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US 2007/0191608 A1Published application
Process for preparing 3-aminothienopyridone derivatives
AssigneeCelltech R&D Limited
InventorsGraham Evans, Ian Smith, Neil Tremayne, Leighton Jones, Marianne Langston
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Abstract
This invention provides a class of 3-amino-7H-thieno[2,3-b]pyridin-6-one derivatives, substituted in the 7-position by an aryl, heteroaryl, cycloalkyl or heterocycloalkyl moiety, and in the 2-position by a specified range of substituent groups; also provided is a process for preparing those compounds, and the use thereof as intermediates in the manufacture of certain p38 MAP kinase inhibitors.
Claims22
A compound of formula (2):
- wherein
- R is a —CN, —NO2, —CO2Alk2, —COC1-6alkyl or —CONHet2 group;
- Alk2 is an optionally substituted alkyl, arylalkyl, aryl, aryloxyalkyl, alkanoyloxyalkyl or aroyloxyalkyl group;
- NHet2 is an optionally substituted 4- to 6-membered heterocycloalkyl group attached through a nitrogen atom to the group —CO;
- R1 is an optionally substituted aryl, heteroaryl, cycloalkyl or heterocycloalkyl group;
- and
- each Ry, which may be the same or different, is each a hydrogen atom or a hydrogen atom precursor;
- or a salt, solvate, hydrate, protected derivative, or N-oxide thereof.
5 more elements
(canceled)
A process for the manufacture of a halide of formula (1):
- wherein
- R is a —CN, —NO2, —CO2Alk2, —COC1-6alkyl or —CONHet2 group;
- Alk2 is an optionally substituted alkyl, arylalkyl, aryl, aryloxyalkyl, alkanoyloxyalkyl or aroyloxyalkyl group;
- NHet2 is an optionally substituted 4- to 6-membered heterocycloalkyl group attached through a nitrogen atom to the group —CO;
- R1 is an optionally substituted aryl, heteroaryl, cycloalkyl or heterocycloalkyl group;
- each Ry, which may be the same or different, is a hydrogen atom or a hydrogen atom precursor;
- and
- T is a halogen atom;
- which comprises diazotization of a compound of formula (2):
- followed by halide displacement.
7 more elements
A process for the manufacture of a compound of formula (1A):
- wherein
- R is a —CN, —NO2, —CO2Alk2, —COC1-6alkyl or —CONHet2 group;
- Alk2 is an optionally substituted alkyl, arylalkyl, aryl, aryloxyalkyl, alkanoyloxyalkyl or aroyloxyalkyl group;
- NHet2 is an optionally substituted 4- to 6-membered heterocycloalkyl group attached through a nitrogen atom to the group —CO;
- R1 is an optionally substituted aryl, heteroaryl, cycloalkyl or heterocycloalkyl group;
- each Ry, which may be the same or different, is a hydrogen atom or a hydrogen atom precursor;
- and
- Ar is an optionally substituted aromatic or heteroaromatic group;
- which comprises reacting a compound of formula (2):
- with a compound ArQ,
- wherein Q is a leaving group, in the presence of a transition metal catalyst.
8 more elements
A process for the manufacture of a compound of formula (2):
- wherein
- R is a —CN, —NO2, —CO2Alk2, —COC1-6alkyl or —CONHet2 group;
- Alk2 is an optionally substituted alkyl, arylalkyl, aryl, aryloxyalkyl, alkanoyloxyalkyl or aroyloxyalkyl group;
- NHet2 is an optionally substituted 4- to 6-membered heterocycloalkyl group attached through a nitrogen atom to the group —CO;
- R1 is an optionally substituted aryl, heteroaryl, cycloalkyl or heterocycloalkyl group;
- each Ry, which may be the same or different, is a hydrogen atom or a hydrogen atom precursor;
- which comprises the steps of:
- a) reacting a compound of formula (2a) or (2b):
- wherein
- Rc is an optionally substituted alkyl group, and
- W is a hydrogen atom, a metal ion or an amine salt;
- with a compound of formula (3):
- b) followed by reaction with a compound of formula (5):
- wherein Z is a leaving group.
11 more elements
A compound of formula (4):
- wherein
- R1 is an optionally substituted aryl, heteroaryl, cycloalkyl or heterocycloalkyl group;
- each Ry, which may be the same or different, is a hydrogen atom or a hydrogen atom precursor;
- and
- W is a hydrogen atom, a metal ion or an amine salt.
2 more elements
A compound of formula (6):
- wherein
- R is a —CN, —NO2, —CO2Alk2, —COC1-6alkyl or —CONHet2 group;
- Alk2 is an optionally substituted alkyl, arylalkyl, aryl, aryloxyalkyl, alkanoyloxyalkyl or aroyloxyalkyl group;
- NHet2 is an optionally substituted 4- to 6-membered heterocycloalkyl group attached through a nitrogen atom to the group —CO;
- R1 is an optionally substituted aryl, heteroaryl, cycloalkyl or heterocycloalkyl group;
- and
- each Ry, which may be the same or different, is a hydrogen atom or a hydrogen atom precursor.
4 more elements
Dependencies are inferred from the claim text.