Back to results
US 2003/0232891 A1Published application
Substituted C-cyclohexylmethylamine derivatives
AssigneeGruenenthal GmbH
InventorsBernd Sundermann, Corinna Maul, Helmut Buschmann, Michael Finkam, Babette-Yvonne Koegel
Life of this patent
Estimating the term…
Abstract
Substituted C-cyclohexylmethylamine derivatives, methods for the production thereof, pharmaceuticals containing said compounds, the use of substituted C-cyclohexylmethylamine derivatives for producing pharmaceuticals, and method of pain treatment using the pharmaceuticals.
Claims56
A compound of formula I,
- 56
- wherein
- A is H;
- or singly or multiply substituted or unsubstituted aryl or heteroaryl;
- R1 is saturated or unsaturated, branched or unbranched, C1-10 alkyl or C3-10 cycloalkyl;
- aryl;
- heteroaryl;
- aryl bound by C1-3 alkyl or C1-3 alkylene or C1-3 ethinyl;
- C3-10 cycloalkyl bound by C1-3 alkyl or C1-3 alkylene or C1-3 ethinyl;
- or heteroaryl bound by C1-3 alkyl or C1-3 alkylene or C1-3 ethinyl, wherein R1 is unsubstituted, or singly or independently multiply substituted by:
- F, Cl, Br, I, OR18, SR18, SO2R18, SO2OR18, CN, COOR18, NR19R20;
- unsubstituted or singly or multiply substituted C1-10 alkyl, C3-10 cycloalkyl or silyl;
- unsubstituted or singly or multiply substituted aryl or heteroaryl;
- and unsubstituted or singly or multiply substituted aryl bound by saturated or unsaturated C1-3 alkyl, C1-3 alkylene, C3-10 cycloalkyl or heteroaryl;
- wherein
- R18 is H;
- saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C1-10 alkyl or C3-10 cycloalkyl;
- unsubstituted or singly or multiply substituted aryl or heteroaryl;
- or unsubstituted or singly or multiply substituted aryl, C3-10 cycloalkyl or heteroaryl bound by C1-3 alkyl, C1-3 alkylene;
- and
- R19 and R20 independently of one another are H;
- saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C1-10 alkyl or C3-10 cycloalkyl;
- unsubstituted or singly or multiply substituted aryl or heteroaryl;
- or unsubstituted or singly or multiply substituted aryl bound by C1-3 alkyl, C1-3 alkylene, C3-10 cycloalkyl or heteroaryl;
- or
- R19 and R20 together form CH2CH2OCH2CH2, CH2CH2NR21CH2CH2 or (CH2)3-6,
- wherein R21 is H;
- unsubstituted or substituted phenyl;
- or saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C1-10 alkyl;
- R2 and R3 independently of one another are H;
- saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C1-10 alkyl or C3-10 cycloalkyl;
- singly or multiply substituted or unsubstituted aryl or heteroaryl;
- or singly or multiply substituted or unsubstituted aryl bound by C1-3 alkyl, C1-3 alkylene, C3-10 cycloalkyl or heteroaryl;
- or
- R2 and R3 together represent CH2CH2OCH2CH2, CH2CH2NR6CH2CH2 or (CH2)3-6,
- wherein R6 is H;
- saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C1-10 alkyl or C3-10 cycloalkyl;
- singly or multiply substituted or unsubstituted aryl or heteroaryl;
- or singly or multiply substituted or unsubstituted aryl bound by C1-3 alkyl, C1-3 alkylene, C3-10 cycloalkyl or heteroaryl;
- X has such a meaning that partial formula Ia:
- 57
- partial formula Ia
- which is a part of formula I, is
- 58
- wherein B is OH, OR7, H, F, Cl or NR8R9,
- wherein R is saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C1-10 alkyl or C3-10 cycloalkyl;
- singly or multiply substituted or unsubstituted aryl or heteroaryl;
- or singly or multiply substituted or unsubstituted aryl bound by C1-3 alkyl, C1-3 alkylene, C3-10 cycloalkyl or heteroaryl;
- and
- R8 and R9 independently of one another are H;
- saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C1-10 alkyl or C3-10 cycloalkyl;
- singly or multiply substituted or unsubstituted aryl or heteroaryl;
- or singly or multiply substituted or unsubstituted aryl bound by C1-3 alkyl, C1-3 alkylene, C3-10 cycloalkyl or heteroaryl;
- or
- R8 and R9 together form CH2CH2OCH2CH2, CH2CH2NR10CH2CH2 or (CH2)3-6,
- wherein R10 is H;
- saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C1-10 alkyl or C3-10 cycloalkyl;
- singly or multiply substituted or unsubstituted aryl or heteroaryl;
- or singly or multiply substituted or unsubstituted aryl bound by C1-3 alkyl, C1-3 alkylene, C3-10 cycloalkyl or heteroaryl,
- and formula Ib,
- 59
- formula Ib
- which is also part of formula I, is
- 60
- wherein R4 is H, COR5, SO2R5;
- saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C1-10 alkyl or C3-10 cycloalkyl;
- singly or multiply substituted or unsubstituted aryl or heteroaryl;
- or singly or multiply substituted or unsubstituted aryl bound by C1-3 alkyl, C1-3 alkylene, C3-10 cycloalkyl or heteroaryl,
- wherein R5 is saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C1-10 alkyl or C3-10 cycloalkyl;
- singly or multiply substituted or unsubstituted aryl or heteroaryl;
- or singly or multiply substituted or unsubstituted aryl bound by C1-3 alkyl. C1-3 alkylene, C3-10 cycloalkyl or heteroaryl,
- wherein V is OR4 or NR4R11, and
- wherein W is R11, OR12 or NR11R12,
- wherein R11 and R12 independently of one another are H;
- saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C7-10 alkyl or C3-10 cycloalkyl;
- singly or multiply substituted or unsubstituted aryl or heteroaryl;
- or singly or multiply substituted or unsubstituted aryl bound by C1-3 alkyl, C1-3 alkylene, C3-10 cycloalkyl or heteroaryl,
- wherein the compound is in the form of a racemate, a pure stereoisomer, a mixture of stereoisomers in any mixing ratio, in the illustrated form or in the form of its acid, base or a salt, or in the form of a solvate,
- provided that the following compounds are excluded,
- in which
- A is hydrogen,
- R1 is a phenyl ring O- or S-substituted singly in the 3 position,
- R2 and R3 are both methyl,
- partial formula Ia is:
- 61
- wherein B is OH, and
- partial formula Ib is
- 62
- wherein R4 is C1-6 alkyl, C2-6 alkenyl, C5-7 cycloalkyl methyl, substituted or unsubstituted phenyl or substituted or unsubstituted benzyl, or in which
- R2, R3 independently of one another are H;
- branched or unbranched, singly or multiply substituted or unsubstituted, saturated or unsaturated C1-C10 alkyl;
- saturated or unsaturated, singly or multiply substituted or unsubstituted C3-C7 cycloalkyl or C3-C7 heterocycle in which a carbon atom is replaced by N, S or O in the ring;
- saturated or unsaturated, singly or multiply substituted or unsubstituted alkylaryl or alkylheteroaryl;
- or singly or multiply substituted or unsubstituted aryl or heteroaryl;
- or
- R2 and R3 together form a ring and represent CH2CH2OCH2CH2, CH2CH2NR6CH2CH2 or (CH2)3-6;
- partial formula Ia is
- 63
- wherein A is hydrogen,
- R1 is an unsubstituted or singly or doubly substituted phenyl ring,
- B is H, F, Cl, OH or OR7, wherein R7 is branched or unbranched, singly or multiply substituted or unsubstituted, saturated or unsaturated C1-C10 alkyl;
- singly or multiply substituted or unsubstituted saturated or unsaturated C3-C7 cycloalkyl or a C3-C7 heterocycle, in which a carbon atom is replaced in the ring by N, S or O;
- saturated or unsaturated, singly or multiply substituted or unsubstituted alkylaryl or alkylheteroaryl;
- or singly or multiply substituted or unsubstituted aryl or heteroaryl;
- and partial formula Ib is
- 64
- wherein V is OR4 wherein R4 is COR5 and wherein R5 is unsubstituted or singly or multiply substituted C1-6 alkyl.
104 more elements
Dependencies are inferred from the claim text.