AU2005214373B2 - Quinazoline derivatives and therapeutic use thereof - Google Patents
Quinazoline derivatives and therapeutic use thereof Download PDFInfo
- Publication number
- AU2005214373B2 AU2005214373B2 AU2005214373A AU2005214373A AU2005214373B2 AU 2005214373 B2 AU2005214373 B2 AU 2005214373B2 AU 2005214373 A AU2005214373 A AU 2005214373A AU 2005214373 A AU2005214373 A AU 2005214373A AU 2005214373 B2 AU2005214373 B2 AU 2005214373B2
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- Australia
- Prior art keywords
- fluorophenyl
- compound
- phenyl
- chlorophenyl
- tumors
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title abstract 2
- 230000001225 therapeutic effect Effects 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 330
- 239000000203 mixture Substances 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 28
- 238000011282 treatment Methods 0.000 claims abstract description 28
- 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- -1 4-substituted phenyl Chemical group 0.000 claims description 340
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 97
- 206010028980 Neoplasm Diseases 0.000 claims description 62
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 44
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 40
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 22
- 208000035475 disorder Diseases 0.000 claims description 21
- 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 19
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 14
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 10
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 8
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 7
- 210000000481 breast Anatomy 0.000 claims description 7
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 201000001441 melanoma Diseases 0.000 claims description 7
- 210000001672 ovary Anatomy 0.000 claims description 7
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 6
- 210000004185 liver Anatomy 0.000 claims description 6
- 210000002307 prostate Anatomy 0.000 claims description 6
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 206010061968 Gastric neoplasm Diseases 0.000 claims description 5
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
- 208000029742 colonic neoplasm Diseases 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 5
- 208000037841 lung tumor Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 201000002528 pancreatic cancer Diseases 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 208000024719 uterine cervix neoplasm Diseases 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 101100338491 Oryza sativa subsp. japonica HCT1 gene Proteins 0.000 claims description 2
- 101100495309 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CDH1 gene Proteins 0.000 claims description 2
- 229940088597 hormone Drugs 0.000 claims description 2
- 239000005556 hormone Substances 0.000 claims description 2
- 125000006178 methyl benzyl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 125000004212 difluorophenyl group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 208
- 238000005160 1H NMR spectroscopy Methods 0.000 description 109
- 229910004298 SiO 2 Inorganic materials 0.000 description 95
- 238000006243 chemical reaction Methods 0.000 description 87
- 238000004587 chromatography analysis Methods 0.000 description 85
- 150000003246 quinazolines Chemical class 0.000 description 50
- 210000004027 cell Anatomy 0.000 description 45
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 44
- 239000000243 solution Substances 0.000 description 36
- TZYWCYJVHRLUCT-VABKMULXSA-N N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal Chemical compound CC(C)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1 TZYWCYJVHRLUCT-VABKMULXSA-N 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 230000002829 reductive effect Effects 0.000 description 26
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
- 238000010992 reflux Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 238000004440 column chromatography Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 12
- 230000008685 targeting Effects 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
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- 201000011510 cancer Diseases 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
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- PHHRKRGXWSEXFZ-UHFFFAOYSA-N n-(pyridin-3-ylmethyl)-3-[[2-[(2,3,4-trifluorophenoxy)methyl]-1,3-benzoxazol-4-yl]oxy]propan-1-amine Chemical compound FC1=C(F)C(F)=CC=C1OCC(OC1=CC=C2)=NC1=C2OCCCNCC1=CC=CN=C1 PHHRKRGXWSEXFZ-UHFFFAOYSA-N 0.000 description 10
