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US 7,598,279 B2Granted
Neurotherapeutic azole compounds
AssigneeSK Holdings Co., Ltd.
InventorsYong Moon Choi, Choon-Gil Kim, Han-Ju Yi, Young-Sun Kang, Hyun-Seok Lee
Life of this patent
Estimating the term…
Abstract
Azole compounds containing carbamoyl group and pharmaceutically useful salts thereof are described. The compounds are effective anticonvulsants which are used in the treatment of disorders of the central nervous system, especially as anxiety, depression, convulsion, epilepsy, migraine, bipolar disorder, drug abuse, smoking, ADHD, obesity, sleep disorder, neuropathic pain, stroke, cognitive impairment, neurodegeneration, stroke and muscle spasm.
Claims60
An azole compound of the formula:
- wherein, G is a ring selected from the group consisting of piperonyl, indanyl, naphtyl, phenyl and phenoxy methyl which ring may be substituted with one or more identical or different substituents selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen, alkoxy containing 1 to 8 carbon atoms, thioalkoxy containing 1 to 8 carbon atoms, hydroxy, perfluoroalkyl, phenoxy, phenylalkyloxy of 1 to 8 carbon atoms or phenoxyalkyl of 1 to 8 carbon atoms, wherein the phenyl moiety of phenoxy, phenoxyalkyl and phenylalkyloxy is unsubstituted or substituted with amino, mono- or di-substituted amino with lower alkyl of 1 to 8 carbon atoms, amido, sulfonamido, nitro, carboxyl, or perfluoroalkyl of 1 to 8 carbon atoms;
- m is an integer from 0 to 6;
- Y is selected from the group consisting of hydrogen, halogen, and lower alkyl of 1 to 8 carbon atoms;
- n is an integer from 0 to 6;
- A is azole group represented by the following structural formula (X-1) or (X-2):
- wherein, A1 is selected from the group consisting of nitrogen atom and CH;
- Q is selected from the group consisting of hydrogen, perfluoroalkyl, halogen, amino, mono- or di-substituted alkyl amino with alkyl of 1 to 8 carbon atoms, amido, linear or branched alkyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, arylalkyl, morpholino, piperidino, pyrrolidino, thioalkoxy of 1 to 8 carbon atoms, benzylthio, thienyl, aminoalkyl, hydroxyalkyl, styryl, carboxylic, pyridyl, unsubstituted phenyl and phenyl substituted with one or more identical or different substituents selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, arylalkyl, halogen, alkoxy containing 1 to 8 carbon atoms, phenoxy, amino, mono- or di-substituted amino with alkyl of 1 to 8 carbon atoms, nitro, hydroxy, thioalkoxy, furanyl, sulfonamido, or perfluoroalkyl;
- R1 and R2 are independently selected from the group consisting of hydrogen, C(═O)NH2, lower alkyl of 1 to 8 carbon atoms, non-substituted or substituted phenyl, and non-substituted or substituted phenylalkyl of 1 to 8 carbon atoms, or taken together with attached nitrogen form a imidazole, piperazine or phenyl piperazine ring or cyclic amine ring represented by the following structural formula (XI):
- wherein, A2 is selected from the group consisting of nitrogen atom and carbon atom;
- E and U are independently selected from the group consisting of hydrogen, hydroxy and O-carbamoyl or taken together form oxo;
- W is selected from a ring consisting of piperonyl, indanyl, naphtyl, tetrazolyl, triazolyl, pyridyl and phenyl which ring may be substituted with one or more identical or different substituents selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen, alkoxy containing 1 to 8 carbon atoms, thioalkoxy containing 1 to 8 carbon atoms, phenoxy, phenylalkyloxy of 1 to 8 carbon atoms, phenyloxyalkyl of 1 to 8 carbon atoms, where the phenyl moiety of phenoxy, phenylalkyloxy and phenoxyalkyl is unsubstituted or substituted with amino, mono- or di-substituted amino with alkyl of 1 to 8 carbon atoms, amido, sulfonamido, nitro, carboxyl, hydroxy, or perfluoroalkyl of 1 to 8 carbon atoms;
- j is an integer from 0 to 4;
- and
- t is an integer from 0 to 4;
- or a pharmaceutically acceptable salt thereof.
12 more elements
An azole compound of the formula:
- wherein A1 is selected from the group consisting of a nitrogen atom and CH;
- R11 is hydrogen, lower alkyl, amino carbonyl, phenyl or phenyl lower alkyl wherein the phenyl group can be unsubstituted or mono or disubstituted with a lower alkyl, hydroxy, lower alkoxy, halo, cyclo lower alkyl;
- R12 is hydrogen or lower alkyl;
- or R12 taken together with R11 and their attached nitrogen atom form a 4 to 6 membered heteroarmatic ring containing at most 3 additional hetero nitrogen atoms;
- R13 is hydrogen, amino, mono or dilower lower alkylamino hetero aromatic, amino carbonyl or phenyl where the phenyl group can be unsubstituted or mono or disubstituted with a lower alkyl, hydroxy, lower alkoxy, or halo;
- and R′15 and R′16 when taken together with their attached carbon atoms form a cycloalkyl or phenyl ring which can be unsubstituted or substituted with halo, lower alkyl, lower alkoxy, hydroxy, halogen or trifluoromethyl.
3 more elements
Dependencies are inferred from the claim text.