JP2009528989A - Ｔｌｒ７変調剤としての３−デアザプリン誘導体 - Google Patents
Ｔｌｒ７変調剤としての３−デアザプリン誘導体 Download PDFInfo
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- JP2009528989A JP2009528989A JP2008554875A JP2008554875A JP2009528989A JP 2009528989 A JP2009528989 A JP 2009528989A JP 2008554875 A JP2008554875 A JP 2008554875A JP 2008554875 A JP2008554875 A JP 2008554875A JP 2009528989 A JP2009528989 A JP 2009528989A
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- Prior art keywords
- alkyl
- alkylene
- compound
- pyridin
- formula
- 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.)
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- 101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 title description 3
- 102100039390 Toll-like receptor 7 Human genes 0.000 title description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 202
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- -1 tetrahydrofuranoxy Chemical group 0.000 claims description 110
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 91
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 82
- 150000003839 salts Chemical class 0.000 claims description 68
- 125000005843 halogen group Chemical group 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 54
- 125000000623 heterocyclic group Chemical group 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 125000002947 alkylene group Chemical group 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 48
- 229910052757 nitrogen Inorganic materials 0.000 claims description 45
- 239000012453 solvate Substances 0.000 claims description 44
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 41
- 229910052760 oxygen Inorganic materials 0.000 claims description 39
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 38
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 38
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 36
- 229910052717 sulfur Inorganic materials 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 31
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 239000001301 oxygen Substances 0.000 claims description 24
- 238000011282 treatment Methods 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 21
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- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 19
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- 125000005842 heteroatom Chemical group 0.000 claims description 15
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- 125000006239 protecting group Chemical group 0.000 claims description 13
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- 230000008569 process Effects 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 239000003223 protective agent Substances 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- 150000003852 triazoles Chemical class 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- YWWWOUJIAZDIRH-UHFFFAOYSA-N 4-amino-1-benzyl-6-(1,3-oxazol-2-yl)-3h-imidazo[4,5-c]pyridin-2-one Chemical compound O=C1NC=2C(N)=NC(C=3OC=CN=3)=CC=2N1CC1=CC=CC=C1 YWWWOUJIAZDIRH-UHFFFAOYSA-N 0.000 claims description 3
- GOOQRUJALRQYES-UHFFFAOYSA-N 4-amino-1-benzyl-6-cyclopropyl-3h-imidazo[4,5-c]pyridin-2-one Chemical compound O=C1NC=2C(N)=NC(C3CC3)=CC=2N1CC1=CC=CC=C1 GOOQRUJALRQYES-UHFFFAOYSA-N 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 102000004169 proteins and genes Human genes 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- ZJSVBILSBHWRTN-UHFFFAOYSA-N 1,3-dihydroimidazo[4,5-c]pyridin-2-one Chemical compound C1=NC=C2NC(=O)NC2=C1 ZJSVBILSBHWRTN-UHFFFAOYSA-N 0.000 claims description 2
- 241000711573 Coronaviridae Species 0.000 claims description 2
- 241000711950 Filoviridae Species 0.000 claims description 2
- 241000710831 Flavivirus Species 0.000 claims description 2
- 102000005741 Metalloproteases Human genes 0.000 claims description 2
- 108010006035 Metalloproteases Proteins 0.000 claims description 2
- 108060004795 Methyltransferase Proteins 0.000 claims description 2
- 101800001019 Non-structural protein 4B Proteins 0.000 claims description 2
- 101800001014 Non-structural protein 5A Proteins 0.000 claims description 2
- 241001631646 Papillomaviridae Species 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
- 102000012479 Serine Proteases Human genes 0.000 claims description 2
- 108010022999 Serine Proteases Proteins 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 241000701161 unidentified adenovirus Species 0.000 claims description 2
- 241001529453 unidentified herpesvirus Species 0.000 claims description 2
- 241001430294 unidentified retrovirus Species 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 5
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- 101800000440 Non-structural protein NS3A Proteins 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 233
- 239000000543 intermediate Substances 0.000 abstract description 29
- 102000002689 Toll-like receptor Human genes 0.000 abstract description 9
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- 206010028980 Neoplasm Diseases 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 5
- 208000015181 infectious disease Diseases 0.000 abstract description 4
- 230000008484 agonism Effects 0.000 abstract description 3
- 230000001225 therapeutic effect Effects 0.000 abstract description 3
- 201000011510 cancer Diseases 0.000 abstract description 2
- 208000006454 hepatitis Diseases 0.000 abstract 1
- 231100000283 hepatitis Toxicity 0.000 abstract 1
- 230000028993 immune response Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 349
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 219
- 239000007787 solid Substances 0.000 description 188
- 239000000243 solution Substances 0.000 description 163
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 154
- 235000019439 ethyl acetate Nutrition 0.000 description 146
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 137
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 127
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 122
- 238000005481 NMR spectroscopy Methods 0.000 description 105
- 239000011541 reaction mixture Substances 0.000 description 90
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 81
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 74
- 239000012044 organic layer Substances 0.000 description 73
- 239000002904 solvent Substances 0.000 description 69
- 238000005160 1H NMR spectroscopy Methods 0.000 description 66
- 238000006243 chemical reaction Methods 0.000 description 66
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 64
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 64
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
- 239000003921 oil Substances 0.000 description 56
- 235000019198 oils Nutrition 0.000 description 56
- 239000000047 product Substances 0.000 description 52
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 50
