IP Library › Granted Patent US 7,579,341

Granted Patent B2

US 7,579,341 · App. 11/462,511 · Granted Aug 25, 2009

Selected CGRP antagonists, processes for preparing them and their use as pharmaceutical compositions

Assignee: Boehringer Ingelheim International GmbH

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Quick Facts

Patent No.: US 7,579,341
App. No.: 11/462,511
Granted: Aug 25, 2009
Kind: B2

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Abstract

The present invention relates to the CGRP antagonists of general formula I wherein R 1 , R 2 , R 3 and R 4 are as defined in claim 1 , the tautomers, the isomers, the diastereomers, the enantiomers, the hydrates thereof, the mixtures thereof and the salts thereof and the hydrates of the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, as well as those compounds of general formula I wherein one or more hydrogen atoms are replaced by deuterium, pharmaceutical compositions containing these compounds, their use and processes for preparing them.

Claims (738)

1. A compound of the formula I

wherein

R 1 denotes a group of the formula

wherein

R 1.1 denotes H or H 3 C—O,

R 2 denotes a group selected from

R 3 denotes a group of general formula II

wherein

X denotes N or C,

R 3.1 denotes H, C 1-3 -alkyl or R 3.1.1 —O—C(O),

R 3.1.1 denotes H, C 1-6 -alkyl, H 2 N—C 2-4 -alkylene, (C 1-3 -alkyl)-NH—C 2-4 -alkylene, (C 1-3 -alkyl) 2 N—C 2-4 -alkylene, H 2 N—C(O)—C 1-3 -alkylene, (C 1-3 -alkyl)-NH—C(O)—C 1-3 -alkylene, (C 1-3 -alkyl) 2 N—C(O)—C 1-3 -alkylene or R 3.1.1.1 —C 2-4 -alkylene,

R 3.1.1.1 denotes a group selected from

R 3.2 denotes a pair of free electrons, if X=N, or

R 3.2 denotes H, C 1-3 -alkyl or R 3,2,1 —O—C(O), if X=C,

R 3,2,1 denotes H, C 1-6 -alkyl, H 2 N—C 2-4 -alkylene, (C 1-3 -alkyl)-NH—C 2-4 -alkylene, (C 1-3 -alkyl) 2 N—C 2-4 -alkylene, H 2 N—C(O)—C 1-3 -alkylene, (C 1-3 -alkyl)-NH—C(O)—C 1-3 -alkylene, (C 1-3 -alkyl) 2 N—C(O)—C 1-3 -alkylene or R 3,2,1.1 —C 2-4 -alkylene,

R 3,2,1.1 denotes a group selected from

R 4 denotes a group of general formulae III

wherein

Y denotes C and

R 4.1 denotes H or C 1-3 -alkyl, or

Y denotes N and

R 4.1 denotes a pair of free electrons,

with the proviso that X and Y do not simultaneously represent N,

R 4.2 denotes H, C 1-3 -alkyl or R 4.2.1 —O—C(O),

R 4.2.1 denotes H, C 1-6 -alkyl, H 2 N—C 2-4 -alkylene, (C 1-3 -alkyl)-NH—C 2-4 -alkylene, (C 1-3 -alkyl) 2 N—C 2-4 -alkylene, H 2 N—C(O)—C 1-3 -alkylene, (C 1-3 -alkyl)-NH—C(O)—C 1-3 -alkylene, (C 1-3 -alkyl) 2 N—C(O)—C 1-3 -alkylene or R 4.2.1.1 —C 2-4 -alkylene,

R 4.2.1.1 denotes a group selected from

R 4.3 denotes H, C 1-6 -alkyl, H 2 N—C 2-4 -alkylene, (C 1-3 -alkyl)-NH—C 2-4 -alkylene, (C 1-3 -alkyl) 2 N—C 2-4 -alkylene, H 2 N—C(O)—C 1-3 -alkylene, (C 1-3 -alkyl)-NH—C(O)—C 1-3 -alkylene, (C 1-3 -alkyl) 2 N—C(O)—C 1-3 -alkylene or R 4.3.1 —C 2-4 -alkylene- and

