CA2516418A1 - 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-alkoxy-3-quinolinecarbonitriles for the treatment of ischemic injury - Google Patents
4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-alkoxy-3-quinolinecarbonitriles for the treatment of ischemic injury Download PDFInfo
- Publication number
- CA2516418A1 CA2516418A1 CA002516418A CA2516418A CA2516418A1 CA 2516418 A1 CA2516418 A1 CA 2516418A1 CA 002516418 A CA002516418 A CA 002516418A CA 2516418 A CA2516418 A CA 2516418A CA 2516418 A1 CA2516418 A1 CA 2516418A1
- Authority
- CA
- Canada
- Prior art keywords
- dichloro
- methoxyphenyl
- amino
- methoxy
- ethoxy
- 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
- -1 2,4-dichloro-5-methoxyphenyl Chemical group 0.000 title claims description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims description 8
- 238000011282 treatment Methods 0.000 title description 20
- 208000037906 ischaemic injury Diseases 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 230000008728 vascular permeability Effects 0.000 claims abstract description 19
- 208000014674 injury Diseases 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 8
- 230000008733 trauma Effects 0.000 claims abstract description 5
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- 238000000034 method Methods 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 230000000302 ischemic effect Effects 0.000 claims description 20
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
- 206010061216 Infarction Diseases 0.000 claims description 11
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- NPTUGALLOCBPCM-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-ethoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCC3CCN(C)CC3)C(OCC)=CC2=C1NC1=CC(OC)=C(Cl)C=C1Cl NPTUGALLOCBPCM-UHFFFAOYSA-N 0.000 claims description 4
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- JQGPWNQWNMMMAS-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-ethoxy-7-[2-(1-methylpiperidin-4-yl)ethoxy]quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCC3CCN(C)CC3)C(OCC)=CC2=C1NC1=CC(OC)=C(Cl)C=C1Cl JQGPWNQWNMMMAS-UHFFFAOYSA-N 0.000 claims description 3
- PCSXTJQETYJEOI-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-ethoxy-7-[2-(4-methylpiperazin-1-yl)ethoxy]quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCN3CCN(C)CC3)C(OCC)=CC2=C1NC1=CC(OC)=C(Cl)C=C1Cl PCSXTJQETYJEOI-UHFFFAOYSA-N 0.000 claims description 3
- OSJKQGUEJYZHQM-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-ethoxy-7-[3-(1-methylpiperidin-4-yl)propoxy]quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCC3CCN(C)CC3)C(OCC)=CC2=C1NC1=CC(OC)=C(Cl)C=C1Cl OSJKQGUEJYZHQM-UHFFFAOYSA-N 0.000 claims description 3
- FEPWXPAVJHFWGS-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-ethoxy-7-[3-(4-ethylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCN3CCN(CC)CC3)C(OCC)=CC2=C1NC1=CC(OC)=C(Cl)C=C1Cl FEPWXPAVJHFWGS-UHFFFAOYSA-N 0.000 claims description 3
- SNJXHAGNHXWXDO-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-ethoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCN3CCN(C)CC3)C(OCC)=CC2=C1NC1=CC(OC)=C(Cl)C=C1Cl SNJXHAGNHXWXDO-UHFFFAOYSA-N 0.000 claims description 3
- FCIILWHQWNLPJU-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[2-(1-methylpiperidin-4-yl)ethoxy]quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCC4CCN(C)CC4)C=C3N=CC=2C#N)=C1Cl FCIILWHQWNLPJU-UHFFFAOYSA-N 0.000 claims description 3
- QXWCRBMAGJJKTO-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[3-(1-methylpiperidin-4-yl)propoxy]quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCC4CCN(C)CC4)C=C3N=CC=2C#N)=C1Cl QXWCRBMAGJJKTO-UHFFFAOYSA-N 0.000 claims description 3
- HOHWAQXKWAAULM-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-7-[(1-ethylpiperidin-4-yl)methoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound C1CN(CC)CCC1COC1=CC2=NC=C(C#N)C(NC=3C(=CC(Cl)=C(OC)C=3)Cl)=C2C=C1OC HOHWAQXKWAAULM-UHFFFAOYSA-N 0.000 claims description 3
