AR008756A1 - Proceso enzimatico para la preparacion estereoselectiva de amidas terapeuticas - Google Patents
Proceso enzimatico para la preparacion estereoselectiva de amidas terapeuticasInfo
- Publication number
- AR008756A1 AR008756A1 ARP970101401A ARP970101401A AR008756A1 AR 008756 A1 AR008756 A1 AR 008756A1 AR P970101401 A ARP970101401 A AR P970101401A AR P970101401 A ARP970101401 A AR P970101401A AR 008756 A1 AR008756 A1 AR 008756A1
- Authority
- AR
- Argentina
- Prior art keywords
- cyano
- alkoxy
- hydroxy
- nitrogen
- alkyl
- Prior art date
Links
- 230000002255 enzymatic effect Effects 0.000 title abstract 2
- 150000001408 amides Chemical class 0.000 title 1
- 230000000707 stereoselective effect Effects 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 4
- 125000001424 substituent group Chemical group 0.000 abstract 4
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 102000004157 Hydrolases Human genes 0.000 abstract 1
- 108090000604 Hydrolases Proteins 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Chemical group 0.000 abstract 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 1
- -1 phenylthio, phenylsulfinyl Chemical group 0.000 abstract 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 abstract 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 1
- 229910052717 sulfur Chemical group 0.000 abstract 1
- 239000011593 sulfur Chemical group 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/11—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/11—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton
- C07C255/14—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton containing cyano groups and esterified hydroxy groups bound to the carbon skeleton
-
- 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
-
- 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
- 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
- C12P41/005—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 carboxylic acid 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/42—Hydroxy-carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Analytical Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicinal Preparation (AREA)
Abstract
Un método para preparar un compuesto opticamente activo de formula I donde E se selecciona entre nitrogeno y CZ, donde C es un carbono de anillo y Z es unsustituyente tal como se define más adelante, donde: cuando E es CZ, X y Z se seleccionan delgrupo formado por: (A) X es ArY donde Y es un grupo de enlaceseleccionado entre carbonilo, sulfinilo y sulfonilo y Ar se selecciona entre el grupo formado por fenilo sustituido con 0-2 sustituyentes seleccionados entrehalo, hidroxi, ciano C1-C4 alquilo, y C1-C4 alcoxi; anillos heteroarilo de seis miembros que contienen 1-2 átomos de nitrogeno como los unicos heteroátomos;anillos heteroarilo de cinco miembros que contienen 1-2 heteroátomos seleccionados entre nitrogeno, oxígeno y azufre; y Z se selecciona entrehidrogeno, ciano, halo, hidroxi, C1-C4 alquilo y C1-C4 alcoxi; y (B) X es ciano y Z se selecciona entre el grupo formado por feniltio, fenilsulfinilo, yfenilsulfonilo cuyos anillos fenilo están sustituidos con 0-2 sustituyentes seleccionados entre halo, hidroxi, ciano, nitro, C1-C4 alquilo, y C1-C4 alcoxi;y cuando E es nitrogeno, X es independientemente seleccionado entre cualquiera de los valores de X mencionados precedentemente (A); y * es uncentro quiral opticamente activo, que comprende el paso de tratar un compuesto racémico de formula II donde X y E son los definidos precedentemente y R1 esalquilo opcionalmente sustituido por uno o más sustituyentes independientemente seleccionados entre hidroxi, halogeno, C1-C4 alcoxi, ciano, C1-C4 alquilamino yC1-C4 con una enzima hidrolasa. La invencion provee asimismo intermediarios quirales utiles para preparar el compuesto de formula I y procesos enzimáticospara preparar dichos intermediariosquirales.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9607458.8A GB9607458D0 (en) | 1996-04-10 | 1996-04-10 | Enzymatic process for stereoselective preparation of therapeutic amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR008756A1 true AR008756A1 (es) | 2000-02-23 |
