JP2020079307A5 - - Google Patents
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- Publication number
- JP2020079307A5 JP2020079307A5 JP2020029699A JP2020029699A JP2020079307A5 JP 2020079307 A5 JP2020079307 A5 JP 2020079307A5 JP 2020029699 A JP2020029699 A JP 2020029699A JP 2020029699 A JP2020029699 A JP 2020029699A JP 2020079307 A5 JP2020079307 A5 JP 2020079307A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- hydroxy
- acetamide
- inden
- dimethoxybenzylidene
- 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.)
- Withdrawn
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- -1 thiazepanyl Chemical group 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 239000000651 prodrug Substances 0.000 claims 10
- 229940002612 prodrug Drugs 0.000 claims 10
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000001425 triazolyl group Chemical group 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 3
- 239000005711 Benzoic acid Substances 0.000 claims 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 3
- 229910000147 aluminium phosphate Chemical class 0.000 claims 3
- 150000001413 amino acids Chemical class 0.000 claims 3
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims 3
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims 3
- 235000010233 benzoic acid Nutrition 0.000 claims 3
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 2
- 238000001727 in vivo Methods 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 102000016914 ras Proteins Human genes 0.000 claims 2
- 108010014186 ras Proteins Proteins 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- XAUGGEJFEMACPG-FBHDLOMBSA-N 2-[(3Z)-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-6-methoxy-2-methylinden-1-yl]-N-(1H-pyrrol-2-ylmethyl)acetamide Chemical compound N1C(=CC=C1)CNC(CC1=C(/C(/C2=CC=C(C=C12)OC)=C/C1=CC(=C(C(=C1)OC)O)OC)C)=O XAUGGEJFEMACPG-FBHDLOMBSA-N 0.000 claims 1
- UAKZJXKRCGQOGT-UKWGHVSLSA-N 2-[(3Z)-6-fluoro-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-methylinden-1-yl]-N-(1H-pyrrol-2-ylmethyl)acetamide Chemical compound N1C(=CC=C1)CNC(CC1=C(/C(/C2=CC=C(C=C12)F)=C/C1=CC(=C(C(=C1)OC)O)OC)C)=O UAKZJXKRCGQOGT-UKWGHVSLSA-N 0.000 claims 1
- QGUQCLKABYTHQG-UKWGHVSLSA-N 2-[(3Z)-6-fluoro-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-methylinden-1-yl]-N-(furan-2-ylmethyl)-N-(trifluoromethyl)acetamide Chemical compound FC=1C=C2C(=C(/C(/C2=CC=1)=C/C1=CC(=C(C(=C1)OC)O)OC)C)CC(=O)N(C(F)(F)F)CC=1OC=CC=1 QGUQCLKABYTHQG-UKWGHVSLSA-N 0.000 claims 1
- CJBUOVAXMPVXFB-UKWGHVSLSA-N 2-[(3Z)-6-fluoro-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-methylinden-1-yl]-N-(furan-2-ylmethyl)acetamide Chemical compound FC=1C=C2C(=C(/C(/C2=CC=1)=C/C1=CC(=C(C(=C1)OC)O)OC)C)CC(=O)NCC=1OC=CC=1 CJBUOVAXMPVXFB-UKWGHVSLSA-N 0.000 claims 1
- GEGVKQRPGNRAIH-FBHDLOMBSA-N 2-[(3Z)-6-fluoro-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-methylinden-1-yl]-N-[(1-methylpyrrol-2-yl)methyl]acetamide Chemical compound FC=1C=C2C(=C(/C(/C2=CC=1)=C/C1=CC(=C(C(=C1)OC)O)OC)C)CC(=O)NCC=1N(C=CC=1)C GEGVKQRPGNRAIH-FBHDLOMBSA-N 0.000 claims 1
- OJOZWNKVCAHSQU-NHDPSOOVSA-N 2-[(3Z)-6-fluoro-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-methylinden-1-yl]-N-phenoxyacetamide Chemical compound FC=1C=C2C(=C(/C(/C2=CC=1)=C/C1=CC(=C(C(=C1)OC)O)OC)C)CC(=O)NOC1=CC=CC=C1 OJOZWNKVCAHSQU-NHDPSOOVSA-N 0.000 claims 1
- PYPMRDWDNXBVHT-NHDPSOOVSA-N N-(furan-2-ylmethyl)-2-[(3Z)-3-[(4-hydroxy-3-methoxyphenyl)methylidene]-6-methoxy-2-methylinden-1-yl]acetamide Chemical compound O1C(=CC=C1)CNC(CC1=C(/C(/C2=CC=C(C=C12)OC)=C/C1=CC(=C(C=C1)O)OC)C)=O PYPMRDWDNXBVHT-NHDPSOOVSA-N 0.000 claims 1
- IWYGOZQVWOCZNE-JJFYIABZSA-N N-benzyl-2-[(3Z)-6-fluoro-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-methylinden-1-yl]acetamide Chemical compound C(C1=CC=CC=C1)NC(CC1=C(/C(/C2=CC=C(C=C12)F)=C/C1=CC(=C(C(=C1)OC)O)OC)C)=O IWYGOZQVWOCZNE-JJFYIABZSA-N 0.000 claims 1
- 101150040459 RAS gene Proteins 0.000 claims 1
- RBCKJOAMDLCFEH-UHFFFAOYSA-N SN=[N+]=[N-] Chemical compound SN=[N+]=[N-] RBCKJOAMDLCFEH-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 125000005325 aryloxy aryl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000003725 azepanyl group Chemical group 0.000 claims 1
- 125000002785 azepinyl group Chemical group 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 claims 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 1
