Halogen-substituted heterocyclic compound salt
The invention provides a novel α-halogen-substituted thiophene compound salt that has a potent LPA receptor antagonistic action and is useful as a medicament. The salt is represented by the general formula (I): (wherein R is a hydrogen atom or a methoxy group; X is a halogen atom; A is selected from the group consisting of: M is an alkali metal or an alkaline earth metal; and n is 1 when M is an alkali metal and is 2 when M is an alkaline earth metal).
1. A salt of formula (I):
wherein
R is a hydrogen atom or a methoxy group,
X is a halogen atom,
A is selected from the group consisting of:
M is an alkali metal or an alkaline earth metal, and
n is 1 when M is an alkali metal and is 2 when M is an alkaline earth metal.
2. The salt according to claim 1 , wherein the alkali metal or the alkaline earth metal is sodium, potassium or calcium.
3. A salt of (R)-1-[4′-(5-chloro-3-{[(1-phenylethoxy)carbonyl]amino}thiophen-2-yl)-2′-methoxy[1,1′-biphenyl]-4-yl]cyclopropanecarboxylic acid with an alkali metal or an alkaline earth metal.
4. The salt according to claim 3 , wherein the alkali metal or the alkaline earth metal is sodium, potassium or calcium.
5. A salt of (R)-1-{4′-[5-chloro-3-({[1-(2,5-difluorophenyl)ethoxy]carbonyl}amino)thiophen-2-yl]-2′-methoxy-[1,1′-biphenyl]-4-yl}cyclopropanecarboxylic acid with an alkali metal or an alkaline earth metal.
6. The salt according to claim 5 , wherein the alkali metal or the alkaline earth metal is sodium, potassium or calcium.
7. A salt of (R)-1-{4′-[3-({[1-(2-chlorophenyl)ethoxy]carbonyl}amino)-5-fluorothiophen-2-yl]-2′-methoxy-[ 1,1′-biphenyl]-4-yl}cyclopropanecarboxylic acid with an alkali metal or an alkaline earth metal.
8. The salt according to claim 7 , wherein the alkali metal or the alkaline earth metal is sodium, potassium or calcium.
9. A salt of (R)-1-{4′-[5-chloro-3-({[1-(thiophen-3-yl)ethoxy]carbonyl}amino)thiophen-2-yl]-[1,1′-biphenyl]-4-yl}cyclopropanecarboxylic acid with an alkali metal or an alkaline earth metal.
10. The salt according to claim 9 , wherein the alkali metal or the alkaline earth metal is sodium, potassium or calcium.
11. A salt of (R)-1-{4′-[5-fluoro-3-({[1-(4-methylthiophen-3-yl)ethoxy]carbonyl}amino)thiophen-2-yl]-[1,1′-biphenyl]-4-yl}cyclopropanecarboxylic acid with an alkali metal or an alkaline earth metal.
12. The salt according to claim 11 , wherein the alkali metal or the alkaline earth metal is sodium, potassium or calcium.
13. An LPA receptor antagonist comprising the salt according to claim 1 as an active ingredient.
14. A pharmaceutical composition comprising the salt according to claim 1 as an active ingredient.
15. The pharmaceutical composition according to claim 14 for the treatment of fibrosis, rheumatoid arthritis or cancer.