JP2019533687A5 - - Google Patents
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- Publication number
- JP2019533687A5 JP2019533687A5 JP2019522484A JP2019522484A JP2019533687A5 JP 2019533687 A5 JP2019533687 A5 JP 2019533687A5 JP 2019522484 A JP2019522484 A JP 2019522484A JP 2019522484 A JP2019522484 A JP 2019522484A JP 2019533687 A5 JP2019533687 A5 JP 2019533687A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- methyl
- pyrazole
- pyrazol
- carboxamide
- 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
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- -1 heteroaliphatic Chemical group 0.000 claims description 254
- 150000001875 compounds Chemical class 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 150000001408 amides Chemical group 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 102100036342 Interleukin-1 receptor-associated kinase 1 Human genes 0.000 claims description 9
- 101710199015 Interleukin-1 receptor-associated kinase 1 Proteins 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 8
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 6
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229940124530 sulfonamide Drugs 0.000 claims description 6
- 150000003456 sulfonamides Chemical class 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 230000000302 ischemic effect Effects 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- QBFMYJJUPUMKPO-UHFFFAOYSA-N N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)-6-pyridin-4-ylpyridine-2-carboxamide Chemical compound CN1N=C(C(=C1)NC(=O)C1=CC=CC(=N1)C1=CC=NC=C1)C1=NC=CC=C1 QBFMYJJUPUMKPO-UHFFFAOYSA-N 0.000 claims description 4
- AOHILUYMWBKTMB-UHFFFAOYSA-N N-[1-[1-[2-(2-methoxyethoxy)ethyl]-3-pyridin-2-ylpyrazol-4-yl]-2-methyl-2H-pyridin-6-yl]-1H-indazol-5-amine Chemical compound N1N=CC2=CC(=CC=C12)NC1=CC=CC(N1C=1C(=NN(C=1)CCOCCOC)C1=NC=CC=C1)C AOHILUYMWBKTMB-UHFFFAOYSA-N 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 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 description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000003566 oxetanyl group Chemical group 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 208000035143 Bacterial infection Diseases 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 230000002519 immonomodulatory effect Effects 0.000 claims description 3
- 208000023504 respiratory system disease Diseases 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 238000002054 transplantation Methods 0.000 claims description 3
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims description 2
- RMHQDKYZXJVCME-UHFFFAOYSA-N 2-pyridin-4-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=NC=C1 RMHQDKYZXJVCME-UHFFFAOYSA-N 0.000 claims description 2
- QBEHIFVLFLZXTF-UHFFFAOYSA-N 5-[6-[[1-(oxetan-3-yl)-3-pyridin-2-ylpyrazol-4-yl]carbamoyl]pyridin-2-yl]pyridine-3-carboxylic acid Chemical compound O1CC(C1)N1N=C(C(=C1)NC(=O)C1=CC=CC(=N1)C=1C=NC=C(C=1)C(=O)O)C1=NC=CC=C1 QBEHIFVLFLZXTF-UHFFFAOYSA-N 0.000 claims description 2
- AQKKKMXHUZDXQZ-UHFFFAOYSA-N 6-(2-carbamoylpyridin-4-yl)-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound CN1N=C(C(=C1)NC(=O)C1=CC=CC(=N1)C1=CC(=NC=C1)C(=O)N)C1=NC=CC=C1 AQKKKMXHUZDXQZ-UHFFFAOYSA-N 0.000 claims description 2
