CA3061650A1 - Heteroaryl compounds that inhibit g12c mutant ras proteins - Google Patents
Heteroaryl compounds that inhibit g12c mutant ras proteins Download PDFInfo
- Publication number
- CA3061650A1 CA3061650A1 CA3061650A CA3061650A CA3061650A1 CA 3061650 A1 CA3061650 A1 CA 3061650A1 CA 3061650 A CA3061650 A CA 3061650A CA 3061650 A CA3061650 A CA 3061650A CA 3061650 A1 CA3061650 A1 CA 3061650A1
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- 4alkyl
- halo
- heteroaryl
- heterocyclyl
- 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.)
- Abandoned
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- 125000001072 heteroaryl group Chemical group 0.000 title claims description 181
- 102000016914 ras Proteins Human genes 0.000 title description 40
- 108010014186 ras Proteins Proteins 0.000 title description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 251
- 150000003839 salts Chemical class 0.000 claims abstract description 117
- 238000011282 treatment Methods 0.000 claims abstract description 55
- 238000000034 method Methods 0.000 claims abstract description 41
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 250
- 125000005843 halogen group Chemical group 0.000 claims description 246
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 220
- 125000001424 substituent group Chemical group 0.000 claims description 209
- 125000000623 heterocyclic group Chemical group 0.000 claims description 175
- -1 cyano, acetylenyl Chemical group 0.000 claims description 166
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 132
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 101
- 229910052757 nitrogen Inorganic materials 0.000 claims description 59
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 54
- 206010028980 Neoplasm Diseases 0.000 claims description 37
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 35
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 31
- 241001465754 Metazoa Species 0.000 claims description 27
- 125000001153 fluoro group Chemical group F* 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 20
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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- FPQSSQQQKLJLPA-SECBINFHSA-N tert-butyl (3r)-3-(2-hydroxyethyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN[C@H](CCO)C1 FPQSSQQQKLJLPA-SECBINFHSA-N 0.000 description 1
- IPDNIMSJXOMDAF-ZDUSSCGKSA-N tert-butyl (7S)-12-bromo-11-chloro-16-[2-(dimethylamino)ethylamino]-9-oxa-2,5,15,17-tetrazatetracyclo[8.7.1.02,7.014,18]octadeca-1(17),10(18),11,13,15-pentaene-5-carboxylate Chemical compound N(C)(CCNC1=NC2=CC(Br)=C(Cl)C=3OC[C@H]4N(C(=N1)C2=3)CCN(C4)C(=O)OC(C)(C)C)C IPDNIMSJXOMDAF-ZDUSSCGKSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
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|---|---|---|---|
| US201762504638P | 2017-05-11 | 2017-05-11 | |
| US62/504,638 | 2017-05-11 | ||
| PCT/EP2018/061787 WO2018206539A1 (en) | 2017-05-11 | 2018-05-08 | Heteroaryl compounds that inhibit g12c mutant ras proteins |
Publications (1)
| Publication Number | Publication Date |
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| CA3061650A1 true CA3061650A1 (en) | 2018-11-15 |
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| CA3061650A Abandoned CA3061650A1 (en) | 2017-05-11 | 2018-05-08 | Heteroaryl compounds that inhibit g12c mutant ras proteins |
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| US (2) | US20200109153A1 (enExample) |
| EP (1) | EP3621968A1 (enExample) |
| JP (1) | JP2020519589A (enExample) |
| CN (1) | CN110603258A (enExample) |
| AR (1) | AR111776A1 (enExample) |
| CA (1) | CA3061650A1 (enExample) |
| TW (1) | TW201906848A (enExample) |
| WO (1) | WO2018206539A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2546727C (en) * | 2003-11-20 | 2012-10-02 | Children's Hospital Medical Center | Gtpase inhibitors and methods of use |
| WO2011121350A1 (en) * | 2010-04-01 | 2011-10-06 | Astrazeneca Ab | 4 -amino -7,8- dihydropyrimido [5, 4 - f] [1, 4] oxazepin- 5 ( 6h) - one based dgat1 inhibitors |
| EA028122B1 (ru) * | 2013-03-14 | 2017-10-31 | Новартис Аг | 3-пиримидин-4-илоксазолидин-2-оны в качестве ингибиторов мутантного idh |
| US9862701B2 (en) * | 2014-09-25 | 2018-01-09 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
| EP3356354A1 (en) * | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
-
2018
- 2018-05-08 AR ARP180101198A patent/AR111776A1/es unknown
- 2018-05-08 US US16/611,538 patent/US20200109153A1/en not_active Abandoned
- 2018-05-08 WO PCT/EP2018/061787 patent/WO2018206539A1/en not_active Ceased
- 2018-05-08 TW TW107115513A patent/TW201906848A/zh unknown
- 2018-05-08 CA CA3061650A patent/CA3061650A1/en not_active Abandoned
- 2018-05-08 EP EP18728518.4A patent/EP3621968A1/en not_active Withdrawn
- 2018-05-08 CN CN201880030263.3A patent/CN110603258A/zh active Pending
- 2018-05-08 JP JP2019561278A patent/JP2020519589A/ja not_active Withdrawn
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2021
- 2021-10-05 US US17/449,974 patent/US20220127281A1/en not_active Abandoned
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|---|---|
| TW201906848A (zh) | 2019-02-16 |
| WO2018206539A1 (en) | 2018-11-15 |
| US20220127281A1 (en) | 2022-04-28 |
| AR111776A1 (es) | 2019-08-21 |
| CN110603258A (zh) | 2019-12-20 |
| JP2020519589A (ja) | 2020-07-02 |
| EP3621968A1 (en) | 2020-03-18 |
| US20200109153A1 (en) | 2020-04-09 |
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