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
- C07D491/04—Ortho-condensed systems
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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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
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- Veterinary Medicine (AREA)
- Public Health (AREA)
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- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Dermatology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Vascular Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40200802P | 2002-08-08 | 2002-08-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200500864B true ZA200500864B (en) | 2006-04-26 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200500864A ZA200500864B (en) | 2002-08-08 | 2005-01-28 | Thiophene compounds |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US20060074119A1 (https=) |
| EP (1) | EP1546137A1 (https=) |
| JP (1) | JP2006505522A (https=) |
| KR (1) | KR20050071471A (https=) |
| CN (1) | CN1688576A (https=) |
| AU (1) | AU2003265348B2 (https=) |
| BR (1) | BR0313160A (https=) |
| CA (1) | CA2493908A1 (https=) |
| IL (1) | IL166328A0 (https=) |
| IS (1) | IS7657A (https=) |
| MA (1) | MA27427A1 (https=) |
| MX (1) | MXPA05001544A (https=) |
| NO (1) | NO20050525L (https=) |
| NZ (1) | NZ538134A (https=) |
| PL (1) | PL375532A1 (https=) |
| RU (1) | RU2296758C2 (https=) |
| WO (1) | WO2004014899A1 (https=) |
| ZA (1) | ZA200500864B (https=) |
Families Citing this family (92)
| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
| JP4769720B2 (ja) * | 2003-08-21 | 2011-09-07 | オーエスアイ・ファーマシューテイカルズ・エル・エル・シー | Ｎ−置換ベンズイミダゾリルｃ−Ｋｉｔ阻害剤 |
| 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 |
| MXPA06007017A (es) | 2003-12-18 | 2006-08-31 | Janssen Pharmaceutica Nv | Derivados de pirido y pirimidopirimidina como agentes antiproliferativos. |
| EP1711496A4 (en) * | 2004-01-28 | 2009-02-11 | Smithkline Beecham Corp | THIAZOLE COMPOUNDS |
| 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 |
| US20060058311A1 (en) | 2004-08-14 | 2006-03-16 | Boehringer Ingelheim International Gmbh | Combinations for the treatment of diseases involving cell proliferation |
| US20060074088A1 (en) | 2004-08-14 | 2006-04-06 | Boehringer Ingelheim International Gmbh | Dihydropteridinones for the treatment of cancer diseases |
| 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 |
| US7759485B2 (en) | 2004-08-14 | 2010-07-20 | Boehringer Ingelheim International Gmbh | Process for the manufacture of dihydropteridinones |
| EP1632493A1 (de) | 2004-08-25 | 2006-03-08 | Boehringer Ingelheim Pharma GmbH & Co.KG | Dihydropteridinonderivative, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| EP1630163A1 (de) | 2004-08-25 | 2006-03-01 | Boehringer Ingelheim Pharma GmbH & Co.KG | Dihydropteridinonderivative, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| AU2005278292B2 (en) | 2004-08-31 | 2011-09-08 | Msd K.K. | Novel substituted imidazole derivatives |
| JP4935357B2 (ja) | 2004-11-08 | 2012-05-23 | Ｍｓｄ株式会社 | 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 |
| EP1831207B1 (en) | 2004-12-17 | 2012-11-14 | Amgen Inc. | Aminopyrimidine compounds as plk inhibitors |
| US20080214563A1 (en) * | 2005-09-06 | 2008-09-04 | Mui Cheung | Benzimidazole Thiophene Compounds As Plk Modulators |
| EA014111B1 (ru) | 2005-09-06 | 2010-10-29 | Смитклайн Бичем Корпорейшн | Бензимидазолтиофеновые соединения в качестве ингибиторов polo-подобных киназ (plk) |
| 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 |
| MX2008003172A (es) * | 2005-09-06 | 2008-03-18 | Smithkline Beecham Corp | Proceso regioselectivo para la preparacion de bencimidazol-tiofenos. |
| 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 |
| WO2007120760A2 (en) * | 2006-04-13 | 2007-10-25 | Vertex Pharmaceuticals Incorporated | Thiophene-carboxamides useful as inhibitors of protein kinases |
| WO2007139816A2 (en) * | 2006-05-23 | 2007-12-06 | Vertex Pharmaceuticals Incorporated | Thiophene-carboxamides useful as inhibitors of protein kinases |
| WO2007139795A1 (en) * | 2006-05-23 | 2007-12-06 | Vertex Pharmaceuticals Incorporated | Thiophene-carboxamides useful as inhibitors of protein kinases |
| JP2009539771A (ja) * | 2006-06-02 | 2009-11-19 | スミスクライン ビーチャム コーポレーション | 置換ベンゾイミダゾールチオフェンベンジルエーテル化合物 |
| US7615643B2 (en) | 2006-06-02 | 2009-11-10 | Smithkline Beecham Corporation | Benzimidazole thiophene compounds |
| EP2032563B1 (en) * | 2006-06-02 | 2010-06-02 | GlaxoSmithKline LLC | Benzimidazol substituted thiophene derivatives with activity on plk |
| JP2009542778A (ja) | 2006-07-13 | 2009-12-03 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Ｍｔｋｉキナゾリン誘導体 |
| WO2008021338A2 (en) | 2006-08-15 | 2008-02-21 | Wyeth | Tricyclic oxazolidone derivatives useful as pr modulators |
| WO2008021309A1 (en) | 2006-08-15 | 2008-02-21 | Wyeth | Imidazolidin-2-one derivatives useful as pr modulators |
| TW200815428A (en) | 2006-08-15 | 2008-04-01 | Wyeth Corp | Oxazolidone derivatives as PR modulators |
| US7538107B2 (en) | 2006-08-15 | 2009-05-26 | Wyeth | Oxazinan-2-one derivatives useful as PR modulators |
| US7649007B2 (en) | 2006-08-15 | 2010-01-19 | Wyeth Llc | Oxazolidine derivatives as PR modulators |
| JP2010508301A (ja) * | 2006-10-31 | 2010-03-18 | スミスクライン ビーチャム コーポレーション | ５−置換及び６−置換ベンゾイミダゾールチオフェン化合物 |
| WO2008153701A1 (en) * | 2007-05-24 | 2008-12-18 | Schering Corporation | Compounds for inhibiting ksp kinesin activity |
| EP2170871A2 (en) * | 2007-06-26 | 2010-04-07 | GlaxoSmithKline LLC | Processes for preparing benzimidazole thiophenes |
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-
2003
- 2003-08-04 BR BR0313160-2A patent/BR0313160A/pt not_active IP Right Cessation
- 2003-08-04 WO PCT/US2003/024272 patent/WO2004014899A1/en not_active Ceased
- 2003-08-04 CA CA002493908A patent/CA2493908A1/en not_active Abandoned
- 2003-08-04 RU RU2005102390/04A patent/RU2296758C2/ru not_active IP Right Cessation
- 2003-08-04 CN CNA038237555A patent/CN1688576A/zh active Pending
- 2003-08-04 KR KR1020057002244A patent/KR20050071471A/ko not_active Ceased
- 2003-08-04 JP JP2004527723A patent/JP2006505522A/ja active Pending
- 2003-08-04 MX MXPA05001544A patent/MXPA05001544A/es unknown
- 2003-08-04 NZ NZ538134A patent/NZ538134A/en unknown
- 2003-08-04 US US10/522,958 patent/US20060074119A1/en not_active Abandoned
- 2003-08-04 PL PL03375532A patent/PL375532A1/xx not_active Application Discontinuation
- 2003-08-04 EP EP03784888A patent/EP1546137A1/en not_active Ceased
- 2003-08-04 AU AU2003265348A patent/AU2003265348B2/en not_active Ceased
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- 2005-01-20 IS IS7657A patent/IS7657A/is unknown
- 2005-01-28 ZA ZA200500864A patent/ZA200500864B/en unknown
- 2005-01-31 NO NO20050525A patent/NO20050525L/no not_active Application Discontinuation
- 2005-03-04 MA MA28130A patent/MA27427A1/fr unknown
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|---|---|
| MA27427A1 (fr) | 2005-07-01 |
| RU2005102390A (ru) | 2006-01-10 |
| EP1546137A1 (en) | 2005-06-29 |
| US20060074119A1 (en) | 2006-04-06 |
| NZ538134A (en) | 2006-03-31 |
| AU2003265348A1 (en) | 2004-02-25 |
| AU2003265348B2 (en) | 2007-08-16 |
| MXPA05001544A (es) | 2005-04-19 |
| CN1688576A (zh) | 2005-10-26 |
| KR20050071471A (ko) | 2005-07-07 |
| BR0313160A (pt) | 2005-07-12 |
| US20080269298A1 (en) | 2008-10-30 |
| CA2493908A1 (en) | 2004-02-19 |
| NO20050525L (no) | 2005-05-06 |
| IS7657A (is) | 2005-01-20 |
| PL375532A1 (en) | 2005-11-28 |
| WO2004014899A1 (en) | 2004-02-19 |
| IL166328A0 (en) | 2006-01-15 |
| JP2006505522A (ja) | 2006-02-16 |
| RU2296758C2 (ru) | 2007-04-10 |
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