SK285872B6 - Imidazonaftyridíny a ich použitie na indukovanie biosyntézy cytokínu - Google Patents
Imidazonaftyridíny a ich použitie na indukovanie biosyntézy cytokínu Download PDFInfo
- Publication number
- SK285872B6 SK285872B6 SK835-2000A SK8352000A SK285872B6 SK 285872 B6 SK285872 B6 SK 285872B6 SK 8352000 A SK8352000 A SK 8352000A SK 285872 B6 SK285872 B6 SK 285872B6
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- aryl
- heteroaryl
- heterocyclyl
- phenyl
- Prior art date
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- 102000004127 Cytokines Human genes 0.000 title claims abstract description 28
- 108090000695 Cytokines Proteins 0.000 title claims abstract description 28
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 18
- 230000001939 inductive effect Effects 0.000 title claims description 11
- VFTLXHXYGQSOEN-UHFFFAOYSA-N 1h-imidazo[4,5-b][1,8]naphthyridine Chemical class C1=CN=C2NC3=NC=NC3=CC2=C1 VFTLXHXYGQSOEN-UHFFFAOYSA-N 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 289
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 234
- 229910052799 carbon Inorganic materials 0.000 claims description 171
- 125000000217 alkyl group Chemical group 0.000 claims description 145
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 128
- -1 2-hydroxy-2-methylpropyl Chemical group 0.000 claims description 89
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 64
- 239000004305 biphenyl Substances 0.000 claims description 64
- 235000010290 biphenyl Nutrition 0.000 claims description 64
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 64
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 64
- 125000001624 naphthyl group Chemical group 0.000 claims description 64
- 125000002541 furyl group Chemical group 0.000 claims description 60
- 125000004076 pyridyl group Chemical group 0.000 claims description 60
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 60
- 125000001544 thienyl group Chemical group 0.000 claims description 60
- 125000003118 aryl group Chemical group 0.000 claims description 59
- 239000001257 hydrogen Substances 0.000 claims description 59
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 57
- 125000002757 morpholinyl group Chemical group 0.000 claims description 53
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 53
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 53
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 52
- 125000001072 heteroaryl group Chemical group 0.000 claims description 49
- 125000000623 heterocyclic group Chemical group 0.000 claims description 46
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 45
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 241001465754 Metazoa Species 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 208000036142 Viral infection Diseases 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 230000009385 viral infection Effects 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 58
- 125000005493 quinolyl group Chemical group 0.000 claims 44
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000005024 alkenyl aryl group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 229910052681 coesite Inorganic materials 0.000 claims 1
- 229910052906 cristobalite Inorganic materials 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 235000012239 silicon dioxide Nutrition 0.000 claims 1
- 229910052682 stishovite Inorganic materials 0.000 claims 1
- 229910052905 tridymite Inorganic materials 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 abstract description 23
- 102000014150 Interferons Human genes 0.000 abstract description 23
- 229940079322 interferon Drugs 0.000 abstract description 21
- 238000000034 method Methods 0.000 abstract description 19
- 239000000543 intermediate Substances 0.000 abstract description 18
- 108060008682 Tumor Necrosis Factor Proteins 0.000 abstract description 9
- 102000003390 tumor necrosis factor Human genes 0.000 abstract description 6
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- 230000000840 anti-viral effect Effects 0.000 abstract description 2
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 453
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- LFYHTJJDBDTWEN-UHFFFAOYSA-N tert-butyl n-[1-[2-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)ethylamino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCNC(=O)C(CC(C)C)NC(=O)OC(C)(C)C)C3=C(N)N=C21 LFYHTJJDBDTWEN-UHFFFAOYSA-N 0.000 description 1
- UVRYAPOGGJJJJX-UHFFFAOYSA-N tert-butyl n-[4-(2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]carbamate Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCCCNC(=O)OC(C)(C)C)C3=CN=C21 UVRYAPOGGJJJJX-UHFFFAOYSA-N 0.000 description 1
- DTDCSSCKPBHWCA-UHFFFAOYSA-N tert-butyl n-[4-[(3-nitro-1,5-naphthyridin-4-yl)amino]butyl]carbamate Chemical compound C1=CN=C2C(NCCCCNC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=NC2=C1 DTDCSSCKPBHWCA-UHFFFAOYSA-N 0.000 description 1
- YODGHDMNQOTUPL-UHFFFAOYSA-N tetrazolo[1,5-a][1,7]naphthyridin-5-amine Chemical compound N1=CC=C2C(N)=CC3=NN=NN3C2=C1 YODGHDMNQOTUPL-UHFFFAOYSA-N 0.000 description 1
- PHXUIGRGPODXIF-UHFFFAOYSA-N tetrazolo[1,5-a][1,7]naphthyridine-4,5-diamine Chemical compound NC1=C(N)C2=CC=NC=C2N2C1=NN=N2 PHXUIGRGPODXIF-UHFFFAOYSA-N 0.000 description 1
- WVOUCGZOQPSJCR-UHFFFAOYSA-N tetrazolo[1,5-a][1,8]naphthyridine-4,5-diamine Chemical compound NC1=C(N)C2=CC=CN=C2N2C1=NN=N2 WVOUCGZOQPSJCR-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| US6927697P | 1997-12-11 | 1997-12-11 | |
| PCT/US1998/026473 WO1999029693A1 (en) | 1997-12-11 | 1998-12-11 | Imidazonaphthyridines and their use in inducing cytokine biosynthesis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK8352000A3 SK8352000A3 (en) | 2001-03-12 |
| SK285872B6 true SK285872B6 (sk) | 2007-10-04 |
Family
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| Application Number | Title | Priority Date | Filing Date |
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| SK835-2000A SK285872B6 (sk) | 1997-12-11 | 1998-12-11 | Imidazonaftyridíny a ich použitie na indukovanie biosyntézy cytokínu |
| SK5035-2007A SK286304B6 (en) | 1997-12-11 | 1998-12-11 | Imidazonaphthyridines and their use in inducing cytokine biosynthesis |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK5035-2007A SK286304B6 (en) | 1997-12-11 | 1998-12-11 | Imidazonaphthyridines and their use in inducing cytokine biosynthesis |
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| US (14) | US6194425B1 (cs) |
| EP (1) | EP1040112B1 (cs) |
| JP (4) | JP4283438B2 (cs) |
| KR (3) | KR100642702B1 (cs) |
| CN (1) | CN1154647C (cs) |
| AT (3) | ATE338757T1 (cs) |
| AU (1) | AU753864B2 (cs) |
| BR (1) | BR9814275A (cs) |
| CA (1) | CA2311456C (cs) |
| CZ (1) | CZ307184B6 (cs) |
| DE (3) | DE69835309T2 (cs) |
| DK (1) | DK1512686T3 (cs) |
| EE (1) | EE04314B1 (cs) |
| ES (3) | ES2270249T3 (cs) |
| HR (1) | HRP20000363B1 (cs) |
| HU (1) | HUP0101155A3 (cs) |
| IL (4) | IL136556A0 (cs) |
| NO (3) | NO316687B1 (cs) |
| NZ (1) | NZ504776A (cs) |
| PL (1) | PL193915B1 (cs) |
| PT (3) | PT1512686E (cs) |
| RU (3) | RU2221798C2 (cs) |
| SI (1) | SI1512686T1 (cs) |
| SK (2) | SK285872B6 (cs) |
| TR (1) | TR200001705T2 (cs) |
| UA (1) | UA67760C2 (cs) |
| WO (1) | WO1999029693A1 (cs) |
Families Citing this family (225)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| ATE304852T1 (de) | 1999-01-08 | 2005-10-15 | 3M Innovative Properties Co | Zubereitungen, umfassend imiquimod oder andere immunantwort modifizierenden verbindungen, zur behandlung von zervikaler dysplasie |
| US6486168B1 (en) | 1999-01-08 | 2002-11-26 | 3M Innovative Properties Company | Formulations and methods for treatment of mucosal associated conditions with an immune response modifier |
| US6558951B1 (en) * | 1999-02-11 | 2003-05-06 | 3M Innovative Properties Company | Maturation of dendritic cells with immune response modifying compounds |
| US6573273B1 (en) * | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6756382B2 (en) | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| EP1438958A1 (en) * | 1999-06-10 | 2004-07-21 | 3M Innovative Properties Company | Carbamate substituted imidazoquinolines |
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| US6451810B1 (en) * | 1999-06-10 | 2002-09-17 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| EP1642580B8 (en) * | 1999-06-10 | 2009-11-18 | Coley Pharmaceutical Group, Inc. | Sulfonamide 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 |
| US6894060B2 (en) | 2000-03-30 | 2005-05-17 | 3M Innovative Properties Company | Method for the treatment of dermal lesions caused by envenomation |
| US20040209877A1 (en) * | 2000-04-13 | 2004-10-21 | Shelby Nancy J. | Methods for augmenting immune defenses contemplating the administration of phenolic and indoleamine-like compounds for use in animals ans humans |
| US6660747B2 (en) * | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
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| US6664265B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| AU2006216669A1 (en) * | 2000-12-08 | 2006-08-31 | 3M Innovative Properties Company | Compositions and methods for targeted delivery of immune response modifiers |
| US6545017B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Urea substituted imidazopyridines |
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- 1998-12-11 ES ES04022441T patent/ES2273138T3/es not_active Expired - Lifetime
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| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20091211 |