Patent EP-3607945-A1 (EP)
Inventor: KELLIHER ADAM
IPC: A61K31/202
Filed: 2010-04-29
Abstract: The invention provides a compound which is a polyunsaturated fatty acid (PUFA) derivative of formula (I),or a pharmaceutically acceptable salt, or solvate thereof, wherein- -Alk- is -CH(OR<sub>2</sub>)-[trans]CH=CH-[cis]CH=CH-CH<sub>2</sub>-[cis]CH=CH-C<sub>3</sub>H<sub>6</sub>-,-(CH<sub>2</sub>)<sub>3</sub>-CH(OR<sub>2</sub>)-[trans]CH=CH-[cis]CH=CH-CH<sub>2</sub>-[cis]CH=CH-, -(CH<sub>2</sub>)<sub>3</sub>-[cis]CH=CH-CH<sub>2</sub>-[cis]CH=CH-[trans]CH=CH-CH(OR<sub>2</sub>)- or -CH<sub>2</sub>-[cis]CH=CH-CH<sub>2</sub>-[cis]CH=CH-[trans]CH=CH-CH(OR<sub>2</sub>)-;- R<sub>1</sub>is a hydrogen atom; orR<sub>1</sub>is a C<sub>1</sub>-C<sub>6</sub>alkyl, C<sub>2</sub>-C<sub>6</sub>alkenyl, C<sub>2</sub>-C<sub>6</sub>alkynyl, C<sub>6</sub>-C<sub>10</sub>aryl, 5- to 10-membered heteroaryl, C<sub>3</sub>-C<sub>7</sub>carbocyclyl or 5- to 10-membered heterocyclyl group; or R<sub>1</sub>is a group of formula -CH<sub>2</sub>-CH(OR<sub>3</sub>)-CH<sub>2</sub>-(OR<sub>4</sub>), wherein R<sub>3</sub>and R<sub>4</sub>are each independently hydrogen atoms or -(C=O)-R<sub>6</sub>, wherein R<sub>6</sub>is an aliphatic group having from 3 to 29 carbon atoms; orR<sub>1</sub>is a group of formula -(CH<sub>2</sub>OCH<sub>2</sub>)<sub>m</sub>OH, wherein m is an integer of from 1 to 200;- R<sub>2</sub>is a hydrogen atom; orR<sub>2</sub>is a group -(C=O)-R<sub>5</sub>, wherein R<sub>5</sub>is a C<sub>1</sub>-C<sub>6</sub>alkyl, C<sub>2</sub>-C<sub>6</sub>alkenyl, C<sub>2</sub>-C<sub>6</sub>alkynyl, C<sub>6</sub>-C<sub>10</sub>aryl, 5- to 10-membered heteroaryl, C<sub>3</sub>-C<sub>7</sub>carbocyclyl or 5- to 10-membered heterocyclyl group, or R<sub>5</sub>is an aliphatic group having from 3 to 29 carbon atoms; orR<sub>2</sub>is a group of formula -(CH<sub>2</sub>OCH<sub>2</sub>)<sub>n</sub>OH, wherein n is an integer of from 1 to 200;and wherein- said alkyl, alkenyl, alkynyl and aliphatic groups are the same or different and are each unsubstituted or substituted with 1, 2 or 3 unsubstituted substituents which are the same or different and are selected from halogen atoms and C<sub>1</sub>-C<sub>4</sub>alkoxy, C<sub>2</sub>-C<sub>4</sub>alkenyloxy, C<sub>1</sub>-C<sub>4</sub>haloalkyl, C<sub>2</sub>-C<sub>4</sub>haloalkenyl, C<sub>1</sub>-C<sub>4</sub>haloalkoxy, C<sub>2</sub>-C<sub>4</sub>haloalkenyloxy, hydroxyl, -SR', and -NR'R" groups where R' and R" are the same or different and represent hydrogen or unsubstituted C<sub>1</sub>-C<sub>2</sub>alkyl;- said aryl, heteroaryl, carbocyclyl and heterocyclyl groups are the same or different and are each unsubstituted or substituted by 1, 2, 3 or 4 unsubstituted substituents which are the same or different and are selected from halogen atoms, and cyano, nitro, C<sub>1</sub>-C<sub>4</sub>alkyl, C<sub>1</sub>-C<sub>4</sub>alkoxy, C<sub>2</sub>-C<sub>4</sub>alkenyl, C<sub>2</sub>-C<sub>4</sub>alkenyloxy, Ci-C<sub>4</sub>haloalkyl, C<sub>2</sub>-C<sub>4</sub>haloalkenyl, C<sub>1</sub>-C<sub>4</sub>haloalkoxy, C<sub>2</sub>-C<sub>4</sub>haloalkenyloxy, hydroxyl, C<sub>1</sub>-C<sub>4</sub>hydroxyalkyl, -SR' and -NR'R" groups wherein each R' and R" is the same or different and represents hydrogen or unsubstituted C<sub>1</sub>-C<sub>4</sub>alkyl;and wherein the PUFA derivative is in the form of a racemate, a stereoisomer or a mixture of stereoisomers,which compound is for use in treating skin inflammation in a mammal, by topical administration.