Certain 5,6-dihydro-prostacyclin analogs

Claim 2

A cyclic ether of the formula ##STR185## wherein D is (1) a valence bond; (2) --(CH 2 ) d -- where d is 1, 2, 3, 4, or 5; (3) --CH═CH--A-- where A is a valence bond or --(CH 2 ) h -- where h is 1, 2, or 3; or (4) --CH 2 --O--CH 2 --Y-- where Y is a valence bond or --(CH 2 ) k -- where k is 1 or 2; wherein R 2 is ##STR186## wherein C g H 2 .sbsb.g is alkylene of 1 to 9 carbon atoms, inclusive, with 1 to 5 carbon atoms, inclusive, in the chain between --CR 5 R 6 -- and terminal methyl, wherein R 5 and R 6 are hydrogen, alkyl of one to 4 carbon atoms, inclusive, or fluoro, being the same or different, with the proviso that one of R 5 and R 6 is fluoro only when the other is hydrogen or fluoro; or ##STR187## wherein R 5 and R 6 are as defined above with the proviso that neither R 5 nor R 6 is fluoro when Z is oxa (--O--); wherein Z represents an oxa atom (--O--) or C j H 2 .sbsb.j wherein C j H 2 .sbsb.j is a valence bond or alkylene of one to 9 carbon atoms, inclusive, with one to 6 carbon atoms, inclusive between --CR 5 R 6 -- and the phenyl ring; wherein T is alkyl of one to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR 7 wherein R 7 is alkyl of 1 to 4 carbon atoms, inclusive, and s is 0, 1, 2 or 3, with the proviso that not more than two T's are other than alkyl and when s is 2 or 3 the T's are either the same or different; wherein Q 3 is ##STR188## wherein R 3 is hydrogen or alkyl of one to 4 carbon atoms, inclusive; wherein R 23 is ##STR189## wherein R 31 is (1) --COOR 32 (2) --ch 2 n(r 18 ) 2 ##STR190## wherein R 32 is wherein R 32 is (a) cycloalkyl of 3 to 10 carbon atoms, inclusive, (b) aralkyl of 7 to 12 carbon atoms, inclusive (c) phenyl, (d) phenyl substituted with 1, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive, ##STR191## wherein R 34 is phenyl, p-bromophenyl, p-biphenylyl, p-nitrophenyl, p-benzamido phenyl, or 2-naphthyl, wherein R 35 is hydrogen or benzoyl, and wherein R 18 is hydrogen, alkyl of one to 12 carbon atoms, inclusive, benzyl, or phenyl, being the same or different; wherein ˜ indicates attachment in alpha or beta configuration; including the lower alkanoates thereof.

Claim 3

A compound according to claim 1 wherein Q 3 is ##STR192## wherein R 3 is as defined in claim 1.

Claim 4

A compound according to claim 2 wherein R 3 is hydrogen and R 23 is ##STR193##

Claim 5

A compound according to claim 3 wherein D is a valence bond or --(CH 2 ) 3 -- wherein d is 1, 2, 3, 4, or 5.

Claim 6

A compound according to claim 4 wherein D is trimethylene.

Claim 7

A compound according to claim 5 wherein R 2 is n-pentyl.

Claim 8

A compound according to claim 6 wherein R 31 is ##STR194## wherein R 18 is hydrogen, alkyl of 1 to 12 carbon atoms, inclusive, benzyl, or phenyl, being the same or different.

Claim 9

A compound according to claim 7 wherein one R 18 is hydrogen, methyl, or phenyl and the other R 18 is hydrogen.

Claim 10

9-Deoxy-6ξ,9α-epoxy-PGF 1 , amide, less polar and more polar isomers, compounds according to claim 8.

Claim 11

(6S)-PGI 1 , amide, a compound according to claim 9.

Claim 12

(6R)-PGI 1 , amide, a compound according to claim 9.

Claim 13

9-Deoxy-6ξ,9α-epoxy-PGF 1 , methylamide, less polar and more polar isomers, compounds according to claim 8.

Claim 14

(6S)-PGI 1 , methylamide, a compound according to claim 12.

Claim 15

(6R)-PGI 1 , methylamide, a compound according to claim 12.

Claim 16

9-Deoxy-6ξ,9α-epoxy-PGF 1 , anilide, less polar and more polar isomers, compounds according to claim 8.

Claim 17

(6S)-PGI 1 , anilide, a compound according to claim 15.

Claim 18

(6R)-PGI 1 , anilide, a compound according to claim 15.

Claim 19

9-Deoxy-6ξ,9α-epoxy-PGF 1 , n-butylamide, less polar and more polar isomers, compounds according to claim 7.

Claim 20

9-Deoxy-6ξ,9α-epoxy-PGF 1 , benzylamide, less polar and more polar isomers, compounds according to claim 7.

Claim 21

A compound according to claim 6 wherein R 31 is --COOR 32 wherein R 32 is ##STR195## (g) p-phenylphenacyl.

Claim 22

A compound according to claim 5 wherein R 2 is ##STR196##

Claim 23

A compound according to claim 2 wherein Q 3 is ##STR197##

Claim 24

A compound according to claim 22 wherein R 31 is ##STR198## wherein R 18 is hydrogen, alkyl of 1 to 12 carbon atoms, inclusive, benzyl, or phenyl, being the same or different.

Claim 25

A compound according to claim 23 wherein one R 18 is hydrogen, methyl, or phenyl and the other R 18 is hydrogen.

Claim 26

9-Deoxy-6ξ,9α-epoxy-15(S)-15-methyl-PGF 1 , amide, less polar and more polar isomers, compounds according to claim 24.

Claim 27

(6S,15S)-15-Methyl-PGI 1 , amide, a compound according to claim 25.

Claim 28

(6R,15S)-15-Methyl-PGI 1 , amide, a compound according to claim 25.

Claim 29

A cyclic ether of the formula ##STR199## wherein D is (1) a valence bond; (2) --(CH 2 ) d --where d is 1, 2, 3, 4, or 5; (3) --CH═CH--A-- where A is a valence bond, or --(CH 2 ) h -- where h is 1, 2, or 3; or (4) --CH 2 --O--CH 2 --Y-- where Y is a valence bond or --(CH 2 ) k -- where k is 1 or 2; wherein Q 3 is ##STR200## wherein R 3 is hydrogen or alkyl of 1 to 4 carbon atoms, inclusive; wherein R 23 is ##STR201## wherein R 30 is (1) --COOR 19 (2) --ch 2 n(r 18 ) 2 ##STR202## wherein R 19 is (a) alkyl of 1 to 12 carbon atoms, inclusive, (b) cycloalkyl of 3 to 10 carbon atoms, inclusive, (c) aralkyl of 7 to 12 carbon atoms, inclusive, (d) phenyl, (e) phenyl substituted with 1, 2, or 3 chloro or alkyl of 1 to 4 carbon atoms, inclusive, ##STR203## wherein R 34 is phenyl, p-bromophenyl, p-biphenylyl, p-nitrophenyl, p-benzamidophenyl, or 2-naphthyl, and wherein R 35 is hydrogen or benzoyl, (m) hydrogen; or (n) a pharmacologically acceptable cation; and wherein R 18 is hydrogen, alkyl of 1 to 12 carbon atoms, inclusive, benzyl, or phenyl, being the same or different; and wherein ˜ indicates attachment in alpha or beta configuration; including the lower alkanoates thereof.

Claim 30

A cyclic ether of the formula ##STR199## wherein D is (1) a valence bond; (2) --(CH 2 ) d --where d is 1, 2, 3, 4, or 5; (3) --CH═CH--A-- where A is a valence bond, or --(CH 2 ) h -- where h is 1, 2, or 3; or (4) --CH 2 --O--CH 2 --Y-- where Y is a valence bond or --(CH 2 ) k -- where k is 1 or 2; wherein Q 3 is ##STR200## wherein R 3 is hydrogen or alkyl of 1 to 4 carbon atoms, inclusive; wherein R 23 is ##STR201## wherein R 30 is (1) --COOR 19 (2) --ch 2 n(r 18 ) 2 ##STR202## wherein R 19 is (a) alkyl of 1 to 12 carbon atoms, inclusive, (b) cycloalkyl of 3 to 10 carbon atoms, inclusive, (c) aralkyl of 7 to 12 carbon atoms, inclusive, (d) phenyl, (e) phenyl substituted with 1, 2, or 3 chloro or alkyl of 1 to 4 carbon atoms, inclusive, ##STR203## wherein R 34 is phenyl, p-bromophenyl, p-biphenylyl, p-nitrophenyl, p-benzamidophenyl, or 2-naphthyl, and wherein R 35 is hydrogen or benzoyl, (m) hydrogen; or (n) a pharmacologically acceptable cation; and wherein R 18 is hydrogen, alkyl of 1 to 12 carbon atoms, inclusive, benzyl, or phenyl, being the same or different; and wherein ˜ indicates attachment in alpha or beta configuration; including the lower alkanoates thereof.

Claim 31

A compound according to claim 28 wherein Q 3 is ##STR204## wherein R 3 is as defined in claim 29.

Claim 32

A compound according to claim 29 wherein R 23 is ##STR205##

Claim 33

A compound according to claim 30 wherein D is a valence bond or --(CH 2 ) d --wherein d is 1, 2, 3, 4, or 5.

Claim 34

A compound according to claim 31, where, if R 30 is --CH 2 N(R 18 ) 2 or ##STR206## one R 18 is hydrogen, methyl, or phenyl, and the other R 18 is hydrogen, or, if R 30 is --COOR 19 , R 19 is (a) hydrogen, (b) methyl, (c) ethyl, ##STR207## (j) p-phenylphenacyl, or (k) a pharmacologically acceptable cation.

Claim 35

A cyclic ether of the formula ##STR208## wherein D' is --CH 2 --CH═CH--A-- or --(CH 2 ) T --CF 2 -- wherein A is a valence bond or --(CH 2 ) h -- where h is 1, 2, or 3; and wherein t is 2, 3, or 4; wherein Q 3 is ##STR209## wherein R 3 is hydrogen or alkyl of 1 to 4 carbon atoms, inclusive, wherein R 23 is ##STR210## wherein R 25 is ##STR211## wherein C g H 2 .sbsb.g is alkylene of 1 to 9 carbon atoms, inclusive, with 1 to 5 carbon atoms, inclusive, in the chain between -CR 5 R 6 - and terminal methyl, wherein R 5 and R 6 are hydrogen, alkyl of 1 to 4 carbon atoms, inclusive, or fluoro, being the same or different, with the proviso that one of R 5 and R 6 is fluoro only when the other is hydrogen or fluoro; ##STR212## wherein R 5 and R 6 are as defined above with the proviso that neither R 5 nor R 6 is fluoro when Z is oxa (--O--); wherein Z represents an oxa atom (--O--) or C j H 2 .sbsb.j wherein C j H 2 .sbsb.j is a valence bond or alkylene of 1 to 9 carbon atoms, inclusive, with 1 to 6 carbon atoms, inclusive between --CR 5 R 6 -- and the phenyl ring; wherein T is alkyl of one to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR 7 -- wherein R 7 is alkyl of one to 4 carbon atoms, inclusive, and s is 0, 1, 2, or 3, with the proviso that not more than two T's are other than alkyl and when s is 2 or 3 and T's are either the same or different; or ##STR213## wherein R 30 is (1) --COOR 19 (2 ) --ch 2 n(r 18 ) 2 ##STR214## wherein R 19 is (a) alkyl of one to 12 carbon atoms, inclusive, (b) cycloalkyl of 3 to 10 carbon atoms, inclusive, (c) aralkyl of 7 to 12 carbon atoms, inclusive, (d) phenyl, (e) phenyl substituted with 1, 2, or 3 chloro or alkyl of 1 to 4 carbon atoms, inclusive, ##STR215## wherein R 34 is phenyl, p-bromophenyl, p-biphenylyl, p-nitrophenyl, p-benzamidophenyl, or 2-naphthyl, and wherein R 35 is hydrogen or benzoyl, (m) hydrogen; or (n) a pharmacologically acceptable cation; and wherein R 18 is hydrogen, alkyl of one to 12 carbon atoms, inclusive, benzyl, or phenyl, being the same or different; and wherein ˜ indicates attachment in alpha or beta configuration; including the lower alkanoates thereof.

Claim 36

A cyclic ether of the formula ##STR208## wherein D' is --CH 2 --CH═CH--A-- or --(CH 2 ) T --CF 2 -- wherein A is a valence bond or --(CH 2 ) h -- where h is 1, 2, or 3; and wherein t is 2, 3, or 4; wherein Q 3 is ##STR209## wherein R 3 is hydrogen or alkyl of 1 to 4 carbon atoms, inclusive, wherein R 23 is ##STR210## wherein R 25 is ##STR211## wherein C g H 2 .sbsb.g is alkylene of 1 to 9 carbon atoms, inclusive, with 1 to 5 carbon atoms, inclusive, in the chain between -CR 5 R 6 - and terminal methyl, wherein R 5 and R 6 are hydrogen, alkyl of 1 to 4 carbon atoms, inclusive, or fluoro, being the same or different, with the proviso that one of R 5 and R 6 is fluoro only when the other is hydrogen or fluoro; ##STR212## wherein R 5 and R 6 are as defined above with the proviso that neither R 5 nor R 6 is fluoro when Z is oxa (--O--); wherein Z represents an oxa atom (--O--) or C j H 2 .sbsb.j wherein C j H 2 .sbsb.j is a valence bond or alkylene of 1 to 9 carbon atoms, inclusive, with 1 to 6 carbon atoms, inclusive between --CR 5 R 6 -- and the phenyl ring; wherein T is alkyl of one to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR 7 -- wherein R 7 is alkyl of one to 4 carbon atoms, inclusive, and s is 0, 1, 2, or 3, with the proviso that not more than two T's are other than alkyl and when s is 2 or 3 and T's are either the same or different; or ##STR213## wherein R 30 is (1) --COOR 19 (2 ) --ch 2 n(r 18 ) 2 ##STR214## wherein R 19 is (a) alkyl of one to 12 carbon atoms, inclusive, (b) cycloalkyl of 3 to 10 carbon atoms, inclusive, (c) aralkyl of 7 to 12 carbon atoms, inclusive, (d) phenyl, (e) phenyl substituted with 1, 2, or 3 chloro or alkyl of 1 to 4 carbon atoms, inclusive, ##STR215## wherein R 34 is phenyl, p-bromophenyl, p-biphenylyl, p-nitrophenyl, p-benzamidophenyl, or 2-naphthyl, and wherein R 35 is hydrogen or benzoyl, (m) hydrogen; or (n) a pharmacologically acceptable cation; and wherein R 18 is hydrogen, alkyl of one to 12 carbon atoms, inclusive, benzyl, or phenyl, being the same or different; and wherein ˜ indicates attachment in alpha or beta configuration; including the lower alkanoates thereof.

Claim 37

A compound according to claim 33 wherein Q 3 is ##STR216## wherein R 3 is as defined in claim 35.

Claim 38

A compound according to claim 34 wherein R 23 is ##STR217##

Claim 39

A compound according to claim 35 wherein D' is --(CH 2 ) t --CF 2 where t is 2, 3, or 4.

Claim 40

A compound according to claim 36 wherein t is 2, and where, if R 30 is --CH 2 N(R 18 ) 2 or ##STR218## one R 18 is hydrogen, methyl, or phenyl, and the other R 18 is hydrogen, or, if R 30 is --COOR 19 , R 19 is (a) hydrogen, (b) methyl, (c) ethyl, ##STR219## (j) p-phenylphenacyl, or (k) a pharmacologically acceptable cation.

Claim 41

A compound according to claim 37 wherein R 25 is n-pentyl.

Claim 42

A compound according to claim 37 wherein R 25 is ##STR220##

Claim 43

A compound according to claim 37 wherein R 25 is ##STR221##

Claim 44

A compound according to claim 37 wherein R 25 is ##STR222##

Claim 45

A compound according to claim 35 wherein D' is --CH 2 --CH═CH--A-- wherein A is a valence bond or --(CH 2 ) h wherein h is 1, 2, or 3.

Claim 46

A compound according to claim 42 wherein A is a valance bond, and where, if R 30 is --CH 2 N(R 18 ) or ##STR223## one R 18 is hydrogen, methyl, or phenyl, and the other R 18 is hydrogen, or, if R 30 is --COOR 19 , R 19 is (a) hydrogen, (b) methyl, (c) ethyl, ##STR224## (j) p-phenylphenacyl, or (k) a pharmacologically acceptable cation.

Claim 47

A compound according to claim 43 wherein R 25 is n-pentyl.

Claim 48

9-Deoxy-6ξ, 9α-epoxy-2,3-trans-didehydro-PGF 1 , methyl ester, less polar and more polar isomers, compounds according to claim 44.

Claim 49

(2E,6S)-Δ 2 -PGI 1 , methyl ester, a compound according to claim 45.

Claim 50

(2E,6R)-Δ-PGI 1 , methyl ester, a compound according to claim 45.

Claim 51

A compound according to claim 46 wherein R 25 is ##STR225##

Claim 52

9-Deoxy-6ξ,9α-epoxy-2,3-trans-didehydro-16,16-dimethyl-PGF.sub.1, methyl ester, less polar and more polar isomers, compounds according to claim 48.

Claim 53

(2E, 6S)-16,16-Dimethyl-Δ 2 -PGI, methyl ester, a compound according to claim 49.

Claim 54

(2E,6R)-16,16-Dimethyl-Δ 2 -PGI 1 , methyl ester, a compound according to claim 49.

Claim 55

9-Deoxy-6ξ,9α-epoxy-2,3-trans-didehydro-16,16-dimethyl-PGF 1 , less polar and more polar isomers, compounds according to claim 48.

Claim 56

(2E,6s)-16,16-dimethyl-Δ 2 -PGI 1 , a compound according to claim 52.

Claim 57

(2E,6R)-16,16-dimethyl-Δ 2 -PGI 1 , a compound according to claim 52.

Claim 58

A compound according to claim 43 wherein R 25 is ##STR226##

Claim 59

A comound according to claim 43 wherein R 25 is ##STR227##

Claim 60

A cyclic ether of the formula ##STR228## wherein L is (1) a valence bond, (2) --(CH 2 ) d -- wherein d is 1 to 5 inclusive, (3) --(CH 2 ) t --CF 2 -- wherein t is 2, 3, or 4, (4) --CH 2 --CH═CH--A-- wherein A is a valence bond or --(CH 2 ) h -- wherein h is 1, 2, or 3, or (5) --CH 2 --O--CH 2 --Y-- wherein Y is a valence bond or --(CH 2 ) k -- wherein k is 1 or 2; wherein Q 3 is ##STR229## wherein R 3 is hydrogen or alkyl of 1 to 4 carbon atoms, inclusive; wherein R 23 is ##STR230## wherein R 25 is ##STR231## wherein C g H 2 .sbsb.g is alkylene of 1 to 9 carbon atoms, inclusive, with 1 to 5 carbon atoms, inclusive, in the chain between --CR 5 R 6 -- and terminal methyl, wherein R 5 and R 6 are hydrogen, alkyl of 1 to 4 carbon atoms, inclusive, or fluoro, being the same or different, with the proviso that one of R 5 and R 6 is fluoro only when the other is hydrogen or fluoro; ##STR232## wherein R 5 and R 6 are as defined above with the proviso that neither R 5 nor R 6 is fluoro when Z is oxa (--O--); wherein Z represents an oxa atom (--O--) or C j H 2 .sbsb.j wherein C j H 2 .sbsb.j is a valence bond or alkylene of 1 to 9 carbon atoms, inclusive, with 1 to 6 carbon atoms, inclusive between --CR 5 R 6 -- and the phenyl ring; wherein T is alkyl of 1 to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR 7 -- wherein R 7 is alkyl of 1 to 4 carbon atoms, inclusive, and s is 0, 1, 2, or 3, with the proviso that not more than two T's are other than alkyl and when s is 2 or 3 the T's are either the same or different; or ##STR233## wherein R 30 is (1) --COOR 19 (2) --(ch 2 n(r 18 ) 2 ##STR234## wherein R 19 is (a) alkyl of 1 to 12 carbon atoms, inclusive, (b) cycloalkyl of 3 to 10 carbon atoms, inclusive, (c) aralkyl of 7 to 12 carbon atoms, inclusive, (d) phenyl, (e) phenyl substituted with 1, 2, or 3 chloro or alkyl of 1 to 4 carbon atoms, inclusive, ##STR235## wherein R 34 is phenyl, p-bromophenyl, p-biphenylyl, p-nitrophenyl, p-benzamidophenyl, or 2-napththyl, and wherein R 35 is hydrogen or benzoyl, (m) hydrogen, or (n) a pharmacologically acceptable cation; and wherein R 18 hydrogen, alkyl of 1 to 12 carbon atoms, inclusive, benzyl, or phenyl, being the same or different; wherein X'is cis--CH═CH--, --C.tbd.C--, or --CH 2 CH 2 --; and wherein ˜ indicates attachment in alpha or beta configuration; including the lower alkanoates thereof.

Claim 61

A cyclic ether of the formula ##STR228## wherein L is (1) a valence bond, (2) --(CH 2 ) d -- wherein d is 1 to 5 inclusive, (3) --(CH 2 ) t --CF 2 -- wherein t is 2, 3, or 4, (4) --CH 2 --CH═CH--A-- wherein A is a valence bond or --(CH 2 ) h -- wherein h is 1, 2, or 3, or (5) --CH 2 --O--CH 2 --Y-- wherein Y is a valence bond or --(CH 2 ) k -- wherein k is 1 or 2; wherein Q 3 is ##STR229## wherein R 3 is hydrogen or alkyl of 1 to 4 carbon atoms, inclusive; wherein R 23 is ##STR230## wherein R 25 is ##STR231## wherein C g H 2 .sbsb.g is alkylene of 1 to 9 carbon atoms, inclusive, with 1 to 5 carbon atoms, inclusive, in the chain between --CR 5 R 6 -- and terminal methyl, wherein R 5 and R 6 are hydrogen, alkyl of 1 to 4 carbon atoms, inclusive, or fluoro, being the same or different, with the proviso that one of R 5 and R 6 is fluoro only when the other is hydrogen or fluoro; ##STR232## wherein R 5 and R 6 are as defined above with the proviso that neither R 5 nor R 6 is fluoro when Z is oxa (--O--); wherein Z represents an oxa atom (--O--) or C j H 2 .sbsb.j wherein C j H 2 .sbsb.j is a valence bond or alkylene of 1 to 9 carbon atoms, inclusive, with 1 to 6 carbon atoms, inclusive between --CR 5 R 6 -- and the phenyl ring; wherein T is alkyl of 1 to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR 7 -- wherein R 7 is alkyl of 1 to 4 carbon atoms, inclusive, and s is 0, 1, 2, or 3, with the proviso that not more than two T's are other than alkyl and when s is 2 or 3 the T's are either the same or different; or ##STR233## wherein R 30 is (1) --COOR 19 (2) --(ch 2 n(r 18 ) 2 ##STR234## wherein R 19 is (a) alkyl of 1 to 12 carbon atoms, inclusive, (b) cycloalkyl of 3 to 10 carbon atoms, inclusive, (c) aralkyl of 7 to 12 carbon atoms, inclusive, (d) phenyl, (e) phenyl substituted with 1, 2, or 3 chloro or alkyl of 1 to 4 carbon atoms, inclusive, ##STR235## wherein R 34 is phenyl, p-bromophenyl, p-biphenylyl, p-nitrophenyl, p-benzamidophenyl, or 2-napththyl, and wherein R 35 is hydrogen or benzoyl, (m) hydrogen, or (n) a pharmacologically acceptable cation; and wherein R 18 hydrogen, alkyl of 1 to 12 carbon atoms, inclusive, benzyl, or phenyl, being the same or different; wherein X'is cis--CH═CH--, --C.tbd.C--, or --CH 2 CH 2 --; and wherein ˜ indicates attachment in alpha or beta configuration; including the lower alkanoates thereof.

Claim 62

A compound according to claim 57 wherein X' is cis--CH═CH--.

Claim 63

A compound according to claim 57 wherein X' is --C.tbd.C--.

Claim 64

A compound according to claim 59 wherein Q 3 is ##STR236## wherein R 3 is as defined in claim 61.

Claim 65

A compound according to claim 60 wherein R 23 is ##STR237##

Claim 66

A compound according to claim 61 wherein L is trimethylene, and where, if R 30 is --CH 2 N(R 18 ) 2 or ##STR238## one R 18 is hydrogen, methyl, or phenyl, and the other R 18 is hydrogen, or, if R 30 is --COOR 19 , R 19 is (a) hydrogen, (b) methyl, (c) ethyl, ##STR239## (j) p-phenylphenacyl, or (k) a pharmacologically acceptable cation.

