SK10412003A3 - 8-{4-[3-(5-Fluór-1H-indol-3-yl)propyl]piperazín-1-yl}-2-metyl-4H- benzo[1,4]oxazin-3-ón-mesylát a farmaceutický prostriedok, ktorý ho obsahuje - Google Patents

8-{4-[3-(5-Fluór-1H-indol-3-yl)propyl]piperazín-1-yl}-2-metyl-4H- benzo[1,4]oxazin-3-ón-mesylát a farmaceutický prostriedok, ktorý ho obsahuje Download PDF

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Publication number
SK10412003A3
SK10412003A3 SK1041-2003A SK10412003A SK10412003A3 SK 10412003 A3 SK10412003 A3 SK 10412003A3 SK 10412003 A SK10412003 A SK 10412003A SK 10412003 A3 SK10412003 A3 SK 10412003A3
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Slovakia
Prior art keywords
mesylate
oxazin
piperazin
indol
benzo
Prior art date
Application number
SK1041-2003A
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English (en)
Inventor
Cornelis Bakker
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Solvay Pharmaceuticals B. V.
Priority date (The priority date 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 date listed.)
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Application filed by Solvay Pharmaceuticals B. V. filed Critical Solvay Pharmaceuticals B. V.
Publication of SK10412003A3 publication Critical patent/SK10412003A3/sk

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A61P25/18—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
    • A61P25/22—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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • 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)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Virology (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

Oblasť techniky
Predložený vynález sa týka nového vátu vzorca I fenylpiperazínového deri-
,ch3so3h a farmaceutického prostriedku, ktorý ho obsahuj e.
Doterajší stav techniky
Patentová prihláška č. PCT/EP00/08090 (doteraz nepublikovaná) sa týka skupiny nových fenylpiperazínov. Zlúčeniny z tejto skupiny vykazujú vysokú afinitu ako voči dopamínovému D2 receptoru, tak voči miestu reabsorpcie sérotonínu. Táto kombinácia je použitelná na liečenie schizofrénie a ďalších psychotických ochorení a umožňuje kompletnejšiu liečbu všetkých symptómov ochorení (napr. pozitívnych symptómov a negatívnych symptómov).
Zlúčeniny vykazujú účinky antagonistov dopamínových D2 receptorov, lebo potenciálne antagonizujú apomorfínom vyvolané správanie v zmysle šplhania u myši. Zlúčeniny tiež vykazujú účinky inhibítorov reabsorpcie sérotonínu, keďže zosilňujú u myši správanie vyvolané 5-HTP.
Zlúčeniny sú účinné v terapeutických modeloch senzitívnych na klinicky relevantné antipsychotiká (napr. podmienená vyhýbacia reakcia; Van der Heyden & Bradford, Behav. Brain Res., 1988,
31: 61 až 67) a antidepresiva alebo anxiolytiká (napr. supresia stresom vyvolanej vokalizácie; van der Poel a kol., Psychofarmacology, 1989, 97: 147 až 148) .
Oproti klinicky relevantným antagonistom dopaminových D2 receptorov majú opisované zlúčeniny nízky sklon vyvolať katalepsiu u hlodavcov a samotné pravdepodobne vyvolávajú menej extrapyramidálne vedľajšie účinky ako existujúce antipsychotické činidlá .
Inhibičná aktivita na reabsorpciu sérotonínu vlastná týmto zlúčeninám môže zodpovedať terapeutickým účinkom pozorovaným na modeloch správania senzitívnych buď na antidepresiva alebo na anxiolytiká.
Zlúčeniny sa môžu použiť na liečenie afekcií alebo ochorení centrálneho nervového systému spôsobených buď poruchami dopamínergného alebo sérotonergného systému, napr.: agresie, úzkostných porúch, autizmu, vertiga, depresie, kognitívnych porúch alebo porúch pamäti, Parkinsonovej choroby a najmä schizofrénie a ďalších psychotických ochorení.
Podstata vynálezu
Teraz sa zistilo, že mesylát skôr uvedeného vzorca vykazuje, v porovnaní s voľnou zásadou (to znamená zlúčeninou č. 89 z EP 99202710.2), výhodné vlastnosti.
Táto mesylátová zlúčenina je oveľa lepšie rozpustná vo vode ako voľná zásada, čo vedie k dobrej biologickej dostupnosti.
Zlúčenina obsahuje chirálne centrum, k predmetu vynálezu patria ako racemické zmesi, tak jednotlivé enantioméry.
Zlúčeninu je možné vhodnými spôsobmi, s použitím pomocných látok, ako sú kvapalné alebo pevné nosné látky, upraviť do formy vhodnej na podávanie.
Volná zásada zlúčeniny sa môže pripraviť spôsobom opísaným v EP 99202710.2.
Volná zásada sa môže previesť na mesylát v súlade so známymi spôsobmi vytvárania solí.
Vynález je ilustrovaný pomocou nasledujúceho príkladu uskutočnenia vynálezu.
Príklady uskutočnenia vynálezu
Príklad
2,0 g (4,7 mmol) volnej zásady, ktorá sa môže získať spôsobom opísaným v EP 99202710.2 (zlúčenina č. 89) sa suspenduje v 40 ml metanolu. Suspenzia sa zahreje na 60°C a v priebehu asi dvoch minút sa pridá roztok 0,45 g (4,7 mmol) kyseliny metánsulfónovej v 10 ml metanolu. Získa sa číry roztok. Po miešaní počas 5 minút pri 60°C začína kryštalizácia. Roztok sa pomaly, v priebehu 60 minút, ochladí na 20°C a mieša sá pri tejto teplore počas 30 minút. V priebehu 60 minút sa uskutoční ďalšie ochladenie na 0°C a mieša sa počas 90 minút. Pevná látka sa izoluje filtráciou, premyje 5 ml metanolu a v priebehu noci sa suší pri 50°C za zníženého tlaku. Výťažok predstavuje 2,17 g (88%) bielo sfarbeného mesylátu.

Claims (3)

  1. PATENTOVÉ NÁROKY
    1. 8-(4-(3-(5-fluór-ltf-indol-3-yl)propyl]piperazin-l-yl}-2-me tyl-4H-benzo[1,4]oxazin-3-ón-mesylát vzorca I
    H-N O
    N
    I
    H
  2. 2. Farmaceutická kompozícia na liečenie porúch centrálneho ner vového systému, vyznačujúca sa tým, že obsahuj zlúčeninu podľa nároku 1 ako účinnú látku.
  3. 3. Spôsob liečenia porúch centrálneho nervového systému, v y z načujúci sa tým, že sa použije zlúčenina podlá ná roku 1.
SK1041-2003A 2001-02-21 2002-02-19 8-{4-[3-(5-Fluór-1H-indol-3-yl)propyl]piperazín-1-yl}-2-metyl-4H- benzo[1,4]oxazin-3-ón-mesylát a farmaceutický prostriedok, ktorý ho obsahuje SK10412003A3 (sk)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP01200610 2001-02-21
PCT/EP2002/001795 WO2002066473A1 (en) 2001-02-21 2002-02-19 8’4-’3-(5-fluoro-1h-indol-3yl) propyl!-1-piperazynyl!-2-methyl-2h-1,4-benzoxazin -3 (4h)- one methanesulfonate with high affinity for the dopamine d 2 receptor and the serotonin reuptake site

Publications (1)

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SK10412003A3 true SK10412003A3 (sk) 2004-03-02

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SK1041-2003A SK10412003A3 (sk) 2001-02-21 2002-02-19 8-{4-[3-(5-Fluór-1H-indol-3-yl)propyl]piperazín-1-yl}-2-metyl-4H- benzo[1,4]oxazin-3-ón-mesylát a farmaceutický prostriedok, ktorý ho obsahuje

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US (2) US6958396B2 (sk)
EP (1) EP1366044B1 (sk)
JP (1) JP4216072B2 (sk)
KR (1) KR100859107B1 (sk)
CN (1) CN1284780C (sk)
AR (1) AR032712A1 (sk)
AT (1) ATE472545T1 (sk)
AU (1) AU2002250983B2 (sk)
BR (1) BR0206162A (sk)
CA (1) CA2430707C (sk)
CZ (1) CZ20032171A3 (sk)
DE (1) DE60236848D1 (sk)
DZ (1) DZ3490A1 (sk)
ES (1) ES2347321T3 (sk)
HK (1) HK1078569A1 (sk)
HU (1) HUP0303330A3 (sk)
IL (1) IL155720A0 (sk)
MX (1) MXPA03007430A (sk)
NO (1) NO325298B1 (sk)
NZ (1) NZ526018A (sk)
PL (1) PL201176B1 (sk)
RU (1) RU2281945C2 (sk)
SK (1) SK10412003A3 (sk)
WO (1) WO2002066473A1 (sk)
ZA (1) ZA200304267B (sk)

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JP4216072B2 (ja) 2009-01-28
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CN1284780C (zh) 2006-11-15
DZ3490A1 (fr) 2002-08-29
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US20040024207A1 (en) 2004-02-05
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