US4734416A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Pharmaceutically useful carbostyril derivatives
Assignee: Otsuka Pharmaceutical Co Ltd
•
Filing: 1979-03-28
•
Granted: 1988-03-29
•
Expires: 1999-03-28
Abstract
Abstract Carbostyril derivatives having antihistamic action and central nervous controlling action are useful as antihistamic agents or central nervous controlling agents. The derivatives are represented by the general formula, ##STR1## wherein R 1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms or a phenylalkyl group having an alkylene group containing 1 to 4 carbon atoms; R 2 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a phenyl group; R 3 is a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkanolyoxy group having 1 to 4 carbon atoms or a 3,4,5-trimethoxybenzoyloxy group; R 4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 5 is a cycloalkyl group having 3 to 8 carbon atoms, a phenyl group (which may have 1 to 3 substituted groups selected from the group consisting of halogen atoms, alkyl groups having 1 to 4 carbon atoms and alkoxy groups having 1 to 4 carbon atoms), an alkyl group having 1 to 4 carbon atoms (having one substituted group such as a hydroxy group, a phenyl group or an alkanoyloxy group having 1 to 4 carbon atoms), an alkanoyl group having 1 to 4 carbon atoms or benzoyl group; X is a halogen atom; n is 0, or an integer of 1 or 2; Q is an integer of 2 or 3, l and m are respectively an integer of 0 or 1-6, but the sum of l and m should not exceed 6; the carbon-carbon bond at the 3- and 4-positions in the carbostyril skeleton is a single or double bond; and the substituted position of the side chain of ##STR2## is any one of the 4-, 5-, 6-, 7- or 8-positions.
Inventors
- 👤 Kazuo Banno
- 👤 Takafuni Fujioka
- 👤 Yasuo Oshiro
- 👤 Kazuyuki Nakagawa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 14:57
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/20; C07D215/22; C07D215/227; A; A61; A61P; A61P25/00; A61P25/20; A61P29/00; A61P37/00; A61P37/08; A61P43/00; C07D215/24; C07D215/26; C07D215/28
Claims Analysis
Total Claims: 146
Claim 1
Independent Claim
251 words
A carbostyril derivative represented by the formula, ##STR25## wherein R 1 is a hydrogen atom, an alkyl group having 1 to 6 carbon alkynyl group having 2 to 4 carbon atoms or a phenyl alkyl group having an alkylene group having 1 to 4 carbon atoms; R 2 is a hydrogen atom; R 3 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R 4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 5 is a phenyl group which may be substituted by 1 to 3 identical or different groups selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms; X is a halogen atom; n is 0 or an integer of 1 or 2; Q is an integer of 2; l and m are respectively 0 or an integer of 1 to 6, but the sum of l and m should not exceed 6; the carbon-carbon bond at the 3- and 4-positions in the carbostyril skeleton in a single or double bond; the substituted position of the side chain of ##STR26## is any one of the 4-, 5-, 6-, 7- or 8-positions; or an acid addition salt thereof, with the proviso that when said side chain is substituted at the 4-position and said carbon-carbon bond at the 3- or 4-positions is a double bond, then R 2 does not exist.
Claim 2
Dependent Claim
251 words
A carbostyril derivative represented by the formula, ##STR25## wherein R 1 is a hydrogen atom, an alkyl group having 1 to 6 carbon alkynyl group having 2 to 4 carbon atoms or a phenyl alkyl group having an alkylene group having 1 to 4 carbon atoms; R 2 is a hydrogen atom; R 3 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R 4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 5 is a phenyl group which may be substituted by 1 to 3 identical or different groups selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms; X is a halogen atom; n is 0 or an integer of 1 or 2; Q is an integer of 2; l and m are respectively 0 or an integer of 1 to 6, but the sum of l and m should not exceed 6; the carbon-carbon bond at the 3- and 4-positions in the carbostyril skeleton in a single or double bond; the substituted position of the side chain of ##STR26## is any one of the 4-, 5-, 6-, 7- or 8-positions; or an acid addition salt thereof, with the proviso that when said side chain is substituted at the 4-position and said carbon-carbon bond at the 3- or 4-positions is a double bond, then R 2 does not exist.
Claim 3
Dependent Claim
34 words
A carbostyril derivative or an acid addition salt thereof according to claim 1, wherein the substituted position of the side chain represented by the formula, ##STR27## is 5- or 7-position in the carbostyril skeleton.
Claim 4
Dependent Claim
35 words
A carbostyril derivative or an acid addition salt thereof according to claim 1, wherein the substituted position of the side chain represented by the formula, ##STR28## is 4-, 6- or 8-position in the carbostyril skeleton.
Claim 5
Dependent Claim
32 words
A carbostyril derivative or an acid addition salt thereof according to claim 2, wherein the substituted position of the side chain represented by the formula, ##STR29## is 5-position in the carbostyril skeleton.
Claim 6
Dependent Claim
32 words
A carbostyril derivative or an acid addition salt thereof according to claim 2, wherein the substituted position of the side chain represented by the formula, ##STR30## is 7-position in the carbostyril skeleton.
Claim 7
Dependent Claim
1 words
7-[3-(4-Phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.
Claim 8
Dependent Claim
1 words
7-[3-(4-Phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.
Claim 9
Dependent Claim
1 words
7-{3-[4-(2-Methoxyphenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 10
Dependent Claim
1 words
7-{3-[4-(2-Methoxyphenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 11
Dependent Claim
1 words
7-{3-[4-(3-Chlorophenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 12
Dependent Claim
1 words
7-{3-[4-(3-Chlorophenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 13
Dependent Claim
1 words
7-{3-[4-(2-Fluorophenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 14
Dependent Claim
1 words
7-{3-[4-(2-Fluorophenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 15
Dependent Claim
1 words
7-[3-(4-Phenylpiperazinyl)propoxy]carbostyril.
Claim 16
Dependent Claim
1 words
7-[3-(4-Phenylpiperazinyl)propoxy]carbostyril.
Claim 17
Dependent Claim
1 words
7-{3-[4-(2-Ethoxyphenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 18
Dependent Claim
1 words
7-{3-[4-(2-Ethoxyphenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 19
Dependent Claim
1 words
1-Methyl-7-[3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.
Claim 20
Dependent Claim
1 words
1-Methyl-7-[3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.
Claim 21
Dependent Claim
1 words
7-[4-(4-Phenylpiperazinyl)butoxy]-3,4-dihydrocarbostyril.
Claim 22
Dependent Claim
1 words
7-[4-(4-Phenylpiperazinyl)butoxy]-3,4-dihydrocarbostyril.
Claim 23
Dependent Claim
1 words
5-[3-(4-Phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.
Claim 24
Dependent Claim
1 words
5-[3-(4-Phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.
Claim 25
Dependent Claim
1 words
6-[3-(4-Phenylpiperazinyl)propoxy]carbostyril.
Claim 26
Dependent Claim
1 words
6-[3-(4-Phenylpiperazinyl)propoxy]carbostyril.
Claim 27
Dependent Claim
1 words
7-{3-[4-(2-Chlorophenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 28
Dependent Claim
1 words
7-{3-[4-(2-Chlorophenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 29
Dependent Claim
1 words
8-Bromo-5-[3-(4-phenylpiperazinyl)propoxy]carbostyril.
Claim 30
Dependent Claim
1 words
8-Bromo-5-[3-(4-phenylpiperazinyl)propoxy]carbostyril.
Claim 31
Dependent Claim
1 words
7-{3-[4-(2-Methoxyphenyl)piperazinyl]propoxy}carbostyril.
Claim 32
Dependent Claim
1 words
7-{3-[4-(2-Methoxyphenyl)piperazinyl]propoxy}carbostyril.
Claim 33
Dependent Claim
1 words
7-{3-[4-(4-Methylphenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 34
Dependent Claim
1 words
7-{3-[4-(4-Methylphenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 35
Dependent Claim
1 words
1-Benzyl-5-[3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.
Claim 36
Dependent Claim
1 words
1-Benzyl-5-[3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.
Claim 37
Dependent Claim
31 words
A central nervous controlling agent, containing a suitable amount of a carbostyril derivative or acid addition salt thereof according to claim 1 as an active ingredient and a pharmaceutically acceptable carrier.
Claim 38
Dependent Claim
22 words
A carbostyril derivative or an acid addition salt thereof according to claim 1 or 2, wherein R 1 is a hydrogen atom.
Claim 39
Dependent Claim
59 words
A carbostyril derivative or an acid addition salt thereof according to claim 1, wherein R 1 is an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms or a phenyl alkyl group having an alkylene group having 1 to 4 carbon atoms.
Claim 40
Dependent Claim
26 words
A carbostyril derivative or an acid addition salt thereof according to claim 1 or 2, wherein R 1 is a hydrogen atom and n is 0.
Claim 41
Dependent Claim
113 words
A carbostyril derivative or a salt thereof as claimed in claim 1, wherein the carbon-carbon bond at the 3- and 4-positions in the carbostyril skeleton is a single bond, the substituted position of the side chain of ##STR31## is the 6-position, l and m are each 1, R 4 is hydrogen, n is 0, R 1 denotes a hydrogen atom or a C 1 -C 6 alkyl group, R 5 denotes a phenyl group having one to three, identical or different substituents selected from the group consisting of a C 1 -C 4 -alkyl group, a C 1 -C 4 -alkoxy group and a halogen atom and R 3 denotes a hydrogen atom.
Claim 42
Dependent Claim
53 words
A carbostyril derivative or a salt thereof as claimed in claim 25, wherein R 5 is a phenyl group which is substituted by a group selected from the group consisting of a halogen atom, an alkyl group having 1 to 3 carbon atoms and an alkoxy group having 1 to 3 carbon atoms.
Claim 43
Dependent Claim
16 words
A composition having a central nervous controlling effect comprising a compound as defined in claim 26.
Claim 44
Dependent Claim
39 words
The method of treating a human patient to produce a central nervous controlling effect which comprises orally administering to said patient a dosage of about 40 ug to 2 mg/kg day of a compound as defined in claim 26.
Claim 45
Dependent Claim
39 words
The method of treating a human patient to produce a central nervous controlling effect which comprises intravenously administering to said patient a dosage of about 40 ug to 2 mg/kg day of a compound as defined in claim 26.
Claim 46
Dependent Claim
17 words
The compound of claim 1 wherein R 5 is a phenyl group substituted by two halogen atoms.
