CA2451932A1 - Pyrrolopyrimidines as protein kinase inhibitors - Google Patents
Pyrrolopyrimidines as protein kinase inhibitors Download PDFInfo
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- CA2451932A1 CA2451932A1 CA002451932A CA2451932A CA2451932A1 CA 2451932 A1 CA2451932 A1 CA 2451932A1 CA 002451932 A CA002451932 A CA 002451932A CA 2451932 A CA2451932 A CA 2451932A CA 2451932 A1 CA2451932 A1 CA 2451932A1
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- ny1y2
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- ny3y4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- 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
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- 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
- A61P11/02—Nasal agents, e.g. decongestants
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- 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
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- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Ophthalmology & Optometry (AREA)
- Otolaryngology (AREA)
- Orthopedic Medicine & Surgery (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
This invention is directed to compounds of the formula (I) to N-oxides, prodrugs, acid bioisosteres, pharmaceutically acceptable salts or solvates of such compounds, or N-oxides, prodrugs, or acid bioisosteres of such salts or solvates, to compositions comprising such compounds, and to methods of treatment comprising administering, to a patient in need thereof, such compounds and compositions.
Claims (25)
1. A compound of the formula wherein R1 represents hydrogen, -C(=O)-NY1Y2, -C(=O)-OR5, -SO2-NY1Y2, -SO2-R7, -C(=O)R7, or R1 represents alkenyl, alkenyloxy, alkyl, alkynyl, aryl, heteroaryl, heterocycloalkyl, cycloalkyl or cycloalkylalkyl, each optionally substituted by one or more groups selected from aryl, cycloalkyl, cyano, halo, heteroaryl, heterocycloalkyl, -CHO or a 5-, 6- or 7-membered cyclic acetal derivative of such -CHO, -C(=O)-NY1Y2, -C(=O)-OR5, -NY1Y2, -N(R6)-C(=O)-R7, -N(R6)-C(=O)-NY3Y4, -N(R6)-SO2-R7, -N(R6)-SO2-NY3Y4, -OR7, -C(=O)-R7, hydroxy, alkoxy and carboxy;
R2 represents one or more groups selected from hydrogen, acyl, alkylenedioxy, alkenyl, alkenyloxy, alkynyl, aryl, cyano, halo, hydroxy, heteroaryl, heterocycloalkyl, nitro, R4, -C(=O)-NY1Y2, -C(=O)-OR5, -NY1Y2, -N(R6)-C(=O)-R7, -N(R6)-C(=O)-NY3Y4, -N(R6)-C(=O)-OR7, -N(R6)-SO2-R7, -N(R6)-SO2-NY3Y4, -SO2-NY1Y2 and -ZR4;
R3 represents H, cyano, halo, hydroxy, nitro, R4, NY1Y2, -ZR4, -C(=O)-OR5, -C(=O)-R7, -C(=O)-NY1Y2, -N(R8)-C(=O)-R4, -N(R8)-C(=O)-NY1Y2, -N(R8)-C(=O)-OR5, -SO2-NY3Y4, or -N(R8)-SO2-R7, or R3 represents aryl, heteroaryl, alkenyl or alkynyl, each optionally substituted by one or more groups selected from aryl, cyano, halo, hydroxy, heteroaryl, heterocycloalkyl, nitro, -C(=O)-NY1Y2, -C(=O)-OR5, -NY1Y2, -N(R6)-C(=O)-R7, -N(R6)-C(=O)-NY3Y4, -N(R6)-C(=O)-OR7, -N(R6)-SO2-R7, -N(R6)-SO2-NY3Y4, -SO2-NY1Y2 and -ZR4;
R4 represents alkyl, cycloalkyl or cycloalkylalkyl each optionally substituted by one or more groups selected from aryl, cycloalkyl, cyano, halo, heteroaryl, heterocycloalkyl, hydroxy, -CHO or a 5-, 6- or 7-membered cyclic acetal derivative of such -CHO, -C(=O)-NY1Y2, -C(=O)-OR5, -NY1Y2, -N(R6)-C(=O)-R7, -N(R6)-C(=O)-NY3Y4, -N(R6)-SO2-R7, -N(R6)-SO2-NY3Y4, -OR7 and -C(=O)-R7 where R4 is optionally interspersed with a group selected from O, S(O)n, and NR6;
R5 represents hydrogen, alkyl, alkenyl, aryl, arylalkyl, heteroaryl or heteroarylalkyl;
R6 represents hydrogen or lower alkyl;
R7 represents alkyl, aryl, arylalkyl, cycloalkyl, cycloalkylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl or heterocycloalkylalkyl;
R8 represents hydrogen or lower alkyl;
Y1 and Y2 are independently hydrogen, alkenyl, aryl, cycloalkyl, heteroaryl or alkyl optionally substituted by one or more groups selected from aryl, halo, heteroaryl, hydroxy, -C(=O)-NY3Y4, -C(=O)-OR5, -NY3Y4, -N(R6)-C(=O)-R7, -N(R6)-C(=O)-NY3Y4, -N(R6)-SO2-R7, -N(R6)-SO2-NY3Y4 and -OR7; or the group -NY1Y2 may form a cyclic amine;
Y3 and Y4 are independently hydrogen, alkenyl, alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl or heteroarylalkyl; or the group -NY3Y4 may form a cyclic amine;
Z represents O or S(O)n;
n is zero or an integer 1 or 2; or an N-oxide, prodrug, acid bioisostere, pharmaceutically acceptable salt or solvate of such compound;
or an N-oxide, prodrug, or acid bioisostere of such salt or solvate.
R2 represents one or more groups selected from hydrogen, acyl, alkylenedioxy, alkenyl, alkenyloxy, alkynyl, aryl, cyano, halo, hydroxy, heteroaryl, heterocycloalkyl, nitro, R4, -C(=O)-NY1Y2, -C(=O)-OR5, -NY1Y2, -N(R6)-C(=O)-R7, -N(R6)-C(=O)-NY3Y4, -N(R6)-C(=O)-OR7, -N(R6)-SO2-R7, -N(R6)-SO2-NY3Y4, -SO2-NY1Y2 and -ZR4;
R3 represents H, cyano, halo, hydroxy, nitro, R4, NY1Y2, -ZR4, -C(=O)-OR5, -C(=O)-R7, -C(=O)-NY1Y2, -N(R8)-C(=O)-R4, -N(R8)-C(=O)-NY1Y2, -N(R8)-C(=O)-OR5, -SO2-NY3Y4, or -N(R8)-SO2-R7, or R3 represents aryl, heteroaryl, alkenyl or alkynyl, each optionally substituted by one or more groups selected from aryl, cyano, halo, hydroxy, heteroaryl, heterocycloalkyl, nitro, -C(=O)-NY1Y2, -C(=O)-OR5, -NY1Y2, -N(R6)-C(=O)-R7, -N(R6)-C(=O)-NY3Y4, -N(R6)-C(=O)-OR7, -N(R6)-SO2-R7, -N(R6)-SO2-NY3Y4, -SO2-NY1Y2 and -ZR4;
R4 represents alkyl, cycloalkyl or cycloalkylalkyl each optionally substituted by one or more groups selected from aryl, cycloalkyl, cyano, halo, heteroaryl, heterocycloalkyl, hydroxy, -CHO or a 5-, 6- or 7-membered cyclic acetal derivative of such -CHO, -C(=O)-NY1Y2, -C(=O)-OR5, -NY1Y2, -N(R6)-C(=O)-R7, -N(R6)-C(=O)-NY3Y4, -N(R6)-SO2-R7, -N(R6)-SO2-NY3Y4, -OR7 and -C(=O)-R7 where R4 is optionally interspersed with a group selected from O, S(O)n, and NR6;
R5 represents hydrogen, alkyl, alkenyl, aryl, arylalkyl, heteroaryl or heteroarylalkyl;
R6 represents hydrogen or lower alkyl;
R7 represents alkyl, aryl, arylalkyl, cycloalkyl, cycloalkylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl or heterocycloalkylalkyl;
R8 represents hydrogen or lower alkyl;
Y1 and Y2 are independently hydrogen, alkenyl, aryl, cycloalkyl, heteroaryl or alkyl optionally substituted by one or more groups selected from aryl, halo, heteroaryl, hydroxy, -C(=O)-NY3Y4, -C(=O)-OR5, -NY3Y4, -N(R6)-C(=O)-R7, -N(R6)-C(=O)-NY3Y4, -N(R6)-SO2-R7, -N(R6)-SO2-NY3Y4 and -OR7; or the group -NY1Y2 may form a cyclic amine;
Y3 and Y4 are independently hydrogen, alkenyl, alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl or heteroarylalkyl; or the group -NY3Y4 may form a cyclic amine;
Z represents O or S(O)n;
n is zero or an integer 1 or 2; or an N-oxide, prodrug, acid bioisostere, pharmaceutically acceptable salt or solvate of such compound;
or an N-oxide, prodrug, or acid bioisostere of such salt or solvate.
2. A compound according to claim 1 wherein R1 is hydrogen, C1-4alkyl, C1-4alkyl substituted by halo, C1-4alkyl substituted by hydroxy, C1-4alkyl substituted by -N(R6)C(=O)-R7, C1-4alkyl substituted by -C(=O)-NY1Y2, or cycloalkylalkyl substituted by hydroxy.
3. A compound according to claim 1 wherein R1 is hydrogen, -CH3, -CH2CH3, -CH2CF3 or
4. A compound according to claim 1 wherein R1 is hydrogen.
5. A compound according to any one of claims 1 to 4 wherein R2 is carboxy or an acid bioisostere, hydroxy, alkyl substituted by carboxy, heteroaryl, or R2 is -OR4 in which R4 is alkyl, -OR4 in which R4 is alkyl or cycloalkylalkyl substituted by one or more hydroxy groups, -OR4 in which R4 is alkyl substituted by one or more alkoxy groups, -OR4 in which R4 is alkyl or cycloalkyl substituted by one or more carboxy groups, -OR4 in which R4 is cycloalkyl substituted by -C(=O)-NY1Y2 or R2 is -C(=O)-R in which R is alkyl, or R2 is -C(=O)-NY1Y2, or -N(R6)-C(=O)-R7.
6. A compound according to any one of claims 1 to 4 wherein R2 is -OCH3 or -CONHC(CH3)2CH2OH.
7. A compound according to any one of claims 1 to 4 wherein R2 is -OCH3.
8. A compound according to any one of claims 1 to 7 wherein R3 is hydrogen, cyano, optionally substituted aryl, optionally substituted heteroaryl, alkyl, alkyl substituted by one or more halogen atoms, alkyl substituted by -C(=O)-NY1Y2, alkyl substituted by -OR7, or R3 is -ZR4, -C(=O)-OR5, -C(=O)-NY1Y2, or -NY1Y2.
9. A compound according to any one of claims 1 to 7 wherein R3 is hydrogen, cyano, pyridyl, trifluoromethyl, -CH2-CH2-C(=O)NHCH3, -OCF2H, -C(=O)-NH-C(CH3)2-CH2OH or
10. A compound according to any one of claims 1 to 7 wherein R3 is -OCH3.
11. A compound according to claim any one of claims 1 to 10 wherein R2 is attached at the 5-position of the indole ring.
12. A compound according to any one of claims 1 to 11 wherein the group is attached to the 3-position of the indole ring.
13. A compound according to claim 1 which is an N-oxide, prodrug, pharmaceutically acceptable salt or solvate of such compound; or an N-oxide or prodrug of such salt or solvate.
14, A compound according to claim 1 which is an N-oxide, prodrug, pharmaceutically acceptable salt or solvate of such compound; or an N-oxide or prodrug of such salt or solvate.
15. A pharmaceutical composition comprising a pharmaceutically effective amount of a compound according to any one of claims 1 to 14, together with one or more pharmaceutically acceptable carriers or excipients.
16. A method of treating a patient suffering from, or subject to, conditions which can be ameliorated by the administration of an inhibitor of the catalytic activity of Syk comprising administering to said patient a pharmaceutically effective amount of a compound according to any one of claims 1 to 14, or a pharmaceutically effective amount of a composition according to claim 15.
17. A method of treating inflammatory disease in a patient in need thereof, comprising administering to said patient a pharmaceutically effective amount of a compound according to any one of claims 1 to 14, or a pharmaceutically effective amount of a composition according to claim 15.
18. A method of treating a patient suffering from, or subject to, conditions which can be ameliorated by the administration of an inhibitor of the catalytic activity of FAK comprising administering to said patient a pharmaceutically effective amount of a compound according to any one of claims 1 to 14, or a pharmaceutically effective amount of a composition according to claim 15.
19. A method of treating a patient suffering from, or subject to, conditions which can be ameliorated by the administration of an inhibitor of the catalytic activity of KDR comprising administering to said patient a pharmaceutically effective amount of a compound according to any one of claims 1 to 14, or a pharmaceutically effective amount of a composition according to claim 15.
20. A method of treating a patient suffering from, or subject to, conditions which can be ameliorated by the administration of an inhibitor of the catalytic activity of Aurora2 comprising administering to said patient a pharmaceutically effective amount of a compound according to any one of claims 1 to 14, or a pharmaceutically effective amount of a composition according to claim 15.
21. A method of treating cancer in a patient in need thereof, comprising administering to said patient a pharmaceutically effective amount of a compound according to any one of claims 1 to 14, or a pharmaceutically effective amount of a composition according to claim 15.
22. A method according to claim 17 wherein the inflammatory disease is asthma, inflammatory dermatosis, allergic rhinitis, allergic conjunctivitis or joint inflammation.
23. A method according to claim 17 wherein the inflammatory disease is asthma, psoriasis, dermatitis herpetiformis, eczema, necrotizing vasculitis, cutaneous vasculitis, bullous disease, allergic rhinitis, allergic conjunctivitis, arthritis, rheumatoid arthritis, rubella arthritis, psoriatic arthritis or osteoarthritis.
24. A method of treating Chronic Obstructive Pulmonary Disease, in a patient in need thereof, comprising administering to said patient a pharmaceutically effective amount of a compound according to any one of claims 1 to 14, or a pharmaceutically effective amount of a composition according to claim 15.
25. A method according to claim 21 wherein the cancer being treated is colorectal, prostate, breast, thyroid, skin, colon or lung cancer.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0115393.1 | 2001-06-23 | ||
| GBGB0115393.1A GB0115393D0 (en) | 2001-06-23 | 2001-06-23 | Chemical compounds |
| US30167801P | 2001-06-28 | 2001-06-28 | |
| US60/301,678 | 2001-06-28 | ||
| PCT/GB2002/002835 WO2003000695A1 (en) | 2001-06-23 | 2002-06-21 | Pyrrolopyrimidines as protein kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2451932A1 true CA2451932A1 (en) | 2003-01-03 |
| CA2451932C CA2451932C (en) | 2009-12-29 |
Family
ID=9917225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002451932A Expired - Fee Related CA2451932C (en) | 2001-06-23 | 2002-06-21 | Pyrrolopyrimidines as protein kinase inhibitors |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP1404676A1 (en) |
| JP (1) | JP4344607B2 (en) |
| CN (1) | CN1294135C (en) |
| AU (1) | AU2002314325B8 (en) |
| BR (1) | BR0210652A (en) |
| CA (1) | CA2451932C (en) |
| CZ (1) | CZ20033443A3 (en) |
| EA (1) | EA007415B1 (en) |
| EC (1) | ECSP034922A (en) |
| EE (1) | EE05432B1 (en) |
| GB (1) | GB0115393D0 (en) |
| HU (1) | HUP0400300A3 (en) |
| ME (1) | MEP19308A (en) |
| NZ (1) | NZ529766A (en) |
| OA (1) | OA12632A (en) |
| PL (1) | PL374096A1 (en) |
| RS (1) | RS51698B (en) |
| SK (1) | SK15882003A3 (en) |
| TN (1) | TNSN03144A1 (en) |
| TR (1) | TR200302242T2 (en) |
| UA (1) | UA76760C2 (en) |
| WO (1) | WO2003000695A1 (en) |
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| JP2007511596A (en) * | 2003-11-17 | 2007-05-10 | ファイザー・プロダクツ・インク | Pyrrolopyrimidine compounds useful in the treatment of cancer |
| EP1689407A1 (en) * | 2003-11-25 | 2006-08-16 | Pfizer Products Inc. | Method of treatment of atherosclerosis |
| EP1763524A1 (en) * | 2004-04-23 | 2007-03-21 | Takeda San Diego, Inc. | Indole derivatives and use thereof as kinase inhibitors |
| FR2876103B1 (en) * | 2004-10-01 | 2008-02-22 | Aventis Pharma Sa | NOVEL BIS-AZAINDOL DERIVATIVES, THEIR PREPARATION AND THEIR PHARMACEUTICAL USE AS INHIBITORS OF KINASES |
| US7713973B2 (en) | 2004-10-15 | 2010-05-11 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| FR2878849B1 (en) | 2004-12-06 | 2008-09-12 | Aventis Pharma Sa | SUBSTITUTED INDOLES, COMPOSITIONS CONTAINING SAME, METHOD OF MANUFACTURE AND USE |
| CA2607901C (en) | 2005-06-13 | 2016-08-16 | Rigel Pharmaceuticals, Inc. | Methods and compositions for treating degenerative bone disorders using a syk inhibitory 2,4-pyrimidinediamine |
| US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
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| ES2560611T3 (en) | 2011-06-20 | 2016-02-22 | Incyte Holdings Corporation | Phenyl azetidinyl, pyridyl or pyrazinyl carboxamide derivatives as JAK inhibitors |
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| WO1997027199A1 (en) * | 1996-01-23 | 1997-07-31 | Novartis Ag | Pyrrolopyrimidines and processes for their preparation |
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| PA8474101A1 (en) * | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | PYROLEUM [2,3-D] PIRIMIDINE COMPOUNDS |
| KR20010085822A (en) * | 1998-09-18 | 2001-09-07 | 스타르크, 카르크 | 4-aminopyrrolopyrimidines as kinase inhibitors |
| JP4078074B2 (en) * | 1999-12-10 | 2008-04-23 | ファイザー・プロダクツ・インク | Pyrrolo [2,3-d] pyrimidine compound |
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| RS51698B (en) | 2011-10-31 |
| JP2005508300A (en) | 2005-03-31 |
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| AU2002314325B2 (en) | 2009-01-08 |
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| HUP0400300A2 (en) | 2007-08-28 |
| JP4344607B2 (en) | 2009-10-14 |
| RS99203A (en) | 2006-12-15 |
| AU2002314325B8 (en) | 2009-01-29 |
| EA200400073A1 (en) | 2004-08-26 |
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| UA76760C2 (en) | 2006-09-15 |
| EP1404676A1 (en) | 2004-04-07 |
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| EE200400003A (en) | 2004-02-16 |
| ECSP034922A (en) | 2004-04-28 |
| PL374096A1 (en) | 2005-09-19 |
| TNSN03144A1 (en) | 2005-12-23 |
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