CA2338504C - Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof - Google Patents
Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof Download PDFInfo
- Publication number
- CA2338504C CA2338504C CA2338504A CA2338504A CA2338504C CA 2338504 C CA2338504 C CA 2338504C CA 2338504 A CA2338504 A CA 2338504A CA 2338504 A CA2338504 A CA 2338504A CA 2338504 C CA2338504 C CA 2338504C
- Authority
- CA
- Canada
- Prior art keywords
- quinolin
- amine
- quinoline
- thiazolo
- oxide
- 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.)
- Expired - Fee Related
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- HLVNSLBJOPUZKV-UHFFFAOYSA-N [1,3]selenazolo[4,5-c]quinolin-4-amine Chemical class NC1=NC2=CC=CC=C2C2=C1N=C[se]2 HLVNSLBJOPUZKV-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 116
- 102000004127 Cytokines Human genes 0.000 claims abstract description 30
- 108090000695 Cytokines Proteins 0.000 claims abstract description 30
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
- 201000010099 disease Diseases 0.000 claims abstract description 12
- 230000003612 virological effect Effects 0.000 claims abstract description 12
- 230000001613 neoplastic effect Effects 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 97
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 229910052717 sulfur Chemical group 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- 239000011593 sulfur Chemical group 0.000 claims description 18
- NFYMGJSUKCDVJR-UHFFFAOYSA-N 2-propyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(SC(CCC)=N3)C3=C(N)N=C21 NFYMGJSUKCDVJR-UHFFFAOYSA-N 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- QAYNDFKXOSVCGF-UHFFFAOYSA-N [1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound NC1=NC2=CC=CC=C2C2=C1N=CS2 QAYNDFKXOSVCGF-UHFFFAOYSA-N 0.000 claims description 6
- 125000001475 halogen functional group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- ZDENTSZZTCBRAM-UHFFFAOYSA-N 2-ethyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(SC(CC)=N3)C3=C(N)N=C21 ZDENTSZZTCBRAM-UHFFFAOYSA-N 0.000 claims description 5
- LYXUZFHABUMMBT-UHFFFAOYSA-N 2-methyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(SC(C)=N3)C3=C(N)N=C21 LYXUZFHABUMMBT-UHFFFAOYSA-N 0.000 claims description 5
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 230000001939 inductive effect Effects 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- OYCXOBUNIUHNOK-UHFFFAOYSA-N (4-amino-[1,3]thiazolo[4,5-c]quinolin-2-yl)methanol Chemical compound NC1=NC2=CC=CC=C2C2=C1N=C(CO)S2 OYCXOBUNIUHNOK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- XQLMDBAFMZFEDT-UHFFFAOYSA-N 2-(2-methylpropyl)-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(SC(CC(C)C)=N3)C3=C(N)N=C21 XQLMDBAFMZFEDT-UHFFFAOYSA-N 0.000 claims description 4
- MSNAZIXEJBMXLW-UHFFFAOYSA-N 2-(2-phenylethyl)-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound N=1C=2C(N)=NC3=CC=CC=C3C=2SC=1CCC1=CC=CC=C1 MSNAZIXEJBMXLW-UHFFFAOYSA-N 0.000 claims description 4
- SFXDSTAXTMUOLE-UHFFFAOYSA-N 2-(ethoxymethyl)-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(SC(COCC)=N3)C3=C(N)N=C21 SFXDSTAXTMUOLE-UHFFFAOYSA-N 0.000 claims description 4
- CZHVSPXZCDPPAX-UHFFFAOYSA-N 2-butyl-7-methyl-[1,3]oxazolo[4,5-c]quinolin-4-amine Chemical compound C1=C(C)C=CC2=C(OC(CCCC)=N3)C3=C(N)N=C21 CZHVSPXZCDPPAX-UHFFFAOYSA-N 0.000 claims description 4
- XGNXMXDDPAAWFU-UHFFFAOYSA-N 2-butyl-[1,3]oxazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(OC(CCCC)=N3)C3=C(N)N=C21 XGNXMXDDPAAWFU-UHFFFAOYSA-N 0.000 claims description 4
- JJRZRZALFNCOGE-UHFFFAOYSA-N 2-butyl-[1,3]thiazolo[4,5-c][1,5]naphthyridin-4-amine Chemical compound C1=CC=NC2=C(SC(CCCC)=N3)C3=C(N)N=C21 JJRZRZALFNCOGE-UHFFFAOYSA-N 0.000 claims description 4
- XQXNQKAEROQGAD-UHFFFAOYSA-N 2-butyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(SC(CCCC)=N3)C3=C(N)N=C21 XQXNQKAEROQGAD-UHFFFAOYSA-N 0.000 claims description 4
- KRBOVPGWEOHVEY-UHFFFAOYSA-N 2-propyl-7-(trifluoromethyl)-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=C(C(F)(F)F)C=CC2=C(SC(CCC)=N3)C3=C(N)N=C21 KRBOVPGWEOHVEY-UHFFFAOYSA-N 0.000 claims description 4
- PYMPOEYXOAZHNH-UHFFFAOYSA-N 2-propyl-[1,3]thiazolo[4,5-c][1,5]naphthyridin-4-amine Chemical compound C1=CC=NC2=C(SC(CCC)=N3)C3=C(N)N=C21 PYMPOEYXOAZHNH-UHFFFAOYSA-N 0.000 claims description 4
- DEUBWEBVMICKDO-UHFFFAOYSA-N 7-chloro-2-propyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=C(Cl)C=CC2=C(SC(CCC)=N3)C3=C(N)N=C21 DEUBWEBVMICKDO-UHFFFAOYSA-N 0.000 claims description 4
- UMMVLGBNCBOQTO-UHFFFAOYSA-N 7-fluoro-2-propyl-[1,3]oxazolo[4,5-c]quinolin-4-amine Chemical compound C1=C(F)C=CC2=C(OC(CCC)=N3)C3=C(N)N=C21 UMMVLGBNCBOQTO-UHFFFAOYSA-N 0.000 claims description 4
- QMDADVZFXOAXPO-UHFFFAOYSA-N 7-methyl-2-propyl-[1,3]oxazolo[4,5-c]quinolin-4-amine Chemical compound C1=C(C)C=CC2=C(OC(CCC)=N3)C3=C(N)N=C21 QMDADVZFXOAXPO-UHFFFAOYSA-N 0.000 claims description 4
- KTHVEAHLDBJOSB-UHFFFAOYSA-N 8-bromo-2-propyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC(Br)=CC2=C(SC(CCC)=N3)C3=C(N)N=C21 KTHVEAHLDBJOSB-UHFFFAOYSA-N 0.000 claims description 4
- ODROCHXONQTZJZ-UHFFFAOYSA-N 2-(2-phenylethenyl)-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound N=1C=2C(N)=NC3=CC=CC=C3C=2SC=1C=CC1=CC=CC=C1 ODROCHXONQTZJZ-UHFFFAOYSA-N 0.000 claims description 3
- DMQSUTMWSINPAJ-UHFFFAOYSA-N 2-ethyl-[1,3]oxazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(OC(CC)=N3)C3=C(N)N=C21 DMQSUTMWSINPAJ-UHFFFAOYSA-N 0.000 claims description 3
- YADNUSVTPCOPJG-UHFFFAOYSA-N 2-methyl-[1,3]oxazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(OC(C)=N3)C3=C(N)N=C21 YADNUSVTPCOPJG-UHFFFAOYSA-N 0.000 claims description 3
- PBONJZGAWAMDRZ-UHFFFAOYSA-N 2-pentyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(SC(CCCCC)=N3)C3=C(N)N=C21 PBONJZGAWAMDRZ-UHFFFAOYSA-N 0.000 claims description 3
- VRIPIWGHFQQNBF-UHFFFAOYSA-N 2-propan-2-yl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(SC(C(C)C)=N3)C3=C(N)N=C21 VRIPIWGHFQQNBF-UHFFFAOYSA-N 0.000 claims description 3
- NMMLQAFPZXWZKG-UHFFFAOYSA-N 2-propyl-[1,3]oxazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(OC(CCC)=N3)C3=C(N)N=C21 NMMLQAFPZXWZKG-UHFFFAOYSA-N 0.000 claims description 3
- CRWUJLHZQANQJV-UHFFFAOYSA-N 2-propyl-[1,3]thiazolo[4,5-c]quinoline-4,8-diamine Chemical compound C1=CC(N)=CC2=C(SC(CCC)=N3)C3=C(N)N=C21 CRWUJLHZQANQJV-UHFFFAOYSA-N 0.000 claims description 3
- MKMMMNNPXSQTDW-UHFFFAOYSA-N 7-fluoro-2-propyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=C(F)C=CC2=C(SC(CCC)=N3)C3=C(N)N=C21 MKMMMNNPXSQTDW-UHFFFAOYSA-N 0.000 claims description 3
- FPUDMHYTEWTZKG-UHFFFAOYSA-N 7-methoxy-2-propyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=C(OC)C=CC2=C(SC(CCC)=N3)C3=C(N)N=C21 FPUDMHYTEWTZKG-UHFFFAOYSA-N 0.000 claims description 3
- YLQAXUQWWPUTKB-UHFFFAOYSA-N 7-methyl-2-propyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=C(C)C=CC2=C(SC(CCC)=N3)C3=C(N)N=C21 YLQAXUQWWPUTKB-UHFFFAOYSA-N 0.000 claims description 3
- KUVYHEWNVJZLEX-UHFFFAOYSA-N 8-methyl-2-propyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC(C)=CC2=C(SC(CCC)=N3)C3=C(N)N=C21 KUVYHEWNVJZLEX-UHFFFAOYSA-N 0.000 claims description 3
- VBBVAGFDWSHCDE-UHFFFAOYSA-N [1-(4-amino-[1,3]thiazolo[4,5-c]quinolin-2-yl)-2-methylpropan-2-yl] carbamate Chemical compound C1=CC=CC2=C(SC(CC(C)(C)OC(N)=O)=N3)C3=C(N)N=C21 VBBVAGFDWSHCDE-UHFFFAOYSA-N 0.000 claims description 3
- RZTIVRXSSDUJCX-UHFFFAOYSA-N 2-benzyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound N=1C=2C(N)=NC3=CC=CC=C3C=2SC=1CC1=CC=CC=C1 RZTIVRXSSDUJCX-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 241000124008 Mammalia Species 0.000 claims 3
- 230000000699 topical effect Effects 0.000 claims 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 abstract description 24
- 108010050904 Interferons Proteins 0.000 abstract description 24
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- 229940121354 immunomodulator Drugs 0.000 abstract description 4
- 230000017074 necrotic cell death Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 377
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Classifications
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- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D517/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains two hetero rings
- C07D517/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
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- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9434698P | 1998-07-28 | 1998-07-28 | |
| US09/361,544 | 1999-07-27 | ||
| US60/094,346 | 1999-07-27 | ||
| US09/361,544 US6110929A (en) | 1998-07-28 | 1999-07-27 | Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof |
| PCT/US1999/017027 WO2000006577A1 (en) | 1998-07-28 | 1999-07-28 | OXAZOLO, THIAZOLO AND SELENAZOLO [4,5-c]-QUINOLIN-4-AMINES AND ANALOGS THEREOF |
Publications (2)
| Publication Number | Publication Date |
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| CA2338504A1 CA2338504A1 (en) | 2000-02-10 |
| CA2338504C true CA2338504C (en) | 2011-03-08 |
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| CA2338504A Expired - Fee Related CA2338504C (en) | 1998-07-28 | 1999-07-28 | Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof |
Country Status (24)
| Country | Link |
|---|---|
| US (9) | US6110929A (enExample) |
| EP (1) | EP1100802B1 (enExample) |
| JP (1) | JP4662630B2 (enExample) |
| KR (1) | KR100696349B1 (enExample) |
| CN (1) | CN1147493C (enExample) |
| AT (2) | ATE320435T1 (enExample) |
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| BR (1) | BR9912448A (enExample) |
| CA (1) | CA2338504C (enExample) |
| CZ (1) | CZ291753B6 (enExample) |
| DE (2) | DE69930327T2 (enExample) |
| DK (1) | DK1100802T3 (enExample) |
| ES (2) | ES2260554T3 (enExample) |
| HU (1) | HUP0103137A3 (enExample) |
| IL (1) | IL140822A0 (enExample) |
| MX (1) | MXPA01000757A (enExample) |
| NO (1) | NO20010497L (enExample) |
| NZ (1) | NZ509420A (enExample) |
| PL (1) | PL347590A1 (enExample) |
| PT (2) | PT1100802E (enExample) |
| RU (1) | RU2244717C2 (enExample) |
| SK (1) | SK1402001A3 (enExample) |
| TR (1) | TR200100278T2 (enExample) |
| WO (1) | WO2000006577A1 (enExample) |
Families Citing this family (269)
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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 |
| US6110929A (en) * | 1998-07-28 | 2000-08-29 | 3M Innovative Properties Company | Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof |
| 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 |
| NZ512628A (en) | 1999-01-08 | 2004-03-26 | 3M Innovative Properties Co | Formulations and methods for treatment of mucosal associated conditions with an immune response modifier |
| 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 |
| US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide 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 |
| US6756382B2 (en) | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6451810B1 (en) | 1999-06-10 | 2002-09-17 | 3M Innovative Properties Company | Amide 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 |
| US6660747B2 (en) * | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6525064B1 (en) | 2000-12-08 | 2003-02-25 | 3M Innovative Properties Company | Sulfonamido substituted imidazopyridines |
| US6545017B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Urea substituted imidazopyridines |
| US6664260B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Heterocyclic ether substituted imidazoquinolines |
| US6545016B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Amide substituted imidazopyridines |
| US6664265B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6677347B2 (en) | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamido ether substituted imidazoquinolines |
| US6664264B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US6677348B2 (en) * | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Aryl ether substituted imidazoquinolines |
| UA75622C2 (en) | 2000-12-08 | 2006-05-15 | 3M Innovative Properties Co | Aryl ether substituted imidazoquinolines, pharmaceutical composition based thereon |
| US6660735B2 (en) * | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Urea substituted imidazoquinoline ethers |
| US20020110840A1 (en) * | 2000-12-08 | 2002-08-15 | 3M Innovative Properties Company | Screening method for identifying compounds that selectively induce interferon alpha |
| US6667312B2 (en) * | 2000-12-08 | 2003-12-23 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US20060142202A1 (en) * | 2000-12-08 | 2006-06-29 | 3M Innovative Properties Company | Compositions and methods for targeted delivery of immune response modifiers |
| US7226928B2 (en) * | 2001-06-15 | 2007-06-05 | 3M Innovative Properties Company | Methods for the treatment of periodontal disease |
| WO2003020889A2 (en) * | 2001-08-30 | 2003-03-13 | 3M Innovative Properties Company | Methods of maturing plasmacytoid dendritic cells using immune response modifier molecules |
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