Claim 47
Dependent Claim
1 words
5-{3-[4-(2-Ethoxyphenyl)piperazinyl]propoxy}3,4-dihydrocarbostyril.
Claim 48
Dependent Claim
1 words
5-{3-[4-(2-Ethoxyphenyl)piperazinyl]propoxy}3,4-dihydrocarbostyril.
Claim 49
Dependent Claim
11 words
A carbostyril derivative in accordance with claim 1 consisting of: 7-{3-[4-(3-Fluorophenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 50
Dependent Claim
103 words
A (4-substituted-piperazin-1-yl)alkoxy-2-oxo-1,2-dihydroquinoline of the formula: ##STR32## in which R 1 is a hydrogen atom or an alkyl radical with 1 to 6 carbon atoms, R 3 is a hydrogen atom or an alkyl radical having 1 to 4 carbon atoms, R 4 is a hydrogen atom, a halogen atom, or an alkyl or alkoxy radical with 1 to 4 carbon atoms, n is 2, 3, 4 or 5 and A is a valency bond or a methylene radical with the proviso that when A is a methylene radical, R 4 is a hydrogen atom; or a salt thereof with a pharmacologically acceptable acid.
Claim 51
Dependent Claim
103 words
A (4-substituted-piperazin-1-yl)alkoxy-2-oxo-1,2-dihydroquinoline of the formula: ##STR32## in which R 1 is a hydrogen atom or an alkyl radical with 1 to 6 carbon atoms, R 3 is a hydrogen atom or an alkyl radical having 1 to 4 carbon atoms, R 4 is a hydrogen atom, a halogen atom, or an alkyl or alkoxy radical with 1 to 4 carbon atoms, n is 2, 3, 4 or 5 and A is a valency bond or a methylene radical with the proviso that when A is a methylene radical, R 4 is a hydrogen atom; or a salt thereof with a pharmacologically acceptable acid.
Claim 52
Dependent Claim
142 words
A carbostyril derivative or a salt thereof as claimed in claim 1, wherein R 1 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R 3 is a hydrogen atom; R 4 is a hydrogen atom; R 5 is a phenyl group which may be substituted by a group selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms; n is 0; l and m are respectively 0 or an integer, wherein the sum of l and m is from 1 to 4; the carbon-carbon bond at the 3- and 4-positions in the carbostyril skeleton is a double bond; and the substituted position of the side chain of ##STR33## is any one of the 5-, 6-, 7- or 8-positions.
Claim 53
Dependent Claim
75 words
A compound or salt thereof according to claim 34 in which R 1 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 2 is a hydrogen atom; and R 5 is a phenyl group which may be substituted by a group selected from the group consisting of a chlorine atom, an alkyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms.
Claim 54
Dependent Claim
61 words
A compound or salt thereof according to claim 33 wherein such compound is ##STR34## in which R 3 is a hydrogen atom or a methyl radical, R 4 is a hydrogen atom or a chlorine atom, and A is a valency bond or methylene radical, with the proviso that when A is a methylene radical, R 4 is a hydrogen atom.
Claim 55
Dependent Claim
32 words
A compound or salt thereof according to claim 33 wherein such compound is ##STR35## in which R 3 is a hydrogen atom or a methyl radical, and A is a valency bond.
Claim 56
Dependent Claim
36 words
A compound or salt thereof according to claim 33 wherein such compound is: ##STR36## in which R 3 is a hydrogen atom or a methyl radical, and A is a valency bond or a methylene radical.
Claim 57
Dependent Claim
32 words
A compound or salt thereof according to claim 33 wherein such compound is: ##STR37## in which R 3 is a hydrogen atom or a methyl radical, and A is a valency bond.
Claim 58
Dependent Claim
25 words
A composition having an antihistaminic and a central nervous controlling effect comprising an effective amount of a compound or salt as defined in claim 34.
Claim 59
Dependent Claim
37 words
A method of treating a patient to produce a central nervous controlling effect or an antihistaminic effect comprising the step of administering to said patient an effective amount of a compound or salt according to claim 34.
Claim 60
Dependent Claim
254 words
A carbostyril derivative represented by the formula, ##STR38## wherein R 1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms or a phenyl alkyl group having an alkylene group having 1 to 4 carbon atoms; R 2 is an alkyl group having 1 to 4 carbon atoms or a phenyl group; R 3 is a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkanoyloxy group having 1 to 4 carbon atoms or a 3,4,5-trimethoxybenzoyloxy group; R 4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 5 is a phenyl group which may be substituted by 1 to 3 identical or different groups selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms; X is a halogen atom; n is 0 or an integer of 1 to 2; Q is an integer of 2, l and m are respectively 0 or an integer of 1 to 6, but the sum of l and m should not exceed 6; the carbon-carbon bond at the 3- and 4-positions in the carbostyril skeleton is a single or double bond; the substituted position of the side chain of ##STR39## is any one of the 5-, 6-, 7- or 8-positions; or an acid addition salt thereof.
