CA2488220A1 - Medicament with delayed active constituent release containing 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol - Google Patents

Medicament with delayed active constituent release containing 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol Download PDF

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Publication number
CA2488220A1
CA2488220A1 CA002488220A CA2488220A CA2488220A1 CA 2488220 A1 CA2488220 A1 CA 2488220A1 CA 002488220 A CA002488220 A CA 002488220A CA 2488220 A CA2488220 A CA 2488220A CA 2488220 A1 CA2488220 A1 CA 2488220A1
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CA
Canada
Prior art keywords
dimethylamino
methylpentan
methoxyphenyl
pharmaceutical formulation
hours
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002488220A
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French (fr)
Other versions
CA2488220C (en
Inventor
Johannes Bartholomause
Iris Ziegler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Gruenenthal GmbH
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Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2488220A1 publication Critical patent/CA2488220A1/en
Application granted granted Critical
Publication of CA2488220C publication Critical patent/CA2488220C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
    • A61K9/5042—Cellulose; Cellulose derivatives, e.g. phthalate or acetate succinate esters of hydroxypropyl methylcellulose
    • A61K9/5047—Cellulose ethers containing no ester groups, e.g. hydroxypropyl methylcellulose
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

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  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Neurology (AREA)
  • Rheumatology (AREA)
  • Urology & Nephrology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)

Abstract

The invention relates to a pharmaceutical formulation with delayed release o f the agent, containing 1-dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3 - ol or one of the pharmaceutically acceptable salts thereof in a matrix. Said matrix contains 1 to 80 percent by weight of one or several hydrophilic or hydrophobic polymer/s as pharmaceutically acceptable matrix-forming substance/s and has the following dissolution rate: 3-35 percent by weight (relative to 100 percent by weight of active substance) of 1-dimethylamino-3 - (3-methoxy-phenyl)-2-methyl-pentan-3-ol are released after 0.5 hours; 5-50 percent by weight of % 1-dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan- 3- ol are released after 1 hour; 10-75 percent by weight of 1-dimethylamino-3-( 3- methoxy-phenyl)-2-methyl-pentan-3-ol are released after 2 hours; 15-82 perce nt by weight of 1-dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol are released after 3 hours; 30-97 percent by weight of 1-dimethylamino-3-(3- methoxy-phenyl)-2-methyl-pentan-3-ol are released after 6 hours; more than 5 0 percent by weight of 1-dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3- ol are released after 12 hours; more than 70 percent by weight of 1-dimethylami no- 3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol are released after 18 hours; more than 80 percent by weight of 1-dimethylamino-3-(3-methoxy-phenyl)-2-methyl- pentan-3-ol are released after 24 hours.

Claims (15)

1. Pharmaceutical formulation with delayed release, that contains 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol or a pharmaceutically acceptable salt thereof in a matrix with delayed release of active constituent, wherein the matrix contains 1 to 80 wt.% of one or more hydrophilic or hydrophobic polymers as pharmaceutically acceptable matrix-forming agents, and exhibits the following in vitro release rates measured using the Ph. Eur. paddle method at 75 rpm in a buffer (according to Ph. Eur.) at a pH value of 6.8 at 37°C and with UV spectrometric detection:
3-35 wt.% of 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol (referred to 100 wt.% of active constituent) released after 0.5 hour, 5-50 wt.% of 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol released after 1 hour 10-75 wt.% of 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol released after 2 hours 15-82 wt.% of 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol released after 3 hours 30-97 wt.% of 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol released after 6 hours more than 50 wt.% of 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol released after 12 hours, more than 70 wt.% of 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol released after 18 hours, more than 80 wt.% of 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol released after 24 hours.
2. Pharmaceutical formulation with delayed release, that contains 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol or a pharmaceutically acceptable salt thereof in a matrix with delayed release of active constituent, wherein the matrix contains 1 to 80 wt.% of one or more hydrophilic or hydrophobic polymers as pharmaceutically acceptable matrix-forming agents and comprises as pharmaceutically acceptable matrix-forming agents cellulose ethers and/or cellulose esters that in a 2 wt.% aqueous solution at 20°C have a viscosity of 3000 to 150,000 mPa.cndot.s.
3. Pharmaceutical formulation according to one of claims 1 and 2, characterised in that it comprises as pharmaceutically acceptable matrix-forming agents cellulose ethers and/or cellulose esters that in a 2 wt.% solution at 20°C have a viscosity of 10,000 to 150,000 mPa.cndot.s.
4. Pharmaceutical formulation according to one of claims 1 to 3, characterised in that it comprises as pharmaceutically acceptable matrix-forming agents cellulose ethers and/or cellulose esters that in a 2 wt.% solution at 20°C have a viscosity of 50,000 to 150,000 mPa.cndot.s.
5. Pharmaceutical formulation according to one of claims 1 to 4, characterised in that it contains as pharmaceutically acceptable matrix-forming agents at least one substance that is selected from the group comprising hydroxypropylmethylcelluloses (HPMC), hydroxyethylcelluloses, hydroxypropylcelluloses (HPC), methylcelluloses, ethylcelluloses and carboxymethylcelluloses.
6. Pharmaceutical formulation according to one of claims 1 to 5, characterised in that it contains as pharmaceutically acceptable matrix-forming agents at least one substance that is selected from the group comprising hydroxypropylmethylcelluloses, hydroxyethylcelluloses and hydroxypropylcelluloses.
7. Pharmaceutical formulation according to one of claims 1 to 6, characterised in that the content of the delayed release active constituent is between 0.5 and 85 wt.% and the content of pharmaceutically acceptable matrix-forming agent is between 8 and 40 wt.%.
8. Pharmaceutical formulation according to one of claims 1 to 7, characterised in that the content of the delayed release active constituent is between 3 and 70 wt.%, in particular between 8 and 66 wt.%, and the content of pharmaceutically acceptable matrix-forming agent is between 10 and 35 wt.%, in particular between 10 and 30 wt.%.
9. Pharmaceutical formulation according to one of claims 1 to 8, characterised in that the peak plasma level of the active constituent in vivo is reached after 2 hours to 10 hours, in particular after 3.5 hours to 6 hours.
10. Pharmaceutical formulation according to one of claims 1 to 9, characterised in that it contains (+)-(2R,3R)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol or a pharmaceutically acceptable salt thereof.
11. Tablet for twice daily oral administration of 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol, containing a pharmaceutical formulation according to one of claims 1 to 10.
12. Use of a pharmaceutical formulation according to one of claims 1 to 10 or a tablet according to claim 11 for the production of a medicament for treating increased urinary urgency or urinary incontinence.
13. Use of 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol for producing a medicament for treating increased urinary urgency or urinary incontinence, characterised in that 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol is contained in a pharmaceutical formulation according to one of claims 1 to 10.
14. Use of a pharmaceutical formulation according to one of claims 1 to 10 or a tablet according to claim 11 for the production of a medicament for treating pain, in particular chronic, visceral, neuropathic or acute pain or inflammation pain.
15. Use of 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol for the production of a medicament for treating pain, in particular chronic, visceral, neuropathic or acute pain or inflammation pain, characterised in that 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol is contained in a pharmaceutical formulation according to one of claims 1 to 10.
CA2488220A 2002-05-29 2003-05-26 Medicament with delayed active constituent release containing 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol Expired - Fee Related CA2488220C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10224108.2 2002-05-29
DE10224108A DE10224108A1 (en) 2002-05-29 2002-05-29 1-Dimethylamino-3- (3-methoxyphenyl) -2-methylpentan-3-ol containing sustained-release drug
PCT/EP2003/005488 WO2003099267A1 (en) 2002-05-29 2003-05-26 Medicament with delayed release of the active substance, containing 1-dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol

Publications (2)

Publication Number Publication Date
CA2488220A1 true CA2488220A1 (en) 2003-12-04
CA2488220C CA2488220C (en) 2011-02-01

Family

ID=29557413

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2488220A Expired - Fee Related CA2488220C (en) 2002-05-29 2003-05-26 Medicament with delayed active constituent release containing 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol

Country Status (14)

Country Link
EP (1) EP1507519B1 (en)
JP (1) JP5459818B2 (en)
AR (1) AR039900A1 (en)
AT (1) ATE326218T1 (en)
AU (1) AU2003238397A1 (en)
CA (1) CA2488220C (en)
DE (2) DE10224108A1 (en)
DK (1) DK1507519T3 (en)
ES (1) ES2263976T3 (en)
MY (1) MY134311A (en)
PE (1) PE20040529A1 (en)
PL (1) PL218397B1 (en)
PT (1) PT1507519E (en)
WO (1) WO2003099267A1 (en)

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4389393A (en) * 1982-03-26 1983-06-21 Forest Laboratories, Inc. Sustained release therapeutic compositions based on high molecular weight hydroxypropylmethylcellulose
US5032406A (en) * 1989-02-21 1991-07-16 Norwich Eaton Pharmaceuticals, Inc. Dual-action tablet
US5582837A (en) * 1992-03-25 1996-12-10 Depomed, Inc. Alkyl-substituted cellulose-based sustained-release oral drug dosage forms
JPH06172161A (en) * 1992-12-10 1994-06-21 Shin Etsu Chem Co Ltd Sustained release tablet
DE4329794C2 (en) * 1993-09-03 1997-09-18 Gruenenthal Gmbh Tramadol salt-containing drugs with delayed release
DE4426245A1 (en) * 1994-07-23 1996-02-22 Gruenenthal Gmbh 1-phenyl-3-dimethylamino-propane compounds with pharmacological activity
JPH1017497A (en) * 1996-07-02 1998-01-20 Takeda Chem Ind Ltd Sustained release pharmaceutical preparation and its production
DE10059412A1 (en) * 2000-11-30 2002-06-13 Gruenenthal Gmbh Use of 1-phenyl-3-dimethylamino-propane compounds for the treatment of urinary incontinence
DE10146275A1 (en) * 2001-09-18 2003-04-24 Gruenenthal Gmbh Combination of selected opioids with muscarinic antagonists for the treatment of urinary incontinence

Also Published As

Publication number Publication date
PL374186A1 (en) 2005-10-03
JP2005534640A (en) 2005-11-17
AR039900A1 (en) 2005-03-09
MY134311A (en) 2007-12-31
PL218397B1 (en) 2014-11-28
PE20040529A1 (en) 2004-08-24
ATE326218T1 (en) 2006-06-15
ES2263976T3 (en) 2006-12-16
DE50303372D1 (en) 2006-06-22
JP5459818B2 (en) 2014-04-02
AU2003238397A1 (en) 2003-12-12
DK1507519T3 (en) 2006-08-28
WO2003099267A1 (en) 2003-12-04
DE10224108A1 (en) 2004-01-29
PT1507519E (en) 2006-08-31
EP1507519B1 (en) 2006-05-17
EP1507519A1 (en) 2005-02-23
CA2488220C (en) 2011-02-01

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Effective date: 20160526