US5677346A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Treating urinary incontinence using (S)-desethyloxybutynin
Assignee: Sumitomo Pharma America Inc
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Filing: 1995-06-07
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Granted: 1997-10-14
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Expires: 2015-06-07
Abstract
Abstract A method for treating urinary incontinence while avoiding concomitant liability of adverse effects associated with racemic oxybutynin is disclosed. The method comprises administering a therapeutically effective amount of (S)-oxybutynin, (S)-desethyloxybutynin or a pharmaceutically acceptable salt thereof, substantially free of the corresponding R enantiomer. Pharmaceutical compositions in the form of tablets and transdermal devices comprising (S)-oxybutynin or (S)-desethyloxybutynin and an acceptable carrier are also disclosed, as is a synthesis of desethyloxybutynin.
Inventors
- 👤 Gunnar Aberg
- 👤 John R. McCullough
- 👤 Yue Fang
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 14:00
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/21; A61K31/215; A61K31/216; A61P; A61P13/00; A61P13/10
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
42 words
A method for treating urinary incontinence while avoiding concomitant liability of adverse effects, which comprises administering to a human in need of such treatment a therapeutically effective amount of (S)-desethyloxybutynin or a pharmaceutically acceptable salt thereof, substantially free of its (R) enantiomer.
Claim 2
Independent Claim
42 words
A method for treating urinary incontinence while avoiding concomitant liability of adverse effects, which comprises administering to a human in need of such treatment a therapeutically effective amount of (S)-desethyloxybutynin or a pharmaceutically acceptable salt thereof, substantially free of its (R) enantiomer.
Claim 3
Dependent Claim
19 words
The method of claim 1 wherein (S)-desethyloxybutynin is administered by inhalation or by parenteral, transdermal, rectal or oral administration.
Claim 4
Dependent Claim
28 words
The method of claim 2 wherein the amount of (S)-desethyloxybutynin or a pharmaceutically acceptable salt thereof administered is from about 1 mg to about 100 mg per day.
Claim 5
Dependent Claim
16 words
The method according to claim 1 wherein (S)-desethyloxybutynin, or pharmaceutically acceptable salt thereof, is administered orally.
Claim 6
Dependent Claim
16 words
The method according to claim 1 wherein (S)-desethyloxybutynin, or pharmaceutically acceptable salt thereof, is administered transdermally.
Claim 7
Dependent Claim
16 words
The method of claim 1, wherein (S)-desethyloxybutynin, or a pharmaceutically acceptable salt thereof, is administered parenterally.
Claim 8
Dependent Claim
16 words
The method of claim 6 wherein (S)-desethyloxybutynin, or a pharmaceutically acceptable salt thereof, is administered intravenously.
Claim 9
Dependent Claim
16 words
The method of claim 6 wherein (S)-desethyloxybutynin, or a pharmaceutically acceptable salt thereof, is administered subcutaneously.
Claim 10
Dependent Claim
16 words
The method of claim 6 wherein (S)-desethyloxybutynin, or a pharmaceutically acceptable salt thereof, is administered intramuscularly.
Claim 11
Dependent Claim
38 words
A pharmaceutical unit dosage form in the form of a tablet or capsule which comprises a therapeutically effective amount of (S)-desethyloxybutynin, or a pharmaceutically acceptable salt thereof, substantially free of its (R) stereoisomer, and a pharmaceutically acceptable carrier.
Claim 12
Dependent Claim
38 words
A pharmaceutical unit dosage form in the form of a tablet or capsule which comprises a therapeutically effective amount of (S)-desethyloxybutynin, or a pharmaceutically acceptable salt thereof, substantially free of its (R) stereoisomer, and a pharmaceutically acceptable carrier.
Claim 13
Dependent Claim
17 words
A pharmaceutical unit dosage form according to claim 10 comprising from 0.5 to 25 mg of (S)-desethyloxybutynin.
Claim 14
Dependent Claim
37 words
A pharmaceutical dosage form in the form of a transdermal delivery device which comprises a therapeutically effective amount of (S)-desethyloxybutynin, or a pharmaceutically acceptable salt thereof, substantially free of its (R) stereoisomer, and a pharmaceutically acceptable carrier.
Claim 15
Dependent Claim
37 words
A pharmaceutical dosage form in the form of a transdermal delivery device which comprises a therapeutically effective amount of (S)-desethyloxybutynin, or a pharmaceutically acceptable salt thereof, substantially free of its (R) stereoisomer, and a pharmaceutically acceptable carrier.
