JP2005522458A5 - - Google Patents
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- Publication number
- JP2005522458A5 JP2005522458A5 JP2003571263A JP2003571263A JP2005522458A5 JP 2005522458 A5 JP2005522458 A5 JP 2005522458A5 JP 2003571263 A JP2003571263 A JP 2003571263A JP 2003571263 A JP2003571263 A JP 2003571263A JP 2005522458 A5 JP2005522458 A5 JP 2005522458A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- optionally
- hydroxy
- substituted
- optionally substituted
- 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.)
- Granted
Links
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 101
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 90
- 229910052757 nitrogen Inorganic materials 0.000 claims 66
- 125000005842 heteroatom Chemical group 0.000 claims 56
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 52
- 229910052760 oxygen Inorganic materials 0.000 claims 52
- 239000001301 oxygen Substances 0.000 claims 52
- 125000000623 heterocyclic group Chemical group 0.000 claims 48
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 42
- 239000001257 hydrogen Substances 0.000 claims 42
- 229910052739 hydrogen Inorganic materials 0.000 claims 42
- 239000011593 sulfur Substances 0.000 claims 42
- 229910052717 sulfur Inorganic materials 0.000 claims 42
- 150000001875 compounds Chemical class 0.000 claims 38
- -1 hydroxy, amino Chemical group 0.000 claims 38
- 229910052736 halogen Inorganic materials 0.000 claims 34
- 150000002367 halogens Chemical class 0.000 claims 34
- 125000000217 alkyl group Chemical group 0.000 claims 33
- 150000002825 nitriles Chemical group 0.000 claims 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 27
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 13
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 8
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 7
- 239000000460 chlorine Substances 0.000 claims 7
- 150000003839 salts Chemical group 0.000 claims 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 claims 1
- 108091007960 PI3Ks Proteins 0.000 claims 1
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims 1
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
- 150000003624 transition metals Chemical class 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0204765A GB0204765D0 (en) | 2002-02-28 | 2002-02-28 | Organic compounds |
| GB0229626A GB0229626D0 (en) | 2002-12-19 | 2002-12-19 | Organic compounds |
| PCT/EP2003/002036 WO2003072557A1 (en) | 2002-02-28 | 2003-02-27 | 5-phenylthiazole derivatives and use as pi3 kinase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009187248A Division JP2009298799A (ja) | 2002-02-28 | 2009-08-12 | ５−フェニルチアゾール誘導体およびｐｉ３キナーゼインヒビターとしての使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005522458A JP2005522458A (ja) | 2005-07-28 |
| JP2005522458A5 true JP2005522458A5 (https=) | 2005-12-22 |
| JP4408701B2 JP4408701B2 (ja) | 2010-02-03 |
Family
ID=27767104
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003571263A Expired - Fee Related JP4408701B2 (ja) | 2002-02-28 | 2003-02-27 | ５−フェニルチアゾール誘導体およびｐｉ３キナーゼインヒビターとしての使用 |
| JP2009187248A Pending JP2009298799A (ja) | 2002-02-28 | 2009-08-12 | ５−フェニルチアゾール誘導体およびｐｉ３キナーゼインヒビターとしての使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009187248A Pending JP2009298799A (ja) | 2002-02-28 | 2009-08-12 | ５−フェニルチアゾール誘導体およびｐｉ３キナーゼインヒビターとしての使用 |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US7687637B2 (https=) |
| EP (1) | EP1480962B1 (https=) |
| JP (2) | JP4408701B2 (https=) |
| KR (1) | KR100688370B1 (https=) |
| CN (1) | CN100548996C (https=) |
| AR (1) | AR038703A1 (https=) |
| AT (1) | ATE521598T1 (https=) |
| AU (1) | AU2003214080A1 (https=) |
| BR (1) | BR0308030A (https=) |
| CA (1) | CA2477601C (https=) |
| CO (1) | CO5611131A2 (https=) |
| CY (2) | CY1112084T1 (https=) |
| DK (2) | DK2311818T3 (https=) |
| EC (2) | ECSP045253A (https=) |
| ES (2) | ES2405816T3 (https=) |
| IL (2) | IL163691A0 (https=) |
| MX (1) | MXPA04008362A (https=) |
| MY (1) | MY156407A (https=) |
| NO (1) | NO329175B1 (https=) |
| NZ (1) | NZ534657A (https=) |
| PE (1) | PE20030968A1 (https=) |
| PL (2) | PL215581B1 (https=) |
| PT (2) | PT1480962E (https=) |
| RU (2) | RU2378263C2 (https=) |
| SI (1) | SI1480962T1 (https=) |
| TW (1) | TWI314928B (https=) |
| WO (1) | WO2003072557A1 (https=) |
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| JP2006517234A (ja) | 2003-02-10 | 2006-07-20 | アムジエン・インコーポレーテツド | バニロイド受容体リガンドおよび治療におけるこれらのリガンドの使用 |
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| US20060229346A1 (en) * | 2003-03-31 | 2006-10-12 | Sucampo Ag | Method for treating vascular hyperpermeable disease |
| AR044519A1 (es) | 2003-05-02 | 2005-09-14 | Novartis Ag | Derivados de piridin-tiazol amina y de pirimidin-tiazol amina |
| GB0320197D0 (en) | 2003-08-28 | 2003-10-01 | Novartis Ag | Organic compounds |
| AU2005205201B2 (en) * | 2004-01-12 | 2011-05-12 | Merck Serono Sa | Thiazole derivatives and use thereof |
| EP2311827A1 (en) | 2004-08-28 | 2011-04-20 | AstraZeneca AB | Thiopyrimidine derivative, useful as an intermediate for chemokine receptor modulators. |
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| EP2343303A1 (de) | 2004-10-07 | 2011-07-13 | Boehringer Ingelheim International GmbH | PI3-Kinase Inhibitoren |
| SE0402735D0 (sv) * | 2004-11-09 | 2004-11-09 | Astrazeneca Ab | Novel compounds |
| AU2006243000B2 (en) * | 2005-05-05 | 2011-05-26 | Macrophage Pharma Limited | Alpha aminoacid ester-drug conjugates hydrolysable by carboxylesterase |
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| CN101248054B (zh) * | 2005-05-24 | 2012-05-09 | 默克雪兰诺有限公司 | 噻唑衍生物及其应用 |
| US8846393B2 (en) | 2005-11-29 | 2014-09-30 | Gamida-Cell Ltd. | Methods of improving stem cell homing and engraftment |
| US8105581B2 (en) * | 2005-12-01 | 2012-01-31 | The Scripps Research Institute | Compositions and methods for inducing neuronal differentiation |
| GB0525671D0 (en) * | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
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| US7517995B2 (en) | 2006-04-06 | 2009-04-14 | Boehringer Ingelheim International Gmbh | Thiazolyl-dihydro-cyclopentapyrazole |
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| GB0610243D0 (en) * | 2006-05-23 | 2006-07-05 | Novartis Ag | Organic compounds |
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| EP2581081A3 (en) | 2007-06-01 | 2013-07-31 | The Trustees Of Princeton University | Treatment of viral infections by modulation of host cell metabolic pathways |
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| WO2013052845A1 (en) | 2011-10-05 | 2013-04-11 | The Board Of Trustees Of The Leland Stanford Junior University | Pi-kinase inhibitors with broad spectrum anti-infective activity |
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| OA01933A (fr) | 1965-04-06 | 1970-02-04 | Pechiney Saint Gobain | Dérivés du thiazole. |
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| FR2429210A1 (fr) | 1978-06-19 | 1980-01-18 | Fabre Sa Pierre | Derives de phenyl-4 thiazolyl-2 oxamates utiles dans le traitement de l'asthme |
| JPS57136579A (en) | 1981-01-21 | 1982-08-23 | Mitsui Toatsu Chem Inc | Thiazolylurea derivative, its preparation, and pharmaceutical composition containing the same |
| EP0068033B1 (en) | 1981-01-08 | 1985-07-10 | Mitsui Toatsu Kagaku Kabushiki Kaisha | N-(4-phenyl-2-thiazolyl)carbamate derivatives, process for their preparation, and medicinal composition containing same |
| DE3413755A1 (de) | 1984-04-12 | 1985-10-24 | Basf Ag, 6700 Ludwigshafen | Thiazolylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
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| EP0321115B1 (en) | 1987-12-14 | 1991-08-14 | Sawai Pharmaceutical Co., Ltd. | Carboxamide derivatives having tetrazole and thiazole rings and their use |
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| CA2074933C (en) | 1990-11-30 | 2002-12-03 | Masatoshi Chihiro | Thiazole derivatives as active superoxide radical inhibitors |
| DE4401911A1 (de) | 1994-01-24 | 1995-08-03 | Basf Ag | Verwendung von Aryl- oder Heteroarylazoanilinen in der nichtlinearen Optik |
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| GB9625843D0 (en) * | 1996-12-12 | 1997-01-29 | Merck & Co Inc | Phenyl spiroethercycloalkyl tachykinn receptor antagonists |
| DE69831013T2 (de) | 1997-12-22 | 2006-04-20 | Bayer Pharmaceuticals Corp., West Haven | Inhibierung der raf-kinase durch substituierte heterocyclische harnstoffverbindungen |
| EP0928790B1 (en) | 1998-01-02 | 2003-03-05 | F. Hoffmann-La Roche Ag | Thiazole derivatives |
| US6100282A (en) * | 1998-01-02 | 2000-08-08 | Hoffman-La Roche Inc. | Thiazole derivatives |
| US6043254A (en) | 1998-04-03 | 2000-03-28 | Boehringer Ingelheim Pharma Kg | Indolinones having kinase-inhibiting activity |
| GB9823873D0 (en) * | 1998-10-30 | 1998-12-30 | Pharmacia & Upjohn Spa | 2-ureido-thiazole derivatives,process for their preparation,and their use as antitumour agents |
| CN1891693A (zh) | 2000-01-24 | 2007-01-10 | 基纳西亚股份有限公司 | 用于治疗的吗啉代基取代的化合物 |
| GEP20084317B (en) | 2000-04-25 | 2008-02-25 | Icos Corp | Inhibitors of human phosphatidyl-inositol 3-kinase delta |
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| AR039059A1 (es) * | 2001-08-06 | 2005-02-09 | Sanofi Aventis | Compuesto derivado de acilaminotiazol, su utilizacion, procedimientos para prepararlo, composicion farmaceutica que lo comprende, y compuestos intermediarios |
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