Oxygenated amino- or ammonium-containing sulfonic acid, phosphonic acid and carboxylic acid derivatives and their medical use
The present invention relates to oxygenated amino or ammonium-containing sulfonic acid, phosphoric 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 the treatment, prevention or amelioration of an inflammatory, autoimmune and/or allergic disorder, or a proliferative, neoplastic or dysplastic disease or disorder.
1. A compound of the following formula 1
wherein
R 1 is a C 10-20 hydrocarbon group;
R 2 is a C 1-4 alkyl group, and R 3 is —H, or R 3 is absent;
R 4 is a C 3-6 alkylene group which is substituted with one or more groups independently selected from OH, —O(C 1-3 alkyl), —O—C(O)—(C 1-3 alkyl), —O—C(O)—O(C 1-3 alkyl), —O—C(O)—NH 2 , —O—C(O)—NH(C 1-3 alkyl), —O—C(O)—N(C 1-3 alkyl)(C 1-3 alkyl), —O(CH 2 ) 2 OH, or —O(CH 2 ) 3 OH;
R 5 is —PO 3 2− , —PO 3 H − , or —PO 3 H 2 ; and
X is N + or, if R 3 is absent, X is N;
or a pharmaceutically acceptable salt, or solvate thereof.
2. A compound of the following formula 1b:
or a pharmaceutically acceptable salt, or solvate thereof.
3. A compound of the following formula 1
wherein
R 1 is a C 10-20 hydrocarbon group;
R 2 is a C 1-4 alkyl group, and R 3 is —H, or R 3 is absent;
R 4 is a C 3-6 alkylene group which is substituted with one or more groups independently selected from —OH, —O(C 1-3 alkyl), —O—C(O)—(C 1-3 alkyl), —O—C(O)—C(C 1-3 alkyl), —O—C(O)—NH 2 , —O—C(O)—NH(C 1-3 alkyl), —O—C(O)—N(C 1-3 alkyl)(C 1-3 alkyl), —O(CH 2 ) 2 OH, or —O(CH 2 ) 3 OH;
R 5 is —SO 3 − , —SO 3 H, —PO 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 + or, if R 3 is absent, X is N;
or a pharmaceutically acceptable salt, or solvate thereof, wherein the compound does not comprise formula 1a:
4. A compound of the following formula 1c:
or a pharmaceutically acceptable salt, or solvate thereof.
5. A compound of the following formula 1d or 1e:
or a pharmaceutically acceptable salt or solvate thereof.