GB1257960A - - Google Patents

Info

Publication number
GB1257960A
GB1257960A GB1257960DA GB1257960A GB 1257960 A GB1257960 A GB 1257960A GB 1257960D A GB1257960D A GB 1257960DA GB 1257960 A GB1257960 A GB 1257960A
Authority
GB
United Kingdom
Prior art keywords
substituted
compounds
tetrahydropyridine
hydroxymethyl
hexyl
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
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 filed Critical
Publication of GB1257960A publication Critical patent/GB1257960A/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
    • C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Abstract

1,257,960. Esters of N-substituted 3-hydroxymethyl - 1,2,5,6 - tetrahydropyridine. BOEHRINGER INGELHEIM G.m.b.H. 25 June, 1969 [25 June, 1968], No. 32090/69. Heading C2C. The invention comprises compounds of formula and their acid addition salts and quaternary ammonium derivatives, wherein R 1 is C 2-10 alkyl (possibly CN- or alkyl-substituted), C 2-3 alkenyl (possibly halogen-substituted), C 2-3 alkynyl, C 3-6 cycloalkyl, or phenylalkyl; R 2 is H, Cl, Me or OH and R 3 is H, Ph or C 5-6 cycloalkyl, or CR 2 R 3 is a 5- or 6-membered cycloaliphatic ring ; and R 4 is Ph provided that when both R 3 and R 4 are Ph these groups may be joined through their o-positions either directly or via an O atom. These compounds are prepared by an esterification or N-substitution method. Details are also given for the preparation of 1-hexyl-3-hydroxymethylpyridinium bromide and 1 - hexyl - 3 - hydroxymethyl - 1,2,5,6 - tetrahydropyridine. Therapeutic compositions for oral, parenteral, rectal or topical administration, comprise compounds of the above formula, which have spasmolytic and CNS-sedative activity, in association with a pharmaceutical carrier or diluent.
GB1257960D 1968-06-25 1969-06-25 Expired GB1257960A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
AT609868A AT287711B (en) 1968-06-25 1968-06-25 Process for the preparation of new 1-alkyl-1,2,5,6-tetrahydro-3-pyridylmethyl-carboxylic acid esters and their acid addition salts and quaternary ammonium compounds

Publications (1)

Publication Number Publication Date
GB1257960A true GB1257960A (en) 1971-12-22

Family

ID=3582843

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1257960D Expired GB1257960A (en) 1968-06-25 1969-06-25

Country Status (11)

Country Link
US (1) US3627775A (en)
AT (1) AT287711B (en)
BE (1) BE735141A (en)
BR (1) BR6910094D0 (en)
CH (1) CH513164A (en)
DE (1) DE1929921A1 (en)
ES (3) ES368698A1 (en)
FR (1) FR2014218A1 (en)
GB (1) GB1257960A (en)
IL (1) IL32469A0 (en)
NL (1) NL6909425A (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4467095A (en) * 1969-02-10 1984-08-21 Fmc Corporation Anticholinergic compounds
US3879556A (en) * 1970-09-02 1975-04-22 Boehringer Sohn Ingelheim Pharmaceutical compositions containing a 1,2,3,6-tetrahydro-4-pyridylmethyl carboxylate and method of use
DE2043455A1 (en) * 1970-09-02 1972-03-09 CH. Boehringer Sohn, 6507 Ingelheim New l, 2,3,6-tetrahydro-4-pyridylmethyl-carboxylic acid esters, as well as their acid addition salts and quaternary ammonium compounds
FR2501682A1 (en) * 1981-03-11 1982-09-17 Sanofi Sa TRIPLUOROMETHYLPHENYLPYRIDINES WITH ANOREXIGENE ACTIVITY, A PREPARATION PROCESS AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME
DE3801659A1 (en) * 1988-01-21 1989-07-27 Boehringer Ingelheim Kg TETRAHYDROPYRIDINE DERIVATIVES

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2607777A (en) * 1947-04-10 1952-08-19 Searle & Co N-alkyl piperidyl alkyl esters of diphenyl acetic acid and 9-fluorenyl carboxylic acid
GB886437A (en) * 1959-07-15 1962-01-10 Beecham Res Lab Improvements in or relating to basic esters of etherified benzilic acids

Also Published As

Publication number Publication date
CH513164A (en) 1971-09-30
ES374408A1 (en) 1972-01-01
ES374407A1 (en) 1972-01-01
AT287711B (en) 1971-02-10
DE1929921A1 (en) 1970-01-02
BR6910094D0 (en) 1973-04-05
IL32469A0 (en) 1969-08-27
US3627775A (en) 1971-12-14
NL6909425A (en) 1969-12-30
FR2014218A1 (en) 1970-04-17
ES368698A1 (en) 1971-07-01
BE735141A (en) 1969-12-29

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees