US4436748A
Expired / Lapsed
US
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Benzo[b]thiophenes
Assignee: Aventis Pharmaceuticals Inc
•
Filing: 1981-04-22
•
Granted: 1984-03-13
•
Expires: 2001-04-22
Abstract
Abstract Novel benzo[b]thiophenes, compositions containing same, process for the preparation thereof and methods of reducing blood pressure and producing diuresis by administration of the compounds and compositions are disclosed.
Inventors
- 👤 Helen H. Ong
- 👤 James A. Profitt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 12:12
CPC Classifications
C; C07; C07D; C07D333/00; C07D333/50; C07D333/52; C07D333/54; A; A61; A61P; A61P7/00; A61P7/10; A61P9/00; A61P9/12; C07C; C07C309/00; C07C323/00; C07C45/00; C07C45/61; C07C45/63; C07C49/00; C07C49/76; C07C49/80; C07D333/56; C07D333/62; C07D333/64; C07D333/76
Claims Analysis
Total Claims: 114
Claim 1
Independent Claim
153 words
A compound of the formula wherein R 1 is lower alkanoyl, formyl or a group of the formula ##STR31## wherein R 19 and R 20 are each independently hydrogen or lower alkyl; R 1 and R 2 are hydrogen, lower alkyl, lower cycloalkyl, or a group of the formula ##STR32## wherein Y is hydrogen, halogen, lower alkyl, lower alkoxy or hydroxy and p is 1 or 2, with the proviso that R 1 and R 2 are not simultaneously hydrogen; R 3 is Z wherein Z is a group of the formula ##STR33## wherein R 4 and R 5 are hydrogen or lower alkyl; R 6 is carboxy, hydroxymethyl, lower alkoxycarbonyl, or hydroxyaminocarbonyl; X is halogen; n is 2 and m is 0, 1 or 2; and the O-R 3 substituent is attached to the 5-position of the benzo[b]thiophene nucleus, or a pharmaceutically acceptable basic addition salt thereof when R 6 is carboxy.
Claim 2
Dependent Claim
153 words
A compound of the formula wherein R 1 is lower alkanoyl, formyl or a group of the formula ##STR31## wherein R 19 and R 20 are each independently hydrogen or lower alkyl; R 1 and R 2 are hydrogen, lower alkyl, lower cycloalkyl, or a group of the formula ##STR32## wherein Y is hydrogen, halogen, lower alkyl, lower alkoxy or hydroxy and p is 1 or 2, with the proviso that R 1 and R 2 are not simultaneously hydrogen; R 3 is Z wherein Z is a group of the formula ##STR33## wherein R 4 and R 5 are hydrogen or lower alkyl; R 6 is carboxy, hydroxymethyl, lower alkoxycarbonyl, or hydroxyaminocarbonyl; X is halogen; n is 2 and m is 0, 1 or 2; and the O-R 3 substituent is attached to the 5-position of the benzo[b]thiophene nucleus, or a pharmaceutically acceptable basic addition salt thereof when R 6 is carboxy.
Claim 3
Dependent Claim
35 words
The compound of claim 1 wherein Z is a group of the formula ##STR34## wherein R 4 and R 5 are hydrogen; R 6 is carboxy or lower alkoxycarbonyl; and m is 0 or 2.
Claim 4
Dependent Claim
16 words
The compound of claim 2 wherein R 1 and R 2 are hydrogen or lower alkyl.
Claim 5
Dependent Claim
9 words
The compound of claim 2 which is [(6,7-dichloro-3-phenylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 6
Dependent Claim
9 words
The compound of claim 3 which is ethyl [(6,7-dichloro-2-ethylbenzo[b]thien-5-yl)oxy]acetate.
Claim 7
Dependent Claim
9 words
The compound of claim 3 which is [(6,7-dichloro-2-ethylbenzo-[b]thien-5-yl)oxy]acetic acid.
Claim 8
Dependent Claim
9 words
The compound of claim 2 which is ethyl [(6,7-dichloro-3-(4-chlorophenyl)benzo[b]thien-5-yl)oxy]acetate.
Claim 9
Dependent Claim
9 words
The compound of claim 2 which is [(6,7-dichloro-3-(4-chlorophenyl)-benzo[b]thien-5-yl)oxy]acetic acid.
Claim 10
Dependent Claim
10 words
The compound of claim 2 which is ethyl [(6,7-dichloro-3-(4-chlorophenyl)benzo[b]thien-5-yl)oxy]acetate 1,1-dioxide.
Claim 11
Dependent Claim
9 words
The compound of claim 3 which is ethyl [(6,7-dichloro-3-methylbenzo[b]thien-5-yl)oxy]acetate.
Claim 12
Dependent Claim
9 words
The compound of claim 3 which is [(6,7-dichloro-3-methylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 13
Dependent Claim
9 words
The compound of claim 2 which is ethyl [(6,7-dichloro-3-methyl-2-phenylbenzo[b]thien-5-yl)oxy]acetate.
Claim 14
Dependent Claim
9 words
The compound of claim 2 which is [(6,7-dichloro-3-methyl-2-phenylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 15
Dependent Claim
9 words
The compound of claim 3 which is ethyl [(6,7-dichloro-2-isopropylbenzo[b]thien-5-yl)oxy]acetate.
Claim 16
Dependent Claim
9 words
The compound of claim 3 which is ethyl [(6,7-dichloro-2-methylbenzo[b]thien-5-yl)oxy]acetate.
Claim 17
Dependent Claim
9 words
The compound of claim 3 which is [(6,7-dichloro-2-methylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 18
Dependent Claim
9 words
The compound of claim 3 which is [(6,7-dichloro-2-isopropylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 19
Dependent Claim
9 words
The compound of claim 2 which is ethyl [(6,7-dichloro-2-phenylbenzo[b]thien-5-yl)]acetate.
Claim 20
Dependent Claim
9 words
The compound of claim 2 which is [(6,7-dichloro-2-phenylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 21
Dependent Claim
10 words
The compound of claim 3 which is [6,7-dichloro-2-methylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 22
Dependent Claim
10 words
The compound of claim 2 which is [6,7-dichloro-3-methyl-2-phenylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 23
Dependent Claim
9 words
The compound of claim 2 which is {[6,7-dichloro-2-(2'-fluorophenyl)benzo[b]thien-5-yl]oxy}acetic acid.
Claim 24
Dependent Claim
10 words
The compound of claim 3 which is [(6,7-dichloro-2-isopropylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 25
Dependent Claim
9 words
The compound of claim 2 which is ethyl [(6,7-dichloro-2-(2'-fluorophenyl)benzo[b]thien-5-yl)oxy]acetate.
Claim 26
Dependent Claim
9 words
The compound of claim 2 which is [(6,7-dichloro-2-(2'-fluorophenyl)benzo[b]thien-5-yl)oxy]acetic acid.
Claim 27
Dependent Claim
9 words
The compound of claim 2 which is ethyl [(6,7-dichloro-2-cyclopentylbenzo[b]thien-5-yl)oxy]acetate.
Claim 28
Dependent Claim
9 words
The compound of claim 2 which is [(6,7-dichloro-2-cyclopentylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 29
Dependent Claim
8 words
The compound of claim 1 which is 2-acetyl-6,7-dichloro-5-methoxybenzo[b]thiophene.
Claim 30
Dependent Claim
9 words
The compound of claim 2 which is ethyl [(6,7-dichloro-2-acetylbenzo[b]thien-5-yl)oxy]acetate.
Claim 31
Dependent Claim
9 words
The compound of claim 2 which is ethyl [(6,7-dichloro-2-hydroxymethylbenzo]b]thien-5-yl)oxy]acetate.
