GB1434871A - 10-piperazinyl-dibenzo-b,f-thiepin derivatives methods for their preparation and compositions containing them - Google Patents

10-piperazinyl-dibenzo-b,f-thiepin derivatives methods for their preparation and compositions containing them

Info

Publication number
GB1434871A
GB1434871A GB1401774A GB1401774A GB1434871A GB 1434871 A GB1434871 A GB 1434871A GB 1401774 A GB1401774 A GB 1401774A GB 1401774 A GB1401774 A GB 1401774A GB 1434871 A GB1434871 A GB 1434871A
Authority
GB
United Kingdom
Prior art keywords
compounds
compound
reacting
piperazinyl
substituted
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
GB1401774A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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 CH460473A external-priority patent/CH576469A5/en
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1434871A publication Critical patent/GB1434871A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
    • C07D337/02—Seven-membered rings
    • C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
    • C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
    • C07D337/14—[b,f]-condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)

Abstract

1434871 Piperazinyl-dibenz[b,1]thiepin derivatives F HOFFMANN-LA ROCHE & CO AG 29 March 1974 [30 March 1973 16 Jan 1974] 14017/74 Heading C2C Novel compounds I and salts thereof in which n is 1 to 3, R is H or when n is 2 or 3, R is also OH or C 1-18 alkanoyloxy, one of R 1 and R 2 is H and the other is Cl, Me, MeO, MeS, Me 2 NSO 2 or CF 3 and one of R 3 and R 4 is H and the other is Me, MeO, MeS, Me 2 NSO 2 or CF 3 and the dotted line represents an optional bond are prepared by (1) reacting a compound II where Y is a leaving atom or group (preferably Cl) with an R-(CH 2 ) n -substituted piperazine to form a 10,11-dihydro derivative (2) reacting a compound IX with an R-(CH 2 ) n -substituted piperazine (3) reacting a compound V with ethylene oxide propylene oxide or a compound Y-(CH 2 ) n -R to form a 10,11-dihydro derivative (4) for compounds I in which R is C 1-18 alkanoyloxy, acylating the corresponding compound in which R is hydroxy or (5) for 10,11- dihydro derivatives hydrogenating the corresponding compound I containing the 10,11 double bond. Compounds IX (R 3 or R 4 =Mi or SMe) are prepared by diazotizing on R 1 or R 2 substituted anthranilic acid and reacting the diazonium salt with potassium iodide to form the corresponding 2-iodo-benzoic acid which is reacted in the presence of copper with an appropriately substituted thiophenol, converting the carboxyl group of the diphenyl ether to carboxyl methyl group by the Standard homologation procedure and cyclizing the acid under acidic conditions. Compounds IX are reduced to the alcohol which is chlorinated to form compounds V (Y = Cl). Compounds I are CNS depressants and have neuroleptic properties and form with a carrier a pharmaceutical composition which may be administered orally or parenterally. Reference has been directed by the Comptroller to Specification 1,369,525.
GB1401774A 1973-03-30 1974-03-29 10-piperazinyl-dibenzo-b,f-thiepin derivatives methods for their preparation and compositions containing them Expired GB1434871A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH460473A CH576469A5 (en) 1973-03-30 1973-03-30 Central-inhibitory and neuroleptic tricyclic cpds. - prepd. by reacting a 10-halo substd. dibenzothiepin with a substd. piperazine
CH56774 1974-01-16

Publications (1)

Publication Number Publication Date
GB1434871A true GB1434871A (en) 1976-05-05

Family

ID=25684979

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1401774A Expired GB1434871A (en) 1973-03-30 1974-03-29 10-piperazinyl-dibenzo-b,f-thiepin derivatives methods for their preparation and compositions containing them

Country Status (4)

Country Link
JP (1) JPS49135984A (en)
DE (1) DE2412521A1 (en)
FR (1) FR2223040B1 (en)
GB (1) GB1434871A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CS196893B1 (en) * 1977-12-22 1980-04-30 Miroslav Protiva 3-fluor-10-piperazino-8-substituted 10,11-dihydro-dibenzothiepines

Also Published As

Publication number Publication date
FR2223040A1 (en) 1974-10-25
DE2412521A1 (en) 1974-10-10
FR2223040B1 (en) 1977-08-19
JPS49135984A (en) 1974-12-27

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee