Substituted pyrroles

Claim 2

A compound of the formula ##STR8## wherein R 1 and R 3 together form a bond and R 2 is hydrogen or R 1 and R 2 together form a bond and R 3 is hydrogen; R 4 , R 5 , R 6 and R 7 each independently are hydrogen, halogen, C 1-7 alkyl, halo C 1-7 alkyl, C 1-7 alkoxy, nitro, amino, C 1-7 alkanoylamino, aroylamino, C 1-7 alkylthio or C 1-7 alkylsulfonyl; R 8 is hydrogen, C 1-7 alkyl or aryl C 1-7 alkyl; X is --N(R 9 )-- or --CHN(R 10 ,R 11 )-- in which R 9 , R 10 and R 11 each are hydrogen, C 1-7 alkyl, aryl C 1-7 alkyl or C 1-7 alkanoyl; m is 0-2 and n is 1-3, with the proviso that the sum of m and n is 1-3; p is 0-4 and q is 0-4, with the proviso that the sum of p and q is 2-4 when X is --N(R 9 )--, that the sum of p and q is 1-5 when X is --CHN(R 10 , R 11 )-- and R 1 and R 2 together form a bond, that the sum of p and q is 0-4 when X is --CHN(R 10 , R 11 )-- and R 1 and R 3 together form a bond, and that p is 1-4 when X is --N(R 9 )--, R 1 and R 3 together represent a bond and m is 0, or a pharmaceutically acceptable salt of an acidic compound of formula I with a base or of a basic compound of formula I with an acid.

Claim 3

A compound according to claim 1, wherein R 1 and R 3 together form a bond and R 2 is hydrogen, X is --N(R 9 )-- and m, n, p and q each are 1.

Claim 4

A compound according to claim 1, wherein R 1 and R 2 together form a bond and R 3 is hydrogen, X is --N(R 9 )--, m, n and q are 1 and p is 2.

Claim 5

A compound according to any one of claims 2, 3, or 1 wherein R 4 , R 5 , R 6 , and R 7 each are hydrogen.

Claim 6

A compound according to any one of claims 2, 3, 4 or 1, wherein R 8 is alkyl.

Claim 7

A compound according to claim 5, wherein R 8 is methyl.

Claim 8

A compound according to any one of claims 2, 3, 4, 5 or 1, wherein R 9 is hydrogen or C 1-7 alkyl.

Claim 9

A compound according to claim 7, wherein R 9 is hydrogen or methyl.

Claim 10

A compound according to claim 1, wherein R 10 and R 11 each are hydrogen or alkyl C 1-7 .

Claim 11

A compound according to claim 9, wherein R 10 and R 11 each are methyl.

Claim 12

A compound according to claim 1 selected from the group consisting of 3-[6,7,8,9-Tetrahydrospiro[pyrido[1,2-a]indole-8,3'-pyrrolidin]-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione, cis-3-[2,3,3a,4,11,11a-Hexahydro-2-methyl-1H-pyrrolo[3',4':4,5]pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione, trans-3-[2,3,3a,4,11,11a-Hexahydro-2-methyl-1H-pyrrolo[3',4':4,5]pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione.

Claim 13

A compound of the formula ##STR9## wherein R 1 and R 3 together form a bond and R 2 is hydrogen or R 1 and R 2 together form a bond and R 3 is hydrogen; R 4 , R 5 , R 6 and R 7 each independently are hydrogen, halogen, C 1-7 alkyl, halo C 1-7 alkyl, C 1-7 alkoxy, nitro, amino, C 1-7 alkanoylamino, aroylamino, C 1-7 alkylthio or C 1-7 alkylsulfonyl; R 8 is hydrogen, C 1-7 alkyl or aryl-C 1-7 -alkyl; m is 0-2 and n is 1-3, with the proviso that the sum of m and n is 1-3; p is 0-4 and q is 0-4, with the proviso that the sum of p and q is 2-4 when X' is --N(R 9' )--, that the sum of p and q is 1-5 when X' is --CHN(R 10' , 11'" )-- and R 1 and R 2 together form a bond, that the sum of p and q is 0-4 when X' is --CHN(R 10' ,R 11' )-- and R 1 and R 3 together form a bond, and that p is 1-4 when X' is --N(R 9' )--, R 1 and R 3 together represent a bond and m is O, X' is --N(R 9' )-- or --CHN(R 10' ,R 11' )-- in which R 9' , R 10' and R 11' each are hydrogen, C 1-7 alkyl, aryl-C 1-7 -alkyl, C 1-7 alkanoyl, alkoxycarbonyl or aryloxycarbonyl.

Claim 14

A compound of the formula ##STR9## wherein R 1 and R 3 together form a bond and R 2 is hydrogen or R 1 and R 2 together form a bond and R 3 is hydrogen; R 4 , R 5 , R 6 and R 7 each independently are hydrogen, halogen, C 1-7 alkyl, halo C 1-7 alkyl, C 1-7 alkoxy, nitro, amino, C 1-7 alkanoylamino, aroylamino, C 1-7 alkylthio or C 1-7 alkylsulfonyl; R 8 is hydrogen, C 1-7 alkyl or aryl-C 1-7 -alkyl; m is 0-2 and n is 1-3, with the proviso that the sum of m and n is 1-3; p is 0-4 and q is 0-4, with the proviso that the sum of p and q is 2-4 when X' is --N(R 9' )--, that the sum of p and q is 1-5 when X' is --CHN(R 10' , 11'" )-- and R 1 and R 2 together form a bond, that the sum of p and q is 0-4 when X' is --CHN(R 10' ,R 11' )-- and R 1 and R 3 together form a bond, and that p is 1-4 when X' is --N(R 9' )--, R 1 and R 3 together represent a bond and m is O, X' is --N(R 9' )-- or --CHN(R 10' ,R 11' )-- in which R 9' , R 10' and R 11' each are hydrogen, C 1-7 alkyl, aryl-C 1-7 -alkyl, C 1-7 alkanoyl, alkoxycarbonyl or aryloxycarbonyl.

Claim 15

A pharmaceutical composition comprising an effective amount of a compound of the formula ##STR10## wherein R 1 and R 3 together form a bond and R 2 is hydrogen or R 1 and R 2 together form a bond and R 3 is hydrogen; R 4 , R 5 , R 6 and R 7 each independently are hydrogen, halogen, C 1-7 alkyl, halo C 1-7 alkyl, C 1-7 alkoxy, nitro, amino, C 1-7 alkanoylamino, aroylamino, C 1-7 alkylthio or C 1-7 alkylsulfonyl; R 8 is hydrogen, C 1-7 alkyl or aryl C 1-7 alkyl; X is --N(R 9 )-- or --CHN(R 10 ,R 11 )-- in which R 9 , R 10 and R 11 each are hydrogen, C 1-7 alkyl, aryl C 1-7 alkyl or C 1-7 alkanoyl; m is 0-2 and n is 1-3, with the proviso that the sum of m and n is 1-3; p is 0-4 and q is 0-4, with the proviso that the sum of p and q is 2-4 when X is --N(R 9 )--, that the sum of p and q is 1-5 when X is --CHN(R 10 ,R 11 )-- and R 1 and R 2 together form a bond, that the sum of p and q is 0-4 when X is --CHN(R 10 ,R 11 )-- and R 1 and R 3 together form a bond, and that p is 1-4 when X is --N(R 9 )--, R 1 and R 3 together represent a bond and m is 0, or a pharmaceutically acceptable salt of an acidic compound of formula I with a base or a basic compound of formula I with an acid, and a therapeutically inert carrier.

Claim 16

A pharmaceutical composition comprising an effective amount of a compound of the formula ##STR10## wherein R 1 and R 3 together form a bond and R 2 is hydrogen or R 1 and R 2 together form a bond and R 3 is hydrogen; R 4 , R 5 , R 6 and R 7 each independently are hydrogen, halogen, C 1-7 alkyl, halo C 1-7 alkyl, C 1-7 alkoxy, nitro, amino, C 1-7 alkanoylamino, aroylamino, C 1-7 alkylthio or C 1-7 alkylsulfonyl; R 8 is hydrogen, C 1-7 alkyl or aryl C 1-7 alkyl; X is --N(R 9 )-- or --CHN(R 10 ,R 11 )-- in which R 9 , R 10 and R 11 each are hydrogen, C 1-7 alkyl, aryl C 1-7 alkyl or C 1-7 alkanoyl; m is 0-2 and n is 1-3, with the proviso that the sum of m and n is 1-3; p is 0-4 and q is 0-4, with the proviso that the sum of p and q is 2-4 when X is --N(R 9 )--, that the sum of p and q is 1-5 when X is --CHN(R 10 ,R 11 )-- and R 1 and R 2 together form a bond, that the sum of p and q is 0-4 when X is --CHN(R 10 ,R 11 )-- and R 1 and R 3 together form a bond, and that p is 1-4 when X is --N(R 9 )--, R 1 and R 3 together represent a bond and m is 0, or a pharmaceutically acceptable salt of an acidic compound of formula I with a base or a basic compound of formula I with an acid, and a therapeutically inert carrier.

Claim 17

A pharmaceutical composition according to claim 13, wherein R 1 and R 3 together form a bond and R 2 is hydrogen, X is --N(R 9 )-- and m, n, p and q each are 1.

Claim 18

A pharmaceutical composition according to claim 13, wherein R 1 and R 2 together form a bond and R 3 is hydrogen, X is --N(R 9 )--, m, n and q are 1 and p is 2.

Claim 19

A pharmaceutical composition according to claim 13, wherein R 4 , R 5 , R 6 , and R 7 each are hydrogen.

Claim 20

A pharmaceutical composition according to claim 13, wherein R 8 is alkyl C 1-7 .

Claim 21

A pharmaceutical composition according to claim 17, wherein R 8 is methyl.

Claim 22

A pharmaceutical composition according to claim 13, wherein R 9 is hydrogen or alkyl C 1-7 .

Claim 23

A pharmaceutical composition according to claim 19, wherein R 9 is hydrogen or methyl.

Claim 24

A pharmaceutical composition according to claim 13, wherein R 10 and R 11 each are hydrogen or alkyl C 1-7 .

Claim 25

A pharmaceutical composition according to claim 21, wherein R 10 and R 11 each are methyl.

Claim 26

A pharmaceutical composition according to claim 13, wherein the compound of formula I is selected from the group consisting of 3-[6,7,8,9-Tetrahydrospiro[pyrido[1,2-a]indole-8,3'-pyrrolidin]-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione, cis-3-[2,3,3a,4,11,11a-Hexahydro-2-methyl-1H-pyrrolo[3',4':4,5]pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione, and trans-3-[2,3,3a,4,11,11a-Hexahydro-2-methyl-1H-pyrrolo[3',4':4,5]pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione.

Claim 27

The compound, trans-3-[2,3,3a,4,11,11a-Hexahydro-2-methyl-1H-pyrrolo[3',4':4,5]pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione.

Claim 28

The compound, trans-3-[2,3,3a,4,11,11a-Hexahydro-2-methyl-1H-pyrrolo[3',4':4,5]pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione.