CA2594484A1 - Cinnamate salts of a beta-2 adrenergic agonist - Google Patents
Cinnamate salts of a beta-2 adrenergic agonist Download PDFInfo
- Publication number
- CA2594484A1 CA2594484A1 CA002594484A CA2594484A CA2594484A1 CA 2594484 A1 CA2594484 A1 CA 2594484A1 CA 002594484 A CA002594484 A CA 002594484A CA 2594484 A CA2594484 A CA 2594484A CA 2594484 A1 CA2594484 A1 CA 2594484A1
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- methyl
- phenyl
- cinnamate
- salt
- 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.)
- Abandoned
Links
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- 239000000048 adrenergic agonist Substances 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 58
- 150000003839 salts Chemical class 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 33
- JRRKWFRTDFOWAB-SANMLTNESA-N 5-[(1r)-2-[2-[4-[4-(2-amino-2-methylpropoxy)anilino]phenyl]ethylamino]-1-hydroxyethyl]-8-hydroxy-1h-quinolin-2-one Chemical compound C1=CC(OCC(C)(N)C)=CC=C1NC(C=C1)=CC=C1CCNC[C@H](O)C1=CC=C(O)C2=C1C=CC(=O)N2 JRRKWFRTDFOWAB-SANMLTNESA-N 0.000 claims description 25
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 claims description 18
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- -1 4- [4- (2-amino-2-methyl-propoxy) -phenyl amino] -phenyl Chemical group 0.000 abstract description 16
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- IXTCZMJQGGONPY-XJAYAHQCSA-N rofleponide Chemical compound C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3O[C@@H](CCC)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O IXTCZMJQGGONPY-XJAYAHQCSA-N 0.000 description 1
- 229960002586 roflumilast Drugs 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 229960004017 salmeterol Drugs 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229950004351 telenzepine Drugs 0.000 description 1
- 229960000195 terbutaline Drugs 0.000 description 1
- 229960000351 terfenadine Drugs 0.000 description 1
- YUSMZDVTEOAHDL-NTMALXAHSA-N tert-butyl (3z)-3-(dimethylaminomethylidene)-4-oxopiperidine-1-carboxylate Chemical compound CN(C)\C=C1\CN(C(=O)OC(C)(C)C)CCC1=O YUSMZDVTEOAHDL-NTMALXAHSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 238000011200 topical administration Methods 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 229960001205 tridihexethyl chloride Drugs 0.000 description 1
- QDWJJTJNXAKQKD-UHFFFAOYSA-N trihexyphenidyl hydrochloride Chemical compound Cl.C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 QDWJJTJNXAKQKD-UHFFFAOYSA-N 0.000 description 1
- 229960004479 trihexyphenidyl hydrochloride Drugs 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 229960003223 tripelennamine Drugs 0.000 description 1
- 229960002147 tripelennamine citrate Drugs 0.000 description 1
- 229960004791 tropicamide Drugs 0.000 description 1
- 239000002750 tryptase inhibitor Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 229950000339 xinafoate Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4704—2-Quinolinones, e.g. carbostyril
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Pregnancy & Childbirth (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Gynecology & Obstetrics (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Golf Clubs (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64284405P | 2005-01-11 | 2005-01-11 | |
| GB0500513A GB0500513D0 (en) | 2005-01-11 | 2005-01-11 | Novel compounds |
