NO309600B1 - Forbedret fremgangsmåte for fremstilling av 4-hydroksy-2- pyrrolidon - Google Patents
Forbedret fremgangsmåte for fremstilling av 4-hydroksy-2- pyrrolidon Download PDFInfo
- Publication number
- NO309600B1 NO309600B1 NO975281A NO975281A NO309600B1 NO 309600 B1 NO309600 B1 NO 309600B1 NO 975281 A NO975281 A NO 975281A NO 975281 A NO975281 A NO 975281A NO 309600 B1 NO309600 B1 NO 309600B1
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy
- hydroxybutyrate
- pyrrolidone
- compound
- azide
- Prior art date
Links
- IOGISYQVOGVIEU-UHFFFAOYSA-N 4-hydroxypyrrolidin-2-one Chemical compound OC1CNC(=O)C1 IOGISYQVOGVIEU-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title description 8
- -1 alkaline earth metal azide Chemical class 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 9
- YURPXDJXGNHJIR-UHFFFAOYSA-N 4-azido-3-hydroxybutanoic acid Chemical compound OC(=O)CC(O)CN=[N+]=[N-] YURPXDJXGNHJIR-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 7
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 16
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000003905 agrochemical Substances 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- YQGDEPYYFWUPGO-UHFFFAOYSA-N gamma-amino-beta-hydroxybutyric acid Chemical compound [NH3+]CC(O)CC([O-])=O YQGDEPYYFWUPGO-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229960002298 aminohydroxybutyric acid Drugs 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 3
- AKDAXGMVRMXFOO-UHFFFAOYSA-N 4-chloro-3-hydroxybutanoic acid Chemical compound ClCC(O)CC(O)=O AKDAXGMVRMXFOO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- WMRINGSAVOPXTE-UHFFFAOYSA-N methyl 4-chloro-3-hydroxybutanoate Chemical compound COC(=O)CC(O)CCl WMRINGSAVOPXTE-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 3
- 230000006340 racemization Effects 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IOGISYQVOGVIEU-VKHMYHEASA-N (4s)-4-hydroxypyrrolidin-2-one Chemical compound O[C@@H]1CNC(=O)C1 IOGISYQVOGVIEU-VKHMYHEASA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229960002591 hydroxyproline Drugs 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- AKDAXGMVRMXFOO-VKHMYHEASA-N (3s)-4-chloro-3-hydroxybutanoic acid Chemical compound ClC[C@@H](O)CC(O)=O AKDAXGMVRMXFOO-VKHMYHEASA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- GYHZLNKMZPYTFB-UHFFFAOYSA-N 2-(oxiran-2-yl)acetamide Chemical compound NC(=O)CC1CO1 GYHZLNKMZPYTFB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OEFYMRNJCRZYKF-UHFFFAOYSA-N butyl 4-bromo-3-hydroxybutanoate Chemical compound CCCCOC(=O)CC(O)CBr OEFYMRNJCRZYKF-UHFFFAOYSA-N 0.000 description 1
- KUWKPNMTVKBQTH-UHFFFAOYSA-N butyl 4-chloro-3-hydroxybutanoate Chemical compound CCCCOC(=O)CC(O)CCl KUWKPNMTVKBQTH-UHFFFAOYSA-N 0.000 description 1
- XQPRBTXUXXVTKB-UHFFFAOYSA-M caesium iodide Chemical compound [I-].[Cs+] XQPRBTXUXXVTKB-UHFFFAOYSA-M 0.000 description 1
