ZA200301510B - Quinazoline derivatives as kinase inhibitors. - Google Patents
Quinazoline derivatives as kinase inhibitors. Download PDFInfo
- Publication number
- ZA200301510B ZA200301510B ZA200301510A ZA200301510A ZA200301510B ZA 200301510 B ZA200301510 B ZA 200301510B ZA 200301510 A ZA200301510 A ZA 200301510A ZA 200301510 A ZA200301510 A ZA 200301510A ZA 200301510 B ZA200301510 B ZA 200301510B
- Authority
- ZA
- South Africa
- Prior art keywords
- methoxy
- quinazolin
- piperazinyl
- carboxamide
- amended sheet
- Prior art date
Links
- 229940043355 kinase inhibitor Drugs 0.000 title description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
- -1 nitrogen-containing heterocyclic compound Chemical class 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 23
- 125000004546 quinazolin-4-yl group Chemical group N1=CN=C(C2=CC=CC=C12)* 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 14
- 125000004193 piperazinyl group Chemical group 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 230000002401 inhibitory effect Effects 0.000 claims description 12
- 150000004677 hydrates Chemical class 0.000 claims description 10
- 229940002612 prodrug Drugs 0.000 claims description 10
- 239000000651 prodrug Substances 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
- 230000026731 phosphorylation Effects 0.000 claims description 8
- 238000006366 phosphorylation reaction Methods 0.000 claims description 8
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 108091008606 PDGF receptors Proteins 0.000 claims description 6
- 102000011653 Platelet-Derived Growth Factor Receptors Human genes 0.000 claims description 6
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 206010061989 glomerulosclerosis Diseases 0.000 claims description 6
- 230000002792 vascular Effects 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 230000002159 abnormal effect Effects 0.000 claims description 4
- 230000010261 cell growth Effects 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 claims description 2
- WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 9
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims 5
- 208000037803 restenosis Diseases 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- YNQJCOMRDQJVNA-UHFFFAOYSA-N 4-[6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yl]-n-(4-naphthalen-2-yloxyphenyl)piperazine-1-carboxamide Chemical compound C1=CC=CC2=CC(OC3=CC=C(C=C3)NC(=O)N3CCN(CC3)C=3N=CN=C4C=C(C(=CC4=3)OC)OCCOC)=CC=C21 YNQJCOMRDQJVNA-UHFFFAOYSA-N 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- AJYMYKJMGGNMHX-UHFFFAOYSA-N n-(4-cyanophenyl)-4-[6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yl]piperazine-1-carboxamide Chemical compound C=12C=C(OC)C(OCCOC)=CC2=NC=NC=1N(CC1)CCN1C(=O)NC1=CC=C(C#N)C=C1 AJYMYKJMGGNMHX-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 description 16
- 108091000080 Phosphotransferase Proteins 0.000 description 9
- 102000020233 phosphotransferase Human genes 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 108010038512 Platelet-Derived Growth Factor Proteins 0.000 description 4
- 102000010780 Platelet-Derived Growth Factor Human genes 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- 108091007914 CDKs Proteins 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000006229 amino acid addition Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Chemical class 0.000 description 3
- ZQFCWMFRQFAQPO-UHFFFAOYSA-N n-(4-propan-2-yloxyphenyl)formamide Chemical compound CC(C)OC1=CC=C(NC=O)C=C1 ZQFCWMFRQFAQPO-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 102000003903 Cyclin-dependent kinases Human genes 0.000 description 2
- 108090000266 Cyclin-dependent kinases Proteins 0.000 description 2
- 108060006698 EGF receptor Proteins 0.000 description 2
- 102000001301 EGF receptor Human genes 0.000 description 2
- 108050007372 Fibroblast Growth Factor Proteins 0.000 description 2
- 102000018233 Fibroblast Growth Factor Human genes 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 102000001253 Protein Kinase Human genes 0.000 description 2
- 108091008605 VEGF receptors Proteins 0.000 description 2
- 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 description 2
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940126864 fibroblast growth factor Drugs 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 108060006633 protein kinase Proteins 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229940124676 vascular endothelial growth factor receptor Drugs 0.000 description 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- QJNRQJGEIYYPRW-UHFFFAOYSA-N 2,3-dimethoxyquinoline Chemical class C1=CC=C2N=C(OC)C(OC)=CC2=C1 QJNRQJGEIYYPRW-UHFFFAOYSA-N 0.000 description 1
- RVZMPNMUBCAPQO-UHFFFAOYSA-N 2,4-dimethoxyquinazoline Chemical class C1=CC=CC2=NC(OC)=NC(OC)=C21 RVZMPNMUBCAPQO-UHFFFAOYSA-N 0.000 description 1
- MYVWRUJLVWFNKC-UHFFFAOYSA-N 4-(6,7-dimethoxyquinazolin-4-yl)-n,n-dimethylpiperazine-1-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N1CCN(C(=O)N(C)C)CC1 MYVWRUJLVWFNKC-UHFFFAOYSA-N 0.000 description 1
- MPDJGCLHGADASW-UHFFFAOYSA-N 4-(6-methoxy-7-prop-2-enoxyquinazolin-4-yl)-n-(4-phenoxyphenyl)piperazine-1-carboxamide Chemical compound N1=CN=C2C=C(OCC=C)C(OC)=CC2=C1N(CC1)CCN1C(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 MPDJGCLHGADASW-UHFFFAOYSA-N 0.000 description 1
- YDVWNTXBGIEREW-UHFFFAOYSA-N 4-(7-ethoxy-6-methoxyquinazolin-4-yl)-n-(4-phenoxyphenyl)piperazine-1-carboxamide Chemical compound C=12C=C(OC)C(OCC)=CC2=NC=NC=1N(CC1)CCN1C(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 YDVWNTXBGIEREW-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 102000001291 MAP Kinase Kinase Kinase Human genes 0.000 description 1
- 108091054455 MAP kinase family Proteins 0.000 description 1
- 102000043136 MAP kinase family Human genes 0.000 description 1
- 108060006687 MAP kinase kinase kinase Proteins 0.000 description 1
- 102100028198 Macrophage colony-stimulating factor 1 receptor Human genes 0.000 description 1
- 101710150918 Macrophage colony-stimulating factor 1 receptor Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 101100335081 Mus musculus Flt3 gene Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000002141 anti-parasite Effects 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007887 coronary angioplasty Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000003176 fibrotic effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- MLVFPRGCMGYZDX-UHFFFAOYSA-N n-(4-cyanophenyl)-4-(6-methoxy-7-prop-2-enoxyquinazolin-4-yl)piperazine-1-carboxamide Chemical compound N1=CN=C2C=C(OCC=C)C(OC)=CC2=C1N(CC1)CCN1C(=O)NC1=CC=C(C#N)C=C1 MLVFPRGCMGYZDX-UHFFFAOYSA-N 0.000 description 1
- HAIISKATUKQKSB-UHFFFAOYSA-N n-(4-cyanophenyl)-4-(7-ethoxy-6-methoxyquinazolin-4-yl)piperazine-1-carboxamide Chemical compound C=12C=C(OC)C(OCC)=CC2=NC=NC=1N(CC1)CCN1C(=O)NC1=CC=C(C#N)C=C1 HAIISKATUKQKSB-UHFFFAOYSA-N 0.000 description 1
- FLWVPBCUGYXRMY-UHFFFAOYSA-N n-(4-cyanophenyl)-4-[6-methoxy-7-[2-(2h-tetrazol-5-yl)ethoxy]quinazolin-4-yl]piperazine-1-carboxamide Chemical compound COC1=CC2=C(N3CCN(CC3)C(=O)NC=3C=CC(=CC=3)C#N)N=CN=C2C=C1OCCC1=NN=NN1 FLWVPBCUGYXRMY-UHFFFAOYSA-N 0.000 description 1
- IIHNRXKTMNLPSH-UHFFFAOYSA-N n-[4-(1h-indol-4-yloxy)phenyl]-4-[6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yl]piperazine-1-carboxamide Chemical compound C=12C=C(OC)C(OCCOC)=CC2=NC=NC=1N(CC1)CCN1C(=O)NC(C=C1)=CC=C1OC1=CC=CC2=C1C=CN2 IIHNRXKTMNLPSH-UHFFFAOYSA-N 0.000 description 1
- JDPYFIGKIIQSSF-UHFFFAOYSA-N n-[4-(1h-indol-5-yloxy)phenyl]-4-[6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yl]piperazine-1-carboxamide Chemical compound C1=C2NC=CC2=CC(OC2=CC=C(C=C2)NC(=O)N2CCN(CC2)C=2N=CN=C3C=C(C(=CC3=2)OC)OCCOC)=C1 JDPYFIGKIIQSSF-UHFFFAOYSA-N 0.000 description 1
- 230000027405 negative regulation of phosphorylation Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 102000037979 non-receptor tyrosine kinases Human genes 0.000 description 1
- 108091008046 non-receptor tyrosine kinases Proteins 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical class N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 108091008598 receptor tyrosine kinases Proteins 0.000 description 1
- 102000027426 receptor tyrosine kinases Human genes 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- 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
- C07D401/14—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 three or more hetero rings
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
-
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22612200P | 2000-08-18 | 2000-08-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200301510B true ZA200301510B (en) | 2004-06-22 |
Family
ID=22847639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200301510A ZA200301510B (en) | 2000-08-18 | 2003-02-26 | Quinazoline derivatives as kinase inhibitors. |
Country Status (24)
| Country | Link |
|---|---|
| US (5) | US6982266B2 (cs) |
| EP (3) | EP2277877A1 (cs) |
| JP (1) | JP5073147B2 (cs) |
| KR (1) | KR100831116B1 (cs) |
| CN (1) | CN100358890C (cs) |
| AT (1) | ATE402169T1 (cs) |
| AU (1) | AU8544901A (cs) |
| BR (1) | BR0113356A (cs) |
| CA (1) | CA2426440C (cs) |
| CY (1) | CY1110460T1 (cs) |
| CZ (1) | CZ304061B6 (cs) |
| DE (1) | DE60134990D1 (cs) |
| DK (1) | DK1315715T3 (cs) |
| EA (1) | EA005809B1 (cs) |
| ES (1) | ES2311023T3 (cs) |
| HU (1) | HU228668B1 (cs) |
| IL (2) | IL154514A0 (cs) |
| MX (1) | MXPA03001359A (cs) |
| NO (1) | NO323782B1 (cs) |
| NZ (1) | NZ524461A (cs) |
| PT (1) | PT1315715E (cs) |
| SI (1) | SI1315715T1 (cs) |
| WO (1) | WO2002016351A1 (cs) |
