JP2013532727A5 - - Google Patents
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- JP2013532727A5 JP2013532727A5 JP2013523213A JP2013523213A JP2013532727A5 JP 2013532727 A5 JP2013532727 A5 JP 2013532727A5 JP 2013523213 A JP2013523213 A JP 2013523213A JP 2013523213 A JP2013523213 A JP 2013523213A JP 2013532727 A5 JP2013532727 A5 JP 2013532727A5
- Authority
- JP
- Japan
- Prior art keywords
- substituent
- amino
- alkyl
- pharmaceutically acceptable
- acceptable salt
- 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.)
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- 125000001424 substituent group Chemical group 0.000 claims 45
- 125000000217 alkyl group Chemical group 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000005466 alkylenyl group Chemical group 0.000 claims 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 16
- 125000001931 aliphatic group Chemical group 0.000 claims 13
- -1 amino, hydroxy Chemical group 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 239000004480 active ingredient Substances 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 102100024299 Maternal embryonic leucine zipper kinase Human genes 0.000 claims 3
- 101710154611 Maternal embryonic leucine zipper kinase Proteins 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 230000002018 overexpression Effects 0.000 claims 3
- 230000000069 prophylactic effect Effects 0.000 claims 3
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims 3
- 230000001225 therapeutic effect Effects 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 1
- UFJXIZSDRSWGHH-UHFFFAOYSA-N 1-[4-[[6-(3-aminopiperidin-1-yl)pyridin-3-yl]amino]-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-3-yl]ethanone Chemical compound CC(=O)C1=CN=C2C=CC(C=3C=C(Cl)C(O)=C(Cl)C=3)=CC2=C1NC(C=N1)=CC=C1N1CCCC(N)C1 UFJXIZSDRSWGHH-UHFFFAOYSA-N 0.000 claims 1
- DLMHQUGZXIWVLQ-UHFFFAOYSA-N 1-[4-[[6-(3-aminopiperidin-1-yl)pyridin-3-yl]amino]-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-3-yl]propan-1-one Chemical compound CCC(=O)C1=CN=C2C=CC(C=3C=C(Cl)C(O)=C(Cl)C=3)=CC2=C1NC(C=N1)=CC=C1N1CCCC(N)C1 DLMHQUGZXIWVLQ-UHFFFAOYSA-N 0.000 claims 1
- DLMHQUGZXIWVLQ-SFHVURJKSA-N 1-[4-[[6-[(3s)-3-aminopiperidin-1-yl]pyridin-3-yl]amino]-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-3-yl]propan-1-one Chemical compound CCC(=O)C1=CN=C2C=CC(C=3C=C(Cl)C(O)=C(Cl)C=3)=CC2=C1NC(C=N1)=CC=C1N1CCC[C@H](N)C1 DLMHQUGZXIWVLQ-SFHVURJKSA-N 0.000 claims 1
- DKZYXHCYPUVGAF-UHFFFAOYSA-N 1-[6-(3,5-dichloro-4-hydroxyphenyl)-4-[[4-[(dimethylamino)methyl]cyclohexyl]amino]-1,5-naphthyridin-3-yl]ethanone Chemical compound CN(C)CC1CCC(CC1)Nc1c(cnc2ccc(nc12)-c1cc(Cl)c(O)c(Cl)c1)C(C)=O DKZYXHCYPUVGAF-UHFFFAOYSA-N 0.000 claims 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- PEAZQTKOWOEYCZ-UKIBZPOASA-N C1C[C@@H](CN(C)C)CC[C@@H]1NC1=C(C(=O)C2CC2)C=NC2=CC=C(C=3C=C(Cl)C(O)=C(Cl)C=3)C=C12 Chemical compound C1C[C@@H](CN(C)C)CC[C@@H]1NC1=C(C(=O)C2CC2)C=NC2=CC=C(C=3C=C(Cl)C(O)=C(Cl)C=3)C=C12 PEAZQTKOWOEYCZ-UKIBZPOASA-N 0.000 claims 1
- YFBRRBWSRJPOIT-RUCARUNLSA-N C1C[C@@H](CN(C)C)CC[C@@H]1NC1=C(C(C)=O)C=NC2=CC=C(C=3C=C(Cl)C(O)=C(Cl)C=3)C=C12 Chemical compound C1C[C@@H](CN(C)C)CC[C@@H]1NC1=C(C(C)=O)C=NC2=CC=C(C=3C=C(Cl)C(O)=C(Cl)C=3)C=C12 YFBRRBWSRJPOIT-RUCARUNLSA-N 0.000 claims 1
- UYIMHVQEXCPIKN-RUCARUNLSA-N C1C[C@@H](CN(C)C)CC[C@@H]1NC1=C(C(C)=O)C=NC2=CC=C(C=3C=C(Cl)C(O)=C(F)C=3)C=C12 Chemical compound C1C[C@@H](CN(C)C)CC[C@@H]1NC1=C(C(C)=O)C=NC2=CC=C(C=3C=C(Cl)C(O)=C(F)C=3)C=C12 UYIMHVQEXCPIKN-RUCARUNLSA-N 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 229940124787 MELK inhibitor Drugs 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 1
- LCFDWDAPNUMZKM-UHFFFAOYSA-N [4-[[6-(3-aminopiperidin-1-yl)pyridin-3-yl]amino]-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-3-yl]-cyclopropylmethanone Chemical compound C1C(N)CCCN1C(N=C1)=CC=C1NC1=C(C(=O)C2CC2)C=NC2=CC=C(C=3C=C(Cl)C(O)=C(Cl)C=3)C=C12 LCFDWDAPNUMZKM-UHFFFAOYSA-N 0.000 claims 1
- LCFDWDAPNUMZKM-LJQANCHMSA-N [4-[[6-[(3r)-3-aminopiperidin-1-yl]pyridin-3-yl]amino]-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-3-yl]-cyclopropylmethanone Chemical compound C1[C@H](N)CCCN1C(N=C1)=CC=C1NC1=C(C(=O)C2CC2)C=NC2=CC=C(C=3C=C(Cl)C(O)=C(Cl)C=3)C=C12 LCFDWDAPNUMZKM-LJQANCHMSA-N 0.000 claims 1
- LCFDWDAPNUMZKM-IBGZPJMESA-N [4-[[6-[(3s)-3-aminopiperidin-1-yl]pyridin-3-yl]amino]-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-3-yl]-cyclopropylmethanone Chemical compound C1[C@@H](N)CCCN1C(N=C1)=CC=C1NC1=C(C(=O)C2CC2)C=NC2=CC=C(C=3C=C(Cl)C(O)=C(Cl)C=3)C=C12 LCFDWDAPNUMZKM-IBGZPJMESA-N 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 201000011199 bladder lymphoma Diseases 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004431 deuterium atom Chemical group 0.000 claims 1
- 230000014509 gene expression Effects 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000003449 preventive effect Effects 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 206010046766 uterine cancer Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36951910P | 2010-07-30 | 2010-07-30 | |
| US61/369,519 | 2010-07-30 | ||
| PCT/US2011/045792 WO2012016082A1 (en) | 2010-07-30 | 2011-07-28 | Quinoline derivatives and melk inhibitors containing the same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013532727A JP2013532727A (ja) | 2013-08-19 |
| JP2013532727A5 true JP2013532727A5 (enExample) | 2014-09-11 |
| JP5849303B2 JP5849303B2 (ja) | 2016-01-27 |
Family
ID=45530500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013523213A Active JP5849303B2 (ja) | 2010-07-30 | 2011-07-28 | キノリン誘導体および同一物を含むｍｅｌｋ阻害剤 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US9120749B2 (enExample) |
| EP (1) | EP2597955B1 (enExample) |
| JP (1) | JP5849303B2 (enExample) |
| KR (1) | KR101826382B1 (enExample) |
| CN (1) | CN103153063B (enExample) |
| AU (1) | AU2011282588B2 (enExample) |
| BR (1) | BR112013002182B8 (enExample) |
| CA (1) | CA2806332C (enExample) |
| DK (1) | DK2597955T3 (enExample) |
| ES (1) | ES2565627T3 (enExample) |
| IL (1) | IL223871A (enExample) |
| MX (1) | MX342879B (enExample) |
| RU (1) | RU2582610C2 (enExample) |
| SG (2) | SG10201505951VA (enExample) |
| TW (1) | TWI532483B (enExample) |
| WO (1) | WO2012016082A1 (enExample) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US20130225524A1 (en) * | 2010-11-05 | 2013-08-29 | Deping Chai | Chemical Compounds |
| RU2645339C1 (ru) | 2012-01-19 | 2018-02-21 | Онкотерапи Сайенс, Инк. | Производные 1,5-нафтиридина и ингибиторы melk, содержащие их |
| US9227978B2 (en) | 2013-03-15 | 2016-01-05 | Araxes Pharma Llc | Covalent inhibitors of Kras G12C |
| US9745319B2 (en) | 2013-03-15 | 2017-08-29 | Araxes Pharma Llc | Irreversible covalent inhibitors of the GTPase K-Ras G12C |
| TWI659021B (zh) | 2013-10-10 | 2019-05-11 | 亞瑞克西斯製藥公司 | Ｋｒａｓ ｇ１２ｃ之抑制劑 |
| US10254283B2 (en) | 2013-11-12 | 2019-04-09 | Dana-Farber Cancer Institute, Inc. | Biomarker for MELK activity and methods of using same |
| EP3085700B1 (en) * | 2013-12-20 | 2018-10-31 | Institute of Pharmacology and Toxicology Academy of Military Medical Sciences P.L.A. China | Novel piperidine carboxamide compound, preparation method, and usage thereof |
| JO3556B1 (ar) | 2014-09-18 | 2020-07-05 | Araxes Pharma Llc | علاجات مدمجة لمعالجة السرطان |
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| US10882847B2 (en) | 2015-09-28 | 2021-01-05 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
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2011
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