JP2007516244A5 - - Google Patents
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- JP2007516244A5 JP2007516244A5 JP2006542053A JP2006542053A JP2007516244A5 JP 2007516244 A5 JP2007516244 A5 JP 2007516244A5 JP 2006542053 A JP2006542053 A JP 2006542053A JP 2006542053 A JP2006542053 A JP 2006542053A JP 2007516244 A5 JP2007516244 A5 JP 2007516244A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- acyl
- integer
- cell activator
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- 229940126530 T cell activator Drugs 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- -1 W is —CH— or —N— Chemical compound 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 9
- 239000012190 activator Substances 0.000 claims description 8
- 150000004676 glycans Chemical class 0.000 claims description 5
- 229920001282 polysaccharide Polymers 0.000 claims description 5
- 239000005017 polysaccharide Substances 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000002772 monosaccharides Chemical class 0.000 claims description 3
- 229920001542 oligosaccharide Polymers 0.000 claims description 3
- 150000002482 oligosaccharides Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 12
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- 210000001744 T-lymphocyte Anatomy 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 150000002148 esters Chemical class 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000005466 alkylenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 150000001767 cationic compounds Chemical class 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 229910001411 inorganic cation Inorganic materials 0.000 claims 4
- 239000002777 nucleoside Substances 0.000 claims 4
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 4
- 150000002892 organic cations Chemical class 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 125000003172 aldehyde group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- MCQILDHFZKTBOD-UHFFFAOYSA-N diethoxy-hydroxy-imino-$l^{5}-phosphane Chemical compound CCOP(N)(=O)OCC MCQILDHFZKTBOD-UHFFFAOYSA-N 0.000 claims 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 150000002466 imines Chemical class 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 150000002632 lipids Chemical class 0.000 claims 2
- 150000002825 nitriles Chemical class 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 150000003457 sulfones Chemical class 0.000 claims 2
- 150000003462 sulfoxides Chemical class 0.000 claims 2
- 125000004001 thioalkyl group Chemical group 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- 239000012646 vaccine adjuvant Substances 0.000 claims 2
- 229940124931 vaccine adjuvant Drugs 0.000 claims 2
- MSTNYGQPCMXVAQ-KIYNQFGBSA-N 5,6,7,8-tetrahydrofolic acid Chemical compound N1C=2C(=O)NC(N)=NC=2NCC1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 MSTNYGQPCMXVAQ-KIYNQFGBSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 claims 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 claims 1
- 108091034117 Oligonucleotide Proteins 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 239000012455 biphasic mixture Substances 0.000 claims 1
- 239000005515 coenzyme Substances 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 229930003935 flavonoid Natural products 0.000 claims 1
- 150000002215 flavonoids Chemical class 0.000 claims 1
- 235000017173 flavonoids Nutrition 0.000 claims 1
- 229960000304 folic acid Drugs 0.000 claims 1
- 235000019152 folic acid Nutrition 0.000 claims 1
- 239000011724 folic acid Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000003944 halohydrins Chemical class 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 claims 1
- 229960000367 inositol Drugs 0.000 claims 1
- 108020004707 nucleic acids Proteins 0.000 claims 1
- 102000039446 nucleic acids Human genes 0.000 claims 1
- 150000007523 nucleic acids Chemical class 0.000 claims 1
- 239000003444 phase transfer catalyst Substances 0.000 claims 1
- 229960004838 phosphoric acid Drugs 0.000 claims 1
- 230000026731 phosphorylation Effects 0.000 claims 1
- 238000006366 phosphorylation reaction Methods 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
- 229960005486 vaccine Drugs 0.000 claims 1
- 229940088594 vitamin Drugs 0.000 claims 1
- 239000011782 vitamin Substances 0.000 claims 1
- 229930003231 vitamin Natural products 0.000 claims 1
- 235000013343 vitamin Nutrition 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 0 CC(C)(N*(C)(C)C(*)(C*)O)P([*+])(OC(C)(C)P(*)([*+])=O)=O Chemical compound CC(C)(N*(C)(C)C(*)(C*)O)P([*+])(OC(C)(C)P(*)([*+])=O)=O 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- NJTBJCGFHPFCQL-UHFFFAOYSA-N 3-methylbut-3-en-1-amine Chemical compound CC(=C)CCN NJTBJCGFHPFCQL-UHFFFAOYSA-N 0.000 description 3
- SVDQODWSLJQLQW-UHFFFAOYSA-N 4-azido-2-methylbut-1-ene Chemical compound CC(=C)CCN=[N+]=[N-] SVDQODWSLJQLQW-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical class OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- UYJATFHLTKEYNK-UHFFFAOYSA-N 5-but-1-enyl-4,5-dimethylcyclohexa-1,3-diene-1-sulfonic acid Chemical compound CCC=CC1(C)CC(S(O)(=O)=O)=CC=C1C UYJATFHLTKEYNK-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000001116 FEMA 4028 Substances 0.000 description 1
- KCOWBCKUDHEPFW-UHFFFAOYSA-N [amino(3-methylbut-3-enoxy)phosphoryl] dihydrogen phosphate Chemical compound CC(=C)CCOP(N)(=O)OP(O)(O)=O KCOWBCKUDHEPFW-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229960004853 betadex Drugs 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- MHNHYTDAOYJUEZ-UHFFFAOYSA-N triphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 MHNHYTDAOYJUEZ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IB2003/006375 WO2004050096A2 (en) | 2002-12-02 | 2003-12-02 | Phosphoantigens for regulating an immune response |
| US57923704P | 2004-06-15 | 2004-06-15 | |
| PCT/IB2004/004311 WO2005054258A2 (en) | 2003-12-02 | 2004-12-02 | New class of gamma delta t cells activators and use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007516244A JP2007516244A (ja) | 2007-06-21 |
| JP2007516244A5 true JP2007516244A5 (https=) | 2008-01-24 |
Family
ID=34655260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006542053A Withdrawn JP2007516244A (ja) | 2003-12-02 | 2004-12-02 | 新しいクラスのガンマデルタｔ細胞アクチベーターおよびその使用 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7767842B2 (https=) |
| EP (1) | EP1689758A2 (https=) |
| JP (1) | JP2007516244A (https=) |
| CN (1) | CN1890252A (https=) |
| AU (1) | AU2004295194A1 (https=) |
| BR (1) | BRPI0417088A (https=) |
| CA (1) | CA2547008A1 (https=) |
| WO (1) | WO2005054258A2 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0212666D0 (en) | 2002-05-31 | 2002-07-10 | Secr Defence | Immunogenic sequences |
| JP2007534743A (ja) | 2004-04-26 | 2007-11-29 | イネイト・ファーマ | アジュバント組成物およびその使用方法 |
| WO2006067635A2 (en) * | 2004-12-20 | 2006-06-29 | Innate Pharma S.A. | USE OF Ϝδ T LYMPHOCYTE ACTIVATORS AS VACCINE ADJUVANT |
| EP1933848A2 (en) * | 2005-10-06 | 2008-06-25 | Innate Pharma | Phosphoantigen salts of organic bases and methods for their crystallization |
| WO2007057440A2 (en) * | 2005-11-17 | 2007-05-24 | Innate Pharma | Improved methods of using phosphoantigen for the treatment of cancer |
| EP1878440A1 (en) * | 2006-07-13 | 2008-01-16 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and compositions for increasing the efficiency of therapeutic antibodies using gamma delta cell activator compounds |
| WO2008012538A2 (en) | 2006-07-25 | 2008-01-31 | The Secretary Of State For Defence | Live vaccine strains of francisella |
| US20100029674A1 (en) | 2006-11-17 | 2010-02-04 | Innate Pharma, S.A. | Methods of Using Phosphoantigen for the Treatment of Cancer |
| EP2123285A1 (en) * | 2008-05-21 | 2009-11-25 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Nucleosidic phosphoantigens for use in VGAMMA9DELTA2 T cell-mediated therapy |
| GB0906234D0 (en) | 2009-04-14 | 2009-05-20 | Secr Defence | Vaccine |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997021452A2 (en) * | 1995-12-14 | 1997-06-19 | Advanced Magnetics, Inc. | Macromolecular prodrugs of nucleotide analogs |
| DE19815864A1 (de) * | 1998-04-08 | 1999-10-14 | Europ Lab Molekularbiolog | 5'-modifizierte Nukleotide und ihre Anwendung in der Molekularbiologie und Medizin |
| ATE431428T1 (de) | 1998-10-01 | 2009-05-15 | Variagenics Inc | Ein verfahren zur analyse von polynukleotiden |
| WO2000036151A1 (en) | 1998-12-14 | 2000-06-22 | Li-Cor, Inc. | A heterogeneous assay for pyrophosphate detection |
| FR2791981B1 (fr) * | 1999-04-06 | 2001-07-20 | Inst Nat Sante Rech Med | Composes inhibant selectivement les lymphocytes tgamma9delta2, et leurs applications |
| DE10201458A1 (de) | 2001-04-11 | 2002-10-17 | Adelbert Bacher | Intermediate und Enzyme des Mevalonat-unabhängigen Isoprenoidbiosyntheseweg |
| ATE411805T1 (de) * | 2001-07-20 | 2008-11-15 | Bioagency Ag | Organo-phosphorverbindungen zur aktivierung von gamma/delta-t-zellen |
| FR2833266B1 (fr) * | 2001-12-11 | 2004-10-22 | Mayoly Spindler Lab | Nouveaux derives phosphonates, leur procede de preparation, leur utilisation comme modulateurs de l'activite des lymphocytes tgamma9 delta2 |
| DE60233576D1 (de) * | 2002-12-02 | 2009-10-15 | Innate Pharma | Interleukin-2 und Gamma Delta T Zellaktivator enthaltende Zusammensetzungen und deren Verwendungen |
| CA2587676A1 (en) * | 2004-11-19 | 2006-05-26 | Institut Gustave Roussy | Improved treatment of cancer by double-stranded rna |
| ITMI20060366A1 (it) | 2006-03-01 | 2007-09-02 | C4T S C A R L | Composti organo tiopirosfosfati metodo per prepararli e composizioni che li contengono |
-
2004
- 2004-12-02 CA CA002547008A patent/CA2547008A1/en not_active Abandoned
- 2004-12-02 EP EP04806475A patent/EP1689758A2/en not_active Withdrawn
- 2004-12-02 AU AU2004295194A patent/AU2004295194A1/en not_active Abandoned
- 2004-12-02 JP JP2006542053A patent/JP2007516244A/ja not_active Withdrawn
- 2004-12-02 WO PCT/IB2004/004311 patent/WO2005054258A2/en not_active Ceased
- 2004-12-02 CN CNA2004800356576A patent/CN1890252A/zh active Pending
- 2004-12-02 US US10/581,144 patent/US7767842B2/en not_active Expired - Fee Related
- 2004-12-02 BR BRPI0417088-1A patent/BRPI0417088A/pt not_active IP Right Cessation
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