Home / Articles / Anti-ulcer agents: chemical aspect of solving the problem

Anti-ulcer agents: chemical aspect of solving the problem

Ludmila Nikolaevna Rogoza 1
Ludmila Nikolaevna Rogoza
, 
Nariman Faridovich Salakhutdinov 1
Nariman Faridovich Salakhutdinov
1 N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistryof the Siberian Branch of Russian Academy of Sciences
Published 30 November 2014
Communication , Volume 84, Issue 1, 98-120
3
Share
Cite this
GOST
 | 
Cite this
GOST
Rogoza L. N., Salakhutdinov N. F. Anti-ulcer agents: chemical aspect of solving the problem // Russian Chemical Reviews. 2015. Vol. 84. No. 1. pp. 98-120.
GOST all authors (up to 50)
Rogoza L. N., Salakhutdinov N. F. Anti-ulcer agents: chemical aspect of solving the problem // Russian Chemical Reviews. 2015. Vol. 84. No. 1. pp. 98-120.
RIS
 | 
Cite this
RIS
TY - JOUR
DO - 10.1070/RCR4430
UR - https://rcr.colab.ws/publications/10.1070/RCR4430
TI - Anti-ulcer agents: chemical aspect of solving the problem
T2 - Russian Chemical Reviews
AU - Rogoza, Ludmila Nikolaevna
AU - Salakhutdinov, Nariman Faridovich
PY - 2015
DA - 2014/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 98-120
IS - 1
VL - 84
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
@article{2015_Rogoza,
author = {Ludmila Nikolaevna Rogoza and Nariman Faridovich Salakhutdinov},
title = {Anti-ulcer agents: chemical aspect of solving the problem},
journal = {Russian Chemical Reviews},
year = {2015},
volume = {84},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4430},
number = {1},
pages = {98--120},
doi = {10.1070/RCR4430}
}
MLA
Cite this
MLA
Rogoza, Ludmila Nikolaevna, and Nariman Faridovich Salakhutdinov. “Anti-ulcer agents: chemical aspect of solving the problem.” Russian Chemical Reviews, vol. 84, no. 1, Nov. 2015, pp. 98-120. https://rcr.colab.ws/publications/10.1070/RCR4430.
Views / Visits / Downloads
32 / 32 / 11

Abstract

The data on chemical structures and specific activities of compounds functioning as histamine $H_2$-receptor antagonists, H+/K+-ATPase inhibitors at the exchange sites of hydrogen ions (proton pump inhibitors) and potassium ions (K+-competitive acid blockers) published from 1990 to 2013 are surveyed. The antisecretory agents with studied cytoprotective activity or with additional therapeutic properties compensating for disorders of internal defence mechanisms are presented. A separate section is devoted to the drugs that prevent or mitigate the NSAID-induced intestinal damage. All of the considered structures are classified according to the type of biological mechanism of action. Some aspects of the structure--activity relationships for such compounds are considered. The bibliography includes 83 references.

References

4.
Studies on Antiulcer Drugs. IV. Synthesis and Antiulcer Activities of Imidazo(1,2-a)pyridinylethylbenzothiazoles and -benzimidazoles.
KATSURA Y., INOUE Y., NISHINO S., TOMOI M., TAKASUGI H.
Chemical and Pharmaceutical Bulletin , 2011
5.
Studies on Antiulcer Drugs. V. Synthesis and Antiulcer Activity of Aralkylbenzazoles.
KATSURA Y., INOUE Y., TOMOI M., TAKASUGI H.
Chemical and Pharmaceutical Bulletin , 2011
6.
Studies on Antiulcer Drugs. VI. 4-Furyl-2-guanidinothiazoles and Related Compounds as Potent Histamine H2-Receptor Antagonists.
KATSURA Y., INOUE Y., TOMISI T., ITOH H., ISHIKAWA H., TAKASUGI H.
Chemical and Pharmaceutical Bulletin , 2011
8.
8
V. N. Kondrat'ev
"Kinetika Reaktsii v Gazovoi Faze" (Kinetics of Reactions in the Gas Phase) , 1959
9.
