FI94413B - Förfarande för framställning av terapeutiskt aktiva 2-(1-piperazinyl)-4-fenylcykloalkanopyridinderivat - Google Patents

Förfarande för framställning av terapeutiskt aktiva 2-(1-piperazinyl)-4-fenylcykloalkanopyridinderivat Download PDF

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Publication number
FI94413B
FI94413B FI901030A FI901030A FI94413B FI 94413 B FI94413 B FI 94413B FI 901030 A FI901030 A FI 901030A FI 901030 A FI901030 A FI 901030A FI 94413 B FI94413 B FI 94413B
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FI
Finland
Prior art keywords
alkyl
piperazinyl
formula
compound
hydrogen atom
Prior art date
Application number
FI901030A
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English (en)
Finnish (fi)
Other versions
FI94413C (sv
FI901030A0 (sv
Inventor
Tatsuya Kon
Katsuhiko Hino
Naoki Kai
Masato Sakamoto
Makoto Oka
Kiyoshi Furukawa
Yoshiaki Ochi
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Dainippon Pharmaceutical Co
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.)
Filing date
Publication date
Application filed by Dainippon Pharmaceutical Co filed Critical Dainippon Pharmaceutical Co
Publication of FI901030A0 publication Critical patent/FI901030A0/sv
Publication of FI94413B publication Critical patent/FI94413B/sv
Application granted granted Critical
Publication of FI94413C publication Critical patent/FI94413C/sv

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D221/04—Ortho- or peri-condensed ring systems
    • 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
    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (10)

1. Förfarande för framställning av terapeutiskt aktiva 2-(1-piperazinyl)-4-fenylcykloalkanopyridinderivat med formeln 5 (I) R2 R3
10 R< v ς -7 d) R -Γ- Il I (CHo) R' ««2)n Li,/ \ <>-R R6 ' ^\R8 15 där n är 3, 4, 5, 6 eller 7, R1 är en väteatom, C1-C10 alkyl, C2-Cg alkenyl, C2-Cg alkynyl,
20 C3-C8 cykloalkyl, C3-Cg cykloalkyl-(1~C4)alkyl, hydroxi-C2-Cg alkyl, C^-C-j alkoxi-C2-Cg alkyl, osubstituerad eller monohalo-gensubstituerad bensoyl-C1-Cg alkyl, osubstituerad eller raono-halogensubstituerad fenyl, pyridyl, pyrimidyl, C2-C4 alkänoyl, bensoyl eller furoyl,
25 R2 och R3, som är lika eller olika, är var och en en väteatom, : halogenatom, C^-Cg alkyl, C1-Cg alkoxi eller trifluormetyl, R4, R5 och R6, som kan vara lika eller olika, är var och en en väteatom, C^-Cg alkyl eller fenyl, eller tvä av grupperna R4, R5 och R6 bildar tillsammans en enkel bindning eller C-^-C^ 30 alkylen, R7 och R8, som kan vara lika eller olika, är var och en en väteatom, alkyl, m är 2 eller 3, förutsatt, att dä R1 är pyridyl eller pyrimidyl, sä är m 2 eller dess syraadditionssalt, k ä n n e -35 tecknat därav, att l! 57 94413 (a) en förening med formeln (II): R2 R3 R di) R5 -/— Y| <c«2>n L A 10 \ZA N x R6^ där X är en avgäende atom eller grupp och R2, R3, R4, R5, R6 och n 15 avser det samma som ovan, omsätts med en forening med formeln (III) : ,(CH2U/R7
20 HN ^N-R1 (III) där R1, R7, R8 och m avser det samma som ovan 25 :·' (b) i fall, att R1 är en väteatom Λ c·. -, ' νιη* omsatts en forening med formeln (1-5) : R2 R3 30 ' R4 7^\X R5 -/— HI ACH2) 1 (I"5) <CH2)n I Λ/ A—R7 35 ^ ΝχΟ>Α*15 R6 \ \8 där 58 94413 R15 är metyl eller osubstituerad eller substituerad bensyl (substituenten i bensylens fenylring är vald bland lägre alkyl, lägre alkoxi eller en halogenatom), och R2, R3, R4, R5,
5 R6, R7, R8, m och n avser det samma som ovan, omsätts med etylklorkarbonat eller 1-kloretylkarbonat sä, att en förening med formeln (1-6) erhälls: R2 R3 r5 -(CH2U/r7 ,= “y- KM Hli. R6 där R16 är etoxikarbonyl eller 1-kloretoxikarbonyl och R2, R3, R4,
20 R5, R6, R7, R8, m och n avser det samma som ovan, varefter en förening med formeln (1-6) hydrolyseras, eller (c) i fall, att R1 är nägot annat än en väteatom, osubstituerad eller monohalogensubstituerad fenyl, pyridyl, pyrimidyl,
25 C2-C4-alkanoyl, bensoyl eller furoyl, omsätts en förening med : formeln (1-8) R2 R3 > 5 R A,H^ ciy N \ v.N-H
35 R6 ' ^^R8 59 94413 där R2, R3, R4, R5, R6, R7, R8, m och n avser det samma som ovan, med med en förening med forraeln (IV):
5 R18 - Z (IV) där Z är en reaktiv rest av en alkohol, och R18 avser det samma som R1 med undantag för en väteatom, osubstituerad eller 10 monohalogensubstituerad fenyl, pyridyl, pyrimidyl, C2-C4-alkanoyl, bensoyl eller furoyl, ja eventuell omvandlas en förening med formeln (I) tili sitt syraadditionssalt. 15 2. Förfarande enligt patentkravet 1, kännetecknat därav, att 2-(4-etyl-l-piperazinyl)-4-(4-fluorfenyl)-5,6,7,8,- 9.10- hexahydrocyklo-okta[b]pyridin eller dess syraadditionssalt framställs. 20 3. Förfarande enligt patentkravet 1, kännetecknat därav, att 2-(4-etyl-l-piperazinyl)-4-(2,4-difluorfenyl)-5,6,- 7.8.9.10- hexahydrocyklo-okta[b]pyridin eller dess syraadditionssalt framställs. 25 4. Förfarande enligt patentkravet 1, kännetecknat »" därav, att 2-(4-n-propyl-l-piperazinyl)-4-(4-fluorfenyl)-5,6,- 7.8.9.10- hexahydrocyklo-okta[b]pyridin eller dess syraadditionssalt framställs. »
FI901030A 1989-03-03 1990-03-01 Förfarande för framställning av terapeutiskt aktiva 2-(1-piperazinyl)-4-fenylcykloalkanopyridinderivat FI94413C (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP5254489 1989-03-03
JP5254489 1989-03-03

