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US 6,958,357 B2Granted
Substituted benzimidazoles, processes for their preparation, their use as medicaments, and medicaments comprising them
AssigneeAventis Pharma Deutschland GmbH
InventorsArmin Hofmeister, Uwe Heinelt, Hans-Jochen Lang, Markus Bleich, Klaus Wirth, Michael Gekle
Life of this patent
Estimating the term…
Abstract
The invention relates to the use of compounds of formula I for the production of a medicament for the treatment of illnesses which can be influenced by inhibition of the Na+/H+ exchanger, and to a medicament comprising them. in which R1 to R9 have the meanings shown in the claims.
Claims18
A method for treating disorders of the respiratory drive, comprising administering to a patient in need thereof an effective amount of at least one compound of Formula I
- in which:
- R1 and R5 are, independently of one another, H, F, Cl, Br, I, CN, alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are OH or O-alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are OCOR10, NR11R12, COR13, COOH, COOR14, CONR11R12, or —(O)n—SOmR15, in which n is 0 or 1 and m is 0, 1, or 2;
- or
- R1 and R5 are O-phenyl, in which phenyl is unsubstituted or substituted by one to three substituents selected from F, Cl, Br, I, alkyl having 1 to 4 carbon atoms, OH, O-alkyl having 1 to 4 carbon atoms, NR16R17, CN, or (C1-C4)-alkylsulfonyl, in which the alkyl groups are unsubstituted or partially or completely substituted by fluorine;
- R16 and R17 are H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R10 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R11 and R12 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH2 group of said alkyl is optionally replaced be by O or NR18;
- or
- R11 and R12, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
- or
- R11 and R12 are COR19 or SO2R20;
- R18, R19, and R20 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R13 and R14 are alkyl having 1 to 4 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- R15 is alkyl or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine;
- or
- R15 is OH or NR21R22;
- R21 and R22 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH2 group of said alkyl is optionally replaced by O— or NR23;
- R23 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R21 and R22, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
- R2, R3, and R4 are, independently of one another, H or F;
- R6, R7, R8, and R9 are, independently of one another, H, F, Cl, Br, I, CN, alkyl, or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine;
- or
- R6, R7, R8, and R9 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- or
- R6, R7, R8, and R9 are OH, OCOR24, or NR25R26;
- R24 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R25 and R26 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R25 and R26 are COR27;
- or
- R25 and R26, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring, and at least one CH2 group thereof is optionally replaced by O or NR18;
- R27 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- a pharmaceutically tolerable salt thereof.
38 more elements
A method for treating acute and chronic kidney diseases, comprising administering to a patient in need thereof an effective amount of at least one compound of Formula I
- in which:
- R1 and R5 are, independently of one another, H, F, Cl, Br, I, CN, alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are OH or O-alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are OCOR10, NR11R12, COR13, COOH, COOR14, CONR11R12, or —(O)n—SOmR15, in which n is 0 or 1 and m is 0, 1, or 2;
- or
- R1 and R5 are O-phenyl, in which phenyl is unsubstituted or substituted by one to three substituents selected from F, Cl, Br, I, alkyl having 1 to 4 carbon atoms, OH, O-alkyl having 1 to 4 carbon atoms, NR16R17, CN, or (C1-C4)-alkylsulfonyl, in which the alkyl groups are unsubstituted or partially or completely substituted by fluorine;
- R16 and R17 are H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R10 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R11 and R12 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH2 group of said alkyl is optionally replaced be by O or NR18;
- or
- R11 and R12, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
- or
- R11 and R12 are COR19 or SO2R20;
- R18, R19, and R20 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R13 and R14 are alkyl having 1 to 4 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- R15 is alkyl or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine;
- or
- R15 is OH or NR21R22;
- R21 and R22 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH2 group of said alkyl is optionally replaced by O— or NR23;
- R23 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R21 and R22, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
- R2, R3, and R4 are, independently of one another, H or F;
- R6, R7, R8, and R9 are, independently of one another, H, F, Cl, Br, I, CN, alkyl, or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine;
- or
- R6, R7, R8, and R9 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- or
- R6, R7, R8, and R9 are OH, OCOR24, or NR25R26;
- R24 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R25 and R26 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R25 and R26 are COR27;
- or
- R25 and R26, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring, and at least one CH2 group thereof is optionally replaced by O or NR18;
- R27 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- a pharmaceutically tolerable salt thereof.
38 more elements
A method for treating disorders of intestinal function, comprising administering to a patient in need thereof an effective amount of at least one compound of Formula I
- in which:
- R1 and R5 are, independently of one another, H, F, Cl, Br, I, CN, alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are OH or O-alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are OCOR10, NR11R12, COR13, COOH, OCOR14, CONR11R12, or —(O)n—SOmR15, in which n is 0 or 1 and m is 0, 1, or 2;
- or
- R1 and R5 are O-phenyl, in which phenyl is unsubstituted or substituted by one to three substituents selected from F, Cl, Br, I, alkyl having 1 to 4 carbon atoms, OH, O-alkyl having 1 to 4 carbon atoms, NR16R17, CN, or (C1-C4)-alkvlsulfonyl, in which the alkyl groups are unsubstituted or partially or completely substituted by fluorine;
- R16 and R17 are H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R10 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R11 and R12 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH2 group of said alkyl is optionally replaced be by O or NR18;
- or
- R11 and R12, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
- or
- R11 and R12 are COR19 or SO2R20;
- R18, R19, and R20 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R13 and R14 are alkyl having 1 to 4 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- R15 is alkyl or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine;
- or
- R15 is OH or NR21R22;
- R21 and R22 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH2 group of said alkyl is optionally replaced by O— or NR23;
- R23 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R21 and R22, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
- R2, R3, and R4 are, independently of one another, H or F;
- R6, R7, R8, and R9 are, independently of one another, H, F, Cl, Br, I, CN, alkyl, or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine;
- or
- R6, R7, R8, and R9 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- or
- R6, R7, R8, and R9 are OH, OCOR24, or NR25R26;
- R24 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R25 and R26 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R25 and R26 are COR27;
- or
- R25 and R26, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring, and at least one CH2 group thereof is optionally replaced by O or NR18;
- R27 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- a pharmaceutically tolerable salt thereof.
38 more elements
A method for treating disorders of bile function, comprising administering to a patient in need thereof an effective amount of at least one compound of Formula I
- in which:
- R1 and R5 are, independently of one another, H, F, Cl, Br, I, CN, alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are OH or O-alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are OCOR10, NR11R12, COR13, COOH, COOR14, CONR11R12, or —(O)n—SOmR15, in which n is 0 or 1 and m is 0, 1, or 2;
- or
- R1 and R5 are O-phenyl, in which phenyl is unsubstituted or substituted by one to three substituents selected from F, Cl, Br, I, alkyl having 1 to 4 carbon atoms, OH, O-alkyl having 1 to 4 carbon atoms, NR16R17, CN, or (C1-C4)-alkylsulfonyl, in which the alkyl groups are unsubstituted or partially or completely substituted by fluorine;
- R16 and R17 are H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R10 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R11 and R12 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH2 group of said alkyl is optionally replaced be by O or NR18;
- or
- R11 and R12, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
- or
- R11 and R12 are COR19 or SO2R20;
- R18, R19, and R20 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R13 and R14 are alkyl having 1 to 4 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- R15 is alkyl or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine;
- or
- R15 is OH or NR21R22;
- R21 and R22 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH2 group of said alkyl is optionally replaced by O— or NR23;
- R23 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R21 and R22, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
- R2, R3, and R4 are, independently of one another, H or F;
- R6, R7, R8, and R9 are, independently of one another, H, F, Cl, Br, I, CN, alkyl, or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine;
- or
- R6, R7, R8, and R9 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- or
- R6, R7, R8, and R9 are OH, OCOR24, or NR25R26;
- R24 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R25 and R26 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R25 and R26 are COR27;
- or
- R25 and R26, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring, and at least one CH2 group thereof is optionally replaced by O or NR18;
- R27 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- a pharmaceutically tolerable salt thereof.
38 more elements
A method for treating ischemic conditions of peripheral organs and limbs, comprising administering to a patient in need thereof an effective amount of at least one compound of Formula I
- in which:
- R1 and R5 are, independently of one another, H, F, Cl, Br, I, CN, alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are OH or O-alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are OCOR10, NR11R12, COR13, COOH, COOR14, CONR11R12, or —(O)n—SOmR15, in which n is 0 or 1 and m is 0, 1, or 2;
- or
- R1 and R5 are O-phenyl, in which phenyl is unsubstituted or substituted by one to three substituents selected from F, Cl, Br, I, alkyl having 1 to 4 carbon atoms, OH, O-alkyl having 1 to 4 carbon atoms, NR16R17, CN, or (C1-C4)-alkylsulfonyl, in which the alkyl groups are unsubstituted or partially or completely substituted by fluorine;
- R16 and R17 are H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R10 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R11 and R12 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH2 group of said alkyl is optionally replaced be by O or NR18;
- or
- R11 and R12, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
- or
- R11 and R12 are COR19 or SO2R20;
- R18, R19, and R20 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R13 and R14 are alkyl having 1 to 4 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- R15 is alkyl or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine;
- or
- R15 is OH or NR21R22;
- R21 and R22 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH2 group of said alkyl is optionally replaced by O— or NR23;
- R23 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R21 and R22, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
- R2, R3, and R4 are, independently of one another, H or F;
- R6, R7, R8, and R9 are, independently of one another, H, F, Cl, Br, I, CN, aikyl, or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine;
- or
- R6, R7, R8, and R9 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- or
- R6, R7, R8, and R9 are OH, OCOR24, or NR25R26;
- R24 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R25 and R26 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R25 and R26 are COR27;
- or
- R25 and R26, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring, and at least one CH2 group thereof is optionally replaced by O or NR18;
- R27 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- a pharmaceutically tolerable salt thereof.
38 more elements
A method for treating a patient during surgical operations, comprising administering to a patient in need thereof an effective amount of at least one compound of Formula I
- in which:
- R1 and R5 are, independently of one another, H, F, Cl, Br, I, CN, alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are OH or O-alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are OCOR10, NR11R12, COR13, COOH, COOR14, CONR11R12, or —(O)n—SOmR15, in which n is 0 or 1 and m is 0, 1, or 2;
- or
- R1 and R5 are O-phenyl, in which phenyl is unsubstituted or substituted by one to three substituents selected from F, CI, Br, I, alkyl having 1 to 4 carbon atoms, OH, O-alkyl having 1 to 4 carbon atoms, NR16R17, CN, or (C1-C4)-alkylsulfonyl, in which the alkyl groups are unsubstituted or partially or completely substituted by fluorine;
- R16 and R17 are H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R10 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R11 and R12 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH2 group of said alkyl is optionally replaced be by O or NB18;
- or
- R11 and R12, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
- or
- R11 and R12 are COR19 or SO2R20;
- R18, R19, and R20 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R13 and R14 are alkyl having 1 to 4 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- R15 is alkyl or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine;
- or
- R15 is OH or NR21R22;
- R21 and R22 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH2 group of said alkyl is optionally replaced by O— or NR23;
- R23 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R21 and R22, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
- R2, R3, and R4 are, independently of one another, H or F;
- R6, R7, R8, and R9 are, independently of one another, H, F, Cl, Br, I, CN, alkyl, or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine;
- or
- R6, R7, R8, and R9 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- or
- R6, R7, R8, and R9 are OH, OCOR24, or NR25R26;
- R24 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R25 and R26 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R25 and R26 are COR27;
- or
- R25 and R26, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring, and at least one CH2 group thereof is optionally replaced by O or NR18;
- R27 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- a pharmaceutically tolerable salt thereof.
38 more elements
A method for treating an organ transplant, which comprises contacting an organ transplant with an effective amount of at least one compound of Formula I
- in which:
- R1 and R5 are, independently of one another, H, F, Cl, Br, I, CN, alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are OH or O-alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are OCOR10, NR11R12, COR13, COOH, COOR14, CONR11R12, or —(O)n—SOmR15, in which n is 0 or 1 and m is 0, 1, or 2;
- or
- R1 and R5 are O-phenyl, in which phenyl is unsubstituted or substituted by one to three substituents selected from F, Cl, Br, I, alkyl having 1 to 4 carbon atoms, OH, O-alkyl having 1 to 4 carbon atoms, NR16R17, CN, or (C1-C4)-alkylsulfonyl, in which the alkyl groups are unsubstituted or partially or completely substituted by fluorine;
- R16 and R17 are H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R10 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R11 and R12 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH2 group of said alkyl is optionally replaced be by O or NR18;
- or
- R11 and R12, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
- or
- R11 and R12 are COR19 or SO2R20;
- R18, R19, and R20 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R13 and R14 are alkyl having 1 to 4 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- R15 is alkyl or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine;
- or
- R15 is OH or NR21R22;
- R21 and R22 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH2 group of said alkyl is optionally replaced by O— or NR23;
- R23 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R21 and R22, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
- R2, R3, and R4 are, independently of one another, H or F;
- R6, R7, R8, and R9 are, independently of one another, H, F, Cl, Br, I, CN, alkyl, or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine;
- or
- R6, R7, R8, and R9 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- or
- R6, R7, R8, and R9 are OH, OCOR24, or NR25R26;
- R24 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R25 and R26 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R25 and R26 are COR27;
- or
- R25 and R26, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring, and at least one CH2 group thereof is optionally replaced by O or NR18;
- R27 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- a pharmaceutically tolerable salt thereof.
38 more elements
A method for treating illnesses in which cell proliferation is a primary or secondary cause, comprising administering to a patient in need thereof an effective amount of at least one compound of Formula I
- in which:
- R1 and R5 are, independently of one another, H, F, Cl, Br, I, CN, alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are OH or O-alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are OCOR10, NR11R12, COR13, COOH, COOR14, CONR11R12, or —(O)n—SOmR15, in which n is 0 or 1 and m is 0, 1, or 2;
- or
- R1 and R5 are O-phenyl, in which phenyl is unsubstituted or substituted by one to three substituents selected from F, Cl, Br, I, alkyl having 1 to 4 carbon atoms, OH, O-alkyl having 1 to 4 carbon atoms, NR16R17, CN, or (C1-C4)-alkylsulfonyl, in which the alkyl groups are unsubstituted or partially or completely substituted by fluorine;
- R16 and R17 are H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R10 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R11 and R12 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH2 group of said alkyl is optionally replaced be by O or NR18;
- or
- R11 and R12, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
- or
- R11 and R12are COR 19 or SO2R20;
- R18, R19, and R20 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R13 and R14 are alkyl having 1 to 4 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- R15 is alkyl or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine;
- or
- R15 is OH or NR21R22;
- R21 and R22 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH2 group of said alkyl is optionally replaced by O— or NR23;
- R23 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R21 and R22, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
- R2, R3, and R4 are, independently of one another, H or F;
- R6, R7, R8, and R9 are, independently of one another, H, F, Cl, Br, I, CN, alkyl, or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine;
- or
- R6, R7, R8, and R9 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- or
- R6, R7, R8, and R9 are OH, OCOR24, or NR25R26;
- R24 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R25 and R26 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by flourine;
- or
- R25 and R26 are COR27;
- or
- R25 and R26, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring, and at least one CH2 group thereof is optionally replaced by O or NR18;
- R27 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- a pharmaceutically tolerable salt thereof.
38 more elements
A method for treating attack by ectoparasites in human and veterinary medicine, comprising administering to a patient in need thereof an effective amount of at least one compound of Formula I
- in which:
- R1 and R5 are, independently of one another, H, F, Cl, Br, I, CN, alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are OH or O-alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R1 and R5 are OCOR10, NR11R12, COR13, COOH, COOR14, CONR11R12, or —(O)n—SOmR15, in which n is 0 or 1 and m is 0, 1, or 2;
- or
- R1 and R5 are O-phenyl, in which phenyl is unsubstituted or substituted by one to three substituents selected from F, Cl, Br, I, alkyl having 1 to 4 carbon atoms, OH, O-alkyl having 1 to 4 carbon atoms, NR16R17, CN, or (C1-C4)-alkylsulfonyl, in which the alkyl groups are unsubstituted or partially or completely substituted by fluorine;
- R16 and R17 are H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R10 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R11 and R12 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH2 group of said alkyl is optionally replaced be by O or NR18;
- or
- R11 and R12, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
- or
- R11 and R12 are COR19 or SO2R20;
- R18, R19, and R20 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R13 and R14 are alkyl having 1 to 4 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- R15 is alkyl or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine;
- or
- R15 is OH or NR21R22;
- R21 and R22 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH2 group of said alkyl is optionally replaced by O— or NR23;
- R23 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R21 and R22, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
- R2, R3, and R4 are, independently of one another, H or F;
- R6, R7, R8, and R9 are, independently of one another, H, F, Cl, Br, I, CN, alkyl, or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine;
- or
- R6, R7, R8, and R9 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
- or
- R6, R7, R8, and R9 are OH, OCOR24, or NR25R26;
- R24 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- R25 and R26 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- R25 and R26 are COR27;
- or
- R25 and R26, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring, and at least one CH2 group thereof is optionally replaced by O or NR18;
- R27 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
- or
- a pharmaceutically tolerable salt thereof.
38 more elements
Dependencies are inferred from the claim text.