Novel cellular metabolic regulatory compounds and their uses

Abstract

This invention provides a compound that binds to FABP4, regulates the metabolism of adipocytes, and improves glucose utilization. [Solution] The compound of formula I, or a pharmaceutically acceptable salt or stereoisomer thereof. TIFF2026097884000085.tif77170

Claims

1. A compound of formula I, 【Chemistry 1】 [In the formula, W １～４ and Z １ ~Z ５ These are, independently, -C, -CH, and CH. ２ , O, S, or N; X is independently CH ２ , N, or CHR ４ And; Y is independent of CH ２ , or CHR ５ And: n is a number between 0 and 3; One or more Rs on ring Z １ ’s are, independently, CN, OH, COOH, OCH ３ , CF ３ , CONH ２ , B(OH) ２ , B(OR) ２ , an isostere of an acid, a substituted amine, an ether, and a halogen, a substituted or unsubstituted alkyl, a substituted or unsubstituted cyclic or heterocyclic, a substituted or unsubstituted cycloaryl or cycloheteroaryl (where the substituted cycloaryl or cycloheteroaryl is hydrogen, CN, OH, COOH, OCH ３ , CF ３ , CONH ２ , B(OH) ２ , B(OR) ２ , an isostere of an acid, a substituted amine, an ether, and a halogen, a substituted or unsubstituted alkyl, a substituted or unsubstituted cyclic or heterocyclic, a substituted or unsubstituted cycloaryl or cycloheteroaryl, and SO ２ NH ２ and may be substituted with) and are selected from the group consisting of; One or more R on ring W ２ ' is independently CN, OH, CHF2, CH2F, CF ３ , COOH, CONH ２ , B(OH) ２ , B (OR) ２ , selected from the group consisting of acid isosteres, halogens, and bicyclic heteroaryls; R ７ This is hydrogen, or CN, COOH, CONH ２ , B(OH) ２ , B (OR) ２ or is an acid isoster; R is an alkyl group; R ３ , R ４ , R ５ Or R ８ , or R ６ If n is not zero, then each is independently selected from the following: (1) Hydrogen, (2) A substituted or unsubstituted alkyl or ether having 1 to 12 carbon atoms, (3) Substituted amines, (4) - (CH ２ ) ｍ G (where m is between 1 and 12, and G is independently selected from the following): (a) Cycloalkyl having 3 to 6 carbon atoms, (b) Aryl or heteroaryl, (c) CF ３ CF ２ H, or CFH ２ , or (d) complex algebras, However, R ３ , R ４ , R ５ , R ８ , or R ６ [It's not all hydrogen.] Alternatively, pharmaceutically acceptable salts or stereoisomers thereof. A compound containing [this compound].

2. R １ and R ２ Both exist, and each is independent of CN, COOH, or CONH ２ The compound according to claim 1.

3. The above formula I is a plurality of R １ 'and R ２ The compound according to claim 1, comprising '.

4. R ３ , R ４ , R ５ , R ８ , or R ６ The compound according to claim 1, wherein, when n is not zero, each is an alkyl group having four carbon atoms independently.

5. R ３ , R ４ , R ５ , R ８ , or R ６ However, if n is not zero, the compound according to claim 1 is an alkyl group having five carbon atoms, each independently.

6. R ３ , R ４ , R ５ , R ８ , or R ６ The compound according to claim 1, wherein, when n is not zero, each is an alkyl group having six carbon atoms independently.

7. The ring Z is Z １ ~Z ４ The compound according to claim 1, comprising:

8. The ring Z is Z １ ~Z ５ The compound according to claim 1, comprising:

9. One or more R on the ring Z １ The compound according to claim 1, wherein the compound is a halogen.

10. One or more R on the ring Z １ The compound according to claim 1, wherein the compound is CN.

11. One or more R on the ring Z １ However, CF ３ The compound according to claim 1.

12. One or more R on the ring W ２ The compound according to claim 1, wherein the compound is a halogen.

13. One or more R on the ring Z １ The compound according to claim 1, wherein it contains CN and / or halogen.

14. One or more R on the ring Z １ However, it includes CN and / or halogens, and one or more R on the ring W. ２ The compound according to claim 1, further comprising another halogen.

