CA2562859A1 - Novel enantiomerically pure beta-agonists, method for the production and the use thereof in the form of a drug - Google Patents
Novel enantiomerically pure beta-agonists, method for the production and the use thereof in the form of a drug Download PDFInfo
- Publication number
- CA2562859A1 CA2562859A1 CA002562859A CA2562859A CA2562859A1 CA 2562859 A1 CA2562859 A1 CA 2562859A1 CA 002562859 A CA002562859 A CA 002562859A CA 2562859 A CA2562859 A CA 2562859A CA 2562859 A1 CA2562859 A1 CA 2562859A1
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- denotes hydrogen
- fluorine
- hydrogen
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/536—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines ortho- or peri-condensed with carbocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Abstract
The invention relates to enantiomerically pure compound of formula 1 (see formula 1) wherein R1 denotes hydrogen, C1-C4-alkyl, C1-C4-alkoxy or halogen;
R2 denotes hydrogen, C1-C4-alkyl, C1-C4-alkoxy or halogen;
R3 denotes hydrogen, C1-C4-alkyl, C1-C4-alkoxy, halogen, OH, -O-C1-C4-alkylene-COOH or -O-C1-C4-alkylene-COO-C1-C4-alkyl;
R4 denotes hydrogen, C1-C4-alkyl, C1-C4-alkoxy or halogen; and X denotes an anion with a single negative charge, optionally in the form of a tautomer, mixture of tautomers, hydrate or solvate thereof.
A method for producing said compounds and the use thereof in the form of a drug, in particular as a drug for treating respiratory tract diseases are also disclosed. The synthesis of the compounds is carried out by means of a chiral epoxide.
R2 denotes hydrogen, C1-C4-alkyl, C1-C4-alkoxy or halogen;
R3 denotes hydrogen, C1-C4-alkyl, C1-C4-alkoxy, halogen, OH, -O-C1-C4-alkylene-COOH or -O-C1-C4-alkylene-COO-C1-C4-alkyl;
R4 denotes hydrogen, C1-C4-alkyl, C1-C4-alkoxy or halogen; and X denotes an anion with a single negative charge, optionally in the form of a tautomer, mixture of tautomers, hydrate or solvate thereof.
A method for producing said compounds and the use thereof in the form of a drug, in particular as a drug for treating respiratory tract diseases are also disclosed. The synthesis of the compounds is carried out by means of a chiral epoxide.
Claims (15)
1) Enantiomerically pure compounds of general formula 1 wherein R1 denotes hydrogen, C1 -C4-alkyl, C1-C4-alkoxy or halogen;
R2 denotes hydrogen, C1-C4-alkyl, C1 -C4-alkoxy or halogen;
R3 denotes hydrogen, C1-C4-alkyl, C1-C4-alkoxy, halogen, OH, -O-C1-C4-alkylene-COOH or -O-C1-C4-alkylene-COO-C1-C4-alkyl;
R4 denotes hydrogen, C1-C4-alkyl, C1-C4-alkoxy or halogen;
X- denotes an anion with a single negative charge, preferably an anion with a single negative charge selected from among chloride, bromide, iodide, sulphate, phosphate, methanesulphonate, nitrate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate, oxalate, succinate, benzoate and p-toluenesulphonate, optionally in the form of the tautomers, mixtures of the tautomers, hydrates or solvates thereof.
R2 denotes hydrogen, C1-C4-alkyl, C1 -C4-alkoxy or halogen;
R3 denotes hydrogen, C1-C4-alkyl, C1-C4-alkoxy, halogen, OH, -O-C1-C4-alkylene-COOH or -O-C1-C4-alkylene-COO-C1-C4-alkyl;
R4 denotes hydrogen, C1-C4-alkyl, C1-C4-alkoxy or halogen;
X- denotes an anion with a single negative charge, preferably an anion with a single negative charge selected from among chloride, bromide, iodide, sulphate, phosphate, methanesulphonate, nitrate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate, oxalate, succinate, benzoate and p-toluenesulphonate, optionally in the form of the tautomers, mixtures of the tautomers, hydrates or solvates thereof.
2) Enantiomerically pure compounds of general formula 1 according to C1aim 1, wherein R1 denotes hydrogen or halogen;
R2 denotes hydrogen or halogen;
R3 denotes hydrogen, C1-C4-alkoxy or halogen;
R4 denotes hydrogen or halogen;
X- denotes an anion with a single negative charge, preferably an anion with a single negative charge selected from among chloride, bromide, iodide, sulphate, phosphate, methanesulphonate, nitrate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate, oxalate, succinate, benzoate and p-toluenesulphonate, optionally in the form of the tautomers, mixtures of the tautomers, hydrates or solvates thereof.
R2 denotes hydrogen or halogen;
R3 denotes hydrogen, C1-C4-alkoxy or halogen;
R4 denotes hydrogen or halogen;
X- denotes an anion with a single negative charge, preferably an anion with a single negative charge selected from among chloride, bromide, iodide, sulphate, phosphate, methanesulphonate, nitrate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate, oxalate, succinate, benzoate and p-toluenesulphonate, optionally in the form of the tautomers, mixtures of the tautomers, hydrates or solvates thereof.
3) Enantiomerically pure compounds of general formula 1 according to claim 1 or 2, wherein R1 denotes hydrogen, fluorine or chlorine, preferably hydrogen or fluorine;
R2 denotes hydrogen, fluorine or chlorine, preferably hydrogen or fluorine;
R3 denotes hydrogen, methoxy, ethoxy, fluorine or chlorine, preferably hydrogen, methoxy, ethoxy or fluorine;
R4 denotes hydrogen, fluorine or chlorine, preferably hydrogen or fluorine;
X- denotes an anion with a single negative charge, preferably an anion with a single negative charge selected from among chloride, bromide, iodide, sulphate, phosphate, methanesulphonate, nitrate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate, oxalate, succinate, benzoate and p-toluenesulphonate, optionally in the form of the tautomers, mixtures of the tautomers, hydrates or solvates thereof.
R2 denotes hydrogen, fluorine or chlorine, preferably hydrogen or fluorine;
R3 denotes hydrogen, methoxy, ethoxy, fluorine or chlorine, preferably hydrogen, methoxy, ethoxy or fluorine;
R4 denotes hydrogen, fluorine or chlorine, preferably hydrogen or fluorine;
X- denotes an anion with a single negative charge, preferably an anion with a single negative charge selected from among chloride, bromide, iodide, sulphate, phosphate, methanesulphonate, nitrate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate, oxalate, succinate, benzoate and p-toluenesulphonate, optionally in the form of the tautomers, mixtures of the tautomers, hydrates or solvates thereof.
4) Enantiomerically pure compounds of general formula 1 according to one of claims 1 to 3, wherein R1 denotes hydrogen or fluorine;
R2 denotes hydrogen;
R3 denotes methoxy, ethoxy or fluorine;
R4 denotes hydrogen;
X- denotes an anion with a single negative charge selected from among chloride, bromide, sulphate, methanesulphonate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate and succinate;
optionally in the form of the tautomers, mixtures of the tautomers, hydrates or solvates thereof.
R2 denotes hydrogen;
R3 denotes methoxy, ethoxy or fluorine;
R4 denotes hydrogen;
X- denotes an anion with a single negative charge selected from among chloride, bromide, sulphate, methanesulphonate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate and succinate;
optionally in the form of the tautomers, mixtures of the tautomers, hydrates or solvates thereof.
5) Enantiomerically pure compounds of general formula 1 according to one of claims 1 to 3, wherein R1 denotes hydrogen;
R2 denotes hydrogen, fluorine or chlorine, preferably hydrogen or fluorine;
R3 denotes hydrogen;
R4 denotes hydrogen, fluorine or chlorine, preferably hydrogen or fluorine;
X- denotes an anion with a single negative charge selected from among chloride, bromide, sulphate, methanesulphonate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate and succinate;
optionally in the form of the tautomers, mixtures of the tautomers, hydrates or solvates thereof.
R2 denotes hydrogen, fluorine or chlorine, preferably hydrogen or fluorine;
R3 denotes hydrogen;
R4 denotes hydrogen, fluorine or chlorine, preferably hydrogen or fluorine;
X- denotes an anion with a single negative charge selected from among chloride, bromide, sulphate, methanesulphonate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate and succinate;
optionally in the form of the tautomers, mixtures of the tautomers, hydrates or solvates thereof.
6) Enantiomerically pure compounds of general formula 1 according to one of claims 1 to 5, characterised in that they are in crystalline form, optionally in the form of their crystalline tautomers, crystalline hydrates or crystalline solvates.
7) Enantiomerically pure compounds of general formula 1 according to one of claims 1 to 6 as pharmaceutical compositions.
8) Use of enantiomerically pure compounds of general formula 1 according to one of claims 1 to 6 for preparing a pharmaceutical composition for the treatment of respiratory complaints.
9) Pharmaceutical formulation, characterised in that it contains a compound of formula 1 according to one of claims 1 to 6.
10) Compounds of formula 5 wherein OPG denotes a hydroxyl function protected by a protective group PG, preferably a group which is selected from -O-C1-C4-alkyl, -O-benzyl and -O-CO-C1-C4-alkyl.
11) Use of a compound of formula 5 according to claim 10 as a starting compound for preparing a compound of formula 1 according to one of claims 1 to 6.
