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US3901966A Expired / Lapsed US ⏱️ 0.0 years remaining

Sustained release of methantheline

Assignee: AO Inc 14 MECHANIC ST A CORP OF
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Filing: 1973-09-10
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Granted: 1975-08-26
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Expires: 1993-09-10
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Abstract

Abstract A sustained release pharmaceutical composition which includes methantheline bromide and two different polymers of a monoester of acrylic acid and/or methacrylic acid and a polyhydric alcohol.

Inventors

  • 👤 James S Y Sim
  • 👤 Horn Maurice H Van
  • 👤 Arthur I Cohen
  • 👤 Stanley E Gordesky
  • 👤 Stanley I Gordon

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 22:29
CPC Classifications
A; A61; A61K; A61K9/00; A61K9/20; A61K9/2004; A61K9/2022; A61K9/2027

Claims Analysis

Total Claims: 40
Claim 1
Independent Claim 32 words
A SUSTAINED RELEASE 864 HOUR AFTER ADMINISTRATION METHANTHELINE ELUTING MULTIBARRIER PHARMACEUTICAL COMPOSITION COMPRISING: A. A POLYMERIZED AND CURED OUTER MATRIX OF A WATER-INSOLUBLE BUT WATER-SWELLABLE HYDROPHILIC POLYMER OF A MONOMER MIXTURE CONTAINING:
Claim 2
Dependent Claim 32 words
A SUSTAINED RELEASE 864 HOUR AFTER ADMINISTRATION METHANTHELINE ELUTING MULTIBARRIER PHARMACEUTICAL COMPOSITION COMPRISING: A. A POLYMERIZED AND CURED OUTER MATRIX OF A WATER-INSOLUBLE BUT WATER-SWELLABLE HYDROPHILIC POLYMER OF A MONOMER MIXTURE CONTAINING:
Claim 3
Dependent Claim 22 words
POLYMERIZABLE MONOESTER OF A MEMBER SELECTED FROM THE GROUP CONSISTING OF ACRYLIC ACID, METHACRYLIC ACID, AND MIXTURES THEREOF, AND A POLYHYDRIC ALCOHOL,
Claim 4
Dependent Claim 22 words
POLYMERIZABLE MONOESTER OF A MEMBER SELECTED FROM THE GROUP CONSISTING OF ACRYLIC ACID, METHACRYLIC ACID, AND MIXTURES THEREOF, AND A POLYHYDRIC ALCOHOL,
Claim 5
Dependent Claim 22 words
POLYMERIZABLE MONOESTER OF A MEMBER SELECTED FROM THE GROUP CONSISTING OF ACRYLIC ACID, METHACRYLIC ACID, AND MIXTURES THEREOF, AND A POLYHYDRIC ALCOHOL,
Claim 6
Dependent Claim 22 words
POLYMERIZABLE MONOESTER OF A MEMBER SELECTED FROM THE GROUP CONSISTING OF ACRYLIC ACID, METHACRYLIC ACID, AND MIXTURES THEREOF, AND A POLYHYDRIC ALCOHOL,
Claim 7
Dependent Claim 88 words
polymerizable diester of a member selected from the group consisting of acrylic acid, methacrylic acid, and mixtures thereof; and a polyhydric alcohol; and wherein the monomer mixture contains from about 70 to about 35% by weight of (D)(1) and from about 15 to about 49.8% by weight of (D)(2) based upon the total weight of (D)(1) and (D)(2) in said monomer mixture; and E. then polymerizing to provide an outer matrix of the water-insoluble but water-swellable hydrophilic polymer of the monomer mixture containing the polymerizable monoester and diester.
Claim 8
Dependent Claim 88 words
polymerizable diester of a member selected from the group consisting of acrylic acid, methacrylic acid, and mixtures thereof; and a polyhydric alcohol; and wherein the monomer mixture contains from about 70 to about 35% by weight of (D)(1) and from about 15 to about 49.8% by weight of (D)(2) based upon the total weight of (D)(1) and (D)(2) in said monomer mixture; and E. then polymerizing to provide an outer matrix of the water-insoluble but water-swellable hydrophilic polymer of the monomer mixture containing the polymerizable monoester and diester.
Claim 9
Dependent Claim 31 words
a polymerizable sulfur-containing material selected from the group consisting of vinyl sulfonic acid, vinylpropane sulfonic acid, and p-vinylbenzene sulfonic acid, ammonium salts thereof, alkali metal salts thereof; and mixtures thereof; and
Claim 10
Dependent Claim 31 words
a polymerizable sulfur-containing material selected from the group consisting of vinyl sulfonic acid, vinylpropane sulfonic acid, and p-vinylbenzene sulfonic acid, ammonium salts thereof, alkali metal salts thereof; and mixtures thereof; and
Claim 11
Dependent Claim 65 words
The composition of claim 1 wherein each of said polymerizable monoesters (A)(1) and (B)(1) is a monoester of a member selected from the group consisting of acrylic acid, methacrylic acid, and mixtures thereof; and a polyhydric alcohol selected from the group consisting of ethylene glycol, 1,3-propanediol, diethylene glycol, dipropylene glycol, polyethylene glycol, polypropylene glycol, 1,6-hexamethylene glycol, 1,4-butanediol, glycerol, trimethylol propane, trimethylolethane, pentaerythritol, mannitol, and sorbitol.
Claim 12
Dependent Claim 32 words
a polymerizable sulfur-containing material selecteD from the group consisting of vinyl sulfonic acid, vinylpropane sulfonic acid, and p-vinylbenzene sulfonic acid, and ammonium salts thereof; alkali metal salts thereof; and mixtures thereof; and
Claim 13
Dependent Claim 32 words
a polymerizable sulfur-containing material selecteD from the group consisting of vinyl sulfonic acid, vinylpropane sulfonic acid, and p-vinylbenzene sulfonic acid, and ammonium salts thereof; alkali metal salts thereof; and mixtures thereof; and
Claim 14
Dependent Claim 87 words
polymerizable diester of a member selected from the group consisting of acrylic acid, methacrylic acid, and mixtures thereof; and a polyhydric alcohol; and wherein the monomer mixture contains from about 70 to about 35% by weight of (A)(1); and from about 15 to about 49.8% by weight of (A)(2) based upon the total weight of (A)(1) and (A)(2) in the monomer mixture; B. a polymerized and cured inner matrix within said outer matrix and being a water-insoluble but water swellable hydrophilic polymer of a monomer mixture containing:
Claim 15
Dependent Claim 87 words
polymerizable diester of a member selected from the group consisting of acrylic acid, methacrylic acid, and mixtures thereof; and a polyhydric alcohol; and wherein the monomer mixture contains from about 70 to about 35% by weight of (A)(1); and from about 15 to about 49.8% by weight of (A)(2) based upon the total weight of (A)(1) and (A)(2) in the monomer mixture; B. a polymerized and cured inner matrix within said outer matrix and being a water-insoluble but water swellable hydrophilic polymer of a monomer mixture containing:
Claim 16
Dependent Claim 32 words
A POLYMERIZABLE SULFUR-CONTAINING MATERIAL SELECTED FROM THE GROUP CONSISTING OF VINYL SULFONIC ACID, VINYLPROPANE SULFONIC ACID, AND P-VINYLBENZENE SULFONIC ACID, AND AMMONIUM SALTS THEREOF, ALKALI MTAL SALTS THEREOF, AND MIXTURES THEREOF, AND
Claim 17
Dependent Claim 32 words
A POLYMERIZABLE SULFUR-CONTAINING MATERIAL SELECTED FROM THE GROUP CONSISTING OF VINYL SULFONIC ACID, VINYLPROPANE SULFONIC ACID, AND P-VINYLBENZENE SULFONIC ACID, AND AMMONIUM SALTS THEREOF, ALKALI MTAL SALTS THEREOF, AND MIXTURES THEREOF, AND
Claim 18
Dependent Claim 87 words
POLYMERIZABLE DIESTER OF A MEMBER SELECTED FROM THE GROUP CONSISTING OF ACRYLIC ACID, METHACRYLIC ACID, AND MIXTURES THEREOF, AND A POLYHYDRIC ALCOHOL, AND WHEREIN THE MONOMER MIXTURE CONTAINS FROM ABOUT 70 TO ABOUT 35% BY WEIGHT OF (A)(1), AND FROM ABOUT 15 TO ABOUT 49.8% BY WEIGHT OF (A)(2) BASED UPON THE TOTAL WEIGHT OF (A)(1) AND (A)(2) IN THE MONOMER MIXTURE, B. A POLYMERIZED AND CURED INNER MATRIX WITHIN SAID OUTER MATRIX AND BEING A WATER-INSOLUBLE BU WATER SWELLABLE HYDROPHILIC POLYMER OF A MONOMER MIXTURE CONTAINING:
Claim 19
Dependent Claim 87 words
POLYMERIZABLE DIESTER OF A MEMBER SELECTED FROM THE GROUP CONSISTING OF ACRYLIC ACID, METHACRYLIC ACID, AND MIXTURES THEREOF, AND A POLYHYDRIC ALCOHOL, AND WHEREIN THE MONOMER MIXTURE CONTAINS FROM ABOUT 70 TO ABOUT 35% BY WEIGHT OF (A)(1), AND FROM ABOUT 15 TO ABOUT 49.8% BY WEIGHT OF (A)(2) BASED UPON THE TOTAL WEIGHT OF (A)(1) AND (A)(2) IN THE MONOMER MIXTURE, B. A POLYMERIZED AND CURED INNER MATRIX WITHIN SAID OUTER MATRIX AND BEING A WATER-INSOLUBLE BU WATER SWELLABLE HYDROPHILIC POLYMER OF A MONOMER MIXTURE CONTAINING:
Claim 20
Dependent Claim 139 words
POLYMERIZABLE DIESTER OF A MEMBER SELECTED FROM THE GROUP CONSISTING OF ACRYLIC ACID, METHACRYLIC ACID, AND MIXTURES THEREOF, AND A POLYHYDRIC ALCOHOL, AND WHEREIN THE MONOMER MIXTURE CONTAINS FROM ABOUT 25 TO ABOUT 44.4% BY WEIGHT OF(B)(1), FROM ABOUT 5 TO ABOUT 30% BY WEIGHT OF (B)(2), AND FROM ABOUT 5 TO ABOUT 25.2% BY WEIGHT OF (B)(3) BASED UPON THE TOTAL WEIGHT OF (B)(1), (B)(2), AND (B)(3) IN THE MONOMER MIXTURE, AND C. SAID POLYMERIZED AND CURED MATRIX HAVING BEEN SOAKED FOR ABOUT 12 HOURS IN ISOTONIC SALINE SOLUTION CONTAINING PER 5 ML OF ISOTONIC SALINE SOLUTION AT LEAST ABOUT 100 MG OF METHANTHELINE BROMIDE IN AN AMOUNT AT LEAST SUFFICIENT FOR THE TOTAL DOSAGE REQUIREMENT ADAPTED TO GRADUALLY ELUTE, UPON ADMINISTRATION DURING 864 HOURS OF A TREATMENT PERIOD, AND THEREBY ENTRAPPING THE METHANTHELINE IN SAID INNER MATRIX.
Claim 21
Dependent Claim 139 words
POLYMERIZABLE DIESTER OF A MEMBER SELECTED FROM THE GROUP CONSISTING OF ACRYLIC ACID, METHACRYLIC ACID, AND MIXTURES THEREOF, AND A POLYHYDRIC ALCOHOL, AND WHEREIN THE MONOMER MIXTURE CONTAINS FROM ABOUT 25 TO ABOUT 44.4% BY WEIGHT OF(B)(1), FROM ABOUT 5 TO ABOUT 30% BY WEIGHT OF (B)(2), AND FROM ABOUT 5 TO ABOUT 25.2% BY WEIGHT OF (B)(3) BASED UPON THE TOTAL WEIGHT OF (B)(1), (B)(2), AND (B)(3) IN THE MONOMER MIXTURE, AND C. SAID POLYMERIZED AND CURED MATRIX HAVING BEEN SOAKED FOR ABOUT 12 HOURS IN ISOTONIC SALINE SOLUTION CONTAINING PER 5 ML OF ISOTONIC SALINE SOLUTION AT LEAST ABOUT 100 MG OF METHANTHELINE BROMIDE IN AN AMOUNT AT LEAST SUFFICIENT FOR THE TOTAL DOSAGE REQUIREMENT ADAPTED TO GRADUALLY ELUTE, UPON ADMINISTRATION DURING 864 HOURS OF A TREATMENT PERIOD, AND THEREBY ENTRAPPING THE METHANTHELINE IN SAID INNER MATRIX.
Claim 22
Dependent Claim 140 words
polymerizable diester of a member selected from the group consisting of acrylic acid, methacrylic acid, and mixtures thereof; and a polyhydric alcohol; and wherein the monomer mixture contains from about 25 to about 44.4% by weight of (B)(1); from about 5 to about 30% by weight of (B)(2); and from about 5 to about 25.2% by weight of (B)(3) based upon the total weight of (B)(1), (B)(2), and (B)(3) in the monomer mixture; and C. said polymerized and cured matrix having been soaked for about 12 hours in isotonic saline solution containing per 5 ml of isotonic saline solution at least about 100 mg of methantheline bromide in an amount at least sufficient for the total dosage requirement adapted to gradually elute, upon administration during 864 hours of a treatment period; and thereby entrapping the methantheline in said inner matrix.
Claim 23
Dependent Claim 140 words
polymerizable diester of a member selected from the group consisting of acrylic acid, methacrylic acid, and mixtures thereof; and a polyhydric alcohol; and wherein the monomer mixture contains from about 25 to about 44.4% by weight of (B)(1); from about 5 to about 30% by weight of (B)(2); and from about 5 to about 25.2% by weight of (B)(3) based upon the total weight of (B)(1), (B)(2), and (B)(3) in the monomer mixture; and C. said polymerized and cured matrix having been soaked for about 12 hours in isotonic saline solution containing per 5 ml of isotonic saline solution at least about 100 mg of methantheline bromide in an amount at least sufficient for the total dosage requirement adapted to gradually elute, upon administration during 864 hours of a treatment period; and thereby entrapping the methantheline in said inner matrix.
Claim 24
Dependent Claim 98 words
polymerizable diester of a member selected from the group consisting of acrylic acid, methacrylic acid, and mixtures thereof; and a polyhydric alcohol; and wherein tHe monomer mixture contains from about 25 to about 44.4% by weight of (B)(1); from about 5 to about 30% by weight of (B)(2); and from about 5 to about 25.2% by weight of (B)(3) based upon the total weight of (B)(1), (B)(2), and (B)(3) in the monomer mixture; C. grinding the resulting composition of the methantheline bromide and inner mixture into a powder; D. admixing said powder and a polymerizable monomer mixture containing:
Claim 25
Dependent Claim 98 words
polymerizable diester of a member selected from the group consisting of acrylic acid, methacrylic acid, and mixtures thereof; and a polyhydric alcohol; and wherein tHe monomer mixture contains from about 25 to about 44.4% by weight of (B)(1); from about 5 to about 30% by weight of (B)(2); and from about 5 to about 25.2% by weight of (B)(3) based upon the total weight of (B)(1), (B)(2), and (B)(3) in the monomer mixture; C. grinding the resulting composition of the methantheline bromide and inner mixture into a powder; D. admixing said powder and a polymerizable monomer mixture containing:
Claim 26
Dependent Claim 144 words
The composition of claim 1 wherein each of said polymerizable monoesters (A)(1) and (B)(1) is a monoester of a member selected from the group consisting of acrylic acid, methacrylic acid, and mixtures thereof; and a polyhydric alcohol selected from the group consisting of ethylene glycol, 1,3-propanediol, diethylene glycol, dipropylene glycol, polyethylene glycol, polypropylene glycol, 1,6-hexamethylene glycol, 1,4-butanediol, glycerol, trimethylol propane, trimethylolethane, pentaerythritol, mannitol, and sorbitol; wherein said polymerizable sulfur-containing material (B)(2) is selected from the group consisting of p-vinylbenzene sulfonic acid, ammonium salts thereof, alkali metal salts thereof, and mixtures thereof; and wherein each of said diesters (A)(2) and (B)(3) is selected from the group consisting of ethylene glycol diacrylate, ethylene glycol dimethacrylate, 1,2-butylene dimethacrylate, 1,3-butylene dimethacrylate, 1,4-butylene dimethacrylate, propylene glycol diacrylate, propylene glycol dimethacrylate, diethylene glycol dimethacrylate, dipropylene glycol dimethacrylate, diethylene glycol diacrylate, dipropylene glycol diacrylate, tetraethylene glycol dimethacrylate, and tetraethylene glycol diacrylate.
Claim 27
Dependent Claim 54 words
The method for preparing the sustained release pharmaceutical composition of claim 1 which comprises: A. entrapping the methantheline bromide in an inner matrix in an amount at least sufficient for the total dosage requirement during a treatment period; B. the inner matrix being a water-insoluble but water-swellable hydrophilic polymer of a monomer mixture containing:
Claim 28
Dependent Claim 53 words
The composition of claim 1 wherein each of said polymerizable monoesters (A)(1) and (B)(1) is selected from the group consisting of 2-hydroxy ethyl methacrylate, 2-hydroxy ethyl acrylate, 2-hydroxy propyl methacrylate, diethylene glycol monomethacrylate, diethylene glycol monoacrylate, 2-hydroxy propyl acrylate, 3-hydroxy propyl methacrylate, 3-hydroxy propyl acrylate, dipropylene glycol monomethacrylate, glyceryl methacrylate, and pentaerythritol methacrylate.
Claim 29
Dependent Claim 17 words
The composition of claim 1 wherein each of said monoesters (A)(1) and (B)(1) is 2-hydroxy ethyl methacrylate.
Claim 30
Dependent Claim 57 words
The composition of claim 1 wherein each of said diesters (A)(2) and (B)(3) is selected from the group consisting of ethylene glycol diacrylate, ethylene gylcol dimethacrylate, 1,2-butylene dimethacrylate, 1,3-butylene dimethacrylate, 1,4-butylene dimethacrylate, propylene glycol diacrylate, propylene glycol dimethacrylate, diethylene glycol dimethacrylate, dipropylene glycol dimethacrylate, diethylene glycol diacrylate, dipropylene glycol diacrylate, tetraethylene glycol dimethacrylate, and tetraethylene glycol diacrylate.
Claim 31
Dependent Claim 21 words
The composition of claim 1 wherein said diester (A)(2) is ethylene glycol dimethacrylate and said diester (B)(3) is tetraethylene glycol dimethacrylate.
Claim 32
Dependent Claim 30 words
The composition of claim 1 wherein said polymerizable sulfur-containing material is selected from the group consisting of p-vinylbenzene sulfonic acid, ammonium salts thereof, alkali metal salts thereof, and mixtures thereof.
Claim 33
Dependent Claim 15 words
The composition of claim 1 wherein said polymerizable sulfur-containing material is sodium p-vinylbenzene sulfonic acid.
Claim 34
Dependent Claim 107 words
The composition of claim 1 wherein the monomer mixture of the outer matrix contains from about 40 to about 70% by weight of (A)(1) and from about 20 to about 49.8% by weight of (A)(2) based upon the total weight of (A)(1) and (A)(2) in said monomer mixture; and wherein the monomer mixture of the inner matrix contains from about 30 to about 44.4% by weight of (B)(1); from about 22 to about 30% by weight of (B)(2); and from about 22 to about 25.2% by weight of (B)(3) based upon the total weight of (B)(1), (B)(2), and (B)(3) in the monomer mixture of the inner matrix.
