Amino- or ammonium-containing sulfonic acid, phosphonic acid and carboxylic acid derivatives and their medical use
The present invention relates to amino- or ammonium-containing sulfonic acid, phosphonic acid and carboxylic acid derivatives, in particular the compounds of formula 1, 2, 3, 4, 5 or 6 and their medical use, including their use in treatment, prevention or amelioration of an inflammatory, autoimmune and/or allergic disorder.
1. A compound of the following formula 1
or a pharmaceutically acceptable salt, solvate, or prodrug thereof, wherein:
R 1 is a C 10-20 hydrocarbon group;
R 2 is a C 1-4 alkyl group, and R 3 is H;
R 4 is a C 1-6 hydrocarbon group;
R 5 is —SO 3 , —SO 3 H, —PO 3 2− , —PO 3 H 2 , —PO 2 (OC 1-3 alkyl), —PO 2 H(OC 1-3 alkyl), —PO(OC 1-3 alkyl) 2 , —CO 2 , —CO 2 H or —CO 2 (C 1-3 alkyl; and
X is N + .
2. The compound of claim 1 , wherein R 5 is —SO 3 or —SO 3 H.
3. The compound of claim 1 , wherein R 5 is —PO 3 2− ″, —PO 3 H − , or —PO 3 H 2 .
4. The compound of claim 1 , wherein R 4 is —(CH 2 ) 3 —.
5. The compound of claim 1 , wherein R 1 is a linear C 10-20 alkyl group, a linker C 10-20 alkenyl group, or a linear C 10-20 alkynyl group.
6. The compound of claim 1 , wherein R 1 is —(CH 2 ) 11 —CH 3 , —(CH 2 ) 13 —CH 3 , or —(CH 2 ) 15 —CH 3 .
7. The compound of claim 1 , wherein R 2 is methyl.
8. The compound of claim 1 , wherein the compound is a compound of any of the following formulae:
9. A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable excipient.