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Details for Patent: 5,225,439

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Details for Patent: 5,225,439

Title: Prostaglandins E and anti ulcers containing same
Abstract:The novel 13, 14-dihydro-15-keto prostaglandins E of the invention have remarkable preventive effects against ulcers. Further, the novel 13,14-dihydro-15-keto-prostaglandins E of the invention have an advatage that they have none of side effects which prostaglandin E intrinsically has, or can remarakably reduce such effects of the prostaglandin E. Therefore, the novel 13, 14-dihydro-15-keto prostaglandins E of the invention are effective for animal and human use for treatment and prevention of ulcers, such as duodenal ulcer and gastric ulcer.
Inventor(s): Ueno; Ryuzo (Nishinomiya, JP), Ueno; Ryuji (Kyoto, JP), Kato; Ichie (Kawanishi, JP), Oda; Tomio (Itami, JP)
Assignee: K.K. Ueno Seiyaku Oyo Kenkyujo (Osaka, JP)
Filing Date:Apr 05, 1991
Application Number:07/681,031
Claims:1. Prostaglandins E represented by a general formula:

in which

X represents: ##STR46## R.sub.1 represents: a hydrogen atom, a physiologically acceptable salt residue, or an ester residue selected from the group consisting of alkyl, benzyl, hydroxyalkyl, alkoxyalkyl, alkylsilyl and tetrahydropyranyl group;

R.sub.2 represents: a hydrogen atom or a methyl group;

R.sub.3 represents: a hydroxyl or hydroxymethyl group;

R.sub.4 represents: a hydroxyl group;

R.sub.5 represents: a hydrogen atom or a methyl group; and

R.sub.6 represents: a C.sub.1 -C.sub.9 alkyl group which may have a branch or a double bond, or a C.sub.1 -C.sub.9 alkyl group having an alkoxy substituent group,

in which the C.sub.2 -C.sub.3 bond is a single or a double bond.

2. An anti-ulcer composition comprising an anti-ulcer effective amount of a prostaglandin E represented by a general formula: ##STR47## in which represents: ##STR48## R.sub.1 represents: a hydrogen atom, a physiologically acceptable salt residue, or an ester residue selected from the group consisting of alkyl, benzyl, hydroxyalkyl, alkoxyalkyl, alkylsilyl and tetrahydropyranyl group;

R.sub.2 represents: a hydrogen atom or a methyl group;

R.sub.3 represents: a hydroxyl or hydroxymethyl group;

R.sub.4 represents: a hydroxyl group;

R.sub.5 represents: a hydrogen atom or a methyl group; and

R.sub.6 represents: a C.sub.1 -C.sub.9 alkyl group which may have a branch or a double bond, or a C.sub.1 -C.sub.9 alkyl group having an alkoxy substituent group,

in which the C.sub.2 -C.sub.3 bond is a single or a double bond.

3. Prostaglandins E represented by a general formula: ##STR49## in which X represents: ##STR50## R.sub.1 represents: a hydrogen atom, a physiologically acceptable salt residue, or an ester residue selected from the group consisting of alkyl, benzyl, hydroxyalkyl, alkoxyalkyl, alkylsilyl and tetrahydropyranyl group;

R.sub.2 represents: a hydrogen atom or a methyl group;

R.sub.3 represents: a hydroxyl or hydroxymethyl group;

R.sub.4 represents: a hydrogen atom or a methyl group;

R.sub.5 represents: a hydrogen atom or a methyl group; and

R.sub.6 represents: a C.sub.1 -C.sub.9 alkyl group having an alkoxy substituent group,

in which the C.sub.2 -C.sub.3 bond is a single or a double bond.

4. Prostaglandins E as described in claim 3, being 13,14-dihydro-15-keto-5,6-dehydro-20-methoxy-PGE.sub.2 or alkyl ester thereof.

5. An anti-ulcer composition comprising an anti-ulcer effective amount of a prostaglandin E represented by a general formula: ##STR51## in which X represents: ##STR52## R.sub.1 represents: a hydrogen atom, a physiologically acceptable salt residue, or an ester residue selected from the group consisting of alkyl, benzyl, hydroxyalkyl, alkoxyalkyl, alkylsilyl and tetrahydropyranyl group;

R.sub.2 represents: a hydrogen atom or a methyl group;

R.sub.3 represents: a hydroxyl or hydroxymethyl group;

R.sub.4 represents: a hydrogen atom or a methyl group;

R.sub.5 represents: a hydrogen atom or a methyl group; and

R.sub.6 represents: a C.sub.1 -C.sub.9 alkyl group having an alkoxy substituent group,

in which the C.sub.2 -C.sub.3 bond is a single or a double bond.

6. An anti-ulcer composition as described in claim 5, wherein the prostaglandin E is 13,14-dihydro-15-keto-5,6-dehydro-20-methoxy-PGE.sub.2 or alkyl ester thereof.

7. Prostaglandins E represented by a general formula: ##STR53## in which X represents: ##STR54## R.sub.1 represents: a hydrogen atom, a physiologically acceptable salt residue, or an ester residue selected from the group consisting of alkyl, benzyl, hydroxyalkyl, alkoxyalkyl, alkylsilyl and tetrahydropyranyl group;

R.sub.2 represents: a hydrogen atom or a methyl group;

R.sub.3 represents: a hydroxyl or hydroxymethyl group;

R.sub.4 represents: a hydrogen atom or a methyl group;

R.sub.5 represents: a hydrogen atom or a methyl group; and

R.sub.6 represents: a C.sub.1 -C.sub.9 alkyl group which may have a branch or a double bond,

in which the C.sub.2 --C.sub.3 bond is a double bond.

8. Prostaglandins E as described in claim 7, being 13,14-dihydro-15-keto-.DELTA..sup.2 -PGE.sub.2 or alkyl ester thereof.

9. An anti-ulcer composition comprising an anti-ulcer effective amount of a prostaglandin E represented by a general formula: ##STR55## in which X represents: ##STR56## R.sub.1 represents: a hydrogen atom, a physiologically acceptable salt residue, or an ester residue selected from the group consisting of alkyl, benzyl, hydroxyalkyl, alkoxyalkyl, alkylsilyl and tetrahydropyranyl group;

R.sub.2 represents: a hydrogen atom or a methyl group;

R.sub.3 represents: a hydroxyl or hydroxymethyl group;

R.sub.4 represents: a hydrogen atom or a methyl group;

R.sub.5 represents: a hydrogen atom or a methyl group; and

R.sub.6 represents: a C.sub.1 -C.sub.9 alkyl group which may have a branch or a double bond,

in which the C.sub.2 -C.sub.3 bond is a double bond.

10. An anti-ulcer composition as described in claim 9, wherein the prostaglandin E is 13,14-dihydro-15-keto-.DELTA..sup.2 -PGE.sub.2 or alkyl ester thereof.

11. Prostaglandins E represented by a general formula: ##STR57## in which X represents: ##STR58## R.sub.1 represents: a hydrogen atom, a physiologically acceptable salt residue, or an ester residue selected from the group consisting of alkyl, benzyl, hydroxyalkyl, alkoxyalkyl, alkylsilyl and tetrahydropyranyl group;

R.sub.2 represents: a hydrogen atom or a methyl group;

R.sub.3 represents: a hydroxyl or hydroxymethyl group;

R.sub.4 represents: a methyl group;

R.sub.5 represents: a hydrogen atom or a methyl group; and

R.sub.6 represents: a C.sub.1 -C.sub.9 alkyl group which may have a branch or a double bond,

in which the C.sub.2 -C.sub.3 bond is a single bond.

12. Prostaglandins E as described in claim 11, wherein R.sub.5 is a methyl group.

13. Prostaglandins E as described in claim 11, wherein R.sub.6 is a C.sub.6 -C.sub.9 alkyl group.

14. Prostaglandins E as described in claim 11, wherein R.sub.6 is a hexyl group.

15. Prostaglandins E as described in claim 11, wherein the carboxyl group on the terminal position of the .alpha.-chain is esterified with an alkyl group.

16. An anti-ulcer composition comprising an anti-ulcer effective amount of a prostaglandin E represented by a general formula: ##STR59## in which X represents: ##STR60## R.sub.1 represents: a hydrogen atom, a physiologically acceptable salt residue, or an ester residue selected from the group consisting of alkyl, benzyl, hydroxyalkyl, alkoxyalkyl, alkylsilyl and tetrahydropyranyl group;

R.sub.2 represents: a hydrogen atom or a methyl group;

R.sub.3 represents: a hydroxyl or hydroxymethyl group;

R.sub.4 represents: a methyl group;

R.sub.5 represents: a hydrogen atom or a methyl group; and

R.sub.6 represents: a C.sub.1 -C.sub.9 alkyl group which may have a branch or a double bond,

in which the C.sub.2 -C.sub.3 bond is a single bond.

17. An anti-ulcer composition as described in claim 16, wherein R.sub.5 is a methyl group.

18. An anti-ulcer composition as described in claim 16, wherein R.sub.6 is a C.sub.6 -C.sub.9 alkyl group.

19. An anti-ulcer composition as described in claim 16, wherein R.sub.6 is a hexyl group.

20. An anti-ulcer composition as described in claim 16, wherein the carboxyl group on the terminal position of the .alpha.-chain is esterified with an alkyl group.

21. An anti-ulcer composition as described in claim 16, wherein the prosaglandin E is 13, 14-dihydro-15-keto-6R,S-methyl-PGE.sub.2 alkyl ester.

22. A method of treating an ulcer comprising administering to a patient in need of such treatment an anti-ulcer effective amount of a prostaglandin E represented by a general formula: ##STR61## in which X represents ##STR62## R.sub.1 represents: a hydrogen atom, a physiologically acceptable salt residue, or an ester residue selected from the group consisting of alkyl, benzyl, hydroxyalkyl, alkoxyalkyl, alkylsilyl and tetrahydropyranyl group;

R.sub.2 represents: a hydrogen atom or a methyl group;

R.sub.3 represents: a hydroxyl or hydroxymethyl group;

R.sub.4 represents: a hydrogen atom, a methyl group or a hydroxyl group;

R.sub.5 represents: a hydrogen atom or a methyl group; and

R.sub.6 represents: a C.sub.1 -C.sub.9 alkyl group which may have a branch or a double bond, or a C.sub.1 -C.sub.9 alkyl group having an alkoxy substituent group, in which the C.sub.2 -C.sub.3 bond is a single or a double bond; provided that when R.sub.4 and R.sub.5 are each hydrogen, R.sub.6 is a C.sub.5 -C.sub.9 alkyl group which may have a branch or a double bond, or a C.sub.1 -C.sub.9 alkyl group having an alkoxy substituent group.
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