- UETLMBWMVIQIGU-UHFFFAOYSA-N calcium azide Chemical compound [Ca+2].[N-]=[N+]=[N-].[N-]=[N+]=[N-] UETLMBWMVIQIGU-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- KTHXBEHDVMTNOH-UHFFFAOYSA-N cyclobutanol Chemical class OC1CCC1 KTHXBEHDVMTNOH-UHFFFAOYSA-N 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 238000005828 desilylation reaction Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- MTAYETVPZNVYFE-YFKPBYRVSA-N ethyl (3s)-4-azido-3-hydroxybutanoate Chemical compound CCOC(=O)C[C@H](O)CN=[N+]=[N-] MTAYETVPZNVYFE-YFKPBYRVSA-N 0.000 description 1
- ZAJNMXDBJKCCAT-YFKPBYRVSA-N ethyl (3s)-4-chloro-3-hydroxybutanoate Chemical compound CCOC(=O)C[C@H](O)CCl ZAJNMXDBJKCCAT-YFKPBYRVSA-N 0.000 description 1
- AIZRKZQHJNWBEI-UHFFFAOYSA-N ethyl 4-bromo-3-hydroxybutanoate Chemical compound CCOC(=O)CC(O)CBr AIZRKZQHJNWBEI-UHFFFAOYSA-N 0.000 description 1
- ZAJNMXDBJKCCAT-UHFFFAOYSA-N ethyl 4-chloro-3-hydroxybutanoate Chemical compound CCOC(=O)CC(O)CCl ZAJNMXDBJKCCAT-UHFFFAOYSA-N 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- OCHWGGFGBGWTAV-UHFFFAOYSA-N methyl 4-azido-3-hydroxybutanoate Chemical compound COC(=O)CC(O)CN=[N+]=[N-] OCHWGGFGBGWTAV-UHFFFAOYSA-N 0.000 description 1
- MBBQAVVBESBLGH-UHFFFAOYSA-N methyl 4-bromo-3-hydroxybutanoate Chemical compound COC(=O)CC(O)CBr MBBQAVVBESBLGH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- WUFHKFWXUZJOTL-UHFFFAOYSA-N propan-2-yl 4-bromo-3-hydroxybutanoate Chemical compound CC(C)OC(=O)CC(O)CBr WUFHKFWXUZJOTL-UHFFFAOYSA-N 0.000 description 1
- BZXNYWHUGJDAFS-UHFFFAOYSA-N propan-2-yl 4-chloro-3-hydroxybutanoate Chemical compound CC(C)OC(=O)CC(O)CCl BZXNYWHUGJDAFS-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JOLRPTUDEYUBRN-UHFFFAOYSA-N tert-butyl 4-bromo-3-hydroxybutanoate Chemical compound CC(C)(C)OC(=O)CC(O)CBr JOLRPTUDEYUBRN-UHFFFAOYSA-N 0.000 description 1
- FTNVTERIGHWULD-UHFFFAOYSA-N tert-butyl 4-chloro-3-hydroxybutanoate Chemical compound CC(C)(C)OC(=O)CC(O)CCl FTNVTERIGHWULD-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12167595A JP3831954B2 (ja) | 1995-05-19 | 1995-05-19 | ４−ヒドロキシ−２−ピロリドンの製法 |
| PCT/JP1996/001259 WO1996036603A1 (fr) | 1995-05-19 | 1996-05-14 | Procede ameliore pour preparer la 4-hydroxy-2-pyrrolidone |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO975281D0 NO975281D0 (no) | 1997-11-18 |
| NO975281L NO975281L (no) | 1997-11-18 |
| NO309600B1 true NO309600B1 (no) | 2001-02-26 |
Family
ID=14817108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO975281A NO309600B1 (no) | 1995-05-19 | 1997-11-18 | Forbedret fremgangsmåte for fremstilling av 4-hydroksy-2- pyrrolidon |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5869694A (ja) |
| EP (1) | EP0829472B1 (ja) |
| JP (1) | JP3831954B2 (ja) |
| KR (1) | KR100369274B1 (ja) |
| AT (1) | ATE222585T1 (ja) |
