HRP960465A2 - Heterocyclic compounds - Google Patents
Heterocyclic compounds Download PDFInfo
- Publication number
- HRP960465A2 HRP960465A2 HR9614757.4A HRP960465A HRP960465A2 HR P960465 A2 HRP960465 A2 HR P960465A2 HR P960465 A HRP960465 A HR P960465A HR P960465 A2 HRP960465 A2 HR P960465A2
- Authority
- HR
- Croatia
- Prior art keywords
- pyrimidine
- alkyl
- pyrido
- alkoxy
- compound
- Prior art date
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- 150000002391 heterocyclic compounds Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 125
- 238000000034 method Methods 0.000 claims description 85
- -1 trifluoromethoxy, nitro, amino Chemical group 0.000 claims description 62
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 39
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 28
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 238000011282 treatment Methods 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 125000003282 alkyl amino group Chemical group 0.000 claims description 22
- 230000000694 effects Effects 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 19
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000002837 carbocyclic group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
- 230000001594 aberrant effect Effects 0.000 claims description 10
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- QXOVLZVIYMRNAV-UHFFFAOYSA-N 6-chloro-n-(4-phenylmethoxyphenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2C=NC(Cl)=CC2=C1NC(C=C1)=CC=C1OCC1=CC=CC=C1 QXOVLZVIYMRNAV-UHFFFAOYSA-N 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 125000004989 dicarbonyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- WXTYHXBDAUYJQS-UHFFFAOYSA-N n-[4-(benzenesulfonyl)phenyl]-6-chloropyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2C=NC(Cl)=CC2=C1NC(C=C1)=CC=C1S(=O)(=O)C1=CC=CC=C1 WXTYHXBDAUYJQS-UHFFFAOYSA-N 0.000 claims description 6
- DOKKMZLPMGLGJX-UHFFFAOYSA-N 6-(3-methylimidazol-4-yl)-n-(4-phenylmethoxyphenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound CN1C=NC=C1C(N=CC1=NC=N2)=CC1=C2NC(C=C1)=CC=C1OCC1=CC=CC=C1 DOKKMZLPMGLGJX-UHFFFAOYSA-N 0.000 claims description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- BQNICBAZEPWTNW-UHFFFAOYSA-N 4-n-[4-(1,3-dioxolan-2-ylmethoxy)phenyl]-6-n,6-n-dimethylpyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1)=CC=C1OCC1OCCO1 BQNICBAZEPWTNW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- JAKTZPDFCZIXQM-UHFFFAOYSA-N 6-n,6-n-dimethyl-4-n-(4-phenylmethoxyphenyl)pyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1)=CC=C1OCC1=CC=CC=C1 JAKTZPDFCZIXQM-UHFFFAOYSA-N 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- YTKICSVFCXOIJB-UHFFFAOYSA-N n-(4-phenylmethoxyphenyl)-6-thiomorpholin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound C=1C=CC=CC=1COC(C=C1)=CC=C1NC(C1=C2)=NC=NC1=CN=C2N1CCSCC1 YTKICSVFCXOIJB-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- PAQYIEZTLSDLQO-UHFFFAOYSA-N pyrido[3,4-d]pyrimidine Chemical compound N1=CN=C2C=NC=CC2=C1 PAQYIEZTLSDLQO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 208000037803 restenosis Diseases 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- NGGKKVSEPYCGNW-UHFFFAOYSA-N 2-[[4-[4-(benzenesulfonyl)anilino]pyrido[3,4-d]pyrimidin-6-yl]-methylamino]ethanol Chemical compound N1=CN=C2C=NC(N(CCO)C)=CC2=C1NC(C=C1)=CC=C1S(=O)(=O)C1=CC=CC=C1 NGGKKVSEPYCGNW-UHFFFAOYSA-N 0.000 claims description 3
