JP2000509068A - エナンチオマーとして純粋なアゼチジン―２―カルボン酸の改良された製造方法 - Google Patents
エナンチオマーとして純粋なアゼチジン―２―カルボン酸の改良された製造方法Info
- Publication number
- JP2000509068A JP2000509068A JP9538797A JP53879797A JP2000509068A JP 2000509068 A JP2000509068 A JP 2000509068A JP 9538797 A JP9538797 A JP 9538797A JP 53879797 A JP53879797 A JP 53879797A JP 2000509068 A JP2000509068 A JP 2000509068A
- Authority
- JP
- Japan
- Prior art keywords
- azeoh
- tartaric acid
- aldehyde
- acid
- tartrate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- IADUEWIQBXOCDZ-VKHMYHEASA-N Azetidine-2-carboxylic acid Natural products OC(=O)[C@@H]1CCN1 IADUEWIQBXOCDZ-VKHMYHEASA-N 0.000 title claims abstract description 52
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- IADUEWIQBXOCDZ-UHFFFAOYSA-N azetidine-2-carboxylic acid Chemical compound OC(=O)C1CCN1 IADUEWIQBXOCDZ-UHFFFAOYSA-N 0.000 title claims description 10
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims abstract description 29
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000007524 organic acids Chemical class 0.000 claims abstract description 15
- 235000002906 tartaric acid Nutrition 0.000 claims abstract description 15
- 239000011975 tartaric acid Substances 0.000 claims abstract description 15
- 229940095064 tartrate Drugs 0.000 claims abstract description 14
- 150000001413 amino acids Chemical class 0.000 claims abstract description 12
- 239000012456 homogeneous solution Substances 0.000 claims abstract description 8
- 238000010956 selective crystallization Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 150000001299 aldehydes Chemical class 0.000 claims description 17
- 229960001367 tartaric acid Drugs 0.000 claims description 14
- 229960001270 d- tartaric acid Drugs 0.000 claims description 13
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical group CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 8
- 235000005985 organic acids Nutrition 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 2
- 239000001110 calcium chloride Substances 0.000 claims description 2
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims 1
- 230000001588 bifunctional effect Effects 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229940024606 amino acid Drugs 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- MWIXENPCUPDSOS-QMMMGPOBSA-N (2s)-2-amino-3-(4-hydroxyphenyl)propanehydrazide Chemical compound NNC(=O)[C@@H](N)CC1=CC=C(O)C=C1 MWIXENPCUPDSOS-QMMMGPOBSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 1
- ZJBDIQUABBYJRD-UHFFFAOYSA-N 2-amino-2-chlorobutanoic acid Chemical compound CCC(N)(Cl)C(O)=O ZJBDIQUABBYJRD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
- 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 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-L D-tartrate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O FEWJPZIEWOKRBE-LWMBPPNESA-L 0.000 description 1
- OGNSCSPNOLGXSM-VKHMYHEASA-N L-2,4-diaminobutyric acid Chemical compound NCC[C@H](N)C(O)=O OGNSCSPNOLGXSM-VKHMYHEASA-N 0.000 description 1
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 1
