HUT59134A - Process for produicng heterocyclic compounds and pharmaceutical compositions comprising same - Google Patents
Process for produicng heterocyclic compounds and pharmaceutical compositions comprising sameInfo
- Publication number
- HUT59134A HUT59134A HU906252A HU625290A HUT59134A HU T59134 A HUT59134 A HU T59134A HU 906252 A HU906252 A HU 906252A HU 625290 A HU625290 A HU 625290A HU T59134 A HUT59134 A HU T59134A
- Authority
- HU
- Hungary
- Prior art keywords
- same
- produicng
- pharmaceutical compositions
- heterocyclic compounds
- sulphinyl
- Prior art date
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- -1 oxy, thio, sulphinyl Chemical group 0.000 abstract 2
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 abstract 1
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 1
- 125000006413 ring segment Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Quinoline Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP89402699 | 1989-09-29 | ||
| EP90401183 | 1990-05-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HU906252D0 HU906252D0 (en) | 1991-03-28 |
| HUT59134A true HUT59134A (en) | 1992-04-28 |
Family
ID=26123295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU906252A HUT59134A (en) | 1989-09-29 | 1990-09-28 | Process for produicng heterocyclic compounds and pharmaceutical compositions comprising same |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US5221677A (hu) |
| EP (1) | EP0420511B1 (hu) |
| JP (1) | JP2996708B2 (hu) |
| AT (1) | ATE110073T1 (hu) |
| AU (1) | AU632356B2 (hu) |
| CA (1) | CA2024258A1 (hu) |
| DD (1) | DD300434A5 (hu) |
| DE (1) | DE69011609T2 (hu) |
| DK (1) | DK0420511T3 (hu) |
| ES (1) | ES2058809T3 (hu) |
| FI (1) | FI904591A0 (hu) |
| GB (1) | GB9018134D0 (hu) |
| HU (1) | HUT59134A (hu) |
| IE (1) | IE64251B1 (hu) |
| IL (1) | IL95481A (hu) |
| MY (1) | MY107266A (hu) |
| NO (1) | NO904249L (hu) |
| NZ (1) | NZ235016A (hu) |
| PT (1) | PT95455A (hu) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5236919A (en) * | 1989-02-28 | 1993-08-17 | Imperial Chemical Industries Plc | Quinoxalinyl derivatives suitable for use in leukotriene mediated disease |
| US5254581A (en) * | 1990-06-21 | 1993-10-19 | Imperial Chemical Industries Plc | Pyran derivatives and their use as inhibitors of 5-lipoxygenase |
| GB9113137D0 (en) * | 1990-07-13 | 1991-08-07 | Ici Plc | Thioxo heterocycles |
| IE913655A1 (en) * | 1990-11-06 | 1992-05-22 | Zeneca Ltd | Synergistic agents |
| IE913866A1 (en) * | 1990-11-28 | 1992-06-03 | Ici Plc | Aryl derivatives |
| IE914005A1 (en) * | 1990-12-14 | 1992-06-17 | Zeneca Ltd | Novel intermediates |
| AU645159B2 (en) * | 1991-01-17 | 1994-01-06 | Ici Pharma | Sulphonamide derivatives |
| EP0532239B1 (en) * | 1991-09-10 | 1995-12-13 | Zeneca Limited | Benzenesulphonamide derivatives as 5-lipoxygenase inhibitors |
| CA2094465A1 (en) * | 1992-04-23 | 1993-10-24 | Pierre Andre Raymond Bruneau | Cycloalkane derivatives |
| CA2095005A1 (en) * | 1992-05-12 | 1993-11-13 | Philip Neil Edwards | Hydroxylamine derivatives |
| CA2095006A1 (en) * | 1992-05-12 | 1993-11-13 | Philip Neil Edwards | Oxime derivatives |
| AU4444393A (en) * | 1992-09-01 | 1994-03-10 | Zeneca Limited | Pyrrolidine derivatives |
| EP0586229A1 (en) * | 1992-09-01 | 1994-03-09 | Zeneca Limited | 3-Hydroxy-3-(subst-akyl)-pyrrolidines as 5-lipoxygenase inhibitors |
| ES2055657B1 (es) * | 1992-10-08 | 1995-02-16 | Ici Plc | Derivados de bencenosulfonamida. |
| AP9400632A0 (en) * | 1993-04-29 | 1995-10-07 | Zeneca Ltd | Ether derivatives. |
| JPH08511254A (ja) * | 1993-06-07 | 1996-11-26 | ゼネカ・リミテッド | ２−オキソ−１，２，３，４−テトラヒドロキノリン誘導体 |
| US5410054A (en) * | 1993-07-20 | 1995-04-25 | Merck Frosst Canada, Inc. | Heteroaryl quinolines as inhibitors of leukotriene biosynthesis |
| US5459271A (en) * | 1993-07-20 | 1995-10-17 | Merck Frosst Canada, Inc. | Arylbicyclooctanes as inhibitors of leukotriene biosynthesis |
| EP0636624A1 (en) * | 1993-07-27 | 1995-02-01 | Zeneca Limited | Thiazole derivatives as lipoxygenase inhibitors |
| IL110280A0 (en) * | 1993-07-27 | 1994-10-21 | Zeneca Ltd | Thiazole derivatives |
| ZA945250B (en) * | 1993-07-27 | 1995-01-27 | Zeneca Ltd | Thiazole derivatives |
| US5740861A (en) * | 1996-05-21 | 1998-04-21 | Fmc Corporation | Replaceable consumable erosion detector |
| ATE367379T1 (de) | 2000-08-09 | 2007-08-15 | Hoffmann La Roche | Quinolin-derivate als antientzündungsmittel |
| WO2006045096A2 (en) | 2004-10-20 | 2006-04-27 | Resverlogix Corp. | Flavanoids and isoflavanoids for the prevention and treatment of cardiovascular diseases |
| JP5368792B2 (ja) | 2005-07-29 | 2013-12-18 | レスバーロジックス コーポレイション | 複合疾患の予防および処置のための薬学的組成物および挿入可能な医療用デバイスによるその送達 |
| US8053440B2 (en) | 2007-02-01 | 2011-11-08 | Resverlogix Corporation | Compounds for the prevention and treatment of cardiovascular diseases |
| WO2009158404A1 (en) | 2008-06-26 | 2009-12-30 | Resverlogix Corp. | Methods of preparing quinazolinone derivatives |
| NZ594332A (en) | 2009-01-08 | 2013-09-27 | Resverlogix Corp | Compounds for the prevention and treatment of cardiovascular disease |
| CA3146333A1 (en) | 2009-03-18 | 2010-09-23 | Resverlogix Corp. | Phenyl-quinazolin-4(3h)-one and phenyl-pyrido[2,3-d]pyrimidin-4(3h)-one derivatives and compositions thereof useful as anti-inflammatory agents |
| PL2421533T3 (pl) | 2009-04-22 | 2019-05-31 | Resverlogix Corp | Nowe środki przeciwzapalne |
| EP3791880A1 (en) | 2009-04-29 | 2021-03-17 | Amarin Pharmaceuticals Ireland Limited | Pharmaceutical compositions comprising epa |
| AU2012330885B2 (en) | 2011-11-01 | 2016-10-06 | Resverlogix Corp. | Oral immediate release formulations for substituted quinazolinones |
| US9073878B2 (en) | 2012-11-21 | 2015-07-07 | Zenith Epigenetics Corp. | Cyclic amines as bromodomain inhibitors |
| US9765039B2 (en) | 2012-11-21 | 2017-09-19 | Zenith Epigenetics Ltd. | Biaryl derivatives as bromodomain inhibitors |
| US9271978B2 (en) | 2012-12-21 | 2016-03-01 | Zenith Epigenetics Corp. | Heterocyclic compounds as bromodomain inhibitors |
| US10111885B2 (en) | 2015-03-13 | 2018-10-30 | Resverlogix Corp. | Compositions and therapeutic methods for the treatment of complement-associated diseases |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1216878B (de) * | 1963-04-02 | 1966-05-18 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung von coronargefaesserweiternden Derivaten des 7-Hydroxy-2-oxo-1, 2-dihydrochinolins |
| US3661917A (en) * | 1970-05-21 | 1972-05-09 | Smith Kline French Lab | 3-sulfonamido-4-hydroxyphenyl-2-piperidylcarbinols |
| US3743737A (en) * | 1970-05-21 | 1973-07-03 | Smith Kline French Lab | 3-sulfonamido-4-hydroxyphenyl-2-piperindinylcarbinol compositions |
| DE2901336A1 (de) * | 1979-01-15 | 1980-07-24 | Boehringer Mannheim Gmbh | Neue arylether, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel |
| US4567184A (en) * | 1982-12-01 | 1986-01-28 | Usv Pharmaceutical Corporation | Certain aryl or hetero-aryl derivatives of 1-hydroxy-pentane or 1-hydroxy-hexane which are useful for treating inflammation and allergies |
| IE56702B1 (en) * | 1982-12-01 | 1991-11-06 | Usv Pharma Corp | Antiinflammatory antiallergic compounds |
| US4794188A (en) * | 1982-12-01 | 1988-12-27 | Usv Pharmaceutical Corporation | Certain unsymmetrical quinolinyl ethers having anti-inflammatory and anti-allergic activity |
| NO174506B (no) * | 1984-10-30 | 1994-02-07 | Usv Pharma Corp | Analogifremgangsmaate ved fremstilling av terapeutisk aktive forbindelser |
| US4625034A (en) * | 1985-02-04 | 1986-11-25 | Usv Pharmaceutical Corp. | 1,2-Dihydro; 1,2,3,4-tetrahydro; 5,8 dihydro; and 5,6,7,8-tetrahydroquinoline derivatives |
| US4725619A (en) * | 1985-04-16 | 1988-02-16 | Usv Pharmaceutical Corporation | Aryl and heteroaryl ethers as agents for the treatment of hypersensitive ailments |
| US4728668A (en) * | 1985-04-16 | 1988-03-01 | Usv Pharmaceutical Corporation | Aryl and heteroaryl ethers as agents for the treatment of hypersensitive ailments |
| US4839369A (en) * | 1985-04-16 | 1989-06-13 | Rorer Pharmaceutical Corporation | Aryl and heteroaryl ethers as agents for the treatment of hypersensitive ailments |
| US4631287A (en) * | 1985-04-16 | 1986-12-23 | Usv Pharmaceutical Corp. | Aryl and heteroaryl ethers as agents for the treatment of hypersensitive ailments |
| US4876346A (en) * | 1985-05-02 | 1989-10-24 | American Home Products Corporation | Quinoline compounds |
| EP0271287A3 (en) * | 1986-12-11 | 1990-06-13 | Merck Frosst Canada Inc. | Quinoline dioic acids and amides |
| US4920130A (en) * | 1987-11-02 | 1990-04-24 | Rorer Pharamceutical Corp. | Quinoline derivatives and use thereof as antagonists of leukotriene D4 |
| US4920132A (en) * | 1987-11-03 | 1990-04-24 | Rorer Pharmaceutical Corp. | Quinoline derivatives and use thereof as antagonists of leukotriene D4 |
| US4920133A (en) * | 1987-11-03 | 1990-04-24 | Rorer Pharmaceutical Corp. | Quinoline derivatives and use thereof as antagonists of leukotriene D4 |
| US4920131A (en) * | 1987-11-03 | 1990-04-24 | Rorer Pharmaceutical Corp. | Quinoline derivatives and use thereof as antagonists of leukotriene D4 |
| US4918081A (en) * | 1988-06-20 | 1990-04-17 | Rorer Pharmaceutical Corp. | Quinoline derivatives and use thereof as antagonists of leukotriene d4 |
| EP0349062A1 (en) * | 1988-06-27 | 1990-01-03 | Merck Frosst Canada Inc. | Quinoline ether alkanoic acid |
