US4515786A
Expired / Lapsed
US
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11α-Amino-androstanes
Assignee: Glaxo Group Ltd
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Filing: 1983-06-30
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Granted: 1985-05-07
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Expires: 2003-06-30
Abstract
Abstract ##STR1## wherein R 1 is a C 1-8 alkyl group or a C 3-7 cycloalkyl group; R 2 is a hydrogen atom, a C 1-6 alkoxy group or a C 2-5 alkanoyloxy group; R 3 is a C 1-6 alkyl group or a C 3-7 cycloalkyl group; and R 4 is a group --OR 5 or --OCOR 6 where R 5 is an optionally substituted alkyl or alkenyl group which may contain up to 6 carbon atoms, an optionally substituted C 3-7 cycloalkyl group, a phenyl group or a carbon-attached 5-7 membered heterocyclic ring in which the hetero-atom is selected from nitrogen, oxygen and sulphur, and R 6 is a hydrogen atom or a group R 5 as defined above; provided that when the compounds contain a 5β-hydrogen atom, R 2 is a hydrogen atom and salts thereof, which compounds have activity as antidysthythmic agents.
Inventors
- 👤 Gordon H. Phillipps
- 👤 David C. Humber
- 👤 George B. Ewan
- 👤 Barry A. Coomber
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 13:57
CPC Classifications
C; C07; C07J; C07J63/00; C07J63/008; A; A61; A61P; A61P9/00; A61P9/06; C07J41/00; C07J41/0005; C07J41/0011
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
177 words
Compounds of the formula ##STR4## wherein R 1 is a C 3-8 alkyl group or a C 3-7 cycloalkyl group; R 2 is a hydrogen atom, a C 1-6 alkoxy group or a C 2-5 alkanoyloxy group; R 3 is a C 1-6 alkyl group or a C 3-7 cycloalkyl group; and R 4 is a group --OR 5 or --OCOR 6 where R 5 is an alkyl or alkenyl group which may contain up to 6 carbon atoms (or such a group substituted by halogen, C 1-6 alkoxy, carboxy, phenyl, phenyl substituted by nitro, halo, C 1-4 alkoxy or C 1-4 alkyl), a C 3-7 cycloalkyl group, a phenyl group (or such a group substituted by nitro, halo, C 1-4 alkoxy or C 1-4 alkyl), or a carbon-attached 5-7 membered heterocyclic ring in which the heteroatom is selected from nitrogen, oxygen and sulphur, and R 6 is a hydrogen atom or a group R 5 as defined above; provided that when the compounds contain a 5β-hydrogen atom, R 2 is a hydrogen atom; and salts thereof.
Claim 2
Dependent Claim
177 words
Compounds of the formula ##STR4## wherein R 1 is a C 3-8 alkyl group or a C 3-7 cycloalkyl group; R 2 is a hydrogen atom, a C 1-6 alkoxy group or a C 2-5 alkanoyloxy group; R 3 is a C 1-6 alkyl group or a C 3-7 cycloalkyl group; and R 4 is a group --OR 5 or --OCOR 6 where R 5 is an alkyl or alkenyl group which may contain up to 6 carbon atoms (or such a group substituted by halogen, C 1-6 alkoxy, carboxy, phenyl, phenyl substituted by nitro, halo, C 1-4 alkoxy or C 1-4 alkyl), a C 3-7 cycloalkyl group, a phenyl group (or such a group substituted by nitro, halo, C 1-4 alkoxy or C 1-4 alkyl), or a carbon-attached 5-7 membered heterocyclic ring in which the heteroatom is selected from nitrogen, oxygen and sulphur, and R 6 is a hydrogen atom or a group R 5 as defined above; provided that when the compounds contain a 5β-hydrogen atom, R 2 is a hydrogen atom; and salts thereof.
Claim 3
Dependent Claim
19 words
Compounds as claimed in claim 1 wherein R 1 is an isopentyl, hexyl, isohexyl, neohexyl, cyclopentyl or cyclohexyl group.
Claim 4
Dependent Claim
15 words
Compounds as claimed in claim 1 wherein R 3 is a methyl or ethyl group.
Claim 5
Dependent Claim
16 words
Compounds as claimed in claim 1 wherein R 4 is a methoxy, ethoxy or acetoxy group.
Claim 6
Dependent Claim
10 words
Compounds as claimed in claim 1 having a 5α-hydrogen atom.
Claim 7
Dependent Claim
15 words
Compounds as claimed in claim 1 in the form of physiologically acceptable acid addition salts.
Claim 8
Dependent Claim
30 words
Compounds as claimed in claim 6 in the form of hydrochloride, hydrobromide, phosphate, sulphate, p-toluenesulphonate, methanesulphonate, citrate, tartrate, acetate, ascorbate, lactate, maleate, succinate, tricarballylate, glutarate and glutaconate acid addition salts.
