DE69911622T2 - Oxazolo, thiazolo und selenazolo [4,5-c]-chinolin-4-amine und derivate davon - Google Patents
Oxazolo, thiazolo und selenazolo [4,5-c]-chinolin-4-amine und derivate davon Download PDFInfo
- Publication number
- DE69911622T2 DE69911622T2 DE69911622T DE69911622T DE69911622T2 DE 69911622 T2 DE69911622 T2 DE 69911622T2 DE 69911622 T DE69911622 T DE 69911622T DE 69911622 T DE69911622 T DE 69911622T DE 69911622 T2 DE69911622 T2 DE 69911622T2
- Authority
- DE
- Germany
- Prior art keywords
- quinolin
- amine
- radical
- quinoline
- alkyl
- 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 - Lifetime
Links
- HLVNSLBJOPUZKV-UHFFFAOYSA-N [1,3]selenazolo[4,5-c]quinolin-4-amine Chemical compound NC1=NC2=CC=CC=C2C2=C1N=C[se]2 HLVNSLBJOPUZKV-UHFFFAOYSA-N 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 110
- 102000004127 Cytokines Human genes 0.000 claims abstract description 29
- 108090000695 Cytokines Proteins 0.000 claims abstract description 29
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 claims abstract description 16
- 201000010099 disease Diseases 0.000 claims abstract description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
- 230000003612 virological effect Effects 0.000 claims abstract description 11
- 230000001613 neoplastic effect Effects 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 257
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 claims description 144
- 239000000203 mixture Substances 0.000 claims description 90
- -1 alkyl radical Chemical class 0.000 claims description 64
- CMOIEFFAOUQJPS-UHFFFAOYSA-N 2-propyl-1,3-thiazole Chemical compound CCCC1=NC=CS1 CMOIEFFAOUQJPS-UHFFFAOYSA-N 0.000 claims description 34
- 239000003814 drug Substances 0.000 claims description 23
- 150000003254 radicals Chemical class 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 14
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims description 14
- 102000006992 Interferon-alpha Human genes 0.000 claims description 13
- 108010047761 Interferon-alpha Proteins 0.000 claims description 13
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000004434 sulfur atom Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- SUCDHPJUXCCMDN-UHFFFAOYSA-N 2-ethyl-1,3-oxazole Chemical compound CCC1=NC=CO1 SUCDHPJUXCCMDN-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- QHHHLHCCVDMOJI-UHFFFAOYSA-N 1,3-thiazol-4-amine Chemical compound NC1=CSC=N1 QHHHLHCCVDMOJI-UHFFFAOYSA-N 0.000 claims description 8
- KEWBUOMVBFMGNS-UHFFFAOYSA-N 2-(2-phenylethyl)-1,3-thiazole Chemical compound N=1C=CSC=1CCC1=CC=CC=C1 KEWBUOMVBFMGNS-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 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 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 230000001939 inductive effect Effects 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 241000700605 Viruses Species 0.000 claims description 5
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 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 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052711 selenium Inorganic materials 0.000 claims description 4
- 239000011669 selenium Substances 0.000 claims description 4
- 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 3
- 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 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
- 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 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 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 2
- 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 2
- 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 2
- 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 2
- FACMROYHRCEAMW-UHFFFAOYSA-N 2-(methoxymethyl)-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(SC(COC)=N3)C3=C(N)N=C21 FACMROYHRCEAMW-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 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
- 241000124008 Mammalia Species 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 43
- 102000014150 Interferons Human genes 0.000 abstract description 22
- 108010050904 Interferons Proteins 0.000 abstract description 22
- 229940079322 interferon Drugs 0.000 abstract description 19
- 206010028980 Neoplasm Diseases 0.000 abstract description 5
- 230000028993 immune response Effects 0.000 abstract description 5
- 239000000543 intermediate Substances 0.000 abstract description 5
- 239000002955 immunomodulating agent Substances 0.000 abstract description 4
- 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 387
- 239000011541 reaction mixture Substances 0.000 description 171
- 239000007787 solid Substances 0.000 description 167
- 229910052739 hydrogen Inorganic materials 0.000 description 157
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 154
- 229910052757 nitrogen Inorganic materials 0.000 description 152
- 229910052799 carbon Inorganic materials 0.000 description 150
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 123
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 113
- 239000000243 solution Substances 0.000 description 99
- 238000004458 analytical method Methods 0.000 description 88
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 87
- 238000002844 melting Methods 0.000 description 83
- 230000008018 melting Effects 0.000 description 83
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 80
- 239000002244 precipitate Substances 0.000 description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 62
- 238000001914 filtration Methods 0.000 description 58
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
- 238000006243 chemical reaction Methods 0.000 description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 49
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
- 239000000463 material Substances 0.000 description 42
- 239000000725 suspension Substances 0.000 description 42
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 41
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 40
- 239000000706 filtrate Substances 0.000 description 35
- 238000010992 reflux Methods 0.000 description 35
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 33
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 33
- 235000019341 magnesium sulphate Nutrition 0.000 description 33
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 32
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 28
- GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 description 27
- 239000003921 oil Substances 0.000 description 25
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- 238000003756 stirring Methods 0.000 description 25
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
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- 150000001204 N-oxides Chemical class 0.000 description 21
- UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical compound OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 description 19
- VZWOXDYRBDIHMA-UHFFFAOYSA-N 2-methyl-1,3-thiazole Chemical compound CC1=NC=CS1 VZWOXDYRBDIHMA-UHFFFAOYSA-N 0.000 description 19
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- 239000003795 chemical substances by application Substances 0.000 description 18
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
- 235000017557 sodium bicarbonate Nutrition 0.000 description 18
- CGZDWVZMOMDGBN-UHFFFAOYSA-N 2-Ethylthiazole Chemical compound CCC1=NC=CS1 CGZDWVZMOMDGBN-UHFFFAOYSA-N 0.000 description 17
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 17
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 17
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 17
- 239000000908 ammonium hydroxide Substances 0.000 description 17
- 239000012043 crude product Substances 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000000284 extract Substances 0.000 description 16
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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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- 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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- C07—ORGANIC CHEMISTRY
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- 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
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Orthopedic Medicine & Surgery (AREA)
- Dermatology (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US361544 | 1982-03-24 | ||
| US9434698P | 1998-07-28 | 1998-07-28 | |
| US94346P | 1998-07-28 | ||
| 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 |
|---|---|
| DE69911622D1 DE69911622D1 (de) | 2003-10-30 |
| DE69911622T2 true DE69911622T2 (de) | 2004-06-17 |
Family
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| DE69911622T Expired - Lifetime DE69911622T2 (de) | 1998-07-28 | 1999-07-28 | Oxazolo, thiazolo und selenazolo [4,5-c]-chinolin-4-amine und derivate davon |
| DE69930327T Expired - Lifetime DE69930327T2 (de) | 1998-07-28 | 1999-07-28 | Oxazolo-, Thiazolo- und Selenazolo-Ä4,5-cÜnaphthyridin-4-amine und Analoge davon |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69930327T Expired - Lifetime DE69930327T2 (de) | 1998-07-28 | 1999-07-28 | Oxazolo-, Thiazolo- und Selenazolo-Ä4,5-cÜnaphthyridin-4-amine und Analoge davon |
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| TR (1) | TR200100278T2 (enExample) |
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