ZA200604247B - Dual molecules containing peroxy derivative, the synthesis and therapeutic applications thereof - Google Patents

Dual molecules containing peroxy derivative, the synthesis and therapeutic applications thereof Download PDF

Info

Publication number: ZA200604247B
Authority: ZA; South Africa
Prior art keywords: formula; groups; compound; cyclic; alkyl
Prior art date: 2003-11-14

Application number

ZA200604247A

Other languages

English (en)

Inventor

Jerome Cazelles

Frederic Cosledan

Bernard Meunier

Alain Pellet

Original Assignee

Centre Nat Rech Scient

Palumed S A Sanofi Aventis

Priority date (The priority date 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 date listed.)

2003-11-14

Filing date

2004-11-09

Publication date

2008-05-28

2004-11-09 Application filed by Centre Nat Rech Scient, Palumed S A Sanofi Aventis filed Critical Centre Nat Rech Scient

2008-05-28 Publication of ZA200604247B publication Critical patent/ZA200604247B/en

Links

230000009977 dual effect Effects 0.000 title claims description 20
238000003786 synthesis reaction Methods 0.000 title description 53
230000015572 biosynthetic process Effects 0.000 title description 52
230000001225 therapeutic effect Effects 0.000 title description 3
125000000864 peroxy group Chemical group O(O*)* 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 106
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 98
-1 thioether radicals Chemical class 0.000 claims description 67
125000004122 cyclic group Chemical group 0.000 claims description 60
125000000217 alkyl group Chemical group 0.000 claims description 36
150000003839 salts Chemical class 0.000 claims description 36
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
150000002978 peroxides Chemical group 0.000 claims description 30
239000012453 solvate Substances 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 26
125000004432 carbon atom Chemical group C* 0.000 claims description 24
238000005859 coupling reaction Methods 0.000 claims description 21
125000005843 halogen group Chemical group 0.000 claims description 21
230000008878 coupling Effects 0.000 claims description 19
238000010168 coupling process Methods 0.000 claims description 19
150000003254 radicals Chemical class 0.000 claims description 19
229910052799 carbon Inorganic materials 0.000 claims description 18
238000000034 method Methods 0.000 claims description 18
229920006395 saturated elastomer Polymers 0.000 claims description 18
150000001412 amines Chemical class 0.000 claims description 17
229910052757 nitrogen Inorganic materials 0.000 claims description 17
125000002947 alkylene group Chemical group 0.000 claims description 16
230000000078 anti-malarial effect Effects 0.000 claims description 16
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
150000001408 amides Chemical class 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 10
125000004429 atom Chemical group 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
125000001072 heteroaryl group Chemical group 0.000 claims description 10
239000001301 oxygen Substances 0.000 claims description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
150000005010 aminoquinolines Chemical class 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
229940126601 medicinal product Drugs 0.000 claims description 9
125000004036 acetal group Chemical group 0.000 claims description 8
125000004430 oxygen atom Chemical group O* 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
239000005864 Sulphur Substances 0.000 claims description 7
150000001721 carbon Chemical group 0.000 claims description 7
201000004792 malaria Diseases 0.000 claims description 7
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 6
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 6
125000000524 functional group Chemical group 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
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125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
230000002265 prevention Effects 0.000 claims description 4
229910052698 phosphorus Inorganic materials 0.000 claims description 3
125000003367 polycyclic group Chemical group 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
150000005840 aryl radicals Chemical class 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
101000706020 Nicotiana tabacum Pathogenesis-related protein R minor form Proteins 0.000 claims 1
241000283984 Rodentia Species 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 84
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
239000000047 product Substances 0.000 description 45
239000000203 mixture Substances 0.000 description 44
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
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239000012074 organic phase Substances 0.000 description 26
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
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HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000003480 eluent Substances 0.000 description 18
239000012429 reaction media Substances 0.000 description 17
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
239000012071 phase Substances 0.000 description 15
238000003756 stirring Methods 0.000 description 15
238000003760 magnetic stirring Methods 0.000 description 14
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238000000921 elemental analysis Methods 0.000 description 12
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OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
238000001035 drying Methods 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
241000223960 Plasmodium falciparum Species 0.000 description 8
BLUAFEHZUWYNDE-NNWCWBAJSA-N artemisinin Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2OC(=O)[C@@H]4C BLUAFEHZUWYNDE-NNWCWBAJSA-N 0.000 description 8
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238000004587 chromatography analysis Methods 0.000 description 8
239000011521 glass Substances 0.000 description 8
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KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 8
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238000012360 testing method Methods 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
230000005587 bubbling Effects 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
238000010992 reflux Methods 0.000 description 6
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 5
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238000010790 dilution Methods 0.000 description 5
239000012895 dilution Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
125000004076 pyridyl group Chemical group 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000001117 sulphuric acid Substances 0.000 description 5
235000011149 sulphuric acid Nutrition 0.000 description 5
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
102100034871 C-C motif chemokine 8 Human genes 0.000 description 4
101000946794 Homo sapiens C-C motif chemokine 8 Proteins 0.000 description 4
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000012980 RPMI-1640 medium Substances 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 4
239000003430 antimalarial agent Substances 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
210000002966 serum Anatomy 0.000 description 4
MAAKQSASDHJHIR-UHFFFAOYSA-N trioxolane Chemical compound C1COOO1 MAAKQSASDHJHIR-UHFFFAOYSA-N 0.000 description 4
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238000005406 washing Methods 0.000 description 4
WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 3
JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 description 3
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125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
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WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Tropical Medicine & Parasitology (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

ZA200604247A 2003-11-14 2004-11-09 Dual molecules containing peroxy derivative, the synthesis and therapeutic applications thereof ZA200604247B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR0313371A FR2862304A1 (fr)	2003-11-14	2003-11-14	Molecules duales racemiques ou achirales contenant un derive peroxydique, leur synthese et leurs applications therapeutiques

Publications (1)

Publication Number	Publication Date
ZA200604247B true ZA200604247B (en)	2008-05-28

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ZA200604247A ZA200604247B (en)	2003-11-14	2004-11-09	Dual molecules containing peroxy derivative, the synthesis and therapeutic applications thereof

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Country	Link
US (1)	US7947701B2 (de)
EP (1)	EP1687312B1 (de)
JP (1)	JP2007511489A (de)
CN (1)	CN100448878C (de)
AP (1)	AP2006003626A0 (de)
AR (1)	AR046449A1 (de)
AT (1)	ATE473983T1 (de)
AU (1)	AU2004291374A1 (de)
BR (1)	BRPI0416593A (de)
CA (1)	CA2545491A1 (de)
DE (1)	DE602004028149D1 (de)
DK (1)	DK1687312T3 (de)
ES (1)	ES2348624T3 (de)
FR (1)	FR2862304A1 (de)
HR (1)	HRP20100557T1 (de)
IL (1)	IL175589A0 (de)
MX (1)	MXPA06005409A (de)
NO (1)	NO20062740L (de)
NZ (1)	NZ547805A (de)
PL (1)	PL1687312T3 (de)
PT (1)	PT1687312E (de)
SI (1)	SI1687312T1 (de)
TW (1)	TW200530249A (de)
WO (1)	WO2005049619A1 (de)
ZA (1)	ZA200604247B (de)

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FR2902100A1 (fr) *	2006-06-13	2007-12-14	Sanofi Aventis Sa	Molecules duales contenant un derive peroxydique, leur synthese et leurs applications en therapeutique
FR2924343A1 (fr) *	2007-12-04	2009-06-05	Palumed Sa	Nouvelles utilisations therapeutiques de molecules duales contenant un derive peroxydique.
US20170000784A1 (en) *	2013-12-08	2017-01-05	Van Andel Research Institute	Autophagy Inhibitors
WO2015123595A1 (en)	2014-02-14	2015-08-20	The Regents Of The University Of California	Cyclic peroxides as prodrugs for selective delivery of agents
BR112020018094A2 (pt)	2018-03-08	2020-12-22	Incyte Corporation	Compostos de aminopirazina diol como inibidores de pi3k-¿
US11046658B2 (en)	2018-07-02	2021-06-29	Incyte Corporation	Aminopyrazine derivatives as PI3K-γ inhibitors

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Publication number	Priority date	Publication date	Assignee	Title
FR2807433B1 (fr) *	2000-04-06	2002-09-20	Centre Nat Rech Scient	Molecules duales contenant un derives peroxydique, leur synthese et leurs applications therapeutiques
US6486199B1 (en) *	2001-06-21	2002-11-26	Medicines For Malaria Venture Mmv International Centre Cointrin	Spiro and dispiro 1,2,4-trioxolane antimalarials

2003
- 2003-11-14 FR FR0313371A patent/FR2862304A1/fr not_active Withdrawn
2004
- 2004-11-09 JP JP2006538893A patent/JP2007511489A/ja active Pending
- 2004-11-09 MX MXPA06005409A patent/MXPA06005409A/es not_active Application Discontinuation
- 2004-11-09 DE DE602004028149T patent/DE602004028149D1/de not_active Expired - Lifetime
- 2004-11-09 ZA ZA200604247A patent/ZA200604247B/en unknown
- 2004-11-09 CN CNB2004800372615A patent/CN100448878C/zh not_active Expired - Fee Related
- 2004-11-09 WO PCT/FR2004/002874 patent/WO2005049619A1/fr not_active Ceased
- 2004-11-09 DK DK04805417.5T patent/DK1687312T3/da active
- 2004-11-09 PL PL04805417T patent/PL1687312T3/pl unknown
- 2004-11-09 SI SI200431519T patent/SI1687312T1/sl unknown
- 2004-11-09 AU AU2004291374A patent/AU2004291374A1/en not_active Abandoned
- 2004-11-09 AP AP2006003626A patent/AP2006003626A0/xx unknown
- 2004-11-09 HR HR20100557T patent/HRP20100557T1/hr unknown
- 2004-11-09 AT AT04805417T patent/ATE473983T1/de active
- 2004-11-09 CA CA002545491A patent/CA2545491A1/fr not_active Abandoned
- 2004-11-09 EP EP04805417A patent/EP1687312B1/de not_active Expired - Lifetime
- 2004-11-09 BR BRPI0416593-4A patent/BRPI0416593A/pt not_active IP Right Cessation
- 2004-11-09 PT PT04805417T patent/PT1687312E/pt unknown
- 2004-11-09 ES ES04805417T patent/ES2348624T3/es not_active Expired - Lifetime
- 2004-11-09 NZ NZ547805A patent/NZ547805A/en unknown
- 2004-11-12 TW TW093134762A patent/TW200530249A/zh unknown
- 2004-11-12 AR ARP040104170A patent/AR046449A1/es unknown
2006
- 2006-05-11 IL IL175589A patent/IL175589A0/en unknown
- 2006-05-12 US US11/433,890 patent/US7947701B2/en not_active Expired - Fee Related
- 2006-06-13 NO NO20062740A patent/NO20062740L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
CN100448878C (zh)	2009-01-07
JP2007511489A (ja)	2007-05-10
NZ547805A (en)	2010-05-28
EP1687312A1 (de)	2006-08-09
PT1687312E (pt)	2010-10-18
CN1910189A (zh)	2007-02-07
US7947701B2 (en)	2011-05-24
WO2005049619A1 (fr)	2005-06-02
DK1687312T3 (da)	2010-11-08
NO20062740L (no)	2006-08-11
MXPA06005409A (es)	2007-11-22
SI1687312T1 (sl)	2010-11-30
CA2545491A1 (fr)	2005-06-02
DE602004028149D1 (de)	2010-08-26
US20070021423A1 (en)	2007-01-25
HRP20100557T1 (hr)	2011-03-31
IL175589A0 (en)	2006-09-05
FR2862304A1 (fr)	2005-05-20
ATE473983T1 (de)	2010-07-15
ES2348624T3 (es)	2010-12-09
EP1687312B1 (de)	2010-07-14
PL1687312T3 (pl)	2011-07-29
AU2004291374A1 (en)	2005-06-02
BRPI0416593A (pt)	2007-01-30
AP2006003626A0 (en)	2006-06-30
TW200530249A (en)	2005-09-16
AR046449A1 (es)	2005-12-07

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