JP6763769B2 - ウイルス感染症および他の疾病の処置のためのピロロ［３，２−ｄ］ピリミジン誘導体 - Google Patents
ウイルス感染症および他の疾病の処置のためのピロロ［３，２−ｄ］ピリミジン誘導体 Download PDFInfo
- Publication number
- JP6763769B2 JP6763769B2 JP2016522487A JP2016522487A JP6763769B2 JP 6763769 B2 JP6763769 B2 JP 6763769B2 JP 2016522487 A JP2016522487 A JP 2016522487A JP 2016522487 A JP2016522487 A JP 2016522487A JP 6763769 B2 JP6763769 B2 JP 6763769B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- pharmaceutically acceptable
- solvate
- aryl
- 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
Links
- 150000003230 pyrimidines Chemical class 0.000 title description 5
- 208000036142 Viral infection Diseases 0.000 title description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 4
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 4
- 230000009385 viral infection Effects 0.000 title description 4
- 201000010099 disease Diseases 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 29
- 239000012453 solvate Substances 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 150000002825 nitriles Chemical class 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 102100039390 Toll-like receptor 7 Human genes 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- -1 substituted Chemical class 0.000 claims description 6
- 230000004913 activation Effects 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 229940044616 toll-like receptor 7 agonist Drugs 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 21
- 210000004027 cell Anatomy 0.000 description 18
- 102000002689 Toll-like receptor Human genes 0.000 description 13
- 108020000411 Toll-like receptor Proteins 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000002552 dosage form Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001733 carboxylic acid esters Chemical class 0.000 description 6
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- 101000800483 Homo sapiens Toll-like receptor 8 Proteins 0.000 description 4
- 108060001084 Luciferase Proteins 0.000 description 4
- 239000005089 Luciferase Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- 150000003456 sulfonamides Chemical class 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 102100033110 Toll-like receptor 8 Human genes 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 230000033228 biological regulation Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 239000000411 inducer Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000013612 plasmid Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000711549 Hepacivirus C Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 108010078049 Interferon alpha-2 Proteins 0.000 description 2
- 108010047761 Interferon-alpha Proteins 0.000 description 2
- 102000006992 Interferon-alpha Human genes 0.000 description 2
- 108010050904 Interferons Proteins 0.000 description 2
- 102000014150 Interferons Human genes 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229940079322 interferon Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- QJIMTLTYXBDJFC-UHFFFAOYSA-N (4-methylphenyl)-diphenylphosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJIMTLTYXBDJFC-UHFFFAOYSA-N 0.000 description 1
- MDYHWQQHEWDJKR-UHFFFAOYSA-N (5-methyl-1,2-oxazol-3-yl)methanol Chemical compound CC1=CC(CO)=NO1 MDYHWQQHEWDJKR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 0 CCC=C(C)*NCCOc1c2[n](Cc3ncccc3)ccc2nc(N)n1 Chemical compound CCC=C(C)*NCCOc1c2[n](Cc3ncccc3)ccc2nc(N)n1 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 101100166531 Drosophila melanogaster CycC gene Proteins 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 229920001917 Ficoll Polymers 0.000 description 1
- 108090000331 Firefly luciferases Proteins 0.000 description 1
- 101000852870 Homo sapiens Interferon alpha/beta receptor 1 Proteins 0.000 description 1
- 101000763579 Homo sapiens Toll-like receptor 1 Proteins 0.000 description 1
- 101000763537 Homo sapiens Toll-like receptor 10 Proteins 0.000 description 1
- 102100036714 Interferon alpha/beta receptor 1 Human genes 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101100481581 Mus musculus Tlr13 gene Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 239000012979 RPMI medium Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 229940124613 TLR 7/8 agonist Drugs 0.000 description 1
- 241001441722 Takifugu rubripes Species 0.000 description 1
- 102100027010 Toll-like receptor 1 Human genes 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical class N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000008484 agonism Effects 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- 238000007630 basic procedure Methods 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000006143 cell culture medium Substances 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- MWWQOUGXCWIOSR-UHFFFAOYSA-N ethyl 3-amino-1h-pyrrole-2-carboxylate;hydrochloride Chemical compound [Cl-].CCOC(=O)C=1NC=CC=1[NH3+] MWWQOUGXCWIOSR-UHFFFAOYSA-N 0.000 description 1
- XWRLQRLQUKZEEU-UHFFFAOYSA-N ethyl(hydroxy)silicon Chemical class CC[Si]O XWRLQRLQUKZEEU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000105 evaporative light scattering detection Methods 0.000 description 1
- 239000013604 expression vector Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 102000050028 human TLR10 Human genes 0.000 description 1
- 102000045715 human TLR7 Human genes 0.000 description 1
- 102000045720 human TLR8 Human genes 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 210000002865 immune cell Anatomy 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 230000005847 immunogenicity Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000015788 innate immune response Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- DAZSWUUAFHBCGE-KRWDZBQOSA-N n-[(2s)-3-methyl-1-oxo-1-pyrrolidin-1-ylbutan-2-yl]-3-phenylpropanamide Chemical compound N([C@@H](C(C)C)C(=O)N1CCCC1)C(=O)CCC1=CC=CC=C1 DAZSWUUAFHBCGE-KRWDZBQOSA-N 0.000 description 1
- 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 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 210000001539 phagocyte Anatomy 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000004544 spot-on Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 239000012096 transfection reagent Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 102000035160 transmembrane proteins Human genes 0.000 description 1
- 108091005703 transmembrane proteins Proteins 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 239000012646 vaccine adjuvant Substances 0.000 description 1
- 229940124931 vaccine adjuvant Drugs 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13174108.4 | 2013-06-27 | ||
| EP13174108 | 2013-06-27 | ||
| PCT/EP2014/063467 WO2014207082A1 (en) | 2013-06-27 | 2014-06-26 | Pyrrolo[3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020151192A Division JP2020203929A (ja) | 2013-06-27 | 2020-09-09 | ウイルス感染症および他の疾病の処置のためのピロロ［３，２−ｄ］ピリミジン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016526550A JP2016526550A (ja) | 2016-09-05 |
| JP6763769B2 true JP6763769B2 (ja) | 2020-09-30 |
Family
ID=48692351
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016522487A Expired - Fee Related JP6763769B2 (ja) | 2013-06-27 | 2014-06-26 | ウイルス感染症および他の疾病の処置のためのピロロ［３，２−ｄ］ピリミジン誘導体 |
| JP2020151192A Withdrawn JP2020203929A (ja) | 2013-06-27 | 2020-09-09 | ウイルス感染症および他の疾病の処置のためのピロロ［３，２−ｄ］ピリミジン誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020151192A Withdrawn JP2020203929A (ja) | 2013-06-27 | 2020-09-09 | ウイルス感染症および他の疾病の処置のためのピロロ［３，２−ｄ］ピリミジン誘導体 |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US10385054B2 (OSRAM) |
| EP (1) | EP3030563B1 (OSRAM) |
| JP (2) | JP6763769B2 (OSRAM) |
| KR (1) | KR102311234B1 (OSRAM) |
| CN (2) | CN105473592B (OSRAM) |
| AU (2) | AU2014301089B2 (OSRAM) |
| BR (1) | BR112015032546B1 (OSRAM) |
| CA (1) | CA2913028C (OSRAM) |
| CL (1) | CL2015003686A1 (OSRAM) |
| DK (1) | DK3030563T3 (OSRAM) |
| EA (2) | EA202090258A3 (OSRAM) |
| ES (1) | ES2645950T3 (OSRAM) |
| HR (1) | HRP20171720T1 (OSRAM) |
| HU (1) | HUE037125T2 (OSRAM) |
| IL (3) | IL242655B (OSRAM) |
| MX (2) | MX392130B (OSRAM) |
| MY (1) | MY176142A (OSRAM) |
| NO (1) | NO3030563T3 (OSRAM) |
| PH (1) | PH12015502780B1 (OSRAM) |
| PL (1) | PL3030563T3 (OSRAM) |
| PT (1) | PT3030563T (OSRAM) |
| SG (2) | SG11201510637UA (OSRAM) |
| SI (1) | SI3030563T1 (OSRAM) |
| UA (1) | UA117590C2 (OSRAM) |
| WO (1) | WO2014207082A1 (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020203929A (ja) * | 2013-06-27 | 2020-12-24 | ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー | ウイルス感染症および他の疾病の処置のためのピロロ［３，２−ｄ］ピリミジン誘導体 |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LT3590928T (lt) | 2011-04-08 | 2021-08-25 | Janssen Sciences Ireland Unlimited Company | Pirimidino dariniai, skirti virusinės infekcijos gydymui |
| JOP20150177B1 (ar) | 2014-08-01 | 2021-08-17 | Janssen Pharmaceutica Nv | مركبات 6 ، 7 ثاني هيدرو بيرازولو [ 1، 5 الفا ] بيرازين – 4 (5 يد) – اون واستخدامها كمنظمات الوسترية سلبية لمستقبلات ملجور 2 |
| MA44334A (fr) | 2015-10-29 | 2018-09-05 | Novartis Ag | Conjugués d'anticorps comprenant un agoniste du récepteur de type toll |
| PL3389727T3 (pl) | 2015-12-18 | 2021-02-08 | Janssen Pharmaceutica Nv | RADIOZNAKOWANE LIGANDY mGluR2/3 DO PET |
| EP3389728B1 (en) | 2015-12-18 | 2020-08-05 | Janssen Pharmaceutica NV | Radiolabelled mglur2/3 pet ligands |
| CA3027471A1 (en) * | 2016-07-01 | 2018-01-04 | Janssen Sciences Ireland Unlimited Company | Dihydropyranopyrimidines for the treatment of viral infections |
| KR102450287B1 (ko) | 2016-09-29 | 2022-09-30 | 얀센 사이언시즈 아일랜드 언리미티드 컴퍼니 | 바이러스 감염 및 추가적인 질환의 치료를 위한 피리미딘 프로드러그 |
| TW202415645A (zh) | 2018-03-01 | 2024-04-16 | 愛爾蘭商健生科學愛爾蘭無限公司 | ２，４－二胺基喹唑啉衍生物及其醫學用途 |
| WO2019209811A1 (en) | 2018-04-24 | 2019-10-31 | Bristol-Myers Squibb Company | Macrocyclic toll-like receptor 7 (tlr7) agonists |
| US11554120B2 (en) | 2018-08-03 | 2023-01-17 | Bristol-Myers Squibb Company | 1H-pyrazolo[4,3-d]pyrimidine compounds as toll-like receptor 7 (TLR7) agonists and methods and uses therefor |
| JP7287708B2 (ja) | 2019-02-08 | 2023-06-06 | プロジェニア インコーポレイテッド | Ｔｏｌｌ－ｌｉｋｅ受容体７または８アゴニストとコレステロールの結合体およびその用途 |
| JP2023512207A (ja) | 2020-01-27 | 2023-03-24 | ブリストル－マイヤーズ スクイブ カンパニー | トール様受容体７（ＴＬＲ７）アゴニストとしての１Ｈ－ピラゾロ［４，３－ｄ］ピリミジン化合物 |
| JP7712941B2 (ja) | 2020-01-27 | 2025-07-24 | ブリストル－マイヤーズ スクイブ カンパニー | トール様受容体７（ＴＬＲ７）アゴニストとしての１Ｈ－ピラゾロ［４，３－ｄ］ピリミジン化合物 |
| EP4097105A1 (en) | 2020-01-27 | 2022-12-07 | Bristol-Myers Squibb Company | 1h-pyrazolo[4,3-d]pyrimidine compounds as toll-like receptor 7 (tlr7) agonists |
| WO2021154663A1 (en) | 2020-01-27 | 2021-08-05 | Bristol-Myers Squibb Company | 1H-PYRAZOLO[4,3-d]PYRIMIDINE COMPOUNDS AS TOLL-LIKE RECEPTOR 7 (TLR7) AGONISTS |
