JP4167726B2 - 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 - Google Patents
エナンチオマーとして純粋なアゼチジン−２−カルボン酸の製造方法 Download PDFInfo
- Publication number
- JP4167726B2 JP4167726B2 JP50505797A JP50505797A JP4167726B2 JP 4167726 B2 JP4167726 B2 JP 4167726B2 JP 50505797 A JP50505797 A JP 50505797A JP 50505797 A JP50505797 A JP 50505797A JP 4167726 B2 JP4167726 B2 JP 4167726B2
- Authority
- JP
- Japan
- Prior art keywords
- azeoh
- tartrate
- carboxylic acid
- azetidine
- tartaric acid
- 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.)
- Expired - Fee Related
Links
- IADUEWIQBXOCDZ-VKHMYHEASA-N Azetidine-2-carboxylic acid Natural products OC(=O)[C@@H]1CCN1 IADUEWIQBXOCDZ-VKHMYHEASA-N 0.000 title claims description 34
- 238000000034 method Methods 0.000 title claims description 34
- IADUEWIQBXOCDZ-UHFFFAOYSA-N azetidine-2-carboxylic acid Chemical compound OC(=O)C1CCN1 IADUEWIQBXOCDZ-UHFFFAOYSA-N 0.000 title claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 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 description 11
- 239000011975 tartaric acid Substances 0.000 claims description 11
- 235000002906 tartaric acid Nutrition 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 9
- 150000001413 amino acids Chemical class 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 7
- 239000012456 homogeneous solution Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 238000010956 selective crystallization Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 2
- -1 L-tartaric acid azetidine-2-carboxylic acid tartrate Chemical compound 0.000 claims description 2
- 239000001110 calcium chloride Substances 0.000 claims description 2
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 22
- 229960001270 d- tartaric acid Drugs 0.000 description 12
- 229940095064 tartrate Drugs 0.000 description 11
- 229960001367 tartaric acid Drugs 0.000 description 8
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229940024606 amino acid Drugs 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000005119 centrifugation Methods 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
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 1
- IADUEWIQBXOCDZ-GSVOUGTGSA-N (R)-azetidine-2-carboxylic acid Chemical compound OC(=O)[C@H]1CCN1 IADUEWIQBXOCDZ-GSVOUGTGSA-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 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
- QJPWUUJVYOJNMH-VKHMYHEASA-N L-homoserine lactone Chemical compound N[C@H]1CCOC1=O QJPWUUJVYOJNMH-VKHMYHEASA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 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
- ZMZINYUKVRMNTG-UHFFFAOYSA-N acetic acid;formic acid Chemical compound OC=O.CC(O)=O ZMZINYUKVRMNTG-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000016337 monopotassium tartrate Nutrition 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 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
- 229940086065 potassium hydrogentartrate Drugs 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
Classifications
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9502381A SE9502381D0 (sv) | 1995-06-30 | 1995-06-30 | Process for the production of enantiomerically-pure azetidine-2-carboxylic acid |
| SE9600435A SE9600435D0 (sv) | 1996-02-06 | 1996-02-06 | Process for the production of enantiomerically-pure azetidine-2-carboxylic acid |
| SE9502381-8 | 1996-02-06 | ||
| SE9600435-3 | 1996-02-06 | ||