R 4.3.1 denotes a group selected from

R 5.1 denotes H, C 1-3 -alkyl, R 5.1.1 —O—C(O), R 5.1.1 —O—C(O)—C 1-3 -alkylene-NH, R 5.1.1 —O—C(O)—C 1-3 -alkylene-N(C 1-3 -alkyl), R 5.1.1 —O—C(O)—C 1-3 -alkylene-O, R 5.1.1 —O—C(O)—C 1-3 -alkylene, R 5.1.1 —O—C(O)—C(O), R 5.1.1 —O—C(O)—C(O)—O, R 5.1.1 —O—C(O)—C 1-3 -alkylene-C(O) or R 5.1.1 —O—C(O)—C 1-3 -alkylene-C(O)—O,

R 5.1.1 denotes H, C 1-8 -alkyl, phenyl, indanyl, pyridyl-C 1-3 -alkylene, HO—C 2-4 -alkylene, C 1-6 -alkyl-O—C 2-4 -alkylene, H 2 N—C 2-4 -alkylene, (C 1-6 -alkyl)-NH—C 2-4 -alkylene, (C 1-6 -alkyl) 2 N—C 2-4 -alkylene, H 2 N—C(O)—C 1-3 -alkylene, (C 1-6 -alkyl)-NH—C(O)—C 1-3 -alkylene, (C 1-6 -alkyl) 2 N—C(O)—C 1-3 -alkylene, C 1-6 -alkyl-C(O)—O—C 1-3 -alkylene, C 1-6 -alkyl-O—C(O)—O—C 1-3 -alkylene, R 5.1.1.1 —C(O)—C 1-3 -alkylene or R 5.1.1,2- C 2-4 -alkylene,

R 5.1.1.1 denotes a group selected from

R 5.1.1.2 denotes a group selected from

R 5.2 denotes H, C 1-3 -alkyl, R 5.2.1 —O—C(O)—C 1-3 -alkylene-NH, R 5.2.1 —O—C(O)—C 1-3 -alkylene-O, R 5.2.1 —O—C(O)—C 1-3 -alkylene, R 5.2.1 —O—C(O)—C(O) or R 5.2.1 —O—C(O)—C 1-3 -alkylene-C(O),

R 5.2.1 denotes H, C 1-8 -alkyl, phenyl, indanyl, pyridyl-C 1-3 -alkylene, HO—C 2-4 -alkylene, C 1-6 -alkyl-O—C 2-4 -alkylene, C 1-6 -alkyl-O—C 2-4 -alkylene -O—C 2-4 -alkylene, H 2 N—C 2-4 -alkylene, (C 1-6 -alkyl)-NH—C 2-4 -alkylene, (C 1-6 -alkyl) 2 N—C 2-4 -alkylene, H 2 N—C(O)—C 1-3 -alkylene, (C 1-6 -alkyl)-NH—C(O)—C 1-3 -alkylene, (C 1-6 -alkyl) 2 N—C(O)—C 1-3 -alkylene, C 1-6 -alkyl-C(O)—O—C 1-3 -alkylene, C 1-6 -alkyl-O—C(O)—O—C 1-3 -alkylene, R 5.2.1.1 —C(O)—C 1-3 -alkylene or R 5.2.1,2- C 2-4 -alkylene,

R 5.2.1.1 denotes a group selected from

R 5.2.1.2 denotes a group selected from

R 5.2.1 denotes a group of formula

with the proviso that at least one of the groups R 3.1 , R 3.2 , R 4.2 , R 5.1 or R 5.2 denotes a group other than H or C 1-3 -alkyl,

or a tautomer or salt thereof.

