Patent ID: 6552025
Filing Date: 2003-04-22
Classification: A61K,C07D

Abstract:
A composition comprising a diimino compound that inhibits, in a cationic form, sphingolipid metabolism; wherein the diimino compound has a molecular weight between 112 and 3000 Daltons; and wherein the diimino compound has the following structural formula: whereinR is independently H, alkyl, aryl, heteroaryl, â€”C(O)R, â€”C(NR)OR, â€”C(O)NR2, â€”C(NR)NR2, â€”C(NR)SR or â€”C(S)NR2; R1, R2, R3 and R4 are independently H, R, (CH2)nOR, (CH2)nNR2, CH2O(CH2)nOR, or CH2O(CH2)nNR2 where n=1 to 6; and wherein H+ or other cationic species can form an association between any electronegative atom of the diimino compound; and wherein the term alkyl refers to a saturated straight, branched, or cyclic, primary, secondary, or tertiary hydrocarbon, typically of C1 to C18 and specifically includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, cyclopentyl, isopentyl, neopentyl, hexyl, isohexyl, cyclohexyl, cyclohexylmethyl, 3-methylpentyl, 2,2-dimethylbutyl and 2,3-dimethylbutyl; and wherein the alkyl group can be optionally substituted with one or more moieties selected from halo, hydroxyl, carboxylic acid or ester, amino, alkylamino, arylamino, alkoxy, aryloxy, nitro, cyano, sulfonic acid, sulfate, phosphonic acid, phosphate, or phosphonate, either unprotected or protected; and wherein the term aryl refers to phenyl, biphenyl, or naphthyl, and wherein the aryl group can be optionally substituted with one or more moieties selected from the group consisting of halo, hydroxyl, amino, alkylamino, arylamino, alkoxy, aryloxy, nitro, cyano, sulfonic acid, sulfate, phosphonic acid, phosphate or phosphonate, either unprotected, or protected; and wherein the aryl group can be substituted with an alkyl group as described above, and/or a halo group; and wherein the term heteroaryl refers to a cyclic moiety that includes at least one sulfur, oxygen, or nitrogen in the ring, including, but not limited to, furyl, pyridyl, pyrimidyl, thienyl, isothiazolyl, imidazolyl, tetrazolyl, pyrazinyl, benzofuranyl, benzothiophenyl, quinolyl, isoquinolyl, benzothienyl, isobenzofuryl, pyrazolyl, indolyl, isoindolyl, benzimidazolyl, purinyl, carbazolyl, oxazolyl, thiazolyl, isothiazolyl, 1,2,4-thiadiazolyl, isoxazolyl, pyrrolyl, quinazolinyl, pyridazinyl, pyrazinyl, cinnolinyl, phthalazinyl, quinoxalinyl, xanthinyl, hypoxanthinyl, and pteridinyl; and wherein the oxygen and nitrogen groups on the heteroaryl group can be protected or unprotected; and wherein the heteroaryl can be substituted with an alkyl group as described above; and, wherein the term â€œprotectedâ€  refers to a group that is added to an oxygen, nitrogen, or phosphorus atom to prevent its further reaction, or for other purposes; and wherein suitable protecting groups include, but are not limited to, trimethylsilyl, triethylsilyl, dimethylhexylsilyl, t-butyldimethylsilyl, t-butyldiphenylsilyl and triisopropylsilyl.