Claims
- 1. A compound of the formula I wherein R1 is —H or —CH3; wherein R2 is —H or —CH3; or wherein R1 and R2 taken together are wherein p is 1 to 4 inclusive; or wherein R6 is a) —H, b) —CH3, c) —F, or d) —OCH3; wherein R3 is a) —CH2C6H5, b) —CH2CH2C6H5, c) —CH2CH2CH2C6H5, d) —CH2CH2CH2CH2C6H5, e) —CH2CH(CH3)C6H5, f) —CH2CH2C6H4X, wherein X may occupy either the ortho, meta or para-positions and is i) F ii) Cl, iii) Br, iv) OCH2R1, v) N(CH3)2, vi) NHSO2CH2R1, vii) SCH3 viii) NHCOCH2R1, or ix) NHSO2C6H4X1, wherein X1 is a. H, b. CH3, c. F, or d. CN; g) —CH═CH—C6H5, (cis or trans); h) —CH≡C—C6H5); i) CH═CH—C6H3X2 wherein X2 is a. F, b. Cl, c. OCH3, or d. OCH2O; wherein CH2CH2 is appended to the 1- or 2-positions; or wherein i) —CH2CH2— appended to the 2- or 3-positions, ii) X3 is a. O, b. S, c. NH, d. NCH3, and iii) R7 is a. CH3, or b. CH3CH2; wherein R4 is —H or —CH3; and wherein R5 is —H or —CH3; provided that when R1 is —CH3 and R2 is —H or —CH3, R4 is not —H.
- 2. The compound of claim 1wherein R1 is —H or —CH3; wherein R2 is —H or —CH3; wherein R3 is a) —CH2C6H5, b) —CH2CH2C6H5, c) —CH2CH2CH2C6H5, d) —CH2CH2CH2CH2C6H5, e) —CH2CH(CH3)C6H5, f) —CH2CH2C6H4X, wherein X is i) F, ii) Cl, or iii) Br, g) —CH═CH—C6H5, (cis or trans) or h) —C≡C—C6H5; wherein R4 is —H or —CH3; and wherein R5 is —H or —CH3; provided that when R1 is —CH3 and R2 is —H or —CH3, R4 is not —H.
- 3. The compound of claim 1 of the formula I wherein R1 and R2 taken together are wherein R6 is a) —H b) —CH3, c) —F, or d) —OCH3.
- 4. The compound of claim 1 of the formula I wherein R1 and R2 taken together are wherein p is 1 to 4 inclusive.
- 5. The compound of claim 1 selected from the group consisting of:2,3-Dimethyl-α-(2-phenylethynyl)imidazo-[2,1-b]thiazole-5-methanol, 2,3-Dimethyl-α-(2-phenylmethyl)imidazo-[2,1-b]thiazole-5-methanol, 2,3-Dimethyl-α-(3-phenylpropyl)imidazo-[2,1b]thiazole-5-methanol, 2,3-Dimethyl-α-Di(2-phenylethyl)imidazo-[2,1-b]thiazole-5-methanol, α,3-Dimethyl-α-(E-2-phenyl-E-ethenyl)imidazo[2,1-b]thiazole-5-methanol, 3-Methyl-α-(2-phenylpropyl)imidazo[2,1-b]thiazole-5-methanol, α,3-Dimethyl-α-(2-phenylethyl)imidazo[2,1-b]thiazole-5-methanol, 3-Methyl-α-(2-phenylethyl)imidazo[2,1-b]thiazole-5-methanol, 3-Methyl-α-(4-bromophenylethyl)imidazo[2,1-b]thiazole-5-methanol, 3-Methyl-α-(4-phenylbutyl)imidazo-[2,1-b]thiazole-5-methanol, 2,3-Dimethyl-α-(2-phenylethyl)imidazo[2,1-b]thiazole-5-methanol, 2,3-Dimethyl-α-(2-phenylethenyl)imidazo[2,1-b]thiazole-5-methanol, 6,7-Dihydro-α-(2-phenylethyl)-5H-cyclopent[d]imidazo[2,1-b]thiazole-3-methanol, 5,6,7,8-Tetrahydro-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol, 6,7,8,9-Tetrahydro-α-(2-phenylethyl)-5H-cyclohept[d]imidazo[2,1-b]thiazole-3-methanol, 6,7,8,9-Tetrahydro-α-(4-phenylbutyl)-5H-cyclohept[d]imidazo[2,1-b]thiazole-3-methanol, 5,6,7,8,9,10-Hexahydro-α-(2-phenylethyl)cyclooct[d]imidazo-[2,1-b]thiazole-3-methanol, α-(2-phenylethyl)-imidazo[2,1-b]benzothiazole-3-methanol, 7-Methyl-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol, 