FI78480B - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara n-(bicyklis heterocyklyl)-4-piperidinaminderivat. - Google Patents

Foerfarande foer framstaellning av nya terapeutiskt anvaendbara n-(bicyklis heterocyklyl)-4-piperidinaminderivat. Download PDF

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FI78480B
FI78480B FI832521A FI832521A FI78480B FI 78480 B FI78480 B FI 78480B FI 832521 A FI832521 A FI 832521A FI 832521 A FI832521 A FI 832521A FI 78480 B FI78480 B FI 78480B
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FI832521A
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Frans Eduard Janssens
Joseph Leo Ghislanus Torremans
Offenwert Theophilus There Van
Josef Francis Hens
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Janssen Pharmaceutica Nv
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed 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
    • C07D401/14—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 three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
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    • 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
    • C07D211/36—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 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
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C07D417/14—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 three or more hetero 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)
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  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Claims (12)

1. Förfarande för framställning av terapeutiskt användbara N-(bicyklis heterocyklyl)-4-piperidinaminderivat 5 med formeln I och farmaceutiskt godtagbara syraadditions-salter och stereokemiskt isomera former därav, R R1 “C/aio i vilken formel A är en bivalent radikal med formeln 15 -CH=CH-CH=CH- (a), -N=CH-CH=CH- (b), -CH=N-CH=CH- (c), -CH=CH-N-CH- (d), eller -CH=CH-CH=N- (e) 20 varvid i radikalen (a) en väteatom kan vara ersatt med halogen, lägre alkoxi eller hydroxi, R är väte eller lägre alkyl, R^" är väte, lägre alkyl, Ar^ eller lägre alkyl, som är substituerad med en Ar^"-radikal,
25 R^ är väte, lägre alkyl eller fenyl-lägre-alkyl, och L är en radikal med formeln Het-CsH2s“NA/ (f)' 30 \-' Het-C -Y-Alk- (g), eller s 2s X Het-C H0 -Z-C-Y-Alk- (h) S 2S 35 i vilka formler 77 78480 s är 0 eller 1, Alk är lägre alkandiyl, 3 3 Y är O, S, NR eller en direkt bindning, varvid R är väte, lägre alkyl, acetyl, bensoyl eller bensyl,
5 X är O eller S, Z är NH, N(lägre alkyl) eller en direkt bindning, och Het är en pyridinyl-, pyridinyloxid-, kinolinyl-, pyrimidi- nyl-, kinazolinyl-, pyridazinyl-, kinoxalinyl-, pyrazinyl- eller ftalazinylradikal, som är bunden vid gruppen -C H„ - S 6 s 10 via en kolatom och som kan vara mono- eller disubstituerad med lägre alkyl, halogen, amino, lägre alkyltio, lägre alkoxi, oxo, bensyl, 4-klorbensyl, hydroxi, nitro och/eller aminokarbonyl, eller Het är en 5,6-dihydro-4H-l,3-tiazin-2-ylradikal,förutsatt att Het är annat än pyridinyl, d& L 15 är en radikal (g), där Y är NR^, eller dä L är en radikal (h), där X är 0 och Z är NH eller en direkt bindning, och Ar^ är fenyl, som kan vara monosubstituerad med halogen, hydroxi, lägre alkyl eller lägre alkoxi, eller Ar^ är tien-yl, furanyl, med lägre alkyl substituerad furanyl, pyri-20 dinyl, pyrazinyl, tiazolyl eller imidazolyl, som kan vara substituerad med lägre alkyl, kännetecknat där-av, att a) ett piperidinderivat med formeln “ nA i Ö2"Cy ΙΐΧ> (iii> 30 alkyleras med en förening med formeln Het-Q1 (II) 35. ett i förhällande till reaktionen inert lösningsmedel, varvid 78 78480
1. Qj är väte och tillsammans raed gruppen Het bildar en radikal med formeln L-W (Il-a), där W är en lämp-lig reaktiv, avgäende grupp, säsom halogen, t.ex. klor, brora eller jod, eller en sulfonyloxigrupp, t.ex. en metyl- 5 sulfonyloxi- eller 4-metylfenylsulfonyloxigrupp; eller
2. Q. är en radikal med formeln -C H0 -W, där 1 s 2s W betecknar samma som W och, dä s är 0, kan W även vara en lägre alkoxi- eller lägre alkyltiogrupp, och Q2 är en radikal med formeln 10 Of 15 varvid erh&lls en förening med formeln _ R ± Het-C H. -N Λ /7\ jj ............. 20 3) är en radikal med formeln -<~sH2s-W', och Q2 är en radikal med formeln HY'-Alk-, där Y' betecknar samma 25 som Y, förutsatt att Y är annat än en direkt bindning, varvid erhälls en förening med formeln /"V ?1
30 S 2S \ / ?2 I | (I-a-2) ; eller 4) är en radikal med formeln och ^2 är en radikal med formeln HZ1-C(X)-Y-Alk-, där Z' beteck- 35 nar samma som Z, förutsatt att Z är annat än en direkt bindning, varvid erhälls en förening med formeln 79 78480 x ί1 Het-cs„2s-Z.-5-x-MX-K^»^Q(i_a_3)! ® eller 5) är en radikal med formeln “csH2s~YH och Qj är en radikal med formeln W-Alk-, varvid erhälls en före-ning med formeln
10 Rl /“Λ ’ Het-C0H0 -Y'-Alk-N Vn“, 2 2s \ / VHl _|X (I-a-2); eller 15
6. Q, är en radikal med formeln -C H- -Z-C(X)-ΥΉ 1 s «s och Q2 är en radikal med formeln W-Alk, varvid erhälls en förening med formeln
20 R 1 X · " / \ Het-C-H0 -Z-C-Y' -Alk-N >~ Ν~ίΐ Π ' 2 2s \ / VJ1 I a (I-a-4); R N-eller 25 b) en förening med formeln Het-C H0 -Z1 H (IV) s Zs omsätts med ett piperidinderivat med formeln 30 rÄ. f X=C=N-Alk-N \ N / ^ «2tXj (v) so 78480 i ett lämpligt i förhällande till reaktionen inert lös-ningsmedel, varvid erhälls en förening med formeln R R1
5 Het-C -Z ' -C-N-Alk-N V . TN V""'' s 2s H \_J Voi } A (I-b-1) , eller R N-\__/ c) en förening med formeln 10 Het-C H- -N=C=X (VI) S 2S omsätts med ett piperidinderivat med formeln R R2 15 / ? /ΓΓΛ n HY'-Alk-N^^V2^j]^A (VII) 20. ett lämpligt i förhällande tili reaktionen inert lös-ningsmedel, varvid erhälls en förening med formeln / Het-CaH2s-N„-C-y-Älk-N 25 '-' vr ^eller d) en förening med formeln X
30 Het-C H0 -C-OH (VIII) S 2S omsätts med ett piperidinderivat med formeln ,R R1 ” öo 81 78480 i ett lämpligt i förhällande till reaktionen inert lös-ningsmedel, eventuellt efter att en OH-grupp i föreningen med formeln (VIII) omvandlats tili en lämplig avgäende grupp, varvid erhllls en förening med formeln 5 R i Het-csH2s-g-Y'-Aik-N^y Nxq (i'c)i eiier 10 e) ett piperidinderivat med formeln _/R R1 „ -0- v(X} omsätts med ett reagens med formeln
20 Het-lägre-alkandiyl-H (IX) i ett lämpligt i förhällande tili reaktionen inert lös-ningsmedel, varvid erhälls en förening med formeln 25 /R R1 Het-Alk-N^^N2^J0A (I.d). eller 30 f) en förening med formeln R1 R NH rA s >~\ L-N Vn-C-NIT a (X) 35 \_V .2
FI832521A 1982-07-12 1983-07-11 Förfarande för framställning av nya terapeutiskt användbara N-(bicykli s heterocyklyl)-4-piperidinaminderivat FI78480C (sv)

