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US4227014A
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4-[(Cycloalkyl or cycloalkenyl substituted)amino, alkylamino or alkenylamino]benzoic acids and salts thereof
Assignee: Wyeth Holdings LLC
•
Filing: 1978-02-27
•
Granted: 1980-10-07
•
Expires: 1998-02-27
Abstract
Abstract This disclosure describes novel 4-[(cycloalkyl or cycloalkenyl substituted)amino, alkylamino or alkenylamino]-benzoic acids, salts and derivatives of these such as cycloalkylamino, cycloalkenylamino, cycloalkyl-alkylamino, cycloalkylalkenylamino, cycloalkenyl-alkylamino, and cycloalkyl-cycloalkylamino benzoic acids and derivatives and suitable salts of these; these compounds are useful as hypolipidemic and antiatherosclerotic agents.
Inventors
- 👤 Robert G. Shepherd
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 00:56
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/28; C07D213/30; C07C; C07C17/00; C07C17/093; C07C323/00; C07C323/23; C07C323/24; C07C323/25; C07C327/00; C07C327/20; C07C327/22; C07C45/00; C07C45/45; C07D207/00; C07D207/02; C07D207/30; C07D207/34; C07D207/42; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/46; C07D213/60; C07D213/62; C07D213/63; C07D213/65; C07D213/78; C07D213/79; C07D213/80; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/32; C07D239/42; C07D263/00; C07D263/02; C07D263/08; C07D263/10; C07D265/00; C07D265/04; C07D265/06; C07D277/00; C07D277/02; C07D277/04; C07D277/06; C07D303/00; C07D303/02; C07D303/12; C07D303/16; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/54; C07D307/56; C07D307/66; C07D307/68; C07D307/70; C07D307/71; C07D309/00; C07D309/02; C07D309/08; C07D309/10; C07D309/12; C07D317/00; C07D317/08; C07D317/10; C07D317/14; C07D317/28; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/14; C07D333/16; C07D333/20; C07D333/22; C07D333/24; C07D333/26; C07D333/30; C07D333/36; C07D333/38; C07D333/42; C07D333/44
Claims Analysis
Total Claims: 105
Claim 1
Independent Claim
169 words
A compound of the formula: ##STR8## wherein Z is a moiety of the formula: ##STR9## wherein R 1 is hydrogen; R is hydrogen; n is either zero or one; Y is a divalent radical selected from the group consisting of unbranched or branced C 1 -C 13 alkylene or alkenylene and is either unsubstituted or substituted with at least one C 1 -C 4 alkyl group; and D is selected from the group consisting of C 3 -C 16 cycloalkyl or C 4 -C 17 cycloalkenyl and is either unsubstituted or substituted with at least one C 1 -C 13 alkyl, C 4 -C 8 cycloalkyl, decahydronaphthyl, methylene, ethylidene, or isopropylidine group; with the proviso that the total number of carbon atoms in D and Y shall not exceed twenty; and with the further proviso that when n is 1, D is not an unsubstituted cyclopropyl nor a cyclopropyl substituted with at least one C 1 -C 13 alkyl; and the pharmaceutically acceptable non-toxic acid-addition and cationic salts thereof.
Claim 2
Dependent Claim
169 words
A compound of the formula: ##STR8## wherein Z is a moiety of the formula: ##STR9## wherein R 1 is hydrogen; R is hydrogen; n is either zero or one; Y is a divalent radical selected from the group consisting of unbranched or branced C 1 -C 13 alkylene or alkenylene and is either unsubstituted or substituted with at least one C 1 -C 4 alkyl group; and D is selected from the group consisting of C 3 -C 16 cycloalkyl or C 4 -C 17 cycloalkenyl and is either unsubstituted or substituted with at least one C 1 -C 13 alkyl, C 4 -C 8 cycloalkyl, decahydronaphthyl, methylene, ethylidene, or isopropylidine group; with the proviso that the total number of carbon atoms in D and Y shall not exceed twenty; and with the further proviso that when n is 1, D is not an unsubstituted cyclopropyl nor a cyclopropyl substituted with at least one C 1 -C 13 alkyl; and the pharmaceutically acceptable non-toxic acid-addition and cationic salts thereof.
