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US 7,582,769 B2Granted
Dicycloalkyl urea glucokinase activators
AssigneeNovo Nordisk A/S
InventorsAnthony Murray, Jesper Lau, Per Vedso, Marit Kristiansen, Lone Jeppesen
Life of this patent
Estimating the term…
Abstract
Dicycloalkyl urea glucokinase activators compounds are glucokinase inhibitors useful for the treatment of diabetes. (I)
Claims11
A compound of formula (I)
- wherein R1 is
- and R2 is cyclohexyl;
- and
- A is
- and
- R5 is selected from the group consisting of C3-6-alkenyloxy, aryloxy-C1-6-alkyl, C3-8-cycloalkyl-C1-6-alkyloxy-C1-6-alkyl, aryl-C1-6-alkyloxy-C1-6-alkyl, heteroaryl-C1-6-alkyloxy-C1-6-alkyl, C3-6-alkenylthio, arylthio-C1-6-alkyl, C3-8-cycloalkyl-C1-6-alkylthio-C1-6-alkyl, or heteroaryloxy-C1-6-alkyl, each of which is optionally substituted with one or more substituents independently selected from R12, and wherein each aryl is phenyl and heteroaryl is pyridyl;
- and
- R12 is halogen, cyano, hydroxy, carboxy, —CF3, C1-6-alkyloxy, C3-8-cycloalkyloxy, aryloxy, aryl-C1-6-alkyloxy or C1-6-alkyl;
- and
- R8 is selected from halogen, carboxy, —CF3, —S—CH3, —S—CH2CH3, —S—CH2CH2CH3, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, —CH2—C(O)—O—CH3, —CH2—C(O)—O—CH2CH3, —CH2CH2—C(O)—O—CH3, —CH2CH2—C(O)—O—CH2CH3, —CH2—O—C(O)—CH3, —CH2—O—C(O)—CH2CH3, —CH2CH2—O—C(O)—CH3, —CH2CH2—O—C(O)—CH2CH3, —C(O)—O—CH3, —C(O)—O—CH2CH3, each of which is optionally substituted with one or more substituents independently selected from R16;
- or heteroarylthio, wherein heteroaryl is pyridyl or imidazolyl, each optionally substituted on the heteroaryl part with one or more substituents independently selected from R17 , or pyrrolidinyl, piperidyl, piperazinyl, or morpholinyl, each of which is optionally substituted with one or more substituents independently selected from R16;
- or —S(O)2—NR19R20 or —S(O)2—R21
- R16 and R17 are independently C1-6-alkyl, halogen, nitro, cyano, hydroxy, carboxy, oxo, —CF3, carboxy-C1-6-alkyl, hydroxy-C1-6-alkyl, —C1-6-alkyl-C(O)—O—C1-6-alkyl, —C1-6-alkyl-C(O)—NR19R20, —C(O)—O—C1-6-alkyl, —C(O)—C1-6-alkyl-C(O)—C1-6-alkyl, —NR19R20, —NHS(O)2C1-6-alkyl, —NHS(O)2CF3, —NHS(O)2CH2CF3, —C(O)NR19R20, —S(O)2C1-6-alkyl, —S(O)2CF3, —S(O)2CH2CF3 or —S(O)2NR19R20;
- and
- R19 and independently represent hydrogen, methyl, ethyl, or propyl, S(O)2—CH3, or R19 and R20 together with the nitrogen to which they are attached form a 3 to 8 membered heterocyclic ring with the said nitrogen atom, wherein the heterocyclic ring is pyrrolidyl, piperidyl, piperazinyl, homopiperazinyl, or morpholinyl, the heterocyclic ring is optionally substituted with one or more substituents independently selected from R24;
- and
- R21 is selected from carboxy-methyl, carboxy-ethyl, or carboxy-propyl;
- and
- R24 is halogen, carboxy, C1-6-alkyl, carboxy-C1-6-alkyl, or —C(O)—O—C1-6-alkyl;
- and
- as well as any salt hereof with a pharmaceutically acceptable acid or base, or any optical isomer or mixture of optical isomers, racemic mixture, or any tautomeric forms thereof.
18 more elements
Dependencies are inferred from the claim text.