US4191694A
Expired / Lapsed
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Prostaglandin-I2 derivatives
Assignee: Bayer Pharma AG
•
Filing: 1978-07-26
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Granted: 1980-03-04
•
Expires: 1998-07-26
Abstract
Abstract Prostane derivatives of the formula ##STR1## wherein R 1 is OR 2 or NHR 3 ; R 2 is hydrogen, C 1-10 alkyl, C 4-10 cycloalkyl, C 6-10 aryl, or a 5 or 6 membered heterocyclic ring having 1-3 hetero atoms selected from O, N and S; R 3 is the residue of a hydrocarbon carboxylic or sulfonic acid of 1-15 carbon atoms; W is (a) an OH-substituted methylene group, (b) a ##STR2## wherein the OH-groups in (a) or (b) can be in the α- or β-position, or (c) such a group wherein the H atom of the OH group is replaced by the residue of a hydrocarbon carboxylic or sulfonic acid of 1-15 carbon atoms or by a conventional etherifying OH-blocking group; R 4 is OH or hydroxy whose H atom is replaced as defined for W; and R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 each independently is hydrogen or alkyl of 1-5 carbon atoms; or R 9 and R 10 together represent a direct bond; and, when R 11 is alkyl, R 10 can also be chlorine; and, for a derivative wherein R 2 is hydrogen, the salts thereof with physiologically compatible bases, have improved prostaglandin activity.
Inventors
- 👤 Werner Skuballa
- 👤 Bernd Raduchel
- 👤 Norbert Schwarz
- 👤 Helmut Vorbruggen
- 👤 Bernd Muller
- 👤 Gerda Mannesmann
- 👤 Olaf Loge
- 👤 Ekkehardt Schillinger
- 👤 Jorge Casals-Stenzel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 23:11
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/77; C07D307/93; C07D307/935; C07D307/937; A; A61; A61P; A61P43/00; A61P7/00; A61P7/02; A61P7/10; A61P9/00; A61P9/06; A61P9/12; C07C; C07C405/00
Claims Analysis
Total Claims: 61
Claim 1
Independent Claim
310 words
A prostane derivative of the formula ##STR12## wherein R 1 is OR 2 or NHR 3 ; R 2 is hydrogen; C 1-10 alkyl; C 1-10 alkyl substituted by 1-3 of (a) halogen, (b) C 1-4 alkoxy, (c) C 6-10 aryl, (d) C 6-10 aryl substituted by 1-3 halogen atoms, phenyl, 1-3 C 1-4 alkyl groups, chloromethyl, fluoromethyl, trifluoromethyl, carboxyl, hydroxy or C 1-4 alkoxy, (e) di-C 1-4 -alkyl amino or (f) tri-C 1-4 -alkyl ammonium; C 4-10 cycloalkyl; C 4-10 cycloalkyl substituted by C 1-4 alkyl, the total number of C-atoms being 4-10; C 6-10 aryl; C 6-10 aryl substituted by 1-3 halogen atoms, phenyl, 1-3 C 1-4 alkyl groups, chloromethyl, fluoromethyl, trifluoromethyl, carboxyl, hydroxy or C 1-4 alkoxy; or a 5 or 6 membered heterocyclic ring having one hetero atom selected from O, N and S; R 3 is the acyl residue of a hydrocarbon carboxylic or sulfonic acid of 1-15 carbon atoms; W is (a) an OH-substituted methylene group, (b) a ##STR13## wherein the OH-groups in (a) or (b) can be in the α- or β-position, or (c) such a group wherein the H atom of the OH group is replaced by the acyl residue of a hydrocarbon carboxylic or sulfonic acid of 1-15 carbon atoms or by a conventional etherifying OH-blocking group selected from tetrahydropyranyl, tetrahydrofuranyl, α-ethoxyethyl, trimethylsilyl, dimethyl-tert-butylsilyl and tri-p-benzylsilyl; R 4 is OH or hydroxy whose H atom is replaced as defined for W; and R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 each independently is hydrogen or alkyl of 1-5 carbon atoms; or R 9 and R 10 together represent a direct bond; and when R 11 is alkyl, R 10 can also be chlorine; and for a derivative wherein R 2 is hydrogen, the salts thereof with physiologically compatible bases.
Claim 2
Dependent Claim
310 words
A prostane derivative of the formula ##STR12## wherein R 1 is OR 2 or NHR 3 ; R 2 is hydrogen; C 1-10 alkyl; C 1-10 alkyl substituted by 1-3 of (a) halogen, (b) C 1-4 alkoxy, (c) C 6-10 aryl, (d) C 6-10 aryl substituted by 1-3 halogen atoms, phenyl, 1-3 C 1-4 alkyl groups, chloromethyl, fluoromethyl, trifluoromethyl, carboxyl, hydroxy or C 1-4 alkoxy, (e) di-C 1-4 -alkyl amino or (f) tri-C 1-4 -alkyl ammonium; C 4-10 cycloalkyl; C 4-10 cycloalkyl substituted by C 1-4 alkyl, the total number of C-atoms being 4-10; C 6-10 aryl; C 6-10 aryl substituted by 1-3 halogen atoms, phenyl, 1-3 C 1-4 alkyl groups, chloromethyl, fluoromethyl, trifluoromethyl, carboxyl, hydroxy or C 1-4 alkoxy; or a 5 or 6 membered heterocyclic ring having one hetero atom selected from O, N and S; R 3 is the acyl residue of a hydrocarbon carboxylic or sulfonic acid of 1-15 carbon atoms; W is (a) an OH-substituted methylene group, (b) a ##STR13## wherein the OH-groups in (a) or (b) can be in the α- or β-position, or (c) such a group wherein the H atom of the OH group is replaced by the acyl residue of a hydrocarbon carboxylic or sulfonic acid of 1-15 carbon atoms or by a conventional etherifying OH-blocking group selected from tetrahydropyranyl, tetrahydrofuranyl, α-ethoxyethyl, trimethylsilyl, dimethyl-tert-butylsilyl and tri-p-benzylsilyl; R 4 is OH or hydroxy whose H atom is replaced as defined for W; and R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 each independently is hydrogen or alkyl of 1-5 carbon atoms; or R 9 and R 10 together represent a direct bond; and when R 11 is alkyl, R 10 can also be chlorine; and for a derivative wherein R 2 is hydrogen, the salts thereof with physiologically compatible bases.
Claim 3
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-7-Acetoxy-6-[(E)-(3S)-3-hydroxy-1-octen-6-ynyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 4
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-3-(4-Carboxy-1-butyl)-7-hydroxy-6-[(E)-(3S)-3-hydroxy-1-octen-6-ynyl]-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 5
Dependent Claim
6 words
(1S,5R,6R,7R,3S)-7-Acetoxy-6-[(E)-(3S)-3-hydroxy-1-octen-6-ynyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 6
Dependent Claim
6 words
(1S,5R,6R,7R,3S)-3-(4-Carboxy-1-butyl)-7-hydroxy-6-[(E)-(3S)-3-hydroxy-1-octen-6-ynyl]-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 7
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-7-Acetoxy-6-[(1E)-(3S)-3-hydroxy-7-methyl-1,6-octadienyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 8
Dependent Claim
6 words
(1S,5R,6R,3R)-3-(4-Carboxy-1-butyl)-7-hydroxy-6-[(1E)-(3S)-3-hydroxy-7-methyl-1,6-octadienyl]-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 9
Dependent Claim
6 words
(1S,5R,6R,7R,3S)-7-Acetoxy-6-[(1E)-(3S)-3-hydroxy-7-methyl-1,6-octadienyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 10
Dependent Claim
6 words
(1S,5R,6R,7R,3S)-3-(4-Carboxy-1-butyl)-7-hydroxy-6-[(1E)-(3S)-3-hydroxy-7-methyl-1,6-octadienyl]-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 11
Dependent Claim
6 words
(1S,5R,6R,3R)-7-Acetoxy-6-[(E)-(3RS)-3-hydroxy-3-methyl-1-octen-6-ynyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 12
Dependent Claim
6 words
(1S,5R,7R,3R)-3-(4-Carboxy-1-butyl)-7-hydroxy-6-[(E)-(3RS)-3-hydroxy-3-methyl-1-octen-6-ynyl]-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 13
Dependent Claim
6 words
(1S,5R,6R,7R,3S)-7-Acetoxy-6-[(E)-(3RS)-3-hydroxy-3-methyl-1-octen-6-ynyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 14
Dependent Claim
6 words
(1S,5R,6R,3S)-3-(4-Carboxy-1-butyl)-7-hydroxy-6-[(E)-(3RS)-3-hydroxy-3-methyl-1-octen-6-ynyl]-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 15
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-7-Acetoxy-6-[(1E)-(3RS)-3,7-dimethyl-3-hydroxy-1,6-octadienyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 16
Dependent Claim
6 words
(1S,5R,7R,3R)-3-(4-Carboxy-1-butyl)-7-hydroxy-6-[(1E)-(3RS)-3,7-dimethyl-3-hydroxy-1,6-octadienyl]-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 17
Dependent Claim
6 words
(1S,5R,6R,3S)-7-Acetoxy-6-[(1E)-(3RS)-3,7-dimethyl-3-hydroxy-1,6-octadienyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 18
Dependent Claim
6 words
(1S,5R,6R,7R,3S)-3-(4-Carboxy-1-butyl)-7-hydroxy-6-[(1E)-(3RS)-3,7-dimethyl-3-hydroxy-1,6-octadienyl]-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 19
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-7-Acetoxy-6-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-ynyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 20
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-3-(4-Carboxy-1-butyl)-7-hydroxy-6-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-ynyl]-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 21
Dependent Claim
6 words
(1S,5R,6R,3S)-7-Acetoxy-6-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-ynyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 22
Dependent Claim
6 words
(1S,5R,6R,7R,3S)-3-(4-Carboxy-1-butyl)-7-hydroxy-6-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-ynyl]-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 23
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-7-Acetoxy-6-[(1E)-(3S,4RS)-4,7-dimethyl-3-hydroxy-1,6-octadienyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 24
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-3-(4-Carboxy-1-butyl)-7-hydroxy-6-[(1E)-(3S,4RS)-4,7-dimethyl-3-hydroxy-1,6-octadienyl]-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 25
Dependent Claim
6 words
(1S,5R,6R,7R,3S)-7-Acetoxy-6-[(1E)-(3S,4RS)-4,7-dimethyl-3-hydroxy-1,6-octadienyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 26
Dependent Claim
6 words
(1S,5R,6R,7R,3S)-3-(4-Carboxy-1-butyl)-7-hydroxy-6-[(1E)-(3S,4RS)-4,7-dimethyl-3-hydroxy-1,6-octadienyl]-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 27
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-7-Acetoxy-6-[(E)-(3R)-4,4-dimethyl-3-hydroxy-1-octen-6-ynyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 28
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-3-(4-Carboxy-1-butyl)-7-hydroxy-6-[(E)-(3R)-4,4-dimethyl-3-hydroxy-1-octen-6-ynyl]-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 29
Dependent Claim
6 words
(1S,5R,6R,3S)-7-Acetoxy-6-[(E)-(3R)-4,4-dimethyl-3-hydroxy-1-octen-6-ynyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 30
Dependent Claim
6 words
(1S,5R,6R,7R,3S)-3-(4-Carboxy-1-butyl)-7-hydroxy-6-[(E)-(3R)-4,4-dimethyl-3-hydroxy-1-octen-6-ynyl]-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 31
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-7-Acetoxy-6-[(1E)-(3R)-3-hydroxy-4,4,7-trimethyl-1,6-octadienyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 32
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-3-(4-Carboxy-1-butyl)-7-hydroxy-6-[(1E)-(3R)-3-hydroxy-4,4,7-trimethyl-1,6-octadienyl]-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 33
Dependent Claim
6 words
(1S,5R,6R,7R,3S)-7-Acetoxy-6-[(1E)-(3R)-3-hydroxy-4,4,7-trimethyl-1,6-octadienyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 34
Dependent Claim
6 words
(1S,5R,7R,3S)-3-(4-Carboxy-1-butyl)-7-hydroxy-6-[(1E)-(3R)-3-hydroxy-4,4,7-trimethyl-1,6-octadienyl]-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 35
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-6-[(E)-(3S)-3-Hydroxy-1-octen-6-ynyl]-7-hydroxy-3-(4-methylsulfonylcarbamoyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 36
Dependent Claim
6 words
(1S,5R,6R,7R,3S)-6-[(E)-(3S)-3-Hydroxy-1-octen-6-ynyl]-7-hydroxy-3-(4-methylsulfonylcarbamoyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 37
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-6-[(E)-(3S)-3-Hydroxy-7-methyl-1,6-octadien-1-yl]-7-hydroxy-3-(4-methylsulfonylcarbamoyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 38
Dependent Claim
6 words
(1S,5R,6R,7R,3S)-6-[(E)-(3S)-3-Hydroxy-7-methyl-1,6-octadien-1-yl]-7-hydroxy-3-(4-methylsulfonylcarbamoyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 39
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-6-[(E)-(3R)-4,4-Dimethyl-3-hydroxy-1-octen-6-ynyl]-7-hydroxy-3-(4-methylsulfonylcarbamoyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 40
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-6-[(E)-(3S)-3-Hydroxy-1-octen-6-ynyl]-7-hydroxy-3-(4-isopropylsulfonylcarbamoyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 41
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-6-[(E)-(3S)-3-Hydroxy-7-methyl-1,6-octadien-1-yl]-7-hydroxy-3-(4-isopropylsulfonylcarbamoyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 42
