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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| JOP20180011A1 (ar) | 2017-02-16 | 2019-01-30 | Gilead Sciences Inc | مشتقات بيرولو [1، 2-b]بيريدازين |
| 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 |
| CA3147443A1 (en) * | 2019-08-08 | 2021-02-11 | Rigel Pharmaceuticals, Inc. | Compounds and method for treating cytokine release syndrome |
| JP7386576B2 (ja) * | 2019-10-02 | 2023-11-27 | カイノス・メディスン・インコーポレイテッド | Ｎ－（１ｈ－イミダゾール－２－イル）ベンズアミド化合物および該化合物を活性成分として含む医薬組成物 |
| CN115484954A (zh) * | 2020-03-23 | 2022-12-16 | 达纳-法伯癌症研究所股份有限公司 | Irak1的有效和选择性不可逆抑制剂 |
| AU2022343550A1 (en) * | 2021-09-08 | 2024-03-28 | Dana-Farber Cancer Institute, Inc. | Potent and selective inhibitors of irak4 |
| JP2025513716A (ja) | 2022-03-23 | 2025-04-30 | ライジェル・ファーマシューティカルズ・インコーポレイテッド | Ｉｒａｋ阻害剤としてのピリミド－２－イル－ピラゾール化合物 |
| KR20250004740A (ko) | 2022-04-12 | 2025-01-08 | 젠자임 코포레이션 | 유전자 요법을 위한 irak4 조절제의 용도 |
| 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 |
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