TWI224590B - Novel tri-substituted phenyl derivatives and pharmaceutical compositions comprising the same - Google Patents
Novel tri-substituted phenyl derivatives and pharmaceutical compositions comprising the same Download PDFInfo
- Publication number
- TWI224590B TWI224590B TW089124657A TW89124657A TWI224590B TW I224590 B TWI224590 B TW I224590B TW 089124657 A TW089124657 A TW 089124657A TW 89124657 A TW89124657 A TW 89124657A TW I224590 B TWI224590 B TW I224590B
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- TW
- Taiwan
- Prior art keywords
- phenyl
- oxy
- ethoxy
- methylsulfo
- acid
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- -1 tri-substituted phenyl Chemical class 0.000 title claims abstract description 70
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 17
- 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 239000002253 acid Substances 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 11
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- CBUGXMQJNKGCIB-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-(4-hydroxyphenyl)ethoxy]-3-methylphenyl]propanoic acid Chemical compound CC1=CC(CC(OCC)C(O)=O)=CC=C1OCCC1=CC=C(O)C=C1 CBUGXMQJNKGCIB-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 20
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 89
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 58
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- 238000011049 filling Methods 0.000 description 42
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- 125000000217 alkyl group Chemical group 0.000 description 41
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 27
- 238000005481 NMR spectroscopy Methods 0.000 description 26
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 23
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 21
- 125000002877 alkyl aryl group Chemical group 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
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- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 14
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- 239000000651 prodrug Chemical group 0.000 description 9
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- 239000005695 Ammonium acetate Substances 0.000 description 8
- 235000019257 ammonium acetate Nutrition 0.000 description 8
- 229940043376 ammonium acetate Drugs 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 8
- 150000002367 halogens Chemical group 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 5
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- 150000003003 phosphines Chemical class 0.000 description 1
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
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- 239000012279 sodium borohydride Substances 0.000 description 1
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- 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 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
-
- 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
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Emergency Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9904421A SE9904421D0 (sv) | 1999-12-03 | 1999-12-03 | New compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI224590B true TWI224590B (en) | 2004-12-01 |
Family
ID=20417986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW089124657A TWI224590B (en) | 1999-12-03 | 2000-11-21 | Novel tri-substituted phenyl derivatives and pharmaceutical compositions comprising the same |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6750252B2 (enExample) |