9
V. H. Lynch
Carnegie Inst. Year Book , 1954
10.
10
T. A. Kryukova
"Polyaro-graficheskii Analiz" (Polarographic Analysis) , 1959
11.
11
T. T. Bannister
Diss. Abstr. , 1959
12.
12
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
13.
13
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
14.
A Novel Histamine 2(H2) Receptor Antagonist with Gastroprotective Activity. I. Synthesis and Pharmacological Evaluation of N-Phenoxypropylacetamide Derivatives with Thioether Function.
16.
16
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
17.
Effect of a novel histamine H2 receptor antagonist, IT-066, on acute gastric injury induced by ischemia-reperfusion in rats, and its antioxidative properties.
Naito Y., Yoshikawa T., Matsuyama K., Yagi N., Arai M., Nakamura Y., Kaneko T., Yoshida N., Kondo M.
European Journal of Pharmacology , 1995
18.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
20.
20
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
21.
Acute liver injury related to the use of niperotidine
Gasbarrini G., Gentiloni N., Febbraro S., Gasbarrini A., Di Campli C., Cesana M., Miglio F., Miglioli M., Ghinelli F., D'Ambrosi A., Amoroso P., Pacini F., Salvadori G.
Journal of Hepatology , 1997
22.
10.1002/(SICI)1522-2675(20000119)83:1<287::AID-HLCA287>3.0.CO;2-2
23.
The Gastric H,K ATPase as a Drug Target
Sachs G., Shin J.M., Vagin O., Lambrecht N., Yakubov I., Munson K.
Journal of Clinical Gastroenterology , 2007
24.
Chemistry of Covalent Inhibition of the Gastric (H+, K+)-ATPase by Proton Pump Inhibitors
Shin J.M., Cho Y.M., Sachs G.
Journal of the American Chemical Society , 2004
27.
Stereoselective metabolism of rabeprazole-thioether to rabeprazole by human liver microsomes
Miura M., Satoh S., Tada H., Habuchi T., Suzuki T.
European Journal of Clinical Pharmacology , 2005
28.
28
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
30.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
31.
31
A. A. Krasnovskii
Biokhimiya , 1960
32.
STEREOSELECTIVE METABOLISM OF LANSOPRAZOLE BY HUMAN LIVER CYTOCHROME P450 ENZYMES
Kim K., Kim M., Park J., Shon J., Yoon Y., Lee S., Liu K., Chun J., Hyun M., Shin J.
Drug Metabolism and Disposition , 2003
34.
Rabeprazole: a second-generation proton pump inhibitor in the treatment of acid-related disease
Pallotta S., Pace F., Marelli S.
Expert Review of Gastroenterology and Hepatology , 2008
35.
Rabeprazole: a pharmacologic and clinical review for acid-related disorders
Dadabhai A., Friedenberg F.K.
Expert Opinion on Drug Safety , 2009
36.
The effect of rabeprazole and its isomers on aspirin and histamine-induced ulcers in rats
Bodhankar S., Jain B., Ahire B., Daude R., Shitole P.
Indian Journal of Pharmacology , 2006
38.
Proton pump inhibitors: the beginning of the end or the end of the beginning?
39.
Review article: the clinical pharmacology of proton pump inhibitors
SACHS G., SHIN J.M., HOWDEN C.W.
Alimentary Pharmacology and Therapeutics , 2006
40.
Characterization of the inhibitory activity of tenatoprazole on the gastric H+,K+-ATPase in vitro and in vivo
Shin J.M., Homerin M., Domagala F., Ficheux H., Sachs G.
Biochemical Pharmacology , 2006
41.
Tenatoprazole, a novel proton pump inhibitor with a prolonged plasma half-life: effects on intragastric pH and comparison with esomeprazole in healthy volunteers
Galmiche J.P., Bruley Des Varannes S., Ducrotté P., Sacher-Huvelin S., Vavasseur F., Taccoen A., Fiorentini P., Homerin M.
Alimentary Pharmacology and Therapeutics , 2004
42.
Effect on Intragastric pH of a PPI with a Prolonged Plasma Half-Life: Comparison between Tenatoprazole and Esomeprazole on the Duration of Acid Suppression in Healthy Male Volunteers
Hunt R.H., Armstrong D., James C., Chowdhury S.K., Yuan Y., Fiorentini P., Taccoen A., Cohen P.
American Journal of Gastroenterology , 2005
43.
A comparative study of the early effects of tenatoprazole 40 mg and esomeprazole 40 mg on intragastric pH in healthy volunteers
Galmiche J.P., Sacher-Huvelin S., Bruley des Varannes S., Vavasseur F., Taccoen A., Fiorentini P., Homerin M.
Alimentary Pharmacology and Therapeutics , 2005
44.
44
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
45.
45
W. Hendrich
Roczniki Chemii , 1958
46.
A New PPI, Ilaprazole Compared With Omeprazole in the Treatment of Duodenal Ulcer
Wang L., Zhou L., Lin S., Hu H., Xia J.
Journal of Clinical Gastroenterology , 2010
47.
Ilaprazole for the treatment of duodenal ulcer: a randomized, double-blind and controlled phase III trial
48.
Predictable prolonged suppression of gastric acidity with a novel proton pump inhibitor, AGN 201904-Z
HUNT R.H., ARMSTRONG D., YAGHOOBI M., JAMES C., CHEN Y., LEONARD J., SHIN J.M., LEE E., TANG-LIU D., SACHS G.
Alimentary Pharmacology and Therapeutics , 2008
49.
Nitric oxide in mucosal defense: A little goes a long way
Wallace J.L., Miller M.J.
Gastroenterology , 2000
50.
Enhanced gastroprotective and anti-ulcerogenic activities in rats of a new class of proton pump inhibitor containing nitrosothiol nitric oxide donor
Saha J.K., Wang T., Stewart R., Trocha M., Shumway M., Garvey D., Gordon Letts L., Michael Wolfe M., William Tam S.
Gastroenterology , 2001
51.
A New Furoxan NO-Donor Rabeprazole Derivative and Related Compounds
Sorba G., Galli U., Cena C., Fruttero R., Gasco A., Morini G., Adami M., Coruzzi G., Brenciaglia M.I., Dubini F.
ChemBioChem , 2003
53.
Novel approaches to the pharmacological blockade of gastric acid secretion
Parsons M.E., Keeling D.J.
Expert Opinion on Investigational Drugs , 2005
54.
Mechanism of action of AZD0865, a K+-competitive inhibitor of gastric H+,K+-ATPase
Gedda K., Briving C., Svensson K., Maxvall I., Andersson K.
Biochemical Pharmacology , 2007
55.
N-(2-Hydroxyethyl)-N,2-dimethyl-8-{[(4R)-5-methyl-3,4-dihydro-2H-chromen-4-yl]amino}imidazo[1,2-a]pyridine-6-carboxamide (PF-03716556), a Novel, Potent, and Selective Acid Pump Antagonist for the Treatment of Gastroesophageal Reflux Disease
Mori H., Tonai-Kachi H., Ochi Y., Taniguchi Y., Ohshiro H., Takahashi N., Aihara T., Hirao A., Kato T., Sakakibara M., Kurebayashi Y.
Journal of Pharmacology and Experimental Therapeutics , 2008
56.
Novel imidazo[1,2-a]pyrazine derivatives as potent reversible inhibitors of the gastric H+/K+-ATPase
Zimmermann P.J., Brehm C., Buhr W., Palmer A.M., Volz J., Simon W.
Bioorganic and Medicinal Chemistry , 2008
57.
Yeo M., Kwak M.S., Kim D.K., Chung I.S., Moon B.S., Song K.S., Hahm K.
Journal of Clinical Biochemistry and Nutrition , 2006
58.
Soraprazan: Setting New Standards in Inhibition of Gastric Acid Secretion
Simon W.A., Herrmann M., Klein T., Shin J.M., Huber R., Senn-Bilfinger J., Postius S.
