JP2020519596A5 - - Google Patents
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- Publication number
- JP2020519596A5 JP2020519596A5 JP2019561740A JP2019561740A JP2020519596A5 JP 2020519596 A5 JP2020519596 A5 JP 2020519596A5 JP 2019561740 A JP2019561740 A JP 2019561740A JP 2019561740 A JP2019561740 A JP 2019561740A JP 2020519596 A5 JP2020519596 A5 JP 2020519596A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- carboxamide
- pyridine
- oxopyrrolidine
- alkyl
- 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 16
- UHADCXYRFWNAIW-UHFFFAOYSA-N thieno[3,2-b]pyridine-6-carboxamide Chemical compound NC(=O)C1=CN=C2C=CSC2=C1 UHADCXYRFWNAIW-UHFFFAOYSA-N 0.000 claims 13
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 125000004432 carbon atom Chemical group C* 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 7
- 239000000651 prodrug Substances 0.000 claims 7
- 229940002612 prodrug Drugs 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- CXAVMJMSOVJRGN-GKAPJAKFSA-N 3-[[(2S)-4-ethyl-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)C1C[C@H](NC1=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC CXAVMJMSOVJRGN-GKAPJAKFSA-N 0.000 claims 2
- KYAUGNGWRPHIKM-HTRCEHHLSA-N 3-[[(2S,3R)-3-(difluoromethyl)-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound FC([C@H]1[C@H](NC(C1)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC)F KYAUGNGWRPHIKM-HTRCEHHLSA-N 0.000 claims 2
- MZIDQIJKMGDYNV-WDEREUQCSA-N 3-[[(2S,3R)-3-ethyl-4,4-dimethyl-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC(C1(C)C)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC MZIDQIJKMGDYNV-WDEREUQCSA-N 0.000 claims 2
- GRIFYPOVVPFKDP-MWLCHTKSSA-N 3-[[(2S,3R)-3-ethyl-5-oxopyrrolidin-2-yl]methoxy]-5-methoxy-2-methylthieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC(C1)=O)COC1=C(SC=2C1=NC(=C(C=2)C(=O)N)OC)C GRIFYPOVVPFKDP-MWLCHTKSSA-N 0.000 claims 2
- JOURHXMSIVDFOM-PSASIEDQSA-N 3-[[(2S,3R)-3-ethyl-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC(C1)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC JOURHXMSIVDFOM-PSASIEDQSA-N 0.000 claims 2
- SGUQRVCNSLWDBQ-DTWKUNHWSA-N 3-[[(2S,3S)-3-ethyl-4,4-difluoro-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC(C1(F)F)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC SGUQRVCNSLWDBQ-DTWKUNHWSA-N 0.000 claims 2
- UCMNRCASMUCEBF-POYBYMJQSA-N 3-[[(2S,3S)-4,4-difluoro-3-methyl-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound FC1([C@H]([C@H](NC1=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC)C)F UCMNRCASMUCEBF-POYBYMJQSA-N 0.000 claims 2
- IDKCWTVRKJKDGD-JIMOISOXSA-N 3-[[(2S,3S,4R)-3-cyclopropyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C1(CC1)[C@H]1[C@H](NC([C@@H]1F)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC IDKCWTVRKJKDGD-JIMOISOXSA-N 0.000 claims 2
- VCFPCGNQQWIFHX-LPBBDHJYSA-N 3-[[(2S,3S,4R)-3-ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC([C@@H]1F)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC VCFPCGNQQWIFHX-LPBBDHJYSA-N 0.000 claims 2
- OMGRBHVIMQPNQG-FMTFEUNWSA-N 3-[[(2S,3S,4R)-4-fluoro-3-methyl-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound F[C@@H]1[C@H]([C@H](NC1=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC)C OMGRBHVIMQPNQG-FMTFEUNWSA-N 0.000 claims 2
- VWWOWLQWHHFXGW-AVZKPZGTSA-N 3-[[(2S,3S,4S)-3-ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy]-5-methoxy-1-benzothiophene-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC([C@H]1F)=O)COC=1C2=C(SC=1)C=C(C(=C2)OC)C(=O)N VWWOWLQWHHFXGW-AVZKPZGTSA-N 0.000 claims 2
- LSDQOYGTTSEFJM-XRNSZHNASA-N 3-[[(2S,3S,4S)-3-ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy]-5-methoxy-2-methylthieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC([C@H]1F)=O)COC1=C(SC=2C1=NC(=C(C=2)C(=O)N)OC)C LSDQOYGTTSEFJM-XRNSZHNASA-N 0.000 claims 2
- VCFPCGNQQWIFHX-VMAXQDLPSA-N 3-[[(2S,3S,4S)-3-ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC([C@H]1F)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC VCFPCGNQQWIFHX-VMAXQDLPSA-N 0.000 claims 2
- OMGRBHVIMQPNQG-QXHCQDJKSA-N 3-[[(2S,3S,4S)-4-fluoro-3-methyl-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC)C OMGRBHVIMQPNQG-QXHCQDJKSA-N 0.000 claims 2
- GSTVNFHWOCHAQX-POYBYMJQSA-N 3-[[(2S,4R)-4-fluoro-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound F[C@@H]1C[C@H](NC1=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC GSTVNFHWOCHAQX-POYBYMJQSA-N 0.000 claims 2
- RCMJGXZWAVXCFC-BDAKNGLRSA-N 3-[[(4R,5S)-5-ethyl-2-oxo-1,3-oxazolidin-4-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC(O1)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC RCMJGXZWAVXCFC-BDAKNGLRSA-N 0.000 claims 2
- DFEJEHBGWWIOHJ-WDEREUQCSA-N 3-[[(6S,7R)-7-ethyl-4-oxo-5-azaspiro[2.4]heptan-6-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC(C11CC1)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC DFEJEHBGWWIOHJ-WDEREUQCSA-N 0.000 claims 2
- 201000005569 Gout Diseases 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- KTEXIXPZKKQNSC-UHFFFAOYSA-N thieno[2,3-b]pyridine-6-carboxamide Chemical compound NC(=O)C1=CC=C2C=CSC2=N1 KTEXIXPZKKQNSC-UHFFFAOYSA-N 0.000 claims 2
- IJVLTWIHDJTMLR-BXKDBHETSA-N 3-[[(2S,3R)-3-ethyl-5-oxopyrrolidin-2-yl]methoxy]-5-methoxy-1-benzothiophene-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC(C1)=O)COC=1C2=C(SC=1)C=C(C(=C2)OC)C(=O)N IJVLTWIHDJTMLR-BXKDBHETSA-N 0.000 claims 1
- GEWAWLWMBOMUII-PXWWUCIGSA-N 3-[[(2S,3S,4S)-3-ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy]-5-propan-2-yloxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC([C@H]1F)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC(C)C GEWAWLWMBOMUII-PXWWUCIGSA-N 0.000 claims 1
- 208000026326 Adult-onset Still disease Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000023328 Basedow disease Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010015150 Erythema Diseases 0.000 claims 1
- 206010016207 Familial Mediterranean fever Diseases 0.000 claims 1
- 206010018634 Gouty Arthritis Diseases 0.000 claims 1
- 208000015023 Graves' disease Diseases 0.000 claims 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 1
- 208000005777 Lupus Nephritis Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 230000000735 allogeneic effect Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 208000022993 cryopyrin-associated periodic syndrome Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 231100000321 erythema Toxicity 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 208000020408 systemic-onset juvenile idiopathic arthritis Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 102000003298 tumor necrosis factor receptor Human genes 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762504956P | 2017-05-11 | 2017-05-11 | |
| US62/504,956 | 2017-05-11 | ||
| PCT/US2018/031945 WO2018209012A1 (en) | 2017-05-11 | 2018-05-10 | Thienopyridines and benzothiophenes useful as irak4 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020519596A JP2020519596A (ja) | 2020-07-02 |
| JP2020519596A5 true JP2020519596A5 (https=) | 2021-06-10 |
| JP7154229B2 JP7154229B2 (ja) | 2022-10-17 |
Family
ID=62245511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019561740A Active JP7154229B2 (ja) | 2017-05-11 | 2018-05-10 | Ｉｒａｋ－４阻害剤として有用なチエノピリジンおよびベンゾチオフェン |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US10829496B2 (https=) |
| EP (1) | EP3621960B1 (https=) |
| JP (1) | JP7154229B2 (https=) |
| KR (1) | KR102604900B1 (https=) |
| CN (1) | CN110612298B (https=) |
| AR (1) | AR111689A1 (https=) |
| AU (1) | AU2018265130B2 (https=) |
| BR (1) | BR112019023290A2 (https=) |
| CA (1) | CA3062602A1 (https=) |
| CL (1) | CL2019003198A1 (https=) |
| CO (1) | CO2019012494A2 (https=) |
| CY (1) | CY1124552T1 (https=) |
| DK (1) | DK3621960T3 (https=) |
| EA (1) | EA039189B1 (https=) |
| ES (1) | ES2889926T3 (https=) |
| HR (1) | HRP20211583T1 (https=) |
| HU (1) | HUE056493T2 (https=) |
| IL (1) | IL270494B (https=) |
| LT (1) | LT3621960T (https=) |
| MX (1) | MX2019012929A (https=) |
| MY (1) | MY200228A (https=) |
| PE (1) | PE20191817A1 (https=) |
| PL (1) | PL3621960T3 (https=) |
| PT (1) | PT3621960T (https=) |
| RS (1) | RS62430B1 (https=) |
| SI (1) | SI3621960T1 (https=) |
| SM (1) | SMT202100568T1 (https=) |
| TW (1) | TW201900640A (https=) |
| WO (1) | WO2018209012A1 (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019060693A1 (en) | 2017-09-22 | 2019-03-28 | Kymera Therapeutics, Inc. | CRBN LIGANDS AND USES THEREOF |
| MX2020003190A (es) | 2017-09-22 | 2020-11-11 | Kymera Therapeutics Inc | Degradadores de proteinas y usos de los mismos. |
| WO2019111218A1 (en) | 2017-12-08 | 2019-06-13 | Cadila Healthcare Limited | Novel heterocyclic compounds as irak4 inhibitors |
| IL315310A (en) | 2017-12-26 | 2024-10-01 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| WO2019140380A1 (en) | 2018-01-12 | 2019-07-18 | Kymera Therapeutics, Inc. | Protein degraders and uses thereof |
| WO2019140387A1 (en) | 2018-01-12 | 2019-07-18 | Kymera Therapeutics, Inc. | Crbn ligands and uses thereof |
| WO2020010227A1 (en) | 2018-07-06 | 2020-01-09 | Kymera Therapeutics, Inc. | Protein degraders and uses thereof |
| US11292792B2 (en) | 2018-07-06 | 2022-04-05 | Kymera Therapeutics, Inc. | Tricyclic CRBN ligands and uses thereof |
| JP7623943B2 (ja) | 2018-11-30 | 2025-01-29 | カイメラ セラピューティクス， インコーポレイテッド | Ｉｒａｋ分解剤およびそれらの使用 |
| BR112021026517A2 (pt) | 2019-06-28 | 2022-05-10 | Kymera Therapeutics Inc | Degradadores de irak e usos dos mesmos |
| TW202115086A (zh) | 2019-06-28 | 2021-04-16 | 美商輝瑞大藥廠 | Bckdk抑制劑 |
| WO2021011868A1 (en) | 2019-07-17 | 2021-01-21 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| CN114127075B (zh) | 2019-07-18 | 2024-05-14 | 百时美施贵宝公司 | 可用作IRAK4抑制剂的吡唑并[3,4-d]吡咯并[1,2-b]哒嗪基化合物 |
| EP3999508B1 (en) | 2019-07-18 | 2023-08-30 | Bristol-Myers Squibb Company | Tricyclic heteroaryl compounds useful as irak4 inhibitors |
