JP2015537010A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2015537010A5 JP2015537010A5 JP2015542134A JP2015542134A JP2015537010A5 JP 2015537010 A5 JP2015537010 A5 JP 2015537010A5 JP 2015542134 A JP2015542134 A JP 2015542134A JP 2015542134 A JP2015542134 A JP 2015542134A JP 2015537010 A5 JP2015537010 A5 JP 2015537010A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- oxy
- ethyl
- purine
- pyrrolidin
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims 117
- -1 chloro, methyl Chemical group 0.000 claims 113
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 56
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 28
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 20
- 229910005965 SO 2 Inorganic materials 0.000 claims 18
- 125000003118 aryl group Chemical group 0.000 claims 16
- 125000001072 heteroaryl group Chemical group 0.000 claims 16
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 15
- 101100219283 Amycolatopsis orientalis cyp165C4 gene Proteins 0.000 claims 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims 13
- 125000004404 heteroalkyl group Chemical group 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 10
- 235000011962 puddings Nutrition 0.000 claims 10
- 208000006673 asthma Diseases 0.000 claims 9
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims 8
- 208000024891 symptom Diseases 0.000 claims 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 7
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 5
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 150000003857 carboxamides Chemical class 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 230000000414 obstructive effect Effects 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical compound NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- OHBFWWOPKCSSBG-UHFFFAOYSA-N (1,5-dimethylpyrazol-3-yl)-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=NN(C)C(C)=C4)=C3N=2)C)=C1C OHBFWWOPKCSSBG-UHFFFAOYSA-N 0.000 claims 1
- PNROKMGVLZFDNK-UHFFFAOYSA-N (1-aminocyclobutyl)-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound C(C)N1C2=NC=NC(=C2N=C1C=1C=NC(=NC1)C)OC1CN(CC1)C(=O)C1(CCC1)N PNROKMGVLZFDNK-UHFFFAOYSA-N 0.000 claims 1
- FGRCNXDLVXRSNJ-UHFFFAOYSA-N (1-ethyl-5-methylpyrazol-4-yl)-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound CCN1N=CC(C(=O)N2CC(CC2)OC=2C=3N=C(N(C)C=3N=CN=2)C2=C(N(CC)N=C2)C)=C1C FGRCNXDLVXRSNJ-UHFFFAOYSA-N 0.000 claims 1
- PGIIPROGPVQANM-UHFFFAOYSA-N (2,2-dimethylcyclopropyl)-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C(=O)C1CC1(C)C PGIIPROGPVQANM-UHFFFAOYSA-N 0.000 claims 1
- KLQNYIBGEORHCA-UHFFFAOYSA-N (2,2-dimethyloxan-4-yl)-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4CC(C)(C)OCC4)=C3N=2)C)=C1C KLQNYIBGEORHCA-UHFFFAOYSA-N 0.000 claims 1
- QSGNAEOTDWWUJE-UHFFFAOYSA-N (2,4-dimethyl-1,3-oxazol-5-yl)-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=C(N=C(C)O4)C)=C3N=2)C)=C1C QSGNAEOTDWWUJE-UHFFFAOYSA-N 0.000 claims 1
- MWEUBUSCQKIUNF-UHFFFAOYSA-N (2,5-dimethyl-1,3-oxazol-4-yl)-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=C(OC(C)=N4)C)=C3N=2)C)=C1C MWEUBUSCQKIUNF-UHFFFAOYSA-N 0.000 claims 1
- FRHULUHOEAUCTL-UHFFFAOYSA-N (2,5-dimethylpyrazol-3-yl)-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4N(N=C(C)C=4)C)=C3N=2)C)=C1C FRHULUHOEAUCTL-UHFFFAOYSA-N 0.000 claims 1
- OTYFUFVMASKSGG-GTPINHCMSA-N (2-aminocyclopentyl)-[(3S)-3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound C(C)N1C2=NC=NC(=C2N=C1C=1C=NC(=NC1)C)O[C@@H]1CN(CC1)C(=O)C1C(CCC1)N OTYFUFVMASKSGG-GTPINHCMSA-N 0.000 claims 1
- OTYFUFVMASKSGG-UHFFFAOYSA-N (2-aminocyclopentyl)-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound C(C)N1C2=NC=NC(=C2N=C1C=1C=NC(=NC1)C)OC1CN(CC1)C(=O)C1C(CCC1)N OTYFUFVMASKSGG-UHFFFAOYSA-N 0.000 claims 1
- ZXMXDYRAOHNSID-UHFFFAOYSA-N (2-ethyl-4-methyl-1,3-oxazol-5-yl)-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound O1C(CC)=NC(C)=C1C(=O)N1CC(OC=2C=3N=C(N(C)C=3N=CN=2)C2=C(N(CC)N=C2)C)CC1 ZXMXDYRAOHNSID-UHFFFAOYSA-N 0.000 claims 1
- NOQYZZAMKVKFBE-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=C(ON=C4)C4CC4)=C3N=2)C)=C1C NOQYZZAMKVKFBE-UHFFFAOYSA-N 0.000 claims 1
- NPCWYNYDQODUOF-UHFFFAOYSA-N (5-tert-butyl-2-methylpyrazol-3-yl)-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4N(N=C(C=4)C(C)(C)C)C)=C3N=2)C)=C1C NPCWYNYDQODUOF-UHFFFAOYSA-N 0.000 claims 1
- CJHWIWKMOZGSGW-UHFFFAOYSA-N (7-chloro-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=NN5C=CC(Cl)=CC5=N4)=C3N=2)C)=C1C CJHWIWKMOZGSGW-UHFFFAOYSA-N 0.000 claims 1
- JFILSIUJMUUEQZ-UHFFFAOYSA-N 1-[2-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-2-oxoethyl]pyrrolidin-2-one Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)CN4C(CCC4)=O)=C3N=2)C)=C1C JFILSIUJMUUEQZ-UHFFFAOYSA-N 0.000 claims 1
- ZKQNLXGACSUWHP-UHFFFAOYSA-N 1-[3-(8-cyclopropyl-9-methylpurin-6-yl)oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C1CC1)N2C ZKQNLXGACSUWHP-UHFFFAOYSA-N 0.000 claims 1
- FBVXSZSWFRWVJX-UHFFFAOYSA-N 1-[3-(8-iodo-9-methylpurin-6-yl)oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(I)N2C FBVXSZSWFRWVJX-UHFFFAOYSA-N 0.000 claims 1
- CAZFONWKQPHLRR-UHFFFAOYSA-N 1-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxycyclopentyl]-3h-imidazo[4,5-b]pyridin-2-one Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CC(CC4)N4C(NC5=NC=CC=C54)=O)=C3N=2)C)=C1C CAZFONWKQPHLRR-UHFFFAOYSA-N 0.000 claims 1
- AJKPXWUEXCBUNA-UHFFFAOYSA-N 1-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-2,2-dimethylpropan-1-one Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C(C)(C)C)=C3N=2)C)=C1C AJKPXWUEXCBUNA-UHFFFAOYSA-N 0.000 claims 1
- UOAMKQFWHKPGKT-UHFFFAOYSA-N 1-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-2-(oxan-4-yl)ethanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)CC4CCOCC4)=C3N=2)C)=C1C UOAMKQFWHKPGKT-UHFFFAOYSA-N 0.000 claims 1
- NQMHBTBFIFFCDC-UHFFFAOYSA-N 1-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-2-methoxyethanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)COC)=C3N=2)C)=C1C NQMHBTBFIFFCDC-UHFFFAOYSA-N 0.000 claims 1
- YPUJIRHWVUBMAH-UHFFFAOYSA-N 1-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-2-methylpropan-1-one Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C(C)C)=C3N=2)C)=C1C YPUJIRHWVUBMAH-UHFFFAOYSA-N 0.000 claims 1
- UFAYXAFDXOSECP-UHFFFAOYSA-N 1-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]ethanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(C)=O)=C3N=2)C)=C1C UFAYXAFDXOSECP-UHFFFAOYSA-N 0.000 claims 1
- CJDZRXISHKCVRN-UHFFFAOYSA-N 1-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]phthalazine Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C=4C5=CC=CC=C5C=NN=4)=C3N=2)C)=C1C CJDZRXISHKCVRN-UHFFFAOYSA-N 0.000 claims 1
- MNGYUMAPTXRHRH-UHFFFAOYSA-N 1-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C1=C(N(CC)N=C1)C)N2C MNGYUMAPTXRHRH-UHFFFAOYSA-N 0.000 claims 1
- LXSZAJKBUWKMOT-UHFFFAOYSA-N 1-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]sulfanylpyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1SC1=NC=NC2=C1N=C(C1=C(N(CC)N=C1)C)N2C LXSZAJKBUWKMOT-UHFFFAOYSA-N 0.000 claims 1
- VZEGOWGYVVJIRL-UHFFFAOYSA-N 1-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]sulfonylpyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1S(=O)(=O)C1=NC=NC2=C1N=C(C1=C(N(CC)N=C1)C)N2C VZEGOWGYVVJIRL-UHFFFAOYSA-N 0.000 claims 1
- CFUCFPVYEDQNTK-UHFFFAOYSA-N 1-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-propylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound N1=CN=C2N(CCC)C(C3=C(N(CC)N=C3)C)=NC2=C1OC1CCN(C(=O)CC)C1 CFUCFPVYEDQNTK-UHFFFAOYSA-N 0.000 claims 1
- JBZHXXPKJHJKGS-UHFFFAOYSA-N 1-[3-[8-(1-tert-butylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C1=CN(N=C1)C(C)(C)C)N2C JBZHXXPKJHJKGS-UHFFFAOYSA-N 0.000 claims 1
- MAGPRRMLAMDPPE-UHFFFAOYSA-N 1-[3-[8-(1h-indazol-5-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=C3C=NNC3=CC=1)N2C MAGPRRMLAMDPPE-UHFFFAOYSA-N 0.000 claims 1
- JGCKEPAGXKCVDS-UHFFFAOYSA-N 1-[3-[8-(1h-indazol-6-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=C3NN=CC3=CC=1)N2C JGCKEPAGXKCVDS-UHFFFAOYSA-N 0.000 claims 1
- BLBBNQVTYJJHDE-UHFFFAOYSA-N 1-[3-[8-(1h-indol-5-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=C3C=CNC3=CC=1)N2C BLBBNQVTYJJHDE-UHFFFAOYSA-N 0.000 claims 1
- BGYCJOBUBJHUBY-UHFFFAOYSA-N 1-[3-[8-(1h-indol-6-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=C3NC=CC3=CC=1)N2C BGYCJOBUBJHUBY-UHFFFAOYSA-N 0.000 claims 1
- IYBXWBAUMUJBPB-UHFFFAOYSA-N 1-[3-[8-(2,3-dimethylphenoxy)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(OC=1C(=C(C)C=CC=1)C)N2C IYBXWBAUMUJBPB-UHFFFAOYSA-N 0.000 claims 1
