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US 9,802,921 B2Granted
Fluoromethyl-substituted pyrrole carboxamides iv
AssigneeGruenenthal GmbH
InventorsMelanie Reich, Stefan Schunk, Florian Jakob, Henning Steinhagen, Nils Damann, Michael Haurand, Richard Hamlyn, Marc Rogers, Kathy MacKenzie
Life of this patent
Estimating the term…
Abstract
The invention relates to pyrrole carboxamides bearing a fluoromethyl-moiety as voltage gated calcium channel blockers, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
Claims12
A compound of general formula (I),
- wherein
- n represents 0, 1 or 2;
- m represents 0;
- R1 represents heteroaryl;
- R2 represents CH2F;
- CHF2 or CF3;
- R3 represents H;
- methyl, ethyl, iso-propyl or cyclopropyl;
- (Het)Aryl represents phenyl, substituted by zero or one or two substituents of the group consisting of R6 and R7, wherein R6 and R7 are each independently of one another selected from the group consisting of F;
- Cl;
- CN;
- CF3;
- CH3;
- OH;
- OCF3;
- OCH;
- S(═O)CH3;
- S(═O)2CH3;
- cyclopropyl and O-cylopropyl;
- R4 represents H or C1-10-alkyl;
- and
- R5 represents H, C1-10-alkyl;
- C3-10-cycloalkyl;
- 3 to 10 membered heterocyclyl, aryl or heteroaryl;
- or C3-10-cycloalkyl;
- 3 to 10 membered heterocyclyl, aryl or heteroaryl in each case connected via a C1-8-alkylene group;
- or
- R4 and R5 together with the nitrogen atom connecting them form a 3 to 10 membered heterocyclyl;
- wherein said C1-6-alkyl, said C1-10-alkyl and said C1-8-alkylene in each case may be branched or unbranched and unsubstituted or mono- or poly-substituted;
- and wherein said C3-6-cycloalkyl, said C3-10-cycloalkyl, said 3 to 7 membered heterocyclyl, said 3 to 10 membered heterocyclyl, said aryl and said heteroaryl in each case may be unsubstituted or mono- or polysubstituted;
- wherein substituents of “C1-10-alkyl” and “C1-8-alkylene” are selected from the group consisting of F;
- Cl;
- Br;
- I;
- CF3;
- C(═O)—NH2;
- C(═O)—N(H)(C1-6-alkyl);
- C(═O)—N(C1-6-alkyl)2;
- OH;
- O—C1-6-alkyl;
- O—(C1-8-alkylene)-OH;
- O—(C1-8-alkylene)-O—C1-6-alkyl;
- NH2;
- N(H)(C1-6-alkyl);
- N(C1-6-alkyl)2;
- N(H)—C(═O)—C1-6-alkyl;
- N(H)—S(═O)2—C1-6-alkyl;
- N(C1-6-alkyl)-S(═O)2—C1-6-alkyl;
- N(H)—S(═O)2—NH2;
- SH;
- S—C1-6-alkyl;
- S(═O)2 C1-6-alkyl and S(═O)2—N(H)(C1-6-alkyl);
- and
- wherein substituents of “C3-10-cycloalkyl” and “3 to 10-membered heterocyclyl” are selected from the group consisting of F;
- Cl;
- Br;
- I;
- NO2;
- CF3;
- CN;
- ═O;
- C1-6-alkyl;
- C3-6-cycloalkyl or 3 to 7 membered heterocyclyl;
- C3-6-cycloalkyl or 3 to 7 membered heterocyclyl, each bridged via a C1-8-alkylene;
- CHO;
- C(═O)—C1-6-alkyl;
- CO2H;
- C(═O)O—C1-6-alkyl;
- CONH2;
- C(═O)NH—C1-6-alkyl;
- C(═O)N(C1-6-alkyl)2;
- OH;
- O—C1-6-alkyl;
- OCF3;
- O—(C1-8-alkylene)-OH;
- O—(C1-8-alkylene)-O—C1-6-alkyl;
- O—C(═O)—C1-6-alkyl;
- NH2;
- NH—C1-6-alkyl;
- N(C1-6-alkyl)2;
- NH—C(═O)—C1-6-alkyl;
- SH;
- alkyl;
- SCF3;
- S(═O)2—C1-6-alkyl;
- S(═O)2OH;
- S(═O)2O—C1-6-alkyl and S(═O)2—NH—C1-6-alkyl;
- wherein substituents of “aryl” and “heteroaryl” are selected from the group consisting of F;
- Cl;
- CF3;
- CN;
- C1-6-alkyl;
- C(═O)—OH;
- C(═O)—O—C1-6-alkyl;
- CO—NH2;
- C(═O)—N(H)C1-6-alkyl;
- C(═O)—N(C1-6-alkyl)2;
- OH;
- O—C1-6-alkyl;
- O—C(═O)—C1-6-alkyl;
- OCF3;
- OCHF2;
- OCH2F;
- NH2;
- N(H)C1-6-alkyl;
- N(C1-6-alkyl)2;
- N(H)—C(═O)—C1-6-alkyl;
- N(C1-6-alkyl)-C(═O)C1-6-alkyl;
- N(H)—S(═O)2—C1-6-alkyl;
- N(C1-6-alkyl)-S(═O)2(C1-6-alkyl);
- N(H)C(═O)NH2;
- N(H)C(═O)—N(H)C1-6-alkyl;
- N(H)—C(═O)—N(C1-6-alkyl)2;
- N(C1-6-alkyl)-C(═O)—NH2;
- N(C1-6-alkyl)C(═O)—N(H)C1-6-alkyl;
- N(C1-6-alkyl)-C(═O)—N(C1-6-alkyl)2;
- S(═O)2C1-6-alkyl;
- S(═O)2—NH2;
- S(═O)2—N(H)C1-6-alkyl and S(═O)2—N(C1-6-alkyl)2;
- optionally in the form of an individual stereoisomer or a mixture of stereoisomers,
- in the form of the free compound and/or a physiologically acceptable salt and/or a physiologically acceptable solvate thereof.
118 more elements
Dependencies are inferred from the claim text.