NO315422B1 - Aminoetylfenoksyeddiksyrederivater og legemidler for smertereduksjon og kalksteinfjerningsfremming i urin lithiasis - Google Patents
Aminoetylfenoksyeddiksyrederivater og legemidler for smertereduksjon og kalksteinfjerningsfremming i urin lithiasis Download PDFInfo
- Publication number
- NO315422B1 NO315422B1 NO20000371A NO20000371A NO315422B1 NO 315422 B1 NO315422 B1 NO 315422B1 NO 20000371 A NO20000371 A NO 20000371A NO 20000371 A NO20000371 A NO 20000371A NO 315422 B1 NO315422 B1 NO 315422B1
- Authority
- NO
- Norway
- Prior art keywords
- ethyl
- pharmaceutically acceptable
- carbon atom
- acceptable salt
- acid
- Prior art date
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- FZBSFRTYISUPFO-UHFFFAOYSA-N 4-amino-2-phenoxybutanoic acid Chemical class NCCC(C(O)=O)OC1=CC=CC=C1 FZBSFRTYISUPFO-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 208000008281 urolithiasis Diseases 0.000 title claims abstract description 17
- 235000019738 Limestone Nutrition 0.000 title abstract description 3
- 239000003814 drug Substances 0.000 title description 16
- 229940079593 drug Drugs 0.000 title description 15
- 239000006028 limestone Substances 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 23
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 22
- 206010007027 Calculus urinary Diseases 0.000 claims abstract description 16
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 10
- 230000001737 promoting effect Effects 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
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- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
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- QJUZJNRWDMQTMY-BUXKBTBVSA-N 2-[3-fluoro-4-[2-[[(1r,2s)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenoxy]acetic acid Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(OCC(O)=O)C=C1F QJUZJNRWDMQTMY-BUXKBTBVSA-N 0.000 claims 1
- 230000004936 stimulating effect Effects 0.000 abstract description 12
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
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- 239000000203 mixture Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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- KKXPBQQLKHBRDA-DJJJIMSYSA-N 2-[4-[2-[[(1r,2s)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenoxy]acetic acid Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(OCC(O)=O)C=C1 KKXPBQQLKHBRDA-DJJJIMSYSA-N 0.000 description 7
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- 238000002474 experimental method Methods 0.000 description 4
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 208000036029 Uterine contractions during pregnancy Diseases 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 102000016959 beta-3 Adrenergic Receptors Human genes 0.000 description 3
- 108010014502 beta-3 Adrenergic Receptors Proteins 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
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- 229910052760 oxygen Inorganic materials 0.000 description 3
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- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 3