2. A compound of the formula I according to claim 1 , wherein

R 1 denotes a group of the formula

wherein

R 1.1 denotes H or H 3 C—O,

R 2 denotes a group selected from

R 3 denotes a group of general formula II

wherein

X denotes N or C,

R 3.1 denotes H, C 1-3 -alkyl or R 3.1.1 —(O)C,

R 3.1.1 denotes HO, C 1-6 -alkyl-O,

R 3.2 denotes a pair of free electrons, if X=N, or

R 3.2 denotes H or C 1-3 -alkyl, if X=C,

R 4 denotes a group of general formulae III

wherein

Y denotes C and

R 4.1 denotes H or C 1-3 -alkyl, or

Y denotes N and

R 4.1 denotes a pair of free electrons,

with the proviso that X and Y do not simultaneously represent N,

R 4.2 denotes H, C 1-3 -alkyl or R 4.2.1 —(O)C,

R 4.2.1 denotes HO, C 1-6 -alkyl-O, and

R 4.3.1 denotes a group selected from

R 5.1 denotes R 5.1.1 —O—C(O), R 5.1.1 —O—C(O)—C 1-3 -alkylene-NH, R 5.1.1 —O—C(O)—C 1-3 -alkylene-O, R 5.1.1 —O—C(O)—C 1-3 -alkylene, R 5.1.1 —O—C(O)—C(O) or R 5.1.1 —O—C(O)—C 1-3 -alkylene-C(O),

R 5.1.1.1 denotes a group selected from

R 5.1.1.2 denotes a group selected from

R 5.2 denotes R 5.2.1 —O—C(O)—C 1-3 -alkylene-NH, R 5.2.1 —O—C(O)—C 1-3 -alkylene-O, R 5.2.1 —O—C(O)—C 1-3 -alkylene, R 5.2.1 —O—C(O)—C(O) or R 5.2.1 —O—C(O)—C 1-3 -alkylene-C(O),

R 5.2.1 denotes H, C 1-8 -alkyl, phenyl, indanyl, pyridyl-C 1-3 -alkylene, HO—C 2-4 -alkylene, C 1-6 -alkyl-O—C 2-4 -alkylene, H 2 N—C 2-4 -alkylene, (C 1-6 -alkyl)-NH—C 2-4 -alkylene, (C 1-6 -alkyl) 2 N—C 2-4 -alkylene, H 2 N—C(O)—C 1-3 -alkylene, (C 1-6 -alkyl)-NH—C(O)—C 1-3 -alkylene, (C 1-6 -alkyl) 2 N—C(O)—C 1-3 -alkylene, C 1-6 -alkyl-C(O)—O—C 1-3 -alkylene, C 1-6 -alkyl-O—C(O)—O—C 1-3 -alkylene, R 5.2.1.1 —C(O)—C 1-3 -alkylene or R 5.2.1,2- C 2-4 -alkylene,

R 5.2.1.1 denotes a group selected from

R 5.2.1.2 denotes a group selected from

or a tautomer or salt thereof.

3. A compound of the formula I according to claim 1 , wherein

R 1 denotes a group of the formula

wherein

R 1.1 denotes H or H 3 C—O,

R 2 denotes a group selected from

R 3 —R 4 together denote a group of general formulae IV

wherein

R 3.1 denotes H, H 3 C or R 3.1.1 —O—C(O),

R 3.1.1 denotes H, C 1-6 -alkyl, (C 1-3 -alkyl) 2 N—C 2-4 -alkylene, (C 1-3 -alkyl) 2 N—C(O)—C 1-3 -alkylene or R 3.1.1.1 —C 2-4 -alkylene,

R 3.1.1.1 denotes a group selected from

R 3.2 denotes H, C 1-3 -alkyl or R 3,2,1 —O—C(O),

R 3,2,1 denotes H, C 1-6 -alkyl, (C 1-3 -alkyl) 2 N—C 2-4 -alkylene, (C 1-3 -alkyl) 2 N—C(O)—C 1-3 -alkylene or R 3,2,1.1 —C 2-4 -alkylene,

R 3,2,1.1 denotes a group selected from

R 4.1 denotes H or C 1-3 -alkyl,

R 4.2 denotes H, C 1-3 -alkyl or R 4.2.1 —O—C(O),

R 4.2.1 denotes H, C 1-6 -alkyl, (C 1-3 -alkyl) 2 N—C 2-4 -alkylene, (C 1-3 -alkyl) 2 N—C(O)—C 1-3 -alkylene or R 4.2.1.1 —C 2-4 -alkylene,

