TWI320786B - Quinazoline derivatives and uses of the same - Google Patents

Info

Publication number

TWI320786B

TWI320786B TW092130284A TW92130284A TWI320786B TW I320786 B TWI320786 B TW I320786B TW 092130284 A TW092130284 A TW 092130284A TW 92130284 A TW92130284 A TW 92130284A TW I320786 B TWI320786 B TW I320786B

Authority

TW

Taiwan

Prior art keywords

group

ethoxy

propoxy

hexahydro

alkyl

Prior art date

2002-11-04

Links

• Espacenet
• Global Dossier
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• 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title description 4
• -1 methoxy, ethoxy Chemical group 0.000 claims description 597
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 199
• 125000001424 substituent group Chemical group 0.000 claims description 127
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 119
• 239000007789 gas Substances 0.000 claims description 110
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 64
• 150000003839 salts Chemical class 0.000 claims description 61
• 239000002253 acid Substances 0.000 claims description 55
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 51
• 125000000623 heterocyclic group Chemical group 0.000 claims description 49
• 239000001257 hydrogen Substances 0.000 claims description 45
• 229910052739 hydrogen Inorganic materials 0.000 claims description 45
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 43
• 206010028980 Neoplasm Diseases 0.000 claims description 37
• 125000003277 amino group Chemical group 0.000 claims description 36
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
• 150000003246 quinazolines Chemical class 0.000 claims description 33
• 150000001412 amines Chemical class 0.000 claims description 28
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 24
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 23
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 21
• 125000001153 fluoro group Chemical group F* 0.000 claims description 20
• 239000003795 chemical substances by application Substances 0.000 claims description 19
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 19
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 17
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
• 125000001246 bromo group Chemical group Br* 0.000 claims description 16
• 125000006612 decyloxy group Chemical group 0.000 claims description 16
• 230000002401 inhibitory effect Effects 0.000 claims description 16
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 15
• 241001465754 Metazoa Species 0.000 claims description 15
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
• 229910052786 argon Inorganic materials 0.000 claims description 14
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 14
• 238000004519 manufacturing process Methods 0.000 claims description 14
• 150000002923 oximes Chemical class 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 11
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 11
• 230000001740 anti-invasion Effects 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 241000790917 Dioxys <bee> Species 0.000 claims description 6
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
• 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
• 125000006012 2-chloroethoxy group Chemical group 0.000 claims description 3
• YIIOTOBXQVQGSV-UHFFFAOYSA-N [1,3]dioxolo[4,5-b]pyridine Chemical group C1=CN=C2OCOC2=C1 YIIOTOBXQVQGSV-UHFFFAOYSA-N 0.000 claims description 3
• 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 claims description 3
• 125000005554 pyridyloxy group Chemical group 0.000 claims description 3
• XXYDEJAJDOABCE-UHFFFAOYSA-N 2-hydrazinyl-n,n-dimethylethanamine Chemical compound CN(C)CCNN XXYDEJAJDOABCE-UHFFFAOYSA-N 0.000 claims description 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 230000007935 neutral effect Effects 0.000 claims description 2
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical class O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 2
• 125000003504 2-oxazolinyl group Chemical class O1C(=NCC1)* 0.000 claims 2
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims 1
• GBHCABUWWQUMAJ-UHFFFAOYSA-N 2-hydrazinoethanol Chemical compound NNCCO GBHCABUWWQUMAJ-UHFFFAOYSA-N 0.000 claims 1
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
• 241000234435 Lilium Species 0.000 claims 1
• NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 claims 1
• 125000004122 cyclic group Chemical group 0.000 claims 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
• ANCBHJKEYPZCTE-UHFFFAOYSA-N ethyl 5-carbamoyl-4-methyl-2-[(2,3,4,5,6-pentafluorobenzoyl)amino]thiophene-3-carboxylate Chemical compound CC1=C(C(N)=O)SC(NC(=O)C=2C(=C(F)C(F)=C(F)C=2F)F)=C1C(=O)OCC ANCBHJKEYPZCTE-UHFFFAOYSA-N 0.000 claims 1
• 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
• 150000004678 hydrides Chemical class 0.000 claims 1
• 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims 1
• 235000012054 meals Nutrition 0.000 claims 1
• 210000003296 saliva Anatomy 0.000 claims 1
• PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims 1
• 125000000217 alkyl group Chemical group 0.000 description 229
• 239000000203 mixture Substances 0.000 description 195
• 150000001875 compounds Chemical class 0.000 description 115
• 239000002585 base Substances 0.000 description 111
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 104
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 86
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
• 239000000243 solution Substances 0.000 description 61
• 238000006243 chemical reaction Methods 0.000 description 58
• 239000011541 reaction mixture Substances 0.000 description 58
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 54