Claim 61
Dependent Claim
254 words
A carbostyril derivative represented by the formula, ##STR38## wherein R 1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms or a phenyl alkyl group having an alkylene group having 1 to 4 carbon atoms; R 2 is an alkyl group having 1 to 4 carbon atoms or a phenyl group; R 3 is a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkanoyloxy group having 1 to 4 carbon atoms or a 3,4,5-trimethoxybenzoyloxy group; R 4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 5 is a phenyl group which may be substituted by 1 to 3 identical or different groups selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms; X is a halogen atom; n is 0 or an integer of 1 to 2; Q is an integer of 2, l and m are respectively 0 or an integer of 1 to 6, but the sum of l and m should not exceed 6; the carbon-carbon bond at the 3- and 4-positions in the carbostyril skeleton is a single or double bond; the substituted position of the side chain of ##STR39## is any one of the 5-, 6-, 7- or 8-positions; or an acid addition salt thereof.
Claim 62
Dependent Claim
30 words
A carbostyril derivative or an acid addition salt thereof according to claim 42, wherein R 3 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Claim 63
Dependent Claim
33 words
A carbostyril derivative or an acid addition salt thereof according to claim 42, wherein R 3 is a hydroxy group, an alkanoyloxy group having 1 to 4 carbon atoms or a 3,4,5-trimethoxybenzoyloxy group.
Claim 64
Dependent Claim
34 words
A carbostyril derivative or an acid addition salt thereof according to claim 43, wherein the substituted position of the side chain represented by the formula, ##STR40## is 5- or 7-position in the carbostyril skeleton.
Claim 65
Dependent Claim
34 words
A carbostyril derivative or an acid addition salt thereof according to claim 43, wherein the substituted position of the side chain represented by the formula, ##STR41## is 6- or 8-position in the carbostyril skeleton.
Claim 66
Dependent Claim
32 words
A carbostyril derivative or an acid addition salt thereof according to claim 45, wherein the substituted position of the side chain represented by the formula, ##STR42## is 5-position in the carbostyril skeleton.
Claim 67
Dependent Claim
32 words
A carbostyril derivative or an acid addition salt thereof according to claim 45, wherein the substituted position of the side chain represented by the formula, ##STR43## is 7-position in the carbostyril skeleton.
Claim 68
Dependent Claim
34 words
A pharmaceutical composition useful as an antihistaminic agent, containing a suitable amount of carbostyril derivative or an acid addition salt thereof according to claim 42 as an active ingredient and a pharmaceutically acceptable carrier.
Claim 69
Independent Claim
371 words
A method for producing an antihistaminic effect in a mammal comprising the step of administering to the mammal for producing said antihistaminic effect a pharmaceutical composition containing a suitable amount of a carbostyril derivative represented by the formula, ##STR44## wherein R 1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms or a phenyl alkyl group having an alkylene group having 1 to 4 carbon atoms; R 2 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a phenyl group; R 3 is a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkanoyloxy group having 1 to 4 carbon atoms or a 3,4,5-trimethoxybenzoyloxy group; R 4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 5 is a cycloalkyl group having 3 to 8 carbon atoms, a phenyl group which may be substituted by 1 to 3 identical or different groups selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms, a substituted alkyl group having 1 to 4 carbon atoms, having one hydroxy group, phenyl group or alkanoyloxy group having 1 to 4 carbon atoms as the substituent, an alkanoyl group having 1 to 4 carbon atoms or a benzoyl group; X is a halogen atom; n is 0 or an integer of 1 or 2; Q is an integer of 2; l and m are respectively 0 or an integer of 1 to 6, but the sum of l and m should not exceed 6; the carbon-carbon bond at the 3- and 4-positions in the carbostyril skeleton is a single or double bond; the substituted position of the side chain of ##STR45## is any one of the 4-, 5-, 6-, 7-, or 8-positions; or an acid addition salt thereof, with the proviso that when said side chain is substituted at the 4-position and said carbon-carbon bond at the 3- and 4-positions is a double bond, then R 2 does not exist.
Claim 70
Independent Claim
371 words
A method for producing an antihistaminic effect in a mammal comprising the step of administering to the mammal for producing said antihistaminic effect a pharmaceutical composition containing a suitable amount of a carbostyril derivative represented by the formula, ##STR44## wherein R 1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms or a phenyl alkyl group having an alkylene group having 1 to 4 carbon atoms; R 2 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a phenyl group; R 3 is a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkanoyloxy group having 1 to 4 carbon atoms or a 3,4,5-trimethoxybenzoyloxy group; R 4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 5 is a cycloalkyl group having 3 to 8 carbon atoms, a phenyl group which may be substituted by 1 to 3 identical or different groups selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms, a substituted alkyl group having 1 to 4 carbon atoms, having one hydroxy group, phenyl group or alkanoyloxy group having 1 to 4 carbon atoms as the substituent, an alkanoyl group having 1 to 4 carbon atoms or a benzoyl group; X is a halogen atom; n is 0 or an integer of 1 or 2; Q is an integer of 2; l and m are respectively 0 or an integer of 1 to 6, but the sum of l and m should not exceed 6; the carbon-carbon bond at the 3- and 4-positions in the carbostyril skeleton is a single or double bond; the substituted position of the side chain of ##STR45## is any one of the 4-, 5-, 6-, 7-, or 8-positions; or an acid addition salt thereof, with the proviso that when said side chain is substituted at the 4-position and said carbon-carbon bond at the 3- and 4-positions is a double bond, then R 2 does not exist.