| CN115135655B (zh) | 2020-01-27 | 2024-07-02 | 百时美施贵宝公司 | 作为Toll样受体7(TLR7)激动剂的1H-吡唑并[4,3-d]嘧啶化合物 |
| CN115151546A (zh) | 2020-01-27 | 2022-10-04 | 百时美施贵宝公司 | 作为Toll样受体7(TLR7)激动剂的C3-取代的1H-吡唑并[4,3-d]嘧啶化合物 |
| CN115643805B (zh) | 2020-01-27 | 2024-11-08 | 百时美施贵宝公司 | 作为Toll样受体7(TLR7)激动剂的1H-吡唑并[4,3-d]嘧啶化合物 |
| WO2021154669A1 (en) | 2020-01-27 | 2021-08-05 | Bristol-Myers Squibb Company | 1H-PYRAZOLO[4,3-d]PYRIMIDINE COMPOUNDS AS TOLL-LIKE RECEPTOR 7 (TLR7) AGONISTS |
| EP4097100A1 (en) | 2020-01-27 | 2022-12-07 | Bristol-Myers Squibb Company | 1h-pyrazolo[4,3-d]pyrimidine compounds as toll-like receptor 7 (tlr7) agonists |
| JP2023516372A (ja) | 2020-03-02 | 2023-04-19 | プロジェニア インコーポレイテッド | 病原菌外壁成分基盤の生病原体模倣ナノ粒子及びその製造方法 |
| WO2022031057A1 (ko) | 2020-08-04 | 2022-02-10 | 성균관대학교산학협력단 | 활성화 부위가 일시적으로 비활성화된 톨-유사 수용체 7 또는 8 작용자와 기능성 약물의 결합체 및 그 용도 |
| EP4194006A4 (en) | 2020-08-04 | 2024-12-04 | Progeneer Inc. | mRNA VACCINE WITH AN ADJUVANT CAPABLE OF KINETIC CONTROL |
| US20230355750A1 (en) | 2020-08-04 | 2023-11-09 | Progeneer Inc. | Kinetically acting adjuvant ensemble |
Family Cites Families (87)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2610889B2 (ja) | 1987-09-03 | 1997-05-14 | 日本臓器製薬株式会社 | 新規架橋アデニン誘導体 |
| ATE283855T1 (de) | 1996-07-03 | 2004-12-15 | Sumitomo Pharma | Neue purinderivate |
| CZ68199A3 (cs) | 1996-08-28 | 1999-11-17 | Pfizer Inc. | 6,5-Heterobicyklické deriváty, farmaceutická kompozice na jejich bázi a způsob léčení chorob |
| EP0989129B1 (en) | 1996-10-04 | 2002-12-11 | Kyorin Pharmaceutical Co., Ltd. | Pyrazolopyridylpyridazinone derivatives and process for the preparation thereof |
| AR012634A1 (es) | 1997-05-02 | 2000-11-08 | Sugen Inc | Compuesto basado en quinazolina, composicion famaceutica que lo comprende, metodo para sintetizarlo, su uso, metodos de modulacion de la funcion deserina/treonina proteinaquinasa con dicho compuesto y metodo in vitro para identificar compuestos que modulan dicha funcion |
| US6339089B2 (en) | 1997-08-13 | 2002-01-15 | Fujirebio Inc. | Pyrimidine nucleus-containing compound and a medicament containing the same for a blood oxygen partial pressure amelioration, and a method for preparing the same |
| US6329381B1 (en) | 1997-11-28 | 2001-12-11 | Sumitomo Pharmaceuticals Company, Limited | Heterocyclic compounds |
| TW572758B (en) | 1997-12-22 | 2004-01-21 | Sumitomo Pharma | Type 2 helper T cell-selective immune response inhibitors comprising purine derivatives |
| US6187777B1 (en) * | 1998-02-06 | 2001-02-13 | Amgen Inc. | Compounds and methods which modulate feeding behavior and related diseases |
| WO1999041253A1 (en) | 1998-02-17 | 1999-08-19 | Tularik Inc. | Anti-viral pyrimidine derivatives |
| 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 |
| JP4342007B2 (ja) | 1998-08-10 | 2009-10-14 | 大日本住友製薬株式会社 | キナゾリン誘導体 |
| JP4315300B2 (ja) | 1998-08-10 | 2009-08-19 | 大日本住友製薬株式会社 | 新規なキナゾリン誘導体 |
| DE69917469T2 (de) | 1998-08-27 | 2005-05-12 | Sumitomo Pharmaceuticals Co., Ltd. | Pyrimidin derivate |
| US6583148B1 (en) | 1999-04-08 | 2003-06-24 | Krenitsky Pharmaceuticals, Inc. | Neurotrophic substituted pyrimidines |
| US6503908B1 (en) | 1999-10-11 | 2003-01-07 | Pfizer Inc | Pharmaceutically active compounds |
| WO2002088079A2 (en) | 2001-05-01 | 2002-11-07 | Bristol-Myers Squibb Company | Dual inhibitors of pde 7 and pde 4 |
| WO2003055890A1 (en) | 2001-12-21 | 2003-07-10 | Bayer Pharmaceuticals Corporation | Thienopyrimidine derivative compounds as inhibitors of prolylpeptidase, inducers of apoptosis and cancer treatment agents |
| TW200407143A (en) | 2002-05-21 | 2004-05-16 | Bristol Myers Squibb Co | Pyrrolotriazinone compounds and their use to treat diseases |
| US7091232B2 (en) | 2002-05-21 | 2006-08-15 | Allergan, Inc. | 4-(substituted cycloalkylmethyl) imidazole-2-thiones, 4-(substituted cycloalkenylmethyl) imidazole-2-thiones, 4-(substituted cycloalkylmethyl) imidazol-2-ones and 4-(substituted cycloalkenylmethyl) imidazol-2-ones and related compounds |
| EP1552842A1 (en) | 2002-06-07 | 2005-07-13 | Kyowa Hakko Kogyo Co., Ltd. | Bicyclic pyrimidine derivatives |
| AU2003271064B2 (en) | 2002-09-27 | 2010-06-17 | Dainippon Sumitomo Pharma Co., Ltd. | Novel adenine compound and use thereof |
| US8455458B2 (en) | 2002-10-16 | 2013-06-04 | Arthrodynamic Technologies, Animal Health Division, Inc. | Composition and method for treating connective tissue damage |
| BRPI0411514A (pt) | 2003-06-20 | 2006-08-01 | Coley Pharm Gmbh | antagonistas de receptor toll-like de molécula pequena |
| NZ545536A (en) | 2003-09-05 | 2010-04-30 | Anadys Pharmaceuticals Inc | TLR7 ligands for the treatment of hepatitis C |
| TWI414525B (zh) | 2004-03-26 | 2013-11-11 | Dainippon Sumitomo Pharma Co | ９-取代-８-氧基腺嘌呤化合物 |
| US20070225303A1 (en) | 2004-03-26 | 2007-09-27 | Haruhisa Ogita | 8-Oxoadenine Compound |
| WO2007084413A2 (en) | 2004-07-14 | 2007-07-26 | Ptc Therapeutics, Inc. | Methods for treating hepatitis c |
| ES2442857T3 (es) | 2004-08-10 | 2014-02-13 | Janssen Pharmaceutica Nv | Derivados de 1,2,4-triazin-6-ona inhibidores de VIH |
| BRPI0517559A (pt) | 2004-11-09 | 2008-10-14 | Hoffmann La Roche | composto, processo para a sua preparação, método para o tratamento terapêutico e/ou profilático de enfermidades que são moduladas por inibidores de ptb-1b e utilização dos compostos |
| US7498409B2 (en) | 2005-03-24 | 2009-03-03 | Schering Corporation | Screening assay for TLR7, TLR8 and TLR9 agonists and antagonists |
| AU2006242920A1 (en) | 2005-05-04 | 2006-11-09 | Pfizer Limited | 2-amido-6-amino-8-oxopurine derivatives as Toll-Like receptor modulators for the treatment of cancer and viral infections, such as hepatitis C |
| WO2006122003A2 (en) * | 2005-05-05 | 2006-11-16 | Ardea Biosciences, Inc. | Diaryl-purine, azapurines and -deazapurines as non-nucleoside reverse transcriptase inhibitors for treatment of hiv |
| AR054122A1 (es) | 2005-05-12 | 2007-06-06 | Tibotec Pharm Ltd | Pirido[2,3-d]pirimidas utiles como inhibidores de hcv, y metodos para la preparacion de las mismas |
| US7994360B2 (en) | 2005-05-16 | 2011-08-09 | Xtl Biopharmaceuticals Ltd. | Benzofuran compounds |
| JP4850911B2 (ja) | 2005-09-01 | 2012-01-11 | エフ．ホフマン−ラ ロシュ アーゲー | Ｐ２ｘ３およびｐ２ｘ２／３モジュレーターとしてのジアミノピリミジン |
| EP1939198A4 (en) | 2005-09-22 | 2012-02-15 | Dainippon Sumitomo Pharma Co | NEW ADENINE CONNECTION |
| WO2007056208A2 (en) | 2005-11-02 | 2007-05-18 | Cytovia, Inc. | N-arylalkyl-thienopyrimidin-4-amines and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| US20090182140A1 (en) | 2005-12-02 | 2009-07-16 | Mitsubishi Tanabe Pharma Corporation | Alicyclic Heterocyclic Compound |
| MX2008010611A (es) | 2006-02-17 | 2008-11-12 | Pfizer Ltd | Derivados de 3-desazapurina como moduladores de receptores similares a toll. |
| US9259426B2 (en) | 2006-07-20 | 2016-02-16 | Gilead Sciences, Inc. | 4,6-di- and 2,4,6-trisubstituted quinazoline derivatives useful for treating viral infections |
| US8673929B2 (en) | 2006-07-20 | 2014-03-18 | Gilead Sciences, Inc. | 4,6-di- and 2,4,6-trisubstituted quinazoline derivatives and pharmaceutical compositions useful for treating viral infections |
| KR101507182B1 (ko) | 2006-12-07 | 2015-03-30 | 제넨테크, 인크. | 포스포이노시타이드 3-키나제 억제제 화합물 및 그의 사용 방법 |
| CN103224506A (zh) | 2006-12-20 | 2013-07-31 | P.安杰莱蒂分子生物学研究所 | 抗病毒的吲哚 |
| EP2510946B1 (en) | 2007-02-07 | 2015-08-05 | The Regents of The University of California | Conjugates of synthetic tlr agonists and uses therefor |
| JP2008222557A (ja) * | 2007-03-08 | 2008-09-25 | Kotobuki Seiyaku Kk | ピロロ［３，２−ｄ］ピリミジン誘導体及びこれを有効成分とする医薬組成物 |
| DK2132209T3 (da) | 2007-03-19 | 2014-04-14 | Astrazeneca Ab | 9-substituerede 8-oxo-adeninforbindelser som modulatorer af tlr7 (toll-like receptor 7) |
| PE20081887A1 (es) * | 2007-03-20 | 2009-01-16 | Dainippon Sumitomo Pharma Co | Nuevo compuesto de adenina |
| US8044056B2 (en) | 2007-03-20 | 2011-10-25 | Dainippon Sumitomo Pharma Co., Ltd. | Adenine compound |
| WO2008147697A1 (en) | 2007-05-22 | 2008-12-04 | Boehringer Ingelheim International Gmbh | Benzimidazolone chymase inhibitors |
| EA021463B1 (ru) | 2007-06-29 | 2015-06-30 | Джилид Сайэнс, Инк. | Пуриновые производные и их применение в качестве модуляторов толл-подобного рецептора 7 |
| US20090176778A1 (en) | 2007-08-10 | 2009-07-09 | Franz Ulrich Schmitz | Certain nitrogen containing bicyclic chemical entities for treating viral infections |
| CA2696824A1 (en) | 2007-08-28 | 2009-03-12 | Irm Llc | Compounds and compositions as kinase inhibitors |
| WO2009030998A1 (en) | 2007-09-05 | 2009-03-12 | Coley Pharmaceutical Group, Inc. | Pyrimidine compounds as toll-like receptor (tlr) agonists |
| PE20091236A1 (es) * | 2007-11-22 | 2009-09-16 | Astrazeneca Ab | Derivados de pirimidina como immunomoduladores de tlr7 |
| PL2238142T3 (pl) | 2007-12-24 | 2012-11-30 | Janssen R&D Ireland | Makrocykliczne indole jako inhibitory wirusa zapalenia wątroby typu C |
| WO2009099650A2 (en) | 2008-02-07 | 2009-08-13 | Carson Dennis A | Treatment of bladder diseases with a tlr7 activator |
| CA2720850A1 (en) | 2008-04-28 | 2009-11-05 | Merck Sharp & Dohme Corp. | Hcv ns3 protease inhibitors |
| WO2009157560A1 (ja) | 2008-06-27 | 2009-12-30 | 京セラ株式会社 | ユーザインタフェース生成装置 |
| US8946239B2 (en) | 2008-07-10 | 2015-02-03 | Duquesne University Of The Holy Spirit | Substituted pyrrolo, -furano, and cyclopentylpyrimidines having antimitotic and/or antitumor activity and methods of use thereof |
| UY31982A (es) | 2008-07-16 | 2010-02-26 | Boehringer Ingelheim Int | Derivados de 1,2-dihidropiridin-3-carboxamidas n-sustituidas |
| EA201101650A1 (ru) | 2009-05-21 | 2012-07-30 | Астразенека Аб | Новые производные пиримидина и их применение в лечении злокачественных новообразований и последующих заболеваний |
| US8637525B2 (en) | 2009-07-31 | 2014-01-28 | Bristol-Myers Squibb Company | Compounds for the reduction of beta-amyloid production |
| TWI468402B (zh) | 2009-07-31 | 2015-01-11 | 必治妥美雅史谷比公司 | 降低β－類澱粉生成之化合物 |
| WO2011049988A2 (en) | 2009-10-20 | 2011-04-28 | Eiger Biopharmaceuticals, Inc. | Indazoles to treat flaviviridae virus infection |
| WO2011049825A1 (en) | 2009-10-22 | 2011-04-28 | Gilead Sciences, Inc. | Derivatives of purine or deazapurine useful for the treatment of (inter alia) viral infections |
| KR101094446B1 (ko) | 2009-11-19 | 2011-12-15 | 한국과학기술연구원 | 단백질 키나아제 저해활성을 가지는 2,4,7-치환된 티에노［3,2-ｄ］피리미딘 화합물 |
| JP2013032290A (ja) | 2009-11-20 | 2013-02-14 | Dainippon Sumitomo Pharma Co Ltd | 新規縮合ピリミジン誘導体 |
| DE102010040233A1 (de) | 2010-09-03 | 2012-03-08 | Bayer Schering Pharma Aktiengesellschaft | Bicyclische Aza-Heterocyclen und ihre Verwendung |
