CA2457976A1 - Combined preparations, containing 1,4-benzothiepine-1,1-dioxide derivatives and other active substances, and the use thereof - Google Patents
Combined preparations, containing 1,4-benzothiepine-1,1-dioxide derivatives and other active substances, and the use thereof Download PDFInfo
- Publication number
- CA2457976A1 CA2457976A1 CA002457976A CA2457976A CA2457976A1 CA 2457976 A1 CA2457976 A1 CA 2457976A1 CA 002457976 A CA002457976 A CA 002457976A CA 2457976 A CA2457976 A CA 2457976A CA 2457976 A1 CA2457976 A1 CA 2457976A1
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- agonists
- residue
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- Abandoned
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- 229960002725 isoflurane Drugs 0.000 description 1
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- ZAOPBCHLHBOUPR-UHFFFAOYSA-N tert-butyl 1-[2-[di(propan-2-yl)amino]ethylcarbamoyl]-6-phenylmethoxy-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C=1C=C2C(C(=O)NCCN(C(C)C)C(C)C)N(C(=O)OC(C)(C)C)CCC2=CC=1OCC1=CC=CC=C1 ZAOPBCHLHBOUPR-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10140169.8 | 2001-08-22 | ||
| DE10140169A DE10140169A1 (de) | 2001-08-22 | 2001-08-22 | Kombinationspräparate von 1,4-Benzothiepin-1,1-dioxidderivaten mit weiteren Wirkstoffen und deren Verwendung |
| DE10142456A DE10142456A1 (de) | 2001-08-31 | 2001-08-31 | Kombinationspräparate von 1,4-Benzothiepin-1,1dioxidderivaten mit weiteren Wirkstoffen und deren Verwendung |
| DE10142456.6 | 2001-08-31 | ||
| PCT/EP2002/008908 WO2003018024A1 (de) | 2001-08-22 | 2002-08-09 | Kombinationspräparate von 1,4- benzothiepin-1,1-dioxidderivaten mit weiteren wirkstoffen und deren verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2457976A1 true CA2457976A1 (en) | 2003-03-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002457976A Abandoned CA2457976A1 (en) | 2001-08-22 | 2002-08-09 | Combined preparations, containing 1,4-benzothiepine-1,1-dioxide derivatives and other active substances, and the use thereof |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US20030158119A1 (https=) |
| EP (1) | EP1425018B1 (https=) |
| JP (1) | JP2005501861A (https=) |
| KR (1) | KR20040032937A (https=) |
| CN (1) | CN1655792A (https=) |
| AR (1) | AR035285A1 (https=) |
| AT (1) | ATE411802T1 (https=) |
| AU (1) | AU2002333373B2 (https=) |
| BR (1) | BR0212031A (https=) |
| CA (1) | CA2457976A1 (https=) |
| CO (1) | CO5560550A2 (https=) |
| DE (1) | DE50212937D1 (https=) |
| HN (1) | HN2002000235A (https=) |
| HR (1) | HRP20040171A2 (https=) |
| HU (1) | HUP0401318A3 (https=) |
| IL (1) | IL160474A0 (https=) |
| MA (1) | MA26317A1 (https=) |
| MX (1) | MXPA04001328A (https=) |
| NO (1) | NO20040702L (https=) |
| NZ (1) | NZ531293A (https=) |
| OA (1) | OA12654A (https=) |
| PA (1) | PA8553201A1 (https=) |
| PE (1) | PE20030361A1 (https=) |
| PL (1) | PL366851A1 (https=) |
| RS (1) | RS11104A (https=) |
| RU (1) | RU2297222C2 (https=) |
| TN (1) | TNSN04034A1 (https=) |
| UY (1) | UY27419A1 (https=) |
| WO (1) | WO2003018024A1 (https=) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6982251B2 (en) | 2000-12-20 | 2006-01-03 | Schering Corporation | Substituted 2-azetidinones useful as hypocholesterolemic agents |
| IL156445A0 (en) | 2001-01-26 | 2004-01-04 | Schering Corp | Combinations of peroxisome proliferator-activated receptor (ppar) activator(s) and sterol absorption inhibitor(s) and treatments for vascular indications |
