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GB1411587A - Dibenzo b,f 1,4 thiazepine derivatives - Google Patents

Dibenzo b,f 1,4 thiazepine derivatives

Info

Publication number
GB1411587A
GB1411587A GB5665972A GB5665972A GB1411587A GB 1411587 A GB1411587 A GB 1411587A GB 5665972 A GB5665972 A GB 5665972A GB 5665972 A GB5665972 A GB 5665972A GB 1411587 A GB1411587 A GB 1411587A
Authority
GB
United Kingdom
Prior art keywords
compound
reaction
prepared
hydrogen
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
GB5665972A
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.)
Wander AG
Original Assignee
Wander 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
Application filed by Wander AG filed Critical Wander AG
Publication of GB1411587A publication Critical patent/GB1411587A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D281/02—Seven-membered rings
    • C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
    • C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D281/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with two six-membered rings
    • C07D281/16—[b, f]-condensed

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1411587 2 - Trifluoromethyl - -11 - piperazinyldibenzo[b,1][1,4]thiazepines WANDER Ltd 8 Dec 1972 [9 Dec 1971] 56659/72 Heading C2C Novel compounds I in which R 1 is hydrogen, C 1-4 alkyl, C 1-4 hydroxyalkyl, C 3-6 acetoxyalkyl or C 2-6 alkoxyalkyl and their salts are prepared by (1) reaction of a compound II in which X is a radical capable of being split off with hydrogen from an N-atom of piperazine, with an R 1 substituted piperazine (2) subjecting a compound IV in which Y is oxygen or sulphur to ring closure, (3) alkylating hydroxy alkylating or alkoxy alkylating a compound I in which R 1 is hydrogen to form a compound I in which R 1 is C 1-4 alkyl C 1-4 hydroxyalkyl or C 2-6 alkoxyalkyl or (4) acetylating a compound I in which R 1 is C 1-4 hydroxyalkyl to form a compound I in which R 1 is C 3-6 acetoxy alkyl. Compounds prepared are those in which R 1 is hydrogen, methyl ethyl, #-hydroxy ethyl, # - or γ-hydroxypropyl, #- methoxyethyl or #-acetoxyethyl. Compounds II (X=C1) are prepared from compound V by (a) reaction with phosphorus oxychloride which compound may be further reacted (i) with an alkali metal alcoholate to form compound II (X=alkoxy) or (ii) with ammonia or an amine (X=amine) or (b) converting compound V into a thiolactam followed by alkylation to form compound II (X=alkylthio). Compound V is obtained by ring closure of compound VI which is obtained by reacting 2-bromo-5-trifluoromethylsulphonyl benzoic acid with 2- aminophenol in presence of an acid-binding agent. 2 - Bromo - 5 - trifluoromethylsulphonyl benzoic acid is obtained from 2-bromo-5-thiomethyl benzoic acid by reaction with chlorine followed by hydrogen fluoride and subsequent oxidation. Compounds IV (Y=O) are prepared from compound X by formation of the acid chloride, reaction with N-R 1 -piperazine and reduction of the nitro group. Compound X is prepared by reaction of 2-nitro thiophenol with 2-bromo-5-trifluoromethylsulphonyl benzoic acid. Compounds I are sedatives and form with a carrier or diluent a pharmaceutical composition which may be administered orally.
GB5665972A 1971-12-09 1972-12-08 Dibenzo b,f 1,4 thiazepine derivatives Expired GB1411587A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1792571A CH560213A5 (en) 1971-12-09 1971-12-09

Publications (1)

Publication Number Publication Date
GB1411587A true GB1411587A (en) 1975-10-29

Family

ID=4429135

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5665972A Expired GB1411587A (en) 1971-12-09 1972-12-08 Dibenzo b,f 1,4 thiazepine derivatives

Country Status (6)

Country Link
JP (1) JPS4864090A (en)
BE (1) BE792426A (en)
CH (1) CH560213A5 (en)
DE (1) DE2259568A1 (en)
FR (1) FR2162575B1 (en)
GB (1) GB1411587A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU595099B2 (en) * 1987-03-10 1990-03-22 Astrazeneca Ab Process for the preparation of a thiazepine compound
WO2007004234A1 (en) * 2005-07-04 2007-01-11 Usv Limited A PROCESS FOR THE PREPARATION OF 2-[2-(4-DIBENZO[b,f] [L,4] THIAZEPIN-11-yl-1- PIPERAZINYL)ETHOXY] ETHANOL FUMARATE

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8607684D0 (en) * 1986-03-27 1986-04-30 Ici America Inc Thiazepine compounds
KR101038389B1 (en) * 2004-06-23 2011-06-01 에스케이바이오팜 주식회사 11- (4- [2- (2-hydroxyethoxy) ethyl] -1-piperazinyl) -dibenzo [VII, VII] [1,4] thiazepine

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3539573A (en) * 1967-03-22 1970-11-10 Jean Schmutz 11-basic substituted dibenzodiazepines and dibenzothiazepines
BE754406A (en) * 1969-08-06 1971-02-04 Wander Ag Dr A NEW DIBENZO-OXAZEPINE DERIVATIVES THEIR PREPARATION AND MEDICINAL PRODUCTS CONTAINING THESE DERIVATIVES

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU595099B2 (en) * 1987-03-10 1990-03-22 Astrazeneca Ab Process for the preparation of a thiazepine compound
WO2007004234A1 (en) * 2005-07-04 2007-01-11 Usv Limited A PROCESS FOR THE PREPARATION OF 2-[2-(4-DIBENZO[b,f] [L,4] THIAZEPIN-11-yl-1- PIPERAZINYL)ETHOXY] ETHANOL FUMARATE

Also Published As

Publication number Publication date
JPS4864090A (en) 1973-09-05
FR2162575A1 (en) 1973-07-20
FR2162575B1 (en) 1976-07-02
BE792426A (en) 1973-06-07
CH560213A5 (en) 1975-03-27
DE2259568A1 (en) 1973-06-14

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees