FI112650B - Förfarande för framställning av nya cykloalkylalkylaminer, vilka är sigmareceptorligander användbara som läkemedel, och aminoalkoholmellanprodukt - Google Patents

Förfarande för framställning av nya cykloalkylalkylaminer, vilka är sigmareceptorligander användbara som läkemedel, och aminoalkoholmellanprodukt Download PDF

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Publication number
FI112650B
FI112650B FI933403A FI933403A FI112650B FI 112650 B FI112650 B FI 112650B FI 933403 A FI933403 A FI 933403A FI 933403 A FI933403 A FI 933403A FI 112650 B FI112650 B FI 112650B
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methyl
amino
formula
ethyl
methylene chloride
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FI933403A
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English (en)
Finnish (fi)
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FI933403A (fi
FI933403A0 (fi
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Jean-Louis Junien
Alain Pierre Calvet
Henri Jacobelli
Francois Joseph Roman
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Jouveinal Inst Rech
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • 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
    • C07C211/34—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 a saturated carbon skeleton
    • C07C211/38—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 a saturated carbon skeleton containing condensed ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/42—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
    • C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
    • C07C225/18—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings the carbon skeleton containing also rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • 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
    • 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
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
    • 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
    • C07C2602/12—One of the condensed rings being a six-membered aromatic ring the other ring being at least seven-membered

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Psychiatry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyrane Compounds (AREA)
  • Steroid Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Medicinal Preparation (AREA)
  • Saccharide Compounds (AREA)

Claims (10)

1. Förfarande för framställning av cykloalkylal-kylaminer, vilka är sigmareceptorligander användbara som 5 läkemedel och vilka har den allmänna formeln (I), och sy-raadditionssalter därav med farmaceutiskt godtagbara sy-ror, V1 V2 R, γ ^(CHgJm-CH^^CH2)n (I) 15 där Ri är H eller lägre alkyl; X och Y, vilka kan vara lika eller olika, är H, OH, lägre alkyl, lägre alkoxi, halogen eller nitril; Vi och V2 tillsammans bildar en dubbelbindning, som är bunden tili en syreatom eller en hydroxiiminoradikal N-20 OH, eller de är bundna under bildande av en etylen-dioxikedja -O-CH2-CH2-O-; • A stär för en valensbindning, en syreatom, en me- : : tylengrupp eller en etylengrupp; ·;· m är 0, 1 eller 2, och 25 n är ett heltal 1-5; kännetecknat av, att (A) vid f ramställning av en cykloalkylalkylamin, ' där Vi och V2 tillsammans bildar en dubbelbindning, som är bunden tili en syreatom, varvid nämnda cykloalkylalkylamin » » • ’ 30 motsvarar formeln (I.a) i‘: 0 R1 *, Il | (I.a) γ [| ~^| CH?)m-CH (CH2)n : 35 J • s 112650 58 i) cykliseras och dekarboxyleras en malonmellan-produkt (VIII) genom upphettning i ett surt medium R1
2. Förfarande enligt patentkrav 1, kanne-. t e c k n a t av, att Vi och V2 tillsammans bildar en dubbelbindning, som är bunden tili en syreatom. • 35
3. Förfarande enligt patentkrav 1 eller 2, k ä n- : netecknat av, att A star för en metylengrupp. 6o 112650
4. Förfarande enligt nägot av patentkraven 1-3, kännetecknat av, att Rx är CH3.
5. Förfarande enligt nagot av de föregäende patentkraven, kännetecknat av, att m = 1 5 eller 2 och n = 2 eller 3.
5 CH^^CCHg ] n (Jb) omsätts den ovan erhällna cykloalkylalkylaminen (I.a) med hydroxylamin, och 10 (C) vid framställning av en cykloalkylalkylamin, i vilken Vi och V2 är bundna under bildande av en etylen-dioxikedja och vilken motsvarar formeln (I.c) 15 ΓΛ x o. /0 I ><c /NL / \ (I.C) Λ ^(CH2)m-CH^JXH2)n 20 bringas den ovan erhällna cykloalkylalkylaminen (I.a) att reagera genom upphettning med etylenglykol i ett surt me-* ',· dium, eller en amidmellanprodukt (III. a) « :;T ΓΛ "i : * : 25 x °\/0 I —‘'s. -CH^JCH2)n (III'a) 30 reduceras medelst en metallhydrid eller en metallorganisk hydrid.
5 VvO-Γ N γ ^(CH21m-CH^JCH2)n (VIII) A OR 10 där R är väte, lägre alkyl eller lägre cykloalkyl, eller (ii) cykliseras en syramellanprodukt (IX) R1 OH I 1 X I I 15 0=0. ' (IX) Y 'P'nS ^(CH2)m CJ^JCH2]n medelst en acyleringsmetod av Friedel-Crafts-typ, eller 20 (iii) oxideras hydroxylfunktionen i en amino- alkohol (II) * * OH R, : i' x, f I : 25 CH (CH2)n (II) :;;; YtAAJ ^ « · a , , genom anvandning av ett oxiderande reagens, som är härlett ; 30 ur krom, och (B) vid framställning av en cykloalkylalkylamin, där Vi och V2 tillsammans bildar en dubbelbinding, som är bunden tili en hydroxiiminoradikal och varvid nämnda cykloalkylalkylamin motsvarar formeln (I.b) : 35 59 1 12650 OH N R, V\ JI N /^\
6. Förfarande enligt patentkrav 1 för framställ-ning av cykloalkylalkylaminer med formeln (I), kännetecknat av, att de är: 2-[2-[(N-cyklobutylmetyl-N-metyl)amino]etyl]-Ι- ΙΟ oxo-1,2,3,4-tetrahydronaftalen eller en hydroklorid därav och 2-[2-[(N-cyklopropyletyl-N-metyl)amino]etyl]-1-oxo-1,2,3,4-tetrahydronaftalen eller en hydroklorid därav.
7. Aminoalkoholförening med formeln (II) 15 OH R, -CH^(CH2)n <n) 2 0 ; ’.· där Ri är H eller lägre alkyl; ( X och Y, vilka är identiska eller olika, är H, OH, '·· lägre alkyl, lägre alkoxi, halogen eller nitril; 25. star för en valensbindning, en syreatom, en me- :v. tylengrupp eller en etylengrupp; m är 0, 1 eller 2; och n är ett heltal 1-5.
FI933403A 1992-07-31 1993-07-29 Förfarande för framställning av nya cykloalkylalkylaminer, vilka är sigmareceptorligander användbara som läkemedel, och aminoalkoholmellanprodukt FI112650B (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR929209536A FR2694287B1 (fr) 1992-07-31 1992-07-31 Nouvelles cycloalkylalkylamines ligands aux récepteurs sigma, leur procédé de préparation et leur application en thérapeutique.
FR9209536 1992-07-31