- 238000004440 column chromatography Methods 0.000 description 49
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 47
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 44
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 41
- 239000010410 layer Substances 0.000 description 40
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 40
- 239000000377 silicon dioxide Substances 0.000 description 39
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- 239000000741 silica gel Substances 0.000 description 35
- 229910002027 silica gel Inorganic materials 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 239000012267 brine Substances 0.000 description 33
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 32
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 31
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 31
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 29
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- 239000002585 base Substances 0.000 description 24
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 24
- 229920006395 saturated elastomer Polymers 0.000 description 24
- 239000000706 filtrate Substances 0.000 description 23
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
- 235000019341 magnesium sulphate Nutrition 0.000 description 23
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 19
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 17
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- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 12
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- 239000001257 hydrogen Substances 0.000 description 12
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- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 10
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- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 9
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- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 8
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- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- KOEUOFPEZFUWRF-LJQANCHMSA-N 4-amino-3-(4-phenoxyphenyl)-1-[(3R)-1-prop-2-enoylpiperidin-3-yl]imidazo[4,5-c]pyridin-2-one Chemical compound C(C=C)(=O)N1C[C@@H](CCC1)N1C(N(C=2C(=NC=CC=21)N)C1=CC=C(C=C1)OC1=CC=CC=C1)=O KOEUOFPEZFUWRF-LJQANCHMSA-N 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
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- NZZFYRREKKOMAT-OUBTZVSYSA-N diiodomethane Chemical group I[13CH2]I NZZFYRREKKOMAT-OUBTZVSYSA-N 0.000 description 1
- VDALIBWXVQVFGZ-UHFFFAOYSA-N dimethyl-[[4-[[3-(4-methylphenyl)-8,9-dihydro-7h-benzo[7]annulene-6-carbonyl]amino]phenyl]methyl]-(oxan-4-yl)azanium;chloride Chemical compound [Cl-].C1=CC(C)=CC=C1C1=CC=C(CCCC(=C2)C(=O)NC=3C=CC(C[N+](C)(C)C4CCOCC4)=CC=3)C2=C1 VDALIBWXVQVFGZ-UHFFFAOYSA-N 0.000 description 1
- 229950010286 diolamine Drugs 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- HCWOVPZEAFLXPL-UHFFFAOYSA-N diphenyl propanedioate Chemical compound C=1C=CC=CC=1OC(=O)CC(=O)OC1=CC=CC=C1 HCWOVPZEAFLXPL-UHFFFAOYSA-N 0.000 description 1
- KBKNTYKHUIHIHZ-UHFFFAOYSA-L dipotassium ethyl N-(2,6-dibromo-3-nitropyridin-4-yl)-N-[(6-methylpyridin-3-yl)methyl]carbamate carbonate Chemical compound C([O-])([O-])=O.[K+].C(C)OC(N(CC=1C=NC(=CC1)C)C1=C(C(=NC(=C1)Br)Br)[N+](=O)[O-])=O.[K+] KBKNTYKHUIHIHZ-UHFFFAOYSA-L 0.000 description 1