Claim 71
Dependent Claim
22 words
The method of claim 50, wherein R 3 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Claim 72
Dependent Claim
25 words
The method of claim 50, wherein R 3 is a hydroxy group, an alkanoyloxy group having 1 to 4 carbon atoms or a 3,4,5-trimethoxybenzoyloxy group.
Claim 73
Dependent Claim
52 words
The method of claim 51, wherein R 5 is a phenyl group which may be substituted by 1 to 3 identical or different groups selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms.
Claim 74
Dependent Claim
26 words
The method of claim 51, wherein R 5 is a substituted alkyl group having 1 to 4 carbon atoms, having one phenyl group as the substituent.
Claim 75
Dependent Claim
57 words
The method of claim 51, wherein R 5 is a cycloalkyl group having 3 to 8 carbon atoms; a substituted alkyl group having 1 to 4 carbon atoms having one hydroxy group or alkanoyloxy group having 1 to 4 carbon atoms as the substituent; an alkanoyl group having 1 to 4 carbon atoms or a benzoyl group.
Claim 76
Dependent Claim
52 words
The method of claim 52, wherein R 5 is a phenyl group which may be substituted by 1 to 3 identical or different groups selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms.
Claim 77
Dependent Claim
59 words
The method of claim 52, wherein R 5 is a cycloalkyl group having 3 to 8 carbon atoms; a substituted alkyl group having 1 to 4 carbon atoms having one hydroxy group, phenyl group or alkanoyloxy group having 1 to 4 carbon atoms as the substituent; an alkanoyl group having 1 to 4 carbon atoms or a benzoyl group.
Claim 78
Dependent Claim
26 words
The method of claim 53, wherein the substituted position of the side chain represented by the formula, ##STR46## is 5- or 7-position in the carbostyril skeleton.
Claim 79
Dependent Claim
27 words
The method of claim 53, wherein the substituted position of the side chain represented by the formula, ##STR47## is 4-, 6- or 8-position in the carbostyril skeleton.
Claim 80
Dependent Claim
24 words
The method of claim 58, wherein the substituted position of the side chain represented by the formula, ##STR48## is 5-position in the carbostyril skeleton.
Claim 81
Dependent Claim
24 words
The method of claim 58, wherein the substituted position of the side chain represented by the formula, ##STR49## is 7-position in the carbostyril skeleton.
Claim 82
Dependent Claim
280 words
A carbostyril derivative represented by the formula, ##STR50## wherein R 1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms or a phenyl alkyl group having an alkylene group having 1 to 4 carbon atoms; R 2 is a hydrogen atom, a C 1 -C 4 alkyl group; R 3 is a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkanoyloxy group having 1 to 4 carbon atoms or a 3,4,5-trimethoxybenzoyloxy group; R 4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 5 is a cycloalkyl group having 3 to 8 carbon atoms, a substituted alkyl group having 1 to 4 carbon atoms, having one phenyl group as the substituent, an alkanoyl group having 1 to 4 carbon atoms or a benzoyl group; X is a halogen atom; n is 0 or an integer of 1 or 2; Q is an integer of 2; l and m are respectively 0 or an integer of 1 to 6, but the sum of l and m should not exceed 6; the carbon-carbon bond at the 3- and 4-positions in the carbostyril skeleton is a single or double bond; the substituted position of the side chain of ##STR51## is any one of the 4-, 5-, 6-, 7-, or 8-positions; or an acid addition salt thereof, with the proviso that when said side chain is substituted at the 4-position and said carbon-carbon bond at the 3- and 4-positions is a double bond, then R 2 does not exist.
Claim 83
Dependent Claim
280 words
A carbostyril derivative represented by the formula, ##STR50## wherein R 1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms or a phenyl alkyl group having an alkylene group having 1 to 4 carbon atoms; R 2 is a hydrogen atom, a C 1 -C 4 alkyl group; R 3 is a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkanoyloxy group having 1 to 4 carbon atoms or a 3,4,5-trimethoxybenzoyloxy group; R 4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 5 is a cycloalkyl group having 3 to 8 carbon atoms, a substituted alkyl group having 1 to 4 carbon atoms, having one phenyl group as the substituent, an alkanoyl group having 1 to 4 carbon atoms or a benzoyl group; X is a halogen atom; n is 0 or an integer of 1 or 2; Q is an integer of 2; l and m are respectively 0 or an integer of 1 to 6, but the sum of l and m should not exceed 6; the carbon-carbon bond at the 3- and 4-positions in the carbostyril skeleton is a single or double bond; the substituted position of the side chain of ##STR51## is any one of the 4-, 5-, 6-, 7-, or 8-positions; or an acid addition salt thereof, with the proviso that when said side chain is substituted at the 4-position and said carbon-carbon bond at the 3- and 4-positions is a double bond, then R 2 does not exist.
Claim 84
Dependent Claim
30 words
A carbostyril derivative or an acid addition salt thereof according to claim 62, wherein R 3 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Claim 85
Dependent Claim
33 words
A carbostyril derivative or an acid addition salt thereof according to claim 62, wherein R 3 is a hydroxy group, an alkanoyloxy group having 1 to 4 carbon atoms or a 3,4,5-trimethoxybenzoyloxy group.
Claim 86
Dependent Claim
34 words
A carbostyril derivative or an acid addition salt thereof according to claim 63, wherein the substituted position of the side chain represented by the formula, ##STR52## is 5- or 7-position in the carbostyril skeleton.
Claim 87
Dependent Claim
35 words
A carbostyril derivative or an acid addition salt thereof according to claim 63, wherein the substituted position of the side chain represented by the formula, ##STR53## is 4-, 6- or 8-position in the carbostyril skeleton.
Claim 88
Dependent Claim
32 words
A carbostyril derivative or an acid addition salt thereof according to claim 63, wherein the substituted position of the side chain represented by the formula, ##STR54## is 5-position in the carbostyril skeleton.
Claim 89
Dependent Claim
32 words
A carbostyril derivative or an acid addition salt thereof according to claim 63, wherein the substituted position of the side chain represented by the formula, ##STR55## is 7-position in the carbostyril skeleton.
Claim 90
Dependent Claim
33 words
A pharmaceutical composition usable as an antihistaminic agent, containing a suitable amount of the carbostyril derivative or acid addition salt thereof of claim 62 as an active ingredient and a pharmaceutically acceptable carrier.
Claim 91
Dependent Claim
1 words
7-[3-(4-Benzylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.
Claim 92
Dependent Claim
1 words
7-[3-(4-Benzylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.
Claim 93
Dependent Claim
1 words
7-[3-(4-Cyclohexylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.
Claim 94
Dependent Claim
1 words
7-[3-(4-Cyclohexylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.
Claim 95
Dependent Claim
1 words
5-[3-(4-Benzylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.
Claim 96
Dependent Claim
1 words
5-[3-(4-Benzylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.
Claim 97
Dependent Claim
1 words
5-[3-(4-Benzoylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.
Claim 98
Dependent Claim
1 words
5-[3-(4-Benzoylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.
Claim 99
Dependent Claim
34 words
The method of treating a human patient to produce a central nervous controlling effect which comprises administering to said patient an effective dosage of a compound or salt thereof as defined in claim 26.
Claim 100
Dependent Claim
35 words
The method of treating a human patient to produce a central nervous controlling effect which comprises orally administering to said patient an effective dosage of a compound or salt thereof as defined in claim 26.
Claim 101
Dependent Claim
35 words
The method of treating a human patient to produce a central nervous controlling effect which comprises intravenously administering to said patient an effective dosage of a compound or salt thereof as defined in claim 26.
Claim 102
Dependent Claim
25 words
A composition having an antihistaminic and a central nervous controlling effect comprising an effective amount of a compound or salt as defined in claim 26.
Claim 103
Dependent Claim
37 words
A method of treating a patient to produce a central nervous controlling effect or an antihistaminic effect comprising the step of administering to said patient an effective amount of a compound or salt according to claim 26.
Claim 104
Dependent Claim
33 words
A (4-substituted-piperazin-1-yl)alkoxy-2-oxo,1,2-dihydroquinoline or a salt thereof as claimed in claim 33, wherein R 4 is a hydrogen atom, a halogen atom, or an alkyl or alkoxy group having 1 to 3 carbon atoms.
Claim 105
Dependent Claim
25 words
A composition having an antihistaminic and a central nervous controlling effect comprising an effective amount of a compound or salt as defined in claim 79.
Claim 106
Dependent Claim
37 words
A method of treating a patient to produce a central nervous controlling effect or an antihistaminic effect comprising the step of administering to said patient an effective amount of a compound or salt according to claim 79.
Claim 107
Dependent Claim
25 words
A (4-substituted-piperazin-1-yl)alkoxy-2-oxo-1,2-dihydroquinoline or a salt thereof as claimed in claim 33, in which R 4 is a hydrogen atom, and A is a methylene radical.
Claim 108
Dependent Claim
27 words
A compound or salt thereof according to claim 82, in which R 1 is a hydrogen atom or an alkyl radical with 1 to 4 carbon atoms.
Claim 109
Dependent Claim
33 words
A compound or salt thereof according to claim 82, wherein such compound is ##STR56## in which R 3 is a hydrogen atom or a methyl radical, and R 4 is a hydrogen atom.
Claim 110
Dependent Claim
26 words
A compound or salt thereof according to claim 82 wherein such compound is ##STR57## in which R 3 is a hydrogen atom or a methyl radical.
Claim 111
Dependent Claim
26 words
A compound or salt thereof according to claim 82 wherein such compound is: ##STR58## in which R 3 is a hydrogen atom or a methyl radical.
Claim 112
Dependent Claim
26 words
A compound or salt thereof according to claim 82 wherein such compound is: ##STR59## in which R 3 is a hydrogen atom or a methyl radical.
Claim 113
Dependent Claim
25 words
A composition having an antihistaminic and a central nervous controlling effect comprising an effective amount of a compound or salt as defined in claim 82.
Claim 114
Dependent Claim
37 words
A method of treating a patient to produce a central nervous controlling effect or an antihistaminic effect comprising the step of administering to said patient an effective amount of a compound or salt according to claim 82.
Claim 115
Dependent Claim
30 words
The method according to claim 89, wherein said compound is: ##STR60## in which R 3 is a hydrogen atom or a methyl radical, and R 4 is a hydrogen atom.
Claim 116
Dependent Claim
18 words
A (4-substituted-piperazin-1-yl)alkoxy-2-oxo-1,2-dihydroquinoline or a salt thereof as claimed in claim 33, in which A is a valency bond.
Claim 117
Dependent Claim
25 words
A composition having an antihistaminic and a central nervous controlling effect comprising an effective amount of a compound or salt as defined in claim 91.
Claim 118
Dependent Claim
37 words
A method of treating a patient to produce a central nervous controlling effect or an antihistaminic effect comprising the step of administering to said patient an effective amount of a compound or salt according to claim 91.
Claim 119
Dependent Claim
66 words
The compound of claim 1, wherein R 1 , R 2 , R 3 and R 4 are hydrogen atoms; l and m are each 1; Q is 2; R 5 is a phenyl group containing 1 to 3 identical or different substituents selected from an alkyl group having 1 to 4 carbon atoms; and the side chain on the carbostyril skeleton is in the 7-position.
Claim 120
Dependent Claim
19 words
The compound of claim 94, wherein the R 5 substituted phenyl group contains two methyl groups as the substituents.
Claim 121
Dependent Claim
19 words
The compound of claim 94, wherein the R 5 substituted phenyl group contains one methyl group as the substituent.
Claim 122
Dependent Claim
9 words
The compound of claim 95, wherein n is 0.
Claim 123
Dependent Claim
9 words
The compound of claim 96, wherein n is 0.
Claim 124
Dependent Claim
9 words
An acid-addition salt of the compound of claim 94.
Claim 125
Dependent Claim
68 words
The compound of claim 1, wherein R 1 , R 2 , R 3 and R 4 are hydrogen atoms; l and m are each 1; n is 0; Q is 2; R 5 is a phenyl group containing one halogen atom; the side chain on the carbostyril skeleton is in the 7-position; and there is a single bond between the 3- and 4-positions in the carbostyril skeleton.
Claim 126
Dependent Claim
15 words
The compound of claim 100, wherein the R 5 halogen substituent is a chlorine atom.
Claim 127
Dependent Claim
15 words
The compound of claim 100, wherein the R 5 halogen substituent is a fluorine atom.
Claim 128
Dependent Claim
90 words
The compound of claim 1, wherein R 1 , R 2 , R 3 and R 4 are hydrogen; l and m are each 1; n is 0; Q is 2; R 5 is a phenyl group containing 1 to 3 identical or different substituents selected from the group consisting of a halogen atom and an alkyl group having 1 to 4 carbon atoms; the side chain on the carbostyril skeleton is in the 7-position and there is a single bond between the 3- and 4-positions in the carbostyril skeleton.
Claim 129
Dependent Claim
15 words
The compound of claim 103, wherein the R 5 substituted phenyl group is 4-chloro-3-methylphenyl group.
Claim 130
Dependent Claim
79 words
The compound of claim 1, wherein R 1 , R 2 , R 3 and R 4 are hydrogen atoms; l and m are each 1; Q is 2; n is 0; R 5 is a phenyl group containing 1 to 3 identical or different substituents selected from a halogen atom; the side chain on the carbostyril skeleton is in the 5-position; and the carbon-carbon bond between the 3- and 4-positions in the carbostyril skeleton is a single bond.
Claim 131
Dependent Claim
15 words
The compound of claim 105, wherein the R 5 halogen substituent is a fluorine atom.
Claim 132
Dependent Claim
1 words
7-{3-[4-(4-Chlorophenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 133
Dependent Claim
1 words
7-{3-[4-(4-Chlorophenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 134
Dependent Claim
1 words
7-{3-[4-(3,4-Dimethylphenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 135
Dependent Claim
1 words
7-{3-[4-(3,4-Dimethylphenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 136
Dependent Claim
1 words
5-{3-[4-(2-Fluorophenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 137
Dependent Claim
1 words
5-{3-[4-(2-Fluorophenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 138
Dependent Claim
22 words
The compound of claim 95, wherein the carbon-carbon bond at the 3- and 4-positions in the carbostyril skeleton is a double bond.
Claim 139
Dependent Claim
22 words
A phenylpiperazine compound in accordance with claim 25, wherein said compound is selected from the group consisting of 6-{3-[4-(4-methylphenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril, 6-{3-[4-(4-bromophenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril, and 1-methyl-6-{3-[4-(4-methylphenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 140
Dependent Claim
25 words
A compound in accordance with claim 33, wherein said compound is selected from the group consisting of, 5-[2-(4-phenylpiperazinyl)ethoxy]carbostyril, 7-[2-(4-phenylpiperazinyl)ethoxy]carbostyril, 8-[2-(4-phenylpiperazinyl)ethoxy]carbostyril, 5-[3-(4-phenylpiperazinyl)propoxy]carbostyril, 5-[4-(4-phenylpiperazinyl)propoxy]carbostyril, 7-[4-(4-phenylpiperazinyl)butoxy]carbostyril, 6-[5-(4-phenylpiperazinyl)pentyloxy]carbostyril, 8-[5-(4-phenylpiperazinyl)pentyloxy]carbostyril.
Claim 141
Dependent Claim
25 words
A compound in accordance with claim 33, wherein said compound is selected from the group consisting of, 1-methyl-5-[2-(4-phenylpiperazinyl)ethoxy]carbostyril, 1-methyl-6-[3-(4-phenylpiperazinyl)propoxy]carbostyril, 1-methyl-7-[3-(4-phenylpiperazinyl)propoxy]carbostyril, 1-hexyl-6-[3-(4-phenylpiperazinyl)propoxy]carbostyril, 1-methyl-5-{3-[4-(4-chlorophenyl)piperazinyl]propoxy}-carbostyril, 1-methyl-6-{3-[4-(4-methylphenyl)piperazinyl]propoxy}-carbostyril, and 1-methyl-7-{3-[4-(4-methoxyphenyl)piperazinyl]propoxy}-carbostyril.
Claim 142
Dependent Claim
33 words
A compound or salt thereof in accordance with claim 33, wherein said compound or salt is selected from the group consisting of, 5-{3-[4-(2-methoxyphenyl)piperazinyl]propoxy}carbostyril, 5-{3-[4-(3-methylphenyl)piperazinyl]propoxy}carbostyril, 6-{3-[4-(4-methylphenyl)piperazinyl]propoxy}carbostyril, 7-{2-[4-(4-propylphenyl)piperazinyl]ethoxy}carbostyril, 5-{3-[4-(4-chlorophenyl)piperazinyl]propoxy}carbostyril, 6-{3-[4-(4-bromophenyl)piperazinyl]propoxy}carbostyril, 7-{2-[4-(2-chlorophenyl)piperazinyl]ethoxy}carbostyril, 6-{3-[4-(2-methoxyphenyl)piperazinyl]propoxy}carbostyril.dihydrochloride, 8-{3-[4-(2-methoxyphenyl)piperazinyl]propoxy}carbostyril.dihydrochloride, and 7-{3-[4-(3-chlorophenyl)piperazinyl]propoxy}carbostyril.
Claim 143
Dependent Claim
24 words
A carbostyril derivative in accordance with claim 42, wherein said compound is selected from the group consisting of, 4-methyl-7-[3-(4-phenylpiperazinyl)propoxy]-3,4-dihydro-carbostyril 4-phenyl-7-[3-(4-phenylpiperazinyl)propoxy]carbostyril, 4-phenyl-7-[3-(4-phenylpiperazinyl)propoxy]-3,4-dihydro-carbostyril, 4-phenyl-7-{3-[4-(2-methoxyphenyl)piperazinyl]propoxy}-carbostyril, and 4-methyl-7-[3-(4-phenylpiperazinyl)propoxy]carbostyril.
Claim 144
Dependent Claim
26 words
The method of claim 50, wherein the carbostyril derivative is selected from the group consisting of: 7-[3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostryril, 7-[3-(4-phenylpiperazinyl)propoxy]carbostyril, 1-Methyl-7-[3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril, 7-[4-(4-phenylpiperazinyl)butoxy]-3,4-dihydrocarbostyril, 5-[3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril, 6-[3-(4-phenylpiperazinyl)propoxy]carbostyril, 8-bromo-5-[3-(4-phenylpiperazinyl]propoxy]carbostyril, 7-[3-(4-benzylpiperazinyl)propoxy]-3,4-dihydrocarbostyril, and 1-benzyl-5-[3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.
Claim 145
Dependent Claim
24 words
The method of claim 50, wherein the carbostyril derivative is selected from the group consisting of: 7-{3-[4-(2-methoxyphenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril, 7-{3-[4-(3-chlorophenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril, 7-{3-[4-(2-fluorophenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril, 7-{3-[4-(2-ethyoxyphenyl)piperazinyl]propoxy}-3,4-hydrocarbostyril, 7-{3-[4-(2-chlorophenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril, 7-{3-[4-(2-methoxyphenyl)piperazinyl]propoxy}carbostyril and 7-{3-[4-(4-methylphenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril.
Claim 146
Dependent Claim
19 words
The method of claim 50, wherein the carbostyril derivative is selected from the group consisting of: 7-[2-hydroxy-3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril, and 1-benzyl-5-[2-hydroxy-3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.
References Cited (Backward Citations)
CA801037A
Cited
FR1561911A
Cited
GB1075156A
Cited
GB1111785A
Cited
US3362956A
Cited
US3703522A
Cited
US3706749A
Cited
US3511841A
Cited
US4060526A
Cited
DE1932384A1
Cited
GB1212174A
Cited
US3654277A
Cited
US3810898A
Cited
US3810896A
Cited
FR2179715A1
Cited
US3910924A
Cited
US4256890A
Cited
DE2354145A1
Cited
US3919226A
Cited
US3932411A
Cited
US3981864A
Cited
US4117228A
Cited
US4026895A
Cited
GB1451900A
Cited
US3936459A
Cited
US4032528A
Cited
US3983121A
Cited
US3940397A
Cited
DE2631317A1
Cited
US3994900A
Cited
DE2706752A1
Cited
GB1572920A
Cited
FR2344538A1
Cited
US4210753A
Cited
US4147869A
Cited
US4110449A
Cited
US4166116A
Cited
EP0005828A1
Cited
US4234584A
Cited
US4234585A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-03-29 | 1991-09-28 | 1992-03-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-03-29 | 1995-09-28 | 1996-03-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-03-29 | 1999-09-28 | 2000-03-29 | $7700.00 | Window Closed / Lapsed |