Family
ID=10791844
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP970101401A AR008756A1 (es) | 1996-04-10 | 1997-04-09 | Proceso enzimatico para la preparacion estereoselectiva de amidas terapeuticas |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US6110729A (es) |
| EP (1) | EP0904400B1 (es) |
| JP (3) | JP3896162B2 (es) |
| KR (1) | KR20000005286A (es) |
| CN (1) | CN1215434A (es) |
| AR (1) | AR008756A1 (es) |
| AT (1) | ATE291095T1 (es) |
| AU (1) | AU723526B2 (es) |
| BR (1) | BR9708532A (es) |
| CA (1) | CA2251634A1 (es) |
| CZ (1) | CZ324698A3 (es) |
| DE (1) | DE69732772T2 (es) |
| GB (1) | GB9607458D0 (es) |
| IL (1) | IL126451A0 (es) |
| MY (1) | MY133666A (es) |
| NO (1) | NO984712D0 (es) |
| NZ (1) | NZ331401A (es) |
| PL (1) | PL329290A1 (es) |
| SK (1) | SK140198A3 (es) |
| TR (1) | TR199802019T2 (es) |
| WO (1) | WO1997038124A2 (es) |
| ZA (1) | ZA973019B (es) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1175889A (ja) * | 1997-07-15 | 1999-03-23 | Mitsubishi Rayon Co Ltd | 光学活性α−トリフルオロメチル乳酸及びその対掌体エステルの製造方法及び精製方法 |
| GB9804648D0 (en) | 1998-03-06 | 1998-04-29 | Zeneca Ltd | Chemical compounds |
| GB9805520D0 (en) | 1998-03-17 | 1998-05-13 | Zeneca Ltd | Chemical compounds |
| GB9811427D0 (en) | 1998-05-29 | 1998-07-22 | Zeneca Ltd | Chemical compounds |
| DE60036758T2 (de) * | 1999-08-04 | 2008-07-24 | Sumitomo Chemical Co., Ltd. | Verfahren zur Herstellung von optisch aktiver 3,3,3-Trifluor-2-hydroxy-2-methylpropionsäure und deren Salze |
| DE60009319T2 (de) | 1999-09-04 | 2005-03-31 | Astrazeneca Ab | Substituierte n-phenyl-2-hydroxy-2-methyl-3,3,3-trifluorpropanamid-derivative zur erhöhung der pyruvatdehydrogenaseaktivität |
| ES2307528T3 (es) | 1999-09-04 | 2008-12-01 | Astrazeneca Ab | Amidas como inhibidores para la piruvato deshidrogenasa. |
| EP1214295B1 (en) | 1999-09-04 | 2006-11-02 | AstraZeneca AB | Hydroxyacetamidobenzenesulphonamide derivatives |
| JP4529419B2 (ja) * | 2002-11-25 | 2010-08-25 | 東ソー株式会社 | 光学活性含フッ素化合物類、及びこれらの製造方法 |
| EP1422226A1 (en) * | 2002-11-25 | 2004-05-26 | Tosoh Corporation | Optically active fluorine-containing compounds and processes for their production |
| JP2007217440A (ja) * | 2007-06-06 | 2007-08-30 | Mitsubishi Rayon Co Ltd | 光学活性α−トリフルオロメチル乳酸の精製方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2541466A (en) * | 1949-05-21 | 1951-02-13 | Eastman Kodak Co | Alpha-fluoromethyl acrylonitriles and copolymers thereof |
| JPS59205989A (ja) * | 1983-05-09 | 1984-11-21 | Sumitomo Chem Co Ltd | 光学活性なアルコ−ル化合物の生化学的製法 |
| DE3528265A1 (de) * | 1985-08-07 | 1987-02-12 | Bayer Ag | Phosphonsaeureester |
| US4929760A (en) * | 1987-11-24 | 1990-05-29 | Showa Shell Sekiyu Kabushiki Kaisha | Fluorine-containing carbonyl compounds and method for preparing the same |
| JPH03254694A (ja) * | 1990-03-01 | 1991-11-13 | Kurita Water Ind Ltd | 光学活性な含フッ素アルコールの製造方法 |
| GB9005467D0 (en) * | 1990-03-12 | 1990-05-09 | Ici Plc | Process for the preparation of optically active intermediates for insecticidal compounds |
| JP3010497B2 (ja) * | 1990-05-31 | 2000-02-21 | チッソ株式会社 | 光学活性α―ヒドロキシエステル類の製造方法 |
| GB9214120D0 (en) * | 1991-07-25 | 1992-08-12 | Ici Plc | Therapeutic amides |
| JP3133480B2 (ja) * | 1992-04-15 | 2001-02-05 | 昭和シェル石油株式会社 | 光学活性ハロゲン含有アルコールの製造方法 |
| US5334534A (en) * | 1992-04-15 | 1994-08-02 | The Board Of Governors For Higher Education, State Of Rhode Island And Providence Plantations | Enzymatic preparation of optically active propanolol and β-adrenergic blockers using esterase |
| GB9304256D0 (en) * | 1993-03-03 | 1993-04-21 | Chiros Ltd | Arylalkanoic acid resolution |
| GB9309716D0 (en) * | 1993-05-12 | 1993-06-23 | Zeneca Ltd | Heterocyclic derivatives |
| ES2121212T3 (es) * | 1993-07-02 | 1998-11-16 | Unichema Chemie Bv | Proceso para la esterificacion de acidos carboxilicos con alcoholes terciarios. |
| BE1007297A3 (nl) * | 1993-07-19 | 1995-05-09 | Dsm Nv | Werkwijze voor de bereiding van optisch aktieve alcoholen en esters, en alcoholen en esters toegepast en bereid in dergelijke werkwijzen. |
| GB9322472D0 (en) * | 1993-11-01 | 1993-12-22 | Chiros Ltd | Chiral compounds and their preparation |
-
1996
- 1996-04-10 GB GBGB9607458.8A patent/GB9607458D0/en active Pending
-
1997
- 1997-04-07 CN CN97193598A patent/CN1215434A/zh active Pending
- 1997-04-07 KR KR1019980707994A patent/KR20000005286A/ko not_active Withdrawn
- 1997-04-07 BR BR9708532A patent/BR9708532A/pt not_active Application Discontinuation
- 1997-04-07 AU AU23028/97A patent/AU723526B2/en not_active Ceased
- 1997-04-07 DE DE69732772T patent/DE69732772T2/de not_active Expired - Fee Related
- 1997-04-07 PL PL97329290A patent/PL329290A1/xx unknown
- 1997-04-07 CZ CZ983246A patent/CZ324698A3/cs unknown
- 1997-04-07 IL IL12645197A patent/IL126451A0/xx unknown
- 1997-04-07 SK SK1401-98A patent/SK140198A3/sk unknown
- 1997-04-07 TR TR1998/02019T patent/TR199802019T2/xx unknown
- 1997-04-07 AT AT97915612T patent/ATE291095T1/de not_active IP Right Cessation
- 1997-04-07 WO PCT/GB1997/000965 patent/WO1997038124A2/en not_active Ceased
- 1997-04-07 NZ NZ331401A patent/NZ331401A/en unknown
- 1997-04-07 JP JP53596797A patent/JP3896162B2/ja not_active Expired - Fee Related
- 1997-04-07 EP EP97915612A patent/EP0904400B1/en not_active Expired - Lifetime
- 1997-04-07 CA CA002251634A patent/CA2251634A1/en not_active Abandoned
- 1997-04-07 US US09/171,039 patent/US6110729A/en not_active Expired - Fee Related
- 1997-04-09 MY MYPI97001553A patent/MY133666A/en unknown
- 1997-04-09 AR ARP970101401A patent/AR008756A1/es not_active Application Discontinuation
- 1997-04-09 ZA ZA9703019A patent/ZA973019B/xx unknown
-
1998
- 1998-10-09 NO NO984712A patent/NO984712D0/no not_active Application Discontinuation
-
2000
- 2000-05-31 US US09/584,288 patent/US6261830B1/en not_active Expired - Fee Related
-
2005
- 2005-04-28 JP JP2005133634A patent/JP2005287514A/ja not_active Withdrawn
-
2006
- 2006-09-12 JP JP2006247390A patent/JP2006345873A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| NO984712L (no) | 1998-10-09 |
| EP0904400A2 (en) | 1999-03-31 |
| DE69732772T2 (de) | 2005-10-27 |
| ATE291095T1 (de) | 2005-04-15 |
| CN1215434A (zh) | 1999-04-28 |
| PL329290A1 (en) | 1999-03-15 |
| US6261830B1 (en) | 2001-07-17 |
| IL126451A0 (en) | 1999-08-17 |
| DE69732772D1 (de) | 2005-04-21 |
| ZA973019B (en) | 1997-10-10 |
| CZ324698A3 (cs) | 1999-01-13 |
| US6110729A (en) | 2000-08-29 |
| KR20000005286A (ko) | 2000-01-25 |
| WO1997038124A3 (en) | 1997-12-18 |
| JP3896162B2 (ja) | 2007-03-22 |
| JP2006345873A (ja) | 2006-12-28 |
| GB9607458D0 (en) | 1996-06-12 |
| EP0904400B1 (en) | 2005-03-16 |
| CA2251634A1 (en) | 1997-10-16 |
| BR9708532A (pt) | 1999-08-03 |
| AU2302897A (en) | 1997-10-29 |
| NZ331401A (en) | 2000-06-23 |
| TR199802019T2 (xx) | 1999-04-21 |
| AU723526B2 (en) | 2000-08-31 |
| JP2000509254A (ja) | 2000-07-25 |
| SK140198A3 (en) | 1999-03-12 |
| MY133666A (en) | 2007-11-30 |
| NO984712D0 (no) | 1998-10-09 |
| WO1997038124A2 (en) | 1997-10-16 |
| JP2005287514A (ja) | 2005-10-20 |
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