TW321649B

TW321649B -

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Publication number: TW321649B
Authority: TW; Taiwan
Prior art keywords: group; formula; gas; amino; methyl
Prior art date: 1994-11-12

Application number

TW084111357A

Other languages

English (en)

Chinese (zh)

Original Assignee

Zeneca Ltd

Priority date

1994-11-12

Filing date

1995-10-27

Publication date

1997-12-01

1994-11-12 Priority claimed from GB9422866A external-priority patent/GB9422866D0/en

1995-04-07 Priority claimed from GBGB9507308.6A external-priority patent/GB9507308D0/en

1995-10-27 Application filed by Zeneca Ltd filed Critical Zeneca Ltd

1997-12-01 Application granted granted Critical

1997-12-01 Publication of TW321649B publication Critical patent/TW321649B/zh

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125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 145
150000001875 compounds Chemical class 0.000 claims abstract description 124
238000000034 method Methods 0.000 claims abstract description 106
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 48
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 17
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims abstract description 12
229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
229910052717 sulfur Chemical group 0.000 claims abstract description 12
239000001301 oxygen Substances 0.000 claims abstract description 10
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
-1 hexahydropyridyl Chemical group 0.000 claims description 429
239000007789 gas Substances 0.000 claims description 183
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 108
238000011049 filling Methods 0.000 claims description 106
125000003545 alkoxy group Chemical group 0.000 claims description 101
125000000217 alkyl group Chemical group 0.000 claims description 82
125000003282 alkyl amino group Chemical group 0.000 claims description 79
125000003277 amino group Chemical group 0.000 claims description 79
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 72
150000003839 salts Chemical class 0.000 claims description 65
238000006243 chemical reaction Methods 0.000 claims description 45
239000002253 acid Substances 0.000 claims description 43
150000001412 amines Chemical class 0.000 claims description 43
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 41
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
125000001424 substituent group Chemical group 0.000 claims description 39
239000011737 fluorine Substances 0.000 claims description 33
229910052731 fluorine Inorganic materials 0.000 claims description 33
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 26
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 24
230000002829 reductive effect Effects 0.000 claims description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 20
230000001028 anti-proliverative effect Effects 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 17
125000001153 fluoro group Chemical group F* 0.000 claims description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
229910052794 bromium Inorganic materials 0.000 claims description 15
241001465754 Metazoa Species 0.000 claims description 14
150000003973 alkyl amines Chemical class 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 14
125000001072 heteroaryl group Chemical group 0.000 claims description 14
230000009467 reduction Effects 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 13
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 13
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical group CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000004076 pyridyl group Chemical group 0.000 claims description 12
229910002091 carbon monoxide Inorganic materials 0.000 claims description 11
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 10
125000006308 propyl amino group Chemical group 0.000 claims description 10
230000002079 cooperative effect Effects 0.000 claims description 9
125000002541 furyl group Chemical group 0.000 claims description 9
125000002883 imidazolyl group Chemical group 0.000 claims description 9
125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 8
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
150000001335 aliphatic alkanes Chemical group 0.000 claims description 8
239000003085 diluting agent Substances 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000003226 pyrazolyl group Chemical group 0.000 claims description 6
125000004423 acyloxy group Chemical group 0.000 claims description 5
125000005530 alkylenedioxy group Chemical group 0.000 claims description 5
HSMPSHPWCOOUJH-UHFFFAOYSA-N anilinyl Chemical group [NH]C1=CC=CC=C1 HSMPSHPWCOOUJH-UHFFFAOYSA-N 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
125000002971 oxazolyl group Chemical group 0.000 claims description 5
230000003647 oxidation Effects 0.000 claims description 5
238000007254 oxidation reaction Methods 0.000 claims description 5
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 4
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
PPQDYOBQQWPTIS-UHFFFAOYSA-N 2-(diethylamino)acetamide Chemical compound CCN(CC)CC(N)=O PPQDYOBQQWPTIS-UHFFFAOYSA-N 0.000 claims description 3
WKJOQYHMXRVQDK-UHFFFAOYSA-N 2-(dimethylamino)acetamide Chemical compound CN(C)CC(N)=O WKJOQYHMXRVQDK-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 3
229940100198 alkylating agent Drugs 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 3
125000006525 methoxy ethyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])OC([H])([H])[H] 0.000 claims description 3
125000000335 thiazolyl group Chemical group 0.000 claims description 3
125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 2
WVFZXCIIJBHBAA-UHFFFAOYSA-N 3-amino-1-morpholin-4-ylpropan-1-one Chemical compound NCCC(=O)N1CCOCC1 WVFZXCIIJBHBAA-UHFFFAOYSA-N 0.000 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
102000017795 Perilipin-1 Human genes 0.000 claims description 2
108010067162 Perilipin-1 Proteins 0.000 claims description 2
229910021529 ammonia Inorganic materials 0.000 claims description 2
239000012298 atmosphere Chemical group 0.000 claims description 2
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
150000001448 anilines Chemical class 0.000 claims 18
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 8
PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 3
