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US 6,653,508 B2Granted
3-amino-2-benzyl-1-phenylpropane derivatives
AssigneeGruenenthal GmbH
InventorsMichael Sattlegger, Helmut Buschmann, Babette-Yvonne Koegel
Life of this patent
Estimating the term…
Abstract
Substituted 3-amino-2-benzyl-1-phenlypropane derivatives, methods for preparing them, pharmaceutical compositions containing them, and methods of using them to treat various medical conditions.
Claims61
A substituted 3-amino-2-benzyl-1-phenylpropane compound of formula I,
- wherein
- R0 denotes OH or a single bond,
- R1 denotes H, a C1-10-alkyl, an aryl or an aryl radical bound via a C1-6-alkylene group
- R2 denotes H, a C1-10-alkyl, an aryl, or an aryl radical bound via a C1-6-alkylene group
- R3 denotes H, OH, NH2, halogen, OR7, CHR9, a C1-10-alkyl, a C2-10-alkenyl, an aryl or an aryl radical bound via a C1-6-alkylene group
- or together with R0 denote a group ═O, ═CHR11 or ═N—OH,
- R4-radicals, which may be identical or different, denote H, OH, CN, OR7, SR7, halogen, a C1-10-alkyl, a PO(OR10)3—, an aryl, a heterocyclyl, or an aryl or heterocyclyl radical bound via a C1-6-alkylene group,
- R5-radicals, which may be identical or different, denote H, OH, CN, OR7, SR7, halogen, a C1-10-alkyl, a PO(OR10)3—, an aryl, a heterocyclyl, or an aryl or heterocyclyl radical bound via a C1-6-alkylene group
- R6-radicals, which may be identical or different, denote H, OH, CN, OR7, SR7, halogen, a C1-10-alkyl, a PO(OR10)3—, an aryl, a heterocyclyl, or an aryl or heterocyclyl radical bound via a C1-6-alkylene group
- R7-radicals, which may be identical or different, denote a C1-10-alkyl, an aryl or an aryl radical bound via a C1-6 alkylene group,
- R8 denotes a C1-10-alkyl, an aryl or an aryl radical bound via a C1-6-alkylene group,
- R9 denotes OH, halogen, OR10, SR10 or a C1-10-alkyl radical,
- R10 denotes a C1-10-alkyl or a C4-8-cycloalkyl radical,
- R11 denotes a C1-10-alkyl radical
- R12 radicals, which may be identical or different, denote H, a C1-10-alkyl, a C4-8-cycloalkyl, an aryl or an aryl radical bound via a C1-6-alkylene group,
- and/or their enantiomers, diastereomers, bases or salts of physiologically compatible acids,
- the compounds of formula I′ being excluded
- wherein the radicals R0 and R3 together denote the group ═O, and R1, R2, R4 to R6 and R4′ to R6′ denote H, and also the radicals R12 in each case denote CH3, as well as the corresponding hydrochloride,
- wherein R0 and R3 together denote the group ═O, R6 denotes the group OCH3 and R1, R2, R4, R5 and R4′ to
- R6′ denote H, and also the radicals R12 in each case denote CH3, as hydrochloride,
- wherein R0 and R3 together denote the group ═O, R6′ denotes the group OCH3 and R1, R2, R4 to R6, R4′ and R5′ denote H, and also the radicals R12 in each case denote CH3, as well as the corresponding hydrochloride,
- wherein R0 and R3 together denote the group ═O, R6′ denotes Cl and R1, R2, R4 to R6, R4′ and R5′ denote H, and also the radicals R12 in each case denote CH3,
- wherein R0 and R3 together denote the group ═O, R5′ and R6′ in each case denote the group OCH3, and R1, R2, R4 to R6 and R4′ denote H, and also the radicals R12 in each case denote CH3, as hydrochloride,
- wherein R0 and R3 together denote the group ═O, R4, R6 and R6′ in each case denote the group OCH3, and R1, R2, R5, R4′ and R5′ denote H, and also the radicals R12 in each case denote CH3, as hydrochloride,
- wherein R0 denotes OH, R3 denotes H, CH3, unbranched C3H7, unbranched C5H11, cyclohexyl, phenyl or benzyl, and R1, R2, R4 to R6 and R4′ to R6′ denote H, and also the radicals R12 in each case denote CH3, as well as the corresponding hydrochlorides,
- wherein R0 denotes OH, R3 denotes C2H5 and R1, R2, R4 to R6 and R4′ to R6′ denote H and also the radicals R12 in each case denote CH3, as well as the corresponding hydrochloride and the corresponding methyl iodide,
- wherein R0 denotes OH, R3 denotes phenyl, R6 denotes Cl, R1, R2, R4, R5 and R4′ to R6′ denote H, and also the radicals R12 in each case denote CH3, as well as the corresponding hydrochloride,
- wherein R0 denotes OH, R3 denotes phenyl, R6′ denotes Cl, R1, R2, R4 to R6, R4′ and R5′ denote H, and also the radicals R12 in each case denote CH3, as well as the corresponding hydrochloride,
- wherein R0 denotes OH, R3 denotes phenyl, R5′, R6′ in each case denote the group OCH3, R1, R2, R4 to R6 and R4′ denote H, and also the radicals R12 in each case denote CH3, as hydrochloride,
- wherein R0 denotes OH, R3 denotes phenyl, R6 denotes the group OCH3, R1, R2, R4, R5 and R4′ to R6′ denote H, and also the radicals R12 in each case denote CH3, as well as the corresponding hydrochloride,
- wherein R0 denotes OH, R3 denotes phenyl, R6′ denotes the group OCH3, R1, R2, R4 to R6, R4′ and R5′ denote H, and also the radicals R12 in each case denote CH3, as well as the corresponding hydrochloride and the corresponding methyl iodide,
- wherein R0 denotes OH, R3 denotes phenyl, R6 and R6′ in each case denote the group OCH3, R1, R2, R4, R5, R4′ and R5′ denote H, and also the radicals R12 in each case denote CH3, as well as the corresponding hydrochloride,
- wherein R0 denotes OH, R6′ denotes OCH3, R1 to R6, R4′ and R5′ denote H, and also the radicals R12 in each case denote CH3, as well as the corresponding hydrochloride,
- wherein R1, R2, the radicals R4 to R6, the radicals R4′ to R6′ in each case denote H, the radicals R3 and R0 together denote the group ═CHR11, and also the radical R11 and in each case the radicals R12 denote CH3, as hydrochloride
- wherein R1, R2, the radicals R4 to R6, the radicals R4′ to R6′ in each case denote H, the radicals R3 and R0 together denote the group ═N—OH, and also the radicals R12 in each case denote CH3, as well as the corresponding hydrochloride, and
- wherein R1, R2, the radicals R4 to R6, the radicals R4′ to R6′ in each case denote H, the radicals R3 and R0 together denote the group ═O, and also the radicals R12 in each case denote C2H5, as hydrochloride.
33 more elements
Dependencies are inferred from the claim text.