IL165790A - Cationically substituted diphenyl azetidinones, method for their production, medicaments containing said compounds and use thereof - Google Patents

Cationically substituted diphenyl azetidinones, method for their production, medicaments containing said compounds and use thereof

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Publication number
IL165790A
IL165790A IL165790A IL16579004A IL165790A IL 165790 A IL165790 A IL 165790A IL 165790 A IL165790 A IL 165790A IL 16579004 A IL16579004 A IL 16579004A IL 165790 A IL165790 A IL 165790A
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alkyl
phenyl
crc6
agonists
radical
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IL165790A
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IL165790A0 (en
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Sanofi Aventis Deutschland
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Publication of IL165790A0 publication Critical patent/IL165790A0/en
Publication of IL165790A publication Critical patent/IL165790A/en

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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
    • C07D487/08—Bridged systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

The invention relates to compounds of formula (I), in which R1, R2, R3, R4, R5 and R6 are defined as cited, in addition to their physiologically compatible salts. The compounds are suitable for use e.g. as hypolipidaemics.

Claims (18)

165790/2 36 Patent claims:
1. A compound of the formula I in which R1 , R2, R3, R4, R5, R6 independently of one another are (C0-C3o)- alkylene-(LAG)n, where n may be 1 - 5 and where one or more carbon atoms of the alkylene radical may be replaced by -S(0)n-, where n = 0 - 2, -0-, -(C=Oh -(C=S)-, -CH=CH-, -C≡C-, -N((C C6)-alkyl)-, -N(phenyl)- , -N((CrC6)-alkyl-phenyl)- , -N(CO-(CH2)i-io-COOH)- or -NH-; H, F, CI, Br, I, CF3l Q2, N3, CN, COOH, COOid-Ce alkyl, CONH2, CONH(C C6)-alkyl, CON[(C C6)-alkyl]2, (C C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, 0-(CrC6)-alkyl, where one, more or all hydrogens in the alkyl radicals may be replaced by fluorine; PO3H2, SO3H, S02-NH2( S02NH(C C6)-alkyl, S02N[(C C6)-alkyl]2 , S-(C C6)-alkyl, S-(CH2)n-phenyl, SO-(CrC6)-alkyl, SO- (CH2)n-phenyl, S02-(CrC6)-alkyl, S02-(CH2)n-phenyl, where n = 0 - 6 165790/2 37 and the phenyl radical may be substituted up to two times by F, CI, Br, OH, CF3, N02, CN, OCF3, 0-(CrC6)-alkyl, (d-Ce^alkyl, NH2; NH2, NH-(C C6)-alkyl, N((C C6)-alkyl)2, NH(C C7)-acyl, phenyl, O- (CH2)n-phenyl, where n = 0 - 6, where the phenyl ring may be mono- to trisubstituted by F, CI, Br, I, OH, CF3, N02, CN, OCF3, 0-(C C6)-alkyl, (Ci-CB)-alkyl, NH2, NH(C C6)-alkyl, N((CrC6)-alkyl)2l S02-CH3, COOH, COO-(CrC6)-alkyl, CONH2; (LAG)n is a mono-, di- or tricyclic trialkylammonium radical, a mono-, di- or tricyclic trialkylammoniumalkyl radical, -(CH2)0-io-C(=NH)(NH2), -(CH2)0. 1D-C(=NH)(NHOH) or -NR7-C(=NR8)(NR9R10); R7, R8, R9 and R10 independently of one another are H, (C C6)-alkyl, (C C6)- alkyl-phenyl, phenyl, (C3-Ce)-cycloalkyl); is 1 , 2, 3, 4, 5; where in each case at least one of the radicals R1 to R6 must have the meaning (Co-C3o)-alkylene-(LAG)n, where n = 1 - 5 and where one or more carbon atoms of the alkylene radical may be replaced by -S(0)n-, where n = 0 - 2, -0-, -(C=0)-, -( C=S)-, -CH=CH-, -C≡C-, -N((C C6)-alkyl)-, -N(phenyl)-, -N((C C6)-alkyl-phenyl)- , -N(CO-(CH2)i.10-COOH)- or -NH-; and its pharmaceutically acceptable salts.
2. A compound of the formula I as claimed in claim 1 , wherein R2, R4, R5, R6 independently of one another are H, F, CI, Br, I, CF3, N02l N3, CN, COOH, COO(CrC6)-alkyl, CONH2) CONH(CrC6)-alkyl, CON[(CrC6)-alkyl]2, (C C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, 0- (CrC6)-alkyl, where one, more or all hydrogens in the alkyl radicals may be replaced by fluorine; 165790/2 38 C(=NH)(NH2), PO3H2, S03H, SO2-NH2, S02NH(CrC6)-alkyl, S02N[(d- C6)-alkyl]2 , S-(C C6)-alkyl, S-(CH2)n-phenyl, SO-(CrC6)-alkyl, SO- (CH2)n-phenyl, S02-(Ci-C6)-alkyl, S02-(CH2)n-phenyl, where n = 0 - 6 and the phenyl radical may be substituted up to two times by F, CI, Br, OH, CF3) N02) CN, OCF3, 0-(C C6)-alkyl, (C C6)-alkyl, NH2; NH2l NH-(C C6)-alkyl, N((C C6)-alkyl)2l