DK2769980T3 - Pyrazolquinolinderivat som pde9-inhibitorer - Google Patents
Pyrazolquinolinderivat som pde9-inhibitorer Download PDFInfo
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- DK2769980T3 DK2769980T3 DK12837953.4T DK12837953T DK2769980T3 DK 2769980 T3 DK2769980 T3 DK 2769980T3 DK 12837953 T DK12837953 T DK 12837953T DK 2769980 T3 DK2769980 T3 DK 2769980T3
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- 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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
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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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61P25/28—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
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- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (18)
1. Forbindelse eller farmakologisk acceptabelt salt deraf med formel (1):
(l) hvor R1 er et hydrogenatom; R2 er en aromatisk ringgruppe, der er udvalgt fra gruppen, der består af en phenylgruppe, en pyridinylgruppe og en pyrimidinylgruppe, hvor de to atomer på den aromatiske ring, der grænser op til carbonatomet, der er bundet til pyrazol[4,3-c]quinolinringen, hver uafhængigt har en substituent, der er udvalgt fra gruppe Al, og de andre atomer på den aromatiske ring uafhængigt eventuelt har en substituent, der er udvalgt fra gruppe Bl; R3 er et hydrogenatom eller et fluoratom; R4 er et hydrogenatom; R5 er en oxepanylgruppe, en dioxepanylgruppe, en tetrahydropyranylgruppe eller en tetrahydrofuranylgruppe, der eventuelt har en methoxygruppe; R6 er et hydrogenatom; gruppe Al består af et halogenatom, en Cl-6-alkylgruppe, der eventuelt har 1 til 3 halogenatomer, og en Cl-6-alkoxygruppe; og gruppe Bl består af et halogenatom, en cyanogruppe, en Cl-6-alkylgruppe, der eventuelt har 1 til 3 halogenatomer, en Cl-6-alkoxy-Cl-6-alkylgruppe, en Cl-6-alkoxygruppe, der eventuelt har 1 til 3 halogenatomer, og en tetrahydropyranylgruppe, med det forbehold, at når R2 er en 3-pyridinylgruppe, så er substituenten i 4-positionen et halogenatom eller en Cl-6-alkylgruppe, der eventuelt har 1 til 3 halogenatomer.
2. Forbindelse eller farmakologisk acceptabelt salt deraf ifølge krav 1, hvor R2 er en aromatisk ringgruppe, der er udvalgt fra gruppen, der består af en phenylgruppe, en 3-pyridinylgruppe, en 4-pyridinylgruppe og en 5-pyrimidinylgruppe, hvor de to atomer på den aromatiske ring, der grænser op til carbonatomet, der er bundet til pyrazol[4,3-c]quinolinringen, hver uafhængigt har en substituent, der er udvalgt fra gruppe A2, og de andre atomer på den aromatiske ring uafhængigt eventuelt har en substituent, der er udvalgt fra gruppe B2; R5 er en 4-oxepanylgruppe, en 1,4-dioxepan-6-ylgruppe, en 3, 4,5, 6-tetrahydro-2H-3-pyranylgruppe, en 3,4,5,6-tetrahydro-2H-4-pyranylgruppe eller en 3-tetrahydrofuranylgruppe; gruppe A2 består af et chloratom og en methylgruppe, der eventuelt har 1 til 2 fluoratomer, en ethylgruppe, en methoxygruppe og en ethoxygruppe; og gruppe B2 består af et fluoratom, et chloratom, en cyanogruppe, en methylgruppe, der eventuelt har 1 til 3 fluoratomer, en ethylgruppe, en methoxymethylgruppe, en methoxygruppe, der eventuelt har 1 til 3 fluoratomer, en ethoxygruppe, en isopropyloxygruppe og en 3,4,5,6-tetrahydro-2H-4-pyranylgruppe.
3. Forbindelse eller farmakologisk acceptabelt salt deraf ifølge krav 2, hvor R3 er et fluoratom.
4. Forbindelse eller farmakologisk acceptabelt salt deraf ifølge krav 1, hvor R3 er et hydrogenatom; og R5 er en tetrahydropyranylgruppe eller en tetrahydrofuranylgruppe, der eventuelt har en methoxygruppe.
5. Forbindelse eller farmakologisk acceptabelt salt deraf ifølge krav 2, hvor R3 er et hydrogenatom; og R5 er en 3,4,5, 6-tetrahydro-2H-3-pyranylgruppe, en 3,4,5,6-tetrahydro-2H-4-pyranylgruppe eller en 3- tetrahydrofuranylgruppe.
6. Forbindelse eller farmakologisk acceptabelt salt deraf ifølge krav 1, hvor R2 er en aromatisk ringgruppe, der er udvalgt fra gruppen, der består af en phenylgruppe, en 3-pyridinylgruppe og en 4-pyridinylgruppe, hvor de to atomer på den aromatiske ring, der grænser op til carbonatomet, der er bundet til pyrazol[4,3-c]quinolinringen, hver uafhængigt har en substituent, der er udvalgt fra gruppe A3, og de andre atomer på den aromatiske ring uafhængigt eventuelt har en substituent, der er udvalgt fra gruppe B3; R3 er et hydrogenatom; R4 er et hydrogenatom; R5 er en 3,4,5, 6-tetrahydro-2H-4-pyranylgruppe eller en 3-tetrahydrofuranylgruppe; gruppe A3 består af en methylgruppe og en methoxygruppe; og gruppe B3 består af en methylgruppe, en methoxygruppe og en methoxymethylgruppe.
7. Forbindelse eller farmakologisk acceptabelt salt deraf ifølge krav 1, der er udvalgt fra følgende gruppe: 1) 7-(6-methoxy-2,4-dimethylpyridin-3-yl)-1-(tetrahydro-2H-pyran-4-yl)-lH-pyrazol[4,3-c]quinolin-4(5H)-on, 2) 7-(2-methoxy-4,6-dimethylpyridin-3-yl)-1-(tetrahydro-2H-pyran-4-yl)-lH-pyrazol[4,3-c]quinolin-4 (5H)-on, 3) (S)-7- ( 6-isopropyloxy-2,4-dimethylpyridin-3-yl)-1-(tetrahydrofuran-3-yl)-lH-pyrazol[4,3-c]quinolin-4(5H)-on, 4) 8-fluor-7-(2-methoxy-4,6-dimethylpyridin-3-yl)-1-(tetrahydro-2H-pyran-4-yl)-lH-pyrazol[4,3-c]quinolin-4(5H)-on, 5) 1-(1,4-dioxepan-6-yl)-7-(2-methoxy-3,5-dimethylpyridin-4-yl)-lH-pyrazol[4,3-c]quinolin-4(5H)-on, 6) 1-(1,4-dioxepan-6-yl)-7-(2-methoxy-4,6-dimethylpyridin-3-yl)-lH-pyrazol[4,3-c]quinolin-4(5H)-on, 7) (S)-8-fluor-7-(2-methoxy-3,5-dimethylpyridin-4-yl)-1-(tetrahydrofuran-3-yl)-lH-pyrazol[4,3-c]quinolin-4(5H)-on, 8) 7-(2-methoxy-3,5-dimethylpyridin-4-yl)-1-(tetrahydro-2H-pyran-4-yl)-lH-pyrazol[4,3-c]quinolin-4(5H)-on, 9) (-)-7-(2-methoxy-4,6-dimethylpyridin-3-yl)-1-(tetrahydrofuran-3-yl)-lH-pyrazol[4,3-c]quinolin-4(5H)-on, 10) (-)-7-(6-methoxy-2,4-dimethylpyridin-3-yl)-1- (tetrahydrofuran-3-yl)-lH-pyrazol[4,3-c]quinolin-4(5H)-on, 11) (S)-8-fluor-7-(2-methoxy-4,6-dimethylpyridin-3-yl)-1-(tetrahydrofuran-3-yl)-lH-pyrazol[4,3-c]quinolin-4(5H)-on, 12) (S)-7-(6-ethoxy-2,4-dimethylpyridin-3-yl)-1-(tetrahydrofuran-3-yl)-lH-pyrazol[4,3-c]quinolin-4(5H)-on, 13) (S)-8-fluor-7-(6-methoxy-2,4-dimethylpyridin-3-yl)-1-(tetrahydrofuran-3-yl)-lH-pyrazol[4,3-c]quinolin-((5H)-on og 14) (S)-7-(2-methoxy-3,5-dimethylpyridin-4-yl)-1-(tetrahydrofuran-3-yl)-lH-pyrazol[4,3-c]quinolin-4(5H)-on.
8. Forbindelse eller farmakologisk acceptabelt salt deraf ifølge krav 7, som er 7-(6-isopropyloxy-2,4-dimethylpyridin-3-yl)-1-(tetrahydrofuran-3-yl)-lH-pyrazol[4,3-c]quinolin-4(5H)-on.
9. Forbindelse eller farmakologisk acceptabelt salt deraf ifølge krav 7, som er (S)-7-(6-isopropyloxy-2,4-dimethylpyridin-3-yl)-1-(tetrahydrofuran-3-yl)-lH-pyrazol[4,3— c]quinolin-4(5H)-on:
10. Forbindelse eller farmakologisk acceptabelt salt deraf ifølge krav 7, som er 8-fluor-7-(2-methoxy-3,5- dimethylpyridin-4-yl)-1-(tetrahydrofuran-3-yl)-lH-pyrazol[4,3— c]quinolin-4(5H)-on.
