JP5719779B2 - キナゾリノン化合物 - Google Patents
キナゾリノン化合物 Download PDFInfo
- Publication number
- JP5719779B2 JP5719779B2 JP2011542631A JP2011542631A JP5719779B2 JP 5719779 B2 JP5719779 B2 JP 5719779B2 JP 2011542631 A JP2011542631 A JP 2011542631A JP 2011542631 A JP2011542631 A JP 2011542631A JP 5719779 B2 JP5719779 B2 JP 5719779B2
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- Japan
- Prior art keywords
- compound
- optionally substituted
- formula
- acid
- alkyl
- 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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- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 223
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- 239000000203 mixture Substances 0.000 claims description 50
- 125000000623 heterocyclic group Chemical group 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 40
- -1 aryl compound Chemical class 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 239000003814 drug Substances 0.000 claims description 31
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 29
- 208000018737 Parkinson disease Diseases 0.000 claims description 28
- 238000011282 treatment Methods 0.000 claims description 27
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 17
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 238000005576 amination reaction Methods 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 238000003556 assay Methods 0.000 description 23
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- 229940079593 drug Drugs 0.000 description 23
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
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- PLRACCBDVIHHLZ-UHFFFAOYSA-N 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine Chemical compound C1N(C)CCC(C=2C=CC=CC=2)=C1 PLRACCBDVIHHLZ-UHFFFAOYSA-N 0.000 description 10
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 10
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 10
- 102000001708 Protein Isoforms Human genes 0.000 description 10
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- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 10
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 9
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- 229910017604 nitric acid Inorganic materials 0.000 description 9
- TXZVRLLCMSPNOH-UHFFFAOYSA-N 2,4-dichloro-5-nitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=C(Cl)C=C1Cl TXZVRLLCMSPNOH-UHFFFAOYSA-N 0.000 description 8
- WKTGFYBNDVOWML-UHFFFAOYSA-N 4,6-dichloro-3-hydroxy-2-nitrobenzoic acid Chemical compound OC(=O)C1=C(Cl)C=C(Cl)C(O)=C1[N+]([O-])=O WKTGFYBNDVOWML-UHFFFAOYSA-N 0.000 description 8
- IRKGRJJRILPYMF-UHFFFAOYSA-N 4,6-dichloro-3-methoxy-2-nitro-n-propylbenzamide Chemical compound CCCNC(=O)C1=C(Cl)C=C(Cl)C(OC)=C1[N+]([O-])=O IRKGRJJRILPYMF-UHFFFAOYSA-N 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
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- GIKFYMHXEKEQEC-UHFFFAOYSA-N methyl 4,6-dichloro-3-methoxy-2-nitrobenzoate Chemical compound COC(=O)C1=C(Cl)C=C(Cl)C(OC)=C1[N+]([O-])=O GIKFYMHXEKEQEC-UHFFFAOYSA-N 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- SSVLJYCXCSNJDT-UHFFFAOYSA-N 4,6-dichloro-3-methoxy-2-nitrobenzoic acid Chemical compound COC1=C(Cl)C=C(Cl)C(C(O)=O)=C1[N+]([O-])=O SSVLJYCXCSNJDT-UHFFFAOYSA-N 0.000 description 5
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- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 5
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- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 229940100613 topical solution Drugs 0.000 description 1
- 229940061102 topical suspension Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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Classifications
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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
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/91—Oxygen atoms with aryl or aralkyl radicals attached in position 2 or 3
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2008906650 | 2008-12-24 | ||
| AU2008906650A AU2008906650A0 (en) | 2008-12-24 | Quinazolinone compounds | |
| PCT/AU2009/001701 WO2010071944A1 (en) | 2008-12-24 | 2009-12-23 | Quinazolinone compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015058888A Division JP2015143249A (ja) | 2008-12-24 | 2015-03-23 | キナゾリノン化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012513416A JP2012513416A (ja) | 2012-06-14 |
| JP2012513416A5 JP2012513416A5 (enExample) | 2013-02-14 |
| JP5719779B2 true JP5719779B2 (ja) | 2015-05-20 |
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| JP2011542631A Expired - Fee Related JP5719779B2 (ja) | 2008-12-24 | 2009-12-23 | キナゾリノン化合物 |
| JP2015058888A Pending JP2015143249A (ja) | 2008-12-24 | 2015-03-23 | キナゾリノン化合物 |
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| JP2015058888A Pending JP2015143249A (ja) | 2008-12-24 | 2015-03-23 | キナゾリノン化合物 |
