Phthalazine-containing antidiabetic compounds

A compound of formula

• or a pharmaceutically acceptable salt thereof,
• wherein:
• G is a N—N containing heteroaryl group G selected from the group consisting of
• which is optionally substituted by at least one R2;
• L is —O—, —C(O)—, —S(O)q—, —N(R3)—;
• X is —O—, —C(O)—, —S(O)q, —C(Ra)(Rb)— or —N(R8)-;
• Y is —[C(Ra)(Rb)]n—O—[C(Ra)(Rb)]n, —[C(Ra)(Rb)]n-C(O)-[C(Ra)(Rb)]n, —[C(Ra)(Rb)]n-S(O)q-[C(Ra)(Rb)]n—, —[C(Ra)(Rb)]m— or —N(R8)-,
• provided that when X is —O—, Y cannot be —O—[C(Ra)(Rb)]n—;
• R is a group selected from the group consisting of
• (i)
• (ii)
• (iii)
• (iv)
• (v)
• tetrazolyl;
• and
• (vii)
• wherein
• Q is —CH— or —N—, and
• J is —S—, —CH2-, —O— or N(R8)-;
• Ra is independently selected from the group consisting of H, —OH, halo, alkoxy, cycloalkyl, and cycloalkylalkyl;
• Rb is independently selected from the group consisting of H, —OH, halo, alkoxy, cycloalkyl, and cycloalkylalkyl;
• R1 is independently selected from the group consisting of H, halogen, —SF5, —CN, —NO2, —N(R6)(R7), —OH, alkyl, alkoxy, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, and —S(O)q-alkyl, wherein said alkyl, alkoxy, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, and cycloalkylalkoxy are optionally substituted with one or more groups selected from the group consisting of —OH, halo, alkyl, —S(O)q-alkyl, haloalkyl, alkoxy, haloalkoxy, and cycloalkyl;
• R2 is independently selected from the group consisting of halogen, —CN, —NO2, —N(R6)(R7), OH, alkyl, alkoxy, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, aryl, arylalkyl, heteroaryl, heteroarylalkyl and —S(O)q-alkyl, wherein said alkyl, alkoxy, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, aryl, arylalkyl, heteroaryl, and heteroarylalkyl are optionally substituted with one or more groups selected from the group consisting of —OH, halo, alkyl, —S(O)q-alkyl, haloalkyl, alkoxy, haloalkoxy, and cycloalkyl;
• R3 is independently selected from the group consisting of H, alkyl and haloalkyl;
• R4 is independently selected from the group consisting of H, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocycloalkyl, heterocycloalkylalkyl, heteroaryl, and heteroarylalkyl;
• R5 is independently selected from the group consisting of H, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocycloalkyl, heterocycloalkylalkyl, heteroaryl, and heteroarylalkyl;
• R6 is independently selected from the group consisting of H, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocycloalkyl, heterocycloalkylalkyl, heteroaryl and heteroarylalkyl;
• R7 is independently selected from the group consisting of H, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocycloalkyl, heterocycloalkylalkyl, heteroaryl, and heteroarylalkyl;
• or R6 and R7 together form a 4- to 7-membered heterocycloalkyl or a 5-membered heteroaryl ring optionally having, in addition to the N atom, 1 or 2 heteroatoms selected from the group consisting of O, N(R8), N or S, wherein said rings are optionally substituted by one or more R12 moieties;
• R8 is independently selected from the group consisting of H, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocycloalkyl, heterocycloalkylalkyl, heteroaryl, heteroarylalkyl, —C(O)—R5, —C(O)O—R5, —C(O)N(R6)(R7), —C(O)-alkylene-OR4, —C(O)-alkylene-N(R6)(R7), —C(O)-alkylene-S(O)q-R5, —S(O)q-R5, —S(O)q-alkylene-OR4, —S(O)q-alkylene-N(R6)(R7), -alkylene-OR4, -alkylene-S(O)q-R5, -alkylene-N(R6)(R7), and —S(O)2N(R6)(R7) wherein said alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocycloalkyl, heterocycloalkylalkyl, heteroaryl, heteroarylalkyl and alkylene are optionally substituted with one or more groups selected from the group consisting of —OH, halo, alkyl, haloalkyl, alkoxy, haloalkoxy and cycloalkyl;
• R9 is independently selected from the group consisting of H, alkyl, haloalkyl;
• R10 is independently selected from the group consisting of H, —OH, alkyl, alkyl, cycloalkyl or alkoxy wherein said alkyl, alkyl, cycloalkyl or alkoxy groups are optionally substituted with at least one substituents selected from the group consisting of halo and —OR5;
• R11 is independently selected from the group consisting of H, alkyl, and haloalkyl;
• wherein each of the alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocycloalkyl, heterocycloalkylalkyl, heteroaryl, and heteroarylalkyl groups in R4, R5, R6 and R7 are independently unsubstituted or substituted by one or more R12 groups, where
• R12 is independently selected from the group consisting of alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocycloalkyl, heterocycloalkylalkyl, heteroaryl, heteroarylalkyl, —OR4, —C(O)—R5, C(O)O—R5, —S(O)q-R5, —N(R5)(R6), —C(O)N(R6)(R7), and —S(O)2N(R6)(R7), —NO2, —SF5, —CN, and halo and wherein each alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocycloalkyl, heterocycloalkylalkyl, heteroaryl, and heteroarylalkyl group in R12 is independently unsubstituted or substituted by one or more R13 groups where
• R13 is independently selected from the group consisting of alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocycloalkyl, heterocycloalkylalkyl, heteroaryl, heteroarylalkyl, —OR4, —C(O)—R5, —C(O)O—R5, —S(O)q-R5, —C(O)N(R6)(R7), and —S(O)2N(R6)(R7), —NO2, —SF5, —CN, and halo;
• m is independently 1, 2, or 3;
• n is independently 0, 1 or 2;
• p is 0, 1, 2, or 3;
• q is independently 0, 1, or 2;
• heteroaryl is independently selected from the group consisting of pyridyl, pyrazinyl, furanyl, thienyl, pyrimidinyl, isoxazolyl, isothiazolyl, oxazolyl, thiazolyl, pyrazolyl, furazanyl, pyrrolyl, pyrazolyl, triazolyl, 1,2,4-thiadiazolyl, pyrazinyl, pyridazinyl, quinoxalinyl, phthalazinyl, imidazo[1,2-a]pyridinyl, imidazo[2,1-b]thiazolyl, benzofurazanyl, indolyl, azaindolyl, benzimidazolyl, benzothienyl, quinolinyl, imidazolyl, thienopyridyl, quinazolinyl, thienopyrimidyl, pyrrolopyridyl, imidazopyridyl, isoquinolinyl, benzoazaindolyl, 1,2,4-triazinyl and benzothiazolyl;
• and
• heterocycloalkyl or heterocyclyl is independently selected from piperidyl, piperazinyl, morpholinyl, thiomorpholinyl, thiazolidinyl, 1,4-dioxanyl, tetrahydrofuranyl, tetrahydrothiophenyl, imidazolidinyl and pyrazolidinyl.