JP6416275B2 - ヘテロアリールsyk阻害剤 - Google Patents
ヘテロアリールsyk阻害剤 Download PDFInfo
- Publication number
- JP6416275B2 JP6416275B2 JP2016557952A JP2016557952A JP6416275B2 JP 6416275 B2 JP6416275 B2 JP 6416275B2 JP 2016557952 A JP2016557952 A JP 2016557952A JP 2016557952 A JP2016557952 A JP 2016557952A JP 6416275 B2 JP6416275 B2 JP 6416275B2
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- Prior art keywords
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- het
- alkyl
- oxo
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 0 C*=*1C(O[C@](*)[C@@](CC=N)NC(C)=O)=*C(**)=C*1 Chemical compound C*=*1C(O[C@](*)[C@@](CC=N)NC(C)=O)=*C(**)=C*1 0.000 description 7
- QSQWENQPOSRWLP-UHFFFAOYSA-N CC(C)(C)OC(N(CC1)CCC1[n]1ncc(B2OC(C)(C)C(C)(C)O2)c1)=O Chemical compound CC(C)(C)OC(N(CC1)CCC1[n]1ncc(B2OC(C)(C)C(C)(C)O2)c1)=O QSQWENQPOSRWLP-UHFFFAOYSA-N 0.000 description 1
- HCUPWGDFMZTHSA-UHFFFAOYSA-N CC(C)(C)OC(NN=C(CC1)CCC1(F)F)=O Chemical compound CC(C)(C)OC(NN=C(CC1)CCC1(F)F)=O HCUPWGDFMZTHSA-UHFFFAOYSA-N 0.000 description 1
- WOENHMHUZMWRJY-UHFFFAOYSA-N CC(C)(C)OC(NNC(CC1)CCC1(F)F)=O Chemical compound CC(C)(C)OC(NNC(CC1)CCC1(F)F)=O WOENHMHUZMWRJY-UHFFFAOYSA-N 0.000 description 1
- LOVCXYIMSRTGAR-TVKKRMFBSA-N CC(c(cc1)ccc1OC)N(C[C@@H](C1)C(NOC)=O)C1=O Chemical compound CC(c(cc1)ccc1OC)N(C[C@@H](C1)C(NOC)=O)C1=O LOVCXYIMSRTGAR-TVKKRMFBSA-N 0.000 description 1
- JBOIQIRJYOXYDQ-HCCKASOXSA-N CC(c(cc1)ccc1OC)N(C[C@@H](C1)C(O)=O)C1=O Chemical compound CC(c(cc1)ccc1OC)N(C[C@@H](C1)C(O)=O)C1=O JBOIQIRJYOXYDQ-HCCKASOXSA-N 0.000 description 1
- VCMSGGJUFFRKBZ-UHFFFAOYSA-N CC1(C)OB(c2c[n](C3CCNCC3)nc2)OC1(C)C Chemical compound CC1(C)OB(c2c[n](C3CCNCC3)nc2)OC1(C)C VCMSGGJUFFRKBZ-UHFFFAOYSA-N 0.000 description 1
- XJHHJKRQUDXIKL-UHFFFAOYSA-N CC1(C)OB(c2cnc(C3CC3)cc2)OC1(C)C Chemical compound CC1(C)OB(c2cnc(C3CC3)cc2)OC1(C)C XJHHJKRQUDXIKL-UHFFFAOYSA-N 0.000 description 1
- PVPKAOUYPAEICK-UHFFFAOYSA-N CCOC(c1c[n](C)nc1N)=O Chemical compound CCOC(c1c[n](C)nc1N)=O PVPKAOUYPAEICK-UHFFFAOYSA-N 0.000 description 1
- ISAHHKIFSLXUBO-UHFFFAOYSA-N CN(C)C(c([n](C)c1c2)cc1ccc2Br)=O Chemical compound CN(C)C(c([n](C)c1c2)cc1ccc2Br)=O ISAHHKIFSLXUBO-UHFFFAOYSA-N 0.000 description 1