Claim 3
Dependent Claim
142 words
A compound of the formula: ##STR10## wherein Z is a moiety of the formula: ##STR11## wherein R 1 is hydrogen, R is hydrogen; Y is a divalent radical selected from the group consisting of branched or unbranched C 1 -C 13 alkylene or alkenylene and is either unsubstituted or substituted with at least one C 1 -C 4 alkyl; D is a moiety selected from the group consisting of C 3 -C 8 cycloalkyl and is either unsubstituted or substituted with at least one C 1 -C 3 alkyl, C 3 -C 8 cycloalkyl which is either unsubstituted or substituted with a C 5 -C 7 cycloalkyl, or decahydronaphthyl; with the proviso that D is not an unsubstituted cyclopropyl nor a cyclopropyl substituted with at least one C 1 -C 3 alkyl; and the pharmaceutically acceptable non-toxic acid-addition and cationic salts thereof.
Claim 4
Dependent Claim
142 words
A compound of the formula: ##STR10## wherein Z is a moiety of the formula: ##STR11## wherein R 1 is hydrogen, R is hydrogen; Y is a divalent radical selected from the group consisting of branched or unbranched C 1 -C 13 alkylene or alkenylene and is either unsubstituted or substituted with at least one C 1 -C 4 alkyl; D is a moiety selected from the group consisting of C 3 -C 8 cycloalkyl and is either unsubstituted or substituted with at least one C 1 -C 3 alkyl, C 3 -C 8 cycloalkyl which is either unsubstituted or substituted with a C 5 -C 7 cycloalkyl, or decahydronaphthyl; with the proviso that D is not an unsubstituted cyclopropyl nor a cyclopropyl substituted with at least one C 1 -C 3 alkyl; and the pharmaceutically acceptable non-toxic acid-addition and cationic salts thereof.
Claim 5
Dependent Claim
26 words
A compound according to claim 2, wherein R, D and Z are as previously defined; and Y is a divalent straight-chain C 1 -C 13 alkylene.
Claim 6
Dependent Claim
24 words
A compound according to claim 3, wherein R, Z and Y are as previously defined; and D is a C 5 -C 8 cycloalkyl.
Claim 7
Dependent Claim
26 words
A compound according to claim 4, wherein R, D and Z are as previously defined; and Y is a divalent straight-chain C 6 -C 8 alkylene.
Claim 8
Dependent Claim
8 words
The compound according to claim 2, p-[1-(1,3-dimethylcyclohexyl)-2-propylamino]benzoic acid.
Claim 9
Dependent Claim
8 words
The compound according to claim 2, p-[(2-cyclopentyl)hexylamino]benzoic acid.
Claim 10
Dependent Claim
8 words
The compound according to claim 2, p-[(3-cyclohexyl)pentylamino]benzoic acid.
Claim 11
Dependent Claim
8 words
The compound according to claim 2, p-[(4-cyclohexyl)hexylamino]benzoic acid.
Claim 12
Dependent Claim
8 words
The compound according to claim 2, p-[(4-cyclohexyl)2-ethyl)butylamino]benzoic acid.
Claim 13
Dependent Claim
8 words
The compound according to claim 3, p-[2-methylcyclohexyl)methylamino]benzoic acid.
Claim 14
Dependent Claim
8 words
The compound according to claim 3, p-[2-(1-ethylcyclohexyl)ethylamino]benzoic acid.
Claim 15
Dependent Claim
8 words
The compound according to claim 3, p-[3-(4-methylcyclohexyl)propylamino]benzoic acid.
Claim 16
Dependent Claim
8 words
The compound according to claim 3, p-[4-(4-ethylcyclohexyl)butylamino]benzoic acid.
Claim 17
Dependent Claim
8 words
The compound according to claim 4, p-[(cyclohexyl)methylamino]benzoic acid.
Claim 18
Dependent Claim
8 words
The compound according to claim 4, p-[(2-cyclohexyl)ethylamino]benzoic acid.
Claim 19
Dependent Claim
8 words
The compound according to claim 4, p-[(3-cyclopentyl)propylamino]benzoic acid.
Claim 20
Dependent Claim
8 words
The compound according to claim 4, p-[(4-cycloheptyl)butylamino]benzoic acid.
Claim 21
Dependent Claim
8 words
The compound according to claim 4, p-[(5-cyclohexyl)pentylamino]benzoic acid.
Claim 22
Dependent Claim
8 words
The compound according to claim 4, p-[(6-cyclopentyl)hexylamino]benzoic acid.
Claim 23
Dependent Claim
8 words
The compound according to claim 5, p-[(7-cyclopentyl)heptylamino]benzoic acid.
Claim 24
Dependent Claim
8 words
The compound according to claim 5, p-[(8-cyclohexyl)octylamino]benzoic acid.
Claim 25
Dependent Claim
8 words
The compound according to claim 5, p-[(9-cyclopentyl)nonylamino]benzoic acid.
Claim 26
Dependent Claim
8 words
The compound according to claim 5, p-[(13-cyclopentyl)tridecylamino]benzoic acid.
Claim 27
Dependent Claim
64 words
A compound of the formula: ##STR12## wherein R is hydrogen; D is a moiety selected from the group consisting of C 4 -C 7 cycloalkyl and is either unsubstituted or substituted with at least one C 4 -C 7 cycloalkyl, and decahydronaphthyl unsubstituted or substituted with at least one C 1 -C 4 alkyl, and the pharmaceutically acceptable non-toxic, acid-addition and cationic salts thereof.
Claim 28
Dependent Claim
64 words
A compound of the formula: ##STR12## wherein R is hydrogen; D is a moiety selected from the group consisting of C 4 -C 7 cycloalkyl and is either unsubstituted or substituted with at least one C 4 -C 7 cycloalkyl, and decahydronaphthyl unsubstituted or substituted with at least one C 1 -C 4 alkyl, and the pharmaceutically acceptable non-toxic, acid-addition and cationic salts thereof.
Claim 29
Dependent Claim
52 words
A compound according to claim 25, wherein R is as previously defined; and D is selected from the group consisting of C 5 -C 6 cycloalkyl unsubstituted or substituted with at least one C 5 -C 6 cycloalkyl, and decahydronaphthyl unsubstituted or substituted with at least one C 1 -C 4 alkyl.
Claim 30
Dependent Claim
8 words
The compound according to claim 26, p-[(3-cyclopentyl)cyclopentylamino]benzoic acid.
Claim 31
Dependent Claim
8 words
The compound according to claim 26, p-[(3-cyclohexyl)cyclopentylamino]benzoic acid.
Claim 32
Dependent Claim
8 words
The compound according to claim 26, p-[(2-cyclopentyl)cyclopentylamino]benzoic acid.
Claim 33
Dependent Claim
8 words
The compound according to claim 26, p-[(1-cyclohexyl)cyclohexylamino]benzoic acid.
Claim 34
Dependent Claim
8 words
The compound according to claim 26, p-[(1-cyclopentyl)cyclopentylamino]benzoic acid.
Claim 35
Dependent Claim
8 words
The compound according to claim 26, p-[1-(4α-methyldecahydronaphthyl)amino]benzoic acid.
Claim 36
Dependent Claim
47 words
A compound of the formula: ##STR13## wherein R is hydrogen; D is a moiety selected from the group consisting of C 3 -C 16 cycloalkyl unsubstituted or substituted with at least one C 1 -C 5 alkyl; and the pharmaceutically acceptable non-toxic acid-addition and cationic salts thereof.
Claim 37
Dependent Claim
47 words
A compound of the formula: ##STR13## wherein R is hydrogen; D is a moiety selected from the group consisting of C 3 -C 16 cycloalkyl unsubstituted or substituted with at least one C 1 -C 5 alkyl; and the pharmaceutically acceptable non-toxic acid-addition and cationic salts thereof.
Claim 38
Dependent Claim
38 words
A compound according to claim 33, wherein R is as previously defined; and D is selected from the group consisting of C 3 -C 6 cycloalkyl unsubstituted or substituted with at least one C 1 -C 5 alkyl.
Claim 39
Dependent Claim
22 words
A compound according to claim 33, wherein R is as previously defined; and D is a C 3 -C 16 cycloalkyl group.
Claim 40
Dependent Claim
22 words
A compound according to claim 35, wherein R is as previously defined; and D is a C 5 -C 12 cycloalkyl group.
Claim 41
Dependent Claim
8 words
The compound according to claim 34, p-[(2-pentyl)cyclopropylamino]benzoic acid.
Claim 42
Dependent Claim
8 words
The compound according to claim 34, p-[(1-propyl)cyclopentylamino]benzoic acid.
Claim 43
Dependent Claim
8 words
The compound according to claim 34, p-[(4-propyl)cyclohexylamino]benzoic acid.
Claim 44
Dependent Claim
8 words
The compound according to claim 36, p-cyclopentylaminobenzoic acid.
Claim 45
Dependent Claim
8 words
The compound according to claim 36, p-cyclohexylaminobenzoic acid.
Claim 46
Dependent Claim
8 words
The compound according to claim 36, p-cycloheptylaminobenzoic acid.
Claim 47
Dependent Claim
8 words
The compound according to claim 36, p-cyclooctylaminobenzoic acid.
Claim 48
Dependent Claim
8 words
The compound according to claim 36, p-cyclodecylaminobenzoic acid.
Claim 49
Dependent Claim
8 words
The compound according to claim 36, p-cyclododecylaminobenzoic acid.
Claim 50
Dependent Claim
104 words
A compound of the formula: ##STR14## wherein R is hydrogen; D is a moiety selected from the group consisting of C 4 -C 9 cycloalkenyl, C 4 -C 9 cycloalkenyl substituted with at least one C 1 -C 2 alkyl, and C 5 -C 8 cycloalkyl substituted with a methylene moiety or at least one C 1 -C 2 alkyl; Y is a divalent radical selected from the group consisting of branched or unbranched C 1 -C 13 alkylene or alkenylene and is either unsubstituted or substituted with at least one C 1 -C 2 alkyl; and the pharmaceutically acceptable non-toxic acid-addition salts thereof.
Claim 51
Dependent Claim
104 words
A compound of the formula: ##STR14## wherein R is hydrogen; D is a moiety selected from the group consisting of C 4 -C 9 cycloalkenyl, C 4 -C 9 cycloalkenyl substituted with at least one C 1 -C 2 alkyl, and C 5 -C 8 cycloalkyl substituted with a methylene moiety or at least one C 1 -C 2 alkyl; Y is a divalent radical selected from the group consisting of branched or unbranched C 1 -C 13 alkylene or alkenylene and is either unsubstituted or substituted with at least one C 1 -C 2 alkyl; and the pharmaceutically acceptable non-toxic acid-addition salts thereof.
Claim 52
Dependent Claim
43 words
A compound according to claim 46, wherein R is as previously defined; and D is a C 5 -C 8 cycloalkenyl unsubstituted or substituted with at least one C 1 -C 2 alkyl; and Y is a divalent C 1 -C 13 alkylene.
Claim 53
Dependent Claim
24 words
A compound according to claim 47, wherein R and D are as previously defined; and Y is a divalent C 4 -C 13 alkylene.
Claim 54
Dependent Claim
24 words
A compound according to claim 48, wherein R and Y are as previously defined; and D is a C 5 -C 6 cycloalkenyl group.
Claim 55
Dependent Claim
61 words
A compound according to claim 46, wherein R is as previously defined; and D is selected from the group consisting of C 5 -C 8 cycloalkyl substituted with a methylene moiety and unsubstituted or substituted with at least one C 1 -C 2 alkyl; and Y is a divalent radical selected from the group consisting of --CH 2 -- and ##STR15##
Claim 56
Dependent Claim
8 words
The compound according to claim 46, p-[(cyclobut-2-enyl)methylamino]benzoic acid.
Claim 57
Dependent Claim
8 words
The compound according to claim 46, p-[1-(cyclopent-1-enyl)propylamino]benzoic acid.
Claim 58
Dependent Claim
8 words
The compound according to claim 46, p-[1-(cyclohex-3-enyl)propylamino]benzoic acid.
Claim 59
Dependent Claim
8 words
The compound according to claim 46, p-[1-(cyclohept-1-enyl)ethylamino]benzoic acid.
Claim 60
Dependent Claim
8 words
The compound according to claim 46, p-[1-(cyclooct-1-enyl)ethylamino]benzoic acid.
Claim 61
Dependent Claim
8 words
The compound according to claim 46, p-[2-(2-ethyl-2-cyclopent-3-enyl)ethylamino]benzoic acid.
Claim 62
Dependent Claim
8 words
The compound according to claim 46, p-[2-(4-methylcyclohex-3-enyl)ethylamino]benzoic acid.
Claim 63
Dependent Claim
8 words
The compound according to claim 46, p-[2-cyclonon-1-enyl)ethylamino]benzoic acid.
Claim 64
Dependent Claim
8 words
The compound according to claim 46, p-[3-methyl-3-(4-methylcyclohex-3-enyl)propylamino]benzoic acid.
Claim 65
Dependent Claim
8 words
The compound according to claim 46, p-[(1,3,3-trimethylcyclohex-2-enyl)methylamino]benzoic acid.
Claim 66
Dependent Claim
8 words
The compound according to claim 47, p-(cyclopent-3-enyl)methylamino)benzoic acid.
Claim 67
Dependent Claim
8 words
The compound according to claim 47, p-(cyclooct-2-enyl)methylamino)benzoic acid.
Claim 68
Dependent Claim
8 words
The compound according to claim 47, p-(cyclohept-1-enyl)methylamino)benzoic acid.
Claim 69
Dependent Claim
8 words
The compound according to claim 47, p-(cyclooct-4-enyl)methylamino)benzoic acid.
Claim 70
Dependent Claim
8 words
The compound according to claim 47, p-[2-(cyclooct-1-enyl)ethylamino]benzoic acid.
Claim 71
Dependent Claim
8 words
The compound according to claim 47, p-[3-(cyclohex-2-enyl)propylamino]benzoic acid.
Claim 72
Dependent Claim
8 words
The compound according to claim 48, p-[4-(cyclohex-3-enyl)butylamino]benzoic acid.
Claim 73
Dependent Claim
8 words
The compound according to claim 49, p-[4-(3-cyclopentenyl)butylamino]benzoic acid.
Claim 74
Dependent Claim
8 words
The compound according to claim 49, p-[4-(1-cyclohexenyl)butylamino]benzoic acid.
Claim 75
Dependent Claim
8 words
The compound according to claim 49, p-[5-(1-cyclopentenyl)pentylamino]benzoic acid.
Claim 76
Dependent Claim
8 words
The compound according to claim 49, p-[11-(3-cyclopentenyl)undecylamino]benzoic acid.
Claim 77
Dependent Claim
8 words
The compound according to claim 49, p-[13-(1-cyclopentenyl)tridecylamino]benzoic acid.
Claim 78
Dependent Claim
8 words
The compound according to claim 49, p-[13-(3-cyclopentenyl)tridecylamino]benzoic acid.
Claim 79
Dependent Claim
8 words
The compound according to claim 50, p-[1-(5-methylenecyclooctyl)ethylamino]benzoic acid.
Claim 80
Dependent Claim
8 words
The compound according to claim 50, p-[(5-methylenecyclooctyl)methylamino]benzoic acid.
Claim 81
Dependent Claim
8 words
The compound according to claim 50, p-[(1,3-dimethyl-2-methylenecyclopentyl)methylamino]benzoic acid.
Claim 82
Dependent Claim
76 words
A compound of the formula: ##STR16## wherein R is hydrogen; D is a moiety selected from the group consisting of C 4 -C 17 cycloalkenyl unsubstituted or substituted with at least one C 1 -C 4 alkyl, and C 4 -C 10 cycloalkyl substituted with a moiety selected from the group consisting of methylene, ethylidene and isopropylidene or at least one C 1 -C 3 alkyl; and the pharmaceutically acceptable non-toxic acid-addition and cationic salts thereof.
Claim 83
Dependent Claim
76 words
A compound of the formula: ##STR16## wherein R is hydrogen; D is a moiety selected from the group consisting of C 4 -C 17 cycloalkenyl unsubstituted or substituted with at least one C 1 -C 4 alkyl, and C 4 -C 10 cycloalkyl substituted with a moiety selected from the group consisting of methylene, ethylidene and isopropylidene or at least one C 1 -C 3 alkyl; and the pharmaceutically acceptable non-toxic acid-addition and cationic salts thereof.
Claim 84
Dependent Claim
45 words
A compound according to claim 77, wherein R is as previously defined; and D is a moiety selected from the group consisting of C 4 -C 17 cycloalkenyl, and C 4 -C 8 cyclo alkenyl substituted with at least one C 1 -C 4 alkyl.
Claim 85
Dependent Claim
21 words
A compound according to claim 78, wherein R is as previously defined; and D is a C 5 -C 17 cycloalkenyl.
Claim 86
Dependent Claim
21 words
A compound according to claim 79, wherein R is as previously defined; and D is a C 6 -C 15 cycloalkenyl.
Claim 87
Dependent Claim
27 words
A compound according to claim 77, wherein R is as previously defined; and D is a C 4 -C 10 cycloalkyl substituted with methylene, ethylidene or isopropylidene.
Claim 88
Dependent Claim
24 words
A compound according to claim 81, wherein R is as previously defined; and D is a C 5 -C 10 cycloalkyl substituted with methylene.
Claim 89
Dependent Claim
8 words
The compound according to claim 77, p-(2,2-dimethyl-4-isopropylidenecyclobutylamino)benzoic acid.
Claim 90
Dependent Claim
9 words
The compound according to claim 78, p-(4-isopropyl cyclohex-2-enylamino)benzoic acid.
Claim 91
Dependent Claim
8 words
The compound according to claim 78, p-(2-methylcyclooct-2-enylamino)benzoic acid.
Claim 92
Dependent Claim
8 words
The compound according to claim 78, p-(2-methylcyclohept-2-enylamino)benzoic acid.
Claim 93
Dependent Claim
8 words
The compound according to claim 78, p-(3,7-dimethylcyclohept-3-enylamino)benzoic acid.
Claim 94
Dependent Claim
8 words
The compound according to claim 79, p-(cyclohept-8-enylamino)benzoic acid.
Claim 95
Dependent Claim
8 words
The compound according to claim 79, p-(cycloheptadec-9-enylamino)benzoic acid.
Claim 96
Dependent Claim
8 words
The compound according to claim 79, p-(cyclopent-2-enylamino)benzoic acid.
Claim 97
Dependent Claim
8 words
The compound according to claim 79, p-(cyclopent-3-enylamino)benzoic acid.
Claim 98
Dependent Claim
8 words
The compound according to claim 80, p-(cyclohex-2-enylamino)benzoic acid.
Claim 99
Dependent Claim
8 words
The compound according to claim 80, p-(cyclonon-2-enylamino)benzoic acid.
Claim 100
Dependent Claim
8 words
The compound according to claim 80, p-(cyclonon-3-enylamino)benzoic acid.
Claim 101
Dependent Claim
8 words
The compound according to claim 80, p-(E-cyclodec-3-enylamino)benzoic acid.
Claim 102
Dependent Claim
8 words
The compound according to claim 80, p-(Z-cyclodec-3-enylamino)benzoic acid.
Claim 103
Dependent Claim
8 words
The compound according to claim 82, p-(4-methylenecyclooctylamino)benzoic acid.
Claim 104
Dependent Claim
8 words
The compound according to claim 82, p-(2-methylenecyclodecylamino)benzoic acid.
Claim 105
Dependent Claim
8 words
The compound according to claim 82, p-(2-methylenecycloheptylamino)benzoic acid.
References Cited (Backward Citations)
SU331058A1
Cited
US3787478A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-10-07 | 1984-04-07 | 1984-10-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-07 | 1988-04-07 | 1988-10-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-07 | 1992-04-07 | 1992-10-07 | $7700.00 | Window Closed / Lapsed |