CA2993013A1 - Substituted quinazoline compounds and their use as inhibitors of g12c mutant kras, hras and/or nras proteins - Google Patents

Info

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

Authority

CA

Canada

Prior art keywords

compound

alkyl

cancer

halo

cyano

Prior art date

2015-07-22

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

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 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
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• 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
• 102000008300 Mutant Proteins Human genes 0.000 claims description 15
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 15
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
• 125000004043 oxo group Chemical group O=* 0.000 claims description 14
• 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
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• 208000020816 lung neoplasm Diseases 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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• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 9
• 201000005202 lung cancer Diseases 0.000 claims description 9
• 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
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 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
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 6
• 230000005764 inhibitory process Effects 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
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• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• 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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• 201000002528 pancreatic cancer Diseases 0.000 claims description 5
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 5
• 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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• 125000003282 alkyl amino group Chemical group 0.000 claims description 3
• 125000001769 aryl amino group Chemical group 0.000 claims description 3
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• 125000005241 heteroarylamino group Chemical group 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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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• 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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• 235000011152 sodium sulphate Nutrition 0.000 description 32
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