GB969518A - Tetrahydrodibenzocyclo-octene derivatives - Google Patents

Tetrahydrodibenzocyclo-octene derivatives

Info

Publication number
GB969518A
GB969518A GB15358/61A GB1535861A GB969518A GB 969518 A GB969518 A GB 969518A GB 15358/61 A GB15358/61 A GB 15358/61A GB 1535861 A GB1535861 A GB 1535861A GB 969518 A GB969518 A GB 969518A
Authority
GB
United Kingdom
Prior art keywords
acid
group
tetrahydrodibenzo
carbon atoms
alkyl
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
GB15358/61A
Inventor
August Franciscus Harms
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.)
Koninklijke Pharmaceutische Fabrieken NV
Original Assignee
Koninklijke Pharmaceutische Fabrieken NV
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 Koninklijke Pharmaceutische Fabrieken NV filed Critical Koninklijke Pharmaceutische Fabrieken NV
Priority to GB15358/61A priority Critical patent/GB969518A/en
Priority to BR138474/62A priority patent/BR6238474D0/en
Priority to DK188462AA priority patent/DK102908C/en
Priority to FR904989A priority patent/FR2191M/en
Publication of GB969518A publication Critical patent/GB969518A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/33Polycyclic acids
    • C07C63/331Polycyclic acids with all carboxyl groups bound to non-condensed rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention comprises tetrahydrodibenzo [a, d] cyclooctene derivatives of the general formula <FORM:0969518/C1/1> (wherein A represents an alkylene group containing 2 to 6 carbon atoms, B represents an alkylamino or dialkylamino group, on a saturated mononuclear 5- or 6-membered heterocyclic group attached to A through a nitrogen atom, which heterocyclic group may carry alkyl substituents and-when alkyl substituted-contains at most 12 carbon atoms, or A and B taken together represent a 3-tropanyl or 3-pseudo-tropanyl radical, the word "alkyl" being defined as an alkyl group containing at most 6 carbon atoms) and their acid addition salts, by heating a compound of formula <FORM:0969518/C1/2> with a compound of formula Y-A-B, wherein one of X and Y represents a halogen atom and the other an -O-alkali metal group, or X represents a halogen atom or hydroxyl group and Y represents a hydroxyl group, preferably (when X=halogen and Y=OH) in the presence of an acid-binding agent or (when X=Y=OH), a dehydrating agent. The starting materials may be prepared as follows:- The g -lactone of 2-(1-hydroxy -3- phenylpropyl) benzoic acid (prepared by condensing o-carboxy-acetophenone with benzaldehyde and hydrogenating the resulting 2-cinnamoylbenzoic acid) is reacted with red phosphorus and HI to give 2-(3-phenylpropyl)-benzoic acid which is cyclised to 5, 10, 11, 12-tetrahydrodibenzo [a, d] cycloocten -5- one by direct treatment with P2O5 or first converted to the acid chloride which is then cyclised using AlCl3. The ketone is reduced using LiAlH4 to give 5, 10, 11, 12-tetrahydrodibenzo [a, d] cyclo-octen-5- ol which may be converted to the corresponding halide or to its alkali metal derivative. Pharmaceutical preparations comprise the compounds of the invention in association with a pharmacologically acceptable carrier. They have antiallergic, anticholinergic, psychotropic and analgesic activity, and may take the form of tablets, pills, capsules, solutions, suspensions, emulsions, syrups or elixirs.
GB15358/61A 1961-04-27 1961-04-27 Tetrahydrodibenzocyclo-octene derivatives Expired GB969518A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB15358/61A GB969518A (en) 1961-04-27 1961-04-27 Tetrahydrodibenzocyclo-octene derivatives
BR138474/62A BR6238474D0 (en) 1961-04-27 1962-04-26 PROCESS FOR THE PREPARATION OF NEW BASICLY REPLACED TETRA-HYDRO-DI-BENZO CYCLE-OCTENS AND ITS NON-TOXIC ACID ADDITION SALTS
DK188462AA DK102908C (en) 1961-04-27 1962-04-26 Process for the preparation of derivatives of tetrahydrodibenzocylooctene or salts thereof.
FR904989A FR2191M (en) 1961-04-27 1962-07-25 Tetrahydrodibenzocyclooctenes.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB15358/61A GB969518A (en) 1961-04-27 1961-04-27 Tetrahydrodibenzocyclo-octene derivatives

Publications (1)

Publication Number Publication Date
GB969518A true GB969518A (en) 1964-09-09

Family

ID=10057759

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15358/61A Expired GB969518A (en) 1961-04-27 1961-04-27 Tetrahydrodibenzocyclo-octene derivatives

Country Status (4)

Country Link
BR (1) BR6238474D0 (en)
DK (1) DK102908C (en)
FR (1) FR2191M (en)
GB (1) GB969518A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009513491A (en) * 2003-06-24 2009-04-02 ノイロサーチ アクティーゼルスカブ Novel 8-aza-bicyclo [3.2.1] octane derivatives and their use as monoamine neurotransmitter reuptake inhibitors

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009513491A (en) * 2003-06-24 2009-04-02 ノイロサーチ アクティーゼルスカブ Novel 8-aza-bicyclo [3.2.1] octane derivatives and their use as monoamine neurotransmitter reuptake inhibitors

Also Published As

Publication number Publication date
BR6238474D0 (en) 1973-05-24
DK102908C (en) 1965-10-25
FR2191M (en) 1963-12-09

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