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Details for Patent: 4,087,621

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Details for Patent: 4,087,621

Title: 7-{3-Hydroxy-2.beta.-[4-hydroxy-4-(lower alkyl)-trans-1-octen-1-yl]-5-oxocyclopent-1.alpha.-yl}hept-5-cis-enoic acids and related compounds
Abstract:7-{3-Hydroxy-2.beta.-[4-hydroxy-4-(lower alkyl)-trans-1-octen-1-yl]-5-oxocyclopent-1.alpha.-yl}hept-5-cis-enoic acids, displaying valuable pharmacological properties, e.g., gastric anti-secretory, are produced by the reaction of 7-(3-oxygenated-5-oxocyclopent-1-en-1-yl)hept-5-cis-enoic acid or ester with the appropriate organometallic reagent.
Inventor(s): Collins; Paul W. (Deerfield, IL), Pappo; Raphael (Skokie, IL)
Assignee: G. D. Searle & Co. (Chicago, IL)
Filing Date:Nov 10, 1975
Application Number:05/630,394
Claims:1. A compound of the formula

wherein R.sub.1 is hydrogen or lower alkyl; R.sub.2 is hydrogen or a lower alkanoyl, tetrahydropyran-2-yl, or tri(lower alkyl)silyl radical; R.sub.3 is hydrogen or a lower alkanoyl, or tri(lower alkyl)-silyl radical; R.sub.4 is a lower alkyl radical; and the wavy lines represent the

2. The compound according to claim 1 which is 7-[(3(R)-hydroxy-2.beta.-(4(R)-4-hydroxy-4-methyl-trans-1-octen-1-yl)-5-ox

3. The compound according to claim 1 which is racemic 7-[(3(R)-hydroxy-2.beta.-(4(S)-4-hydroxy-4-methyl-trans-1-octen-1-yl)-5-ox

4. The compound according to claim 1 which is racemic methyl 7-[3(S)-hydroxy-2.beta.-(4(RS)-4-hydroxy-4-methyl-trans-1-octen-1-yl)-5-ox

5. The compound according to claim 1 of the formula ##STR20## wherein R.sub.1 is hydrogen or lower alkyl; R.sub.2 is hydrogen or a lower alkanoyl or tetrahydropyran-2-yl radical; R.sub.3 is hydrogen or a lower alkanoyl radical; R.sub.4 is lower alkyl; and the wavy lines represent the alternative R or S configuration.

6. The compound according to claim 1 which is racemic methyl [3(R)-acetoxy-2.beta.-(4(S)-4-acetoxy-4-methyl-trans-1-octen-1-yl)-5-oxocy clopent-1.alpha.-yl]hept-5-cis-enoate.

7. The compound according to claim 1 which is methyl 7-[(3(R)-hydroxy-2.beta.-(4(R)-4-hydroxy-4-methyl-trans-1-octen-1-yl-5-oxo cyclopent-1.alpha.-yl]hept-5-cis-enoate.

8. The compound according to claim 1 which is methyl 7-[(3(R)-hydroxy-2.beta.-(4(S)-4-hydroxy-4-methyl-trans-1-octen-1-yl)-5-ox ocyclopent-1.alpha.-yl]hept-5-cis-enoate.

9. The compound according to claim 1 which is racemic methyl 7-[3(R)-hydroxy-2.beta.-(4(RS)-4-ethyl-4-hydroxy-trans-1-octen-1-yl)-5-oxo cyclopent-1.alpha.-yl]hept-5-cis-enoate.
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