| JP7573596B2 (ja) * | 2019-07-23 | 2024-10-25 | ブリストル－マイヤーズ スクイブ カンパニー | Ｉｒａｋ４阻害剤として有用なチエノピリジニルおよびチアゾロピリジニル化合物 |
| WO2021026181A1 (en) | 2019-08-06 | 2021-02-11 | Bristol-Myers Squibb Company | Bicyclic heterocyclic compounds useful as irak4 inhibitors |
| ES3059914T3 (en) | 2019-08-13 | 2026-03-24 | Bristol Myers Squibb Co | Bicyclic heteroaryl compounds useful as irak4 inhibitors |
| US12551564B2 (en) | 2019-12-10 | 2026-02-17 | Kymera Therapeutics, Inc. | IRAK degraders and uses thereof |
| WO2021127190A1 (en) | 2019-12-17 | 2021-06-24 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| WO2021127283A2 (en) | 2019-12-17 | 2021-06-24 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| WO2021158495A1 (en) | 2020-02-03 | 2021-08-12 | Bristol-Myers Squibb Company | Benzo[5,6][1,4]dioxino[2,3-b]pyridine compounds useful as irak4 inhibitors |
| CN111285844B (zh) * | 2020-02-24 | 2022-08-12 | 河南师范大学 | 具有生物活性的苯并噻吩取代酰胺类化合物及其合成方法和应用 |
| 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 |
| PH12023500015A1 (en) | 2020-12-30 | 2024-03-11 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| WO2022174268A1 (en) | 2021-02-15 | 2022-08-18 | Kymera Therapeutics, Inc. | Irak4 degraders and uses thereof |
| AU2022271290A1 (en) | 2021-05-07 | 2023-11-23 | Kymera Therapeutics, Inc. | Cdk2 degraders and uses thereof |
| US12187744B2 (en) | 2021-10-29 | 2025-01-07 | Kymera Therapeutics, Inc. | IRAK4 degraders and synthesis thereof |
| EP4472967A4 (en) | 2022-01-31 | 2026-04-15 | Kymera Therapeutics Inc | Iraqi Degradation Agents and Their Uses |
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| CN104254533B (zh) | 2012-01-13 | 2017-09-08 | 百时美施贵宝公司 | 用作激酶抑制剂的噻唑或噻二唑取代的吡啶基化合物 |
| KR20150079963A (ko) | 2012-11-08 | 2015-07-08 | 브리스톨-마이어스 스큅 컴퍼니 | 키나제 조절제로서 유용한 헤테로아릴 치환된 피리딜 화합물 |
| CN104781251B (zh) | 2012-11-08 | 2016-12-14 | 百时美施贵宝公司 | 可作为激酶调节剂的经双环杂环取代的吡啶基化合物 |
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| AR094537A1 (es) | 2013-11-07 | 2015-08-12 | Bristol Myers Squibb Co | COMPUESTOS DE PIRIDILO SUSTITUIDOS CON ALQUILAMIDA ÚTILES COMO MODULADORES DE LAS RESPUESTAS DE IL-12, IL-23 Y/O IFNa |
| MA39838B1 (fr) | 2014-04-04 | 2019-05-31 | Pfizer | Composés bicycliques hétéroaryle ou aryle fusionnés et leur utilisation en tant qu'inhibiteurs irak4 |
| EP3268003B1 (en) * | 2015-03-12 | 2020-07-29 | Merck Sharp & Dohme Corp. | Thienopyrazine inhibitors of irak4 activity |
| US10155765B2 (en) * | 2015-03-12 | 2018-12-18 | Merck Sharp & Dohme Corp. | Carboxamide inhibitors of IRAK4 activity |
| ES2822956T3 (es) | 2015-06-24 | 2021-05-05 | Bristol Myers Squibb Co | Compuestos de aminopiridina sustituidos con heteroarilo |
| TW201718571A (zh) | 2015-06-24 | 2017-06-01 | 必治妥美雅史谷比公司 | 經雜芳基取代之胺基吡啶化合物 |
| ES2865199T3 (es) * | 2015-08-27 | 2021-10-15 | Pfizer | Compuestos de heteroarilo o arilo condensados bicíclicos como moduladores de IRAK4 |
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2018
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- 2018-05-10 EA EA201992674A patent/EA039189B1/ru unknown
- 2018-05-10 CN CN201880031240.4A patent/CN110612298B/zh active Active
- 2018-05-10 US US16/612,478 patent/US10829496B2/en active Active
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