CA2993013A1 - Composes de quinazoline substitues et leur utilisation en tant qu'inhibiteurs de proteines kras, hras et/ou nras mutantes g12c - Google Patents
Composes de quinazoline substitues et leur utilisation en tant qu'inhibiteurs de proteines kras, hras et/ou nras mutantes g12c Download PDFInfo
- Publication number
- CA2993013A1 CA2993013A1 CA2993013A CA2993013A CA2993013A1 CA 2993013 A1 CA2993013 A1 CA 2993013A1 CA 2993013 A CA2993013 A CA 2993013A CA 2993013 A CA2993013 A CA 2993013A CA 2993013 A1 CA2993013 A1 CA 2993013A1
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- CA
- Canada
- Prior art keywords
- compound
- alkyl
- cancer
- halo
- cyano
- 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
Links
- 239000003112 inhibitor Substances 0.000 title abstract description 15
- 101150105104 Kras gene Proteins 0.000 title description 3
- 101150117869 Hras gene Proteins 0.000 title description 2
- 101150073096 NRAS gene Proteins 0.000 title description 2
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 392
- 238000000034 method Methods 0.000 claims abstract description 118
- 102100030708 GTPase KRas Human genes 0.000 claims abstract description 76
- 101000584612 Homo sapiens GTPase KRas Proteins 0.000 claims abstract description 76
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 59
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 56
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 201000011510 cancer Diseases 0.000 claims abstract description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 33
- 102200006538 rs121913530 Human genes 0.000 claims abstract description 31
- 229940002612 prodrug Drugs 0.000 claims abstract description 29
- 239000000651 prodrug Substances 0.000 claims abstract description 29
- 208000035475 disorder Diseases 0.000 claims abstract description 16
- -1 cyano, amino Chemical group 0.000 claims description 201
- 102100029974 GTPase HRas Human genes 0.000 claims description 83
- 101000584633 Homo sapiens GTPase HRas Proteins 0.000 claims description 82
- 125000000623 heterocyclic group Chemical group 0.000 claims description 74
- 125000005843 halogen group Chemical group 0.000 claims description 71
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 58
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 56
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 50
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 50
- 125000002837 carbocyclic group Chemical group 0.000 claims description 47
- 125000001072 heteroaryl group Chemical group 0.000 claims description 46
- 102200124918 rs121913250 Human genes 0.000 claims description 45
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 40
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 34
- 125000002947 alkylene group Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 230000035772 mutation Effects 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 125000001188 haloalkyl group Chemical group 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 230000002401 inhibitory effect Effects 0.000 claims description 25
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 238000002347 injection Methods 0.000 claims description 18
- 239000007924 injection Substances 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 16
- 108010021466 Mutant Proteins Proteins 0.000 claims description 15
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- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 15
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- 229910019142 PO4 Inorganic materials 0.000 claims description 13
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 13
- 239000010452 phosphate Substances 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 11
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 11
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- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- 230000001404 mediated effect Effects 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
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- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims description 7
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- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 6
- 230000005764 inhibitory process Effects 0.000 claims description 6
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
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- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 3
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 3
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- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
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- 239000000243 solution Substances 0.000 description 63
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 43
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- 101000744505 Homo sapiens GTPase NRas Proteins 0.000 description 40
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 38
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 32
- 239000003814 drug Substances 0.000 description 32
- 229910052938 sodium sulfate Inorganic materials 0.000 description 32
- 235000011152 sodium sulphate Nutrition 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
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- NMDYYWFGPIMTKO-HBVLKOHWSA-N vinflunine Chemical compound C([C@@](C1=C(C2=CC=CC=C2N1)C1)(C2=C(OC)C=C3N(C)[C@@H]4[C@@]5(C3=C2)CCN2CC=C[C@]([C@@H]52)([C@H]([C@]4(O)C(=O)OC)OC(C)=O)CC)C(=O)OC)[C@H]2C[C@@H](C(C)(F)F)CN1C2 NMDYYWFGPIMTKO-HBVLKOHWSA-N 0.000 description 1
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- 239000011720 vitamin B Substances 0.000 description 1
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- 239000011710 vitamin D Substances 0.000 description 1
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- 239000011712 vitamin K Substances 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Abstract
La présente invention concerne des composés ayant une activité en tant qu'inhibiteurs de la protéine KRAS mutante G12C. L'invention concerne des composés ayant la structure suivante (I) ou un sel pharmaceutiquement acceptable, un stéréoisomère ou un promédicament associé; R, R1, R2a, R2b, R2c, A, B, L1 et E étant tels que présentement définis. L'invention concerne en outre des procédés associés à la préparation et à l'utilisation de ces composés, des compositions pharmaceutiques comprenant de tels composés et des procédés pour moduler l'activité de la protéine KRAS mutante G12C à des fins de traitement de troubles, tels que le cancer.
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562195636P | 2015-07-22 | 2015-07-22 | |
| US62/195,636 | 2015-07-22 | ||
| US201662342078P | 2016-05-26 | 2016-05-26 | |
| US62/342,078 | 2016-05-26 | ||
| GC201631750 | 2016-07-21 | ||
| JO150/2016 | 2016-07-21 | ||
| GCGC-2016-31750 | 2016-07-21 | ||
| JOP/2016/0150A JOP20160150B1 (ar) | 2015-07-22 | 2016-07-21 | مركبات كينازولين مستبدلة وطرق استعمالها |
| PCT/US2016/043568 WO2017015562A1 (fr) | 2015-07-22 | 2016-07-22 | Composés de quinazoline substitués et leur utilisation en tant qu'inhibiteurs de protéines kras, hras et/ou nras mutantes g12c |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2993013A1 true CA2993013A1 (fr) | 2017-01-26 |
Family
ID=57821530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2993013A Abandoned CA2993013A1 (fr) | 2015-07-22 | 2016-07-22 | Composes de quinazoline substitues et leur utilisation en tant qu'inhibiteurs de proteines kras, hras et/ou nras mutantes g12c |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP3325447A1 (fr) |
| JP (1) | JP6869947B2 (fr) |
| CA (1) | CA2993013A1 (fr) |
| MX (1) | MX388781B (fr) |
| WO (1) | WO2017015562A1 (fr) |
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| TWI271406B (en) * | 1999-12-13 | 2007-01-21 | Eisai Co Ltd | Tricyclic condensed heterocyclic compounds, preparation method of the same and pharmaceuticals comprising the same |
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2016
- 2016-07-22 EP EP16747678.7A patent/EP3325447A1/fr not_active Withdrawn
- 2016-07-22 MX MX2018000777A patent/MX388781B/es unknown
- 2016-07-22 JP JP2018502355A patent/JP6869947B2/ja active Active
- 2016-07-22 CA CA2993013A patent/CA2993013A1/fr not_active Abandoned
- 2016-07-22 WO PCT/US2016/043568 patent/WO2017015562A1/fr not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP3325447A1 (fr) | 2018-05-30 |
| WO2017015562A1 (fr) | 2017-01-26 |
| MX388781B (es) | 2025-03-20 |
| JP6869947B2 (ja) | 2021-05-12 |
| JP2018520195A (ja) | 2018-07-26 |
| MX2018000777A (es) | 2018-03-23 |
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Effective date: 20210722 |
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| EEER | Examination request |
Effective date: 20210722 |
|
| EEER | Examination request |
Effective date: 20210722 |
|
| FZDE | Discontinued |
Effective date: 20240123 |