JP2019501134A5 - - Google Patents
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- Publication number
- JP2019501134A5 JP2019501134A5 JP2018526717A JP2018526717A JP2019501134A5 JP 2019501134 A5 JP2019501134 A5 JP 2019501134A5 JP 2018526717 A JP2018526717 A JP 2018526717A JP 2018526717 A JP2018526717 A JP 2018526717A JP 2019501134 A5 JP2019501134 A5 JP 2019501134A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- pyrrolidin
- acetamide
- amino
- thiadiazol
- 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
- 150000001875 compounds Chemical class 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 11
- -1 5-methylpyridazin-3-yl Chemical group 0.000 claims 10
- 239000003814 drug Substances 0.000 claims 5
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- QFAHGXFMNKFWKL-KDOFPFPSSA-N (2S)-2-(4-fluoro-3-methoxyphenyl)-2-methoxy-N-[5-[[(3R)-1-(6-methylpyridazin-3-yl)pyrrolidin-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)C)OC)OC QFAHGXFMNKFWKL-KDOFPFPSSA-N 0.000 claims 2
- 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 2
- HXFKMUYISOOFNN-WBVHZDCISA-N (2S)-2-(4-fluorophenyl)-2-methoxy-N-[5-[[(3R)-1-(6-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(=CC=1)C)OC HXFKMUYISOOFNN-WBVHZDCISA-N 0.000 claims 2
- PWHLVMVNBKXNML-APWZRJJASA-N (2S)-2-ethoxy-2-(3-methoxyphenyl)-N-[5-[[(3R)-1-(6-methylpyridazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)O[C@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC(=CC=1)C)C1=CC(=CC=C1)OC PWHLVMVNBKXNML-APWZRJJASA-N 0.000 claims 2
- CJPDRLNNFXCJTE-QAPCUYQASA-N (2S)-2-methoxy-2-(3-methoxyphenyl)-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)OC CJPDRLNNFXCJTE-QAPCUYQASA-N 0.000 claims 2
- SKUZHMFUXHGQQW-DYVFJYSZSA-N (2S)-N-[5-[[(3R)-1-(6-fluoropyridazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]-2-methoxy-2-(3-methoxyphenyl)acetamide Chemical compound FC1=CC=C(N=N1)N1C[C@@H](CC1)NC1=NN=C(S1)NC([C@H](C1=CC(=CC=C1)OC)OC)=O SKUZHMFUXHGQQW-DYVFJYSZSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- BILNGVPSJLOCKW-CJNGLKHVSA-N (2S)-N-[5-[[(3R)-1-(6-fluoropyridazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]-2-methoxy-2-phenylacetamide Chemical compound FC1=CC=C(N=N1)N1C[C@@H](CC1)NC1=NN=C(S1)NC([C@H](C1=CC=CC=C1)OC)=O BILNGVPSJLOCKW-CJNGLKHVSA-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
- FURBCBVZJOABRQ-XPCCGILXSA-N N-[5-[[(3R)-1-(5-chloropyridazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]-2-methoxy-2-(4-methoxyphenyl)acetamide Chemical compound ClC=1C=C(N=NC=1)N1C[C@@H](CC1)NC1=NN=C(S1)NC(C(C1=CC=C(C=C1)OC)OC)=O FURBCBVZJOABRQ-XPCCGILXSA-N 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562260787P | 2015-11-30 | 2015-11-30 | |
| US62/260,787 | 2015-11-30 | ||
| PCT/EP2016/079251 WO2017093300A1 (en) | 2015-11-30 | 2016-11-30 | 1,3,4-thiadiazole compounds and their use in treating cancer |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019501134A JP2019501134A (ja) | 2019-01-17 |
| JP2019501134A5 true JP2019501134A5 (OSRAM) | 2020-01-16 |
| JP6873132B2 JP6873132B2 (ja) | 2021-05-19 |
Family
ID=57421876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018526717A Active JP6873132B2 (ja) | 2015-11-30 | 2016-11-30 | １，３，４−チアジアゾール化合物および癌の治療におけるその使用 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US9938265B2 (OSRAM) |
| EP (1) | EP3383871B1 (OSRAM) |
| JP (1) | JP6873132B2 (OSRAM) |
| KR (1) | KR20180083412A (OSRAM) |
| CN (1) | CN108349967B (OSRAM) |
| AR (1) | AR106876A1 (OSRAM) |
| AU (1) | AU2016363719B2 (OSRAM) |
| BR (1) | BR112018010812A2 (OSRAM) |
| CA (1) | CA3005516C (OSRAM) |
| CL (1) | CL2018001408A1 (OSRAM) |
| CO (1) | CO2018006929A2 (OSRAM) |
| DK (1) | DK3383871T3 (OSRAM) |
| DO (1) | DOP2018000134A (OSRAM) |
| EA (1) | EA201891240A1 (OSRAM) |
| ES (1) | ES2759940T3 (OSRAM) |
| IL (1) | IL258644A (OSRAM) |
| MX (1) | MX2018006528A (OSRAM) |
| NI (1) | NI201800065A (OSRAM) |
| PE (1) | PE20181450A1 (OSRAM) |
| PH (1) | PH12018501132A1 (OSRAM) |
| SG (1) | SG11201803813UA (OSRAM) |
| SV (1) | SV2018005701A (OSRAM) |
| TN (1) | TN2018000126A1 (OSRAM) |
| TW (1) | TW201730188A (OSRAM) |
| WO (1) | WO2017093300A1 (OSRAM) |
Families Citing this family (5)
| 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 |
| 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 |
| JP7026852B2 (ja) * | 2018-10-16 | 2022-02-28 | メッドシャイン ディスカバリー インコーポレイテッド | チアジアゾール誘導体及びｇｌｓ１阻害剤としてのその使用 |
| WO2025196446A1 (en) * | 2024-03-22 | 2025-09-25 | Sitryx Therapeutics Limited | Thiadiazoles as glutaminase 1 inhibitors |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1242426B1 (en) * | 1999-11-24 | 2007-10-31 | Merck & Co., Inc. | Gamma-hydroxy-2-(fluoroalkylaminocarbonyl)-1-piperazinepentanamides as hiv protease inhibitors |
| US6451828B1 (en) * | 2000-08-10 | 2002-09-17 | Elan Pharmaceuticals, Inc. | Selective inhibition of glutaminase by bis-thiadiazoles |
| MY142655A (en) * | 2003-06-12 | 2010-12-15 | Euro Celtique Sa | Therapeutic agents useful for treating pain |
| EP1828144A2 (en) * | 2004-11-12 | 2007-09-05 | OSI Pharmaceuticals, Inc. | Integrin antagonists useful as anticancer agents |
| PE20120911A1 (es) * | 2009-04-20 | 2012-08-06 | Hoffmann La Roche | Derivados de prolina como inhibidores de catepsina |
| WO2013078123A1 (en) * | 2011-11-21 | 2013-05-30 | Calithera Biosciences Inc. | Heterocyclic inhibitors of glutaminase |
| RS62447B1 (sr) * | 2012-11-16 | 2021-11-30 | Calithera Biosciences Inc | Heterociklični inhibitori glutaminaze |
| US9029531B2 (en) | 2012-11-22 | 2015-05-12 | Agios Pharmaceuticals, Inc. | Compounds and their methods of use |
| CN105960405B (zh) * | 2014-01-06 | 2021-02-19 | 理森制药股份公司 | 谷氨酰胺酶抑制剂 |
| EP3116872A4 (en) * | 2014-03-14 | 2017-08-30 | 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 |
| 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 US15/363,018 patent/US9938265B2/en active Active
- 2016-11-29 TW TW105139312A patent/TW201730188A/zh unknown
- 2016-11-30 DK DK16802102.0T patent/DK3383871T3/da active
- 2016-11-30 KR KR1020187017164A patent/KR20180083412A/ko not_active Withdrawn
- 2016-11-30 WO PCT/EP2016/079251 patent/WO2017093300A1/en not_active Ceased
- 2016-11-30 SG SG11201803813UA patent/SG11201803813UA/en unknown
- 2016-11-30 AR ARP160103665A patent/AR106876A1/es unknown
- 2016-11-30 PE PE2018001021A patent/PE20181450A1/es unknown
- 2016-11-30 TN TNP/2018/000126A patent/TN2018000126A1/en unknown
- 2016-11-30 EP EP16802102.0A patent/EP3383871B1/en active Active
- 2016-11-30 MX MX2018006528A patent/MX2018006528A/es unknown
- 2016-11-30 AU AU2016363719A patent/AU2016363719B2/en active Active
- 2016-11-30 CA CA3005516A patent/CA3005516C/en active Active
- 2016-11-30 CN CN201680067261.2A patent/CN108349967B/zh active Active
- 2016-11-30 JP JP2018526717A patent/JP6873132B2/ja active Active
- 2016-11-30 EA EA201891240A patent/EA201891240A1/ru unknown
- 2016-11-30 BR BR112018010812A patent/BR112018010812A2/pt not_active Application Discontinuation
- 2016-11-30 ES ES16802102T patent/ES2759940T3/es active Active
-
2018
- 2018-04-11 IL IL258644A patent/IL258644A/en unknown
- 2018-05-24 CL CL2018001408A patent/CL2018001408A1/es unknown
- 2018-05-29 NI NI201800065A patent/NI201800065A/es unknown
- 2018-05-29 SV SV2018005701A patent/SV2018005701A/es unknown
- 2018-05-29 DO DO2018000134A patent/DOP2018000134A/es unknown
- 2018-05-29 PH PH12018501132A patent/PH12018501132A1/en unknown
- 2018-06-29 CO CONC2018/0006929A patent/CO2018006929A2/es unknown