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 activity

Info

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
Application number
FR7242783A
Other languages
French (fr)
Other versions
FR2208649B1 (en
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.)
Synthelabo SA
Original Assignee
Synthelabo SA
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 Synthelabo SA filed Critical Synthelabo SA
Priority to FR7242783A priority Critical patent/FR2208649A1/en
Publication of FR2208649A1 publication Critical patent/FR2208649A1/en
Application granted granted Critical
Publication of FR2208649B1 publication Critical patent/FR2208649B1/fr
Granted legal-status Critical Current

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.
FR7242783A 1972-12-01 1972-12-01 1-(2-Thienyl)cycloalkane carboxylic ester salts - with spasmolytic and anticholinergic activity Granted FR2208649A1 (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (5)

* Cited by examiner, † Cited by third party
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