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims 1
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 claims 1
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- 125000000597 dioxinyl group Chemical group 0.000 claims 1
- 125000005879 dioxolanyl group Chemical group 0.000 claims 1
- 125000005883 dithianyl group Chemical group 0.000 claims 1
- 125000005303 dithiazolyl group Chemical group S1SNC(=C1)* 0.000 claims 1
- 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000005961 oxazepanyl group Chemical group 0.000 claims 1
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000003585 oxepinyl group Chemical group 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 108700042226 ras Genes Proteins 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000005458 thianyl group Chemical group 0.000 claims 1
- 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 claims 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 claims 1
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000001583 thiepanyl group Chemical group 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- 125000005455 trithianyl group Chemical group 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021145211A JP2021185193A (ja) | 2014-12-16 | 2021-09-07 | インデニル化合物、医薬組成物、およびその医学的使用 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14/571,647 US9862698B2 (en) | 2014-12-16 | 2014-12-16 | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
| US14/571,647 | 2014-12-16 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017533501A Division JP6698089B2 (ja) | 2014-12-16 | 2015-12-16 | インデニル化合物、医薬組成物、およびその医学的使用 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021145211A Division JP2021185193A (ja) | 2014-12-16 | 2021-09-07 | インデニル化合物、医薬組成物、およびその医学的使用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2020079307A JP2020079307A (ja) | 2020-05-28 |
| JP2020079307A5 true JP2020079307A5 (https=) | 2020-07-09 |
Family
ID=55085918
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017533501A Active JP6698089B2 (ja) | 2014-12-16 | 2015-12-16 | インデニル化合物、医薬組成物、およびその医学的使用 |
| JP2020029699A Withdrawn JP2020079307A (ja) | 2014-12-16 | 2020-02-25 | インデニル化合物、医薬組成物、およびその医学的使用 |
| JP2021145211A Withdrawn JP2021185193A (ja) | 2014-12-16 | 2021-09-07 | インデニル化合物、医薬組成物、およびその医学的使用 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017533501A Active JP6698089B2 (ja) | 2014-12-16 | 2015-12-16 | インデニル化合物、医薬組成物、およびその医学的使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021145211A Withdrawn JP2021185193A (ja) | 2014-12-16 | 2021-09-07 | インデニル化合物、医薬組成物、およびその医学的使用 |
Country Status (16)
| Country | Link |
|---|---|
| US (7) | US9862698B2 (https=) |
| EP (2) | EP4053105A1 (https=) |
| JP (3) | JP6698089B2 (https=) |
| KR (1) | KR20170135820A (https=) |
| CN (2) | CN107531615B (https=) |
| AU (1) | AU2015364696B2 (https=) |
| BR (1) | BR112017013012A2 (https=) |
| CA (1) | CA2970803A1 (https=) |
| CL (1) | CL2017001539A1 (https=) |
| CO (1) | CO2017007076A2 (https=) |
| IL (1) | IL252897A0 (https=) |
| MX (2) | MX2021012096A (https=) |
| PH (1) | PH12017501130A1 (https=) |
| RU (1) | RU2017125024A (https=) |
| SG (1) | SG11201704934YA (https=) |
| WO (1) | WO2016100542A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20160168108A1 (en) | 2014-12-16 | 2016-06-16 | Adt Pharmaceuticals, Inc. | Method of treating or preventing ras-mediated diseases |
| US9862698B2 (en) * | 2014-12-16 | 2018-01-09 | Adt Pharmaceuticals, Inc. | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
| ES2928773T3 (es) | 2017-01-17 | 2022-11-22 | Heparegenix Gmbh | Inhibidores de proteína cinasas para fomentar la regeneración hepática o reducir o prevenir la muerte de hepatocitos |
| US11186534B2 (en) * | 2017-03-17 | 2021-11-30 | University Of South Alabama | Derivatives of sulindac can protect normal cells against oxidative damage |
| JP7330168B2 (ja) * | 2017-08-31 | 2023-08-21 | エムユーエスシー ファウンデーション フォー リサーチ ディベロップメント | インデン誘導体およびその使用 |
| JP7169008B2 (ja) * | 2018-04-26 | 2022-11-10 | エーディーティー ファーマシューティカルズ，エルエルシー | 抗がんインデン、インダン、アザインデン、アザインダン、医薬組成物および使用 |
| CN113289020B (zh) * | 2021-05-17 | 2023-04-18 | 福州大学 | 蛋白质二硫键异构酶小分子抑制剂及其应用 |
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- 2015-12-16 AU AU2015364696A patent/AU2015364696B2/en not_active Ceased
- 2015-12-16 WO PCT/US2015/066146 patent/WO2016100542A1/en not_active Ceased
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