Claim 16
Dependent Claim
17 words
A pharmaceutical dosage form according to claim 12 wherein said pharmaceutically acceptable carrier comprises a permeation enhancer.
Claim 17
Dependent Claim
20 words
The pharmaceutical unit dosage form of claim 10 wherein said table or capsule is formulated for controlled release upon administration.
Claim 18
Dependent Claim
45 words
A process for preparing desethyloxybutynin comprising the steps of: (a) reacting methyl α-cyclohexyl-α-hydroxybenzeneacetate with 4- N-ethyl-(4-methoxyphenyl)methylamino!-2-butyn-1-ol in the presence of an anhydrous base to produce 4- N-ethyl-(4-methoxyphenyl)methylamino!-2-butynyl α-cyclohexyl-α-hydroxybenzeneacetate; and (b) reacting said 4- N-ethyl-(4-methoxyphenyl)methylamino!-2-butynyl α-cyclohexyl-α-hydroxybenzeneacetate sequentially with a carbonochloridate and methanol to produce 4-(ethylamino)-2-butynyl α-cyclohexyl-α-hydroxybenzeneacetate.
Claim 19
Dependent Claim
45 words
A process for preparing desethyloxybutynin comprising the steps of: (a) reacting methyl α-cyclohexyl-α-hydroxybenzeneacetate with 4- N-ethyl-(4-methoxyphenyl)methylamino!-2-butyn-1-ol in the presence of an anhydrous base to produce 4- N-ethyl-(4-methoxyphenyl)methylamino!-2-butynyl α-cyclohexyl-α-hydroxybenzeneacetate; and (b) reacting said 4- N-ethyl-(4-methoxyphenyl)methylamino!-2-butynyl α-cyclohexyl-α-hydroxybenzeneacetate sequentially with a carbonochloridate and methanol to produce 4-(ethylamino)-2-butynyl α-cyclohexyl-α-hydroxybenzeneacetate.
Claim 20
Dependent Claim
32 words
A process according to claim 15 comprising the additional step of reacting N-ethyl-4-methoxybenzenemethanamine with 2-propyn-1-ol and formaldehyde or a formaldehyde equivalent in the presence of a copper(I) salt to produce 4- N-ethyl-(4-methoxyphenyl)methylamino!-2-butyn-1-ol.
Claim 21
Dependent Claim
70 words
A process according to claim 18 comprising: (a) reacting N-ethyl-4-methoxybenzenemethanamine with 2-propyn-1-ol and paraformaldehyde in an inert solvent in the presence of cuprous chloride to produce 4- N-ethyl-(4-methoxyphenyl)methylamino!-2-butyn-1-ol; (b) reacting methyl α-cyclohexyl-α-hydroxybenzeneacetate with said 4- N-ethyl-(4-methoxyphenyl)methylamino!-2-butyn-1-ol in the presence of sodium methoxide in toluene to produce 4- N-ethyl-(4-methoxyphenyl)methylamino!-2-butynyl α-cyclohexyl-α-hydroxybenzeneacetate; and (c) reacting said 4- N-ethyl-(4-methoxyphenyl)methylamino!-2-butynyl α-cyclohexyl-α-hydroxybenzeneacetate sequentially with α-chloroethyl carbonochloridate in dichloroethane, followed by methanol to produce 4-(ethylamino)-2-butynyl α-cyclohexyl-α-hydroxybenzeneacetate (desethyloxybutyin).
Claim 22
Dependent Claim
32 words
A process according to claim 15 wherein said methyl α-cyclohexyl-α-hydroxybenzeneacetate employed in step (a) contains an excess of one enantiomer over its opposite enantiomer, thereby producing desethyloxybutynin enriched in a single enantiomer.
Claim 23
Dependent Claim
21 words
A process according to claim 18 wherein said methyl α-cyclohexyl-α-hydroxybenzeneacetate is predominantly of the S configuration and said desethyloxybutynin is S-desethyloxybutynin.
Claim 24
Dependent Claim
20 words
A pharmaceutical composition for treating urinary incontinence comprising (S)-desethyloxybutynin, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
Claim 25
Dependent Claim
20 words
A pharmaceutical composition for treating urinary incontinence comprising (S)-desethyloxybutynin, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
Claim 26
Dependent Claim
17 words
The pharmaceutical composition of claim 20 wherein the pharmaceutically acceptable carrier is a solid pharmaceutically acceptable carrier.
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) | 2000-10-13 | 2001-04-14 | 2001-10-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2004-10-13 | 2005-04-14 | 2005-10-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2008-10-13 | 2009-04-14 | 2009-10-14 | $7700.00 | Window Closed / Lapsed |