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Claims for Patent: 5,284,858

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Claims for Patent: 5,284,858

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-ketoprostaglandins 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: Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo (Osaka, JP)
Application Number:07/925,220
Patent Claims: 1. Prostaglandins E represented by a general formula:

in which

X represents: ##STR47## R.sub.1 represents: a hydrogen atom, a physiologically acceptable sat 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 and R.sub.5 each represents: a hydrogen atom, a methyl group or a halogen atom provided that at least one of R4 and R5 is a halogen atom; 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, the C.sub.2 -C.sub.3 bond being a single or double bond.

2. Prostaglandins E as described in claim 1, wherein R.sub.4 and R.sub.5 are halogen atoms.

3. Prostaglandins E as described in claim 1, wherein R.sub.4 and/or R.sub.5 is a fluorine atom.

4. Prostaglandins E as described in claim 1, wherein R.sub.4 or R.sub.5 is a methyl group.

5. Prostaglandins E as described in claim 1, which is 13,14-dihydro-15-keto-PGE having one or more fluorine atom(s) on 16-position or alkyl ester thereof.

6. Prostaglandins E as described in claim 1, being 13,14-dihydro-6,15-diketo-16R,S-fluoro-PGE.sub.1 or alkyl ester thereof.

7. An anti-ulcer composition comprising an anti-ulcer effective amount of a prostaglandin E expressed by a general formula: ##STR48## in which X represents: ##STR49## R.sub.1 represents: a hydrogen atom, a physiologically acceptable sat 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 and R.sub.5 each represents: a hydrogen atom, a methyl group or a halogen atom provided that at least one of R.sub.4 and R.sub.5 is a halogen atom; 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, the C.sub.2 -C.sub.3 bond being a single or double bond.

8. An anti-ulcer composition as in claim 7, wherein R.sub.4 and R.sub.5 are halogen atoms.

9. An anti-ulcer composition as in claim 7, wherein R.sub.4 and/or R.sub.5 is a fluorine atom.

10. An anti-ulcer composition as in claim 7, wherein R.sub.4 or R.sub.5 is a methyl group.

11. An anti-ulcer composition as in claim 7, wherein the prostaglandin E is 13,14-dihydro-15-PGE having one or more fluorine atom(s) on 16-position or alkyl ester thereof.

12. An anti-ulcer composition as in claim 7, wherein the prostaglandin E is 13,14-dihydro-6,15-diketo-16R,S-fluoro-PGE.sub.1 or alkyl ester thereof.

13. A treatment of ulcer by administering an anti-ulcer treating effective amount of prostaglandin E to a patient, wherein the prostaglandin E is represented by a formula: ##STR50## in which X represents: ##STR51## 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 and R.sub.5 each represents: a hydrogen atom, a methyl group or a halogen atom provided that at least one of R.sub.4 and R.sub.5 is a halogen atom; 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, the C.sub.2 -C.sub.3 bond being a single or double bond.
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