- AQYCUMQONQZZEU-UHFFFAOYSA-N 1-[3-[8-(2-methylpyrimidin-5-yl)-9-propylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound N1=CN=C2N(CCC)C(C=3C=NC(C)=NC=3)=NC2=C1OC1CCN(C(=O)CC)C1 AQYCUMQONQZZEU-UHFFFAOYSA-N 0.000 claims 1
- JTHONZVZMDZBJR-UHFFFAOYSA-N 1-[3-[8-(2-tert-butyl-1,3-thiazol-5-yl)-9-ethylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C(C)(C)(C)C=1SC(=CN1)C=1N(C2=NC=NC(=C2N1)OC1CN(CC1)C(CC)=O)CC JTHONZVZMDZBJR-UHFFFAOYSA-N 0.000 claims 1
- KZVLUYWRJIUXEP-UHFFFAOYSA-N 1-[3-[8-(2-tert-butyl-1,3-thiazol-5-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1SC(=NC=1)C(C)(C)C)N2C KZVLUYWRJIUXEP-UHFFFAOYSA-N 0.000 claims 1
- NQSSKRZDCWPXMA-UHFFFAOYSA-N 1-[3-[8-(3,6-dihydro-2h-pyran-4-yl)-9-ethylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1CCOCC=1)N2CC NQSSKRZDCWPXMA-UHFFFAOYSA-N 0.000 claims 1
- IDQMQFUODDQCGQ-UHFFFAOYSA-N 1-[3-[8-(3-fluoro-4-methoxyphenoxy)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(OC=1C=C(F)C(OC)=CC=1)N2C IDQMQFUODDQCGQ-UHFFFAOYSA-N 0.000 claims 1
- YDOQNNQYXJGZFF-UHFFFAOYSA-N 1-[3-[8-(3-fluoro-4-methoxyphenyl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=C(F)C(OC)=CC=1)N2C YDOQNNQYXJGZFF-UHFFFAOYSA-N 0.000 claims 1
- SYBCUOVCLVVGGZ-UHFFFAOYSA-N 1-[3-[8-(3-fluoro-5-hydroxyphenyl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=C(F)C=C(O)C=1)N2C SYBCUOVCLVVGGZ-UHFFFAOYSA-N 0.000 claims 1
- XPWCASWTMFFOAW-UHFFFAOYSA-N 1-[3-[8-(3-fluoro-5-methoxyphenoxy)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(OC=1C=C(OC)C=C(F)C=1)N2C XPWCASWTMFFOAW-UHFFFAOYSA-N 0.000 claims 1
- QQYOXUCLCCYTCB-UHFFFAOYSA-N 1-[3-[8-(4-methoxy-3-methylphenyl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=C(C)C(OC)=CC=1)N2C QQYOXUCLCCYTCB-UHFFFAOYSA-N 0.000 claims 1
- GAJGCKUQEDUZLE-UHFFFAOYSA-N 1-[3-[8-(5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-3-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C1=C3CCCN3N=C1)N2C GAJGCKUQEDUZLE-UHFFFAOYSA-N 0.000 claims 1
- UYHMJQWCKNOWPI-UHFFFAOYSA-N 1-[3-[8-(5-aminopyridin-3-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=C(N)C=NC=1)N2C UYHMJQWCKNOWPI-UHFFFAOYSA-N 0.000 claims 1
- BRCHZFYEKARLPL-UHFFFAOYSA-N 1-[3-[8-(5-fluoro-6-methoxypyridin-3-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=C(F)C(OC)=NC=1)N2C BRCHZFYEKARLPL-UHFFFAOYSA-N 0.000 claims 1
- GTKSBHRIRKXPRM-UHFFFAOYSA-N 1-[3-[8-(6-chloropyridin-3-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=NC(Cl)=CC=1)N2C GTKSBHRIRKXPRM-UHFFFAOYSA-N 0.000 claims 1
- QSQWBLGJRMXEAK-UHFFFAOYSA-N 1-[3-[8-(6-methoxy-5-methylpyridin-3-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound COC1=C(C=C(C=N1)C=1N(C2=NC=NC(=C2N1)OC1CN(CC1)C(CC)=O)C)C QSQWBLGJRMXEAK-UHFFFAOYSA-N 0.000 claims 1
- SHSWEZJMUGMIGS-UHFFFAOYSA-N 1-[3-[8-(6-methoxypyridin-3-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=NC(OC)=CC=1)N2C SHSWEZJMUGMIGS-UHFFFAOYSA-N 0.000 claims 1
- DUAHEWVIPDLLGK-UHFFFAOYSA-N 1-[3-[8-(difluoromethyl)-9-ethylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C(F)F)N2CC DUAHEWVIPDLLGK-UHFFFAOYSA-N 0.000 claims 1
- MHJGPHWENGUXEN-UHFFFAOYSA-N 1-[3-[8-[4-methoxy-3-(trifluoromethyl)phenyl]-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=C(C(OC)=CC=1)C(F)(F)F)N2C MHJGPHWENGUXEN-UHFFFAOYSA-N 0.000 claims 1
- XGRMAKCCLMTNRD-UHFFFAOYSA-N 1-[3-[8-[6-methoxy-5-(trifluoromethyl)pyridin-3-yl]-9-methylpurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound COC1=C(C=C(C=N1)C=1N(C2=NC=NC(=C2N1)OC1CN(CC1)C(CC)=O)C)C(F)(F)F XGRMAKCCLMTNRD-UHFFFAOYSA-N 0.000 claims 1
- IGYUICHDHPDRRX-UHFFFAOYSA-N 1-[3-[9-cyclopropyl-8-(1-ethyl-5-methylpyrazol-4-yl)purin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C1=C(N(CC)N=C1)C)N2C1CC1 IGYUICHDHPDRRX-UHFFFAOYSA-N 0.000 claims 1
- JYZPZLYBEYSKAY-UHFFFAOYSA-N 1-[3-[9-ethyl-8-(1-ethyl-5-methylpyrazol-4-yl)purin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C1=C(N(CC)N=C1)C)N2CC JYZPZLYBEYSKAY-UHFFFAOYSA-N 0.000 claims 1
- NYHAFWSIXMKBSR-UHFFFAOYSA-N 1-[3-[9-ethyl-8-(2-methylpropyl)purin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(CC(C)C)N2CC NYHAFWSIXMKBSR-UHFFFAOYSA-N 0.000 claims 1
- AZBPJWIFVPUIAI-UHFFFAOYSA-N 1-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]-3-methylbut-2-en-1-one Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC1CCN(C(=O)C=C(C)C)C1 AZBPJWIFVPUIAI-UHFFFAOYSA-N 0.000 claims 1
- YNOLINLXOHNAOX-UHFFFAOYSA-N 1-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=NC(C)=NC=1)N2CC YNOLINLXOHNAOX-UHFFFAOYSA-N 0.000 claims 1
- RNJZPAKBVTUDGV-UHFFFAOYSA-N 1-[3-[9-ethyl-8-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-yl)purin-6-yl]oxypyrrolidin-1-yl]-2-methylpropan-1-one Chemical compound N1=CN=C2N(CC)C(C3=C4CCCCN4N=C3)=NC2=C1OC1CCN(C(=O)C(C)C)C1 RNJZPAKBVTUDGV-UHFFFAOYSA-N 0.000 claims 1
- QXFTUJTUBUSHAI-UHFFFAOYSA-N 1-[3-[9-ethyl-8-(5-fluoro-6-methoxypyridin-3-yl)purin-6-yl]oxypyrrolidin-1-yl]-2-methylpropan-1-one Chemical compound N1=CN=C2N(CC)C(C=3C=C(F)C(OC)=NC=3)=NC2=C1OC1CCN(C(=O)C(C)C)C1 QXFTUJTUBUSHAI-UHFFFAOYSA-N 0.000 claims 1
- URFIWTIRLSPDOP-UHFFFAOYSA-N 1-[3-[9-ethyl-8-(6-methoxy-5-methylpyridin-3-yl)purin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=C(C)C(OC)=NC=1)N2CC URFIWTIRLSPDOP-UHFFFAOYSA-N 0.000 claims 1
- YSNFQMYIOFYSQP-UHFFFAOYSA-N 1-[3-[9-ethyl-8-(6-methoxypyridin-3-yl)purin-6-yl]oxypyrrolidin-1-yl]-2-methylpropan-1-one Chemical compound N1=CN=C2N(CC)C(C=3C=NC(OC)=CC=3)=NC2=C1OC1CCN(C(=O)C(C)C)C1 YSNFQMYIOFYSQP-UHFFFAOYSA-N 0.000 claims 1
- PZNJWWCYQHJKQH-UHFFFAOYSA-N 1-[3-[9-ethyl-8-(trifluoromethyl)purin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C(F)(F)F)N2CC PZNJWWCYQHJKQH-UHFFFAOYSA-N 0.000 claims 1
- PECPLZJZYKUHKH-UHFFFAOYSA-N 1-[3-[9-methyl-8-(1-phenylpyrazol-4-yl)purin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C1=CN(N=C1)C=1C=CC=CC=1)N2C PECPLZJZYKUHKH-UHFFFAOYSA-N 0.000 claims 1
- XRLPGPKYSLXLEM-UHFFFAOYSA-N 1-[3-[9-methyl-8-(1h-pyrrolo[2,3-b]pyridin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=C3C=CNC3=NC=1)N2C XRLPGPKYSLXLEM-UHFFFAOYSA-N 0.000 claims 1
- BLIKUWWKRGOCGS-UHFFFAOYSA-N 1-[3-[9-methyl-8-(2-methylpropyl)purin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(CC(C)C)N2C BLIKUWWKRGOCGS-UHFFFAOYSA-N 0.000 claims 1
- VLXPWSLFJZYRMM-UHFFFAOYSA-N 1-[3-[9-methyl-8-(2-methylpyrimidin-5-yl)oxypurin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(OC=1C=NC(C)=NC=1)N2C VLXPWSLFJZYRMM-UHFFFAOYSA-N 0.000 claims 1
- HJUDSEREIMMUTN-UHFFFAOYSA-N 1-[3-[9-methyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=NC(C)=NC=1)N2C HJUDSEREIMMUTN-UHFFFAOYSA-N 0.000 claims 1
- GEUYQVAHKSANAT-UHFFFAOYSA-N 1-[3-[9-methyl-8-(3-methyl-2h-pyrazolo[3,4-b]pyridin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C1=CC3=C(C)NN=C3N=C1)N2C GEUYQVAHKSANAT-UHFFFAOYSA-N 0.000 claims 1
- YKZHMKAMGZQYLG-UHFFFAOYSA-N 1-[3-[9-methyl-8-(4-methylsulfonylphenyl)purin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=CC(=CC=1)S(C)(=O)=O)N2C YKZHMKAMGZQYLG-UHFFFAOYSA-N 0.000 claims 1
- AQEIWFRZEFTHIM-UHFFFAOYSA-N 1-[3-[9-methyl-8-(5-methyl-1-phenylpyrazol-4-yl)purin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C1=C(N(N=C1)C=1C=CC=CC=1)C)N2C AQEIWFRZEFTHIM-UHFFFAOYSA-N 0.000 claims 1
- CGMBLXAYLNQDKR-UHFFFAOYSA-N 1-[3-[9-methyl-8-(6-methylpyridin-3-yl)purin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=NC(C)=CC=1)N2C CGMBLXAYLNQDKR-UHFFFAOYSA-N 0.000 claims 1
- QXCDAKCDUTWWFF-UHFFFAOYSA-N 1-[3-[9-methyl-8-(trifluoromethyl)purin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C(F)(F)F)N2C QXCDAKCDUTWWFF-UHFFFAOYSA-N 0.000 claims 1
- FQHFXMMUJZNMJR-UHFFFAOYSA-N 1-[3-[9-methyl-8-[6-(trifluoromethyl)pyridin-3-yl]purin-6-yl]oxypyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=NC(=CC=1)C(F)(F)F)N2C FQHFXMMUJZNMJR-UHFFFAOYSA-N 0.000 claims 1
- WJCVCEFMJZIVDX-UHFFFAOYSA-N 1-[3-[[8-(1-ethyl-5-methylpyrazol-4-yl)-7h-purin-6-yl]oxy]pyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1NC(C1=C(N(CC)N=C1)C)=N2 WJCVCEFMJZIVDX-UHFFFAOYSA-N 0.000 claims 1
- LYTDGSQZQNZFER-UHFFFAOYSA-N 1-[3-[[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]methyl]pyrrolidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC1CC1=NC=NC2=C1N=C(C1=C(N(CC)N=C1)C)N2C LYTDGSQZQNZFER-UHFFFAOYSA-N 0.000 claims 1
- ZDGNLHKLCQVHPS-UHFFFAOYSA-N 1-[4-[8-(1-ethyl-5-methylpyrazol-3-yl)-9-methylpurin-6-yl]oxypiperidin-1-yl]propan-1-one Chemical compound C1CN(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C1=NN(CC)C(C)=C1)N2C ZDGNLHKLCQVHPS-UHFFFAOYSA-N 0.000 claims 1
