RU2378268C2 - Производные хиназолина в качестве ингибиторов тирозинкиназы - Google Patents
Производные хиназолина в качестве ингибиторов тирозинкиназы Download PDFInfo
- Publication number
- RU2378268C2 RU2378268C2 RU2006112599/04A RU2006112599A RU2378268C2 RU 2378268 C2 RU2378268 C2 RU 2378268C2 RU 2006112599/04 A RU2006112599/04 A RU 2006112599/04A RU 2006112599 A RU2006112599 A RU 2006112599A RU 2378268 C2 RU2378268 C2 RU 2378268C2
- Authority
- RU
- Russia
- Prior art keywords
- formula
- pharmaceutically acceptable
- piperidin
- oxy
- chloro
- Prior art date
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- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title abstract 2
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title abstract 2
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 title abstract 2
- 239000005483 tyrosine kinase inhibitor Substances 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 35
- 150000002148 esters Chemical class 0.000 claims abstract 27
- -1 hydroxy, amino Chemical group 0.000 claims abstract 16
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract 6
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 3
- 239000000460 chlorine Substances 0.000 claims abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052794 bromium Inorganic materials 0.000 claims abstract 2
- 201000011510 cancer Diseases 0.000 claims abstract 2
- 201000010099 disease Diseases 0.000 claims abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 2
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 2
- 239000011737 fluorine Substances 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
- 230000002062 proliferating effect Effects 0.000 claims abstract 2
- 150000003246 quinazolines Chemical class 0.000 claims 43
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000000524 functional group Chemical group 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 229910052740 iodine Inorganic materials 0.000 claims 5
- 125000006239 protecting group Chemical group 0.000 claims 5
- 230000015572 biosynthetic process Effects 0.000 claims 4
- HKPQKTRFULBKRH-ZDUSSCGKSA-N (2s)-1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-hydroxypropan-1-one Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)[C@H](C)O)C(OC)=CC2=C1NC1=CC=CC(Cl)=C1F HKPQKTRFULBKRH-ZDUSSCGKSA-N 0.000 claims 3
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims 3
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims 3
- HVAFDEWTWXYBEI-UHFFFAOYSA-N 1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-hydroxyethanone Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)CO)C(OC)=CC2=C1NC1=CC=CC(Cl)=C1F HVAFDEWTWXYBEI-UHFFFAOYSA-N 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 3
- HAKPDIYCVPGVFD-CYBMUJFWSA-N (2r)-1-[4-[4-(3-bromo-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-hydroxypropan-1-one Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)[C@@H](C)O)C(OC)=CC2=C1NC1=CC=CC(Br)=C1F HAKPDIYCVPGVFD-CYBMUJFWSA-N 0.000 claims 2
- HAKPDIYCVPGVFD-ZDUSSCGKSA-N (2s)-1-[4-[4-(3-bromo-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-hydroxypropan-1-one Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)[C@H](C)O)C(OC)=CC2=C1NC1=CC=CC(Br)=C1F HAKPDIYCVPGVFD-ZDUSSCGKSA-N 0.000 claims 2
- NJAVGTVVSVDFBS-UHFFFAOYSA-N 1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-ethoxyethanone Chemical compound C1CN(C(=O)COCC)CCC1OC1=CC2=NC=NC(NC=3C(=C(Cl)C=CC=3)F)=C2C=C1OC NJAVGTVVSVDFBS-UHFFFAOYSA-N 0.000 claims 2
- ZGMRFKHEJQIHAC-UHFFFAOYSA-N 1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-methoxyethanone Chemical compound C1CN(C(=O)COC)CCC1OC1=CC2=NC=NC(NC=3C(=C(Cl)C=CC=3)F)=C2C=C1OC ZGMRFKHEJQIHAC-UHFFFAOYSA-N 0.000 claims 2
- NBVMYRZKSWXDGP-UHFFFAOYSA-N 1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-3-hydroxy-2,2-dimethylpropan-1-one Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)C(C)(C)CO)C(OC)=CC2=C1NC1=CC=CC(Cl)=C1F NBVMYRZKSWXDGP-UHFFFAOYSA-N 0.000 claims 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 230000001028 anti-proliverative effect Effects 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000003551 oxepanyl group Chemical group 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- GZLIERPQHXYFPW-CQSZACIVSA-N (2r)-1-[4-[4-(3-bromoanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-hydroxypropan-1-one Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)[C@@H](C)O)C(OC)=CC2=C1NC1=CC=CC(Br)=C1 GZLIERPQHXYFPW-CQSZACIVSA-N 0.000 claims 1
- CQMVEBHVXXRLHJ-HXUWFJFHSA-N (2r)-1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-(dimethylamino)-3-hydroxypropan-1-one Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)[C@@H](CO)N(C)C)C(OC)=CC2=C1NC1=CC=CC(Cl)=C1F CQMVEBHVXXRLHJ-HXUWFJFHSA-N 0.000 claims 1
- HKPQKTRFULBKRH-CYBMUJFWSA-N (2r)-1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-hydroxypropan-1-one Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)[C@@H](C)O)C(OC)=CC2=C1NC1=CC=CC(Cl)=C1F HKPQKTRFULBKRH-CYBMUJFWSA-N 0.000 claims 1
- GKAQAIGUPWXDDZ-CQSZACIVSA-N (2r)-1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-methoxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](C)OC)CCC1OC1=CC2=NC=NC(NC=3C(=C(Cl)C=CC=3)F)=C2C=C1OC GKAQAIGUPWXDDZ-CQSZACIVSA-N 0.000 claims 1
- GZLIERPQHXYFPW-AWEZNQCLSA-N (2s)-1-[4-[4-(3-bromoanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-hydroxypropan-1-one Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)[C@H](C)O)C(OC)=CC2=C1NC1=CC=CC(Br)=C1 GZLIERPQHXYFPW-AWEZNQCLSA-N 0.000 claims 1
- OMWBEABLDPYCPY-HSZRJFAPSA-N (2s)-1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-hydroxy-3,3-dimethylbutan-1-one Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)[C@@H](O)C(C)(C)C)C(OC)=CC2=C1NC1=CC=CC(Cl)=C1F OMWBEABLDPYCPY-HSZRJFAPSA-N 0.000 claims 1
- GKAQAIGUPWXDDZ-AWEZNQCLSA-N (2s)-1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-methoxypropan-1-one Chemical compound C1CN(C(=O)[C@H](C)OC)CCC1OC1=CC2=NC=NC(NC=3C(=C(Cl)C=CC=3)F)=C2C=C1OC GKAQAIGUPWXDDZ-AWEZNQCLSA-N 0.000 claims 1
- BULJPQYHBWJOTR-OWJWWREXSA-N (2s,3s)-1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-hydroxy-3-methylpentan-1-one Chemical compound C1CN(C(=O)[C@@H](O)[C@@H](C)CC)CCC1OC1=CC2=NC=NC(NC=3C(=C(Cl)C=CC=3)F)=C2C=C1OC BULJPQYHBWJOTR-OWJWWREXSA-N 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- UBMJNXJLCOXAPQ-ZHRRBRCNSA-N 1-[(2s,4r)-2-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidine-1-carbonyl]-4-hydroxypyrrolidin-1-yl]ethanone Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)[C@H]3N(C[C@H](O)C3)C(C)=O)C(OC)=CC2=C1NC1=CC=CC(Cl)=C1F UBMJNXJLCOXAPQ-ZHRRBRCNSA-N 0.000 claims 1
- BBWHNPBFCSESKS-UHFFFAOYSA-N 1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-(2-methoxyethoxy)ethanone Chemical compound C1CN(C(=O)COCCOC)CCC1OC1=CC2=NC=NC(NC=3C(=C(Cl)C=CC=3)F)=C2C=C1OC BBWHNPBFCSESKS-UHFFFAOYSA-N 0.000 claims 1
- PZZCHOWGOUUGLJ-UHFFFAOYSA-N 1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-(4-methylpiperazin-1-yl)ethanone Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)CN3CCN(C)CC3)C(OC)=CC2=C1NC1=CC=CC(Cl)=C1F PZZCHOWGOUUGLJ-UHFFFAOYSA-N 0.000 claims 1
- MZVZZNYVRCEGDS-UHFFFAOYSA-N 1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)CN(C)C)C(OC)=CC2=C1NC1=CC=CC(Cl)=C1F MZVZZNYVRCEGDS-UHFFFAOYSA-N 0.000 claims 1
- POPHFBPAYSUVDB-UHFFFAOYSA-N 1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-3-hydroxy-3-methylbutan-1-one Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)CC(C)(C)O)C(OC)=CC2=C1NC1=CC=CC(Cl)=C1F POPHFBPAYSUVDB-UHFFFAOYSA-N 0.000 claims 1
- ZWEKFSQMEWHVMO-UHFFFAOYSA-N 1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-3-hydroxypropan-1-one Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)CCO)C(OC)=CC2=C1NC1=CC=CC(Cl)=C1F ZWEKFSQMEWHVMO-UHFFFAOYSA-N 0.000 claims 1
- APYUHEHEVLGNFK-UHFFFAOYSA-N 1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-3-methoxypropan-1-one Chemical compound C1CN(C(=O)CCOC)CCC1OC1=CC2=NC=NC(NC=3C(=C(Cl)C=CC=3)F)=C2C=C1OC APYUHEHEVLGNFK-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- QEZHNZSLNKRLMM-UHFFFAOYSA-N [4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-(oxolan-2-yl)methanone Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)C3OCCC3)C(OC)=CC2=C1NC1=CC=CC(Cl)=C1F QEZHNZSLNKRLMM-UHFFFAOYSA-N 0.000 claims 1
- QEZHNZSLNKRLMM-HXUWFJFHSA-N [4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-[(2r)-oxolan-2-yl]methanone Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)[C@@H]3OCCC3)C(OC)=CC2=C1NC1=CC=CC(Cl)=C1F QEZHNZSLNKRLMM-HXUWFJFHSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 239000010802 sludge Substances 0.000 claims 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
-
- 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
-
- 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
- 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
- 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
- C07D405/14—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 three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Ceramic Engineering (AREA)
- Health & Medical Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Structural Engineering (AREA)
- Materials Engineering (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0321620.7A GB0321620D0 (en) | 2003-09-16 | 2003-09-16 | Quinazoline derivatives |
| GB0321620.7 | 2003-09-16 | ||
| GB0406163A GB0406163D0 (en) | 2004-03-19 | 2004-03-19 | Quinazoline derivatives |
| GB0406163.6 | 2004-03-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2006112599A RU2006112599A (ru) | 2007-11-10 |
| RU2378268C2 true RU2378268C2 (ru) | 2010-01-10 |
Family
ID=34315440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2006112599/04A RU2378268C2 (ru) | 2003-09-16 | 2004-09-13 | Производные хиназолина в качестве ингибиторов тирозинкиназы |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US7569577B2 (https=) |
| EP (1) | EP1667991B1 (https=) |
| JP (1) | JP4795952B2 (https=) |
| AR (1) | AR045663A1 (https=) |
| AT (1) | ATE395346T1 (https=) |
| AU (1) | AU2004272348B2 (https=) |
| BR (1) | BRPI0414489A8 (https=) |
| CA (1) | CA2538884C (https=) |
| CO (1) | CO5690594A2 (https=) |
| CY (1) | CY1108186T1 (https=) |
| DE (1) | DE602004013806D1 (https=) |
| DK (1) | DK1667991T3 (https=) |
| ES (1) | ES2305844T3 (https=) |
| HR (1) | HRP20080329T3 (https=) |
| IL (1) | IL174261A0 (https=) |
