PE20011025A1 - Gamma-hidroxi-2-(fluoroalquilaminocarbonil)-1-piperazinapentanamidas como inhibidores de proteasa del vih - Google Patents
Gamma-hidroxi-2-(fluoroalquilaminocarbonil)-1-piperazinapentanamidas como inhibidores de proteasa del vihInfo
- Publication number
- PE20011025A1 PE20011025A1 PE2000001259A PE0012592000A PE20011025A1 PE 20011025 A1 PE20011025 A1 PE 20011025A1 PE 2000001259 A PE2000001259 A PE 2000001259A PE 0012592000 A PE0012592000 A PE 0012592000A PE 20011025 A1 PE20011025 A1 PE 20011025A1
- Authority
- PE
- Peru
- Prior art keywords
- alkyl
- hydroxy
- cycloalkyl
- hiv protease
- piperazineapentanamides
- Prior art date
Links
- 239000004030 hiv protease inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 2
- NLOLSXYRJFEOTA-OWOJBTEDSA-N (e)-1,1,1,4,4,4-hexafluorobut-2-ene Chemical class FC(F)(F)\C=C\C(F)(F)F NLOLSXYRJFEOTA-OWOJBTEDSA-N 0.000 abstract 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 1
- 208000030507 AIDS Diseases 0.000 abstract 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- -1 PIPERAZINE 2 CARBOXAMIDO Chemical group 0.000 abstract 1
- 108091005804 Peptidases Proteins 0.000 abstract 1
- 239000004365 Protease Substances 0.000 abstract 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 abstract 1
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 abstract 1
- 229960005475 antiinfective agent Drugs 0.000 abstract 1
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 239000003443 antiviral agent Substances 0.000 abstract 1
- 239000002955 immunomodulating agent Substances 0.000 abstract 1
- 229940121354 immunomodulator Drugs 0.000 abstract 1
- 229960001936 indinavir Drugs 0.000 abstract 1
- CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229960000311 ritonavir Drugs 0.000 abstract 1
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 abstract 1
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 abstract 1
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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- A61P37/02—Immunomodulators
-
- 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
-
- 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
- C07D405/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D405/14—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 three or more hetero rings
-
- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Immunology (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16747899P | 1999-11-24 | 1999-11-24 | |
| US17705300P | 2000-01-20 | 2000-01-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20011025A1 true PE20011025A1 (es) | 2001-10-12 |
Family
ID=26863215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2000001259A PE20011025A1 (es) | 1999-11-24 | 2000-11-24 | Gamma-hidroxi-2-(fluoroalquilaminocarbonil)-1-piperazinapentanamidas como inhibidores de proteasa del vih |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6642237B1 (enExample) |
| EP (1) | EP1242426B1 (enExample) |
| JP (1) | JP2003514910A (enExample) |
| AT (1) | ATE377011T1 (enExample) |
| AU (1) | AU777824B2 (enExample) |
| CA (1) | CA2391643C (enExample) |
| CO (1) | CO5261497A1 (enExample) |
| DE (1) | DE60036961T2 (enExample) |
| ES (1) | ES2295068T3 (enExample) |
| PE (1) | PE20011025A1 (enExample) |
| WO (1) | WO2001038332A1 (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9815567D0 (en) * | 1998-07-18 | 1998-09-16 | Glaxo Group Ltd | Antiviral compound |
| WO2001055326A2 (en) * | 2000-01-31 | 2001-08-02 | Human Genome Sciences, Inc. | Nucleic acids, proteins, and antibodies |
| US7049146B2 (en) | 2000-11-14 | 2006-05-23 | Facet Analytical Services And Technology, Llc | Calibration standards, methods, and kits for water determination |
