Derivatives of 3,3-diphenylpropylamines
DC CAFC
First Claim
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1. R-(+)-isobutyric acid 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenyl ester.
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Abstract
The invention concerns novel derivatives of 3,3-diphenylpropylamines, methods for their preparation, pharmaceutical compositions containing the novel compounds, and the use of the compounds for preparing drugs. More particularly, the invention relates to novel prodrugs of antimuscarinic agents with superior pharmacokinetic properties compared to existing drugs such as oxybutynin and tolterodine, methods for their preparation, pharmaceutical compositions containing them, a method of using said compounds and compositions for the treatment of urinary incontinence, gastrointestinal hyperactivity (irritable bowel syndrome) and other smooth muscle contractile conditions.
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Citations
16 Claims
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1. R-(+)-isobutyric acid 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenyl ester.
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2. A salt of R-(+)-isobutyric acid 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenyl ester with a physiologically acceptable acid.
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3. A pharmaceutical composition comprising an effective amount of R-(+)-isobutyric acid 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenyl ester, or a salt thereof with a physiologically acceptable acid and a pharmaceutically acceptable carrier.
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4. A method of antagonizing a muscarinic receptor in a patient in need thereof, the method comprising administering to the patient R-(+)-isobutyric acid 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenyl ester or a salt thereof with a physiologically acceptable acid so as to result in contact of the muscarinic receptor with an effective amount of R-(+)-2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenol.
- 5. A method of treating a disease in a mammal that is amenable to treatment by antagonizing muscarinic receptors in the mammal, the method comprising administering to the mammal a pharmaceutical composition comprising an effective amount of R-(+)-isobutyric acid 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenyl ester or a salt thereof with a physiologically acceptable acid.
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8. A compound selected from the group consisting of:
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acetic acid 4-acetoxy-3-(3-diisopropylamino- 1-phenylpropyl)-benzyl ester, n-butyric acid 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenyl ester, isobutyric acid 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenyl ester, isobutyric acid 2-(3-diisopropylamino-1-phenylpropyl)-4-isobutyryloxymethylphenyl ester, n-butyric acid 4-n-butyryloxymethyl-2-(3-diisopropylamino-1-phenylpropyl)-phenyl ester, propionic acid 2-(3-diisopropylamino-1-phenylpropyl)-4-propionyloxymethylphenyl ester, propionic acid 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenyl ester, and acetic acid 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenyl ester, including racemic mixtures and individual enantiomers of said compounds, and salts of said compounds with a physiologically acceptable acid. - View Dependent Claims (9)
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10. A pharmaceutical composition comprising an effective amount of a compound selected from the group consisting of:
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acetic acid 4-acetoxy-3-(3-diisopropylamino-1-phenylpropyl)-benzyl ester, n-butyric acid 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenyl ester, isobutyric acid 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenyl ester, isobutyric acid 2-(3-diisopropylamino-1-phenylpropyl)-4-isobutyryloxymethylphenyl ester, n-butyric acid 4-n-butyryloxymethyl-2-(3-diisopropylamino-1-phenylpropyl)-phenyl ester, propionic acid 2-(3-diisopropylamino-1-phenylpropyl)-4-propionyloxymethylphenyl ester, propionic acid 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenyl ester, and acetic acid 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenyl ester, including racemic mixtures and individual enantiomers of said compounds, and salts of said compounds with a physiologically acceptable acid, and a pharmaceutically acceptable carrier. - View Dependent Claims (11)
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12. A method of treating a disease or condition in a mammal that is amenable to treatment by antagonizing muscarinic receptors in the mammal, the method comprising administering to the mammal a pharmaceutical composition comprising an effective amount of a compound selected from the group consisting of:
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acetic acid 4-acetoxy-3-(3-diisopropylamino-1-phenylpropyl)-benzyl ester, n-butyric acid 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenyl ester, isobutyric acid 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenyl ester, isobutyric acid 2-(3-diisopropylamino-1-phenylpropyl)-4-isobutyryloxymethylphenyl ester, n-butyric acid 4-n-butyryloxymethyl-2-(3-diisopropylamino- 1-phenylpropyl)-phenyl ester, propionic acid 2-(3-diisopropylamino-1-phenylpropyl)-4-propionyloxymethylphenyl ester, propionic acid 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenyl ester, and acetic acid 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenyl ester, including racemic mixtures and individual enantiomers of said compounds, and salts of said compounds with a physiologically acceptable acid. - View Dependent Claims (13, 14, 15, 16)
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Specification
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Litigation Data
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Current AssigneeUCB Pharma GmbH (UCB SA)
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Original AssigneeSchwarz Pharma Ag (Schwarz Pharma)
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InventorsSparf, Bengt, Meese, Claus
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Primary Examiner(s)Tucker; Zachary C
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Application NumberUS11/201,756Publication NumberTime in Patent Office1,035 DaysField of Search514/551, 560/140US Class Current514/551CPC Class CodesA61P 1/00 Drugs for disorders of the ...A61P 1/04 for ulcers, gastritis or re...A61P 13/00 Drugs for disorders of the ...A61P 13/02 of urine or of the urinary ...A61P 13/10 of the bladderA61P 21/00 Drugs for disorders of the ...A61P 25/02 for peripheral neuropathiesA61P 43/00 Drugs for specific purposes...C07C 217/48 the carbon skeleton being u...C07C 217/62 linked by carbon chains hav...C07C 219/28 having amino groups bound t...C07C 229/34 the carbon skeleton contain...C07C 271/44 to hydrogen atoms or to car...C07C 271/52 to carbon atoms of hydrocar...C07C 307/02 Monoamides of sulfuric acid...