Publications (3)

Publication Number Publication Date
FI901030A0 FI901030A0 (sv) 1990-03-01
FI94413B true FI94413B (sv) 1995-05-31
FI94413C FI94413C (sv) 1995-09-11

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FI901030A FI94413C (sv) 1989-03-03 1990-03-01 Förfarande för framställning av terapeutiskt aktiva 2-(1-piperazinyl)-4-fenylcykloalkanopyridinderivat

Country Status (15)

Country Link
US (1) US5021421A (sv)
EP (1) EP0385237B1 (sv)
KR (1) KR0149649B1 (sv)
AT (1) ATE107922T1 (sv)
AU (1) AU623981B2 (sv)
CA (1) CA2011346C (sv)
DD (1) DD292909A5 (sv)
DE (1) DE69010232T2 (sv)
DK (1) DK0385237T3 (sv)
ES (1) ES2058630T3 (sv)
FI (1) FI94413C (sv)
HK (1) HK1005872A1 (sv)
HU (1) HU204810B (sv)
NO (1) NO177095C (sv)
RU (1) RU2075478C1 (sv)

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Also Published As

Publication number Publication date
EP0385237A3 (en) 1991-03-20
NO177095C (no) 1995-07-19
NO900991D0 (no) 1990-03-01
DD292909A5 (de) 1991-08-14
CA2011346A1 (en) 1990-09-03
CA2011346C (en) 1999-08-03
EP0385237A2 (en) 1990-09-05
DE69010232T2 (de) 1994-12-01
KR0149649B1 (ko) 1998-10-15
AU623981B2 (en) 1992-05-28
ATE107922T1 (de) 1994-07-15
NO900991L (no) 1990-09-04
HUT53361A (en) 1990-10-28
US5021421A (en) 1991-06-04
EP0385237B1 (en) 1994-06-29
HK1005872A1 (en) 1999-01-29
ES2058630T3 (es) 1994-11-01
FI94413C (sv) 1995-09-11
HU204810B (en) 1992-02-28
RU2075478C1 (ru) 1997-03-20
DK0385237T3 (da) 1994-07-25
HU901275D0 (en) 1990-05-28
FI901030A0 (sv) 1990-03-01
DE69010232D1 (de) 1994-08-04
NO177095B (no) 1995-04-10
AU5060490A (en) 1990-09-06
KR900014358A (ko) 1990-10-23

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