RU2006118021A - Замещенные пиридин-2-ил-тетразолы (варианты), фармацевтическая композиция, лекарственное средство, способ лечения расстройств с их использованием, способ ингибирования активации метаботропных глютаматных рецепторов -5 и способ получения пиридилпроизводных - Google Patents
Замещенные пиридин-2-ил-тетразолы (варианты), фармацевтическая композиция, лекарственное средство, способ лечения расстройств с их использованием, способ ингибирования активации метаботропных глютаматных рецепторов -5 и способ получения пиридилпроизводных Download PDFInfo
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- RU2006118021A RU2006118021A RU2006118021/04A RU2006118021A RU2006118021A RU 2006118021 A RU2006118021 A RU 2006118021A RU 2006118021/04 A RU2006118021/04 A RU 2006118021/04A RU 2006118021 A RU2006118021 A RU 2006118021A RU 2006118021 A RU2006118021 A RU 2006118021A
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- RU
- Russia
- Prior art keywords
- tetrazol
- fluoropyridin
- alkyl
- treatment
- benzonitrile
- Prior art date
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- 238000000034 method Methods 0.000 title claims 15
- 239000008194 pharmaceutical composition Substances 0.000 title claims 3
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 title 1
- 230000005764 inhibitory process Effects 0.000 title 1
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 claims 5
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- FBUHFQUZAYMTOM-UHFFFAOYSA-N pyridin-2-ylcyanamide Chemical compound N#CNC1=CC=CC=N1 FBUHFQUZAYMTOM-UHFFFAOYSA-N 0.000 claims 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 3
- 238000000354 decomposition reaction Methods 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- XUICYRFPJOHKGW-UHFFFAOYSA-N 3-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]-5-(methoxymethyl)benzonitrile Chemical compound COCC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 XUICYRFPJOHKGW-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 102000005962 receptors Human genes 0.000 claims 2
- 108020003175 receptors Proteins 0.000 claims 2
- 235000010288 sodium nitrite Nutrition 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- LQWXEEDCMLEVHU-UHFFFAOYSA-N 2-(2h-tetrazol-5-yl)pyridine Chemical class N1=CC=CC=C1C1=NNN=N1 LQWXEEDCMLEVHU-UHFFFAOYSA-N 0.000 claims 1
- AQGCLHIWIZUYPV-UHFFFAOYSA-N 3-(difluoromethoxy)-5-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]benzonitrile Chemical compound FC(F)OC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 AQGCLHIWIZUYPV-UHFFFAOYSA-N 0.000 claims 1
- RNUMNUGYLBCCEU-UHFFFAOYSA-N 3-(ethylamino)-5-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]benzonitrile Chemical compound CCNC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 RNUMNUGYLBCCEU-UHFFFAOYSA-N 0.000 claims 1
- GTANSZNHJARZLJ-UHFFFAOYSA-N 3-[2-(5-chloropyridin-2-yl)tetrazol-5-yl]-5-fluorobenzonitrile Chemical compound FC1=CC(C#N)=CC(C2=NN(N=N2)C=2N=CC(Cl)=CC=2)=C1 GTANSZNHJARZLJ-UHFFFAOYSA-N 0.000 claims 1
- SAWSSPISYVVUPP-UHFFFAOYSA-N 3-[5-(5-chloropyridin-2-yl)tetrazol-2-yl]-5-fluorobenzonitrile Chemical compound FC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(Cl)=CC=2)=C1 SAWSSPISYVVUPP-UHFFFAOYSA-N 0.000 claims 1
- WQWFBZQKKNQGSY-UHFFFAOYSA-N 3-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]-5-(2-methoxyethoxy)benzonitrile Chemical compound COCCOC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 WQWFBZQKKNQGSY-UHFFFAOYSA-N 0.000 claims 1
- UYRBZIYJANWFLG-UHFFFAOYSA-N 3-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]-5-(trifluoromethoxy)benzonitrile Chemical compound N1=CC(F)=CC=C1C1=NN(C=2C=C(C=C(OC(F)(F)F)C=2)C#N)N=N1 UYRBZIYJANWFLG-UHFFFAOYSA-N 0.000 claims 1
