CA2844388A1 - Process and intermediates for preparing macrolactams - Google Patents
Process and intermediates for preparing macrolactams Download PDFInfo
- Publication number
- CA2844388A1 CA2844388A1 CA2844388A CA2844388A CA2844388A1 CA 2844388 A1 CA2844388 A1 CA 2844388A1 CA 2844388 A CA2844388 A CA 2844388A CA 2844388 A CA2844388 A CA 2844388A CA 2844388 A1 CA2844388 A1 CA 2844388A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- salt
- compounds
- added
- making
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/04—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a three or four-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
-
- 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
- C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C271/34—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/013—Esters of alcohols having the esterified hydroxy group bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/12—Cyclic peptides with only normal peptide bonds in the ring
- C07K5/126—Tetrapeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161525462P | 2011-08-19 | 2011-08-19 | |
| US61/525,462 | 2011-08-19 | ||
| US201161533439P | 2011-09-12 | 2011-09-12 | |
| US61/533,439 | 2011-09-12 | ||
| US201161533915P | 2011-09-13 | 2011-09-13 | |
| US61/533,915 | 2011-09-13 | ||
| US201161539540P | 2011-09-27 | 2011-09-27 | |
| US61/539,540 | 2011-09-27 | ||
| PCT/US2012/051177 WO2013028470A1 (en) | 2011-08-19 | 2012-08-16 | Process and intermediates for preparing macrolactams |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2844388A1 true CA2844388A1 (en) | 2013-02-28 |
Family
ID=47746773
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2844388A Abandoned CA2844388A1 (en) | 2011-08-19 | 2012-08-16 | Process and intermediates for preparing macrolactams |
| CA2844386A Abandoned CA2844386A1 (en) | 2011-08-19 | 2012-08-16 | Crystal forms of a hcv protease inhibitor |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2844386A Abandoned CA2844386A1 (en) | 2011-08-19 | 2012-08-16 | Crystal forms of a hcv protease inhibitor |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US9073825B2 (enExample) |
| EP (3) | EP2744336B1 (enExample) |
| JP (2) | JP2014524442A (enExample) |
| KR (2) | KR20140053330A (enExample) |
| CN (2) | CN103889439A (enExample) |
| AU (2) | AU2012299218A1 (enExample) |
| BR (2) | BR112014003802A2 (enExample) |
| CA (2) | CA2844388A1 (enExample) |
| MX (2) | MX2014001945A (enExample) |
| RU (2) | RU2014110400A (enExample) |
| WO (3) | WO2013028465A1 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8828930B2 (en) | 2009-07-30 | 2014-09-09 | Merck Sharp & Dohme Corp. | Hepatitis C virus NS3 protease inhibitors |
| US8957203B2 (en) | 2011-05-05 | 2015-02-17 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| MX2014001945A (es) | 2011-08-19 | 2014-03-27 | Merck Sharp & Dohme | Procedimiento e intermedios para la preparacion de macrolactamas. |
| UA119315C2 (uk) | 2012-07-03 | 2019-06-10 | Гіліад Фармассет Елелсі | Інгібітори вірусу гепатиту с |