7-Fluoro-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol, 7-Methoxy-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol, α-[2-(3-Flurophenyl)ethenyl]-6,7,8,9-tetrahydro-5H-imidazo[2,1-b]thiazole-3-methanol α-[2-(3-Fluorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2, 1-b]thiazol-3-methanol, α-[2-(4-Flurophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2, 1-b]thiazol-3-methanol, [α-[2-(4-Flurophenyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol,]α-[2-(3-Bromophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo-2,1-b]thiazol-3-methanol, α-[2-(3-Chlorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, [α-[2-(3,5-Difluorophenyl)ethyl]-1-6,7,8,9-tetrahydro-5H-cyclohept[d]-imidazothiazol-3-methanol,]α-[2-(4-dimethylaminophenyl)ethyl-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo-2,1-b]thiazol-3-methanol, α-[2-(4-Dimethylaminophenyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]-imidazo[2,1-b]thiazol-3-methanol, N-[3-[3-(2,3-Dimethylimidazo[2, 1-b]thiazol-5-yl)-3-hydroxypropyl]phenyl-4-methylbenzenesulfonamide, N-[2-[3-(2,3-Dimethylimidazo[2, 1-b]thiazol-5-yl)-3-hydroxy-propyl]phenyl-4-methylbenzensulfonamide, [α-[2-(2,3-Difluorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo-thiazol-3-methanol,]α-[2-(4-methoxyphenyl)ethyl]6,7,8,9-tetrahydro-5H-cyclohept-[d]imidazo[2,1b]thiazol-3-methanol, and [α-[2-(4-methoxyphenyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept-[d]imidazo[2, 1-]thiazol-3-methanol,]α-[2-(2-Naphthalenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol], α-[2-(2-Furanyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(2-Furanyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(3-Furanyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(2-Furanyl)ethenyl]2,3-dimethylimidazo[2,1-b]thiazol-3-methanol, and α-[2-(2-Furanyl)ethyl]2,3-dimethylimidazo[2,1-b]thiazol-3-methanol].
- 6. The compound of claim 2 selected from the group consisting of:2,3-Dimethyl-α-(2-phenylethynl)imidazo-[2,1-b]thiazole-5-methanol, 2,3-Dimethyl-α-(2-phenylmethyl)imidazo-[2,1-b]thiazole-5-methanol, 2,3-Dimethyl-α-(3-phenylpropyl)imidazo-[2,1-b]thiazole-5-methanol, 2,3-Dimethyl-α-Di(2-phenylethyl)imidazo-[2,1-b]thiazole-5-methanol, α,3-Dimethyl-α-(E-2-phenyl-E-ethenyl)imidazo[2,1-b]thiazole-5-methanol, 3-Methyl-α-(2-phenylpropyl)imidazo[2,1-b]thiazole-5-methanol, α,3-Dimethyl-α-(2-phenylethyl)imidazo[2,1-b]thiazole-5-methanol, and 3-Methyl-α-(2-phenylethyl)imidazo[2,1-b]thiazole-5-methanol, 3-Methyl-α-(4-bromophenylethyl)imidazo[2,1-b]thiazole-5-methanol, 3-Methyl-α-(4-phenylbutyl)imidazo-[2,1b]thiazole-5-methanol, 2,3-Dimethyl-α-(2-phenylethyl)imidazo[2,1-b]thiazole-5-methanol, 2,3-Dimethyl-α-(2-phenylethenyl)imidazo[2,1-b]thiazole-5-methanol, N-[3-[3-(2,3-Dimethylimidazo[2, 1-b]thiazol-5-yl)-3-hydroxypropyl]phenyl-4-methylbenzenesulfonamide, and N-[2-[3-(2,3-Dimethylimidazo[2, 1-b]thiazol-5-yl)-3-hydroxy-propyl]phenyl-4-methylbenzensulfonamide, [α-[2-(2-Furanyl)ethenyl]2,3-dimethylimidazo[2,1-b]thiazol-3-methanol, and α-[2-(2-Furanyl)ethyl]2,3-dimethylimidazo[2,1-b]thiazol-3-methanol].
- 7. The compound of claim 3 selected from the group consisting of:α- (2phenylethyl)-imidazo[2,1-b]benzothiazole-3-methanol, 7-Methyl-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol, 7-Fluoro-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol, and 7Methoxy-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol.
- 8. The compound of claim 4 selected from the group consisting of:6,7-Dihydro-α-(2-phenylethyl)-5H-cyclopent[d]imidazo[2,1-b]thiazole-3-methanol, 5,6,7,8-Tetrahydro-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol, 6,7,8,9-Tetrahydro-α-(2-phenylethyl)-5H-cyclohept[d]imidazo[2,1-b]thiazole-3-methanol, 6,7,8,9-Tetrahydro-α-(4-phenylbutyl)-5H-cyclohept[d]imidazo[2,1-b]thiazole-3-methanol, 5,6,7,8,9,10-Hexahydro-α-(2-phenylethyl)cyclooct[d]imidazo-[2,1-b]thiazole-3-methanol, α-[2-(3-Fluorophenyl)ethenyl]-6,7,8,9-tetrahydro-5H-imidazo]2,1-b]thiazole-3-methanol α-[2-(3-Fluorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2, 1-b]thiazol-3-methanol, α-[2-(4-Fluorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2, 1-b]thiazol-3-methanol, [α-[2-(4-Fluorophenyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol,]α-[2-(3-Bromophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo-2,1-b]thiazol-3-methanol, α-[2-(3-Chlorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, [α-[2-(3,5-Difluorophenyl)ethyl]-1-6,7,8,9-tetrahydro-5H-cyclohept[d]-imidazothiazol-3-methanol,]α-[2-(4-dimethylaminophenyl)ethyl-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo-[2,1-b]thiazol-3-methanol, α-[2-(4-Dimethylaminophenyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]-imidazo[2,1-b]thiazol-3-methanol, α-[2-(2,3-Difluorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo-thiazol-3-methanol,]α-[2-(4-methoxyphenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept-[d]imidazo[2,1b]thiazol-3-methanol, and [α-[2-(4-methoxyphenyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept-[d]imidazo[2, 1-b]thiazol-3-methanol,]α-[2-(2-Naphthalenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol[, α-[2-(2-Furanyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(2-Furanyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(3-Furanyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol.
- 9. A method for treatment of mammals infected with a retrovirus, said method comprising administering to a mammal infected with said retrovirus a therapeutically effective amount of a compound of the formula I wherein R1 is —H or —CH3; wherein R2 is —H or —CH3; or wherein R1 and R2 taken together are wherein p is 1 to 4 inclusive; or wherein R6 is a) —H b) —CH3, c) —F, or d) —OCH3; wherein R3 is a) —CH2C6H5, b) —CH2CH2C6H5, c) —CH2CH2CH2C6H5, d) —CH2CH2CH2CH2C6H5, e) —CH2CH(CH3)C6H5, f) —CH2CH2C6H4X, wherein X may occupy either the ortho, meta or para-positions and is i) F, ii) Cl, iii) Br, iv) OCH2R1, v) N(CH3)2, vi) NHSO2CH2R1, vii) SCH3 viii) NHCOCH2R1, or ix) NHSO2C6H4X1, wherein X1is a. H, b. CH3, c. F, or d. CN; g) —CH═CH—C6H5, (cis or trans); h) —CH≡C—C6H5); i) —CH═CH—C6H3X2 wherein X2 is a. F, b. Cl, c. OCH3, or d. —O—CH2O; wherein CH2CH2 is appended to the 1- or 2-positions; or wherein i) —CH2CH2— appended to the 2- or 3- positions, ii) X3 is a. O, b. S, c. NH, and d. —NCH3; iii) R7 is a. CH3, or b. CH3CH2; wherein R4 is —H or —CH3; and wherein R5 is —H or —CH3; provided that when R1 is —CH3 and R2 is —H or —CH3, R4 is not —H.
