JP2003501474A5 - - Google Patents
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- JP2003501474A5 JP2003501474A5 JP2001502852A JP2001502852A JP2003501474A5 JP 2003501474 A5 JP2003501474 A5 JP 2003501474A5 JP 2001502852 A JP2001502852 A JP 2001502852A JP 2001502852 A JP2001502852 A JP 2001502852A JP 2003501474 A5 JP2003501474 A5 JP 2003501474A5
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- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- heteroaryl
- aryl
- heterocyclyl
- 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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- 125000000217 alkyl group Chemical group 0.000 description 40
- 125000001072 heteroaryl group Chemical group 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005466 alkylenyl group Chemical group 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000037348 biosynthesis Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Description
【特許請求の範囲】
【請求項1】 式(I)
【化1】
(式中、
R1は、−アルキル−NR3−SO2−X−R4または−アルケニル−NR3−SO2−X−R4であり、
Xは結合または−NR5−であり、
R4は、アリール、ヘテロアリール、ヘテロシクリル、アルキルまたはアルケニルでありその各々は、
−アルキル;
−アルケニル;
−アリール;
−ヘテロアリール;
−ヘテロシクリル;
−置換シクロアルキル;
−置換アリール;
−置換ヘテロアリール;
−置換ヘテロシクリル;
−O−アルキル;
−O−(アルキル)0〜1−アリール;
−O−(アルキル)0〜1−置換アリール;
−O−(アルキル)0〜1−ヘテロアリール;
−O−(アルキル)0〜1−置換ヘテロアリール;
−O−(アルキル)0〜1−ヘテロシクリル;
−O−(アルキル)0〜1−置換ヘテロシクリル;
−COOH;
−CO−O−アルキル;
−CO−アルキル;
−S(O)0〜2−アルキル;
−S(O)0〜2−(アルキル)0〜1−アリール;
−S(O)0〜2−(アルキル)0〜1−置換アリール;
−S(O)0〜2−(アルキル)0〜1−ヘテロアリール;
−S(O)0〜2−(アルキル)0〜1−置換ヘテロアリール;
−S(O)0〜2−(アルキル)0〜1−ヘテロシクリル;
−S(O)0〜2−(アルキル)0〜1−置換ヘテロシクリル;
−(アルキル)0〜1−NR3R3;
−(アルキル)0〜1−NR3−CO−O−アルキル;
−(アルキル)0〜1−NR3−CO−アルキル;
−(アルキル)0〜1−NR3−CO−アリール;
−(アルキル)0〜1−NR3−CO−置換アリール;
−(アルキル)0〜1−NR3−CO−ヘテロアリール;
−(アルキル)0〜1−NR3−CO−置換ヘテロアリール;
−N3;
−ハロゲン;
−ハロアルキル;
−ハロアルコキシ;
−CO−ハロアルキル;
−CO−ハロアルコキシ;
−NO2;
−CN;
−OH;
−SH;および
アルキル、アルケニルまたはヘテロシクリルの場合、オキソ;
からなる群から選択される1種またはそれ以上の置換基で置換されていても未置換であってもよく、
R2は、
−水素;
−アルキル;
−アルケニル;
−アリール;
−置換アリール;
−ヘテロアリール;
−置換ヘテロアリール;
−アルキル−アルキル;
−アルキル−O−アルケニル;および
−OH;−ハロゲン;−N(R3)2;−CO−N(R3)2;−CO−C1〜10アルキル;−CO−O−C1〜10アルキル;−N3;−アリール;−置換アリール;−ヘテロアリール;−置換ヘテロアリール;−ヘテロシクリル;−置換ヘテロシクリル;−CO−アリール;−CO−(置換アリール);−CO−ヘテロアリール;および−CO−(置換ヘテロアリール)からなる群から選択される1種またはそれ以上の置換基で置換された−アルキルまたはアルケニル;
からなる群から選択され、
R3は各々独立に、水素およびC1〜10アルキルからなる群から選択され、
R5は、水素およびC1〜10アルキルからなる群から選択されるか、あるいは、R4とR5との組み合わせで3〜7員環の複素環または置換複素環を形成でき、
nは0〜4であり、存在するRは各々、C1〜10アルキル、C1〜10アルコキシ、ハロゲン、およびトリフルオロメチルからなる群から独立に選択される)で表される化合物、またはそれらの薬学的に許容される塩。
【請求項2】 Xが結合である、請求項1に記載の化合物。
【請求項3】 nが0である、請求項2に記載の化合物。
【請求項4】 R3が各々水素である、請求項2に記載の化合物。
【請求項5】 R1が−(CH2)2〜4−NR3−SO2−R4である、請求項2に記載の化合物。
【請求項6】 R4が、
−アルキル;
−アルケニル;
−アリール;
−ヘテロアリール;
−ヘテロシクリル;
−置換アリール;
−置換ヘテロアリール;
−置換ヘテロシクリル;
−O−アルキル;
−O−(アルキル)0〜1−アリール;
−O−(アルキル)0〜1−置換アリール;
−O−(アルキル)0〜1−ヘテロアリール;
−O−(アルキル)0〜1−置換ヘテロアリール;
−O−(アルキル)0〜1−ヘテロシクリル;
−O−(アルキル)0〜1−置換ヘテロシクリル;
−COOH;
−CO−O−アルキル;
−CO−アルキル;
−S(O)0〜2−アルキル;
−S(O)0〜2−(アルキル)0〜1−アリール;
−S(O)0〜2−(アルキル)0〜1−置換アリール;
−S(O)0〜2−(アルキル)0〜1−ヘテロアリール;
−S(O)0〜2−(アルキル)0〜1−置換ヘテロアリール;
−S(O)0〜2−(アルキル)0〜1−ヘテロシクリル;
−S(O)0〜2−(アルキル)0〜1−置換ヘテロシクリル;
−(アルキル)0〜1−NR3R3;
−(アルキル)0〜1−NR3−CO−O−アルキル;
−(アルキル)0〜1−NR3−CO−アルキル;
−(アルキル)0〜1−NR3−CO−アリール;
−(アルキル)0〜1−NR3−CO−置換アリール;
−(アルキル)0〜1−NR3−CO−ヘテロアリール;
−(アルキル)0〜1−NR3−CO−置換ヘテロアリール;
−N3;
−ハロゲン;
−ハロアルキル;
−ハロアルコキシ;
−CO−ハロアルコキシ;
−NO2;
−CN;
−OH;
−SH;および
アルキルの場合、オキソ;
からなる群から選択される1種またはそれ以上の置換基で置換されているかまたは未置換である、アルキル、アリールおよびヘテロアリールからなる群から選択される、請求項2に記載の化合物。
【請求項7】 R2が、水素、C1〜4アルキルおよびC1〜4アルキル−O−C1〜4アルキルからなる群から選択される、請求項2に記載の化合物。
【請求項8】 請求項1または2に記載の化合物またはそれらの薬学的に許容される塩を治療有効量で含み、かつ、薬学的に許容されるキャリアを含む、医薬組成物。
【請求項9】 動物においてサイトカインの生合成を誘導する医薬組成物を製造するための、請求項1または2に記載の化合物またはそれらの薬学的に許容される塩の使用。
【請求項1】 式(I)
【化1】
(式中、
R1は、−アルキル−NR3−SO2−X−R4または−アルケニル−NR3−SO2−X−R4であり、
Xは結合または−NR5−であり、
R4は、アリール、ヘテロアリール、ヘテロシクリル、アルキルまたはアルケニルでありその各々は、
−アルキル;
−アルケニル;
−アリール;
−ヘテロアリール;
−ヘテロシクリル;
−置換シクロアルキル;
−置換アリール;
−置換ヘテロアリール;
−置換ヘテロシクリル;
−O−アルキル;
−O−(アルキル)0〜1−アリール;
−O−(アルキル)0〜1−置換アリール;
−O−(アルキル)0〜1−ヘテロアリール;
−O−(アルキル)0〜1−置換ヘテロアリール;
−O−(アルキル)0〜1−ヘテロシクリル;
−O−(アルキル)0〜1−置換ヘテロシクリル;
−COOH;
−CO−O−アルキル;
−CO−アルキル;
−S(O)0〜2−アルキル;
−S(O)0〜2−(アルキル)0〜1−アリール;
−S(O)0〜2−(アルキル)0〜1−置換アリール;
−S(O)0〜2−(アルキル)0〜1−ヘテロアリール;
−S(O)0〜2−(アルキル)0〜1−置換ヘテロアリール;
−S(O)0〜2−(アルキル)0〜1−ヘテロシクリル;
−S(O)0〜2−(アルキル)0〜1−置換ヘテロシクリル;
−(アルキル)0〜1−NR3R3;
−(アルキル)0〜1−NR3−CO−O−アルキル;
−(アルキル)0〜1−NR3−CO−アルキル;
−(アルキル)0〜1−NR3−CO−アリール;
−(アルキル)0〜1−NR3−CO−置換アリール;
−(アルキル)0〜1−NR3−CO−ヘテロアリール;
−(アルキル)0〜1−NR3−CO−置換ヘテロアリール;
−N3;
−ハロゲン;
−ハロアルキル;
−ハロアルコキシ;
−CO−ハロアルキル;
−CO−ハロアルコキシ;
−NO2;
−CN;
−OH;
−SH;および
アルキル、アルケニルまたはヘテロシクリルの場合、オキソ;
からなる群から選択される1種またはそれ以上の置換基で置換されていても未置換であってもよく、
R2は、
−水素;
−アルキル;
−アルケニル;
−アリール;
−置換アリール;
−ヘテロアリール;
−置換ヘテロアリール;
−アルキル−アルキル;
−アルキル−O−アルケニル;および
−OH;−ハロゲン;−N(R3)2;−CO−N(R3)2;−CO−C1〜10アルキル;−CO−O−C1〜10アルキル;−N3;−アリール;−置換アリール;−ヘテロアリール;−置換ヘテロアリール;−ヘテロシクリル;−置換ヘテロシクリル;−CO−アリール;−CO−(置換アリール);−CO−ヘテロアリール;および−CO−(置換ヘテロアリール)からなる群から選択される1種またはそれ以上の置換基で置換された−アルキルまたはアルケニル;
からなる群から選択され、
R3は各々独立に、水素およびC1〜10アルキルからなる群から選択され、
R5は、水素およびC1〜10アルキルからなる群から選択されるか、あるいは、R4とR5との組み合わせで3〜7員環の複素環または置換複素環を形成でき、
nは0〜4であり、存在するRは各々、C1〜10アルキル、C1〜10アルコキシ、ハロゲン、およびトリフルオロメチルからなる群から独立に選択される)で表される化合物、またはそれらの薬学的に許容される塩。
【請求項2】 Xが結合である、請求項1に記載の化合物。
【請求項3】 nが0である、請求項2に記載の化合物。
【請求項4】 R3が各々水素である、請求項2に記載の化合物。
【請求項5】 R1が−(CH2)2〜4−NR3−SO2−R4である、請求項2に記載の化合物。
【請求項6】 R4が、
−アルキル;
−アルケニル;
−アリール;
−ヘテロアリール;
−ヘテロシクリル;
−置換アリール;
−置換ヘテロアリール;
−置換ヘテロシクリル;
−O−アルキル;
−O−(アルキル)0〜1−アリール;
−O−(アルキル)0〜1−置換アリール;
−O−(アルキル)0〜1−ヘテロアリール;
−O−(アルキル)0〜1−置換ヘテロアリール;
−O−(アルキル)0〜1−ヘテロシクリル;
−O−(アルキル)0〜1−置換ヘテロシクリル;
−COOH;
−CO−O−アルキル;
−CO−アルキル;
−S(O)0〜2−アルキル;
−S(O)0〜2−(アルキル)0〜1−アリール;
−S(O)0〜2−(アルキル)0〜1−置換アリール;
−S(O)0〜2−(アルキル)0〜1−ヘテロアリール;
−S(O)0〜2−(アルキル)0〜1−置換ヘテロアリール;
−S(O)0〜2−(アルキル)0〜1−ヘテロシクリル;
−S(O)0〜2−(アルキル)0〜1−置換ヘテロシクリル;
−(アルキル)0〜1−NR3R3;
−(アルキル)0〜1−NR3−CO−O−アルキル;
−(アルキル)0〜1−NR3−CO−アルキル;
−(アルキル)0〜1−NR3−CO−アリール;
−(アルキル)0〜1−NR3−CO−置換アリール;
−(アルキル)0〜1−NR3−CO−ヘテロアリール;
−(アルキル)0〜1−NR3−CO−置換ヘテロアリール;
−N3;
−ハロゲン;
−ハロアルキル;
−ハロアルコキシ;
−CO−ハロアルコキシ;
−NO2;
−CN;
−OH;
−SH;および
アルキルの場合、オキソ;
からなる群から選択される1種またはそれ以上の置換基で置換されているかまたは未置換である、アルキル、アリールおよびヘテロアリールからなる群から選択される、請求項2に記載の化合物。
【請求項7】 R2が、水素、C1〜4アルキルおよびC1〜4アルキル−O−C1〜4アルキルからなる群から選択される、請求項2に記載の化合物。
【請求項8】 請求項1または2に記載の化合物またはそれらの薬学的に許容される塩を治療有効量で含み、かつ、薬学的に許容されるキャリアを含む、医薬組成物。
【請求項9】 動物においてサイトカインの生合成を誘導する医薬組成物を製造するための、請求項1または2に記載の化合物またはそれらの薬学的に許容される塩の使用。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13836599P | 1999-06-10 | 1999-06-10 | |
US60/138,365 | 1999-06-10 | ||
US09/589,216 | 2000-06-07 | ||
US09/589,216 US6331539B1 (en) | 1999-06-10 | 2000-06-07 | Sulfonamide and sulfamide substituted imidazoquinolines |
PCT/US2000/015722 WO2000076519A1 (en) | 1999-06-10 | 2000-06-08 | Sulfonamide and sulfamide substituted imidazoquinolines |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2003501474A JP2003501474A (ja) | 2003-01-14 |
JP2003501474A5 true JP2003501474A5 (ja) | 2007-08-02 |
JP4833466B2 JP4833466B2 (ja) | 2011-12-07 |
Family
ID=26836139
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2001502852A Expired - Fee Related JP4833466B2 (ja) | 1999-06-10 | 2000-06-08 | スルホンアミドおよびスルファミド置換イミダゾキノリン |
Country Status (29)
Country | Link |
---|---|
US (5) | US6331539B1 (ja) |
EP (1) | EP1198233B1 (ja) |
JP (1) | JP4833466B2 (ja) |
KR (1) | KR100781428B1 (ja) |
CN (1) | CN1249061C (ja) |
AT (1) | ATE336249T1 (ja) |
AU (1) | AU772179B2 (ja) |
BR (1) | BR0011433B1 (ja) |
CA (1) | CA2376305C (ja) |
CY (1) | CY1108536T1 (ja) |
CZ (1) | CZ303287B6 (ja) |
DE (1) | DE60030126T2 (ja) |
DK (1) | DK1198233T3 (ja) |
EE (1) | EE05074B1 (ja) |
ES (1) | ES2270840T3 (ja) |
HK (1) | HK1086762A1 (ja) |
HR (1) | HRP20010890B1 (ja) |
HU (1) | HU229928B1 (ja) |
IL (2) | IL146486A0 (ja) |
MX (1) | MXPA01012547A (ja) |
NO (1) | NO320747B1 (ja) |
NZ (1) | NZ515967A (ja) |
PL (1) | PL211009B1 (ja) |
PT (1) | PT1198233E (ja) |
RU (1) | RU2248975C2 (ja) |
SK (1) | SK286418B6 (ja) |
TR (1) | TR200103575T2 (ja) |
UA (1) | UA73503C2 (ja) |
WO (1) | WO2000076519A1 (ja) |
Families Citing this family (250)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5741908A (en) | 1996-06-21 | 1998-04-21 | Minnesota Mining And Manufacturing Company | Process for reparing imidazoquinolinamines |
UA67760C2 (uk) * | 1997-12-11 | 2004-07-15 | Міннесота Майнінг Енд Мануфакчурінг Компані | Імідазонафтиридин та тетрагідроімідазонафтиридин, фармацевтична композиція, спосіб індукування біосинтезу цитокінів та спосіб лікування вірусної інфекції, проміжні сполуки |
US6518280B2 (en) | 1998-12-11 | 2003-02-11 | 3M Innovative Properties Company | Imidazonaphthyridines |
US20020058674A1 (en) | 1999-01-08 | 2002-05-16 | Hedenstrom John C. | Systems and methods for treating a mucosal surface |
US6558951B1 (en) * | 1999-02-11 | 2003-05-06 | 3M Innovative Properties Company | Maturation of dendritic cells with immune response modifying compounds |
US6331539B1 (en) | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
US6756382B2 (en) | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
US6573273B1 (en) * | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
US6541485B1 (en) | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
US6916925B1 (en) | 1999-11-05 | 2005-07-12 | 3M Innovative Properties Co. | Dye labeled imidazoquinoline compounds |
US6376669B1 (en) | 1999-11-05 | 2002-04-23 | 3M Innovative Properties Company | Dye labeled imidazoquinoline compounds |
JP3436512B2 (ja) * | 1999-12-28 | 2003-08-11 | 株式会社デンソー | アクセル装置 |
US6664264B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
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