| WO2012066335A1 (en) | 2010-11-19 | 2012-05-24 | Astrazeneca Ab | Phenol compounds als toll -like receptor 7 agonists |
| WO2012067269A1 (en) | 2010-11-19 | 2012-05-24 | Dainippon Sumitomo Pharma Co., Ltd. | Aminoalkoxyphenyl compounds and their use in the treatment of disease |
| LT3590928T (lt) | 2011-04-08 | 2021-08-25 | Janssen Sciences Ireland Unlimited Company | Pirimidino dariniai, skirti virusinės infekcijos gydymui |
| US8916575B2 (en) | 2011-05-18 | 2014-12-23 | Janssen R&D Ireland | Quinazoline derivatives for the treatment of viral infections and further diseases |
| EA036645B1 (ru) | 2011-11-09 | 2020-12-03 | Янссен Сайенсиз Айрлэнд Юси | Производные пурина для лечения вирусных инфекций |
| BR112014019699B1 (pt) | 2012-02-08 | 2021-12-07 | Janssen Sciences Ireland Uc | Derivados de piperidino-pirimidina, seu uso no tratamento de infecções virais e composição farmacêutica que os compreende |
| RS61664B1 (sr) | 2012-04-24 | 2021-04-29 | Vertex Pharma | Inhibitori dna-pk |
| PL2872515T3 (pl) | 2012-07-13 | 2017-05-31 | Janssen Sciences Ireland Uc | Puryny makrocykliczne do leczenia infekcji wirusowych |
| BR112015002524B1 (pt) | 2012-08-10 | 2021-11-03 | Janssen Sciences Ireland Uc | Derivados de alquilpirimidina, composição farmacêutica que os compreende e uso dos mesmos |
| EP2712866A1 (en) | 2012-10-01 | 2014-04-02 | Centre National de la Recherche Scientifique (CNRS) | 1,2,4-triazine derivatives for the treatment of viral infections |
| CA2882786C (en) | 2012-10-05 | 2020-10-20 | Janssen Sciences Ireland Uc | Acylaminopyrimidine derivatives for the treatment of viral infections and further diseases. |
| SI2906563T1 (en) * | 2012-10-10 | 2018-06-29 | Janssen Sciences Ireland Uc | Derivatives of pyrrolo (3,2-d) pyrimidine for the treatment of viral infections and other diseases |
| MY171115A (en) | 2012-11-16 | 2019-09-26 | Janssen Sciences Ireland Uc | Heterocyclic substituted 2-amino-quinazoline derivatives for the treatment of viral infections |
| UA118751C2 (uk) | 2013-02-21 | 2019-03-11 | ЯНССЕН САЙЄНСІЗ АЙРЛЕНД ЮСі | Похідні 2-амінопіримідину для лікування вірусних інфекцій |
| PL2978429T3 (pl) | 2013-03-29 | 2017-08-31 | Janssen Sciences Ireland Uc | Deazapurynony makrocykliczne do leczenia infekcji wirusowych |
| WO2014207082A1 (en) * | 2013-06-27 | 2014-12-31 | Janssen R&D Ireland | Pyrrolo[3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases |
| ES2836881T3 (es) | 2013-07-30 | 2021-06-28 | Janssen Sciences Ireland Unlimited Co | Derivados de tieno[3,2-d]pirimidinas para el tratamiento de infecciones virales |
| WO2016007966A2 (en) | 2014-07-11 | 2016-01-14 | Northwestern University | 2-imidazolyl-pyrimidine scaffolds as potent and selective inhibitors of neuronal nitric oxide synthase |
-
2014
- 2014-06-26 WO PCT/EP2014/063467 patent/WO2014207082A1/en not_active Ceased
- 2014-06-26 UA UAA201600620A patent/UA117590C2/uk unknown
- 2014-06-26 HU HUE14738751A patent/HUE037125T2/hu unknown
- 2014-06-26 CA CA2913028A patent/CA2913028C/en active Active
- 2014-06-26 US US14/392,214 patent/US10385054B2/en not_active Expired - Fee Related
- 2014-06-26 HR HRP20171720TT patent/HRP20171720T1/hr unknown
- 2014-06-26 PL PL14738751T patent/PL3030563T3/pl unknown
- 2014-06-26 MY MYPI2015003051A patent/MY176142A/en unknown
- 2014-06-26 DK DK14738751.8T patent/DK3030563T3/da active
- 2014-06-26 CN CN201480036233.5A patent/CN105473592B/zh not_active Expired - Fee Related
- 2014-06-26 NO NO14738751A patent/NO3030563T3/no unknown
- 2014-06-26 EA EA202090258A patent/EA202090258A3/ru unknown