R 4.2.1.1 denotes a group selected from

R 4.3.1 denotes a group selected from

R 5.1 denotes H, H 3 C, R 5.1.1 —O—C(O), R 5.1.1 —O—C(O)—C 1-3 -alkylene-NH, R 5.1.1 —O—C(O)—C 1-3 -alkylene-N(C 1-3 -alkyl), R 5.1.1 —O—C(O)—C 1-3 -alkylene-O, R 5.1.1 —O—C(O)—C 1-3 -alkylene, R 5.1.1 —O—C(O)—C(O), R 5.1.1 —O—C(O)—C(O)—O, R 5.1.1 —O—C(O)—C 1-3 -alkylene-C(O) or R 5.1.1 —O—C(O)—C 1-3 -alkylene-C(O)—O,

R 5.1.1 denotes H, C 1-8 -alkyl, phenyl, indanyl, pyridyl-CH 2 , HO—C 2-4 -alkylene, C 1-6 -alkyl-O—C 2-4 -alkylene, H 2 N—C 2-4 -alkylene, (C 1-6 -alkyl)-NH—C 2-4 -alkylene, (C 1-6 -alkyl) 2 N—C 2-4 -alkylene, H 2 N—C(O)—C 1-3 -alkylene, (C 1-6 -alkyl)-NH—C(O)—C 1-3 -alkylene, (C 1-6 -alkyl) 2 N—C(O)—C 1-3 -alkylene, C 1-6 -alkyl-C(O)—O—C 1-3 -alkylene, C 1-6 -alkyl-O—C(O)—O—C 1-3 -alkylene, R 5.1.1.1 —C(O)—C 1-3 -alkylene or R 5.1.1,2- C 2-4 -alkylene,

R 5.1.1.1 denotes a group selected from

R 5.1.1.2 denotes a group selected from

R 5.2 denotes H, H 3 C, R 5.2.1 —O—C(O)—C 1-3 -alkylene-NH, R 5.2.1 —O—C(O)—C 1-3 -alkylene-O, R 5.2.1 —O—C(O)—C 1-3 -alkylene, R 5.2.1 —O—C(O)—C(O) or R 5.2.1 —O—C(O)—C 1-3 -alkylene-C(O),

R 5.2.1 denotes H, C 1-8 -alkyl, phenyl, indanyl, pyridyl-CH 2 , HO—C 2-4 -alkylene, C 1-6 -alkyl-O—C 2-4 -alkylene, C 1-6 -alkyl-O—C 2-4 -alkylene-O—C 2-4 -alkylene, H 2 N—C 2-4 -alkylene, (C 1-6 -alkyl)-NH—C 2-4 -alkylene, (C 1-6 -alkyl) 2 N—C 2-4 -alkylene, H 2 N—C(O)—C 1-3 -alkylene, (C 1-6 -alkyl)-NH—C(O)—C 1-3 -alkylene, (C 1-6 -alkyl) 2 N—C(O)—C 1-3 -alkylene, C 1-6 -alkyl-C(O)—O—C 1-3 -alkylene, C 1-6 -alkyl-O—C(O)—O—C 1-3 -alkylene, R 5.2.1.1 —C(O)—C 1-3 -alkylene or R 5.2.1,2- C 2-4 -alkylene,

R 5.2.1.1 denotes a group selected from

R 5.2.1.2 denotes a group selected from

R 5.2.1 denotes a group of formula

with the proviso that at least one of the groups R 3.1 , R 3.2 , R 4.2 , R 5.1 or R 5.2 denotes a group other than H or C 1-3 -alkyl,

or a tautomer or salt thereof.

4. A compound of the formula I according to claim 1 , wherein

R 1 denotes a group of the formula

wherein

R 1.1 denotes H or H 3 C—O,

R 2 denotes a group selected from

R 3 -R 4 together denote a group of general formulae IV

wherein

R 3.1 denotes H,

R 3.2 denotes H or C 1-3 -alkyl,

R 4.1 denotes H or C 1-3 -alkyl,

R 4.2 denotes H,

R 4.3.1 denotes a group selected from

R 5.1 denotes R 5.1.1 —O—C(O), R 5.1.1 —O—C(O)—C 1-3 -alkylene-NH, R 5.1.1 —O—C(O)—C 1-3 -alkylene-O, R 5.1.1 —O—C(O)—C 1-3 -alkylene, R 5.1.1 —O—C(O)C(O)—C(O) or R 5.1.1 —O—C(O)—C 1-3 -alkylene-C(O),

R 5.1.1.1 denotes a group selected from

R 5.1.1.2 denotes a group selected from

R 5.2.1.1 denotes a group selected from

R 5.2.1.2 denotes a group selected from

or a tautomer or salt thereof.

5. A compound of the formula I according to claim 1 , wherein

R 1 denotes a group of the formula

wherein

R 1.1 denotes H or H 3 C—O,

R 2 denotes a group selected from

R 3 -R 4 together denote a group of general formulae IV

wherein

R 3.1 denotes H or R 3.1.1 —O—C(O),

R 3.1.1 denotes H, C 1-6 -alkyl, (C 1-3 -alkyl) 2 N—C 2-4 -alkylene, (C 1-3 -alkyl) 2 N—C(O)—C 1-3 -alkylene or R 3.1.1.1 —C 2-4 -alkylene,

R 3.1.1.1 denotes a group

R 3.2 denotes H, H 3 C or R 3,2,1 —O—C(O),

R 3,2,1 denotes H, C 1-6 -alkyl, (C 1-3 -alkyl) 2 N—C 2-4 -alkylene, (C 1-3 -alkyl) 2 N—C(O)—C 1-3 -alkylene or R 3,2,1.1 —C 2-4 -alkylene,

R 3,2,1.1 denotes a group

R 4.2 denotes H or H 3 C,

R 4.3 denotes H, C 1-6 -alkyl, (C 1-3 -alkyl) 2 N—C 2-4 -alkylene, (C 1-3 -alkyl) 2 N—C(O)—C 1-3 -alkylene or R 4.3.1 —C 2-4 -alkylene, and

R 4.3.1 denotes a group selected from

R 5.1 denotes H, H 3 C, R 5.1.1 —O—C(O), R 5.1.1 —O—C(O)—C 1-3 -alkylene-NH, R 5.1.1 —O—C(O)—C 1-3 -alkylene-N(C 1-3 -alkyl), R 5.1.1 —O—C(O)—C 1-3 -alkylene-O, R 5.1.1 —O—C(O)—C 1-3 -alkylene, R 5.1.1 —O—C(O)—C(O), R 5.1.1 —O—C(O)—C(O)—O—R 5.1.1 —O—C(O)—C 1-3 -alkylene-C(O) or R 5.1.1 —O—C(O)—C 1-3 -alkylene-C(O)—O,

R 5.1.1 denotes H, C 1-8 -alkyl, phenyl, indanyl, pyridyl-methyl, HO—C 2-4 -alkylene, C 1-6 -alkyl-O—C 2-4 -alkylene, H 2 N—C 2-4 -alkylene, (C 1-6 -alkyl)-NH—C 2-4 -alkylene, (C 1-6 -alkyl) 2 N—C 2-4 -alkylene, H 2 N—C(O)—C 1-3 -alkylene, (C 1-6 -alkyl)-NH—C(O)—C 1-3 -alkylene, (C 1-6 -alkyl) 2 N—C(O)—C 1-3 -alkylene, C 1-6 -alkyl-C(O)—O—C 1-3 -alkylene, C 1-6 -alkyl-O—C(O)—O—C 1-3 -alkylene, R 5.1.1.1 —C(O)—C 1-3 -alkylene or R 5.1.1,2- C 2-4 -alkylene,

R 5.1.1.1 denotes a group selected from

R 5.1.1.2 denotes a group selected from

R 5.2 denotes H, H 3 C, R 5.2.1 —O—C(O)—C 1-3 -alkylene, R 5.2.1 —O—C(O)—C(O) or R 5.2.1 —O—C(O)—C 1-3 -alkylene-C(O),

