Derivatives of 9-oxo-13-trans-prostenoic acid esters

Claim 2

An optically active compound of the formula: ##STR27## wherein n is the integer 1 or 2; Y is a divalent radical selected from the group consisting of those of the formulae: ##STR28## R 1 is selected from the group consisting of a straight chain alkyl group having from 3 to 10 carbon atoms, a straight chain alkyl group having from 2 to 6 carbon atoms and having one branched methyl group, a straight chain alkenyl group having from 3 to 6 carbon atoms, a straight chain ω-haloalkyl group having from 3 to 6 carbon atoms, a straight chain ω-mercaptoalkyl group having from 3 to 6 carbon atoms, a straight chain ω-carboxyalkyl group having from 3 to 6 carbon atoms, and moieties of the formulae: ##STR29## wherein p is an integer from 2 to 4, inclusive, q is an integer from 3 to 6, inclusive, R 3 is an alkyl group having from 1 to 3 carbon atoms, R 4 is selected from the group consisting of hydrogen and lower alkyl, R 5 is selected from the group consisting of hydrogen and lower alkyl, and R 4 and R 5 taken together with the N(itrogen) is selected from the group consisting of pyrrolidino, piperidino and morpholino; R 2 is selected from the group consisting of hydroxy, alkoxy having from 1 to 4 carbon atoms, pyridoxy, 2,2,2-trichloroethoxy, and a moiety of the formula: ##STR30## wherein P, R 4 and R 5 are as hereinabove defined; and Z is a divalent radical selected from the group consisting of those of the formulae: ##STR31## wherein m is an integer from 1 to 8, inclusive, and p, q and R 3 are as hereinabove defined; and the pharmaceutically acceptable cationic salts thereof when R 1 is an ω-carboxyalkyl group or when R 2 is hydroxy.

Claim 3

The compound according to claim 1 wherein n is 1, Y is ##STR32## R 1 is n-hexyl, R 2 is hydroxy, and Z is --(CH 2 ) 6 --; 1-9-oxo-13-trans-prostenoic acid.

Claim 4

The compound according to claim 1 wherein n is 1, Y is ##STR33## R 1 is n-hexyl, R 2 is γ-dimethylaminopropyloxy, and Z is --(CH 2 ) 6 --; l-3-dimethylaminopropyl 9-oxo-13-trans-prostenoate.

Claim 5

The compound according to claim 1 wherein n is 1, Y is ##STR34## R 1 is n-hexyl, R 2 is hydroxy, and Z is --CH 2 --CH═CH--(CH 2 ) 3 --; l-9-oxo-5-cis-13-trans-prostadienoic acid.

Claim 6

The compound according to claim 1 wherein n is 1, Y is ##STR35## R 1 is 6-chlorohexyl, R 2 is hydroxy, and Z is --(CH 2 ) 6 --; l-9-oxo-20-chloro-13-trans-prostenoic acid.

Claim 7

The compound according to claim 1 wherein n is 1, Y is ##STR36## R 1 is n-hexyl, R 2 is hydroxy, and Z is --(CH 2 ) 4 --O--CH 2 --; l-9-oxa-13-trans-prostenoic acid.

Claim 8

The compound according to claim 1 wherein n is 1, Y is ##STR37## R 1 is n-hexyl, R 2 is hydroxy, and Z is --(CH 2 ) 4 --S--CH 2 --; l--9-oxo-3-thia-13-trans-prostenoic acid.

Claim 9

The compound according to claim 1 wherein n is 1, Y is ##STR38## R 1 is --(CH 2 ) 3 --S--CH 2 CH 3 , R 2 is hydroxy, and Z is --(CH 2 ) 6 ; l-9-oxo-18-thia-13-trans-prostenoic acid.

Claim 10

The compound according to claim 1 wherein n is 1, Y is ##STR39## R 1 is n-hexyl, R 2 is hydroxy, and Z is --(CH 2 ) 4 --C(CH 3 ) 2 --CH 2 ; l-9-oxo-3,3-dimethyl-13-trans-prostenoic acid.

Claim 11

The compound according to claim 1 wherein n is 1, Y is ##STR40## R 1 is 3-cis-hexenyl, R 2 is hydroxy, and Z is --(CH 2 ) 6 --; l-9-oxo-17-cis-13-trans-prostadienoic acid.

Claim 12

The compound according to claim 1 wherein n is 1, Y is ##STR41## R 1 is n-hexyl, R 2 is hydroxy, and Z is --(CH 2 ) 6 --; l-9α-hydroxy-13-trans-prostenoic acid.

Claim 13

The compound according to claim 1 wherein n is 1, Y is ##STR42## R 1 is n-hexyl, R 2 is γ-diethylaminopropyloxy, and Z is --(CH 2 ) 6 --; l-3-diethylaminopropyl 9α-hydroxy-13-trans-prostenoate.

Claim 14

The compound according to claim 1 wherein n is 1, Y is ##STR43## R 1 is 3-chloropropyl, R 2 is hydroxy, and Z is --(CH 2 ) 6 --; l-9α-hydroxy-20-chloro-17,18,19-trinor-13-transprostenoic acid.

Claim 15

The compound according to claim 1 where n is 2, Y is ##STR44## R 1 is n-hexyl, R 2 is hydroxy, and Z is --(CH 2 ) 6 --;1-9-oxo-10a-homo-13-trans-prostenoic acid.

Claim 16

The compound according to claim 1 wherein n is 2, Y is ##STR45## R 1 is n-hexyl, R 2 is ethoxy, and Z is --(CH 2 ) 6 --; l-ethyl 9-oxo-10a-homo-13-trans-prostenoate.

Claim 17

The compound according to claim 1 wherein n is 2, Y is ##STR46## R 1 is n-hexyl, R 2 is hydroxy, and Z is -(CH 2 ) 6 -; l-9α-hydroxy-10a-homo-13-trans-prostenoic acid.

Claim 18

A racemic compound consisting of an optically active compound of the formula: ##STR47## and the mirror image thereof wherein n is the integer 1 or 2; Y is a divalent radical selected from the group consisting of those of the formulae: ##STR48## R 1 is selected from the group consisting of a straight chain alkyl group having from 3 to 10 carbon atoms, a straight chain alkyl group having from 2 to 6 carbon atoms and having one branched methyl group, a straight chain alkenyl group having from 3 to 6 carbon atoms, a straight chain ω-haloalkyl group having from 3 to 6 carbon atoms, a straight chain ω-mercaptoalkyl group having from 3 to 6 carbon atoms, a straight chain ω-carboxyalkyl group having from 3 to 6 carbon atoms, and moieties of the formulae: ##STR49## wherein p is an integer from 2 to 4, inclusive, q is an integer from 3 to 6, inclusive, R 3 is an alkyl group having from 1 to 3 carbon atoms, R 4 is selected from the group consisting of hydrogen and lower alkyl, R 5 is selected from the group consisting of hydrogen and lower alkyl, and R 4 and R 5 taken together with the N(itrogen) is selected from the group consisting of pyrrolidino, piperidino and morpholino; R 2 is selected from the group consisting of hydroxy, alkoxy having from 1 to 4 carbon atoms, pyridoxy, 2,2,2-trichloroethoxy, and a moiety of the formula: ##STR50## wherein p, R 4 and R 5 are as hereinabove defined; and Z is a divalent radical selected from the group consisting of those of the formulae: ##STR51## wherein m is an integer from 1 to 8, inclusive, and p, q and R 3 are as hereinabove defined; and the pharmaceutically acceptable cationic salts thereof when R 1 is an ω-carboxyalkyl group or when R 2 is hydroxy.

Claim 19

A racemic compound consisting of an optically active compound of the formula: ##STR47## and the mirror image thereof wherein n is the integer 1 or 2; Y is a divalent radical selected from the group consisting of those of the formulae: ##STR48## R 1 is selected from the group consisting of a straight chain alkyl group having from 3 to 10 carbon atoms, a straight chain alkyl group having from 2 to 6 carbon atoms and having one branched methyl group, a straight chain alkenyl group having from 3 to 6 carbon atoms, a straight chain ω-haloalkyl group having from 3 to 6 carbon atoms, a straight chain ω-mercaptoalkyl group having from 3 to 6 carbon atoms, a straight chain ω-carboxyalkyl group having from 3 to 6 carbon atoms, and moieties of the formulae: ##STR49## wherein p is an integer from 2 to 4, inclusive, q is an integer from 3 to 6, inclusive, R 3 is an alkyl group having from 1 to 3 carbon atoms, R 4 is selected from the group consisting of hydrogen and lower alkyl, R 5 is selected from the group consisting of hydrogen and lower alkyl, and R 4 and R 5 taken together with the N(itrogen) is selected from the group consisting of pyrrolidino, piperidino and morpholino; R 2 is selected from the group consisting of hydroxy, alkoxy having from 1 to 4 carbon atoms, pyridoxy, 2,2,2-trichloroethoxy, and a moiety of the formula: ##STR50## wherein p, R 4 and R 5 are as hereinabove defined; and Z is a divalent radical selected from the group consisting of those of the formulae: ##STR51## wherein m is an integer from 1 to 8, inclusive, and p, q and R 3 are as hereinabove defined; and the pharmaceutically acceptable cationic salts thereof when R 1 is an ω-carboxyalkyl group or when R 2 is hydroxy.

Claim 20

The compound according to claim 17 wherein n is 1, Y is ##STR52## R 1 is n-hexyl, R 2 is hydroxy, and Z is --(CH 2 ) 6 --; dl-9-oxo-13-trans-prostenoic acid.

Claim 21

The compound according to claim 17 wherein n is 1, Y is ##STR53## R 1 is n-hexyl, R 2 is γ-dimethylaminopropyloxy, and Z is --(CH 2 ) 6 --; dl-3-dimethylaminopropyl 9-oxo-13-trans-prostenoate.

Claim 22

The compound according to claim 17 wherein n is 1, Y is ##STR54## R 1 is n-hexyl, R 2 is hydroxy, and Z is --CH 2 --CH═CH--(CH 2 ) 3 -; dl-9-oxo-5-cis-13-trans-prostadienoic acid.

Claim 23

The compound according to claim 17 wherein n is 1, Y is ##STR55## R 1 is 6-chlorohexyl, R 2 is hydroxy, and Z is --(CH 2 ) 6 --; dl-9-oxo-20-chloro-13-trans-prostenoic acid.

Claim 24

The compound according to claim 17 wherein n is 1, Y is ##STR56## R 1 is n-hexyl, R 2 is hydroxy, and Z is --(CH 2 ) 4 --O--CH 2 --; dl-9-oxo-3-oxa-13-trans-prostenoic acid.

Claim 25

The compound according to claim 17 wherein n is 1, Y is ##STR57## R 1 is n-hexyl, R 2 is hydroxy, and Z is --(CH 2 ) 4 --S--CH 2 --; dl-9-oxo-3-thia-13-trans-prostenoic acid.

Claim 26

The compound according to claim 17 wherein n is 1, Y is ##STR58## R 1 is --(CH 2 ) 3 --S--CH 2 CH 3 , R 2 is hydroxy, and Z is --(CH 2 ) 6 ; dl-9-oxo-13-thia-18-trans prostenoic acid.

Claim 27

The compound according to claim 17 wherein n is 1, Y is ##STR59## R 1 is n-hexyl, R 2 is hydroxy, and Z is --(CH 2 ) 4 --C(CH 2 --CH 3 --;dl-9-oxo-3,3-dimethyl-13-trans-prostenoic acid.

Claim 28

The compound according to claim 17 wherein n is 1, Y is ##STR60## R 1 is 3-cis-hexenyl, R 2 is hydroxy, and Z is --(CH 2 ) 6 --; dl-9-oxo-17-cis-13-trans-prostadienoic acid.

Claim 29

The compound according to claim 17 wherein n is 1, Y is ##STR61## R 1 is n-hexyl, R 2 is hydroxy, and Z is --(CH 2 ) 6 --; dl-9α-hydroxy-13-trans-prostenoic acid.

Claim 30

The compound according to claim 17 wherein n is 1, Y is ##STR62## R 1 is n-hexyl, R 2 is γ-diethylaminopropyloxy, and Z is --(CH 2 ) 6 --; dl-3-diethylaminopropyl 9α-hydroxy-13-trans-prostenoate.

Claim 31

The compound according to claim 17 wherein n is 1, Y is ##STR63## R 1 is 3-chloroproyl, R 2 is hydroxy, and Z is --(CH 2 ) 6 --; dl-9α-hydroxy-20-chloro-17,18,19-trinor-13-trans-prostenoic acid.

Claim 32

The compound according to claim 17 wherein n is 2, Y is ##STR64## R 1 is n-hexyl, R 2 is hydroxy, and Z is --(CH 2 ) 6 --; dl-9-oxo-10α-homo-13-trans-prostenoic acid.

Claim 33

The compound according to claim 17 wherein n is 2, Y is ##STR65## R 1 is n-hexyl, R 2 is ethoxy, and Z is --(CH 2 ) 6 --; dl-ethyl 9-oxo-10a-homo-13-trans-prostenoate.

Claim 34

The compound according to claim 17 wherein n is 2, Y is ##STR66## R 1 is n-hexyl, R 2 is hydroxy, and Z is --(CH 2 ) 6 --; dl-9α-hydroxy-10a-homo-13-trans-prostenoic acid.

Claim 35

The compound l-9-oxo-2-ethyl-13-trans-prostenoic acid.

Claim 36

The compound l-9-oxo-2-ethyl-13-trans-prostenoic acid.

Claim 37

The compound dl-9-oxo-2-ethyl-13-trans-prostenoic acid.

Claim 38

The compound dl-9-oxo-2-ethyl-13-trans-prostenoic acid.