| ZA (1) | ZA200301510B (cs) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002016362A2 (en) | 2000-08-18 | 2002-02-28 | Cor Therapeutics, Inc. | Nitrogenous heterocyclic compounds |
| EP1309568B1 (en) | 2000-08-18 | 2011-02-16 | Millennium Pharmaceuticals, Inc. | [(quinazolin-4-yl)piperazin-4-yl]thiocarboxamide compounds as inhibitors of the phosphorylation of a PDGF receptor |
| IL154514A0 (en) * | 2000-08-18 | 2003-09-17 | Millennium Pharm Inc | Quinazoline derivatives and pharmaceutical compositions containing the same |
| JP4564713B2 (ja) * | 2000-11-01 | 2010-10-20 | ミレニアム・ファーマシューティカルズ・インコーポレイテッド | 窒素性複素環式化合物、ならびに窒素性複素環式化合物およびその中間体を作製するための方法 |
| US6960580B2 (en) | 2001-03-08 | 2005-11-01 | Millennium Pharmaceuticals, Inc. | Nitrogenous heterocyclic substituted quinoline compounds |
| ATE302771T1 (de) | 2001-12-27 | 2005-09-15 | Theravance Inc | Indolinon-derivative als protein-kinasehemmer |
| AU2003256922A1 (en) * | 2002-07-31 | 2004-02-16 | Smithkline Beecham Corporation | Substituted heterocyclic compounds as modulators of the ccr5 receptor |
| EP1576129A4 (en) | 2002-08-09 | 2008-01-23 | Theravance Inc | ONCOKINASE FUSION POLYPEPTIDES ASSOCIATED WITH HYPERPROLIFERATIVE DISORDERS, NUCLEIC ACIDS ENCODING THESE POLYPEPTIDES AND METHODS OF DETECTION AND IDENTIFICATION THEREOF |
| DK1847539T3 (da) * | 2002-12-24 | 2009-11-09 | Astrazeneca Ab | Quinazolin-derivater |
| EP2277595A3 (en) | 2004-06-24 | 2011-09-28 | Novartis Vaccines and Diagnostics, Inc. | Compounds for immunopotentiation |
| US20070054916A1 (en) * | 2004-10-01 | 2007-03-08 | Amgen Inc. | Aryl nitrogen-containing bicyclic compounds and methods of use |
| CN101189239A (zh) * | 2005-04-28 | 2008-05-28 | 休普基因公司 | 蛋白激酶抑制剂 |
| CA2612459A1 (en) * | 2005-07-20 | 2007-01-25 | Millennium Pharmaceuticals, Inc. | New crystal forms of 4-[6-methoxy-7-(3-piperidin-1-yl-propoxy)quinazolin-4-yl]piperazine-1-carboxylic acid(4-isopropoxyphenyl)-amide |
| CA2643044A1 (en) * | 2006-02-28 | 2007-09-07 | Amgen Inc. | Cinnoline and quinazoline derivates as phosphodiesterase 10 inhibitors |
| UA95641C2 (xx) * | 2006-07-06 | 2011-08-25 | Эррей Биофарма Инк. | Гідроксильовані піримідильні циклопентани як інгібітори акт протеїнкінази$гидроксилированные пиримидильные циклопентаны как ингибиторы акт протеинкиназы |
| EP2077842A2 (en) * | 2006-10-31 | 2009-07-15 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Use of an egfr antagonist for the treatment of glomerolonephritis |
| JP5250901B2 (ja) * | 2007-02-23 | 2013-07-31 | 学校法人慶應義塾 | アニリノキナゾリン系化合物及びその用途 |
| JP2010523712A (ja) * | 2007-04-13 | 2010-07-15 | スーパージェン, インコーポレイテッド | 癌または過剰増殖の治療に有用なaxlキナーゼ阻害剤 |
| US20100273808A1 (en) * | 2008-11-21 | 2010-10-28 | Millennium Pharmaceticals, Inc. | Lactate salt of 4-[6-methoxy-7-(3-piperidin-1-yl-propoxy)quinazolin-4-yl]piperazine-1-carboxylic acid(4-isopropoxyphenyl)-amide and pharmaceutical compositions thereof for the treatment of cancer and other diseases or disorders |
| US9416132B2 (en) | 2011-07-21 | 2016-08-16 | Tolero Pharmaceuticals, Inc. | Substituted imidazo[1,2-b]pyridazines as protein kinase inhibitors |
| CN102942529B (zh) * | 2012-11-09 | 2015-06-24 | 贵州大学 | 4-(4-取代哌嗪)-5,6,7-三烷氧基喹唑啉类化合物及其制备方法和应用 |
| US9227978B2 (en) | 2013-03-15 | 2016-01-05 | Araxes Pharma Llc | Covalent inhibitors of Kras G12C |
| CN103288760B (zh) * | 2013-05-16 | 2015-02-18 | 苏州明锐医药科技有限公司 | 卡奈替尼的制备方法 |
| WO2015009889A1 (en) | 2013-07-18 | 2015-01-22 | Concert Pharmaceuticals, Inc. | Deuterated intedanib derivatives and their use for the treatment of proliferative disorders |
| JO3805B1 (ar) | 2013-10-10 | 2021-01-31 | Araxes Pharma Llc | مثبطات كراس جي12سي |
| JO3556B1 (ar) | 2014-09-18 | 2020-07-05 | Araxes Pharma Llc | علاجات مدمجة لمعالجة السرطان |
| AR102094A1 (es) | 2014-09-25 | 2017-02-01 | Araxes Pharma Llc | Inhibidores de proteínas kras con una mutación g12c |
| US10011600B2 (en) | 2014-09-25 | 2018-07-03 | Araxes Pharma Llc | Methods and compositions for inhibition of Ras |
| US10246424B2 (en) | 2015-04-10 | 2019-04-02 | Araxes Pharma Llc | Substituted quinazoline compounds and methods of use thereof |
| CA2982360A1 (en) | 2015-04-15 | 2016-10-20 | Liansheng Li | Fused-tricyclic inhibitors of kras and methods of use thereof |
| US10144724B2 (en) | 2015-07-22 | 2018-12-04 | Araxes Pharma Llc | Substituted quinazoline compounds and methods of use thereof |
| US10647703B2 (en) | 2015-09-28 | 2020-05-12 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
| US10689356B2 (en) | 2015-09-28 | 2020-06-23 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
| US10975071B2 (en) | 2015-09-28 | 2021-04-13 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
| EP3356354A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| WO2017058792A1 (en) | 2015-09-28 | 2017-04-06 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
| WO2017058728A1 (en) | 2015-09-28 | 2017-04-06 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
| EP3356347A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| WO2017070256A2 (en) | 2015-10-19 | 2017-04-27 | Araxes Pharma Llc | Method for screening inhibitors of ras |
| EP3377481A1 (en) | 2015-11-16 | 2018-09-26 | Araxes Pharma LLC | 2-substituted quinazoline compounds comprising a substituted heterocyclic group and methods of use thereof |
| WO2017100546A1 (en) | 2015-12-09 | 2017-06-15 | Araxes Pharma Llc | Methods for preparation of quinazoline derivatives |
| US10822312B2 (en) | 2016-03-30 | 2020-11-03 | Araxes Pharma Llc | Substituted quinazoline compounds and methods of use |
| CN106083715A (zh) * | 2016-06-01 | 2016-11-09 | 谢阳 | 一种喹啉、喹唑啉类化合物及其药物组合物和应用 |
| US10646488B2 (en) | 2016-07-13 | 2020-05-12 | Araxes Pharma Llc | Conjugates of cereblon binding compounds and G12C mutant KRAS, HRAS or NRAS protein modulating compounds and methods of use thereof |
| CN110036010A (zh) | 2016-09-29 | 2019-07-19 | 亚瑞克西斯制药公司 | Kras g12c突变蛋白的抑制剂 |
| US10377743B2 (en) | 2016-10-07 | 2019-08-13 | Araxes Pharma Llc | Inhibitors of RAS and methods of use thereof |
| US11279689B2 (en) | 2017-01-26 | 2022-03-22 | Araxes Pharma Llc | 1-(3-(6-(3-hydroxynaphthalen-1-yl)benzofuran-2-yl)azetidin-1 yl)prop-2-en-1-one derivatives and similar compounds as KRAS G12C modulators for treating cancer |
| WO2018140512A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | Fused bicyclic benzoheteroaromatic compounds and methods of use thereof |
| EP3573970A1 (en) | 2017-01-26 | 2019-12-04 | Araxes Pharma LLC | 1-(6-(3-hydroxynaphthalen-1-yl)quinazolin-2-yl)azetidin-1-yl)prop-2-en-1-one derivatives and similar compounds as kras g12c inhibitors for the treatment of cancer |
| WO2018140599A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | Benzothiophene and benzothiazole compounds and methods of use thereof |
| JP7327802B2 (ja) | 2017-01-26 | 2023-08-16 | アラクセス ファーマ エルエルシー | 縮合ヘテロ-ヘテロ二環式化合物およびその使用方法 |
| WO2018218069A1 (en) | 2017-05-25 | 2018-11-29 | Araxes Pharma Llc | Quinazoline derivatives as modulators of mutant kras, hras or nras |
| CN110869357A (zh) | 2017-05-25 | 2020-03-06 | 亚瑞克西斯制药公司 | 化合物及其用于治疗癌症的使用方法 |
| MX2019013954A (es) | 2017-05-25 | 2020-08-31 | Araxes Pharma Llc | Inhibidores covalentes de kras. |
| EP3773591A4 (en) | 2018-04-05 | 2021-12-22 | Sumitomo Dainippon Pharma Oncology, Inc. | AXL KINASE INHIBITORS AND THEIR USE |
| CN108570039B (zh) * | 2018-04-25 | 2022-09-23 | 上海美迪西生物医药股份有限公司 | 一类具有抑制抗凋亡蛋白活性的化合物及其制备和应用 |
| CA3107168A1 (en) | 2018-08-01 | 2020-02-06 | Araxes Pharma Llc | Heterocyclic spiro compounds and methods of use thereof for the treatment of cancer |
| CN113412262A (zh) | 2019-02-12 | 2021-09-17 | 大日本住友制药肿瘤公司 | 包含杂环蛋白激酶抑制剂的制剂 |
| CN114920704B (zh) * | 2019-07-26 | 2023-11-03 | 暨南大学 | 一种苯基哌嗪喹唑啉类化合物或其药学上可接受的盐、制法与用途 |
| CN111773440A (zh) * | 2020-05-22 | 2020-10-16 | 南京大学 | 一种基于类酶催化反应的抗凝血材料 |
| CA3237696A1 (en) | 2021-11-08 | 2023-05-11 | Progentos Therapeutics, Inc. | Platelet-derived growth factor receptor (pdgfr) alpha inhibitors and uses thereof |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0584222B1 (en) | 1991-05-10 | 1997-10-08 | Rhone-Poulenc Rorer International (Holdings) Inc. | Bis mono-and bicyclic aryl and heteroaryl compounds which inhibit egf and/or pdgf receptor tyrosine kinase |
| NZ243082A (en) | 1991-06-28 | 1995-02-24 | Ici Plc | 4-anilino-quinazoline derivatives; pharmaceutical compositions, preparatory processes, and use thereof |
| TW225528B (cs) | 1992-04-03 | 1994-06-21 | Ciba Geigy Ag | |
| GB9510757D0 (en) | 1994-09-19 | 1995-07-19 | Wellcome Found | Therapeuticaly active compounds |
| JP4073961B2 (ja) * | 1996-10-01 | 2008-04-09 | 協和醗酵工業株式会社 | 含窒素複素環化合物 |
| AU3053999A (en) * | 1998-03-31 | 1999-10-25 | Kyowa Hakko Kogyo Co. Ltd. | Nitrogenous heterocyclic compounds |
| IL154514A0 (en) * | 2000-08-18 | 2003-09-17 | Millennium Pharm Inc | Quinazoline derivatives and pharmaceutical compositions containing the same |
| WO2002016362A2 (en) | 2000-08-18 | 2002-02-28 | Cor Therapeutics, Inc. | Nitrogenous heterocyclic compounds |
| EP1309568B1 (en) | 2000-08-18 | 2011-02-16 | Millennium Pharmaceuticals, Inc. | [(quinazolin-4-yl)piperazin-4-yl]thiocarboxamide compounds as inhibitors of the phosphorylation of a PDGF receptor |
| EP1309567A2 (en) | 2000-08-18 | 2003-05-14 | Millennium Pharmaceuticals, Inc. | Nitrogenous heterocyclic compounds |
| US6960580B2 (en) | 2001-03-08 | 2005-11-01 | Millennium Pharmaceuticals, Inc. | Nitrogenous heterocyclic substituted quinoline compounds |
| EP1408980A4 (en) * | 2001-06-21 | 2004-10-20 | Ariad Pharma Inc | NEW QUINAZOLINES AND THEIR USE |
| US7456189B2 (en) * | 2003-09-30 | 2008-11-25 | Boehringer Ingelheim International Gmbh | Bicyclic heterocycles, medicaments containing these compounds, their use and processes for their preparation |
-
2001
- 2001-08-17 IL IL15451401A patent/IL154514A0/xx active IP Right Grant
