On May 13, 2004, Linn, David Martin; Wong, Erik Ho Fong published a patent.Safety of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol The title of the patent was Preparation of azabicyclic α7 nicotinic acetylcholine agonists for the treatment of glaucoma and retinal neuropathy. And the patent contained the following:
The invention provides a use or method of treating glaucoma, diabetic retinopathy, or age-related macular degeneration by the administration of azabicycles (azabicyclo-N(R1)C(:X)W (I); X = O, S; R1 = H, alkyl, cycloalkyl, haloalkyl, substituted Ph, substituted naphthyl; W = substituted Ph, (un)substituted 5- or 6-membered heterocyclyl, etc.; addnl. details are given in the claims) that are α7 nAChR agonists (no data) to a mammal in need thereof. Although the methods of preparation are not claimed, many example preparations of intermediates are included. For example, intermediate exo-(4S)-3-amino-1-azabicyclo[2.2.1]heptane bis(p-toluenesulfonate) was prepared in 8 steps (68, 62, 76, 100, 77, 94, 46, 84 % yields, resp.) starting with reaction of benzoyl chloride with 2-nitroethanol to give 2-(benzoyloxy)-1-nitroethane, reaction of Et E-4-bromo-2-butenoate with benzylamine to give Et E-4-(benzylamino)-2-butenoate, reaction of these 2 products to give trans-4-nitro-1-(phenylmethyl)-3-pyrrolidineacetic acid Et ester, reduction to trans-4-amino-1-(phenylmethyl)-3-pyrrolidineacetic acid Et ester, N-protection, reduction to trans-3-(tert-butoxycarbonylamino)-4-(2-hydroxyethyl)-1-(phenylmethyl)pyrrolidine, chromatog. resolution, cyclization of the (+)-enantiomer to give exo-(4S)-3-(tert-butoxycarbonylamino)-1-azabicyclo[2.2.1]heptane and finally deprotection. In another example, N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-4-bromo-1H-pyrazole-1-carboxamide hydrochloride was prepared (25 %) by treating 4-bromopyrazole with phosgene followed by (R)-(+)-3-aminoquinuclidine dihydrochloride and excess Et3N, followed by NaOH. The experimental process involved the reaction of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol(cas: 280752-78-5).Safety of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol
The Article related to azabicycle preparation nicotinic acetylcholine agonist glaucoma retinal neuropathy, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.Safety of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol
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