- NDUDAERNMBXBRF-UHFFFAOYSA-N 3-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]-5-iodobenzonitrile Chemical class N1=CC(F)=CC=C1C1=NN(C=2C=C(C=C(I)C=2)C#N)N=N1 NDUDAERNMBXBRF-UHFFFAOYSA-N 0.000 claims 1
- HVPQJXMCMHHZHI-UHFFFAOYSA-N 3-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]-5-methoxybenzonitrile Chemical compound COC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 HVPQJXMCMHHZHI-UHFFFAOYSA-N 0.000 claims 1
- TUVRMXKPGAJUGF-UHFFFAOYSA-N 3-amino-5-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]benzonitrile Chemical compound NC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 TUVRMXKPGAJUGF-UHFFFAOYSA-N 0.000 claims 1
- CKISQUUTFPIQAX-UHFFFAOYSA-N 3-fluoro-5-[2-(5-fluoropyridin-2-yl)tetrazol-5-yl]benzonitrile Chemical compound N1=CC(F)=CC=C1N1N=C(C=2C=C(C=C(F)C=2)C#N)N=N1 CKISQUUTFPIQAX-UHFFFAOYSA-N 0.000 claims 1
- UQCQFXVIFGQFRL-UHFFFAOYSA-N 3-fluoro-5-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]benzonitrile Chemical compound N1=CC(F)=CC=C1C1=NN(C=2C=C(C=C(F)C=2)C#N)N=N1 UQCQFXVIFGQFRL-UHFFFAOYSA-N 0.000 claims 1
- IFOXWHQFTSCNQB-UHFFFAOYSA-N 5-aminopyridine-2-carbonitrile Chemical group NC1=CC=C(C#N)N=C1 IFOXWHQFTSCNQB-UHFFFAOYSA-N 0.000 claims 1
- QJWNJNTZXKFBKG-UHFFFAOYSA-N 5-fluoro-2-[2-(3-fluoro-5-methoxyphenyl)tetrazol-5-yl]pyridine Chemical compound COC1=CC(F)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 QJWNJNTZXKFBKG-UHFFFAOYSA-N 0.000 claims 1
- BHXHRMVSUUPOLX-UHFFFAOYSA-N 5-fluoropyridine-2-carbonitrile Chemical group FC1=CC=C(C#N)N=C1 BHXHRMVSUUPOLX-UHFFFAOYSA-N 0.000 claims 1
- RFXRMGATCPIUGX-UHFFFAOYSA-N 6-[2-(3-cyano-5-fluorophenyl)tetrazol-5-yl]pyridine-3-carbonitrile Chemical compound FC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(=CC=2)C#N)=C1 RFXRMGATCPIUGX-UHFFFAOYSA-N 0.000 claims 1
- WLBDEBUYJGERNR-UHFFFAOYSA-N 6-[5-(3-cyano-5-fluorophenyl)tetrazol-2-yl]pyridine-3-carbonitrile Chemical compound FC1=CC(C#N)=CC(C2=NN(N=N2)C=2N=CC(=CC=2)C#N)=C1 WLBDEBUYJGERNR-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- -1 methoxy, difluoromethoxy, trifluoromethoxy, 2-methoxyethoxy, ethylamino Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000006396 nitration reaction Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000010792 warming Methods 0.000 claims 1
Classifications
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- 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
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- Addiction (AREA)
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- Immunology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53063303P | 2003-12-19 | 2003-12-19 | |
| US60/530,633 | 2003-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2006118021A true RU2006118021A (ru) | 2007-12-10 |
Family
ID=34748746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2006118021/04A RU2006118021A (ru) | 2003-12-19 | 2004-12-13 | Замещенные пиридин-2-ил-тетразолы (варианты), фармацевтическая композиция, лекарственное средство, способ лечения расстройств с их использованием, способ ингибирования активации метаботропных глютаматных рецепторов -5 и способ получения пиридилпроизводных |
Country Status (20)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1706392A2 (en) * | 2004-01-08 | 2006-10-04 | Syngenta Participations AG | Pesticidal heterocyclic dihaloallyl compounds |
| UY29796A1 (es) | 2005-09-29 | 2007-04-30 | Astrazeneca Ab | Nuevos compuestos para el tratamiento de trastornos neurológicos, psiquiátricos o del dolor |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| US20120095056A1 (en) * | 2009-03-19 | 2012-04-19 | Neurosearch A/S | 2,5-disubstituted tetrazole derivatives and their use as nicotinic acetylcholine receptor modulators |
