FI95465B - Förfarande för framställning av terapeutiskt användbara N-substituerade arylpiperidinderivat - Google Patents

Förfarande för framställning av terapeutiskt användbara N-substituerade arylpiperidinderivat Download PDF

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Publication number
FI95465B
FI95465B FI903829A FI903829A FI95465B FI 95465 B FI95465 B FI 95465B FI 903829 A FI903829 A FI 903829A FI 903829 A FI903829 A FI 903829A FI 95465 B FI95465 B FI 95465B
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Finland
Prior art keywords
methoxyphenyl
piperidinyl
preparation
product
process according
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FI903829A
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English (en)
Finnish (fi)
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FI95465C (sv
FI903829A0 (sv
Inventor
Arthur A Nagel
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Pfizer
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Publication of FI903829A0 publication Critical patent/FI903829A0/sv
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Publication of FI95465C publication Critical patent/FI95465C/sv

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/20—Spiro-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
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22—Bridged ring systems
    • C07D221/24—Camphidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Psychiatry (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Claims (10)

1. Förfarande för framställning av terapeutiskt användbara N-substituerade arylpiperidinföreningar med 5 formeIn I Arsv—^ Λ N-(CH2)n-R (I) io N—' väri Ar är metoxifenyl eller naftyl, n är ett heltal 2 -4 och R Mr 2-amino-4-tiazolylfenyl, 5-oxindolyl, 2-metyl- 4-oxo-4H-pyrido[l,2-a]pyrimidin-3-yl eller 1,8,8-trimetyl-15 2,4-dioxo-3-azabicyklo[3.2.l]oktan-3-yl, förutsatt att Ar är alltid i 4-ställning av piperidinringen, när n är nägot annat heltal än tvä, och farmaceutiskt godtagbara syraad-ditionssalter därav, kännetecknat därav, att man omsätter en arylpiperidinförening med formeln II 20 Ar)c^ ( NH (II) \_/ 25 väri Ar betecknar sanuna som ovan, med ett aralkyl- eller aryloxialkyl- eller heterocyklylalkyleterderivat eller med en motsvarande halogenid med formeln
30 Q( CH2 )nR • « väri R och n betecknar samma som ovan och Q är p-toluen-sulfonyloxi eller en halogenatom som valts bland klor och brom; och därefter, ifali behövligt, omvandlar den resul-35 terande fria organiska basföreningen med formeln I tili ett farmaceutiskt godtagbart syraadditionssalt därav. 95465
2. Förfarande enligt patentkrav 1, känne-t e c k n a t därav, att arylpiperidinutgängsmaterialet behandlas med ätminstone en ekvivalent molmängd av reak-tanten Q(CH2)nR. 5
3. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att omsättningen utförs i ett för reaktionen inert, polärt, organiskt lösningsmedel under väsentligen vattenfria förhällanden i närvaro av ätminsto-ne en ekvivalent mängd av en lämplig standardbas. 10
4. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att omsättningen utförs vid en tem-peratur av ca 50 - ca 150 eC under en tid av ätminstone ca 2 timmar.
5. Förfarande enligt patentkrav 3, känne- 15 tecknat därav, att lösningsmedlet är aceton eller metylisobutylketon ooh standardbasen är kalium- eller nat-riumkarbonat.
6. Förfarande enligt patentkrav 1, känne-tecknat därav, att den framställda föreningen är ' 20 4-{{4-{2-[4-(2-metoxifenyl)-l-piperidinyl]etyl}fenyl}}- tiazol-2-amin.
7. Förfarande enligt patentkrav 1, känne-tecknat därav, att den framställda föreningen är 4- {{4-{4- [4-( 2-metoxifenyl )piperidinyl] -n-butyl}fenyl}}- 25 tiazol-2-amin.
8. Förfarande enligt patentkrav 1, känne-tecknat därav, att den framställda föreningen är 3-{4-[4-(2-metoxifenyl )-l-piperidinyl] -n-butyl}-l, 8,8-tri-metyl-3-azabicyclo[3.2.1]oktan-2,4-dion. 30
9. Förfarande enligt patentkrav 1, känne- V tecknat därav, att den framställda föreningen är 5- {2-[4-(2-metoxifenyl)-l-piperidinyl]etyl}oxindol.
10. Förfarande enligt patentkrav 1, känne-tecknat därav, att den framställda föreningen är 35 3-{2-[4-(1-naftyl)-l-piperidinyl]etyl}-2-metyl-4H-pyrido- [1,2-a]pyrimidin-4-on.
FI903829A 1988-12-02 1990-08-01 Förfarande för framställning av terapeutiskt användbara N-substituerade arylpiperidinderivat FI95465C (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US8804300 1988-12-02
PCT/US1988/004300 WO1990006303A1 (en) 1988-12-02 1988-12-02 Arylpiperidine derivatives

Publications (3)

Publication Number Publication Date
FI903829A0 FI903829A0 (sv) 1990-08-01
FI95465B true FI95465B (sv) 1995-10-31
FI95465C FI95465C (sv) 1996-02-12

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
FI903829A FI95465C (sv) 1988-12-02 1990-08-01 Förfarande för framställning av terapeutiskt användbara N-substituerade arylpiperidinderivat

Country Status (20)

Country Link
US (2) US5153206A (sv)
EP (1) EP0372776B1 (sv)
JP (1) JPH0710850B2 (sv)
KR (1) KR910006980B1 (sv)
AT (1) ATE143366T1 (sv)
AU (1) AU633858B2 (sv)
CA (1) CA2004249C (sv)
DE (1) DE68927254T2 (sv)
DK (1) DK606889A (sv)
ES (1) ES2092475T3 (sv)
FI (1) FI95465C (sv)
GR (1) GR3021496T3 (sv)
HU (1) HU207310B (sv)
IE (1) IE75359B1 (sv)
IL (1) IL92466A (sv)
NO (1) NO175257C (sv)
NZ (1) NZ231612A (sv)
PT (1) PT92468B (sv)
WO (1) WO1990006303A1 (sv)
ZA (1) ZA899192B (sv)

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Also Published As

Publication number Publication date
ATE143366T1 (de) 1996-10-15
US5153206A (en) 1992-10-06
GR3021496T3 (en) 1997-01-31
FI95465C (sv) 1996-02-12
NZ231612A (en) 1991-02-26
CA2004249C (en) 1996-09-17
JPH02275853A (ja) 1990-11-09
CA2004249A1 (en) 1990-06-02
WO1990006303A1 (en) 1990-06-14
KR910011783A (ko) 1991-08-07
DE68927254T2 (de) 1997-02-06
NO903383D0 (no) 1990-08-01
HU207310B (en) 1993-03-29
PT92468A (pt) 1990-06-29
IE893813L (en) 1990-06-02
HUT59127A (en) 1992-04-28
DK606889A (da) 1990-07-18
IL92466A0 (en) 1990-08-31
FI903829A0 (sv) 1990-08-01
IL92466A (en) 1994-02-27
ZA899192B (en) 1991-07-31
ES2092475T3 (es) 1996-12-01
JPH0710850B2 (ja) 1995-02-08
AU4586989A (en) 1990-06-28
US5294619A (en) 1994-03-15
NO903383L (no) 1990-10-01
EP0372776B1 (en) 1996-09-25
PT92468B (pt) 1995-07-18
AU633858B2 (en) 1993-02-11
HU892324D0 (en) 1990-12-28
IE75359B1 (en) 1997-08-27
DE68927254D1 (de) 1996-10-31
EP0372776A2 (en) 1990-06-13
NO175257C (no) 1994-09-21
DK606889D0 (da) 1989-12-01
EP0372776A3 (en) 1991-10-23
KR910006980B1 (ko) 1991-09-14
NO175257B (no) 1994-06-13

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