Rosacea: An Introduction

Detailed Compound Description

In one embodiment, the invention is directed to compounds of the Formula I wherein each of R.sub.1, R.sub.2, and R.sub.3 is independently hydrogen, halogen, alkyl, preferably, unsubstituted alkyl, or alkoxy, preferably, unsubstituted alkoxy; each of R.sub.4 and R.sub.5 is independently hydrogen, alkyl, preferably, unsubstituted alkyl, or alkoxy, preferably, unsubstituted alkoxy; and each of R.sub.6 and R.sub.7 is independently hydrogen, nitro, alkyl, preferably, unsubstituted alkyl, or alkoxy, preferably, unsubstituted alkoxy. In a preferred embodiment of the compounds of Formula I, R.sub.6 and R.sub.7 are both hydrogen. In another preferred embodiment, R.sub.4 and R.sub.5 are both hydrogen.

In another embodiment, the invention is directed to compounds of the Formula wherein each of R.sub.1, R.sub.2, and R.sub.3 is independently hydrogen, halogen, alkyl, preferably, unsubstituted alkyl, or alkoxy, preferably, unsubstituted alkoxy; each of R.sub.4 and R.sub.5 is independently hydrogen, alkyl, preferably, unsubstituted alkyl, or alkoxy, preferably, unsubstituted alkoxy; and each of R.sub.6 and R.sub.7 is independently hydrogen, nitro, alkyl, preferably, unsubstituted alkyl, or alkoxy, preferably, unsubstituted alkoxy. In a preferred embodiment of the compounds of Formula Ia, R.sub.6 and R.sub.7 are both hydrogen. In another preferred embodiment, R.sub.4 and R.sub.5 are both hydrogen. In still another preferred embodiment of the compounds of Formula Ia, R.sub.2 and R.sub.3 are both hydrogen and R.sub.1 is halo, preferably, bromo.

In another embodiment, the invention relates to compounds of the Formula Ib wherein each of R.sub.1, R.sub.2, and R.sub.3 is independently hydrogen, halogen, alkyl, preferably, unsubstituted alkyl, or alkoxy, preferably, unsubstituted alkoxy. In a preferred embodiment of the compounds of Formula Ib, R.sub.2 and R.sub.3 are both hydrogen and R.sub.1 is halo, preferably, bromo.

In another embodiment. the invention relates to compounds of the Formula Ic wherein R.sub.1 is hydrogen, halogen, alkyl, preferably, unsubstituted alkyl, or alkoxy, preferably unsubstituted alkoxy. In a preferred embodiment R.sub.1 is halo, more preferably, bromo; and each of R.sub.4 and R.sub.5 is independently hydrogen, alkyl, preferably, unsubstituted alkyl, or alkoxy, preferably, unsubstituted alkoxy. In a preferred embodiment of the compounds of Formula Ic, at least one of R.sub.4 and R.sub.5 is hydrogen.

In another embodiment, the invention relates to compounds of the Formula Id wherein R.sub.1 is hydrogen, halogen, alkyl, preferably, unsubstituted alkyl, or alkoxy, preferably, unsubstituted alkoxy. In a preferred embodiment, R.sub.1 is halo, more preferably, bromo.

In another embodiment, the invention relates to compounds of the Formula II wherein each of A.sub.1, A.sub.3, and A.sub.4 is independently hydrogen or alkyl, and A.sub.2 is hydrogen or hydroxyl.

In another embodiment, the invention relates to compounds of the Formula III wherein each of B.sub.1, B.sub.2, and B.sub.3 is independently hydrogen, hydroxy, or methoxy; each of B.sub.4 and B.sub.5 is independently hydrogen or alkyl.

Preferred compounds of the invention are listed in Table 1 below.

TABLE 1 Compounds Of The Invention Compound of the Invention Name 13 (5-Bromo- quinoxalin-6-yl)- (4,5-dihydro-1H- imidazol-2-yl)- amine (Brimonidine) 14 (8-Bromo- quinoxalin-6-yl)- (4,5-dihydro-1H- imidazol-2-yl)- amine 15 (8-Bromo- quinoxalin-5-yl)- (4,5-dihydro-1H- imidazol-2-yl)- amine 16 (5-Bromo-3- methyl- quinoxalin-6-yl)- (4,5-dihydro- 1H-imidazol- 2-yl)-amine 17 (5-Bromo-2- methoxy- quinoxalin-6-yl)- (4,5-dihydro- 1H-imidazol-2-yl)- amine 18 (4,5-dihydro- 1H-imidazol-2-yl)- (8-methyl- quinoxalin-6-yl)- amine 19 (4,5-dihydro- 1H-imidazol-2-yl)- quinoxalin-5- yl-amine 20 Tetrahydrozaline 21 Naphazoline 22 Oxymetazoline 23 Xylometazoline 24 Epinephrine 25 Norepinephrine 26 Phenylephrine 27 Methoxyamine

The most preferred compound is (5-Bromo-quinoxalin-6-yl)-(4,5-dihyd- ro-1H-imidazol-2-yl)-amine (commonly referred to as brimonidine) and pharmaceutically acceptable salts thereof, particularly the tartrate salt. Other compounds of the invention include naphazoline, tetra-hydrozaline, oxymetazoline, xylometazoline, epinephrine, norepinephrine, phenylephrine and methoxamine and their pharmaceutically acceptable salts.

The compounds of the invention are well known in the art to be .alpha..sub.2 adrenergic receptor agonists. As such the compounds have powerful vasoconstricting effects when introduced into the body of mammals, particularly humans.


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