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US 2014/0005392 A1Published application
Method for producing 2-(2-aminopyrimidin-4-yl)-1h-indole-5-carboxylic acid derivatives
AssigneeSanofi
InventorsJoachim GRAESER, Guenter BILLEN, Adolf LINKIES, Tobias METZENTHIN
Life of this patent
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Abstract
This disclosure relates to a novel process for obtaining a compound of formula I: wherein the values of R1, R2, and R3 and P are as described in the specification, and intermediates thereof.
Claims10
A compound of formula II
- or a physiologically compatible salt of the compound of the formula II, where
- R1 is
- a hydrogen atom,
- —(C1-C12)-alkyl,
- —(C6-C14)-aryl,
- —(C3-C8)-cycloalkyl or
- a 4- to 15-membered Het ring,
- with the proviso that R1 is not a hydrogen atom when P is a hydrogen atom and D is —N(R2)-R3 in which R2 is a hydrogen atom and R3 is —(C1-C4)-alkyl;
- P is
- a hydrogen atom;
- —C(O)—O—R6 in which R6 is:
- a hydrogen atom,
- —(C1-C12)-alkyl,
- —(C6-14)-aryl where aryl is unsubstituted or mono-, di- or tri-substituted by —(C1-C6)-alkyl,
- —(C3-C8)-cycloalkyl, or
- a 4- to 15-membered Het ring;
- —SO3—R6;
- —O—SO2—R6;
- —Si—R6;
- or
- benzyl;
- and
- D is
- —N(R2)-R3,
- halogen
- —O—SO2—R2 or
- —O—C(O)—R2,
- in which R2 and R3 are the same or different and are each independently
- a hydrogen atom,
- —(C1-C12)-alkyl,
- —(C6-14)-aryl where aryl is unsubstituted or mono-, di- or trisubstituted by —(C1-C6)-alkyl,
- —(C3-C6)-cycloalkyl or
- a 4- to 15-membered Het ring.
30 more elements
A compound of formula IV
- where
- R1 is
- a hydrogen atom,
- —(C1-C12)-alkyl,
- —(C6-C14)-aryl,
- —(C3-C6)-cycloalkyl or
- a 4- to 15-membered Het ring;
- R4 and R5 are the same or different and are each independently
- —OH,
- —O—(C1-C12)-alkyl,
- —O—(C6-C14)-aryl,
- —O—(C3-8)-cycloalkyl,
- —(C1-C12)-alkyl or
- —O-Het, where Het is a 4- to 15-membered Het ring;
- or
- R4 and R5, together with the boron atom to which they are bonded, form a ring having 4, 5, 6 or 7 carbon atoms in the ring and the ring may, instead of the particular carbon atoms, contain two oxygen atoms or two oxygen atoms and one nitrogen atom;
- P is a hydrogen atom;
- —C(O)—O—R6, where R6 is:
- a hydrogen atom,
- —(C1-C12)-alkyl,
- (C6-C14)-aryl where aryl is unsubstituted or mono-, di- or trisubstituted by —(C1-6)-alkyl, —(C3-C8)-cycloalkyl, or
- a 4- to 15-membered Het ring;
- —SO3—R6;
- —O—SO2—R6;
- —Si—R6;
- or
- benzyl;
- with the proviso that R4 and R5 are not —OH or —O—(C1-C12)-alkyl when P is —C(O)—O—(C1-C12)-alkyl.
25 more elements
A compound of the formula X
- where
- R1 is
- a hydrogen atom,
- —(C1-C12)-alkyl,
- —(C6-C14)-aryl,
- —(C3-C8)-cycloalkyl or
- a 4- to 15-membered Het ring;
- R2 and R3 are the same or different and are each independently
- a hydrogen atom,
- (C1-C12)-alkyl,
- —(C6-C14)-aryl where aryl is unsubstituted or mono-, di- or trisubstituted by —(C1-6)-alkyl,
- —(C3-C8)-cycloalkyl or
- a 4- to 15-membered Het ring.
10 more elements
A compound of formula XVI
- where
- R1 is
- a hydrogen atom,
- —(C1-C12)-alkyl,
- —(C6-C14)-aryl,
- —(C3-C8)-cycloalkyl or
- a 4- to 15-membered Het ring.
4 more elements
Dependencies are inferred from the claim text.