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US 2010/0168151 A1Published application
Novel processes for preparing 6-(difluoromethoxy)[1]benzofuro[3,2-c]pyridine-9-carbaldehyde, a novel intermediate for the synthesis of pde iv inhibitors
AssigneeGlenmark Pharmaceuticals S.A.
InventorsLaxmikant Atmaram Gharat, Jitendra Maganbhai Gajera, Sandip Damodar Patil, Suresh M. Kadam
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Abstract
The present invention relates to novel processes for preparing 6-(difluoromethoxy)[1] benzofuro[3,2-c]pyridine-9-carbaldehyde, which is a novel and useful intermediate for preparing compounds with PDE4 inhibitory activity, such as 3,5-dichloro-4-(6-difluoromethoxybenzo[4,5]furo[3,2-c]pyridin-9-ylcarboxamido)-1-pyridiniumolate.
Claims20
A process for preparing a compound of formula (10):
- or an N-oxide or a pharmaceutically acceptable salt thereof, wherein:
- R1 and R2 are independently hydrogen, alkyl, aryl, heteroaryl or heterocyclyl, or R1 and R2 together, with the nitrogen atom to which they are attached, form a 3-7 membered heterocyclyl optionally containing one or more heteroatoms selected from O, S and N;
- and
- P is selected from an optionally substituted benzyl, alkyl, halogenated alkyl, cycloalkyl, cycloalkylalkyl, silyl, allyl, propargyl, tetrahydropyran, alkoxyalkyl and silyloxyalkyl, the method comprising the steps of:
- (a) converting a compound of formula (5) to a compound of formula (6)
- and
- (b) converting a compound of formula (6) to a compound of formula (10) or an N-oxide or a pharmaceutically acceptable salt thereof.
4 more elements
A process for preparing a compound of formula (7)
- comprising deprotecting a compound of formula (5)
- wherein P is selected from an optionally substituted benzyl, alkyl, halogenated alkyl, cycloalkyl, cycloalkylalkyl, silyl, allyl, propargyl, tetrahydropyran, alkoxyalkyl and silyloxyalkyl.
A process for preparing a compound of formula (6),
- wherein P is selected from an optionally substituted benzyl, alkyl, halogenated alkyl, cycloalkyl, cycloalkylalkyl, silyl, allyl, propargyl, tetrahydropyran, alkoxyalkyl and silyloxyalkyl, wherein the process comprises the step of converting a compound of the formula (5) to form the compound of formula (6)
A pharmaceutical composition comprising:
- (a) a compound of the formula (10)
- an N-oxide or pharmaceutically acceptable salt thereof, wherein:
- P is selected from an optionally substituted benzyl, alkyl, halogenated alkyl, cycloalkyl, cycloalkylalkyl, silyl, allyl, propargyl, tetrahydropyran, alkoxyalkyl and silyloxyalkyl;
- and
- R1 and R2 are independently hydrogen, alkyl, aryl, heteroaryl or heterocyclyl, or R1 and R2 together, with the nitrogen atom to which they are attached, form a 3-7 membered heterocyclyl optionally containing one or more heteroatom(s) selected from O, S and N;
- and
- (b) a compound selected from
- or a salt thereof, wherein P is as defined above.
5 more elements
A compound selected from:
- or salts thereof,
- wherein:
- P is selected from an optionally substituted benzyl, alkyl, halogenated alkyl, cycloalkyl, cycloalkylalkyl, silyl, allyl, propargyl, tetrahydropyran, alkoxyalkyl or silyloxyalkyl.
Dependencies are inferred from the claim text.