Claim 35
Dependent Claim 53 words
The composition of claim 3 wherein each of said polymerizable monoesters (A)(1) and (B)(1) is selected from the group consisting of 2-hydroxy ethyl methacrylate, 2-hydroxy ethyl acrylate, 2-hydroxy propyl methacrylate, diethylene glycol monomethacrylate, diethylene glycol monoacrylate, 2-hydroxy propyl acrylate, 3-hydroxy propyl methacrylate, 3-hydroxy propyl acrylate, dipropylene glycol monomethacrylate, glyceryl methacrylate, and pentaerythritol methacrylate.
Claim 36
Dependent Claim 107 words
The composition of claim 12 wherein the monomer mixture of the outer matrix contains from about 40 to about 70% by weight of (A)(1) and from about 20 to about 49.8% by weight of (A)(2) based upon the total weight of (A)(1) and (A)(2) in said monomer mixture; and wherein the monomer mixture of the inner matrix contains from about 30 to about 44.4% by weight of (B)(1); from about 22 to about 30% by weight of (B)(2); and from about 22 to about 25.2% by weight of (B)(3) based upon the total weight of (B)(1), (B)(2), and (B)(3) in the monomer mixture of the inner matrix.
Claim 37
Dependent Claim 41 words
The composition of claim 1 wherein each of said monomers (A)(1) and (B)(1) is 2-hydroxy ethyl methacrylate, said sulfur-containing monomer (B)(2) is sodium p-toluene sulfonic acid; said diester (A)(2) is ethylene glycol dimethacrylate; and said diester (B)(3) is tetraethylene glycol dimethacrylate.
Claim 38
Dependent Claim 107 words
The composition of claim 14 wherein the monomer mixture of the outer matrix contains from about 40 to about 70% by weight of (A)(1) and from about 20 to about 49.8% by weight of (A)(2) based upon the total weight of (A)(1) and (A)(2) in said monomer mixture; and wherein the monomer mixture of the inner matrix contains from about 30 to about 44.4% by weight of (B)(1); from about 22 to about 30% by weight of (B)(2); and from about 22 to about 25.2% by weight of (B)(3) based upon the total weight of (B)(1), (B)(2), and (B)(3) in the monomer mixture of the inner matrix.
Claim 39
Dependent Claim 58 words
The composition of claim 1 wherein the outer matrix is present in an amount from about 50 to about 80% by weight and said inner matrix is present in an amount from about 5 to about 35% by weight based upon the total weight of said outer matrix, said inner matrix, and said methantheline bromide in the composition.
Claim 40
Dependent Claim 58 words
The composition of claim 1 wherein the outer matrix is present in an amount from about 65 to about 75% by weight and said inner matrix is present in an amount from about 10 to about 25% by weight based upon the total weight of said outer matrix, said inner matrix, and said methantheline bromide in the composition.

References Cited (Backward Citations)

US3331798A Cited
US3432454A Cited
US3551556A Cited
US3689634A Cited
US3577512A Cited
US3775537A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-08-25 1979-02-24 1979-08-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-08-25 1983-02-24 1983-08-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-08-25 1987-02-24 1987-08-26 $7700.00 Window Closed / Lapsed

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