-(4-metoxi-fenil)-3-(fenil-tio)-propionát-származékok előállítására |
| IL109041A IL109041A (en) | 1993-03-24 | 1994-03-18 | Method for the manufacture of optically pure (2s, 3s) - threoalkyl) -2-hydroxy-3- (4-methoxyphenyl)- 3-phenylthiopropionates and (2r, 3r) threo-alkyl- 2-acetoxy-3- (4-methoxyphenyl)-3- phenylthiopropionates |
| US08/215,529 US5514589A (en) | 1993-03-24 | 1994-03-22 | Chiral resolution of an intermediate in diltiazem synthesis using lipase PS immobilized with sucrose |
| EP94104620A EP0617130A3 (en) | 1993-03-24 | 1994-03-23 | Method for solving racemic mixtures. |
| CA002119670A CA2119670A1 (en) | 1993-03-24 | 1994-03-23 | Chiral resolution of an intermediate in diltiazem synthesis using lipase |
| JP6054169A JP2612671B2 (ja) | 1993-03-24 | 1994-03-24 | 光学活性なプロピオン酸エステルの製造法 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI931298A FI93741C (sv) | 1993-03-24 | 1993-03-24 | Förfarande för framställning av optiskt rena (2S,3S)- och (2R,3R)-threo-alkyl-2-hydroxi-3-(4-metoxifenyl)-3-(2-X-fenyltio)propionater eller motsvarande acylerade föreningar |
| FI931298 | 1993-03-24 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI931298A0 FI931298A0 (sv) | 1993-03-24 |
| FI931298L FI931298L (sv) | 1994-09-25 |
| FI93741B true FI93741B (sv) | 1995-02-15 |
| FI93741C FI93741C (sv) | 1995-05-26 |
Family
ID=8537616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI931298A FI93741C (sv) | 1993-03-24 | 1993-03-24 | Förfarande för framställning av optiskt rena (2S,3S)- och (2R,3R)-threo-alkyl-2-hydroxi-3-(4-metoxifenyl)-3-(2-X-fenyltio)propionater eller motsvarande acylerade föreningar |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5514589A (sv) |
| EP (1) | EP0617130A3 (sv) |
| JP (1) | JP2612671B2 (sv) |
| CA (1) | CA2119670A1 (sv) |
| FI (1) | FI93741C (sv) |
| HU (1) | HU216797B (sv) |
| IL (1) | IL109041A (sv) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI97725C (sv) * | 1995-02-17 | 1997-02-10 | Orion Yhtymae Oy | Förfarande för framställning av diltiazem |
| IT1295376B1 (it) * | 1997-10-22 | 1999-05-12 | Zambon Spa | Processo per il riciclo di un sottoprodotto della sintesi del diltiazem |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1152721B (it) * | 1982-10-15 | 1987-01-07 | Luso Farmaco Inst | Risoluzione ottica dell'acido dl-alfa-2-idrossi-3-(4-metossifenil)-3-(2-amminofeniltio)propionico |
| JPS6032775A (ja) * | 1983-07-30 | 1985-02-19 | Daikin Ind Ltd | 含フッ素ベンゾジアゼピン類 |
| CA1329214C (en) * | 1988-05-18 | 1994-05-03 | James T. Palmer | 2-hydroxy-3-(4-methoxyphenyl)-3-(2- aminophenylthio)propionic acid, 8'-phenylmenthyl ester, especially for diltiazem |
| US4908469A (en) * | 1988-05-18 | 1990-03-13 | Marion Laboratories, Inc. | 2-Hydroxy-propanoic acid acyclic alkyl esters for benzothiazepines |
| IT1226300B (it) * | 1988-07-26 | 1990-12-27 | Zambon Spa | Processo per la preparazione di intermedi per la sintesi del diltiazem. |
| JPH02190195A (ja) * | 1989-01-19 | 1990-07-26 | Rikagaku Kenkyusho | 光学活性プロピオン酸エステル類化合物の製法 |
| IT1232306B (it) * | 1989-07-27 | 1992-01-28 | Zambon Spa | Processo di risoluzione di intermedi utili per la preparazione del diltiazem |
| US5210030A (en) * | 1990-06-25 | 1993-05-11 | Merck & Co., Inc. | Process for selectively acylating immunomycin |
| FR2672600B1 (fr) * | 1991-02-08 | 1994-10-14 | Synthelabo | Procede de preparation du (-)-(2r,3s)-2,3-epoxy-3-(4-methoxyphenyl) propionate de methyle. |
-
1993
- 1993-03-24 FI FI931298A patent/FI93741C/sv active
-
1994
- 1994-03-12 HU HU9400762A patent/HU216797B/hu not_active IP Right Cessation
- 1994-03-18 IL IL109041A patent/IL109041A/en not_active IP Right Cessation
- 1994-03-22 US US08/215,529 patent/US5514589A/en not_active Expired - Fee Related
- 1994-03-23 CA CA002119670A patent/CA2119670A1/en not_active Abandoned
- 1994-03-23 EP EP94104620A patent/EP0617130A3/en not_active Ceased
- 1994-03-24 JP JP6054169A patent/JP2612671B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2119670A1 (en) | 1994-09-25 |
| HU216797B (hu) | 1999-08-30 |
| US5514589A (en) | 1996-05-07 |
| EP0617130A3 (en) | 1995-03-08 |
| FI931298L (sv) | 1994-09-25 |
| EP0617130A2 (en) | 1994-09-28 |
| IL109041A0 (en) | 1994-08-26 |
| JPH07303495A (ja) | 1995-11-21 |
| HU9400762D0 (en) | 1994-06-28 |
| IL109041A (en) | 1998-02-08 |
| FI931298A0 (sv) | 1993-03-24 |
| FI93741C (sv) | 1995-05-26 |
| JP2612671B2 (ja) | 1997-05-21 |
| HUT70752A (en) | 1995-10-30 |
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| BB | Publication of examined application |