ES2483728T3 - Derivados terapéuticos de pirazolonafatiridina - Google Patents
Derivados terapéuticos de pirazolonafatiridina Download PDFInfo
- Publication number
- ES2483728T3 ES2483728T3 ES08770412.8T ES08770412T ES2483728T3 ES 2483728 T3 ES2483728 T3 ES 2483728T3 ES 08770412 T ES08770412 T ES 08770412T ES 2483728 T3 ES2483728 T3 ES 2483728T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- compound
- optionally substituted
- aryl
- fluorine atoms
- 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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- 230000001225 therapeutic effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 125000003118 aryl group Chemical group 0.000 claims abstract description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 13
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
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- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 11
- 229910003827 NRaRb Inorganic materials 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 29
- 241001465754 Metazoa Species 0.000 claims description 26
- 230000015654 memory Effects 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 17
- -1 arylC (O) - Chemical group 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 150000002431 hydrogen Chemical group 0.000 claims description 11
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- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
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- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 54
- 238000000034 method Methods 0.000 description 41
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 31
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- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 4
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- 230000027455 binding Effects 0.000 description 4
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- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 3
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- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229940072040 tricaine Drugs 0.000 description 1
- FQZJYWMRQDKBQN-UHFFFAOYSA-N tricaine methanesulfonate Chemical compound CS([O-])(=O)=O.CCOC(=O)C1=CC=CC([NH3+])=C1 FQZJYWMRQDKBQN-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000011870 unpaired t-test Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229960001475 zolpidem Drugs 0.000 description 1
- ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94300007P | 2007-06-08 | 2007-06-08 | |
| US943000P | 2007-06-08 | ||
| PCT/US2008/066211 WO2008154447A1 (en) | 2007-06-08 | 2008-06-06 | Therapeutic pyrazolonaphthyridine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2483728T3 true ES2483728T3 (es) | 2014-08-07 |
Family
ID=40130166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08770412.8T Active ES2483728T3 (es) | 2007-06-08 | 2008-06-06 | Derivados terapéuticos de pirazolonafatiridina |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US7858614B2 (enExample) |
| EP (1) | EP2166853B1 (enExample) |
| JP (1) | JP2010529145A (enExample) |
| KR (1) | KR20100036306A (enExample) |
| CN (1) | CN101754681A (enExample) |
| AU (1) | AU2008261803A1 (enExample) |
| BR (1) | BRPI0812369A2 (enExample) |
| CA (1) | CA2689934A1 (enExample) |
| ES (1) | ES2483728T3 (enExample) |
| IL (1) | IL202287A0 (enExample) |
| MX (1) | MX2009013197A (enExample) |
| WO (1) | WO2008154447A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7863266B2 (en) * | 2007-06-08 | 2011-01-04 | Helicon Therapeutics, Inc. | Therapeutic pyrazoloquinoline urea derivatives |
| US9012470B2 (en) | 2010-10-14 | 2015-04-21 | Dart Neuroscience (Cayman) Ltd. | Therapeutic 5,6,5-tricyclic analogs |
| US20150374705A1 (en) | 2012-02-14 | 2015-12-31 | Shanghai Institues for Biological Sciences | Substances for treatment or relief of pain |
| US10531200B2 (en) * | 2015-10-23 | 2020-01-07 | Harman International Industries, Incorporated | Dual asymmetric compression driver |
| CN106810550A (zh) * | 2017-01-10 | 2017-06-09 | 湖南华腾制药有限公司 | 一种萘啶衍生物的制备方法 |
| US11485733B2 (en) | 2017-06-30 | 2022-11-01 | Bayer Animal Health Gmbh | Azaquinoline derivatives |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3204126A1 (de) * | 1982-02-06 | 1983-08-11 | Bayer Ag, 5090 Leverkusen | Pyrazoloxazine, -thiazine, -chinoline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US4479955A (en) * | 1983-01-10 | 1984-10-30 | Ciba-Geigy Corporation | Heterocycle-fused pyrazolo[3,4-d]pyridin-3-ones as benzodiazepine receptor modulators |
| US4814450A (en) | 1984-07-09 | 1989-03-21 | Ciba-Geigy Corporation | Certain ring-fused pyrazolo[3,4-d]-pyridin-3-one derivatives |
| JPS61112075A (ja) * | 1984-11-05 | 1986-05-30 | Shionogi & Co Ltd | チエニルピラゾロキノリン誘導体 |
| EP0214092A1 (en) | 1985-08-08 | 1987-03-11 | Ciba-Geigy Ag | Enhanced absorption of psychoactive 2-aryl-pyrazolo quinolines as a solid molecular dispersion in polyvinylpyrrolidone |
| US4817450A (en) * | 1987-11-30 | 1989-04-04 | Spedco, Inc. | Pressure/temperature test plug assembly |
| FR2695126B1 (fr) * | 1992-08-27 | 1994-11-10 | Sanofi Elf | Dérivés d'acide thiényl ou pyrrolyl carboxyliques, leur préparation et médicaments les contenant. |
| US5334595A (en) * | 1992-10-23 | 1994-08-02 | Sterling Winthrop Inc. | Pyrazoloquinolones as anticancer agents |
| RU2145606C1 (ru) * | 1994-05-24 | 2000-02-20 | Ф.Хоффманн-Ля Рош Аг | Трициклические дикарбонильные производные и лекарственный препарат на их основе |
| GB9716344D0 (en) * | 1997-08-01 | 1997-10-08 | Merck Sharp & Dohme | Therapeutic compounds |
| GB9716347D0 (en) * | 1997-08-01 | 1997-10-08 | Merck Sharp & Dohme | Therapeutic compounds |
| GB9716345D0 (en) * | 1997-08-01 | 1997-10-08 | Merck Sharp & Dohme | Therapeutic compounds |
| TWI271406B (en) * | 1999-12-13 | 2007-01-21 | Eisai Co Ltd | Tricyclic condensed heterocyclic compounds, preparation method of the same and pharmaceuticals comprising the same |
| GB0108475D0 (en) * | 2001-04-04 | 2001-05-23 | Merck Sharp & Dohme | New compounds |
| JP3896309B2 (ja) * | 2001-07-09 | 2007-03-22 | ファイザー株式会社 | プロテインキナーゼｃ阻害物質としてのピラゾロキノリノン誘導体 |
| ATE425164T1 (de) * | 2002-12-16 | 2009-03-15 | Active Biotech Ab | Tetrazyklische immunmodulierende verbindungen |
| AR045689A1 (es) * | 2003-05-29 | 2005-11-09 | Millennium Pharm Inc | Compuestos derivados de 2,5-dihidro-pirazolo[4,3-c]quinolin-4-ona como inhibidores de chk-1 y composiciones farmaceuticas que los contienen |
| US7544697B2 (en) * | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| CN1893943A (zh) * | 2003-10-03 | 2007-01-10 | 3M创新有限公司 | 吡唑并吡啶和其类似物 |
| AU2006287378A1 (en) * | 2005-09-07 | 2007-03-15 | Braincells, Inc. | Modulation of neurogenesis by HDac inhibition |
| ES2386168T3 (es) * | 2007-06-08 | 2012-08-10 | Helicon Therapeutics, Inc. | Derivados de pirazoloquinolina terapéuticos |
-
2008
- 2008-06-06 ES ES08770412.8T patent/ES2483728T3/es active Active
- 2008-06-06 US US12/135,045 patent/US7858614B2/en not_active Expired - Fee Related
- 2008-06-06 JP JP2010511393A patent/JP2010529145A/ja active Pending
- 2008-06-06 CA CA2689934A patent/CA2689934A1/en not_active Abandoned
- 2008-06-06 MX MX2009013197A patent/MX2009013197A/es active IP Right Grant
- 2008-06-06 BR BRPI0812369A patent/BRPI0812369A2/pt not_active IP Right Cessation
- 2008-06-06 KR KR1020107000331A patent/KR20100036306A/ko not_active Withdrawn
- 2008-06-06 AU AU2008261803A patent/AU2008261803A1/en not_active Abandoned
- 2008-06-06 CN CN200880025152A patent/CN101754681A/zh active Pending
- 2008-06-06 EP EP08770412.8A patent/EP2166853B1/en not_active Not-in-force
- 2008-06-06 WO PCT/US2008/066211 patent/WO2008154447A1/en not_active Ceased
-
2009
- 2009-11-23 IL IL202287A patent/IL202287A0/en unknown
-
2010
- 2010-11-18 US US12/949,619 patent/US8497262B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HK1142774A1 (en) | 2010-12-17 |
| EP2166853B1 (en) | 2014-05-28 |
| EP2166853A4 (en) | 2011-04-06 |
| CN101754681A (zh) | 2010-06-23 |
| MX2009013197A (es) | 2010-04-27 |
| KR20100036306A (ko) | 2010-04-07 |
| US20110065692A1 (en) | 2011-03-17 |
| AU2008261803A1 (en) | 2008-12-18 |
| WO2008154447A1 (en) | 2008-12-18 |
| EP2166853A1 (en) | 2010-03-31 |
| BRPI0812369A2 (pt) | 2016-08-09 |
| JP2010529145A (ja) | 2010-08-26 |
| US8497262B2 (en) | 2013-07-30 |
| IL202287A0 (en) | 2010-06-16 |
| US20090005365A1 (en) | 2009-01-01 |
| US7858614B2 (en) | 2010-12-28 |
| CA2689934A1 (en) | 2008-12-18 |
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