Patent US5095015A successfully refreshed from Google Patents.
US5095015A
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Certain azacycloalkyl imidazopyrimidines; a new class of gaba brain receptor ligands
Assignee: Neurogen Corp
•
Filing: 1990-07-24
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Granted: 1992-03-10
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Expires: 2010-07-24
Abstract
Abstract The invention encompasses compounds of the formula: ##STR1## and the pharmaceutically acceptable non-toxic salts thereof where n is 0, 1, or 2 and x is ##STR2## and R 1 , R 2 , R 3 , Y, Z, W, T are defined variables. These compounds are highly selective agonists or inverse agonists for the GABAa brain receptors and are useful in the diagnosis and treatment of anxiety, sleep, and seizure disorders, overdose with benzodiazepine type drugs, and enhancement of alertness.
Inventors
- 👤 Pamela Albaugh
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 06:37
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/12; C07D471/14; A; A61; A61P; A61P25/00; A61P25/20; A61P39/00; A61P39/02; A61P43/00
Claims Analysis
Total Claims: 73
Claim 1
Independent Claim
317 words
A compound of the formula: ##STR30## and the pharmaceutically acceptable non-toxic salts thereof wherein Z is H 2 , oxygen or sulfur; R 1 and R 2 are hydrogen or straight chain or branched lower alkyl having 1-6 carbon atoms; X is ##STR31## with the proviso that when X is ##STR32## T is oxygen or sulfur, and when X is ##STR33## R 3 is hydrogen, halogen, aryloxy, alkoxy having 1-6 carbon atoms or OCOR 5 where R 5 is hydrogen, straight or branched chain alkyl having 1-6 carbon atoms, alkoxy having 1-6 carbon atoms or dialkylamino wherein the alkyl have 1-6 carbon atoms and R 4 is H, lower alkyl having 1 to 6 carbon atoms or COR 6 where R 6 is hydrogen, straight or branched chain alkyl having 1-6 carbon atoms, alkoxy having 1-6 carbon atoms or dialkylamino wherein the alkyl have 1-6 carbon atoms; W is phenyl, 2 or 3-thienyl or 2, 3 or 4-pyridyl unsubstituted or mono or disubstituted with halogen, lower alkyl having 1 to 6 carbon atoms, or straight or branched chain lower alkoxy having 1-6 carbon atoms; Y is hydrogen, phenyl or pyridyl, straight or branched chain alkyl, having 1-6 carbon atoms, phenylalkyl or pyridylalkyl wherein the alkyl portion is straight or branched chain lower alkyl having 1-6 carbon atoms, amino substituted with one or two straight or branched chain lower alkyl having 1-6 carbon atoms, mono or dialkyl amino alkyl where each alkyl is a straight or branched chain lower alkyl having 1-6 carbon atoms, 1-indanyl, 4-(thio)chromanyl, 1-1, 2, 3, 4-tetrahydronaphthyl unsubstituted or monosubstituted with halogen, lower alkyl, or straight or branch chain lower alkoxy having 1-6 carbon atoms, COR 7 or SO 2 R 7 where R 7 straight or branched chain lower alkyl having 1-6 carbon atoms, phenyl or pyridyl, straight or branched chain lower alkoxy having 1-6 carbon atoms; and n is 0, 1 or 2.
