1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochloride
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- CAS-Nr.
- 903576-44-3
- Englisch Name:
- 1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochloride
- Synonyma:
- Pitolisant HCl;CS-2751;BF 2649;CS-1548;BF2649 HCl;Ciproxidine;Ciproxidine BF2649;Pitolisant HCI salt;BF 2649 hydrochloride;Pitolisant Hcl(BF2.649
- CBNumber:
- CB62518970
- Summenformel:
- C17H26ClNO.HCl
- Molgewicht:
- 332
- MOL-Datei:
- 903576-44-3.mol
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1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochloride Eigenschaften
- storage temp.
- Desiccate at RT
- L?slichkeit
- ≥16.6 mg/mL in DMSO; ≥57.4 mg/mL in H2O; ≥94.2 mg/mL in EtOH
- Aggregatzustand
- solid
- Farbe
- White to off-white
- InChI
- 1S/C17H26ClNO.ClH/c18-17-9-7-16(8-10-17)6-4-14-20-15-5-13-19-11-2-1-3-12-19;/h7-10H,1-6,11-15H2;1H
- InChIKey
- XLFKECRRMPOAQS-UHFFFAOYSA-N
- SMILES
- Clc1ccc(cc1)CCCOCCCN2CCCCC2.Cl
Sicherheit
| WGK Germany |
WGK 3 |
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| Speicherklasse |
11 - Combustible Solids |
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| Hazard Classifications |
Repr. 2 |
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1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochloride Chemische Eigenschaften,Einsatz,Produktion Methoden
Beschreibung
Pitolisant hydrochloride,
a first-in-class inverse agonist of the histamine H3
receptor, was approved in the EU for the treatment of excessive
daytime sleepiness (EDS) in adults with narcolepsy with or
without cataplexy. The drug, which was developed by
Bioprojet and has orphan drug designation in the EU and
US, enhances wakefulness by increasing histaminergic neuron
activity. With once daily oral administration in the morning,
patients taking pitolisant exhibited significantly reduced EDS
versus placebo but not versus modafinil. Plasma levels of the
drug are reduced at the end of the day such that its waking
effect is minimized at night (plasma t1/2 10-12 h). Several
articles have been published detailing the discovery of
pitolisant.
Synthese
The most likely scale preparation of pitolisant hydrochloride
consists of only four synthetic steps starting with the mesylation
of commercial 3-(4-chlorophenyl)propan-1-ol (132). Displacement of the mesylate with the sodium salt of
commercial 3-(piperidin-1-yl)propan-1-ol (133) in warm DMA
assembled the parent drug in 97% yield over two steps. Salt
formation was affected by pH adjustment to 3-4 using HCl gas
in EtOAc. Recrystallization from ethyl acetate and isopropanol
provided pitolisant hydrochloride (XII) on kilogram scale in
78% overall yield across the short four-step protocol.
1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochloride Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochloride Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.
Global( 129)Lieferanten
903576-44-3()Verwandte Suche:
- 1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochloride
- BF 2649
- Ciproxidine
- Pitolisant (hydrochloride)
- 1-[3-[3-(4-Chlorophenyl)propoxy]propyl]piperidine monohydrochloride
- Piperidine, 1-[3-[3-(4-chlorophenyl)propoxy]propyl]-, hydrochloride
- BF 2649 hydrochloride
- Ciproxidine BF2649
- PITOLISANT;CIPROXIDINE BF2649
- Pitolisant hydrochloride (Ciproxidine
- CS-2751
- CS-1548
- Pitolisant Hcl(BF2.649
- CIPROXIDINE;BF 2649;BF2649;BF-2649
- Pitolisant HCI salt
- 1-[3-[3-(4-Chlorophenyl)propoxy]propyl]piperidine HCl
- PITOLISANT HYDROCHLORIDE;BF 2649;BF2649;BF-2649
- Pitolisant (Ciproxidine
- Pitolisant hydrochloride,BF-2649,inhibit,BF2649,Inhibitor,Histamine Receptor,Pitolisant
- BF2649 HCl
- Pitolisant hydrochloride, 10 mM in DMSO
- Pitolisant hydrochloride - Bio-X ?
- Tilorizine Hydrochloride
- Pitolisant HCl
- 903576-44-3
- C17H26ClNOHCl
- Inhibitor