- 10. The method of claim 9 wherein the compound is selected from the group consisting of:2,3-Dimethyl-α-(2-phenylethynyl)imidazo-[2,1-b]thiazole-5-methanol, 2,3-Dimethyl-α-(2-phenylmethyl)imidazo-[2,1-b]thiazole-5-methanol, 2,3-Dimethyl-α-(3-phenylpropyl)imidazo-[2,1-b]thiazole-5-methanol, 2,3-Dimethyl-α-(2-phenylethyl)imidazo-[2,1-b]thiazole-5-methanol, α,3-Dimethyl-α-(E-2-phenyl-E-ethenyl)imidazo[2,1-b]thiazole-5-methanol, 3-Methyl-α-(2-phenylpropyl)imidazo[2,1-b]thiazole-5-methanol, α,3-Dimethyl-α-(2-phenylethyl)imidazo[2,1-b]thiazole-5-methanol, 3-Methyl-α-(2-phenylethyl)imidazo[2,1-b]thiazole-5-methanol, 3-Methyl-α-(4-bromophenylethyl)imidazo[2,1-b]thiazole-5-methanol, 3-Methyl-α-(4-phenylbutyl)imidazo-[2,1-b]thiazole-5-methanol, 2,3-Dimethyl-α-(2-phenylethyl)imidazo[2,1-b]thiazole-5-methanol, 2,3-Dimethyl-α-(2-phenylethenyl)imidazo[2,1-b]thiazole-5-methanol, 6,7-Dihydro-α-(2-phenylethyl)-5H-cyclopent[d]imidazo[2,1-b]thiazole-3-methanol, 5,6,7,8-Tetrahydro-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol, 6,7,8,9-Tetrahydro-α-(2-phenylethyl)-5H-cyclohept[d]imidazo[2,1-b]thiazole-3-methanol, 6,7,8,9-Tetrahydro-α-(4-phenylbutyl)-5H-cyclohept[d]imidazo[2,1-b]thiazole-3-methanol, 5,6,7,8,9,10-Hexahydro-α-(2-phenylethyl)cyclooct[d]imidazo-[2,1-b]thiazole-3-methanol, α-(2-phenylethyl)-imidazo[2,1-b]benzothiazole-3-methanol, 7-Methyl-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol, 7-Fluoro-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol, 7-Methoxy-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol, α[2-(3-Fluorophenyl)ethenyl]-6,7,8,9-tetrahydro-5H-imidazo[2,1-b]thiazole-3-methanol α[2-(3-Fluorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2, 1-b]thiazol-3-methanol, α-[2-(4-Fluorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2, 1-b]thiazol-3-methanol, [α-[2-(4-Fluorophenyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol,]α-[2-(3-Bromophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo-2,1-b]thiazol-3-methanol, α-[2-(3-Chlorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, [α[2-(3,5-Difluorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]-imidazothiazol-3-methanol,]α-[2-(4-dimethylaminophenyl)ethyl-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo-[2,1-b]thiazol-3-methanol, α-[2-(4-Dimethylaminophenyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]-imidazo[2,1-b]thiazol-3-methanol, N-[3-[3-(2,3-Dimethylimidazo[2, 1-b]thiazol-5-yl)-3-hydroxypropyl]phenyl-4-methylbenzenesulfonamide, N-[2-[3-(2,3-Dimethylimidazo[2, 1-b]thiazol-5-yl)-3-hydroxy-propyl]phenyl-4-methylbenzensulfonamide, [α-[2-(2,3-Difluorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo-thiazol-3-methanol,]α-[2-(4-methoxyphenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept-[d]imidazo[2,1-b]thiazol-3-methanol, and [α-[2-(4-methoxyphenyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept-[d]imidazo[2, 1-b]thiazol-3-methanol,]α-[2-(2-Naphthalenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol], α-[2-(2-Furanyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(2-Furanyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(3-Furanyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(2-Furanyl)ethenyl]2,3-dimethylimidazo[2,1-b]thiazol-3-methanol, and α-[2-(2-Furanyl)ethyl]2,3-dimethylimidazo[2,1-b]thiazol-3-methanol].
