AU2004271697A1 - Combination of phenylcarboxamides with beta-adrenergic receptor blockers and use thereof for the treatment of atrial arrhythmias - Google Patents
Combination of phenylcarboxamides with beta-adrenergic receptor blockers and use thereof for the treatment of atrial arrhythmias Download PDFInfo
- Publication number
- AU2004271697A1 AU2004271697A1 AU2004271697A AU2004271697A AU2004271697A1 AU 2004271697 A1 AU2004271697 A1 AU 2004271697A1 AU 2004271697 A AU2004271697 A AU 2004271697A AU 2004271697 A AU2004271697 A AU 2004271697A AU 2004271697 A1 AU2004271697 A1 AU 2004271697A1
- Authority
- AU
- Australia
- Prior art keywords
- beta
- carbon atoms
- blockers
- compounds
- atenolol
- 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
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical class NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title claims description 33
- 238000011282 treatment Methods 0.000 title description 11
- 206010003130 Arrhythmia supraventricular Diseases 0.000 title description 8
- 102000012740 beta Adrenergic Receptors Human genes 0.000 title description 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 83
- 239000002876 beta blocker Substances 0.000 claims description 70
- 229940097320 beta blocking agent Drugs 0.000 claims description 70
- 150000003839 salts Chemical class 0.000 claims description 49
- METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 claims description 48
- 229960002274 atenolol Drugs 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 claims description 28
- 229960002508 pindolol Drugs 0.000 claims description 27
- PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 claims description 27
- 206010003658 Atrial Fibrillation Diseases 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 206010003662 Atrial flutter Diseases 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 238000002560 therapeutic procedure Methods 0.000 claims description 16
- -1 cetiprolol Chemical compound 0.000 claims description 15
- 238000011321 prophylaxis Methods 0.000 claims description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- CEMAWMOMDPGJMB-UHFFFAOYSA-N (+-)-Oxprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1OCC=C CEMAWMOMDPGJMB-UHFFFAOYSA-N 0.000 claims description 14
- GOEMGAFJFRBGGG-UHFFFAOYSA-N acebutolol Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1 GOEMGAFJFRBGGG-UHFFFAOYSA-N 0.000 claims description 14
- 229960002122 acebutolol Drugs 0.000 claims description 14
- 229960002213 alprenolol Drugs 0.000 claims description 14
- PAZJSJFMUHDSTF-UHFFFAOYSA-N alprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1CC=C PAZJSJFMUHDSTF-UHFFFAOYSA-N 0.000 claims description 14
- 229960004195 carvedilol Drugs 0.000 claims description 14
- NPAKNKYSJIDKMW-UHFFFAOYSA-N carvedilol Chemical compound COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=NC3=CC=C[CH]C3=C12 NPAKNKYSJIDKMW-UHFFFAOYSA-N 0.000 claims description 14
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 claims description 14
- 229960002237 metoprolol Drugs 0.000 claims description 14
- 229960004255 nadolol Drugs 0.000 claims description 14
- VWPOSFSPZNDTMJ-UCWKZMIHSA-N nadolol Chemical compound C1[C@@H](O)[C@@H](O)CC2=C1C=CC=C2OCC(O)CNC(C)(C)C VWPOSFSPZNDTMJ-UCWKZMIHSA-N 0.000 claims description 14
- 229960004570 oxprenolol Drugs 0.000 claims description 14
- 229960003712 propranolol Drugs 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 11
- CHDSRMIDIQABTP-UHFFFAOYSA-N 2-[2-[[[2-(4-methoxyphenyl)acetyl]amino]methyl]phenyl]-n-(2-pyridin-3-ylethyl)benzamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NCC1=CC=CC=C1C1=CC=CC=C1C(=O)NCCC1=CC=CN=C1 CHDSRMIDIQABTP-UHFFFAOYSA-N 0.000 claims description 9
- VYUUPUMKBLIKJV-NRFANRHFSA-N 5-fluoro-n-[(1s)-1-phenylpropyl]-2-(quinolin-8-ylsulfonylamino)benzamide Chemical compound C1([C@@H](NC(=O)C=2C(=CC=C(F)C=2)NS(=O)(=O)C=2C3=NC=CC=C3C=CC=2)CC)=CC=CC=C1 VYUUPUMKBLIKJV-NRFANRHFSA-N 0.000 claims description 9
- NXWGWUVGUSFQJC-GFCCVEGCSA-N (2r)-1-[(2-methyl-1h-indol-4-yl)oxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NC[C@@H](O)COC1=CC=CC2=C1C=C(C)N2 NXWGWUVGUSFQJC-GFCCVEGCSA-N 0.000 claims description 6
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 claims description 6
- VHYCDWMUTMEGQY-UHFFFAOYSA-N bisoprolol Chemical compound CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1 VHYCDWMUTMEGQY-UHFFFAOYSA-N 0.000 claims description 6
- 229960002781 bisoprolol Drugs 0.000 claims description 6
- 229960001222 carteolol Drugs 0.000 claims description 6
- LWAFSWPYPHEXKX-UHFFFAOYSA-N carteolol Chemical compound N1C(=O)CCC2=C1C=CC=C2OCC(O)CNC(C)(C)C LWAFSWPYPHEXKX-UHFFFAOYSA-N 0.000 claims description 6
- 229960003134 mepindolol Drugs 0.000 claims description 6
- 229960002035 penbutolol Drugs 0.000 claims description 6
- KQXKVJAGOJTNJS-HNNXBMFYSA-N penbutolol Chemical compound CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1 KQXKVJAGOJTNJS-HNNXBMFYSA-N 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 claims description 5
- XPQIPUZPSLAZDV-UHFFFAOYSA-N 2-pyridylethylamine Chemical compound NCCC1=CC=CC=N1 XPQIPUZPSLAZDV-UHFFFAOYSA-N 0.000 claims description 5
- JOATXPAWOHTVSZ-UHFFFAOYSA-N Celiprolol Chemical compound CCN(CC)C(=O)NC1=CC=C(OCC(O)CNC(C)(C)C)C(C(C)=O)=C1 JOATXPAWOHTVSZ-UHFFFAOYSA-N 0.000 claims description 5
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 5
- 229960000330 bupranolol Drugs 0.000 claims description 5
- HQIRNZOQPUAHHV-UHFFFAOYSA-N bupranolol Chemical compound CC1=CC=C(Cl)C(OCC(O)CNC(C)(C)C)=C1 HQIRNZOQPUAHHV-UHFFFAOYSA-N 0.000 claims description 5
- 229960002320 celiprolol Drugs 0.000 claims description 5
- AQNDDEOPVVGCPG-UHFFFAOYSA-N esmolol Chemical compound COC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C1 AQNDDEOPVVGCPG-UHFFFAOYSA-N 0.000 claims description 5
- 229960003745 esmolol Drugs 0.000 claims description 5
- FLOLVFLAXFXKBU-UHFFFAOYSA-N S9947 Chemical compound C=1C=CC=CC=1COC(=O)NCC1=CC=CC=C1C1=CC=CC=C1C(=O)NCCC1=CC=CC=N1 FLOLVFLAXFXKBU-UHFFFAOYSA-N 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- IXKPEYHRIVQTCU-UHFFFAOYSA-N n-[(2,4-difluorophenyl)methyl]-2-[2-[[[2-(4-methoxyphenyl)acetyl]amino]methyl]phenyl]benzamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NCC1=CC=CC=C1C1=CC=CC=C1C(=O)NCC1=CC=C(F)C=C1F IXKPEYHRIVQTCU-UHFFFAOYSA-N 0.000 claims description 4
- 230000000144 pharmacologic effect Effects 0.000 claims description 3
- MCJOUORSTIRIDM-UHFFFAOYSA-N 2-[2-(phenylmethoxycarbonylaminomethyl)phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1CNC(=O)OCC1=CC=CC=C1 MCJOUORSTIRIDM-UHFFFAOYSA-N 0.000 claims description 2
- HXYRIIDLHHAJHV-UHFFFAOYSA-N 2-[2-[[[2-(4-methoxyphenyl)acetyl]amino]methyl]phenyl]benzoic acid Chemical compound C1=CC(OC)=CC=C1CC(=O)NCC1=CC=CC=C1C1=CC=CC=C1C(O)=O HXYRIIDLHHAJHV-UHFFFAOYSA-N 0.000 claims description 2
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
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- 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
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- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- 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
- A61P9/06—Antiarrhythmics
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10341233A DE10341233A1 (de) | 2003-09-08 | 2003-09-08 | Kombination von Phenylcarbonsäureamiden mit beta-Adrenozeptoren-Blockern und deren Verwendung zur Behandlung von Vorhofarrhythmien |
| DE10341233.6 | 2003-09-08 | ||
| PCT/EP2004/009837 WO2005025674A1 (de) | 2003-09-08 | 2004-09-03 | Kombination von phenylcarbonsäureamiden mit beta-adrenozeptoren-blockern und deren verwendung zur behandlung von vorhofarrhythmien |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2004271697A1 true AU2004271697A1 (en) | 2005-03-24 |