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-6-[(E)-(3RS)-3-Hydroxy-3-methyl-1-octen-6-ynyl]-7-hydroxy-3-(4-isopropylsulfonylcarbamoyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 43
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-6-[(E)-(3S,4RS)-3-Hydroxy-4-methyl-1-octen-6-ynyl]-7-hydroxy-3-(4-isopropylsulfonylcarbamoyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 44
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-6-[(E)-(3S,4RS)-4,7-Dimethyl-3-hydroxy-1,6-octadien-1-yl]-7-hydroxy-3-(4-isopropylsulfonylcarbamoyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 45
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-6-[(E)-(3R)-4,4-Dimethyl-3-hydroxy-1-octen-6-ynyl]-7-hydroxy-3-(4-isopropylsulfonylcarbamoyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 46
Dependent Claim
6 words
(1S,5R,6R,3R)-6-[(E)-(3R)-3-Hydroxy-4,4,7-trimethyl-1,6-octadien-1-yl]-7-hydroxy-3-(4-isopropylsulfonylcarbamoyl-1-butyl)-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 47
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-3-(4-Acetylcarbamoyl-1-butyl)-6-[(E)-(3S)-3-hydroxy-1-octen-6-ynyl]-7-hydroxy-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 48
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-3-(4-Acetylcarbamoyl-1-butyl)-6-[(E)-(3S)-3-hydroxy-7-methyl-1,6-octadien-1-yl]-7-hydroxy-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 49
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-3-(4-Acetylcarbamoyl-1-butyl)-6-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-ynyl]-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 50
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-3-(4-Acetylcarbamoyl-1-butyl)-6-[(E)-(3S,4RS)-4,7-dimethyl-3-hydroxy-1,6-octadien-1-yl]-7-hydroxy-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 51
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-3-(4-Acetylcarbamoyl-1-butyl)-6-[(E)-(3R)-4,4-dimethyl-3-hydroxy-1-octen-6ynyl]-7-hydroxy-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 52
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-3-(4-Acetylcarbamoyl-1-butyl)-6-[(E)-(3R)-3-hydroxy-4,4,7-trimethyl-1,6-octadien-1-yl]-7-hydroxy-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 53
Dependent Claim
6 words
(1S,5R,6R,7R,3R)-3-(4-Methoxycarbonyl-1-butyl)-7-hydroxy-6-[(E)-(3R)-3-hydroxy-4,4,7-trimethyl-1,6-octadien-1-yl]-2-oxabicyclo[3,3,0]octane, a compound of claim 1.
Claim 54
Dependent Claim
8 words
(1S,5R,6R,3R)-3-(4-Carboxy-1-butyl)-7-hydroxy-6-[(E)-(3S)-3-hydroxy-1-octen-6-ynyl]-2-oxabicyclo[3,3,0]octane tris(hydroxymethyl)aminomethane salt, a compound of claim 1.
Claim 55
Dependent Claim
12 words
(1S,5R,6R,7R,3R)-7-Hydroxy-6-[(E)-(3S)-3-hydroxy-7-methyl-1,6-octadien-1-yl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane (polar product) and (1S,5R,6R,7R,3S)-7-Hydroxy-6-[(E)-(3S)-3-hydroxy-7-methyl-1,6-octadien-1-yl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane (nonpolar product), both compounds of claim 1.
Claim 56
Dependent Claim
22 words
A pharmaceutical composition comprising an amount of a compound of claim 1 effective to lower blood pressure and a pharmaceutically acceptable carrier.
Claim 57
Dependent Claim
22 words
A method of lowering blood pressure which comprises administering an amount of a compound of claim 1 effective to lower blood pressure.
Claim 58
Dependent Claim
22 words
A method of inhibiting thrombocyte aggregation which comprises administering an amount of a compound of claim 1 effective to inhibit thrombocyte aggregation.
Claim 59
Dependent Claim
24 words
A method of suppressing gastric acid secretion which comprises administering an amount of a compound of claim 1 effective to suppress gastric acid secretion.
Claim 60
Dependent Claim
22 words
A method of regulating heart rhythm which comprises administering an amount of a compound of claim 1 effective to regulate heart rhythm.
Claim 61
Dependent Claim
20 words
A method of promoting diuresis which comprises administering an amount of a compound of claim 1 effective to promote diuresis.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-03-04 | 1983-09-03 | 1984-03-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-03-04 | 1987-09-03 | 1988-03-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-03-04 | 1991-09-03 | 1992-03-04 | $7700.00 | Window Closed / Lapsed |