Claim 2
Dependent Claim
317 words
A compound of the formula: ##STR30## and the pharmaceutically acceptable non-toxic salts thereof wherein Z is H 2 , oxygen or sulfur; R 1 and R 2 are hydrogen or straight chain or branched lower alkyl having 1-6 carbon atoms; X is ##STR31## with the proviso that when X is ##STR32## T is oxygen or sulfur, and when X is ##STR33## R 3 is hydrogen, halogen, aryloxy, alkoxy having 1-6 carbon atoms or OCOR 5 where R 5 is hydrogen, straight or branched chain alkyl having 1-6 carbon atoms, alkoxy having 1-6 carbon atoms or dialkylamino wherein the alkyl have 1-6 carbon atoms and R 4 is H, lower alkyl having 1 to 6 carbon atoms or COR 6 where R 6 is hydrogen, straight or branched chain alkyl having 1-6 carbon atoms, alkoxy having 1-6 carbon atoms or dialkylamino wherein the alkyl have 1-6 carbon atoms; W is phenyl, 2 or 3-thienyl or 2, 3 or 4-pyridyl unsubstituted or mono or disubstituted with halogen, lower alkyl having 1 to 6 carbon atoms, or straight or branched chain lower alkoxy having 1-6 carbon atoms; Y is hydrogen, phenyl or pyridyl, straight or branched chain alkyl, having 1-6 carbon atoms, phenylalkyl or pyridylalkyl wherein the alkyl portion is straight or branched chain lower alkyl having 1-6 carbon atoms, amino substituted with one or two straight or branched chain lower alkyl having 1-6 carbon atoms, mono or dialkyl amino alkyl where each alkyl is a straight or branched chain lower alkyl having 1-6 carbon atoms, 1-indanyl, 4-(thio)chromanyl, 1-1, 2, 3, 4-tetrahydronaphthyl unsubstituted or monosubstituted with halogen, lower alkyl, or straight or branch chain lower alkoxy having 1-6 carbon atoms, COR 7 or SO 2 R 7 where R 7 straight or branched chain lower alkyl having 1-6 carbon atoms, phenyl or pyridyl, straight or branched chain lower alkoxy having 1-6 carbon atoms; and n is 0, 1 or 2.
Claim 3
Dependent Claim
127 words
A compound according to claim 1 of the formula: ##STR34## and the pharmaceutically acceptable non-toxic salts thereof wherein R 1 and R 2 are hydrogen or straight chain lower alkyl having 1-6 carbon atoms; R 3 is hydrogen, halogen aryloxy, alkoxy having 1-6 carbon atoms or OCOR 5 where R 5 is hydrogen, straight or branched chain alkyl having 1-6 carbon atoms, alkoxy having 1-6 carbon atoms or dialkylamino wherein the alkyl have 1-6 carbon atoms; W is phenyl or phenyl monosubstituted with chlorine or fluorine; and Y is hydrogen, lower alkyl having 1-6 carbon atoms, alkanoyl having 1-6 carbon atoms, mono or disubstituted phenyl alkyl having 1-3 alkyl carbon atoms, carboalkoxy having 1-6 carbon atoms, carbobenzyloxy, and pyridyl alkyl wherein the alkyl has 1-6 carbon atoms.
Claim 4
Dependent Claim
133 words
A compound according to claim 1 of the formula: ##STR35## and the pharmaceutically acceptable non-toxic salts thereof wherein T is oxygen or sulfur; R 1 and R 2 are hydrogen or straight chain lower alkyl having 1-6 carbon atoms; R 4 is hydrogen, lower alkyl having 1 to 6 carbon atoms or COR 5 where R 5 is hydrogen, straight or branched chain alkyl having 1-6 carbon atoms, alkoxy having 1-6 carbon atoms or dialkylamino wherein the alkyl have 1-6 carbon atoms; W is phenyl or phenyl monosubstituted with chlorine or fluorine: and Y is hydrogen, lower alkyl having 1-6 carbon atoms, alkanoyl having 1-6 carbon atoms, mono or disubstituted phenyl alkyl having 1-3 alkyl carbon atoms, carboalkoxy having 1-6 carbon atoms, carbobenzyloxy, and pyridyl alkyl wherein the alkyl has 1-6 carbon atoms.
Claim 5
Dependent Claim
122 words
A compound according to claim 1 of the formula: ##STR36## and the pharmaceutically acceptable non-toxic salts thereof wherein R 1 and R 2 are hydrogen or straight chain lower alkyl having 1-6 carbon atoms; R 4 is hydrogen, lower alkyl or COR 5 wherein R 5 is hydrogen, straight or branched chain alkyl having 1-6 carbon atoms alkoxy having 1-6 carbon atoms or dialkylamino wherein the alkyl have 1-6 carbon atoms; W is phenyl or phenyl monosubstituted with chlorine or fluorine; and Y is hydrogen, lower alkyl having 1-6 carbon atoms, alkanoyl having 1-6 carbon atoms, mono or disubstituted phenyl alkyl having 1-3 alkyl carbon atoms, carboalkoxy having 1-6 carbon atoms, carbobenzyloxy, and pyridyl alkyl wherein the alkyl has 1-6 carbon atoms.
Claim 6
Dependent Claim
21 words
A compound according to claim 1, wherein X is ##STR37## R 1 and R 2 are H and n is 1.
Claim 7
Dependent Claim
15 words
A compound according to claim 2, wherein W is phenyl monosubstituted with chlorine or fluorine.
Claim 8
Dependent Claim
13 words
A compound according to claim 3, wherein W is phenyl monosubstituted with fluorine.
Claim 9
Dependent Claim
10 words
A compound according to claim 4, wherein Y is 3-phenylpropyl.
Claim 10
Dependent Claim
10 words
A compound according to claim 4, wherein Y is acetyl.
Claim 11
Dependent Claim
10 words
A compound according to claim 4, wherein Y is carboethoxy.
Claim 12
Dependent Claim
10 words
A compound according to claim 4, wherein Y is butyl.
Claim 13
Dependent Claim
10 words
A compound according to claim 4, wherein Y is benzyl.
Claim 14
Dependent Claim
10 words
A compound according to claim 4, wherein Y is hexanoyl.
Claim 15
Dependent Claim
10 words
A compound according to claim 4, wherein Y is methyl.
Claim 16
Dependent Claim
10 words
A compound according to claim 4, wherein Y is carbobenzyloxy.
Claim 17
Dependent Claim
10 words
A compound according to claim 4, wherein Y is hydrogen.
Claim 18
Dependent Claim
9 words
A compound according to claim 1, which is 9-Benzoyl-2-(fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 19
Dependent Claim
9 words
A compound according to claim 1, which is 9-Benzoyl-2-(3-chlorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 20
Dependent Claim
9 words
A compound according to claim 1, which is 9-Benzoyl-2-(3-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 21
Dependent Claim
9 words
A compound according to claim 1, which is 9-Benzoyl-2-phenyl-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 22
Dependent Claim
9 words
A compound according to claim 1, which is 9-Benzoyl-2-(4-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 23
Dependent Claim
9 words
A compound according to claim 1, which is 9-Benzoyl-2-(4-methoxyphenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 24
Dependent Claim
9 words
A compound according to claim 1, which is 2-(2-Fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 25
Dependent Claim
11 words
A compound according to claim 1, which is 2-(2-Chlorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one (Compound 8).
Claim 26
Dependent Claim
9 words
A compound according to claim 1, which is 2-(3-Fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 27
Dependent Claim
11 words
A compound according to claim 1, which is 2-Phenyl-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one (Compound 10).
Claim 28
Dependent Claim
9 words
A compound according to claim 1, which is 2-(4-Fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 29
Dependent Claim
9 words
A compound according to claim 1, which is 2-(4-methoxyphenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 30
Dependent Claim
9 words
A compound according to claim 1, which is 9-(2-Fluorobenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 31
Dependent Claim
9 words
A compound according to claim 1, which is 9-Benzyl-2-(3-chlorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 32
Dependent Claim
9 words
A compound according to claim 1, which is 9-Benzyl-2-(3-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 33
Dependent Claim
9 words
A compound according to claim 1, which is 9-Benzyl-2-(4-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 34
Dependent Claim
9 words
A compound according to claim 1, which is 9-Benzyl-2-(4-methoxyphenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 35
Dependent Claim
9 words
A compound according to claim 1, which is 9-Benzyl-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 36
Dependent Claim
9 words
A compound according to claim 1, which is 9-Benzyl-2-phenyl-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 37
Dependent Claim
9 words
A compound according to claim 1, which is 9-(2-Pyrimidinyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 38
Dependent Claim
9 words
A compound according to claim 1, which is ±9-α-Methylbenzyl-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 39
Dependent Claim
9 words
A compound according to claim 1, which is 9-(4-Fluorobenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 40
Dependent Claim
9 words
A compound according to claim 1, which is 9-(4-Methoxybenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 41
Dependent Claim
9 words
A compound according to claim 1, which is 9-(4-Methylbenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 42
Dependent Claim
9 words
A compound according to claim 1, which is 9-(3,4-difluorobenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2c]pyrido[3,4-e]pyrimidin-5-(6H)-one.
Claim 43
Dependent Claim
9 words
A compound according to claim 1, which is 9-(2,4-difluorobenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 44
Dependent Claim
9 words
A compound according to claim 1, which is ±9-(4-Fluoro-α-methylbenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 45
Dependent Claim
9 words
A compound according to claim 1, which is 9-(3-Fluorobenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 46
Dependent Claim
9 words
A compound according to claim 1, which is ±9-(3-Fluoro-α-methylbenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 47
Dependent Claim
9 words
A compound according to claim 1, which is 9-(2-Methylbenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 48
Dependent Claim
9 words
A compound according to claim 1, which is ±9-(2-Fluoro-α-methylbenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 49
Dependent Claim
9 words
A compound according to claim 1, which is ±9-(1-indanyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 50
Dependent Claim
9 words
A compound according to claim 1, which is 9-(2-propyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 51
Dependent Claim
9 words
A compound according to claim 1, which is 9-cyclohexylmethyl-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 52
Dependent Claim
9 words
A compound according to claim 1, which is ±9-benzyl-2-(2-fluorophenyl)-8-methyl-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 53
Dependent Claim
9 words
A compound according to claim 1, which is 9-Propionyl-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 54
Dependent Claim
9 words
A compound according to claim 1, which is 9-Butyryl-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 55
Dependent Claim
9 words
A compound according to claim 1, which is 9-Hexanoyl-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 56
Dependent Claim
9 words
A compound according to claim 1, which is 9-Phenylacetyl-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 57
Dependent Claim
9 words
A compound according to claim 1, which is 9-Acetyl-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 58
Dependent Claim
9 words
A compound according to claim 1, which is 9-Nicotinoyl-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 59
Dependent Claim
9 words
A compound according to claim 1, which is 9-Isonicotinoyl-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 60
Dependent Claim
9 words
A compound according to claim 1, which is 9-Picolinoyl-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 61
Dependent Claim
9 words
A compound according to claim 1, which is 9-Carbobenzyloxy-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 62
Dependent Claim
9 words
A compound according to claim 1, which is 9-Carboethoxy-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 63
Dependent Claim
9 words
A compound according to claim 1, which is 9-Carbobutoxy-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 64
Dependent Claim
9 words
A compound according to claim 1, which is 9-Phenylsulfonyl-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 65
Dependent Claim
9 words
A compound according to claim 1, which is 9-n-Butyl-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 66
Dependent Claim
9 words
A compound according to claim 1, which is 9-Methyl-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 67
Dependent Claim
9 words
A compound according to claim 1, which is 9-(2-Phenylethyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 68
Dependent Claim
9 words
A compound according to claim 1, which is 9-(3-Phenylpropyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 69
Dependent Claim
9 words
A compound according to claim 1, which is 9-(3-Pyridylmethyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 70
Dependent Claim
9 words
A compound according to claim 1, which is 9-(2-Pyridylmethyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 71
Dependent Claim
9 words
A compound according to claim 1, which is 9-(4-Pyridylmethyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 72
Dependent Claim
9 words
A compound according to claim 1, which is 6-Acetyl-9-(2-fluorobenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one.
Claim 73
Dependent Claim
9 words
A compound according to claim 1, which is 5-Acetoxy-9-(2-fluorobenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidine.
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) | 1995-03-10 | 1995-09-09 | 1996-03-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-03-10 | 1999-09-09 | 2000-03-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-03-10 | 2003-09-09 | 2004-03-10 | $7700.00 | Window Closed / Lapsed |