NO317180B1 - Substituerte 3,5-difenyl-1,2,4-triazoler og deres anvendelse som farmasoytiske metallchelatorer - Google Patents
Substituerte 3,5-difenyl-1,2,4-triazoler og deres anvendelse som farmasoytiske metallchelatorer Download PDFInfo
- Publication number
- NO317180B1 NO317180B1 NO19986024A NO986024A NO317180B1 NO 317180 B1 NO317180 B1 NO 317180B1 NO 19986024 A NO19986024 A NO 19986024A NO 986024 A NO986024 A NO 986024A NO 317180 B1 NO317180 B1 NO 317180B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- bis
- hydroxyphenyl
- triazol
- compound
- Prior art date
Links
- 229910052751 metal Inorganic materials 0.000 title description 8
- 239000002184 metal Substances 0.000 title description 8
- KPKQWXGFEKRQQA-UHFFFAOYSA-N 3,5-diphenyl-1h-1,2,4-triazole Chemical class C1=CC=CC=C1C1=NNC(C=2C=CC=CC=2)=N1 KPKQWXGFEKRQQA-UHFFFAOYSA-N 0.000 title description 3
- 239000002738 chelating agent Substances 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 65
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 40
- -1 2-hydroxyphenyl Chemical group 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 229910052742 iron Inorganic materials 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 241001465754 Metazoa Species 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 9
- 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 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- BOFQWVMAQOTZIW-UHFFFAOYSA-N deferasirox Chemical group C1=CC(C(=O)O)=CC=C1N1C(C=2C(=CC=CC=2)O)=NC(C=2C(=CC=CC=2)O)=N1 BOFQWVMAQOTZIW-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
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- DKXUNACJTKLRAK-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-N-(2-hydroxyethyl)acetamide Chemical compound OCCNC(=O)CN1N=C(C=2C(=CC=CC=2)O)N=C1C1=CC=CC=C1O DKXUNACJTKLRAK-UHFFFAOYSA-N 0.000 claims description 3
- HZEHQQRCOFQIFD-UHFFFAOYSA-N 4-[3,5-bis(2-hydroxy-5-methylphenyl)-1,2,4-triazol-1-yl]benzoic acid Chemical compound CC1=CC=C(O)C(C2=NN(C(C=3C(=CC=C(C)C=3)O)=N2)C=2C=CC(=CC=2)C(O)=O)=C1 HZEHQQRCOFQIFD-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
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- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A61P39/00—General protective or antinoxious agents
- A61P39/04—Chelating agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Toxicology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH159396 | 1996-06-25 | ||
| PCT/EP1997/003315 WO1997049395A1 (en) | 1996-06-25 | 1997-06-24 | Substituted 3,5-diphenyl-1,2,4-triazoles and their use as pharmaceutical metal chelators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO986024D0 NO986024D0 (no) | 1998-12-21 |
| NO986024L NO986024L (no) | 1998-12-21 |
| NO317180B1 true NO317180B1 (no) | 2004-09-06 |
Family
ID=4214048
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19986024A NO317180B1 (no) | 1996-06-25 | 1998-12-21 | Substituerte 3,5-difenyl-1,2,4-triazoler og deres anvendelse som farmasoytiske metallchelatorer |
| NO2006017C NO2006017I2 (no) | 1996-06-25 | 2006-11-30 | 4-[3,5-bis(2-hydroksifenyl)-[1,2,4]triazol-l-yl]benzosyre(Deferasirox) |
| NO2018014C NO2018014I2 (no) | 1996-06-25 | 2018-04-17 | Deferasirox eller et farmasøytisk akseptabelt salt derav |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2006017C NO2006017I2 (no) | 1996-06-25 | 2006-11-30 | 4-[3,5-bis(2-hydroksifenyl)-[1,2,4]triazol-l-yl]benzosyre(Deferasirox) |
| NO2018014C NO2018014I2 (no) | 1996-06-25 | 2018-04-17 | Deferasirox eller et farmasøytisk akseptabelt salt derav |