| EP (1) | EP1237856B1 (enExample) |
| JP (1) | JP2003515583A (enExample) |
| KR (1) | KR100787072B1 (enExample) |
| CN (1) | CN1206212C (enExample) |
| AR (1) | AR033957A1 (enExample) |
| AT (1) | ATE266633T1 (enExample) |
| AU (1) | AU766533B2 (enExample) |
| BR (1) | BR0016130A (enExample) |
| CA (1) | CA2392039A1 (enExample) |
| DE (1) | DE60010747T2 (enExample) |
| DK (1) | DK1237856T3 (enExample) |
| ES (1) | ES2219425T3 (enExample) |
| IL (2) | IL149517A0 (enExample) |
| MX (1) | MXPA02005223A (enExample) |
| MY (1) | MY124727A (enExample) |
| NO (1) | NO20022590L (enExample) |
| PT (1) | PT1237856E (enExample) |
| SE (1) | SE9904421D0 (enExample) |
| TR (1) | TR200401716T4 (enExample) |
| TW (1) | TWI224590B (enExample) |
| WO (1) | WO2001040172A1 (enExample) |
| ZA (1) | ZA200203798B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6369067B1 (en) | 1997-10-27 | 2002-04-09 | Dr. Reddy's Research Foundation | Monocyclic compounds and their use in medicine: process for their preparation and pharmaceutical compositions containing them |
| AU1198699A (en) | 1997-10-27 | 1999-04-23 | Dr. Reddy's Research Foundation | Novel heterocyclic compounds and their use in medicine, process for their reparation and pharmaceutical compositions containing them |
| AU749505B2 (en) | 1997-10-27 | 2002-06-27 | Dr. Reddy's Laboratories Limited | Novel tricyclic compounds and their use in medicine; process for their preparation and pharmaceutical compositions containing them |
| US6440961B1 (en) | 1997-10-27 | 2002-08-27 | Dr. Reddy's Research Foundation | Tricyclic compounds and their use in medicine: process for their preparation and pharmaceutical compositions containing them |
| CA2307068C (en) | 1997-10-27 | 2007-04-10 | Dr. Reddy's Research Foundation | Bicyclic compounds, process for their preparation and pharmaceutical compositions containing them |
| US6531596B1 (en) | 1998-10-29 | 2003-03-11 | Dr. Reddy's Laboratories Ltd. | Process for the preparation of new antidiabetic agents |
| JP2002528535A (ja) | 1998-10-29 | 2002-09-03 | ドクター・レディーズ・リサーチ・ファウンデーション | 新規抗糖尿病剤製造の改良方法 |
| US6897199B2 (en) | 2001-02-05 | 2005-05-24 | Dr. Reddy's Laboratories Ltd. | Pharmaceutically acceptable salts of phenoxazine and phenothiazine compounds |
| SE0101386D0 (sv) | 2001-04-20 | 2001-04-20 | Astrazeneca Ab | New compounds |
| CN1589258A (zh) * | 2001-10-16 | 2005-03-02 | 雷迪实验室有限公司 | 新的β－苯基－α－氧取代的丙酸衍生物,它的制备方法和它们制备药学上重要的化合物的应用 |
| UA82835C2 (en) * | 2001-12-03 | 2008-05-26 | Reddys Lab Ltd Dr | ?-aryl-?-oxysubstituted propionuc acid derivatives and pharmaceutical composition based thereon |
| SE0104333D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| FR2872159B1 (fr) * | 2004-06-28 | 2007-10-05 | Merck Sante Soc Par Actions Si | Nouveaux derives acides carboxyliques phenyliques et leur utilisation dans le traitement du diabete |
| TW200817369A (en) * | 2006-05-22 | 2008-04-16 | Elan Pharm Inc | Preparation of polymer conjugates of therapeutic, agricultural and food additive compounds |
| JP5404429B2 (ja) | 2007-03-08 | 2014-01-29 | アルビレオ・アクチボラグ | ２−置換３−フェニルプロピオン酸誘導体および炎症性腸疾患の治療におけるそれらの使用 |
| FR2917086B1 (fr) * | 2007-06-05 | 2009-07-17 | Galderma Res & Dev | Nouveaux derives d'acide 3-phenyl acrylique activateurs des recepteurs de type ppar, leur methode de preparation et leur utilisation dans des compositions cosmetiques ou pharmaceutiques. |
| FR2917084B1 (fr) | 2007-06-05 | 2009-07-17 | Galderma Res & Dev | Nouveaux derives d'acide 3-phenyl propanoique activateurs des recpteurs de type ppar, leur methode de preparation et leur utilisation dans des compositions cosmetiques ou pharmaceutiques. |
