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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- JP
- Japan
- 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 (https=) | 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)
| Country | Link |
|---|---|
| US (3) | US7276521B2 (https=) |
| EP (1) | EP1677795B1 (https=) |
| JP (4) | JP2007508390A (https=) |
| KR (3) | KR20060106821A (https=) |
| CN (3) | CN1893948A (https=) |
| AP (3) | AP2007004239A0 (https=) |
| AR (1) | AR046103A1 (https=) |
| AT (1) | ATE494285T1 (https=) |
| AU (1) | AU2004281724B2 (https=) |
| BR (1) | BRPI0415361A (https=) |
| CA (1) | CA2542657C (https=) |
| CY (1) | CY1111364T1 (https=) |
| DE (1) | DE602004030930D1 (https=) |
| DK (1) | DK1677795T3 (https=) |
| EA (3) | EA013689B1 (https=) |
| EC (1) | ECSP066468A (https=) |
| ES (1) | ES2358673T3 (https=) |
| HR (1) | HRP20110232T1 (https=) |
| IL (2) | IL174843A0 (https=) |
| IS (1) | IS2918B (https=) |
| MA (1) | MA28110A1 (https=) |
| MX (1) | MXPA06004244A (https=) |
| MY (1) | MY143366A (https=) |
| NO (1) | NO20062042L (https=) |
| NZ (2) | NZ546312A (https=) |
| OA (1) | OA13316A (https=) |
| PE (1) | PE20050963A1 (https=) |
| PL (1) | PL1677795T3 (https=) |
| PT (1) | PT1677795E (https=) |
| SG (1) | SG147436A1 (https=) |
| SI (1) | SI1677795T1 (https=) |
| TW (3) | TWI409060B (https=) |
| UA (2) | UA87473C2 (https=) |
| WO (1) | WO2005037280A1 (https=) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200519108A (en) * | 2003-07-17 | 2005-06-16 | Glaxo Group Ltd | Muscarinic acetylcholine receptor antagonists |
| AP2007004239A0 (en) * | 2003-10-14 | 2007-12-31 | Glaxo Group Ltd | Muscarinic acetycholine receptor antagonists |
| BRPI0415281A (pt) * | 2003-10-17 | 2006-12-19 | Glaxo Group Ltd | antagonistas de receptor de acetilcolina muscarìnico |
| PE20050489A1 (es) * | 2003-11-04 | 2005-09-02 | Glaxo Group Ltd | Antagonistas de receptores de acetilcolina muscarinicos |
| US20090253908A1 (en) * | 2004-03-11 | 2009-10-08 | Glaxo Group Limited | Novel m3 muscarinic acetylchoine receptor antagonists |
| WO2005095407A1 (en) * | 2004-03-17 | 2005-10-13 | Glaxo Group Limited | M3 muscarinic acetylcholine receptor antagonists |
| EP1725238A4 (en) * | 2004-03-17 | 2009-04-01 | Glaxo Group Ltd | M 3 MUSCARINACETYLCHOLINE RECEPTOR ANTAGONISTS |
| PE20060259A1 (es) | 2004-04-27 | 2006-03-25 | Glaxo Group Ltd | Compuestos de quinuclidina como antagonistas del receptor de acetilcolina muscarinico |
| JP2007537261A (ja) * | 2004-05-13 | 2007-12-20 | グラクソ グループ リミテッド | ムスカリン性アセチルコリン受容体アンタゴニスト |
| US7932247B2 (en) * | 2004-11-15 | 2011-04-26 | Glaxo Group Limited | M3 muscarinic acetylcholine receptor antagonists |
| WO2007016639A2 (en) * | 2005-08-02 | 2007-02-08 | Glaxo Group Limited | M3 muscarinic acetylcholine receptor antagonists |
| WO2007022351A2 (en) * | 2005-08-18 | 2007-02-22 | Glaxo Group Limited | Muscarinic acetylcholine receptor antagonists |
| MX2008013411A (es) | 2006-04-20 | 2008-11-04 | Glaxo Group Ltd | Nuevos compuestos. |
| GB0611587D0 (en) | 2006-06-12 | 2006-07-19 | Glaxo Group Ltd | Novel compounds |
| SI2046787T1 (sl) | 2006-08-01 | 2011-07-29 | Glaxo Group Ltd | Pirazolo(3,4-b)piridinske spojine in njihova uporaba kot PDE4 inhibitorji |
