JP2007508390A5 - - Google Patents
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- JP2007508390A5 JP2007508390A5 JP2006535591A JP2006535591A JP2007508390A5 JP 2007508390 A5 JP2007508390 A5 JP 2007508390A5 JP 2006535591 A JP2006535591 A JP 2006535591A JP 2006535591 A JP2006535591 A JP 2006535591A JP 2007508390 A5 JP2007508390 A5 JP 2007508390A5
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- Prior art keywords
- alkyl
- compound according
- aryl
- heteroaryl
- group
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 2
- 229940077388 benzenesulfonate Drugs 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- -1 2-cyano-2,2-diphenyl - ethyl Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51100903P | 2003-10-14 | 2003-10-14 | |
| PCT/US2004/033638 WO2005037280A1 (en) | 2003-10-14 | 2004-10-12 | Muscarinic acetycholine receptor antagonists |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007201718A Division JP4796552B2 (ja) | 2003-10-14 | 2007-08-02 | ムスカリン性アセチルコリン受容体アンタゴニスト |
| JP2007201719A Division JP2007314567A (ja) | 2003-10-14 | 2007-08-02 | ムスカリン性アセチルコリン受容体アンタゴニスト |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007508390A JP2007508390A (ja) | 2007-04-05 |
| JP2007508390A5 true JP2007508390A5 (enExample) | 2007-09-20 |
Family
ID=34465175
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006535591A Pending JP2007508390A (ja) | 2003-10-14 | 2004-10-12 | ムスカリン性アセチルコリン受容体アンタゴニスト |
| JP2007201718A Expired - Fee Related JP4796552B2 (ja) | 2003-10-14 | 2007-08-02 | ムスカリン性アセチルコリン受容体アンタゴニスト |
| JP2007201719A Pending JP2007314567A (ja) | 2003-10-14 | 2007-08-02 | ムスカリン性アセチルコリン受容体アンタゴニスト |
| JP2011109756A Expired - Fee Related JP5450509B2 (ja) | 2003-10-14 | 2011-05-16 | ムスカリン性アセチルコリン受容体アンタゴニスト |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007201718A Expired - Fee Related JP4796552B2 (ja) | 2003-10-14 | 2007-08-02 | ムスカリン性アセチルコリン受容体アンタゴニスト |
| JP2007201719A Pending JP2007314567A (ja) | 2003-10-14 | 2007-08-02 | ムスカリン性アセチルコリン受容体アンタゴニスト |
| JP2011109756A Expired - Fee Related JP5450509B2 (ja) | 2003-10-14 | 2011-05-16 | ムスカリン性アセチルコリン受容体アンタゴニスト |
Country Status (34)
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR045914A1 (es) * | 2003-07-17 | 2005-11-16 | Glaxo Group Ltd | Compuesto alcoholico terciario del 8-azoniabiciclo [3.2.1] octano, composicion farmaceutica que lo comprende y su uso para preparar esta ultima |
| SI1677795T1 (sl) * | 2003-10-14 | 2011-04-29 | Glaxo Group Ltd | Antagonisti muskarinskega acetilholinskega receptorja |
| EP1677796A4 (en) * | 2003-10-17 | 2006-12-27 | Glaxo Group Ltd | MUSCARIN ACETYLCHOLIN RECEPTOR ANTAGONISTS |
| PE20050489A1 (es) * | 2003-11-04 | 2005-09-02 | Glaxo Group Ltd | Antagonistas de receptores de acetilcolina muscarinicos |
| WO2005087236A1 (en) * | 2004-03-11 | 2005-09-22 | Glaxo Group Limited | Novel m3 muscarinic acetylcholine receptor antagonists |
| US7384946B2 (en) * | 2004-03-17 | 2008-06-10 | Glaxo Group Limited | M3 muscarinic acetylcholine receptor antagonists |
| EP1725238A4 (en) * | 2004-03-17 | 2009-04-01 | Glaxo Group Ltd | M 3 MUSCARINACETYLCHOLINE RECEPTOR ANTAGONISTS |
| UY28871A1 (es) | 2004-04-27 | 2005-11-30 | Glaxo Group Ltd | Antagonistas del receptor de acetilcolina muscarinico |
| EP1747219A4 (en) * | 2004-05-13 | 2010-05-26 | Glaxo Group Ltd | Antagonists of muscarinic acetylcholine receptor |
| JP2008520579A (ja) * | 2004-11-15 | 2008-06-19 | グラクソ グループ リミテッド | 新規ｍ３ムスカリン性アセチルコリン受容体アンタゴニスト |
| US20080275079A1 (en) * | 2005-08-02 | 2008-11-06 | Glaxo Group Limited | M3 Muscarinic Acetylcholine Receptor Antagonists |
| WO2007022351A2 (en) * | 2005-08-18 | 2007-02-22 | Glaxo Group Limited | Muscarinic acetylcholine receptor antagonists |
| KR20090003349A (ko) | 2006-04-20 | 2009-01-09 | 글락소 그룹 리미티드 | 화합물 |
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| JP5502858B2 (ja) | 2008-06-05 | 2014-05-28 | グラクソ グループ リミテッド | Ｐｉ３キナーゼの阻害剤として有用な４−カルボキサミドインダゾール誘導体 |
| JP5502077B2 (ja) | 2008-06-05 | 2014-05-28 | グラクソ グループ リミテッド | 新規な化合物 |
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| WO2010097114A1 (en) * | 2009-02-26 | 2010-09-02 | Glaxo Group Limited | Novel combination of therapeutic agents |
| JP5809985B2 (ja) | 2009-02-26 | 2015-11-11 | グラクソ グループ リミテッドＧｌａｘｏ Ｇｒｏｕｐ Ｌｉｍｉｔｅｄ | ４−｛（１ｒ）−２−［（６−｛２−［（２，６−ジクロロベンジル）オキシ］エトキシ｝ヘキシル）アミノ］−１−ヒドロキシエチル｝−２−（ヒドロキシメチル）フェノールを含む医薬製剤 |
| EP2406255B1 (en) | 2009-03-09 | 2015-04-29 | Glaxo Group Limited | 4-oxadiazol-2-yl-indazoles as inhibitors of pi3 kinases |
| WO2010102968A1 (en) | 2009-03-10 | 2010-09-16 | Glaxo Group Limited | Indole derivatives as ikk2 inhibitors |
| WO2010106016A1 (en) | 2009-03-17 | 2010-09-23 | Glaxo Group Limited | Pyrimidine derivatives used as itk inhibitors |
| AR076435A1 (es) | 2009-04-30 | 2011-06-08 | Glaxo Group Ltd | Compuestos de indazoles sustituidos, composiciones farmaceuticas que los contienen y procesos de obtencion de los mismos |
| GB0921075D0 (en) | 2009-12-01 | 2010-01-13 | Glaxo Group Ltd | Novel combination of the therapeutic agents |
| WO2011067365A1 (en) | 2009-12-03 | 2011-06-09 | Glaxo Group Limited | Benzpyrazole derivatives as inhibitors of p13 kinases |
| JP2013512878A (ja) | 2009-12-03 | 2013-04-18 | グラクソ グループ リミテッド | 新規化合物 |
| JP2013512880A (ja) | 2009-12-03 | 2013-04-18 | グラクソ グループ リミテッド | Ｐｉ３−キナーゼ阻害剤としてのインダゾール誘導体 |
| WO2011110575A1 (en) | 2010-03-11 | 2011-09-15 | Glaxo Group Limited | Derivatives of 2-[2-(benzo- or pyrido-) thiazolylamino]-6-aminopyridine, useful in the treatment of respiratoric, allergic or inflammatory diseases |
| RS54286B1 (sr) | 2010-09-08 | 2016-02-29 | Glaxosmithkline Intellectual Property Development Limited | Polimorfi i soli n-[5-[4-(5-{[(2r,6s)-2,6-dimetil-4-morfolinil]metil}-1,3-oksazol-2-il)-1h-indazol-6-il]-2(metiloksi)-3-piridinil]-metansulfonamida |
| WO2012035055A1 (en) | 2010-09-17 | 2012-03-22 | Glaxo Group Limited | Novel compounds |
| GB201018124D0 (en) | 2010-10-27 | 2010-12-08 | Glaxo Group Ltd | Polymorphs and salts |
| US9763965B2 (en) | 2012-04-13 | 2017-09-19 | Glaxosmithkline Intellectual Property Development Limited | Aggregate particles |
| GB201222679D0 (en) | 2012-12-17 | 2013-01-30 | Glaxo Group Ltd | Pharmaceutical combination products |
| RU2016112266A (ru) | 2013-10-17 | 2017-11-20 | Глаксосмитклайн Интеллекчуал Проперти Дивелопмент Лимитед | Ингибитор PI3K для лечения респираторного заболевания |
| JP2016537327A (ja) | 2013-10-17 | 2016-12-01 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | 呼吸器疾患の治療のためのｐｉ３ｋ阻害剤 |
| WO2015173701A2 (en) | 2014-05-12 | 2015-11-19 | Glaxosmithkline Intellectual Property (No. 2) Limited | Pharmaceutical compositions for treating infectious diseases |
| GB201602527D0 (en) | 2016-02-12 | 2016-03-30 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
| JP2019524792A (ja) | 2016-08-08 | 2019-09-05 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | 化合物 |
| GB201706102D0 (en) | 2017-04-18 | 2017-05-31 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
| GB201712081D0 (en) | 2017-07-27 | 2017-09-13 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
| BR112022019245A2 (pt) | 2020-03-26 | 2022-11-16 | Glaxosmithkline Ip Dev Ltd | Inibidores de catepsina para prevenir ou tratar infecções virais |
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2004
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2006
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2007
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