- VZSUUNJLYMOIBJ-UHFFFAOYSA-N 1-azabicyclo[2.2.1]heptan-3-yl-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N=1C2=C(OC3CN(CC3)C(=O)C3C4CCN(C4)C3)N=CN=C2N(CC)C=1C1=CN=C(C)N=C1 VZSUUNJLYMOIBJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 1
- HIANLXNMWIDTCX-UHFFFAOYSA-N 2-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]-1,3-thiazole Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C1=NC=CS1 HIANLXNMWIDTCX-UHFFFAOYSA-N 0.000 claims 1
- NXLBIAAHKPNXPP-UHFFFAOYSA-N 2-amino-1-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]-3-methylbutan-1-one Chemical class N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC1CCN(C(=O)C(N)C(C)C)C1 NXLBIAAHKPNXPP-UHFFFAOYSA-N 0.000 claims 1
- OXQQJJYRHLUXHI-UHFFFAOYSA-N 2-methoxy-5-[9-methyl-6-(1-propanoylpyrrolidin-3-yl)oxypurin-8-yl]pyridine-3-carbonitrile Chemical compound C1N(C(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=C(C(OC)=NC=1)C#N)N2C OXQQJJYRHLUXHI-UHFFFAOYSA-N 0.000 claims 1
- QJKJUXRZTOWZBB-UHFFFAOYSA-N 3-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-3-oxopropanenitrile Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)CC#N)=C3N=2)C)=C1C QJKJUXRZTOWZBB-UHFFFAOYSA-N 0.000 claims 1
- GIVOGGAEBFBQRY-UHFFFAOYSA-N 3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-n-methyl-n-phenylpyrrolidine-1-carboxamide Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C(=O)N(C)C1=CC=CC=C1 GIVOGGAEBFBQRY-UHFFFAOYSA-N 0.000 claims 1
- YCZLOSZVWPFBAR-UHFFFAOYSA-N 3-amino-1-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]-3-methylbutan-1-one Chemical class N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC1CCN(C(=O)CC(C)(C)N)C1 YCZLOSZVWPFBAR-UHFFFAOYSA-N 0.000 claims 1
- DCKLNIRVTBDYPE-UHFFFAOYSA-N 3-azabicyclo[3.1.0]hexan-3-yl-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound C12CN(CC2C1)C(=O)N1CC(CC1)OC1=C2N=C(N(C2=NC=N1)CC)C=1C=NC(=NC1)C DCKLNIRVTBDYPE-UHFFFAOYSA-N 0.000 claims 1
- HJXPUTJZHJHDIW-UHFFFAOYSA-N 4-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-5,6-dimethylthieno[2,3-d]pyrimidine Chemical compound CC1=C(SC=2N=CN=C(C21)N2CC(CC2)OC2=C1N=C(N(C1=NC=N2)C)C=2C=NN(C2C)CC)C HJXPUTJZHJHDIW-UHFFFAOYSA-N 0.000 claims 1
- SMKMVJITZFZUHT-UHFFFAOYSA-N 4-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-6-methylthieno[2,3-d]pyrimidine Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C=4C=5C=C(C)SC=5N=CN=4)=C3N=2)C)=C1C SMKMVJITZFZUHT-UHFFFAOYSA-N 0.000 claims 1
- GORRNJPEZPWAHW-UHFFFAOYSA-N 4-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]thieno[2,3-d]pyrimidine Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C=4C=5C=CSC=5N=CN=4)=C3N=2)C)=C1C GORRNJPEZPWAHW-UHFFFAOYSA-N 0.000 claims 1
- JGRNBZQSDIECNJ-UHFFFAOYSA-N 4-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]thieno[3,2-c]pyridine Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C=4C=5C=CSC=5C=CN=4)=C3N=2)C)=C1C JGRNBZQSDIECNJ-UHFFFAOYSA-N 0.000 claims 1
- PCYJGFKHOZGVLF-UHFFFAOYSA-N 4-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]thieno[3,2-d]pyrimidine Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C=4C=5SC=CC=5N=CN=4)=C3N=2)C)=C1C PCYJGFKHOZGVLF-UHFFFAOYSA-N 0.000 claims 1
- DBIYNEBQDMJZTP-UHFFFAOYSA-N 4-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidine-1-carbonyl]-1-methylpyrrolidin-2-one Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4CC(=O)N(C)C4)=C3N=2)C)=C1C DBIYNEBQDMJZTP-UHFFFAOYSA-N 0.000 claims 1
- NXLPLGKPNPLLSM-UHFFFAOYSA-N 4-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidine-1-carbonyl]-1-propan-2-ylpyrrolidin-2-one Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4CC(=O)N(C(C)C)C4)=C3N=2)C)=C1C NXLPLGKPNPLLSM-UHFFFAOYSA-N 0.000 claims 1
- BHXHOQNSZIVOER-UHFFFAOYSA-N 4-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-n-methyl-n-phenylpiperidine-1-carboxamide Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(CC1)CCN1C(=O)N(C)C1=CC=CC=C1 BHXHOQNSZIVOER-UHFFFAOYSA-N 0.000 claims 1
- SKZVKQWUGHCGFA-UHFFFAOYSA-N 4-[[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]methyl]-n,n-dimethylaniline Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC=5C=CC(=CC=5)N(C)C)CC4)=C3N=2)C)=C1C SKZVKQWUGHCGFA-UHFFFAOYSA-N 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- KLCCBXRSFBQLRF-UHFFFAOYSA-N 5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-2-yl-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=NN5CCCC5=C4)=C3N=2)C)=C1C KLCCBXRSFBQLRF-UHFFFAOYSA-N 0.000 claims 1
- XIKVRCRSYNDODR-UHFFFAOYSA-N 5-[6-[1-(cyclopropanecarbonyl)pyrrolidin-3-yl]oxy-9-ethylpurin-8-yl]-2-methoxypyridine-3-carbonitrile Chemical compound N1=CN=C2N(CC)C(C=3C=C(C(OC)=NC=3)C#N)=NC2=C1OC(C1)CCN1C(=O)C1CC1 XIKVRCRSYNDODR-UHFFFAOYSA-N 0.000 claims 1
- WCCIVXASQYQVAW-UHFFFAOYSA-N 6,7-dihydro-5h-pyrrolo[2,1-e]tetrazol-5-yl-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4N5N=NN=C5CC4)=C3N=2)C)=C1C WCCIVXASQYQVAW-UHFFFAOYSA-N 0.000 claims 1
- HLQYMJBLZXMUMO-UHFFFAOYSA-N 6-(1-benzyl-4,4-dimethylpyrrolidin-3-yl)oxy-9-ethyl-8-(2-methylpyrimidin-5-yl)purine Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C(C1)(C)C)CN1CC1=CC=CC=C1 HLQYMJBLZXMUMO-UHFFFAOYSA-N 0.000 claims 1
- AZIYARCXGAAJGS-UHFFFAOYSA-N 6-[1-(benzenesulfonyl)pyrrolidin-3-yl]oxy-8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurine Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)S(=O)(=O)C=4C=CC=CC=4)=C3N=2)C)=C1C AZIYARCXGAAJGS-UHFFFAOYSA-N 0.000 claims 1
- CKPOONGEBVSGTO-UHFFFAOYSA-N 6-[1-(cyclohexylmethyl)pyrrolidin-3-yl]oxy-8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurine Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC5CCCCC5)CC4)=C3N=2)C)=C1C CKPOONGEBVSGTO-UHFFFAOYSA-N 0.000 claims 1
- SQLQTBDMRKDKPE-UHFFFAOYSA-N 6-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]-1,2-benzoxazole Chemical compound N=1C2=C(OC3CN(CC3)C=3C=C4ON=CC4=CC=3)N=CN=C2N(CC)C=1C1=CN=C(C)N=C1 SQLQTBDMRKDKPE-UHFFFAOYSA-N 0.000 claims 1
- GPXGDBXSVGSXSC-UHFFFAOYSA-N 8-(1-ethyl-5-methylpyrazol-4-yl)-6-(1-ethylsulfonylpyrrolidin-3-yl)oxy-9-methylpurine Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)S(=O)(=O)CC)=C3N=2)C)=C1C GPXGDBXSVGSXSC-UHFFFAOYSA-N 0.000 claims 1
- KGKUWEHPOFCBIP-UHFFFAOYSA-N 8-(1-ethyl-5-methylpyrazol-4-yl)-6-[1-[4-(furan-2-yl)pyrimidin-2-yl]pyrrolidin-3-yl]oxy-9-methylpurine Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C=4N=C(C=CN=4)C=4OC=CC=4)=C3N=2)C)=C1C KGKUWEHPOFCBIP-UHFFFAOYSA-N 0.000 claims 1
- NEKGHGLTYMSTER-UHFFFAOYSA-N 8-(1-ethyl-5-methylpyrazol-4-yl)-9-methyl-6-(1-naphthalen-2-ylsulfonylpyrrolidin-3-yl)oxypurine Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)S(=O)(=O)C=4C=C5C=CC=CC5=CC=4)=C3N=2)C)=C1C NEKGHGLTYMSTER-UHFFFAOYSA-N 0.000 claims 1
- OLNWYVKNFPNTJB-UHFFFAOYSA-N 8-(1-ethyl-5-methylpyrazol-4-yl)-9-methyl-6-(1-propylpyrrolidin-3-yl)oxypurine Chemical compound C1N(CCC)CCC1OC1=NC=NC2=C1N=C(C1=C(N(CC)N=C1)C)N2C OLNWYVKNFPNTJB-UHFFFAOYSA-N 0.000 claims 1
- BIKKSFLJMFTBII-UHFFFAOYSA-N 8-(1-ethyl-5-methylpyrazol-4-yl)-9-methyl-6-(1-pyridin-2-ylpyrrolidin-3-yl)oxypurine Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C=4N=CC=CC=4)=C3N=2)C)=C1C BIKKSFLJMFTBII-UHFFFAOYSA-N 0.000 claims 1
- BWSAUFHWENVRHX-UHFFFAOYSA-N 8-(1-ethyl-5-methylpyrazol-4-yl)-9-methyl-6-(1-pyrimidin-2-ylpyrrolidin-3-yl)oxypurine Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C=4N=CC=CN=4)=C3N=2)C)=C1C BWSAUFHWENVRHX-UHFFFAOYSA-N 0.000 claims 1
- ROWKBLNPTYYUKN-UHFFFAOYSA-N 8-(1-ethyl-5-methylpyrazol-4-yl)-9-methyl-6-(1-pyrimidin-4-ylpyrrolidin-3-yl)sulfanylpurine Chemical compound CCN1N=CC(C=2N(C3=NC=NC(SC4CN(CC4)C=4N=CN=CC=4)=C3N=2)C)=C1C ROWKBLNPTYYUKN-UHFFFAOYSA-N 0.000 claims 1
- WJIDJVIPFNAEJB-UHFFFAOYSA-N 8-(1-ethyl-5-methylpyrazol-4-yl)-9-methyl-6-[1-(1-methylpyrazolo[3,4-d]pyrimidin-4-yl)pyrrolidin-3-yl]oxypurine Chemical compound CCn1ncc(c1C)-c1nc2c(OC3CCN(C3)c3ncnc4n(C)ncc34)ncnc2n1C WJIDJVIPFNAEJB-UHFFFAOYSA-N 0.000 claims 1
- GNUJYQONAMTRSL-UHFFFAOYSA-N 8-(1-ethyl-5-methylpyrazol-4-yl)-9-methyl-6-[1-(1-phenylethyl)pyrrolidin-3-yl]oxypurine Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(C)C=4C=CC=CC=4)=C3N=2)C)=C1C GNUJYQONAMTRSL-UHFFFAOYSA-N 0.000 claims 1
- LGXZSQQRXQEAAK-UHFFFAOYSA-N 8-(1-ethyl-5-methylpyrazol-4-yl)-9-methyl-6-[1-(4-phenylphenyl)sulfonylpyrrolidin-3-yl]oxypurine Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)S(=O)(=O)C=4C=CC(=CC=4)C=4C=CC=CC=4)=C3N=2)C)=C1C LGXZSQQRXQEAAK-UHFFFAOYSA-N 0.000 claims 1
- SMPYDQDWYOWFDN-UHFFFAOYSA-N 8-(1-ethyl-5-methylpyrazol-4-yl)-9-methyl-6-[1-(6-pyrazol-1-ylpyrimidin-4-yl)pyrrolidin-3-yl]oxypurine Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C=4N=CN=C(C=4)N4N=CC=C4)=C3N=2)C)=C1C SMPYDQDWYOWFDN-UHFFFAOYSA-N 0.000 claims 1
