JP2019516677A5 - - Google Patents
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- Publication number
- JP2019516677A5 JP2019516677A5 JP2018556376A JP2018556376A JP2019516677A5 JP 2019516677 A5 JP2019516677 A5 JP 2019516677A5 JP 2018556376 A JP2018556376 A JP 2018556376A JP 2018556376 A JP2018556376 A JP 2018556376A JP 2019516677 A5 JP2019516677 A5 JP 2019516677A5
- Authority
- JP
- Japan
- Prior art keywords
- triazol
- sulfanyl
- acetamide
- thiadiazol
- ethyl
- 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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- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 17
- -1 alkoxy halides Chemical class 0.000 claims 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 3
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical group C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims 2
- 206010012442 Dermatitis contact Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 208000002029 allergic contact dermatitis Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- JYVPAIBUQJTZID-UHFFFAOYSA-N 2-[(4,5-diethyl-1,2,4-triazol-3-yl)sulfanyl]-N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide Chemical compound C(C)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=CC=C1)CC JYVPAIBUQJTZID-UHFFFAOYSA-N 0.000 claims 1
- HBURMPNBKOAVLW-UHFFFAOYSA-N 2-[(4,5-diethyl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound CCc1nnc(SCC(=O)Nc2nnc(s2)-c2ccc3OCCc3c2)n1CC HBURMPNBKOAVLW-UHFFFAOYSA-N 0.000 claims 1
- PXVMDWKJRUOEIY-UHFFFAOYSA-N 2-[(4,5-diethyl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(4-ethoxyphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)OCC)CC PXVMDWKJRUOEIY-UHFFFAOYSA-N 0.000 claims 1
- OJZKDMNXROTKJK-UHFFFAOYSA-N 2-[(4,5-diethyl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(4-ethylphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)CC)CC OJZKDMNXROTKJK-UHFFFAOYSA-N 0.000 claims 1
- JOSOMNOHNHFDBA-UHFFFAOYSA-N 2-[(4,5-diethyl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)OC)CC JOSOMNOHNHFDBA-UHFFFAOYSA-N 0.000 claims 1
- ORKWVSPBFJMHJQ-UHFFFAOYSA-N 2-[(4,5-diethyl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(4-methylsulfonylphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)S(=O)(=O)C)CC ORKWVSPBFJMHJQ-UHFFFAOYSA-N 0.000 claims 1
- WKLIMMLZGHORGN-UHFFFAOYSA-N 2-[(4,5-diethyl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(4-propan-2-ylphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)C(C)C)CC WKLIMMLZGHORGN-UHFFFAOYSA-N 0.000 claims 1
- BIZZDYDNZIENET-UHFFFAOYSA-N 2-[(4,5-diethyl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(4-propylphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)CCC)CC BIZZDYDNZIENET-UHFFFAOYSA-N 0.000 claims 1
- WRQGVPWGMBIYOS-UHFFFAOYSA-N 2-[(4,5-diethyl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-[4-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)N1C(=NN=C1CC)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)C(F)(F)F WRQGVPWGMBIYOS-UHFFFAOYSA-N 0.000 claims 1
- LBDZBRLMBJIOHQ-UHFFFAOYSA-N 2-[(4-cyclopropyl-5-ethyl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C1(CC1)N1C(=NN=C1CC)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)OC LBDZBRLMBJIOHQ-UHFFFAOYSA-N 0.000 claims 1
- WLMGVMKKZPBBCY-UHFFFAOYSA-N 2-[(4-cyclopropyl-5-ethyl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(4-methylsulfonylphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C1(CC1)N1C(=NN=C1CC)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)S(=O)(=O)C WLMGVMKKZPBBCY-UHFFFAOYSA-N 0.000 claims 1
- JUUIDXYNHCZLMO-UHFFFAOYSA-N 2-[(4-ethyl-5-methyl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(4-methylsulfonylphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)N1C(=NN=C1C)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)S(=O)(=O)C JUUIDXYNHCZLMO-UHFFFAOYSA-N 0.000 claims 1
- MISLNVCPDYRVIZ-UHFFFAOYSA-N 2-[(4-ethyl-5-propan-2-yl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(4-methylsulfonylphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)N1C(=NN=C1C(C)C)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)S(=O)(=O)C MISLNVCPDYRVIZ-UHFFFAOYSA-N 0.000 claims 1
- XJYLCCBYAFDRNM-UHFFFAOYSA-N 2-[(4-ethyl-5-propan-2-yl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)N1C(=NN=C1C(C)C)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)OC(C)C XJYLCCBYAFDRNM-UHFFFAOYSA-N 0.000 claims 1
- IFLOIXARGBGIMJ-UHFFFAOYSA-N 2-[(4-ethyl-5-propan-2-yl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-[4-(2-fluoroethoxy)phenyl]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)N1C(=NN=C1C(C)C)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)OCCF IFLOIXARGBGIMJ-UHFFFAOYSA-N 0.000 claims 1
- ZVACOPHIRUBZKN-UHFFFAOYSA-N 2-[(4-ethyl-5-propan-2-yl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-[4-(2-methoxyethoxy)phenyl]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)N1C(=NN=C1C(C)C)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)OCCOC ZVACOPHIRUBZKN-UHFFFAOYSA-N 0.000 claims 1
- IZDAJCQJSVQJDW-UHFFFAOYSA-N 2-[(5-benzyl-4-ethyl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C1=CC=CC=C1)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)OC)CC IZDAJCQJSVQJDW-UHFFFAOYSA-N 0.000 claims 1
- GQOKEIUIFFWJFO-UHFFFAOYSA-N 2-[(5-cyclopentyl-4-ethyl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(4-methylsulfonylphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C1(CCCC1)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)S(=O)(=O)C)CC GQOKEIUIFFWJFO-UHFFFAOYSA-N 0.000 claims 1
- ZBXJLFZZHGUAMQ-UHFFFAOYSA-N 2-[(5-cyclopropyl-4-ethyl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(4-methylsulfonylphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C1(CC1)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)S(=O)(=O)C)CC ZBXJLFZZHGUAMQ-UHFFFAOYSA-N 0.000 claims 1
- SLIVTJTWVXQCRG-UHFFFAOYSA-N 2-[(5-cyclopropyl-4-ethyl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-[4-(2-methoxyethoxy)phenyl]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C1(CC1)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)OCCOC)CC SLIVTJTWVXQCRG-UHFFFAOYSA-N 0.000 claims 1
- LRFRGLCJSXXYSW-UHFFFAOYSA-N 2-[(5-ethyl-4-methyl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)OC)C LRFRGLCJSXXYSW-UHFFFAOYSA-N 0.000 claims 1
- UKGZHHBFQPOEOR-UHFFFAOYSA-N 2-[(5-ethyl-4-methyl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(4-methylsulfonylphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)S(=O)(=O)C)C UKGZHHBFQPOEOR-UHFFFAOYSA-N 0.000 claims 1
- IEJDSWHFFVBZGC-UHFFFAOYSA-N 2-[(5-ethyl-4-phenyl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)OC)C1=CC=CC=C1 IEJDSWHFFVBZGC-UHFFFAOYSA-N 0.000 claims 1
- PLKLVWLVVXCWKR-UHFFFAOYSA-N 2-[(5-ethyl-4-propan-2-yl-1,2,4-triazol-3-yl)sulfanyl]-N-[5-(4-methylsulfonylphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)S(=O)(=O)C)C(C)C PLKLVWLVVXCWKR-UHFFFAOYSA-N 0.000 claims 1
- GEXDXNOIQWJTGS-UHFFFAOYSA-N 2-[[4-ethyl-5-(2-methoxyethyl)-1,2,4-triazol-3-yl]sulfanyl]-N-[5-(4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C(C)N1C(=NN=C1CCOC)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)OC(C)C GEXDXNOIQWJTGS-UHFFFAOYSA-N 0.000 claims 1
- OLFMMPGTGIRKJR-UHFFFAOYSA-N 2-[[4-ethyl-5-(morpholin-4-ylmethyl)-1,2,4-triazol-3-yl]sulfanyl]-N-[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound CCn1c(CN2CCOCC2)nnc1SCC(=O)Nc1nnc(s1)-c1ccc(OC)cc1 OLFMMPGTGIRKJR-UHFFFAOYSA-N 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- 208000009304 Acute Kidney Injury Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- SVDBKDXAAHZLJZ-UHFFFAOYSA-N C(C)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)O)CC Chemical compound C(C)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)O)CC SVDBKDXAAHZLJZ-UHFFFAOYSA-N 0.000 claims 1
