GB995964A - New pyridine derivatives - Google Patents

New pyridine derivatives

Info

Publication number
GB995964A
GB995964A GB14094/64A GB1409464A GB995964A GB 995964 A GB995964 A GB 995964A GB 14094/64 A GB14094/64 A GB 14094/64A GB 1409464 A GB1409464 A GB 1409464A GB 995964 A GB995964 A GB 995964A
Authority
GB
United Kingdom
Prior art keywords
carbinol
piperidyl
erythro
pyridyl
phenyl
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
GB14094/64A
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Publication of GB995964A publication Critical patent/GB995964A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

The invention comprises compounds of formula <FORM:0995964/C2/1> where R is a hydrogen or halogen atom, or an alkyl or alkoxy group, and R1 is a hydrogen atom, or alkyl group, and acid-addition salts thereof, which are prepared by cyclizing aryl-a -piperidyl-carbinols of formula <FORM:0995964/C2/2> with cyanogen halides, or by converting the carbinols, preferably in the form of their acid-addition salts, by treatment with cyanates or thiocyanates into the corresponding ureas or thioureas which can then be cyclized by heating with a hydrohalic acid, alcoholic mercury oxide or thionyl chloride. Further, when working at temperatures the cyanides obtained by treating the carbinols with a cyanogen halide can be isolated, and then cyclized. The compounds can be obtained as cis- or trans-isomers and optical antipodes thereof. Phenyl - 2 - (6 - methylpiperidyl) carbinol is prepared by reacting 6-methylpyridine-2-aldehyde with phenyl magnesium bromide to give phenyl - 2 - (6 - methylpyridyl) carbinol which is reduced, (-) -and ( +( - erythro - phenyl - 2 - piperidyl-carbinol and erythro-m-methylphenyl-2-piperidyl carbinol, and the hydrochloride salts thereof, are prepared by hydrogenating the required phenyl-pyridyl-carbinols, and, when required, converting the products to the hydrochloride salts. Erythro-(p-methoxyphenyl)-2-piperidyl -carbinol is produced by the reduction of p-methoxyphenyl-2-pyridyl carbinol. Erythro - (m - methoxyphenyl) - 2 - piperidyl carbinol is similarly prepared from m-methoxyphenyl-2-pyridyl carbinol which is obtained by reacting 2-pyridyl magnesium bromide with m - methoxybenzaldehyde. Erythro - (p - chlorophenyl) -2-piperidyl carbinol is produced by the reduction of p-chlorophenyl-2-pyridyl ketone.
GB14094/64A 1963-04-06 1964-04-06 New pyridine derivatives Expired GB995964A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF0039423 1963-04-06

Publications (1)

Publication Number Publication Date
GB995964A true GB995964A (en) 1965-06-23

Family

ID=7097763

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14094/64A Expired GB995964A (en) 1963-04-06 1964-04-06 New pyridine derivatives

Country Status (9)

Country Link
AT (1) AT250956B (en)
BR (1) BR6458150D0 (en)
CH (3) CH439294A (en)
DE (1) DE1445729A1 (en)
DK (5) DK105338C (en)
FR (1) FR3718M (en)
GB (1) GB995964A (en)
NL (1) NL6403571A (en)
SE (4) SE304515B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3494931A (en) * 1967-10-05 1970-02-10 Sandoz Ag 1-substituted-3-imino-tetrahydro-oxazolo(3,4-a)pyridines
US3496185A (en) * 1968-02-14 1970-02-17 Smithkline Corp Oxazolo- and thiazolo(3,4-a)-pyridine derivatives
US3505340A (en) * 1967-10-05 1970-04-07 Sandoz Ag 1-substituted-3-substituted imino-1,5,6,7,8,8a-hexahydro-3-h-thiazolo (3,4-a) pyridines and intermediates therefor
EP0128120A2 (en) * 1983-06-02 1984-12-12 Ciba-Geigy Ag Trisubstituted oxazolidinones

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3494931A (en) * 1967-10-05 1970-02-10 Sandoz Ag 1-substituted-3-imino-tetrahydro-oxazolo(3,4-a)pyridines
US3505340A (en) * 1967-10-05 1970-04-07 Sandoz Ag 1-substituted-3-substituted imino-1,5,6,7,8,8a-hexahydro-3-h-thiazolo (3,4-a) pyridines and intermediates therefor
US3496185A (en) * 1968-02-14 1970-02-17 Smithkline Corp Oxazolo- and thiazolo(3,4-a)-pyridine derivatives
EP0128120A2 (en) * 1983-06-02 1984-12-12 Ciba-Geigy Ag Trisubstituted oxazolidinones
EP0128120A3 (en) * 1983-06-02 1985-11-13 Ciba-Geigy Ag Trisubstituted oxazolidinones

Also Published As

Publication number Publication date
SE304516B (en) 1968-09-30
SE304517B (en) 1968-09-30
NL6403571A (en) 1964-10-07
DK106279C (en) 1967-01-16
DK105338C (en) 1966-09-19
FR3718M (en) 1965-11-29
AT250956B (en) 1966-12-12
CH437294A (en) 1967-06-15
CH439294A (en) 1967-07-15
BR6458150D0 (en) 1973-08-02
DK106225C (en) 1967-01-09
SE304515B (en) 1968-09-30
DK106280C (en) 1967-01-16
DK109261C (en) 1968-04-08
CH437295A (en) 1967-06-15
SE304757B (en) 1968-10-07
DE1445729A1 (en) 1969-10-02

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