Claim 32
Dependent Claim
9 words
The compound of claim 2 which is [(6,7-dichloro-2-hydroxymethylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 33
Dependent Claim
9 words
The compound of claim 2 which is [(2-acetyl-6,7-dichlorobenzo[b]thien-5-yl)oxy]acetic acid.
Claim 34
Dependent Claim
8 words
The compound of claim 1 which is 6,7-dichloro-5-hydroxy-α,α-dimethylbenzo[b]thiophene-2-methanol.
Claim 35
Dependent Claim
9 words
The compound of claim 2 which is t-butyl [(6,7-dichloro-2-(1-hydroxy-1-methylethyl)benzo[b]thien-5-yl)oxy]acetate.
Claim 36
Dependent Claim
9 words
The compound of claim 2 which is [(6,7-dichloro-2-(1-hydroxy-1-methylethylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 37
Dependent Claim
9 words
The compound of claim 2 which is ethyl [(6,7-dichloro-2-(1-hydroxypropyl)benzo[b]thien-5-yloxy]acetate.
Claim 38
Dependent Claim
9 words
The compound of claim 2 which is [(6,7-dichloro-2-(1-hydroxypropyl)benzo[b]thien-5-yl)oxy]acetic acid.
Claim 39
Dependent Claim
9 words
The compound of claim 2 which is ethyl [(2-n-butyl-6,7-dichlorobenzo[b]thien-5-yl)oxy]acetate.
Claim 40
Dependent Claim
9 words
The compound of claim 2 which is [(2-n-butyl-6,7-dichlorobenzo[b]thien-5-yl)oxy]acetic acid.
Claim 41
Dependent Claim
11 words
The compound of claim 1 which is [(2-n-butyl-6,7-dichlorobenzo[b]thien-5-yl)oxy]acetic acid 1,1 dioxide.
Claim 42
Dependent Claim
9 words
The compound of claim 2 which is ethyl [(6,7-dichloro-2-cyclohexylbenzo[b]thien-5-yl)oxy]acetate.
Claim 43
Dependent Claim
9 words
The compound of claim 2 which is [(6,7-dichloro-2-cyclohexylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 44
Dependent Claim
10 words
The compound of claim 2 which is [(6,7-dichloro-2-cyclohexylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 45
Dependent Claim
10 words
The compound of claim 2 which is [(6,7-dichloro-2-cyclopentylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 46
Dependent Claim
10 words
The compound of claim 2 which is [(6,7-dichloro-2-phenylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 47
Dependent Claim
9 words
The compound of claim 2 which is ethyl [(6,7-dichloro-2-(2'-methylphenyl)benzo[b]thien-5-yl)oxy]acetate.
Claim 48
Dependent Claim
9 words
The compound of claim 2 which is [(6,7-dichloro-2-(2'-methylphenyl)benzo[b]thiophene-5-yl)oxy]acetic acid.
Claim 49
Dependent Claim
10 words
The compound of claim 2 which is [(6,7-dichloro-2-(2'-methylphenyl)benzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 50
Dependent Claim
10 words
The compound of claim 3 which is [(6,7-dichloro-2-ethylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 51
Dependent Claim
9 words
The compound of claim 2 which is ethyl [6,7-dichloro-2-(2'-chlorophenyl)benzo[b]thien-5-yl)oxy]acetate.
Claim 52
Dependent Claim
9 words
The compound of claim 2 which is [6,7-dichloro-2-(2'-chlorophenyl)benzo[b]thien-5-yl)oxy]acetic acid.
Claim 53
Dependent Claim
10 words
The compound of claim 2 which is [(6,7-dichloro-2-(2'-chlorophenyl)benzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 54
Dependent Claim
9 words
The compound of claim 3 which is ethyl [(6,7-dichloro-2,3-dimethylbenzo[b]thien-5-yl)oxy]acetate.
Claim 55
Dependent Claim
9 words
The compound of claim 3 which is [(6,7-dichloro-2,3-dimethylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 56
Dependent Claim
10 words
The compound of claim 1 which is [(6,7-dichloro-2,3-dimethylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 57
Dependent Claim
9 words
The compound of claim 2 which is ethyl [(6,7-dichloro-2-(2',6'-difluorophenyl)benzo[b]thien-5-yl)oxy]acetate.
Claim 58
Dependent Claim
9 words
The compound of claim 2 which is [(6,7-dichloro-2-(2',6'-difluorophenyl)benzo[b]thien-5-yl)oxy]acetic acid.
Claim 59
Dependent Claim
10 words
The compound of claim 2 which is [(6,7-dichloro-2-(2',6'-difluorophenyl)benzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 60
Dependent Claim
9 words
The compound of claim 1 which is ethyl [(6,7-dichloro-2-n-propylbenzo[b]thien-5-yl)oxy]acetate.
Claim 61
Dependent Claim
9 words
The compound of claim 2 which is [(6,7-dichloro-2-n-propylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 62
Dependent Claim
10 words
The compound of claim 1 which is [(6,7-dichloro-2-n-propylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 63
Dependent Claim
9 words
The compound of claim 2 which is ethyl [(6,7-dichloro-2-(1-hydroxyethyl)benzo[b]thien-5-yl)oxy]acetate.
Claim 64
Dependent Claim
9 words
The compound of claim 2 which is [(6,7-dichloro-2-(1-hydroxyethyl)benzo[b]thien-5-yl)oxy]acetic acid.
Claim 65
Dependent Claim
9 words
The compound of claim 2 which is 6,7-dichloro-[2-(1-oxopropyl)-benzo[b]thien-5-yl)oxy]acetic acid.
Claim 66
Dependent Claim
9 words
The compound of claim 3 which is ethyl [(6,7-dichloro-2-isobutylbenzo[b]thien-5-yl)oxy]acetate.
Claim 67
Dependent Claim
9 words
The compound of claim 3 which is [(6,7-dichloro-2-isobutylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 68
Dependent Claim
10 words
The compound of claim 3 which is [(6,7-dichloro-2-isobutylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dixode.
Claim 69
Dependent Claim
187 words
A diuresis producing or blood pressure reducing composition comprising an inert diuresis producing or blood pressure reducing adjuvant and as the active ingredient, an amount effective in producing diuresis or reducing blood pressure of a compound of the formula ##STR35## wherein R 1 is lower alkanoyl, formyl or a group of the formula ##STR36## wherein R 19 and R 20 are each independently hydrogen or lower alkyl; wherein R 1 and R 2 are hydrogen, lower alkyl, lower cycloalkyl or a group of the formula ##STR37## wherein Y is hydrogen, halogen, lower alkyl, alkoxy or hydroxy and p is 1 or 2, with the proviso that R 1 and R 2 are not simultaneously hydrogen; R 3 is Z wherein Z is a group of the formula ##STR38## wherein R 4 and R 5 are hydrogen or lower alkyl; R 6 is carboxy, hydroxymethyl, lower alkoxycarbonyl or hydroxyaminocarbonyl; X is halogen; n is 2; m is 0, 1 or 2; and the O-R 3 substituent is attached to the 5-position of the benzo[b]thiophene nucleus or a pharmaceutically acceptable basic addition salt thereof when R 6 is carboxy.
Claim 70
Dependent Claim
187 words
A diuresis producing or blood pressure reducing composition comprising an inert diuresis producing or blood pressure reducing adjuvant and as the active ingredient, an amount effective in producing diuresis or reducing blood pressure of a compound of the formula ##STR35## wherein R 1 is lower alkanoyl, formyl or a group of the formula ##STR36## wherein R 19 and R 20 are each independently hydrogen or lower alkyl; wherein R 1 and R 2 are hydrogen, lower alkyl, lower cycloalkyl or a group of the formula ##STR37## wherein Y is hydrogen, halogen, lower alkyl, alkoxy or hydroxy and p is 1 or 2, with the proviso that R 1 and R 2 are not simultaneously hydrogen; R 3 is Z wherein Z is a group of the formula ##STR38## wherein R 4 and R 5 are hydrogen or lower alkyl; R 6 is carboxy, hydroxymethyl, lower alkoxycarbonyl or hydroxyaminocarbonyl; X is halogen; n is 2; m is 0, 1 or 2; and the O-R 3 substituent is attached to the 5-position of the benzo[b]thiophene nucleus or a pharmaceutically acceptable basic addition salt thereof when R 6 is carboxy.
Claim 71
Dependent Claim
28 words
The composition of claim 68 wherein Z is a group of the formula ##STR39## wherein R 6 is carboxy or lower alkoxycarbonyl; and m is 0 or 2.
Claim 72
Dependent Claim
16 words
The composition of claim 69 wherein R 1 and R 2 are hydrogen or lower alkyl.
Claim 73
Dependent Claim
12 words
The composition of claim 70 wherein the active ingredient is [(6,7-dichloro-2-methylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 74
Dependent Claim
12 words
The composition of claim 70 wherein the active ingredient is [(6,7-dichloro-2-ethylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 75
Dependent Claim
12 words
The composition of claim 70 wherein the active ingredient is ethyl [(6,7-dichloro-2-methylbenzo[b]thien-5-yl)oxy]acetate.
Claim 76
Dependent Claim
12 words
The composition of claim 70 wherein the active ingredient is ethyl [(6,7-dichloro-2-isopropylbenzo[b]thien-5-yl)oxy]acetate.
Claim 77
Dependent Claim
12 words
The composition of claim 69 wherein the active ingredient is [(6,7-dichloro-3-methyl-2-phenylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 78
Dependent Claim
12 words
The composition of claim 70 wherein the compound is [(2-n-butyl-6-7-dichlorobenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 79
Dependent Claim
12 words
The composition of claim 70 wherein the compound is [(6,7-dichloro-2-ethylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 80
Dependent Claim
12 words
The composition of claim 70 wherein the compound is [(6,7-dichloro-2,3-dimethylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 81
Dependent Claim
12 words
The composition of claim 70 wherein the compound is [(6,7-dichloro-2-n-propylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 82
Dependent Claim
12 words
The composition of claim 70 wherein the compound is [(6,7-dichloro-2-isobutylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 83
Independent Claim
171 words
A method of reducing blood pressure in mammals comprising administering to a mammal requiring blood pressure reduction a blood pressure reducing effective amount of a compound of the formula ##STR40## wherein R 1 is lower alkanoyl, formyl or a group of the formula ##STR41## wherein R 19 and R 20 are each independently hydrogen or lower alkyl; wherein R 1 and R 2 are hydrogen, lower alkyl, lower cycloalkyl or a group of the formula ##STR42## wherein Y is hydrogen, halogen, lower alkyl, alkoxy or hydroxy and p is 1 or 2 with the proviso that R 1 and R 2 are not simultaneously hydrogen; R 3 is Z wherein Z is lower alkyl or a group of the formula ##STR43## wherein R 4 and R 5 are hydrogen or lower alkyl; R 6 is carboxy, hydroxymethyl, lower alkoxycarbonyl, or hydroxyaminocarbonyl; X halogen or lower alkyl, n is 1 or 2 and m is 0, 1 or 2, or a pharmaceutically acceptable basic addition salt thereof when R 6 is carboxy.
Claim 84
Independent Claim
171 words
A method of reducing blood pressure in mammals comprising administering to a mammal requiring blood pressure reduction a blood pressure reducing effective amount of a compound of the formula ##STR40## wherein R 1 is lower alkanoyl, formyl or a group of the formula ##STR41## wherein R 19 and R 20 are each independently hydrogen or lower alkyl; wherein R 1 and R 2 are hydrogen, lower alkyl, lower cycloalkyl or a group of the formula ##STR42## wherein Y is hydrogen, halogen, lower alkyl, alkoxy or hydroxy and p is 1 or 2 with the proviso that R 1 and R 2 are not simultaneously hydrogen; R 3 is Z wherein Z is lower alkyl or a group of the formula ##STR43## wherein R 4 and R 5 are hydrogen or lower alkyl; R 6 is carboxy, hydroxymethyl, lower alkoxycarbonyl, or hydroxyaminocarbonyl; X halogen or lower alkyl, n is 1 or 2 and m is 0, 1 or 2, or a pharmaceutically acceptable basic addition salt thereof when R 6 is carboxy.
Claim 85
Dependent Claim
46 words
The method of claim 81 wherein Z is a group of the formula ##STR44## wherein R 6 is carboxy or lower alkoxycarbonyl; X is halogen; m is 0 or 2; n is 2 and the O-R 3 substituent is attached to the 5-position of the benzo[b]thiophene.
Claim 86
Dependent Claim
15 words
The method of claim 82 wherein R 1 and R 2 are hydrogen or loweralkyl.
Claim 87
Dependent Claim
11 words
The method of claim 83 wherein the compound is [(6,7-dichloro-2-methylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 88
Dependent Claim
11 words
The method of claim 83 wherein the compound is [(6,7-dichloro-2-ethylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 89
Dependent Claim
11 words
The method of claim 83 wherein the compound is ethyl [(6,7-dichloro-2-methylbenzo[b]thien-5-yl)oxy]acetate.
Claim 90
Dependent Claim
11 words
The method of claim 83 wherein the compound is [(6,7-dichloro-2-isopropylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 91
Dependent Claim
11 words
The method of claim 83 wherein the compound is ethyl [(6,7-dichloro-2-isopropylbenzo[b]thien-5-yl)oxy]acetate.
Claim 92
Dependent Claim
11 words
The method of claim 82 wherein the compound is [(6,7-dichloro-3-methyl-2-phenylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 93
Dependent Claim
11 words
The method of claim 83 wherein the compound is [(2-n-butyl-6,7-dichlorobenzo[b]thien-5-yl)oxy]acetic acid.
Claim 94
Dependent Claim
12 words
The method of claim 82 wherein the compound is [(6,7-dichloro-2-cyclohexylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 95
Dependent Claim
12 words
The method of claim 82 wherein the compound is [(6,7-dichloro-2-cyclopentyllbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 96
Dependent Claim
12 words
The method of claim 83 wherein the compound is [(6,7-dichloro-2-ethylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 97
Dependent Claim
12 words
The method of claim 83 wherein the compound is [(6,7-dichloro-2,3-dimethylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 98
Dependent Claim
12 words
The method of claim 83 wherein the compound is [(6,7-dichloro-2-n-propylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 99
Dependent Claim
12 words
The method of claim 83 wherein the compound is [(6,7-dichloro-2-ixobutylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 100
Independent Claim
152 words
A method of producing diuresis in mammals comprising administering to a mammal requiring diuresis a diuretically effective amount of a compound of the formula ##STR45## wherein R 1 is lower alkanoyl, formyl or a group of the formula ##STR46## wherein R 1 and R 2 are hydrogen, lower alkyl, lower cycloalkyl or a group of the formula ##STR47## wherein Y is hydrogen, halogen, lower alkyl, alkoxy or hydroxy and p is 1 or 2, with the proviso that R 1 and R 2 are not simultaneously hydrogen; R 3 is Z wherein Z is lower a group of the formula ##STR48## wherein R 4 and R 5 are hydrogen or lower alkyl; R 6 is carboxy, hydroxymethyl, lower alkylcarbonyl or hydroxyaminocarbonyl; X is halogen or lower alkyl, n is 1 or 2 and m is 0, 1 or 2; or a pharmaceutically acceptable basic addition salt thereof when R 6 is carboxy.
Claim 101
Independent Claim
152 words
A method of producing diuresis in mammals comprising administering to a mammal requiring diuresis a diuretically effective amount of a compound of the formula ##STR45## wherein R 1 is lower alkanoyl, formyl or a group of the formula ##STR46## wherein R 1 and R 2 are hydrogen, lower alkyl, lower cycloalkyl or a group of the formula ##STR47## wherein Y is hydrogen, halogen, lower alkyl, alkoxy or hydroxy and p is 1 or 2, with the proviso that R 1 and R 2 are not simultaneously hydrogen; R 3 is Z wherein Z is lower a group of the formula ##STR48## wherein R 4 and R 5 are hydrogen or lower alkyl; R 6 is carboxy, hydroxymethyl, lower alkylcarbonyl or hydroxyaminocarbonyl; X is halogen or lower alkyl, n is 1 or 2 and m is 0, 1 or 2; or a pharmaceutically acceptable basic addition salt thereof when R 6 is carboxy.
Claim 102
Dependent Claim
46 words
The method of claim 97 wherein Z is a group of the formula ##STR49## wherein R 6 is carboxy or lower alkoxycarbonyl; X is halogen, m is 0 or 2; n is 2 and the O-R 3 substituent is attached to the 5-position of the benzo[b]thiophene.
Claim 103
Dependent Claim
16 words
The method of claim 98 wherein R 1 and R 2 are hydrogen or lower alkyl.
Claim 104
Dependent Claim
11 words
The method of claim 99 wherein the compound is [(6,7-dichloro-2-methylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 105
Dependent Claim
11 words
The method of claim 99 wherein the compound is [(6,7-dichloro-2-ethylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 106
Dependent Claim
11 words
The method of claim 99 wherein the compound is ethyl [(6,7-dichloro-2-methylbenzo[b]thien-5-yl)oxy]acetate.
Claim 107
Dependent Claim
11 words
The method of claim 99 wherein the compound is ethyl [(6,7-dichloro-2-isopropylbenzo[b]thien-5-yl)oxy]acetate.
Claim 108
Dependent Claim
11 words
The method of claim 98 wherein the compound is [(6,7-dichloro-3-methyl-2-phenylbenzo[b]thien-5-yl)oxy]acetic acid.
Claim 109
Dependent Claim
12 words
The method of claim 99 wherein the compound is [(2-n-butyl-6,7-dichlorobenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 110
Dependent Claim
12 words
The method of claim 98 wherein the compound is [(6,7-dichloro-2-cyclohexylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 111
Dependent Claim
12 words
The method of claim 99 wherein the compound is [(6,7-dichloro-2-ethylbenzo[b]thien-5-yl)]acetic acid 1,1-dioxide.
Claim 112
Dependent Claim
12 words
The method of claim 99 wherein the compound is [(6,7-dichloro-2,3-dimethylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 113
Dependent Claim
12 words
The method of claim 99 wherein the compound is [(6,7-dichloro-2-n-propylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
Claim 114
Dependent Claim
12 words
The method of claim 99 wherein the compound is [(6,7-dichloro-2-isobutylbenzo[b]thien-5-yl)oxy]acetic acid 1,1-dioxide.
References Cited (Backward Citations)
US2645572A
Cited
CH416206A
Cited
US3288808A
Cited
GB1138163A
Cited
US3636050A
Cited
US3480671A
Cited
US3784602A
Cited
US3836542A
Cited
US3953601A
Cited
US4075227A
Cited
DE2909754A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-03-13 | 1987-09-12 | 1988-03-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-03-13 | 1991-09-12 | 1992-03-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-03-13 | 1995-09-12 | 1996-03-13 | $7700.00 | Window Closed / Lapsed |