| US60/642,844 | 2005-01-11 | ||
| GB0500513.7 | 2005-01-11 | ||
| GB0514200.5 | 2005-07-11 | ||
| GB0514199.9 | 2005-07-11 | ||
| GB0514199A GB0514199D0 (en) | 2005-07-11 | 2005-07-11 | Novel compounds |
| GB0514200A GB0514200D0 (en) | 2005-07-11 | 2005-07-11 | Novel compounds |
| PCT/EP2006/000141 WO2006074897A1 (en) | 2005-01-11 | 2006-01-09 | Cinnamate salts of a beta-2 adrenergic agonist |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2594484A1 true CA2594484A1 (en) | 2006-07-20 |
Family
ID=36046933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002594484A Abandoned CA2594484A1 (en) | 2005-01-11 | 2006-01-09 | Cinnamate salts of a beta-2 adrenergic agonist |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7772250B2 (OSRAM) |
| EP (1) | EP1846374A1 (OSRAM) |
| JP (1) | JP2008526805A (OSRAM) |
| KR (1) | KR20070097106A (OSRAM) |
| CN (1) | CN101137625A (OSRAM) |
| AU (1) | AU2006205933A1 (OSRAM) |
| BR (1) | BRPI0606712A2 (OSRAM) |
| CA (1) | CA2594484A1 (OSRAM) |
| EA (1) | EA200701260A1 (OSRAM) |
| IL (1) | IL184246A0 (OSRAM) |
| MA (1) | MA29167B1 (OSRAM) |
| MX (1) | MX2007008459A (OSRAM) |
| NO (1) | NO20073282L (OSRAM) |
| NZ (1) | NZ556335A (OSRAM) |
| WO (1) | WO2006074897A1 (OSRAM) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006074897A1 (en) * | 2005-01-11 | 2006-07-20 | Glaxo Group Limited | Cinnamate salts of a beta-2 adrenergic agonist |
| TW200738658A (en) | 2005-08-09 | 2007-10-16 | Astrazeneca Ab | Novel compounds |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| TW200745067A (en) | 2006-03-14 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| EP2064174B1 (en) | 2006-08-10 | 2016-10-26 | The Government of the United States of America as represented by the Secretary of the Department of Health and Human Services | Preparation of (r,r)- or (r,s)-fenoterol analogues and their use in treating congestive heart failure |
| TW200833670A (en) | 2006-12-20 | 2008-08-16 | Astrazeneca Ab | Novel compounds 569 |
| GB0702458D0 (en) | 2007-02-08 | 2007-03-21 | Astrazeneca Ab | Salts 668 |
| EP2231642B1 (en) | 2008-01-11 | 2013-10-23 | Novartis AG | Pyrimidines as kinase inhibitors |
| WO2009154557A1 (en) | 2008-06-18 | 2009-12-23 | Astrazeneca Ab | Benzoxazinone derivatives acting as beta2-adrenoreceptor agonist for the treatment of respiratory disorders |
| JP5837890B2 (ja) | 2010-03-10 | 2015-12-24 | アメリカ合衆国 | 神経膠芽腫および星状細胞腫の治療におけるフェノテロールおよびフェノテロール類似体の使用 |
| WO2012034095A1 (en) | 2010-09-09 | 2012-03-15 | Irm Llc | Compounds and compositions as trk inhibitors |
| US8637516B2 (en) | 2010-09-09 | 2014-01-28 | Irm Llc | Compounds and compositions as TRK inhibitors |
| AU2012220572A1 (en) | 2011-02-25 | 2013-08-29 | Irm Llc | Compounds and compositions as trk inhibitors |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US694568A (en) * | 1901-01-03 | 1902-03-04 | James W Mccarthy | Yarn or thread guide for spinning-machines. |
| US4353656A (en) * | 1980-10-14 | 1982-10-12 | Xerox Corporation | Moving coil, multiple energy print hammer system including a closed loop servo |
| US4778054A (en) * | 1982-10-08 | 1988-10-18 | Glaxo Group Limited | Pack for administering medicaments to patients |
| EP0211595B1 (en) * | 1985-07-30 | 1991-11-13 | Glaxo Group Limited | Devices for administering medicaments to patients |
| GB9004781D0 (en) * | 1990-03-02 | 1990-04-25 | Glaxo Group Ltd | Device |