| CA (1) | CA2221641A1 (ja) |
| DE (1) | DE69623117T2 (ja) |
| NO (1) | NO309600B1 (ja) |
| TW (1) | TW326444B (ja) |
| WO (1) | WO1996036603A1 (ja) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3140698B2 (ja) * | 1996-11-26 | 2001-03-05 | ダイセル化学工業株式会社 | ４−ヒドロキシ−２−ピロリジノンの製造方法ならびに精製方法 |
| US6252089B1 (en) | 1997-11-25 | 2001-06-26 | Daicel Chemical Industries, Ltd. | Method of producing 4-hydroxy-2-pyrrolidinone and method of purifying the same |
| JP4187822B2 (ja) * | 1998-03-31 | 2008-11-26 | 高砂香料工業株式会社 | 光学活性４−ヒドロキシ−２−ピロリドンの製造方法 |
| US6492083B1 (en) | 2001-05-11 | 2002-12-10 | Lexmark International, Inc. | Toner comprising wax and functionalized enhancing agent |
| KR100710558B1 (ko) * | 2001-12-03 | 2007-04-24 | 에스케이 주식회사 | 광학적으로 순수한 (ｓ)-4-히드록시-2-피롤리돈의연속제조방법 |
| CA2602073A1 (en) * | 2005-02-24 | 2006-08-31 | Teva Pharmaceutical Industries Ltd. | Processes for the preparation of linezolid intermediate |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE792181A (fr) * | 1971-12-02 | 1973-06-01 | Hoffmann La Roche | Derives de l'acide citrique |
| JPS5812272B2 (ja) * | 1981-04-28 | 1983-03-07 | 電気化学工業株式会社 | ４−ヒドロキシ−２−ピロリドンの製造法 |
| JPS61176564A (ja) * | 1985-01-30 | 1986-08-08 | Kyowa Hakko Kogyo Co Ltd | ４−ヒドロキシ−２−ピロリドンの製造法 |
| JPS63174957A (ja) * | 1987-01-13 | 1988-07-19 | Osaka Soda Co Ltd | ４−アミノ−３−ヒドロキシ酪酸の製法 |
-
1995
- 1995-05-19 JP JP12167595A patent/JP3831954B2/ja not_active Expired - Fee Related
-
1996
- 1996-05-14 WO PCT/JP1996/001259 patent/WO1996036603A1/ja active IP Right Grant
- 1996-05-14 DE DE69623117T patent/DE69623117T2/de not_active Expired - Fee Related
- 1996-05-14 KR KR1019970707938A patent/KR100369274B1/ko not_active IP Right Cessation
- 1996-05-14 CA CA002221641A patent/CA2221641A1/en not_active Abandoned
- 1996-05-14 AT AT96913738T patent/ATE222585T1/de not_active IP Right Cessation
- 1996-05-14 EP EP96913738A patent/EP0829472B1/en not_active Expired - Lifetime
- 1996-05-14 US US08/973,162 patent/US5869694A/en not_active Expired - Lifetime
- 1996-05-15 TW TW085105722A patent/TW326444B/zh active
-
1997
- 1997-11-18 NO NO975281A patent/NO309600B1/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JPH08311025A (ja) | 1996-11-26 |
| WO1996036603A1 (fr) | 1996-11-21 |
| NO975281D0 (no) | 1997-11-18 |
| NO975281L (no) | 1997-11-18 |
| KR100369274B1 (ko) | 2003-05-17 |
| TW326444B (en) | 1998-02-11 |
| CA2221641A1 (en) | 1996-11-21 |
| JP3831954B2 (ja) | 2006-10-11 |
| EP0829472B1 (en) | 2002-08-21 |
| EP0829472A1 (en) | 1998-03-18 |
| US5869694A (en) | 1999-02-09 |
| EP0829472A4 (en) | 1998-12-02 |
| DE69623117T2 (de) | 2003-05-08 |
| DE69623117D1 (de) | 2002-09-26 |
| KR19990008411A (ko) | 1999-01-25 |
| ATE222585T1 (de) | 2002-09-15 |
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| FC2A | Withdrawal, rejection or dismissal of laid open patent application |