GB908786A - New 10,11-dihydrodibenzazepines and processes for their production - Google Patents
New 10,11-dihydrodibenzazepines and processes for their productionInfo
- Publication number
- GB908786A GB908786A GB25385/60A GB2538560A GB908786A GB 908786 A GB908786 A GB 908786A GB 25385/60 A GB25385/60 A GB 25385/60A GB 2538560 A GB2538560 A GB 2538560A GB 908786 A GB908786 A GB 908786A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- group
- oxo group
- alkanoyl
- reaction
- 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
- ILHYRNCXUBXJRW-UHFFFAOYSA-N 10,11-dihydro-9H-benzo[d][1]benzazepine Chemical class C1=CN=C2C=CC=CC2=C2CCCC=C21 ILHYRNCXUBXJRW-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 9
- 125000004432 carbon atom Chemical group C* 0.000 abstract 7
- 238000006243 chemical reaction Methods 0.000 abstract 7
- -1 hydroxyl compound Chemical class 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- 239000007795 chemical reaction product Substances 0.000 abstract 3
- 230000003301 hydrolyzing effect Effects 0.000 abstract 3
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 3
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical group C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 150000003385 sodium Chemical class 0.000 abstract 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 abstract 1
- QBSUAHGUFKVVTM-UHFFFAOYSA-N 1-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)ethanone Chemical group C1CC2=CC=CC=C2N(C(=O)C)C2=CC=CC=C21 QBSUAHGUFKVVTM-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001339 alkali metal compounds Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000005277 alkyl imino group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 150000004658 ketimines Chemical group 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 208000020016 psychiatric disease Diseases 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises 3-alkanoyl-10,11-dihydrodibenzoazepine compounds of general formula <FORM:0908786/IV (b)/1> wherein R1 represents an alkyl radical (1 to 4 carbon atoms), X is a straight or branched chain alkylene radical having 2-6 carbon atoms, R2 represents an alkyl or alkenyl radical, R3 represents hydrogen or an alkyl or alkenyl radical (each up to 4 carbon atoms), and wherein the radical R2 may be bound to the alkylene radical X, or if R2 and R3 represent alkyl radicals, both can be bound to each other directly or by way of an oxygen atom, an imino, alkylimino (1 to 4 carbon atoms), hydroxyalkylimino (1 to 4 carbon atoms) or alkanoyloxyalkylimino group (the alkanoyl and alkyl moieties of which each have 1 to 4 carbon atoms), and salts thereof with inorganic or organic acids, and the preparation thereof (1) by reacting a 10,11-dihydrodibenzoazepine of the general formula <FORM:0908786/IV (b)/2> or a functional derivative of that general formula with regard to the oxo group, in the presence of an alkaline condensing agent or after conversion into its alkali metal compound, with a reactive ester of an alcohol of general formula <FORM:0908786/IV (b)/3> wherein R13 represents an alkyl, alkenyl or alkanoyl radical, and if necessary hydrolysing any reaction product containing a functionally converted oxo group; (2) by reacting a reactive ester of a hydroxyl compound of the general formula <FORM:0908786/IV (b)/4> or a functional derivative thereof with regard to the oxo group, with an amine of the general formula <FORM:0908786/IV (b)/5> wherein R2 and R3 have the above significance except that R2 cannot be bound to X, and if necessary hydrolysing any reaction product containing a functionally converted oxo group; and (3) by reacting a 10,11-dihydrodibenzoazepine of the second general formula above, or a functional derivative thereof with regard to the oxo group with phosgene and reacting the N - chlorocarbonyl-10,11-dihydrodibenzoazepine compound with an alcohol of general formula <FORM:0908786/IV (b)/6> and heating the resulting N-carboxylic acid ester of the general formula <FORM:0908786/IV (b)/7> to split out carbon dioxide and, if necessary, then hydrolysing the reaction product to liberate the oxo group and/or removing the alkanoyl radical. The functionally converted oxo group may be a cyclic ketal group such as an ethylenedioxy group, or a ketimine group such as a phenylimino group. The products are useful for the treatment of mental disorders. 3-Alkanoyliminodibenzyls of general formula II are obtained by condensation of 5-acetyliminodibenzyl with acetic anhydride or alkanoyl chlorides in the presence of aluminium chloride, and hydrolysis of the resulting 3-alkanoyl-5-acetyliminodibenzyl to remove the 5-acetyl group. Reactive esters of hydroxy compounds of general formula IV, or their functional derivatives with respect to the oxo group, are obtained by treatment of the hydroxy compound with appropriate acid halides, the hydroxy compounds themselves being obtained by reaction of the alkali metal derivatives of function derivatives with regard to the oxo group of compounds of general formula II with alkylene oxides. 5-(g -Chloropropyl)-3-(a ,a -ethylenedioxyethyl)-iminodibenzyl is obtained by reaction of the sodium derivative of 3-(a ,a -ethylenedioxyethyl)-iminodibenzyl with g -bromopropyl chloride. 3 - (a ,a - Ethylenedioxyethyl) - iminodibenzyl is obtained by reaction of 3-acetyl-iminodibenzyl with ethylene glycol in the presence of toluene-p-sulphonic acid, and is converted into the sodium derivative by treatment with sodium amide. 3 - Alkanoyl-5-chlorocarbonyliminodibenzyls are obtained by reaction of phosgene with compounds of general formula II, and are converted into esters of general formula VI by reaction with alcohols of general formula III. Compounds related to general formula I but in which the keto group is protected, the carbon atom thereof occupying the 2-position of a dioxolane ring, are obtained by the methods given above for compounds of general formula I, and are converted thereinto by acid hydrolysis. 3 - (a ,a - ethylenedioxyethyl)-5-[g -(41-formylpiperazinyl-11) propyl]iminodibenzyl is obtained by reaction of 3-(a ,a -ethylenedioxyethyl)-5-sodioiminodibenzyl with 1-formyl-4-(g -chloropropyl)piperazine, and is converted by acid hydrolysis into 3-acetyl-5-[g -(41-formylpiperazinyl-11) propyl]iminodibenzyl.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH7612059A CH374074A (en) | 1959-07-23 | 1959-07-23 | Process for the preparation of new N-heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB908786A true GB908786A (en) | 1962-10-24 |
Family
ID=4534700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25385/60A Expired GB908786A (en) | 1959-07-23 | 1960-07-21 | New 10,11-dihydrodibenzazepines and processes for their production |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE593285A (en) |
| CH (1) | CH374074A (en) |
| FR (1) | FR725M (en) |
| GB (1) | GB908786A (en) |
-
1959
- 1959-07-23 CH CH7612059A patent/CH374074A/en unknown
-
1960
- 1960-07-21 GB GB25385/60A patent/GB908786A/en not_active Expired
- 1960-07-22 BE BE593285A patent/BE593285A/en unknown
- 1960-10-21 FR FR841871A patent/FR725M/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CH374074A (en) | 1963-12-31 |
| BE593285A (en) | 1961-01-23 |
| FR725M (en) | 1961-08-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2008546730A5 (en) | ||
| US4151357A (en) | Polyprenyl piperazines | |
| US3882110A (en) | Novel 2-alkyl-5-thiazole-carboxylic acid derivatives | |
| GB908786A (en) | New 10,11-dihydrodibenzazepines and processes for their production | |
| GB803372A (en) | Hydroxychromone derivatives and methods of preparing the same | |
| GB884760A (en) | Trifluoromethyl phenothiazines | |
| GB776717A (en) | Derivatives of mandelic acid and their salts and process for the preparation thereof | |
| DE50009219D1 (en) | METHOD FOR THE PRODUCTION OF ESTERS | |
| US3202666A (en) | Substituted 9h-pyrido (3-4-b) indole-1 carboxylic acid and derivatives | |
| US3232949A (en) | Process of manufacturing branchedchain mono-olefinic aliphatic acids and intermediates therefor | |
| JPS55151549A (en) | Production of guanidinocaproic ester | |
| KR870007161A (en) | Nitrogen-arylmethoxy-thiophene derivatives and methods for preparing acid addition salts thereof | |
| GB948080A (en) | Benzopyranone derivatives and processes for their production | |
| GB974744A (en) | New 4-substituted 1,2-diaryl-3,5-dioxopyrazolidines and processes for preparing same | |
| GB921513A (en) | Process of making n-acyl derivatives of 6-amino-penicillanic acid | |
| GB813218A (en) | Nor-tropines and nor-pseudo-tropines and process for their production | |
| Carson Jr et al. | Xylitol esters of fatty acids | |
| GB1024650A (en) | Benzofuran derivatives and process for their production | |
| JPS58103379A (en) | Preparation of alpha-acetyl lactone | |
| JPS5813539B2 (en) | Chikantetrazole Sanruino Seizouhou | |
| JPS5576871A (en) | Chromanyloxy fatty acid homolog | |
| GB1018780A (en) | Steroid (2,3í¬c) furazan compounds and the process for the production thereof | |
| GB1119047A (en) | 5-carboxy-2,4-oxazolidinediones and derivatives thereof | |
| GB1025564A (en) | Benzofuran derivatives and process for their production | |
| ES299449A1 (en) | Procedure for the preparation of new derivatives of tiepine (Machine-translation by Google Translate, not legally binding) |