Substituted 2-carboxylindoles having pharmaceutical activity

Claim 1

A compound of the formula ##STR16## or a pharmaceutically acceptable base or acid addition salt thereof; wherein (1) Y is (a) OH; (b) OR 30 wherein R 30 is lower alkyl, phenyl, phenylalkyl wherein the alkyl is an alkylene of from one to four carbons and the phenyl is unsubstituted or substituted by from one to three substituents selected from lower alkyl, halogen, trifluoromethyl, nitro, amino, mono- or di-lower alkylamino, hydroxy, lower alkoxy, C(O)OH, and NHCOR 5 wherein R 5 is lower alkyl, lower alkenyl, phenyl, phenylloweralkyl, phenylloweralkenyl or where the phenyl is substituted as defined above; (c) NR 40 R 50 wherein R 40 and R 50 are independently hydrogen or lower alkyl; or (d) OCH 2 OR 30 wherein R 30 is as defined above; (2) R 1 , R 2 , R 3 , and R 4 are independently hydrogen, lower alkyl, halogen, trifluoromethyl, cyano, nitro, methylthio, lower alkenyl, lower alkynyl, SO 2 NH 2 , S(O) 1-2 R wherein R is hydrogen or lower alkyl, OCF 3 ; (3) A is --(CH 2 ) n --, --(CH 2 ) q CH═CH(CH 2 ) p --, ##STR17## wherein R 11 and R 13 are independently as defined below and n is an integer of 0 through 4, q is an integer of 0 or 1, p is an integer of 1 or 2; (4) R 5 is hydrogen, alkyl of from one to twenty carbons, phenyl or phenyl substituted as defined above; (5) R 6 is (a) CONR 8 R 9 , (b) COOR 8 , (c) CSR 8 , (d) S(O) 1-2 R 8 , (e) S(O) 1-2 NR 8 R 9 , or (f) CONR 8 S(O) 1-2 R 9 , wherein R 8 and R 9 are independently (i) hydrogen; (ii) alkyl of from one to twenty carbons, or alkenyl of from one to twenty carbons; (iii) (C 3 -C 6 ) cycloalkyl or (C 3 -C 6 ) cycloalkylloweralkyl; (iv) phenyl or phenyl substituted by one to three of lower alkyl, halogen, trifluoromethyl, nitro, amino, mono- or di-lower alkylamino, hydroxy, lower alkoxy, C(O)OH, NHCOR 10 wherein R 10 is lower alkyl, lower alkenyl, phenyl, phenylloweralkyl, phenylloweralkenyl, or where the phenyl is substituted as defined above, NHSO 2 R 10 wherein R 10 is as defined above, CN, CONR 10 R 11 wherein R 10 is as defined above and R 11 is hydrogen or lower alkyl, or S(O) 0-2 R 10 wherein R 10 is as defined herein; (v) phenylloweralkyl or where the phenyl is substituted as defined above; (vi) phenylloweralkenyl or where the phenyl is substituted as defined above; (vii) (CH 2 ) q R 12 wherein q is an integer of one to four and R 12 is (A) SO 3 R 13 wherein R 13 is hydrogen or lower alkyl, (B) PO 3 R 13 wherein R 13 is as defined above, (C) CO 2 R 13 wherein R 13 is as defined above, or (D) NR 14 R 15 wherein R 14 and R 15 are independently hydrogen or alkyl; or (6) R 5 and R 6 are taken together with N which form ##STR18## wherein m is an integer one or two and R 16 is lower alkyl, phenyl, phenylloweralkyl or where the phenyl is substituted as defined above.