| JP6154474B2 (ja) | 2012-10-19 | 2017-06-28 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｃ型肝炎ウイルス阻害剤 |
| US9643999B2 (en) | 2012-11-02 | 2017-05-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| EP2914613B1 (en) | 2012-11-02 | 2017-11-22 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| WO2014071007A1 (en) | 2012-11-02 | 2014-05-08 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| EP2914614B1 (en) | 2012-11-05 | 2017-08-16 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| EP2764866A1 (en) | 2013-02-07 | 2014-08-13 | IP Gesellschaft für Management mbH | Inhibitors of nedd8-activating enzyme |
| EP2964664B1 (en) | 2013-03-07 | 2017-01-11 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| JP6511432B2 (ja) | 2013-03-15 | 2019-05-15 | ギリアード サイエンシーズ， インコーポレイテッド | Ｃ型肝炎ウイルスの大環状二環式阻害剤 |
| WO2015057611A1 (en) * | 2013-10-18 | 2015-04-23 | Merck Sharp & Dohme Corp. | Methods and intermediates for preparing macrolactams |
| WO2015095437A1 (en) * | 2013-12-20 | 2015-06-25 | Merck Sharp & Dohme Corp. | Methods and intermediates for the preparation of macrolactams |
| WO2015112806A2 (en) | 2014-01-24 | 2015-07-30 | Tp Therapeutics, Inc. | Diaryl macrocycles as modulators of protein kinases |
| WO2015188045A1 (en) | 2014-06-06 | 2015-12-10 | Abbvie Inc. | Crystal forms |
| RU2732405C2 (ru) | 2015-07-02 | 2020-09-16 | Тёрнинг Поинт Терапьютикс, Инк. | Хиральные диарильные макроциклы в качестве модуляторов протеинкиназ |
| BR112018000297A2 (pt) | 2015-07-06 | 2018-09-04 | Tp Therapeutics Inc | polimorfo de macrociclo de diarila |
| WO2017015367A1 (en) * | 2015-07-21 | 2017-01-26 | Tp Therapeutics, Inc. | Chiral diaryl macrocycles and uses thereof |
| CN109562113A (zh) | 2016-05-10 | 2019-04-02 | C4医药公司 | 用于靶蛋白降解的螺环降解决定子体 |
| WO2017197046A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | C3-carbon linked glutarimide degronimers for target protein degradation |
| CN121974842A (zh) | 2016-05-10 | 2026-05-05 | C4医药公司 | 用于靶蛋白降解的胺连接的c3-戊二酰亚胺降解决定子体 |
| CN109562107A (zh) | 2016-05-10 | 2019-04-02 | C4医药公司 | 用于靶蛋白降解的杂环降解决定子体 |
| AU2017302019A1 (en) | 2016-07-28 | 2019-02-07 | Turning Point Therapeutics, Inc. | Macrocycle kinase inhibitors |
| TWI808958B (zh) | 2017-01-25 | 2023-07-21 | 美商特普醫葯公司 | 涉及二芳基巨環化合物之組合療法 |
| EP4717317A3 (en) | 2017-06-20 | 2026-06-03 | C4 Therapeutics, Inc. | N/o-linked degrons and degronimers for protein degradation |
| PT3658148T (pt) | 2017-07-28 | 2024-08-26 | Turning Point Therapeutics Inc | Compostos macrocíclicos e utilizações dos mesmos |
| RS63787B1 (sr) | 2017-12-19 | 2022-12-30 | Turning Point Therapeutics Inc | Makrociklična jedinjenja za lečenje bolesti |
| CN111057045A (zh) * | 2019-12-18 | 2020-04-24 | 安徽红杉生物医药科技有限公司 | Hcv ns3/4a蛋白酶抑制剂中间体及其合成方法、应用 |
| CN112174982A (zh) * | 2020-09-10 | 2021-01-05 | 上海希迈医药科技有限公司 | 一种洛普替尼晶型及其制备方法 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4871868A (en) * | 1987-03-11 | 1989-10-03 | Takeda Chemical Industries, Ltd. | Production of substituted acetylenic compounds |
| GB9207987D0 (en) | 1992-04-10 | 1992-05-27 | Smithkline Beecham Plc | Novel container and closure |