R 5.2.1 denotes H, C 1-8 -alkyl, phenyl, indanyl, pyridyl-methyl, HO—C 2-4 -alkylene, C 1-6 -alkyl-O—C 2-4 -alkylene, C 1-6 -alkyl-O—C 2-4 -alkylene-O—C 2-4 -alkylene, H 2 N—C 2-4 -alkylene, (C 1-6 -alkyl)-NH—C 2-4 -alkylene, (C 1-6 -alkyl) 2 N—C 2-4 -alkylene, H 2 N—C(O)—C 1-3 -alkylene, (C 1-6 -alkyl)-NH—C(O)—C 1-3 -alkylene, (C 1-6 -alkyl) 2 N—C(O)—C 1-3 -alkylene, C 1-6 -alkyl-C(O)—O—C 1-3 -alkylene, C 1-6 -alkyl-O—C(O)—O—C 1-3 -alkylene, R 5.2.1.1 —C(O)—C 1-3 -alkylene or R 5.2.1,2- C 2-4 -alkylene,

R 5.2.1.1 denotes a group selected from

R 5.2.1.2 denotes a group selected from

R 5.2.1 denotes a group of formula

with the proviso that at least one of the groups R 3.1 , R 3.2 , R 4.2 , R 5.1 or R 5.2 denotes a group other than H, H 3 C or C 1-3 -alkyl,

or a tautomer or salt thereof.

6. A compound of the formula I according to claim 1 , wherein

R 1 denotes a group of the formula

wherein

R 1.1 denotes H or H 3 C—O,

R 2 denotes a group selected from

R 3 -R 4 together denote a group of general formulae IV

wherein

R 4.3 denotes H, C 1-6 -alkyl, (C 1-3 -alkyl) 2 N—C 2-4 -alkylene, (C 1-3 -alkyl) 2 N—C(O)—C 1-3 -alkylene or R 4.3.1 —C 2-4 -alkylene,

R 4.3.1 denotes a group selected from

R 5.1 denotes R 5.1.1 —O—C(O), R 5.1.1 —O—C(O)—C 1-3 -alkylenl-NH, R 5.1.1 —O—C(O)—C 1-3 -alkylene-O, R 5.1.1 —O—C(O)—C 1-3 -alkylene, R 5.1.1 —O—C(O)—C(O) or R 5.1.1 —O—C(O)—C 1-3 -alkylene-C(O),

R 5.1.1.1 denotes a group selected from

R 5.1.1.2 denotes a group selected from

R 5.2 denotes R 5.2.1 —O—C(O)—C 1-3 -alkylene, R 5.2.1 —O—C(O)—C(O) or R 5.2.1 —O—C(O)—C 1-3 -alkylene-C(O),

R 5.2.1 denotes H, C 1-8 -alkyl, phenyl, indanyl, pyridyl-CH 2 , HO—C 2-4 -alkylene, C 1-6 -alkyl-O—C 2-4 -alkylene, H 2 N—C 2-4 -alkylene, (C 1-6 -alkyl)-NH—C 2-4 -alkylene, (C 1-6 -alkyl) 2 N—C 2-4 -alkylene, H 2 N—C(O)—C 1-3 -alkylene, (C 1-6 -alkyl)-NH—C(O)—C 1-3 -alkylene, (C 1-6 -alkyl) 2 N—C(O)—C 1-3 -alkylene, C 1-6 -alkyl-C(O)—O—C 1-3 -alkylene, C 1-6 -alkyl-O—C(O)—O—C 1-3 -alkylene, R 5.2.1.1 —C(O)—C 1-3 -alkylene or R 5.2.1,2 —C 2-4 -alkylene,

R 5.2.1.1 denotes a group selected from

R 5.2.1.2 denotes a group selected from

or a tautomer or salt thereof.

7. A compound of the formula I according to claim 1 , wherein

R 1 denotes a group of the formula

wherein

R 1.1 denotes H or H 3 C—O,

R 2 denotes a group selected from

R 3 -R 4 together denote a group of formulae IV

or a tautomer or salt thereof.