- YAAJRVOMNMWRSY-UHFFFAOYSA-N 8-(1-ethyl-5-methylpyrazol-4-yl)-9-methyl-6-[1-(trifluoromethylsulfonyl)pyrrolidin-3-yl]oxypurine Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N1)OC1CN(CC1)S(=O)(=O)C(F)(F)F)C YAAJRVOMNMWRSY-UHFFFAOYSA-N 0.000 claims 1
- ORINDVMYWAOEQW-UHFFFAOYSA-N 8-(1-ethyl-5-methylpyrazol-4-yl)-9-methyl-6-[1-[4-(trifluoromethyl)pyridin-2-yl]pyrrolidin-3-yl]oxypurine Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C=4N=CC=C(C=4)C(F)(F)F)=C3N=2)C)=C1C ORINDVMYWAOEQW-UHFFFAOYSA-N 0.000 claims 1
- CWWDHYLFFAUMFN-UHFFFAOYSA-N 8-(1-ethyl-5-methylpyrazol-4-yl)-9-methyl-6-pyrrolidin-3-yloxypurine Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CNCC4)=C3N=2)C)=C1C CWWDHYLFFAUMFN-UHFFFAOYSA-N 0.000 claims 1
- NSYZIWZUEJHJHC-UHFFFAOYSA-N 9-ethyl-6-(1-ethylsulfonylpyrrolidin-3-yl)oxy-8-(2-methylpyrimidin-5-yl)purine Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC1CCN(S(=O)(=O)CC)C1 NSYZIWZUEJHJHC-UHFFFAOYSA-N 0.000 claims 1
- IFFAUMIRKQDPET-UHFFFAOYSA-N 9-ethyl-6-[1-(2-methylphenyl)pyrrolidin-3-yl]oxy-8-(2-methylpyrimidin-5-yl)purine Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C1=CC=CC=C1C IFFAUMIRKQDPET-UHFFFAOYSA-N 0.000 claims 1
- SDCKOAWCRDBNAB-UHFFFAOYSA-N 9-ethyl-6-[1-(3-fluorophenyl)pyrrolidin-3-yl]oxy-8-(2-methylpyrimidin-5-yl)purine Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C1=CC=CC(F)=C1 SDCKOAWCRDBNAB-UHFFFAOYSA-N 0.000 claims 1
- NMRXFPLAALTHGX-UHFFFAOYSA-N 9-ethyl-6-[1-(3-methoxyazetidine-1-carbonyl)pyrrolidin-3-yl]oxy-n-(2,2,2-trifluoroethyl)purine-8-carboxamide Chemical compound N1=CN=C2N(CC)C(C(=O)NCC(F)(F)F)=NC2=C1OC(C1)CCN1C(=O)N1CC(OC)C1 NMRXFPLAALTHGX-UHFFFAOYSA-N 0.000 claims 1
- ODVVLUBUZHEIGH-UHFFFAOYSA-N 9-ethyl-6-[1-(4-fluorophenyl)pyrrolidin-3-yl]oxy-8-(2-methylpyrimidin-5-yl)purine Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C1=CC=C(F)C=C1 ODVVLUBUZHEIGH-UHFFFAOYSA-N 0.000 claims 1
- AYYVRZSTWQLNCQ-UHFFFAOYSA-N 9-ethyl-6-[1-(4-methylpyridin-2-yl)pyrrolidin-3-yl]oxy-8-(2-methylpyrimidin-5-yl)purine Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C1=CC(C)=CC=N1 AYYVRZSTWQLNCQ-UHFFFAOYSA-N 0.000 claims 1
- HCCKZLORQINBOV-UHFFFAOYSA-N 9-ethyl-8-(2-methylpyrimidin-5-yl)-6-(1-phenylpyrrolidin-3-yl)oxypurine Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C1=CC=CC=C1 HCCKZLORQINBOV-UHFFFAOYSA-N 0.000 claims 1
- SZBMHDCOVGGKPI-UHFFFAOYSA-N 9-ethyl-8-(2-methylpyrimidin-5-yl)-6-(1-pyrazin-2-ylpyrrolidin-3-yl)oxypurine Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C1=CN=CC=N1 SZBMHDCOVGGKPI-UHFFFAOYSA-N 0.000 claims 1
- XNJSHIQIUVFZLL-UHFFFAOYSA-N 9-ethyl-8-(2-methylpyrimidin-5-yl)-6-(1-pyridin-2-ylpiperidin-3-yl)oxypurine Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCCN1C1=CC=CC=N1 XNJSHIQIUVFZLL-UHFFFAOYSA-N 0.000 claims 1
- XDAONEQQEZTBBL-UHFFFAOYSA-N 9-ethyl-8-(2-methylpyrimidin-5-yl)-6-(1-pyridin-2-ylpyrrolidin-3-yl)oxypurine Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C1=CC=CC=N1 XDAONEQQEZTBBL-UHFFFAOYSA-N 0.000 claims 1
- QZZFFVIJUPQWRU-UHFFFAOYSA-N 9-ethyl-8-(2-methylpyrimidin-5-yl)-6-(1-pyridin-3-ylpyrrolidin-3-yl)oxypurine Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C1=CC=CN=C1 QZZFFVIJUPQWRU-UHFFFAOYSA-N 0.000 claims 1
- PUWPBXQOVDGQMG-UHFFFAOYSA-N 9-ethyl-8-(2-methylpyrimidin-5-yl)-6-(1-pyrimidin-5-ylpyrrolidin-3-yl)oxypurine Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C1=CN=CN=C1 PUWPBXQOVDGQMG-UHFFFAOYSA-N 0.000 claims 1
- 208000000884 Airway Obstruction Diseases 0.000 claims 1
- KBEIETXSNRIMCY-UHFFFAOYSA-N C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N1)OC1CN(CC1)C(=O)C1=C2N(N=C1)C=CN2)C Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N1)OC1CN(CC1)C(=O)C1=C2N(N=C1)C=CN2)C KBEIETXSNRIMCY-UHFFFAOYSA-N 0.000 claims 1
- GSDOQSDHVVBCFZ-UHFFFAOYSA-N C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N1)OC1CN(CC1)C1=NC=NC(=C1)N1N=CC(=C1)C)C Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N1)OC1CN(CC1)C1=NC=NC(=C1)N1N=CC(=C1)C)C GSDOQSDHVVBCFZ-UHFFFAOYSA-N 0.000 claims 1
- OULGIZHLOPZVPS-UHFFFAOYSA-N C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N1)S(=O)(=O)C1CN(CC1)C(=O)C1CCOCC1)C Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N1)S(=O)(=O)C1CN(CC1)C(=O)C1CCOCC1)C OULGIZHLOPZVPS-UHFFFAOYSA-N 0.000 claims 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- BRRUONBFBMLXCV-UHFFFAOYSA-N CC1C(C1C)C(=O)N1CC(CC1)OC1=C2N=C(N(C2=NC=N1)CC)C=1C=NC(=NC1)C Chemical compound CC1C(C1C)C(=O)N1CC(CC1)OC1=C2N=C(N(C2=NC=N1)CC)C=1C=NC(=NC1)C BRRUONBFBMLXCV-UHFFFAOYSA-N 0.000 claims 1
- SJBVHXWMIHMJQF-UHFFFAOYSA-N CCn1c(nc2c(OC3CCN(C3)C(=O)C3CC(F)(F)C3)ncnc12)-c1ccc(OC)nc1 Chemical compound CCn1c(nc2c(OC3CCN(C3)C(=O)C3CC(F)(F)C3)ncnc12)-c1ccc(OC)nc1 SJBVHXWMIHMJQF-UHFFFAOYSA-N 0.000 claims 1
- ZRWPCSDPXBRLOU-UHFFFAOYSA-N CCn1c(nc2c(OC3CCN(C3)C(=O)C3CC3C(F)F)ncnc12)-c1cnc(C)nc1 Chemical compound CCn1c(nc2c(OC3CCN(C3)C(=O)C3CC3C(F)F)ncnc12)-c1cnc(C)nc1 ZRWPCSDPXBRLOU-UHFFFAOYSA-N 0.000 claims 1
- DRYBLTNKIICECT-UHFFFAOYSA-N CCn1c(nc2c(OC3CCN(C3)C(=O)N3CC(C3)OC)ncnc12)-c1cnc(C)nc1 Chemical compound CCn1c(nc2c(OC3CCN(C3)C(=O)N3CC(C3)OC)ncnc12)-c1cnc(C)nc1 DRYBLTNKIICECT-UHFFFAOYSA-N 0.000 claims 1
- RHZOOZPJHUGVQE-UHFFFAOYSA-N CCn1c(nc2c(OC3CCN(C3)C(=O)N3CCC(C)(C)C3)ncnc12)-c1cnc(C)nc1 Chemical compound CCn1c(nc2c(OC3CCN(C3)C(=O)N3CCC(C)(C)C3)ncnc12)-c1cnc(C)nc1 RHZOOZPJHUGVQE-UHFFFAOYSA-N 0.000 claims 1
- HFCCQDGBJOVOAY-UHFFFAOYSA-N CCn1ncc(c1C)-c1nc2c(OC3CCN(C3)C(=O)C3CC(F)(F)C3)ncnc2n1C Chemical compound CCn1ncc(c1C)-c1nc2c(OC3CCN(C3)C(=O)C3CC(F)(F)C3)ncnc2n1C HFCCQDGBJOVOAY-UHFFFAOYSA-N 0.000 claims 1
- WAYOYBGLNJJEFY-UHFFFAOYSA-N CCn1ncc(c1C)-c1nc2c(OC3CCN(C3)C(=O)c3c(C)noc3C)ncnc2n1C Chemical compound CCn1ncc(c1C)-c1nc2c(OC3CCN(C3)C(=O)c3c(C)noc3C)ncnc2n1C WAYOYBGLNJJEFY-UHFFFAOYSA-N 0.000 claims 1
- MGPMCLCIYYDECC-UHFFFAOYSA-N CCn1ncc(c1C)-c1nc2c(SC3CCN(C3)c3ncnc4sccc34)ncnc2n1C Chemical compound CCn1ncc(c1C)-c1nc2c(SC3CCN(C3)c3ncnc4sccc34)ncnc2n1C MGPMCLCIYYDECC-UHFFFAOYSA-N 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- XSRJRESMSYHQPL-UHFFFAOYSA-N FC1(CN(CC1)C(=O)N1CC(CC1)OC1=C2N=C(N(C2=NC=N1)CC)C=1C=NC(=NC1)C)F Chemical compound FC1(CN(CC1)C(=O)N1CC(CC1)OC1=C2N=C(N(C2=NC=N1)CC)C=1C=NC(=NC1)C)F XSRJRESMSYHQPL-UHFFFAOYSA-N 0.000 claims 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- IZBUMESVKQMPCE-UHFFFAOYSA-N N-[2-methoxy-5-[9-methyl-6-(1-propanoylpyrrolidin-3-yl)oxypurin-8-yl]pyridin-3-yl]methanesulfonamide Chemical compound COC1=NC=C(C=C1NS(=O)(=O)C)C=1N(C2=NC=NC(=C2N1)OC1CN(CC1)C(CC)=O)C IZBUMESVKQMPCE-UHFFFAOYSA-N 0.000 claims 1
- 208000020410 Psoriasis-related juvenile idiopathic arthritis Diseases 0.000 claims 1
- 208000002200 Respiratory Hypersensitivity Diseases 0.000 claims 1
- RGQPUBJKTHSUSK-NFOMZHRRSA-N [(3s)-3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]-(2-fluorocyclopropyl)methanone Chemical compound C([C@@H](C1)OC2=C3N=C(N(C3=NC=N2)CC)C=2C=NC(C)=NC=2)CN1C(=O)C1CC1F RGQPUBJKTHSUSK-NFOMZHRRSA-N 0.000 claims 1
- NVSPJDGXKBDYIZ-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]pyrazine Chemical compound C1=NC=CN2C=NN=C21 NVSPJDGXKBDYIZ-UHFFFAOYSA-N 0.000 claims 1
- UFNKUHGLNZMSDA-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxycyclopentyl]-morpholin-4-ylmethanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CC(CC4)C(=O)N4CCOCC4)=C3N=2)C)=C1C UFNKUHGLNZMSDA-UHFFFAOYSA-N 0.000 claims 1
- OVNPBWGOPPHPEM-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(1,2,5-oxadiazol-3-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=NON=C4)=C3N=2)C)=C1C OVNPBWGOPPHPEM-UHFFFAOYSA-N 0.000 claims 1
- DNSAXTMMJBNUCH-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(1,2,5-trimethylpyrrol-3-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=C(N(C)C(C)=C4)C)=C3N=2)C)=C1C DNSAXTMMJBNUCH-UHFFFAOYSA-N 0.000 claims 1
- BNKDSVLPQJUWCG-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(1,3,5-trimethylpyrazol-4-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=C(N(C)N=C4C)C)=C3N=2)C)=C1C BNKDSVLPQJUWCG-UHFFFAOYSA-N 0.000 claims 1
- GFLLUKDZOAGSCG-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(1,3-oxazol-4-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4N=COC=4)=C3N=2)C)=C1C GFLLUKDZOAGSCG-UHFFFAOYSA-N 0.000 claims 1
- BXOSGAVMRLMWBH-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(1,3-oxazol-5-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4OC=NC=4)=C3N=2)C)=C1C BXOSGAVMRLMWBH-UHFFFAOYSA-N 0.000 claims 1
- PKDLDRLAKOIYNL-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(1-methyltriazol-4-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4N=NN(C)C=4)=C3N=2)C)=C1C PKDLDRLAKOIYNL-UHFFFAOYSA-N 0.000 claims 1
- KTQXXXUQNXACHX-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(1-propan-2-ylpyrazol-4-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=CN(N=C4)C(C)C)=C3N=2)C)=C1C KTQXXXUQNXACHX-UHFFFAOYSA-N 0.000 claims 1
- OWXOZKNHVVUZBH-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(1h-pyrrolo[3,2-b]pyridin-2-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4NC5=CC=CN=C5C=4)=C3N=2)C)=C1C OWXOZKNHVVUZBH-UHFFFAOYSA-N 0.000 claims 1
- QWDQMQYDBZVEDJ-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(2-methyl-1,3-oxazol-4-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4N=C(C)OC=4)=C3N=2)C)=C1C QWDQMQYDBZVEDJ-UHFFFAOYSA-N 0.000 claims 1
- UARAYYOOELVIRH-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(2-methylpyridin-4-yl)methanone Chemical compound CCn1ncc(c1C)-c1nc2c(OC3CCN(C3)C(=O)c3ccnc(C)c3)ncnc2n1C UARAYYOOELVIRH-UHFFFAOYSA-N 0.000 claims 1
- PXWBVENMFJCAAM-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(2-propan-2-ylpyrazol-3-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)OC1CN(CC1)C(=O)C1=CC=NN1C(C)C)C PXWBVENMFJCAAM-UHFFFAOYSA-N 0.000 claims 1
- AHWAPVULDROPSV-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(2h-triazol-4-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=NNN=C4)=C3N=2)C)=C1C AHWAPVULDROPSV-UHFFFAOYSA-N 0.000 claims 1
- LXRHPAZZKMZEPE-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(3-methyl-1,2-oxazol-4-yl)methanone Chemical compound CCn1ncc(c1C)-c1nc2c(OC3CCN(C3)C(=O)c3conc3C)ncnc2n1C LXRHPAZZKMZEPE-UHFFFAOYSA-N 0.000 claims 1
- WIVGQJVOYWEZAA-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(4-methyl-1,2,5-oxadiazol-3-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4C(=NON=4)C)=C3N=2)C)=C1C WIVGQJVOYWEZAA-UHFFFAOYSA-N 0.000 claims 1
- JHEMBINQJLWKKQ-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(4-methyl-1,2-oxazol-5-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=C(C=NO4)C)=C3N=2)C)=C1C JHEMBINQJLWKKQ-UHFFFAOYSA-N 0.000 claims 1
- KRASATXOEXWLJT-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(4-methyloxan-4-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4(C)CCOCC4)=C3N=2)C)=C1C KRASATXOEXWLJT-UHFFFAOYSA-N 0.000 claims 1
- CDCGUNDUMCUOPP-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(4H-furo[3,2-b]pyrrol-5-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N1)OC1CN(CC1)C(=O)C1=CC2=C(N1)C=CO2)C CDCGUNDUMCUOPP-UHFFFAOYSA-N 0.000 claims 1
- RARZVGXEBXTUFC-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4N5CCCCC5=NN=4)=C3N=2)C)=C1C RARZVGXEBXTUFC-UHFFFAOYSA-N 0.000 claims 1
- WJYURQXGXDESPE-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(5-ethyl-1,2-oxazol-4-yl)methanone Chemical compound O1N=CC(C(=O)N2CC(CC2)OC=2C=3N=C(N(C)C=3N=CN=2)C2=C(N(CC)N=C2)C)=C1CC WJYURQXGXDESPE-UHFFFAOYSA-N 0.000 claims 1
- IENWCXMGZBCZQS-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(5-methyl-1,2-oxazol-4-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=C(ON=C4)C)=C3N=2)C)=C1C IENWCXMGZBCZQS-UHFFFAOYSA-N 0.000 claims 1
- HKXXJJYVZZTRSK-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(5-methyl-1,3,4-oxadiazol-2-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4OC(C)=NN=4)=C3N=2)C)=C1C HKXXJJYVZZTRSK-UHFFFAOYSA-N 0.000 claims 1
- QSRUIFHKGBKYHI-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(5-methyl-1,3-oxazol-4-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=C(OC=N4)C)=C3N=2)C)=C1C QSRUIFHKGBKYHI-UHFFFAOYSA-N 0.000 claims 1
- DZCLVKFRXSERAC-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(5-methylthiadiazol-4-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=C(SN=N4)C)=C3N=2)C)=C1C DZCLVKFRXSERAC-UHFFFAOYSA-N 0.000 claims 1
- GVQPLDZEIWTVOL-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(5-propan-2-yl-1,2-oxazol-4-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=C(ON=C4)C(C)C)=C3N=2)C)=C1C GVQPLDZEIWTVOL-UHFFFAOYSA-N 0.000 claims 1
- TWFWWCZDMIQGHE-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(5-propan-2-yl-1h-pyrazol-3-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=NNC(=C4)C(C)C)=C3N=2)C)=C1C TWFWWCZDMIQGHE-UHFFFAOYSA-N 0.000 claims 1
- KSAWWPJJENWHIZ-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(6-methylpyridin-3-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4C=NC(C)=CC=4)=C3N=2)C)=C1C KSAWWPJJENWHIZ-UHFFFAOYSA-N 0.000 claims 1
- FHKPLLOSJHHKNU-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4CCOCC4)=C3N=2)C)=C1C FHKPLLOSJHHKNU-UHFFFAOYSA-N 0.000 claims 1
- YNTYDNNUXJFLCP-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxolan-2-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4OCCC4)=C3N=2)C)=C1C YNTYDNNUXJFLCP-UHFFFAOYSA-N 0.000 claims 1
- VTSHOJMBFLDBNC-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-[1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N1)OC1CN(CC1)C(=O)C=1C(=NN(C1)C)C(F)(F)F)C VTSHOJMBFLDBNC-UHFFFAOYSA-N 0.000 claims 1
- WQAIYBOZPJLOLS-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4N(N=C(C=4)C(F)(F)F)C)=C3N=2)C)=C1C WQAIYBOZPJLOLS-UHFFFAOYSA-N 0.000 claims 1
- HGPOAXRSXRULKQ-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-[3-(2-hydroxypropan-2-yl)-1,2,4-oxadiazol-5-yl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4ON=C(N=4)C(C)(C)O)=C3N=2)C)=C1C HGPOAXRSXRULKQ-UHFFFAOYSA-N 0.000 claims 1
- PCARUBNJVVALKD-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-[4-(4-methylpiperazin-1-yl)phenyl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4C=CC(=CC=4)N4CCN(C)CC4)=C3N=2)C)=C1C PCARUBNJVVALKD-UHFFFAOYSA-N 0.000 claims 1
- UQCPFNPNEYVNSJ-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-[5-(2-hydroxypropan-2-yl)-1,2,4-oxadiazol-3-yl]methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N1)OC1CN(CC1)C(=O)C1=NOC(=N1)C(C)(C)O)C UQCPFNPNEYVNSJ-UHFFFAOYSA-N 0.000 claims 1
- QTKGVKWBJWFLQC-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-[5-(trifluoromethyl)-1h-pyrazol-4-yl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=C(NN=C4)C(F)(F)F)=C3N=2)C)=C1C QTKGVKWBJWFLQC-UHFFFAOYSA-N 0.000 claims 1
- BBPXSBAONJIJJI-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-naphthalen-1-ylmethanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4C5=CC=CC=C5C=CC=4)=C3N=2)C)=C1C BBPXSBAONJIJJI-UHFFFAOYSA-N 0.000 claims 1
- XFBUOIBLAOVXMA-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-naphthalen-2-ylmethanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4C=C5C=CC=CC5=CC=4)=C3N=2)C)=C1C XFBUOIBLAOVXMA-UHFFFAOYSA-N 0.000 claims 1
- DOVWNBJVPJDBOV-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-phenylmethanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4C=CC=CC=4)=C3N=2)C)=C1C DOVWNBJVPJDBOV-UHFFFAOYSA-N 0.000 claims 1
- OTOGDSJBERYLRB-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-pyrazolo[1,5-a]pyridin-3-ylmethanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=C5C=CC=CN5N=C4)=C3N=2)C)=C1C OTOGDSJBERYLRB-UHFFFAOYSA-N 0.000 claims 1
- XWTIRNKKKCXAJN-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-pyrazolo[1,5-a]pyrimidin-3-ylmethanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4=C5N=CC=CN5N=C4)=C3N=2)C)=C1C XWTIRNKKKCXAJN-UHFFFAOYSA-N 0.000 claims 1
- JJIVCBCYDBVFQZ-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-pyridin-2-ylmethanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4N=CC=CC=4)=C3N=2)C)=C1C JJIVCBCYDBVFQZ-UHFFFAOYSA-N 0.000 claims 1
- VKIHTPNLKOZPFU-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-pyridin-3-ylmethanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4C=NC=CC=4)=C3N=2)C)=C1C VKIHTPNLKOZPFU-UHFFFAOYSA-N 0.000 claims 1
- IEPOJMXOEGSJMH-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-pyridin-4-ylmethanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4C=CN=CC=4)=C3N=2)C)=C1C IEPOJMXOEGSJMH-UHFFFAOYSA-N 0.000 claims 1
- GHJUPLFJQXACRI-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]sulfanylpyrrolidin-1-yl]-(1-methylpyrazol-3-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(SC4CN(CC4)C(=O)C4=NN(C)C=C4)=C3N=2)C)=C1C GHJUPLFJQXACRI-UHFFFAOYSA-N 0.000 claims 1
- MVRSZWVHPXOEDF-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]sulfanylpyrrolidin-1-yl]-(2-methyl-1,3-oxazol-4-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(SC4CN(CC4)C(=O)C=4N=C(C)OC=4)=C3N=2)C)=C1C MVRSZWVHPXOEDF-UHFFFAOYSA-N 0.000 claims 1
- YMPNWOPBPIAKPI-UHFFFAOYSA-N [3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]sulfanylpyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(SC4CN(CC4)C(=O)C4CCOCC4)=C3N=2)C)=C1C YMPNWOPBPIAKPI-UHFFFAOYSA-N 0.000 claims 1
- SAWHZQXWEWBBKZ-UHFFFAOYSA-N [3-[8-(5-chloro-6-methoxypyridin-3-yl)-9-ethylpurin-6-yl]oxypyrrolidin-1-yl]-cyclopropylmethanone Chemical compound N1=CN=C2N(CC)C(C=3C=C(Cl)C(OC)=NC=3)=NC2=C1OC(C1)CCN1C(=O)C1CC1 SAWHZQXWEWBBKZ-UHFFFAOYSA-N 0.000 claims 1
- XGPXKEBTADULEG-UHFFFAOYSA-N [3-[8-[6-amino-5-(trifluoromethyl)pyridin-3-yl]-9-ethylpurin-6-yl]oxypyrrolidin-1-yl]-cyclopropylmethanone Chemical compound N1=CN=C2N(CC)C(C=3C=C(C(N)=NC=3)C(F)(F)F)=NC2=C1OC(C1)CCN1C(=O)C1CC1 XGPXKEBTADULEG-UHFFFAOYSA-N 0.000 claims 1
- SYWDSJRCKJADOW-UHFFFAOYSA-N [3-[9-ethyl-8-(1-ethyl-5-methylpyrazol-4-yl)purin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4CCOCC4)=C3N=2)CC)=C1C SYWDSJRCKJADOW-UHFFFAOYSA-N 0.000 claims 1
- GTDNUYQEEDHPIM-UHFFFAOYSA-N [3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]-(1,3-oxazol-4-yl)methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C(=O)C1=COC=N1 GTDNUYQEEDHPIM-UHFFFAOYSA-N 0.000 claims 1
- SIFZJUXKBMILIA-UHFFFAOYSA-N [3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]-(1-methylcyclobutyl)methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C(=O)C1(C)CCC1 SIFZJUXKBMILIA-UHFFFAOYSA-N 0.000 claims 1
- MDXLUXBVEBQEMB-UHFFFAOYSA-N [3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]-(2-methylcyclopropyl)methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C(=O)C1CC1C MDXLUXBVEBQEMB-UHFFFAOYSA-N 0.000 claims 1
- KMBFSPJWGGNVFB-UHFFFAOYSA-N [3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]-(3-fluoroazetidin-1-yl)methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C(=O)N1CC(F)C1 KMBFSPJWGGNVFB-UHFFFAOYSA-N 0.000 claims 1
- IRRJRASMSTVDRN-UHFFFAOYSA-N [3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]-(3-hydroxyazetidin-1-yl)methanone Chemical compound CCn1c(nc2c(OC3CCN(C3)C(=O)N3CC(O)C3)ncnc12)-c1cnc(C)nc1 IRRJRASMSTVDRN-UHFFFAOYSA-N 0.000 claims 1
- HQASIWKLNZUPMH-UHFFFAOYSA-N [3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]-(3-methoxy-3-methylazetidin-1-yl)methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C(=O)N1CC(C)(OC)C1 HQASIWKLNZUPMH-UHFFFAOYSA-N 0.000 claims 1
- PNGBSTRVQGLGNA-UHFFFAOYSA-N [3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]-(3-methylcyclobutyl)methanone Chemical compound CCN1C(=NC2=C(OC3CCN(C3)C(=O)C3CC(C)C3)N=CN=C12)C1=CN=C(C)N=C1 PNGBSTRVQGLGNA-UHFFFAOYSA-N 0.000 claims 1
- FQCPBYZODMZDKG-UHFFFAOYSA-N [3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C(=O)C1CCOCC1 FQCPBYZODMZDKG-UHFFFAOYSA-N 0.000 claims 1
- ZJOFXUHWYKVIDA-UHFFFAOYSA-N [3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]-(oxolan-3-yl)methanone Chemical compound C(C)N1C2=NC=NC(=C2N=C1C=1C=NC(=NC1)C)OC1CN(CC1)C(=O)C1COCC1 ZJOFXUHWYKVIDA-UHFFFAOYSA-N 0.000 claims 1
- ROQMBEGAZGQYNB-UHFFFAOYSA-N [3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]-[2-(fluoromethyl)cyclopropyl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C(=O)C1CC1CF ROQMBEGAZGQYNB-UHFFFAOYSA-N 0.000 claims 1
- YYOGIZRRHSZDRQ-UHFFFAOYSA-N [3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]-[3-(hydroxymethyl)pyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C(=O)N1CCC(CO)C1 YYOGIZRRHSZDRQ-UHFFFAOYSA-N 0.000 claims 1
- NTHXSXRLPCUXNU-UHFFFAOYSA-N [3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]-piperidin-1-ylmethanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C(=O)N1CCCCC1 NTHXSXRLPCUXNU-UHFFFAOYSA-N 0.000 claims 1
- GDGODIUBGFVMTJ-UHFFFAOYSA-N [3-[9-ethyl-8-(5-fluoro-6-methoxypyridin-3-yl)purin-6-yl]oxypyrrolidin-1-yl]-(3-methylimidazol-4-yl)methanone Chemical compound N1=CN=C2N(CC)C(C=3C=C(F)C(OC)=NC=3)=NC2=C1OC(C1)CCN1C(=O)C1=CN=CN1C GDGODIUBGFVMTJ-UHFFFAOYSA-N 0.000 claims 1
- LYPTYLNYDNBBOV-UHFFFAOYSA-N [3-[9-ethyl-8-(6-methoxypyridin-3-yl)purin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(OC)=CC=3)=NC2=C1OC(C1)CCN1C(=O)C1CCOCC1 LYPTYLNYDNBBOV-UHFFFAOYSA-N 0.000 claims 1
- YTYSIVBLSXQKNP-UHFFFAOYSA-N [3-[9-ethyl-8-[6-(trifluoromethyl)pyridin-3-yl]purin-6-yl]oxypyrrolidin-1-yl]-(3-methoxyazetidin-1-yl)methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(=CC=3)C(F)(F)F)=NC2=C1OC(C1)CCN1C(=O)N1CC(OC)C1 YTYSIVBLSXQKNP-UHFFFAOYSA-N 0.000 claims 1
- HQDBDXZOWDIWKU-UHFFFAOYSA-N [3-[[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]methyl]pyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(CC4CN(CC4)C(=O)C4CCOCC4)=C3N=2)C)=C1C HQDBDXZOWDIWKU-UHFFFAOYSA-N 0.000 claims 1
- GKJSMBPYMQPZBR-UHFFFAOYSA-N [4-[8-(1-ethyl-5-methylpyrazol-3-yl)-9-methylpurin-6-yl]oxypiperidin-1-yl]-(oxan-4-yl)methanone Chemical compound C1=C(C)N(CC)N=C1C(N(C1=NC=N2)C)=NC1=C2OC1CCN(C(=O)C2CCOCC2)CC1 GKJSMBPYMQPZBR-UHFFFAOYSA-N 0.000 claims 1
- AIDYTIZUEIFGTP-UHFFFAOYSA-N [4-[8-(1-ethyl-5-methylpyrazol-3-yl)-9-methylpurin-6-yl]oxypiperidin-1-yl]-phenylmethanone Chemical compound C1=C(C)N(CC)N=C1C(N(C1=NC=N2)C)=NC1=C2OC1CCN(C(=O)C=2C=CC=CC=2)CC1 AIDYTIZUEIFGTP-UHFFFAOYSA-N 0.000 claims 1
- OKLAZDLQOWPJFB-UHFFFAOYSA-N [5-(dimethylamino)-1,3,4-oxadiazol-2-yl]-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C=4OC(=NN=4)N(C)C)=C3N=2)C)=C1C OKLAZDLQOWPJFB-UHFFFAOYSA-N 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 230000010085 airway hyperresponsiveness Effects 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004419 alkynylene group Chemical group 0.000 claims 1
- 201000009961 allergic asthma Diseases 0.000 claims 1
- 230000001668 ameliorated effect Effects 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- SRJXXDDAMCNELH-UHFFFAOYSA-N azetidin-1-yl-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C(=O)N1CCC1 SRJXXDDAMCNELH-UHFFFAOYSA-N 0.000 claims 1
- VKJRJIHIGQSVCI-UHFFFAOYSA-N azetidin-3-yl-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C(=O)C1CNC1 VKJRJIHIGQSVCI-UHFFFAOYSA-N 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 208000023819 chronic asthma Diseases 0.000 claims 1
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims 1
- VMWKZNCZGWIIQF-UHFFFAOYSA-N cyclobutyl-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound CCN1N=CC(=C1C)C1=NC2=C(OC3CCN(C3)C(=O)C3CCC3)N=CN=C2N1C VMWKZNCZGWIIQF-UHFFFAOYSA-N 0.000 claims 1
- LOBLFGNATFREJF-UHFFFAOYSA-N cyclohexyl-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4CCCCC4)=C3N=2)C)=C1C LOBLFGNATFREJF-UHFFFAOYSA-N 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- ODDWBQSVTQFZGW-UHFFFAOYSA-N cyclopentyl-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4CCCC4)=C3N=2)C)=C1C ODDWBQSVTQFZGW-UHFFFAOYSA-N 0.000 claims 1
- MUVDPSUJLRMXOQ-UHFFFAOYSA-N cyclopentyl-[4-[8-(1-ethyl-5-methylpyrazol-3-yl)-9-methylpurin-6-yl]oxypiperidin-1-yl]methanone Chemical compound C1=C(C)N(CC)N=C1C(N(C1=NC=N2)C)=NC1=C2OC1CCN(C(=O)C2CCCC2)CC1 MUVDPSUJLRMXOQ-UHFFFAOYSA-N 0.000 claims 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 1
- XXLXWZKZZCNPJC-UHFFFAOYSA-N cyclopropyl-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(CC4)C(=O)C4CC4)=C3N=2)C)=C1C XXLXWZKZZCNPJC-UHFFFAOYSA-N 0.000 claims 1
- ODZFSEQEKKXAAN-UHFFFAOYSA-N cyclopropyl-[3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]sulfanylpyrrolidin-1-yl]methanone Chemical compound CCN1N=CC(C=2N(C3=NC=NC(SC4CN(CC4)C(=O)C4CC4)=C3N=2)C)=C1C ODZFSEQEKKXAAN-UHFFFAOYSA-N 0.000 claims 1
- MHMDULHMMKCWHI-UHFFFAOYSA-N cyclopropyl-[3-[8-(2,4-dimethylpyrimidin-5-yl)-9-ethylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C(=NC(C)=NC=3)C)=NC2=C1OC(C1)CCN1C(=O)C1CC1 MHMDULHMMKCWHI-UHFFFAOYSA-N 0.000 claims 1
- TWPINMVHKCAGLX-UHFFFAOYSA-N cyclopropyl-[3-[8-[2-(dimethylamino)pyrimidin-5-yl]-9-ethylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(=NC=3)N(C)C)=NC2=C1OC(C1)CCN1C(=O)C1CC1 TWPINMVHKCAGLX-UHFFFAOYSA-N 0.000 claims 1
- WNROTAFRDFHHQG-UHFFFAOYSA-N cyclopropyl-[3-[8-[6-(difluoromethoxy)pyridin-3-yl]-9-ethylpurin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(OC(F)F)=CC=3)=NC2=C1OC(C1)CCN1C(=O)C1CC1 WNROTAFRDFHHQG-UHFFFAOYSA-N 0.000 claims 1
- WVKZOUQEABFQCM-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(1h-pyrrolo[2,3-b]pyridin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=C4C=CNC4=NC=3)=NC2=C1OC(C1)CCN1C(=O)C1CC1 WVKZOUQEABFQCM-UHFFFAOYSA-N 0.000 claims 1
- PIEMGRLPIFKFCC-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(2-methoxypyridin-4-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=C(OC)N=CC=3)=NC2=C1OC(C1)CCN1C(=O)C1CC1 PIEMGRLPIFKFCC-UHFFFAOYSA-N 0.000 claims 1
- FETKZAKWDUVVHD-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(2-methoxypyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(OC)=NC=3)=NC2=C1OC(C1)CCN1C(=O)C1CC1 FETKZAKWDUVVHD-UHFFFAOYSA-N 0.000 claims 1
- KJQHNHJNXPNQRK-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-2-methylpyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1C)CCN1C(=O)C1CC1 KJQHNHJNXPNQRK-UHFFFAOYSA-N 0.000 claims 1
- KWAGUAVWLVQEDU-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-3-methylpyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)(C)CCN1C(=O)C1CC1 KWAGUAVWLVQEDU-UHFFFAOYSA-N 0.000 claims 1
- KMFGXTARPBGMIM-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-4-(fluoromethyl)pyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C(C1)CF)CN1C(=O)C1CC1 KMFGXTARPBGMIM-UHFFFAOYSA-N 0.000 claims 1
- YYFMBLFGZRGPNE-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-4-fluoropyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C(C1)F)CN1C(=O)C1CC1 YYFMBLFGZRGPNE-UHFFFAOYSA-N 0.000 claims 1
- PULXYFGNEXICSE-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-4-hydroxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C(C1)O)CN1C(=O)C1CC1 PULXYFGNEXICSE-UHFFFAOYSA-N 0.000 claims 1
- DFMSPLZYMXNENJ-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-4-methoxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C(C1)OC)CN1C(=O)C1CC1 DFMSPLZYMXNENJ-UHFFFAOYSA-N 0.000 claims 1
- PZPZKFQGUCXWQH-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-4-methylpyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C(C1)C)CN1C(=O)C1CC1 PZPZKFQGUCXWQH-UHFFFAOYSA-N 0.000 claims 1
- UFMYIDKWDRKBAR-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-7-azabicyclo[2.2.1]heptan-7-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC1CC2CCC1N2C(=O)C1CC1 UFMYIDKWDRKBAR-UHFFFAOYSA-N 0.000 claims 1
- KKLHCMCSZHFUHY-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C(=O)C1CC1 KKLHCMCSZHFUHY-UHFFFAOYSA-N 0.000 claims 1
- UUNVASWXAXWTEY-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(3-fluoro-4-methoxyphenyl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=C(F)C(OC)=CC=3)=NC2=C1OC(C1)CCN1C(=O)C1CC1 UUNVASWXAXWTEY-UHFFFAOYSA-N 0.000 claims 1
- WHTCZKIEIJMOSY-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C3=C4CCCCN4N=C3)=NC2=C1OC(C1)CCN1C(=O)C1CC1 WHTCZKIEIJMOSY-UHFFFAOYSA-N 0.000 claims 1
- CNTXNESSHOHLEW-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(5-fluoro-6-methoxypyridin-3-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=C(F)C(OC)=NC=3)=NC2=C1OC(C1)CCN1C(=O)C1CC1 CNTXNESSHOHLEW-UHFFFAOYSA-N 0.000 claims 1
- BYSLNESALSJTON-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(5-fluoro-6-methylpyridin-3-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=C(F)C(C)=NC=3)=NC2=C1OC(C1)CCN1C(=O)C1CC1 BYSLNESALSJTON-UHFFFAOYSA-N 0.000 claims 1
- NGDWEBKYJKMJHO-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(5-methoxypyridin-2-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3N=CC(OC)=CC=3)=NC2=C1OC(C1)CCN1C(=O)C1CC1 NGDWEBKYJKMJHO-UHFFFAOYSA-N 0.000 claims 1
- LTASRDZYZYDOTK-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(6-methoxy-5-methylpyridin-3-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=C(C)C(OC)=NC=3)=NC2=C1OC(C1)CCN1C(=O)C1CC1 LTASRDZYZYDOTK-UHFFFAOYSA-N 0.000 claims 1
- QOXGOSFAOKMVHJ-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-(6-methoxypyridin-3-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(OC)=CC=3)=NC2=C1OC(C1)CCN1C(=O)C1CC1 QOXGOSFAOKMVHJ-UHFFFAOYSA-N 0.000 claims 1
- BIBRYXAKJKJADR-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-[2-(trifluoromethyl)pyrimidin-5-yl]purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound C1(CC1)C(=O)N1CC(CC1)OC1=C2N=C(N(C2=NC=N1)CC)C=1C=NC(=NC=1)C(F)(F)F BIBRYXAKJKJADR-UHFFFAOYSA-N 0.000 claims 1
- ANDMMOADHUFNJW-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-[4-(trifluoromethoxy)phenyl]purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=CC(OC(F)(F)F)=CC=3)=NC2=C1OC(C1)CCN1C(=O)C1CC1 ANDMMOADHUFNJW-UHFFFAOYSA-N 0.000 claims 1
- KHRIEONTLHPNDX-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-[4-(trifluoromethyl)phenyl]purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=CC(=CC=3)C(F)(F)F)=NC2=C1OC(C1)CCN1C(=O)C1CC1 KHRIEONTLHPNDX-UHFFFAOYSA-N 0.000 claims 1
- QSNHBBRYLWUGKQ-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-[6-(trifluoromethyl)pyridin-3-yl]purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(=CC=3)C(F)(F)F)=NC2=C1OC(C1)CCN1C(=O)C1CC1 QSNHBBRYLWUGKQ-UHFFFAOYSA-N 0.000 claims 1
- ZNIDBLRZIIYCDZ-UHFFFAOYSA-N cyclopropyl-[3-[9-ethyl-8-[6-methoxy-5-(trifluoromethyl)pyridin-3-yl]purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=C(C(OC)=NC=3)C(F)(F)F)=NC2=C1OC(C1)CCN1C(=O)C1CC1 ZNIDBLRZIIYCDZ-UHFFFAOYSA-N 0.000 claims 1
- FTOWJKKXVOQWPJ-UHFFFAOYSA-N cyclopropyl-[3-ethyl-4-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxypyrrolidin-1-yl]methanone Chemical compound CCC1CN(C(=O)C2CC2)CC1OC(C=1N=2)=NC=NC=1N(CC)C=2C1=CN=C(C)N=C1 FTOWJKKXVOQWPJ-UHFFFAOYSA-N 0.000 claims 1
- NPOFANAHVMHDDD-UHFFFAOYSA-N cyclopropyl-[4-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-3,3-difluoropyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C(C1)(F)F)CN1C(=O)C1CC1 NPOFANAHVMHDDD-UHFFFAOYSA-N 0.000 claims 1
- PMHPMPPFRACMCA-UHFFFAOYSA-N cyclopropyl-[4-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-3,3-dimethylpyrrolidin-1-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C(C1)(C)C)CN1C(=O)C1CC1 PMHPMPPFRACMCA-UHFFFAOYSA-N 0.000 claims 1
- ACNJOMWVEWCPGQ-UHFFFAOYSA-N cyclopropyl-[7-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-5-azaspiro[2.4]heptan-5-yl]methanone Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC1CN(C(=O)C2CC2)CC11CC1 ACNJOMWVEWCPGQ-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 208000024711 extrinsic asthma Diseases 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 201000010659 intrinsic asthma Diseases 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- BTIHTOMTGBLSBP-UHFFFAOYSA-N n-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxycyclobutyl]ethanesulfonamide Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC1CC(NS(=O)(=O)CC)C1 BTIHTOMTGBLSBP-UHFFFAOYSA-N 0.000 claims 1
- GLAZPZCMSPKPSU-UHFFFAOYSA-N n-[3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxycyclopentyl]oxane-4-carboxamide Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCC1NC(=O)C1CCOCC1 GLAZPZCMSPKPSU-UHFFFAOYSA-N 0.000 claims 1
- HZQFHGHRLIIADU-HNNXBMFYSA-N n-[3-fluoro-5-[9-methyl-6-[(3s)-1-propanoylpyrrolidin-3-yl]oxypurin-8-yl]phenyl]methanesulfonamide Chemical compound C1N(C(=O)CC)CC[C@@H]1OC1=NC=NC2=C1N=C(C=1C=C(NS(C)(=O)=O)C=C(F)C=1)N2C HZQFHGHRLIIADU-HNNXBMFYSA-N 0.000 claims 1
- WIILISIYKGTXPH-UHFFFAOYSA-N n-[4-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxycyclohexyl]cyclopropanecarboxamide Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(CC1)CCC1NC(=O)C1CC1 WIILISIYKGTXPH-UHFFFAOYSA-N 0.000 claims 1
- OJWPCUYSBMLDOJ-UHFFFAOYSA-N n-[4-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxycyclohexyl]propanamide Chemical compound C1CC(NC(=O)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=NC(C)=NC=1)N2CC OJWPCUYSBMLDOJ-UHFFFAOYSA-N 0.000 claims 1
- WLWDUZRDGNSXEF-UHFFFAOYSA-N n-cyclopropyl-3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-n-methylpyrrolidine-1-carboxamide Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC(C1)CCN1C(=O)N(C)C1CC1 WLWDUZRDGNSXEF-UHFFFAOYSA-N 0.000 claims 1
- UDKHLQJHBRZYHS-UHFFFAOYSA-N n-ethyl-3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-n-methylpyrrolidine-1-carboxamide Chemical compound C1N(C(=O)N(C)CC)CCC1OC1=NC=NC2=C1N=C(C=1C=NC(C)=NC=1)N2CC UDKHLQJHBRZYHS-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 230000000306 recurrent effect Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- SQMVFENIZRKNIJ-UHFFFAOYSA-N tert-butyl 3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxyazetidine-1-carboxylate Chemical compound CCN1N=CC(C=2N(C3=NC=NC(OC4CN(C4)C(=O)OC(C)(C)C)=C3N=2)C)=C1C SQMVFENIZRKNIJ-UHFFFAOYSA-N 0.000 claims 1
- RQPODSPSPMZFCA-UHFFFAOYSA-N tert-butyl 3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-2-methylpyrrolidine-1-carboxylate Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC1CCN(C(=O)OC(C)(C)C)C1C RQPODSPSPMZFCA-UHFFFAOYSA-N 0.000 claims 1
- HFNOQOKWCDZPFP-UHFFFAOYSA-N tert-butyl 3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-4-fluoropyrrolidine-1-carboxylate Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC1CN(C(=O)OC(C)(C)C)CC1F HFNOQOKWCDZPFP-UHFFFAOYSA-N 0.000 claims 1
- MFTILFWJXRZNNC-UHFFFAOYSA-N tert-butyl 3-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-4-hydroxypyrrolidine-1-carboxylate Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC1CN(C(=O)OC(C)(C)C)CC1O MFTILFWJXRZNNC-UHFFFAOYSA-N 0.000 claims 1
- HKCMDKQCWXJWKY-UHFFFAOYSA-N tert-butyl 3-[[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]methyl]pyrrolidine-1-carboxylate Chemical compound CCN1N=CC(C=2N(C3=NC=NC(CC4CN(CC4)C(=O)OC(C)(C)C)=C3N=2)C)=C1C HKCMDKQCWXJWKY-UHFFFAOYSA-N 0.000 claims 1