12) Compounds of formula 7 wherein OPG denotes a hydroxyl function protected by a protective group PG, preferably a group which is selected from -O-C1-C4-alkyl, -O-benzyl and -O-CO-C1-C4-alkyl, and wherein the groups R1, R2, R3 and R4 may have the meanings given in claims 1 to 5
13) Use of a compound of formula 7 according to claim 12 as a starting compound for preparing a compound of formula 1 according to one of claims 1 to 6.
14) Compounds of formula 1' wherein the groups R1, R2, R3 and R4 may have the meanings given in claims 1 to 5.
15) Use of a compound of formula 1' according to claim 14 as a starting compound for preparing a compound of formula 1 according to one of claims 1 to 6.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004024454A DE102004024454A1 (en) | 2004-05-14 | 2004-05-14 | Novel enantiomerically pure beta agonists, process for their preparation and their use as pharmaceuticals |
| DE102004024454.5 | 2004-05-14 | ||
| PCT/EP2005/005079 WO2005111005A1 (en) | 2004-05-14 | 2005-05-11 | Novel enantiomerically pure beta-agonists, method for the production and the use thereof in the form of a drug |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2562859A1 true CA2562859A1 (en) | 2005-11-24 |
| CA2562859C CA2562859C (en) | 2012-05-08 |
Family
ID=34966720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2562859A Active CA2562859C (en) | 2004-05-14 | 2005-05-11 | Novel enantiomerically pure beta-agonists, method for the production and the use thereof in the form of a drug |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP1789405B1 (en) |
| JP (1) | JP2007537196A (en) |
| KR (1) | KR101270447B1 (en) |
| CN (4) | CN106146425A (en) |
| AU (1) | AU2005243469B2 (en) |
| BR (1) | BRPI0511102B1 (en) |
| CA (1) | CA2562859C (en) |
| CY (1) | CY1114702T1 (en) |
| DE (1) | DE102004024454A1 (en) |
| DK (1) | DK1789405T3 (en) |
| ES (1) | ES2431118T3 (en) |
| IL (1) | IL179217A (en) |
| MX (1) | MXPA06013218A (en) |
| NZ (1) | NZ551416A (en) |
| PL (1) | PL1789405T3 (en) |
| PT (1) | PT1789405E (en) |
| RU (1) | RU2378262C2 (en) |
| SI (1) | SI1789405T1 (en) |
| WO (1) | WO2005111005A1 (en) |
| ZA (1) | ZA200607152B (en) |
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| US7423036B2 (en) | 2005-02-19 | 2008-09-09 | Boehringer Ingelheim International Gmbh | Long-acting betamimetics for the treatment of respiratory complaints |
| US7423146B2 (en) | 2005-11-09 | 2008-09-09 | Boehringer Ingelheim International Gmbh | Process for the manufacturing of pharmaceutically active 3,1-benzoxazine-2-ones |
| US7491719B2 (en) | 2004-05-14 | 2009-02-17 | Boehringer Ingelheim International Gmbh | Enantiomerically pure beta agonists, process for the manufacture thereof, and use thereof as medicaments |
| US7534789B2 (en) | 2006-03-15 | 2009-05-19 | Boehringer Ingelheim International Gmbh | Enantiomeric pure β agonists, manufacturing and use as a medicament thereof |
| US7709474B2 (en) | 2006-08-22 | 2010-05-04 | Boehringer Ingelheim International Gmbh | Enantiomerically pure beta agonists, manufacturing and use thereof |
| US7727984B2 (en) | 2002-11-15 | 2010-06-01 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | Medicaments for the treatment of chronic obstructive pulmonary disease |
| US7820815B2 (en) | 2004-11-05 | 2010-10-26 | Boehringer Ingelheim International Gmbh | Process for the preparation of chiral 8-(-3-aminopiperidin-1-yl) xanthines |
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| US8119648B2 (en) | 2002-08-21 | 2012-02-21 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
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| US8420809B2 (en) | 2005-08-15 | 2013-04-16 | Boehringer Ingelheim International Gmbh | Process for the manufacturing of betamimetics |
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Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4656168A (en) * | 1980-12-23 | 1987-04-07 | Merck & Co., Inc. | (3-aralkylamino-2-or-propoxy)heterocyclic compounds in method of effecting bronchodilation |
| DE3134590A1 (en) * | 1981-09-01 | 1983-03-10 | Boehringer Ingelheim KG, 6507 Ingelheim | NEW BENZO HETEROCYCLES |