| WO2011073297A1 (en) * | 2009-12-18 | 2011-06-23 | Neurosearch A/S | Tetrazole derivatives as nicotinic acetylcholine receptor moudlators |
| WO2011073298A1 (en) * | 2009-12-18 | 2011-06-23 | Neurosearch A/S | Tetrazole derivatives as nicotinic acetylcholine receptor modulators |
| CN102762572A (zh) | 2010-02-01 | 2012-10-31 | 诺瓦提斯公司 | 作为CRF-1受体拮抗剂的吡唑并[5,1b]*唑衍生物 |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| EP2531490B1 (en) | 2010-02-02 | 2014-10-15 | Novartis AG | Cyclohexyl amide derivatives as crf receptor antagonists |
| GB201312800D0 (en) | 2013-07-17 | 2013-08-28 | Heptares Therapeutics Ltd | mGlu5 modulators |
| WO2016001452A1 (en) | 2014-07-04 | 2016-01-07 | Universität Zürich | Compounds, in particular for use in the treatment of a disease or condition for which a bromodomain inhibitor is indicated |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6660753B2 (en) * | 1999-08-19 | 2003-12-09 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| PL369598A1 (en) * | 2001-02-21 | 2005-05-02 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| CA2462289C (en) * | 2001-10-04 | 2010-02-23 | Nicholas D. Cosford | Heteroaryl substituted tetrazole modulators of metabotropic glutamate receptor-5 |
-
2004
- 2004-12-13 EP EP04813689A patent/EP1713791B1/en not_active Expired - Lifetime
- 2004-12-13 WO PCT/US2004/041401 patent/WO2005066155A1/en not_active Ceased
- 2004-12-13 RU RU2006118021/04A patent/RU2006118021A/ru not_active Application Discontinuation
- 2004-12-13 US US10/582,051 patent/US20070255061A1/en not_active Abandoned
- 2004-12-13 MX MXPA06006674A patent/MXPA06006674A/es unknown
- 2004-12-13 CN CNA2004800406448A patent/CN1906187A/zh active Pending
- 2004-12-13 JP JP2006545760A patent/JP2007514790A/ja active Pending
- 2004-12-13 DE DE602004013469T patent/DE602004013469T9/de not_active Expired - Fee Related
- 2004-12-13 KR KR1020067011449A patent/KR20060126993A/ko not_active Withdrawn
- 2004-12-13 AT AT04813689T patent/ATE393767T1/de not_active IP Right Cessation
- 2004-12-13 ES ES04813689T patent/ES2303969T3/es not_active Expired - Lifetime
- 2004-12-13 AU AU2004312342A patent/AU2004312342A1/en not_active Abandoned
- 2004-12-13 BR BRPI0417308-2A patent/BRPI0417308A/pt not_active IP Right Cessation
- 2004-12-13 CA CA002548039A patent/CA2548039A1/en not_active Abandoned
- 2004-12-16 TW TW093139143A patent/TW200524602A/zh unknown
- 2004-12-16 AR ARP040104711A patent/AR046768A1/es unknown
- 2004-12-17 UY UY28685A patent/UY28685A1/es unknown
-
2006
- 2006-05-25 IL IL175909A patent/IL175909A0/en unknown
- 2006-06-01 NO NO20062533A patent/NO20062533L/no not_active Application Discontinuation
- 2006-06-07 ZA ZA200604681A patent/ZA200604681B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| UY28685A1 (es) | 2005-06-30 |
| HK1095598A1 (en) | 2007-05-11 |
| IL175909A0 (en) | 2008-02-09 |
| EP1713791A1 (en) | 2006-10-25 |
| WO2005066155A1 (en) | 2005-07-21 |
| DE602004013469T2 (de) | 2009-06-18 |
| AR046768A1 (es) | 2005-12-21 |
| ATE393767T1 (de) | 2008-05-15 |
| MXPA06006674A (es) | 2007-04-16 |
| US20070255061A1 (en) | 2007-11-01 |
| AU2004312342A1 (en) | 2005-07-21 |
| EP1713791B1 (en) | 2008-04-30 |
| ZA200604681B (en) | 2007-04-25 |
| CN1906187A (zh) | 2007-01-31 |
| TW200524602A (en) | 2005-08-01 |
| KR20060126993A (ko) | 2006-12-11 |
| JP2007514790A (ja) | 2007-06-07 |
| DE602004013469D1 (de) | 2008-06-12 |
| BRPI0417308A (pt) | 2007-09-11 |
| CA2548039A1 (en) | 2005-07-21 |
| ES2303969T3 (es) | 2008-09-01 |
| NO20062533L (no) | 2006-09-19 |
| DE602004013469T9 (de) | 2009-09-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20090325 |