Compound and pharmacologically acceptable salt thereof

Inventors

Tamura, Keiji • Yamakawa, Takeru • ISSHIKI, Satoshi • Wakiyama, Yoshinari • OUCHI, Shohei • Matsuhira, Takashi • ISHIDA, Natsuki • Tabata, Yuji

Assignees

Meiji Seika Pharma Co Ltd

Abstract

A compound represented by the general formula (1) below or a pharmacologically acceptable salt thereof: [In the formula (1), R1 and R2 may be the same or different and each represents a hydrogen atom, a halogen atom, a hydroxyl group, a carboxy group, a cyano group, an optionally substituted C1-6 alkyl group et al.; R3 represents a hydrogen atom; R4 represents an optionally substituted 4- to 10-membered monocyclic heterocyclic group containing 1 to 4 heteroatoms selected from an oxygen atom, a nitrogen atom, and a sulfur atom; X represents a group represented by the following formula: —CH2—, —CH2—CH2—, —CH2—CH2—CH2—, or —CH2—O—CH2—; and Z represents a hydrogen atom or a hydroxyl group].

Core Innovation

The invention relates to a compound represented by formula (1) or a pharmacologically acceptable salt thereof. The formula defines variable substituents R1 and R2, together with R3, R4, X, and Z, where R1 and R2 are selected from hydrogen, halogen, hydroxyl, carboxy, cyano, and a wide range of optionally substituted alkyl, cycloalkyl, aryl, aralkyl, aromatic heterocyclic, nonaromatic heterocyclic, amino, acylamino, alkyloxy, alkenyloxy, aryloxy, heterocyclyloxy, alkylthio, sulfonyl, sulfinyl, sulfamoyl, carbonyl, aminocarbonyl, alkyloxycarbonyl, and hydroxyaminocarbonyl groups. R3 is hydrogen, R4 is an optionally substituted monocyclic heterocyclic group, X is a defined chain pattern or CH2OCH2, and Z is hydrogen or hydroxyl.

The disclosed scaffold is a benzo[d]oxazole framework with diazabicyclic ring systems and thiazolyl substituents in the exemplified embodiments. Specific embodiments include diazabicyclo[3.1.1]heptane, diazabicyclo[3.2.1]octane, and diazabicyclo[3.3.1]nonane variants, together with thiazol-2-yl or related heteroaryl groups and substituent patterns including chloro, bromo, methyl, trifluoromethyl, trifluoromethoxy, difluoro, methoxy, oxy, sulfonyl, sulfinyl, carboxylate, carboxamide, hydroxyl, and nitrile motifs. The examples further include racemic and optically active compounds, with ESI-MS and 1H NMR characterization reported for named structures.

The document also describes benzo[d]oxazole compounds bearing 5-chloro cores, mercapto and protected thiol derivatives, and alternative heteroaryl substitutions such as pyrazolyl, furyl, pyridyl, and oxazolyl. Some examples are identified as enantiomers or optically active substances, and stereochemical forms, tautomers, hydrates, solvates, and radioisotopes/labeled compounds are included in the described scope. The examples and structural tables collectively support a family of formula (1) compounds with varied diazabicyclic and heteroaryl substitution patterns.

Claims Coverage

The claims cover a formula (1) compound class and a pharmaceutical composition, with four inventive feature groups across the input items.

The claims protect a formula (1) benzo[d]oxazole compound class with broad substituent options at R1 and R2, narrower claims fixing R2 to hydrogen or fixing R1 to hydrogen with limited R2, and dependent claims that enumerate specific diazabicyclo and heteroaryl embodiments. A separate composition claim covers pharmaceutical compositions containing the claim-1 compound or salts as active ingredient.

Stated Advantages

Documented Applications