Indoles as respiratory syncytial virus antiviral agents

A process for preparing a compound of formula I, said process comprising

• coupling a compound of formula II with a compound of formula III
• wherein Y is selected from the group consisting of OH, halogen and sulfonate;
• each X is independently C or N;
• each R1 is independently selected from the group consisting of hydrogen, halogen, C1-C6alkyl, C3-C7cycloalkyl, C1-C6alkoxy, N(R6)2, CO(R7), CH2NH2, CH2OH, CN, C(═NOH)NH2, C(═NOCH3)NH2, C(═NH)NH2, CF3, OCF3, B(OH)2 and B(O—C1-C6alkyl)2;
• R2 is selected from the group consisting of hydrogen, halogen, C1-C6alkyl, C3-C7cycloalkyl, C1-C6alkoxy, and CO(R7);
• R3 is —(CR8R9)n—R10;
• R4 is selected from the group consisting of hydrogen, C1-C10alkyl, C3-C7cycloalkyl, C2-C10alkenyl, SO2-R8, CH2CF3, SO2CH3 or a 4 to 6 membered saturated ring containing an oxygen atom;
• each R5 is independently selected from the group consisting of hydrogen, C1-C6alkyl, C3-C7cycloalkyl, C1-C6alkoxy, CO(R7), CF3 and halogen, wherein R5 is absent if X is N;
• R6 is selected from the group consisting of hydrogen, C1-C6alkyl, COOCH3, and CONHSO2CH3;
• R7 is selected from the group consisting of OH, O(C1-C6alkyl), NH2, NHSO2N(C1-C6alkyl)2, NHSO2NHCH3, NHSO2(C1-C6alkyl), NHSO2(C3-C7cycloalkyl), N(C1-C6-alkyl)2, NR8R9, and NR9R10;
• n is an integer from 2 to 6;
• R8 and R9 are each independently selected from the group consisting of hydrogen, C1-C10alkyl, C3-C7cycloalkyl, and R8 and R9 taken together form a 4 to 6 membered aliphatic ring optionally containing one or more heteroatoms selected from the group consisting of N, S, and O;
• and
• R10 is selected from the group consisting of hydrogen, C1-C6alkyl, OH, CN, F, CF2H, CF3, C(═NOH)NH2, CONR8R9, COOR8, CONR8SO2R9, CON(R8)SO2N(R8R9), NR8R9, NR8COOR9, OCOR8, NR8SO2R9, SO2NR8R9, SO2R8, and a 4 to 6 membered saturated ring containing an oxygen atom.

A compound having the structure of formula II:

• wherein each R1 is independently H or Cl;
• R2 is H;
• R3 is —CR8R9)nR10 wherein R8 and R9 are H, n is 2-4, and R10 is SO2R8, wherein R8 is methyl;
• and Y is selected from the group consisting of OH, halogen, and SO3C1-4alkyl.

A process for preparing a compound of formula I, said process comprising coupling a compound of formula II with a compound of formula III

• wherein:
• R1 is independently H or Cl;
• R2 is H;
• R3 is —(CR8R9)n—R10, wherein R8 and R9 are H;
• n is 2-4, and R10 is SO2R8, wherein R8 is methyl;
• R4 is C3-C7cycloalkyl or CH2CF3;
• X in para position to N-R4 is N, and R5 on said X is absent, and all other X-R5 members are CH;
• and
• Y is selected from the group consisting of OH, halogen and SO3C1-4alkyl.