- TXWCVBYDZOPDHN-UHFFFAOYSA-L dipotassium ethyl N-[2-chloro-3-nitro-6-(trifluoromethyl)pyridin-4-yl]-N-[(6-methylpyridin-3-yl)methyl]carbamate carbonate Chemical compound C([O-])([O-])=O.[K+].C(C)OC(N(CC=1C=NC(=CC1)C)C1=C(C(=NC(=C1)C(F)(F)F)Cl)[N+](=O)[O-])=O.[K+] TXWCVBYDZOPDHN-UHFFFAOYSA-L 0.000 description 1
- JMVOCSLPMGHXPG-UHFFFAOYSA-N dipotassium;dioxido(dioxo)osmium Chemical compound [K+].[K+].[O-][Os]([O-])(=O)=O JMVOCSLPMGHXPG-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000005883 dithianyl group Chemical group 0.000 description 1
- 229940110377 dl- arginine Drugs 0.000 description 1
- CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
- 229960004679 doxorubicin Drugs 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
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- 235000014134 echinacea Nutrition 0.000 description 1
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- XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 description 1
- 238000004520 electroporation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229960003586 elvitegravir Drugs 0.000 description 1
- JUZYLCPPVHEVSV-LJQANCHMSA-N elvitegravir Chemical compound COC1=CC=2N([C@H](CO)C(C)C)C=C(C(O)=O)C(=O)C=2C=C1CC1=CC=CC(Cl)=C1F JUZYLCPPVHEVSV-LJQANCHMSA-N 0.000 description 1
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- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- NXVKRKUGIINGHD-ARJAWSKDSA-N ethyl (z)-3-amino-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)\C=C(/N)C(F)(F)F NXVKRKUGIINGHD-ARJAWSKDSA-N 0.000 description 1
- UBESIXFCSFYQNK-UHFFFAOYSA-N ethyl 1,3-oxazole-4-carboxylate Chemical compound CCOC(=O)C1=COC=N1 UBESIXFCSFYQNK-UHFFFAOYSA-N 0.000 description 1
- OTYLAHDSLZELOT-UHFFFAOYSA-N ethyl 2-chloro-3-oxopentanoate sulfuryl dichloride Chemical compound S(=O)(=O)(Cl)Cl.C(C)OC(C(C(CC)=O)Cl)=O OTYLAHDSLZELOT-UHFFFAOYSA-N 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- ZFQCYBPGYGVBIH-UHFFFAOYSA-N ethyl 2-isocyanoacetate ethyl 5-propan-2-yl-1,3-oxazole-4-carboxylate Chemical compound [N+](#[C-])CC(=O)OCC.C(C)OC(=O)C=1N=COC1C(C)C ZFQCYBPGYGVBIH-UHFFFAOYSA-N 0.000 description 1
- MTMRBCZTOJMQNS-UHFFFAOYSA-N ethyl 3-[(3-ethoxy-3-oxopropanoyl)amino]-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)CC(=O)NC(C(F)(F)F)=CC(=O)OCC MTMRBCZTOJMQNS-UHFFFAOYSA-N 0.000 description 1
- SJAOFPHBAYOIAX-UHFFFAOYSA-N ethyl 3-amino-3-cyclopropylprop-2-enoate Chemical compound CCOC(=O)C=C(N)C1CC1 SJAOFPHBAYOIAX-UHFFFAOYSA-N 0.000 description 1
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 1
- JVFDPSSRCVBVIR-UHFFFAOYSA-N ethyl 4-ethyl-1,3-oxazole-5-carboxylate 4-ethyl-1,3-oxazole-5-carboxylic acid Chemical compound C(C)OC(=O)C1=C(N=CO1)CC.C(C)C=1N=COC1C(=O)O JVFDPSSRCVBVIR-UHFFFAOYSA-N 0.000 description 1
- XCLDSQRVMMXWMS-UHFFFAOYSA-N ethyl 4-methyl-3-oxopentanoate Chemical compound CCOC(=O)CC(=O)C(C)C XCLDSQRVMMXWMS-UHFFFAOYSA-N 0.000 description 1
- ZSLVGOQQQVBFPB-UHFFFAOYSA-N ethyl 5-ethyl-1,3-oxazole-4-carboxylate 5-ethyl-1,3-oxazole Chemical compound C(C)OC(=O)C=1N=COC1CC.C(C)C1=CN=CO1 ZSLVGOQQQVBFPB-UHFFFAOYSA-N 0.000 description 1
- VMCGGJYUSVWETI-UHFFFAOYSA-N ethyl 5-propan-2-yl-1,3-oxazole-4-carboxylate 5-propan-2-yl-1,3-oxazole Chemical compound C(C)OC(=O)C=1N=COC1C(C)C.C(C)(C)C1=CN=CO1 VMCGGJYUSVWETI-UHFFFAOYSA-N 0.000 description 1
- LWGVDCVEVOEFBR-UHFFFAOYSA-N ethyl n-(2,6-dibromo-3-nitropyridin-4-yl)-n-[[6-(trifluoromethyl)pyridin-3-yl]methyl]carbamate Chemical compound C=1C(Br)=NC(Br)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=C(C(F)(F)F)N=C1 LWGVDCVEVOEFBR-UHFFFAOYSA-N 0.000 description 1
- KFATWOQNHFAQHS-UHFFFAOYSA-N ethyl n-(2,6-dichloro-3-nitropyridin-4-yl)carbamate Chemical compound CCOC(=O)NC1=CC(Cl)=NC(Cl)=C1[N+]([O-])=O KFATWOQNHFAQHS-UHFFFAOYSA-N 0.000 description 1
- QBVLPENSLLBHGK-UHFFFAOYSA-N ethyl n-(2-amino-3-nitro-6-propoxypyridin-4-yl)-n-benzylcarbamate Chemical compound NC1=NC(OCCC)=CC(N(CC=2C=CC=CC=2)C(=O)OCC)=C1[N+]([O-])=O QBVLPENSLLBHGK-UHFFFAOYSA-N 0.000 description 1
- BJKJFVNCMMPFJA-UHFFFAOYSA-N ethyl n-(2-amino-6-ethoxy-3-nitropyridin-4-yl)-n-benzylcarbamate Chemical compound C=1C(OCC)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 BJKJFVNCMMPFJA-UHFFFAOYSA-N 0.000 description 1
- DPQMBOXFXFUXBG-UHFFFAOYSA-N ethyl n-(2-amino-6-methylsulfanyl-3-nitropyridin-4-yl)-n-benzylcarbamate Chemical compound C=1C(SC)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 DPQMBOXFXFUXBG-UHFFFAOYSA-N 0.000 description 1
- IVFPNSHMAYYVDT-UHFFFAOYSA-N ethyl n-[(3-cyanophenyl)methyl]-n-(2,6-dibromo-3-nitropyridin-4-yl)carbamate Chemical compound C=1C(Br)=NC(Br)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC(C#N)=C1 IVFPNSHMAYYVDT-UHFFFAOYSA-N 0.000 description 1
- CYMGBQHHDKDEAI-UHFFFAOYSA-N ethyl n-[2-(benzylamino)-3-nitro-6-(trifluoromethyl)pyridin-4-yl]carbamate Chemical compound CCOC(=O)NC1=CC(C(F)(F)F)=NC(NCC=2C=CC=CC=2)=C1[N+]([O-])=O CYMGBQHHDKDEAI-UHFFFAOYSA-N 0.000 description 1
- XGSBUZKTOKFSHN-UHFFFAOYSA-N ethyl n-[2-amino-3-nitro-6-(1,2,4-triazol-1-yl)pyridin-4-yl]-n-benzylcarbamate Chemical compound C=1C(N2N=CN=C2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 XGSBUZKTOKFSHN-UHFFFAOYSA-N 0.000 description 1
- DIHIMZYEVAEPGN-UHFFFAOYSA-N ethyl n-[2-amino-3-nitro-6-(1,3-oxazol-2-yl)pyridin-4-yl]-n-[(3-cyanophenyl)methyl]carbamate Chemical compound C=1C(C=2OC=CN=2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC(C#N)=C1 DIHIMZYEVAEPGN-UHFFFAOYSA-N 0.000 description 1
- MNHUUZQADLZIBH-UHFFFAOYSA-N ethyl n-[2-amino-3-nitro-6-(1,3-oxazol-2-yl)pyridin-4-yl]-n-[[6-(trifluoromethyl)pyridin-3-yl]methyl]carbamate Chemical compound C=1C(C=2OC=CN=2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=C(C(F)(F)F)N=C1 MNHUUZQADLZIBH-UHFFFAOYSA-N 0.000 description 1
- HOSZSKAPLVHWNF-UHFFFAOYSA-N ethyl n-[2-amino-3-nitro-6-(1,3-thiazol-2-yl)pyridin-4-yl]-n-[(6-methylpyridin-3-yl)methyl]carbamate Chemical compound C=1C(C=2SC=CN=2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=C(C)N=C1 HOSZSKAPLVHWNF-UHFFFAOYSA-N 0.000 description 1
- OTGRTJCFCZRCAD-UHFFFAOYSA-N ethyl n-[2-amino-3-nitro-6-(4-propan-2-yl-1,3-oxazol-2-yl)pyridin-4-yl]-n-[(6-methylpyridin-3-yl)methyl]carbamate Chemical compound C=1C(C=2OC=C(N=2)C(C)C)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=C(C)N=C1 OTGRTJCFCZRCAD-UHFFFAOYSA-N 0.000 description 1
- CFIRXENGNFCUIS-UHFFFAOYSA-N ethyl n-[2-amino-3-nitro-6-(5-propan-2-yl-1,3-oxazol-2-yl)pyridin-4-yl]-n-[(6-methylpyridin-3-yl)methyl]carbamate Chemical compound C=1C(C=2OC(=CN=2)C(C)C)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=C(C)N=C1 CFIRXENGNFCUIS-UHFFFAOYSA-N 0.000 description 1
- LEBOMZHLLLYYKS-UHFFFAOYSA-N ethyl n-[2-amino-3-nitro-6-(propylamino)pyridin-4-yl]-n-benzylcarbamate Chemical compound NC1=NC(NCCC)=CC(N(CC=2C=CC=CC=2)C(=O)OCC)=C1[N+]([O-])=O LEBOMZHLLLYYKS-UHFFFAOYSA-N 0.000 description 1