- RWWYLEGWBNMMLJ-YSOARWBDSA-N remdesivir Chemical compound NC1=NC=NN2C1=CC=C2[C@]1([C@@H]([C@@H]([C@H](O1)CO[P@](=O)(OC1=CC=CC=C1)N[C@H](C(=O)OCC(CC)CC)C)O)O)C#N RWWYLEGWBNMMLJ-YSOARWBDSA-N 0.000 description 10
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 229940125807 compound 37 Drugs 0.000 description 9
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- AGNFWIZBEATIAK-UHFFFAOYSA-N 4-phenylbutylamine Chemical compound NCCCCC1=CC=CC=C1 AGNFWIZBEATIAK-UHFFFAOYSA-N 0.000 description 8
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- BGXZIBSLBRKDTP-UHFFFAOYSA-N methyl 9-(4-chloroanilino)-[1,3]thiazolo[5,4-f]quinazoline-2-carboximidate Chemical compound C12=C3SC(C(=N)OC)=NC3=CC=C2N=CN=C1NC1=CC=C(Cl)C=C1 BGXZIBSLBRKDTP-UHFFFAOYSA-N 0.000 description 8
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Classifications
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- 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
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- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- 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
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54548704P | 2004-02-19 | 2004-02-19 | |
| US60/545,487 | 2004-02-19 | ||
| PCT/US2005/005151 WO2005080352A2 (en) | 2004-02-19 | 2005-02-17 | Quinazoline derivatives and therapeutic use thereof |
Publications (2)
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| AU2005214373A1 AU2005214373A1 (en) | 2005-09-01 |
| AU2005214373B2 true AU2005214373B2 (en) | 2011-07-28 |
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|---|---|
| US (2) | US7388014B2 (https=) |
| EP (2) | EP2650286A1 (https=) |
| JP (1) | JP4934432B2 (https=) |
| KR (1) | KR100942865B1 (https=) |
| CN (1) | CN1956966B (https=) |
| AU (1) | AU2005214373B2 (https=) |
| BR (1) | BRPI0507903A (https=) |
| CA (1) | CA2557433C (https=) |
| ES (1) | ES2554330T3 (https=) |
| MX (1) | MXPA06009475A (https=) |
| WO (1) | WO2005080352A2 (https=) |
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| US8039637B2 (en) * | 2005-06-23 | 2011-10-18 | Array Biopharma Inc. | Process for preparing benzimidazole compounds |
| AU2007249762A1 (en) * | 2006-05-15 | 2007-11-22 | Senex Biotechnology, Inc | Identification of CDKI pathway inhibitors |
| WO2008124823A1 (en) * | 2007-04-10 | 2008-10-16 | Myriad Genetics, Inc. | Method of treating melanoma |
| CN101120945B (zh) * | 2007-07-30 | 2010-11-24 | 浙江大学 | 8-芳胺基-3H-咪唑[4,5-g]喹唑啉类衍生物的用途 |
| PH12012500097A1 (en) * | 2009-07-21 | 2011-01-27 | Shanghai Inst Organic Chem | Potent small molecule inhibitors of autophagy, and methods of use thereof |
| WO2012006960A1 (en) * | 2010-07-14 | 2012-01-19 | Zhejiang Beta Pharma Inc. | NOVEL FUSED HETEROCYCLIC DERIVATIVES USEFUL AS c-MET TYROSINE KINASE INHIBITORS |
| US20140309224A1 (en) * | 2011-09-13 | 2014-10-16 | Roninson Igor B | TREATMENT OF DISEASES OR DISORDERS CAUSED BY INDUCED NFkB TRANSCRIPTIONAL ACTIVITY |
| CN103086984A (zh) * | 2011-11-03 | 2013-05-08 | 南京大学 | 一类4-苯氨基喹唑啉类衍生物及其制备方法与用途 |
| WO2013135671A1 (en) | 2012-03-13 | 2013-09-19 | Basf Se | Fungicidal pyrimidine compounds |
| CN102659692B (zh) | 2012-05-04 | 2014-04-09 | 郑州泰基鸿诺药物科技有限公司 | 双联厄洛替尼及其制备方法 |
| CN102875570B (zh) * | 2012-10-23 | 2015-11-04 | 浙江大学 | 喹唑啉衍生物及其制备方法和用途 |
| JP6464139B2 (ja) | 2013-03-14 | 2019-02-06 | コンバージーン・リミテッド・ライアビリティ・カンパニーＣｏｎｖｅｒｇｅｎｅ Ｌｌｃ | ブロモドメイン含有タンパク質の阻害のための方法および組成物 |
| WO2015036058A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
| WO2015036059A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
| RU2016112013A (ru) * | 2013-09-19 | 2017-10-24 | Пьер Фабр Медикамент | Производные хиназолина и их применение в качестве ингибиторов днк-метилтрансферазы |
| CN104926798B (zh) * | 2014-03-21 | 2019-06-18 | 江苏豪森药业集团有限公司 | 阿法替尼中间体的高纯度制备方法 |
| CA3006300C (en) | 2015-11-25 | 2024-02-27 | Convergene Llc | Bicyclic bet bromodomain inhibitors and uses thereof |
| JP7191446B2 (ja) * | 2017-01-30 | 2022-12-19 | 塩野義製薬株式会社 | キナゾリン誘導体を含有する固形製剤 |
| EP3897651A4 (en) * | 2018-12-21 | 2022-09-21 | University of Notre Dame du Lac | DISCOVERY OF BD-OXIDASE INHIBITORS FOR THE TREATMENT OF MYCOBACTERIAL DISEASES |
| EP4424379A3 (en) | 2019-04-24 | 2024-10-30 | Convergene Llc | Small molecule bromodomain inhibitors and uses thereof |
| KR102397359B1 (ko) * | 2019-09-30 | 2022-05-11 | 한국화학연구원 | 4-아미노-퀴나졸린 유도체 및 이를 포함하는 항바이러스용 조성물 |
| KR20220132543A (ko) * | 2019-12-27 | 2022-09-30 | 루핀 리미티드 | 치환된 삼환 화합물 |
| TWI807787B (zh) * | 2021-04-19 | 2023-07-01 | 大陸商昆藥集團股份有限公司 | 苯並嘧啶三環衍生物及製備方法和應用 |
| CN116444443B (zh) * | 2023-03-15 | 2025-09-05 | 广东省中医院（广州中医药大学第二附属医院、广州中医药大学第二临床医学院、广东省中医药科学院） | 一种苯甲酰-喹唑啉酮衍生物及其制备方法与应用 |
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| EP0566226A1 (en) * | 1992-01-20 | 1993-10-20 | Zeneca Limited | Quinazoline derivatives |
| US5296484A (en) * | 1988-01-29 | 1994-03-22 | Dowelanco | Quinoline derivatives |
| EP0635507A1 (en) * | 1993-07-19 | 1995-01-25 | Zeneca Limited | Tricyclic derivatives and their use as anti-cancer agents |
| WO1995019970A1 (en) * | 1994-01-25 | 1995-07-27 | Warner-Lambert Company | Tricyclic compounds capable of inhibiting tyrosine kinases of the epidermal growth factor receptor family |
| US5480883A (en) * | 1991-05-10 | 1996-01-02 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| WO1996029331A1 (de) * | 1995-03-20 | 1996-09-26 | Dr. Karl Thomae Gmbh | Imidazochinazoline, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| US5710158A (en) * | 1991-05-10 | 1998-01-20 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US5721237A (en) * | 1991-05-10 | 1998-02-24 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Protein tyrosine kinase aryl and heteroaryl quinazoline compounds having selective inhibition of HER-2 autophosphorylation properties |
| US6046206A (en) * | 1995-06-07 | 2000-04-04 | Cell Pathways, Inc. | Method of treating a patient having a precancerous lesions with amide quinazoline derivatives |
| US6645969B1 (en) * | 1991-05-10 | 2003-11-11 | Aventis Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
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| CH492395A (de) | 1966-04-26 | 1970-06-30 | Sandoz Ag | Mittel zur Bekämpfung von Pflanzenschädlingen und Verwendung des Mittels |
| US4559157A (en) | 1983-04-21 | 1985-12-17 | Creative Products Resource Associates, Ltd. | Cosmetic applicator useful for skin moisturizing |
| LU84979A1 (fr) | 1983-08-30 | 1985-04-24 | Oreal | Composition cosmetique ou pharmaceutique sous forme aqueuse ou anhydre dont la phase grasse contient un polyether oligomere et polyethers oligomeres nouveaux |
| US4820508A (en) | 1987-06-23 | 1989-04-11 | Neutrogena Corporation | Skin protective composition |
| US4992478A (en) | 1988-04-04 | 1991-02-12 | Warner-Lambert Company | Antiinflammatory skin moisturizing composition and method of preparing same |
| MX9707453A (es) * | 1995-03-30 | 1997-12-31 | Pfizer | Derivados de quinazolina. |
| GB9508565D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quiazoline derivative |
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-
2005
- 2005-02-17 JP JP2006554220A patent/JP4934432B2/ja not_active Expired - Fee Related
- 2005-02-17 CN CN2005800117828A patent/CN1956966B/zh not_active Expired - Fee Related
- 2005-02-17 ES ES05723255.5T patent/ES2554330T3/es not_active Expired - Lifetime
- 2005-02-17 BR BRPI0507903-9A patent/BRPI0507903A/pt not_active IP Right Cessation
- 2005-02-17 KR KR1020067019158A patent/KR100942865B1/ko not_active Expired - Fee Related
- 2005-02-17 EP EP13173085.5A patent/EP2650286A1/en not_active Withdrawn
- 2005-02-17 CA CA2557433A patent/CA2557433C/en not_active Expired - Fee Related
- 2005-02-17 US US11/059,376 patent/US7388014B2/en not_active Expired - Lifetime
- 2005-02-17 MX MXPA06009475A patent/MXPA06009475A/es active IP Right Grant
- 2005-02-17 AU AU2005214373A patent/AU2005214373B2/en not_active Ceased
- 2005-02-17 WO PCT/US2005/005151 patent/WO2005080352A2/en not_active Ceased
- 2005-02-17 EP EP05723255.5A patent/EP1720841B1/en not_active Expired - Lifetime
-
2008
- 2008-06-16 US US12/213,182 patent/US8404698B2/en not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| US8404698B2 (en) | 2013-03-26 |
| EP1720841B1 (en) | 2015-11-04 |
| BRPI0507903A (pt) | 2007-07-10 |
| CN1956966B (zh) | 2012-04-18 |
| JP4934432B2 (ja) | 2012-05-16 |
| KR20070028340A (ko) | 2007-03-12 |
| CA2557433C (en) | 2013-05-14 |
| US20090030021A1 (en) | 2009-01-29 |
| EP1720841A2 (en) | 2006-11-15 |
| WO2005080352A3 (en) | 2006-02-16 |
| JP2007523177A (ja) | 2007-08-16 |
| US20050187231A1 (en) | 2005-08-25 |
| MXPA06009475A (es) | 2007-05-15 |
| EP2650286A1 (en) | 2013-10-16 |
| CA2557433A1 (en) | 2005-09-01 |
| KR100942865B1 (ko) | 2010-02-17 |
| AU2005214373A1 (en) | 2005-09-01 |
| US7388014B2 (en) | 2008-06-17 |
| WO2005080352A2 (en) | 2005-09-01 |
| CN1956966A (zh) | 2007-05-02 |
| ES2554330T3 (es) | 2015-12-18 |
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