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Claims for Patent: 3,896,145

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Claims for Patent: 3,896,145

Title: Carbazoles
Abstract:Carbazoles prepared, inter alia, from the corresponding phenyl hydrazines and corresponding cyclohexanones are described. The carbazoles of the invention are useful anti-inflammatory, analgesic and anti-rheumatic agents.
Inventor(s): Berger; Leo (Montclair, NJ), Corraz; Alfred John (Wayne, NJ)
Assignee: Hoffmann-La Roche Inc. (Nutley, NJ)
Application Number:05/361,103
Patent Claims: 1. A compound of the formula ##SPC23##

wherein R is hydrogen, halogen, hydroxy, cyano, lower alkyl, hydroxy-lower alkyl, lower alkoxy, acetyl, benzyloxy, lower alkylthio, trifuloromethyl, carboxy, carbo-lower alkoxy, nitro, amino, mono-lower alkylamino, di-lower alkylamino, sulfamoyl, di-lower alkylsulfamoyl or difluoromethylsulfonyl; R.sub.1 is halogen, cyano, hydroxy-lower alkyl, lower alkoxy, acetyl, acetamido, benzyloxy, lower alkylthio, trifluoromethyl, hydroxy, carboxy, carbo-lower alkoxy, nitro, amino, mono-lower alkylamino, di-lower alkylamino, sulfamoyl, di-lower alkylsulfamoyl or difluoromethylsulfonyl; or R taken together with an adjacent R.sub.1 is also lower alkylenedioxy; R.sub.2 is ##SPC24##

wherein A is hydroxy, lower alkoxy, amino-lower alkoxy, mono-lower alkylamino-lower alkoxy or di-lower alkylamino-lower alkoxy, X and Y, independently, are hydrogen or lower alkyl, and m is 1 to 7, or R.sub.2 is ##SPC25##

wherein B is hydroxy, lower alkoxy, amino, hydroxyamino, mono-lower alkylamino, di-lower alkylamino, amino-lower alkoxy, mono-lower alkylamino-lower alkoxy or di-lower alkylamino-lower alkoxy, Y and X, independently, are hydrogen or lower alkyl, and n is 1 to 7 and R.sub.3 is hydrogen, lower alkyl, lower alkoxycarbonyl-lower alkyl, carboxy-lower alkyl, lower alkanoyl, halo-substituted lower alkanoyl, benzyl, halo-benzyl, benzoyl or halo-benzoyl; and

when X and Y are different, their enantiomers; when R or R.sub.1 is carboxy and/or when B is hydroxy, salts thereof with pharmaceutically acceptable bases; and when R or R.sub.1 is amino, mono-lower alkylamino or di-lower alkylamino, and/or when B or A is amino-lower alkoxy, mono-lower alkylamino-lower alkoxy or di-lower alkylamino-lower alkoxy, addition salts thereof with pharmaceutically acceptable acids.

2. A compound of the formula ##SPC26##

wherein R is hydrogen, R.sub.1 is halogen, lower alkoxy, trifluoromethyl or di-lower alkylamino; R.sub.2 is ##SPC27##

wherein B is hydroxy, lower alkoxy, amino, hydroxyamino, mono-lower alkylamino, di-lower alkylamino, amino-lower alkoxy, mono-lower alkylamino-lower alkoxy or di-lower alkylamino-lower alkoxy; R.sub.3 is hydrogen or lower alkyl; Y and X, independently, are hydrogen or lower alkyl and n is 1 to 7;

and when X and Y are different, their enantiomers; when B is hydroxy, salts thereof with pharmaceutically acceptable bases; and when R.sub.1 is di-lower alkylamino, and/or B is amino-lower alkoxy, mono-lower alkylamino-lower alkoxy or di-lower alkylamino-lower alkoxy, addition salts thereof with pharmaceutically acceptable acids.

3. A compound in accordance with claim 2, wherein n is 1.

4. A compound in accordance with claim 3, wherein B is hydroxy.

5. A compound in accordance with claim 1, wherein R.sub.1 is chloro.

6. A compound in accordance with claim 5, racemic 6-chloro-.alpha.-methyl-carbazole-2-acetic acid.

7. A compound in accordance with claim 6, (+) 6-chloro-.alpha.-methyl-carbazole-2-acetic acid.

8. A compound in accordance with claim 6, (-) 6-chloro-.alpha.-methyl-carbazole-2-acetic acid.

9. A compound in accordance with claim 5, 6-chloro-carbazole-2-acetic acid.

10. A compound in accordance with claim 5, 6-chloro-9-methyl-carbazole-1-acetic acid.

11. A compound of the formula ##SPC28##

wherein R is hydrogen, R.sub.1 is halogen, R.sub.2 is ##SPC29##

wherein

A is hydroxy or lower alkoxy; X and Y, independently, are hydrogen or lower alkyl, m is 1 to 7, and R.sub.3 is hydrogen,

and when X and Y are different, their enantiomers.

12. A compound in accordance with claim 11, wherein m is 1.

13. A compound in accordance with claim 12, wherein A is hydroxy.

14. A compound in accordance with claim 13, wherein R.sub.1 is chloro.

15. A compound in accordance with claim 14, racemic 2-(6-chloro-2-carbazolyl)-propanol.

16. A compound in accordance with claim 15, (+) 2-(6-chloro-2-carbazolyl)propanol.

17. A compound in accordance with claim 15, (-) 2-(6-chloro-2-carbazolyl)propanol.

18. A compound of the formula ##SPC30##

wherein R is hydrogen; R.sub.1 is halogen; R.sub.2 is ##SPC31##

wherein

B is hydroxy, lower alkoxy, amino, hydroxyamino, mono-lower alkylamino, di-lower alkylamino, amino-lower alkoxy, mono-lower alkylamino-lower alkoxy or di-lower alkylamino-lower alkoxy; Y and X, independently, are hydrogen or lower alkyl; n is 1 to 7, and R.sub.3 is hydrogen;

and when X and Y are different, their enantiomers; when B is hydroxy, salts thereof with pharmaceutically acceptable bases; and when B is amino-lower alkoxy, mono-lower alkylamino-lower alkoxy or di-lower alkylamino-lower alkoxy, addition salts thereof with pharmaceutically acceptable acids.

19. A compound in accordance with claim 2, 6-chloro-.alpha.-methyl-carbazole-2-acetic acid ethyl ester.

20. A compound in accordance with claim 2, 6-chloro-.alpha.-methyl-carbazole-2-acetic acid-2-dimethylamino ethyl ester.
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