Sodium channel blockers

A method of preparing a compound of Formula (I):

• or a salt thereof, the method comprising a step of reacting a compound of the formula:
• or a salt thereof, with a compound of the formula:
• HNR3R4, or a salt thereof, wherein:
• X is hydrogen, halogen, trifluoromethyl, lower alkyl, unsubstituted or substituted phenyl, lower alkyl-thio, phenyl-lower alkyl-thio, lower alkyl-sulfonyl, or phenyl-lower alkyl-sulfonyl;
• Y is hydrogen, hydroxyl, mercapto, lower alkoxy, lower alkyl-thio, halogen, lower alkyl, unsubstituted or substituted mononuclear aryl, or —N(R2)2;
• R1 is hydrogen or lower alkyl;
• each R2 is independently —R7, —(CH2)m—OR8, —(CH2)m—NR7R10, —(CH2)n(CHOR8)(CHOR8)n—CH2OR8, —(CH2CH2O)m—R8, —(CH2CH2O)m—CH2CH2NR7R10, —(CH2)n—C(═O)NR7R10, —(CH2)n—(Z)g-R7, —(CH2)mNR10-CH2(CHOR8)(CHOR8)nCH2OR8, —(CH2)nCO2R7, or
• R3 and R4 are each independently hydrogen, a group represented by Formula (A), lower alkyl, hydroxyl lower alkyl, phenyl, phenyl-lower alkyl, (halophenyl)-lower alkyl, lower-(alkylphenylalkyl), lower (alkoxyphenyl)-lower alkyl, naphthyl-lower alkyl, or pyridyl-lower alkyl, with the proviso that at least one of R3 and R4 is a group represented by Formula (A):
• and wherein:
• each RL is independently —R7, —(CH2)n—OR8, —O—(CH2)m—OR8, —(CH2)n—NR7R10, —O—(CH2)m—NR7R10, —(CH2)n(CHOR8)(CHOR8)n—CH2OR8, —O—(CH2)m(CHOR8)(CHOR8)n—CH2OR8, —(CH2CH2O)m—R8, —O—(CH2CH2O)m—R8, —(CH2CH2O)m—CH2CH2NR7R10, —O—(CH2CH2O)m—CH2CH2NR7R10, —(CH2)n—C(═O)NR7R10, —O—(CH2)m—C(═O)NR7R10, —(CH2)n—(Z)g—R7, —O—(CH2)m—(Z)g—R7, —(CH2)n—NR10-CH2(CHOR8)(CHOR8)n—CH2OR8, —O—(CH2)m—NR10-CH2(CHOR8)(CHOR8)n—CH2OR8, —(CH2)n—CO2R7, —O—(CH2)m—CO2R7, —OSO3H, —O-glucuronide, —O-glucose,
• each o is independently an integer from 0 to 10;
• each p is an integer from 0 to 10;
• with the proviso that the sum of o and p in each contiguous chain is from 1 to 10;
• each x is independently O, NR10, C(═O), CHOH, C(═N—R10), CHNR7R10, or a single bond;
• each R5 is independently —(CH2)m—OR8, —O—(CH2)m—OR8, —(CH2)n—NR7R10, —O—(CH2)m—NR7R10, —(CH2)n(CHOR8)(CHOR8)n—CH2OR8, —O—(CH2)m(CHOR8)(CHOR8)n—CH2OR8, —(CH2CH2O)m—R8, —O—(CH2CH2O)m—R8, —(CH2CH2O)m—CH2CH2NR7R10, —O—(CH2CH2O)m—CH2CH2NR7R10, —(CH2)n—C(═O)NR7R10, —O—(CH2)m—C(═O)NR7R10, —(CH2)n—(Z)g-R7, —O—(CH2)m—(Z)g-R7, —(CH2)n—NR10-CH2(CHOR8)(CHOR8)n—CH2OR8, —O—(CH2)m—NR10-CH2(CHOR8)(CHOR8)n—CH2OR8, —(CH2)n—CO2R7, —O—(CH2)m—CO2R7, —OSO3H, —O-glucuronide, —O-glucose,
• each R6 is independently —R7, —OR11, —N(R7)2, —(CH2)m—OR8, —O—(CH2)m—OR8, —(CH2)n—NR7R10, —O—(CH2)m—NR7R10, —(CH2)n(CHOR8)(CHOR8)n—CH2OR8, —O—(CH2)m(CHOR8)(CHOR8)n—CH2OR8, —(CH2CH2O)m—R8, —O—(CH2CH2O)m-R8, —(CH2CH2O)m—CH2CH2NR7R10, —O—(CH2CH20)m—CH2CH2NR7R10, —(CH2)n—C(═O)NR7R10, —O—(CH2)m—C(═O)NR7R10, —(CH2)n—(Z)g-R7, —O—(CH2)m—(Z)g-R7, —(CH2)n—NR10-CH2(CHOR8)(CHOR8)n—CH2OR8, —O—(CH2)m—NR10-CH2(CHOR8)(CHOR8)n—CH2OR8, —(CH2)n—CO2R7, —O—(CH2)m—CO2R7, —OSO3H, —O-glucuronide, —O-glucose,
• wherein when two R6 are —OR11 and are located adjacent to ech other on a phenyl ring, the alkyl moieties of the two R6 may be bonded together to form a methylenedioxy group;
• each R7 is independently hydrogen or lower alkyl;
• each R8 is independently hydrogen, lower alkyl, —C(═O)-R11, glucuronide, 2-tetrahydropyranyl, or
• each R9 is independently —CO2R7, —CON(R7)2, —SO2CH3, or C(═O)R7;
• each R10 is independently —H, —SO2CH3, —CO2R7, —C(═O)NR7R9, —C(═O)R7, or CH2—(CHOH)nCH2OH;
• each Z is independently CHOH, C(═O), CHNR7R10, C═NR10, or NR10;
• each R11 is independently lower alkyl;
• each g is independently an integer from 1 to 6;
• each m is independently an integer from 1 to 7;
• each n is independently an integer from 0 to 7;
• and
• each Q is independently C—R5 or C—R6, wherein one Q is C—R5.