- AWDYXSREPLLVRG-UHFFFAOYSA-N ethyl n-[2-amino-3-nitro-6-(triazol-1-yl)pyridin-4-yl]-n-benzylcarbamate Chemical compound C=1C(N2N=NC=C2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 AWDYXSREPLLVRG-UHFFFAOYSA-N 0.000 description 1
- SMHNULRHXGTQHQ-UHFFFAOYSA-N ethyl n-[2-amino-3-nitro-6-[3-(trifluoromethyl)pyrazol-1-yl]pyridin-4-yl]-n-benzylcarbamate Chemical compound C=1C(N2N=C(C=C2)C(F)(F)F)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 SMHNULRHXGTQHQ-UHFFFAOYSA-N 0.000 description 1
- AMGRWAQYYQQDGT-UHFFFAOYSA-N ethyl n-[2-amino-6-(2-fluorophenyl)-3-nitropyridin-4-yl]-n-benzylcarbamate Chemical compound C=1C(C=2C(=CC=CC=2)F)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 AMGRWAQYYQQDGT-UHFFFAOYSA-N 0.000 description 1
- XTYPCEYHJLRDSD-UHFFFAOYSA-N ethyl n-[2-amino-6-(2-methoxyethoxy)-3-nitropyridin-4-yl]-n-benzylcarbamate Chemical compound C=1C(OCCOC)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 XTYPCEYHJLRDSD-UHFFFAOYSA-N 0.000 description 1
- RHVKYTTWBITZPS-UHFFFAOYSA-N ethyl n-[2-amino-6-(2-methoxyethylamino)-3-nitropyridin-4-yl]-n-benzylcarbamate Chemical compound C=1C(NCCOC)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 RHVKYTTWBITZPS-UHFFFAOYSA-N 0.000 description 1
- ZQXJVNIPBNTUAW-UHFFFAOYSA-N ethyl n-[2-amino-6-(3,5-dimethylpyrazol-1-yl)-3-nitropyridin-4-yl]-n-benzylcarbamate Chemical compound C=1C(N2C(=CC(C)=N2)C)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 ZQXJVNIPBNTUAW-UHFFFAOYSA-N 0.000 description 1
- PXDVWJZMUBFDCD-UHFFFAOYSA-N ethyl n-[2-amino-6-(3-fluorophenyl)-3-nitropyridin-4-yl]-n-benzylcarbamate Chemical compound C=1C(C=2C=C(F)C=CC=2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 PXDVWJZMUBFDCD-UHFFFAOYSA-N 0.000 description 1
- MCISUKXSRRVUGI-UHFFFAOYSA-N ethyl n-[2-amino-6-(4,5-dimethyl-1,3-oxazol-2-yl)-3-nitropyridin-4-yl]-n-[(6-methylpyridin-3-yl)methyl]carbamate Chemical compound C=1C(C=2OC(C)=C(C)N=2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=C(C)N=C1 MCISUKXSRRVUGI-UHFFFAOYSA-N 0.000 description 1
- GWTLOLVMBPFNSA-UHFFFAOYSA-N ethyl n-[2-amino-6-(4-fluorophenyl)-3-nitropyridin-4-yl]-n-benzylcarbamate Chemical compound C=1C(C=2C=CC(F)=CC=2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 GWTLOLVMBPFNSA-UHFFFAOYSA-N 0.000 description 1
- FGGWSCFSYYRNDE-UHFFFAOYSA-N ethyl n-[2-amino-6-(4-methyl-1,3-oxazol-2-yl)-3-nitropyridin-4-yl]-n-[(6-methylpyridin-3-yl)methyl]carbamate Chemical compound C=1C(C=2OC=C(C)N=2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=C(C)N=C1 FGGWSCFSYYRNDE-UHFFFAOYSA-N 0.000 description 1
- RKRPZIFAAUOLKW-UHFFFAOYSA-N ethyl n-[2-amino-6-(4-methyl-1,3-oxazol-2-yl)-3-nitropyridin-4-yl]-n-[[6-(trifluoromethyl)pyridin-3-yl]methyl]carbamate Chemical compound C=1C(C=2OC=C(C)N=2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=C(C(F)(F)F)N=C1 RKRPZIFAAUOLKW-UHFFFAOYSA-N 0.000 description 1
- BKINKYOZFKLXHS-UHFFFAOYSA-N ethyl n-[2-amino-6-(4-methylpyrazol-1-yl)-3-nitropyridin-4-yl]-n-benzylcarbamate Chemical compound C=1C(N2N=CC(C)=C2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 BKINKYOZFKLXHS-UHFFFAOYSA-N 0.000 description 1
- BVPVWKHDHYLFGF-UHFFFAOYSA-N ethyl n-[2-amino-6-(5-ethyl-1,3-oxazol-2-yl)-3-nitropyridin-4-yl]-n-[(6-methylpyridin-3-yl)methyl]carbamate Chemical compound C=1C(C=2OC(CC)=CN=2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=C(C)N=C1 BVPVWKHDHYLFGF-UHFFFAOYSA-N 0.000 description 1
- GGATZLNJHPAKJR-UHFFFAOYSA-N ethyl n-[2-amino-6-(butylamino)-3-nitropyridin-4-yl]-n-benzylcarbamate Chemical compound NC1=NC(NCCCC)=CC(N(CC=2C=CC=CC=2)C(=O)OCC)=C1[N+]([O-])=O GGATZLNJHPAKJR-UHFFFAOYSA-N 0.000 description 1
