JP2018535986A5 - - Google Patents
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- Publication number
- JP2018535986A5 JP2018535986A5 JP2018526716A JP2018526716A JP2018535986A5 JP 2018535986 A5 JP2018535986 A5 JP 2018535986A5 JP 2018526716 A JP2018526716 A JP 2018526716A JP 2018526716 A JP2018526716 A JP 2018526716A JP 2018535986 A5 JP2018535986 A5 JP 2018535986A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- thiadiazol
- acetamide
- amino
- phenyl
- 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
- -1 1,2,4-triazin-3-yl Chemical group 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 12
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 102100025960 Glutaminase kidney isoform, mitochondrial Human genes 0.000 claims 3
- 101000856990 Homo sapiens Glutaminase kidney isoform, mitochondrial Proteins 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 2
- WDDBMFLLFAMIRF-MLGOLLRUSA-N (2R)-2-[4-fluoro-3-(trifluoromethoxy)phenyl]-2-methoxy-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound FC1=C(C=C(C=C1)[C@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)OC)OC(F)(F)F WDDBMFLLFAMIRF-MLGOLLRUSA-N 0.000 claims 1
- ZFCXIZUETUNJKI-CXAGYDPISA-N (2R)-2-methoxy-2-[3-methoxy-5-(trifluoromethoxy)phenyl]-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound CO[C@@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)C1=CC(=CC(=C1)OC(F)(F)F)OC ZFCXIZUETUNJKI-CXAGYDPISA-N 0.000 claims 1
- SQQHQXXXLATMLV-WBVHZDCISA-N (2R)-3-methoxy-2-(3-methoxyphenyl)-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]propanamide Chemical compound COC[C@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)C1=CC(=CC=C1)OC SQQHQXXXLATMLV-WBVHZDCISA-N 0.000 claims 1
- ORRGLFGRVLUXNY-CJNGLKHVSA-N (2S)-2-(3,5-dimethoxyphenyl)-2-methoxy-N-[5-[[(3R)-1-(1,2,4-triazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound COC=1C=C(C=C(C=1)OC)[C@@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CN=1)OC ORRGLFGRVLUXNY-CJNGLKHVSA-N 0.000 claims 1
- YISJONSTNPDOGI-BEFAXECRSA-N (2S)-2-(3,5-dimethoxyphenyl)-2-methoxy-N-[5-[[(3R)-1-(6-methylpyridazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound COC=1C=C(C=C(C=1)OC)[C@@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC(=CC=1)C)OC YISJONSTNPDOGI-BEFAXECRSA-N 0.000 claims 1
- NKPBNEQDGYAJFW-WBVHZDCISA-N (2S)-2-(4-fluorophenyl)-2-methoxy-N-[5-[[(3R)-1-(5-methylpyridazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound FC1=CC=C(C=C1)[C@@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=C(C=1)C)OC NKPBNEQDGYAJFW-WBVHZDCISA-N 0.000 claims 1
- ZDCKWVSAJLNKEB-APWZRJJASA-N (2S)-2-[3-(3-fluoroazetidin-1-yl)phenyl]-2-methoxy-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound FC1CN(C1)C=1C=C(C=CC=1)[C@@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)OC ZDCKWVSAJLNKEB-APWZRJJASA-N 0.000 claims 1
- RXRILZDMSDDVGK-QRWLVFNGSA-N (2S)-2-[4-fluoro-3-(3-methoxyazetidin-1-yl)phenyl]-2-methoxy-N-[5-[(3R)-3-(pyridazin-3-ylamino)pyrrolidin-1-yl]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound FC1=C(C=C(C=C1)[C@@H](C(=O)NC=1SC(=NN=1)N1C[C@@H](CC1)NC=1N=NC=CC=1)OC)N1CC(C1)OC RXRILZDMSDDVGK-QRWLVFNGSA-N 0.000 claims 1
- WDDBMFLLFAMIRF-WBMJQRKESA-N (2S)-2-[4-fluoro-3-(trifluoromethoxy)phenyl]-2-methoxy-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound FC1=C(C=C(C=C1)[C@@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)OC)OC(F)(F)F WDDBMFLLFAMIRF-WBMJQRKESA-N 0.000 claims 1