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- XGPGXPZFPBTBLJ-QKKBWIMNSA-N ethyl 2-[3-chloro-4-[2-[[(1r,2s)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenoxy]acetate Chemical compound ClC1=CC(OCC(=O)OCC)=CC=C1CCN[C@@H](C)[C@H](O)C1=CC=C(O)C=C1 XGPGXPZFPBTBLJ-QKKBWIMNSA-N 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- XSBAMIXHEIYSMO-KNMWBNGMSA-N ethyl 2-[3-chloro-4-[2-[[(1r,2s)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenoxy]acetate;hydrochloride Chemical compound Cl.ClC1=CC(OCC(=O)OCC)=CC=C1CCN[C@@H](C)[C@H](O)C1=CC=C(O)C=C1 XSBAMIXHEIYSMO-KNMWBNGMSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 238000009212 extracorporeal shock wave lithotripsy Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000007915 intraurethral administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 210000000754 myometrium Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical class C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 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
- 239000000843 powder Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- 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
- A61P13/04—Drugs for disorders of the urinary system for urolithiasis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Urology & Nephrology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23323997 | 1997-07-25 | ||
| PCT/JP1998/003163 WO1999005090A1 (fr) | 1997-07-25 | 1998-07-15 | Derives d'acide aminoethylphenoxyacetique et medicaments qui reduisent la douleur et favorisent la suppression des calculs dans la lithiase urinaire |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20000371D0 NO20000371D0 (no) | 2000-01-25 |
| NO20000371L NO20000371L (no) | 2000-01-25 |
| NO315422B1 true NO315422B1 (no) | 2003-09-01 |
Family
ID=16951956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20000371A NO315422B1 (no) | 1997-07-25 | 2000-01-25 | Aminoetylfenoksyeddiksyrederivater og legemidler for smertereduksjon og kalksteinfjerningsfremming i urin lithiasis |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US6399660B1 (fr) |
| EP (1) | EP1002791B1 (fr) |
| JP (1) | JP4002391B2 (fr) |
| KR (1) | KR100545473B1 (fr) |
| CN (1) | CN1137877C (fr) |
| AR (1) | AR013241A1 (fr) |
| AT (1) | ATE280146T1 (fr) |
| AU (1) | AU754579B2 (fr) |
| BR (1) | BR9811483B1 (fr) |
| CA (1) | CA2298493C (fr) |
| CO (1) | CO4970779A1 (fr) |
| CZ (1) | CZ300389B6 (fr) |
| DE (1) | DE69827137T2 (fr) |
| ES (1) | ES2231996T3 (fr) |
| HK (1) | HK1028016A1 (fr) |
| HU (1) | HUP0004055A3 (fr) |
| ID (1) | ID24062A (fr) |
| IL (1) | IL133863A0 (fr) |
| MY (1) | MY126743A (fr) |
| NO (1) | NO315422B1 (fr) |
| NZ (1) | NZ502366A (fr) |
| PE (1) | PE99899A1 (fr) |
| PL (1) | PL191864B1 (fr) |
| PT (1) | PT1002791E (fr) |
| RU (1) | RU2196130C2 (fr) |
| SA (1) | SA98190661B1 (fr) |
| TW (1) | TW418184B (fr) |
| WO (1) | WO1999005090A1 (fr) |
| ZA (1) | ZA986580B (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69919860T2 (de) | 1998-04-14 | 2005-08-25 | Kissei Pharmaceutical Co., Ltd., Matsumoto | 2-methylpropionsäure-derivate und sie enthaltende medizinische zubereitungen |
| MY126489A (en) * | 1998-07-08 | 2006-10-31 | Kissei Pharmaceutical | Phenoxyacetic acid derivatives and medicinal compositions containing the same |
| RU2237656C2 (ru) * | 1999-01-21 | 2004-10-10 | Киссеи Фармасьютикал Ко., Лтд. | Кристаллический полиморф 2-[4-[2-[[(1s,2r)-2-гидрокси-2-(4-гидроксифенил)-1- метилэтил]амино]этил]фенокси]уксусной кислоты |
| JP4532119B2 (ja) * | 2002-03-22 | 2010-08-25 | キッセイ薬品工業株式会社 | 腎疾患の予防又は治療剤 |
| EP1424079A1 (fr) * | 2002-11-27 | 2004-06-02 | Boehringer Ingelheim International GmbH | Combinaison d'un agoniste du beta-3-récepteur et d'un inhibiteur de recaptage de sérotonine et/ou norépinéphrine |
| DE10333569A1 (de) * | 2003-07-23 | 2005-02-17 | Z & J Technologies Gmbh | Einrichtung zur Verteilung von Schüttgut in wenigstens zwei oberhalb der Gicht eines Hochofens angeordnete Bunker |