NH(C C7)-acyl, phenyl, O- (CH2)n-phenyl, where n = 0 - 6, where the phenyl ring may be mono- to trisubstituted by F, CI, Br, I, OH, CF3, N02, CN, OCF3, 0-(C C6)-alkyl, (Ci-C6)-alkyl, NH2, NH(C C6)-alkyl, N((Ci-C6)-alkyl)2, S02-CH3, COOH, COO-(Ci-C6)-alkyl, CONH2; R1 , R3 independently of one another are (C0-C3o)-alkylene-(LAG) and where one or more carbon atoms of the alkylene radical may be replaced by -0-, -(C=0)-, -N(CH3)- or -NH-, H, F, CI, Br, I, CF3, N02, N3, CN, COOH, COO(CrC6)-alkyl, CONH2, CONH(C1-C6)-alkyl, CON[(C C6)-alkyl]2, (C C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, 0-(CrC6)-alkyl, where one, more or all hydrogens in the alkyl radicals may be replaced by fluorine; PO3H2, SO3H, SO2-NH2, S02NH(CrC6)-alkyl, S02N[(C C6)-alkyl]2 , S-(C C6)-alkyl, S-(CH2)n-phenyl, SO-(C Ce)-alkyl, SO- (CH2)n-phenyl, S02-(C CB)-alkyl, S02-(CH2)n-phenyl, where n = 0 - 6 and the phenyl radical may be substituted up to two times by F, CI, Br, OH, CF3, N02, CN, OCF3, 0-(C C6)-alkyl, (d-CeJ-alkyl, NH2; NH2, NH-(C C6)-alkyl, N((C C6)-alkyl)2, NH(C C7)-acyl, phenyl, O- (CH2)n-phenyl, where n = 0 - 6, where the phenyl ring may be mono- to trisubstituted by F, CI, Br, I, OH, CF3) N02, CN, OCF3, 0-(CrC6)-alkyl, (d-Ce^alkyl, NH2, NH(C C6)-alkyl, N((C C6)-alkyl}2, S02-CH3, COOH, COO-(CrC6)-alkyl, CONH2; (LAG) is a mono-, di- or tricyclic trialkylammonium radical, a mono-, di- or tricyclic trialkylammoniumalkyl radical, -(CH2)o-io-C(=NH)(NH2), -(CH2)o- 10-C(=NH)(NHOH) or -NR7-C(=NR8)(NR9R10); R7, R8, R9 and R10 independently of one another are H, (CrC6)-alkyl, (CrC6)- alkyl-phenyl, phenyl, (C3-C8)-cycloalkyl); where in each case at least one of the radicals R1 or R3 must have the meaning (Co-C3o)-alkylene-(LAG), where one or more carbon atoms of the alkylene radical may be replaced by -0-, -(C=0)-, -N(CH3)- or -NH-; and its physiologically acceptable salts.
3. A compound of the formula I as claimed in claim 1 or 2, wherein R2, R4, R5, R6 independently of one another are H, F, CI, Br, I, CF3, N02> N3l CN, COOH, C00(C C6)-alkyl, CONH2> CONH(Ci-C6)-alkyl, CON[(CrC6)-alkyl]2, (C C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, O- (Ci-C6)-alkyl, where one, more or all hydrogens in the alkyl radicals may be replaced by fluorine; C(=NH)(NH2), P03H2, S03H, S02-NH2, S02NH(CrC6)-alkyl, S02N[(C C6)-alkyl]2 , S-(CrC6)-alkyl, S-(CH2)n-phenyl, SO-(C C6)-alkyl, SO- (CH2)n-phenyl, S02-(C C6)-alkyl, S02-(CH2)n-phenyl, where n = 0 - 6 and the phenyl radical may be substituted up to two times by F, CI, Br, OH, CF3, NO2, CN, OCF3, O-(C.,-C6)-alkyl, (Ci-C6)-alkyl, NH2; NH2, NH-(C C6)-alkyl, N((CrC6)-alkyl)2) NH(C C7)-acyl, phenyl, O- (CH2)n-phenyl, where n = 0 - 6, where the phenyl ring may be mono- to trisubstituted by F, CI, Br, I, OH, CF3, NO2) CN, OCF3, O-(C C6)-alkyl, (C C6)-alkyl, NH2, NH(CrC6)-alkyl, N((CrC6)-alkyl)2, SO2-CH3, COOH, COO-(CrC6)-alkyl, CONH2; 165790/2 40 R1 , R3 independently of one another are -(CH2)o-i-Y-W-(Co-C25)-alkylene-Y'- W'-(LAG), where one or more carbon atoms of the alkylene radical may be replaced by -0-; H, F, CI, Br, I, CF3, N02, N3l CN, COOH, COO(Ci-C6)-alkyl, CONH2, CONH(CrC6)-alkyl, CON[(C C6)-alkyl]2, (CrC6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, 0-(CrC6)-alkyl, where one, more or all hydrogens in the alkyl radicals may be replaced by fluorine; P03H2, SO3H, S02-NH2, S02NH(Ci-C6)-alkyl, S02N[(C C6)-alkyl]2 , S-(CrC6)-alkyl, S-(CH2)n-phenyl, SO-(CrC6)-alkyl, SO- (CH2)n-phenyl, S02-(Ci-C6)-alkyl, S02-(CH2)n-phenyl, where n = 0 - 6 . and the phenyl radical may be substituted up to two times by F, CI, Br, OH, CF3, N02, CN, OCF3, O-id-CeJ-alkyl, (C C6)-alkyl, NH2; NH2, NH-(CrC6)-alkyl, N((CrC6}-alkyl)2, NH(CrC7)-acyl, phenyl, O- (CH2)n-phenyl, where n = 0 - 6, the phenyl ring may be mono- to trisubstituted by F, CI, Br, I, OH, CF3) N02, CN, OCF3, 0-(C C6)-alkyl, (Ci-C6)-alkyl, NH2, NH(C C6)-alkyl, N((Ci-C6)-alkyl)2, S02-CH3) COOH, COO-id-CeJ-alkyl, CONH2; Y, W, Y* W independently of one another are NH, NCH3, C=0, O, a bond or S(0)„, where n=0-2; or Y-W or Y'-W taken together are each a bond. (LAG) is a mono-, di- or tricyclic trialkylammonium radical, a mono-, di- or tricyclic trialkylammoniumalkyl radical, -(CH2)o- 10-C(=NH)(NHOH) or -NR7-C(=NR8)(NR9R10); R7, R8, R9 and R10 independently of one another are H, (CrC6)-alkyl, (CrC6)-alkyl- phenyl, phenyl, (C3-C8)-cycloalkyl); 165790/2 41 where in each case at least one of the radicals R1 or R3 must have the meaning -(CH2)o-rY-W-(Co-C25)-alkylene-Y'-W'-(LAG), where one or more carbon atoms of the alkylene radical may be replaced by -0-; and its pharmaceutically acceptable salts.
4. A compound of the formula I as claimed in one or more of claims 1 to 3, wherein LAG is a tricyclic trialkylammoniumalkyl radical, and its pharmaceutically acceptable salts.
5. A medicament comprising an effective amount of one or more compounds as claimed in one or more of claims 1 to 4.
6. A medicament comprising one or more compounds as claimed in one or more of claims 1 to 4 and at least one further active compound.
7. The medicament as claimed in claim 6, comprising, as further active compound, one or more compounds which normalize lipid metabolism.
8. The medicament as claimed in claim 6 or 7, which comprises, as further active compound, one or more antidiabetics, hypoglycemically active compounds, HMGCoA reductase inhibitors, cholesterol absorption inhibitors, PPAR gamma agonists, PPAR alpha agonists, PPAR alpha/gamma agonists, fibrates, MTP inhibitors, bile acid absorption inhibitors, CETP inhibitors, polymeric bile acid adsorbers, LDL receptor inducers, ACAT inhibitors, antioxidants, lipoprotein lipase inhibitors, ATP citrate lyase inhibitors, squalene synthetase inhibitors, lipoprotein(a) antagonists, lipase inhibitors, insulins, sulfonylureas, biguanides, meglitinides, thiazolidinediones, a-glucosidase inhibitors, active compounds which act on the ATP-dependent potassium channel of the beta cells, CART agonists, NPY agonists, MC4 agonists, orexin agonists, H3 agonists, TNF agonists, CRF agonists, CRF BP antagonists, urocortin agonists, β3 agonists, MSH (melanocyte-stimulating hormone) agonists, CCK agonists, serotonin-reuptake inhibitors, mixed serotonin and noradrenergic compounds, 5HT agonists, bombesin agonists, galanin antagonists, growth hormones, growth hormone-releasing compounds, TRH agonists, decoupling protein 2 or 3 modulators, leptin agonists, DA agonists (bromocriptine, doprexin), lipase/amylase inhibitors, PPAR modulators, RXR modulators or TR-p-agonists or amphetamines.
9. A compound as claimed in one or more of claims 1 to 4 for use as a medicament for the treatment of impaired lipid metabolism.
10. A process for preparing a medicament comprising one or more of the compounds as claimed in one or more of claims 1 to 4, which comprises mixing the. active compound with a pharmaceutically acceptable carrier and bringing this mixture into a form suitable for administration.
11. The use of the compounds as claimed in one or more of claims 1 to 4 for preparing a medicament for treating hyperlipidemia.
12. The use of the compounds as claimed in one or more of claims 1 to 4 for preparing a medicament for lowering the serum cholesterol concentration.
13. The use of the compounds as claimed in one or more of claims 1 to 4 for preparing a medicament for treating arteriosclerotic manifestations.
14. The use of the compounds as claimed in one or more of claims 1 to 4 for preparing a medicament for treating insulin resistance.
15. The compound according to any one of claims 1-4,9 substantially as described hereinabove.
16. The medicament according to any one of claims 5-8 substantially as described hereinabove.
17. The process according to claim 10 substantially as described hereinabove.
18. The use according to any one of claims 11-14 substantially as described hereinabove. P- 7420-IL
IL165790A 2002-06-19 2004-12-15 Cationically substituted diphenyl azetidinones, method for their production, medicaments containing said compounds and use thereof IL165790A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10227507A DE10227507A1 (en) 2002-06-19 2002-06-19 Cationically substituted diphenylazetidinones, processes for their preparation, medicaments containing these compounds and their use
PCT/EP2003/005814 WO2004000803A1 (en) 2002-06-19 2003-06-04 Cationically substituted diphenyl azetidinones, method for their production, medicaments containing said compounds and use thereof

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IL165790A0 IL165790A0 (en) 2006-01-15
IL165790A true IL165790A (en) 2010-04-15

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EP (1) EP1517890B1 (en)
JP (1) JP2005533071A (en)
KR (1) KR20050010061A (en)
CN (1) CN1662494A (en)
AT (1) ATE401304T1 (en)
AU (1) AU2003238209B2 (en)
BR (1) BR0311984A (en)
CA (1) CA2490108A1 (en)
DE (2) DE10227507A1 (en)
DK (1) DK1517890T3 (en)
ES (1) ES2310662T3 (en)
HR (1) HRP20041202A2 (en)
IL (1) IL165790A (en)
MA (1) MA27251A1 (en)
MX (1) MXPA04012308A (en)
NO (1) NO20050088L (en)
PA (1) PA8575601A1 (en)
PL (1) PL372660A1 (en)
PT (1) PT1517890E (en)
RS (1) RS108604A (en)
RU (1) RU2315753C2 (en)
SV (1) SV2004001555A (en)
TW (1) TW200406380A (en)
UY (1) UY27852A1 (en)
WO (1) WO2004000803A1 (en)
ZA (1) ZA200409379B (en)

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US8871758B2 (en) 2011-03-08 2014-10-28 Sanofi Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof
WO2012120052A1 (en) 2011-03-08 2012-09-13 Sanofi Oxathiazine derivatives substituted with carbocycles or heterocycles, method for producing same, drugs containing said compounds, and use thereof
WO2012120055A1 (en) 2011-03-08 2012-09-13 Sanofi Di- and tri-substituted oxathiazine derivates, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof
WO2012120054A1 (en) 2011-03-08 2012-09-13 Sanofi Di- and tri-substituted oxathiazine derivates, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof
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DE10227507A1 (en) 2004-01-08
UY27852A1 (en) 2003-12-31
MA27251A1 (en) 2005-03-01
EP1517890B1 (en) 2008-07-16
PL372660A1 (en) 2005-07-25
BR0311984A (en) 2005-04-26
RU2315753C2 (en) 2008-01-27
NO20050088L (en) 2005-01-06
IL165790A0 (en) 2006-01-15
KR20050010061A (en) 2005-01-26
SV2004001555A (en) 2004-03-19
ZA200409379B (en) 2006-05-31
JP2005533071A (en) 2005-11-04
TW200406380A (en) 2004-05-01
HRP20041202A2 (en) 2005-06-30
AU2003238209A1 (en) 2004-01-06
WO2004000803A1 (en) 2003-12-31
RS108604A (en) 2007-02-05
DK1517890T3 (en) 2008-11-10
PA8575601A1 (en) 2004-02-07
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DE50310161D1 (en) 2008-08-28
AU2003238209B2 (en) 2009-01-22
CN1662494A (en) 2005-08-31
EP1517890A1 (en) 2005-03-30
MXPA04012308A (en) 2005-02-25
ES2310662T3 (en) 2009-01-16
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PT1517890E (en) 2008-10-14
CA2490108A1 (en) 2003-12-31

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