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Literature summary extracted from

  • Eckhardt, M.; Hauel, N.; Himmelsbach, F.; Langkopf, E.; Nar, H.; Mark, M.; Tadayyon, M.; Thomas, L.; Guth, B.; Lotz, R.
    3,5-Dihydro-imidazo[4,5-d]pyridazin-4-ones: a class of potent DPP-4 inhibitors (2008), Bioorg. Med. Chem. Lett., 18, 3158-3162.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.4.14.5 2-(3-aminopiperidin-1-yl)-1-but-2-yn-1-yl-4-cyano-N-(naphthalen-1-ylmethyl)-1H-imidazole-5-carboxamide
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-1-but-2-yn-1-yl-N-(naphthalen-1-ylmethyl)-1H-imidazole-5-carboxamide
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-1-but-2-yn-1-yl-N-methyl-N-(naphthalen-1-ylmethyl)-1H-imidazole-5-carboxamide
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-1-but-2-yn-1-yl-N-methyl-N-[(3-methylisoquinolin-1-yl)methyl]-1H-imidazole-5-carboxamide
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-1-but-2-yn-1-yl-N-[(3-methylisoquinolin-1-yl)methyl]-1H-imidazole-5-carboxamide
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-(10,11-dihydrodibenzo[b,f][1,4]oxazepin-11-ylmethyl)-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-(2-oxo-2-phenylethyl)-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-(naphthalen-1-ylmethyl)-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-(naphthalen-1-ylmethyl)-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-[(11R)-10,11-dihydrodibenzo[b,f][1,4]oxazepin-11-ylmethyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-[(11S)-10,11-dihydrodibenzo[b,f][1,4]oxazepin-11-ylmethyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-[(3-methylisoquinolin-1-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-[(3-methylisoquinolin-1-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-[(4-methylquinazolin-2-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-[(6-methyl-1,3-benzoxazol-2-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-7-methoxy-5-(naphthalen-1-ylmethyl)-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-7-methoxy-5-[(3-methylisoquinolin-1-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-7-methyl-5-(naphthalen-1-ylmethyl)-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-7-methyl-5-[(3-methylisoquinolin-1-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-7-methyl-5-[(4-methylquinazolin-2-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-4-bromo-1-but-2-yn-1-yl-N-(naphthalen-1-ylmethyl)-1H-imidazole-5-carboxamide
-
 Homo sapiens
3.4.14.5 2-(3-aminopiperidin-1-yl)-4-bromo-1-but-2-yn-1-yl-N-[(3-methylisoquinolin-1-yl)methyl]-1H-imidazole-5-carboxamide
-
 Homo sapiens
3.4.14.5 2-[(2-aminoethyl)(methyl)amino]-3-but-2-yn-1-yl-5-[(4-methylquinazolin-2-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
-
 Homo sapiens
3.4.14.5 2-[(3R)-3-aminopiperidin-1-yl]-3-but-2-yn-1-yl-5-[(4-methylquinazolin-2-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
-
 Homo sapiens
3.4.14.5 2-[[(2S)-2-aminopropyl](methyl)amino]-3-but-2-yn-1-yl-5-[(4-methylquinazolin-2-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
-
 Homo sapiens
3.4.14.5 3-but-2-yn-1-yl-2-(1,4-diazepan-1-yl)-5-[(4-methylquinazolin-2-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
-
 Homo sapiens
3.4.14.5 4-[[2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-4-oxo-3,4-dihydro-5H-imidazo[4,5-d]pyridazin-5-yl]methyl]naphthalene-1-carbonitrile
-
 Homo sapiens
3.4.14.5 5-(3-aminopiperidin-1-yl)-4-but-2-yn-1-yl-N-(naphthalen-1-ylmethyl)-4H-1,2,4-triazole-3-carboxamide
-
 Homo sapiens
3.4.14.5 5-(3-aminopiperidin-1-yl)-4-but-2-yn-1-yl-N-[(3-methylisoquinolin-1-yl)methyl]-4H-1,2,4-triazole-3-carboxamide
-
 Homo sapiens
3.4.14.5 8-(3-aminopiperidin-1-yl)-7-but-2-yn-1-yl-3-methyl-1-(naphthalen-1-ylmethyl)-3,7-dihydro-1H-purine-2,6-dione
-
 Homo sapiens
3.4.14.5 8-(3-aminopiperidin-1-yl)-7-but-2-yn-1-yl-3-methyl-1-[(3-methylisoquinolin-1-yl)methyl]-3,7-dihydro-1H-purine-2,6-dione
-
 Homo sapiens
3.4.14.5 BI 1356 proposed trade name ONDERO, highly potent and selective DPP-4 inhibitor Homo sapiens
3.4.14.5 BI 1356 proposed trade name ONDERO, highly potent and selective DPP-4 inhibitor Rattus norvegicus

Organism

EC Number Organism UniProt Comment Textmining
3.4.14.5 Homo sapiens
-
-
-
3.4.14.5 Rattus norvegicus
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.4.14.5 L-Arg-L-Pro-7-amido-4-methylcoumarin + H2O
-
 Homo sapiens L-Arg-L-Pro + 7-amino-4-methylcoumarin
-
 ?
3.4.14.5 L-Glu-L-Pro-4-nitroanilide
-
 Homo sapiens L-Glu-L-Pro + 4-nitroaniline
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.4.14.5 dipeptidyl peptidase IV
-
 Homo sapiens
3.4.14.5 dipeptidyl peptidase IV
-
 Rattus norvegicus
3.4.14.5 DPP-4
-
 Homo sapiens
3.4.14.5 DPP-4
-
 Rattus norvegicus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.4.14.5 0.000001
-
-
 Homo sapiens BI 1356
3.4.14.5 0.000001
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-[(4-methylquinazolin-2-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
3.4.14.5 0.000001
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-7-methyl-5-[(4-methylquinazolin-2-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
3.4.14.5 0.000001
-
-
 Homo sapiens 2-[(2-aminoethyl)(methyl)amino]-3-but-2-yn-1-yl-5-[(4-methylquinazolin-2-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
3.4.14.5 0.000002
-
-
 Homo sapiens 2-[[(2S)-2-aminopropyl](methyl)amino]-3-but-2-yn-1-yl-5-[(4-methylquinazolin-2-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
3.4.14.5 0.000002
-
-
 Homo sapiens 8-(3-aminopiperidin-1-yl)-7-but-2-yn-1-yl-3-methyl-1-[(3-methylisoquinolin-1-yl)methyl]-3,7-dihydro-1H-purine-2,6-dione
3.4.14.5 0.000003
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-[(11S)-10,11-dihydrodibenzo[b,f][1,4]oxazepin-11-ylmethyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
3.4.14.5 0.000003
-
-
 Homo sapiens 3-but-2-yn-1-yl-2-(1,4-diazepan-1-yl)-5-[(4-methylquinazolin-2-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
3.4.14.5 0.000004
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-[(6-methyl-1,3-benzoxazol-2-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
3.4.14.5 0.000004
-
-
 Homo sapiens 4-[[2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-4-oxo-3,4-dihydro-5H-imidazo[4,5-d]pyridazin-5-yl]methyl]naphthalene-1-carbonitrile
3.4.14.5 0.000005
-
-
 Homo sapiens 2-[(3R)-3-aminopiperidin-1-yl]-3-but-2-yn-1-yl-5-[(4-methylquinazolin-2-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
3.4.14.5 0.000005
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-[(3-methylisoquinolin-1-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
3.4.14.5 0.000007
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-7-methyl-5-[(3-methylisoquinolin-1-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
3.4.14.5 0.000013
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-(naphthalen-1-ylmethyl)-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
3.4.14.5 0.000014
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-(10,11-dihydrodibenzo[b,f][1,4]oxazepin-11-ylmethyl)-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
3.4.14.5 0.000015
-
-
 Homo sapiens 8-(3-aminopiperidin-1-yl)-7-but-2-yn-1-yl-3-methyl-1-(naphthalen-1-ylmethyl)-3,7-dihydro-1H-purine-2,6-dione
3.4.14.5 0.000019
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-7-methoxy-5-[(3-methylisoquinolin-1-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
3.4.14.5 0.000021
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-[(3-methylisoquinolin-1-yl)methyl]-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one
3.4.14.5 0.000024
-
-
 Homo sapiens 5-(3-aminopiperidin-1-yl)-4-but-2-yn-1-yl-N-[(3-methylisoquinolin-1-yl)methyl]-4H-1,2,4-triazole-3-carboxamide
3.4.14.5 0.000025
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-[(11R)-10,11-dihydrodibenzo[b,f][1,4]oxazepin-11-ylmethyl]-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
3.4.14.5 0.000026
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-(2-oxo-2-phenylethyl)-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
3.4.14.5 0.000052
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-7-methoxy-5-(naphthalen-1-ylmethyl)-3,5-dihydro-4H-imidazo[4,5-d]pyridazin-4-one
3.4.14.5 0.000089
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-3-but-2-yn-1-yl-5-(naphthalen-1-ylmethyl)-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one
3.4.14.5 0.000099
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-1-but-2-yn-1-yl-N-[(3-methylisoquinolin-1-yl)methyl]-1H-imidazole-5-carboxamide
3.4.14.5 0.000107
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-1-but-2-yn-1-yl-N-(naphthalen-1-ylmethyl)-1H-imidazole-5-carboxamide
3.4.14.5 0.000559
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-4-bromo-1-but-2-yn-1-yl-N-(naphthalen-1-ylmethyl)-1H-imidazole-5-carboxamide
3.4.14.5 0.000582
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-1-but-2-yn-1-yl-4-cyano-N-(naphthalen-1-ylmethyl)-1H-imidazole-5-carboxamide
3.4.14.5 0.003059
-
-
 Homo sapiens 2-(3-aminopiperidin-1-yl)-1-but-2-yn-1-yl-N-methyl-N-(naphthalen-1-ylmethyl)-1H-imidazole-5-carboxamide