| US7071181B2 (en) | 2001-01-26 | 2006-07-04 | Schering Corporation | Methods and therapeutic combinations for the treatment of diabetes using sterol absorption inhibitors |
| AR035533A1 (es) | 2001-01-26 | 2004-06-02 | Schering Corp | Uso de por lo menos un inhibidor de la absorcion de los esteroles o sus sales, solvatos, prodrogas farmaceuticamente aceptables o mezclas de los mismos para la preparacion de un medicamento para el tratamiento de la sitosterolemia, composiciones farmaceuticas, el uso de dichas composiciones para la |
| US7053080B2 (en) | 2001-09-21 | 2006-05-30 | Schering Corporation | Methods and therapeutic combinations for the treatment of obesity using sterol absorption inhibitors |
| US7056906B2 (en) | 2001-09-21 | 2006-06-06 | Schering Corporation | Combinations of hormone replacement therapy composition(s) and sterol absorption inhibitor(s) and treatments for vascular conditions in post-menopausal women |
| MXPA04002573A (es) | 2001-09-21 | 2004-06-18 | Schering Corp | Tratamiento de xantoma con derivados de azetidinona como inhibidores de la absorcion de esterol. |
| WO2004043457A1 (en) | 2002-11-06 | 2004-05-27 | Schering Corporation | Cholesterol absorptions inhibitors for the treatment of autoimmune disorders |
| JP2006519869A (ja) | 2003-03-07 | 2006-08-31 | シェーリング コーポレイション | 置換アゼチジノン化合物、置換アゼチジノン化合物を調製するためのプロセス、それらの処方物および使用 |
| US7459442B2 (en) | 2003-03-07 | 2008-12-02 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof |
| EP1601668B1 (en) | 2003-03-07 | 2008-08-27 | Schering Corporation | Substituted azetidinone compounds, formulations and uses thereof for the treatment of hypercholesterolemia |
| CA2517572C (en) | 2003-03-07 | 2011-12-13 | Schering Corporation | Substituted azetidinone compounds, formulations and uses thereof for the treatment of hypercholesterolemia |
| JP2010509252A (ja) | 2006-11-14 | 2010-03-25 | サノフィ−アベンティス・ドイチュラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 改善された特性を有する新規な１，４−ベンゾチエピン−１，１−ジオキシド誘導体、それらの製造方法、上記化合物を含有する薬物、及びそれらの使用 |
| DE102006053637B4 (de) * | 2006-11-14 | 2011-06-30 | Sanofi-Aventis Deutschland GmbH, 65929 | Neue mit Fluor substituierte 1,4-Benzothiepin-1,1-Dioxidderivate, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
| DE102006053636B4 (de) * | 2006-11-14 | 2008-09-18 | Sanofi-Aventis Deutschland Gmbh | Neue mit Cyclohexylresten substituierte 1,4-Benzothiepin-1,1-Dioxidderivate und deren Verwendung |
| DE102006053635B4 (de) * | 2006-11-14 | 2011-06-30 | Sanofi-Aventis Deutschland GmbH, 65929 | Neue mit Benzylresten substituierte 1,4-Benzothiepin-1,1-Dioxidderivate, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
| CA2744817C (en) | 2008-11-26 | 2020-07-07 | Satiogen Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of obesity and diabetes |
| EP2575821B1 (en) | 2010-05-26 | 2015-08-12 | Satiogen Pharmaceuticals, Inc. | Bile acid recycling inhibitors and satiogens for treatment of diabetes, obesity, and inflammatory gastrointestinal conditions |
| WO2013055609A1 (en) * | 2011-10-12 | 2013-04-18 | Merck Sharp & Dohme Corp. | Pharmaceutical compositions that inhibit disproportionation |
| CA2852957C (en) | 2011-10-28 | 2020-08-04 | Lumena Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of hypercholemia and cholestatic liver disease |
| CN104023727B (zh) | 2011-10-28 | 2017-04-05 | 鲁美纳医药公司 | 用于治疗小儿胆汁淤积性肝病的胆汁酸再循环抑制剂 |
| CN105228615A (zh) | 2013-03-15 | 2016-01-06 | 鲁美纳医药公司 | 用于治疗巴雷特食管和胃食管返流疾病的胆汁酸再循环抑制剂 |