- UBPYILGKFZZVDX-UHFFFAOYSA-N bosutinib Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCN4CCN(C)CC4)C=C3N=CC=2C#N)=C1Cl UBPYILGKFZZVDX-UHFFFAOYSA-N 0.000 claims description 3
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- TXAYKQMEBQBGLR-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCC4CCN(C)CC4)C=C3N=CC=2C#N)=C1Cl TXAYKQMEBQBGLR-UHFFFAOYSA-N 0.000 claims description 2
- UNVLTPQRCHRNDB-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[2-(4-methylpiperazin-1-yl)ethoxy]quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCN4CCN(C)CC4)C=C3N=CC=2C#N)=C1Cl UNVLTPQRCHRNDB-UHFFFAOYSA-N 0.000 claims description 2
- SUGCHLACYQMXHH-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[3-(4-propylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile Chemical compound C1CN(CCC)CCN1CCCOC1=CC2=NC=C(C#N)C(NC=3C(=CC(Cl)=C(OC)C=3)Cl)=C2C=C1OC SUGCHLACYQMXHH-UHFFFAOYSA-N 0.000 claims description 2
- 206010002660 Anoxia Diseases 0.000 claims description 2
- 241000976983 Anoxia Species 0.000 claims description 2
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- 230000007953 anoxia Effects 0.000 claims description 2
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Classifications
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/4706—4-Aminoquinolines; 8-Aminoquinolines, e.g. chloroquine, primaquine
-
- 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
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- 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
-
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44931603P | 2003-02-21 | 2003-02-21 | |
| US60/449,316 | 2003-02-21 | ||
| PCT/US2004/004904 WO2004075898A1 (en) | 2003-02-21 | 2004-02-19 | 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-alkoxy-3-quinolinecarbonitriles for the treatment of ischemic injury |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2516418A1 true CA2516418A1 (en) | 2004-09-10 |
Family
ID=32927510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002516418A Abandoned CA2516418A1 (en) | 2003-02-21 | 2004-02-19 | 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-alkoxy-3-quinolinecarbonitriles for the treatment of ischemic injury |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US20040229880A1 (https=) |
| EP (1) | EP1594502A1 (https=) |
| JP (1) | JP2006522023A (https=) |
| KR (1) | KR20050102133A (https=) |
| CN (1) | CN1750824A (https=) |
| AR (1) | AR043253A1 (https=) |
| AU (1) | AU2004216235A1 (https=) |
| BR (1) | BRPI0407441A (https=) |
| CA (1) | CA2516418A1 (https=) |
| CO (1) | CO5640114A2 (https=) |
| CR (1) | CR7931A (https=) |
| EC (1) | ECSP055972A (https=) |
| MX (1) | MXPA05008706A (https=) |
| NO (1) | NO20054070L (https=) |
| RU (1) | RU2005129333A (https=) |
| TW (1) | TW200423938A (https=) |
| UA (1) | UA80472C2 (https=) |
| WO (1) | WO2004075898A1 (https=) |
| ZA (1) | ZA200506621B (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1680119A1 (en) | 2003-11-06 | 2006-07-19 | Wyeth | 4-anilino-3-quinolinecarbonitriles for the treatment of chronic myelogenous leukemia (cml) |
| JP2008517924A (ja) * | 2004-10-22 | 2008-05-29 | ワイス | 虚血傷害を処置するための４−［（２，４−ジクロロ−５−メトキシフェニル）アミノ］−６−アルコキシ−７−エチニル−３−キノリンカルボニトリル |
| EP1902029B2 (en) * | 2005-07-01 | 2022-02-16 | Wyeth LLC | Crystalline forms of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]-3-quinolinecarb-onitrile and methods of preparing the same |
| ES2565627T3 (es) * | 2010-07-30 | 2016-04-06 | Oncotherapy Science, Inc. | Derivados de quinolina e inhibidores de MELK que contienen los mismos |
| CN103772392A (zh) * | 2012-10-23 | 2014-05-07 | 杨子娇 | 一类治疗房角狭窄的化合物及其用途 |
| WO2015123758A1 (en) * | 2014-02-20 | 2015-08-27 | Apotex Inc. | Bosutinib forms and preparation methods thereof |
| US10231965B2 (en) | 2014-02-20 | 2019-03-19 | Ignyta, Inc. | Molecules for administration to ROS1 mutant cancer cells |
| US20160256457A1 (en) * | 2014-06-10 | 2016-09-08 | Beth Israel Deaconess Medical Center, Inc. | Methods for treating or preventing acute vascular leak |
| EP3227276B1 (en) | 2014-12-02 | 2021-09-01 | Ignyta, Inc. | Combinations for the treatment of neuroblastoma |
| WO2017029584A1 (en) * | 2015-08-19 | 2017-02-23 | Sun Pharmaceutical Industries Limited | Amorphous form of bosutinib |
| BR112018012255A2 (pt) | 2015-12-18 | 2018-12-04 | Ignyta Inc | método para tratar câncer |
| CN107814769B (zh) * | 2016-09-14 | 2021-05-07 | 正大天晴药业集团股份有限公司 | 一种博舒替尼的纯化方法 |
| AU2018302170B2 (en) | 2017-07-19 | 2024-02-29 | Ignyta, Inc. | Pharmaceutical compositions comprising entrectinib |
| CN111225662B (zh) | 2017-10-17 | 2022-11-22 | 伊尼塔公司 | 药物组合物和剂型 |
| CN111646940B (zh) * | 2019-03-04 | 2024-01-30 | 鲁南制药集团股份有限公司 | 一种博舒替尼中间体的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6002008A (en) * | 1997-04-03 | 1999-12-14 | American Cyanamid Company | Substituted 3-cyano quinolines |
| US6297258B1 (en) * | 1998-09-29 | 2001-10-02 | American Cyanamid Company | Substituted 3-cyanoquinolines |
| US6521618B2 (en) * | 2000-03-28 | 2003-02-18 | Wyeth | 3-cyanoquinolines, 3-cyano-1,6-naphthyridines, and 3-cyano-1,7-naphthyridines as protein kinase inhibitors |
| TWI275390B (en) * | 2002-04-30 | 2007-03-11 | Wyeth Corp | Process for the preparation of 7-substituted-3- quinolinecarbonitriles |
| CA2500368A1 (en) * | 2002-10-04 | 2004-04-22 | Caritas St. Elizabeth's Medical Center Of Boston, Inc. | Inhibition of src for treatment of reperfusion injury related to revascularization |
-
2004
- 2004-02-18 TW TW093103901A patent/TW200423938A/zh unknown
- 2004-02-18 US US10/780,973 patent/US20040229880A1/en not_active Abandoned
- 2004-02-19 AU AU2004216235A patent/AU2004216235A1/en not_active Withdrawn
- 2004-02-19 RU RU2005129333/04A patent/RU2005129333A/ru not_active Application Discontinuation
- 2004-02-19 KR KR1020057015377A patent/KR20050102133A/ko not_active Withdrawn
- 2004-02-19 MX MXPA05008706A patent/MXPA05008706A/es unknown
- 2004-02-19 CA CA002516418A patent/CA2516418A1/en not_active Abandoned
- 2004-02-19 WO PCT/US2004/004904 patent/WO2004075898A1/en not_active Ceased
- 2004-02-19 BR BR0407441-6A patent/BRPI0407441A/pt not_active IP Right Cessation
- 2004-02-19 EP EP04712889A patent/EP1594502A1/en not_active Withdrawn
- 2004-02-19 UA UAA200508924A patent/UA80472C2/uk unknown
- 2004-02-19 JP JP2006503706A patent/JP2006522023A/ja not_active Withdrawn
- 2004-02-19 CN CNA2004800046743A patent/CN1750824A/zh active Pending
- 2004-02-20 AR ARP040100546A patent/AR043253A1/es not_active Application Discontinuation
-
2005
- 2005-08-03 CR CR7931A patent/CR7931A/es not_active Application Discontinuation
- 2005-08-17 CO CO05081472A patent/CO5640114A2/es not_active Application Discontinuation
- 2005-08-18 ZA ZA200506621A patent/ZA200506621B/en unknown
- 2005-08-19 EC EC2005005972A patent/ECSP055972A/es unknown
- 2005-09-01 NO NO20054070A patent/NO20054070L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200506621B (en) | 2008-02-27 |
| JP2006522023A (ja) | 2006-09-28 |
| ECSP055972A (es) | 2006-01-16 |
| NO20054070L (no) | 2005-11-14 |
| AU2004216235A1 (en) | 2004-09-10 |
| KR20050102133A (ko) | 2005-10-25 |
| AR043253A1 (es) | 2005-07-20 |
| EP1594502A1 (en) | 2005-11-16 |
| BRPI0407441A (pt) | 2006-01-31 |
| WO2004075898A1 (en) | 2004-09-10 |
| TW200423938A (en) | 2004-11-16 |
| US20040229880A1 (en) | 2004-11-18 |
| CO5640114A2 (es) | 2006-05-31 |
| NO20054070D0 (no) | 2005-09-01 |
| CR7931A (es) | 2006-02-07 |
| RU2005129333A (ru) | 2006-01-27 |
| CN1750824A (zh) | 2006-03-22 |
| MXPA05008706A (es) | 2005-10-05 |
| UA80472C2 (en) | 2007-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |