JP2007501252A - 免疫応答調整剤を含有する製剤 - Google Patents
免疫応答調整剤を含有する製剤 Download PDFInfo
- Publication number
- JP2007501252A JP2007501252A JP2006522714A JP2006522714A JP2007501252A JP 2007501252 A JP2007501252 A JP 2007501252A JP 2006522714 A JP2006522714 A JP 2006522714A JP 2006522714 A JP2006522714 A JP 2006522714A JP 2007501252 A JP2007501252 A JP 2007501252A
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- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- imidazo
- quinolin
- amine
- 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.)
- Pending
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- 239000000203 mixture Substances 0.000 title claims abstract description 118
- 238000009472 formulation Methods 0.000 title claims abstract description 106
- 230000028993 immune response Effects 0.000 title claims abstract description 56
- 239000003607 modifier Substances 0.000 title claims abstract description 54
- -1 oxazolopyridine amines Chemical class 0.000 claims abstract description 182
- 239000013011 aqueous formulation Substances 0.000 claims abstract description 34
- WSIZDLIFQIDDKA-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinolin-2-amine Chemical compound C1=CC=NC2=C(NC(N)=N3)C3=CC=C21 WSIZDLIFQIDDKA-UHFFFAOYSA-N 0.000 claims abstract description 17
- 206010039085 Rhinitis allergic Diseases 0.000 claims abstract description 12
- 201000010105 allergic rhinitis Diseases 0.000 claims abstract description 12
- 150000001412 amines Chemical class 0.000 claims abstract description 11
- BZBQNDWAMYFNIE-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-h]quinolin-2-amine Chemical compound C1C=C2C=CC=NC2=C2C1NC(N)N2 BZBQNDWAMYFNIE-UHFFFAOYSA-N 0.000 claims abstract description 10
- KXQPVJRJUJJWQJ-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyridin-2-amine Chemical compound C1=CN=C2NC(N)=NC2=C1 KXQPVJRJUJJWQJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 208000036142 Viral infection Diseases 0.000 claims abstract description 8
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- 230000009385 viral infection Effects 0.000 claims abstract description 8
- JWLAFIOGOBJKEP-UHFFFAOYSA-N 1h-imidazo[4,5-b][1,8]naphthyridin-2-amine Chemical compound C1=CN=C2NC3=NC(N)=NC3=CC2=C1 JWLAFIOGOBJKEP-UHFFFAOYSA-N 0.000 claims abstract description 7
- QOOXNMYDCWUEHW-UHFFFAOYSA-N [1,3]oxazolo[4,5-h]quinolin-2-amine Chemical compound C1=CC=NC2=C(OC(N)=N3)C3=CC=C21 QOOXNMYDCWUEHW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000539 dimer Substances 0.000 claims abstract description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 80
- 150000001875 compounds Chemical class 0.000 claims description 66
- 229940124669 imidazoquinoline Drugs 0.000 claims description 46
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 37
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- 150000003456 sulfonamides Chemical group 0.000 claims description 13
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 12
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- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 11
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
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- YSQNOJMVGVZJRJ-UHFFFAOYSA-N [1,3]oxazolo[5,4-b]pyridin-2-amine Chemical compound C1=CN=C2OC(N)=NC2=C1 YSQNOJMVGVZJRJ-UHFFFAOYSA-N 0.000 claims description 5
- 229960000686 benzalkonium chloride Drugs 0.000 claims description 5
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 5
- 229920003086 cellulose ether Polymers 0.000 claims description 5
- NVNWHRIYBUUBAJ-UHFFFAOYSA-N n-[1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-yl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)NS(C)(=O)=O)C3=C(N)N=C21 NVNWHRIYBUUBAJ-UHFFFAOYSA-N 0.000 claims description 5
- 201000009890 sinusitis Diseases 0.000 claims description 5
- QWTGJQJILBSXEC-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,8-naphthyridin-2-amine Chemical compound C1=CN=C2NC(N)CCC2=C1 QWTGJQJILBSXEC-UHFFFAOYSA-N 0.000 claims description 4
- XGKHUHWWPFOKMN-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinolin-2-amine Chemical compound C1=CC=C2NC(N)CCC2=C1 XGKHUHWWPFOKMN-UHFFFAOYSA-N 0.000 claims description 4
- GCMNJUJAKQGROZ-UHFFFAOYSA-N 1,2-Dihydroquinolin-2-imine Chemical compound C1=CC=CC2=NC(N)=CC=C21 GCMNJUJAKQGROZ-UHFFFAOYSA-N 0.000 claims description 4
- MBIIMZGOLXUTTO-UHFFFAOYSA-N 1-[1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-yl]-3-cyclohexylurea Chemical compound CCOCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CC(C)(C)NC(=O)NC1CCCCC1 MBIIMZGOLXUTTO-UHFFFAOYSA-N 0.000 claims description 4
- BXUVSPUTCNMBJE-UHFFFAOYSA-N 1-[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]-2,2-dimethylpropyl]-3-phenylurea Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CC(C)(C)CNC(=O)NC1=CC=CC=C1 BXUVSPUTCNMBJE-UHFFFAOYSA-N 0.000 claims description 4
- QOFBARJUFKOMTB-UHFFFAOYSA-N 1-[4-amino-2-(ethoxymethyl)-7-[5-(hydroxymethyl)pyridin-3-yl]imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol Chemical compound C1=CC2=C3N(CC(C)(C)O)C(COCC)=NC3=C(N)N=C2C=C1C1=CN=CC(CO)=C1 QOFBARJUFKOMTB-UHFFFAOYSA-N 0.000 claims description 4
- YQUGGLAFTLRIOP-UHFFFAOYSA-N 2-butyl-1-(2-propylsulfonylethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCS(=O)(=O)CCC)C3=C(N)N=C21 YQUGGLAFTLRIOP-UHFFFAOYSA-N 0.000 claims description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 4
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- OVBJJZOQPCKUOR-UHFFFAOYSA-L EDTA disodium salt dihydrate Chemical group O.O.[Na+].[Na+].[O-]C(=O)C[NH+](CC([O-])=O)CC[NH+](CC([O-])=O)CC([O-])=O OVBJJZOQPCKUOR-UHFFFAOYSA-L 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
- YUDGNSDTJOJYBS-UHFFFAOYSA-N [1,3]oxazolo[5,4-b][1,8]naphthyridin-2-amine Chemical compound C1=CN=C2N=C(OC(N)=N3)C3=CC2=C1 YUDGNSDTJOJYBS-UHFFFAOYSA-N 0.000 claims description 4
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 4
- 150000004676 glycans Chemical class 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 4
- PNECXIFPGGDANB-UHFFFAOYSA-N n-[1-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-yl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CC(C)(C)NS(C)(=O)=O)C3=C(N)N=C21 PNECXIFPGGDANB-UHFFFAOYSA-N 0.000 claims description 4
- YWWACDRMTXQASG-UHFFFAOYSA-N n-[1-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-yl]methanesulfonamide Chemical compound C1CCCC2=C(N(C(CCOC)=N3)CC(C)(C)NS(C)(=O)=O)C3=C(N)N=C21 YWWACDRMTXQASG-UHFFFAOYSA-N 0.000 claims description 4
- OMKBWMAPAIGGNW-UHFFFAOYSA-N n-[1-[4-amino-2-(ethoxymethyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-yl]methanesulfonamide Chemical compound C1CCCC2=C(N(C(COCC)=N3)CC(C)(C)NS(C)(=O)=O)C3=C(N)N=C21 OMKBWMAPAIGGNW-UHFFFAOYSA-N 0.000 claims description 4
- BCYBSHJYJXUUOS-UHFFFAOYSA-N n-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl]morpholine-4-carboxamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCNC(=O)N1CCOCC1 BCYBSHJYJXUUOS-UHFFFAOYSA-N 0.000 claims description 4
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 3
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- GTUCHIHDDSGYMP-UHFFFAOYSA-N 1-[4-amino-2-(ethoxymethyl)-7-pyridin-3-ylimidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol Chemical compound C1=CC2=C3N(CC(C)(C)O)C(COCC)=NC3=C(N)N=C2C=C1C1=CC=CN=C1 GTUCHIHDDSGYMP-UHFFFAOYSA-N 0.000 claims description 2
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012006976A (ja) * | 2003-11-25 | 2012-01-12 | Three M Innovative Properties Co | 置換されたイミダゾ環系および方法 |
| JP2018525427A (ja) * | 2015-08-31 | 2018-09-06 | スリーエム イノベイティブ プロパティズ カンパニー | 置換グアニジン基を含有するイミダゾ［４，５−ｃ］環状化合物 |
| JP2018525426A (ja) * | 2015-08-31 | 2018-09-06 | スリーエム イノベイティブ プロパティズ カンパニー | グアニジン置換イミダゾ［４，５−ｃ］環状化合物 |
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| JP2012006976A (ja) * | 2003-11-25 | 2012-01-12 | Three M Innovative Properties Co | 置換されたイミダゾ環系および方法 |
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| JP2018525426A (ja) * | 2015-08-31 | 2018-09-06 | スリーエム イノベイティブ プロパティズ カンパニー | グアニジン置換イミダゾ［４，５−ｃ］環状化合物 |
Also Published As
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| JP2007501251A (ja) | 2007-01-25 |
| WO2005016273A2 (en) | 2005-02-24 |
| CN1852711A (zh) | 2006-10-25 |
| CA2534625A1 (en) | 2005-02-24 |
| US20050070460A1 (en) | 2005-03-31 |
| AU2004264336B2 (en) | 2010-12-23 |
| WO2005016275A2 (en) | 2005-02-24 |
| US20070292456A1 (en) | 2007-12-20 |
| EP1651216A2 (en) | 2006-05-03 |
| CA2534313C (en) | 2013-03-19 |
| EP1651190B1 (en) | 2012-09-19 |
| WO2005016273A3 (en) | 2005-12-29 |
| AU2004264336A1 (en) | 2005-02-24 |
| EP1651190A4 (en) | 2009-07-15 |
| CA2534313A1 (en) | 2005-02-24 |
| AU2004264330A1 (en) | 2005-02-24 |
| EP1651190A2 (en) | 2006-05-03 |
| US8221771B2 (en) | 2012-07-17 |
| WO2005016275A3 (en) | 2005-04-14 |
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