Process for preparing indane carboxylate and cyclopentano [6] pyridine derivatives

A process for the preparation of a compound of Formula (19),

• wherein three of A, B, C and D are carbon atoms and one is a nitrogen atom;
• R1 is
• where R3 and R4 are independently H, OH, protected OH, C1-8alkoxy, Br, F, I, Cl, CF3 or C1-6alkyl and R5 is —OCH2CO2H;
• R2 is
• where R3 and R4 are as indicated above and Z is H, OH, or C1-5alkoxy;
• or a pharmaceutically acceptable salt thereof, wherein said method comprises converting a compound of Formula (13),
• wherein three of A, B, C and D are carbon atoms and one is a nitrogen atom;
• R3 and R4 are independently H, OH, protected OH, C1-8alkoxy, Br, F, I, Cl, CF3 or C1-6alkyl;
• and R is H, OH, C1-5alkoxy or a protected oxy group into the compound of Formula (19), and thereafter optionally forming a pharmaceutically acceptable salt thereof.

A process for the preparation of a compound of Formula (19),

• wherein three of A, B, C and D are carbon atoms and one is a nitrogen atom;
• R1 is
• where R3 and R4 are independently H, OH, protected OH, C1-8alkoxy, Br, F, I, Cl, CF3 or C1-6alkyl and R5 is —OCH2CO2H;
• R2 is
• where R3 and R4 are as indicated above and Z is H, OH, or C1-5alkoxy;
• or a pharmaceutically acceptable salt thereof, wherein said method comprises converting a compound of Formula (16),
• wherein three of A, B, C and D are carbon atoms and one is a nitrogen atom;
• R3 and R4 are independently H, OH, protected OH, C1-8alkoxy, Br, F, I, Cl, CF3 or C1-6alkyl, R is H, OH, C1-5alkoxy or a protected oxy group and Xc is a chiral auxiliary group;
• into the compound of Formula (19), and thereafter optionally forming a pharmaceutically acceptable salt thereof.

A process for the preparation of a compound of Formula (19),

• wherein three of A, B, C and D are carbon atoms and one is a nitrogen atom;
• R1 is
• where R3 and R4 are independently H, OH, protected OH, C1-8alkoxy, Br, F, I, Cl, CF3 or C1-6alkyl and R5 is —OCH2CO2H;
• R2 is
• where R3 and R4 are as indicated above and Z is H, OH, or C1-5alkoxy;
• or a pharmaceutically acceptable salt thereof, wherein said method comprises converting a compound of Formula (25),
• wherein three of A, B, C and D are carbon atoms and one is a nitrogen atom;
• R3 and R4 are independently H, OH, protected OH, C1-8alkoxy, Br, F, I, Cl, CF3 or C1-6alkyl;
• R is H, OH, C1-5alkoxy or a protected oxy group and Xc is a chiral auxiliary group;
• into the compound of Formula (19), and thereafter optionally forming a pharmaceutically acceptable salt thereof.