N-substituted anilines

Details N-substituted anilines N-substituted anilines

C - Chemistry, Metallurgy

07

C

C07C 229/42 (2006.01) A61K 31/195 (2006.01) A61K 31/225 (2006.01) A61K 31/435 (2006.01) C07C 229/18 (2006.01) C07C 229/60 (2006.01) C07C 229/64 (2006.01) C07C 233/43 (2006.01) C07C 237/30 (2006.01) C07C 237/38 (2006.01) C07C 271/44 (2006.01) C07C 275/42 (2006.01) C07C 311/09 (2006.01) C07C 317/22 (2006.01) C07C 317/36 (2006.01) C07C 317/44 (2006.01) C07C 317/48 (2006.01) C07C 323/36 (2006.01) C07C 323/63 (2006.01) C07D 213/65 (2006.01) C07D 215/14 (2006.01) C07F 9/38 (2006.01) C07F 9/40 (2006.01)

Patent

CA 2099294

ABSTRACT Compounds of the formula Image 1 wherein R1 is hydrogen or -(CH2)mCOOR2; R2 is hydrogen, (R6)2N(CH2)2-, R6COOCH2- or -CH2CON(CH2CH2OH)2; R3 is hydrogen, nitro, hydroxy, amino, CH3(CH2)nS(O)0-2-, CH3(CH2)n- , CH3(CH2)nO- ,R5COO-, R5OOC- ,R5HNCOO-, R5NHCO-, R5CONH-, R5NHCONH-, [CH3(CH2)n]2NCO- , CH3(CH2)nCHOHCH2O-, (2-quinolinyl)methoxy, oleyloxy, linoleyloxy, R8OOC(CH2)tO-, (R6O)2PO(CH2)pO-, (HO) (R6O)PO(CH2)pO-, R6[O(CH2)2]qO-, R7(CH2)pO-, or -O(CH2)p-pyridinium+(OH-); R4 is CH3(CH2)n- , CH3(CH2)nO-, CF3SO2NH-, R5COO-, R5OOC- ,R5HNCOO-, R5NHCO-, R5CONH- R5NHCONH-, [CH3(CH2)n]2NCO-, CH3(CH2)nCHOHCH2O-, carboxy, (2-quinolinyl)methoxy, oleyloxy, linoleyloxy, R8OOC(CH2)tO-, R6[O(CH2)2]qO-, or R7(CH2)pO-; R5 is CH3(CH2)n-, 1-adamantyl or diphenylmethyl; R6 is lower alkyl; R7 is 1- or 2 -naphthyloxy, 1- 2- or 3-pyridinyloxy, 2,3- or 3,4- dihydroxyphenyl, 6,7-dihydroxy-2-naphthyl, phenyl, phenoxy or substituted phenyl or phenoxy, wherein the substituent is selected from the-group consisting of lower alkyl, lower alkoxy, hydroxy, nitro, amino, halo, R6 S(O)0-2-, carboxy, carboxy-lower alkyl or phenyl; R8 is hydrogen or lower alkyl; n is an integer from 0 to 17; m is an integer from 1 to 3; t is an integer from 1 to 10; p is an integer from 2 to 18, and q is an integer from 1 to 6; and when R2 is hydrogen, a pharmaceutically acceptable salt thereof with a base, are potent inhibitors of phospholipases A2 (PLA2's) and are therefore useful in the treatment of inflammatory diseases, such as psosiasis, inflammatory bowel disease, asthma, allergy, arthritis, dermatitis, gout, pulmonary disease, myocardial ischemia/reperfusion, and trauma induced inflammation, such as spinal cord injury.

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