DE60010747T2 - Neue trisubstituierte phenyl-derivate und analoga - Google Patents
Neue trisubstituierte phenyl-derivate und analoga Download PDFInfo
- Publication number
- DE60010747T2 DE60010747T2 DE60010747T DE60010747T DE60010747T2 DE 60010747 T2 DE60010747 T2 DE 60010747T2 DE 60010747 T DE60010747 T DE 60010747T DE 60010747 T DE60010747 T DE 60010747T DE 60010747 T2 DE60010747 T2 DE 60010747T2
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- oxy
- methylsulfonyl
- ethoxy
- benzyl
- 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
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- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 101
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- -1 {4 - [(methylsulfonyl) oxy] phenethyl} oxy Chemical group 0.000 claims description 24
- 206010022489 Insulin Resistance Diseases 0.000 claims description 14
- 150000003839 salts Chemical group 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- 239000000651 prodrug Chemical group 0.000 claims description 13
- 229940002612 prodrug Drugs 0.000 claims description 13
- KJJASSOVFFYOHM-UHFFFAOYSA-N 3-[3-benzyl-4-[2-(4-methylsulfonyloxyphenyl)ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C=1C=CC=CC=1CC1=CC(CC(OCC)C(O)=O)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 KJJASSOVFFYOHM-UHFFFAOYSA-N 0.000 claims description 7
- QJSQEBHZCMIOPS-UHFFFAOYSA-N 3-[4-benzyl-3-[2-(4-methylsulfonyloxyphenyl)ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C=1C=C(OS(C)(=O)=O)C=CC=1CCOC1=CC(CC(OCC)C(O)=O)=CC=C1CC1=CC=CC=C1 QJSQEBHZCMIOPS-UHFFFAOYSA-N 0.000 claims description 7
- KJJASSOVFFYOHM-SANMLTNESA-N (2s)-3-[3-benzyl-4-[2-(4-methylsulfonyloxyphenyl)ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C=1C=CC=CC=1CC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 KJJASSOVFFYOHM-SANMLTNESA-N 0.000 claims description 5
- YRJFDAZUSIHIQN-UHFFFAOYSA-N 3-[3-benzyl-4-[2-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C=1C=CC=CC=1CC1=CC(CC(OCC)C(O)=O)=CC=C1OCCC1=CC=C(NC(=O)OC(C)(C)C)C=C1 YRJFDAZUSIHIQN-UHFFFAOYSA-N 0.000 claims description 5
- WBHUENAVXUPZDB-UHFFFAOYSA-N 3-[3-tert-butyl-4-[2-(4-methylsulfonyloxyphenyl)ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound CC(C)(C)C1=CC(CC(OCC)C(O)=O)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 WBHUENAVXUPZDB-UHFFFAOYSA-N 0.000 claims description 5
- JOZJRLWJUJMJOG-UHFFFAOYSA-N 2-ethoxy-3-[3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-[2-(4-methylsulfonyloxyphenyl)ethoxy]phenyl]propanoic acid Chemical compound CC(C)(C)OC(=O)NC1=CC(CC(OCC)C(O)=O)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 JOZJRLWJUJMJOG-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- QHBGILWAQKUUAU-UHFFFAOYSA-N 2-ethoxy-3-[4-methoxy-3-[2-(4-methylsulfonyloxyphenyl)ethoxy]phenyl]propanoic acid Chemical compound CCOC(C(O)=O)CC1=CC=C(OC)C(OCCC=2C=CC(OS(C)(=O)=O)=CC=2)=C1 QHBGILWAQKUUAU-UHFFFAOYSA-N 0.000 claims description 4
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- 239000012453 solvate Chemical group 0.000 claims description 4
- KJJASSOVFFYOHM-AREMUKBSSA-N (2r)-3-[3-benzyl-4-[2-(4-methylsulfonyloxyphenyl)ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C=1C=CC=CC=1CC1=CC(C[C@@H](OCC)C(O)=O)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 KJJASSOVFFYOHM-AREMUKBSSA-N 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 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
- 235000019260 propionic acid Nutrition 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
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- 238000006243 chemical reaction Methods 0.000 description 37
- 238000005160 1H NMR spectroscopy Methods 0.000 description 35
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 32
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 235000019439 ethyl acetate Nutrition 0.000 description 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
- 235000019341 magnesium sulphate Nutrition 0.000 description 17
- 125000006239 protecting group Chemical group 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 238000010992 reflux Methods 0.000 description 16
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- 125000000217 alkyl group Chemical group 0.000 description 15
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 description 13
- 238000010561 standard procedure Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 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 12
- CBLURUVVHKBIPR-UHFFFAOYSA-N 2-(4-methylsulfonyloxyphenyl)ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCC1=CC=C(OS(C)(=O)=O)C=C1 CBLURUVVHKBIPR-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 9
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
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- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 6
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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
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- 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)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9904421A SE9904421D0 (sv) | 1999-12-03 | 1999-12-03 | New compounds |
| SE9904421 | 1999-12-03 | ||
| PCT/SE2000/002385 WO2001040172A1 (en) | 1999-12-03 | 2000-11-29 | New tri-substituted phenyl derivatives and analogues |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60010747D1 DE60010747D1 (de) | 2004-06-17 |
| DE60010747T2 true DE60010747T2 (de) | 2005-05-19 |
Family
ID=20417986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60010747T Expired - Fee Related DE60010747T2 (de) | 1999-12-03 | 2000-11-29 | Neue trisubstituierte phenyl-derivate und analoga |
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 |
-
1999
- 1999-12-03 SE SE9904421A patent/SE9904421D0/xx unknown
-
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
-
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 |
| TWI224590B (en) | 2004-12-01 |
| US6750252B2 (en) | 2004-06-15 |
| CA2392039A1 (en) | 2001-06-07 |
| EP1237856B1 (en) | 2004-05-12 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |