Methods of making N-desmethylzopiclone
AssigneeSepracor Inc.
InventorsThomas P. Jerussi, Chrisantha H. Senanayake, Paul D. Rubin, Yaping Hong, Roger A. Bakale, Tingjian Xiang, Fran A. McConville
Life of this patent
Estimating the term…
Abstract
The invention is directed to compositions comprising, and methods of using, racemic N-desmethylzopiclone, optically pure (+)-N-desmethylzopiclone, and optically pure (−)-N-desmethylzopiclone in the treatment and prevention of diseases and conditions in mammals. The invention is further directed to novel methods of preparing N-desmethylzopiclone, optically pure (+)-N-desmethylzopiclone, and optically pure (−)-N-desmethylzopiclone.
Claims68
A method of treating or preventing anxiety in a patient, which comprises administering to a patient suffering from anxiety a therapeutically or prophylactically effective amount of N-desmethylzopiclone, or a pharmaceutically acceptable salt, solvate, hydrate, or clathrate thereof.
A method of treating or preventing a convulsive state in a patient, which comprises administering to a patient suffering from, or prone to suffer from, convulsions a therapeutically or prophylactically effective amount of N-desmethylzopiclone, or a pharmaceutically acceptable salt, solvate, hydrate, or clathrate thereof.
A method of treating or preventing spasticity or acute muscle spasms in a patient, which comprises administering to a patient suffering from spasticity or acute muscle spasms a therapeutically or prophylactically effective amount of N-desmethylzopiclone, or a pharmaceutically acceptable salt, solvate, hydrate, or clathrate thereof.
A method of treating or preventing an affective disorder in a patient, which comprises administering to a patient suffering from an affective disorder a therapeutically or prophylactically effective amount of N-desmethylzopiclone, or a pharmaceutically acceptable salt, solvate, hydrate, or clathrate thereof.
A method of treating or preventing a behavioral disorder in a patient, which comprises administering to a patient suffering from a behavioral disorder a therapeutically or prophylactically effective amount of N-desmethylzopiclone, or a pharmaceutically acceptable salt, solvate, hydrate, or clathrate thereof.
A method of treating or preventing schizophrenic disorder in a patient, which comprises administering to a patient suffering from schizophrenic disorder a therapeutically or prophylactically effective amount of N-desmethylzopiclone, or a pharmaceutically acceptable salt, solvate, hydrate, or clathrate thereof.
A method of treating or preventing aggressive behavior in a patient, which comprises administering to a patient suffering from aggressive behavior a therapeutically or prophylactically effective amount of N-desmethylzopiclone, or a pharmaceutically acceptable salt, solvate, hydrate, or clathrate thereof.
A method of treating or preventing alcohol or drug addiction in a patient, which comprises administering to a patient suffering from alcohol or drug addiction a therapeutically or prophylactically effective amount of N-desmethylzopiclone, or a pharmaceutically acceptable salt, solvate, hydrate, or clathrate thereof.
A method of treating or preventing abnormal plasma hormone levels in a patient, which comprises administering to a patient suffering from abnormal plasma hormone levels a therapeutically or prophylactically effective amount of N-desmethylzopiclone, or a pharmaceutically acceptable salt, solvate, hydrate, or clathrate thereof.
A method of treating or preventing a sleep disorder in a patient, which comprises administering to a patient suffering from a sleep disorder a therapeutically or prophylactically effective amount of N-desmethylzopiclone, or a pharmaceutically acceptable salt, solvate, hydrate, or clathrate thereof.
A method of treating or preventing a disease or condition or symptom thereof in a patient affected by the modulation of one or more central or peripheral benzodiazepine receptors, which comprises administering to said patient a therapeutically or prophylactically effective amount of N-desmethylzopiclone, or a pharmaceutically acceptable salt, solvate, hydrate, or clathrate thereof.
A pharmaceutical composition comprising N-desmethylzopiclone, or a pharmaceutically acceptable salt, solvate, hydrate, or clathrate thereof.
An individual dosage form of N-desmethylzopiclone which comprises N-desmethylzopiclone, or a pharmaceutically acceptable salt, solvate, hydrate, or clathrate thereof.
A method of preparing N-desmethylzopiclone which comprises contacting zopiclone with an azodicarboxylate under conditions sufficient to form a product and hydrolyzing the product under mild conditions.
A method of preparing racemic N-desmethylzopiclone which comprises contacting racemic zopiclone with α-chloroethyl chloroformate to form a mixture and refluxing said mixture in methanol.
A method of preparing (+)-N-desmethyl zopiclone which comprises contacting (+)-zopiclone with α-chloroethyl chloroformate to form a mixture and refluxing said mixture in methanol.
A method of preparing (−)-N-desmethylzopiclone which comprises contacting (−)-zopiclone with α-chloroethyl chloroformate to form a mixture and refluxing said mixture in methanol.
A method of increasing the optical purity of zopiclone or desmethylzopiclone which comprises contacting zopiclone or desmethylzopiclone with L-N-benzyloxycarbonyl phenyl alanine in a water and ethanol solvent system, and isolating optically enriched zopiclone or desmethylzopiclone.
Dependencies are inferred from the claim text.