| CN101663262B (zh) * | 2006-12-01 | 2014-03-26 | 百时美施贵宝公司 | 用于治疗动脉粥样硬化和心血管疾病的作为cetp抑制剂的n-(3-苄基)-2,2-(二苯基)-丙-1胺衍生物 |
| PE20081889A1 (es) | 2007-03-23 | 2009-03-05 | Smithkline Beecham Corp | Indol carboxamidas como inhibidores de ikk2 |
| RU2010108640A (ru) * | 2007-09-12 | 2011-10-20 | Глаксо Груп Лимитед (GB) | Новая комбинация терапевтических агентов |
| UY31637A1 (es) | 2008-02-06 | 2009-08-03 | Farmacoforos duales-antagonistas muscarinicos de pde4 | |
| PE20091553A1 (es) | 2008-02-06 | 2009-10-30 | Glaxo Group Ltd | Farmacoforos duales - antagonistas muscarinicos de pde4 |
| AR070563A1 (es) | 2008-02-06 | 2010-04-21 | Glaxo Group Ltd | Compuesto de un biciclo condensado pirazol-piridin-amina, composicion farmaceutica que lo comprende y su uso para preparar un medicamento util para el tratamiento de enfermedades respiratorias. |
| ES2566339T3 (es) | 2008-06-05 | 2016-04-12 | Glaxo Group Limited | Derivados de 4-carboxamida indazol útiles como inhibidores de PI3-quinasas |
| ES2383246T3 (es) | 2008-06-05 | 2012-06-19 | Glaxo Group Limited | 4-amino-indazoles |
| WO2010094643A1 (en) | 2009-02-17 | 2010-08-26 | Glaxo Group Limited | Quinoline derivatives and their uses for rhinitis and urticaria |
| LT2400950T (lt) | 2009-02-26 | 2019-08-26 | Glaxo Group Limited | Farmacinės kompozicijos, apimančios 4-{(1 r)-2-[(6-{2-[(2,6-dichlorbenzil)oksi]etoksi}heksil)amino]-1-hidroksetil}-2-(hidroksimetil)fenolį |
| WO2010097114A1 (en) * | 2009-02-26 | 2010-09-02 | Glaxo Group Limited | Novel combination of therapeutic agents |
| JP5656880B2 (ja) | 2009-03-09 | 2015-01-21 | グラクソ グループ リミテッドＧｌａｘｏ Ｇｒｏｕｐ Ｌｉｍｉｔｅｄ | Ｐｉ３キナーゼの阻害剤としての４−オキサジアゾール−２−イル−インダゾール |
| 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 |
| WO2010125082A1 (en) | 2009-04-30 | 2010-11-04 | Glaxo Group Limited | Oxazole substituted indazoles as pi3-kinase inhibitors |
| GB0921075D0 (en) | 2009-12-01 | 2010-01-13 | Glaxo Group Ltd | Novel combination of the therapeutic agents |
| US20120245171A1 (en) | 2009-12-03 | 2012-09-27 | Glaxo Group Limited | Benzpyrazole derivatives as inhibitors of pi3 kinases |
| EP2507226A1 (en) | 2009-12-03 | 2012-10-10 | Glaxo Group Limited | Novel compounds |
| EP2507231A1 (en) | 2009-12-03 | 2012-10-10 | Glaxo Group Limited | Indazole derivatives as pi 3 - kinase inhibitors |
| 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 |
| RU2666963C2 (ru) | 2012-04-13 | 2018-09-13 | Глаксосмитклайн Интеллекчуал Проперти Дивелопмент Лимитед | Агрегированные частицы |
| GB201222679D0 (en) | 2012-12-17 | 2013-01-30 | Glaxo Group Ltd | Pharmaceutical combination products |
| KR20160062178A (ko) | 2013-10-17 | 2016-06-01 | 글락소스미스클라인 인털렉츄얼 프로퍼티 디벨로프먼트 리미티드 | 호흡기 질병의 치료를 위한 ｐｉ３ｋ 억제제 |
| 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 |
| US20170100385A1 (en) | 2014-05-12 | 2017-04-13 | Glaxosmithkline Intellectual Property (No. 2) Limited | Pharmaceutical compositions comprising danirixin for treating infectious diseases |
| GB201602527D0 (en) | 2016-02-12 | 2016-03-30 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
| WO2018029126A1 (en) | 2016-08-08 | 2018-02-15 | Glaxosmithkline Intellectual Property Development Limited | Chemical compounds |
| 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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