GB1087099A - New azepine derivatives, their production and use - Google Patents
New azepine derivatives, their production and useInfo
- Publication number
- GB1087099A GB1087099A GB2694365A GB2694365A GB1087099A GB 1087099 A GB1087099 A GB 1087099A GB 2694365 A GB2694365 A GB 2694365A GB 2694365 A GB2694365 A GB 2694365A GB 1087099 A GB1087099 A GB 1087099A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dibenz
- azepine
- dihydro
- formula
- reacting
- 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
- 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
- C07D223/24—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
- C07D223/28—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom having a single bond between positions 10 and 11
-
- 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
-
- 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
- C07D223/24—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the formula <FORM:1087099/C2/1> in which X is ethylene or vinylene, R1 is C1- 4 alkyl or phenyl, R2 is H or C1- 4 alkyl, R3 is H, C1- 4 alkyl or benzyl and R4 is C1- 4\t alkyl or, when taken together with R2, it represents an alkylene radical with (3-n) or (4-n) chain members or, when taken together with R3, it represents an alkylene radical having 4 to 6 chain members, m is 1 or 2, n is 0, 1 or 2 and (m+n) is 1, 2 or 3; their salts with inorganic and organic acids; and their preparation by (a) reacting a compound of the formula <FORM:1087099/C2/2> with a reactive ester of an amino alcohol of the formula <FORM:1087099/C2/3> in the presence of a basic condensing agent or (b) reacting a reactive ester of a hydroxy compound of the formula <FORM:1087099/C2/4> with a amine of the formula HNR3R4, or (c) reducing, by means of a complex metal hydride, the carbonyl group to the methylene group in a compound of the formula <FORM:1087099/C2/5> in which R14 is H or an alkyl group containing one methylene group less than R4, or (d) heating a compound of the formula <FORM:1087099/C2/6> wherein R13 is C1- 4 alkyl or benzyl until the equimolar amount of carbon dioxide is split off, or (e) hydrolysing or thermolysing a compound of the formula <FORM:1087099/C2/7> in which R5 represents a carboxylic acid radical or the radical of a monofunctional derivative of carbonic acid. 3 - Methylthio - (or 3 - ethylthio) - 10,11 - dihydro - 5H - dibenz[b,f]azepine is prepared by hydrolysing 3 - methylthio- (or 3 - ethylthio)-5-acetyl - 10,11 - dihydro - 5H - dibenz[b,f] azepine with potassium hydroxide in diethylene glycol monomethyl ether. 3 - Isopropylthio - 10,11 - dihydro - 5H - dibenz [b,f]azepine-5-carbonyl chloride is prepared by reacting 3 - isopropylthio - 10,11 - dihydro - 5H-dibenz[b,f]azepine with phosgene. 5 - (31 - Chloropropyl) - 3 - ethylthio - 10,11-dihydro - 5H - dibenz[b,f]azepine is prepared by reacting 3 - ethylthio - 10,11 - dihydro - 5H - dibenz[b,f]azepine with 1,3-chlorobromopropane. 5 - (31 - Acetyl - methylamino - propyl) - 3 - methylthio -10,11 - dihydro - 5H - dibenz[b,f]-azepine is prepared by reacting 5-(31-methylamino - propyl) - 3 - methylthio - 10,11 - di-hydro - 5H - dibenz[b,f]azepine with acetic anhydride. 5 - [31 - (N - ethoxycarbonyl - methylamino-propyl)] - 3 - methythio - 10,11 - dihydro - 5H - dibenz[b,f]azepine is prepared by reacting 5 - (31 - dimethylamino - propyl) - 3 - methylthio - 10,11 - dihydro - 5H - dibenz[b,f]azepine with chloroformic acid ethyl ester. The corresponding 3-ethylthio and 3-isopropylthio compounds are similarly prepared. Pharmaceutical compositions having adrenolytic, hypotensive, serotonin-antagonistic, reserpine - antagonistic, tetrabenazine - antagonistic, spasmolytic, sedative and catecholamine-potentiating activity, for peroral, rectal and parenteral administration, comprise a compound of the invention together with a pharmaceutical carrier.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH842464A CH442317A (en) | 1964-06-26 | 1964-06-26 | Process for the production of azepine derivatives |
CH842564A CH440287A (en) | 1964-06-26 | 1964-06-26 | Process for the production of new azepine derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1087099A true GB1087099A (en) | 1967-10-11 |
Family
ID=25703296
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2694365A Expired GB1087099A (en) | 1964-06-26 | 1965-06-25 | New azepine derivatives, their production and use |
Country Status (2)
Country | Link |
---|---|
GB (1) | GB1087099A (en) |
IL (2) | IL31132A (en) |
-
1965
- 1965-06-25 IL IL3113265A patent/IL31132A/en unknown
- 1965-06-25 GB GB2694365A patent/GB1087099A/en not_active Expired
- 1965-06-25 IL IL2380565A patent/IL23805A/en unknown
Also Published As
Publication number | Publication date |
---|---|
IL23805A (en) | 1969-02-27 |
IL31132A (en) | 1969-07-30 |
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