US4536508A
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Triazoleamine derivatives having histamine H2 -antagonist properties
Assignee: Glaxo Group Ltd
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Filing: 1983-02-18
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Granted: 1985-08-20
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Expires: 2003-02-18
Abstract
Abstract The invention relates to compounds of the general formula (I) ##STR1## and physiologically acceptable salts, hydrates and bioprecursors thereof, which show pharmacological activity as selective histamine H 2 -antagonists.
Inventors
- 👤 John W. Clitherow
- 👤 Barry J. Price
- 👤 John Bradshaw
- 👤 Michael Martin-Smith
- 👤 John W. M. Mackinnon
- 👤 Duncan B. Judd
- 👤 Roger Hayes
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 00:45
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/08; C07D295/096; A; A61; A61P; A61P43/00; C07D249/00; C07D249/02; C07D249/08; C07D249/10; C07D249/14; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/52; C07D317/00; C07D317/08; C07D317/10; C07D317/14; C07D317/18; C07D317/22; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/30; C07D333/36
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
450 words
Compounds of the general formula (I) ##STR24## and physiologically acceptable salts, hydrates; and tautomers thereof, in which R 1 and R 2 , which may be the same or different, each represent hydrogen, C 1-10 alkyl, C 3-8 cycloalkyl, C 3-6 alkenyl, aralkyl in which the alkyl moiety contains 1 to 6 carbon atoms; trifluoro C 1-6 alkyl, or C 1-6 alkyl substituted by hydroxy, C 1-6 alkoxy, amino, C 1-6 alkylamino or di C 1-6 alkylamino or R 1 and R 2 may together with the nitrogen atom to which they are attached form a heterocyclic ring which is pyrrolidine, piperidine optionally substituted in the 4-position by C 1-3 alkyl or hydroxy; tetrahydropyridine, morpholine, 2,6-di C 1-6 alkylmorpholine, hexamethyleneimine or heptamethylenimine; Alk represents a straight or branched alkylene chain of 1 to 6 carbon atoms; Q represents a furan or thiophene ring in which incorporation into the rest of the molecule is through bonds at the 2- and 5-positions, the furan ring optionally bearing a further substituent R 6 adjacent to the group R 1 R 2 N--Alk--, or Q represents a benzene ring in which incorporation into the rest of the molecule is through bonds at the 1- and 3- or 1- and 4-positions; R 6 represents halogen or C 1-4 alkyl which may be substituted by hydroxy or C 1-4 alkoxy; X represents --CH 2 --, --O--, --S-- or ##STR25## where R 5 represents hydrogen or methyl; n represents zero, 1 or 2; m represents 2, 3 or 4; R 3 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, ar C 1-6 alkyl, hydroxy C 2-6 alkyl, C 1-6 alkoxy C 1-6 alkyl or phenyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms; and R 4 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, phenyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms; aralkyl in which the alkyl moiety contains 1 to 6 carbon atoms; hydroxy C 1-6 alkyl, acyloxy C 1-6 alkyl in which the acyl portion is C 1-6 alkanoyl, benzoyl optionally substituted by 1 or more C 1-3 alkyl or alkoxy groups or halogen atoms, or aralkanoyl in which the alkyl moiety contains 1 to 6 carbon atoms; C 1-6 alkoxy C 1-6 alkyl, aryloxy C 1-6 alkyl, ar C 1-6 alkyloxy C 1-6 alkyl; amino C 1-6 alkyl, C 1-6 alkyl-amino C 1-6 alkyl, di C 1-6 alkylamino C 1-6 alkyl, hydroxy, C 1-6 alkoxy, C 1-6 alkythio or halogen and wherein aryl or as a group or part of a group is phenyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms.
Claim 2
Dependent Claim
450 words
Compounds of the general formula (I) ##STR24## and physiologically acceptable salts, hydrates; and tautomers thereof, in which R 1 and R 2 , which may be the same or different, each represent hydrogen, C 1-10 alkyl, C 3-8 cycloalkyl, C 3-6 alkenyl, aralkyl in which the alkyl moiety contains 1 to 6 carbon atoms; trifluoro C 1-6 alkyl, or C 1-6 alkyl substituted by hydroxy, C 1-6 alkoxy, amino, C 1-6 alkylamino or di C 1-6 alkylamino or R 1 and R 2 may together with the nitrogen atom to which they are attached form a heterocyclic ring which is pyrrolidine, piperidine optionally substituted in the 4-position by C 1-3 alkyl or hydroxy; tetrahydropyridine, morpholine, 2,6-di C 1-6 alkylmorpholine, hexamethyleneimine or heptamethylenimine; Alk represents a straight or branched alkylene chain of 1 to 6 carbon atoms; Q represents a furan or thiophene ring in which incorporation into the rest of the molecule is through bonds at the 2- and 5-positions, the furan ring optionally bearing a further substituent R 6 adjacent to the group R 1 R 2 N--Alk--, or Q represents a benzene ring in which incorporation into the rest of the molecule is through bonds at the 1- and 3- or 1- and 4-positions; R 6 represents halogen or C 1-4 alkyl which may be substituted by hydroxy or C 1-4 alkoxy; X represents --CH 2 --, --O--, --S-- or ##STR25## where R 5 represents hydrogen or methyl; n represents zero, 1 or 2; m represents 2, 3 or 4; R 3 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, ar C 1-6 alkyl, hydroxy C 2-6 alkyl, C 1-6 alkoxy C 1-6 alkyl or phenyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms; and R 4 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, phenyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms; aralkyl in which the alkyl moiety contains 1 to 6 carbon atoms; hydroxy C 1-6 alkyl, acyloxy C 1-6 alkyl in which the acyl portion is C 1-6 alkanoyl, benzoyl optionally substituted by 1 or more C 1-3 alkyl or alkoxy groups or halogen atoms, or aralkanoyl in which the alkyl moiety contains 1 to 6 carbon atoms; C 1-6 alkoxy C 1-6 alkyl, aryloxy C 1-6 alkyl, ar C 1-6 alkyloxy C 1-6 alkyl; amino C 1-6 alkyl, C 1-6 alkyl-amino C 1-6 alkyl, di C 1-6 alkylamino C 1-6 alkyl, hydroxy, C 1-6 alkoxy, C 1-6 alkythio or halogen and wherein aryl or as a group or part of a group is phenyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms.
Claim 3
Dependent Claim
401 words
Compounds of the general formula (I) ##STR26## and physiologically acceptable salts, hydrates; and tautomers thereof, in which R 1 and R 2 , which may be the same or different, each represent hydrogen, C 1-10 alkyl, C 3-8 cycloalkyl, C 3-6 alkenyl, ar C 1-6 alkyl; trifluoro C 1-6 alkyl, or C 1-6 alkyl substituted by hydroxy, C 1-6 alkoxy, amino, C 1-6 alkylamino or di C 1-6 alkylamino or R 1 and R 2 may together with the nitrogen atom to which they are attached form a heterocyclic ring which is pyrrolidine, piperidine optionally substituted in the 4-position by C 1-3 alkyl or hydroxy; tetrahydropyridine, morpholine, 2,6-dialkylmorpholine, hexamethyleneimine or heptamethylenimine; Alk represents a straight or branched alkylene chain of 1 to 6 carbon atoms; Q represents a furan or thiophene ring in which incorporation into the rest of the molecule is through bonds at the 2- and 5-positions, the furan ring optionally bearing a further substituent R 6 adjacent to the group R 1 R 2 N--Alk--, or Q represents a benzene ring in which incorporation into the rest of the molecule is through bonds at the 1- and 3- or 1- and 4-positions; R 6 represents halogen or C 1-4 alkyl which may be substituted by hydroxy or C 1-4 alkoxy; X represents --CH 2 --, --O--, --S-- or ##STR27## where R 5 represents hydrogen or methyl; n represents zero, 1 or 2; m represents 2, 3 or 4; R 3 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, ar C 1-6 alkyl; hydroxy C 2-6 alkyl, C 1-6 alkoxy C 1-6 alkyl or phenyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms; and R 4 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, phenyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms; ar C 1-6 alkyl, hydroxy C 1-6 alkyl, C 1-6 alkoxy C 1-6 alkyl, aryloxy C 1-6 alkyl, amino C 1-6 alkyl, C 1-6 alkyl-amino C 1-6 alkyl, di C 1-6 alkylamino C 1-6 alkyl, hydroxy, C 1-6 alkoxy, or halogen; provided that when X represents an oxygen atom or --NR 5 -- and when n is zero then Q represents benzene; and wherein aryl or ar as a group or part of a group is phenyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms.