| US20140275090A1 (en) | 2013-03-15 | 2014-09-18 | Lumena Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of primary sclerosing cholangitis and inflammatory bowel disease |
| KR20150079373A (ko) | 2013-12-30 | 2015-07-08 | 한미약품 주식회사 | 에제티미브 및 로수바스타틴을 포함하는 경구용 복합제제 |
| PL3923943T3 (pl) | 2019-02-12 | 2024-12-09 | Mirum Pharmaceuticals, Inc. | Zależna od genotypu i dawki odpowiedź na asbti u pacjentów z niedoborem pompy eksportu soli żółciowych |
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| FR2663336B1 (fr) * | 1990-06-18 | 1992-09-04 | Adir | Nouveaux derives peptidiques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| AU727775B2 (en) | 1996-01-17 | 2000-12-21 | Novo Nordisk A/S | Fused 1,2,4-thiadiazine and fused 1,4-thiazine derivatives, their preparation and use |
| IL128332A0 (en) | 1996-08-30 | 2000-01-31 | Novo Nordisk As | GLP-1 derivatives |
| IL127296A (en) | 1996-12-31 | 2003-01-12 | Reddy Research Foundation | Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them |
| DE19726167B4 (de) * | 1997-06-20 | 2008-01-24 | Sanofi-Aventis Deutschland Gmbh | Insulin, Verfahren zu seiner Herstellung und es enthaltende pharmazeutische Zubereitung |
| PL338013A1 (en) | 1997-07-16 | 2000-09-25 | Novo Nordisk As | Derivatives of condensed 1,2,4-thiadiazine, their production and application |
| CO4970713A1 (es) * | 1997-09-19 | 2000-11-07 | Sanofi Synthelabo | Derivados de carboxamidotiazoles, su preparacion, composiciones farmaceuticas que los contienen |
| US6221897B1 (en) * | 1998-06-10 | 2001-04-24 | Aventis Pharma Deutschland Gmbh | Benzothiepine 1,1-dioxide derivatives, a process for their preparation, pharmaceuticals comprising these compounds, and their use |
| DE19825804C2 (de) * | 1998-06-10 | 2000-08-24 | Aventis Pharma Gmbh | 1,4-Benzothiepin-1,1-dioxidderivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE19845405C2 (de) * | 1998-10-02 | 2000-07-13 | Aventis Pharma Gmbh | Arylsubstituierte Propanolaminderivate und deren Verwendung |
| DE69911058T2 (de) * | 1998-12-23 | 2004-06-03 | G.D. Searle Llc, Chicago | Kombinationen einem ibat inhibitor und einem mtp inhibitor für kardiovaskuläre indikationen |
| GB9900416D0 (en) | 1999-01-08 | 1999-02-24 | Alizyme Therapeutics Ltd | Inhibitors |
| JP2002542245A (ja) | 1999-04-16 | 2002-12-10 | ノボ ノルディスク アクティーゼルスカブ | 置換イミダゾール、それらの製造および使用 |
| WO2000066585A1 (en) | 1999-04-30 | 2000-11-09 | Neurogen Corporation | 9H-PYRIMIDO[4,5-b]INDOLE DERIVATIVES: CRF1 SPECIFIC LIGANDS |
| GB9911863D0 (en) | 1999-05-21 | 1999-07-21 | Knoll Ag | Therapeutic agents |
| DE60029446T2 (de) | 1999-06-18 | 2007-02-08 | Merck & Co., Inc. | Arylthiazolidindione und aryloxazolidindion-derivate |
| BR0012752A (pt) | 1999-07-29 | 2002-04-02 | Lilly Co Eli | Benzofuril piperazinas e benzofuril homopiperazinas: agonistas de serotonina |
| HUP0202472A3 (en) * | 1999-09-01 | 2005-03-29 | Aventis Pharma Gmbh | Sulfonyl carboxiamide derivatives, method for their production and their use as medicaments |
| AU5257401A (en) * | 2000-04-28 | 2001-11-12 | Asahi Chemical Ind | Novel bicyclic compounds |
| DE60115227T2 (de) | 2000-05-11 | 2006-08-24 | Bristol-Myers Squibb Co. | Tetrahydroisochinolin-analoga als wachstumshormon-sekretagoga |
| EP1289526A4 (en) | 2000-05-30 | 2005-03-16 | Merck & Co Inc | MELANOCORTIN RECEPTOR AGONISTS |
| IL156552A0 (en) * | 2000-12-21 | 2004-01-04 | Aventis Pharma Gmbh | Diphenyl azetidinone derivatives, method for the production thereof, medicaments containing these compounds, and their use |