- SYDDUVPHHRKPDS-UHFFFAOYSA-N 6-(2-cyanopyridin-4-yl)-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound C(#N)C1=NC=CC(=C1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CC=C1 SYDDUVPHHRKPDS-UHFFFAOYSA-N 0.000 claims description 2
- KNKKUSAYDDZVCV-UHFFFAOYSA-N 6-(2-methoxypyridin-4-yl)-N-(1-methyl-3-pyrazin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound COC1=NC=CC(=C1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CN=C1 KNKKUSAYDDZVCV-UHFFFAOYSA-N 0.000 claims description 2
- FEXNXLHQERMJCY-UHFFFAOYSA-N 6-(2-methoxypyridin-4-yl)-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound COC1=NC=CC(=C1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CC=C1 FEXNXLHQERMJCY-UHFFFAOYSA-N 0.000 claims description 2
- PYDKXYPIVUBFFI-UHFFFAOYSA-N 6-(2-methylpyridin-4-yl)-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound CC1=NC=CC(=C1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CC=C1 PYDKXYPIVUBFFI-UHFFFAOYSA-N 0.000 claims description 2
- XEHNDXZRJSEGMY-UHFFFAOYSA-N 6-(5-aminopyridin-3-yl)-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound NC=1C=C(C=NC=1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CC=C1 XEHNDXZRJSEGMY-UHFFFAOYSA-N 0.000 claims description 2
- ZTKBSDIZABEXSU-UHFFFAOYSA-N 6-(5-carbamoylpyridin-3-yl)-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound CN1N=C(C(=C1)NC(=O)C1=CC=CC(=N1)C=1C=NC=C(C=1)C(=O)N)C1=NC=CC=C1 ZTKBSDIZABEXSU-UHFFFAOYSA-N 0.000 claims description 2
- INCSVMCMRPKSKB-UHFFFAOYSA-N 6-(5-carbamoylpyridin-3-yl)-N-[1-(oxetan-3-yl)-3-pyridin-2-ylpyrazol-4-yl]pyridine-2-carboxamide Chemical compound O1CC(C1)N1N=C(C(=C1)NC(=O)C1=CC=CC(=N1)C=1C=NC=C(C=1)C(=O)N)C1=NC=CC=C1 INCSVMCMRPKSKB-UHFFFAOYSA-N 0.000 claims description 2
- FJSYAJRSQGIJQE-UHFFFAOYSA-N 6-(5-cyanopyridin-3-yl)-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound C(#N)C=1C=C(C=NC=1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CC=C1 FJSYAJRSQGIJQE-UHFFFAOYSA-N 0.000 claims description 2
- XOYAYZMHQUHOBA-UHFFFAOYSA-N 6-(5-cyclopropylpyridin-3-yl)-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound C1(CC1)C=1C=C(C=NC=1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CC=C1 XOYAYZMHQUHOBA-UHFFFAOYSA-N 0.000 claims description 2
- XSLDPQKBOPPWOQ-UHFFFAOYSA-N 6-(5-fluoropyridin-3-yl)-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound FC=1C=C(C=NC=1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CC=C1 XSLDPQKBOPPWOQ-UHFFFAOYSA-N 0.000 claims description 2
- MAGPVJYVFDLJOB-UHFFFAOYSA-N 6-(5-methoxypyridin-3-yl)-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound COC=1C=C(C=NC=1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CC=C1 MAGPVJYVFDLJOB-UHFFFAOYSA-N 0.000 claims description 2
- WBGXDYKTCIQOCS-UHFFFAOYSA-N 6-(5-methylpyridin-3-yl)-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound CC=1C=C(C=NC=1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CC=C1 WBGXDYKTCIQOCS-UHFFFAOYSA-N 0.000 claims description 2
- VWSQZAUEFLVYHM-UHFFFAOYSA-N 6-(5-methylpyridin-3-yl)-N-(1-propan-2-yl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound C(C)(C)N1N=C(C(=C1)NC(=O)C1=CC=CC(=N1)C=1C=NC=C(C=1)C)C1=NC=CC=C1 VWSQZAUEFLVYHM-UHFFFAOYSA-N 0.000 claims description 2
- APUJOSAJKMFDLV-UHFFFAOYSA-N 6-(5-methylpyridin-3-yl)-N-[1-(2-morpholin-4-ylethyl)-3-pyridin-2-ylpyrazol-4-yl]pyridine-2-carboxamide Chemical compound CC=1C=C(C=NC=1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)CCN1CCOCC1)C1=NC=CC=C1 APUJOSAJKMFDLV-UHFFFAOYSA-N 0.000 claims description 2
- HYAOKGQVLFOURI-UHFFFAOYSA-N 6-(5-methylpyridin-3-yl)-N-[1-(oxan-4-yl)-3-pyridin-2-ylpyrazol-4-yl]pyridine-2-carboxamide Chemical compound CC=1C=C(C=NC=1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C1CCOCC1)C1=NC=CC=C1 HYAOKGQVLFOURI-UHFFFAOYSA-N 0.000 claims description 2
- FTBVODWLCFBWJG-UHFFFAOYSA-N 6-(5-methylpyridin-3-yl)-N-[1-(oxetan-3-yl)-3-pyridin-2-ylpyrazol-4-yl]pyridine-2-carboxamide Chemical compound CC=1C=C(C=NC=1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C1COC1)C1=NC=CC=C1 FTBVODWLCFBWJG-UHFFFAOYSA-N 0.000 claims description 2
- DFHQGQLEUPPPOZ-UHFFFAOYSA-N 6-(6-aminopyridin-3-yl)-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound NC1=CC=C(C=N1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CC=C1 DFHQGQLEUPPPOZ-UHFFFAOYSA-N 0.000 claims description 2
- MWHQKWCDDQOMFJ-UHFFFAOYSA-N 6-(6-methoxypyridin-3-yl)-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound COC1=CC=C(C=N1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CC=C1 MWHQKWCDDQOMFJ-UHFFFAOYSA-N 0.000 claims description 2
- WGZGEHTYEYFSMZ-UHFFFAOYSA-N 6-(6-methylpyridin-3-yl)-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound CC1=CC=C(C=N1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CC=C1 WGZGEHTYEYFSMZ-UHFFFAOYSA-N 0.000 claims description 2
- FBCUDIMIYUIGPI-UHFFFAOYSA-N 6-[1-(3-chlorophenyl)pyrazol-4-yl]-1-[1-[2-(2-methoxyethoxy)ethyl]-3-pyridin-2-ylpyrazol-4-yl]-2-methyl-2H-pyridine Chemical compound ClC=1C=C(C=CC=1)N1N=CC(=C1)C1=CC=CC(N1C=1C(=NN(C=1)CCOCCOC)C1=NC=CC=C1)C FBCUDIMIYUIGPI-UHFFFAOYSA-N 0.000 claims description 2
- DVXJDONJRNPQFV-UHFFFAOYSA-N 6-[2-(cyclopropylmethylamino)pyridin-4-yl]-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound C1(CC1)CNC1=NC=CC(=C1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CC=C1 DVXJDONJRNPQFV-UHFFFAOYSA-N 0.000 claims description 2
- XXLDLSQLGWAJCH-UHFFFAOYSA-N 6-[5-(2-hydroxypropan-2-yl)pyridin-3-yl]-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound OC(C)(C)C=1C=C(C=NC=1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CC=C1 XXLDLSQLGWAJCH-UHFFFAOYSA-N 0.000 claims description 2
- CLURMQRDVHKAOY-UHFFFAOYSA-N 6-[5-(2-methoxyethylamino)pyridin-3-yl]-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound COCCNC=1C=C(C=NC=1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CC=C1 CLURMQRDVHKAOY-UHFFFAOYSA-N 0.000 claims description 2
- NGGCNCSANXVJMK-UHFFFAOYSA-N 6-[5-(4-methylpiperazin-1-yl)pyridin-3-yl]-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound CN1N=C(C(=C1)NC(=O)C1=CC=CC(=N1)C=1C=NC=C(C=1)N1CCN(CC1)C)C1=NC=CC=C1 NGGCNCSANXVJMK-UHFFFAOYSA-N 0.000 claims description 2