- QJPWUUJVYOJNMH-VKHMYHEASA-N L-homoserine lactone Chemical compound N[C@H]1CCOC1=O QJPWUUJVYOJNMH-VKHMYHEASA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- 229930195722 L-methionine Natural products 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- -1 carbonates Chemical compound 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229960004452 methionine Drugs 0.000 description 1
- 235000016337 monopotassium tartrate Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- KYKNRZGSIGMXFH-ZVGUSBNCSA-M potassium bitartrate Chemical compound [K+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O KYKNRZGSIGMXFH-ZVGUSBNCSA-M 0.000 description 1
- 229940081543 potassium bitartrate Drugs 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9601600A SE9601600D0 (sv) | 1996-04-26 | 1996-04-26 | Improved process |
| SE9601600-1 | 1996-04-26 | ||
| PCT/SE1997/000675 WO1997041084A1 (en) | 1996-04-26 | 1997-04-22 | Improved process for the production of enantiomerically-pure azetidine-2-carboxylic acid |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008290436A Division JP2009120611A (ja) | 1996-04-26 | 2008-11-13 | エナンチオマーとして純粋なアゼチジン−２−カルボン酸の改良された製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000509068A true JP2000509068A (ja) | 2000-07-18 |
| JP2000509068A5 JP2000509068A5 (en, 2012) | 2004-12-09 |
Family
ID=20402360
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9538797A Pending JP2000509068A (ja) | 1996-04-26 | 1997-04-22 | エナンチオマーとして純粋なアゼチジン―２―カルボン酸の改良された製造方法 |
| JP2008290436A Pending JP2009120611A (ja) | 1996-04-26 | 2008-11-13 | エナンチオマーとして純粋なアゼチジン−２−カルボン酸の改良された製造方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008290436A Pending JP2009120611A (ja) | 1996-04-26 | 2008-11-13 | エナンチオマーとして純粋なアゼチジン−２−カルボン酸の改良された製造方法 |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US6143903A (en, 2012) |
| EP (1) | EP0906255B1 (en, 2012) |
| JP (2) | JP2000509068A (en, 2012) |
| KR (1) | KR100447072B1 (en, 2012) |
| CN (1) | CN1071292C (en, 2012) |
| AR (1) | AR006639A1 (en, 2012) |
| AT (1) | ATE200889T1 (en, 2012) |
| AU (1) | AU713519B2 (en, 2012) |
| BR (1) | BR9708872A (en, 2012) |
| CA (1) | CA2253711C (en, 2012) |
| CZ (1) | CZ339998A3 (en, 2012) |
| DE (1) | DE69704708T2 (en, 2012) |
| DK (1) | DK0906255T3 (en, 2012) |
| EE (1) | EE9800365A (en, 2012) |
| EG (1) | EG20975A (en, 2012) |
| ES (1) | ES2158557T3 (en, 2012) |
| GR (1) | GR3036303T3 (en, 2012) |
| HU (1) | HUP9901665A3 (en, 2012) |
| ID (1) | ID16840A (en, 2012) |
| IL (1) | IL126717A (en, 2012) |
| IN (1) | IN186439B (en, 2012) |
| IS (1) | IS4860A (en, 2012) |
| MY (1) | MY132450A (en, 2012) |
| NO (1) | NO310404B1 (en, 2012) |
| NZ (1) | NZ332155A (en, 2012) |
| PL (1) | PL329685A1 (en, 2012) |
| PT (1) | PT906255E (en, 2012) |
| SE (1) | SE9601600D0 (en, 2012) |
| SK (1) | SK140898A3 (en, 2012) |
| TR (1) | TR199802146T2 (en, 2012) |
| WO (1) | WO1997041084A1 (en, 2012) |
| ZA (1) | ZA973156B (en, 2012) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005103005A1 (ja) * | 2004-04-26 | 2005-11-03 | Astellas Pharma Inc. | β－ピリジルアラニンの光学活性体の選択的製造方法 |
| WO2012033188A1 (ja) * | 2010-09-09 | 2012-03-15 | 三菱瓦斯化学株式会社 | 光学活性アミノ酸の製造方法 |
| WO2012033187A1 (ja) * | 2010-09-09 | 2012-03-15 | 三菱瓦斯化学株式会社 | 光学活性２－アミノ酪酸の製造方法 |