8. A compound of the formula I according to claim 1 , selected from the group consisting of:

No.

Structure

(1)

(2)

(3)

(4)

(5)

(6)

(7)

(8)

(9)

(10)

(11)

(12)

(13)

(14)

(15)

(16)

(17)

(18)

(19)

(20)

(21)

(22)

(23)

(24)

(25)

(26)

(27)

(28)

(29)

(32)

(33)

(34)

(35)

(36)

(37)

(40)

(41)

(42)

(43)

(44)

(45)

(46)

(47)

(48)

(49)

(50)

(51)

(52)

(53)

(54)

(55)

(56)

(57)

(58)

(59)

(60)

(61)

(62)

(63)

(64)

(65)

(66)

(67)

(68)

(69)

(70)

(71)

(72)

(73)

(74)

(75)

(76)

(77)

(78)

(79)

(80)

(81)

(82)

(83)

(84)

(85)

(86)

(87)

(88)

(89)

(90)

(91)

(92)

(93)

(94)

(95)

(96)

(97)

(98)

(99)

(100)

(101)

(102)

(103)

(104)

(105)

(106)

(107)

(108)

(109)

(110)

(111)

(112)

(113)

(114)

(115)

(116)

(117)

(118)

(119)

(120)

(121)

(122)

(123)

(124)

(125)

(126)

(127)

(128)

(129)

(130)

(131)

(132)

(133)

(134)

(135)

(136)

(137)

(138)

(139)

(140)

(141)

(142)

(143)

(144)

(145)

(146)

(147)

(148)

(149)

(150)

(151)

(152)

(153)

(154)

(155)

(156)

(157)

(158)

(159)

(160)

(161)

(162)

(163)

(164)

(165)

(166)

(167)

(168)

(169)

(170)

(171)

(172)

(173)

(174)

(175)

(176)

(177)

(178)

(179)

(180)

(181)

(182)

(183)

(184)

(185)

(186)

(187)

(188)

(189)

(190)

(191)

(192)

(193)

(194)

(195)

(196)

(197)

(198)

(199)

(200)

(201)

(202)

(203)

(204)

(205)

(206)

(207)

(208)

(209)

(210)

(211)

(212)

(213)

(214)

(215)

(216)

(217)

(218)

(219)

(220)

(221)

(222)

(223)

(224)

(225)

(226)

(227)

(228)

(229)

(230)

(231)

(232)

(233)

(234)

(235)

(236)

(237)

(238)

(239)

(240)

(241)

(242)

(243)

(244)

(245)

(246)

(247)

(248)

(249)

(250)

(251)

(252)

(253)

(254)

(255)

(256)

(257)

(258)

(259)

(260)

(261)

(262)

(263)

(264)

(265)

(266)

(267)

(268)

(269)

(270)

(271)

(272)

(273)

(274)

(275)

(276)

(277)

(278)

(279)

(280)

(281)

(282)

(283)

(284)

(285)

(286)

(287)

(288)

(289)

(290)

(291)

(292)

(293)

(294)

(295)

(296)

(297)

(298)

(299)

(300)

(301)

(302)

(303)

(304)

(305)

(306)

(307)

(308)

(309)

(310)

(311)

(312)

(313)

(314)

(315)

(316)

(317)

(318)

(319)

(320)

(321)

(322)

(323)

(324)

(325)

(326)

(327)

(328)

(329)

(330)

(331)

(332)

(333)

(334)

(335)

(336)

(337)

(338)

(339)

(340)

(341)

(342)

(343)

(344)

(345)

(346)

(347)

(348)

(349)

(386)

(387)

(388)

(389)

(390)

(391)

(392)

(393)

(394)

(395)

(396)

(397)

(398)

(399)

(400)

(401)

(402)

(403)

(404)

(405)

(406)

(407)

(408)

(409)

(410)

(411)

(412)

(413)

(414)

(415)

(416)

(417)

(418)

(419)

(420)

(421)

(422)

(423)

(424)

(425)

(426)

(427)

(428)

(429)

(430)

(431)

(432)

(433)

(434)

(435)

(436)

(437)

(438)

(439)