Journal of Pharmacology and Experimental Therapeutics , 2007
59.
Pharmacological Profile of Novel Acid Pump Antagonist 7-(4-Fluorobenzyloxy)-2,3-dimethyl-1-{[(1S,2S)-2-methyl cyclopropyl]methyl}-1H-pyrrolo[2,3-d]pyridazine (CS-526)
Ito K., Kinoshita K., Tomizawa A., Inaba F., Morikawa-Inomata Y., Makino M., Tabata K., Shibakawa N.
Journal of Pharmacology and Experimental Therapeutics , 2007
60.
Evaluation of basic, heterocyclic ring systems as templates for use as potassium competitive acid blockers (pCABs)
Panchal T., Bailey N., Bamford M., Demont E., Elliott R., Farre-Gutierrez I., Garton N., Hayhow T., Hutley G., Naylor A.
Bioorganic and Medicinal Chemistry Letters , 2009
61.
Novel 1H-pyrrolo[2,3-c]pyridines as acid pump antagonists (APAs)
Yoon Y.A., Kim D.H., Lee B.M., Kim T.K., Cha M.H., Sim J.Y., Kim J.G.
Bioorganic and Medicinal Chemistry Letters , 2010
62.
Tetrahydrochromenoimidazoles as Potassium-Competitive Acid Blockers (P-CABs): Structure−Activity Relationship of Their Antisecretory Properties and Their Affinity toward the hERG Channel
Palmer A.M., Chiesa V., Schmid A., Münch G., Grobbel B., Zimmermann P.J., Brehm C., Buhr W., Simon W., Kromer W., Postius S., Volz J., Hess D.
Journal of Medicinal Chemistry , 2010
63.
Discovery of biaryl inhibitors of H+/K+ ATPase
Garton N., Bailey N., Bamford M., Demont E., Farre-Gutierrez I., Hutley G., Bravi G., Pickering P.
Bioorganic and Medicinal Chemistry Letters , 2010
64.
Antiulcer agents. 1. Gastric antisecretory and cytoprotective properties of substituted imidazo[1,2-a]pyridines
Kaminski J.J., Bristol J.A., Puchalski C., Lovey R.G., Elliott A.J., Guzik H., Solomon D.M., Conn D.J., Domalski M.S.
Journal of Medicinal Chemistry , 1985
65.
Antiulcer agents. 2. Gastric antisecretory, cytoprotective, and metabolic properties of substituted imidazo[1,2-a]pyridines and analogs
Kaminski J.J., Hilbert J.M., Pramanik B.N., Solomon D.M., Conn D.J., Rizvi R.K., Elliott A.J., Guzik H., Lovey R.G.
Journal of Medicinal Chemistry , 1987
66.
Antiulcer agents. 4. Conformational considerations and the antiulcer activity of substituted imidazo[1,2-a]pyridines and related analogs
Kaminski J.J., Puchalski C., Solomon D.M., Rizvi R.K., Conn D.J., Elliott A.J., Lovey R.G., Guzik H., Chiu P.J.
Journal of Medicinal Chemistry , 1989
67.
Synthesis and Evaluation of 7H-8,9-Dihydropyrano[2,3-c]imidazo[1,2-a]pyridines as Potassium-Competitive Acid Blockers
Palmer A.M., Grobbel B., Jecke C., Brehm C., Zimmermann P.J., Buhr W., Feth M.P., Simon W., Kromer W.
Journal of Medicinal Chemistry , 2007
68.
Spiro(imidazo[1,2-a]pyrano[2,3-c]pyridine-9-indenes) as inhibitors of gastric acid secretion
Palmer A.M., Chrismann S., Münch G., Brehm C., Zimmermann P.J., Buhr W., Senn-Bilfinger J., Feth M.P., Simon W.A.
Bioorganic and Medicinal Chemistry , 2009
69.
Glucuronide conjugates of Soraprazan (BY359), a new potassium-competitive acid blocker (P-CAB) for the treatment of acid-related diseases
Senn-Bilfinger J., Ferguson J.R., Holmes M.A., Lumbard K.W., Huber R., Zech K., Hummel R., Zimmermann P.J.
Tetrahedron Letters , 2006
70.
Early Stellate Cell Activation and Veno-occlusive-disease (VOD)–like Hepatotoxicity in Dogs Treated with AR-H047108, an Imidazopyridine Proton Pump Inhibitor
Berg A., Böttcher G., Andersson K., Carlsson E., Lindström A., Huby R., Håkansson H., Skånberg-Wilhelmsson I., Hellmold H.
Toxicologic Pathology , 2008
71.
Orally active C-6 heteroaryl- and heterocyclyl-substituted imidazo[1,2-a]pyridine acid pump antagonists (APAs)
Bailey N., Bamford M.J., Brissy D., Brookfield J., Demont E., Elliott R., Garton N., Farre-Gutierrez I., Hayhow T., Hutley G., Naylor A., Panchal T.A., Seow H., Spalding D., Takle A.K., et. al.
Bioorganic and Medicinal Chemistry Letters , 2009
72.
5-Substituted 1H-pyrrolo[3,2-b]pyridines as inhibitors of gastric acid secretion☆
Palmer A.M., Münch G., Brehm C., Zimmermann P.J., Buhr W., Feth M.P., Simon W.A.
Bioorganic and Medicinal Chemistry , 2008
73.
Pharmacodynamic and Pharmacokinetic Evaluation of CS-526 in Cynomolgus Monkeys
Ito K., Kinoshita K., Yamamura N., Tomizawa A., Inaba F., Morikawa-Inomata Y., Tabata K., Shibakawa N.
Biological and Pharmaceutical Bulletin , 2009
74.
Pharmacokinetic and Pharmacodynamic Evaluation of a Novel Proton Pump Inhibitor, YH1885, in Healthy Volunteers
Yu K., Bae K., Shon J., Cho J., Yi S., Chung J., Lim H., Jang I., Shin S., Song K., Moon B.
Journal of Clinical Pharmacology , 2004
75.
Novel pyrimidines as acid pump antagonists (APAs)
Yoon Y.A., Park C.S., Cha M.H., Choi H., Sim J.Y., Kim J.G.
Bioorganic and Medicinal Chemistry Letters , 2010
76.
Discovery, synthesis, and biological evaluation of novel pyrrole derivatives as highly selective potassium-competitive acid blockers
Nishida H., Hasuoka A., Arikawa Y., Kurasawa O., Hirase K., Inatomi N., Hori Y., Sato F., Tarui N., Imanishi A., Kondo M., Takagi T., Kajino M.
Bioorganic and Medicinal Chemistry , 2012
77.
Discovery of a Novel Pyrrole Derivative 1-[5-(2-Fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine Fumarate (TAK-438) as a Potassium-Competitive Acid Blocker (P-CAB)
Arikawa Y., Nishida H., Kurasawa O., Hasuoka A., Hirase K., Inatomi N., Hori Y., Matsukawa J., Imanishi A., Kondo M., Tarui N., Hamada T., Takagi T., Takeuchi T., Kajino M., et. al.
Journal of Medicinal Chemistry , 2012
78.
1-[5-(2-Fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine Monofumarate (TAK-438), a Novel and Potent Potassium-Competitive Acid Blocker for the Treatment of Acid-Related Diseases
Hori Y., Imanishi A., Matsukawa J., Tsukimi Y., Nishida H., Arikawa Y., Hirase K., Kajino M., Inatomi N.
Journal of Pharmacology and Experimental Therapeutics , 2010
80.
A Study Comparing the Antisecretory Effect of TAK-438, a Novel Potassium-Competitive Acid Blocker, with Lansoprazole in Animals
Hori Y., Matsukawa J., Takeuchi T., Nishida H., Kajino M., Inatomi N.
Journal of Pharmacology and Experimental Therapeutics , 2011
81.
81
J. C. Ghosh
J. Indian Chem. Soc. , 1934
83.
83
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947