| WO2005077355A1 (fr) * | 2004-02-12 | 2005-08-25 | Kissei Pharmaceutical Co., Ltd. | Compositions pharmaceutiques pour la prévention ou le traitement de maladies s’accompagnant de dyskinésie de l'œsophage |
| WO2007004639A1 (fr) * | 2005-07-06 | 2007-01-11 | Daiichi Fine Chemical Co., Ltd. | PROCÉDÉ POUR LA PRODUCTION D'UN ÉRYTHRO-β-AMINOALCOOL OPTIQUEMENT ACTIF |
| BRPI0615339A2 (pt) * | 2005-08-29 | 2011-05-17 | Kissei Pharmaceutical | Combinação farmacêutica para a prevenção ou tratamento de doenças associadas com a diminuição de lágrimas |
| EP1769792A1 (fr) * | 2005-09-30 | 2007-04-04 | Boehringer Ingelheim Pharma GmbH & Co.KG | Utilisation d'un du récepteur béta-3-adrénergique pour le traitement des troubles rénaux et vésicaux |
| ES2302447B1 (es) * | 2006-10-20 | 2009-06-12 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4338333A (en) * | 1979-06-16 | 1982-07-06 | Beecham Group Limited | Ethanamine derivatives their preparation and use in pharmaceutical compositions |
| US5776983A (en) * | 1993-12-21 | 1998-07-07 | Bristol-Myers Squibb Company | Catecholamine surrogates useful as β3 agonists |
| ES2195021T3 (es) * | 1995-11-30 | 2003-12-01 | Kissei Pharmaceutical | Medicamento para aliviar el dolor y favorecer la eliminacion de calculos en la urolitiasis. |
| WO1998013333A1 (fr) * | 1996-09-26 | 1998-04-02 | Kissei Pharmaceutical Co., Ltd. | Derives de 2-amino-1-(4-hydroxy-2-methylphenyl)propanol |
-
1997
- 1997-07-25 ID IDW20000131A patent/ID24062A/id unknown
-
1998
- 1998-07-15 CA CA002298493A patent/CA2298493C/fr not_active Expired - Fee Related
- 1998-07-15 WO PCT/JP1998/003163 patent/WO1999005090A1/fr active IP Right Grant
- 1998-07-15 BR BRPI9811483-2A patent/BR9811483B1/pt not_active IP Right Cessation
- 1998-07-15 HU HU0004055A patent/HUP0004055A3/hu unknown
- 1998-07-15 RU RU2000101840/04A patent/RU2196130C2/ru not_active IP Right Cessation
- 1998-07-15 CN CNB988075482A patent/CN1137877C/zh not_active Expired - Fee Related
- 1998-07-15 ES ES98932517T patent/ES2231996T3/es not_active Expired - Lifetime
- 1998-07-15 DE DE69827137T patent/DE69827137T2/de not_active Expired - Lifetime
- 1998-07-15 IL IL13386398A patent/IL133863A0/xx not_active IP Right Cessation
- 1998-07-15 NZ NZ502366A patent/NZ502366A/xx not_active IP Right Cessation
- 1998-07-15 AU AU82419/98A patent/AU754579B2/en not_active Ceased
- 1998-07-15 CZ CZ20000272A patent/CZ300389B6/cs not_active IP Right Cessation
- 1998-07-15 AT AT98932517T patent/ATE280146T1/de active
- 1998-07-15 EP EP98932517A patent/EP1002791B1/fr not_active Expired - Lifetime
- 1998-07-15 KR KR1020007000694A patent/KR100545473B1/ko not_active IP Right Cessation
- 1998-07-15 PT PT98932517T patent/PT1002791E/pt unknown
- 1998-07-15 PL PL338234A patent/PL191864B1/pl not_active IP Right Cessation
- 1998-07-15 JP JP2000504092A patent/JP4002391B2/ja not_active Expired - Fee Related
- 1998-07-16 MY MYPI98003263A patent/MY126743A/en unknown
- 1998-07-20 TW TW087111774A patent/TW418184B/zh not_active IP Right Cessation
- 1998-07-22 PE PE1998000659A patent/PE99899A1/es not_active Application Discontinuation
- 1998-07-22 AR ARP980103575A patent/AR013241A1/es active IP Right Grant
- 1998-07-23 ZA ZA986580A patent/ZA986580B/xx unknown
- 1998-07-23 CO CO98041910A patent/CO4970779A1/es unknown
- 1998-10-19 SA SA98190661A patent/SA98190661B1/ar unknown
-
1999
- 1999-05-21 US US09/463,432 patent/US6399660B1/en not_active Expired - Lifetime
-
2000
- 2000-01-25 NO NO20000371A patent/NO315422B1/no not_active IP Right Cessation
- 2000-11-13 HK HK00107213A patent/HK1028016A1/xx not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |