Process for preparing crystalline form I of cabergoline

Details Process for preparing crystalline form I of cabergoline Process for preparing crystalline form I of cabergoline

2003-02-03

2004-04-27

Aulakh, Charanjit (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S067000, C546S061000

Reexamination Certificate

active

06727363

ABSTRACT:

The present invention concerns a new process for preparing crystalline Form I of cabergoline.
Cabergoline is an ergoline derivative interacting with D2 dopamine receptors and is endowed with different useful pharmaceutical activities and it is used in the treatment of hyperprolactinemia, central nervous system disorders (CNS) and other related diseases.
Cabergoline is the generic name of 1((6-allylergolin-8beta-yl)-carbonyl)-1-(3-dimethylaminopropyl)-3-ethylurea, described and claimed in U.S. Pat No. 4,526,892. The synthesis of cabergoline molecule is reported also in Eur. J. Med. Chem., 24,421, (1989) and in GB-
2,103,603-
B. Crystalline cabergoline Form I, an anhydrous not solvated form of cabergoline, was prepared by crystallization from diethyl ether, as described in Il Farmaco, 50 (3), 175-178 (1995).
Cabergoline Form I, like cabergoline, displays a significant inhibitory effect with regard prolactine and has therapeutic properties that make it possible to treat patients who have pathological conditions associated with an abnormal prolactin level, thus is useful in human and/or veterinary medicine. Cabergoline is also active, alone or in combination, in the treatment of reversible obstructive airways diseases, for controlling intraocular pressure and for the treament of glaucoma. It is also employed in the veterinary field, as antiprolactin agent and in cutting down drastically the proliferation of vertebrate animals. The several uses of cabergoline are for example described in WO9948484, WO9936095, U.S. Pat No. 5705510, WO9505176, EP040,325.
Cabergoline Form I is particularly useful in the treatment of Parkinson's disease (PD), Restless Legs Syndrome (RLS), treatment of diseases like Progressive Supranuclear Palsy (PSP) and Multysystemic atrophy (MSA).
During our development work we discovered a new process for preparing crystalline Form I.
Thus, the present invention concerns a new process for preparing Form I of cabergoline and a new solvate Form V of cabergoline useful as intermediate.


REFERENCES:
patent: 4526892 (1985-07-01), Salvati et al.
patent: 5382669 (1995-01-01), Candiani et al.
patent: 2 103 603 (1983-02-01), None
P. Sabatino et al.: “X-ray crystal structure and conformational analysis of N-(3-Dimethylaminopropyl)-N-(ethylaminocarbonyl)-6-(2-propenl)ergoli NE-8Beta-carboxamine (cabergoline): Comparison with bromocriptine and lisuride and a hypothesis for its high dopaminergic activity” Farmaco, Societa Chimica Italiana, vol. 50, No. 3, pp. 175-178, 1995.
E. Brambilla et al.: “Synthesis and nidation inhibitory activity of a new class of ergoline derivatives synthese et activite inhibitrice sur la nidation d′une nouvelle classe de derives de l'ergoline” European Journal of Medicinal Chemistry, Chimica Therapeutica, vol. 24, pp. 421-426, 1989.

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