(440)

(441)

(442)

(443)

(444)

(445)

(446)

(447)

(448)

(449)

(450)

(451)

(452)

(453)

(454)

(455)

(456)

(457)

(458)

(459)

(460)

(461)

(462)

(463)

(464)

(465)

(466)

(467)

(468)

(469)

(470)

(471)

(472)

(473)

(474)

(475)

(476)

(477)

(478)

(479)

(480)

(481)

(482)

(483)

(484)

(485)

(486)

(487)

(488)

(489)

(490)

(491)

(492)

(493)

(494)

(495)

(496)

(497)

(498)

(499)

(500)

(501)

(502)

(503)

(504)

(505)

(506)

(507)

(508)

(509)

(510)

(511)

(512)

(513)

(514)

(515)

(516)

(517)

(518)

(519)

(520)

(521)

(522)

(523)

(524)

(525)

(526)

(527)

(528)

(529)

(530)

(531)

(532)

(533)

(534)

(535)

(536)

(537)

(538)

(539)

(540)

(541)

(542)

(543)

(544)

(545)

(546)

(547)

(548)

(549)

(550)

(551)

(552)

(553)

(554)

(555)

(556)

(557)

or a tautomer or salt thereof.

9. A compound of the formula I according to claim 1 , selected from the group consisting of:

No.

Structure

(3)

(4)

(7)

(59)

(112)

(113)

(462)

(463)

or a tautomer or salt thereof.

10. The following compound of the formula I according to claim 1 :

(3)

or a tautomer or salt thereof.

11. The following compound of the formula I according to claim 1 :

(4)

or a tautomer or salt thereof.

12. The following compound of the formula I according to claim 1 :

(7)

or a tautomer or salt thereof.

13. The following compound of the formula I according to claim 1 :

(59)

or a tautomer or salt thereof.

14. The following compound of the formula I according to claim 1 :

(112)

or a tautomer or salt thereof.

15. The following compound of the formula I according to claim 1 :

(113)

or a tautomer or salt thereof.

16. The following compound of the formula I according to claim 1 :

(462)

or a tautomer or salt thereof.

17. The following compound of the formula I according to claim 1 :

(463)

or a tautomer or salt thereof.

18. A physiologically acceptable salt of a compound according to claim 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 14 , 15 , 16 or 17 .

19. A pharmaceutical composition, containing a compound according to claim 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 14 , 15 , 16 or 17 , or a pharmaceutically acceptable salt thereof, together with one or more inert carriers and/or diluents.

20. A method for treating a condition selected from the group consisting of migraine, cluster headaches and tension headaches, which method comprises administering a therapeutically effective amount of a compound according to claim 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 14 , 15 , 16 or 17 , or a pharmaceutically acceptable salt thereof.

21. A method for treating non-insulin-dependent diabetes mellitus (NIDDM), which method comprises administering a therapeutically effective amount of a compound according to claim 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 14 , 15 , 16 or 17 , or a pharmaceutically acceptable salt thereof.

22. A method for treating irritable bowel syndrome (IBS), which method comprises administering a therapeutically effective amount of a compound according to claim 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 14 , 15 , 16 or 17 , or a pharmaceutically acceptable salt thereof.

23. A method for treating hot flushes in an oestrogen-deficient woman, which method comprises administering a therapeutically effective amount of a compound according to claim 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 14 , 15 , 16 or 17 , or a pharmaceutically acceptable salt thereof.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 29, 2008

From: MUELLER, STEPHAN GEORG; RUDOLF, KLAUS; LUSTENBERGER, PHILIPP; SCHAENZLE, GERHARD; SANTAGOSTINO, MARCO; STENKAMP, DIRK; ARNDT, KIRSTEN; DOODS, HENRI

To: BOEHRINGER INGELHEIM INTERNATIONAL GMBH

Reel/Frame 021756/0049 →

Priority Claims (2)

DE 10 2005 038 831 · Aug 17, 2005 · national

DE 10 2005 050 953 · Oct 25, 2005 · national

Continuity (1)

Related Publication 20070049581A1 · Mar 1, 2007