NO311358B1 - Kinazolin-derivater, anvendelse og fremstilling derav samt farmasöytisk preparat - Google Patents
Kinazolin-derivater, anvendelse og fremstilling derav samt farmasöytisk preparat Download PDFInfo
- Publication number
- NO311358B1 NO311358B1 NO19982784A NO982784A NO311358B1 NO 311358 B1 NO311358 B1 NO 311358B1 NO 19982784 A NO19982784 A NO 19982784A NO 982784 A NO982784 A NO 982784A NO 311358 B1 NO311358 B1 NO 311358B1
- Authority
- NO
- Norway
- Prior art keywords
- methoxy
- quinazoline
- chloro
- mmol
- hydroxy
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 147
- 150000003839 salts Chemical class 0.000 claims abstract description 74
- 238000000034 method Methods 0.000 claims abstract description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 46
- 239000001257 hydrogen Substances 0.000 claims abstract description 46
- -1 cyano, amino Chemical group 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 230000000694 effects Effects 0.000 claims abstract description 23
- 125000005843 halogen group Chemical group 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- 125000006615 aromatic heterocyclic group Chemical class 0.000 claims abstract description 5
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical class O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
- 230000008569 process Effects 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 150000003246 quinazolines Chemical class 0.000 claims description 22
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 238000010511 deprotection reaction Methods 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000001425 triazolyl group Chemical group 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000005518 carboxamido group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 230000002792 vascular Effects 0.000 claims description 4
- QWNUZVPAXFYUNL-UHFFFAOYSA-N 1-[2-[4-(4-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxyethyl]pyridin-2-one Chemical compound N1=CN=C2C=C(OCCN3C(C=CC=C3)=O)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F QWNUZVPAXFYUNL-UHFFFAOYSA-N 0.000 claims description 3
- DVMIOQFDVDENHJ-UHFFFAOYSA-N 1-[3-[4-(4-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypropyl]pyridin-2-one Chemical compound N1=CN=C2C=C(OCCCN3C(C=CC=C3)=O)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F DVMIOQFDVDENHJ-UHFFFAOYSA-N 0.000 claims description 3
- VQUUMWJYJNQUDX-UHFFFAOYSA-N 2-chloro-4-fluoro-5-[(6-methoxy-7-phenylmethoxyquinazolin-4-yl)amino]phenol Chemical compound N1=CN=C2C=C(OCC=3C=CC=CC=3)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F VQUUMWJYJNQUDX-UHFFFAOYSA-N 0.000 claims description 3
- XTJQMHZWPVZEHX-UHFFFAOYSA-N 4-(4-chloro-2-fluorophenoxy)-6-methoxy-7-(pyridin-4-ylmethoxy)quinazoline Chemical compound N1=CN=C2C=C(OCC=3C=CN=CC=3)C(OC)=CC2=C1OC1=CC=C(Cl)C=C1F XTJQMHZWPVZEHX-UHFFFAOYSA-N 0.000 claims description 3
- RPEWRZHZDKCHAS-UHFFFAOYSA-N 4-fluoro-5-(6-methoxy-7-phenylmethoxyquinazolin-4-yl)oxy-2-methylphenol Chemical compound N1=CN=C2C=C(OCC=3C=CC=CC=3)C(OC)=CC2=C1OC1=CC(O)=C(C)C=C1F RPEWRZHZDKCHAS-UHFFFAOYSA-N 0.000 claims description 3
- HRJXNLVYDUPXRU-UHFFFAOYSA-N 5-[[6-methoxy-7-(pyridin-3-ylmethoxy)quinazolin-4-yl]amino]-2-methylphenol Chemical compound N1=CN=C2C=C(OCC=3C=NC=CC=3)C(OC)=CC2=C1NC1=CC=C(C)C(O)=C1 HRJXNLVYDUPXRU-UHFFFAOYSA-N 0.000 claims description 3
- HXFKORYWVZYGRC-UHFFFAOYSA-N n-(4-chloro-2-fluorophenyl)-6-methoxy-7-(2-pyridin-2-yloxyethoxy)quinazolin-4-amine Chemical compound N1=CN=C2C=C(OCCOC=3N=CC=CC=3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F HXFKORYWVZYGRC-UHFFFAOYSA-N 0.000 claims description 3
- GVVDIHOYJPJAON-UHFFFAOYSA-N n-(4-chloro-2-fluorophenyl)-6-methoxy-7-(2-pyridin-3-yloxyethoxy)quinazolin-4-amine Chemical compound N1=CN=C2C=C(OCCOC=3C=NC=CC=3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F GVVDIHOYJPJAON-UHFFFAOYSA-N 0.000 claims description 3
- KQFJCJGCVGPNSI-UHFFFAOYSA-N n-(4-chloro-2-fluorophenyl)-6-methoxy-7-(2-pyridin-4-yloxyethoxy)quinazolin-4-amine Chemical compound N1=CN=C2C=C(OCCOC=3C=CN=CC=3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F KQFJCJGCVGPNSI-UHFFFAOYSA-N 0.000 claims description 3
- GLHFVQYRKOSWGB-UHFFFAOYSA-N n-(4-chloro-2-fluorophenyl)-6-methoxy-7-(2-pyridin-4-ylsulfanylethoxy)quinazolin-4-amine Chemical compound N1=CN=C2C=C(OCCSC=3C=CN=CC=3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F GLHFVQYRKOSWGB-UHFFFAOYSA-N 0.000 claims description 3
- XZKFOQGZJJFUIZ-UHFFFAOYSA-N n-(4-chloro-2-fluorophenyl)-6-methoxy-7-(3-pyridin-4-yloxypropoxy)quinazolin-4-amine Chemical compound N1=CN=C2C=C(OCCCOC=3C=CN=CC=3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F XZKFOQGZJJFUIZ-UHFFFAOYSA-N 0.000 claims description 3
- GVOJLNCKUYCXME-UHFFFAOYSA-N n-(4-chloro-2-fluorophenyl)-6-methoxy-7-[(2-methylpyridin-4-yl)methoxy]quinazolin-4-amine Chemical compound N1=CN=C2C=C(OCC=3C=C(C)N=CC=3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F GVOJLNCKUYCXME-UHFFFAOYSA-N 0.000 claims description 3
- QCAQIDNWNCBYQM-UHFFFAOYSA-N n-(4-chloro-2-fluorophenyl)-6-methoxy-7-[2-(1-methylimidazol-2-yl)sulfanylethoxy]quinazolin-4-amine Chemical compound N1=CN=C2C=C(OCCSC=3N(C=CN=3)C)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F QCAQIDNWNCBYQM-UHFFFAOYSA-N 0.000 claims description 3
- HEHSEBKIHUALBC-UHFFFAOYSA-N n-[4-[[4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxyquinazolin-7-yl]oxymethyl]-1,3-thiazol-2-yl]acetamide Chemical compound N1=CN=C2C=C(OCC=3N=C(NC(C)=O)SC=3)C(OC)=CC2=C1NC1=CC(O)=C(C)C=C1F HEHSEBKIHUALBC-UHFFFAOYSA-N 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- YJYLNMCGMNDUGM-UHFFFAOYSA-N 1-[2-[4-(4-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxyethyl]pyridin-4-one Chemical compound N1=CN=C2C=C(OCCN3C=CC(=O)C=C3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F YJYLNMCGMNDUGM-UHFFFAOYSA-N 0.000 claims description 2
- PWOHZMHBOWXIRW-UHFFFAOYSA-N 2-chloro-4-fluoro-5-[(7-phenylmethoxyquinazolin-4-yl)amino]phenol Chemical compound C1=C(Cl)C(O)=CC(NC=2C3=CC=C(OCC=4C=CC=CC=4)C=C3N=CN=2)=C1F PWOHZMHBOWXIRW-UHFFFAOYSA-N 0.000 claims description 2
- AZROWFRYJGNGJB-UHFFFAOYSA-N 2-chloro-4-fluoro-5-[[6-methoxy-7-(2-pyridin-4-ylethoxy)quinazolin-4-yl]amino]phenol Chemical compound N1=CN=C2C=C(OCCC=3C=CN=CC=3)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F AZROWFRYJGNGJB-UHFFFAOYSA-N 0.000 claims description 2
- NOZFQQJWPKNCJA-UHFFFAOYSA-N 2-chloro-4-fluoro-5-[[6-methoxy-7-(3-pyridin-4-ylpropoxy)quinazolin-4-yl]amino]phenol Chemical compound N1=CN=C2C=C(OCCCC=3C=CN=CC=3)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F NOZFQQJWPKNCJA-UHFFFAOYSA-N 0.000 claims description 2
- CAXHRBNFALMYCM-UHFFFAOYSA-N 2-chloro-4-fluoro-5-[[6-methoxy-7-(pyridin-4-ylmethoxy)quinazolin-4-yl]amino]phenol Chemical compound N1=CN=C2C=C(OCC=3C=CN=CC=3)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F CAXHRBNFALMYCM-UHFFFAOYSA-N 0.000 claims description 2
- JEPZGYZEFVPCKU-UHFFFAOYSA-N 2-chloro-4-fluoro-5-[[6-methoxy-7-(thiophen-3-ylmethoxy)quinazolin-4-yl]amino]phenol Chemical compound N1=CN=C2C=C(OCC3=CSC=C3)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F JEPZGYZEFVPCKU-UHFFFAOYSA-N 0.000 claims description 2
- AITNQYZBIQPEGS-UHFFFAOYSA-N 2-chloro-4-fluoro-5-[[6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]quinazolin-4-yl]amino]phenol Chemical compound N1=CN=C2C=C(OCC=3N(C=CN=3)C)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F AITNQYZBIQPEGS-UHFFFAOYSA-N 0.000 claims description 2
- HKYVCHKCMQICPG-UHFFFAOYSA-N 2-chloro-4-fluoro-5-[[6-methoxy-7-[(2-methyl-1,3-thiazol-4-yl)methoxy]quinazolin-4-yl]amino]phenol Chemical compound N1=CN=C2C=C(OCC=3N=C(C)SC=3)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F HKYVCHKCMQICPG-UHFFFAOYSA-N 0.000 claims description 2
- PAPGGNWOGWVEGR-UHFFFAOYSA-N 2-chloro-4-fluoro-5-[[7-(2-imidazol-1-ylethoxy)-6-methoxyquinazolin-4-yl]amino]phenol Chemical compound N1=CN=C2C=C(OCCN3C=NC=C3)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F PAPGGNWOGWVEGR-UHFFFAOYSA-N 0.000 claims description 2
- HJTXROVEBQVPNY-UHFFFAOYSA-N 3-[[7-(2-imidazol-1-ylethoxy)-6-methoxyquinazolin-4-yl]amino]phenol Chemical compound N1=CN=C2C=C(OCCN3C=NC=C3)C(OC)=CC2=C1NC1=CC=CC(O)=C1 HJTXROVEBQVPNY-UHFFFAOYSA-N 0.000 claims description 2
- PPODXRSVLLAFKK-UHFFFAOYSA-N 4-[[4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxyquinazolin-7-yl]oxymethyl]benzonitrile Chemical compound N1=CN=C2C=C(OCC=3C=CC(=CC=3)C#N)C(OC)=CC2=C1NC1=CC(O)=C(C)C=C1F PPODXRSVLLAFKK-UHFFFAOYSA-N 0.000 claims description 2
- GXUZCXHQQSFIEV-UHFFFAOYSA-N 4-fluoro-2-methyl-5-[[7-(pyridin-4-ylmethoxy)quinazolin-4-yl]amino]phenol Chemical compound C1=C(O)C(C)=CC(F)=C1NC1=NC=NC2=CC(OCC=3C=CN=CC=3)=CC=C12 GXUZCXHQQSFIEV-UHFFFAOYSA-N 0.000 claims description 2
- QTJJVAOWCGCHGL-UHFFFAOYSA-N 4-fluoro-5-[(6-methoxy-7-phenylmethoxyquinazolin-4-yl)amino]-2-methylphenol Chemical compound N1=CN=C2C=C(OCC=3C=CC=CC=3)C(OC)=CC2=C1NC1=CC(O)=C(C)C=C1F QTJJVAOWCGCHGL-UHFFFAOYSA-N 0.000 claims description 2
- RLELBWLVWSGXMA-UHFFFAOYSA-N 4-fluoro-5-[[6-methoxy-7-(2-pyridin-4-ylethoxy)quinazolin-4-yl]amino]-2-methylphenol Chemical compound N1=CN=C2C=C(OCCC=3C=CN=CC=3)C(OC)=CC2=C1NC1=CC(O)=C(C)C=C1F RLELBWLVWSGXMA-UHFFFAOYSA-N 0.000 claims description 2
- NHSHOQSKIOKHDT-UHFFFAOYSA-N 4-fluoro-5-[[6-methoxy-7-(3-pyridin-4-ylpropoxy)quinazolin-4-yl]amino]-2-methylphenol Chemical compound N1=CN=C2C=C(OCCCC=3C=CN=CC=3)C(OC)=CC2=C1NC1=CC(O)=C(C)C=C1F NHSHOQSKIOKHDT-UHFFFAOYSA-N 0.000 claims description 2
- FOJARYAZSBLSFZ-UHFFFAOYSA-N 4-fluoro-5-[[6-methoxy-7-(thiophen-3-ylmethoxy)quinazolin-4-yl]amino]-2-methylphenol Chemical compound N1=CN=C2C=C(OCC3=CSC=C3)C(OC)=CC2=C1NC1=CC(O)=C(C)C=C1F FOJARYAZSBLSFZ-UHFFFAOYSA-N 0.000 claims description 2
- SPZITRLPIMIDFC-UHFFFAOYSA-N 4-fluoro-5-[[7-(2-imidazol-1-ylethoxy)-6-methoxyquinazolin-4-yl]amino]-2-methylphenol Chemical compound N1=CN=C2C=C(OCCN3C=NC=C3)C(OC)=CC2=C1NC1=CC(O)=C(C)C=C1F SPZITRLPIMIDFC-UHFFFAOYSA-N 0.000 claims description 2
- UYYMNTGKAHEONS-UHFFFAOYSA-N 5-[[6-methoxy-7-(3-pyridin-4-ylpropoxy)quinazolin-4-yl]amino]-2-methylphenol Chemical compound N1=CN=C2C=C(OCCCC=3C=CN=CC=3)C(OC)=CC2=C1NC1=CC=C(C)C(O)=C1 UYYMNTGKAHEONS-UHFFFAOYSA-N 0.000 claims description 2
- INXCAKZSZWSSSN-UHFFFAOYSA-N 5-[[6-methoxy-7-(pyridin-2-ylmethoxy)quinazolin-4-yl]amino]-2-methylphenol Chemical compound N1=CN=C2C=C(OCC=3N=CC=CC=3)C(OC)=CC2=C1NC1=CC=C(C)C(O)=C1 INXCAKZSZWSSSN-UHFFFAOYSA-N 0.000 claims description 2
- PDBVAFBKHKEWJV-UHFFFAOYSA-N 5-[[6-methoxy-7-(pyridin-4-ylmethoxy)quinazolin-4-yl]amino]-2-methylphenol Chemical compound N1=CN=C2C=C(OCC=3C=CN=CC=3)C(OC)=CC2=C1NC1=CC=C(C)C(O)=C1 PDBVAFBKHKEWJV-UHFFFAOYSA-N 0.000 claims description 2
- XVQUHUORWOJDGB-UHFFFAOYSA-N 5-[[6-methoxy-7-(thiophen-3-ylmethoxy)quinazolin-4-yl]amino]-2-methylphenol Chemical compound N1=CN=C2C=C(OCC3=CSC=C3)C(OC)=CC2=C1NC1=CC=C(C)C(O)=C1 XVQUHUORWOJDGB-UHFFFAOYSA-N 0.000 claims description 2
- GTUUUFCZMXZIFG-UHFFFAOYSA-N 5-[[6-methoxy-7-[(1-methylbenzimidazol-2-yl)methoxy]quinazolin-4-yl]amino]-2-methylphenol Chemical compound N1=CN=C2C=C(OCC=3N(C4=CC=CC=C4N=3)C)C(OC)=CC2=C1NC1=CC=C(C)C(O)=C1 GTUUUFCZMXZIFG-UHFFFAOYSA-N 0.000 claims description 2
- PPMHKYHSFBSCMB-UHFFFAOYSA-N 5-[[6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]quinazolin-4-yl]amino]-2-methylphenol Chemical compound N1=CN=C2C=C(OCC=3N(C=CN=3)C)C(OC)=CC2=C1NC1=CC=C(C)C(O)=C1 PPMHKYHSFBSCMB-UHFFFAOYSA-N 0.000 claims description 2
- QKWMETRCZNPHLY-UHFFFAOYSA-N 5-[[7-[(2-chloropyridin-4-yl)methoxy]-6-methoxyquinazolin-4-yl]amino]-4-fluoro-2-methylphenol Chemical compound N1=CN=C2C=C(OCC=3C=C(Cl)N=CC=3)C(OC)=CC2=C1NC1=CC(O)=C(C)C=C1F QKWMETRCZNPHLY-UHFFFAOYSA-N 0.000 claims description 2
- YTHLPDILQOAQNK-UHFFFAOYSA-N 5-[[7-[(3,4-difluorophenyl)methoxy]-6-methoxyquinazolin-4-yl]amino]-4-fluoro-2-methylphenol Chemical compound N1=CN=C2C=C(OCC=3C=C(F)C(F)=CC=3)C(OC)=CC2=C1NC1=CC(O)=C(C)C=C1F YTHLPDILQOAQNK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 2
- NVBNDZZLJRYRPD-UHFFFAOYSA-N ZM 323881 Chemical compound C1=C(O)C(C)=CC(F)=C1NC1=NC=NC2=CC(OCC=3C=CC=CC=3)=CC=C12 NVBNDZZLJRYRPD-UHFFFAOYSA-N 0.000 claims description 2
- 230000002491 angiogenic effect Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- QJQYPZZUKLQGGT-UHFFFAOYSA-N methyl hypobromite Chemical compound COBr QJQYPZZUKLQGGT-UHFFFAOYSA-N 0.000 claims description 2
- IVENRKYGZWVTEK-UHFFFAOYSA-N n-(4-bromo-2-fluorophenyl)-6-methoxy-7-[2-(1,2,4-triazol-1-yl)ethoxy]quinazolin-4-amine Chemical compound N1=CN=C2C=C(OCCN3N=CN=C3)C(OC)=CC2=C1NC1=CC=C(Br)C=C1F IVENRKYGZWVTEK-UHFFFAOYSA-N 0.000 claims description 2
- VHFMXQUBHSIGCQ-UHFFFAOYSA-N n-(4-chloro-2-fluorophenyl)-6-methoxy-7-(2-pyridin-4-ylethoxy)quinazolin-4-amine Chemical compound N1=CN=C2C=C(OCCC=3C=CN=CC=3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F VHFMXQUBHSIGCQ-UHFFFAOYSA-N 0.000 claims description 2
- CAXCHMGHVXPTAD-UHFFFAOYSA-N n-(4-chloro-2-fluorophenyl)-6-methoxy-7-(3-pyridin-4-ylpropoxy)quinazolin-4-amine Chemical compound N1=CN=C2C=C(OCCCC=3C=CN=CC=3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F CAXCHMGHVXPTAD-UHFFFAOYSA-N 0.000 claims description 2
- GKGQZMWDXTVJQI-UHFFFAOYSA-N n-(4-chloro-2-fluorophenyl)-6-methoxy-7-(pyridin-4-ylmethoxy)quinazolin-4-amine Chemical compound N1=CN=C2C=C(OCC=3C=CN=CC=3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F GKGQZMWDXTVJQI-UHFFFAOYSA-N 0.000 claims description 2
- ORADRWKXLYIOGS-UHFFFAOYSA-N n-(4-chloro-2-fluorophenyl)-6-methoxy-7-(thiophen-3-ylmethoxy)quinazolin-4-amine Chemical compound N1=CN=C2C=C(OCC3=CSC=C3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F ORADRWKXLYIOGS-UHFFFAOYSA-N 0.000 claims description 2
- SXCPGBVLGDVEHO-UHFFFAOYSA-N n-(4-chloro-2-fluorophenyl)-6-methoxy-7-[2-(1,2,4-triazol-1-yl)ethoxy]quinazolin-4-amine Chemical compound N1=CN=C2C=C(OCCN3N=CN=C3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F SXCPGBVLGDVEHO-UHFFFAOYSA-N 0.000 claims description 2
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- 229960001278 teniposide Drugs 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
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- 229960000303 topotecan Drugs 0.000 description 1
- XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 description 1
- 229960005026 toremifene Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
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Classifications
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- 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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- C07D239/93—Sulfur atoms
-
- 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
- C07D239/94—Nitrogen 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP95402846 | 1995-12-18 | ||
EP96402190 | 1996-10-15 | ||
PCT/GB1996/003075 WO1997022596A1 (en) | 1995-12-18 | 1996-12-13 | Quinazoline derivatives |
Publications (3)
Publication Number | Publication Date |
---|---|
NO982784D0 NO982784D0 (no) | 1998-06-17 |
NO982784L NO982784L (no) | 1998-08-17 |
NO311358B1 true NO311358B1 (no) | 2001-11-19 |
Family
ID=26140602
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19982784A NO311358B1 (no) | 1995-12-18 | 1998-06-17 | Kinazolin-derivater, anvendelse og fremstilling derav samt farmasöytisk preparat |
Country Status (29)
Country | Link |
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US (4) | US5962458A (da) |
EP (1) | EP0873319B1 (da) |
JP (1) | JP4291413B2 (da) |
KR (1) | KR100530311B1 (da) |
CN (1) | CN1133625C (da) |
AT (1) | ATE203524T1 (da) |
AU (1) | AU712370B2 (da) |
BR (1) | BR9612043A (da) |
CA (1) | CA2237005C (da) |
CZ (1) | CZ291100B6 (da) |
DE (1) | DE69614147T2 (da) |
DK (1) | DK0873319T3 (da) |
ES (1) | ES2162656T3 (da) |
GB (1) | GB9624482D0 (da) |
GR (1) | GR3036954T3 (da) |
HU (1) | HUP9901243A3 (da) |
IL (1) | IL124925A0 (da) |
MX (1) | MX9804247A (da) |
MY (1) | MY132405A (da) |
NO (1) | NO311358B1 (da) |
NZ (1) | NZ324007A (da) |
PL (1) | PL192309B1 (da) |
PT (1) | PT873319E (da) |
RU (1) | RU2194701C2 (da) |
SI (1) | SI0873319T1 (da) |
SK (1) | SK282443B6 (da) |
TR (1) | TR199801115T2 (da) |
TW (1) | TW411274B (da) |
WO (1) | WO1997022596A1 (da) |
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IL125686A (en) | 1996-02-13 | 2002-11-10 | Zeneca Ltd | Quinazoline derivatives, processes for their preparation, pharmaceutical preparations containing them and their use in the manufacture of a drug with an anti-angiogenic effect and / or an effect of reducing vascular permeability |
DE69709319T2 (de) | 1996-03-05 | 2002-08-14 | Astrazeneca Ab | 4-anilinochinazolin derivate |
DE69710712T3 (de) | 1996-04-12 | 2010-12-23 | Warner-Lambert Co. Llc | Umkehrbare inhibitoren von tyrosin kinasen |
GB9707800D0 (en) | 1996-05-06 | 1997-06-04 | Zeneca Ltd | Chemical compounds |
ATE229019T1 (de) | 1996-06-27 | 2002-12-15 | Janssen Pharmaceutica Nv | N-4-(heteroarylmethyl)phenyl- heteroarylaminderivate |
JP2001500890A (ja) | 1996-09-25 | 2001-01-23 | ゼネカ リミテッド | Vegfのような成長因子の作用を阻害するキノリン誘導体 |
GB9718972D0 (en) * | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
JP2009007364A (ja) * | 1996-10-15 | 2009-01-15 | Astrazeneca Uk Ltd | キナゾリン誘導体 |
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-
1996
- 1996-11-25 GB GBGB9624482.7A patent/GB9624482D0/en active Pending
- 1996-12-13 DK DK96941787T patent/DK0873319T3/da active
- 1996-12-13 CZ CZ19981882A patent/CZ291100B6/cs not_active IP Right Cessation
- 1996-12-13 SI SI9630354T patent/SI0873319T1/xx unknown
- 1996-12-13 CN CNB961991100A patent/CN1133625C/zh not_active Expired - Fee Related
- 1996-12-13 JP JP52256897A patent/JP4291413B2/ja not_active Expired - Fee Related
- 1996-12-13 TR TR1998/01115T patent/TR199801115T2/xx unknown
- 1996-12-13 PT PT96941787T patent/PT873319E/pt unknown
- 1996-12-13 WO PCT/GB1996/003075 patent/WO1997022596A1/en not_active Application Discontinuation
- 1996-12-13 SK SK828-98A patent/SK282443B6/sk not_active IP Right Cessation
- 1996-12-13 DE DE69614147T patent/DE69614147T2/de not_active Expired - Lifetime
- 1996-12-13 PL PL327310A patent/PL192309B1/pl not_active IP Right Cessation
- 1996-12-13 RU RU98113300/04A patent/RU2194701C2/ru not_active IP Right Cessation
- 1996-12-13 IL IL12492596A patent/IL124925A0/xx not_active IP Right Cessation
- 1996-12-13 EP EP96941787A patent/EP0873319B1/en not_active Expired - Lifetime
- 1996-12-13 HU HU9901243A patent/HUP9901243A3/hu unknown
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- 1996-12-13 KR KR1019980704613A patent/KR100530311B1/ko not_active IP Right Cessation
- 1996-12-13 ES ES96941787T patent/ES2162656T3/es not_active Expired - Lifetime
- 1996-12-13 BR BR9612043-6A patent/BR9612043A/pt not_active IP Right Cessation
- 1996-12-13 NZ NZ324007A patent/NZ324007A/xx not_active IP Right Cessation
- 1996-12-13 AT AT96941787T patent/ATE203524T1/de active
- 1996-12-13 AU AU11061/97A patent/AU712370B2/en not_active Ceased
- 1996-12-17 TW TW085115569A patent/TW411274B/zh not_active IP Right Cessation
- 1996-12-17 US US08/768,887 patent/US5962458A/en not_active Expired - Lifetime
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1998
- 1998-05-28 MX MX9804247A patent/MX9804247A/es unknown
- 1998-06-17 NO NO19982784A patent/NO311358B1/no not_active IP Right Cessation
- 1998-12-02 US US09/203,764 patent/US6071921A/en not_active Expired - Lifetime
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2000
- 2000-02-09 US US09/500,470 patent/US6258951B1/en not_active Expired - Lifetime
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