Country Status (37)
| Country | Link |
|---|---|
| US (3) | US6465504B1 (de) |
| EP (1) | EP0914118B1 (de) |
| JP (1) | JP3541042B2 (de) |
| KR (1) | KR100616378B1 (de) |
| CN (1) | CN1146415C (de) |
| AP (1) | AP1127A (de) |
| AR (1) | AR007479A1 (de) |
| AT (1) | ATE226435T1 (de) |
| AU (1) | AU718037B2 (de) |
| BG (1) | BG64248B1 (de) |
| BR (1) | BR9709973A (de) |
| CA (1) | CA2255951C (de) |
| CY (2) | CY2429B1 (de) |
| CZ (1) | CZ291470B6 (de) |
| DE (3) | DE122007000020I2 (de) |
| DK (1) | DK0914118T3 (de) |
| ES (1) | ES2187785T3 (de) |
| FR (1) | FR06C0049I2 (de) |
| GE (1) | GEP20084355B (de) |
| HK (1) | HK1020530A1 (de) |
| HU (1) | HU226232B1 (de) |
| IL (1) | IL127212A0 (de) |
| LT (1) | LTC0914118I2 (de) |
| LU (1) | LU91291I2 (de) |
| MY (1) | MY129541A (de) |
| NL (1) | NL300248I2 (de) |
| NO (3) | NO317180B1 (de) |
| NZ (1) | NZ333308A (de) |
| OA (1) | OA10946A (de) |
| PL (1) | PL194758B1 (de) |
| PT (1) | PT914118E (de) |
| RU (1) | RU2208010C2 (de) |
| SI (1) | SI0914118T1 (de) |
| SK (1) | SK284319B6 (de) |
| TR (1) | TR199802693T2 (de) |
| TW (1) | TW533205B (de) |
| WO (1) | WO1997049395A1 (de) |
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| ES2192494B1 (es) * | 2002-03-27 | 2005-02-16 | Consejo Superior De Investigaciones Cientificas | Derivados de 1,2,4-triazol con propiedades cannabinoides. |
| US8829198B2 (en) * | 2007-10-31 | 2014-09-09 | Proteotech Inc | Compounds, compositions and methods for the treatment of beta-amyloid diseases and synucleinopathies |
| GB0223978D0 (en) * | 2002-10-15 | 2002-11-20 | Novartis Ag | Organic compound |
| US20090227647A1 (en) | 2008-03-05 | 2009-09-10 | Thomas Lake | Compounds, Compositions and Methods for the Treatment of Islet Amyloid Polypeptide (IAPP) Accumulation in Diabetes |
| US20050008699A1 (en) * | 2003-07-11 | 2005-01-13 | Fred Wehling | Effervescent glucosamine composition |
| JP2007514699A (ja) * | 2003-12-19 | 2007-06-07 | ノバルティス アクチエンゲゼルシャフト | （ａ）Ｎ−｛５−［４−（４−メチル−ピペラジノ−メチル）−ベンゾイルアミド］−２−メチルフェニル｝−４−（３−ピリジル）−２−ピリミジン−アミンおよび（ｂ）少なくとも１個のハイプシン化阻害剤を含む組み合わせ物およびその使用 |
| GB0408078D0 (en) * | 2004-04-08 | 2004-05-12 | Novartis Ag | Organic compounds |
| US8829051B2 (en) * | 2004-05-24 | 2014-09-09 | Geoffrey C. GURTNER | Method of treating or preventing pathologic effects of acute increases in hyperglycemia and/or acute increases of free fatty acid flux |
| US9737511B2 (en) * | 2004-05-24 | 2017-08-22 | Geoffrey C. GURTNER | Method of treating or preventing pathologic effects of acute increases in hyperglycemia and/or acute increases of free fatty acid flux |
| CA2594687C (en) * | 2005-01-28 | 2013-10-29 | Novartis Ag | Use of pyrimidylaminobenzamides for the treatment of diseases that respond to modulation of tie-2 kinase activity |
| US20080187510A1 (en) * | 2005-02-10 | 2008-08-07 | Camenisch Gian P | Methods for Improving Drug Disposition |
| CA2608709A1 (en) * | 2005-05-31 | 2006-12-07 | Novartis Ag | Treatment of liver diseases in which iron plays a role in pathogenesis |
| JP2009512652A (ja) * | 2005-10-19 | 2009-03-26 | ノバルティス アクチエンゲゼルシャフト | 安息香酸誘導体含有分散錠 |
| EP1945272B1 (de) | 2005-11-01 | 2013-09-11 | Novartis AG | Szintigraphie-verfahren |
| US20090317489A1 (en) | 2006-05-09 | 2009-12-24 | Hanspeter Nick | Combination Comprising an Iron Chelator and an Anti-Neoplastic Agent and Use Thereof |
| WO2008005624A2 (en) | 2006-05-23 | 2008-01-10 | Novartis Ag | Method of treatment of hereditary hemochromatosis |