| WO2016021711A1 (ja) * | 2014-08-07 | 2016-02-11 | 株式会社エーピーアイ コーポレーション | アミノ酸誘導体の製造方法 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69834276T2 (de) * | 1997-01-24 | 2007-04-12 | Sumitomo Chemical Co. Ltd. | Verfahren zur Verbesserung der optischen Reinheit von Azetidin-2-carbonsäure |
| SE9802939D0 (sv) | 1998-09-01 | 1998-09-01 | Astra Ab | New process |
| SE9901712D0 (sv) * | 1999-05-11 | 1999-05-11 | Astra Ab | New process |
| EP2334620B1 (en) * | 2008-09-05 | 2018-09-05 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Process for enantioseparation of chiral systems with compound formation using two subsequent crystallization steps |
| CN103204783B (zh) * | 2013-04-18 | 2015-09-02 | 张家港市华昌药业有限公司 | 一种d-赖氨酸盐酸盐的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795874A (fr) * | 1972-02-25 | 1973-08-23 | Glaxo Lab Ltd | Procede de preparation d'esters optiquement actifs d'alpha-amino-acides |
| JPS5139219B2 (en, 2012) * | 1972-06-08 | 1976-10-26 | ||
| US4072698A (en) * | 1976-12-02 | 1978-02-07 | The Upjohn Company | Resolution of aminonitriles |
| JPS56104866A (en) * | 1980-01-24 | 1981-08-20 | Mitsubishi Chem Ind Ltd | Production of (2r,4r)-4-alkyl-2-piperidinecarboxylic acid or its l-tartarate salt |
| DE3303112A1 (de) * | 1983-01-31 | 1984-08-09 | Hoechst Ag, 6230 Frankfurt | Verfahren zur racemattrennung optisch aktiver bicyclischer imino-(alpha)-carbonsaeuren |
| US4923983A (en) * | 1989-07-31 | 1990-05-08 | Eli Lilly And Company | Method of resolving cis 3-amino-4-[2-(2-furyl)eth-1-yl]-1-methoxycarbonylmethyl-azetidin-2-one |
| EP0499376A1 (en) * | 1991-01-31 | 1992-08-19 | Hoechst Celanese Corporation | Precipitation-induced asymmetric transformation of chiral alpha-amino acids and salts thereof |
| GB9420246D0 (en) * | 1994-10-07 | 1994-11-23 | Chiroscience Ltd | Asymmetric crystallisation |
| IN187238B (en, 2012) * | 1995-06-30 | 2002-03-09 | Astra Ab | |
| DE69722538T2 (de) * | 1996-09-06 | 2004-04-29 | Sumitomo Chemical Co., Ltd. | Verfahren zur Herstellung von optisch aktiver Azetidin-2-Carbonsäure |
-
1996
- 1996-04-26 SE SE9601600A patent/SE9601600D0/xx unknown
-
1997
- 1997-04-14 ZA ZA9703156A patent/ZA973156B/xx unknown
- 1997-04-14 AR ARP970101487A patent/AR006639A1/es unknown
- 1997-04-22 CZ CZ983399A patent/CZ339998A3/cs unknown
- 1997-04-22 SK SK1408-98A patent/SK140898A3/sk unknown
- 1997-04-22 EE EE9800365A patent/EE9800365A/xx unknown
- 1997-04-22 ES ES97921046T patent/ES2158557T3/es not_active Expired - Lifetime
- 1997-04-22 US US08/913,016 patent/US6143903A/en not_active Expired - Fee Related
- 1997-04-22 NZ NZ332155A patent/NZ332155A/xx not_active IP Right Cessation
- 1997-04-22 HU HU9901665A patent/HUP9901665A3/hu unknown
- 1997-04-22 BR BR9708872A patent/BR9708872A/pt not_active Application Discontinuation
- 1997-04-22 EP EP97921046A patent/EP0906255B1/en not_active Expired - Lifetime
- 1997-04-22 DK DK97921046T patent/DK0906255T3/da active
- 1997-04-22 PT PT97921046T patent/PT906255E/pt unknown
- 1997-04-22 WO PCT/SE1997/000675 patent/WO1997041084A1/en active IP Right Grant
- 1997-04-22 CN CN97194111A patent/CN1071292C/zh not_active Expired - Fee Related
- 1997-04-22 PL PL97329685A patent/PL329685A1/xx unknown
- 1997-04-22 DE DE69704708T patent/DE69704708T2/de not_active Expired - Lifetime
- 1997-04-22 KR KR10-1998-0708557A patent/KR100447072B1/ko not_active Expired - Fee Related
- 1997-04-22 IL IL12671797A patent/IL126717A/en not_active IP Right Cessation
- 1997-04-22 AU AU27194/97A patent/AU713519B2/en not_active Ceased
- 1997-04-22 CA CA002253711A patent/CA2253711C/en not_active Expired - Fee Related
- 1997-04-22 TR TR1998/02146T patent/TR199802146T2/xx unknown
- 1997-04-22 JP JP9538797A patent/JP2000509068A/ja active Pending
- 1997-04-22 AT AT97921046T patent/ATE200889T1/de not_active IP Right Cessation
- 1997-04-23 MY MYPI97001747A patent/MY132450A/en unknown
- 1997-04-23 EG EG32897A patent/EG20975A/xx active
- 1997-04-24 IN IN1060DE1997 patent/IN186439B/en unknown
- 1997-04-25 ID IDP971396A patent/ID16840A/id unknown
-
1998
- 1998-10-06 IS IS4860A patent/IS4860A/is unknown
- 1998-10-07 NO NO19984681A patent/NO310404B1/no not_active IP Right Cessation
-
2001
- 2001-07-31 GR GR20010401153T patent/GR3036303T3/el unknown
-
2008
- 2008-11-13 JP JP2008290436A patent/JP2009120611A/ja active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005103005A1 (ja) * | 2004-04-26 | 2005-11-03 | Astellas Pharma Inc. | β－ピリジルアラニンの光学活性体の選択的製造方法 |
| WO2012033188A1 (ja) * | 2010-09-09 | 2012-03-15 | 三菱瓦斯化学株式会社 | 光学活性アミノ酸の製造方法 |
| WO2012033187A1 (ja) * | 2010-09-09 | 2012-03-15 | 三菱瓦斯化学株式会社 | 光学活性２－アミノ酪酸の製造方法 |
| WO2016021711A1 (ja) * | 2014-08-07 | 2016-02-11 | 株式会社エーピーアイ コーポレーション | アミノ酸誘導体の製造方法 |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009120611A (ja) | エナンチオマーとして純粋なアゼチジン−２−カルボン酸の改良された製造方法 | |
| JP2008179645A (ja) | ピリダジノン誘導体の純粋なエナンチオマーの取得方法 | |
| JP2008247922A (ja) | エナンチオマーとして純粋なアゼチジン−２−カルボン酸の製造方法 | |
| US6054594A (en) | Process for the production of enantiomerically enriched N-acylazetidine-2-carboxylic acids | |
| JPH0859517A (ja) | 光学分割剤およびそれを用いた光学活性テトラヒドロフランカルボン酸類の製造法 | |
| JP2001505210A (ja) | 炭素環式立体異性体混合物の分割方法 | |
| MXPA06006522A (es) | Un proceso para la resolucion de nefopam. | |
| US20050065367A1 (en) | Method for producing optically active beta-phenylalanine | |
| MXPA98008788A (en) | Improved process for the production of azetidin-2- carboxylic acid enantiomerically p | |
| MXPA97010269A (es) | Proceso para la produccion de acido azetidin-2-carboxilico enantiomericamente puro | |
| JPH10507173A (ja) | レボブピバカインとその類似体のｌ−リシンからの製造法 | |
| CH380153A (fr) | Procédé de préparation de stéréoisomères en 5 de la 5-méthyl-réserpine | |
| WO1999058493A2 (en) | Process for the preparation of optically pure phenylalanine | |
| JPH0525180A (ja) | 光学活性ピラノベンゾオキサジアゾール化合物及びその製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20040415 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20040415 |
|
| A72 | Notification of change in name of applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A721 Effective date: 20040415 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20071127 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20080222 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20080331 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080527 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20080715 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20081226 |