Claim 67

A compound according to claim 62 wherein R 25 is n-pentyl.

Claim 68

9-Deoxy-6δ,9α-epoxy-13,14-didehydro-PGF 1 , methyl ester, less polar and more polar isomers, compounds according to claim 63.

Claim 69

(6S)-13,14-Didehydro-PGI 1 , methyl ester, a compound according to claim 64.

Claim 70

(6R)-13,14-Didehydro-PGI 1 , methyl ester, a compound according to claim 64.

Claim 71

9-Deoxy-6δ,9α-epoxy-13,14-didehydro-PGF 1 , less polar and more polar isomers, compounds according to claim 63.

Claim 72

(6S)-13,14-Didehydro-PGI 1 , a compound according to claim 67.

Claim 73

(6R)-13,14-Didehydro-PGI 1 , a compound according to claim 67.

Claim 74

A compound according to claim 59 wherein Q 3 is ##STR240## wherein R 3 is as defined in claim 57.

Claim 75

A compound according to claim 70 wherein R 23 is ##STR241##

Claim 76

A compound according to claim 71 wherein L is trimethylene, and where, if R 30 is --CH 2 N(R 18 ) 2 or ##STR242## one R 18 is hydrogen, methyl, or phenyl, and the other R 18 is hydrogen, or if R 30 is --COOR 19 , R 19 is (a) hydrogen, (b) methyl, (c) ethyl, ##STR243## (j) p-phenylphenacyl, or (k) a pharmacologically acceptable cation.

Claim 77

A compound according to claim 72 wherein R 25 is n-pentyl.

Claim 78

9-Deoxy-6δ,9α-epoxy-13,14-didehydro-(15R)-PGF 1 , methyl ester, less polar and more polar isomers, compounds according to claim 73.

Claim 79

(6S,15R)-13,14-Didehydro-PGF 1 , methyl ester, a compound according to claim 74.

Claim 80

(6R,15R)-13,14-Didehydro-PGF 1 , methyl ester, a compound according to claim 74.

Claim 81

9-Deoxy-6ξ,9α-epoxy-13,14-didehydro-(15R)-PGF 1 , less polar and more polar isomers, compounds according to claim 73.

Claim 82

(6S,15R)-13,14-Didehydro-PGF 1 , a compound according to claim 77.

Claim 83

(6R,15R)-13,14-Didehydro-PGF 1 , a compound according to claim 77.

Claim 84

A compound according to claim 57 wherein X' is --CH 2 CH 2 --.

Claim 85

A compound according to claim 80 wherein Q 3 is ##STR244## wherein R 3 is defined as in claim 57.

Claim 86

A compound according to claim 81 wherein R 23 is ##STR245##

Claim 87

A compound according to claim 82 wherein L is --(CH 2 ) d -- wherein d is 1 to 5, inclusive.

Claim 88

A compound according to claim 83 wherein L is trimethylene and where, if R 30 is --CH 2 N(R 18 ) 2 or ##STR246## one R 18 is hydrogen, methyl, or phenyl, and the other R 18 is hydrogen, or if R 30 is --COOR 19 , R 19 is (a) hydrogen, (b) methyl, (c) ethyl, ##STR247## (j) p-phenylphenacyl, or (k) a pharmacologically acceptable cation.

Claim 89

A compound according to claim 84 wherein R 25 is n-pentyl.

Claim 90

9-Deoxy-6ξ,9α-epoxy-13,14-dihydro-PGF 1 , methyl ester, less polar and more polar isomers, compounds according to claim 85.

Claim 91

(6S)-13,14-Dihydro-PGI 1 , methyl ester, a compound according to claim 86.

Claim 92

(6R)-13,14-Dihydro-PGI 1 , methyl ester, a compound according to claim 86.

Claim 93

9-Deoxy-6ξ,9α-epoxy-13,14-dihydro-PGF 1 , less polar and more polar isomers, compounds according to claim 85.

Claim 94

(6S)-13,14-Dihydro-PGI 1 , a compound according to claim 89.

Claim 95

(6R)-13,14-Dihydro-PGI 1 , a compound according to claim 89.

Claim 96

A compound according to claim 84 wherein R 25 is ##STR248##

Claim 97

A compound according to claim 84 wherein R 25 is ##STR249##

Claim 98

A compound according to claim 82 wherein L is --(CH 2 ) t --CF 2 wherein t is 2, 3, or 4.

Claim 99

A compound according to claim 94 wherein t is 2, and where, if R 30 is --CH 2 N(R 18 ) 2 or ##STR250## one R 18 is hydrogen, methyl, or phenyl, and the other R 18 is hydrogen, or if R 30 is --COOR 19 , R 19 is (a) hydrogen, (b) methyl, (c) ethyl, ##STR251## (j) p-phenylphenacyl, or (k) a pharmacologically acceptable cation.

Claim 100

A compound according to claim 95 wherein R 25 is n-pentyl.

Claim 101

2,2-Difluoro-9-deoxy-6ξ,9α-epoxy-13,14-dihydro-PGF 1 , methyl ester, less polar and more polar compounds according to claim 96.

Claim 102

2,2-Difluoro-9-deoxy-6ξ,9α-epoxy-13,14-dihydro-PGF 1 , sodium salt, less polar and more polar compounds according to claim 96.

Claim 103

2,2-Difluoro-9-deoxy-6ξ,9α-epoxy-13,14-dihydro-PGF 1 , amide, less polar and more polar compounds according to claim 96.

Claim 104

A compound according to claim 95 wherein R 25 is ##STR252##

Claim 105

2,2-Difluoro-9-deoxy-6ξ,9α-epoxy-13,14-dihydro-16-phenoxy-17,18,19,20-tetranor-PGF 1 , methyl ester, less polar and more polar compounds according to claim 100.

Claim 106

2,2-Difluoro-9-deoxy-6ξ,9.alpha.-deoxy-13,14-dihydro-16-phenoxy-17,18,19,20-tetranor-PGF 1 , sodium salt, less polar and more polar compounds according to claim 100.

Claim 107

2,2-Difluoro-9-deoxy-6ξ,9α-epoxy-13,14-dihydro-16-phenoxy-17,18,19,20-tetranor-PGF 1 , amide, less polar and more polar compounds according to claim 100.

Claim 108

A compound according to claim 95 wherein R 25 is ##STR253##

Claim 109

2,2-Difluoro-9-deoxy-6ξ, 9α-epoxy-13,14-dihydro-17-phenyl-18,19,20-trinor-PGF 1 , methyl ester, less polar and more polar compounds according to claim 104.

Claim 110

2,2-Difluoro-9-deoxy-6ξ,9α-epoxy-13,14-dihydro-17-phenyl-18,19,20-trinor-PGF 1 , sodium salt, less polar and more polar compounds according to claim 104.

Claim 111

2,2-Difluoro-9-deoxy-6ξ,9.alpha.-epoxy-13,14-dihydro-17-phenyl-18,19,20-trinor-PGF 1 , amide, less polar and more polar compounds according claim 104.

Claim 112

A compound according to claim 82 wherein L is --CH 2 -CH═CH--A-- wherein A is a valence bond or --(CH 2 ) h -- wherein h is 1, 2, or 3.

Claim 113

A compound according to claim 108 wherein A is a valence bond and where, if R 30 is --CH 2 N(R 18 ) 2 or ##STR254## one R 18 is hydrogen, methyl, or phenyl, and the other R 18 is hydrogen, or if R 30 is --COOR 19 , R 19 is (a) hydrogen, (b) methyl, (c) ethyl, ##STR255## (j) p-phenylphenacyl, or (k) a pharmacologically acceptable salt.

Claim 114

A compound according to claim 109 wherein R 25 is n-pentyl.

Claim 115

A compound according to claim 109 wherein R 25 is ##STR256##

Claim 116

A compound according to claim 109 wherein R 25 is ##STR257##

Claim 117

A compound according to claim 80 wherein Q 3 is ##STR258##

Claim 118

9-Deoxy-6ξ,9α-epoxy-13,14-dihydro-15-deoxy-PGF 1 , methyl ester, less polar and more polar compounds according to claim 113.

Claim 119

(6S)-13,14-Dihydro-15-deoxy-PGI 1 , methyl ester, a compound according to claim 114.

Claim 120

(6R)-13,14-Dihydro-15-deoxy-PGI 1 , methyl ester, a compound according to claim 114.