FI113262B - Förfarande för framställning av fluorerade derivat av N-propargyl-1-amonoindan - Google Patents

Förfarande för framställning av fluorerade derivat av N-propargyl-1-amonoindan Download PDF

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Publication number
FI113262B
FI113262B FI924458A FI924458A FI113262B FI 113262 B FI113262 B FI 113262B FI 924458 A FI924458 A FI 924458A FI 924458 A FI924458 A FI 924458A FI 113262 B FI113262 B FI 113262B
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FI
Finland
Prior art keywords
aminoindan
fluorinated
fluoro
mao
propargyl
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Application number
FI924458A
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English (en)
Finnish (fi)
Other versions
FI924458A (fi
FI924458A0 (fi
Inventor
Jeff Sterling
Ruth Levy
Alex Veinberg
Willy Goldenberg
John Finberg
Musa Youdim
Arieh Gutman
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Teva Pharma
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Application filed by Teva Pharma filed Critical Teva Pharma
Publication of FI924458A0 publication Critical patent/FI924458A0/fi
Publication of FI924458A publication Critical patent/FI924458A/fi
Application granted granted Critical
Publication of FI113262B publication Critical patent/FI113262B/sv

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
    • C07C211/41—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems
    • C07C211/42—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems with six-membered aromatic rings being part of the condensed ring 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
    • 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
    • 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
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychology (AREA)
  • Pain & Pain Management (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (8)

1. Förfarande för framställning av som läkemedel användbart fluorerat N-propar-5 gyl-1 -aminoindan med formeln I (I) HN-CH
2-OCH och av dess farmaceutiskt acceptabla additionssalter eller en optiskt ren enantiomer, kännetecknat av att I) (a) ett racemiskt fluorerat 1-aminoindan med formeln 10 : :i* nh2 ai) : ·* fär reagera med propargylbromid eller propargylklorid i närvaro av en organisk eller oorganisk bas, eventuellt i närvaro av ett lämpligt lösningsmedel, och * * * • *, ϊ (b) om sä önskas, omvandlas den fria basen av reaktionsprodukten frän skede (a) :’: 15 tili sitt syraadditionssalt; och • * :: (c) om sä önskas, isoleras den (+)-enantiomera formen av den fria basen av (a) ske- ':: dets reaktionsprodukt kromatografiskt, genom destillering, genom selektiv urlakning . eller genom att omvandla den fria basen tili ett lämpligt syraadditionssalt och genom , [. [; dess fraktionsrekristallisation; eller
20 II) (i) ett racemiskt fluorerat 1-aminoindan enligt följande formel acyleras selektivt 113262 r^X~) nh2 med ett lämpligt acyleringsmedel i närvaro av subtiilein A -enzym, som isolerats frän Bacillus licheniformis, varvid det bildas en blandning innefattande en acylerad (+)-enantiomer av fluorerat 1-aminoindan och en oacylerad (-)-enantiomer av fluo-5 rerat 1-aminoindan; (ii) det fluorerade (-)-l-aminoindanet separeras frän det acylerade fluorerade (+)-1-aminoindanet kromatografiskt, genom destillering, genom selektiv urlakning eller genom att omvandla den fria basen till ett lämpligt syraadditionssalt och genom dess fraktionsrekristallisation; 10 (iii) den fluorerade 1-aminoindanproduktens (-)-enantiomer frän skede (ii) far reage-ra med en propargylbromid eller en propargylklorid i närvaro av en organisk eller oorganisk bas, eventuellt i närvaro av ett lämpligt lösningsmedel; och (iv) om sä önskas, omvandlas den fria basen av (+)-enantiomerfbreningen frän ske-, de (iii) tili sitt syraadditionssalt. 9 ; ; 15 2. Förfarande enligt patentkrav 1, kännetecknat av att det fluorerade 1-amino- • · indanet är ett 4-fluor-1 -aminoidan.
3. Förfarande enligt patentkrav 1, kännetecknat av att det fluorerade 1-amino- '; ’ * indanet är ett 5-fluor-1 -aminoindan.
4. Förfarande enligt patentkrav 1, kännetecknat av att det fluorerade 1- : v. 20 aminoindanet är ett 6-fluor-1 -aminoindan.
'·;* 5. Förfarande enligt nägot av patentkraven 1-4, kännetecknat av att en optiskt ; ; ’; ren (+)-enantiomer framställs.
6. Förfarande enligt nägot av patentkraven 1-4, kännetecknat av att en optiskt , ·' ren (-)-enantiomer framställs. 25 113262
7. Förfarande enligt patentkrav 1, kännetecknat av att det innefattar skedena I (a)-(c).
8. Förfarande enligt patentkrav 1, kännetecknat av att det innefattar skedena II (i)-(iv). • * * 2 » I %
FI924458A 1991-10-16 1992-10-02 Förfarande för framställning av fluorerade derivat av N-propargyl-1-amonoindan FI113262B (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IL99759A IL99759A (en) 1991-10-16 1991-10-16 Mono-fluorinated derivatives of n-propargyl-1-aminoindan, their preparation and pharmaceutical compositions containing them
IL9975991 1991-10-16

Publications (3)

Publication Number Publication Date
FI924458A0 FI924458A0 (fi) 1992-10-02
FI924458A FI924458A (fi) 1993-04-17
FI113262B true FI113262B (sv) 2004-03-31

Family

ID=11062970

Family Applications (1)

Application Number Title Priority Date Filing Date
FI924458A FI113262B (sv) 1991-10-16 1992-10-02 Förfarande för framställning av fluorerade derivat av N-propargyl-1-amonoindan

Country Status (16)

Country Link
US (1) US5486541A (sv)
EP (1) EP0538134B1 (sv)
JP (1) JP3247165B2 (sv)
CN (1) CN1038928C (sv)
AT (1) ATE149999T1 (sv)
AU (1) AU649565B2 (sv)
CA (1) CA2079968C (sv)
DE (1) DE69218101T2 (sv)
DK (1) DK0538134T3 (sv)
ES (1) ES2101063T3 (sv)
FI (1) FI113262B (sv)
GR (1) GR3023556T3 (sv)
HU (1) HU217589B (sv)
IL (2) IL99759A (sv)
NZ (1) NZ244616A (sv)
ZA (1) ZA927570B (sv)

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Also Published As

Publication number Publication date
HU217589B (hu) 2000-02-28
IL99759A0 (en) 1992-08-18
CN1038928C (zh) 1998-07-01
IL112819A (en) 2001-11-25
AU649565B2 (en) 1994-05-26
FI924458A (fi) 1993-04-17
ES2101063T3 (es) 1997-07-01
EP0538134A2 (en) 1993-04-21
CN1073427A (zh) 1993-06-23
NZ244616A (en) 1995-04-27
ATE149999T1 (de) 1997-03-15
DE69218101T2 (de) 1997-09-25
GR3023556T3 (en) 1997-08-29
HU9203162D0 (en) 1992-12-28
EP0538134B1 (en) 1997-03-12
DK0538134T3 (da) 1997-04-01
EP0538134A3 (en) 1993-06-16
FI924458A0 (fi) 1992-10-02
JPH05262701A (ja) 1993-10-12
IL99759A (en) 1997-06-10
CA2079968A1 (en) 1993-04-17
JP3247165B2 (ja) 2002-01-15
ZA927570B (en) 1993-04-14
HUT67218A (en) 1995-03-28
CA2079968C (en) 2004-12-21
DE69218101D1 (de) 1997-04-17
US5486541A (en) 1996-01-23
AU2606392A (en) 1993-04-22

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