GB1087099A - New azepine derivatives, their production and use - Google Patents

New azepine derivatives, their production and use

Info

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
Application number
GB2694365A
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.)
Novartis AG
Original Assignee
JR Geigy AG
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
Priority claimed from CH842464A external-priority patent/CH442317A/en
Application filed by JR Geigy AG filed Critical JR Geigy AG
Publication of GB1087099A publication Critical patent/GB1087099A/en
Expired legal-status Critical Current

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.
GB2694365A 1964-06-26 1965-06-25 New azepine derivatives, their production and use Expired GB1087099A (en)

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) IL23805A (en)

Also Published As

Publication number Publication date
IL23805A (en) 1969-02-27
IL31132A (en) 1969-07-30

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