Claim 9
Dependent Claim
45 words
Compounds of formula (I) as claimed in claim 1 selected from: (a) ethyl 3α-acetoxy-2β-ethoxy-11α-(3-methylbutylamino)-5α-androstane-17β-carboxylate; (b) methyl 3α-acetoxy-2β-ethoxy-11α-(3-methylbutylamino)-5α-androstane-17β-carboxylate; (c) methyl 2β,3α-diethoxy-11α-(3-methylbutylamino)-5α-androstane-17β-carboxylate; (d) methyl 11α-cyclohexylamino-2β,3α-diacetoxy-5α-androstane-17β-carboxylate; (e) methyl 3α-acetoxy-11α-cyclohexylamino-5α-androstane-17β-carboxylate; (f) methyl 3α-acetoxy-11α-cyclohexylamino-2β-methoxy-5α-androstane-17β-carboxylate; (g) methyl 2β,3α-diacetoxy-11α-(3-methylbutylamino)-5α-androstane-17β-carboxylate; (h) methyl 3α-acetoxy-11α-(3-methylbutylamino)-5α-androstane-17.beta.-carboxylate; (i) methyl 3α-ethoxy-11α-(3-methylbutylamino)-5α-androstane-17.beta.-carboxylate; and their physiologically acceptable acid addition salts.
Claim 10
Dependent Claim
12 words
Compounds as claimed in claim 8 in the form of their hydrochlorides.
Claim 11
Dependent Claim
31 words
Pharmaceutical compositions comprising at least one compound of formula (I) as claimed in claim 1 or a physiologically acceptable salt thereof in admixture with one or more pharmaceutical carriers or excipients.
Claim 12
Dependent Claim
47 words
A method of therapy or prophylaxis of a human or animal body suffering from or liable to cardiac dysrhythmias which method comprises administering to the said body an effective amount of a compound of formula (I), or a physiologically acceptable salt thereof as claimed in claim 1.
Claim 13
Dependent Claim
20 words
Compounds as claimed in claim 1 wherein R 2 is a hydrogen atom or a methoxy, ethoxy or propoxy group.
Claim 14
Dependent Claim
202 words
Compounds of the formula ##STR5## wherein R 7 is a hydrogen atom, a C 3-8 alkyl group or a C 3-7 cycloalkyl group; R 8 is a hydrogen atom, a C 1-6 alkyl group or a C 3-7 cycloalkyl group; and R 2 is a hydrogen atom, a C 1-6 alkoxy group or a C 2-5 alkanoyloxy group; and R 4 is a group --OR 5 or --OCOR 6 where R 5 is an alkyl or alkenyl group which may contain up to 6 carbon atoms (or such a group substituted by halogen, C 1-6 alkoxy, carboxy, phenyl, phenyl substituted by nitro, halo, C 1-4 alkoxy or C 1-4 alkyl), a C 3-7 cycloalkyl group, a phenyl group (or such a group substituted by nitro, halo, C 1-4 alkoxy or C 1-4 alkyl), or a carbon-attached 5-7 membered heterocyclic ring in which the heteroatom is selected from nitrogen, oxygen and suplhur, and R 6 is a hydrogen atom or a group R 5 as defined above; with the provisos that at least one of R 7 and R 8 is a hydrogen atom and that when the compounds contain a 5β hydrogen atom R 2 is a hydrogen atom; and salts thereof.
Claim 15
Dependent Claim
202 words
Compounds of the formula ##STR5## wherein R 7 is a hydrogen atom, a C 3-8 alkyl group or a C 3-7 cycloalkyl group; R 8 is a hydrogen atom, a C 1-6 alkyl group or a C 3-7 cycloalkyl group; and R 2 is a hydrogen atom, a C 1-6 alkoxy group or a C 2-5 alkanoyloxy group; and R 4 is a group --OR 5 or --OCOR 6 where R 5 is an alkyl or alkenyl group which may contain up to 6 carbon atoms (or such a group substituted by halogen, C 1-6 alkoxy, carboxy, phenyl, phenyl substituted by nitro, halo, C 1-4 alkoxy or C 1-4 alkyl), a C 3-7 cycloalkyl group, a phenyl group (or such a group substituted by nitro, halo, C 1-4 alkoxy or C 1-4 alkyl), or a carbon-attached 5-7 membered heterocyclic ring in which the heteroatom is selected from nitrogen, oxygen and suplhur, and R 6 is a hydrogen atom or a group R 5 as defined above; with the provisos that at least one of R 7 and R 8 is a hydrogen atom and that when the compounds contain a 5β hydrogen atom R 2 is a hydrogen atom; and salts thereof.
Claim 16
Dependent Claim
38 words
Compounds as claimed in claim 2 wherein R 2 is a hydrogen atom or a methoxy, ethoxy or propoxy group; R 3 is a methyl or ethyl group; and R 4 is a methoxy, ethoxy or acetoxy group.
Claim 17
Dependent Claim
10 words
Compounds as claimed in claim 14 having a 5α-hydrogen atom.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-05-06 | 1988-11-05 | 1989-05-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-05-06 | 1992-11-05 | 1993-05-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-05-06 | 1996-11-05 | 1997-05-07 | $7700.00 | Window Closed / Lapsed |