Family
ID=34202398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004271697A Abandoned AU2004271697A1 (en) | 2003-09-08 | 2004-09-03 | Combination of phenylcarboxamides with beta-adrenergic receptor blockers and use thereof for the treatment of atrial arrhythmias |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1670551A1 (de) |
| JP (1) | JP2007505036A (de) |
| AR (1) | AR045601A1 (de) |
| AU (1) | AU2004271697A1 (de) |
| BR (1) | BRPI0414203A (de) |
| CA (1) | CA2538009A1 (de) |
| DE (1) | DE10341233A1 (de) |
| IL (1) | IL173919A0 (de) |
| MX (1) | MXPA06002103A (de) |
| PE (1) | PE20050373A1 (de) |
| TW (1) | TW200526580A (de) |
| WO (1) | WO2005025674A1 (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005028862A1 (de) * | 2005-06-22 | 2007-01-11 | Sanofi-Aventis Deutschland Gmbh | Substituierte Heterocyclen, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
| TW200812962A (en) * | 2006-07-12 | 2008-03-16 | Astrazeneca Ab | New compounds I/418 |
| CN105130957A (zh) * | 2009-05-29 | 2015-12-09 | 拉夸里亚创药株式会社 | 作为钙或钠通道阻滞剂的芳基取代羧酰胺衍生物 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6194458B1 (en) * | 1998-10-30 | 2001-02-27 | Merck & Co., Inc. | Benzamide potassium channel inhibitors |
| DE19947457A1 (de) * | 1999-10-02 | 2001-04-05 | Aventis Pharma Gmbh | 2'-Substituierte 1,1'-Biphenyl-2-carbonamide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie enthaltende pharmazeutische Zubereitungen |
| DE10059418A1 (de) * | 2000-11-30 | 2002-06-20 | Aventis Pharma Gmbh | Ortho, meta-substituierte Bisarylverbindungen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
| DE10060807A1 (de) * | 2000-12-07 | 2002-06-20 | Aventis Pharma Gmbh | Ortho, ortho-substituierte stickstoffhaltige Bisarylverbindungen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
| DE10121003A1 (de) * | 2001-04-28 | 2002-12-19 | Aventis Pharma Gmbh | Anthranilsäureamide, Verfahren zur Herstellung, ihrer Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
| DE10128331A1 (de) * | 2001-06-12 | 2002-12-19 | Aventis Pharma Gmbh | Anthranilsäureamide mit Heteroarylsulfonyl-Seitenkette, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen |
-
2003
- 2003-09-08 DE DE10341233A patent/DE10341233A1/de not_active Withdrawn
-
2004
- 2004-09-02 PE PE2004000848A patent/PE20050373A1/es not_active Application Discontinuation
- 2004-09-03 MX MXPA06002103A patent/MXPA06002103A/es not_active Application Discontinuation
- 2004-09-03 CA CA002538009A patent/CA2538009A1/en not_active Abandoned
- 2004-09-03 AU AU2004271697A patent/AU2004271697A1/en not_active Abandoned
- 2004-09-03 WO PCT/EP2004/009837 patent/WO2005025674A1/de active Application Filing
- 2004-09-03 BR BRPI0414203-9A patent/BRPI0414203A/pt not_active Application Discontinuation
- 2004-09-03 JP JP2006525115A patent/JP2007505036A/ja not_active Abandoned
- 2004-09-03 EP EP04764792A patent/EP1670551A1/de not_active Withdrawn
- 2004-09-06 TW TW093126817A patent/TW200526580A/zh unknown
- 2004-09-06 AR ARP040103199A patent/AR045601A1/es unknown
-
2006
- 2006-02-23 IL IL173919A patent/IL173919A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1670551A1 (de) | 2006-06-21 |
| DE10341233A1 (de) | 2005-03-24 |
| TW200526580A (en) | 2005-08-16 |
| IL173919A0 (en) | 2006-07-05 |
| JP2007505036A (ja) | 2007-03-08 |
| AR045601A1 (es) | 2005-11-02 |
| BRPI0414203A (pt) | 2006-10-31 |
| WO2005025674A1 (de) | 2005-03-24 |
| CA2538009A1 (en) | 2005-03-24 |
| PE20050373A1 (es) | 2005-07-05 |
| MXPA06002103A (es) | 2006-05-31 |
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Legal Events
| Date | Code | Title | Description |
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| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |