TW548274B - Dihydropyrimidines having hepatitis B therapeutic efficacy - Google Patents
Dihydropyrimidines having hepatitis B therapeutic efficacy Download PDFInfo
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- TW548274B TW548274B TW088106067A TW88106067A TW548274B TW 548274 B TW548274 B TW 548274B TW 088106067 A TW088106067 A TW 088106067A TW 88106067 A TW88106067 A TW 88106067A TW 548274 B TW548274 B TW 548274B
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- A—HUMAN NECESSITIES
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D213/84—Nitriles
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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
- C07D401/04—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
-
- 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
- C07D401/14—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 three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
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- Communicable Diseases (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Gastroenterology & Hepatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19817264A DE19817264A1 (de) | 1998-04-18 | 1998-04-18 | Neue Dihydropyrimidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW548274B true TW548274B (en) | 2003-08-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW088106067A TW548274B (en) | 1998-04-18 | 1999-04-16 | Dihydropyrimidines having hepatitis B therapeutic efficacy |
Country Status (36)
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000058302A1 (de) * | 1999-03-25 | 2000-10-05 | Bayer Aktiengesellschaft | Dihydropyrimidine und ihre verwendung zur behandlung von hepatitis b |
| AU5568400A (en) | 1999-06-23 | 2001-01-09 | Ajinomoto Co., Inc. | Novel dihydropyrimidine derivatives |
| AU3009801A (en) * | 1999-12-22 | 2001-07-03 | Bayer Aktiengesellschaft | Combinations of medicaments for treating viral diseases |
| DE10012823A1 (de) | 2000-03-16 | 2001-09-20 | Bayer Ag | Arzneimittel gegen virale Erkrankungen |
| DE10013126A1 (de) * | 2000-03-17 | 2001-09-20 | Bayer Ag | Arzneimittel gegen virale Erkrankungen |
| DE10013125A1 (de) * | 2000-03-17 | 2001-09-20 | Bayer Ag | Arzneimittel gegen virale Erkrankungen |
| DE10125131A1 (de) | 2001-05-23 | 2002-12-05 | Bayer Ag | Verfahren zur Spaltung des Methyl 4-(2-chlor-4-fluorphenyl)-2-(3,5-difluor-2-pyridinyl)-6-methyl-1,4-dihydro-5-pyrmidincarboxylat-Racemats |
| US20040092735A1 (en) * | 2002-11-08 | 2004-05-13 | Orchid Chemicals & Pharmaceuticals Limited | Process for the preparation of cefuroxime sodium |
| CN101104604B (zh) * | 2006-07-10 | 2011-03-02 | 北京摩力克科技有限公司 | 光学纯二氢嘧啶类化合物及其用于制备治疗和预防病毒性疾病的药物的用途 |
| CN101104617B (zh) | 2006-07-10 | 2010-06-23 | 北京摩力克科技有限公司 | 二氢嘧啶类化合物及其用于制备治疗和预防病毒性疾病的药物的用途 |
| RU2452733C2 (ru) * | 2007-04-27 | 2012-06-10 | Пэдью Фарма Л.П. | Антагонисты trpv1 и их применение |
| PT2159224E (pt) * | 2007-06-18 | 2012-10-24 | Sunshine Lake Pharma Co Ltd | Tiazolil dihidropirimidinas substituídas com bromo-fenilo |
| EP2178503A1 (en) | 2007-07-12 | 2010-04-28 | Novartis Ag | Oral pharmaceutical solutions containing telbivudine |
| US20130267517A1 (en) | 2012-03-31 | 2013-10-10 | Hoffmann-La Roche Inc. | Novel 4-methyl-dihydropyrimidines for the treatment and prophylaxis of hepatitis b virus infection |
| JP6263533B2 (ja) * | 2012-08-24 | 2018-01-17 | サンシャイン・レイク・ファーマ・カンパニー・リミテッドＳｕｎｓｈｉｎｅ Ｌａｋｅ Ｐｈａｒｍａ Ｃｏ．，Ｌｔｄ． | ジヒドロピリミジン化合物及び医薬におけるその適用 |
| WO2014037480A1 (en) | 2012-09-10 | 2014-03-13 | F. Hoffmann-La Roche Ag | 6-amino acid heteroaryldihydropyrimidines for the treatment and prophylaxis of hepatitis b virus infection |
| CN103664899B (zh) * | 2012-09-11 | 2017-06-16 | 广东东阳光药业有限公司 | 杂芳基取代的二氢嘧啶类化合物及其在药物中的应用 |
| US20150292045A1 (en) * | 2012-11-09 | 2015-10-15 | Indiana University Research And Technology Corporation | Alternative uses for hbv assembly effectors |
| TW201609652A (zh) * | 2013-11-12 | 2016-03-16 | 陶氏農業科學公司 | 用於氟化化合物之過程（三） |
| CA2920415A1 (en) | 2013-11-19 | 2015-05-28 | Sunshine Lake Pharma Co., Ltd. | Dihydropyrimidine compounds and their application in pharmaceuticals |
| CA2927373C (en) | 2013-11-27 | 2021-07-13 | Sunshine Lake Pharma Co., Ltd. | Processes for preparing dihydropyrimidine derivatives and intermediates thereof |
| SG11201605896WA (en) | 2014-03-28 | 2016-08-30 | Sunshine Lake Pharma Co Ltd | Dihydropyrimidine compounds and their application in pharmaceuticals |
| CN105153164B (zh) * | 2014-05-30 | 2018-10-30 | 齐鲁制药有限公司 | 作为hbv抑制剂的二氢嘧啶并环衍生物 |
| ES2687606T3 (es) * | 2014-05-30 | 2018-10-26 | Qilu Pharmaceutical Co., Ltd. | Derivado de bucle de dihidropirimido como inhibidor de HBV |
| WO2016124126A1 (en) | 2015-02-07 | 2016-08-11 | Sunshine Lake Pharma Co., Ltd. | Complexes and salts of dihydropyrimidine derivatives and their application in pharmaceuticals |
| AU2018291688B2 (en) * | 2017-06-27 | 2022-02-03 | Janssen Pharmaceutica Nv | Heteroaryldihydropyrimidine derivatives and methods of treating hepatitis B infections |
| US10759774B2 (en) | 2017-09-28 | 2020-09-01 | The Curators Of The University Of Missouri | Inhibitors of hepatitis B virus targeting capsid assembly |
| MA50524A (fr) | 2017-11-02 | 2020-09-09 | Aicuris Gmbh & Co Kg | Nouveaux indole-2-carboxamides à substitution amino-thiazole hautement actifs agissant contre le virus de l'hépatite b (vhb) |
| BR112020008765A2 (pt) | 2017-11-02 | 2020-10-20 | Aicuris Gmbh & Co. Kg | indol-2-carboxamidas pirazolo-piperidina substituídas altamente ativas inovadoras ativas contra o vírus da hepatite b (hbv) |
| WO2019214610A1 (en) * | 2018-05-08 | 2019-11-14 | Janssen Sciences Ireland Unlimited Company | Dihydropyrimidine derivatives and uses thereof in the treatment of hbv infection or of hbv-induced diseases |
| US11053235B2 (en) | 2018-08-09 | 2021-07-06 | Janssen Sciences Ireland Unlimited Company | Substituted 1,4-dihydropyrimidines for the treatment of HBV infection or HBV-induced diseases |
| AR116948A1 (es) | 2018-11-02 | 2021-06-30 | Aicuris Gmbh & Co Kg | Derivados de urea 6,7-dihidro-4h-pirazolo[1,5-a]pirazinas activas contra el virus de la hepatitis b (vhb) |
| UY38437A (es) | 2018-11-02 | 2020-05-29 | Aicuris Gmbh & Co Kg | Nuevas urea 6,7-dihidro-4h-pirazolo[1,5-a]pirazinas activas contra el virus de la hepatitis b (hbv) |
| UY38434A (es) | 2018-11-02 | 2020-05-29 | Aicuris Gmbh & Co Kg | Nuevas 6,7-dihidro-4h-pirazolo[1,5-a]pirazin indol-2-carboxamidas activas contra el virus de la hepatitis b (hbv) |
| AR116946A1 (es) | 2018-11-02 | 2021-06-30 | Aicuris Gmbh & Co Kg | Derivados de urea 6,7-dihidro-4h-pirazolo[4,3-c]piridinas activas contra el virus de la hepatitis b (vhb) |
| AR116947A1 (es) | 2018-11-02 | 2021-06-30 | Aicuris Gmbh & Co Kg | Derivados de urea 6,7-dihidro-4h-pirazolo[1,5-a]pirazinas-indol-2-carboxamidas activas contra el virus de la hepatitis b (vhb) |
| WO2020089460A1 (en) * | 2018-11-02 | 2020-05-07 | Aicuris Gmbh & Co. Kg | Novel urea 6,7-dihydro-4h-thiazolo[5,4-c]pyridines active against the hepatitis b virus (hbv) |
| CN113227090A (zh) | 2018-12-20 | 2021-08-06 | 詹森药业有限公司 | 杂芳基二氢嘧啶衍生物和治疗乙型肝炎感染的方法 |
| WO2020221811A1 (en) | 2019-04-30 | 2020-11-05 | Aicuris Gmbh & Co. Kg | Novel oxalyl piperazines active against the hepatitis b virus (hbv) |
| KR20220004131A (ko) | 2019-04-30 | 2022-01-11 | 아이쿠리스 게엠베하 운트 코. 카게 | B형 간염 바이러스 (hbv)에 대해 활성인 신규 인돌-2-카르복스아미드 |
| MX2021013086A (es) | 2019-04-30 | 2021-11-17 | Aicuris Gmbh & Co Kg | Nuevas fenil y piridil ureas activas contra el virus de la hepatitis b (vhb). |
| WO2020221824A1 (en) | 2019-04-30 | 2020-11-05 | Aicuris Gmbh & Co. Kg | Novel indolizine-2-carboxamides active against the hepatitis b virus (hbv) |
| WO2020255016A1 (en) | 2019-06-18 | 2020-12-24 | Janssen Sciences Ireland Unlimited Company | Combination of hepatitis b virus (hbv) vaccines and dihydropyrimidine derivatives as capsid assembly modulators |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL130304C (cg-RX-API-DMAC7.html) * | 1964-02-12 | |||
| CH550189A (de) | 1971-01-08 | 1974-06-14 | Ciba Geigy Ag | Verfahren zur herstellung von neuen dibenzo (b,f) thiepincarbonsaeuren. |
| CH569043A5 (cg-RX-API-DMAC7.html) | 1973-01-23 | 1975-11-14 | Ciba Geigy Ag | |
| US4371537A (en) * | 1981-08-13 | 1983-02-01 | The Dow Chemical Company | Sulfur-substituted phenoxypyridines having antiviral activity |
| DE3234684A1 (de) * | 1982-09-18 | 1984-03-22 | Bayer Ag, 5090 Leverkusen | Neue dihydropyrimidine, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| JPS60185764A (ja) * | 1984-03-05 | 1985-09-21 | Wako Pure Chem Ind Ltd | ピリジン誘導体の新規な製造法 |
| US4698340A (en) | 1984-07-19 | 1987-10-06 | Fujisawa Pharmaceutical Co., Ltd. | Pyrimidine derivatives, processes for preparation thereof and composition containing the same |
| US4727073A (en) | 1984-10-01 | 1988-02-23 | Fujisawa Pharmaceutical Co., Ltd. | Pyrimidine derivatives and composition of the same |
| GB8906168D0 (en) * | 1989-03-17 | 1989-05-04 | Pfizer Ltd | Therapeutic agents |
| US6204221B1 (en) * | 1996-11-12 | 2001-03-20 | Syngenta Crop Protection, Inc. | Herbicides |
| SE9702564D0 (sv) | 1997-07-02 | 1997-07-02 | Astra Ab | New compounds |
-
1998
- 1998-04-18 DE DE19817264A patent/DE19817264A1/de not_active Withdrawn
-
1999
- 1999-04-07 NZ NZ507569A patent/NZ507569A/en not_active IP Right Cessation
- 1999-04-07 TR TR2000/03011T patent/TR200003011T2/xx unknown
- 1999-04-07 DK DK99920603T patent/DK1080086T3/da active
- 1999-04-07 PL PL99343481A patent/PL193898B1/pl unknown
- 1999-04-07 ID IDW20002111A patent/ID27263A/id unknown
- 1999-04-07 BR BRPI9909730-3A patent/BR9909730B1/pt not_active IP Right Cessation
- 1999-04-07 AU AU38133/99A patent/AU740318B2/en not_active Expired
- 1999-04-07 CN CNB998074950A patent/CN1159311C/zh not_active Expired - Lifetime
- 1999-04-07 ES ES99920603T patent/ES2183548T3/es not_active Expired - Lifetime
- 1999-04-07 WO PCT/EP1999/002344 patent/WO1999054326A1/de not_active Ceased
- 1999-04-07 US US09/673,592 patent/US6696451B1/en not_active Expired - Lifetime
- 1999-04-07 KR KR1020007011527A patent/KR100636771B1/ko not_active Expired - Lifetime
- 1999-04-07 PT PT99920603T patent/PT1080086E/pt unknown
- 1999-04-07 IL IL13858499A patent/IL138584A0/xx active IP Right Grant
- 1999-04-07 DE DE59902573T patent/DE59902573D1/de not_active Expired - Lifetime
- 1999-04-07 CA CA002328780A patent/CA2328780C/en not_active Expired - Lifetime
- 1999-04-07 CZ CZ20003871A patent/CZ293482B6/cs not_active IP Right Cessation
- 1999-04-07 BR BRPI9917862A patent/BRPI9917862B8/pt not_active IP Right Cessation
- 1999-04-07 CU CU20000220A patent/CU23049A3/es unknown
- 1999-04-07 SI SI9930139T patent/SI1080086T1/xx unknown
- 1999-04-07 RU RU2000129148/04A patent/RU2245881C9/ru active
- 1999-04-07 HU HU0102372A patent/HUP0102372A3/hu unknown
- 1999-04-07 AT AT99920603T patent/ATE223401T1/de active
- 1999-04-07 EP EP99920603A patent/EP1080086B1/de not_active Expired - Lifetime
- 1999-04-07 JP JP2000544665A patent/JP4590097B2/ja not_active Expired - Lifetime
- 1999-04-07 SK SK1565-2000A patent/SK286407B6/sk not_active IP Right Cessation
- 1999-04-15 PE PE1999000309A patent/PE20000427A1/es not_active IP Right Cessation
- 1999-04-16 GT GT199900056A patent/GT199900056A/es unknown
- 1999-04-16 MY MYPI99001481A patent/MY126527A/en unknown
- 1999-04-16 SV SV1999000047A patent/SV1999000047A/es active IP Right Grant
- 1999-04-16 TW TW088106067A patent/TW548274B/zh active
- 1999-04-16 CO CO99022937A patent/CO5021127A1/es unknown
- 1999-04-16 AR ARP990101779A patent/AR018187A1/es active IP Right Grant
- 1999-07-04 UA UA2000116511A patent/UA63998C2/uk unknown
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2000
- 2000-09-20 IL IL138584A patent/IL138584A/en not_active IP Right Cessation
- 2000-09-26 ZA ZA200005136A patent/ZA200005136B/xx unknown
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- 2000-10-17 NO NO20005215A patent/NO321985B1/no not_active IP Right Cessation
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2004
- 2004-02-17 US US10/781,075 patent/US20040167135A1/en not_active Abandoned
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2006
- 2006-12-15 US US11/639,955 patent/US7514565B2/en not_active Expired - Fee Related
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2010
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