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
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- 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 (cg-RX-API-DMAC7.html) | 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)
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019060742A1 (en) | 2017-09-22 | 2019-03-28 | Kymera Therapeutics, Inc | AGENTS FOR DEGRADING PROTEINS AND USES THEREOF |
| US11358948B2 (en) | 2017-09-22 | 2022-06-14 | Kymera Therapeutics, Inc. | CRBN ligands and uses thereof |
| 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 |
| WO2019140387A1 (en) | 2018-01-12 | 2019-07-18 | Kymera Therapeutics, Inc. | Crbn ligands and uses thereof |
| WO2019140380A1 (en) | 2018-01-12 | 2019-07-18 | Kymera Therapeutics, Inc. | Protein degraders and uses thereof |
| WO2020010227A1 (en) | 2018-07-06 | 2020-01-09 | Kymera Therapeutics, Inc. | Protein degraders and uses thereof |
| WO2020010177A1 (en) | 2018-07-06 | 2020-01-09 | Kymera Therapeutics, Inc. | Tricyclic crbn ligands and uses thereof |
| CA3119773A1 (en) | 2018-11-30 | 2020-06-04 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| TW202115086A (zh) | 2019-06-28 | 2021-04-16 | 美商輝瑞大藥廠 | Bckdk抑制劑 |
| PH12022500002A1 (en) | 2019-06-28 | 2023-04-03 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| WO2021011868A1 (en) | 2019-07-17 | 2021-01-21 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| EP3999508B1 (en) | 2019-07-18 | 2023-08-30 | Bristol-Myers Squibb Company | Tricyclic heteroaryl compounds useful as irak4 inhibitors |
| WO2021011727A1 (en) | 2019-07-18 | 2021-01-21 | Bristol-Myers Squibb Company | PYRAZOLO[3,4-d]PYRROLO[1,2-b]PYRIDAZINYL COMPOUNDS USEFUL AS IRAK4 INHIBITORS |
| US12304916B2 (en) | 2019-07-23 | 2025-05-20 | Bristol-Myers Squibb Company | Thienopyridinyl and thiazolopyridinyl compounds useful as IRAK4 inhibitors |
| 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 |
| WO2021119159A1 (en) | 2019-12-10 | 2021-06-17 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| EP4076524A4 (en) | 2019-12-17 | 2023-11-29 | Kymera Therapeutics, Inc. | IRAQ DEGRADERS AND USES THEREOF |
| KR20220145325A (ko) | 2019-12-17 | 2022-10-28 | 카이메라 쎄라퓨틱스 인코포레이티드 | Irak 분해제 및 이의 용도 |
| 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 |
| CN116867758A (zh) | 2020-12-30 | 2023-10-10 | 凯麦拉医疗公司 | Irak降解剂和其用途 |
| US12171768B2 (en) | 2021-02-15 | 2024-12-24 | Kymera Therapeutics, Inc. | IRAK4 degraders and uses thereof |
| KR20240020735A (ko) | 2021-05-07 | 2024-02-15 | 카이메라 쎄라퓨틱스 인코포레이티드 | Cdk2 분해제 및 그 용도 |
| CA3236265A1 (en) | 2021-10-29 | 2023-05-04 | William Leong | Irak4 degraders and synthesis thereof |
| CA3243560A1 (en) | 2022-01-31 | 2023-08-03 | Kymera Therapeutics, Inc. | Iraqi Degradation Agents and Their Uses |
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| WO2016144849A1 (en) * | 2015-03-12 | 2016-09-15 | Merck Sharp & Dohme Corp. | Thienopyrazine inhibitors of irak4 activity |
| ES2822956T3 (es) | 2015-06-24 | 2021-05-05 | Bristol Myers Squibb Co | Compuestos de aminopiridina sustituidos con heteroarilo |
| EP3313840B1 (en) | 2015-06-24 | 2019-07-24 | Bristol-Myers Squibb Company | Heteroaryl substituted aminopyridine compounds |
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2018
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2019
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2021
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