15. The compound according to claim 14, wherein the halogen is the same as the other halogen.

16. The compound according to claim 14, wherein the halogen is different from the other halogens.

17. A compound of formula II, 【Chemistry 2】 [In the formula, n = 0, 1, or 2; R １ , CN, COOH, CONH ２ , B(OH) ２ , B (OR) ２ Selected from the group consisting of acid isosteres and halogens; R ２ , CN, COOH, CONH ２ , B(OH) ２ , B (OR) ２ , selected from the group consisting of acid isosteres, halogens, and bicyclic compounds; R ７ This is hydrogen, or CN, COOH, CONH ２ , B(OH) ２ , B (OR) ２ or is an acid isoster; R is an alkyl group; R ３ 、 R ４ 、 R ５ or R ８ 、 or R ６ is, when n is not zero, each independently selected from the following: (1) Hydrogen, (2) an alkyl having 1 to 12 carbon atoms, (3) - (CH ２ ) ｍ G (where m is between 1 and 12, and G is independently selected from the following): (a) Cycloalkyl having 3 to 6 carbon atoms, (b) Aryl or heteroaryl, (c) CF ３ , CF ２ H, or CFH ２ ; However, G is not a nitrogen or oxygen-containing group; However, R ３ , R ４ , R ５ , R ８ , or R ６ [It's not all hydrogen.] or their pharmaceutically acceptable salts A compound containing [this compound].

18. R １ and R ２ Both exist, and each is independent of CN, COOH, or CONH ２ The compound according to claim 17.

19. The above equation II is for multiple R １ 'and R ２ The compound according to claim 17, comprising '.

20. R ３ , R ４ , R ５ , R ８ , or R ６ However, if n is not zero, each is an alkyl group having four carbon atoms, as per claim 17.

21. R ３ , R ４ , R ５ , R ８ , or R ６ However, if n is not zero, each is an alkyl group having five carbon atoms, as per claim 17.

22. R ３ , R ４ , R ５ , R ８ , or R ６ The compound according to claim 17, wherein, when n is not zero, each is an alkyl group having six carbon atoms independently.

23. A compound of formula III, 【Transformation 3】 [In the formula, n = 0, 1, or 2; R １ and R ２ These are, independently, CN, COOH, or CONH ２ And; R ３ These are independently selected from the following: (1) Alkyl groups having 1 to 12 carbon atoms; (2) - (CH ２ ) ｍ G (where m is between 1 and 12, and G is independently selected from the following): (a) Cycloalkyl groups having 3 to 6 carbon atoms; (b) Phenyl; However, G is not a nitrogen or oxygen-containing group. or their pharmaceutically acceptable salts A compound containing [this compound].

24. n = 0, R ３ The compound according to claim 23, wherein the compound is bonded at the h-, i-, or j-position.

25. n=1, R ３ The compound according to claim 23, wherein the compound is bonded at the h-, i-, or j-position.

26. n = 2, R ３ The compound according to claim 23, wherein the compound is bonded at the h-, i-, or j-position.

27. The compound according to claim 1, 17, or 23, which is a pure optical isomer.

28. The compound according to claim 23, which is a (+) isomer.

29. The compound according to claim 23, which is a (-) isomer.

30. It is a compound, 5-[(3-cyanophenyl)methyl]-2-fluoro-7-hexyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(6-cyanopyridine-2-yl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(6-carbamoylpyridine-2-yl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 6-({4-carboxy-7- Hexyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-5-yl}methyl)pyridine-2-carboxylic acid, 5-[(3-cyano-2-fluorophenyl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(1,3-benzoxazol-6-yl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(1,3-benzoxazol-5-yl)methyl]-7- Hexyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(6-fluoropyridine-2-yl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(2-fluoropyridine-4-yl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 7-hexyl-5-{[6-(trifluoromethyl)pyridine-2-yl]methyl}-5H,6 H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid,7-hexyl-5-{[2-(trifluoromethyl)pyridine-4-yl]methyl}-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid,5-[(5-cyanopyridine-3-yl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid,5-[(5-cyanothiophen-2-yl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 5-[(4-cyanothiophen-2-yl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 5-[(5-cyanofuran-2-yl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 5-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole- 4-carboxylic acid, 5-(3-cyanobenzoyl)-7-hexyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(1,3-benzoxazol-7-yl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(5-cyanothiophen-3-yl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 7-hexyl-5-[(1H-indole-4-yl)methyl 5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(3-carbamoylphenyl)methyl]-7-propyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 7-butyl-5-[(3-carbamoylphenyl)methyl]-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 7-butyl-5-[(3-cyanophenyl)methyl]-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4- Carboxylic acid, 7-butyl-5-[(pyridine-3-yl)methyl]-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 7-butyl-5-[(3-methylphenyl)methyl]-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 7-butyl-5-[(3-methoxyphenyl)methyl]-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 7-butyl-5-[(3-chlorophenyl)methyl]-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 7-Butyl-5-[(3-hydroxyphenyl)methyl]-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 7-Butyl-5-[(2-methoxypyridine-4-yl)methyl]-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 7-Butyl-5-[(4-carbamoylphenyl)methyl]-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 7-Butyl- 5-[(2-carbamoylphenyl)methyl]-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 7-butyl-5-[(4-methylphenyl)methyl]-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 7-butyl-5-[(2-cyanophenyl)methyl]-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 7-butyl-5-[(2-methylphenyl)methyl]-5H,6H,7H,8H,9H,10H-cyclohepta 10H-cyclohepta[b]indole-4-carboxylic acid, 7-butyl-5-[(2-fluorophenyl)methyl]-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(3-carbamoylphenyl)methyl]-7-pentyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(3-cyanophenyl)methyl]-7-pentyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(3-carbamoylphenyl)methyl [(3-cyanophenyl)methyl]-7-(2-phenylethyl)-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(3-cyanophenyl)methyl]-7-(2-phenylethyl)-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(3-carbamoylphenyl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(3-cyanophenyl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 5-[(3-carbamoylphenyl)methyl]-7-octyl-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 5-[(3-cyanophenyl)methyl]-7-octyl-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 5-[(3-fluorophenyl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 7-hexyl- 5-[(pyridine-3-yl)methyl]-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid,7-hexyl-5-[(3-methylphenyl)methyl]-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid,7-hexyl-5-[(3-methoxyphenyl)methyl]-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid,5-[(3-chlorophenyl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H- Cyclohepta[b]indole-4-carboxylic acid, 7-hexyl-5-[(2-methoxypyridine-4-yl)methyl]-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 5-[(3-carboxyphenyl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 5-[(4-carbamoylphenyl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 5-[(2 -Carbamoylphenyl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid,7-hexyl-5-[(4-methylphenyl)methyl]-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid,5-[(4-cyanophenyl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid,5-[(2-cyanophenyl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 7-hexyl-5-[(2-methylphenyl)methyl]-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 5-[(2-fluorophenyl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 5-[(4-fluorophenyl)methyl]-7-hexyl-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 9-[(3-carbamoylphenyl )methyl]-2-hexyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid,9-[(3-cyanophenyl)methyl]-2-hexyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid,9-[(3-carboxyphenyl)methyl]-2-hexyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid,9-[(3-fluorophenyl)methyl]-2-hexyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid,2-hexyl-9-[(pyridine-3-yl)methyl 2-H-tetrahydro-1H-carbazole-8-carboxylic acid, 2-hexyl-9-[(3-methylphenyl)methyl]-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 2-hexyl-9-[(3-methoxyphenyl)methyl]-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-chlorophenyl)methyl]-2-hexyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 2-hexyl-9-[(3-hydroxyphenyl)methyl]-2,3,4,9 -Tetrahydro-1H-carbazole-8-carboxylic acid, 2-hexyl-9-[(2-methoxypyridine-4-yl)methyl]-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-carboxyphenyl)methyl]-2-hexyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(4-carbamoylphenyl)methyl]-2-hexyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(2-carbamoylphenyl)methyl]-2-hexyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 2-hexyl-9-[(4-methylphenyl)methyl]-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(4-cyanophenyl)methyl]-2-hexyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(2-cyanophenyl)methyl]-2-hexyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 2-hexyl-9-[(2-methylphenyl)methyl]-, 2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(2-fluorophenyl)methyl]-2-hexyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-carbamoylphenyl)methyl]-2-(2-phenylethyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-cyanophenyl)methyl]-2-(2-phenylethyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-carbamoylphenyl)methyl [(3-Cyanophenyl)methyl]-4-(2-phenylethyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-Cyanophenyl)methyl]-4-(2-phenylethyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-Carbamoylphenyl)methyl]-2-propyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-Cyanophenyl)methyl]-2-propyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid Rubonic acid, 2-butyl-9-[(3-carbamoylphenyl)methyl]-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-carbamoylphenyl)methyl]-2-pentyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-cyanophenyl)methyl]-2-pentyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 1-butyl-9-[(3-carbamoylphenyl)methyl]-2,3,4,9-tetrahydro-1H-carbazole- 8-carboxylic acid, 9-[(3-carbamoylphenyl)methyl]-1-(pentyloxy)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-cyanophenyl)methyl]-1-(pentyloxy)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 1-butyl-9-[(3-cyanophenyl)methyl]-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 6-butyl-5-[(3-carbamoylphenyl)methyl]-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 6-butyl-5-[(3-cyanophenyl)methyl]-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, 9-[(3-carbamoylphenyl)methyl]-1-ethyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-cyanophenyl)methyl]-1-ethyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-carboxyphenyl)methyl]-1-ethyl Tyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-carbamoylphenyl)methyl]-1-propoxy-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-carbamoylphenyl)methyl]-4-ethyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 4-[(3-carbamoylphenyl)methyl]-3-ethyl-1H,2H,3H,4H-cyclopenta[b]indole-5-carboxylic acid, 4-[(3-cyanophenyl)methyl] [Tyl]-3-ethyl-1H,2H,3H,4H-cyclopenta[b]indole-5-carboxylic acid, 3-butyl-4-[(3-carbamoylphenyl)methyl]-1H,2H,3H,4H-cyclopenta[b]indole-5-carboxylic acid, 3-butyl-4-[(3-cyanophenyl)methyl]-1H,2H,3H,4H-cyclopenta[b]indole-5-carboxylic acid, 2-butyl-4-[(3-carbamoylphenyl)methyl]-1H,2H,3H,4H-cyclopenta[b]indole-5-carboxylic acid, 2-butyl- 4-[(3-cyanophenyl)methyl]-1H,2H,3H,4H-cyclopenta[b]indole-5-carboxylic acid, 5-[(3-carbamoylphenyl)methyl]-10-ethyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(3-cyanophenyl)methyl]-10-ethyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(3-carbamoylphenyl)methyl]-10-propyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(3-cyanophenyl)methyl]-10-propyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 9-[(3-carboxyphenyl)methyl]-4-ethyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-carbamoylphenyl)methyl]-3-ethyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 10-butyl-5-[(3-carbamoylphenyl)methyl 5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 10-butyl-5-[(3-cyanophenyl)methyl]-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(3-carbamoylphenyl)methyl]-10-pentyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(3-cyanophenyl)methyl]-10-pentyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(3-cyanophenyl)methyl]-10-pentyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid 4-carboxylate, 4-[(3-carbamoylphenyl)methyl]-2-pentyl-1H,2H,3H,4H-cyclopenta[b]indole-5-carboxylic acid, 4-[(3-cyanophenyl)methyl]-2-pentyl-1H,2H,3H,4H-cyclopenta[b]indole-5-carboxylic acid, 9-[(3-carbamoylphenyl)methyl]-2-ethyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-carboxyphenyl)methyl]-2-ethyl-2,3,4,9-tetrahydro-1H-carbazole Lubazole-8-carboxylic acid, 5-[(3-carbamoylphenyl)methyl]-7-ethyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 5-[(3-cyanophenyl)methyl]-7-ethyl-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid, 9-[(3-cyanophenyl)methyl]-3-ethyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-carbamoylphenyl)methyl]-4-propyl-2,3,4,9-Tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-carbamoylphenyl)methyl]-3-propyl-2,3,4,9-Tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-cyanophenyl)methyl]-3-propyl-2,3,4,9-Tetrahydro-1H-carbazole-8-carboxylic acid, 4-Butyl-9-[(3-carbamoylphenyl)methyl]-2,3,4,9-Tetrahydro-1H-carbazole-8-carboxylic acid, 4-Butyl-9-[(3-cyanophenyl)methyl]-2,3,4,9- Tetrahydro-1H-carbazole-8-carboxylic acid, 3-butyl-9-[(3-carbamoylphenyl)methyl]-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 3-butyl-9-[(3-cyanophenyl)methyl]-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-carbamoylphenyl)methyl]-4-pentyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-cyanophenyl)methyl]-4-pentyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-cyanophenyl)methyl]-4-pentyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid Lahydro-1H-carbazole-8-carboxylic acid, 9-[(3-carbamoylphenyl)methyl]-3-pentyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 9-[(3-cyanophenyl)methyl]-3-pentyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid, 4-[(3-carbamoylphenyl)methyl]-3-propyl-1H,2H,3H,4H-cyclopenta[b]indole-5-carboxylic acid, 4-[(3-cyanophenyl)methyl]-3-propyl-1H,2H,3H , 4H-cyclopenta[b]indole-5-carboxylic acid, 2-({7-butyl-5-[(3-carbamoylphenyl)methyl]-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-yl}formamide)acetic acid, 2-({7-butyl-5-[(3-cyanophenyl)methyl]-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-yl}formamide)acetic acid, 7-butyl-5-[(3-carbamoylphenyl)methyl]-N-(2-hydroxyethyl)-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxamide, 7-Butyl-5-[(3-cyanophenyl)methyl]-N-(2-hydroxyethyl)-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxamide, 7-Butyl-5-[(3-fluorophenyl)methyl]-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, and 7-Butyl-5-[(3-carboxyphenyl)methyl]-5H,6H,7H,8H,9H,10H-Cyclohepta[b]indole-4-carboxylic acid, or pharmaceutically acceptable salts or stereoisomers thereof A compound selected from the group consisting of the following.

31. The compound according to claim 30, which is a pure optical isomer.

32. A method for inhibiting the fatty acid-binding protein FABP4 in a mammal, comprising administering an effective amount of the compound described in claim 1, 17, or 23 to the mammal.

33. The method according to claim 32, wherein the subject is a human being.

34. The compound according to claim 1, 17, or 23, for use in the prevention or treatment of disorders based on fatty acid-binding protein FABP4.

35. The compound according to claim 34, wherein the disorder is selected from type 2 diabetes, hyperglycemia, metabolic syndrome, obesity, atherosclerosis, intracranial atherosclerosis, non-alcoholic steatohepatitis, asthma, vascular dementia, multiple sclerosis, Alzheimer's disease, other chronic inflammatory and autoimmune / inflammatory diseases, chronic heart disease, polycystic ovary syndrome, pre-eclampsia, and cancer.

36. A pharmaceutical composition comprising the compound described in claim 1, 17, or 23 as an active ingredient, in combination with an acceptable diluent or carrier.

37. A pharmaceutical composition for use in the prevention or treatment of disorders based on fatty acid-binding protein FABP4.

38. The pharmaceutical composition according to claim 37, wherein the disorder is selected from type 2 diabetes, hyperglycemia, metabolic syndrome, obesity, atherosclerosis, intracranial atherosclerosis, non-alcoholic steatohepatitis, asthma, vascular dementia, multiple sclerosis, Alzheimer's disease, other chronic inflammatory and autoimmune / inflammatory diseases, chronic heart disease, polycystic ovary syndrome, pre-eclampsia, and cancer.

39. A pharmaceutical composition according to any one of claims 36 to 38, further comprising a drug having further therapeutic activity.

40. A method for preventing or treating a fatty acid-binding protein FABP4-based disorder, comprising administering an effective amount of the compound described in claim 1, 17, or 23 to a subject in need of such treatment.

41. The method according to claim 40, wherein the subject is a human being.

42. The method according to any one of claims 40 and 41, wherein the disorder is selected from type 2 diabetes, hyperglycemia, metabolic syndrome, obesity, atherosclerosis, intracranial atherosclerosis, non-alcoholic steatohepatitis, asthma, vascular dementia, multiple sclerosis, Alzheimer's disease, other chronic inflammatory and autoimmune / inflammatory diseases, chronic heart disease, polycystic ovary syndrome, pre-eclampsia, and cancer.

43. A method for inhibiting FABP4, comprising administering an effective amount of the compound described in claim 1, 17, or 23 to a subject in need of such treatment.

44. The method according to claim 43, wherein the subject is a human being.

45. Use of the compound according to claim 1, 17, or 23 for the production of a pharmaceutical product for use in the prevention or treatment of a fatty acid-binding protein FABP4 disorder.

46. The use according to claim 45, wherein the disorder is selected from type 2 diabetes, hyperglycemia, metabolic syndrome, obesity, atherosclerosis, intracranial atherosclerosis, non-alcoholic steatohepatitis, asthma, vascular dementia, multiple sclerosis, Alzheimer's disease, other chronic inflammatory and autoimmune / inflammatory diseases, chronic heart disease, polycystic ovary syndrome, pre-eclampsia, and cancer.

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