Publications (3)

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FI933403A0 FI933403A0 (fi) 1993-07-29
FI933403A FI933403A (fi) 1994-02-01
FI112650B true FI112650B (sv) 2003-12-31

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FI933403A FI112650B (sv) 1992-07-31 1993-07-29 Förfarande för framställning av nya cykloalkylalkylaminer, vilka är sigmareceptorligander användbara som läkemedel, och aminoalkoholmellanprodukt

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US (1) US5326784A (sv)
EP (1) EP0581677B1 (sv)
JP (1) JP3179942B2 (sv)
KR (1) KR100314102B1 (sv)
AT (1) ATE147373T1 (sv)
AU (1) AU660829B2 (sv)
CA (1) CA2101575C (sv)
DE (1) DE69307210T2 (sv)
ES (1) ES2099395T3 (sv)
FI (1) FI112650B (sv)
FR (1) FR2694287B1 (sv)
MX (1) MX9304578A (sv)
NO (1) NO179512C (sv)
NZ (1) NZ248279A (sv)
TW (1) TW230190B (sv)
ZA (2) ZA935482B (sv)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5504253A (en) * 1994-07-15 1996-04-02 Nps Pharmaceuticals, Inc. Amine preparation
US5648541A (en) * 1995-09-28 1997-07-15 Nps Pharmaceuticals, Inc. Chiral reductions of imines leading to the syntheses of optically active amines
FR2751645B1 (fr) * 1996-07-29 1998-12-24 Sanofi Sa Amines pour la fabrication de medicaments destines a empecher la proliferation de cellules tumorales
CA3192518A1 (en) 2020-09-17 2022-03-24 Xavier MANIERE Compounds for treating virus infections

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0038388A1 (en) * 1980-04-17 1981-10-28 Exxon Research And Engineering Company Foam dispensing nozzle and method and apparatus for transporting laminates comprising a foamable plastics material using a nozzle
JP2931986B2 (ja) * 1989-02-17 1999-08-09 武田薬品工業株式会社 アラルキルアミン誘導体
CA2071897A1 (en) * 1989-12-28 1991-06-29 Richard A. Glennon Sigma receptor ligands and the use thereof

Also Published As

Publication number Publication date
FR2694287A1 (fr) 1994-02-04
CA2101575A1 (en) 1994-02-01
AU660829B2 (en) 1995-07-06
JPH06206851A (ja) 1994-07-26
NO932728D0 (no) 1993-07-29
MX9304578A (es) 1994-01-31
CA2101575C (en) 2004-03-23
JP3179942B2 (ja) 2001-06-25
NO932728L (no) 1994-02-01
TW230190B (sv) 1994-09-11
DE69307210D1 (de) 1997-02-20
ZA935434B (en) 1994-02-22
FI933403A (fi) 1994-02-01
ES2099395T3 (es) 1997-05-16
KR100314102B1 (ko) 2002-08-28
FR2694287B1 (fr) 1994-09-16
NZ248279A (en) 1995-12-21
DE69307210T2 (de) 1997-05-15
US5326784A (en) 1994-07-05
KR940005550A (ko) 1994-03-21
NO179512B (no) 1996-07-15
ZA935482B (en) 1994-02-28
NO179512C (no) 1996-10-23
EP0581677A1 (fr) 1994-02-02
ATE147373T1 (de) 1997-01-15
FI933403A0 (fi) 1993-07-29
EP0581677B1 (fr) 1997-01-08
AU4427993A (en) 1994-02-03

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