- XXKCPVIIXOPXEP-UHFFFAOYSA-N 4-n-[4-(benzenesulfonyl)phenyl]-6-n,6-n-dimethylpyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1)=CC=C1S(=O)(=O)C1=CC=CC=C1 XXKCPVIIXOPXEP-UHFFFAOYSA-N 0.000 claims description 3
- UPIYTHRGZLPZQS-UHFFFAOYSA-N 5-[4-(4-phenylmethoxyanilino)pyrido[3,4-d]pyrimidin-6-yl]furan-2-carbaldehyde Chemical compound O1C(C=O)=CC=C1C(N=CC1=NC=N2)=CC1=C2NC(C=C1)=CC=C1OCC1=CC=CC=C1 UPIYTHRGZLPZQS-UHFFFAOYSA-N 0.000 claims description 3
- DNAQHZRAPBUFQJ-UHFFFAOYSA-N 6-(1-methylimidazol-2-yl)-n-(4-phenylmethoxyphenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound CN1C=CN=C1C(N=CC1=NC=N2)=CC1=C2NC(C=C1)=CC=C1OCC1=CC=CC=C1 DNAQHZRAPBUFQJ-UHFFFAOYSA-N 0.000 claims description 3
- LZQOJWXKGWWUSQ-UHFFFAOYSA-N 6-(furan-2-yl)-n-(4-phenylmethoxyphenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound C=1C=CC=CC=1COC(C=C1)=CC=C1NC(C1=C2)=NC=NC1=CN=C2C1=CC=CO1 LZQOJWXKGWWUSQ-UHFFFAOYSA-N 0.000 claims description 3
- GXFDHJDKDGVBRU-UHFFFAOYSA-N 6-chloro-n-[4-(1,3-dioxolan-2-ylmethoxy)phenyl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2C=NC(Cl)=CC2=C1NC(C=C1)=CC=C1OCC1OCCO1 GXFDHJDKDGVBRU-UHFFFAOYSA-N 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 208000007536 Thrombosis Diseases 0.000 claims description 3
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 150000007942 carboxylates Chemical class 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- YQQXWIQTZVBINC-UHFFFAOYSA-N n-[4-(benzenesulfonyl)phenyl]-6-(4-methylpiperazin-1-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C(N=CC1=NC=N2)=CC1=C2NC1=CC=C(S(=O)(=O)C=2C=CC=CC=2)C=C1 YQQXWIQTZVBINC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 229930192474 thiophene Chemical group 0.000 claims description 3
- 229910052721 tungsten Inorganic materials 0.000 claims description 3
- TYOJYLRMQHRNOX-UHFFFAOYSA-N 2-[4-[[6-(dimethylamino)pyrido[3,4-d]pyrimidin-4-yl]amino]phenyl]-2-phenylacetonitrile Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1)=CC=C1C(C#N)C1=CC=CC=C1 TYOJYLRMQHRNOX-UHFFFAOYSA-N 0.000 claims description 2
- ZMCMFEUHXKDHQG-UHFFFAOYSA-N 4-n-[4-(benzenesulfonyl)phenyl]-6-n-[2-(dimethylamino)ethyl]-6-n-methylpyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)CCN(C)C)=CC2=C1NC(C=C1)=CC=C1S(=O)(=O)C1=CC=CC=C1 ZMCMFEUHXKDHQG-UHFFFAOYSA-N 0.000 claims description 2
- IQJVEWGFUVNHPS-UHFFFAOYSA-N 4-n-[4-[(3-fluorophenyl)methoxy]phenyl]-6-n,6-n-dimethylpyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1)=CC=C1OCC1=CC=CC(F)=C1 IQJVEWGFUVNHPS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
- ZUCRFFRRDPTULV-UHFFFAOYSA-N 6-(4-methylpiperazin-1-yl)-n-(4-phenylmethoxyphenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C(N=CC1=NC=N2)=CC1=C2NC(C=C1)=CC=C1OCC1=CC=CC=C1 ZUCRFFRRDPTULV-UHFFFAOYSA-N 0.000 claims description 2
- BRJBLARSOFKJME-UHFFFAOYSA-N 6-chloro-n-(4-phenylsulfanylphenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2C=NC(Cl)=CC2=C1NC(C=C1)=CC=C1SC1=CC=CC=C1 BRJBLARSOFKJME-UHFFFAOYSA-N 0.000 claims description 2
- HCFTYUFPNVXOJF-UHFFFAOYSA-N 6-phenylmethoxy-n-(4-phenylmethoxyphenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound C=1C=CC=CC=1COC(C=C1)=CC=C1NC(C1=C2)=NC=NC1=CN=C2OCC1=CC=CC=C1 HCFTYUFPNVXOJF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- MJQAMWVEPJHQQZ-UHFFFAOYSA-N n-(4-phenylmethoxyphenyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound C=1C=C(NC=2C3=CC=CN=C3N=CN=2)C=CC=1OCC1=CC=CC=C1 MJQAMWVEPJHQQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- 125000005554 pyridyloxy group Chemical group 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 3
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 2
- HGVWHDUJXWPIFH-UHFFFAOYSA-N 4-n-(3-chloro-4-phenylmethoxyphenyl)-6-n,6-n-dimethylpyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=C1 HGVWHDUJXWPIFH-UHFFFAOYSA-N 0.000 claims 1
- DVOJKAZVHWAKET-UHFFFAOYSA-N 7-methyl-n-(4-phenoxyphenyl)thieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=CSC2=C1NC(C=C1)=CC=C1OC1=CC=CC=C1 DVOJKAZVHWAKET-UHFFFAOYSA-N 0.000 claims 1
- QCNWIOGBGNQTAN-UHFFFAOYSA-N 7-methyl-n-[4-phenylmethoxy-3-(trifluoromethyl)phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=CSC2=C1NC(C=C1C(F)(F)F)=CC=C1OCC1=CC=CC=C1 QCNWIOGBGNQTAN-UHFFFAOYSA-N 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- GWELHWZVDHWXOD-UHFFFAOYSA-N n-(4-benzylphenyl)thieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C(NC=2C=3SC=CC=3N=CN=2)C=CC=1CC1=CC=CC=C1 GWELHWZVDHWXOD-UHFFFAOYSA-N 0.000 claims 1
- MLGCIGKABIXNCH-UHFFFAOYSA-N n-(4-phenoxyphenyl)-5-thiophen-2-ylthieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C=NC=2SC=C(C=3SC=CC=3)C=2C=1NC(C=C1)=CC=C1OC1=CC=CC=C1 MLGCIGKABIXNCH-UHFFFAOYSA-N 0.000 claims 1
- ZSWUAMCGOVXUQL-UHFFFAOYSA-N n-(4-phenoxyphenyl)thieno[3,2-d]pyrimidin-4-amine Chemical compound N=1C=NC=2C=CSC=2C=1NC(C=C1)=CC=C1OC1=CC=CC=C1 ZSWUAMCGOVXUQL-UHFFFAOYSA-N 0.000 claims 1
- FZALGTPXQZDQND-UHFFFAOYSA-N n-(4-phenylmethoxyphenyl)thieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C(NC=2C=3SC=CC=3N=CN=2)C=CC=1OCC1=CC=CC=C1 FZALGTPXQZDQND-UHFFFAOYSA-N 0.000 claims 1
- LJILSPYXOKMTGZ-UHFFFAOYSA-N n-[3-chloro-4-[(2-fluorophenyl)methoxy]phenyl]-5-methylthieno[2,3-d]pyrimidin-4-amine Chemical compound C=12C(C)=CSC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=C1F LJILSPYXOKMTGZ-UHFFFAOYSA-N 0.000 claims 1
- KKGIBJKTQQCUSF-UHFFFAOYSA-N n-[3-chloro-4-[(2-fluorophenyl)methoxy]phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound FC1=CC=CC=C1COC(C(=C1)Cl)=CC=C1NC1=NC=NC2=C1SC=C2 KKGIBJKTQQCUSF-UHFFFAOYSA-N 0.000 claims 1
- FIEPNGQUUSUAPN-UHFFFAOYSA-N n-[3-chloro-4-[(2-methoxyphenyl)methoxy]phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound COC1=CC=CC=C1COC(C(=C1)Cl)=CC=C1NC1=NC=NC2=C1SC=C2 FIEPNGQUUSUAPN-UHFFFAOYSA-N 0.000 claims 1
- FMHSSZBRISKOBK-UHFFFAOYSA-N n-[3-methoxy-4-[(2-methoxyphenyl)methoxy]phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound COC1=CC=CC=C1COC(C(=C1)OC)=CC=C1NC1=NC=NC2=C1SC=C2 FMHSSZBRISKOBK-UHFFFAOYSA-N 0.000 claims 1
- PRRAODUKSVKQQJ-UHFFFAOYSA-N n-[4-(cyclohexylmethoxy)phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C(NC=2C=3SC=CC=3N=CN=2)C=CC=1OCC1CCCCC1 PRRAODUKSVKQQJ-UHFFFAOYSA-N 0.000 claims 1
- MFQDINXHDBLVFM-UHFFFAOYSA-N n-[4-(thiophen-2-ylmethoxy)phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C(NC=2C=3SC=CC=3N=CN=2)C=CC=1OCC1=CC=CS1 MFQDINXHDBLVFM-UHFFFAOYSA-N 0.000 claims 1
- JOXKCVILYFDEMM-UHFFFAOYSA-N n-[4-[(2-bromophenyl)methoxy]-3-chlorophenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound ClC1=CC(NC=2C=3SC=CC=3N=CN=2)=CC=C1OCC1=CC=CC=C1Br JOXKCVILYFDEMM-UHFFFAOYSA-N 0.000 claims 1
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 claims 1
- 125000005505 thiomorpholino group Chemical group 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 59
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 47
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 34
- 239000000047 product Substances 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
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- VLVBWLMDBNOBMM-UHFFFAOYSA-N n-(4-phenoxyphenyl)-5-thiophen-2-ylthieno[2,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.N=1C=NC=2SC=C(C=3SC=CC=3)C=2C=1NC(C=C1)=CC=C1OC1=CC=CC=C1 VLVBWLMDBNOBMM-UHFFFAOYSA-N 0.000 description 1
- ROXSUURCAZHEPB-UHFFFAOYSA-N n-(4-phenoxyphenyl)thieno[3,2-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.N=1C=NC=2C=CSC=2C=1NC(C=C1)=CC=C1OC1=CC=CC=C1 ROXSUURCAZHEPB-UHFFFAOYSA-N 0.000 description 1
- RVPKUUULOAKIRM-UHFFFAOYSA-N n-[3-chloro-4-[(2-fluorophenyl)methoxy]phenyl]-5-methylthieno[2,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C=12C(C)=CSC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=C1F RVPKUUULOAKIRM-UHFFFAOYSA-N 0.000 description 1
- XKKIPRNFABKBDW-UHFFFAOYSA-N n-[3-chloro-4-[(2-fluorophenyl)methoxy]phenyl]thieno[3,2-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.FC1=CC=CC=C1COC(C(=C1)Cl)=CC=C1NC1=NC=NC2=C1SC=C2 XKKIPRNFABKBDW-UHFFFAOYSA-N 0.000 description 1
- TXEVAORXZXOVAP-UHFFFAOYSA-N n-[3-chloro-4-[(2-methoxyphenyl)methoxy]phenyl]thieno[3,2-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.COC1=CC=CC=C1COC(C(=C1)Cl)=CC=C1NC1=NC=NC2=C1SC=C2 TXEVAORXZXOVAP-UHFFFAOYSA-N 0.000 description 1
- QAXVWZBEQAHKRO-UHFFFAOYSA-N n-[3-methoxy-4-[(2-methoxyphenyl)methoxy]phenyl]thieno[3,2-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.COC1=CC=CC=C1COC(C(=C1)OC)=CC=C1NC1=NC=NC2=C1SC=C2 QAXVWZBEQAHKRO-UHFFFAOYSA-N 0.000 description 1
- QZHRWYONEKRKIV-UHFFFAOYSA-N n-[4-(cyclohexylmethoxy)phenyl]-5-methylthieno[2,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C=12C(C)=CSC2=NC=NC=1NC(C=C1)=CC=C1OCC1CCCCC1 QZHRWYONEKRKIV-UHFFFAOYSA-N 0.000 description 1
- VCHIWKNEEJOWDH-UHFFFAOYSA-N n-[4-(cyclohexylmethoxy)phenyl]thieno[3,2-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C=1C=C(NC=2C=3SC=CC=3N=CN=2)C=CC=1OCC1CCCCC1 VCHIWKNEEJOWDH-UHFFFAOYSA-N 0.000 description 1
- XOEBIPHQEASZSY-UHFFFAOYSA-N n-[4-(thiophen-2-ylmethoxy)phenyl]thieno[3,2-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C=1C=C(NC=2C=3SC=CC=3N=CN=2)C=CC=1OCC1=CC=CS1 XOEBIPHQEASZSY-UHFFFAOYSA-N 0.000 description 1
- NHQXBUYAPLBXDL-UHFFFAOYSA-N n-[4-[(2-bromophenyl)methoxy]-3-chlorophenyl]thieno[3,2-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.ClC1=CC(NC=2C=3SC=CC=3N=CN=2)=CC=C1OCC1=CC=CC=C1Br NHQXBUYAPLBXDL-UHFFFAOYSA-N 0.000 description 1
- QRLOPDIVUDLFSZ-UHFFFAOYSA-N n-benzylpyrimidin-4-amine Chemical class C=1C=CC=CC=1CNC1=CC=NC=N1 QRLOPDIVUDLFSZ-UHFFFAOYSA-N 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000011369 optimal treatment Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- RKOZEGQZEADBAT-UHFFFAOYSA-N pyrido[3,4-d]pyrimidine hydrochloride Chemical compound Cl.N1=CN=C2C=NC=CC2=C1 RKOZEGQZEADBAT-UHFFFAOYSA-N 0.000 description 1
- IDXKTTNFXPPXJY-UHFFFAOYSA-N pyrimidin-1-ium;chloride Chemical compound Cl.C1=CN=CN=C1 IDXKTTNFXPPXJY-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000009703 regulation of cell differentiation Effects 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- LSJNBGSOIVSBBR-UHFFFAOYSA-N thionyl fluoride Chemical compound FS(F)=O LSJNBGSOIVSBBR-UHFFFAOYSA-N 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 229940100615 topical ointment Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- SANWDQJIWZEKOD-UHFFFAOYSA-N tributyl(furan-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CO1 SANWDQJIWZEKOD-UHFFFAOYSA-N 0.000 description 1
- CUTVPKSVLXXPII-UHFFFAOYSA-N tributyl-(1-methyl-3h-pyrazol-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)N1CC=CN1C CUTVPKSVLXXPII-UHFFFAOYSA-N 0.000 description 1
- KFWFYOPKNSYTMV-UHFFFAOYSA-N tributyl-(1-methylimidazol-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=NC=CN1C KFWFYOPKNSYTMV-UHFFFAOYSA-N 0.000 description 1
- OGYWKJKAIAEDQX-UHFFFAOYSA-N tributyl-(3-methylimidazol-4-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CN=CN1C OGYWKJKAIAEDQX-UHFFFAOYSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
- 231100000588 tumorigenic Toxicity 0.000 description 1
- 230000000381 tumorigenic effect Effects 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/10—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
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9520845.0A GB9520845D0 (en) | 1995-10-11 | 1995-10-11 | Therapeutically active compounds |
GBGB9614757.4A GB9614757D0 (en) | 1996-07-13 | 1996-07-13 | Therapeutically active compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP960465A2 true HRP960465A2 (en) | 1998-02-28 |
Family
ID=26307933
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR9614757.4A HRP960465A2 (en) | 1995-10-11 | 1996-10-10 | Heterocyclic compounds |
Country Status (8)
Country | Link |
---|---|
US (1) | US6169091B1 (fr) |
EP (1) | EP0861253A1 (fr) |
JP (1) | JPH11513398A (fr) |
AR (1) | AR004010A1 (fr) |
AU (1) | AU7289696A (fr) |
HR (1) | HRP960465A2 (fr) |
ID (1) | ID16345A (fr) |
WO (1) | WO1997013771A1 (fr) |
Families Citing this family (242)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7772432B2 (en) | 1991-09-19 | 2010-08-10 | Astrazeneca Ab | Amidobenzamide derivatives which are useful as cytokine inhibitors |
TW321649B (fr) * | 1994-11-12 | 1997-12-01 | Zeneca Ltd | |
GB9424233D0 (en) * | 1994-11-30 | 1995-01-18 | Zeneca Ltd | Quinazoline derivatives |
GB9508565D0 (en) * | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quiazoline derivative |
GB9508537D0 (en) * | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
EP0824525B1 (fr) * | 1995-04-27 | 2001-06-13 | AstraZeneca AB | Derives de quinazoline |
GB9508538D0 (en) * | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
GB9508535D0 (en) * | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivative |
GB9624482D0 (en) * | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
KR19990082463A (ko) | 1996-02-13 | 1999-11-25 | 돈 리사 로얄 | 혈관 내피 성장 인자 억제제로서의 퀴나졸린유도체 |
GB9603097D0 (en) * | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline compounds |
DK0885198T3 (da) | 1996-03-05 | 2002-03-25 | Astrazeneca Ab | 4-Anilinoquinazolinderivater |
EP0892789B2 (fr) | 1996-04-12 | 2009-11-18 | Warner-Lambert Company LLC | Inhibiteurs irreversibles de tyrosine kinases |
GB9607729D0 (en) * | 1996-04-13 | 1996-06-19 | Zeneca Ltd | Quinazoline derivatives |
DE69718472T2 (de) * | 1996-07-13 | 2003-11-06 | Glaxo Group Ltd | Bicyclische heteroaromatische verbindungen als protein tyrosine kinase inhibitoren |
HRP970371A2 (en) | 1996-07-13 | 1998-08-31 | Kathryn Jane Smith | Heterocyclic compounds |
US7863444B2 (en) | 1997-03-19 | 2011-01-04 | Abbott Laboratories | 4-aminopyrrolopyrimidines as kinase inhibitors |
EP1028964A1 (fr) | 1997-11-11 | 2000-08-23 | Pfizer Products Inc. | Derives de thienopyrimidine et thienopyridine utiles comme agents anticancereux |
AU2002301080B2 (en) * | 1997-11-11 | 2005-04-28 | Pfizer Products Inc. | Thienopyrimidine and Thienopyridine Derivatives Useful as Anticancer Agents |
JPH11236333A (ja) * | 1997-12-30 | 1999-08-31 | Pfizer Prod Inc | 抗ガン剤として有用なイミダゾリン−4−オン誘導体 |
GB9800575D0 (en) * | 1998-01-12 | 1998-03-11 | Glaxo Group Ltd | Heterocyclic compounds |
GB9800569D0 (en) * | 1998-01-12 | 1998-03-11 | Glaxo Group Ltd | Heterocyclic compounds |
DE19802377A1 (de) * | 1998-01-22 | 1999-08-19 | Max Planck Gesellschaft | Verwendung von Inhibitoren für die Behandlung von RTK-Überfunktions-bedingten Störungen, insbesondere von Krebs |
DE69943144D1 (de) | 1998-03-31 | 2011-03-03 | Kyowa Hakko Kirin Co Ltd | Stickstoffenthaltende heterocyclische verbindungen |
US6706721B1 (en) * | 1998-04-29 | 2004-03-16 | Osi Pharmaceuticals, Inc. | N-(3-ethynylphenylamino)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine mesylate anhydrate and monohydrate |
WO1999059959A1 (fr) | 1998-05-15 | 1999-11-25 | Astrazeneca Ab | Derives de benzamide pour le traitement de maladies dont la mediation est assuree par les cytokines |
PA8474101A1 (es) | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
CZ20004727A3 (cs) | 1998-06-19 | 2002-03-13 | Pfizer Products Inc. | Deriváty pyrrolo[2,3-d] pyrimidinu |
US6713474B2 (en) | 1998-09-18 | 2004-03-30 | Abbott Gmbh & Co. Kg | Pyrrolopyrimidines as therapeutic agents |
DK1115707T3 (da) | 1998-09-25 | 2004-03-01 | Astrazeneca Ab | Benzamidderivater og deres anvendelse som cytokininhibitorer |
NZ510210A (en) | 1998-10-01 | 2003-06-30 | Astrazeneca Ab | 4-phenylamino substituted quinazoline or quinoline derivatives useful for treating cytokine mediated diseases or conditions |
US6174903B1 (en) | 1998-12-28 | 2001-01-16 | Pfizer Inc. | Imidazolidin-4-one derivatives useful as anticancer agents |
EP1396489A1 (fr) * | 1999-01-27 | 2004-03-10 | Pfizer Products Inc. | Composés hétéroaromatiques bicycliques a activité anticancereuse |
UA71945C2 (en) * | 1999-01-27 | 2005-01-17 | Pfizer Prod Inc | Substituted bicyclic derivatives being used as anticancer agents |
DE60010448T2 (de) | 1999-03-17 | 2005-04-07 | Astrazeneca Ab | Amid-derivate |
GB9906566D0 (en) * | 1999-03-23 | 1999-05-19 | Zeneca Ltd | Chemical compounds |
US6933299B1 (en) | 1999-07-09 | 2005-08-23 | Smithkline Beecham Corporation | Anilinoquinazolines as protein tyrosine kinase inhibitors |
WO2001004111A1 (fr) | 1999-07-09 | 2001-01-18 | Glaxo Group Limited | Anilino-quinazolines comme inhibiteurs de la proteine tyrosine kinase |
CN1390219A (zh) | 1999-09-17 | 2003-01-08 | 艾博特股份有限两合公司 | 作为治疗剂的吡唑并嘧啶类 |
US7071199B1 (en) | 1999-09-17 | 2006-07-04 | Abbott Gmbh & Cco. Kg | Kinase inhibitors as therapeutic agents |
UA72946C2 (uk) | 1999-11-05 | 2005-05-16 | Астразенека Аб | Похідні хіназоліну як інгібітори васкулярного ендотеліального фактора росту (vegf) |
US7087613B2 (en) * | 1999-11-11 | 2006-08-08 | Osi Pharmaceuticals, Inc. | Treating abnormal cell growth with a stable polymorph of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine hydrochloride |
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EP0222839A4 (fr) | 1985-05-17 | 1988-11-09 | Univ Australian | Composes antipaludiques. |
US5141941A (en) | 1988-11-21 | 1992-08-25 | Ube Industries, Ltd. | Aralkylamine derivatives, and fungicides containing the same |
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CA2039411A1 (fr) | 1990-03-30 | 1991-10-01 | Ronnie Gerald Edie | Derives de la thienopyrimidine |
DE4131924A1 (de) | 1991-09-25 | 1993-07-08 | Hoechst Ag | Substituierte 4-alkoxypyrimidine, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
GB9127252D0 (en) | 1991-12-23 | 1992-02-19 | Boots Co Plc | Therapeutic agents |
WO1993017682A1 (fr) | 1992-03-04 | 1993-09-16 | Abbott Laboratories | Antagonistes des recepteurs de l'angiotensine ii |
WO1993018035A1 (fr) | 1992-03-04 | 1993-09-16 | Abbott Laboratories | Antagonistes des recepteurs de l'angiotensine ii |
US5326766A (en) | 1992-08-19 | 1994-07-05 | Dreikorn Barry A | 4-(2-(4-(2-pyridinyloxy)phenyl)ethoxy)quinazoline and analogues thereof |
DE4308014A1 (de) * | 1993-03-13 | 1994-09-15 | Hoechst Schering Agrevo Gmbh | Kondensierte Stickstoffheterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel und Fungizide |
DE4308104A1 (de) | 1993-03-15 | 1994-09-22 | Daniel Spitzer | Vorrichtung zum Gewindeschneiden |
GB9312891D0 (en) | 1993-06-22 | 1993-08-04 | Boots Co Plc | Therapeutic agents |
IL112249A (en) * | 1994-01-25 | 2001-11-25 | Warner Lambert Co | Pharmaceutical compositions containing di and tricyclic pyrimidine derivatives for inhibiting tyrosine kinases of the epidermal growth factor receptor family and some new such compounds |
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1996
- 1996-09-10 AR ARP960104659A patent/AR004010A1/es unknown
- 1996-10-10 ID IDP962893A patent/ID16345A/id unknown
- 1996-10-10 US US09/051,324 patent/US6169091B1/en not_active Expired - Fee Related
- 1996-10-10 HR HR9614757.4A patent/HRP960465A2/hr not_active Application Discontinuation
- 1996-10-10 AU AU72896/96A patent/AU7289696A/en not_active Abandoned
- 1996-10-10 JP JP9514711A patent/JPH11513398A/ja active Pending
- 1996-10-10 EP EP96934612A patent/EP0861253A1/fr not_active Withdrawn
- 1996-10-10 WO PCT/EP1996/004399 patent/WO1997013771A1/fr not_active Application Discontinuation
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ID16345A (id) | 1997-09-25 |
AR004010A1 (es) | 1998-09-30 |
US6169091B1 (en) | 2001-01-02 |
EP0861253A1 (fr) | 1998-09-02 |
JPH11513398A (ja) | 1999-11-16 |
AU7289696A (en) | 1997-04-30 |
WO1997013771A1 (fr) | 1997-04-17 |
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