Natural product analogs including an anti-inflammatory cyanoenone pharmacore and methods of use
US-2018237383-A1 · Aug 23, 2018 · US
US8987239B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-8987239-B2 |
| Application number | US-201313738751-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jan 10, 2013 |
| Priority date | Dec 29, 2007 |
| Publication date | Mar 24, 2015 |
| Grant date | Mar 24, 2015 |
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The 15α,16α-methylene-17-hydroxy-19-nor-17-pregna-4-en-3-one-21-carboxylic acid γ-lactone derivatives of the present invention possess progestational efficacy. They have the general chemical formula I, in which Z is selected from the group comprising an oxygen atom, two hydrogen atoms, NOR and NNHSO 2 R, where R is hydrogen, C 1 -C 10 -alkyl, aryl or C 7 -C 20 -aralkyl, R 4 is hydrogen or halogen, and moreover either: R 6a , R 6b together form methylene or 1,2-ethanediyl or R 6a is hydrogen and R 6b is selected from the group comprising hydrogen, C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl or C 2 -C 10 -alkynyl, and R 7 is selected from the group comprising hydrogen, C 1 -C 10 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 10 -alkenyl or C 2 -C 10 -alkynyl, or: R 6a is hydrogen and R 6b and R 7 , together, denote a bond, an oxygen or form methylene, R 18 represents hydrogen or C 1 -C 3 -alkyl and in addition include their solvates, hydrates, stereoisomers and salts.
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The invention claimed is: 1. 15α,16α-Methylene-17-hydroxy-19-nor-17-pregna-4-en-3-one-21-carboxylic acid γ-lactone namely 17βHydroxy-15α,16α-methylene-19-nor-17α-pregna-4-en-3-one-21-carboxylic acid γ-lactone; 17β-Hydroxy-7α-methyl-15α,16α-methylene-19-nor-17α-pregna-4-en-3-one-21-carboxylic acid γ-lactone; 17β-Hydroxy-7β-methyl-15α,16α-methylene-19-nor-17α-pregna-4-en-3-one-21-carboxylic acid γ-lactone; 17β-Hydroxy-7α-ethyl-15α,16α-methylene-19-nor-17α-pregna-4-en-3-one-21-…
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