3-Hydroxymethyldibenzo[b,f]thiepins as prostaglandin antagonists

Claim 2

A compound of the formula: ##STR27## or an ester or acetal thereof, wherein n is an integer from 1 to 4; Z is thio, sulfinyl, or sulfonyl; R 1 and/or R 2 is hydrogen, halogen including chloro, bromo, fluoro and iodo, amino, C 1 to C 4 alkyl, C 1 to C 4 alkanoyl, hydroxyl, C 1 to C 4 alkoxy, thiol, C 1 to C 4 alkylthio, C 1 to C 4 alkylsulfinyl, C 1 to C 4 alkylsulfonyl, trifluoromethyl, trifluoromethylthio, cyano, nitro, and C 1 to C 4 alkyl or dialkylamino, aralkyl including benzyl and phenethyl, hydroxyalkyl as CH 3 CHOH; and the dotted line indicates either an olefinic bond or saturation at the 10-, 11-position.

Claim 3

A compound according to claim 1 where Z is thio.

Claim 4

A compound according to claim 1 where the dotted line indicates an olefinic bond.

Claim 5

A compound according to claim 1 where the dotted line indicates saturation.

Claim 6

A compound according to claim 3, 3-hydroxymethyldibenzo[b,f]thiepin.

Claim 7

A compound according to claim 3, 3-hydroxymethyldibenzo[b,f]thiepin-5-oxide.

Claim 8

A compound according to claim 3, which is 3-hydroxymethyldibenzo[b,f]thiepin-5,5-dioxide.

Claim 9

A compound according to claim 3, which is 8-fluoro-3-hydroxymethyl-dibenzo[b,f]thiepin.

Claim 10

A compound according to claim 2, which is 8-fluoro-3-hydroxymethyl-dibenzo[b,f]thiepin-5-oxide.

Claim 11

A compound according to claim 3, which is 8-fluoro-3-hydroxymethyl-dibenzo[b,f]thiepin-5,5-dioxide.

Claim 12

A compound according to claim 4, which is 3-hydroxymethyl-10,11-dihydrodibenzo[b,f]thiepin.

Claim 13

A compound according to claim 4, which is 3-hydroxymethyl-10,11-dihydrodibenzo[b,f]thiepin-5-oxide.

Claim 14

A compound according to claim 4, which is 3-hydroxymethyl-10,11-dihydrodibenzo[b,f]thiepin-5,5-dioxide.

Claim 15

A compound according to claim 4, which is 8-fluoro-3-hydroxymethyl-10,11-dihydrodibenzo[b,f]thiepin.

Claim 16

A compound according to claim 4, which is 8-fluoro-3-hydroxymethyl-10,11-dihydrodibenzo[b,f]thiepin 5-oxide.

Claim 17

A compound according to claim 4, which is 8-fluoro-3-hydroxymethyl-10,11-dihydrodibenzo[b,f]thiepin-5,5-dioxide.

Claim 18

A composition for treating undesirable contractile activity of prostaglandins consisting essentially of a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of the formula: ##STR28## or an ester or acetal thereof, wherein n is an integer from 1 to 4; Z is thio, sulfinyl, or sulfonyl; R 1 and/or R 2 is hydrogen, halogen including chloro, bromo, fluoro and iodo, amino, C 1 to C 4 alkyl, C 1 to C 4 alkanoyl, hydroxyl, C 1 to C 4 alkoxy, thiol, C 1 to C 4 alkylthio, C 1 to C 4 alkylsulfinyl, C 1 to C 4 alkylsulfonyl, trifluoromethyl, trifluoromethylthio, cyano, nitro, and C 1 to C 4 alkyl or dialkylamino, aralkyl including benzyl and phenethyl, hydroxyalkyl as CH 3 CHOH; and the dotted line indicates either an olefinic bond or saturation at the 10-, 11-position.

Claim 19

A composition for treating undesirable contractile activity of prostaglandins consisting essentially of a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of the formula: ##STR28## or an ester or acetal thereof, wherein n is an integer from 1 to 4; Z is thio, sulfinyl, or sulfonyl; R 1 and/or R 2 is hydrogen, halogen including chloro, bromo, fluoro and iodo, amino, C 1 to C 4 alkyl, C 1 to C 4 alkanoyl, hydroxyl, C 1 to C 4 alkoxy, thiol, C 1 to C 4 alkylthio, C 1 to C 4 alkylsulfinyl, C 1 to C 4 alkylsulfonyl, trifluoromethyl, trifluoromethylthio, cyano, nitro, and C 1 to C 4 alkyl or dialkylamino, aralkyl including benzyl and phenethyl, hydroxyalkyl as CH 3 CHOH; and the dotted line indicates either an olefinic bond or saturation at the 10-, 11-position.

Claim 20

A process for preparing a compound of the formula: ##STR29## or an ester or acetal thereof, wherein n is an integer from 1 to 4; Z is thio, sulfinyl, or sulfonyl; R 1 and/or R 2 is hydrogen, halogen including chloro, bromo, fluoro and iodo, amino, C 1 to C 4 alkyl, C 1 to C 4 alkanoyl, hydroxyl, C 1 to C 4 alkoxy, thiol, C 1 to C 4 alkylthio, C 1 to C 4 alkylsulfinyl, C 1 to C 4 alkylsulfonyl, trifluoromethyl, trifluoromethylthio, cyano, nitro, and C 1 to C 4 alkyl or dialkylamino, aralkyl including benzyl and phenethyl, hydroxyalkyl as CH 3 CHOH; and the dotted line indicates either an olefinic bond or saturation at the 10-, 11-position; which comprises reducing a compound of the formula: ##STR30## with an alkali metal aluminum hydride or borane to convert the COOH substituent into a hydroxymethyl substituent.

Claim 21

A process for preparing a compound of the formula: ##STR29## or an ester or acetal thereof, wherein n is an integer from 1 to 4; Z is thio, sulfinyl, or sulfonyl; R 1 and/or R 2 is hydrogen, halogen including chloro, bromo, fluoro and iodo, amino, C 1 to C 4 alkyl, C 1 to C 4 alkanoyl, hydroxyl, C 1 to C 4 alkoxy, thiol, C 1 to C 4 alkylthio, C 1 to C 4 alkylsulfinyl, C 1 to C 4 alkylsulfonyl, trifluoromethyl, trifluoromethylthio, cyano, nitro, and C 1 to C 4 alkyl or dialkylamino, aralkyl including benzyl and phenethyl, hydroxyalkyl as CH 3 CHOH; and the dotted line indicates either an olefinic bond or saturation at the 10-, 11-position; which comprises reducing a compound of the formula: ##STR30## with an alkali metal aluminum hydride or borane to convert the COOH substituent into a hydroxymethyl substituent.

Claim 22

The compound according to claim 1 wherein R 1 is hydrogen and R 2 is fluoro.

Claim 23

The compound according to claim 1 wherein R 1 is hydrogen and R 2 is amino.

Claim 24

The compound according to claim 1 wherein R 1 is hydrogen and R 2 is chloro.

Claim 25

The compound according to claim 1 wherein R 1 is hydrogen and R 2 is acetyl.