- OILCSRYERXEJDA-UHFFFAOYSA-N 6-[5-(cyclopropylamino)pyridin-3-yl]-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound C1(CC1)NC=1C=C(C=NC=1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CC=C1 OILCSRYERXEJDA-UHFFFAOYSA-N 0.000 claims description 2
- QSHZGNXMEVFJQT-UHFFFAOYSA-N 6-[5-(dimethylamino)pyridin-3-yl]-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound CN(C=1C=C(C=NC=1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CC=C1)C QSHZGNXMEVFJQT-UHFFFAOYSA-N 0.000 claims description 2
- HHJXVVMBYBZUEV-UHFFFAOYSA-N 6-[5-(methylamino)pyridin-3-yl]-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound CN1N=C(C(=C1)NC(=O)C1=CC=CC(=N1)C=1C=NC=C(C=1)NC)C1=NC=CC=C1 HHJXVVMBYBZUEV-UHFFFAOYSA-N 0.000 claims description 2
- QIXDTJIVVDJWOJ-UHFFFAOYSA-N 6-[5-(tert-butylamino)pyridin-3-yl]-N-(1-methyl-3-pyridin-2-ylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound C(C)(C)(C)NC=1C=C(C=NC=1)C1=NC(=CC=C1)C(=O)NC=1C(=NN(C=1)C)C1=NC=CC=C1 QIXDTJIVVDJWOJ-UHFFFAOYSA-N 0.000 claims description 2
- CPYLBJMFBYFBTC-UHFFFAOYSA-N 6-methoxy-2-[1-[1-[2-(2-methoxyethoxy)ethyl]-3-pyridin-2-ylpyrazol-4-yl]-2-methyl-2H-pyridin-6-yl]-1H-indole Chemical compound COC1=CC=C2C=C(NC2=C1)C1=CC=CC(N1C=1C(=NN(C=1)CCOCCOC)C1=NC=CC=C1)C CPYLBJMFBYFBTC-UHFFFAOYSA-N 0.000 claims description 2
- XMEVRHDZSJABSC-UHFFFAOYSA-N 6-pyridin-4-yl-N-(5-pyridin-2-yl-1H-pyrazol-4-yl)pyridine-2-carboxamide Chemical compound N1=C(C=CC=C1)C1=NNC=C1NC(=O)C1=CC=CC(=N1)C1=CC=NC=C1 XMEVRHDZSJABSC-UHFFFAOYSA-N 0.000 claims description 2
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| TW202340194A (zh) | 2017-02-16 | 2023-10-16 | 美商基利科學股份有限公司 | 吡咯并[1,2-b]嗒𠯤衍生物 |
| TWI842978B (zh) | 2018-07-13 | 2024-05-21 | 美商基利科學股份有限公司 | 衍生物 |
| CN110862375B (zh) * | 2018-08-27 | 2022-10-25 | 深圳铂立健医药有限公司 | 吡唑化合物及其药物组合物和应用 |
| MX2022001596A (es) * | 2019-08-08 | 2022-03-11 | Rigel Pharmaceuticals Inc | Compuestos y metodos para tratar sindrome de liberacion de citocinas. |
| WO2021066559A1 (en) * | 2019-10-02 | 2021-04-08 | Kainos Medicine, Inc. | N-(1h-imidazol-2-yl)benzamide compound and pharmaceutical composition comprising the same as active ingredient |
| US20240043405A1 (en) * | 2020-03-23 | 2024-02-08 | Dana-Farber Cancer Institute, Inc. | Potent and selective irreversible inhibitors of irak1 |
| US20240308980A1 (en) * | 2021-03-17 | 2024-09-19 | Merck Sharp & Dohme Llc | Heteroaryl amides as lrrk2 inhibitors, pharmaceutical compositions, and uses thereof |
| EP4399204A4 (en) * | 2021-09-08 | 2025-07-16 | Dana Farber Cancer Inst Inc | POTENT AND SELECTIVE IRAK4 INHIBITORS |
| IL315677A (en) | 2022-03-23 | 2024-11-01 | Rigel Pharmaceuticals Inc | Pyrimid-2-yl-pyrazole compounds as irak inhibitors |
| JP2025513850A (ja) | 2022-04-12 | 2025-04-30 | ジェンザイム・コーポレーション | 遺伝子治療のためのｉｒａｋ４モジュレーターの使用 |
| CN116751195B (zh) * | 2023-06-21 | 2025-03-07 | 杭州科兴生物化工有限公司 | 联吡啶类化合物、其可药用的盐以及制备方法和应用 |
| CN121270516A (zh) * | 2024-07-03 | 2026-01-06 | 科辉智药(深圳)新药研究中心有限公司 | 一种irak抑制剂化合物的晶型及其制备方法和应用 |
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- 2017-10-25 CN CN201780080550.0A patent/CN110234637B/zh active Active
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