- LOVCXYIMSRTGAR-NUHJPDEHSA-N C[C@@H](c(cc1)ccc1OC)N(CC(C1)C(NOC)=O)C1=O Chemical compound C[C@@H](c(cc1)ccc1OC)N(CC(C1)C(NOC)=O)C1=O LOVCXYIMSRTGAR-NUHJPDEHSA-N 0.000 description 1
- XZXAYJGAMIYAIZ-GXFFZTMASA-N C[C@@H](c(cc1)ccc1OC)N(C[C@@H](C1)C(C)=O)C1=O Chemical compound C[C@@H](c(cc1)ccc1OC)N(C[C@@H](C1)C(C)=O)C1=O XZXAYJGAMIYAIZ-GXFFZTMASA-N 0.000 description 1
- WEAPUKHGRBTBGN-KEKZHRQWSA-N C[C@H](C(C1)CNC1=O)Oc1nc(-c2cnc(C3CC3)cc2)cc2n[n](C)cc12 Chemical compound C[C@H](C(C1)CNC1=O)Oc1nc(-c2cnc(C3CC3)cc2)cc2n[n](C)cc12 WEAPUKHGRBTBGN-KEKZHRQWSA-N 0.000 description 1
- BJEAPGNDANNBOF-ZGHZLVQRSA-O C[C@H]([C@H](C1)CNC1=O)OC(/C1=C/NC)=NC(/C(/C=N)=C/NC(CC2)CCC2(F)F)=CC1=[NH2+] Chemical compound C[C@H]([C@H](C1)CNC1=O)OC(/C1=C/NC)=NC(/C(/C=N)=C/NC(CC2)CCC2(F)F)=CC1=[NH2+] BJEAPGNDANNBOF-ZGHZLVQRSA-O 0.000 description 1
- ZPDPHHVQONAXJZ-INTUZXOQSA-O C[C@H]([C@H](C1)CNC1=O)OC(/C1=C/NC)=NC(B(O)O)=CC1=[NH2+] Chemical compound C[C@H]([C@H](C1)CNC1=O)OC(/C1=C/NC)=NC(B(O)O)=CC1=[NH2+] ZPDPHHVQONAXJZ-INTUZXOQSA-O 0.000 description 1
- RLGUKVTXXJPYSA-INTUZXOQSA-O C[C@H]([C@H](C1)CNC1=O)OC(/C1=C/NC)=NC(Cl)=CC1=[NH2+] Chemical compound C[C@H]([C@H](C1)CNC1=O)OC(/C1=C/NC)=NC(Cl)=CC1=[NH2+] RLGUKVTXXJPYSA-INTUZXOQSA-O 0.000 description 1
- HLVQIKPORSSRAI-DGCLKSJQSA-N C[C@H]([C@H](C1)CNC1=O)Oc1nc(-c(cc2OC)ccc2O)cc2n[n](C)cc12 Chemical compound C[C@H]([C@H](C1)CNC1=O)Oc1nc(-c(cc2OC)ccc2O)cc2n[n](C)cc12 HLVQIKPORSSRAI-DGCLKSJQSA-N 0.000 description 1
- RHKFNBPBFDOJOE-CHWSQXEVSA-N C[C@H]([C@H](C1)CNC1=O)Oc1nc(-c2c[n](C(C)(C)C)nc2)cc2n[n](C)cc12 Chemical compound C[C@H]([C@H](C1)CNC1=O)Oc1nc(-c2c[n](C(C)(C)C)nc2)cc2n[n](C)cc12 RHKFNBPBFDOJOE-CHWSQXEVSA-N 0.000 description 1
- FTICWADNPRYZIE-ZIAGYGMSSA-N C[C@H]([C@H](C1)CNC1=O)Oc1nc(-c2c[n](C3CCNCC3)nc2)cc2n[n](C)cc12 Chemical compound C[C@H]([C@H](C1)CNC1=O)Oc1nc(-c2c[n](C3CCNCC3)nc2)cc2n[n](C)cc12 FTICWADNPRYZIE-ZIAGYGMSSA-N 0.000 description 1
- AOYPDQJNZQBEDW-UHFFFAOYSA-N C[n]1c2cc(Br)ccc2cc1C(O)=O Chemical compound C[n]1c2cc(Br)ccc2cc1C(O)=O AOYPDQJNZQBEDW-UHFFFAOYSA-N 0.000 description 1
- UVRACNCWSYZQCC-CQSZACIVSA-N C[n]1nc(cc(-c(cc2OC)ccc2OC)nc2OC([C@H](C3)CNC3=O)=C)c2c1 Chemical compound C[n]1nc(cc(-c(cc2OC)ccc2OC)nc2OC([C@H](C3)CNC3=O)=C)c2c1 UVRACNCWSYZQCC-CQSZACIVSA-N 0.000 description 1
- MWRBFSOZKDMYIS-UHFFFAOYSA-N Cc(cc1)ccc1S(C)(=O)=[O]C Chemical compound Cc(cc1)ccc1S(C)(=O)=[O]C MWRBFSOZKDMYIS-UHFFFAOYSA-N 0.000 description 1
- ALUPRDWIMCMTAH-LUAWRHEFSA-N Cc(cc1)ccc1S(O/C=C1\COCC1)=O Chemical compound Cc(cc1)ccc1S(O/C=C1\COCC1)=O ALUPRDWIMCMTAH-LUAWRHEFSA-N 0.000 description 1
- HHOCNDRXKKGAEA-RJMHLRASSA-N N=C/C(/Br)=C\[N-]C(CC1)CCC1(F)F Chemical compound N=C/C(/Br)=C\[N-]C(CC1)CCC1(F)F HHOCNDRXKKGAEA-RJMHLRASSA-N 0.000 description 1
Classifications
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
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- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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| CN105503730B (zh) * | 2015-12-25 | 2018-06-22 | 山东大学 | 吡唑类衍生物及其制备方法与应用 |
| MY193511A (en) * | 2016-11-02 | 2022-10-17 | Janssen Pharmaceutica Nv | [1,2,4]triazolo[1,5-a]pyrimidine derivatives as pde2 inhibitors |
| MA46690A (fr) | 2016-11-02 | 2019-09-11 | Janssen Pharmaceutica Nv | Composés de [1,2,4]triazolo [1,5-a]pyrimidine en tant qu'inhibiteurs de pde2 |
| CN109937202B (zh) | 2016-11-02 | 2022-12-30 | 詹森药业有限公司 | 作为pde2抑制剂的[1,2,4]三唑并[1,5-a]嘧啶化合物 |
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| JP7065951B2 (ja) | 2017-09-22 | 2022-05-12 | ジュビラント エピパッド エルエルシー | Pad阻害剤としての複素環式化合物 |
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| EP3707135A1 (en) | 2017-11-06 | 2020-09-16 | Jubilant Prodel LLC | Pyrimidine derivatives as inhibitors of pd1/pd-l1 activation |
| IL274762B2 (en) | 2017-11-24 | 2023-10-01 | Jubilant Episcribe Llc | Novel heterocyclic compounds as prmt5 inhibitors |
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| WO2019175897A1 (en) | 2018-03-13 | 2019-09-19 | Jubilant Biosys Limited | Bicyclic compounds as inhibitors of pd1/pd-l1 interaction/activation |
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| TW202210483A (zh) | 2020-06-03 | 2022-03-16 | 美商凱麥拉醫療公司 | Irak降解劑之結晶型 |
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| JP2024506656A (ja) | 2021-02-15 | 2024-02-14 | カイメラ セラピューティクス, インコーポレイテッド | Irak4分解剤およびその使用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018529679A (ja) * | 2015-09-11 | 2018-10-11 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ピラゾリル置換ヘテロアリール及び医薬としてのその使用 |
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