Compounds and methods for treating urinary incontinence

A compound selected from the group consisting of:

• (a) 2-(6-bromo-3-dimethylamino-2-methylphenylimino)imidazolidine,
• (b) 2-(2-methyl-3-phthalimidophenylimino)imidazolidine,
• (c) 2-(3-acetylamino-6-chlorophenylimino)imidazolidine,
• (d) 2-(3-amino-2-methylphenylimino)imidazolidine,
• (e) 2-(3-amino-4,6-dibromo-2-methylphenylimino)imidazolidine,
• (f) 2-(3-amino-4-methylphenylimino)imidazolidine,
• (g) 2-(4,6-dibromo-3-dimethylamino-2-methylphenylimino)imidazolidine,
• (h) 2-(4-bromo-3-dimethylamino-2-methylphenylimino)imidazolidine,
• (i) 2-(6-chloro-3-dimethylamino-2-methylphenylimino)imidazolidine, and
• (j) 2-(6-chloro-3-phthalimidophenylimino)imidazolidine,
• or a pharmaceutically acceptable salt thereof.

A pharmaceutical composition comprising:

• (a) a compound selected from the group consisting of:
• 2-(3-dimethylamino-2-methylphenylimino)imidazolidine,
• 2-(6-bromo-3-dimethylamino-2-methylphenylimino)imidazolidine,
• 2-(5-amino-2-chloro-4-dimethylamino-2-methylphenylimino)imidazolidine, and
• 2-(3-amino-2-methylphenylimino)imidazolidine,
• or a pharmaceutically acceptable salt thereof, and
• (b) one or more pharmaceutically acceptable excipients, adjuvants, carriers, or preservatives.

A pharmaceutical composition comprising:

• (a) a compound selected from the group consisting of:
• 2-(3-dimethylamino-2-methylphenylimino)imidazolidine,
• 2-(6-bromo-3-dimethylamino-2-methylphenylimino)imidazolidine,
• 2-(2-methyl-3-phthalimidophenylimino)imidazolidine,
• 2-(3-acetylamino-6-chlorophenylimino)imidazolidine,
• 2-(3-amino-2-methylphenylimino)imidazolidine,
• 2-(3-amino-4,6-dibromo-2-methylphenylimino)imidazolidine,
• 2-(3-amino-4-methylphenylimino)imidazolidine,
• 2-(4,6-dibromo-3-dimethylamino-2-methylphenylimino)imidazolidine,
• 2-(4-bromo-3-dimethylamino-2-methylphenylimino)imidazolidine,
• 2-(6-chloro-3-dimethylamino-2-methylphenylimino)imidazolidine,
• 2-(6-chloro-3-phthalimidophenylimino)imidazolidine,
• or a pharmaceutically acceptable salt thereof;
• and
• (b) one or more pharmaceutically acceptable excipients, adjuvants, carriers, or preservatives.

A compound of the formula (II)

• wherein:
• R1 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, C3-6-cycloalkyl, C1-6-alkoxy, fluorine, bromine, iodine, —CF3, or —OCF3;
• R2 is —NR6R7, wherein R6 and R7 together with the nitrogen between them form a 5- or 6-membered, saturated or unsaturated ring containing 0, 1, or 2 additional heteroatoms selected from the group consisting of oxygen, sulfur, and nitrogen, wherein each additional nitrogen atom is unsubstituted or substituted by methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, or R6 and R7 together with the nitrogen between them form phthalimido;
• R3 is hydrogen, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, C1-6-alkoxy, —CF3, or —OCF3;
• R4 is hydrogen, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl;
• and
• R5 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, C1-6-alkoxy, halogen, —CF3, or —OCF3;
• or a pharmaceutically acceptable salt thereof.

A compound of the formula (II)

• wherein:
• R1 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, C1-4-alkoxy, fluorine, bromine, iodine, —CF3, or —OCF3;
• R2 is —NR6R7, wherein R6 and R7 together with the nitrogen between them form phthalimido;
• R3 is hydrogen, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, C1-4-alkoxy, —CF3, or —OCF3;
• R4 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, or halogen;
• and,
• R5 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, C1-4-alkoxy, halogen, —CF3, or —OCF3;
• or a pharmaceutically acceptable salt thereof.

A compound of the formula (II)

• wherein:
• R1 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, cyclopropyl, C1-3-alkoxy, fluorine, bromine, iodine, or —CF3;
• R2 is —NR6R7, wherein R6 and R7 together with the nitrogen between them form phthalimido;
• R3 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, C1-3-alkoxy, halogen, or —CF3;
• R4 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or halogen;
• and,
• R5 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, C1-3-alkoxy, halogen, or —CF3;
• or a pharmaceutically acceptable salt thereof.

A compound of the formula (II)

• wherein:
• R1 is hydrogen, methyl, ethyl, n-propyl, isopropyl, fluorine, bromine, or iodine;
• R2 is —NR6R7, wherein R6 and R7 together with the nitrogen between them form phthalimido;
• R3 is hydrogen, methyl, fluorine, chlorine, or bromine;
• R4 is hydrogen;
• and
• R5 is hydrogen, methyl, chlorine, or bromine;
• or a pharmaceutically acceptable salt thereof.

A compound of the formula (II)

• wherein:
• R1 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, C3-6-cycloalkyl, C1-6-alkoxy, halogen, —CF3, or —OCF3;
• R2 is —NR6R7, wherein R6 and R7 together with the nitrogen between them form a 5- or 6-membered, saturated or unsaturated ring containing 0, 1, or 2 additional heteroatoms selected from the group consisting of oxygen, sulfur, and nitrogen, wherein each additional nitrogen atom is unsubstituted or substituted by methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, or R6 and R7 together with the nitrogen between them form phthalimido;
• R3 is hydrogen, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, C1-6-alkoxy, —CF3, or —OCF3;
• R4 is hydrogen, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl;
• and
• R5 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, C1-6-alkoxy, fluorine, bromine, iodine, —CF3, or —OCF3;
• or a pharmaceutically acceptable salt thereof.

A compound of the formula (II)

• wherein:
• R1 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, C14-alkoxy, halogen, —CF3, or —OCF3;
• R2 is —NR6R7, wherein R6 and R7 together with the nitrogen between them form phthalimido;
• R3 is hydrogen, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, C1-4-alkoxy, —CF3, or —OCF3;
• R4 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, or halogen;
• and,
• R5 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, C1-4-alkoxy, fluorine, bromine, iodine, —CF3, or —OCF3;
• or a pharmaceutically acceptable salt thereof.

A compound of the formula (II)

• wherein:
• R1 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, cyclopropyl, C1-3-alkoxy, halogen, or —CF3;
• R2 is —NR6R7, wherein R6 and R7 together with the nitrogen between them form phthalimido;
• R3 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, C1-3-alkoxy, halogen, or —CF3;
• R4 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or halogen;
• and,
• R5 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, C1-3-alkoxy, fluorine, bromine, iodine, or —CF3;
• or a pharmaceutically acceptable salt thereof.

A compound of the formula (II)

• wherein:
• R1 is hydrogen, methyl, ethyl, n-propyl, isopropyl, or halogen;
• R2 is —NR6R7, wherein R6 and R7 together with the nitrogen between them form phthalimido;
• R3 is hydrogen, methyl, fluorine, chlorine, or bromine;
• R4 is hydrogen;
• and
• R5 is hydrogen, methyl, fluorine, or bromine;
• or a pharmaceutically acceptable salt thereof.