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EP0260613A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Imidazopyridine derivatives, their preparation and their use as PAF-antagonists

Assignee: GD Searle LLC
•
Filing: 1987-09-11
•
Granted: —
•
Expires: 2007-09-11
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Abstract

Abstract This invention relates to novel imidazopyridine derivatives useful in the treatment of diseases or disorders mediated by platelet-activating factor. This invention further relates to pharmaceutical compositions of such imidazopyridine derivatives.

Inventors

  • 👤 Paul William Manley
  • 👤 Roderick Alan Porter

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-10-27 07:14
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; A; A61; A61P; A61P11/00; A61P29/00; A61P7/00; A61P9/00

Claims Analysis

Total Claims: 260
Claim 1
Independent Claim 170 words
A compound of the formula or a pharmaceutically acceptable acid addition salt thereof; wherein one of W, X, Y, and Z is -N-and the others of W, X, Y, and Z are each -CH-; A is a) a group wherein m is 0 or 1, or b) a -(CH 2 ) n -(CR 5 R 6 ) p -group wherein n is an integer from 0 to 8, p is an integer from 0 to 2, and R 5 and R 6 are independently hydrogen or C 1 -C 4 alkyl; and R is - a) a group wherein R 1 is C 1 -C 8 alkyl; b) group wherein R 2 and R 3 are independently hydrogen, C 1 -C 8 alkyl, or C 3 -C 8 cycloalkyl; c) group wherein t and u are independently integers from 1 to 3 and M is -0-, -5-, or -CH 2 -; or d) group wherein R 4 is hydrogen, C 1 -C 8 alkyl, or C 3 -C 8 cycloalkyl.
Claim 2
Dependent Claim 170 words
A compound of the formula or a pharmaceutically acceptable acid addition salt thereof; wherein one of W, X, Y, and Z is -N-and the others of W, X, Y, and Z are each -CH-; A is a) a group wherein m is 0 or 1, or b) a -(CH 2 ) n -(CR 5 R 6 ) p -group wherein n is an integer from 0 to 8, p is an integer from 0 to 2, and R 5 and R 6 are independently hydrogen or C 1 -C 4 alkyl; and R is - a) a group wherein R 1 is C 1 -C 8 alkyl; b) group wherein R 2 and R 3 are independently hydrogen, C 1 -C 8 alkyl, or C 3 -C 8 cycloalkyl; c) group wherein t and u are independently integers from 1 to 3 and M is -0-, -5-, or -CH 2 -; or d) group wherein R 4 is hydrogen, C 1 -C 8 alkyl, or C 3 -C 8 cycloalkyl.
Claim 3
Dependent Claim 9 words
A compound according to Claim 1 having the formula
Claim 4
Dependent Claim 9 words
A compound according to Claim 2 having the formula
Claim 5
Dependent Claim 11 words
A compound according to Claim 3 wherein R is a group.
Claim 6
Dependent Claim 10 words
A compound according to Claim 4 wherein m is 0.
Claim 7
Dependent Claim 11 words
A compound according to Claim 4 wherein R 1 is ethyl.
Claim 8
Dependent Claim 10 words
A compound according to Claim 4 which is ethyl 4-(1H-imidazo[4,5-c]pyridin-1-ylmethyl)benzoate.
Claim 9
Dependent Claim 10 words
A compound according to Claim 4 which is ethyl 3-(1H-imidazo[4,5-c]pyridin-1-ylmethyl)benzoate.
Claim 10
Dependent Claim 11 words
A compound according to Claim 3 wherein R is a group.
Claim 11
Dependent Claim 10 words
A compound according to Claim 9 wherein m is 0.
Claim 12
Dependent Claim 25 words
A compound according to Claim 9 wherein R 2 and R 3 are independently C 1 -C 8 alkyl or C 3 -C 8 cycloalkyl.
Claim 13
Dependent Claim 9 words
A compound according to Claim 9 which is N-cyclohexyl-N-methyl-4-[1H-imidazo[4,5-c]pyridin-1-ylmethyl)benzamide.
Claim 14
Dependent Claim 11 words
A compound according to Claim 3 wherein R is a group.
Claim 15
Dependent Claim 10 words
A compound according to Claim 13 wherein m is 0.
Claim 16
Dependent Claim 10 words
A compound according to Claim 13 wherein M is -0-.
Claim 17
Dependent Claim 9 words
A compound according to Claim 13 which is [4-(IH-imidazo[4,5-c]pyridin-1-ylmethyl)phenyl](4-morpholinyl)methanone.
Claim 18
Dependent Claim 9 words
A compound according to Claim 2 having the formula
Claim 19
Dependent Claim 11 words
A compound according to Claim 17 wherein R is a group.
Claim 20
Dependent Claim 10 words
A compound according to Claim 18 wherein m is 0.
Claim 21
Dependent Claim 11 words
A compound according to Claim 18 wherein R 1 is ethyl.
Claim 22
Dependent Claim 10 words
A compound according to Claim 18 which is ethyl 4-(3H-imidazo[4,5-c]pyridin-3-ylmethyl)benzoate.
Claim 23
Dependent Claim 10 words
A compound according to Claim 18 which is ethyl 3-(3H-imidazo[4,5-c]pyridin-3-ylmethyl)benzoate.
Claim 24
Dependent Claim 11 words
A compound according to Claim 17 wherein R is a group.
Claim 25
Dependent Claim 10 words
A compound according to Claim 23 wherein m is 0.
Claim 26
Dependent Claim 10 words
A compound according to Claim 23 wherein M is -0-.
Claim 27
Dependent Claim 9 words
A compound according to Claim 23 which is [4-(3H-imidazo[4,5-c]pyridin-3-ylmethyl)phenyl](4-morpholinyl)methanone.
