CN1960969B - 组胺h3受体药物、其制备方法及治疗用途 - Google Patents
组胺h3受体药物、其制备方法及治疗用途 Download PDFInfo
- Publication number
- CN1960969B CN1960969B CN2005800171466A CN200580017146A CN1960969B CN 1960969 B CN1960969 B CN 1960969B CN 2005800171466 A CN2005800171466 A CN 2005800171466A CN 200580017146 A CN200580017146 A CN 200580017146A CN 1960969 B CN1960969 B CN 1960969B
- Authority
- CN
- China
- Prior art keywords
- tetramethyleneimine
- ylmethyl
- ketone
- biphenyl
- fluoro
- 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.)
- Expired - Lifetime
Links
- 0 *C(C=C1)=*=C1C(O*)=O Chemical compound *C(C=C1)=*=C1C(O*)=O 0.000 description 7
- GKQRYNKNGUXFAM-UHFFFAOYSA-N CC1N(CC(CCC2)N2C(c(c(F)c2)ccc2-c(cc2)ccc2S(C)(=O)=O)O)CCC1 Chemical compound CC1N(CC(CCC2)N2C(c(c(F)c2)ccc2-c(cc2)ccc2S(C)(=O)=O)O)CCC1 GKQRYNKNGUXFAM-UHFFFAOYSA-N 0.000 description 1
- VMBDRTUOQYTNLE-UHFFFAOYSA-N CCS(c(cc1)ncc1Cl)(=O)=O Chemical compound CCS(c(cc1)ncc1Cl)(=O)=O VMBDRTUOQYTNLE-UHFFFAOYSA-N 0.000 description 1
- JYQBCMSSLAAZCP-NRFANRHFSA-N CCS(c(nc1)ccc1-c(cc1)ccc1C(N1[C@H](CN2CCCC2)CCC1)=O)(=O)=O Chemical compound CCS(c(nc1)ccc1-c(cc1)ccc1C(N1[C@H](CN2CCCC2)CCC1)=O)(=O)=O JYQBCMSSLAAZCP-NRFANRHFSA-N 0.000 description 1
- FDUZRCBLAHNILK-FQEVSTJZSA-N CS(Nc(cc1)ccc1-c(cc1)cc(F)c1C(N1[C@H](CN2CCCC2)CCC1)=O)(=O)=O Chemical compound CS(Nc(cc1)ccc1-c(cc1)cc(F)c1C(N1[C@H](CN2CCCC2)CCC1)=O)(=O)=O FDUZRCBLAHNILK-FQEVSTJZSA-N 0.000 description 1
- QGZHIQSJYSTPJP-QFIPXVFZSA-N CS(Nc1cc(-c(cc2)ccc2C(N2[C@H](CN3CCCC3)CCC2)=O)ccc1)(=O)=O Chemical compound CS(Nc1cc(-c(cc2)ccc2C(N2[C@H](CN3CCCC3)CCC2)=O)ccc1)(=O)=O QGZHIQSJYSTPJP-QFIPXVFZSA-N 0.000 description 1
- IPCPNGSAHHVVRF-IBGZPJMESA-N CS(c(cc1)ccc1-c(cc1)cc(F)c1C(N1[C@H](CN2CCCC2)CCC1)=O)(=O)=O Chemical compound CS(c(cc1)ccc1-c(cc1)cc(F)c1C(N1[C@H](CN2CCCC2)CCC1)=O)(=O)=O IPCPNGSAHHVVRF-IBGZPJMESA-N 0.000 description 1
- NYXUPJCNRNCHSZ-IBGZPJMESA-N CS(c(cc1)ccc1-c1ccc(C(N2[C@H](CN3CCCC3)CCC2)=O)c(C(F)(F)F)c1)(=O)=O Chemical compound CS(c(cc1)ccc1-c1ccc(C(N2[C@H](CN3CCCC3)CCC2)=O)c(C(F)(F)F)c1)(=O)=O NYXUPJCNRNCHSZ-IBGZPJMESA-N 0.000 description 1
- POZQSXUCDHVQLL-YPMHNXCESA-N C[C@H]1N(C[C@H](CCC2)N2C(c(c(F)cc(Br)c2)c2F)=O)CCC1 Chemical compound C[C@H]1N(C[C@H](CCC2)N2C(c(c(F)cc(Br)c2)c2F)=O)CCC1 POZQSXUCDHVQLL-YPMHNXCESA-N 0.000 description 1
- KOXPHWUZZWVCLW-SFQUDFHCSA-N O/C=C(\CCC1)/N1C(C(CC1)=CC=C1c1ccc(C(F)(F)F)cc1)=O Chemical compound O/C=C(\CCC1)/N1C(C(CC1)=CC=C1c1ccc(C(F)(F)F)cc1)=O KOXPHWUZZWVCLW-SFQUDFHCSA-N 0.000 description 1
- ZZBFREXYPAZUGC-FQEVSTJZSA-N O=C(c(cc1)ccc1-c1ccncc1)N1[C@H](CN2CCCC2)CCC1 Chemical compound O=C(c(cc1)ccc1-c1ccncc1)N1[C@H](CN2CCCC2)CCC1 ZZBFREXYPAZUGC-FQEVSTJZSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N OC(C(F)(F)F)=O Chemical compound OC(C(F)(F)F)=O DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- GBAJKJNGCONQII-UHFFFAOYSA-N OC(c(ccc(Br)c1)c1F)Cl Chemical compound OC(c(ccc(Br)c1)c1F)Cl GBAJKJNGCONQII-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- A—HUMAN NECESSITIES
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- 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
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- 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
- C07D401/10—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 aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- C07D405/10—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 aromatic 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Psychiatry (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Reproductive Health (AREA)
- Pulmonology (AREA)
- Otolaryngology (AREA)
- Gynecology & Obstetrics (AREA)
- Anesthesiology (AREA)
- Addiction (AREA)
- Heart & Thoracic Surgery (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Rheumatology (AREA)
- Vascular Medicine (AREA)
- Psychology (AREA)
- Pregnancy & Childbirth (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55854204P | 2004-04-01 | 2004-04-01 | |
| US60/558,542 | 2004-04-01 | ||
| US61710104P | 2004-10-08 | 2004-10-08 | |
| US60/617,101 | 2004-10-08 | ||
| PCT/US2005/010240 WO2005097740A1 (en) | 2004-04-01 | 2005-03-25 | Histamine h3 receptor agents, preparation and therapeutic uses |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1960969A CN1960969A (zh) | 2007-05-09 |
| CN1960969B true CN1960969B (zh) | 2012-03-28 |
Family
ID=34964070
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2005800171466A Expired - Lifetime CN1960969B (zh) | 2004-04-01 | 2005-03-25 | 组胺h3受体药物、其制备方法及治疗用途 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7632857B2 (enExample) |
| EP (1) | EP1735278B1 (enExample) |
| JP (1) | JP4777974B2 (enExample) |
| CN (1) | CN1960969B (enExample) |
| AT (1) | ATE454372T1 (enExample) |
| AU (1) | AU2005230881B9 (enExample) |
| BR (1) | BRPI0509298A (enExample) |
| CA (1) | CA2561628C (enExample) |
| CY (1) | CY1109860T1 (enExample) |
| DE (1) | DE602005018758D1 (enExample) |
| DK (1) | DK1735278T3 (enExample) |
| ES (1) | ES2337376T3 (enExample) |
| MX (1) | MXPA06011167A (enExample) |
| PL (1) | PL1735278T3 (enExample) |
| PT (1) | PT1735278E (enExample) |
| SI (1) | SI1735278T1 (enExample) |
| WO (1) | WO2005097740A1 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8008301B2 (en) * | 2004-04-01 | 2011-08-30 | Eli Lilly And Company | Histamine H3 receptor agents, preparation and therapeutic uses |
| EP1784400B1 (en) * | 2004-08-23 | 2015-01-14 | Eli Lilly And Company | Histamine h3 receptor agents, preparation and therapeutic uses |
| GT200600042A (es) * | 2005-02-10 | 2006-09-27 | Aventis Pharma Inc | Compuestos de bis arilo y heteroarilo sustituido como antagonistas selectivos de 5ht2a |
| CN101151244B (zh) * | 2005-04-01 | 2014-09-03 | 伊莱利利公司 | 组胺h3受体活性剂、制备和治疗用途 |
| JP5193033B2 (ja) * | 2005-07-01 | 2013-05-08 | イーライ リリー アンド カンパニー | ヒスタミンｈ３受容体薬剤、製剤及び治療的使用 |
| US8158673B2 (en) * | 2005-10-27 | 2012-04-17 | Pfizer Inc. | Histamine-3 receptor antagonists |
| WO2007055418A1 (ja) * | 2005-11-10 | 2007-05-18 | Banyu Pharmaceutical Co., Ltd. | アザ置換スピロ誘導体 |
| ATE485294T1 (de) | 2005-11-18 | 2010-11-15 | Hoffmann La Roche | Azaindol-2-carboxamid-derivate |
| US7351708B2 (en) | 2005-12-16 | 2008-04-01 | Hoffmann-La Roche Inc. | Pyrrolo [2,3-b] pyridine derivatives |
| AU2007227681A1 (en) * | 2006-03-15 | 2007-09-27 | Wyeth | N-substituted-azacyclylamines as histamine-3 antagonists |
| WO2008005338A1 (en) * | 2006-06-29 | 2008-01-10 | Arena Pharmaceuticals, Inc. | Modulators of the histamine h3-receptor useful for the treatment of disorders related thereto |
| TW200823204A (en) * | 2006-10-17 | 2008-06-01 | Arena Pharm Inc | Biphenyl sulfonyl and phenyl-heteroaryl sulfonyl modulators of the histamine H3-receptor useful for the treatment of disorders related thereto |
| JP2010529130A (ja) * | 2007-06-08 | 2010-08-26 | アリーナ ファーマシューティカルズ， インコーポレイテッド | （ｒ）−１−｛２−［４’−（３−メトキシ−プロパン−１−スルホニル）−ビフェニル−４−イル］−エチル｝−２−メチル−ピロリジンの結晶形、およびその組成物ならびにそれに関連する方法 |
| CA2700691A1 (en) * | 2007-10-01 | 2009-04-09 | F. Hoffmann-La Roche Ag | New biaryl derivatives |
| ES2479440T3 (es) * | 2008-01-30 | 2014-07-24 | Cephalon, Inc. | Derivados de piridazina sustituidos que tienen actividad antagonista de histamina H3 |
| JP5805792B2 (ja) * | 2011-02-23 | 2015-11-10 | スヴェン・ライフ・サイエンシズ・リミテッド | ヒスタミンｈ３レセプターリガンドとしての新規な化合物 |
| WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
| MD20140130A2 (ro) | 2012-06-29 | 2015-04-30 | Pfizer Inc. | 4-(amino-substituite)-7H-pirolo[2,3-d]pirimidine noi ca inhibitori de LRRK2 |
| CN112521369A (zh) | 2013-03-13 | 2021-03-19 | 福马治疗股份有限公司 | 用于抑制fasn的化合物及组合物 |
| WO2015092592A1 (en) | 2013-12-17 | 2015-06-25 | Pfizer Inc. | Novel 3,4-disubstituted-1h-pyrrolo[2,3-b]pyridines and 4,5-disubstituted-7h-pyrrolo[2,3-c]pyridazines as lrrk2 inhibitors |
| JP6633618B2 (ja) * | 2014-08-21 | 2020-01-22 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 強力なｒｏｃｋ阻害剤としてのタイドバックのベンズアミド誘導体 |
| MY189453A (en) | 2015-06-03 | 2022-02-14 | Bristol Myers Squibb Co | 4-hydroxy-3-(heteroaryl)pyridine-2-one apj agonists for use in the treatment of cardiovascular disorders |
| RS62639B1 (sr) | 2015-07-06 | 2021-12-31 | Alkermes Inc | Hetero-halo inhibitori histonskih deacetilaza |
| EP3319968A1 (en) | 2015-07-06 | 2018-05-16 | Rodin Therapeutics, Inc. | Heterobicyclic n-aminophenyl-amides as inhibitors of histone deacetylase |
| RU2722149C1 (ru) | 2015-09-14 | 2020-05-27 | Пфайзер Инк. | Новые производные имидазо[4,5-c] хинолинов и имидазо[4,5-c][1,5] нафтиридинов в качестве ингибиторов LRRK2 |
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| WO2002076925A2 (en) * | 2001-03-23 | 2002-10-03 | Eli Lilly And Company | Non-imidazole aryl alkylamines compounds as histamine h3 receptor antagonists, preparation and therapeutic uses |
| WO2003064411A1 (en) * | 2002-02-01 | 2003-08-07 | Novo Nordisk A/S | Amides of aminoalkyl-substituted azetidines, pyrrolidines, piperidines and azepanes |
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| FR2671083B1 (fr) | 1990-12-31 | 1994-12-23 | Inst Nat Sante Rech Med | Nouvelles 4-(4-imidazolyl) piperidines substituees en 1, leur preparation ainsi que leurs applications therapeutiques. |
| US5652258A (en) | 1995-05-30 | 1997-07-29 | Gliatech, Inc. | 2-(4-imidazoyl) cyclopropyl derivatives |
| CA2222099A1 (en) | 1995-05-30 | 1996-12-05 | Gliatech, Inc. | 1h-4(5)-substituted imidazole derivatives |
| PL328369A1 (en) | 1996-02-09 | 1999-01-18 | Black James Foundation | Ligands of histamin h receptor |
| US6620839B2 (en) * | 2000-07-13 | 2003-09-16 | Abbott Laboratories | 1,3-disubstituted and 1,3,3-trisubstituted pyrrolidines as histamine-3 receptor ligands and their therapeutic applications |
| EP1720861A2 (en) | 2004-02-25 | 2006-11-15 | Eli Lilly And Company | Histamine h3 receptor antagonists, preparation and therapeutic uses |
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2005
- 2005-03-25 CA CA2561628A patent/CA2561628C/en not_active Expired - Fee Related
- 2005-03-25 SI SI200530961T patent/SI1735278T1/sl unknown
- 2005-03-25 DE DE602005018758T patent/DE602005018758D1/de not_active Expired - Lifetime
- 2005-03-25 PT PT05730691T patent/PT1735278E/pt unknown
- 2005-03-25 US US10/599,488 patent/US7632857B2/en not_active Expired - Fee Related
- 2005-03-25 MX MXPA06011167A patent/MXPA06011167A/es active IP Right Grant
- 2005-03-25 AU AU2005230881A patent/AU2005230881B9/en not_active Ceased
- 2005-03-25 CN CN2005800171466A patent/CN1960969B/zh not_active Expired - Lifetime
- 2005-03-25 PL PL05730691T patent/PL1735278T3/pl unknown
- 2005-03-25 BR BRPI0509298-1A patent/BRPI0509298A/pt not_active IP Right Cessation
- 2005-03-25 ES ES05730691T patent/ES2337376T3/es not_active Expired - Lifetime
- 2005-03-25 WO PCT/US2005/010240 patent/WO2005097740A1/en not_active Ceased
- 2005-03-25 JP JP2007506412A patent/JP4777974B2/ja not_active Expired - Fee Related
- 2005-03-25 EP EP05730691A patent/EP1735278B1/en not_active Expired - Lifetime
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| WO2002076925A2 (en) * | 2001-03-23 | 2002-10-03 | Eli Lilly And Company | Non-imidazole aryl alkylamines compounds as histamine h3 receptor antagonists, preparation and therapeutic uses |
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| WO2004076412A2 (en) * | 2003-02-26 | 2004-09-10 | Sugen, Inc. | Aminoheteroaryl compounds as protein kinase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1735278A1 (en) | 2006-12-27 |
| MXPA06011167A (es) | 2007-01-25 |
| JP2007530698A (ja) | 2007-11-01 |
| US7632857B2 (en) | 2009-12-15 |
| PL1735278T3 (pl) | 2010-06-30 |
| AU2005230881B2 (en) | 2011-03-31 |
| JP4777974B2 (ja) | 2011-09-21 |
| ES2337376T3 (es) | 2010-04-23 |
| DE602005018758D1 (de) | 2010-02-25 |
| US20070208024A1 (en) | 2007-09-06 |
| EP1735278B1 (en) | 2010-01-06 |
| CN1960969A (zh) | 2007-05-09 |
| SI1735278T1 (sl) | 2010-05-31 |
| DK1735278T3 (da) | 2010-04-12 |
| AU2005230881A1 (en) | 2005-10-20 |
| WO2005097740A1 (en) | 2005-10-20 |
| CA2561628A1 (en) | 2005-10-20 |
| BRPI0509298A (pt) | 2007-09-18 |
| ATE454372T1 (de) | 2010-01-15 |
| AU2005230881B9 (en) | 2011-08-25 |
| CY1109860T1 (el) | 2014-09-10 |
| CA2561628C (en) | 2012-05-08 |
| PT1735278E (pt) | 2010-03-09 |
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