| PCT/SE1996/000826 WO1997002241A1 (en) | 1995-06-30 | 1996-06-24 | Process for the production of enantiomerically-pure azetidine-2-carboxylic acid |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008127145A Division JP2008247922A (ja) | 1995-06-30 | 2008-05-14 | 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH11508589A JPH11508589A (ja) | 1999-07-27 |
| JPH11508589A5 JPH11508589A5 (enEXAMPLES) | 2004-08-05 |
| JP4167726B2 true JP4167726B2 (ja) | 2008-10-22 |
Family
ID=26662332
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50505797A Expired - Fee Related JP4167726B2 (ja) | 1995-06-30 | 1996-06-24 | 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 |
| JP2008127145A Pending JP2008247922A (ja) | 1995-06-30 | 2008-05-14 | 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 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008127145A Pending JP2008247922A (ja) | 1995-06-30 | 2008-05-14 | 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 |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US5942630A (enEXAMPLES) |
| EP (1) | EP0840724B1 (enEXAMPLES) |
| JP (2) | JP4167726B2 (enEXAMPLES) |
| KR (1) | KR100441571B1 (enEXAMPLES) |
| CN (1) | CN100439333C (enEXAMPLES) |
| AR (2) | AR002573A1 (enEXAMPLES) |
| AT (1) | ATE224871T1 (enEXAMPLES) |
| AU (1) | AU699338B2 (enEXAMPLES) |
| BR (1) | BR9609451A (enEXAMPLES) |
| CA (1) | CA2225896C (enEXAMPLES) |
| CZ (1) | CZ388397A3 (enEXAMPLES) |
| DE (1) | DE69623966T2 (enEXAMPLES) |
| DK (1) | DK0840724T3 (enEXAMPLES) |
| EE (1) | EE03393B1 (enEXAMPLES) |
| ES (1) | ES2181899T3 (enEXAMPLES) |
| HU (1) | HUP9901713A3 (enEXAMPLES) |
| IL (1) | IL122708A (enEXAMPLES) |
| IN (1) | IN187238B (enEXAMPLES) |
| IS (1) | IS4636A (enEXAMPLES) |
| MY (1) | MY132147A (enEXAMPLES) |
| NO (1) | NO308949B1 (enEXAMPLES) |
| NZ (1) | NZ311834A (enEXAMPLES) |
| PL (1) | PL324403A1 (enEXAMPLES) |
| PT (1) | PT840724E (enEXAMPLES) |
| RU (1) | RU2163595C2 (enEXAMPLES) |
| SK (1) | SK179097A3 (enEXAMPLES) |
| TR (1) | TR199701742T1 (enEXAMPLES) |
| TW (1) | TW338035B (enEXAMPLES) |
| WO (1) | WO1997002241A1 (enEXAMPLES) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008247922A (ja) * | 1995-06-30 | 2008-10-16 | Astrazeneca Ab | 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 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9601600D0 (sv) * | 1996-04-26 | 1996-04-26 | Astra Ab | Improved process |
| DE69834276T2 (de) * | 1997-01-24 | 2007-04-12 | Sumitomo Chemical Co. Ltd. | Verfahren zur Verbesserung der optischen Reinheit von Azetidin-2-carbonsäure |
| JP3757629B2 (ja) * | 1998-07-17 | 2006-03-22 | 住友化学株式会社 | 光学活性ｎ−置換アゼチジン−２−カルボン酸化合物の製造方法 |
| SE9802939D0 (sv) * | 1998-09-01 | 1998-09-01 | Astra Ab | New process |
| SE9901712D0 (sv) | 1999-05-11 | 1999-05-11 | Astra Ab | New process |
| AU4613100A (en) | 1999-05-14 | 2000-12-05 | Kaneka Corporation | Process for producing optically active azetidine-2-carboxylic acids |
| JP2000344739A (ja) | 1999-06-01 | 2000-12-12 | Sumitomo Chem Co Ltd | Ｎ−保護−アゼチジン−２−カルボン酸の製造方法 |
| WO2003072770A1 (fr) * | 2002-02-28 | 2003-09-04 | Mitsubishi Chemical Corporation | Nouvelle deshydrogenase et gene codant cette derniere |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE435499B (sv) * | 1974-12-13 | 1984-10-01 | Merck & Co Inc | Diastereomert salt av s-1-t-butylamino-2,3-dihydroxipropan |
| 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 |
| FR2610323B1 (fr) * | 1987-02-04 | 1989-06-23 | Delalande Sa | Enantiomeres de configuration absolue s de derives amide de l'amino-3 quinuclidine, leur procede de preparation et leur application en therapeutique |
| GB2206880B (en) * | 1987-07-16 | 1991-04-24 | Farmos Oy | Optical isomers of an imidazole derivative |
| IT1231158B (it) * | 1989-07-20 | 1991-11-19 | Dompe Farmaceutici Spa | Procedimento per la risoluzione ottica della dropropizina. |
| JPH04108774A (ja) * | 1990-08-25 | 1992-04-09 | Mitsubishi Kasei Corp | 光学活性なｎ―インダニルニコチン酸アミド誘導体及びこれを有効成分とする農園芸用殺菌剤 |
| US5095014A (en) * | 1990-12-07 | 1992-03-10 | A. H. Robins Company, Incorporated | 3-(2-chloro-4-(trifluoromethyl)phenoxy)-1-azetidine carboxamides having anticonvulsant activity |
| JPH05286933A (ja) * | 1992-04-10 | 1993-11-02 | Dai Ichi Seiyaku Co Ltd | アザスピロオクタン誘導体の塩 |
| FR2690161B1 (fr) * | 1992-04-16 | 1995-06-30 | Esteve Labor Dr | Derives de pyridone azetidinyl substitues avec activite antimicrobienne. |
| IN187238B (enEXAMPLES) * | 1995-06-30 | 2002-03-09 | Astra Ab |
-
1996
- 1996-06-17 IN IN1325DE1996 patent/IN187238B/en unknown
- 1996-06-21 AR ARP960103279A patent/AR002573A1/es unknown
- 1996-06-24 BR BR9609451A patent/BR9609451A/pt not_active IP Right Cessation
- 1996-06-24 CA CA002225896A patent/CA2225896C/en not_active Expired - Fee Related
- 1996-06-24 HU HU9901713A patent/HUP9901713A3/hu unknown
- 1996-06-24 EE EE9700353A patent/EE03393B1/xx unknown
- 1996-06-24 IL IL12270896A patent/IL122708A/xx not_active IP Right Cessation
- 1996-06-24 DE DE69623966T patent/DE69623966T2/de not_active Expired - Lifetime
- 1996-06-24 DK DK96922327T patent/DK0840724T3/da active
- 1996-06-24 JP JP50505797A patent/JP4167726B2/ja not_active Expired - Fee Related
- 1996-06-24 AU AU63232/96A patent/AU699338B2/en not_active Ceased
- 1996-06-24 CN CNB961951133A patent/CN100439333C/zh not_active Expired - Fee Related
- 1996-06-24 US US08/716,388 patent/US5942630A/en not_active Expired - Fee Related
- 1996-06-24 PT PT96922327T patent/PT840724E/pt unknown
- 1996-06-24 NZ NZ311834A patent/NZ311834A/en not_active IP Right Cessation
- 1996-06-24 AT AT96922327T patent/ATE224871T1/de not_active IP Right Cessation
- 1996-06-24 ES ES96922327T patent/ES2181899T3/es not_active Expired - Lifetime
- 1996-06-24 SK SK1790-97A patent/SK179097A3/sk unknown
- 1996-06-24 KR KR1019970709849A patent/KR100441571B1/ko not_active Expired - Fee Related
- 1996-06-24 RU RU98101507/04A patent/RU2163595C2/ru active
- 1996-06-24 CZ CZ973883A patent/CZ388397A3/cs unknown
- 1996-06-24 EP EP96922327A patent/EP0840724B1/en not_active Expired - Lifetime
- 1996-06-24 WO PCT/SE1996/000826 patent/WO1997002241A1/en active IP Right Grant
- 1996-06-24 PL PL96324403A patent/PL324403A1/xx unknown
- 1996-06-24 TR TR97/01742T patent/TR199701742T1/xx unknown
- 1996-06-29 MY MYPI96002683A patent/MY132147A/en unknown
- 1996-08-15 TW TW085109938A patent/TW338035B/zh active
-
1997
- 1997-04-18 AR ARP970101587A patent/AR006711A2/es unknown
- 1997-12-19 IS IS4636A patent/IS4636A/is unknown
- 1997-12-23 NO NO976056A patent/NO308949B1/no not_active IP Right Cessation
-
2008
- 2008-05-14 JP JP2008127145A patent/JP2008247922A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008247922A (ja) * | 1995-06-30 | 2008-10-16 | Astrazeneca Ab | 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 |
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