C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
167/207, 167/242
C07D 333/62 (2006.01) C07D 333/54 (2006.01) C07D 333/70 (2006.01) C07D 409/04 (2006.01) C07D 409/12 (2006.01) C07D 417/02 (2006.01) C07F 9/6553 (2006.01)
Patent
CA 1253151
ABSTRACT OF THE DISCLOSURE The invention relates to novel 2-sulfamoyl- benzo[b]thiophenes which are useful in the reduction of elevated intraocular pressure and having the formula: Image wherein X is hydrogen, halo, such as chloro, bromo or fluoro, C1-3 alkyl, hydroxy or C1-3 alkoxy; and R is 1) hydroxY, 2) R1 wherein R? is a) C1-18 alkyl either straight or branched chain substituted with one or more of i) C3-6 cycloalkyl, ii) halo, such as chloro, bromo or fluoro, iii) aryl, wherein the aryl group is carbo- cyclic such as phenyl or naphthyl, or heterocyclic such as pyridinyl, furanyl, pyrazinyl, morpholinyl, oxazol- inyl, dioxolinonyl, imidazolyl, thienyl or the like and wherein the aryl group can be substituted with one or more of C1-10 alkyl, halo, C1-4 alkoxy, C2-5 alkanoyl, or trifluoromethyl, iv) hydroxy, v) C1-3 alkoxy, vi) aryl-C1-3 alkoxy, vii) C1-4 alkoxy-C1-3 alkoxy, viii) amino, ix) (C1-3 alkyl)amino, x) di(C1-3 alkyl)amino, xi) R2-?-, wherein R2 is 1) HO-, 2) M+O-, wherein M+ is a pharmaceutically acceptable cation such as that from an alkali metal, or an ammonium, 3) C1-10 alkoxy, 4) R3R4N- wherein R3 and R4 are independently hydrogen, hydroxy, C1-15 alkyl, or taken together form a 3-7 membered heterocycle with the nitrogen to which they are attached such as piperidino or pyrrolidino, or xii) C2-5 alkanoyl; b) C3-6 cycloalkyl, c) C1-18 alkyl-C3-6 cycloalkyl, d) aryl as previously defined, e) R3R4N-, f) C2-6 alkenyl, g) aryl-C2-6 alkenyl, h) C2-6 alkynyl, or i) heterocyclyl of 5 or 6 members with one or two heteroatoms selected from O, N and S, such as tetra- hydropyrrolyl, tetrahydrofuranyl, or imidazolidinyl, 3) R?-O-, 4) R1-?-, wherein R1 is R? or C1-18 alkyl, 5) R1-?-O-, 6) R1-O-?-O, 7) Image wherein x is 0-2; y is 0-3; z is 0 or 1; and A is a heteroatom such as S, O or N, 8) Image where R5 and R6 are independently: a) hydrogen, b) C1-18 alkyl, either straight or branched chain, c) C3-6 cycloalkyl, d) C3-6 cycloalkyl-C1-3 alkyl, e) aryl-C1-3 alkyl wherein the aryl group is either unsubstituted or substituted with one or more of chloro, bromo, fluoro, C1-3 alkyl or C1-3 alkoxy, f) R7?-, or R7O?- wherein R7 is i) C1-18 alkyl, either straight or branched chain, ii) aryl, either unsubstituted or substituted with one or more of chloro, bromo, fluoro, C1-3 alkyl, or C1-3 alkoxy, iii) aryl-C1-3 alkyl wherein the aryl group is either unsubstituted or substituted with one or more of chloro, bromo, fluoro, C1-3 alkyl or C1-3 alkoxy, iv) amino-C1-18 alkyl either straight or branched chain; or g) R5 and R6 if lower alkyl, are joined together directly or through a heteroatom selected from O or N to form a 5 or 6 membered heterocycle with the nitrogen to which they are attached such as pyrrolidine, piperidine, morpholine, or piperazine, 9) Image , wherein ? is an ophthalmologically acceptable cation selected from sodium, potassium, ammonium, tetra(C1-4 alkyl)ammonium, pyridinium, imidazolium, pralidoxime, and thiamine, 10) Image wherein ? is as previously defined; 11) Image , wherein R8 is C1-3 alkyl or phenyl-C1-3 alkyl; or 12) (R8O)2 ?-O-, wherein R8 is as previously defined, and the two may be the same or different; and R and X, joined together, represent methylenedioxy, as well as the pharmaceutically and ophthalmologically acceptable salts thereof.
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Czaja Robert F.
Graham Samuel L.
Hoffman Jacob M. Jr.
Melillo David G.
Shepard Kenneth L.
Goudreau Gage Dubuc
Merck & Co. Inc.
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