-
2002
- 2002-08-09 NZ NZ531293A patent/NZ531293A/en not_active IP Right Cessation
- 2002-08-09 WO PCT/EP2002/008908 patent/WO2003018024A1/de not_active Ceased
- 2002-08-09 PL PL02366851A patent/PL366851A1/xx not_active Application Discontinuation
- 2002-08-09 AT AT02796213T patent/ATE411802T1/de not_active IP Right Cessation
- 2002-08-09 BR BR0212031-3A patent/BR0212031A/pt not_active IP Right Cessation
- 2002-08-09 HR HR20040171A patent/HRP20040171A2/xx not_active Application Discontinuation
- 2002-08-09 OA OA1200400057A patent/OA12654A/en unknown
- 2002-08-09 KR KR10-2004-7002440A patent/KR20040032937A/ko not_active Ceased
- 2002-08-09 IL IL16047402A patent/IL160474A0/xx unknown
- 2002-08-09 CN CNA028163109A patent/CN1655792A/zh active Pending
- 2002-08-09 CA CA002457976A patent/CA2457976A1/en not_active Abandoned
- 2002-08-09 RU RU2004108119/15A patent/RU2297222C2/ru not_active IP Right Cessation
- 2002-08-09 RS YU11104A patent/RS11104A/sr unknown
- 2002-08-09 MX MXPA04001328A patent/MXPA04001328A/es active IP Right Grant
- 2002-08-09 EP EP02796213A patent/EP1425018B1/de not_active Expired - Lifetime
- 2002-08-09 AU AU2002333373A patent/AU2002333373B2/en not_active Ceased
- 2002-08-09 HU HU0401318A patent/HUP0401318A3/hu unknown
- 2002-08-09 DE DE50212937T patent/DE50212937D1/de not_active Expired - Lifetime
- 2002-08-09 JP JP2003522542A patent/JP2005501861A/ja active Pending
- 2002-08-16 PE PE2002000742A patent/PE20030361A1/es not_active Application Discontinuation
- 2002-08-20 UY UY27419A patent/UY27419A1/es unknown
- 2002-08-20 PA PA20028553201A patent/PA8553201A1/es unknown
- 2002-08-20 AR ARP020103125A patent/AR035285A1/es not_active Application Discontinuation
- 2002-08-20 HN HN2002000235A patent/HN2002000235A/es unknown
- 2002-08-22 US US10/225,841 patent/US20030158119A1/en not_active Abandoned
-
2003
- 2003-11-03 US US10/699,967 patent/US7179792B2/en not_active Expired - Lifetime
-
2004
- 2004-02-11 MA MA27524A patent/MA26317A1/fr unknown
- 2004-02-18 NO NO20040702A patent/NO20040702L/no not_active Application Discontinuation
- 2004-02-19 CO CO04014418A patent/CO5560550A2/es not_active Application Discontinuation
- 2004-02-20 TN TNP2004000034A patent/TNSN04034A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HRP20040171A2 (en) | 2004-10-31 |
| EP1425018A1 (de) | 2004-06-09 |
| WO2003018024A1 (de) | 2003-03-06 |
| DE50212937D1 (de) | 2008-12-04 |
| NO20040702L (no) | 2004-05-19 |
| AU2002333373B2 (en) | 2006-12-14 |
| ATE411802T1 (de) | 2008-11-15 |
| HUP0401318A3 (en) | 2008-03-28 |
| TNSN04034A1 (en) | 2006-06-01 |
| US20030158119A1 (en) | 2003-08-21 |
| MXPA04001328A (es) | 2004-05-05 |
| IL160474A0 (en) | 2004-07-25 |
| HN2002000235A (es) | 2003-02-18 |
| JP2005501861A (ja) | 2005-01-20 |
| BR0212031A (pt) | 2004-08-03 |
| US7179792B2 (en) | 2007-02-20 |
| RS11104A (sr) | 2006-12-15 |
| CN1655792A (zh) | 2005-08-17 |
| OA12654A (en) | 2006-06-15 |
| EP1425018B1 (de) | 2008-10-22 |
| UY27419A1 (es) | 2003-04-30 |
| PA8553201A1 (es) | 2004-08-31 |
| RU2004108119A (ru) | 2005-04-10 |
| AR035285A1 (es) | 2004-05-05 |
| KR20040032937A (ko) | 2004-04-17 |
| NZ531293A (en) | 2005-08-26 |
| RU2297222C2 (ru) | 2007-04-20 |
| CO5560550A2 (es) | 2005-09-30 |
| PE20030361A1 (es) | 2003-05-27 |
| HUP0401318A2 (hu) | 2004-10-28 |
| MA26317A1 (fr) | 2004-10-01 |
| US20040097424A1 (en) | 2004-05-20 |
| PL366851A1 (en) | 2005-02-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |