JP5209312B2 - １−アルコキシ１ｈ−イミダゾ環系および方法 - Google Patents
１−アルコキシ１ｈ−イミダゾ環系および方法 Download PDFInfo
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- JP5209312B2 JP5209312B2 JP2007530396A JP2007530396A JP5209312B2 JP 5209312 B2 JP5209312 B2 JP 5209312B2 JP 2007530396 A JP2007530396 A JP 2007530396A JP 2007530396 A JP2007530396 A JP 2007530396A JP 5209312 B2 JP5209312 B2 JP 5209312B2
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- alkyl
- aryl
- alkenyl
- heteroaryl
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- 238000000034 method Methods 0.000 title abstract description 70
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- 125000000217 alkyl group Chemical group 0.000 claims description 255
- -1 arylalkylenyl Chemical group 0.000 claims description 121
- 229910052739 hydrogen Inorganic materials 0.000 claims description 105
- 239000001257 hydrogen Substances 0.000 claims description 105
- 125000003118 aryl group Chemical group 0.000 claims description 97
- 125000000623 heterocyclic group Chemical group 0.000 claims description 97
- 125000003342 alkenyl group Chemical group 0.000 claims description 92
- 125000001072 heteroaryl group Chemical group 0.000 claims description 86
- 150000002431 hydrogen Chemical class 0.000 claims description 79
- 150000003839 salts Chemical class 0.000 claims description 74
- 125000001424 substituent group Chemical group 0.000 claims description 64
- 125000000304 alkynyl group Chemical group 0.000 claims description 58
- 125000002947 alkylene group Chemical group 0.000 claims description 56
- 125000003545 alkoxy group Chemical group 0.000 claims description 49
- 229910052736 halogen Inorganic materials 0.000 claims description 46
- 150000002367 halogens Chemical group 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
- 125000001188 haloalkyl group Chemical group 0.000 claims description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000000732 arylene group Chemical group 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 125000003282 alkyl amino group Chemical group 0.000 claims description 19
- 125000004414 alkyl thio group Chemical group 0.000 claims description 19
- 125000005466 alkylenyl group Chemical group 0.000 claims description 19
- 125000005553 heteroaryloxy group Chemical group 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
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- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 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 11
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 6
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 6
- 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 6
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- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([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 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- 230000011987 methylation Effects 0.000 claims 1
- 238000007069 methylation reaction Methods 0.000 claims 1
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- 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 390
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 245
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 66
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- 239000000463 material Substances 0.000 description 44
- 229910000027 potassium carbonate Inorganic materials 0.000 description 41
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 38
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 37
- 235000017557 sodium bicarbonate Nutrition 0.000 description 37
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 36
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
- 238000010992 reflux Methods 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 238000001914 filtration Methods 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
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- 238000004440 column chromatography Methods 0.000 description 30
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- 238000004458 analytical method Methods 0.000 description 28
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 26
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 24
- 108010047761 Interferon-alpha Proteins 0.000 description 23
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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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- OHDXDNUPVVYWOV-UHFFFAOYSA-N n-methyl-1-(2-naphthalen-1-ylsulfanylphenyl)methanamine Chemical compound CNCC1=CC=CC=C1SC1=CC=CC2=CC=CC=C12 OHDXDNUPVVYWOV-UHFFFAOYSA-N 0.000 description 19
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 18
- ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical group C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 description 17
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 17
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
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Classifications
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Landscapes
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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 |
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| JP2008511677A JP2008511677A (ja) | 2008-04-17 |
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| WO2003103584A2 (en) | 2002-06-07 | 2003-12-18 | 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 |
| RU2006105101A (ru) | 2003-08-27 | 2007-10-10 | 3М Инновейтив Пропертиз Компани (US) | Арилокси и арилалкиленокси замещенные имидазохинолины |
| WO2005023190A2 (en) | 2003-09-05 | 2005-03-17 | 3M Innovative Properties Company | Treatment for cd5+ b cell lymphoma |
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Also Published As
| Publication number | Publication date |
|---|---|
| EP1789042A2 (en) | 2007-05-30 |
| AU2005282726B2 (en) | 2011-06-02 |
| US20090005376A1 (en) | 2009-01-01 |
| WO2006028962A3 (en) | 2006-10-26 |
| WO2006028962A2 (en) | 2006-03-16 |
| EP1789042B1 (en) | 2012-05-02 |
| ATE555786T1 (de) | 2012-05-15 |
| CA2578741A1 (en) | 2006-03-16 |
| JP2008511677A (ja) | 2008-04-17 |
| US7579359B2 (en) | 2009-08-25 |
| EP1789042A4 (en) | 2009-07-22 |
| PL1789042T3 (pl) | 2012-09-28 |
| CA2578741C (en) | 2014-01-14 |
| ES2384390T3 (es) | 2012-07-04 |
| AU2005282726A1 (en) | 2006-03-16 |
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