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| Country | Link |
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| US (3) | US8889695B2 (enExample) |
| EP (1) | EP2379510B1 (enExample) |
| JP (2) | JP5719779B2 (enExample) |
| DK (1) | DK2379510T3 (enExample) |
| ES (1) | ES2634492T3 (enExample) |
| WO (1) | WO2010071944A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015143249A (ja) * | 2008-12-24 | 2015-08-06 | プラナ バイオテクノロジー リミティッド | キナゾリノン化合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6667300B2 (en) * | 2000-04-25 | 2003-12-23 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
| LT2612862T (lt) | 2004-05-13 | 2017-01-25 | Icos Corporation | Chinazolinonai kaip žmogaus fosfatidilinozitol-3-kinazės delta inhibitoriai |
| US9492449B2 (en) | 2008-11-13 | 2016-11-15 | Gilead Calistoga Llc | Therapies for hematologic malignancies |
| KR20170060179A (ko) | 2008-11-13 | 2017-05-31 | 길리아드 칼리스토가 엘엘씨 | 혈액 종양에 대한 요법 |
| JP2012524126A (ja) * | 2009-04-20 | 2012-10-11 | ギリアド カリストガ リミテッド ライアビリティ カンパニー | 固形腫瘍の治療方法 |
| CA2768843A1 (en) | 2009-07-21 | 2011-01-27 | Gilead Calistoga Llc | Treatment of liver disorders with pi3k inhibitors |
| ES2848273T3 (es) | 2012-03-05 | 2021-08-06 | Gilead Calistoga Llc | Formas polimórficas de (S)-2-(1-(9H-purin-6-ilamino)propilo)-5-fluoro-3-fenilquinazolina-4(3H)-ona |
| EP2938600B1 (en) | 2012-12-27 | 2017-01-25 | F. Hoffmann-La Roche AG | Comt inhibitors |
| JP2017500319A (ja) | 2013-12-20 | 2017-01-05 | ギリアード カリストガ エルエルシー | （ｓ）−２−（１−（９ｈ−プリン−６−イルアミノ）プロピル）−５−フルオロ−３−フェニルキナゾリン−４（３ｈ）−オンの塩酸塩の多形形態 |
| EP3083630B1 (en) | 2013-12-20 | 2019-08-21 | Gilead Calistoga LLC | Process methods for phosphatidylinositol 3-kinase inhibitors |
| US11021467B2 (en) | 2014-06-13 | 2021-06-01 | Gilead Sciences, Inc. | Phosphatidylinositol 3-kinase inhibitors |
| CN104016929B (zh) * | 2014-06-25 | 2016-03-30 | 北京理工大学 | 一种合成喹唑啉-4(3h)-酮的方法 |
| US10781178B2 (en) | 2015-08-12 | 2020-09-22 | The General Hospital Corporation | 8-hydroxyquinoline derivatives as diagnostic and therapeutic agents |
| WO2025059726A1 (en) * | 2023-09-22 | 2025-03-27 | Alterity Therapeutics Limited | Novel therapy |
| WO2026011229A1 (en) * | 2024-07-12 | 2026-01-15 | Alterity Therapeutics Limited | Novel therapy |
| WO2026011223A1 (en) * | 2024-07-12 | 2026-01-15 | Alterity Therapeutics Limited | Novel salt and crystalline form |
| WO2026020054A1 (en) * | 2024-07-18 | 2026-01-22 | Neumora Therapeutics, Inc. | Compounds and methods for treating neurological disorders |
| US12703688B1 (en) | 2025-03-14 | 2026-08-11 | Alterity Therapeutics Limited | Crystalline form, and process for its production |
Family Cites Families (8)
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| DE60336901D1 (de) * | 2002-03-07 | 2011-06-09 | X Ceptor Therapeutics Inc | Chinazolinon modulatoren von nukleinrezeptoren |
| ES2440217T3 (es) * | 2002-10-04 | 2014-01-28 | Prana Biotechnology Limited | Compuestos neurológicamente activos |
| ATE440825T1 (de) * | 2003-06-06 | 2009-09-15 | Vertex Pharma | Pyrimidin-derivate zur verwendung als modulatoren von atp-bindende kassette transportern |
| DK1737831T3 (da) | 2004-04-02 | 2013-08-19 | Prana Biotechnology Ltd | Neurologisk aktive forbindelser |
| BRPI0722382A2 (pt) * | 2006-04-14 | 2012-06-05 | Prana Biotechnology Ltd | compostos úteis para o tratamento de cáncer |
| JP5415942B2 (ja) * | 2006-06-22 | 2014-02-12 | プラナ バイオテクノロジー リミティッド | 処置の方法およびその処置に有用な薬剤 |
| WO2008074068A1 (en) * | 2006-12-20 | 2008-06-26 | Prana Biotechnology Limited | Substituted quinoline derivatives as antiamyloidogeneic agents |
| WO2010071944A1 (en) * | 2008-12-24 | 2010-07-01 | Prana Biotechnology Limited | Quinazolinone compounds |
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2009
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- 2009-12-23 ES ES09833944.3T patent/ES2634492T3/es active Active
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2014
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2015
- 2015-03-23 JP JP2015058888A patent/JP2015143249A/ja active Pending
- 2015-08-21 US US14/832,130 patent/US20150359796A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015143249A (ja) * | 2008-12-24 | 2015-08-06 | プラナ バイオテクノロジー リミティッド | キナゾリノン化合物 |
Also Published As
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|---|---|
| US20150359796A1 (en) | 2015-12-17 |
| ES2634492T3 (es) | 2017-09-28 |
| JP2015143249A (ja) | 2015-08-06 |
| US20150025072A1 (en) | 2015-01-22 |
| AU2009329833A2 (en) | 2011-07-14 |
| JP2012513416A (ja) | 2012-06-14 |
| US20120040980A1 (en) | 2012-02-16 |
| EP2379510B1 (en) | 2016-10-26 |
| AU2009329833A1 (en) | 2011-07-14 |
| DK2379510T3 (en) | 2016-12-19 |
| US8889695B2 (en) | 2014-11-18 |
| EP2379510A4 (en) | 2012-08-08 |
| EP2379510A1 (en) | 2011-10-26 |
| WO2010071944A1 (en) | 2010-07-01 |
| US9145375B2 (en) | 2015-09-29 |
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