| TWI448285B (zh) * | 2006-07-13 | 2014-08-11 | Los Angeles Biomed Res Inst | 用以治療白黴菌症（ｍｕｃｏｒｍｙｃｏｓｉｓ）及其他真菌類疾病之組合物及方法 |
| KR20090035737A (ko) * | 2006-08-04 | 2009-04-10 | 노파르티스 아게 | 철 킬레이터를 이용한 내분비 기능장애의 치료 |
| JP2010511012A (ja) * | 2006-11-29 | 2010-04-08 | ノバルティス アーゲー | デフェラシロックス（ｉｃｌ６７０ａ）の多形形態 |
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| US20080262060A1 (en) * | 2007-01-29 | 2008-10-23 | Toth Zoltan G | Crystalline forms of Deferasirox |
| CA2685043A1 (en) * | 2007-05-14 | 2008-11-20 | Novartis Ag | Use of iron chelator for the treatment of myocardial infarction |
| EP1994930A1 (de) | 2007-05-22 | 2008-11-26 | Novartis AG | Triazol-Verbindungen zur Behandlung der Biofilm Bildung |
| WO2009016359A1 (en) * | 2007-07-27 | 2009-02-05 | Pliva Hrvatska D.O.O. | New forms of deferasirox |
| US20090082412A1 (en) * | 2007-09-26 | 2009-03-26 | Protia, Llc | Deuterium-enriched deferasirox |
| EP2062572A1 (de) | 2007-11-19 | 2009-05-27 | Teva Pharmaceutical Industries Ltd. | Pharmazeutische Zusammensetzungen |
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| KR20190110771A (ko) | 2018-03-21 | 2019-10-01 | 주식회사 한국팜비오 | 데페라시록스를 함유하는 소형 분산성 정제 |
| CN108727287B (zh) * | 2018-05-10 | 2020-10-27 | 东南大学 | 1,2,4-三唑类化合物及其盐和应用 |
| UY38247A (es) | 2018-05-30 | 2019-12-31 | Novartis Ag | Anticuerpos frente a entpd2, terapias de combinación y métodos de uso de los anticuerpos y las terapias de combinación |
| GR1009592B (el) * | 2018-07-03 | 2019-09-11 | Φαρματεν Α.Β.Ε.Ε. | Φαρμακευτικο σκευασμα που περιλαμβανει εναν χηλικο παραγοντα συμπλεκτικο του σιδηρου και μεθοδος για την παρασκευη αυτου |
| KR20200113116A (ko) | 2019-03-22 | 2020-10-06 | 주식회사 한국팜비오 | 데페라시록스를 포함하는 필름코팅정제 |
| TW202102478A (zh) | 2019-04-01 | 2021-01-16 | 瑞士商威佛（國際）股份有限公司 | 新穎的鐵螯合物 |
| JP2022548881A (ja) | 2019-09-18 | 2022-11-22 | ノバルティス アーゲー | Ｅｎｔｐｄ２抗体、組合せ療法並びに抗体及び組合せ療法を使用する方法 |
| IT202000000922A1 (it) | 2020-01-20 | 2021-07-20 | Cage Chemicals S R L | Complessi di ferro e relativi sali come agenti di contrasto per MRI |
| EP4052698A1 (de) | 2021-03-05 | 2022-09-07 | Sanovel Ilac Sanayi Ve Ticaret A.S. | Filmbeschichtete tablette mit deferasirox |
| CN114276305B (zh) * | 2021-12-28 | 2023-11-17 | 中山大学 | 一种三取代苯基-1,2,4-三氮唑衍生物及其制备和治疗神经元损伤的应用 |
| CN114478410B (zh) * | 2022-03-31 | 2022-11-29 | 中山大学 | 一种二取代苯基-1,2,4-三氮唑衍生物及其制备和应用 |
| CN114591254B (zh) * | 2022-03-31 | 2023-10-13 | 中山大学 | 一种3,5-二取代苯基-1,2,4-三氮唑衍生物及其制备方法和应用 |
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|---|---|---|---|---|
| CH84663A4 (de) | 1963-01-24 | 1964-11-14 | ||
| DE2628152C2 (de) | 1976-06-23 | 1985-03-28 | Bayer Ag, 5090 Leverkusen | Fungizide und nematizide Mittel |
| US4528196A (en) * | 1981-02-23 | 1985-07-09 | The United States Of America As Represented By The Department Of Health And Human Services | Chelating agents for the treatment of iron overload |
| GB8429307D0 (en) | 1984-11-20 | 1984-12-27 | Shell Int Research | Heterocyclic herbicides |
| IL84331A0 (en) * | 1987-11-02 | 1988-04-29 | Yissum Res Dev Co | Pyridoxyl hydrazone derivatives and pharmaceutical compositions containing the same |
| US5260322A (en) | 1990-10-08 | 1993-11-09 | Merck & Co., Inc. | Angiotension II antagonists in the treatment of hyperuricemia |
| DE4320801A1 (de) * | 1993-06-23 | 1995-01-05 | Fahlberg List Pharma Gmbh | 2-Hydroxyphenylsubstituierte 1,2,4-Triazole und 1,2,4-Oxadiazole, ihre Verwendung als pharmazeutische Wirkstoffe und sie enthaltende Arzneimittel |
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