| US5716960A (en) * | 1995-01-13 | 1998-02-10 | U.S. Bioscience Inc. And Individuals | Crystalline trimetrexate salts and the process for making the same |
| ZA98879B (en) * | 1997-02-04 | 1998-08-03 | Ono Pharmaceutical Co | Omega-cycloalkyl-prostaglandin e2 derivatives |
| NO317155B1 (no) | 1997-02-04 | 2004-08-30 | Ono Pharmaceutical Co | <omega>-cykloalkyl-prostagladin-E<N>2</N>-derivater |
| KR20130076903A (ko) | 2005-02-18 | 2013-07-08 | 미쓰비시 타나베 파마 코퍼레이션 | 프롤린 유도체의 염 또는 그 용매화물 및 그 제조 방법 |
| US7834145B2 (en) | 2005-03-22 | 2010-11-16 | Merck Sharp & Dohme Corp. | HCV protease substrates |
| AU2006242475B2 (en) | 2005-05-02 | 2011-07-07 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
| AR057456A1 (es) | 2005-07-20 | 2007-12-05 | Merck & Co Inc | Inhibidores de la proteasa ns3 del vhc |
| UA90909C2 (en) * | 2005-07-20 | 2010-06-10 | Мерк Шарп Энд Домэ Корп. | Hcv ns3 protease inhibitors |
| US8278322B2 (en) | 2005-08-01 | 2012-10-02 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
| CA2645234A1 (en) * | 2006-03-07 | 2007-09-13 | The Procter & Gamble Company | Compositions for oxidatively dyeing keratin fibers and methods for using such compositions |
| GB0609492D0 (en) | 2006-05-15 | 2006-06-21 | Angeletti P Ist Richerche Bio | Therapeutic agents |
| GB0612423D0 (en) | 2006-06-23 | 2006-08-02 | Angeletti P Ist Richerche Bio | Therapeutic agents |
| CN101583372A (zh) | 2006-10-24 | 2009-11-18 | 默克公司 | Hcv ns3蛋白酶抑制剂 |
| CA2667165A1 (en) | 2006-10-24 | 2008-05-02 | Merck & Co., Inc. | Hcv ns3 protease inhibitors |
| JP5268927B2 (ja) | 2006-10-27 | 2013-08-21 | メルク・シャープ・アンド・ドーム・コーポレーション | Ｈｃｖｎｓ３プロテアーゼ阻害剤 |
| WO2008057208A2 (en) | 2006-10-27 | 2008-05-15 | Merck & Co., Inc. | Hcv ns3 protease inhibitors |
| WO2008137779A2 (en) * | 2007-05-03 | 2008-11-13 | Intermune, Inc. | Novel macrocyclic inhibitors of hepatitis c virus replication |
| CN101754974B (zh) | 2007-07-19 | 2016-02-03 | Msd意大利有限公司 | 作为抗病毒剂的大环化合物 |
| CA2714604A1 (en) | 2008-02-25 | 2009-09-03 | Merck Sharp & Dohme Corp. | Macrocyclic hcv ns3 protease inhibitors |
| WO2009131196A1 (ja) * | 2008-04-24 | 2009-10-29 | 武田薬品工業株式会社 | 置換ピロリジン誘導体およびその用途 |
| CA2722326A1 (en) | 2008-04-24 | 2009-10-29 | Incyte Corporation | Macrocyclic compounds and their use as kinase inhibitors |
| CN102014911A (zh) | 2008-04-28 | 2011-04-13 | 默沙东公司 | Hcv ns3蛋白酶抑制剂 |
| ES2392611T3 (es) | 2008-07-22 | 2012-12-12 | Merck Sharp & Dohme Corp. | Compuestos de quinoxalina macrocíclica como inhibidores de la proteasa NS3 del VHC |
| US8828930B2 (en) | 2009-07-30 | 2014-09-09 | Merck Sharp & Dohme Corp. | Hepatitis C virus NS3 protease inhibitors |
| EP2470189A4 (en) * | 2009-08-27 | 2013-01-23 | Merck Sharp & Dohme | METHOD FOR PRODUCING PROTEASE INHIBITORS OF HEPATITIS C VIRUS |
| MX2014001945A (es) | 2011-08-19 | 2014-03-27 | Merck Sharp & Dohme | Procedimiento e intermedios para la preparacion de macrolactamas. |
-
2012
- 2012-08-16 MX MX2014001945A patent/MX2014001945A/es unknown
- 2012-08-16 MX MX2014001944A patent/MX2014001944A/es unknown
- 2012-08-16 RU RU2014110400/04A patent/RU2014110400A/ru not_active Application Discontinuation
- 2012-08-16 CN CN201280050382.8A patent/CN103889439A/zh active Pending
- 2012-08-16 KR KR1020147006858A patent/KR20140053330A/ko not_active Withdrawn
- 2012-08-16 CA CA2844388A patent/CA2844388A1/en not_active Abandoned
- 2012-08-16 BR BR112014003802A patent/BR112014003802A2/pt not_active IP Right Cessation
- 2012-08-16 BR BR112014003798A patent/BR112014003798A2/pt not_active IP Right Cessation
- 2012-08-16 WO PCT/US2012/051168 patent/WO2013028465A1/en not_active Ceased
- 2012-08-16 AU AU2012299218A patent/AU2012299218A1/en not_active Abandoned
- 2012-08-16 EP EP12826404.1A patent/EP2744336B1/en not_active Not-in-force
- 2012-08-16 US US14/239,391 patent/US9073825B2/en active Active
- 2012-08-16 CN CN201280050361.6A patent/CN103874414A/zh active Pending
- 2012-08-16 EP EP12825540.3A patent/EP2744507A4/en not_active Withdrawn
- 2012-08-16 WO PCT/US2012/051177 patent/WO2013028470A1/en not_active Ceased
- 2012-08-16 JP JP2014526215A patent/JP2014524442A/ja active Pending
- 2012-08-16 CA CA2844386A patent/CA2844386A1/en not_active Abandoned
- 2012-08-16 US US14/239,393 patent/US9238604B2/en active Active
- 2012-08-16 KR KR1020147006888A patent/KR20140059236A/ko not_active Withdrawn
- 2012-08-16 WO PCT/US2012/051182 patent/WO2013028471A1/en not_active Ceased
- 2012-08-16 EP EP12825726.8A patent/EP2744331A4/en not_active Withdrawn
- 2012-08-16 US US14/239,389 patent/US9242917B2/en active Active
- 2012-08-16 RU RU2014110399/04A patent/RU2014110399A/ru not_active Application Discontinuation
- 2012-08-16 AU AU2012299223A patent/AU2012299223A1/en not_active Abandoned
- 2012-08-16 JP JP2014526217A patent/JP2014521750A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| MX2014001944A (es) | 2014-03-27 |
| RU2014110399A (ru) | 2015-09-27 |
| KR20140053330A (ko) | 2014-05-07 |
| US20140243519A1 (en) | 2014-08-28 |
| AU2012299218A1 (en) | 2014-02-20 |
| US20140200343A1 (en) | 2014-07-17 |
| EP2744331A1 (en) | 2014-06-25 |
| BR112014003802A2 (pt) | 2017-06-13 |
| EP2744336A4 (en) | 2014-12-31 |
| US20140206605A1 (en) | 2014-07-24 |
| RU2014110400A (ru) | 2015-09-27 |
| JP2014524442A (ja) | 2014-09-22 |
| EP2744336B1 (en) | 2017-07-05 |
| EP2744336A1 (en) | 2014-06-25 |
| WO2013028470A1 (en) | 2013-02-28 |
| AU2012299223A1 (en) | 2014-02-27 |
| US9238604B2 (en) | 2016-01-19 |
| EP2744507A1 (en) | 2014-06-25 |
| US9073825B2 (en) | 2015-07-07 |
| KR20140059236A (ko) | 2014-05-15 |
| EP2744331A4 (en) | 2015-01-21 |
| US9242917B2 (en) | 2016-01-26 |
| CN103889439A (zh) | 2014-06-25 |
| WO2013028471A1 (en) | 2013-02-28 |
| EP2744507A4 (en) | 2015-01-28 |
| CA2844386A1 (en) | 2013-02-28 |
| BR112014003798A2 (pt) | 2017-03-01 |
| JP2014521750A (ja) | 2014-08-28 |
| WO2013028465A1 (en) | 2013-02-28 |
| MX2014001945A (es) | 2014-03-27 |
| CN103874414A (zh) | 2014-06-18 |
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| WO2015095437A1 (en) | Methods and intermediates for the preparation of macrolactams |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20180816 |