125000001725 pyrenyl group Chemical group 0.000 claims 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
KJZUUHBRCBCMNK-UHFFFAOYSA-N 3-(4-methylpiperidin-1-yl)propan-1-amine Chemical group CC1CCN(CCCN)CC1 KJZUUHBRCBCMNK-UHFFFAOYSA-N 0.000 claims 1
YGTHBVOCTPFJHQ-UHFFFAOYSA-N 4-(dimethylamino)butanamide Chemical compound CN(C)CCCC(N)=O YGTHBVOCTPFJHQ-UHFFFAOYSA-N 0.000 claims 1
241000088885 Chlorops Species 0.000 claims 1
241000219112 Cucumis Species 0.000 claims 1
235000015510 Cucumis melo subsp melo Nutrition 0.000 claims 1
RZKYEQDPDZUERB-UHFFFAOYSA-N Pindone Chemical compound C1=CC=C2C(=O)C(C(=O)C(C)(C)C)C(=O)C2=C1 RZKYEQDPDZUERB-UHFFFAOYSA-N 0.000 claims 1
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims 1
230000021736 acetylation Effects 0.000 claims 1
238000006640 acetylation reaction Methods 0.000 claims 1
150000001555 benzenes Chemical class 0.000 claims 1
150000002440 hydroxy compounds Chemical class 0.000 claims 1
UAJNJISUUJMOHT-UHFFFAOYSA-N n-(4-benzyl-3-chlorophenyl)-6,7-dimethoxyquinazolin-4-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1NC(C=C1Cl)=CC=C1CC1=CC=CC=C1 UAJNJISUUJMOHT-UHFFFAOYSA-N 0.000 claims 1
OFIVTYIJGCSXQF-UHFFFAOYSA-N n-[3-fluoro-4-(pyridin-2-ylmethoxy)phenyl]-6,7-dimethoxyquinazolin-4-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1NC(C=C1F)=CC=C1OCC1=CC=CC=N1 OFIVTYIJGCSXQF-UHFFFAOYSA-N 0.000 claims 1
238000006722 reduction reaction Methods 0.000 claims 1
238000006268 reductive amination reaction Methods 0.000 claims 1
229910052711 selenium Inorganic materials 0.000 claims 1
239000011669 selenium Substances 0.000 claims 1
206010028980 Neoplasm Diseases 0.000 abstract description 32
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 19
238000011282 treatment Methods 0.000 abstract description 18
201000011510 cancer Diseases 0.000 abstract description 14
229910052757 nitrogen Inorganic materials 0.000 abstract description 13
201000010099 disease Diseases 0.000 abstract description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 9
239000011593 sulfur Chemical group 0.000 abstract description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 7
125000005842 heteroatom Chemical group 0.000 abstract description 5
230000002062 proliferating effect Effects 0.000 abstract description 3
229940121358 tyrosine kinase inhibitor Drugs 0.000 abstract description 3
239000005483 tyrosine kinase inhibitor Substances 0.000 abstract description 3
125000001624 naphthyl group Chemical group 0.000 abstract 1
239000000203 mixture Substances 0.000 description 245
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 144
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 112
239000007858 starting material Substances 0.000 description 97
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 82
239000000243 solution Substances 0.000 description 77
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 76
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 75
238000002844 melting Methods 0.000 description 58
230000008018 melting Effects 0.000 description 58
239000000047 product Substances 0.000 description 56
238000012360 testing method Methods 0.000 description 55
238000010992 reflux Methods 0.000 description 52
238000005481 NMR spectroscopy Methods 0.000 description 48
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
239000002585 base Substances 0.000 description 43
239000000463 material Substances 0.000 description 43
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
238000000921 elemental analysis Methods 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
239000012074 organic phase Substances 0.000 description 35
238000004440 column chromatography Methods 0.000 description 34
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
239000003480 eluent Substances 0.000 description 30
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 28
229910052943 magnesium sulfate Inorganic materials 0.000 description 26
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 24
239000000126 substance Substances 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 22
108091008598 receptor tyrosine kinases Proteins 0.000 description 22
102000027426 receptor tyrosine kinases Human genes 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
210000004027 cell Anatomy 0.000 description 20
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 19
239000011541 reaction mixture Substances 0.000 description 19
239000002244 precipitate Substances 0.000 description 17
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
239000007787 solid Substances 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
229910052786 argon Inorganic materials 0.000 description 14
150000002576 ketones Chemical class 0.000 description 14
BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 14
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 13
229910052751 metal Inorganic materials 0.000 description 13
239000002184 metal Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 12
229910052736 halogen Inorganic materials 0.000 description 12
230000002401 inhibitory effect Effects 0.000 description 12
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 11
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
125000003368 amide group Chemical group 0.000 description 10
238000000354 decomposition reaction Methods 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
150000002367 halogens Chemical class 0.000 description 10
239000012442 inert solvent Substances 0.000 description 10
102000005962 receptors Human genes 0.000 description 10
108020003175 receptors Proteins 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
229910052783 alkali metal Inorganic materials 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
239000003701 inert diluent Substances 0.000 description 9
238000000746 purification Methods 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
238000003756 stirring Methods 0.000 description 9
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
238000002309 gasification Methods 0.000 description 8
239000003102 growth factor Substances 0.000 description 8
238000002347 injection Methods 0.000 description 8
239000007924 injection Substances 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
102000001301 EGF receptor Human genes 0.000 description 7
108060006698 EGF receptor Proteins 0.000 description 7
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