Claim 28
Dependent Claim 9 words
A compound according to Claim 2 having the formula
Claim 29
Dependent Claim 11 words
A compound accordina to Claim 27 wherein R is a group.
Claim 30
Dependent Claim 10 words
A compound according to Claim 28 wherein m is 0.
Claim 31
Dependent Claim 11 words
A compound according to Claim 28 wherein R I is ethyl.
Claim 32
Dependent Claim 10 words
A compound according to Claim 28 which is ethyl 4-(1H-imidazo[4,5-b]pyridin-1-ylmethyl)benzoate.
Claim 33
Dependent Claim 11 words
A compound according to Claim 27 wherein R is a group.
Claim 34
Dependent Claim 10 words
A compound according to Claim 32 wherein m is 0.
Claim 35
Dependent Claim 10 words
A compound according to Claim 32 wherein M is -0-.
Claim 36
Dependent Claim 9 words
A compound according to Claim 32 which is [4-(1H-imidazo[4,5-b]pyridin-1-ylmethyl)phenyl](4-morpholinyl)methanone.
Claim 37
Dependent Claim 9 words
A compound according to Claim 2 having the formula
Claim 38
Dependent Claim 11 words
A compound according to Claim 36 wherein R is a group.
Claim 39
Dependent Claim 10 words
A compound according to Claim 37 wherein m is 0.
Claim 40
Dependent Claim 10 words
A compound according to Claim 37 wherein R' is ethyl.
Claim 41
Dependent Claim 10 words
A compound according to Claim 37 which is ethyl 4-(3H-imidazo[4,5-b]pyridin-3-ylmethyl)benzoate.
Claim 42
Dependent Claim 9 words
A compound according to Claim 1 having the formula
Claim 43
Dependent Claim 9 words
A compound according to Claim 41 having the formula
Claim 44
Dependent Claim 21 words
A compound according to Claim 42 wherein n is an integer from 2 to 5 and p is 0 or 1.
Claim 45
Dependent Claim 11 words
A compound according to Claim 42 wherein R is a group.
Claim 46
Dependent Claim 11 words
A compound according to Claim 44 wherein R 1 is ethyl.
Claim 47
Dependent Claim 10 words
A compound according to Claim 44 wherein p is 0.
Claim 48
Dependent Claim 28 words
A compound according to Claim 44 wherein said compound is selected from the group consisting of: ethyl 4-(1 H-imidazo[4,5-c]pyridin-1-yl)butanoate, ethyl 5-(1 H-imidazo[4,5-c]pyridin-1-yl)pentanoate, ethyl 6-(1H-imidazo[4,5-c]pyridin-1-yl)hexanoate, and ethyl 7-(1 H-imidazo[4,5-c]pyridin-1-yl)heptanoate.
Claim 49
Dependent Claim 10 words
A compound according to Claim 44 wherein p is 1.
Claim 50
Dependent Claim 11 words
A compound according to Claim 44 which is ethyl 2,2-dimethyl-6-(1H-imidazo[4,5-c]pyridin-1-ylr hexanoate.
Claim 51
Dependent Claim 11 words
A compound according to Claim 43 wherein R is a group.
Claim 52
Dependent Claim 25 words
A compound according to Claim 50 wherein R 2 and R 3 are independently C 1 -C 8 alkyl or C 3 -C 8 cycloalkyl.
Claim 53
Dependent Claim 10 words
A compound according to Claim 50 wherein p is 0.
Claim 54
Dependent Claim 9 words
A compound according to Claim 50 which is N-cyclohexyl-N-methyl-7-(1H-imidazo[4,5-c]pyridin-1-yl)heptanamide.
Claim 55
Dependent Claim 11 words
A compound according to Claim 43 wherein R is a group.
Claim 56
Dependent Claim 11 words
A compound according to Claim 54 wherein R 4 is cyclohexyl.
Claim 57
Dependent Claim 10 words
A compound according to Claim 54 wherein p is 0.
Claim 58
Dependent Claim 21 words
A compound according to Claim 54 wherein said compound is selected from the group consisting of: 1-[4-(1-cyciohexyl-1H-tetrazo)-5-y))butyl-1H-imidazo[4,5-c]pyridine and 1-[5-(1-cyclohexyl-1 H-tetrazol-5-yl)pentyl-1 H-imidazo[4,5-c]pyridine.
Claim 59
Dependent Claim 9 words
A compound according to Claim 41 having the formula
Claim 60
Dependent Claim 21 words
A compound according to Claim 58 wherein n is an integer from 2 to 5 and p is 0 or 1.
Claim 61
Dependent Claim 11 words
A compound according to Claim 59 wherein R is a group.
Claim 62
Dependent Claim 11 words
A compound according to Claim 60 wherein R 1 is ethyl.
Claim 63
Dependent Claim 10 words
A compound according to Claim 60 wherein p is 0.
Claim 64
Dependent Claim 25 words
A compound according to Claim 60 wherein said compound is selected from the group consisting of: ethyl 4-(3H-imidazo[4,5-c]pyridin-3-yi)butanoate, ethyl 5-(3H-imidazo[4,5-c]pyridin-3-yl)pentanoate, ethyl 6-(3H-imidazo[4,5-c]pyridin-3-yl)hexanoate, and ethyl 7-(3H-imidazo[4,5-c]pyridin-3-yl)heptanoate.
Claim 65
Dependent Claim 10 words
A compound according to Claim 60 wherein p is 1.
Claim 66
Dependent Claim 10 words
A compound according to Claim 60 which is ethyl 2,2-dimethyl-6-(3H-imidazo[4,5-c]pyridin-3-yl)-hexanoate.
Claim 67
Dependent Claim 11 words
A compound according to Claim 59 wherein R is a group.
Claim 68
Dependent Claim 25 words
A compound according to Claim 66 wherein R 2 and R 3 are independently C 1 -C 8 alkyl or C 3 -C 8 cycloalkyl.
Claim 69
Dependent Claim 10 words
A compound according to Claim 66 wherein p is 0.
Claim 70
Dependent Claim 9 words
A compound according to Claim 66 which is N-cyclohexyl-N-methyl-7-(3H-imidazo[4,5-c]pyridin-3-yl)heptanamide.
Claim 71
Dependent Claim 11 words
A compound according to Claim 59 wherein R is a group.
Claim 72
Dependent Claim 11 words
A compound according to Claim 70 wherein R 4 is cyclohexyl.
Claim 73
Dependent Claim 10 words
A compound according to Claim 70 wherein p is 0.
Claim 74
Dependent Claim 9 words
A compound according to Claim 70 which is 3-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butyl-3H-imidazo-[4,5-c]pyridine.
Claim 75
Dependent Claim 9 words
A compound according to Claim 41 having the formula
Claim 76
Dependent Claim 21 words
A compound according to Claim 74 wherein n is an integer from 2 to 5 and p is 0 to 1.
Claim 77
Dependent Claim 11 words
A compound according to Claim 75 wherein R is a group.
Claim 78
Dependent Claim 11 words
A compound according to Claim 76 wherein R 4 is cyclohexyl.
Claim 79
Dependent Claim 10 words
A compound according to Claim 75 wherein p is 0.
Claim 80
Dependent Claim 9 words
A compound according to Claim 75 which is 1-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butyl-1H-imidazo-[4,5-b]pyridine.
Claim 81
Dependent Claim 9 words
A compound according to Claim 41 having the formula
Claim 82
Dependent Claim 21 words
A compound according to Claim 80 wherein n is an integer from 2 to 5 and p is 0 or 1.
Claim 83
Dependent Claim 11 words
A compound according to Claim 81 wherein R is a group.
Claim 84
Dependent Claim 11 words
A compound according to Claim 82 wherein R 4 is cyclohexyl.
Claim 85
Dependent Claim 10 words
A compound according to Claim 81 wherein p is 0.
Claim 86
Dependent Claim 9 words
A compound according to Claim 81 which is 3-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butyl-3H-imidazo-[4,5-b]pyridine.
Claim 87
Dependent Claim 33 words
Use of a compound according to Claim 1 together with one or more non-toxic pharmaceutically acceptable carriers for the manufacturing of a medicament for treating of diseases or disorders mediated by platelat-activating factor.
Claim 88
Dependent Claim 71 words
Use of a medicament according to Claim 86 wherein said compound is selected from the group consisting of: ethyl 4-(1H-imidazo[4,5-c]pyridin-1-ytmethyl)benzoate, ethyl 3-(1 H-imidazo[4.5-c]pyridin-1-ylmethyl)benzoate, ethyl 4-(3H-imidazo[4,5-c]pyridin-3-ylmethyl]benzoate, ethyl 3-(3H-imidazo[4,5-c]pyridin-3-ylmethyl)benzoate, ethyl 4-(1 H-imidazo[4,5-b]pyridin-1-ylmethyl)benzoate, ethyl 4-(3H-imidazo[4,5-b]pyridin-3-ylmethyl)benzoate, N-cyclohexyl-N-methyl-4-[1 H-imidazo[4,5-c]pyridin-1-ylmethyl)benzamide, [4-(1H-imidazo[4,5-c]pyridin-1-ylmethyl)phenyl](4-morpholinyl)methanone, [4-(3H-imidazo(4,5-c]pyridin-3-ylmethyl)phenyl](4-morpholinyl]methanone, [4-(1H-imidazo[4,5-b]pyridin-1-ylmethyl)phenyl](4-morpholinyl)methanone, ethyl 4-(1H-imidazo[4,5-c]pyridin-1-yl)butanoate, ethyl 4-(3H-imidazo[4,5-c]pyridin-3-yl)butanoate, ethyl 5-(1 H-imidazo[4,5-c]pyridin-1-yi)pentanoate, ethyl 5-(3H-imidazo[4,5-c]pyridin-3-yl)pentanoate, ethyl 6-(1 H-imidazo[4,5-c]pyridin-1-yl)hexanoate, ethyl 6-(3H-imidazo[4,5-c]pyridin-3-yl)hexanoate, ethyl 7-(1 H-imidazo[4,5-c]pyridin-1-yl)heptanoate, ethyl 7-(3H-imidazo[4,5-c]pyridin-3-yl)heptanoate, ethyl 2,2-dimethyl-6-(1H-imidazo[4,5-c]pyridin-1-yl)hexanoate, ethyl 2,2-dimethyl-6-(3H-imidazo[4;5-c]pyridin-3-yl)hexanoate, N-cyclohexyl-N-methyl-7-(1H-imidazo[4,5-c]pyridin-1-yl)heptanamide, N-cyclohexyl-N-methyl-7-(3H-imidazo[4,5-c]pyridin-3-yl)heptanamide, 1-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butyl-1 H-imidazo[4,5-c]pyridine, 3-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butyl-3H-imidazo[4,5-c]pyridine, 1-[5-(1-cyclohexyl-1H-tetrazol-5-yl)butyl-1 H-imidazo[4,5-c]pyridine, 1-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butyl-1 H-imidazo[4,5-b]pyridine, and 3-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butyl-3H-imidazo[4,5-b]pyridine.
Claim 89
Dependent Claim 24 words
Use of a compound according to Claim 1 for the manufacturing of a medicament for treating of diseases or disorders mediated by platelet-activating factor.
Claim 90
Dependent Claim 82 words
Use of a compound for the manufacturing of a medicament according to Claim 88 wherein said compound is selected from the group consisting of: ethyl 4-(1 H-imidazo[4;5-c]pyridin-1-ylmethyl)benzoate, ethyl 3-(1 H-imidazo[4,5-c]pyridin-1-ylmethyl)benzoate, ethyl 4-(3H-imidazo[4,5-c]pyridin-3-ylmethyl)benzoate, ethyl 3-(3H-imidazo[4,5-c]pyridin-3-ylmethyl)benzoate, ethyl 4-(1 H-imidazo[4,5-b]pyridin-1-ylmethyl)benzoate, ethyl 4-(3H-imidazo[4,5-b]pyridin-3-ylmethyl)benzoate, N-cyclohexyl-N-methyl-4-[1 H-imidazo[4,5-c]pyridin-1-ylmethyl)benzamide, [4-(1 H-imidazo[4,5-c]pyridin-1-ylmethyl)phenyl](4-morpholinyl)methanone, [4-(3H-imidazo(4,5-c]pyridin-3-ylmethyl)phenyl](4-morpholinyl]methanone, [4-(1 H-imidazo[4,5-b]pyridin-1-ylmethyl)phenyl](4-morpholinyl)methanone, ethyl 4-(1 H-imidazo[4,5-c]pyridin-1-yl)butanoate, ethyl 4-(3H-imidazo[4,5-c]pyridin-3-yl)butanoate, ethyl 5-(1 H-imidazo[4,5-c]pyridin-1-yl)pentanoate, ethyl 5-(3H-imidazo[4,5-c]pyridin-3-yl)pentanoate, ethyl 6-(1 H-imidazo[4,5-c]pyridin-1-yl)hexanoate, ethyl 6-(3H-imidazo[4,5-c]pyridin-3-yl)hexanoate, ethyl 7-(1 H-imidazo[4,5-c]pyridin-1-yl)heptanoate, ethyl 7-(3H-imidazo[4,5-c]pyridin-3-yl)heptanoate, ethyl 2,2-dimethyl-6-(1 H-imidazo[4,5-c]pyridin-1-yl)hexanoate, ethyl 2,2-dimethyl-6-(3H-imidazo[4,5-c]pyridin-3-yl)hexanoate, N-cyclohexyl-N-methyl-7-(1H-imidazo[4,5-c]pyridin-1-yl)heptanamide, N-cyclohexyl-N-methyl-7-(3H-imidazo[4,5-c]pyridin-3-yl)heptanamide, 1-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butyl-1H-imidazo[4,5-c]pyridine, 3-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butyl-3H-imidazo[4,5-c]pyridine, 1-[5-(1-cyclohexyl-1 H-tetrazol-5-yl)butyl-1 H-imidazo[4,5-c]pyridine, 1-[4-(1-cyclohexyl-1H-tetrazo)-5-yl)butyl-1H-imidazo[4,5-b]pyridine, and 3-[4-(1-cyclohexyl-1 H-tetrazol-5-yl)butyl-3H-imidazo[4,5-b]pyridine.
Claim 91
Dependent Claim 175 words
Claims for the following contracting State:GR 1. A compound of the formula or a pharmaceutically acceptable acid addition salt thereof; wherein one of W, X, Y, and Z is -N-and the others of W, X, Y, and Z are each -CH-; A is a) a group wherein m is 0 or 1, or b) a -(CH 2 ) n -(CR 5 R 6 ) p -group wherein n is an integer from 0 to 8, p is an integer from 0 to 2, and R 5 and R 6 are independently hydrogen or C 1 -C 4 alkyl; and R is a) a group wherein R' is C 1 -C 8 alkyl; b) group wherein R 2 and R 3 are independently hydrogen, C 1 -C 8 alkyl, or C 3 -C 8 cycloalkyl; c) group wherein t and u are independently integers from 1 to 3 and M is -0-, -5-, or -CH 2 -; or d) group wherein R 4 is hydrogen, C 1 -C 8 alkyl, or C 3 -C 8 cycloalkyl.
Claim 92
Dependent Claim 9 words
A compound according to Claim 1 having the formula
Claim 93
Dependent Claim 9 words
A compound according to Claim 2 having the formula
Claim 94
Dependent Claim 11 words
A compound according to Claim 3 wherein R is a group.
Claim 95
Dependent Claim 10 words
A compound according to Claim 4 wherein m is 0.
Claim 96
Dependent Claim 11 words
A compound according to Claim 4 wherein R 1 is ethyl.
Claim 97
Dependent Claim 10 words
A compound according to Claim 4 which is ethyl 4-(1H-imidazo[4,5-c]pyridin-1-ylmethyl)benzoate.
Claim 98
Dependent Claim 11 words
A compound according to Claim 4 which is ethyl 3-(1 H-imidazo[4,5-c]pyridin-1-ylmelhyl)benzoate.
Claim 99
Dependent Claim 11 words
A compound according to Claim 3 wherein R is a group.
Claim 100
Dependent Claim 10 words
A compound according to Claim 9 wherein m is 0.
Claim 101
Dependent Claim 25 words
A compound according to Claim 9 wherein R 2 and R 3 are independently C 1 -C 8 alkyl or C 3 -C 8 cycloalkyl.
Claim 102
Dependent Claim 9 words
A compound according to Claim 9 which is N-cyclohexyl-N-methyl-4-[1H-imidazo[4,5-c]pyridin-1-ylmethyl)benzamide.
Claim 103
Dependent Claim 11 words
A compound according to Claim 3 wherein R is a group.
Claim 104
Dependent Claim 10 words
A compound according to Claim 13 wherein m is 0.
Claim 105
Dependent Claim 10 words
A compound according to Claim 13 wherein M is -0-.
Claim 106
Dependent Claim 9 words
A compound according to Claim 13 which is [4-(1H-imidazo[4,5-c]pyridin-1-ylmethyl)phenyl](4-morpholinyl)methanone.
Claim 107
Dependent Claim 9 words
A compound according to Claim 2 having the formula
Claim 108
Dependent Claim 11 words
A compound according to Claim 17 wherein R is a group.
Claim 109
Dependent Claim 10 words
A compouna accoraing to claim 18 wnerem m is u.
Claim 110
Dependent Claim 11 words
A compound according to Claim 18 wherein R 1 is ethyl.
Claim 111
Dependent Claim 10 words
A compound according to Claim 18 which is ethyl 4-(3H-imidazo(4,5-c]pyridin-3-ylmethyl)benzoate.
Claim 112
Dependent Claim 10 words
A compound according to Claim 18 which is ethyl 3-(3H-imidazo[4,5-c]pyridin-3-ylmethyl)benzoate.
Claim 113
Dependent Claim 11 words
A compound according to Claim 17 wherein R is a group.
Claim 114
Dependent Claim 10 words
A compound according to Claim 23 wherein m is 0.
Claim 115
Dependent Claim 10 words
A compound according to Claim 23 wherein M is -0-.
Claim 116
Dependent Claim 9 words
A compound according to Claim 23 which is [4-(3H-imidazo[4,5-c]pyridin-3-ylmethyl)phenyl)(4-morpholinyl)methanone.
Claim 117
Dependent Claim 9 words
A compound according to Claim 2 having the formula
Claim 118
Dependent Claim 13 words
- 28. A compound according to Claim 27 wherein R is a group.
Claim 119
Dependent Claim 10 words
A compound according to Claim 28 wherein m is 0.
Claim 120
Dependent Claim 11 words
A compound according to Claim 28 wherein R 1 is ethyl.
Claim 121
Dependent Claim 10 words
A compound according to Claim 28 which is ethyl 4-(1H-imidazo[4,5-b]pyridin-1-ylmethyl)benzoate.
Claim 122
Dependent Claim 11 words
A compound according to Claim 27 wherein R is a group.
Claim 123
Dependent Claim 10 words
A compound according to Claim 32 wherein m is 0.
Claim 124
Dependent Claim 10 words
A compound according to Claim 32 wherein M is -0-.
Claim 125
Dependent Claim 9 words
A compound according to Claim 32 which is [4-(1H-imidazo[4,5-bjpyridin-1-ylmethyl)phenyl](4-morpholinyl)methanone.
Claim 126
Dependent Claim 9 words
A compound according to Claim 2 having the formula
Claim 127
Dependent Claim 11 words
A compound according to Claim 36 wherein R is a group.
Claim 128
Dependent Claim 10 words
A compound according to Claim 37 wherein m is 0.
Claim 129
Dependent Claim 10 words
A compound according to Claim 37 wherein R1 is ethyl.
Claim 130
Dependent Claim 10 words
A compound according to Claim 37 which is ethyl 4-(3H-imidazo[4,5-b]pyridin-3-ylmethyl)benzoate.
Claim 131
Dependent Claim 9 words
A compound according to Claim 1 having the formula
Claim 132
Dependent Claim 9 words
A compound according to Claim 41 having the formula
Claim 133
Dependent Claim 21 words
A compound according to Claim 42 wherein n is an integer from 2 to 5 and p is 0 or 1.
Claim 134
Dependent Claim 12 words
-44. A comoound accordina to Claim 42 wherein R is a group.
Claim 135
Dependent Claim 11 words
A compound according to Claim 44 wherein R 1 is ethyl.
Claim 136
Dependent Claim 10 words
A compound according to Claim 44 wherein p is 0.
Claim 137
Dependent Claim 28 words
A compound according to Claim 44 wherein said compound is selected from the group consisting of: ethyl 4-(1 H-imidazo[4,5-c]pyridin-1-yl)butanoate, ethyl 5-(1 H-imidazo[4,5-c]pyridin-1-yl)pentanoate, ethyl 6-(1H-imidazo[4,5-c]pyridin-1-yl)hexanoate, and ethyl 7-(1 H-imidazo[4,5-c]pyridin-1-yl)heptanoate.
Claim 138
Dependent Claim 10 words
A compound according to Claim 44 wherein p is 1.
Claim 139
Dependent Claim 10 words
A compound according to Claim 44 which is ethyl 2,2-dimethyl-6-(1H-imidazo[4,5-c]pyridin-1-yl)-hexanoate.
Claim 140
Dependent Claim 11 words
A compound according to Claim 43 wherein R is a group.
Claim 141
Dependent Claim 25 words
A compound according to Claim 50 wherein R 2 and R 3 are independently C 1 -C 8 alkyl or C 3 -C 8 cycloalkyl.
Claim 142
Dependent Claim 10 words
A compound according to Claim 50 wherein p is 0.
Claim 143
Dependent Claim 9 words
A compound according to Claim 50 which is N-cyclohexyl-N-methyl-7-(1H-imidazo[4,5-c]pyridin-1-yl)heptanamide.
Claim 144
Dependent Claim 11 words
A compound according to Claim 43 wherein R is a group.
Claim 145
Dependent Claim 11 words
A compound according to Claim 54 wherein R 4 is cyclohexyl.
Claim 146
Dependent Claim 10 words
A compound according to Claim 54 wherein p is 0.
Claim 147
Dependent Claim 23 words
A compound according to Claim 54 wherein said compound is selected from the group consisting of: 1-[4-(1-cyclohexyl-1 H-tetrazol-5-yl)butyl-1 H-imidazo[4,5-c]pyridine and 1-[5-(1-cyclohexyl-1 H-tetrazol-5-yl)pentyl-1 H-imidazo[4,5-c]pyridine.
Claim 148
Dependent Claim 9 words
A compound according to Claim 41 having the formula
Claim 149
Dependent Claim 21 words
A compound according to Claim 58 wherein n is an integer from 2 to 5 and p is 0 or 1.
Claim 150
Dependent Claim 14 words
A compound according to Claim 59 wherein R is a - C OR1 group.
Claim 151
Dependent Claim 11 words
A compound according to Claim 60 wherein R 1 is ethyl.
Claim 152
Dependent Claim 10 words
A compound according to Claim 60 wherein p is 0.
Claim 153
Dependent Claim 25 words
A compound according to Claim 60 wherein said compound is selected from the group consisting of: ethyl 4-(3H-imidazo[4,5-c]pyridin-3-yl)butanoate, ethyl 5-(3H-imidazo[4,5-c]pyridin-3-yl)pentanoate, ethyl 6-(3H-imidazo[4,5-c]pyridin-3-yl)hexanoate, and ethyl 7-(3H-imidazo[4,5-c]pyridin-3-yl)heptanoate.
Claim 154
Dependent Claim 10 words
A compound according to Claim 60 wherein p is 1.
Claim 155
Dependent Claim 10 words
A compound according to Claim 60 which is ethyl 2,2-dimethyl-6-(3H-imidazo[4,5-c]pyridin-3-yl)-hexanoate.
Claim 156
Dependent Claim 11 words
A compound according to Claim 59 wherein R is a group.
Claim 157
Dependent Claim 25 words
A compound according to Claim 66 wherein R 2 and R 3 are independently C 1 -C 8 alkyl or C 3 -C 8 cycloalkyl.
Claim 158
Dependent Claim 10 words
A compound according to Claim 66 wherein p is 0.
Claim 159
Dependent Claim 9 words
A compound according to Claim 66 which is N-cyclohexyl-N-methyl-7-(3H-imidazo[4,5-c]pyridin-3-yl)heptanamide.
Claim 160
Dependent Claim 11 words
A compound according to Claim 59 wherein R is a group.
Claim 161
Dependent Claim 11 words
A compound according to Claim 70 wherein R 4 is cyclohexyl.
Claim 162
Dependent Claim 10 words
A compound according to Claim 70 wherein p is 0.
Claim 163
Dependent Claim 9 words
A compound according to Claim 70 which is 3-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butyl-3H-imidazo-[4,5-c]pyridine.
Claim 164
Dependent Claim 9 words
A compound according to Claim 41 having the formula
Claim 165
Dependent Claim 21 words
A compound according to Claim 74 wherein n is an integer from 2 to 5 and p is 0 or 1.
Claim 166
Dependent Claim 11 words
A compound according to Claim 75 wherein R is a group.
Claim 167
Dependent Claim 11 words
A compound according to Claim 76 wherein R 4 is cyclohexyl.
Claim 168
Dependent Claim 10 words
A compound according to Claim 75 wherein p is 0.
Claim 169
Dependent Claim 9 words
A compound according to Claim 75 which is 1-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butyl-1H-imidazo-[4,5-b]pyridine.
Claim 170
Dependent Claim 9 words
A compound according to Claim 41 having the formula
Claim 171
Dependent Claim 21 words
A compound according to Claim 80 wherein n is an integer from 2 to 5 and p is 0 or 1.
Claim 172
Dependent Claim 11 words
A compound according to Claim 81 wherein R is a group.
Claim 173
Dependent Claim 11 words
A compound according to Claim 82 wherein R 4 is cyclohexyl.
Claim 174
Dependent Claim 10 words
A compound according to Claim 81 wherein p is 0.
Claim 175
Dependent Claim 9 words
A compound according to Claim 81 which is 3-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butyl-3H-imidazo-[4,5-b]pyridine.
Claim 176
Dependent Claim 410 words
Claims for the following contracting States: AT and ES 1. Process for preparing a compound of the formula or a pharmaceutically acceptable acid addition salt thereof; wherein one of W, X, Y, and Z is -N-and the others of W, X, Y, and Z are each -CH-; A is a) a group wherein m is 0 or 1, or b) a -(CH 2 ) n -(CR 5 R 6 ) p -group wherein n is an integer from 0 to 8, p is an integer from 0 to 2, and R 5 and R 6 are independently hydrogen or C 1 -C 4 alkyl; and R is group wherein R 1 is C 1 -C 8 alkyl; group wherein R 2 and R 3 are independently hydrogen, C 1 -C 8 alkyl, or C 3 - C 8 cycloalkyl; group wherein t and u are independently integers from 1 to 3 and M is -0-, -5-, or -CH 2 -; or group wherein R 4 is hydrogen, C 1 -C 8 alkyl, or C 3 -C 8 cycloalkyl characterized in that imidazo[4,5-b]pyridine, represented as a tautomeric mixture of the formula or imidazo[4,5-c]pyridine, represented as a tautomeric mixture of the formula is treated with a compound of the formula D-CH2-A-R wherein A and R are above defined and D is chloro, bromo, iodo, methanesulfonyloxy or p-toluenesulfonyloxy in the presence of a base, preferably sodium or potassium hydride, and an aprotic solvent, preferably dimethylformamide, to yield an isomeric mixture which is separated or a substituted nitropyridine of the formula wherein W, X, Y, and Z are as above defined and B is halo or C 1 -C 4 alkoxy; is treated with a substituted amine of the formula H2N-CH2-A-R wherein A and R are as above defined to yield a substituted amino nitropyridine of the formula that is reduced, for example in the presence of hydrogen and a catalyst such as palladium or platinum, to yield a substituted diaminopyridine of the formula that is treated with dimethylformamide and triethyl orthoformate in the presence of a catalytic amount of concentrated hydrochlorid acid at room temperature, alternatively the substituted diaminopyridines may be prepared by treating a substituted pyridine of formula with a substituted aldehyde of the formula wherein A and R are as above defined; to yield an imino nitropyridine of the formula and then reducing the imino nitropyridine, for example in the presence of hydrogen and a catalyst such as palladium or platinum.
Claim 177
Dependent Claim 12 words
Process according to Claim 1 wherein the compound prepared has the formula
Claim 178
Dependent Claim 12 words
Process according to Claim 2 wherein the compound prepared has the formula
Claim 179
Dependent Claim 10 words
Process according to Claim 3 wherein R is a group.
Claim 180
Dependent Claim 9 words
Process according to Claim 4 wherein m is 0.
Claim 181
Dependent Claim 10 words
Process according to Claim 4 wherein R 1 is ethyl.
Claim 182
Dependent Claim 12 words
Process according to Claim 4 wherein the compound prepared is ethyl 4-(1H-imidazo[4,5-c]pyridin-1-ylmethyl)benzoate.
Claim 183
Dependent Claim 12 words
Process according to Claim 4 wherein the compound prepared is ethyl 3-(1H-imidazo[4,5-c]pyridin-1-ylmethyl)benzoate.
Claim 184
Dependent Claim 10 words
Process according to Claim 3 wherein R is a group.
Claim 185
Dependent Claim 9 words
Process according to Claim 9 wherein m is 0.
Claim 186
Dependent Claim 24 words
Process according to Claim 9 wherein R 2 and R 3 are independently C 1 -C 8 alkyl or C 3 -C 8 cycloalkyl.
Claim 187
Dependent Claim 12 words
Process according to Claim 9 wherein the compound prepared is N-cyclohexyl-N-methyl-4-[l H-imidazo[4,5-c]pyridin-1-ylmethyl)benzamide.
Claim 188
Dependent Claim 10 words
Process according to Claim 3 wherein R is a group.
Claim 189
Dependent Claim 9 words
Process according to Claim 13 wherein m is 0.
Claim 190
Dependent Claim 9 words
Process according to Claim 13 wherein M is -0-.
Claim 191
Dependent Claim 11 words
Process according to Claim 13 wherein the compound prepared is [4-(1H-imidazo[4,5-c]pyridin-1-ylmethyl)phenyl](4-morpholinyl)methanone.
Claim 192
Dependent Claim 12 words
Process according to Claim 2 wherein the compound prepared has the formula
Claim 193
Dependent Claim 10 words
Process according to Claim 17 wherein R is a group.
Claim 194
Dependent Claim 9 words
Process according to Claim 18 wherein m is 0.
Claim 195
Dependent Claim 10 words
Process according to Claim 18 wherein R 1 is ethyl.
Claim 196
Dependent Claim 12 words
Process according to Claim 18 wherein the compound prepared is ethyl 4-(3H-imidazo[4,5-c]pyridin-3-ylmethyl)benzoate.
Claim 197
Dependent Claim 12 words
Process according to Claim 18 wherein the compound prepared is ethyl 3-(3H-imidazo[4,5,c]pyridin-3-ylmethyl)benzoate.
Claim 198
Dependent Claim 10 words
Process according to Claim 17 wherein R is a group.
Claim 199
Dependent Claim 9 words
Process according to Claim 23 wherein m is 0.
Claim 200
Dependent Claim 9 words
Process according to Claim 23 wherein M is -0-.
Claim 201
Dependent Claim 11 words
Process according to Claim 23 wherein the compound prepared is [4-(3H-imidazo[4,5-c]pyridin-3-ylmethyl)phenyl](4-morpholinyl)methanone.
Claim 202
Dependent Claim 12 words
Process according to Claim 2 wherein the compound prepared has the formula
Claim 203
Dependent Claim 10 words
Process according to Claim 27 wherein R is a group.
Claim 204
Dependent Claim 9 words
Process according to Claim 28 wherein m is 0.
Claim 205
Dependent Claim 10 words
Process according to Claim 28 wherein R 1 is ethyl.
Claim 206
Dependent Claim 12 words
Process according to Claim 28 wherein the compound prepared is ethyl 4-(1H-imidazo[4,5-b]-pyridin-1-ylmethyl)benzoate.
Claim 207
Dependent Claim 10 words
Process according to Claim 27 wherein R is a group.
Claim 208
Dependent Claim 9 words
Process according to Claim 32 wherein m is 0.
Claim 209
Dependent Claim 9 words
Process according to Claim 32 wherein M is -0-.
Claim 210
Dependent Claim 11 words
Processs according to Claim 32 wherein the compound prepared is [4-(1H-imidazo[4,5-b]pyridin-1-ylmethyl)phenyl](4-morpholinyl)methanone.
Claim 211
Dependent Claim 12 words
Process according to Claim 2 wherein the compound prepared has the formula
Claim 212
Dependent Claim 10 words
Process according to Claim 36 wherein R is a group.
Claim 213
Dependent Claim 9 words
Process according to Claim 37 wherein m is 0.
Claim 214
Dependent Claim 10 words
Process according to Claim 37 wherein R I is ethyl.
Claim 215
Dependent Claim 12 words
Process according to Claim 37 wherein the compound prepared is ethyl 4-(3H-imidazo[4,5-b]-pyridin-3-ylmethyl)benzoate.
Claim 216
Dependent Claim 12 words
Process according to Claim 1 wherein the compound prepared has the formula
Claim 217
Dependent Claim 12 words
Process according to Claim 41 wherein the compound prepared has the formula
Claim 218
Dependent Claim 20 words
Process according to Claim 42 wherein n is an integer from 2 to 5 and p is 0 or 1.
Claim 219
Dependent Claim 10 words
Process according to Claim 42 wherein R is a group.
Claim 220
Dependent Claim 10 words
Process according to Claim 44 wherein R 1 is ethyl.
Claim 221
Dependent Claim 9 words
Process according to Claim 44 wherein p is 0.
Claim 222
Dependent Claim 26 words
Process according to Claim 44 wherein said compound is selected from the group consisting of: ethyl 4-(1 H-imidazo[4,5-c]pyridin-1-yl)butanoate, ethyl 5-(1H-imidazo[4,5-c]pyridin-1-yl)pentanoate, ethyl 6-(1H-imidazo[4,5-c]pyridin-1-yl)hexanoate, and ethyl 7-(1 H-imidazo[4,5-c]pyridin-1-yl)heptanoate.
Claim 223
Dependent Claim 9 words
Process according to Claim 44 wherein p is 1.
Claim 224
Dependent Claim 13 words
Process according to Claim 44 wherein the compound prepared is ethyl 2,2-dimethyl-6-(l H-imidazo-[4,5-c]pyridin-1-yl)hexanoate.
Claim 225
Dependent Claim 10 words
Process according to Claim 43 wherein R is a group.
Claim 226
Dependent Claim 24 words
Process according to Claim 50 wherein R 2 and R 3 are independently C 1 -C 8 alkyl or C 3 -C 8 cycloalkyl.
Claim 227
Dependent Claim 9 words
Process according to Claim 50 wherein p is 0.
Claim 228
Dependent Claim 11 words
Process according to Claim 50 wherein the compound prepared is N-cyclohexyl-N-methyl-7-(1H-imidazo[4,5-c]pyridin-1-yl)heptanamide.
Claim 229
Dependent Claim 10 words
Process according to Claim 43 wherein R is a group.
Claim 230
Dependent Claim 10 words
Process according to Claim 54 wherein R 4 is cyclohexyl.
Claim 231
Dependent Claim 9 words
Process according to Claim 54 wherein p is 0.
Claim 232
Dependent Claim 22 words
Process according to Claim 54 wherein said compound is selected from the group consisting of: 1-[4-(1-cyclohexyl-1 H-tetrazol-5-yl)butyl-1 H-imidazo[4,5-c]pyridine and 1-[5-(1-cyclohexyl-1 H-tetrazol-5-yl)pentyl-1 H-imidazo[4,5-c]pyridine.
Claim 233
Dependent Claim 12 words
Process according to Claim 54 wherein the compound prepared has the formula
Claim 234
Dependent Claim 20 words
Process according to Claim 58 wherein n is an integer from 2 to 5 and p is 0 or 1.
Claim 235
Dependent Claim 10 words
Process accordina to Claim 59 wherein R is a group.
Claim 236
Dependent Claim 9 words
Process according to Claim 60 wherein R1 is ethyl.
Claim 237
Dependent Claim 9 words
Process according to Claim 60 wherein p is 0.
Claim 238
Dependent Claim 23 words
according to Claim 60 wherein said compound is selected from the group consisting of: ethyl 4-(3H-imidazo[4,5-c]pyridin-3-yl)butanoate, ethyl 5-(3H-imidazo[4,5-c]pyridin-3-yl)pentanoate, ethyl 6-(3H-imidazo[4,5-c]pyridin-3-yl)hexanoate, and ethyl 7-(3H-imidazo[4,5-c]pyridin-3-yi)heptanoate.
Claim 239
Dependent Claim 9 words
Process according to Claim 60 wherein p is 1.
Claim 240
Dependent Claim 12 words
Process according to Claim 60 wherein the compound prepared is ethyl 2,2-dimethyl-6-(3H-imidazo-[4,5-c]pyridin-3-yl)hexanoate.
Claim 241
Dependent Claim 10 words
Process according to Claim 59 wherein R is a group.
Claim 242
Dependent Claim 21 words
Process according to Claim 66 wherein R 2 and R 3 are independently C 1 -Ca alkyl or CrC 8 cycloalkyl.
Claim 243
Dependent Claim 9 words
Process according to Claim 66 wherein p is 0.
Claim 244
Dependent Claim 11 words
Process according to Claim 66 wherein the compound prepared is N-cyclohexyl-N-methyl-7-(3H-imidazo[4,5-c]pyridin-3-yl)heptanamide.
Claim 245
Dependent Claim 10 words
Process according to Claim 59 wherein R is a group.
Claim 246
Dependent Claim 10 words
Process according to Claim 70 wherein R 4 is cyclohexyl.
Claim 247
Dependent Claim 9 words
Process according to Claim 70 wherein p is 0.
Claim 248
Dependent Claim 11 words
Process according to Claim 40 wherein the compound prepared is 3-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butyl-3H-imidazo[4,5-c]pyridine.
Claim 249
Dependent Claim 12 words
Process according to Claim 41 wherein the compound prepared has the formula
Claim 250
Dependent Claim 20 words
Process according to Claim 74 wherein n is an integer from 2 to 5 and p is 0 or 1.
Claim 251
Dependent Claim 10 words
Process according to Claim 75 wherein R is a group.
Claim 252
Dependent Claim 10 words
Process according to Claim 76 wherein R 4 is cyclohexyl.
Claim 253
Dependent Claim 9 words
Process according to Claim 75 wherein p is 0.
Claim 254
Dependent Claim 12 words
Process according to Claim 75 wherein the compound prepared is 1-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butyl-1 H-imidazo[4,5-b]pyridine.
Claim 255
Dependent Claim 12 words
Process according to Claim 41 wherein the compound prepared has the formula
Claim 256
Dependent Claim 20 words
Process according to Claim 80 wherein n is an integer from 2 to 5 and p is 0 or 1.
Claim 257
Dependent Claim 10 words
Process according to Claim 81 wherein R is a group.
Claim 258
Dependent Claim 10 words
Process according to Claim 82 wherein R 4 is cyclohexyl.
Claim 259
Dependent Claim 9 words
Process according to Claim 81 wherein p is 0.
Claim 260
Dependent Claim 11 words
Process according to Claim 81 wherein the compound prepared is 3-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butyl-3H-imidazo[4,5-b]pyridine.

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