11. Forbindelse eller farmakologisk acceptabelt salt deraf ifølge krav 7, som er (S)-8-fluor-7-(2-methoxy-3,5-dimethylpyridin-4-yl)-1-(tetrahydrofuran-3-yl)-lH-pyrazol[4,3-c]quinolin-4(5H)-on:
12. Forbindelse eller farmakologisk acceptabelt salt deraf ifølge krav 7, som er 7-(2-methoxy-3,5-dimethylpyridin-4-yl)-1-(tetrahydrofuran-3-yl)-lH-pyrazol[4,3-c]quinolin-4(5H)-on.
13. Forbindelse eller farmakologisk acceptabelt salt deraf ifølge krav 7, som er (S)-7-(2-methoxy-3,5-dimethylpyridin-4-yl)-1-(tetrahydrofuran-3-yl)-lH-pyrazol[4,3-c]quinolin-4(5H)- on:
14. Forbindelse eller farmakologisk acceptabelt salt deraf ifølge krav 7, som er 1-(1,4-dioxepan-6-yl)-7-(2-methoxy-3,5-dimethylpyridin-4-yl)-lH-pyrazol[4,3-c]quinolin-4(5H)-on:
15. Farmaceutisk sammensætning, der omfatter forbindelsen eller det farmakologisk acceptable salt deraf ifølge krav 1 som en aktiv bestanddel.
16. Farmaceutisk sammensætning ifølge krav 15 til anvendelse som en PDE9-inhibitor.
17. Farmaceutisk sammensætning ifølge krav 15 til anvendelse i en fremgangsmåde til forøgelse af den intracerebrale cGMP-koncentration.
18. Forbindelse eller farmakologisk acceptabelt salt deraf ifølge krav 1 til anvendelse til forbedring af kognitiv svækkelse ved Alzheimers sygdom.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161544860P | 2011-10-07 | 2011-10-07 | |
| US201161550623P | 2011-10-24 | 2011-10-24 | |
| US201161558110P | 2011-11-10 | 2011-11-10 | |
| US201161580903P | 2011-12-28 | 2011-12-28 | |
| PCT/JP2012/075748 WO2013051639A1 (ja) | 2011-10-07 | 2012-10-04 | ピラゾロキノリン誘導体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2769980T3 true DK2769980T3 (da) | 2016-04-11 |
Family
ID=48043792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK12837953.4T DK2769980T3 (da) | 2011-10-07 | 2012-10-04 | Pyrazolquinolinderivat som pde9-inhibitorer |
Country Status (33)
| Country | Link |
|---|---|
| US (2) | US8563565B2 (da) |
| EP (1) | EP2769980B1 (da) |
| JP (1) | JP5546693B2 (da) |
| KR (1) | KR101943680B1 (da) |
| CN (1) | CN103930423B (da) |
| AR (1) | AR088235A1 (da) |
| AU (1) | AU2012319549B2 (da) |
| BR (1) | BR112014007912B1 (da) |
| CA (1) | CA2861795C (da) |
| CL (1) | CL2014000821A1 (da) |
| CO (1) | CO6910200A2 (da) |
| CY (1) | CY1117427T1 (da) |
| DK (1) | DK2769980T3 (da) |
| ES (1) | ES2568015T3 (da) |
| HR (1) | HRP20160273T1 (da) |
| HU (1) | HUE028555T2 (da) |
| IL (1) | IL231650A (da) |
| IN (1) | IN2014CN02463A (da) |
| JO (1) | JO3116B1 (da) |
| ME (1) | ME02394B (da) |
| MX (1) | MX358149B (da) |
| MY (1) | MY167698A (da) |
| PE (1) | PE20141557A1 (da) |
| PH (1) | PH12014500580A1 (da) |
| PL (1) | PL2769980T3 (da) |
| RS (1) | RS54702B1 (da) |
| RU (1) | RU2605096C2 (da) |
| SG (1) | SG11201400717QA (da) |
| SI (1) | SI2769980T1 (da) |
| SM (1) | SMT201600108B (da) |
| TW (1) | TWI562993B (da) |
| WO (1) | WO2013051639A1 (da) |
| ZA (1) | ZA201402439B (da) |
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| WO2017046606A1 (en) * | 2015-09-18 | 2017-03-23 | Redx Pharma Plc | Antibacterial compounds |
| CN107056690A (zh) * | 2017-03-22 | 2017-08-18 | 上海康鹏科技有限公司 | 一种6‑溴吡啶‑3‑甲醛的制备方法 |
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2012
- 2012-10-04 JO JOP/2012/0302A patent/JO3116B1/ar active
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