- GGOGUIWWVYJQDK-UHFFFAOYSA-N ethyl n-[2-amino-6-(ethylamino)-3-nitropyridin-4-yl]-n-benzylcarbamate Chemical compound NC1=NC(NCC)=CC(N(CC=2C=CC=CC=2)C(=O)OCC)=C1[N+]([O-])=O GGOGUIWWVYJQDK-UHFFFAOYSA-N 0.000 description 1
- BJWKNQFJLSJZKM-UHFFFAOYSA-N ethyl n-[2-amino-6-[4-(2-hydroxyethyl)pyrazol-1-yl]-3-nitropyridin-4-yl]-n-benzylcarbamate Chemical compound C=1C(N2N=CC(CCO)=C2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 BJWKNQFJLSJZKM-UHFFFAOYSA-N 0.000 description 1
- DLHSESSOPNITIF-UHFFFAOYSA-N ethyl n-[2-amino-6-[4-(methoxymethyl)-1,3-oxazol-2-yl]-3-nitropyridin-4-yl]-n-benzylcarbamate Chemical compound C=1C(C=2OC=C(COC)N=2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 DLHSESSOPNITIF-UHFFFAOYSA-N 0.000 description 1
- HBVZDKPXMPGOKP-UHFFFAOYSA-N ethyl n-[2-amino-6-[4-[(dimethylamino)methyl]-1,3-oxazol-2-yl]-3-nitropyridin-4-yl]-n-benzylcarbamate Chemical compound C=1C(C=2OC=C(CN(C)C)N=2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 HBVZDKPXMPGOKP-UHFFFAOYSA-N 0.000 description 1
- HBAFBEWPQWHTIK-UHFFFAOYSA-N ethyl n-[2-amino-6-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-3-nitropyridin-4-yl]-n-benzylcarbamate Chemical compound C=1C(N2C(=CC(=N2)C(F)(F)F)C)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 HBAFBEWPQWHTIK-UHFFFAOYSA-N 0.000 description 1
- GUIRQHMBFGPGOY-UHFFFAOYSA-N ethyl n-[2-chloro-3-nitro-6-(trifluoromethyl)pyridin-4-yl]carbamate Chemical compound CCOC(=O)NC1=CC(C(F)(F)F)=NC(Cl)=C1[N+]([O-])=O GUIRQHMBFGPGOY-UHFFFAOYSA-N 0.000 description 1
- AXEXKQIHDOEGGE-UHFFFAOYSA-N ethyl n-benzyl-n-(2,3-diamino-6-pyrazol-1-ylpyridin-4-yl)carbamate Chemical compound C=1C(N2N=CC=C2)=NC(N)=C(N)C=1N(C(=O)OCC)CC1=CC=CC=C1 AXEXKQIHDOEGGE-UHFFFAOYSA-N 0.000 description 1
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- 239000012467 final product Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- RFHAOTPXVQNOHP-UHFFFAOYSA-N fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 description 1
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- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 description 1
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Classifications
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
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- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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| PCT/IB2007/000368 WO2007093901A1 (en) | 2006-02-17 | 2007-02-05 | 3 -deazapurine derivatives as tlr7 modulators |
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Also Published As
| Publication number | Publication date |
|---|---|
| NL2000480A1 (nl) | 2007-08-20 |
| US7691877B2 (en) | 2010-04-06 |
| IL193173A0 (en) | 2009-02-11 |
| AU2007216247A1 (en) | 2007-08-23 |
| BRPI0707945A2 (pt) | 2011-05-17 |
| PE20070983A1 (es) | 2007-10-24 |
| EP1987030A1 (en) | 2008-11-05 |
| CA2640672A1 (en) | 2007-08-23 |
| US20070197478A1 (en) | 2007-08-23 |
| UY30169A1 (es) | 2007-09-28 |
| ES2374455T3 (es) | 2012-02-16 |
| ATE532784T1 (de) | 2011-11-15 |
| NL2000480C2 (nl) | 2012-09-17 |
| KR20080085232A (ko) | 2008-09-23 |
| TW200800995A (en) | 2008-01-01 |
| EP1987030B1 (en) | 2011-11-09 |
| WO2007093901A1 (en) | 2007-08-23 |
| AR059481A1 (es) | 2008-04-09 |
| MX2008010611A (es) | 2008-11-12 |
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