| MX (1) | MXPA06002964A (https=) |
| NO (1) | NO20061322L (https=) |
| PL (1) | PL1667991T3 (https=) |
| PT (1) | PT1667991E (https=) |
| RU (1) | RU2378268C2 (https=) |
| SI (1) | SI1667991T1 (https=) |
| TW (1) | TW200519104A (https=) |
| UA (1) | UA84167C2 (https=) |
| WO (1) | WO2005026150A1 (https=) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005515176A (ja) * | 2001-11-03 | 2005-05-26 | アストラゼネカ アクチボラグ | 抗腫瘍剤としてのキナゾリン誘導体 |
| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
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- 2004-09-13 AT AT04768469T patent/ATE395346T1/de not_active IP Right Cessation
- 2004-09-13 PT PT04768469T patent/PT1667991E/pt unknown
- 2004-09-13 US US10/573,090 patent/US7569577B2/en not_active Expired - Fee Related
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- 2004-09-13 BR BRPI0414489A patent/BRPI0414489A8/pt not_active Application Discontinuation
- 2004-09-13 DK DK04768469T patent/DK1667991T3/da active
- 2004-09-13 WO PCT/GB2004/003923 patent/WO2005026150A1/en not_active Ceased
- 2004-09-13 DE DE602004013806T patent/DE602004013806D1/de not_active Expired - Lifetime
- 2004-09-13 PL PL04768469T patent/PL1667991T3/pl unknown
- 2004-09-13 SI SI200430769T patent/SI1667991T1/sl unknown
- 2004-09-13 UA UAA200604148A patent/UA84167C2/ru unknown
- 2004-09-13 EP EP04768469A patent/EP1667991B1/en not_active Expired - Lifetime
- 2004-09-13 CA CA2538884A patent/CA2538884C/en not_active Expired - Fee Related
- 2004-09-13 AU AU2004272348A patent/AU2004272348B2/en not_active Ceased
- 2004-09-13 RU RU2006112599/04A patent/RU2378268C2/ru not_active IP Right Cessation
- 2004-09-13 MX MXPA06002964A patent/MXPA06002964A/es active IP Right Grant
- 2004-09-13 JP JP2006526682A patent/JP4795952B2/ja not_active Expired - Fee Related
- 2004-09-14 TW TW093127785A patent/TW200519104A/zh unknown
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- 2008-07-10 CY CY20081100724T patent/CY1108186T1/el unknown
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| WO2001032651A1 (en) * | 1999-11-05 | 2001-05-10 | Astrazeneca Ab | Quinazoline derivatives as vegf inhibitors |
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Also Published As
| Publication number | Publication date |
|---|---|
| AU2004272348B2 (en) | 2008-09-04 |
| ES2305844T3 (es) | 2008-11-01 |
| JP4795952B2 (ja) | 2011-10-19 |
| JP2007505872A (ja) | 2007-03-15 |
| AU2004272348A1 (en) | 2005-03-24 |
| NO20061322L (no) | 2006-06-15 |
| MXPA06002964A (es) | 2006-06-14 |
| CY1108186T1 (el) | 2014-02-12 |
| SI1667991T1 (sl) | 2008-10-31 |
| UA84167C2 (ru) | 2008-09-25 |
| US20070043009A1 (en) | 2007-02-22 |
| CA2538884C (en) | 2010-09-21 |
| ATE395346T1 (de) | 2008-05-15 |
| CO5690594A2 (es) | 2006-10-31 |
| CA2538884A1 (en) | 2005-03-24 |
| US20090312343A1 (en) | 2009-12-17 |
| RU2006112599A (ru) | 2007-11-10 |
| PL1667991T3 (pl) | 2008-12-31 |
| HRP20080329T3 (en) | 2008-08-31 |
| US7569577B2 (en) | 2009-08-04 |
| AR045663A1 (es) | 2005-11-02 |
| EP1667991A1 (en) | 2006-06-14 |
| WO2005026150A1 (en) | 2005-03-24 |
| PT1667991E (pt) | 2008-07-14 |
| EP1667991B1 (en) | 2008-05-14 |
| BRPI0414489A8 (pt) | 2019-01-15 |
| DE602004013806D1 (en) | 2008-06-26 |
| DK1667991T3 (da) | 2008-08-18 |
| HK1091480A1 (en) | 2007-01-19 |
| BRPI0414489A (pt) | 2006-11-14 |
| IL174261A0 (en) | 2006-08-01 |
| TW200519104A (en) | 2005-06-16 |
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