ZA200500864B - Thiophene compounds - Google Patents
Thiophene compounds Download PDFInfo
- Publication number
- ZA200500864B ZA200500864B ZA200500864A ZA200500864A ZA200500864B ZA 200500864 B ZA200500864 B ZA 200500864B ZA 200500864 A ZA200500864 A ZA 200500864A ZA 200500864 A ZA200500864 A ZA 200500864A ZA 200500864 B ZA200500864 B ZA 200500864B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- alkyl
- benzimidazol
- formula
- compound according
- Prior art date
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- 150000003577 thiophenes Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 166
- 125000000217 alkyl group Chemical group 0.000 claims description 83
- 125000005842 heteroatom Chemical group 0.000 claims description 50
- 125000005843 halogen group Chemical group 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 44
- 206010028980 Neoplasm Diseases 0.000 claims description 41
- 125000003342 alkenyl group Chemical group 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 239000012453 solvate Substances 0.000 claims description 38
- 229910052717 sulfur Inorganic materials 0.000 claims description 36
- 125000000304 alkynyl group Chemical group 0.000 claims description 34
- 229910052760 oxygen Inorganic materials 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 33
- 241001465754 Metazoa Species 0.000 claims description 32
- 230000002401 inhibitory effect Effects 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- -1 -N(alkyl)2 Chemical group 0.000 claims description 27
- 230000011278 mitosis Effects 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 230000004663 cell proliferation Effects 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 208000035269 cancer or benign tumor Diseases 0.000 claims description 16
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
- 230000035755 proliferation Effects 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 230000001404 mediated effect Effects 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims description 12
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 4
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- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004419 alkynylene group Chemical group 0.000 claims description 4
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
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- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims description 2
- IKXRPCSTOHNEPH-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methoxy]-5-(5,6-dimethoxybenzimidazol-1-yl)thiophene-2-carboxamide Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(N)=O)=CC=1OCC1=C(Cl)C=CC=C1Cl IKXRPCSTOHNEPH-UHFFFAOYSA-N 0.000 claims description 2
- ZLNYTTROVPFOPQ-UHFFFAOYSA-N 3-[(3-aminophenyl)methoxy]-5-(5,6-dimethoxybenzimidazol-1-yl)thiophene-2-carboxamide Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(N)=O)=CC=1OCC1=CC=CC(N)=C1 ZLNYTTROVPFOPQ-UHFFFAOYSA-N 0.000 claims description 2
- IFTFEAPCQSZQTC-UHFFFAOYSA-N 3-[(3-bromopyridin-4-yl)methoxy]-5-(5,6-dimethoxybenzimidazol-1-yl)thiophene-2-carboxamide Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(N)=O)=CC=1OCC1=CC=NC=C1Br IFTFEAPCQSZQTC-UHFFFAOYSA-N 0.000 claims description 2
- WDJVBZGRDHWJGN-UHFFFAOYSA-N 3-[[2-(difluoromethoxy)phenyl]methoxy]-5-(5,6-dimethoxybenzimidazol-1-yl)thiophene-2-carboxamide Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(N)=O)=CC=1OCC1=CC=CC=C1OC(F)F WDJVBZGRDHWJGN-UHFFFAOYSA-N 0.000 claims description 2
- 125000006244 carboxylic acid protecting group Chemical group 0.000 claims description 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 claims 1
- JBLFNIIYPZPUJB-UHFFFAOYSA-N 3-[(2-aminopyridin-4-yl)methoxy]-5-(5,6-dimethoxybenzimidazol-1-yl)thiophene-2-carboxamide Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(N)=O)=CC=1OCC1=CC=NC(N)=C1 JBLFNIIYPZPUJB-UHFFFAOYSA-N 0.000 claims 1
- LOZDFLFAJKGZSO-UHFFFAOYSA-N 3-[(2-chloropyridin-3-yl)methoxy]-5-(5,6-dimethoxybenzimidazol-1-yl)thiophene-2-carboxamide Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(N)=O)=CC=1OCC1=CC=CN=C1Cl LOZDFLFAJKGZSO-UHFFFAOYSA-N 0.000 claims 1
- OPIDSVQKVZWDPM-UHFFFAOYSA-N 3-[(6-chloro-1,3-benzodioxol-5-yl)methoxy]-5-(5,6-dimethoxybenzimidazol-1-yl)thiophene-2-carboxamide Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(N)=O)=CC=1OCC(C(=C1)Cl)=CC2=C1OCO2 OPIDSVQKVZWDPM-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
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- Engineering & Computer Science (AREA)
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- Hematology (AREA)
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- Gastroenterology & Hepatology (AREA)
- Psychiatry (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| US40200802P | 2002-08-08 | 2002-08-08 |
Publications (1)
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Country Status (18)
| Country | Link |
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| US (2) | US20060074119A1 (enExample) |
| EP (1) | EP1546137A1 (enExample) |
| JP (1) | JP2006505522A (enExample) |
| KR (1) | KR20050071471A (enExample) |
| CN (1) | CN1688576A (enExample) |
| AU (1) | AU2003265348B2 (enExample) |
| BR (1) | BR0313160A (enExample) |
| CA (1) | CA2493908A1 (enExample) |
| IL (1) | IL166328A0 (enExample) |
| IS (1) | IS7657A (enExample) |
| MA (1) | MA27427A1 (enExample) |
| MX (1) | MXPA05001544A (enExample) |
| NO (1) | NO20050525L (enExample) |
| NZ (1) | NZ538134A (enExample) |
| PL (1) | PL375532A1 (enExample) |
| RU (1) | RU2296758C2 (enExample) |
| WO (1) | WO2004014899A1 (enExample) |
| ZA (1) | ZA200500864B (enExample) |
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| US6861422B2 (en) | 2003-02-26 | 2005-03-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Dihydropteridinones, processes for preparing them and their use as pharmaceutical compositions |
| BRPI0413746A (pt) * | 2003-08-21 | 2006-10-24 | Osi Pharm Inc | composto ou um seu n-óxido ou seu sal farmaceuticamente aceitável, composição, e, método de tratamento de distúrbio hiperproliferativo |
| EP1685128A1 (en) | 2003-10-16 | 2006-08-02 | Smithkline Beecham Corporation | Process for preparing benzimidazole thiophenes |
| US20070167499A1 (en) * | 2003-10-27 | 2007-07-19 | A*Bio Pte Ltd. | Biaryl linked hydroxamates: preparation and pharmaceutical applications |
| AU2004298448B2 (en) | 2003-12-18 | 2010-09-09 | Janssen Pharmaceutica N.V. | Pyrido- and pyrimidopyrimidine derivatives as anti- proliferative agents |
| JP2007519720A (ja) * | 2004-01-28 | 2007-07-19 | スミスクライン ビーチャム コーポレーション | チアゾール化合物 |
| GB0402809D0 (en) * | 2004-02-09 | 2004-03-10 | Glaxo Group Ltd | Chemical compounds |
| DE102004029784A1 (de) | 2004-06-21 | 2006-01-05 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue 2-Benzylaminodihydropteridinone, Verfahren zur deren Herstellung und deren Verwendung als Arzneimittel |
| DE102004033670A1 (de) | 2004-07-09 | 2006-02-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Pyridodihydropyrazinone, Verfahren zu Ihrer Herstellung und Ihre Verwendung als Arzneimittel |
| US20060035903A1 (en) | 2004-08-14 | 2006-02-16 | Boehringer Ingelheim International Gmbh | Storage stable perfusion solution for dihydropteridinones |
| US7728134B2 (en) | 2004-08-14 | 2010-06-01 | Boehringer Ingelheim International Gmbh | Hydrates and polymorphs of 4[[(7R)-8-cyclopentyl-7-ethyl-5,6,7,8-tetrahydro-5-methyl-6-oxo-2-pteridinyl]amino]-3-methoxy-N-(1-methyl-4-piperidinyl)-benzamide, process for their manufacture and their use as medicament |
| US20060074088A1 (en) | 2004-08-14 | 2006-04-06 | Boehringer Ingelheim International Gmbh | Dihydropteridinones for the treatment of cancer diseases |
| US20060058311A1 (en) | 2004-08-14 | 2006-03-16 | Boehringer Ingelheim International Gmbh | Combinations for the treatment of diseases involving cell proliferation |
| US7759485B2 (en) | 2004-08-14 | 2010-07-20 | Boehringer Ingelheim International Gmbh | Process for the manufacture of dihydropteridinones |
| EP1630163A1 (de) | 2004-08-25 | 2006-03-01 | Boehringer Ingelheim Pharma GmbH & Co.KG | Dihydropteridinonderivative, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| EP1632493A1 (de) | 2004-08-25 | 2006-03-08 | Boehringer Ingelheim Pharma GmbH & Co.KG | Dihydropteridinonderivative, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| CA2577947A1 (en) | 2004-08-31 | 2006-03-09 | Banyu Pharmaceutical Co., Ltd. | Novel substituted imidazole derivative |
| WO2006049339A1 (ja) | 2004-11-08 | 2006-05-11 | Banyu Pharmaceutical Co., Ltd. | 新規縮環イミダゾール誘導体 |
| DE102004058337A1 (de) | 2004-12-02 | 2006-06-14 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung von annelierten Piperazin-2-on Derivaten |
| NI200700147A (es) | 2004-12-08 | 2019-05-10 | Janssen Pharmaceutica Nv | Derivados de quinazolina inhibidores de cinasas dirigidos a multip |
| AU2005316312B2 (en) | 2004-12-17 | 2009-10-22 | Amgen, Inc. | Aminopyrimidine compounds and methods of use |
| MX2008003173A (es) * | 2005-09-06 | 2008-03-18 | Smithkline Beecham Corp | Compuestos de bencimidazol-tiofeno como inhibidores de plk. |
| JP2009507020A (ja) * | 2005-09-06 | 2009-02-19 | スミスクライン ビーチャム コーポレーション | Ｐｌｋ調節物質としてのルベンゾイミダゾールチオフェン化合物 |
| CN101300251B (zh) * | 2005-09-06 | 2011-08-03 | 史密丝克莱恩比彻姆公司 | 作为plk抑制剂的苯并咪唑噻吩化合物 |
| EP1924572B1 (en) * | 2005-09-06 | 2009-12-30 | SmithKline Beecham Corporation | Regioselective process for preparing benzimidazole thiophenes |
| EP2474546A1 (en) * | 2006-01-23 | 2012-07-11 | Vertex Pharmaceuticals Inc. | Thiophene-carboxamides useful as inhibitors of protein kinases |
| US7439358B2 (en) | 2006-02-08 | 2008-10-21 | Boehringer Ingelheim International Gmbh | Specific salt, anhydrous and crystalline form of a dihydropteridione derivative |
| US7504513B2 (en) * | 2006-02-27 | 2009-03-17 | Hoffman-La Roche Inc. | Thiazolyl-benzimidazoles |
| EP2007757B1 (en) | 2006-04-13 | 2012-10-03 | Vertex Pharmceuticals Incorporated | Thiophene-carboxamides useful as inhibitors of protein kinases |
| CA2652816A1 (en) * | 2006-05-23 | 2007-12-06 | Vertex Pharmaceuticals Incorporated | Thiophene-carboxamides useful as inhibitors of protein kinases |
| JP2009538305A (ja) * | 2006-05-23 | 2009-11-05 | バーテックス ファーマシューティカルズ インコーポレイテッド | プロテインキナーゼのインヒビターとして有用なチオフェンカルボキサミド |
| US20090326029A1 (en) * | 2006-06-02 | 2009-12-31 | Kevin Wayne Kuntz | Non-cyclic substituted benzimidazole thiophene benzyl ether compounds |
| PE20080710A1 (es) * | 2006-06-02 | 2008-08-07 | Smithkline Beecham Corp | Compuestos de tiofeno de bencimidazol |
| US7615643B2 (en) | 2006-06-02 | 2009-11-10 | Smithkline Beecham Corporation | Benzimidazole thiophene compounds |
| CA2654583C (en) | 2006-07-13 | 2015-11-24 | Janssen Pharmaceutica N.V. | Mtki quinazoline derivatives |
| US7649007B2 (en) | 2006-08-15 | 2010-01-19 | Wyeth Llc | Oxazolidine derivatives as PR modulators |
| US7618989B2 (en) | 2006-08-15 | 2009-11-17 | Wyeth | Tricyclic oxazolidone derivatives useful as PR modulators |
| TW200815428A (en) | 2006-08-15 | 2008-04-01 | Wyeth Corp | Oxazolidone derivatives as PR modulators |
| WO2008021309A1 (en) | 2006-08-15 | 2008-02-21 | Wyeth | Imidazolidin-2-one derivatives useful as pr modulators |
| WO2008021337A1 (en) | 2006-08-15 | 2008-02-21 | Wyeth | Oxazinan-2-one derivatives useful as pr modulators |
| WO2008070354A2 (en) * | 2006-10-31 | 2008-06-12 | Smithkline Beecham Corporation | 5- and 6- substituted benzimidazole thiophene compounds |
| WO2008153701A1 (en) * | 2007-05-24 | 2008-12-18 | Schering Corporation | Compounds for inhibiting ksp kinesin activity |
| JP2010531887A (ja) * | 2007-06-26 | 2010-09-30 | グラクソスミスクライン エルエルシー | ベンズイミダゾールチオフェンの調製方法 |
| WO2009003911A1 (en) * | 2007-06-29 | 2009-01-08 | 4Sc Ag | Thiophene-imidazopyridines |
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-
2003
- 2003-08-04 MX MXPA05001544A patent/MXPA05001544A/es unknown
- 2003-08-04 AU AU2003265348A patent/AU2003265348B2/en not_active Ceased
- 2003-08-04 KR KR1020057002244A patent/KR20050071471A/ko not_active Ceased
- 2003-08-04 BR BR0313160-2A patent/BR0313160A/pt not_active IP Right Cessation
- 2003-08-04 US US10/522,958 patent/US20060074119A1/en not_active Abandoned
- 2003-08-04 CN CNA038237555A patent/CN1688576A/zh active Pending
- 2003-08-04 RU RU2005102390/04A patent/RU2296758C2/ru not_active IP Right Cessation
- 2003-08-04 CA CA002493908A patent/CA2493908A1/en not_active Abandoned
- 2003-08-04 NZ NZ538134A patent/NZ538134A/en unknown
- 2003-08-04 EP EP03784888A patent/EP1546137A1/en not_active Ceased
- 2003-08-04 PL PL03375532A patent/PL375532A1/xx not_active Application Discontinuation
- 2003-08-04 WO PCT/US2003/024272 patent/WO2004014899A1/en not_active Ceased
- 2003-08-04 JP JP2004527723A patent/JP2006505522A/ja active Pending
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- 2005-01-20 IS IS7657A patent/IS7657A/is unknown
- 2005-01-28 ZA ZA200500864A patent/ZA200500864B/en unknown
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- 2005-03-04 MA MA28130A patent/MA27427A1/fr unknown
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| KR20050071471A (ko) | 2005-07-07 |
| WO2004014899A1 (en) | 2004-02-19 |
| RU2005102390A (ru) | 2006-01-10 |
| AU2003265348A1 (en) | 2004-02-25 |
| US20080269298A1 (en) | 2008-10-30 |
| US20060074119A1 (en) | 2006-04-06 |
| CA2493908A1 (en) | 2004-02-19 |
| JP2006505522A (ja) | 2006-02-16 |
| CN1688576A (zh) | 2005-10-26 |
| MA27427A1 (fr) | 2005-07-01 |
| NZ538134A (en) | 2006-03-31 |
| NO20050525L (no) | 2005-05-06 |
| IS7657A (is) | 2005-01-20 |
| EP1546137A1 (en) | 2005-06-29 |
| IL166328A0 (en) | 2006-01-15 |
| PL375532A1 (en) | 2005-11-28 |
| RU2296758C2 (ru) | 2007-04-10 |
| MXPA05001544A (es) | 2005-04-19 |
| AU2003265348B2 (en) | 2007-08-16 |
| BR0313160A (pt) | 2005-07-12 |
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