AU2005282726B2 - 1-alkoxy 1H-imidazo ring systems and methods - Google Patents
1-alkoxy 1H-imidazo ring systems and methods Download PDFInfo
- Publication number
- AU2005282726B2 AU2005282726B2 AU2005282726A AU2005282726A AU2005282726B2 AU 2005282726 B2 AU2005282726 B2 AU 2005282726B2 AU 2005282726 A AU2005282726 A AU 2005282726A AU 2005282726 A AU2005282726 A AU 2005282726A AU 2005282726 B2 AU2005282726 B2 AU 2005282726B2
- Authority
- AU
- Australia
- Prior art keywords
- group
- alkyl
- aryl
- alkenyl
- hydrogen
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 72
- 150000001875 compounds Chemical class 0.000 claims abstract description 216
- 102000004127 Cytokines Human genes 0.000 claims abstract description 43
- 108090000695 Cytokines Proteins 0.000 claims abstract description 43
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 32
- 201000010099 disease Diseases 0.000 claims abstract description 30
- 241001465754 Metazoa Species 0.000 claims abstract description 28
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 23
- 230000003612 virological effect Effects 0.000 claims abstract description 12
- 230000001613 neoplastic effect Effects 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 230000001939 inductive effect Effects 0.000 claims abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 390
- 125000000217 alkyl group Chemical group 0.000 claims description 267
- -1 -N3 Chemical group 0.000 claims description 169
- 229910052739 hydrogen Inorganic materials 0.000 claims description 121
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- 125000003342 alkenyl group Chemical group 0.000 claims description 99
- 125000000623 heterocyclic group Chemical group 0.000 claims description 99
- 125000003118 aryl group Chemical group 0.000 claims description 86
- 125000001072 heteroaryl group Chemical group 0.000 claims description 80
- 150000003839 salts Chemical class 0.000 claims description 78
- 125000001424 substituent group Chemical group 0.000 claims description 61
- 125000000304 alkynyl group Chemical group 0.000 claims description 57
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 57
- 125000002947 alkylene group Chemical group 0.000 claims description 55
- 229910052736 halogen Inorganic materials 0.000 claims description 50
- 150000002367 halogens Chemical class 0.000 claims description 49
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 125000001188 haloalkyl group Chemical group 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 24
- 125000003282 alkyl amino group Chemical group 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000000732 arylene group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims description 19
- 125000005466 alkylenyl group Chemical group 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 19
- 125000004104 aryloxy group Chemical group 0.000 claims description 18
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 18
- 125000005549 heteroarylene group Chemical group 0.000 claims description 18
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 18
- 125000004450 alkenylene group Chemical group 0.000 claims description 17
- 125000004043 oxo group Chemical group O=* 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 125000004419 alkynylene group Chemical group 0.000 claims description 14
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 12
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 6
- 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 12
- 239000002955 immunomodulating agent Substances 0.000 abstract description 4
- 229940121354 immunomodulator Drugs 0.000 abstract description 4
- 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 abstract description 3
- RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 abstract 1
- 150000005232 imidazopyridines Chemical class 0.000 abstract 1
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 66
- 150000002431 hydrogen Chemical class 0.000 description 64
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 63
- 239000000203 mixture Substances 0.000 description 62
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 59
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- 238000010992 reflux Methods 0.000 description 34
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- FWICNGJRPKVYQV-UHFFFAOYSA-N 4-chloroquinolin-3-amine Chemical compound C1=CC=CC2=C(Cl)C(N)=CN=C21 FWICNGJRPKVYQV-UHFFFAOYSA-N 0.000 description 21
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Classifications
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Landscapes
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- Nitrogen Condensed Heterocyclic Rings (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US60662904P | 2004-09-02 | 2004-09-02 | |
| US60/606,629 | 2004-09-02 | ||
| PCT/US2005/031310 WO2006028962A2 (en) | 2004-09-02 | 2005-09-01 | 1-alkoxy 1h-imidazo ring systems and methods |
Publications (2)
| Publication Number | Publication Date |
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| AU2005282726A1 AU2005282726A1 (en) | 2006-03-16 |
| AU2005282726B2 true AU2005282726B2 (en) | 2011-06-02 |
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| AU2005282726A Ceased AU2005282726B2 (en) | 2004-09-02 | 2005-09-01 | 1-alkoxy 1H-imidazo ring systems and methods |
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| Country | Link |
|---|---|
| US (1) | US7579359B2 (OSRAM) |
| EP (1) | EP1789042B1 (OSRAM) |
| JP (1) | JP5209312B2 (OSRAM) |
| AT (1) | ATE555786T1 (OSRAM) |
| AU (1) | AU2005282726B2 (OSRAM) |
| CA (1) | CA2578741C (OSRAM) |
| ES (1) | ES2384390T3 (OSRAM) |
| PL (1) | PL1789042T3 (OSRAM) |
| WO (1) | WO2006028962A2 (OSRAM) |
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| AU2003237386A1 (en) | 2002-06-07 | 2003-12-22 | 3M Innovative Properties Company | Ether substituted imidazopyridines |
| US20040265351A1 (en) | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| PH12006500401A1 (en) | 2003-08-27 | 2005-03-10 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| EP1660026A4 (en) | 2003-09-05 | 2008-07-16 | 3M Innovative Properties Co | TREATMENT FOR CD5 + B CELL LYMPHOMA |
| CA2540598C (en) | 2003-10-03 | 2013-09-24 | 3M Innovative Properties Company | Pyrazolopyridines and analogs thereof |
| EP1673087B1 (en) | 2003-10-03 | 2015-05-13 | 3M Innovative Properties Company | Alkoxy substituted imidazoquinolines |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| CA2547020C (en) | 2003-11-25 | 2014-03-25 | 3M Innovative Properties Company | 1h-imidazo[4,5-c]pyridine-4-amine derivatives as immune response modifier |
| US8541438B2 (en) | 2004-06-18 | 2013-09-24 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| WO2006065280A2 (en) | 2004-06-18 | 2006-06-22 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and methods |
| ATE555786T1 (de) | 2004-09-02 | 2012-05-15 | 3M Innovative Properties Co | 1-alkoxy 1h-imidazo-ringsysteme und verfahren |
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2005
- 2005-09-01 AT AT05794068T patent/ATE555786T1/de active
- 2005-09-01 WO PCT/US2005/031310 patent/WO2006028962A2/en not_active Ceased
- 2005-09-01 US US11/574,463 patent/US7579359B2/en active Active
- 2005-09-01 AU AU2005282726A patent/AU2005282726B2/en not_active Ceased
- 2005-09-01 CA CA2578741A patent/CA2578741C/en not_active Expired - Lifetime
- 2005-09-01 ES ES05794068T patent/ES2384390T3/es not_active Expired - Lifetime
- 2005-09-01 JP JP2007530396A patent/JP5209312B2/ja not_active Expired - Fee Related
- 2005-09-01 EP EP05794068A patent/EP1789042B1/en not_active Expired - Lifetime
- 2005-09-01 PL PL05794068T patent/PL1789042T3/pl unknown
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| US20020173654A1 (en) * | 1997-12-11 | 2002-11-21 | 3M Innovative Properties Company | Imidazonaphthyridines |
| US20040023932A1 (en) * | 1997-12-11 | 2004-02-05 | 3M Innovative Properties Company | Imidazonaphthyridines |
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Also Published As
| Publication number | Publication date |
|---|---|
| ATE555786T1 (de) | 2012-05-15 |
| CA2578741A1 (en) | 2006-03-16 |
| US7579359B2 (en) | 2009-08-25 |
| US20090005376A1 (en) | 2009-01-01 |
| PL1789042T3 (pl) | 2012-09-28 |
| EP1789042A4 (en) | 2009-07-22 |
| CA2578741C (en) | 2014-01-14 |
| ES2384390T3 (es) | 2012-07-04 |
| WO2006028962A2 (en) | 2006-03-16 |
| AU2005282726A1 (en) | 2006-03-16 |
| EP1789042B1 (en) | 2012-05-02 |
| JP2008511677A (ja) | 2008-04-17 |
| EP1789042A2 (en) | 2007-05-30 |
| JP5209312B2 (ja) | 2013-06-12 |
| WO2006028962A3 (en) | 2006-10-26 |
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