| HU225869B1 (en) * | 1992-04-02 | 2007-11-28 | Smithkline Beecham Corp | Compounds with antiallergic and antiinflammatory activity and pharmaceutical compns. contg. them |
| US5998428A (en) * | 1995-05-31 | 1999-12-07 | Smithkline Beecham Corporation | Compounds and methods for treating PDE IV-related diseases |
| GB9700226D0 (en) * | 1997-01-08 | 1997-02-26 | Glaxo Group Ltd | Inhalation device |
| US6632666B2 (en) * | 2000-01-14 | 2003-10-14 | Biolife Solutions, Inc. | Normothermic, hypothermic and cryopreservation maintenance and storage of cells, tissues and organs in gel-based media |
| US6653323B2 (en) | 2001-11-13 | 2003-11-25 | Theravance, Inc. | Aryl aniline β2 adrenergic receptor agonists |
| TWI249515B (en) * | 2001-11-13 | 2006-02-21 | Theravance Inc | Aryl aniline beta2 adrenergic receptor agonists |
| US20030229058A1 (en) | 2001-11-13 | 2003-12-11 | Moran Edmund J. | Aryl aniline beta2 adrenergic receptor agonists |
| EP1622875B1 (en) | 2003-05-08 | 2009-12-02 | Theravance, Inc. | Crystalline forms of an arylaniline beta-2 adrenergic receptor agonist |
| TW200526547A (en) | 2003-09-22 | 2005-08-16 | Theravance Inc | Amino-substituted ethylamino β2 adrenergic receptor agonists |
| TW200531692A (en) * | 2004-01-12 | 2005-10-01 | Theravance Inc | Aryl aniline derivatives as β2 adrenergic receptor agonists |
| US7317023B2 (en) * | 2004-07-21 | 2008-01-08 | Theravance, Inc. | Diaryl ether β2 adrenergic receptor agonists |
| WO2006074897A1 (en) * | 2005-01-11 | 2006-07-20 | Glaxo Group Limited | Cinnamate salts of a beta-2 adrenergic agonist |
-
2006
- 2006-01-09 WO PCT/EP2006/000141 patent/WO2006074897A1/en not_active Ceased
- 2006-01-09 EP EP06700503A patent/EP1846374A1/en not_active Withdrawn
- 2006-01-09 US US11/327,886 patent/US7772250B2/en not_active Expired - Fee Related
- 2006-01-09 US US11/722,801 patent/US20080125462A1/en not_active Abandoned
- 2006-01-09 JP JP2007549866A patent/JP2008526805A/ja active Pending
- 2006-01-09 EA EA200701260A patent/EA200701260A1/ru unknown
- 2006-01-09 CA CA002594484A patent/CA2594484A1/en not_active Abandoned
- 2006-01-09 CN CNA2006800073097A patent/CN101137625A/zh active Pending
- 2006-01-09 KR KR1020077018424A patent/KR20070097106A/ko not_active Withdrawn
- 2006-01-09 MX MX2007008459A patent/MX2007008459A/es not_active Application Discontinuation
- 2006-01-09 AU AU2006205933A patent/AU2006205933A1/en not_active Abandoned
- 2006-01-09 NZ NZ556335A patent/NZ556335A/en not_active IP Right Cessation
- 2006-01-09 BR BRPI0606712-3A patent/BRPI0606712A2/pt not_active IP Right Cessation
-
2007
- 2007-06-26 IL IL184246A patent/IL184246A0/en unknown
- 2007-06-27 NO NO20073282A patent/NO20073282L/no not_active Application Discontinuation
- 2007-07-26 MA MA30100A patent/MA29167B1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US7772250B2 (en) | 2010-08-10 |
| EP1846374A1 (en) | 2007-10-24 |
| EA200701260A1 (ru) | 2008-02-28 |
| CN101137625A (zh) | 2008-03-05 |
| MX2007008459A (es) | 2007-07-25 |
| NZ556335A (en) | 2009-07-31 |
| NO20073282L (no) | 2007-09-04 |
| MA29167B1 (fr) | 2008-01-02 |
| KR20070097106A (ko) | 2007-10-02 |
| US20080125462A1 (en) | 2008-05-29 |
| JP2008526805A (ja) | 2008-07-24 |
| IL184246A0 (en) | 2007-10-31 |
| AU2006205933A1 (en) | 2006-07-20 |
| BRPI0606712A2 (pt) | 2010-03-16 |
| US20060189654A1 (en) | 2006-08-24 |
| WO2006074897A1 (en) | 2006-07-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |