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US4593029A
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Novel ω-(N-imidazolyl)alkyl ethers of 1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-ones
Assignee: Syntex USA LLC
•
Filing: 1984-02-15
•
Granted: 1986-06-03
•
Expires: 2004-02-15
Abstract
Abstract Novel compound of the formula <IMAGE> (I) wherein n is an integer of 1 to 8; R1 is hydrogen or alkyl of 1-6 carbons; R2 is hydrogen; R3 is hydrogen, alkyl of 1-6 carbons, phenyl, benzyl, hydroxy lower alkyl, carbamoyl alkyl, carboxyalkyl, alkoxycarbonylalkyl; R4 is hydrogen, alkyl of 1-6 carbons, benzyl, or hydroxy lower alkyl; Y is hydrogen, alkyl of 1 to 4 carbon atoms, halo or lower alkoxy; any of its optical isomers, the mixture thereof, or the pharmaceutically acceptable acid addition salt. These compounds are inhibitors of thromboxane synthetase and cyclic AMP phosphodiesterase and are therefore potential cardiovascular agents particularly useful as platelet aggregation inhibitors and anti-thrombotic agents. Accordingly, these compounds will preferably be useful in treating cardiovascular disorders with thrombotic complications. However, they also possess vasodilatory, antisecretory, antihypertensive, inotropic and antimetastatic activities.
Inventors
- 👤 Michael C. Venuti
- 👤 John J. Bruno
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 19:14
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04
Claims Analysis
Total Claims: 151
Claim 1
Independent Claim
86 words
A compound of the formula ##STR8## wherein: n is an integer of 1 to 8; R 1 is hydrogen or alkyl of 1-6 carbons; R 2 is hydrogen; R 3 is hydrogen, alkyl of 1-6 carbons, phenyl, benzyl, hydroxy lower alkyl, carbamoylalkyl, carboxyalkyl, alkoxycarbonylalkyl; R 4 is hydrogen, alkyl of 1-6 carbons, benzyl, or hydroxy lower alkyl; Y is hydrogen, alkyl of 1 to 4 carbon atoms, halo or lower alkoxy; any of its optical isomers, the mixture thereof, or a pharmaceutically acceptable acid addition salt.
Claim 2
Dependent Claim
86 words
A compound of the formula ##STR8## wherein: n is an integer of 1 to 8; R 1 is hydrogen or alkyl of 1-6 carbons; R 2 is hydrogen; R 3 is hydrogen, alkyl of 1-6 carbons, phenyl, benzyl, hydroxy lower alkyl, carbamoylalkyl, carboxyalkyl, alkoxycarbonylalkyl; R 4 is hydrogen, alkyl of 1-6 carbons, benzyl, or hydroxy lower alkyl; Y is hydrogen, alkyl of 1 to 4 carbon atoms, halo or lower alkoxy; any of its optical isomers, the mixture thereof, or a pharmaceutically acceptable acid addition salt.
Claim 3
Dependent Claim
14 words
The compound of claim 1 wherein n is an integer of 2 to 6.
Claim 4
Dependent Claim
20 words
The compound of claim 2 wherein n is 2 and R 1 , R 2 and R 4 are hydrogen.
Claim 5
Dependent Claim
10 words
The compound of claim 3 wherein R 3 is hydrogen.
Claim 6
Dependent Claim
11 words
The compound of claim 4 wherein Y is hydrogen, namely 7-[2-(N-imidazolyl)ethyl]oxy-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 7
Dependent Claim
11 words
The compound of claim 4 wherein Y is chloro, namely 7-[2-(N-imidazolyl)ethyl]oxy-6-chloro-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 8
Dependent Claim
11 words
The compound of claim 4 wherein Y is methoxy, namely 7-[2-(N-imidazolyl)ethyl]oxy-6-methoxy-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 9
Dependent Claim
10 words
The compound of claim 3 wherein R 3 is methyl.
Claim 10
Dependent Claim
11 words
The compound of claim 8 wherein Y is hydrogen, namely 7-[2-(N-imidazolyl)ethyl]oxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 11
Dependent Claim
11 words
The compound of claim 8 wherein Y is chloro, namely 7-[2-(N-imidazolyl)ethyl]oxy-6-chloro-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 12
Dependent Claim
11 words
The compound of claim 8 wherein Y is methoxy, namely 7-[2-(N-imidazolyl)ethyl]oxy-6-methoxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 13
Dependent Claim
10 words
The compound of claim 3 wherein R 3 is ethyl.
Claim 14
Dependent Claim
11 words
The compound of claim 12 wherein Y is hydrogen, namely 7-[2-(N-imidazolyl)ethyl]oxy-3-ethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 15
Dependent Claim
11 words
The compound of claim 12 wherein Y is chloro, namely 7-[2-(N-imidazolyl)ethyl]oxy-6-chloro-3-ethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 16
Dependent Claim
11 words
The compound of claim 12 wherein Y is methoxy, namely 7-[2-(N-imidazolyl)ethyl]oxy-6-methoxy-3-ethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 17
Dependent Claim
10 words
The compound of claim 3 wherein R 3 is hydroxymethyl.
Claim 18
Dependent Claim
11 words
The compound of claim 16 wherein Y is hydrogen, namely 7-[2-(N-imidazolyl)ethyl]oxy-3-hydroxy-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 19
Dependent Claim
11 words
The compound of claim 16 wherein Y is chloro, namely 7-[2-(N-imidazolyl)ethyl]oxy-6-chloro-3-hydroxy-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 20
Dependent Claim
11 words
The compound of claim 12 wherein Y is methoxy, namely 7-[2-(N-imidazolyl)ethyl]oxy-6-methoxy-3-hydroxy-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 21
Dependent Claim
20 words
The compound of claim 2 wherein n is 3 and R 1 , R 2 and R 4 are hydrogen.
Claim 22
Dependent Claim
10 words
The compound of claim 20 wherein R 3 is hydrogen.
Claim 23
Dependent Claim
11 words
The compound of claim 21 wherein Y is hydrogen, namely 7-[3-(N-imidazolyl)propyl]oxy-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 24
Dependent Claim
11 words
The compound of claim 21 wherein Y is chloro, namely 7-[3-(N-imidazolyl)propyl]oxy-6-chloro-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 25
Dependent Claim
11 words
The compound of claim 21 wherein Y is methoxy, namely 7-[3-(N-imidazolyl)propyl]oxy-6-methoxy-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 26
Dependent Claim
10 words
The compound of claim 20 wherein R 3 is methyl.
Claim 27
Dependent Claim
11 words
The compound of claim 25 wherein Y is hydrogen, namely 7-[3-(N-imidazolyl)propyl]oxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 28
Dependent Claim
11 words
The compound of claim 25 wherein Y is chloro, namely 7-[3-(N-imidazolyl)propyl]oxy-6-chloro-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 29
Dependent Claim
11 words
The compound of claim 25 wherein Y is methoxy, namely 7-[3-(N-imidazolyl)propyl]oxy-6-methoxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 30
Dependent Claim
10 words
The compound of claim 20 wherein R 3 is ethyl.
Claim 31
Dependent Claim
11 words
The compound of claim 29 wherein Y is hydrogen, namely 7-[3-(N-imidazolyl)propyl]oxy-3-ethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 32
Dependent Claim
11 words
The compound of claim 29 wherein Y is chloro, namely 7-[3-(N-imidazolyl)propyl]oxy-6-chloro-3-ethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 33
Dependent Claim
11 words
The compound of claim 29 wherein Y is methoxy, namely 7-[3-(N-imidazolyl)propyl]oxy-6-methoxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 34
Dependent Claim
10 words
The compound of claim 20 wherein R 3 is hydroxymethyl.
Claim 35
Dependent Claim
11 words
The compound of claim 33 wherein Y is hydrogen, namely 7-[3-(N-imidazolyl)propyl]oxy-3-hydroxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 36
Dependent Claim
11 words
The compound of claim 33 wherein Y is chloro, namely 7-[3-(N-imidazolyl)propyl]oxy-6-chloro-3-hydroxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 37
Dependent Claim
11 words
The compound of claim 33 wherein Y is methoxy, namely 7-[3-(N-imidazolyl)propyl]oxy-6-methoxy-3-hydroxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 38
Dependent Claim
20 words
The compound of claim 2 wherein n is 4 and R 1 , R 2 and R 4 are hydrogen.
Claim 39
Dependent Claim
10 words
The compound of claim 37 wherein R 3 is hydrogen.
Claim 40
Dependent Claim
11 words
The compound of claim 38 wherein Y is hydrogen, namely 7-[4-(N-imidazolyl)butyl]oxy-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 41
Dependent Claim
11 words
The compound of claim 38 wherein Y is chloro, namely 7-[4-(N-imidazolyl)butyl]oxy-6-chloro-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 42
Dependent Claim
11 words
The compound of claim 38 wherein Y is methoxy, namely 7-[4-(N-imidazolyl)butyl]oxy-6-methoxy-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 43
Dependent Claim
10 words
The compound of claim 37 wherein R 3 is methyl.
Claim 44
Dependent Claim
11 words
The compound of claim 42 wherein Y is hydrogen, namely 7-[4-(N-imidazolyl)butyl]oxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 45
Dependent Claim
11 words
The compound of claim 42 wherein Y is chloro, namely 7-[4-(N-imidazolyl)butyl]oxy-6-chloro-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 46
Dependent Claim
11 words
The compound of claim 42 wherein Y is methoxy, namely 7-[4-(N-imidazolyl)butyl]oxy-6-methoxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 47
Dependent Claim
10 words
The compound of claim 37 wherein R 3 is ethyl.
Claim 48
Dependent Claim
11 words
The compound of claim 46 wherein Y is hydrogen, namely 7-[4-(N-imidazolyl)butyl]oxy-3-ethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 49
Dependent Claim
11 words
The compound of claim 46 wherein Y is chloro, namely 7-[4-(N-imidazolyl)butyl]oxy-6-chloro-3-ethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 50
Dependent Claim
11 words
The compound of claim 46 wherein Y is methoxy, namely 7-[4-(N-imidazolyl)butyl]oxy-6-methoxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 51
Dependent Claim
10 words
The compound of claim 37 wherein R 3 is hydroxymethyl.
Claim 52
Dependent Claim
11 words
The compound of claim 50 wherein Y is hydrogen, namely 7-[4-(N-imidazolyl)butyl]oxy-3-hydroxy-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 53
Dependent Claim
11 words
The compound of claim 50 wherein Y is chloro, namely 7-[4-(N-imidazolyl)butyl]oxy-6-chloro-3-hydroxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 54
Dependent Claim
11 words
The compound of claim 50 wherein Y is methoxy, namely 7-[4-(N-imidazolyl)butyl]oxy-6-methoxy-3-hydroxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 55
Dependent Claim
20 words
The compound of claim 2 wherein n is 5 and R 1 , R 2 and R 4 are hydrogen.
Claim 56
Dependent Claim
10 words
The compound of claim 54 wherein R 3 is hydrogen.
Claim 57
Dependent Claim
11 words
The compound of claim 55 wherein Y is hydrogen, namely 7-[5-(N-imidazolyl)pentyl]oxy-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 58
Dependent Claim
11 words
The compound of claim 55 wherein Y is chloro, namely 7-[5-(N-imidazolyl)pentyl]oxy-6-chloro-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 59
Dependent Claim
11 words
The compound of claim 55 wherein Y is methoxy, namely 7-[5-(N-imidazolyl)pentyl]oxy-6-methoxy-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 60
Dependent Claim
10 words
The compound of claim 54 wherein R 3 is methyl.
Claim 61
Dependent Claim
11 words
The compound of claim 59 wherein Y is hydrogen, namely 7-[5-(N-imidazolyl)pentyl]oxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 62
Dependent Claim
11 words
The compound of claim 59 wherein Y is chloro, namely 7-[5-(N-imidazolyl)pentyl]oxy-6-chloro-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 63
Dependent Claim
11 words
The compound of claim 59 wherein Y is methoxy, namely 7-[5-(N-imidazolyl)pentyl]oxy-6-methoxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 64
Dependent Claim
10 words
The compound of claim 54 wherein R 3 is ethyl.
Claim 65
Dependent Claim
11 words
The compound of claim 63 wherein Y is hydrogen, namely 7-[5-(N-imidazolyl)pentyl]oxy-3-ethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 66
Dependent Claim
11 words
The compound of claim 63 wherein Y is chloro, namely 7-[5-(N-imidazolyl)pentyl]oxy-6-chloro-3-ethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 67
Dependent Claim
11 words
The compound of claim 63 wherein Y is methoxy, namely 7-[5-(N-imidazolyl)pentyl]oxy-6-methoxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 68
Dependent Claim
10 words
The compound of claim 54 wherein R 3 is hydroxymethyl.
Claim 69
Dependent Claim
11 words
The compound of claim 67 wherein Y is hydrogen, namely 7-[5-(N-imidazolyl)pentyl]oxy-3-hydroxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 70
Dependent Claim
11 words
The compound of claim 67 wherein Y is chloro, namely 7-[5-(N-imidazolyl)pentyl]oxy-6-chloro-3-hydroxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 71
Dependent Claim
11 words
The compound of claim 67 wherein Y is methoxy, namely 7-[5-(N-imidazolyl)pentyl]oxy-6-methoxy-3-hydroxy-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 72
Dependent Claim
20 words
The compound of claim 2 wherein n is 6 and R 1 , R 2 and R 4 are hydrogen.
Claim 73
Dependent Claim
10 words
The compound of claim 71 wherein R 3 is hydrogen.
Claim 74
Dependent Claim
11 words
The compound of claim 72 wherein Y is hydrogen, namely 7-[6-(N-imidazolyl)hexyl]oxy-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 75
Dependent Claim
11 words
The compound of claim 72 wherein Y is chloro, namely 7-[6-(N-imidazolyl)hexyl]oxy-6-chloro-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 76
Dependent Claim
11 words
The compound of claim 72 wherein Y is methoxy, namely 7-[6-(N-imidazolyl)hexyl]oxy-6-methoxy-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 77
Dependent Claim
10 words
The compound of claim 71 wherein R 3 is methyl.
Claim 78
Dependent Claim
11 words
The compound of claim 76 wherein Y is hydrogen, namely 7-[6-(N-imidazolyl)hexyl]oxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 79
Dependent Claim
11 words
The compound of claim 76 wherein Y is chloro, namely 7-[6-(N-imidazolyl)hexyl]oxy-6-chloro-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 80
Dependent Claim
11 words
The compound of claim 76 wherein Y is methoxy, namely 7-[6-(N-imidazolyl)hexyl]oxy-6-methoxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 81
Dependent Claim
10 words
The compound of claim 71 wherein R 3 is ethyl.
Claim 82
Dependent Claim
11 words
The compound of claim 80 wherein Y is hydrogen, namely 7-[6-(N-imidazolyl)hexyl]oxy-3-ethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 83
Dependent Claim
11 words
The compound of claim 80 wherein Y is chloro, namely 7-[6-(N-imidazolyl)hexyl]oxy-6-chloro-3-ethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 84
Dependent Claim
11 words
The compound of claim 80 wherein Y is methoxy, namely 7-[6-(N-imidazolyl)hexyl]oxy-6-methoxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 85
Dependent Claim
10 words
The compound of claim 71 wherein R 3 is hydroxymethyl.
Claim 86
Dependent Claim
11 words
The compound of claim 84 wherein Y is hydrogen, namely 7-[6-(N-imidazolyl)hexyl]oxy-3-hydroxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 87
Dependent Claim
11 words
The compound of claim 84 wherein Y is chloro, namely 7-[6-(N-imidazolyl)hexyl]oxy-6-chloro-3-hydroxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 88
Dependent Claim
11 words
The compound of claim 84 wherein Y is methoxy, namely 7-[6-(N-imidazolyl)hexyl]oxy-6-methoxy-3-hydroxy-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 89
Dependent Claim
20 words
The compound of claim 2 wherein n is 1 and R 1 , R 2 and R 4 are hydrogen.
Claim 90
Dependent Claim
10 words
The compound of claim 88 wherein R 3 is hydrogen.
Claim 91
Dependent Claim
11 words
The compound of claim 89 wherein Y is hydrogen, namely 7-[1-(N-imidazolyl)methyl]oxy-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 92
Dependent Claim
11 words
The compound of claim 89 wherein Y is chloro, namely 7-[1-(N-imidazolyl)methyl]oxy-6-chloro-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 93
Dependent Claim
11 words
The compound of claim 89 wherein Y is methoxy, namely 7-[1-(N-imidazolyl)methyl]oxy-6-methoxy-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 94
Dependent Claim
10 words
The compound of claim 88 wherein R 3 is methyl.
Claim 95
Dependent Claim
11 words
The compound of claim 93 wherein Y is hydrogen, namely 7-[1-(N-imidazolyl)methyl]oxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 96
Dependent Claim
11 words
The compound of claim 93 wherein Y is chloro, namely 7-[1-(N-imidazolyl)methyl]oxy-6-chloro-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 97
Dependent Claim
11 words
The compound of claim 93 wherein Y is methoxy, namely 7-[1-(N-imidazolyl)methyl]oxy-6-methoxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 98
Dependent Claim
10 words
The compound of claim 88 wherein R 3 is ethyl.
Claim 99
Dependent Claim
11 words
The compound of claim 97 wherein Y is hydrogen, namely 7-[1-(N-imidazolyl)methyl]oxy-3-ethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 100
Dependent Claim
11 words
The compound of claim 97 wherein Y is chloro, namely 7-[1-(N-imidazolyl)methyl]oxy-6-chloro-3-ethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 101
Dependent Claim
11 words
The compound of claim 97 wherein Y is methoxy, namely 7-[1-(N-imidazolyl)methyl]oxy-6-methoxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 102
Dependent Claim
10 words
The compound of claim 88 wherein R 3 is hydroxymethyl.
Claim 103
Dependent Claim
11 words
The compound of claim 101 wherein Y is hydrogen, namely 7-[1-(N-imidazolyl)methyl]oxy-3-hydroxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 104
Dependent Claim
11 words
The compound of claim 101 wherein Y is chloro, namely 7-[1-(N-imidazolyl)methyl]oxy-6-chloro-3-hydroxy-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 105
Dependent Claim
11 words
The compound of claim 101 wherein Y is methoxy, namely 7-[1-(N-imidazolyl)methyl]oxy-6-methoxy-3-hydroxy-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 106
Dependent Claim
20 words
The compound of claim 2 wherein n is 7 and R 1 , R 2 and R 4 are hydrogen.
Claim 107
Dependent Claim
10 words
The compound of claim 105 wherein R 3 is hydrogen.
Claim 108
Dependent Claim
11 words
The compound of claim 106 wherein Y is hydrogen, namely 7-[7-(N-imidazolyl)heptyl]oxy-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 109
Dependent Claim
11 words
The compound of claim 106 wherein Y is chloro, namely 7-[7-(N-imidazolyl)heptyl]oxy-6-chloro-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 110
Dependent Claim
11 words
The compound of claim 106 wherein Y is methoxy, namely 7-[7-(N-imidazolyl)heptyl]oxy-6-methoxy-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 111
Dependent Claim
10 words
The compound of claim 105 wherein R 3 is methyl.
Claim 112
Dependent Claim
11 words
The compound of claim 110 wherein Y is hydrogen, namely 7-[7-(N-imidazolyl)heptyl]oxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 113
Dependent Claim
11 words
The compound of claim 110 wherein Y is chloro, namely 7-[7-(N-imidazolyl)heptyl]oxy-6-chloro-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 114
Dependent Claim
11 words
The compound of claim 110 wherein Y is methoxy, namely 7-[7-(N-imidazolyl)heptyl]oxy-6-methoxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 115
Dependent Claim
10 words
The compound of claim 105 wherein R 3 is ethyl.
Claim 116
Dependent Claim
11 words
The compound of claim 114 wherein Y is hydrogen, namely 7-[7-(N-imidazolyl)heptyl]oxy-3-ethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 117
Dependent Claim
11 words
The compound of claim 114 wherein Y is chloro, namely 7-[7-(N-imidazolyl)heptyl]oxy-6-chloro-3-ethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 118
Dependent Claim
11 words
The compound of claim 114 wherein Y is methoxy, namely 7-[7-(N-imidazolyl)heptyl]oxy-6-methoxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 119
Dependent Claim
10 words
The compound of claim 105 wherein R 3 is hydroxymethyl.
Claim 120
Dependent Claim
11 words
The compound of claim 118 wherein Y is hydrogen, namely 7-[7-(N-imidazolyl)heptyl]oxy-3-hydroxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 121
Dependent Claim
11 words
The compound of claim 118 wherein Y is chloro, namely 7-[7-(N-imidazolyl)heptyl]oxy-6-chloro-3-hydroxy-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 122
Dependent Claim
11 words
The compound of claim 118 wherein Y is methoxy, namely 7-[7-(N-imidazolyl)heptyl]oxy-6-methoxy-3-hydroxy-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 123
Dependent Claim
20 words
The compound of claim 2 wherein n is 8 and R 1 , R 2 and R 4 are hydrogen.
Claim 124
Dependent Claim
10 words
The compound of claim 122 wherein R 3 is hydrogen.
Claim 125
Dependent Claim
11 words
The compound of claim 123 wherein Y is hydrogen, namely 7-[8-(N-imidazolyl)octyl]oxy-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 126
Dependent Claim
11 words
The compound of claim 123 wherein Y is chloro, namely 7-[8-(N-imidazolyl)octyl]oxy-6-chloro-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 127
Dependent Claim
11 words
The compound of claim 123 wherein Y is methoxy, namely 7-[8-(N-imidazolyl)octyl]oxy-6-methoxy-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 128
Dependent Claim
10 words
The compound of claim 122 wherein R 3 is methyl.
Claim 129
Dependent Claim
11 words
The compound of claim 127 wherein Y is hydrogen, namely 7-[8-(N-imidazolyl)octyl]oxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 130
Dependent Claim
11 words
The compound of claim 127 wherein Y is chloro, namely 7-[8-(N-imidazolyl)octyl]oxy-6-chloro-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 131
Dependent Claim
11 words
The compound of claim 127 wherein Y is methoxy, namely 7-[8-(N-imidazolyl)octyl]oxy-6-methoxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]equianzolin-2-one.
Claim 132
Dependent Claim
10 words
The compound of claim 122 wherein R 3 is ethyl.
Claim 133
Dependent Claim
11 words
The compound of claim 131 wherein Y is hydrogen, namely 7-[8-(N-imidazolyl)octyl]oxy-3-ethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 134
Dependent Claim
11 words
The compound of claim 131 wherein Y is chloro, namely 7-[8-(N-imidazolyl)octyl]oxy-6-chloro-3-ethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 135
Dependent Claim
11 words
The compound of claim 131 wherein Y is methoxy, namely 7-[8-(N-imidazolyl)octyl]oxy-6-methoxy-3-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 136
Dependent Claim
10 words
The compound of claim 122 wherein R 3 is hydroxymethyl.
Claim 137
Dependent Claim
11 words
The compound of claim 135 wherein Y is hydrogen, namely 7-[8-(N-imidazolyl)octyl]oxy-3-hydroxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 138
Dependent Claim
11 words
The compound of claim 135 wherein Y is chloro, namely 7-[8-(N-imidazolyl)octyl]oxy-6-chloro-3-hydroxy-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 139
Dependent Claim
11 words
The compound of claim 135 wherein Y is methoxy, namely 7-[8-(N-imidazolyl)octyl]oxy-6-methoxy-3-hydroxy-methyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one.
Claim 140
Dependent Claim
45 words
The compound of claim 1 wherein R 1 , R 2 , R 3 , and R 4 are hydrogen, Y is hydrogen and n is an integer of 1-8 wherein the imidazolylalkyloxy is attached to the 1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one at the position 6, 8 or 9.
Claim 141
Dependent Claim
46 words
The compound of claim 1 wherein R 1 , R 2 , R 3 , and R 4 are hydrogen, Y is chloro and n is an integer of 1-8 and wherein the imidazolylalkyloxy is attached to the 1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one at the position 6, 8 or 9.
Claim 142
Dependent Claim
46 words
The compound of claim 1 wherein R 1 , R 2 , R 3 , and R 4 are hydrogen, Y is methoxy and n is an integer of 1-8 and wherein the imidazolylalkyloxy is attached to the 1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one at the position 6, 8 or 9.
Claim 143
Dependent Claim
43 words
The compound of claim 1 wherein R 1 , R 2 , R 3 , and R 4 are hydrogen, n is an integer of 1-8 and wherein the imidazolylalkyloxy is attached to the 1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one at the position 6, 7, 8 or 9.
Claim 144
Dependent Claim
41 words
The compound of claim 1 wherein R 1 , R 2 , R 4 and Y are hydrogen, n is an integer of 1-8 and wherein the imidazolylalkyloxy is attached to the 1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one at the position 6, 7, 8 or 9.
Claim 145
Independent Claim
104 words
A method for inhibiting 3',5'-cyclic AMP phosphodiesterase which method comprises administering a cyclic AMP phosphodiesterase inhibiting amount of a compound of the formula ##STR9## wherein: n is an integer of 1 to 8; R 1 is hydrogen or alkyl of 1-6 carbons; R 2 is hydrogen; R 3 is hydrogen, alkyl of 1-6 carbons, phenyl, benzyl, hydroxy lower alkyl, carbamoylalkyl, carboxyalkyl, alkoxycarbonylalkyl; R 4 is hydrogen, alkyl of 1-6 carbons, benzyl, or hydroxy lower alkyl; Y is hydrogen, alkyl of 1 to 4 carbon atoms, halo or lower alkoxy; any of its optical isomers, the mixture thereof, or the pharmaceutically acceptable acid addition salt.
Claim 146
Independent Claim
104 words
A method for inhibiting 3',5'-cyclic AMP phosphodiesterase which method comprises administering a cyclic AMP phosphodiesterase inhibiting amount of a compound of the formula ##STR9## wherein: n is an integer of 1 to 8; R 1 is hydrogen or alkyl of 1-6 carbons; R 2 is hydrogen; R 3 is hydrogen, alkyl of 1-6 carbons, phenyl, benzyl, hydroxy lower alkyl, carbamoylalkyl, carboxyalkyl, alkoxycarbonylalkyl; R 4 is hydrogen, alkyl of 1-6 carbons, benzyl, or hydroxy lower alkyl; Y is hydrogen, alkyl of 1 to 4 carbon atoms, halo or lower alkoxy; any of its optical isomers, the mixture thereof, or the pharmaceutically acceptable acid addition salt.
Claim 147
Dependent Claim
16 words
The method of claim 144 wherein the inhibition of said phosphodiesterase activity results in antithrombotic activity.
Claim 148
Independent Claim
109 words
A method for treating heart failure which method comprises administering to a subject in need of such treatment a therapeutically effective amount of a compound of the formula ##STR10## wherein: n is an integer of 1 to 8; R 1 is hydrogen or alkyl of 1-6 carbons; R 2 is hydrogen; R 3 is hydrogen, alkyl of 1-6 carbons, phenyl, benzyl, hydroxy lower alkyl, carbamoylalkyl, carboxyalkyl, alkoxycarbonylalkyl; R 4 is hydrogen, alkyl of 1-6 carbons, benzyl, or hydroxy lower alkyl; Y is hydrogen, alkyl of 1 to 4 carbon atoms, halo or lower alkoxy; any of its optical isomers, the mixture thereof, or the pharmaceutically acceptable acid addition salt.
Claim 149
Independent Claim
109 words
A method for treating heart failure which method comprises administering to a subject in need of such treatment a therapeutically effective amount of a compound of the formula ##STR10## wherein: n is an integer of 1 to 8; R 1 is hydrogen or alkyl of 1-6 carbons; R 2 is hydrogen; R 3 is hydrogen, alkyl of 1-6 carbons, phenyl, benzyl, hydroxy lower alkyl, carbamoylalkyl, carboxyalkyl, alkoxycarbonylalkyl; R 4 is hydrogen, alkyl of 1-6 carbons, benzyl, or hydroxy lower alkyl; Y is hydrogen, alkyl of 1 to 4 carbon atoms, halo or lower alkoxy; any of its optical isomers, the mixture thereof, or the pharmaceutically acceptable acid addition salt.
Claim 150
Independent Claim
108 words
A method for treating hypertension which method comprises administering to a subject in need of such treatment a therapeutically effective amount of a compound of the formula ##STR11## wherein: n is an integer of 1 to 8; R 1 is hydrogen or alkyl of 1-6 carbons; R 2 is hydrogen; R 3 is hydrogen, alkyl of 1-6 carbons, phenyl, benzyl, hydroxy lower alkyl, carbamoylalkyl, carboxyalkyl, alkoxycarbonylalkyl; R 4 is hydrogen, alkyl of 1-6 carbons, benzyl, or hydroxy lower alkyl; Y is hydrogen, alkyl of 1 to 4 carbon atoms, halo or lower alkoxy; any of its optical isomers, the mixture thereof, or the pharmaceutically acceptable acid addition salt.
Claim 151
Independent Claim
108 words
A method for treating hypertension which method comprises administering to a subject in need of such treatment a therapeutically effective amount of a compound of the formula ##STR11## wherein: n is an integer of 1 to 8; R 1 is hydrogen or alkyl of 1-6 carbons; R 2 is hydrogen; R 3 is hydrogen, alkyl of 1-6 carbons, phenyl, benzyl, hydroxy lower alkyl, carbamoylalkyl, carboxyalkyl, alkoxycarbonylalkyl; R 4 is hydrogen, alkyl of 1-6 carbons, benzyl, or hydroxy lower alkyl; Y is hydrogen, alkyl of 1 to 4 carbon atoms, halo or lower alkoxy; any of its optical isomers, the mixture thereof, or the pharmaceutically acceptable acid addition salt.
References Cited (Backward Citations)
US4416895A
Cited
US4490371A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-06-02 | 1989-12-02 | 1990-06-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-06-02 | 1993-12-02 | 1994-06-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-06-02 | 1997-12-02 | 1998-06-03 | $7700.00 | Window Closed / Lapsed |