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GB983859A - New derivatives of azocine - Google Patents

New derivatives of azocine

Info

Publication number
GB983859A
GB983859A GB2402461A GB2402461A GB983859A GB 983859 A GB983859 A GB 983859A GB 2402461 A GB2402461 A GB 2402461A GB 2402461 A GB2402461 A GB 2402461A GB 983859 A GB983859 A GB 983859A
Authority
GB
United Kingdom
Prior art keywords
formula
group
compound
piperazino
compounds
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
GB2402461A
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.)
Rhone Poulenc SA
Original Assignee
Rhone Poulenc SA
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
Application filed by Rhone Poulenc SA filed Critical Rhone Poulenc SA
Publication of GB983859A publication Critical patent/GB983859A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
    • C07D225/02—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • 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
    • C07D223/20—Dibenz [b, e] azepines; Hydrogenated dibenz [b, e] azepines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
    • C07D225/04—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D225/08—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with two six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

The invention comprises compounds of general formula <FORM:0983859/C2/1> wherein: A represents a straight or branched saturated aliphatic hydrocarbon group containing 1 to 6 carbon atoms; Z represents an amino, monoalkylamino, dialkylamino, pyrrolidino, piperidino, morpholino, thiomorpholino, piperazino or N-alkylpiperazino group, or an N-alkylpiperidyl or N-alkylpyrrolidyl group attached to the hydrocarbon radical A by a carbon atom of the heterocyclic nucleus, or a group of general formula <FORM:0983859/C2/2> where R represents a hydrogen atom or a hydroxyalkyl group, n represents 0, 1, 2 or 3 and m represents 2 or 3; B represents hydrogen or a group Z; and, where Z or B represents piperazino, N-alkylpiperazino or a piperazino group (IV), then the piperazine ring may be substituted on one or more carbon atoms by an alkyl group, and the word alkyl means an alkyl group containing not more than 4 carbon atoms; and their acid addition salts; and their preparation by (1) reacting 5,10,11,12-tetrahydrodibenz[b,g]azocine with a compound of formula Y-A(B)-Z where Y represents the acid residue of a reactive ester, (2) reacting a compound of formula HZ with a compound of formula <FORM:0983859/C2/3> where B1 represents hydrogen or a group Y, and (3) decarboxylating a compound of formula <FORM:0983859/C2/4> by heating to a temperature above 100 DEG C. until evolution of carbon dioxide ceases. Other processes referred to are (4) the reaction of compounds of formula <FORM:0983859/C2/5> where T is piperazino and B2 is hydrogen or piperazino, either with a compound of formula YCmH2mOR or with ethylene oxide or propylene oxide, and (5) the reaction of compounds of formula <FORM:0983859/C2/6> where X is <FORM:0983859/C2/7> and B3 is hydrogen or a group X, either with a compound of formula Y-R1, where R1 is hydroxyalkyl, or with ethylene or propylene oxide. Esters (A) above may be prepared from corresponding carboxylic acid halides by reaction with an alcohol of formula HO-A(B)-Z. 5 - (3 - Chloro - 2 - methylpropyl) - 5,10,11,12 - tetrahydrodibenz[b,g]azocine is obtained by reacting the 5-unsubstituted compound with butyl-lithium in ether and adding 1-chloro-2-methyl - 3 - toluene - p - sulphonyloxypropane. 5 - (3 - Chloropropyl) - 5,10,11,12 - tetrahydrodibenz[b,g]azocine is obtained similarly. 5 - (2 - Hydroxyethyl) - 5,10,11,12 - tetrahydrodibenz[b,g]azocin is obtained by reacting the 5-unsubstituted compound with butyl-lithium in ether and adding ethylene oxide. Pharmaceutical compositions comprise compounds (I) and salts of the invention together with pharmaceutical carriers. Oral, parenteral and rectal administration is described (e.g. as tablets, capsules, pills, powders, granules, syrups, elixirs, suspensions, solutions, emulsions, suppositories). The compounds are useful in psychic disorders and as antiemetics, spasmolytics, muscle-relaxants, local anaesthetics, antihistaminics and sedatives. Specification 926,335 is referred to.
GB2402461A 1960-07-05 1961-07-03 New derivatives of azocine Expired GB983859A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR832058A FR1403603A (en) 1960-07-05 1960-07-05 New derivatives of tetrahydro-5, 10, 11, 12 dibenz [b, g] azocine and processes for their preparation
FR863626A FR1339M (en) 1960-07-05 1961-06-01 Dibenzazocin derivatives.
FR863760A FR85301E (en) 1960-07-05 1961-06-02 New derivatives of tetrahydro-5, 10, 11, 12 dibenzo [b, g] azocine and processes for their preparation

Publications (1)

Publication Number Publication Date
GB983859A true GB983859A (en) 1965-02-17

Family

ID=39275492

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2402461A Expired GB983859A (en) 1960-07-05 1961-07-03 New derivatives of azocine

Country Status (8)

Country Link
BE (1) BE605628A (en)
CH (2) CH422795A (en)
DE (1) DE1180751B (en)
ES (1) ES268769A1 (en)
FR (3) FR1403603A (en)
GB (1) GB983859A (en)
LU (1) LU40250A1 (en)
NL (1) NL113370C (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT196879B (en) * 1955-10-26 1958-03-25 Rhone Poulenc Sa Process for the preparation of new derivatives of iminodibenzyl

Also Published As

Publication number Publication date
CH439300A (en) 1967-07-15
CH422795A (en) 1966-10-31
LU40250A1 (en) 1961-08-14
DE1180751B (en) 1964-11-05
BE605628A (en) 1962-01-02
NL113370C (en)
FR85301E (en) 1965-07-23
ES268769A1 (en) 1961-12-16
FR1403603A (en) 1965-06-25
FR1339M (en) 1962-06-04

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