GB969518A - Tetrahydrodibenzocyclo-octene derivatives - Google Patents
Tetrahydrodibenzocyclo-octene derivativesInfo
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/33—Polycyclic acids
- C07C63/331—Polycyclic 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.
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)
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 |
-
1961
- 1961-04-27 GB GB15358/61A patent/GB969518A/en not_active Expired
-
1962
- 1962-04-26 DK DK188462AA patent/DK102908C/en active
- 1962-04-26 BR BR138474/62A patent/BR6238474D0/en unknown
- 1962-07-25 FR FR904989A patent/FR2191M/en active Active
Cited By (1)
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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