ZA200102655B - Quinazoline derivatives. - Google Patents
Quinazoline derivatives. Download PDFInfo
- Publication number
- ZA200102655B ZA200102655B ZA200102655A ZA200102655A ZA200102655B ZA 200102655 B ZA200102655 B ZA 200102655B ZA 200102655 A ZA200102655 A ZA 200102655A ZA 200102655 A ZA200102655 A ZA 200102655A ZA 200102655 B ZA200102655 B ZA 200102655B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- methoxy
- compound
- sub
- quinazoline
- Prior art date
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- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title description 11
- -1 cyano, amino Chemical group 0.000 claims abstract description 231
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 230
- 150000001875 compounds Chemical class 0.000 claims abstract description 208
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 116
- 239000001257 hydrogen Substances 0.000 claims abstract description 110
- 150000003839 salts Chemical class 0.000 claims abstract description 93
- 238000000034 method Methods 0.000 claims abstract description 75
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 62
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 56
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 54
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 46
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 42
- 230000008569 process Effects 0.000 claims abstract description 32
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 claims abstract description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 28
- 230000008728 vascular permeability Effects 0.000 claims abstract description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 23
- 241001465754 Metazoa Species 0.000 claims abstract description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 20
- 230000001772 anti-angiogenic effect Effects 0.000 claims abstract description 19
- 239000003814 drug Substances 0.000 claims abstract description 19
- 230000001603 reducing effect Effects 0.000 claims abstract description 18
- 238000011282 treatment Methods 0.000 claims abstract description 18
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 12
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 9
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 93
- 125000001424 substituent group Chemical group 0.000 claims description 69
- 125000005843 halogen group Chemical group 0.000 claims description 63
- 229910052757 nitrogen Inorganic materials 0.000 claims description 45
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 229910052799 carbon Inorganic materials 0.000 claims description 33
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 32
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- 150000001721 carbon Chemical group 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 22
- 125000004043 oxo group Chemical group O=* 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000003386 piperidinyl group Chemical group 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 241000282412 Homo Species 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 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 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 7
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 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 6
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- ZMOXRVVUBDCFRG-UHFFFAOYSA-N 4-[3-[6-methoxy-4-[(5-pyridin-4-yl-1h-pyrazol-3-yl)oxy]quinazolin-7-yl]oxypropyl]morpholine Chemical compound N1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(=NN1)C=C1C1=CC=NC=C1 ZMOXRVVUBDCFRG-UHFFFAOYSA-N 0.000 claims description 4
- CEXSLCSYMIGRRU-UHFFFAOYSA-N 6-methoxy-7-(2-methoxyethoxy)-4-[(5-phenyl-1h-pyrazol-3-yl)oxy]quinazoline Chemical compound C=12C=C(OC)C(OCCOC)=CC2=NC=NC=1OC(=NN1)C=C1C1=CC=CC=C1 CEXSLCSYMIGRRU-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- LDRQIAPESKISGW-UHFFFAOYSA-N 4-[3-[4-[[5-(2-fluorophenyl)-1h-pyrazol-3-yl]oxy]-6-methoxyquinazolin-7-yl]oxypropyl]morpholine Chemical compound N1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(=NN1)C=C1C1=CC=CC=C1F LDRQIAPESKISGW-UHFFFAOYSA-N 0.000 claims description 3
- XRAIRKLUFOYIFQ-UHFFFAOYSA-N 4-[3-[4-[[5-(4-chlorophenyl)-1h-pyrazol-3-yl]oxy]-6-methoxyquinazolin-7-yl]oxypropyl]morpholine Chemical compound N1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(=NN1)C=C1C1=CC=C(Cl)C=C1 XRAIRKLUFOYIFQ-UHFFFAOYSA-N 0.000 claims description 3
- MDBVRWFEYLAMBA-UHFFFAOYSA-N 6-methoxy-4-[[5-(4-methoxyphenyl)-1h-pyrazol-3-yl]oxy]-7-[(1-methylpiperidin-4-yl)methoxy]quinazoline Chemical compound C1=CC(OC)=CC=C1C1=CC(OC=2C3=CC(OC)=C(OCC4CCN(C)CC4)C=C3N=CN=2)=NN1 MDBVRWFEYLAMBA-UHFFFAOYSA-N 0.000 claims description 3
- KVLWZXBOPQRIQZ-UHFFFAOYSA-N 6-methoxy-4-[[5-(4-methoxyphenyl)-1h-pyrazol-3-yl]oxy]-7-[3-(4-methylpiperazin-1-yl)propoxy]quinazoline Chemical compound C1=CC(OC)=CC=C1C1=CC(OC=2C3=CC(OC)=C(OCCCN4CCN(C)CC4)C=C3N=CN=2)=NN1 KVLWZXBOPQRIQZ-UHFFFAOYSA-N 0.000 claims description 3
- CNDJEHZZDXTJAD-UHFFFAOYSA-N 6-methoxy-7-[2-(2-methoxyethoxy)ethoxy]-4-[(5-phenyl-1h-pyrazol-3-yl)oxy]quinazoline Chemical compound C=12C=C(OC)C(OCCOCCOC)=CC2=NC=NC=1OC(=NN1)C=C1C1=CC=CC=C1 CNDJEHZZDXTJAD-UHFFFAOYSA-N 0.000 claims description 3
- TWYLGVCHEXWXMH-UHFFFAOYSA-N 7-(2-methoxyethoxy)-4-[(5-phenyl-1h-pyrazol-3-yl)oxy]quinazoline Chemical compound N=1C=NC2=CC(OCCOC)=CC=C2C=1OC(=NN1)C=C1C1=CC=CC=C1 TWYLGVCHEXWXMH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 3
- DOQOAOBWHHEXSW-UHFFFAOYSA-N 4-[3-[6-methoxy-4-[(5-phenyl-1h-pyrazol-3-yl)oxy]quinazolin-7-yl]oxypropyl]morpholine Chemical compound N1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(=NN1)C=C1C1=CC=CC=C1 DOQOAOBWHHEXSW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 2
- VXGFRTSSUJBKEZ-UHFFFAOYSA-N 6-methoxy-4-[[5-(4-methoxyphenyl)-1h-pyrazol-3-yl]oxy]-7-[2-(triazol-1-yl)ethoxy]quinazoline Chemical compound C1=CC(OC)=CC=C1C1=CC(OC=2C3=CC(OC)=C(OCCN4N=NC=C4)C=C3N=CN=2)=NN1 VXGFRTSSUJBKEZ-UHFFFAOYSA-N 0.000 claims 1
- XQXJCZQAVUTNBQ-UHFFFAOYSA-N 6-methoxy-4-[[5-(4-methoxyphenyl)-1h-pyrazol-3-yl]oxy]-7-[[1-(2-methylsulfonylethyl)piperidin-4-yl]methoxy]quinazoline Chemical compound C1=CC(OC)=CC=C1C1=CC(OC=2C3=CC(OC)=C(OCC4CCN(CCS(C)(=O)=O)CC4)C=C3N=CN=2)=NN1 XQXJCZQAVUTNBQ-UHFFFAOYSA-N 0.000 claims 1
- LATNIDZFEFGNMI-UHFFFAOYSA-N 7-(2-imidazol-1-ylethoxy)-6-methoxy-4-[(5-phenyl-1h-pyrazol-3-yl)oxy]quinazoline Chemical compound N1=CN=C2C=C(OCCN3C=NC=C3)C(OC)=CC2=C1OC(=NN1)C=C1C1=CC=CC=C1 LATNIDZFEFGNMI-UHFFFAOYSA-N 0.000 claims 1
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 22
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- 206010028980 Neoplasm Diseases 0.000 abstract description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 10
- 125000001589 carboacyl group Chemical group 0.000 abstract description 10
- 201000011510 cancer Diseases 0.000 abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 8
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 abstract description 6
- 201000010099 disease Diseases 0.000 abstract description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 abstract description 4
- 125000005647 linker group Chemical group 0.000 abstract description 3
- 125000004849 alkoxymethyl group Chemical group 0.000 abstract description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 153
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
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- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D403/14—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 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Immunology (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Reproductive Health (AREA)
- Pain & Pain Management (AREA)
- Communicable Diseases (AREA)
- Ophthalmology & Optometry (AREA)
- Emergency Medicine (AREA)
- Oncology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Seal Device For Vehicle (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP98402496 | 1998-10-08 |
Publications (1)
Publication Number | Publication Date |
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ZA200102655B true ZA200102655B (en) | 2002-09-30 |
Family
ID=8235527
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200102655A ZA200102655B (en) | 1998-10-08 | 2001-03-30 | Quinazoline derivatives. |
Country Status (19)
Country | Link |
---|---|
US (1) | US7262201B1 (de) |
EP (1) | EP1119567B1 (de) |
JP (2) | JP2002527436A (de) |
KR (1) | KR100860295B1 (de) |
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AT (1) | ATE294796T1 (de) |
AU (1) | AU756556B2 (de) |
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CA (1) | CA2344290C (de) |
DE (1) | DE69925141T2 (de) |
DK (1) | DK1119567T3 (de) |
ES (1) | ES2241324T3 (de) |
HK (1) | HK1039126B (de) |
IL (2) | IL142359A0 (de) |
NO (1) | NO322644B1 (de) |
NZ (1) | NZ510434A (de) |
PT (1) | PT1119567E (de) |
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CN110818633A (zh) | 2009-01-16 | 2020-02-21 | 埃克塞里艾克西斯公司 | 一种苹果酸盐及其晶型 |
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1999
- 1999-10-05 JP JP2000575861A patent/JP2002527436A/ja not_active Withdrawn
- 1999-10-05 BR BR9914326-7A patent/BR9914326A/pt not_active Application Discontinuation
- 1999-10-05 KR KR1020017004370A patent/KR100860295B1/ko not_active IP Right Cessation
- 1999-10-05 DE DE69925141T patent/DE69925141T2/de not_active Expired - Lifetime
- 1999-10-05 WO PCT/GB1999/003295 patent/WO2000021955A1/en active IP Right Grant
- 1999-10-05 AT AT99947758T patent/ATE294796T1/de active
- 1999-10-05 DK DK99947758T patent/DK1119567T3/da active
- 1999-10-05 AU AU61128/99A patent/AU756556B2/en not_active Ceased
- 1999-10-05 EP EP99947758A patent/EP1119567B1/de not_active Expired - Lifetime
- 1999-10-05 IL IL14235999A patent/IL142359A0/xx unknown
- 1999-10-05 CN CNB998118613A patent/CN1161352C/zh not_active Expired - Fee Related
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- 1999-10-05 US US09/806,836 patent/US7262201B1/en not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
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NZ510434A (en) | 2003-10-31 |
JP2011126888A (ja) | 2011-06-30 |
AU6112899A (en) | 2000-05-01 |
EP1119567B1 (de) | 2005-05-04 |
IL142359A0 (en) | 2002-03-10 |
ES2241324T3 (es) | 2005-10-16 |
CN1161352C (zh) | 2004-08-11 |
JP2002527436A (ja) | 2002-08-27 |
US7262201B1 (en) | 2007-08-28 |
HK1039126A1 (en) | 2002-04-12 |
AU756556B2 (en) | 2003-01-16 |
NO20011739D0 (no) | 2001-04-06 |
HK1039126B (zh) | 2005-09-30 |
CA2344290C (en) | 2009-06-02 |
CN1322202A (zh) | 2001-11-14 |
CA2344290A1 (en) | 2000-04-20 |
PT1119567E (pt) | 2005-08-31 |
NO322644B1 (no) | 2006-11-13 |
NO20011739L (no) | 2001-06-07 |
KR20010085890A (ko) | 2001-09-07 |
ATE294796T1 (de) | 2005-05-15 |
DK1119567T3 (da) | 2005-07-25 |
IL142359A (en) | 2008-11-03 |
BR9914326A (pt) | 2001-06-26 |
DE69925141T2 (de) | 2006-04-27 |
WO2000021955A1 (en) | 2000-04-20 |
DE69925141D1 (de) | 2005-06-09 |
KR100860295B1 (ko) | 2008-09-25 |
EP1119567A1 (de) | 2001-08-01 |
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