GB813218A - Nor-tropines and nor-pseudo-tropines and process for their production - Google Patents

Nor-tropines and nor-pseudo-tropines and process for their production

Info

Publication number
GB813218A
GB813218A GB4261/57A GB426157A GB813218A GB 813218 A GB813218 A GB 813218A GB 4261/57 A GB4261/57 A GB 4261/57A GB 426157 A GB426157 A GB 426157A GB 813218 A GB813218 A GB 813218A
Authority
GB
United Kingdom
Prior art keywords
tropine
hydrochloride
methylmercaptoethyl
converted
ester
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
GB4261/57A
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.)
Merck KGaA
Original Assignee
E Merck 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 E Merck AG filed Critical E Merck AG
Publication of GB813218A publication Critical patent/GB813218A/en
Expired 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
    • 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

Abstract

The invention comprises esters of N-(b -methylmercaptoethyl)-nor-tropine and -nor-q -tropine, of the general formula: <FORM:0813218/IV (b)/1> (wherein R represents an aryl, aralkyl or alkaryl radical, which may contain oxygen), and their water-soluble, physiologically acceptable acid addition salts, and the preparation thereof by condensing acetone dicarboxylic acid, succindialdehyde and b -methylmercaptoethylamine under the conditions of the tropinone synthesis, and reducing the resulting tropionone derivative to the corresponding tropine and/or q -tropine derivative, which is or are then esterified with an organic acid RCOOH and the product converted, if desired, into a water-soluble, physiologically acceptable acid addition salt by means of an inorganic or organic acid. In examples: (1) acetone dicarboxylic acid and methylmercaptoethylamine are added to an aqueous solution of succindialdehyde, the pH being periodically adjusted to 6 by adding acetic acid; after standing, N-(b -methylmercaptoethyl) - nor - tropinone hydrochloride is isolated, or the free base is isolated and may be converted to hydrochloride or picrate; the base is reduced with lithium aluminium hydride in ether, and the resulting nor-tropine and nor-q -tropine compounds are separated as hydrochlorides (the picrates also being described); N-(b -methylmercaptoethyl)-nor-q -tropine is esterified with anisoyl chloride and the ester is converted into its hydrochloride; (2) N-(b -methylmercaptoethyl)-nor-tropinone hydrochloride is reduced with hydrogen in the presence of rhenium sulphide to the corresponding nor - q - tropine hydrochloride, from which the base is liberated and is esterified with benzoyl chloride, the ester being converted to its hydrochloride; (3) N-(b -methylmercaptoethyl) - nor - q - tropine is heated with the ethyl ester of diphenylglycollic acid and sodium, and the resulting ester is converted into its hydrochloride and ethanesulphonate; (4) the same ester is obtained by melting the base with diphenylglycollic acid and passing in dry hydrogen chloride gas, the basic ester being isolated and converted to its hydrochloride, sulphate and nitrate; (5) N-(b -methylmercaptoethyl)nor-tropine is esterified as in (3); (6) N-(b - methylmercaptoethyl) - nor - tropine is heated with the methyl ester of 9-hydroxyfluorenecarboxylic acid-(9) and sodium and the product is converted to its hydrochloride. The products are useful in pharmacy for their local an sthetic and parasympatholytic effects.
GB4261/57A 1956-03-08 1957-02-07 Nor-tropines and nor-pseudo-tropines and process for their production Expired GB813218A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE813218X 1956-03-08

Publications (1)

Publication Number Publication Date
GB813218A true GB813218A (en) 1959-05-13

Family

ID=6732696

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4261/57A Expired GB813218A (en) 1956-03-08 1957-02-07 Nor-tropines and nor-pseudo-tropines and process for their production

Country Status (1)

Country Link
GB (1) GB813218A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007500148A (en) * 2003-07-28 2007-01-11 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Medicament containing PDEIV inhibitor and novel anticholinergic agent and use of the medicament for treating respiratory diseases
JP2007500146A (en) * 2003-07-28 2007-01-11 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Drugs for inhalation containing beta receptor stimulants and anticholinergics
JP2007500147A (en) * 2003-07-28 2007-01-11 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Inhalable medicine containing steroid and fluorene carboxylic acid ester

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007500148A (en) * 2003-07-28 2007-01-11 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Medicament containing PDEIV inhibitor and novel anticholinergic agent and use of the medicament for treating respiratory diseases
JP2007500146A (en) * 2003-07-28 2007-01-11 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Drugs for inhalation containing beta receptor stimulants and anticholinergics
JP2007500147A (en) * 2003-07-28 2007-01-11 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Inhalable medicine containing steroid and fluorene carboxylic acid ester

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