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US 7,244,845 B2Granted
Process for preparing cyclic N-substituted alpha-imino carboxylic acids
AssigneeSanofi-Aventis Deutschland GmbH
InventorGerrit Schubert
Life of this patent
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Abstract
The present invention relates to the novel methods of making matrix metalloproteinase inhibitors of Formula (I):
Claims23
A process for preparing a compound of Formula (I):
- and/or all stereoisomeric forms of the compound of the Formula (I) and/or mixtures of these forms in any ratio, and/or a physiologically tolerated salt of the compound of the Formula (I), wherein:
- R1 is —(C1–C10)-alkyl where alkyl is linear or branched;
- or —(C2–C10)-alkenyl where alkenyl is linear or branched;
- or —(C2–C10)-alkynyl where alkynyl is linear or branched;
- or —(C1–C4)-alkylphenyl;
- or —(C1–C4)-alkyl-(C3–C7)-cycloalkyl;
- or —(C3–C7)-cycloalkyl;
- or —CH2CF3;
- and
- Q is a radical selected from
- wherein R2 is —(C1–C4)-alkyl, and a is 0, 1, 2, or 3;
- wherein said process comprises
- a) reacting a heterocyclic carboxylic acid of Formula (V)
- where Q is as defined in Formula (I), with a silylating reagent;
- and
- b) reacting the product of step a) with chlorosulfonylbiphenylcarbamate of Formula (IV)
- where R1 is as defined in Formula (I).
14 more elements
A compound of Formula (III)
- wherein:
- R1 is —(C1–C10)-alkyl where alkyl is linear or branched, or —(C2–C10)-alkenyl where alkenyl is linear or branched, or —(C2–C10)-alkynyl where alkynyl is linear or branched, or —(C1–C4)-alkylphenyl, or —(C1–C4)-alkyl-(C3–C7)-cycloalkyl, —(C3–C7)-cycloalkyl or —CH2CF3;
- and
- X is Li, Na, K, Rb, and Cs.
1 more element
A Compound of the Formula IV
- wherein:
- R1 is —(C1–C10)-alkyl where alkyl is linear or branched, or —(C2–C10)-alkenyl where alkenyl is linear or branched, —(C2–C10)-alkynyl where alkynyl is linear or branched, —(C1–C4)-alkylphenyl, —(C1–C4)-alkyl-(C3–C7)-cycloalkyl, —(C3–C7)-cycloalkyl or —CH2CF3.
Dependencies are inferred from the claim text.