- RZACPCSTHBDOLY-PBHICJAKSA-N (2S)-2-ethoxy-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]-2-[3-(trifluoromethoxy)phenyl]acetamide Chemical compound C(C)O[C@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)C1=CC(=CC=C1)OC(F)(F)F RZACPCSTHBDOLY-PBHICJAKSA-N 0.000 claims 1
- SMLCGOSBZPGHOV-UTKZUKDTSA-N (2S)-2-methoxy-2-[3-(3-methoxyazetidin-1-yl)phenyl]-N-[5-[[(3R)-1-(6-methylpyridazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound CO[C@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC(=CC=1)C)C1=CC(=CC=C1)N1CC(C1)OC SMLCGOSBZPGHOV-UTKZUKDTSA-N 0.000 claims 1
- YNGDVDDWQYYAAN-UZLBHIALSA-N (2S)-2-methoxy-2-[3-(3-methoxyazetidin-1-yl)phenyl]-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound CO[C@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)C1=CC(=CC=C1)N1CC(C1)OC YNGDVDDWQYYAAN-UZLBHIALSA-N 0.000 claims 1
- ZFCXIZUETUNJKI-DYVFJYSZSA-N (2S)-2-methoxy-2-[3-methoxy-5-(trifluoromethoxy)phenyl]-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound CO[C@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)C1=CC(=CC(=C1)OC(F)(F)F)OC ZFCXIZUETUNJKI-DYVFJYSZSA-N 0.000 claims 1
- BVXKPJNFBXKDMN-QRWLVFNGSA-N (2S)-N-[5-[[(3R)-1-(6-fluoropyridazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]-2-methoxy-2-[3-(3-methoxyazetidin-1-yl)phenyl]acetamide Chemical compound FC1=CC=C(N=N1)N1C[C@@H](CC1)NC1=NN=C(S1)NC([C@H](C1=CC(=CC=C1)N1CC(C1)OC)OC)=O BVXKPJNFBXKDMN-QRWLVFNGSA-N 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- FDWSDOCCHCRUFJ-SECBINFHSA-N N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1 FDWSDOCCHCRUFJ-SECBINFHSA-N 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562260789P | 2015-11-30 | 2015-11-30 | |
| US62/260,789 | 2015-11-30 | ||
| PCT/EP2016/079250 WO2017093299A1 (en) | 2015-11-30 | 2016-11-30 | 1,3,4-thiadiazole compounds and their use in treating cancer |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018535986A JP2018535986A (ja) | 2018-12-06 |
| JP2018535986A5 true JP2018535986A5 (OSRAM) | 2020-01-16 |
| JP6999550B2 JP6999550B2 (ja) | 2022-02-10 |
Family
ID=57485461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018526716A Active JP6999550B2 (ja) | 2015-11-30 | 2016-11-30 | １，３，４－チアジアゾール化合物およびがんの治療におけるその使用 |
Country Status (23)
| Country | Link |
|---|---|
| US (3) | US10323028B2 (OSRAM) |
| EP (1) | EP3383873B1 (OSRAM) |
| JP (1) | JP6999550B2 (OSRAM) |
| KR (1) | KR20180083942A (OSRAM) |
| CN (1) | CN108349966B (OSRAM) |
| AR (1) | AR106874A1 (OSRAM) |
| AU (1) | AU2016363718B2 (OSRAM) |
| BR (1) | BR112018010806A2 (OSRAM) |
| CA (1) | CA3005495C (OSRAM) |
| CL (1) | CL2018001407A1 (OSRAM) |
| CO (1) | CO2018006928A2 (OSRAM) |
| EA (1) | EA201891241A1 (OSRAM) |
| ES (1) | ES2914333T3 (OSRAM) |
| IL (1) | IL259510A (OSRAM) |
| MX (1) | MX2018006532A (OSRAM) |
| NI (1) | NI201800064A (OSRAM) |
| PH (1) | PH12018501131A1 (OSRAM) |
| RU (1) | RU2018123714A (OSRAM) |
| SG (1) | SG11201803810XA (OSRAM) |
| SV (1) | SV2018005702A (OSRAM) |
| TN (1) | TN2018000127A1 (OSRAM) |
| TW (1) | TW201733587A (OSRAM) |
| WO (1) | WO2017093299A1 (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201520959D0 (en) | 2015-11-27 | 2016-01-13 | Astrazeneca Ab And Cancer Res Technology Ltd | Bis-pyridazine compounds and their use in treating cancer |
| US9938265B2 (en) | 2015-11-30 | 2018-04-10 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| US10040789B2 (en) * | 2015-11-30 | 2018-08-07 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| US10323028B2 (en) | 2015-11-30 | 2019-06-18 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| JP7275053B2 (ja) * | 2017-06-13 | 2023-05-17 | メッドシャイン ディスカバリー インコーポレイテッド | Ｇｌｓ１阻害剤としての化合物 |