| DE102007038251A1 (de) * | 2007-08-13 | 2009-02-19 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neues Herstellverfahren |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9801992D0 (sv) | 1998-06-04 | 1998-06-04 | Astra Ab | New 3-aryl-2-hydroxypropionic acid derivative I |
| SE9801990D0 (sv) | 1998-06-04 | 1998-06-04 | Astra Ab | New 3-aryl propionic acid derivatives and analogs |
| MA26634A1 (fr) | 1998-06-04 | 2004-12-20 | Astra Ab | Nouveaux derives de l'acide 3-aryl propionique et analogues |
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1999
- 1999-12-03 SE SE9904421A patent/SE9904421D0/xx unknown
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2000
- 2000-11-21 TW TW089124657A patent/TWI224590B/zh not_active IP Right Cessation
- 2000-11-29 WO PCT/SE2000/002385 patent/WO2001040172A1/en not_active Ceased
- 2000-11-29 US US10/148,850 patent/US6750252B2/en not_active Expired - Fee Related
- 2000-11-29 PT PT00983619T patent/PT1237856E/pt unknown
- 2000-11-29 EP EP00983619A patent/EP1237856B1/en not_active Expired - Lifetime
- 2000-11-29 CN CNB008163812A patent/CN1206212C/zh not_active Expired - Fee Related
- 2000-11-29 IL IL14951700A patent/IL149517A0/xx active IP Right Grant
- 2000-11-29 JP JP2001541859A patent/JP2003515583A/ja active Pending
- 2000-11-29 ES ES00983619T patent/ES2219425T3/es not_active Expired - Lifetime
- 2000-11-29 DE DE60010747T patent/DE60010747T2/de not_active Expired - Fee Related
- 2000-11-29 KR KR1020027007057A patent/KR100787072B1/ko not_active Expired - Fee Related
- 2000-11-29 TR TR2004/01716T patent/TR200401716T4/xx unknown
- 2000-11-29 MX MXPA02005223A patent/MXPA02005223A/es active IP Right Grant
- 2000-11-29 BR BR0016130-6A patent/BR0016130A/pt not_active Application Discontinuation
- 2000-11-29 DK DK00983619T patent/DK1237856T3/da active
- 2000-11-29 AT AT00983619T patent/ATE266633T1/de not_active IP Right Cessation
- 2000-11-29 AU AU20351/01A patent/AU766533B2/en not_active Ceased
- 2000-11-29 CA CA002392039A patent/CA2392039A1/en not_active Abandoned
- 2000-11-30 MY MYPI20005602A patent/MY124727A/en unknown
- 2000-12-01 AR ARP000106386A patent/AR033957A1/es not_active Application Discontinuation
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2002
- 2002-05-07 IL IL149517A patent/IL149517A/en not_active IP Right Cessation
- 2002-05-13 ZA ZA200203798A patent/ZA200203798B/en unknown
- 2002-05-31 NO NO20022590A patent/NO20022590L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL149517A (en) | 2007-07-04 |
| WO2001040172A1 (en) | 2001-06-07 |
| DK1237856T3 (da) | 2004-08-02 |
| AU766533B2 (en) | 2003-10-16 |
| DE60010747D1 (de) | 2004-06-17 |
| KR100787072B1 (ko) | 2007-12-21 |
| MY124727A (en) | 2006-06-30 |
| AU2035101A (en) | 2001-06-12 |
| US6750252B2 (en) | 2004-06-15 |
| CA2392039A1 (en) | 2001-06-07 |
| EP1237856B1 (en) | 2004-05-12 |
| DE60010747T2 (de) | 2005-05-19 |
| SE9904421D0 (sv) | 1999-12-03 |
| ATE266633T1 (de) | 2004-05-15 |
| CN1402703A (zh) | 2003-03-12 |
| IL149517A0 (en) | 2002-11-10 |
| NO20022590L (no) | 2002-07-29 |
| NO20022590D0 (no) | 2002-05-31 |
| EP1237856A1 (en) | 2002-09-11 |
| ZA200203798B (en) | 2003-10-29 |
| BR0016130A (pt) | 2002-08-20 |
| US20030149104A1 (en) | 2003-08-07 |
| JP2003515583A (ja) | 2003-05-07 |
| ES2219425T3 (es) | 2004-12-01 |
| CN1206212C (zh) | 2005-06-15 |
| PT1237856E (pt) | 2004-08-31 |
| TR200401716T4 (tr) | 2004-09-21 |
| MXPA02005223A (es) | 2003-09-25 |
| AR033957A1 (es) | 2004-01-21 |
| KR20020067537A (ko) | 2002-08-22 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |