5-Substituted 1H-pyrrolo[3,2-b]pyridines as inhibitors of gastric acid secretion.
A series of novel 1H-pyrrolo[3,2-b]pyridines was prepared relying on a copper iodide catalyzed cyclization of 2-prop-1-ynylpyridin-3-amines. A structure-activity relationship was established focusing on the influence of the substitution pattern in position 1, 3, and 5 of the heterocycle on anti-secretory activity, lipophilicity, and pK(a) value. Some of the compounds proved to be potent inhibitors of the gastric acid pump.
Palmer
Andreas Marc
AM
NYCOMED GmbH, Byk-Gulden-Str. 2, D-78467 Konstanz, Germany. andreas.palmer@nycomed.com
Münch
Gabriela
G
Brehm
Christof
C
Zimmermann
Peter Jan
PJ
Buhr
Wilm
W
Feth
Martin Philipp
MP
Simon
Wolfgang Alexander
WA
D000818:Animals; D005744:Gastric Acid / Q000378:metabolism*; D005753:Gastric Mucosa / Q000187:drug effects* / Q000378:metabolism*; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D011758:Pyrroles / Q000737:chemistry*; D011817:Rabbits; D013329:Structure-Activity Relationship
D011725:Pyridines; D011758:Pyrroles