| US7122376B2 (en) * | 2001-11-01 | 2006-10-17 | Facet Analytical Services And Technology, Llc | Calibration standards, methods, and kits for water determination |
| WO2002096359A2 (en) * | 2001-05-30 | 2002-12-05 | Merck & Co., Inc. | Piperazine pentanamide hiv protease inhibitors |
| US6649761B2 (en) | 2001-05-30 | 2003-11-18 | Merck & Co., Inc. | Process for preparing piperazinepentaneamide HIV protease inhibitors |
| US6835860B2 (en) | 2002-02-01 | 2004-12-28 | Merck & Co., Inc. | Iodohydroxylation of olefins |
| US20040067216A1 (en) * | 2002-02-22 | 2004-04-08 | Karki Shyam B. | Hiv protease inhibitors supported on cation exchange resins for oral administration |
| GB0218876D0 (en) * | 2002-08-13 | 2002-09-25 | Merck Sharp & Dohme | Therapeutic agents |
| WO2004027361A1 (en) * | 2002-09-17 | 2004-04-01 | University Of Virginia Patent Foundation | Remote temperature sensing of small volume and related apparatus thereof |
| US7199240B2 (en) * | 2002-12-11 | 2007-04-03 | Merck & Co., Inc. | Reductive alkylation of saturated cyclic amines |
| US8030336B2 (en) * | 2002-12-13 | 2011-10-04 | Ym Biosciences Australia Pty Ltd | Nicotinamide-based kinase inhibitors |
| TW574132B (en) * | 2003-04-14 | 2004-02-01 | Univ Nat Cheng Kung | Integrated microfluidic electro-spray chip system and the analysis method thereof |
| US7161015B1 (en) * | 2005-09-08 | 2007-01-09 | The United States Of America As Represented By The Secretary Of The Navy | Method of making 2-furylalkylketones |
| JP2006316049A (ja) * | 2006-04-11 | 2006-11-24 | Tanabe Seiyaku Co Ltd | ２，２−ジアルコキシエチルアミン化合物およびその製造方法 |
| EP2435037B1 (en) | 2009-05-27 | 2014-11-12 | Merck Sharp & Dohme Corp. | Hiv protease inhibitors |
| CN106074411A (zh) | 2009-10-26 | 2016-11-09 | 默沙东公司 | 包含整合酶抑制剂的固体药物组合物 |
| EP3235818A3 (en) | 2010-04-01 | 2018-03-14 | Critical Outcome Technologies, Inc. | Compounds for the treatment of hiv |
| EP2630133A1 (de) | 2010-10-22 | 2013-08-28 | Bayer Intellectual Property GmbH | Neue heterocylische verbindungen als schädlingsbekämpfungsmittel |
| US9079834B2 (en) | 2010-10-28 | 2015-07-14 | Merck Canada Inc. | HIV protease inhibitors |
| GB201100181D0 (en) | 2011-01-06 | 2011-02-23 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
| GB201101139D0 (en) | 2011-01-21 | 2011-03-09 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
| GB201101140D0 (en) | 2011-01-21 | 2011-03-09 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
| WO2013041602A1 (de) | 2011-09-23 | 2013-03-28 | Bayer Intellectual Property Gmbh | Verwendung 4-substituierter 1-phenyl-pyrazol-3-carbonsäurederivate als wirkstoffe gegen abiotischen pflanzenstress |
| US9133157B2 (en) | 2011-10-26 | 2015-09-15 | Merck Canada Inc. | HIV protease inhibitors |
| KR20150053971A (ko) | 2012-09-11 | 2015-05-19 | 머크 샤프 앤드 돔 코포레이션 | Hiv 프로테아제 억제제 |
| WO2015013835A1 (en) | 2013-07-31 | 2015-02-05 | Merck Sharp & Dohme Corp. | Piperazine derivatives as hiv protease inhibitors |
| EP3052132B1 (en) | 2013-09-30 | 2020-07-29 | Beth Israel Deaconess Medical Center, Inc. | Antibody therapies for human immunodeficiency virus (hiv) |
| EP3083609B1 (en) | 2013-12-19 | 2018-08-15 | Merck Sharp & Dohme Corp. | Hiv protease inhibitors |
| US9834526B2 (en) | 2013-12-19 | 2017-12-05 | Merck Sharp & Dohme Corp. | HIV protease inhibitors |
| WO2015134366A1 (en) | 2014-03-06 | 2015-09-11 | Merck Sharp & Dohme Corp. | Hiv protease inhibitors |
| WO2015138220A1 (en) | 2014-03-10 | 2015-09-17 | Merck Sharp & Dohme Corp. | Piperazine derivatives as hiv protease inhibitors |
| EP2944955A1 (en) * | 2014-05-13 | 2015-11-18 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Benchmark for LC-MS systems |
| CA2954268C (en) * | 2014-07-08 | 2022-11-22 | Dow Agrosciences Llc | Process for the preparation of 3-hydroxypicolinic acids |
| CN104311479B (zh) * | 2014-09-15 | 2016-06-15 | 西华大学 | 3,5-二碘-4-羟基吡啶的合成 |
| TW201730188A (zh) * | 2015-11-30 | 2017-09-01 | 阿斯特捷利康公司 | 1,3,4-噻二唑化合物及其在治療癌症中之用途 |
| TW201822637A (zh) | 2016-11-07 | 2018-07-01 | 德商拜耳廠股份有限公司 | 用於控制動物害蟲的經取代磺醯胺類 |
| WO2019175464A1 (en) | 2018-03-14 | 2019-09-19 | Orion Corporation | Compounds useful as inhibitors of sodium-calcium exchanger (ncx) |
| AR114422A1 (es) | 2018-03-30 | 2020-09-02 | Syngenta Participations Ag | Compuestos herbicidas |
| CA3118623A1 (en) | 2018-11-12 | 2020-05-22 | Syngenta Crop Protection Ag | Herbicidal compounds |
| CN112824417A (zh) * | 2019-11-21 | 2021-05-21 | 上海天慈国际药业有限公司 | 一种劳拉替尼的制备方法 |
| US12083099B2 (en) | 2020-10-28 | 2024-09-10 | Accencio LLC | Methods of treating symptoms of coronavirus infection with viral protease inhibitors |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8927913D0 (en) | 1989-12-11 | 1990-02-14 | Hoffmann La Roche | Amino acid derivatives |
| US5413999A (en) | 1991-11-08 | 1995-05-09 | Merck & Co., Inc. | HIV protease inhibitors useful for the treatment of AIDS |
| CA2081970C (en) | 1991-11-08 | 1997-07-08 | Joseph P. Vacca | Hiv protease inhibitors useful for the treatment of aids |
| US5484926A (en) | 1993-10-07 | 1996-01-16 | Agouron Pharmaceuticals, Inc. | HIV protease inhibitors |
| IL110255A (en) | 1993-07-16 | 1998-12-06 | Merck & Co Inc | Formation and resolution of 2-tert-butylcarboxamido-piperazine |
| US5455351A (en) * | 1993-12-13 | 1995-10-03 | Abbott Laboratories | Retroviral protease inhibiting piperazine compounds |
| PL314984A1 (en) | 1993-12-15 | 1996-09-30 | Merck & Co Inc | Hiv protease inhibitors |
| IL111991A (en) | 1994-01-28 | 2000-07-26 | Abbott Lab | Liquid pharmaceutical composition of HIV protease inhibitors in organic solvent |
| TW438799B (en) | 1997-05-29 | 2001-06-07 | Merck & Co Inc | HIV protease inhibitor |
| AU2012199A (en) * | 1997-12-24 | 1999-07-19 | Vertex Pharmaceuticals Incorporated | Prodrugs of aspartyl protease inhibitors |
-
2000
- 2000-11-21 ES ES00980679T patent/ES2295068T3/es not_active Expired - Lifetime
- 2000-11-21 CA CA002391643A patent/CA2391643C/en not_active Expired - Fee Related
- 2000-11-21 US US09/718,223 patent/US6642237B1/en not_active Expired - Fee Related
- 2000-11-21 WO PCT/US2000/032089 patent/WO2001038332A1/en not_active Ceased
- 2000-11-21 EP EP00980679A patent/EP1242426B1/en not_active Expired - Lifetime
- 2000-11-21 JP JP2001540095A patent/JP2003514910A/ja not_active Withdrawn
- 2000-11-21 AU AU17909/01A patent/AU777824B2/en not_active Ceased
- 2000-11-21 AT AT00980679T patent/ATE377011T1/de not_active IP Right Cessation
- 2000-11-21 DE DE60036961T patent/DE60036961T2/de not_active Expired - Lifetime
- 2000-11-23 CO CO00089726A patent/CO5261497A1/es not_active Application Discontinuation
- 2000-11-24 PE PE2000001259A patent/PE20011025A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1242426B1 (en) | 2007-10-31 |
| WO2001038332A1 (en) | 2001-05-31 |
| US6642237B1 (en) | 2003-11-04 |
| AU1790901A (en) | 2001-06-04 |
| CO5261497A1 (es) | 2003-03-31 |
| EP1242426A1 (en) | 2002-09-25 |
| ATE377011T1 (de) | 2007-11-15 |
| JP2003514910A (ja) | 2003-04-22 |
| CA2391643A1 (en) | 2001-05-31 |
| AU777824B2 (en) | 2004-11-04 |
| CA2391643C (en) | 2010-01-12 |
| DE60036961D1 (de) | 2007-12-13 |
| ES2295068T3 (es) | 2008-04-16 |
| DE60036961T2 (de) | 2008-08-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD | Application declared void or lapsed |