GB1004288A - New azepine derivatives and process for their production - Google Patents
New azepine derivatives and process for their productionInfo
- Publication number
- GB1004288A GB1004288A GB1425163A GB1425163A GB1004288A GB 1004288 A GB1004288 A GB 1004288A GB 1425163 A GB1425163 A GB 1425163A GB 1425163 A GB1425163 A GB 1425163A GB 1004288 A GB1004288 A GB 1004288A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dibenz
- chloro
- azepines
- alkoxy
- carbon atoms
- 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
- 150000001538 azepines Chemical class 0.000 title abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 239000000460 chlorine Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- SSBIXUWPVVAYGF-UHFFFAOYSA-N 1-(2,9-dichlorobenzo[b][1]benzazepin-11-yl)ethanone Chemical group C(C)(=O)N1C2=C(C=CC3=C1C=C(C=C3)Cl)C=CC(=C2)Cl SSBIXUWPVVAYGF-UHFFFAOYSA-N 0.000 abstract 1
- OSQPHLCMJMVXLB-UHFFFAOYSA-N 1-(5H-dibenzo[b,f]azepin-5-yl)ethan-1-one Chemical group C1=CC2=CC=CC=C2N(C(=O)C)C2=CC=CC=C21 OSQPHLCMJMVXLB-UHFFFAOYSA-N 0.000 abstract 1
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical class C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000005277 alkyl imino group Chemical group 0.000 abstract 1
- 230000003266 anti-allergic effect Effects 0.000 abstract 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 230000001131 transforming effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Abstract
The invention comprises dibenzazepine derivatives of the formula <FORM:1004288/C2/1> wherein R represents an alkyl radical containing up to 4 carbon atoms or an aralkyl radical, the alkyl moiety of which contains up to 4 carbon atoms, X and Y independently of each other represent hydrogen or chlorine, Z represents a straight or branched chain alkylene radical having 2 to 6 carbon atoms, and Am represents an N-arylmethyl-alkylamino group, the alkyl moiety of which contains up to 4 carbon atoms or a dialkylamino group, each alkyl radical of which contains up to 4 carbon atoms, and which alkyl radicals may be bound to each other direct or by way of an alkylimino group containing up to 3 carbon atoms, and their acid-addition salts. The compounds are prepared by condensing a compound of the formula <FORM:1004288/C2/2> with a reactive ester, e.g. a halide or sulphonate, of an alcohol of the formula HO-Z-Am, in the presence of an alkaline condensing agent. Starting materials of formula II wherein X and Y are both hydrogen or both chlorine, are prepared by adding bromine to the 10- and 11-positions of 5-acetyl-5H-dibenz [b,f] azepine or 5 - acetyl - 3,7 - dichloro - 5H - dibenz [b, f] azepine, converting the dibromine compounds by means of alkali alkanolates into 10-alkoxy - 5H - dibenz [b, f] azepines, substituting these in the S position with an appropriate alkyl or aralkyl group, and hydrolysing the 5 - substituted - 10 - alkoxy - 5H - dibenz [b, f] azepines obtained. The compounds of formula II wherein one of X and Y is chlorine and the other is hydrogen, are prepared by adding bromine to the 10- and 11-positions of 5-alkanoyl - 3 - chloro - 5H - dibenz [b, f] azepines converting the dibromine compounds, transforming these either direct or by way of mixtures of 3 - chloro - 5 - alkanoyl - 10 - bromoand 3 - chloro - 5 - alkanoyl - 11 - bromo - SH-dibenz [b, f] azepines into mixtures of 3-chloro - 10 - alkoxy - and 3 - chloro - 11 - alkoxy-5H - dibenz [b, f] azepines, separating these, substituting the separated products in the 5-position with an appropriate alkyl or aralkyl group and hydrolysing the 3-chloro-10-alkoxy-or 3 - chloro - 11 - alkoxy - 5 - substituted - 5H-dibenz [b, f] azepines obtained. Pharmaceutical compositions for peroral or parenteral administration having reserpin-an-tagonistic and anti-allergic properties comprise a compound of the invention or an acid-addition salt thereof together with a carrier.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH468262 | 1962-04-17 | ||
| CH1421462A CH416642A (en) | 1962-12-04 | 1962-12-04 | Process for the production of new azepine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1004288A true GB1004288A (en) | 1965-09-15 |
Family
ID=25696056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1425163A Expired GB1004288A (en) | 1962-04-17 | 1963-04-10 | New azepine derivatives and process for their production |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT239795B (en) |
| BE (1) | BE631161A (en) |
| DE (1) | DE1445816A1 (en) |
| ES (1) | ES287407A1 (en) |
| FI (1) | FI40383B (en) |
| GB (1) | GB1004288A (en) |
-
1963
- 1963-04-10 FI FI71563A patent/FI40383B/fi active
- 1963-04-10 GB GB1425163A patent/GB1004288A/en not_active Expired
- 1963-04-16 DE DE19631445816 patent/DE1445816A1/en active Pending
- 1963-04-16 ES ES287407A patent/ES287407A1/en not_active Expired
- 1963-04-16 AT AT309563A patent/AT239795B/en active
- 1963-04-17 BE BE631161A patent/BE631161A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1445816A1 (en) | 1969-10-09 |
| FI40383B (en) | 1968-09-30 |
| AT239795B (en) | 1965-04-26 |
| BE631161A (en) | 1963-11-18 |
| ES287407A1 (en) | 1963-12-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1213162A (en) | Serum lipid lowering pyridine derivatives and their preparation | |
| GB961105A (en) | Improvements relating to diazepine compounds | |
| MY100095A (en) | 2-oxo-imidazolidine compounds, a process for preparing the same and a pharmaceutical composition. | |
| HUT38927A (en) | Process for producing 5-alkyl-1-phenyl-2-/piperazino-alkyl/-pyrazolin-3-one derivatives | |
| GB1004288A (en) | New azepine derivatives and process for their production | |
| ES8506304A1 (en) | Piperazine derivatives and a medicine containing the same | |
| GB1212174A (en) | Process for the production of new 2-oxo-1,2-dihydroquinoline derivatives | |
| IE41767L (en) | Dihydroergopeptine derivatives | |
| ES444369A1 (en) | Dienic derivatives of the androstane series and process | |
| GB1239814A (en) | Process for the preparation of 7-aminocephalosporanic acid and its derivatives | |
| IL48790A (en) | Hydroxy-pyrimidines,their preparation and pharmaceutical compositions containing them | |
| AU539348B2 (en) | 5,6,8,9-tetrahydro-7h-dibenz(d,f)azonine derivatives | |
| US3763169A (en) | Isonipecotic acid compounds | |
| GB980592A (en) | Novel benzoxazepine derivatives and a process for the manufacture thereof | |
| DE3362248D1 (en) | Ergoline derivatives, process for producing the ergoline derivatives and pharmaceutical compositions containing them | |
| HU895651D0 (en) | Process for the preparation of substituted 3-amino-nonimine derivatives and pharmaceutical compositions containing said compounds | |
| GB962462A (en) | Substituted 5h-dibenz [b.f] azepines and processes for their production | |
| IL39296A (en) | 10-(4-(hydroxyalkoxy)piperidinoalkyl)-phenothiazine derivatives and process for preparing them | |
| GB1035173A (en) | New azepine derivatives and process for their production | |
| AU560032B2 (en) | Derivatives of r-butyrolactone | |
| GB1114970A (en) | New azepine derivatives and their production | |
| GB1015617A (en) | Substituted iminostilbene and iminodibenzyl derivatives | |
| GB974744A (en) | New 4-substituted 1,2-diaryl-3,5-dioxopyrazolidines and processes for preparing same | |
| FR2364921A1 (en) | ETHERIFIED DIAZEPINE DERIVATIVES USEFUL AS MEDICINAL PRODUCTS | |
| GB1070714A (en) | (alkylaminoethoxy)-dihaloanilines and process of preparation thereof |