Cyclic substituted aminomethyl compounds and medicaments comprising these compounds
AssigneeGruenenthal GmbH
InventorsOswald Karl Zimmer, Babette-Yvonne Koegel, Wolfgang Werner Alfred Strassburger
Life of this patent
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Abstract
Cyclic substituted aminomethyl compounds of general formula IA and IB, methods for production thereof, intermediates in said production methods, a medicament containing at least one of said cyclic substituted aminomethyl compounds, the use of said cyclic substituted aminomethyl compounds for the production of a medicament, pharmaceutical compositions containing said compounds, and methods for the treatment of pain, incontinence, pruritis, tinnitus aurium and/or diarrhea using said pharmaceutical compositions.
Claims28
A cyclic substituted aminomethyl compound of formula IA or IB
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- wherein
- R1 denotes H, F, Cl, OH, O—(C1-6-alkyl), O—(C3-7-cycloalkyl), CH3, C2-6-alkyl, CH2F, CHF2 or CF3,
- R2 denotes H, F, Cl, C1-6-alkyl, CH2F, CHF2 or CF3,
- R3 and R4 independently of one another denote H, F, Cl, OH, O—(C1-6-alkyl), O—(C3-7-cycloalkyl), C1-6-alkyl, CH2F, CHF2, CF3, O-aryl, aryl or heterocyclyl,
- R5 and R6 independently of one another denote C1-6-alkyl, C3-7-cycloalkyl, CH2-(C3-7-cycloalkyl), aryl, (C1-6-alkyl)-aryl, heterocyclyl or (C1-6-alkyl) -heterocyclyl,
- X denotes CH2, O, S, SO or SO2, and
- n is 0, 1, 2 or 3 if X denotes CH2, and is 1, 2 or 3 if X denotes O, S, SO or SO2,
- or a pharmaceutically acceptable salt thereof.
A process for the preparation of a compound of formula IA or IB
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- wherein
- R1 denotes H, F, Cl, OH, O—(C1-6-alkyl), O—(C3-7-cycloalkyl), C1-6-alkyl, CH2F, CHF2 or CF3,
- R2 denotes H, F, Cl, C1-6-alkyl, CH2F, CHF2 or CF3,
- R3 and R4 independently of one another denote H, F, Cl, OH, O—(C1-6-alkyl), O—(C3-7-cycloalkyl), C1-6-alkyl, CH2F, CHF2, CF3, O-aryl, aryl or heterocyclyl,
- R5 and R6 independently of one another denote C1-6-alkyl, C3-7-cycloalkyl, CH2—(C3-7-cycloalkyl), aryl, (C1-6-alkyl)-aryl, heterocyclyl or (C1-6-alkyl)-heterocyclyl,
- X denotes CH2, O, S, SO or SO2, and
- n is 0, 1, 2 or 3 if X denotes CH2;
- and is 1, 2 or 3 if X denotes O, S, SO or SO2,
- the process comprising reacting a tertiary alcohol of formula II
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- wherein R1 to R6, X and n are as defined above,
- with an acid.
A tertiary alcohol of formula II or III
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- wherein
- R1 denotes H, F, Cl, OH, O—(C1-6-alkyl), O—(C3-7-cycloalkyl), C1-6-alkyl, CH2F, CHF2 or CF3,
- R2 denotes H, F, Cl, C1-6-alkyl, CH2F, CHF2 or CF3,
- R3 and R4 independently of one another denote H, F, Cl, OH, O—(C1-6-alkyl), O—(C3-7-cycloalkyl), C1-6-alkyl, CH2F, CHF2, CF3, O-aryl, aryl or heterocyclyl,
- R5 and R6 independently of one another denote C1-6-alkyl, C3-7-cycloalkyl, CH2—(C3-7-cycloalkyl), aryl, (C1-6-alkyl)-aryl, heterocyclyl or (C1-6-alkyl) -heterocyclyl,
- R7 denotes H, F, Cl, O—(C1-6-alkyl), O—(C3-7-cycloalkyl), O—CH2-phenyl, O—SiR10R11R12, wherein R10, R11 and R12 independently of one another are C1-6-alkyl or phenyl, CH2F, CHF2 or CF3,
- R8 and R9 independently of one another denote H, F, Cl, O—CH3, O—(C2-6-alkyl), O—(C3-7-cycloalkyl), O—CH2-phenyl, O—SiR10R11R12, wherein R10, R11 and R12 independently of one another are CH3, C2-6-alkyl or phenyl, CH3, C2-6-alkyl, CH2F, CHF2, CF3, O-aryl, aryl or heterocyclyl, in each case in the α-, β-, γ-and/or δ-position of the aromatic ring,
- and at least one of R7, R8 and R9 is O—CH3, O—(C2-6-alkyl), O—(C3-7-cycloalkyl), O—CH2-phenyl or O—SiR10R11R12,
- X denotes CH2, O, S, SO or SO2, and
- n is 0, 1, 2 or 3 if X denotes CH2, and is 1, 2 or 3 if X denotes O, S, SO or SO2.
Dependencies are inferred from the claim text.