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US39762682A 1982-07-12 1982-07-12
US39762682 1982-07-12
US48777483 1983-04-22
US06/487,774 US4556660A (en) 1982-07-12 1983-04-22 N-(Bicyclic heterocyclyl)-4-piperidinamines

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FI832521A0 FI832521A0 (fi) 1983-07-11
FI832521L FI832521L (fi) 1984-01-13
FI78480B true FI78480B (fi) 1989-04-28
FI78480C FI78480C (sv) 1989-08-10

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EP (1) EP0099139B1 (sv)
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AU (1) AU563363B2 (sv)
BG (1) BG40655A3 (sv)
CA (1) CA1266267A (sv)
DE (1) DE3369784D1 (sv)
DK (1) DK318583A (sv)
ES (1) ES524029A0 (sv)
FI (1) FI78480C (sv)
GR (1) GR81366B (sv)
HU (1) HU203550B (sv)
IE (1) IE56077B1 (sv)
IL (1) IL69198A (sv)
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NO (1) NO160850C (sv)
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RO (1) RO87533A (sv)
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ZW15583A1 (en) 1984-01-30
EP0099139B1 (en) 1987-02-11
EP0099139A3 (en) 1984-02-22
ES8602768A1 (es) 1985-11-16
MA19845A1 (fr) 1984-04-01
FI832521A0 (fi) 1983-07-11
AU1672883A (en) 1985-01-17
SU1297728A3 (ru) 1987-03-15
PH22009A (en) 1988-05-02
IL69198A0 (en) 1983-11-30
DE3369784D1 (en) 1987-03-19
FI832521L (fi) 1984-01-13
PT77012B (en) 1986-02-26
NO160850B (no) 1989-02-27
NO160850C (no) 1989-06-07
IL69198A (en) 1987-01-30
BG40655A3 (en) 1987-01-15
AU563363B2 (en) 1987-07-09
IE831613L (en) 1984-01-12
DK318583A (da) 1984-01-13
NO832524L (no) 1984-01-13
DK318583D0 (da) 1983-07-11
NZ204759A (en) 1985-12-13
KR870001510B1 (ko) 1987-08-20
FI78480C (sv) 1989-08-10
CA1266267A (en) 1990-02-27
RO87533B (ro) 1985-10-01
ES524029A0 (es) 1985-11-16
KR840005446A (ko) 1984-11-12
US4556660A (en) 1985-12-03
RO87533A (ro) 1985-10-31
GR81366B (sv) 1984-12-11
EP0099139A2 (en) 1984-01-25
IE56077B1 (en) 1991-04-10
HU203550B (en) 1991-08-28
PT77012A (en) 1983-08-01

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