FR2208649A1 - 1-(2-Thienyl)cycloalkane carboxylic ester salts - with spasmolytic and anticholinergic activity - Google Patents
1-(2-Thienyl)cycloalkane carboxylic ester salts - with spasmolytic and anticholinergic activityInfo
- Publication number
- FR2208649A1 FR2208649A1 FR7242783A FR7242783A FR2208649A1 FR 2208649 A1 FR2208649 A1 FR 2208649A1 FR 7242783 A FR7242783 A FR 7242783A FR 7242783 A FR7242783 A FR 7242783A FR 2208649 A1 FR2208649 A1 FR 2208649A1
- Authority
- FR
- France
- Prior art keywords
- spasmolytic
- thienyl
- anticholinergic activity
- carboxylic ester
- ester salts
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/10—Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Cpds. of formula: (where n is 3,4,5,6; R1, R2 are H, 1-4C alkyl; A is an organic or inorganic, pharmaceutically acceptable anion) and their stereoisomers, particularly those derived from tropanol. The oral LD50 in mice varies from 700 to >6000 mg/kg. Spasmolytic ED50 in rabbit jejunum varies from 5 to 25 mu g/kg i.v. and 2.5 to 25 mg/kg i.p. The anticholinergic activity in the Shay rat test is less than, but approaches, that of atropine. Dose is 5-200 mg orally to a daily total of 50-1000 mg.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7242783A FR2208649A1 (en) | 1972-12-01 | 1972-12-01 | 1-(2-Thienyl)cycloalkane carboxylic ester salts - with spasmolytic and anticholinergic activity |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7242783A FR2208649A1 (en) | 1972-12-01 | 1972-12-01 | 1-(2-Thienyl)cycloalkane carboxylic ester salts - with spasmolytic and anticholinergic activity |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2208649A1 true FR2208649A1 (en) | 1974-06-28 |
FR2208649B1 FR2208649B1 (en) | 1975-11-28 |
Family
ID=9108058
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR7242783A Granted FR2208649A1 (en) | 1972-12-01 | 1972-12-01 | 1-(2-Thienyl)cycloalkane carboxylic ester salts - with spasmolytic and anticholinergic activity |
Country Status (1)
Country | Link |
---|---|
FR (1) | FR2208649A1 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1992016528A1 (en) * | 1991-03-15 | 1992-10-01 | Boehringer Ingelheim Kg | New bi- and tricyclic aminoalcohol esters, their preparation and their use in medicaments |
US5770738A (en) * | 1992-03-05 | 1998-06-23 | Boehringer Ingelheim Kg | Esters of bi- and tricyclic amino alcohols, their preparation and their use in pharmaceutical compositions |
US7569581B2 (en) | 2000-10-14 | 2009-08-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Anticholinergics which may be used as medicaments as well as processes for preparing them |
US8207193B2 (en) | 2006-11-14 | 2012-06-26 | Astrazeneca Ab | Quiniclidine derivatives of (hetero) arylcycloheptanecarboxylic acid as muscarinic receptor antagonists |
US8329729B2 (en) | 2008-05-13 | 2012-12-11 | Astrazeneca Ab | Quinuclidine derivatives as muscarinic M3 receptor antagonists |
-
1972
- 1972-12-01 FR FR7242783A patent/FR2208649A1/en active Granted
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1992016528A1 (en) * | 1991-03-15 | 1992-10-01 | Boehringer Ingelheim Kg | New bi- and tricyclic aminoalcohol esters, their preparation and their use in medicaments |
US5770738A (en) * | 1992-03-05 | 1998-06-23 | Boehringer Ingelheim Kg | Esters of bi- and tricyclic amino alcohols, their preparation and their use in pharmaceutical compositions |
US7569581B2 (en) | 2000-10-14 | 2009-08-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Anticholinergics which may be used as medicaments as well as processes for preparing them |
US8207193B2 (en) | 2006-11-14 | 2012-06-26 | Astrazeneca Ab | Quiniclidine derivatives of (hetero) arylcycloheptanecarboxylic acid as muscarinic receptor antagonists |
US8329729B2 (en) | 2008-05-13 | 2012-12-11 | Astrazeneca Ab | Quinuclidine derivatives as muscarinic M3 receptor antagonists |
Also Published As
Publication number | Publication date |
---|---|
FR2208649B1 (en) | 1975-11-28 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
ST | Notification of lapse |