| CN112888686B (zh) * | 2018-10-16 | 2022-04-19 | 南京明德新药研发有限公司 | 噻二唑衍生物及其作为gls1抑制剂的应用 |
| WO2025196446A1 (en) * | 2024-03-22 | 2025-09-25 | Sitryx Therapeutics Limited | Thiadiazoles as glutaminase 1 inhibitors |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6451828B1 (en) * | 2000-08-10 | 2002-09-17 | Elan Pharmaceuticals, Inc. | Selective inhibition of glutaminase by bis-thiadiazoles |
| RS59705B1 (sr) | 2011-11-21 | 2020-01-31 | Calithera Biosciences Inc | Heterociklični inhibitori glutaminaze |
| JP6275153B2 (ja) * | 2012-11-16 | 2018-02-07 | キャリセラ バイオサイエンシーズ， インコーポレイテッド | ヘテロ環式グルタミナーゼ阻害剤 |
| US9029531B2 (en) | 2012-11-22 | 2015-05-12 | Agios Pharmaceuticals, Inc. | Compounds and their methods of use |
| EP3092235A2 (en) | 2014-01-06 | 2016-11-16 | Rhizen Pharmaceuticals S.A. | Novel inhibitors of glutaminase |
| WO2015138902A1 (en) * | 2014-03-14 | 2015-09-17 | Calithera Biosciences, Inc. | Combination therapy with glutaminase inhibitors |
| GB201409624D0 (en) | 2014-05-30 | 2014-07-16 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| GB201520959D0 (en) | 2015-11-27 | 2016-01-13 | Astrazeneca Ab And Cancer Res Technology Ltd | Bis-pyridazine compounds and their use in treating cancer |
| US9938265B2 (en) * | 2015-11-30 | 2018-04-10 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| US10040789B2 (en) | 2015-11-30 | 2018-08-07 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| US10323028B2 (en) | 2015-11-30 | 2019-06-18 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
-
2016
- 2016-11-29 US US15/363,030 patent/US10323028B2/en active Active
- 2016-11-29 TW TW105139337A patent/TW201733587A/zh unknown
- 2016-11-30 KR KR1020187018472A patent/KR20180083942A/ko not_active Withdrawn
- 2016-11-30 ES ES16806028T patent/ES2914333T3/es active Active
- 2016-11-30 AU AU2016363718A patent/AU2016363718B2/en active Active
- 2016-11-30 AR ARP160103663A patent/AR106874A1/es unknown
- 2016-11-30 CN CN201680067245.3A patent/CN108349966B/zh active Active
- 2016-11-30 CA CA3005495A patent/CA3005495C/en active Active
- 2016-11-30 JP JP2018526716A patent/JP6999550B2/ja active Active
- 2016-11-30 BR BR112018010806A patent/BR112018010806A2/pt not_active Application Discontinuation
- 2016-11-30 WO PCT/EP2016/079250 patent/WO2017093299A1/en not_active Ceased
- 2016-11-30 EP EP16806028.3A patent/EP3383873B1/en active Active
- 2016-11-30 MX MX2018006532A patent/MX2018006532A/es unknown
- 2016-11-30 SG SG11201803810XA patent/SG11201803810XA/en unknown
- 2016-11-30 EA EA201891241A patent/EA201891241A1/ru unknown
- 2016-11-30 RU RU2018123714A patent/RU2018123714A/ru not_active Application Discontinuation
- 2016-11-30 TN TNP/2018/000127A patent/TN2018000127A1/en unknown
-
2018
- 2018-05-22 IL IL259510A patent/IL259510A/en unknown
- 2018-05-24 CL CL2018001407A patent/CL2018001407A1/es unknown
- 2018-05-29 PH PH12018501131A patent/PH12018501131A1/en unknown
- 2018-05-29 SV SV2018005702A patent/SV2018005702A/es unknown
- 2018-05-29 NI NI201800064A patent/NI201800064A/es unknown
- 2018-06-29 CO CONC2018/0006928A patent/CO2018006928A2/es unknown
-
2019
- 2019-05-03 US US16/402,825 patent/US10981904B2/en active Active
-
2021
- 2021-04-15 US US17/231,164 patent/US11753405B2/en active Active
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