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- Withdrawn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 (enExample) | 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 (enExample) |
| EP (2) | EP3233794B1 (enExample) |
| JP (3) | JP6698089B2 (enExample) |
| KR (1) | KR20170135820A (enExample) |
| CN (2) | CN107531615B (enExample) |
| AU (1) | AU2015364696B2 (enExample) |
| BR (1) | BR112017013012A2 (enExample) |
| CA (1) | CA2970803A1 (enExample) |
| CL (1) | CL2017001539A1 (enExample) |
| CO (1) | CO2017007076A2 (enExample) |
| IL (1) | IL252897A0 (enExample) |
| MX (2) | MX386761B (enExample) |
| PH (1) | PH12017501130A1 (enExample) |
| RU (1) | RU2017125024A (enExample) |
| SG (1) | SG11201704934YA (enExample) |
| WO (1) | WO2016100542A1 (enExample) |
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 |
| JP7300394B2 (ja) | 2017-01-17 | 2023-06-29 | ヘパリジェニックス ゲーエムベーハー | 肝再生の促進又は肝細胞死の低減もしくは予防のためのプロテインキナーゼ阻害 |
| WO2018170410A1 (en) | 2017-03-17 | 2018-09-20 | University Of South Alabama | Derivatives of sulindac can protect normal cells against oxidative damage |
| US11731952B2 (en) | 2017-08-31 | 2023-08-22 | Musc Foundation For Research Development | Indene derivatives and uses thereof |
| 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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