| IE70521B1 (en) * | 1989-02-28 | 1996-12-11 | Zeneca Pharma Sa | Heterocycles with inhibitory activity of 5-lipoxygenase |
| IE64358B1 (en) * | 1989-07-18 | 1995-07-26 | Ici Plc | Diaryl ether heterocycles |
| GB9113137D0 (en) * | 1990-07-13 | 1991-08-07 | Ici Plc | Thioxo heterocycles |
-
1990
- 1990-08-17 GB GB909018134A patent/GB9018134D0/en active Pending
- 1990-08-21 AU AU61182/90A patent/AU632356B2/en not_active Ceased
- 1990-08-21 IE IE302690A patent/IE64251B1/en not_active IP Right Cessation
- 1990-08-22 NZ NZ235016A patent/NZ235016A/xx unknown
- 1990-08-23 IL IL9548190A patent/IL95481A/xx not_active IP Right Cessation
- 1990-08-29 CA CA002024258A patent/CA2024258A1/en not_active Abandoned
- 1990-09-18 FI FI904591A patent/FI904591A0/fi not_active Application Discontinuation
- 1990-09-21 AT AT90310332T patent/ATE110073T1/de not_active IP Right Cessation
- 1990-09-21 EP EP90310332A patent/EP0420511B1/en not_active Expired - Lifetime
- 1990-09-21 ES ES90310332T patent/ES2058809T3/es not_active Expired - Lifetime
- 1990-09-21 US US07/585,944 patent/US5221677A/en not_active Expired - Lifetime
- 1990-09-21 DE DE69011609T patent/DE69011609T2/de not_active Expired - Fee Related
- 1990-09-21 DK DK90310332.3T patent/DK0420511T3/da active
- 1990-09-27 MY MYPI90001669A patent/MY107266A/en unknown
- 1990-09-28 JP JP2260280A patent/JP2996708B2/ja not_active Expired - Fee Related
- 1990-09-28 HU HU906252A patent/HUT59134A/hu unknown
- 1990-09-28 NO NO90904249A patent/NO904249L/no unknown
- 1990-09-28 PT PT95455A patent/PT95455A/pt not_active Application Discontinuation
- 1990-09-28 DD DD344286A patent/DD300434A5/de unknown
-
1993
- 1993-02-08 US US08/014,673 patent/US5302594A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69011609T2 (de) | 1994-11-24 |
| CA2024258A1 (en) | 1991-03-30 |
| NZ235016A (en) | 1993-04-28 |
| HU906252D0 (en) | 1991-03-28 |
| ATE110073T1 (de) | 1994-09-15 |
| FI904591A0 (fi) | 1990-09-18 |
| EP0420511B1 (en) | 1994-08-17 |
| NO904249D0 (no) | 1990-09-28 |
| EP0420511A3 (en) | 1991-08-28 |
| IL95481A (en) | 1994-11-28 |
| IE64251B1 (en) | 1995-07-26 |
| JPH03130281A (ja) | 1991-06-04 |
| AU632356B2 (en) | 1992-12-24 |
| IE903026A1 (en) | 1991-04-10 |
| ES2058809T3 (es) | 1994-11-01 |
| PT95455A (pt) | 1991-05-22 |
| DD300434A5 (de) | 1992-06-11 |
| MY107266A (en) | 1995-10-31 |
| GB9018134D0 (en) | 1990-10-03 |
| JP2996708B2 (ja) | 2000-01-11 |
| US5302594A (en) | 1994-04-12 |
| AU6118290A (en) | 1991-04-11 |
| NO904249L (no) | 1991-04-02 |
| DE69011609D1 (de) | 1994-09-22 |
| EP0420511A2 (en) | 1991-04-03 |
| DK0420511T3 (da) | 1994-09-12 |
| IL95481A0 (en) | 1991-06-30 |
| US5221677A (en) | 1993-06-22 |
Similar Documents
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| HUT59134A (en) | Process for produicng heterocyclic compounds and pharmaceutical compositions comprising same | |
| HUT58083A (en) | Process for producing heterocyclic compounds and pharmaceutical compositions comprising such compounds | |
| FI901010A0 (fi) | Heterocykliska cykliska etrar. | |
| AU626977B2 (en) | Heterocyclic derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DFC4 | Cancellation of temporary protection due to refusal |