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 50
• 239000000047 product Substances 0.000 description 50
• 238000000034 method Methods 0.000 description 47
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
• 238000004440 column chromatography Methods 0.000 description 40
• 238000001819 mass spectrum Methods 0.000 description 40
• 238000012360 testing method Methods 0.000 description 40
• 125000003545 alkoxy group Chemical group 0.000 description 39
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 38
• 239000007787 solid Substances 0.000 description 38
• 210000004027 cell Anatomy 0.000 description 37
• 238000005481 NMR spectroscopy Methods 0.000 description 35
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 35
• 239000000463 material Substances 0.000 description 33
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 32
• 235000019439 ethyl acetate Nutrition 0.000 description 32
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 32
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 29
• 239000002904 solvent Substances 0.000 description 29
• 101150041968 CDC13 gene Proteins 0.000 description 28
• 239000003480 eluent Substances 0.000 description 28
• 125000003118 aryl group Chemical group 0.000 description 25
• 125000001072 heteroaryl group Chemical group 0.000 description 23
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
• 125000005843 halogen group Chemical group 0.000 description 22
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
• 230000000694 effects Effects 0.000 description 21
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 21
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 21
• 235000019341 magnesium sulphate Nutrition 0.000 description 21
• 125000003282 alkyl amino group Chemical group 0.000 description 20
• 229910052799 carbon Inorganic materials 0.000 description 20
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 20
• 239000012074 organic phase Substances 0.000 description 19
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
• 238000011282 treatment Methods 0.000 description 18
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 17
• 201000011510 cancer Diseases 0.000 description 17
• 239000012071 phase Substances 0.000 description 17
• 238000002360 preparation method Methods 0.000 description 17
• 239000002994 raw material Substances 0.000 description 17
• 238000001228 spectrum Methods 0.000 description 17
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
• 125000003342 alkenyl group Chemical group 0.000 description 16
• 125000000304 alkynyl group Chemical group 0.000 description 16
• 230000005764 inhibitory process Effects 0.000 description 16
• 229910052757 nitrogen Inorganic materials 0.000 description 16
• 229960000583 acetic acid Drugs 0.000 description 15
• 239000007795 chemical reaction product Substances 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 14
• 150000002431 hydrogen Chemical class 0.000 description 14
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 14
• 102000037979 non-receptor tyrosine kinases Human genes 0.000 description 14
• 108091008046 non-receptor tyrosine kinases Proteins 0.000 description 14
• 125000006239 protecting group Chemical group 0.000 description 14
• 238000000746 purification Methods 0.000 description 14
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 12
• 239000003112 inhibitor Substances 0.000 description 12
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 12
• 239000012258 stirred mixture Substances 0.000 description 12
• 210000004881 tumor cell Anatomy 0.000 description 12
• 239000003643 water by type Substances 0.000 description 12
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 11
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 11
• 235000011114 ammonium hydroxide Nutrition 0.000 description 11
• 239000012267 brine Substances 0.000 description 11
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
• 238000001914 filtration Methods 0.000 description 11
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• 102000005962 receptors Human genes 0.000 description 11
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• 229910052707 ruthenium Inorganic materials 0.000 description 11
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
• 239000007858 starting material Substances 0.000 description 11
• 239000000126 substance Substances 0.000 description 11
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
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• 239000007864 aqueous solution Substances 0.000 description 10
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 10
• 239000001301 oxygen Substances 0.000 description 10
• 239000002244 precipitate Substances 0.000 description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
• 125000004076 pyridyl group Chemical group 0.000 description 10
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• 102000027426 receptor tyrosine kinases Human genes 0.000 description 10
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 9
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• 102000004190 Enzymes Human genes 0.000 description 9
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• 125000004414 alkyl thio group Chemical group 0.000 description 9
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• 229960005181 morphine Drugs 0.000 description 9
• 239000003208 petroleum Substances 0.000 description 9
• 229910000027 potassium carbonate Inorganic materials 0.000 description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
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• 125000005133 alkynyloxy group Chemical group 0.000 description 7
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