- 2014-06-26 SG SG11201510637UA patent/SG11201510637UA/en unknown
- 2014-06-26 EA EA201690093A patent/EA034893B1/ru unknown
- 2014-06-26 SI SI201430476T patent/SI3030563T1/sl unknown
- 2014-06-26 CN CN201811093750.2A patent/CN109369643B/zh not_active Expired - Fee Related
- 2014-06-26 ES ES14738751.8T patent/ES2645950T3/es active Active
- 2014-06-26 EP EP14738751.8A patent/EP3030563B1/en active Active
- 2014-06-26 MX MX2018015053A patent/MX392130B/es unknown
- 2014-06-26 KR KR1020157035575A patent/KR102311234B1/ko not_active Expired - Fee Related
- 2014-06-26 PT PT147387518T patent/PT3030563T/pt unknown
- 2014-06-26 MX MX2015017671A patent/MX361527B/es active IP Right Grant
- 2014-06-26 JP JP2016522487A patent/JP6763769B2/ja not_active Expired - Fee Related
- 2014-06-26 BR BR112015032546-7A patent/BR112015032546B1/pt not_active IP Right Cessation
- 2014-06-26 AU AU2014301089A patent/AU2014301089B2/en not_active Ceased
- 2014-06-26 SG SG10201803331PA patent/SG10201803331PA/en unknown
-
2015
- 2015-11-18 IL IL242655A patent/IL242655B/en active IP Right Grant
- 2015-12-14 PH PH12015502780A patent/PH12015502780B1/en unknown
- 2015-12-21 CL CL2015003686A patent/CL2015003686A1/es unknown
-
2018
- 2018-03-20 IL IL258253A patent/IL258253B/en active IP Right Grant
- 2018-12-05 AU AU2018274911A patent/AU2018274911B2/en not_active Ceased
-
2019
- 2019-01-22 IL IL264402A patent/IL264402B/en active IP Right Grant
- 2019-06-14 US US16/441,213 patent/US10781216B2/en not_active Expired - Fee Related
-
2020
- 2020-09-09 JP JP2020151192A patent/JP2020203929A/ja not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020203929A (ja) * | 2013-06-27 | 2020-12-24 | ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー | ウイルス感染症および他の疾病の処置のためのピロロ［３，２−ｄ］ピリミジン誘導体 |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6763769B2 (ja) | ウイルス感染症および他の疾病の処置のためのピロロ［３，２−ｄ］ピリミジン誘導体 | |
| JP6293765B2 (ja) | ウイルス感染症および他の疾患の処置のためのピロロ［３，２−ｄ］ピリミジン誘導体 | |
| KR102216479B1 (ko) | 바이러스 감염 또는 추가 질환의 치료를 위한 알킬피리미딘 유도체 | |
| JP2015537020A (ja) | ウイルス感染症の治療のための複素環置換２−アミノ−キナゾリン誘導体 | |
| JP6377139B2 (ja) | ウイルス感染症およびさらなる疾患の処置のためのピリドン誘導体 | |
| HK40004906A (en) | Pyrrolo[3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases | |
| HK40004906B (zh) | 用於治疗病毒感染和其他疾病的吡咯并[3，2-d]嘧啶衍生物 | |
| HK1218116B (zh) | 用於治疗病毒感染和其他疾病的吡咯并[3，2-d]嘧啶衍生物 | |
| EA040150B1 (ru) | Способ получения производных пирроло[3,2-d]пиримидина | |
| NZ714267B2 (en) | Pyrrolo[3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases | |
| NZ754320B2 (en) | Pyrrolo[3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases | |
| HK1209412B (en) | Pyrrolo[3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20170626 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20180717 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20180803 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190117 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190618 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190918 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20200212 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20200507 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20200708 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200811 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20200818 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20200910 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 6763769 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| LAPS | Cancellation because of no payment of annual fees |