GB945824A - ªÏ-(pyridyl-3)-or ªÏ-(piperidyl-3)-propanol and derivatives thereof and processes for their manufacture - Google Patents

ªÏ-(pyridyl-3)-or ªÏ-(piperidyl-3)-propanol and derivatives thereof and processes for their manufacture

Info

Publication number
GB945824A
GB945824A GB30306/61A GB3030661A GB945824A GB 945824 A GB945824 A GB 945824A GB 30306/61 A GB30306/61 A GB 30306/61A GB 3030661 A GB3030661 A GB 3030661A GB 945824 A GB945824 A GB 945824A
Authority
GB
United Kingdom
Prior art keywords
compound
piperidyl
pyridyl
benzyl
alkyl
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB30306/61A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck KGaA
Original Assignee
E Merck AG
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 E Merck AG filed Critical E Merck AG
Publication of GB945824A publication Critical patent/GB945824A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • 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
    • C07D211/20—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 with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—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 with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • 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
    • C07D211/36—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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Abstract

The invention comprises compounds of the formula Z-(CH2)3-OR1 (wherein Z is a 3-pyridylo a 3-(N-R2-piperidyl)-radical, R2 being hydrogen, C1 - 4 alkyl or benzyl, and R1 is -(CH2)n-NR3R4, -CO-NR3R4 or -COR6, R4 is C1-4 alkyl, cyclohexyl, benzyl or phenethyl, or phenyl which may optionally be substituted by a chlorine or bromine atom or a methyl, ethyl, hydroxy, methoxy or ethoxy group, R3 is hydrogen or R4, n is 2 or 3, and R6 is pyridyl, N-R2-piperidyl, piperidino, morpholino or N-methylpiperazino), their acid-addition salts and their quaternary ammonium derivatives; and their preparation by (1) reacting an alkali metal salt of the alcohol Z-(CH2)3-OH with a compound Hal-(CH2)nNR3R4 (wherein Hal is chlorine, bromine or iodine) or reacting the alcohol with an isocyanate R4.NCO, a urea chloride R3R4N.COCI or phosgene and then an amine NHR3R4, piperidine, morpholine or N-methyl-piperazine; or (2) reacting a compound of the formula Z-(CH2)3-Y (wherein Y is OH, O acyl, chlorine, bromine or iodine) with an acid R6. COOH or a derivative thereof; or (3) hydrogenating a compound of the invention wherein Z is pyridyl or a quaternary ammonium derivative thereof to give the corresponding piperidyl compound; or (4) introducing the radical R2 into a compound not containing it by known alkylation or aralkylation and/or reduction methods, e.g. alkylation with an alkyl or aralkyl halide or with an aldehyde followed by hydrogenation, or hydrogenolysis of a benzyl compound. Examples illustrate these methods and also describe the hydrogenation of an N-phenyl-carbamic acid ester of the invention to the corresponding N-cyclohexyl carbamic acid ester. The preparation of acid-addition and quaternary ammonium salts is also described. Omega-(pyridyl-3)-propanol is prepared by condensing b -picoline with ethylene oxide. Omega-(piperidyl-3)-propanol is prepared by catalytic reduction of the pyridyl compound or by chemical reduction of nicotinoylacetic acid ethyl ester. The N-alkyl- or N-benzyl-piperidyl compounds are prepared by catalytic hydrogenation of the corresponding quaternary pyridinium salts.
GB30306/61A 1960-09-02 1961-08-22 ªÏ-(pyridyl-3)-or ªÏ-(piperidyl-3)-propanol and derivatives thereof and processes for their manufacture Expired GB945824A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEM0046443 1960-09-02

Publications (1)

Publication Number Publication Date
GB945824A true GB945824A (en) 1964-01-08

Family

ID=7305601

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30306/61A Expired GB945824A (en) 1960-09-02 1961-08-22 ªÏ-(pyridyl-3)-or ªÏ-(piperidyl-3)-propanol and derivatives thereof and processes for their manufacture

Country Status (2)

Country Link
FR (1) FR1346M (en)
GB (1) GB945824A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3409625A (en) * 1964-12-08 1968-11-05 Ishikawa Masayuki (py)-n-oxides of certain carbamates of 2-pyridinemethanol
WO1996031475A2 (en) * 1995-04-07 1996-10-10 Sibia Neurosciences, Inc. Substituted pyridine derivatives, their preparation and their use as modulators of acetylcholine receptors

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3409625A (en) * 1964-12-08 1968-11-05 Ishikawa Masayuki (py)-n-oxides of certain carbamates of 2-pyridinemethanol
WO1996031475A2 (en) * 1995-04-07 1996-10-10 Sibia Neurosciences, Inc. Substituted pyridine derivatives, their preparation and their use as modulators of acetylcholine receptors
WO1996031475A3 (en) * 1995-04-07 1997-02-06 Sibia Neurosciences Inc Substituted pyridine derivatives, their preparation and their use as modulators of acetylcholine receptors

Also Published As

Publication number Publication date
FR1346M (en) 1962-06-04

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