| US4460581A (en) * | 1982-10-12 | 1984-07-17 | Boehringer Ingelheim Kg | (1-Hydroxy-2-amino-alkyl)-substituted benzoxazinones and benzoxazolinones |
| DE3743265A1 (en) * | 1987-12-19 | 1989-06-29 | Boehringer Ingelheim Kg | NEW AMMONIUM COMPOUNDS, THEIR MANUFACTURE AND USE |
| US5502078A (en) * | 1991-05-28 | 1996-03-26 | Zeneca Limited | Chemical compounds |
| JPH0912518A (en) * | 1995-06-26 | 1997-01-14 | Kanegafuchi Chem Ind Co Ltd | Production of 2-(1-(3'4'-dimethoxyphenlyl)-2-propyamino)-1-(3'-chloropheml)-ethanol |
| JPH11255743A (en) * | 1998-03-06 | 1999-09-21 | Dainippon Pharmaceut Co Ltd | Production of optically active indole derivative and intermediate for producing the same |
| DZ3478A1 (en) | 2000-10-12 | 2002-04-18 | Boehringer Ingelheim Pharma | CRYSTALLINE MONOHYDRATE, PROCESS FOR ITS MANUFACTURE AND ITS USE FOR THE MANUFACTURE OF A MEDICAMENT. |
| HUP0401073A2 (en) * | 2000-12-21 | 2004-09-28 | Aventis Pharma Deutschland Gmbh. | Diphenyl azetidinone derivatives, method for the production thereof, medicaments containing these compounds, and their use |
| ME00412B (en) | 2001-06-22 | 2011-10-10 | Boehringer Ingelheim Pharma | Crystalline anticholinergic, method for its production, and use thereof in the production of a drug |
| DE10253282A1 (en) * | 2002-11-15 | 2004-05-27 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Treatment of chronic obstructive pulmonary disease, using new or known N-substituted 2-amino-1-(benz-(1,4)-oxazin-3-on-8-yl)-ethanol derivative beta-mimetic agents, suitable for once-daily administration |
| EP1789394A1 (en) * | 2004-05-13 | 2007-05-30 | Boehringer Ingelheim International Gmbh | Hydroxy-substituted benzo-condensed heterocycles for use as beta agonists in the treatment of respiratory diseases |
-
2004
- 2004-05-14 DE DE102004024454A patent/DE102004024454A1/en not_active Withdrawn
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2005
- 2005-05-11 CN CN201610262144.3A patent/CN106146425A/en active Pending
- 2005-05-11 CN CN201610884642.1A patent/CN106995414A/en active Pending
- 2005-05-11 SI SI200531756T patent/SI1789405T1/en unknown
- 2005-05-11 JP JP2007512081A patent/JP2007537196A/en active Pending
- 2005-05-11 CN CNA2005800154333A patent/CN101133039A/en active Pending
- 2005-05-11 AU AU2005243469A patent/AU2005243469B2/en active Active
- 2005-05-11 RU RU2006144123/04A patent/RU2378262C2/en active Protection Beyond IP Right Term
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- 2005-05-11 WO PCT/EP2005/005079 patent/WO2005111005A1/en active Application Filing
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- 2005-05-11 ES ES05737938T patent/ES2431118T3/en active Active
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- 2006-08-28 ZA ZA200607152A patent/ZA200607152B/en unknown
- 2006-11-13 IL IL179217A patent/IL179217A/en active IP Right Grant
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Also Published As
| Publication number | Publication date |
|---|---|
| DE102004024454A1 (en) | 2005-12-08 |
| PT1789405E (en) | 2013-08-22 |
| EP1789405A1 (en) | 2007-05-30 |
| CN106146425A (en) | 2016-11-23 |
| MXPA06013218A (en) | 2007-02-08 |
| KR20070011602A (en) | 2007-01-24 |
| RU2378262C2 (en) | 2010-01-10 |
| DK1789405T3 (en) | 2013-10-14 |
| CN102827097B (en) | 2016-11-23 |
| IL179217A (en) | 2012-08-30 |
| AU2005243469B2 (en) | 2011-09-29 |
| WO2005111005A1 (en) | 2005-11-24 |
| IL179217A0 (en) | 2007-03-08 |
| AU2005243469A1 (en) | 2005-11-24 |
| CN101133039A (en) | 2008-02-27 |
| JP2007537196A (en) | 2007-12-20 |
| RU2006144123A (en) | 2008-09-10 |
| CA2562859C (en) | 2012-05-08 |
| NZ551416A (en) | 2011-04-29 |
| PL1789405T3 (en) | 2013-12-31 |
| ZA200607152B (en) | 2008-04-30 |
| EP1789405B1 (en) | 2013-07-17 |
| CY1114702T1 (en) | 2016-10-05 |
| CN102827097A (en) | 2012-12-19 |
| SI1789405T1 (en) | 2013-09-30 |
| CN106995414A (en) | 2017-08-01 |
| KR101270447B1 (en) | 2013-06-04 |
| BRPI0511102B1 (en) | 2021-05-25 |
| ES2431118T3 (en) | 2013-11-25 |
| BRPI0511102A (en) | 2007-11-27 |
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