JP5480637B2 - Toll様受容体(tlr7)モジュレーターとしての9−置換−8−オキソ−アデニン化合物 - Google Patents
Toll様受容体(tlr7)モジュレーターとしての9−置換−8−オキソ−アデニン化合物 Download PDFInfo
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- JP5480637B2 JP5480637B2 JP2009554081A JP2009554081A JP5480637B2 JP 5480637 B2 JP5480637 B2 JP 5480637B2 JP 2009554081 A JP2009554081 A JP 2009554081A JP 2009554081 A JP2009554081 A JP 2009554081A JP 5480637 B2 JP5480637 B2 JP 5480637B2
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- -1 9-Substituted-8-oxo-adenine compounds Chemical class 0.000 title claims description 62
- 102000002689 Toll-like receptor Human genes 0.000 title description 9
- 108020000411 Toll-like receptor Proteins 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims description 145
- 239000001257 hydrogen Substances 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 239000001301 oxygen Substances 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 239000011593 sulfur Substances 0.000 claims description 21
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 19
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 17
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 15
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
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- 150000001721 carbon Chemical group 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 7
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
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- SBZNZOHXGSHSQB-UHFFFAOYSA-N 6-amino-2-butoxy-9-(3-pyrrolidin-1-ylpropyl)-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCCN1CCCC1 SBZNZOHXGSHSQB-UHFFFAOYSA-N 0.000 claims description 5
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 5
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- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 3
- JVOHICCBACWOOI-UHFFFAOYSA-N 1-[3-(6-amino-2-butoxy-8-oxo-7h-purin-9-yl)propyl]pyrrolidine-2,5-dione Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCCN1C(=O)CCC1=O JVOHICCBACWOOI-UHFFFAOYSA-N 0.000 claims description 3
- PPTVLRSWBDCEOH-ZDUSSCGKSA-N 6-amino-2-butoxy-9-[3-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]propyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCCN1CCC[C@H]1COC PPTVLRSWBDCEOH-ZDUSSCGKSA-N 0.000 claims description 3
- ALUXLKBYDRXFMJ-NSHDSACASA-N 6-amino-2-butoxy-9-[3-[[(2s)-1-methoxypropan-2-yl]amino]propyl]-7h-purin-8-one Chemical compound CCCCOC1=NC(N)=C2NC(=O)N(CCCN[C@@H](C)COC)C2=N1 ALUXLKBYDRXFMJ-NSHDSACASA-N 0.000 claims description 3
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- 150000002829 nitrogen Chemical group 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical class O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims description 2
- YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical class O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical class C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
- 230000003612 virological effect Effects 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 2
- 239000007789 gas Substances 0.000 claims 1
- 150000003235 pyrrolidines Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000003960 organic solvent Substances 0.000 description 16
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
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EP2132209B1 (en) | 2014-02-12 |
SI2132209T1 (sl) | 2014-05-30 |
US20100130491A1 (en) | 2010-05-27 |
US8067413B2 (en) | 2011-11-29 |
DK2132209T3 (da) | 2014-04-14 |
ES2457316T3 (es) | 2014-04-25 |
WO2008114008A1 (en) | 2008-09-25 |
EP2132209A1 (en) | 2009-12-16 |
PT2132209E (pt) | 2014-04-15 |
CY1115175T1 (el) | 2016-12-14 |
EP2132209B8 (en) | 2014-04-16 |
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