- 2001-08-17 NZ NZ52446101A patent/NZ524461A/xx not_active IP Right Cessation
- 2001-08-17 EP EP10182322A patent/EP2277877A1/en not_active Withdrawn
- 2001-08-17 EA EA200300265A patent/EA005809B1/ru not_active IP Right Cessation
- 2001-08-17 HU HU0302615A patent/HU228668B1/hu not_active IP Right Cessation
- 2001-08-17 EP EP01964612A patent/EP1315715B1/en not_active Expired - Lifetime
- 2001-08-17 ES ES01964612T patent/ES2311023T3/es not_active Expired - Lifetime
- 2001-08-17 WO PCT/US2001/041752 patent/WO2002016351A1/en active IP Right Grant
- 2001-08-17 EP EP08075237A patent/EP1964839A3/en not_active Ceased
- 2001-08-17 SI SI200130872T patent/SI1315715T1/sl unknown
- 2001-08-17 BR BR0113356-0A patent/BR0113356A/pt active Search and Examination
- 2001-08-17 MX MXPA03001359A patent/MXPA03001359A/es active IP Right Grant
- 2001-08-17 DE DE60134990T patent/DE60134990D1/de not_active Expired - Lifetime
- 2001-08-17 AU AU8544901A patent/AU8544901A/xx active Pending
- 2001-08-17 US US10/344,736 patent/US6982266B2/en not_active Expired - Fee Related
- 2001-08-17 PT PT01964612T patent/PT1315715E/pt unknown
- 2001-08-17 JP JP2002521452A patent/JP5073147B2/ja not_active Expired - Fee Related
- 2001-08-17 CA CA2426440A patent/CA2426440C/en not_active Expired - Fee Related
- 2001-08-17 KR KR1020037002381A patent/KR100831116B1/ko not_active Expired - Fee Related
- 2001-08-17 DK DK01964612T patent/DK1315715T3/da active
- 2001-08-17 AT AT01964612T patent/ATE402169T1/de active
- 2001-08-17 CN CNB018173527A patent/CN100358890C/zh not_active Expired - Fee Related
- 2001-08-17 CZ CZ20030765A patent/CZ304061B6/cs not_active IP Right Cessation
-
2003
- 2003-02-17 NO NO20030747A patent/NO323782B1/no not_active IP Right Cessation
- 2003-02-18 IL IL154514A patent/IL154514A/en not_active IP Right Cessation
- 2003-02-26 ZA ZA200301510A patent/ZA200301510B/en unknown
-
2005
- 2005-08-22 US US11/210,028 patent/US7560461B2/en not_active Expired - Fee Related
-
2008
- 2008-10-21 CY CY20081101177T patent/CY1110460T1/el unknown
-
2009
- 2009-05-22 US US12/471,280 patent/US8324205B2/en not_active Expired - Fee Related
-
2012
- 2012-11-02 US US13/667,489 patent/US20130274252A1/en not_active Abandoned
-
2014
- 2014-07-09 US US14/327,312 patent/US20150133439A1/en not_active Abandoned
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200301510B (en) | Quinazoline derivatives as kinase inhibitors. | |
| ZA200500322B (en) | INdole of benzimidazole derivatives for modulating kB kinase | |
| EP1309569B1 (en) | N-aryl-{4-[7-(alkoxy)quinazolin-4-yl]piperazinyl}carboxamide derivatives as PDGFRs inhibitors | |
| EP1309567A2 (en) | Nitrogenous heterocyclic compounds | |
| EP1309568B1 (en) | [(quinazolin-4-yl)piperazin-4-yl]thiocarboxamide compounds as inhibitors of the phosphorylation of a PDGF receptor | |
| AU2001285449B8 (en) | Quinazoline derivatives as kinase inhibitors | |
| AU2001285449A1 (en) | Quinazoline derivatives as kinase inhibitors | |
| US20040259881A1 (en) | Nitrogenous heterocyclic compounds | |
| HK1124316A (en) | Quinazoline derivatives as kinase inhibitors | |
| HK1057206B (en) | Quinazoline derivatives as kinase inhibitors | |
| KR20050073238A (ko) | 몰폴린기가 치환된 퀴나졸린 유도체 |