- 11. A pharmaceutical composition for use in treatment of a mammal infected with a retrovirus, said composition comprising a pharmaceutically acceptable solvent, diluent, adjuvant or carrier and, as the active ingredient, from about 0.1 mg to 100 mg per kg of body weight per day of a compound of the formula I wherein R1 is —H or —CH3; wherein R2 is —H or —CH3; or wherein R1 and R2 taken together are wherein p is 1 to 4 inclusive; or wherein R6 is a) —H b) —CH3, c) —F, or d) —OCH3; wherein R3 is a) —CH2C6H5, b) —CH2CH2C6H5, c) —CH2CH2CH2C6H5, d) —CH2CH2CH2CH2C6H5, e) —CH2CH(CH3)C6H5, f) —CH2CH2C6H4X, wherein X may occupy either the ortho, meta or para positions and is i) F, ii) Cl, iii) Br, iv) OCH2R1, v) N(CH3)2, vi) NHSO2CH2R1, vii) SCH3 viii) NHCOCH2R1, or ix) NHSO2C6H4X1, wherein X1 is a. H, b. CH3, c. F, or d. CN; g) —CH═CH—C6H5, (cis or trans); h) —CH≡C—C6H5); i) CH═CH—C6H3X2 wherein X2 is a. F, b. Cl, c. OCH3, or d. —O—CH2O; wherein CH2CH2 is appended to the 1- or 2-positions; or wherein i) —CH2CH2— appended to the 2- or 3-positions, ii) X3 is a. O, b. S, c. NH, d. —NCH3, and iii) R7 is a. CH3, or b. CH3CH2; wherein R4 is —H or —CH3; and wherein R5 is —H or —CH3; provided that when R1 is —CH3 and R2 is —H or —CH3, R4 is not —H.
- 12. The composition of claim 11 wherein the compound is selected from the group consisting of:2,3-Dimethyl-α-(2-phenylethynyl)imidazo-[2,1-b]thiazole-5-methanol, 2,3-Dimethyl-α-(2-phenylmethyl)imidazo-[2,1-b]thiazole-5-methanol, 2,3-Dimethyl-α-(3-phenylpropyl)imidazo-[2,1-b]thiazole-5-methanol, 2,3-Dimethyl-α-Di(2-phenylethyl)imidazo-[2,1-b]thiazole-5-methanol, α,3-Dimethyl-α-(E-2-phenyl-E-ethenyl)imidazo[2,1-b]thiazole-5-methanol, 3-Methyl-α-(2-phenylpropyl)imidazo[2,1-b]thiazole-5-methanol, α,3-Dimethyl-α-(2-phenylethyl)imidazo[2,1-b]thiazole-5-methanol, 3-Methyl-α-(2-phenylethyl)imidazo[2,1-b]thiazole-5-methanol, 3-Methyl-α-(4-bromophenylethyl)imidazo[2,1-b]thiazole-5-methanol, 3-Methyl-α-(4-phenylbutyl)imidazo-[2,1-b]thiazole-5-methanol, 2,3-Dimethyl-α-(2-phenylethyl)imidazo[2,1-b]thiazole-5-methanol, 2,3-Dimethyl-α-(2-phenylethenyl)imidazo[2,1-b]thiazole-5-methanol, 6,7-Dihydro-α-(2-phenylethyl)-5H-cyclopent[d]imidazo[2,1-b]thiazole-3-methanol, 5,6,7,8-Tetrahydro-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol, 6,7,8,9-Tetrahydro-α-(2-phenylethyl)-5H-cyclohept[d]imidazo[2,1-b]thiazole-3-methanol, 6,7,8,9-Tetrahydro-α-(4-phenylbutyl)-5H-cyclohept[d]imidazo[2,1-b]thiazole-3-methanol, 5,6,7,8,9,10-Hexahydro-α-(2-phenylethyl)cyclooct[d]imidazo-[2,1-b]thiazole-3-methanol, α-(2-phenylethyl)-imidazo[2,1-b]benzothiazole-3-methanol, 7-Methyl-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol, 7-Fluoro-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol, 7-Methoxy-α-(2-phenylethyl)imidazo[2,1-b]benzothiazole-3-methanol, α-[2-(3-Fluorophenyl)ethenyl]-6,7,8,9-tetrahydro-5H-imidazo[2,1-b]thiazole-3-methanol α-[2-(3-Fluorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2, 1-b]thiazol-3-methanol, α-[2-(4-Fluorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2, 1-b]thiazol-3-methanol, [α-[2-(4-Fluorophenyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(3-Bromophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo-2,1-b]thiazol-3-methanol, α-[2-(3-Chlorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(3,5-Difluorophenyl)ethyl]-1 6,7,8,9-tetrahydro-5H-cyclohept[d]-imidazothiazol-3-methanol,]α-[2-(4-dimethylaminophenyl)ethyl-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo-[2,1-b]thiazol-3methanol, α-[2-(4-Dimethylaminophenyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]-imidazo[2,1-b]thiazol-3-methanol, N-[3-[3-(2,3-Dimethylimidazo[2, 1-b]thiazol-5-yl)-3-hydroxypropyl]phenyl-4-methylbenzenesulfonamide, N-[2-[3-(2,3-Dimethylimidazo[2, 1-b]thiazol-5-yl)-3-hydroxy-propyl]phenyl-4-methylbenzensulfonamide, [α-[2-(2,3-Difluorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo-thiazol-3-methanol,]α-[2-(4-methoxyphenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept-[d]imidazo[2,1-b]thiazol-3-methanol, and [α[2-(4-methoxyphenyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept-[d]imidazo[2, 1-b]thiazol-3-methanol,]α-[2-(2-Naphthalenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol], α-[2-(2-Furanyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(2-Furanyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(3-Furanyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(2-Furanyl)ethenyl]2,3-dimethylimidazo[2,1-b]thiazol-3-methanol, and α-[2-(2-Furanyl)ethyl]2,3-dimethylimidazo[2,1-b]thiazol-3-methanol].
- 13. A compound selected from the group consisting of:α-[2-(4-Fluorophenyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(3,5-Difluorophenyl)ethyl]-1-6,7,8,9-tetrahydro-5H-cyclohept[d]-imidazothiazol-3-methanol, α-[2-(2,3-Difluorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazothiazol-3-methanol, α-[2-(4-methoxyphenyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept-[d]imidazo[2, 1-b]thiazol-3-methanol, α-[2-(2-Furanyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(2-Furanyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(3-Furanyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(2-Furanyl)ethenyl]2,3-dimethylimidazo[2,1-b]thiazol-3-methanol, and α-[2-(2-Furanyl)ethyl]2,3-dimethylimidazo[2,1-b]thiazol-3-methanol.
- 14. A method for treatment of mammals infected with a retrovirus, said method comprising administering to a mammal infected with said retrovirus a therapeutically effective amount of a compound selected from the group consisting of:α-[2-(4-Fluorophenyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(3,5-Difluorophenyl)ethyl]-1-6,7,8,9-tetrahydro-5H-cyclohept[d]-imidazothiazol-3-methanol, α-[2-(2,3-Difluorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazothiazol-3-methanol, α-[2-(4-methoxyphenyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept-[d]imidazo[2, 1-b]thiazol-3-methanol, α-[2-(2-Furanyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(2-Furanyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(3-Furanyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α-[2-(2-Furanyl)ethenyl]2,3-dimethylimidazo[2,1-b]thiazol-3-methanol, and α-[2-(2-Furanyl)ethyl]2,3-dimethylimidazo[2,1-b]thiazol-3-methanol.
- 15. A pharmaceutical composition for use in treatment of a mammal infected with a retrovirus, said composition comprising a pharmaceutically acceptable solvent, diluent, adjuvant or carrier and, as the active ingredient, from about 0.1 mg to 100 mg per kg of body weight per day of a compound selected from the group consisting of:α[2-(4-Fluorophenyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α[2-(3,5-Difluorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]-imidazothiazol-3-methanol, α[2-(2,3-Difluorophenyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]-imidazothiazol-3-methanol, α[2-(4-methoxyphenyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept-[d]imidazo[2, 1-b]thiazol-3-methanol, α[2-(2-Furanyl)ethenyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α[2-(2-Furanyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α[2-(3-Furanyl)ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, α[2-(2-Furanyl)ethenyl]2,3-dimethylimidazo[2,1-b]thiazol-3-methanol, and α[2-(2-Furanyl)ethyl]2,3-dimethylimidazo[2,1-b]thiazol-3-methanol.
Parent Case Info
This application is a 371 of PCT/US95/04444 filed Apr. 20, 1995, and a C-I-P of Ser. No. 08/236,417 filed Apr. 29, 1994 now abandoned.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/US95/04444 |
|
WO |
00 |
4/7/1997 |
4/7/1997 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO95/29922 |
11/9/1995 |
WO |
A |
Foreign Referenced Citations (1)
Number |
Date |
Country |
269 919 |
Jan 1994 |
DE |
Non-Patent Literature Citations (2)
Entry |
Moog, Christiane, et al., Bicyclic imidazo derivatives, a new class of highly selective inhibitors for the human immunodeficiency virus type 1; Antiviral Research 24 (1994) 275-288. |
Science, vol. 265, 1028-1029, Aug. 19, 1994. |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
08/236417 |
Apr 1994 |
US |
Child |
09/180809 |
|
US |