Metabolites of (3-[[4-tert-butyl-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid

The compound:

• 2-{4-[pyridine-N-oxide-3-sulfonylamino)-methyl]-phenyl}-2-methyl-propionic acid;
• (3-{[[4-(2-hydroxy-1,1-dimethyl-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid glucuronide;
• the sulfate conjugate of pyridine-N-oxide-3-sulfonic acid 4-(2-hydroxy-1,1-dimethyl-ethyl)-benzylamide;
• the sulfate conjugate of (3-{[[4-(2-hydroxy-1,1-dimethyl-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• the sulfate conjugate of pyridine-3-sulfonic acid 4-(2-hydroxy-1,1-dimethyl-ethyl)-benzylamide;
• 2-methyl-2-{4-[(pyridine-3-sulfonylamino)-methyl]-phenyl}-propionic acid;
• (3-{[[4-(1,2-dihydroxy-1-methyl-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• (3-{[[4-(1-hydroxy-1-methyl-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• (3-{[[4-(1,1-dimethyl-2-oxo-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• or
• (3-{[(4-isopropenyl-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• or a pharmaceutically acceptable salt thereof.

A method of determining if a patient has been administered (3-{[4-tert-butyl-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid, the method comprising the step of determining if a plasma, urine, bile or fecal sample obtained from the patient shows the presence of one or more of a compound selected from the group consisting of 2-(4-{[(3-carboxymethoxy-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenyl)-2-methyl-propionic acid;

• (3-{[[4-(2-hydroxy-1,1-dimethyl-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• 2-{4-[pyridine-N-oxide-3-sulfonylamino)-methyl]-phenyl}-2-methyl-propionic acid;
• (3-{[[4-(2-hydroxy-1,1-dimethyl-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid glucuronide;
• the sulfate conjugate of pyridine-N-oxide-3-sulfonic acid 4-(2-hydroxy-1,1-dimethyl-ethyl)-benzylamide;
• the sulfate conjugate of (3-{[[4-(2-hydroxy-1,1-dimethyl-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• the sulfate conjugate of pyridine-3-sulfonic acid 4-(2-hydroxy-1,1-dimethyl-ethyl)-benzylamide;
• 2-methyl-2-{4-[(pyridine-3-sulfonylamino)-methyl]-phenyl}-propionic acid;
• (3-{[(4-tert-butyl-benzyl)-(pyridine-N-oxide-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• (5-{[(4-tert-butyl-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-hydroxy-phenoxy)-acetic acid;
• (3-{[[4-(1,2-dihydroxy-1-methyl-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• (3-{([[4-(1-hydroxy-1-methyl-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• (3-{[[4-(1,1-dimethyl-2-oxo-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• and
• (3-{[(4-isopropenyl-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid.

A method of treating osteoporosis or aiding in healing a bone fracture, the method comprising administering to a patient in need thereof a therapeutically effective amount of a compound selected from:

• 2-(4-{[(3-carboxymethoxy-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenyl)-2-methyl-propionic acid;
• (3-{[[4-(2-hydroxy-1,1-dimethyl-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• (3-{[(4-tert-butyl-benzyl)-(pyridine-N-oxide-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• (5-{[(4-tert-butyl-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-hydroxy-phenoxy)-acetic acid;
• (3-{[[4-(1,2-dihydroxy-1-methyl-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• (3-{[[4-(1-hydroxy-1-methyl-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• (3-{[[4-(1,1-dimethyl-2-oxo-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• or
• (3-{[(4-isopropenyl-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• or a pharmaceutically acceptable salt thereof.

A pharmaceutical composition comprising one or more compound selected from

• 2-(4-{[(3-carboxymethoxy-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenyl)-2-methyl-propionic acid;
• (3-{[[4-(2-hydroxy-1,1-dimethyl-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• 2-{4-[pyridine-N-oxide-3-sulfonylamino)-methyl]-phenyl}-2-methyl-propionic acid;
• (3-{[[4-(2-hydroxy-1,1-dimethyl-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid glucuronide;
• the sulfate conjugate of pyridine-N-oxide-3-sulfonic acid 4-(2-hydroxy-1,1-dimethyl-ethyl)-benzylamide;
• the sulfate conjugate of (3-{[[4-(2-hydroxy-1,1-dimethyl-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• the sulfate conjugate of pyridine-3-sulfonic acid 4-(?-hydroxy-1,1-dimethyl-ethyl)-benzylamide;
• 2-methyl-2-{4-[(pyridine-3-sulfonylamino)-methyl]-phenyl}-propionic acid;
• (3-{[(4-tert-butyl-benzyl)-(pyridine-N-oxide-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• (5-{[(4-tert-butyl-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-hydroxy-phenoxy)-acetic acid;
• (3-{[[4-(1,2-dihydroxy-1-methyl-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• (3-{[[4-(1-hydroxy-1-methyl-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• (3-{[[4-(1,1-dimethyl-2-oxo-ethyl)-benzyl]-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• or
• (3-{[(4-isopropenyl-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-acetic acid;
• or a pharmaceutically acceptable salt thereof.