ES368698A1 - 1-alkyl-1,2,5,6-tetrahydro-3-pyridylmethyl carboxylic - Google Patents
1-alkyl-1,2,5,6-tetrahydro-3-pyridylmethyl carboxylicInfo
- Publication number
- ES368698A1 ES368698A1 ES368698A ES368698A ES368698A1 ES 368698 A1 ES368698 A1 ES 368698A1 ES 368698 A ES368698 A ES 368698A ES 368698 A ES368698 A ES 368698A ES 368698 A1 ES368698 A1 ES 368698A1
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- compounds
- hexyl
- cycloalkyl
- substituted
- 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
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
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.
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 |
---|---|
ES368698A1 true ES368698A1 (en) | 1971-07-01 |
Family
ID=3582843
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES368698A Expired ES368698A1 (en) | 1968-06-25 | 1969-06-23 | 1-alkyl-1,2,5,6-tetrahydro-3-pyridylmethyl carboxylic |
ES374407A Expired ES374407A1 (en) | 1968-06-25 | 1969-12-10 | 1-alkyl-1,2,5,6-tetrahydro-3-pyridylmethyl carboxylic |
ES374408A Expired ES374408A1 (en) | 1968-06-25 | 1969-12-10 | 1-alkyl-1,2,5,6-tetrahydro-3-pyridylmethyl carboxylic |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES374407A Expired ES374407A1 (en) | 1968-06-25 | 1969-12-10 | 1-alkyl-1,2,5,6-tetrahydro-3-pyridylmethyl carboxylic |
ES374408A Expired ES374408A1 (en) | 1968-06-25 | 1969-12-10 | 1-alkyl-1,2,5,6-tetrahydro-3-pyridylmethyl carboxylic |
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4467095A (en) * | 1969-02-10 | 1984-08-21 | Fmc Corporation | Anticholinergic compounds |
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 |
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 |
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)
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 |
-
1968
- 1968-06-25 AT AT609868A patent/AT287711B/en not_active IP Right Cessation
-
1969
- 1969-06-12 DE DE19691929921 patent/DE1929921A1/en active Pending
- 1969-06-19 NL NL6909425A patent/NL6909425A/xx unknown
- 1969-06-23 CH CH958769A patent/CH513164A/en not_active IP Right Cessation
- 1969-06-23 ES ES368698A patent/ES368698A1/en not_active Expired
- 1969-06-24 IL IL32469A patent/IL32469A0/en unknown
- 1969-06-24 BR BR210094/69A patent/BR6910094D0/en unknown
- 1969-06-25 US US836658A patent/US3627775A/en not_active Expired - Lifetime
- 1969-06-25 BE BE735141D patent/BE735141A/xx unknown
- 1969-06-25 FR FR6921376A patent/FR2014218A1/fr not_active Withdrawn
- 1969-06-25 GB GB1257960D patent/GB1257960A/en not_active Expired
- 1969-12-10 ES ES374407A patent/ES374407A1/en not_active Expired
- 1969-12-10 ES ES374408A patent/ES374408A1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
ES374407A1 (en) | 1972-01-01 |
US3627775A (en) | 1971-12-14 |
FR2014218A1 (en) | 1970-04-17 |
BR6910094D0 (en) | 1973-04-05 |
NL6909425A (en) | 1969-12-30 |
CH513164A (en) | 1971-09-30 |
ES374408A1 (en) | 1972-01-01 |
IL32469A0 (en) | 1969-08-27 |
GB1257960A (en) | 1971-12-22 |
AT287711B (en) | 1971-02-10 |
BE735141A (en) | 1969-12-29 |
DE1929921A1 (en) | 1970-01-02 |
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