JP2005511643A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2005511643A5 JP2005511643A5 JP2003547402A JP2003547402A JP2005511643A5 JP 2005511643 A5 JP2005511643 A5 JP 2005511643A5 JP 2003547402 A JP2003547402 A JP 2003547402A JP 2003547402 A JP2003547402 A JP 2003547402A JP 2005511643 A5 JP2005511643 A5 JP 2005511643A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- hydroxy
- pyrano
- pyrido
- quinazoline
- 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
- -1 2-n -Hexyl Chemical group 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 19
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 125000003282 alkyl amino group Chemical group 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 8
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 125000001589 carboacyl group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 230000002062 proliferating effect Effects 0.000 claims 4
- 229910052717 sulfur Chemical group 0.000 claims 4
- 239000011593 sulfur Chemical group 0.000 claims 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 125000006715 (C1-C5) alkylthio group Chemical group 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- BTFKXCMSXLSGNR-YCBFMBTMSA-N (9s)-2-(dimethylamino)-9-ethyl-9-hydroxy-1-(2-methylpropyl)-1h,12h-pyrano[3'',4'':6',7']indolizino[1',2':6,5]pyrido[4,3,2-de]quinazoline-10,13(9h,15h)-dione hydrochloride Chemical compound Cl.N1=C(N(C)C)N(CC(C)C)C2=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC3=CC=CC1=C32 BTFKXCMSXLSGNR-YCBFMBTMSA-N 0.000 claims 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000006309 butyl amino group Chemical group 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- 230000020176 deacylation Effects 0.000 claims 1
- 238000005947 deacylation reaction Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 125000004344 phenylpropyl group Chemical group 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- HZDNNJABYXNPPV-UHFFFAOYSA-N (2-chloro-2-oxoethyl) acetate Chemical compound CC(=O)OCC(Cl)=O HZDNNJABYXNPPV-UHFFFAOYSA-N 0.000 description 1
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 1
- 229940127093 camptothecin Drugs 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- HDRXZJPWHTXQRI-BHDTVMLSSA-N diltiazem hydrochloride Chemical compound [Cl-].C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CC[NH+](C)C)C2=CC=CC=C2S1 HDRXZJPWHTXQRI-BHDTVMLSSA-N 0.000 description 1
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01128361 | 2001-11-30 | ||
| PCT/EP2002/013216 WO2003045952A2 (en) | 2001-11-30 | 2002-11-25 | Condensed camptothecins as antitumor agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005511643A JP2005511643A (ja) | 2005-04-28 |
| JP2005511643A5 true JP2005511643A5 (OSRAM) | 2006-01-05 |
| JP4305909B2 JP4305909B2 (ja) | 2009-07-29 |
Family
ID=8179394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003547402A Expired - Fee Related JP4305909B2 (ja) | 2001-11-30 | 2002-11-25 | 六環式化合物 |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US6825194B2 (OSRAM) |
| EP (1) | EP1480984B9 (OSRAM) |
| JP (1) | JP4305909B2 (OSRAM) |
| KR (1) | KR100895746B1 (OSRAM) |
| CN (1) | CN100338066C (OSRAM) |
| AT (1) | ATE398131T1 (OSRAM) |
| AU (1) | AU2002356720B2 (OSRAM) |
| BR (1) | BR0214615A (OSRAM) |
| CA (1) | CA2468824C (OSRAM) |
| DE (1) | DE60227113D1 (OSRAM) |
| ES (1) | ES2307830T3 (OSRAM) |
| GT (1) | GT200200250A (OSRAM) |
| HU (1) | HUP0500062A3 (OSRAM) |
| IL (1) | IL162058A0 (OSRAM) |
| MX (1) | MXPA04005185A (OSRAM) |
| MY (1) | MY136138A (OSRAM) |
| NO (1) | NO329005B1 (OSRAM) |
| NZ (1) | NZ533568A (OSRAM) |
| PA (1) | PA8558901A1 (OSRAM) |
| PE (1) | PE20030725A1 (OSRAM) |
| PL (1) | PL207510B1 (OSRAM) |
| RS (1) | RS51051B (OSRAM) |
| RU (1) | RU2299212C2 (OSRAM) |
| TW (1) | TWI258481B (OSRAM) |
| UA (1) | UA80409C2 (OSRAM) |
| UY (1) | UY27560A1 (OSRAM) |
| WO (1) | WO2003045952A2 (OSRAM) |
| ZA (1) | ZA200404522B (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1777611A (zh) | 2003-02-21 | 2006-05-24 | 中外制药株式会社 | 制备六环喜树碱衍生物的方法 |
| BRPI0509732A (pt) | 2004-04-09 | 2007-09-25 | Chugai Pharmaceutical Co Ltd | pró-fármaco solúvel em água, composição farmacêutica, agente terapêutico, agente antifungo e uso do referido pró-fármaco |
| TW200744603A (en) * | 2005-08-22 | 2007-12-16 | Chugai Pharmaceutical Co Ltd | Novel anticancer concomitant drug |
| US20090118271A1 (en) * | 2005-10-19 | 2009-05-07 | Chugai Seiyaku Kabushiki Kaisha | Preventive or Therapeutic Agents for Pancreatic Cancer, Ovarian Cancer, or Liver Cancer Comprising a Novel Water-Soluble Prodrug |
| RU2439073C1 (ru) * | 2010-07-13 | 2012-01-10 | Государственное образовательное учреждение высшего профессионального образования "Кубанский государственный технологический университет" (ГОУ ВПО "КубГТУ") | СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ ИНДОЛИЗИНО[7,6-b]ИНДОЛА |
| DK3946464T3 (da) | 2019-03-29 | 2022-10-31 | Medimmune Ltd | Forbindelser og konjugater deraf |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4473692A (en) | 1981-09-04 | 1984-09-25 | Kabushiki Kaisha Yakult Honsha | Camptothecin derivatives and process for preparing same |
| US4939255A (en) * | 1987-06-24 | 1990-07-03 | Daiichi Pharmaceutical Co., Ltd. | Hexa-cyclic camptothecin derivatives |
| HU213136B (en) * | 1990-08-14 | 1997-02-28 | Kyorin Seiyaku Kk | Process for producing fluoroethyl camptothecin derivatives and pharmaceutical compositions containing them |
| JP3008226B2 (ja) * | 1991-01-16 | 2000-02-14 | 第一製薬株式会社 | 六環性化合物 |
| JP3359955B2 (ja) * | 1992-07-16 | 2002-12-24 | 第一製薬株式会社 | 抗腫瘍剤 |
| GB9402934D0 (en) * | 1994-02-16 | 1994-04-06 | Erba Carlo Spa | Camptothecin derivatives and process for their preparation |
| US5663177A (en) * | 1995-05-31 | 1997-09-02 | Smithkline Beecham Corporation | Water soluble camptothecin analogs |
| EP1017675B1 (en) | 1997-02-14 | 2006-06-14 | Bionumerik Pharmaceuticals, Inc. | Highly lipophilic camptothecin derivatives |
| GB9715821D0 (en) * | 1997-07-25 | 1997-10-01 | Pharmacia & Upjohn Spa | Amidino-camptothecin derivatives |
-
2002
- 2002-11-25 MX MXPA04005185A patent/MXPA04005185A/es active IP Right Grant
- 2002-11-25 WO PCT/EP2002/013216 patent/WO2003045952A2/en not_active Ceased
- 2002-11-25 AT AT02803790T patent/ATE398131T1/de not_active IP Right Cessation
- 2002-11-25 JP JP2003547402A patent/JP4305909B2/ja not_active Expired - Fee Related
- 2002-11-25 KR KR1020047008223A patent/KR100895746B1/ko not_active Expired - Fee Related
- 2002-11-25 AU AU2002356720A patent/AU2002356720B2/en not_active Ceased
- 2002-11-25 RU RU2004119841/04A patent/RU2299212C2/ru not_active IP Right Cessation
- 2002-11-25 EP EP02803790A patent/EP1480984B9/en not_active Expired - Lifetime
- 2002-11-25 ES ES02803790T patent/ES2307830T3/es not_active Expired - Lifetime
- 2002-11-25 HU HU0500062A patent/HUP0500062A3/hu unknown
- 2002-11-25 RS YUP-470/04A patent/RS51051B/sr unknown
- 2002-11-25 DE DE60227113T patent/DE60227113D1/de not_active Expired - Lifetime
- 2002-11-25 BR BR0214615-0A patent/BR0214615A/pt not_active IP Right Cessation
- 2002-11-25 CA CA2468824A patent/CA2468824C/en not_active Expired - Fee Related
- 2002-11-25 NZ NZ533568A patent/NZ533568A/en not_active IP Right Cessation
- 2002-11-25 CN CNB028277465A patent/CN100338066C/zh not_active Expired - Fee Related
- 2002-11-25 UA UA20040605013A patent/UA80409C2/uk unknown
- 2002-11-25 IL IL16205802A patent/IL162058A0/xx not_active IP Right Cessation
- 2002-11-25 PL PL370479A patent/PL207510B1/pl not_active IP Right Cessation
- 2002-11-26 US US10/304,672 patent/US6825194B2/en not_active Expired - Fee Related
- 2002-11-27 TW TW091134463A patent/TWI258481B/zh not_active IP Right Cessation
- 2002-11-28 PA PA20028558901A patent/PA8558901A1/es unknown
- 2002-11-28 MY MYPI20024479A patent/MY136138A/en unknown
- 2002-11-28 PE PE2002001148A patent/PE20030725A1/es not_active Application Discontinuation
- 2002-11-29 UY UY27560A patent/UY27560A1/es not_active Application Discontinuation
- 2002-11-29 GT GT200200250A patent/GT200200250A/es unknown
-
2004
- 2004-06-08 ZA ZA200404522A patent/ZA200404522B/en unknown
- 2004-06-29 NO NO20042729A patent/NO329005B1/no not_active IP Right Cessation
- 2004-09-16 US US10/942,044 patent/US7109195B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7461390B2 (ja) | メニン－ｍｌｌ相互作用の阻害剤 | |
| US20240124447A1 (en) | Inhibitors of the menin-mll interaction | |
| ES2882495T3 (es) | Derivados de 1H-indazol-3-carboxamida y compuestos relacionados como inhibidores del factor D para el tratamiento de enfermedades caracterizadas por una actividad anómala del sistema del complemento, como por ejemplo, trastornos inmunitarios | |
| JP6367366B2 (ja) | ４−アミノ−イミダゾキノリン化合物 | |
| CN111566095B (zh) | 被取代的吡咯并吡啶jak抑制剂及其制造方法和使用方法 | |
| JP2021522275A (ja) | サイクリン依存性キナーゼ阻害剤としての２−アミノ−ピリジンまたは２−アミノ−ピリミジン誘導体 | |
| ES2655971T9 (es) | Compuestos de aminopirimidinilo como inhibidores de JAK | |
| ES3011282T3 (en) | Imidazo[4,5-c]pyridine derivatives as toll-like receptor agonsits | |
| CN108779116A (zh) | 多发性内分泌瘤蛋白-mll相互作用的抑制剂 | |
| JP2018530539A (ja) | スルフィニルフェニル又はスルホンイミドイルフェニルベンザゼピン | |
| JP2011529918A (ja) | Ｊａｋ３阻害剤としてのピペリジン誘導体 | |
| JP2008535902A5 (OSRAM) | ||
| KR20120085738A (ko) | 야누스 키나제 억제제로서의 피롤로 ［1,2-ｂ］ 피리다진 유도체 | |
| US10023534B2 (en) | Carbazole and tetrahydrocarbazole compounds useful as inhibitors of BTK | |
| CN102574837A (zh) | 新的5-氟尿嘧啶衍生物 | |
| JP4823894B2 (ja) | 新規水溶性プロドラッグ | |
| JP2005511643A5 (OSRAM) | ||
| CN108601773B (zh) | 作为pi3k/mtor抑制剂的稠合喹啉化合物 | |
| JP2010535204A5 (OSRAM) | ||
| RU2299212C2 (ru) | Гексациклические соединения, фармацевтическая композиция, содержащая их и их применение в качестве противоопухолевых средств, способ получения гексациклических соединений | |
| JP2024504788A (ja) | ピラゾールアミド誘導体 | |
| JP2022546340A (ja) | アミン、アミド、フェノールの送達に用いられるプロドラッグプラットフォーム | |
| EP4504209A1 (en) | Method of treatment including kras g12c inhibitors and aurora a inhibitors | |
| RU2829484C2 (ru) | Ингибиторы взаимодействия менин-mll | |
| OA20485A (en) | IMIDAZO[4,5-C]pyridine derivatives as tolllike receptor agonsits |