Dipeptidyl peptidase IV (DP-IV) inhibitors as anti-diabetic...

Details Dipeptidyl peptidase IV (DP-IV) inhibitors as anti-diabetic... Dipeptidyl peptidase IV (DP-IV) inhibitors as anti-diabetic...

2006-12-05

2006-12-05

McKane, Joseph K. (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S343000, C544S406000, C546S279100

Reexamination Certificate

active

07144886

ABSTRACT:
The present invention relates to a series of prodrugs of inhibitors of DP-IV with improved properties. The compounds can be used for the treatment of a number of human diseases, including impaired glucose tolerance and type II diabetes. The compounds of the invention are described by general formula (1); wherein R1is H or CN; R2is selected from CH2R5, CH2CH2R5and C(R3)(R4)—X2—(CH2)aR5; R3and R4are each independently selected from H and Me; R5is selected from CON(R6)(R7), N(R8)C(═O)R9, N(R8)C(═S)R9, N(R8)SO2R10and N(R8)R10; R6and R7are each independently R11(CH2)bor together they are —(CH2)2—Z—(CH2)2— or CH2—o—C6H4—Z—CH2—; R8is H or Me; R9is selected from R11(CH2)b, R11(CH2)bO and N(R6)(R7); R10is R11(CH2)b; R11is selected from H, alkyl, optionally substituted aryl, optionally substituted aroyl, optionally substituted arylsulphonyl and optionally substituted heteroaryl; R12is selected from H2NCH(R13)CO, H2NCH(R14)CONHCH(R15)CO, C(R16)═C(R17)COR18and R19OCO; R13, R14and R15are selected from the side chains of the proteinaceous amino acids; R16is selected from H, lower alkyl (C1–C6) and phenyl; R17is selected from H and lower alkyl (C1–C6); R18is selected from H, lower alkyl (C1–C6), OH, O-(lower alkyl (C1–C6)) and phenyl; R19is selected from lower alkyl (C1–C6), optionally substituted phenyl and R20C(═O)OC(R21)(R22); R20, R21and R22are each independently selected from H and lower alkyl (C1–C6); Z is selected from a covalent bond, —(CH2)c—, —O—, —SOd— and —N(R10)—; X1is S or CH2; X2is O, S or CH2; a is 1, 2 or 3; b is 0–3; c is 1 or 2; and d is 0, 1 or 2.

REFERENCES:
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Gaudron, Sandrine et al., “NAcSDKP Analogs Resistant to Angiotensin-Converting Enzyme”, Journal of Medicinal Chemistry (1997), 40(4), XP002223609, pp. 3963-3968.

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