- Synthesis method of 4-chloro-3-methoxy-2-methylpyridine-N-oxide
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The invention discloses a synthesis method of a pantoprazole intermediate compound 4-chloro-3-methoxy-2-methylpyridine-N-oxide. The synthesis method comprises the following steps: by taking 4-chloro-3-methoxy-2-methylpyridine as a raw material and a phosphotungstic acid solution as a catalyst, performing an oxidation reaction with oxydol; and after the oxidation reaction, regulating the pH value to 7-9 with sodium hydroxide to decompose the excessive oxydol, extracting 4-chloro-3-methoxy-2-methylpyridine-N-oxide with dichloromethane, washing the extract liquid with water to a neutral state, adding anhydrous Na2SO4, drying, and evaporating under reduced pressure to remove the dichloromethane so as to obtain the 4-chloro-3-methoxy-2-methylpyridine-N-oxide. The synthesis method has the advantages of mild reaction conditions, high safety, high yield, high operation convenience, no waste acid discharge, greenness, environment friendliness and low cost, thereby being more suitable for industrial production.
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Paragraph 0026-0040
(2017/09/13)
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- Synthesis of a DOTA (Gd3+)-conjugate of proton-pump inhibitor pantoprazole for gastric wall imaging studies
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Magnetic resonance imaging (MRI) is used to evaluate gastrointestinal (GI) structure and functions in humans. Despite filling the viscus lumen with a contrast agent, visualization of the viscus wall is limited. To overcome this limitation, we de novo synthesized a conjugate that covalently combines a Gd-based MRI contrast agent, encaged with a chelating agent (DOTA), with pantoprazole, which is a widely used proton pump inhibitor that binds to proton pumps in the stomach and colon. The DOTA linkage was installed at a mechanism-based strategic location in the pantoprazole molecule to minimize a possible negative effect of the structural modification on the drug. It is anticipated that by defining the wall of the stomach and colon, this compound will facilitate functional MRI of the GI tract in humans.
- Maharvi, Ghulam M.,Bharucha, Adil E.,Fauq, Abdul H.
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p. 2808 - 2811
(2013/06/27)
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- 4-Oxoquinolizine antimicrobial having 2-pyridone skeleton as partial structure
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A compound represented by the following Formula (I) or a pharmaceutically acceptable salt thereof: 1wherein R1 represents a hydrogen atom or a carboxyl-protecting group, R2 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or a hydroxyl group, R3 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a nitro group, a cyano group, a hydroxyl group or an amino group; R4 represents a hydrogen atom, an amino-protecting group, an alkyl group or a cycloalkyl group, and R5 represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an alkoxy group, an alkylthio group, a hydroxyl group, an imino group or an amino group.
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- SUBSTITUTED HETEROCYCLIC CARBOXAMIDE ESTERS, THEIR PREPARATION AND THEIR USE AS PHARMACEUTICALS
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The invention relates to compounds of the formula I, to a process for their preparation and to their use as pharmaceuticals. The compounds are employed, in particular, as ester prodrugs of prolyl hydroxylase inhibitors for inhibiting collagen biosynthesis and as fibrosuppressive agents
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- (H+,K+)-ATPase inhibiting 2-[(2-pyridylmethyl)sulfinyl]benzimidazoles. 4. A novel series of dimethoxypyridyl-substituted inhibitors with enhanced selectivity. The selection of pantoprazole as a clinical candidate
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[(Pyridylmethyl)sulfinyl]benzimidazoles 1 (PSBs) are a class of highly potent antisecretory (H+,K+)-ATPase inhibitors which need to be activated by acid to form their active principle, the cyclic sulfenamide 4. Selective inhibitors of the (H+,K+)-ATPase in vivo give rise to the nonselective thiophile 4 solely at low pH, thus avoiding interaction with other thiol groups in the body. The propensity to undergo the acid-catalyzed transformation is dependent on the nucleophilic/electrophilic properties of the functional groups involved in the formation of 2 since this step is both rate-determining and pH-dependent. The aim of this study was to identify compounds with high (H+,K+)-ATPase inhibitory activity in stimulated gastric glands possessing acidic pH, but low reactivity (high chemical stability) at neutral pH as reflected by in vitro (Na+,K+)-ATPase inhibitory activity. The critical influence of substituents flanking the pyridine 4-methoxy substituent present in all derivatives was carefully studied. The introduction of a 3-methoxy group gave inhibitors possessing a combination of high potency, similar to omeprazole and lansoprazole, but increased stability. As a result of these studies, compound 1a (INN pantoprazole) was selected as a candidate drug and is currently undergoing phase III clinical studies.
- Kohl,Sturm,Senn-Bilfinger,Simon,Kruger,Schaefer,Rainer,Figala,Klemm
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p. 1049 - 1057
(2007/10/02)
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