6*111DHYDROBENZO *B*E* THIEPINEE111ONES

Japanese Patent JPS51143688

A

1505085 6,11-Dihydro-dibenzo[b,e]thiepin- 11-ones SYNTEX (USA) Inc 16 Jan 1976 [18 Feb 1975 30 June 1975 21 Nov 1975 (2)] 01783/76 Heading C2C Novel compounds I in which R is H, C 1-12 alkyl or a salt-forming group and R11 is H or Me are prepared by (a) reacting 3 - diazoacetyl - 6,11 - dihydrodibenzo[b,e]thiepin - 11 - one with silver benzoate in the presence of a C 1-12 alkanol to form a compound I [R = C 1-12 alkyl ; R11 = H] (b) α-methylating a compound I [R = C 1-12 alkyl; R11 = H] to form a compound I (R = C 1-12 alkyl; R11 = Me) or (c) hydrolysing an ester or converting a salt into the free acid, esterifying a free acid or converting one ester into another by transesterification, converting a salt into another salt by metathesis or salifying a free acid. Compound I (R = H, R11 = Me] is resolved into optical isomers and the lisomers thereof is racemised to the dl form. Nitroterephthalic acid is esterified to form the isopropyl ester which is reacted in the presence of NaH with benzyl mercaptan to form diisopropyl benzylthioterephthalate which is hydrolysed to the free acid and converted to the acid chloride; cyclization of the acid chloride leads to 6,11-dihydro-11-oxo-dibenzo[b,e]thiepin- 3-carbonyl chloride which is reacted with CH 2 N 2 or CH 3 CH 2 N 2 to form the 3-diazoacetyl or 3-(α- diazopropionyl) compound. Compounds I [R11 = H and d and dl compounds where R11 = Me] have anti-inflammatory analgesic, anti-pyretic, platelet aggregation inhibiting, fibrinolytic and smooth-muscle releasing activity; they form with an excipient a pharmaceutical composition which may be administered orally, parenterally, rectally, topically or vaginally.

JIYATSUKU ATSUKURERU

JP1644676A

December 10, 1976

February 17, 1976

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SYNTEX INC

A61K31/38; C07C205/57; C07D337/12; (IPC1-7): A61K31/38; C07D337/12

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