Claim 4
Dependent Claim
401 words
Compounds of the general formula (I) ##STR26## and physiologically acceptable salts, hydrates; and tautomers thereof, in which R 1 and R 2 , which may be the same or different, each represent hydrogen, C 1-10 alkyl, C 3-8 cycloalkyl, C 3-6 alkenyl, ar C 1-6 alkyl; trifluoro C 1-6 alkyl, or C 1-6 alkyl substituted by hydroxy, C 1-6 alkoxy, amino, C 1-6 alkylamino or di C 1-6 alkylamino or R 1 and R 2 may together with the nitrogen atom to which they are attached form a heterocyclic ring which is pyrrolidine, piperidine optionally substituted in the 4-position by C 1-3 alkyl or hydroxy; tetrahydropyridine, morpholine, 2,6-dialkylmorpholine, hexamethyleneimine or heptamethylenimine; Alk represents a straight or branched alkylene chain of 1 to 6 carbon atoms; Q represents a furan or thiophene ring in which incorporation into the rest of the molecule is through bonds at the 2- and 5-positions, the furan ring optionally bearing a further substituent R 6 adjacent to the group R 1 R 2 N--Alk--, or Q represents a benzene ring in which incorporation into the rest of the molecule is through bonds at the 1- and 3- or 1- and 4-positions; R 6 represents halogen or C 1-4 alkyl which may be substituted by hydroxy or C 1-4 alkoxy; X represents --CH 2 --, --O--, --S-- or ##STR27## where R 5 represents hydrogen or methyl; n represents zero, 1 or 2; m represents 2, 3 or 4; R 3 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, ar C 1-6 alkyl; hydroxy C 2-6 alkyl, C 1-6 alkoxy C 1-6 alkyl or phenyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms; and R 4 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, phenyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms; ar C 1-6 alkyl, hydroxy C 1-6 alkyl, C 1-6 alkoxy C 1-6 alkyl, aryloxy C 1-6 alkyl, amino C 1-6 alkyl, C 1-6 alkyl-amino C 1-6 alkyl, di C 1-6 alkylamino C 1-6 alkyl, hydroxy, C 1-6 alkoxy, or halogen; provided that when X represents an oxygen atom or --NR 5 -- and when n is zero then Q represents benzene; and wherein aryl or ar as a group or part of a group is phenyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms.
Claim 5
Dependent Claim
30 words
Compounds according to claims 1 or 2 in which Q represents benzene incorporated into the molecule through bonds at the 1- and 3-positions, n is zero and X is oxygen.
Claim 6
Dependent Claim
14 words
Compounds according to claims 1 or 2 in which m+n is 3 or 4.
Claim 7
Dependent Claim
14 words
Compounds according to claims 1 or 2 in which Alk is --CH 2 --.
Claim 8
Dependent Claim
87 words
Compounds according to claims 1 or 2 in which R 1 represents hydrogen or C 1-4 alkyl and R 2 represents C 3-5 alkenyl, C 5-7 cycloalkyl, benzyl, C 1-8 alkyl or C 1-4 alkyl substituted by C 1-3 alkoxy, hydroxy, di-C 1-3 alkylamino or trifluoromethyl or R 1 and R 2 together with the nitrogen atom to which they are attached form a heterocyclic ring which is pyrrolidine, piperidine optionally substituted in the 4-position by C 1-3 alkyl or hydroxy; tetrahydropyridine, morpholine, 2,6-dialkylmorpholine, hexamethyleneimine or heptamethylenimine.
Claim 9
Dependent Claim
55 words
Compounds according to claim 6 in which R 1 and R 2 represent C 1-3 alkyl, or R 1 and R 2 together with the nitrogen atom to which they are attached form a heterocyclic ring which is pyrrolidine, piperidine optionally substituted in the 4-position by methyl or hydroxy, tetrahydropyridine, morpholine, 2,6-dimethylmorpholine, hexamethyleneimine or heptamethyleneimine.
Claim 10
Dependent Claim
21 words
Compounds according to claims 1 or 2 in which R 3 represents hydrogen, C 1-6 alkyl or hydroxy C 2-4 alkyl.
Claim 11
Dependent Claim
122 words
Compounds according to claim 1 in which R 4 represents hydrogen, C 1-6 alkyl, hydroxy C 1-6 alkyl, C 1-6 alkoxy C 1-6 alkyl, acyloxy C 1-6 alkyl in which the acyl portion is C 1-6 alkanoyl, benzoyl, optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms; or aralkanoyl in which the alkyl moiety contains 1 to 6 carbon atoms and the aryl group is phenyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms, aralkyl in which the alkyl moiety contains 1 to 6 carbon atoms and the aryl group is phenyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms, or hydroxy.
Claim 12
Dependent Claim
52 words
Compounds according to claim 2 in which R 4 represents hydrogen, C 1-6 alkyl, hydroxy C 1-6 alkyl, C 1-6 alkoxy C 1-6 alkyl, ar C 1-6 alkyl in which the aryl group is phenyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms; or hydroxy.
Claim 13
Dependent Claim
26 words
Compounds according to claim 9 or claim 10 in which R 4 represents hydroxy C 1-6 alkyl, hydroxy, C 1-6 alkoxy C 1-6 alkyl, or benzyl.
Claim 14
Dependent Claim
69 words
Compounds according to claims 1 or 2, corresponding to the formula (II) ##STR28## where R 1 and R 2 are methyl groups or together with the nitrogen atom to which they are attached form a pyrrolidino, piperidino or hexamethyleneimino group; m is 3 or 4; R 3 is hydrogen or methyl, and R 4 is a hydroxy C 1-6 alkyl, C 1-6 alkoxy C 1-6 alkyl, benzyl, or hydroxy.
Claim 15
Dependent Claim
11 words
Compounds which are: 1-methyl-5-[[4-[3-(1-piperidinylmethyl)phenoxy]butyl]amino]-1H-1,2,4-triazole-3-methanol, 1-methyl-5-[[3-[3-(1-piperidinylmethyl)phenoxy]propyl]amino]-1H-1,2,4-triazole-3-methanol, 3-methoxy-methyl-1-methyl-5-[[4-[3-(1-piperidinylmethyl)phenoxy]butyl]amino]-1H-1,2,4-triazole or their physiologically acceptable salts.
Claim 16
Dependent Claim
11 words
Compounds which are: 1-methyl-5-[[4-[3-(1-piperidinylmethyl)phenoxy]butyl]amino]-1H-1,2,4-triazole-3-methanol, 1-methyl-5-[[3-[3-(1-piperidinylmethyl)phenoxy]propyl]amino]-1H-1,2,4-triazole-3-methanol, 3-methoxy-methyl-1-methyl-5-[[4-[3-(1-piperidinylmethyl)phenoxy]butyl]amino]-1H-1,2,4-triazole or their physiologically acceptable salts.
Claim 17
Dependent Claim
12 words
Compounds which are: 3-phenylmethyl-N-[3-[3-(dimethylaminomethyl)phenoxy]propyl]-1H-1,2,4-triazole-5-amine 5-[4-[3-(1-piperidinylmethyl)phenoxy]butyl]amino-1H-1,2,4-triazole-3-methanol, 3-phenylmethyl-N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1H-1,2,4-triazole-5-amine, 5-[[3-[3-(1-piperidinylmethyl)phenoxy]propyl]amino]-1H-1,2,4-triazole-3-one, or their physiologically acceptable salts.
Claim 18
Dependent Claim
12 words
Compounds which are: 3-phenylmethyl-N-[3-[3-(dimethylaminomethyl)phenoxy]propyl]-1H-1,2,4-triazole-5-amine 5-[4-[3-(1-piperidinylmethyl)phenoxy]butyl]amino-1H-1,2,4-triazole-3-methanol, 3-phenylmethyl-N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1H-1,2,4-triazole-5-amine, 5-[[3-[3-(1-piperidinylmethyl)phenoxy]propyl]amino]-1H-1,2,4-triazole-3-one, or their physiologically acceptable salts.
Claim 19
Dependent Claim
6 words
5-[[2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thio]ethyl]amino]-1-methyl-1H-1,2,4-triazole-3-methanol and physiologically acceptable salts thereof.
Claim 20
Dependent Claim
6 words
5-[[2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thio]ethyl]amino]-1-methyl-1H-1,2,4-triazole-3-methanol and physiologically acceptable salts thereof.
Claim 21
Dependent Claim
6 words
5-[[2-[[[5-[(dimethylamino)methyl]-4-methyl-2-furanyl]methyl]thio]ethyl]amino]amino]-1-methyl-1H-1,2,4-triazole-3-methanol and physiologically acceptable salts thereof.
Claim 22
Dependent Claim
6 words
5-[[2-[[[5-[(dimethylamino)methyl]-4-methyl-2-furanyl]methyl]thio]ethyl]amino]amino]-1-methyl-1H-1,2,4-triazole-3-methanol and physiologically acceptable salts thereof.
Claim 23
Dependent Claim
6 words
1-methyl-5-[[3-[3-[(dimethylamino)methyl]phenoxy]propyl]amino]-1H-1,2,4-triazole-3-methanol and physiologically acceptable salts thereof.
Claim 24
Dependent Claim
6 words
1-methyl-5-[[3-[3-[(dimethylamino)methyl]phenoxy]propyl]amino]-1H-1,2,4-triazole-3-methanol and physiologically acceptable salts thereof.
Claim 25
Dependent Claim
30 words
Compounds according to any of claims 1, 2, 15, 16 or 17 in the form of a hydrochloride, hydrobromide, sulphate, methanesulphonate, acetate, maleate, succinate, citrate, fumarate, benzoate or tartrate salt.
Claim 26
Dependent Claim
223 words
Compounds according to claim 1 corresponding to the formula ##STR29## where R 1 represents hydrogen or C 1-4 alkyl and R 2 represents C 3-5 alkenyl, C 5-7 cycloalkyl, benzyl, C 1-8 alkyl; C 1-4 alkyl substituted by C 1-3 alkoxy, hydroxy, di-C 1-3 alkylamino or trifluoromethyl, or R 1 and R 2 together with the nitrogen atom to which they are attached form a heterocyclic ring which is pyrrolidine, piperidine optionally substituted in the 4-position by C 1-3 alkyl or hydroxy, tetrahydropyridine, morpholine, 2,6-di C 1-6 alkylmorpholine, hexamethyleneimine or heptamethyleneimine; m is 3 or 4; R 3 represents hydrogen, C 1-6 alkyl or C 2-4 hydroxyalkyl; and R 4 represents hydrogen, C 1-6 alkyl, hydroxy C 1-6 alkyl, C 1-6 alkoxy C 1-6 alkyl, acyloxy C 1-6 alkyl in which the acyl portion is C 1-6 alkanoyl, benzoyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms, or aralkanoyl in which the alkyl moiety contains 1 to 6 carbon atoms and the aryl group is phenyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms; aralkyl in which the alkyl portion contains 1 to 6 carbon atoms and the aryl group is phenyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms; or hydroxy.
Claim 27
Dependent Claim
59 words
Compounds according to claim 2 in which R 4 represents hydrogen, C 1-6 alkyl, hydroxy C 1-6 alkyl, C 1-6 alkoxy C 1-6 alkyl, aralkyl in which the alkyl moiety contains 1 to 6 carbon atoms and the aryl group is phenyl optionally substituted by one or more C 1-3 alkyl or alkoxy groups or halogen atoms; or hydroxy.
Claim 28
Dependent Claim
127 words
Compounds according to claim 20 corresponding to the formula ##STR30## where R 1 represents hydrogen or C 1-4 alkyl and R 2 represents C 3-5 alkenyl, C 5-7 cycloalkyl, benzyl, C 1-8 alkyl; C 1-4 alkyl substituted by C 1-3 alkoxy, hydroxy, di-C 1-3 alkylamino or trifluoromethyl, or R 1 and R 2 together with the nitrogen atom to which they are attached form a heterocyclic ring which is pyrrolidine, piperidine optionally substituted in the 4-position by C 1-3 alkyl or hydroxy, tetrahydropyridine, morpholine, 2,6-di C 1-6 alkylmorpholine, hexamethyleneimine or heptamethyleneimine; m is 3 or 4; R 3 represents hydrogen, C 1-6 alkyl or C 2-4 hydroxyalkyl; and R 4 represents hydrogen, C 1-6 alkyl, hydroxy C 1-6 alkyl, C 1-6 alkoxy C 1-6 alkyl or hydroxy.
Claim 29
Dependent Claim
54 words
A pharmaceutical composition comprising an effective amount of a compound for the treatment of conditions mediated through H 2 receptors wherein said compound is as claimed in any of claims 1, 2, 15, 16 or 17 together with at least one pharmaceutically acceptable carrier or diluent, and optionally one or more further active ingredients.
Claim 30
Dependent Claim
14 words
A pharmaceutical composition according to claim 15 in a form adapted for oral administration.
Claim 31
Dependent Claim
19 words
A pharmaceutical composition according to claim 22 containing 5 mg to 1 g of the compound of formula (I).
Claim 32
Dependent Claim
33 words
A method of treating a condition mediated through histamine H 2 -receptors which comprises administering to a patient an effective amount of a composition as defined in claim 15 to relieve said condition.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-08-19 | 1989-02-18 | 1989-08-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-08-19 | 1993-02-18 | 1993-08-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-08-19 | 1997-02-18 | 1997-08-20 | $7700.00 | Window Closed / Lapsed |