Dipeptidyl peptidase IV inhibitors pharmaceutical compositions containing them, and process for their preparation
AssigneeGlenmark Pharmaceuticals S.A.
InventorsAbraham Thomas, Gopalan Balasubramanian, V. S. Prasada Rao Lingam, Daisy Manish Shah
Life of this patent
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Abstract
The present invention relates to novel compounds useful as dipeptidyl peptidase IV (DPP-IV) inhibitors of the formula: wherein X, Y, a, R1, and R2 are as defined herein.
Claims51
A compound of general formula (I)
- wherein:
- Y is —CH2—, CHF, or —CF2;
- m is 0, 1, or 2;
- X is a bond, C1–C5 alkyl, or —C(═O)—;
- the dotted line [----] in the carbocyclic ring represents an optional double bond;
- R1 is a substituted or unsubstituted heteroaryl ring or substituted or unsubstituted heterocyclic ring, wherein the ring is a five-membered ring having at least one nitrogen atom;
- R2 is hydrogen, nitrile (—CN), or COOH,
- or a tautomeric form, regioisomer, stereoisomer, enantiomer, diastereomer, solvate, N-oxide, or pharmaceutically acceptable salt thereof.
A compound selected from:
- (2S)-1-{2-[(1S,4R)-4-(1H-1,2,4-Triazol-1-ylmethyl)-2-cyclopentylamino]acetyl}-pyrrolidin-2-carbonitrile,
- (2S)-1-{2-[(3SR,1RS)-3-(1H-1,2,4-Triazol-1-ylmethyl)cyclopentylamino]acetyl}-pyrrolidine-2-carbonitrile,
- (2S)-1-{2-[(3S,1R)-3-(1H-1,2,4-Triazol-1-ylmethyl)cyclopentylamino]acetyl}-pyrrolidine-2-carbonitrile,
- (2S)-1-{2-[(3R,1S)-3-(1H-1,2,4-Triazol-1-ylmethyl)cyclopentylamino]acetyl}-pyrrolidine-2-carbonitrile,
- (2S,4S)-1-{2-[(3SR,1RS)-3-(1H-1,2,4-Triazol-1-ylmethyl)cyclopentylamino]acetyl}-4-fluoropyrrolidine-2-carbonitrile,
- (2S,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-Triazol-1-ylmethyl)cyclopentylamino]acetyl}-4-fluoropyrrolidine-2-carbonitrile,
- (2S,4S)-1-{2-[(1S,3R)-3-(1H-1,2,4-Triazol-1-ylmethyl)cyclopentylamino]acetyl}-4-fluoropyrrolidine-2-carbonitrile,
- (2S,4S)-4-Fluoro-1-{2-[(1R,3R)-3-(1H-1,2,4-Triazol-1-ylmethyl)cyclopentylamino]-acetyl}pyrrolidin-2-carbonitrile,
- 1-[(3S)-3-Fluoropyrrolidin-1-yl]-2-[(1S,3S)-3-(1H-1,2,4-Triazol-1-ylmethyl)cyclo-pentylamino]-1-ethanone,
- and pharmaceutically acceptable salts thereof.
1-{2-[3-(1H-1,2,4-triazol-1-ylmethyl)cyclopentylamino]acetyl}-4-fluoropyrrolidine-2-carbonitrile or a pharmaceutically acceptable salt thereof.
A compound selected from
- (2S,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-Triazol-1-ylmethyl)cyclopentylamino]acetyl}-4-fluoropyrrolidine-2-carbonitrile hydrochloride,
- (2S,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-Triazol-1-ylmethyl)cyclopentylamino]acetyl}-4-fluoropyrrolidine-2-carbonitrile methanesulfonate,
- (2S,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-Triazol-1-ylmethyl)cyclopentylamino]acetyl}-4-fluoropyrrolidine-2-carbonitrile oxalate,
- (2S,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-Triazol-1-ylmethyl)cyclopentylamino]acetyl}-4-fluoropyrrolidine-2-carbonitrile succinate,
- (2S,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-Triazol-1-ylmethyl)cyclopentylamino]acetyl}-4-fluoropyrrolidine-2-carbonitrile 2-oxoglutarate,
- (2S,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-Triazol-1-ylmethyl)cyclopentylamino]acetyl}-4-fluoropyrrolidine-2-carbonitrile benzoate,
- (2S,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-Triazol-1-ylmethyl)cyclopentylamino]acetyl}-4-fluoropyrrolidine-2-carbonitrile salicylate,
- (2S,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-Triazol-1-ylmethyl)cyclopentylamino]acetyl}-4-fluoropyrrolidine-2-carbonitrile benzenesulfonate, and
- (2S,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-Triazol-1-ylmethyl)cyclopentylamino]acetyl}-4-fluoropyrrolidine-2-carbonitrile naphthalene-1,5-disulfonic acid.
(2S,4S)-1-{2-[(3SR,1RS)-3-(1H-1,2,4-triazol-1-ylmethyl)cyclopentylamino]-acetyl}-4-fluoropyrrolidine-2-carbonitrile or a pharmaceutically acceptable salt thereof.
(2S,4S)-1-{2-[(3S,R)-3-(1H-1,2,4-triazol-1-ylmethyl)cyclopentylamino]-acetyl}-4-fluoropyrrolidine-2-carbonitrile or a pharmaceutically acceptable salt thereof.
(2S,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-triazol-1-ylmethyl)cyclopentylamino]-acetyl}-4-fluoropyrrolidine-2-carbonitrile hydrochloride.
(2S,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-triazol-1-ylmethyl)cyclopentylamino]-acetyl}-4-fluoropyrrolidine-2-carbonitrile methanesulfonate.
(2S,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-triazol-1-ylmethyl)cyclopentylamino]-acetyl}-4-fluoropyrrolidine-2-carbonitrile oxalate.
(2S,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-triazol-1-ylmethyl)cyclopentylamino]-acetyl}-4-fluoropyrrolidine-2-carbonitrile succinate.
(2S,4S)-1-{2-[(3S, 1R)-3-(1H-1,2,4-triazol-1-ylmethyl)cyclopentylamino]-acetyl}-4-fluoropyrrolidine-2-carbonitrile 2-oxoglutarate.
(2S ,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-triazol-1-ylmethyl)cyclopentylamino]-acetyl}-4-fluoropyrrolidine-2-carbonitrile benzoate.
(2S ,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-triazol-1-ylmethyl)cyclopentylamino]-acetyl}-4-fluoropyrrolidine-2-carbonitrile salicylate.
(2S,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-triazol-1-ylmethyl)cyclopentylamino]-acetyl}-4-fluoropyrrolidine-2-carbonitrile benzenesulfonate.
(2S,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-triazol-1-ylmethyl)cyclopentylamino]-acetyl}-4-fluoropyrrolidine-2-carbonitrile naphthalene-1,5-disulfonic acid.
(2S,4S)-1-{2-[(1S,3R)-3-(1H-1,2,4-triazol-1-ylmethyl)cyclopentylamino]-acetyl}-4-fluoropyrrolidine-2-carbonitrile or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.