- CBNMTESHPFMBOP-UHFFFAOYSA-N C1(CC1)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)O)CC Chemical compound C1(CC1)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)O)CC CBNMTESHPFMBOP-UHFFFAOYSA-N 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- OAWDELVBYYHOJX-UHFFFAOYSA-N N-[5-(4-butylphenyl)-1,3,4-thiadiazol-2-yl]-2-[(4,5-diethyl-1,2,4-triazol-3-yl)sulfanyl]acetamide Chemical compound C(C)C=1N(C(=NN=1)SCC(=O)NC=1SC(=NN=1)C1=CC=C(C=C1)CCCC)CC OAWDELVBYYHOJX-UHFFFAOYSA-N 0.000 claims 1
- MKNHZBMTHVTDKV-UHFFFAOYSA-N N-[5-(4-ethoxyphenyl)-1,3,4-thiadiazol-2-yl]-2-[(4-ethyl-5-propan-2-yl-1,2,4-triazol-3-yl)sulfanyl]acetamide Chemical compound C(C)OC1=CC=C(C=C1)C1=NN=C(S1)NC(CSC1=NN=C(N1CC)C(C)C)=O MKNHZBMTHVTDKV-UHFFFAOYSA-N 0.000 claims 1
- DLJVQTRCMLPCOV-UHFFFAOYSA-N N-[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]-2-[(5-methyl-4-phenyl-1,2,4-triazol-3-yl)sulfanyl]acetamide Chemical compound COC1=CC=C(C=C1)C1=NN=C(S1)NC(CSC1=NN=C(N1C1=CC=CC=C1)C)=O DLJVQTRCMLPCOV-UHFFFAOYSA-N 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 208000033626 Renal failure acute Diseases 0.000 claims 1
- 206010063897 Renal ischaemia Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 150000003869 acetamides Chemical class 0.000 claims 1
- 201000011040 acute kidney failure Diseases 0.000 claims 1
- 208000012998 acute renal failure Diseases 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical group C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16167378 | 2016-04-28 | ||
| EP16167378.5 | 2016-04-28 | ||
| PCT/EP2017/060148 WO2017186893A1 (en) | 2016-04-28 | 2017-04-28 | Compounds for modulating aquaporins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019516677A JP2019516677A (ja) | 2019-06-20 |
| JP2019516677A5 true JP2019516677A5 (enExample) | 2020-05-28 |
| JP6921118B2 JP6921118B2 (ja) | 2021-08-18 |
Family
ID=55854711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018556376A Active JP6921118B2 (ja) | 2016-04-28 | 2017-04-28 | アクアポリンを調節するための化合物 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US10730865B2 (enExample) |
| EP (1) | EP3448853B1 (enExample) |
| JP (1) | JP6921118B2 (enExample) |
| CA (1) | CA3022195C (enExample) |
| DK (1) | DK3448853T3 (enExample) |
| ES (1) | ES2902409T3 (enExample) |
| HR (1) | HRP20212031T1 (enExample) |
| HU (1) | HUE057193T2 (enExample) |
| LT (1) | LT3448853T (enExample) |
| PL (1) | PL3448853T3 (enExample) |
| PT (1) | PT3448853T (enExample) |
| WO (1) | WO2017186893A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111393444B (zh) * | 2019-01-02 | 2022-10-28 | 上海迪赛诺化学制药有限公司 | 一种阿巴卡韦羟基醋酸酯的制备方法 |
| WO2025137265A1 (en) | 2023-12-20 | 2025-06-26 | Saint Michael's College, Inc. | Methods and compositions for reducing gliaptosis: macroglia-induced neuronal cell death |
| CN118001408B (zh) * | 2024-04-08 | 2024-06-25 | 北京大学 | 一种水通道蛋白9磷酸化抑制剂的用途 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US333792A (en) * | 1886-01-05 | Stop watch | ||
| EP1615637A1 (en) * | 2003-04-11 | 2006-01-18 | Novo Nordisk A/S | Pharmaceutical use of substituted 1,2,4-triazoles |
| GB0704394D0 (en) * | 2007-03-07 | 2007-04-11 | Senexis Ltd | Compounds |
| JP6671382B2 (ja) | 2014-10-29 | 2020-03-25 | アポグリクス アクツィエブーラーグＡｐｏＧｌｙｘ ＡＢ | 特に糖尿病の治療に有用である２−（１，２，４−トリアゾール−３−イルスルファニル）−ｎ−１，３，４−チアジアゾール−２−イルアセトアミドの誘導体 |
-
2017
- 2017-04-28 CA CA3022195A patent/CA3022195C/en active Active
- 2017-04-28 PL PL17720125T patent/PL3448853T3/pl unknown
- 2017-04-28 US US16/096,521 patent/US10730865B2/en active Active
- 2017-04-28 DK DK17720125.8T patent/DK3448853T3/da active
- 2017-04-28 WO PCT/EP2017/060148 patent/WO2017186893A1/en not_active Ceased
- 2017-04-28 HU HUE17720125A patent/HUE057193T2/hu unknown
- 2017-04-28 LT LTEPPCT/EP2017/060148T patent/LT3448853T/lt unknown
- 2017-04-28 HR HRP20212031TT patent/HRP20212031T1/hr unknown
- 2017-04-28 EP EP17720125.8A patent/EP3448853B1/en active Active
- 2017-04-28 ES ES17720125T patent/ES2902409T3/es active Active
- 2017-04-28 JP JP2018556376A patent/JP6921118B2/ja active Active
- 2017-04-28 PT PT177201258T patent/PT3448853T/pt unknown
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