- GNYJIINXDSIEJN-UHFFFAOYSA-N tert-butyl 4-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypiperidine-1-carboxylate Chemical compound CCN1N=CC(=C1C)C1=NC2=C(N=CN=C2OC2CCN(CC2)C(=O)OC(C)(C)C)N1C GNYJIINXDSIEJN-UHFFFAOYSA-N 0.000 claims 1
- JCESZEKPEXGAFW-UHFFFAOYSA-N tert-butyl 4-[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]oxy-3,3-difluoropyrrolidine-1-carboxylate Chemical compound N1=CN=C2N(CC)C(C=3C=NC(C)=NC=3)=NC2=C1OC1CN(C(=O)OC(C)(C)C)CC1(F)F JCESZEKPEXGAFW-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261727416P | 2012-11-16 | 2012-11-16 | |
| US61/727,416 | 2012-11-16 | ||
| PCT/CN2013/001394 WO2014075392A1 (en) | 2012-11-16 | 2013-11-15 | Purine inhibitors of human phosphatidylinositol 3-kinase delta |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015537010A JP2015537010A (ja) | 2015-12-24 |
| JP2015537010A5 true JP2015537010A5 (enExample) | 2016-12-22 |
| JP6297582B2 JP6297582B2 (ja) | 2018-03-20 |
Family
ID=50730541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015542134A Expired - Fee Related JP6297582B2 (ja) | 2012-11-16 | 2013-11-15 | ヒトホスファチジルイノシトール３−キナーゼデルタのプリン阻害剤 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9730940B2 (enExample) |
| EP (1) | EP2920171B1 (enExample) |
| JP (1) | JP6297582B2 (enExample) |
| KR (1) | KR20150082613A (enExample) |
| CN (1) | CN104918939B (enExample) |
| AU (1) | AU2013347538B2 (enExample) |
| BR (1) | BR112015011148A8 (enExample) |
| CA (1) | CA2891009A1 (enExample) |
| MX (1) | MX2015006191A (enExample) |
| RU (1) | RU2658006C2 (enExample) |
| WO (1) | WO2014075392A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201444849A (zh) | 2013-03-13 | 2014-12-01 | Janssen Pharmaceutica Nv | 經取代的7-氮雜雙環類及其作為食慾激素受體調節劑之用途 |
| TW201444821A (zh) | 2013-03-13 | 2014-12-01 | Janssen Pharmaceutica Nv | 經取代之哌啶化合物及其作為食慾素受體調節劑之用途 |
| TWI621618B (zh) | 2013-03-13 | 2018-04-21 | 比利時商健生藥品公司 | 經取代２－氮雜雙環類及其作為食慾素受體調控劑之用途 |
| ES2654051T3 (es) | 2013-12-05 | 2018-02-12 | Pfizer Inc. | Pirrolo[2,3-d]pirimidinilo, pirrolo[2,3-b]pirazinilo y pirrolo[2,3-d]piridinil acrilamidas |
| JP6262885B2 (ja) | 2014-03-06 | 2018-01-17 | シャンハイ ハイヤン ファーマシューティカル テクノロジー カンパニー リミテッドＳｈａｎｇｈａｉ Ｈａｉｙａｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌ Ｔｅｃｈｎｏｌｏｇｙ Ｃｏ．， Ｌｔｄ． | オレキシン受容体拮抗剤としてのピペリジン誘導体 |
| CN104030998B (zh) * | 2014-06-05 | 2015-11-18 | 华东师范大学 | 4-多氟烷基-4，5-二取代异噁唑衍生物及其制备方法 |
| WO2016020784A1 (en) | 2014-08-05 | 2016-02-11 | Pfizer Inc. | N-acylpyrrolidine ether tropomyosin-related kinase inhibitors |
| AU2015314851B2 (en) | 2014-09-11 | 2020-01-02 | Janssen Pharmaceutica Nv | Substituted 2-azabicycles and their use as orexin receptor modulators |
| WO2016057924A1 (en) * | 2014-10-10 | 2016-04-14 | Genentech, Inc. | Pyrrolidine amide compounds as histone demethylase inhibitors |
| US10189844B2 (en) | 2016-02-04 | 2019-01-29 | Chiesi Farmaceutici S.P.A. | Pyrazole derivatives as phosphoinositide 3-kinases inhibitors |
| WO2017166104A1 (en) * | 2016-03-30 | 2017-10-05 | Merck Sharp & Dohme Corp. | Purine inhibitors of human phosphatidylinositol 3-kinase delta |
| ES2872003T3 (es) * | 2016-09-14 | 2021-11-02 | Janssen Pharmaceutica Nv | Inhibidores espirobicíclicos de la interacción de menina-MLL |
| US10494370B2 (en) | 2017-08-16 | 2019-12-03 | Bristol-Myers Squibb Company | Toll-like receptor 7 (TLR7) agonists having a pyridine or pyrazine moiety, conjugates thereof, and methods and uses therefor |
| TWI878414B (zh) | 2019-12-19 | 2025-04-01 | 比利時商健生藥品公司 | 經取代之直鏈螺環接衍生物 |
| CN113620976B (zh) * | 2020-05-09 | 2023-09-26 | 中国医学科学院药物研究所 | 噻唑并嘧啶类化合物及其制备方法、用途和药物组合物 |
| JP7736782B2 (ja) * | 2021-03-29 | 2025-09-09 | 株式会社カネカ | （２－メチルピリミジン－５－イル）ボロン酸誘導体の製造方法 |
| CN113072480B (zh) * | 2021-04-13 | 2022-09-30 | 常州佳德医药科技有限公司 | 一种手性(-)-5-氮杂螺[2.4]庚烷-7-醇、制备方法及应用 |
| CN120092008A (zh) * | 2022-10-20 | 2025-06-03 | 上海瑛派药业有限公司 | 取代的杂芳基双环化合物作为usp1抑制剂及其应用 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT95516A (pt) * | 1989-10-06 | 1991-08-14 | Wellcome Found | Processo para a preparacao de derivados de 2',3'-didesoxi nucleosidos 6-substituidos |
| US5670501A (en) | 1994-09-01 | 1997-09-23 | Discovery Therapeutics, Inc. | N-substituted 9-alkyladenines |
| DK2223922T3 (en) * | 2000-04-25 | 2016-06-06 | Icos Corp | Inhibitors of HUMANPHOSPHATIDYL-inositol 3-KINASEDELTA |
| CN1291994C (zh) * | 2000-07-21 | 2006-12-27 | 吉里德科学公司 | 核苷酸膦酸酯类似物前药及其筛选和制备方法 |
| SE0300456D0 (sv) * | 2003-02-19 | 2003-02-19 | Astrazeneca Ab | Novel compounds |
| MXPA05013226A (es) * | 2003-06-12 | 2006-03-09 | Novo Nordisk As | Carbamatos de piperidina sustituidos, para el uso como inhibidores de la lipasa sensible a hormonas. |
| CA2565037A1 (en) | 2004-04-28 | 2005-11-10 | Cv Therapeutics, Inc. | Purine derivatives as a1 adenosine receptor antagonists |
| US8008307B2 (en) * | 2006-08-08 | 2011-08-30 | Millennium Pharmaceuticals, Inc. | Heteroaryl compounds useful as inhibitors of E1 activating enzymes |
| ATE485276T1 (de) * | 2006-08-08 | 2010-11-15 | Millennium Pharm Inc | Heteroarylverbindungen als hemmer der e1- aktivierenden enzyme |
| JP2011527342A (ja) * | 2008-07-07 | 2011-10-27 | エックスカバリー ホールディング カンパニー エルエルシー | Ｐｉ３ｋアイソフォーム選択的阻害剤 |
| US8759359B2 (en) * | 2009-12-18 | 2014-06-24 | Incyte Corporation | Substituted heteroaryl fused derivatives as PI3K inhibitors |
| EP2588473A1 (en) * | 2010-06-30 | 2013-05-08 | Amgen Inc. | Nitrogen containing heterocyclic compounds as pik3 -delta inhibitors |
| UA112517C2 (uk) * | 2010-07-06 | 2016-09-26 | Новартіс Аг | Тетрагідропіридопіримідинові похідні |
| WO2012037204A1 (en) * | 2010-09-14 | 2012-03-22 | Exelixis, Inc. | Inhibitors of pi3k-delta and methods of their use and manufacture |
| ES2612503T3 (es) * | 2010-09-14 | 2017-05-17 | Exelixis, Inc. | Compuestos 9H-purina como inhibidores de PI3K-delta y métodos para su preparación |
| CN102838600A (zh) * | 2011-06-24 | 2012-12-26 | 山东亨利医药科技有限责任公司 | 苯基喹唑啉类PI3Kδ抑制剂 |
-
2013
- 2013-11-15 MX MX2015006191A patent/MX2015006191A/es unknown
- 2013-11-15 CN CN201380070648.XA patent/CN104918939B/zh not_active Expired - Fee Related
- 2013-11-15 EP EP13855335.9A patent/EP2920171B1/en active Active
- 2013-11-15 WO PCT/CN2013/001394 patent/WO2014075392A1/en not_active Ceased
- 2013-11-15 US US14/443,294 patent/US9730940B2/en active Active
- 2013-11-15 BR BR112015011148A patent/BR112015011148A8/pt not_active Application Discontinuation
- 2013-11-15 AU AU2013347538A patent/AU2013347538B2/en not_active Ceased
- 2013-11-15 CA CA2891009A patent/CA2891009A1/en not_active Abandoned
- 2013-11-15 KR KR1020157015530A patent/KR20150082613A/ko not_active Withdrawn
- 2013-11-15 JP JP2015542134A patent/JP6297582B2/ja not_active Expired - Fee Related
- 2013-11-15 RU RU2015122895A patent/RU2658006C2/ru not_active IP Right Cessation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2015122895A (ru) | Пуриновые ингибиторы человеческой фосфатидилинозит 3-киназы дельта | |
| US12331056B2 (en) | SHP2 phosphatase inhibitors and methods of use thereof | |
| US12281101B2 (en) | Bicyclic lactams and methods of use thereof | |
| RU2473549C2 (ru) | Пиримидиновые соединения, композиции и способы применения | |
| RU2015122894A (ru) | Пуриновые ингибиторы фосфатидилинозитол-3-киназы дельта человека | |
| KR101812357B1 (ko) | Ｃｄｋ4/6의 억제제로서의 피롤로피리미딘 화합물 | |
| JP2016502522A5 (enExample) | ||
| JP2015522002A5 (enExample) | ||
| TW202423440A (zh) | Ｋｒａｓ ｇ１２ｃ突變蛋白的系鏈之雜環抑制劑及其用途 | |
| JP2021506941A5 (enExample) | ||
| WO2018218133A1 (en) | Pyrazolo[3,4-b]pyrazine derivatives as shp2 phosphatase inhibitors | |
| HRP20210177T1 (hr) | Supstituirani spojevi pirazolo[1,5-a]piridina kao inhibitori ret kinaze | |
| HRP20120105T1 (hr) | Aminoheterociklički spojevi | |
| JP2014506929A5 (enExample) | ||
| RU2020129785A (ru) | Фармацевтические производные 6,5-гетеробициклического кольца | |
| JP2017505327A5 (enExample) | ||
| JP2015527399A5 (enExample) | ||
| AU2024332123A1 (en) | Compositions comprising werner syndrome helicase inhibitors and methods of using the same | |
| RU2016135637A (ru) | 6-гетероарилокси- и 6-арилоксихинолин-2-карбоксамиды и их применение | |
| JP2021504380A5 (enExample) | ||
| RU2014123316A (ru) | Ингибиторы фосфодиэстеразы типа 10а | |
| WO2025194054A1 (en) | Spirocyclic compounds as modulators of kras and uses thereof | |
| KR20230107291A (ko) | PPARγ 조절제 및 사용 방법 | |
| US20250304577A1 (en) | Tyk2 inhibitors | |
| US20250353841A1 (en) | Heterocyclic compounds for treating huntington's disease |