AP611A - Oral liquid compositions containing paroxetine resinate. - Google Patents

Oral liquid compositions containing paroxetine resinate. Download PDF

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Publication number
AP611A
AP611A APAP/P/1996/000839A AP9600839A AP611A AP 611 A AP611 A AP 611A AP 9600839 A AP9600839 A AP 9600839A AP 611 A AP611 A AP 611A
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AP
ARIPO
Prior art keywords
pharmaceutical composition
paroxetine
depression
oral liquid
composition according
Prior art date
Application number
APAP/P/1996/000839A
Other versions
AP9600839A0 (en
Inventor
Graham Stanley Leonard
David Cooper
Original Assignee
Smithkline Beecham Plc
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 Smithkline Beecham Plc filed Critical Smithkline Beecham Plc
Publication of AP9600839A0 publication Critical patent/AP9600839A0/en
Application granted granted Critical
Publication of AP611A publication Critical patent/AP611A/en

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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
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4525—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/58—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
    • A61K47/585—Ion exchange resins, e.g. polystyrene sulfonic acid resin
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • 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
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents

Abstract

An oral liquid pharmaceutical composition comprising a paroxetine-amberlite irp88 complex.

Description

AP . Ο Ο 6 1 1
ORAL LIQUID COMPOSITIONS CONTAINING PAROXETINE RESINATE
The present invention relates to novel formulations and to the use of such aformulation in the treatment and/or prevention of certain disorders. US Patent 4,007,196 describes certain compounds which possess anti-depressant activity. One specific compound mentioned in this patent is known asparoxetine and which has the following formula:
F
C 10 15 20 c c 25 30
H
This compound has been approved for human use and is being sold in manycountries around the world as an anti-depressant agenL
All paroxetine sold to date has been in the form of oral swallow tablets.
Many physicians have expressed a desire to be able to prescribe an oralliquid containing paroxetine and some have even made their own oral liquid bycrushing conventional swallow tablets and mixing them with water. There arehowever, a number of draw-backs to this oral liquid, firstly paroxetine has a verybitter taste which is highly noticeable when administered as an oral liquid, secondlysuch oral liquids have poor stability qualities and have a shelf-life of only a few days. WO 91/13612 relates to the sustained release of pharmaceuticals usingcompositions in which the drug is complexed with an ion-exchange resin. Thespecific ion-exchange resin described in this published patent application is AmberliteIRP-69.
When Amberlite IRP-69 is used to complex with paroxetine it was foundthat whilst the taste was effectively masked the composition had an unacceptably lowbioavailability when compared to a swallow tablet.
It has now been found that Amberlite IRP-88 can be used to form a stabletaste masted complex with paroxetine and which complex has acceptablebioavailability when compared to the conventional swallow tablet
Accordingly, the present invention provides an oral liquid pharmaceuticalcomposition comprising a paroxetine - Amberlite IRP-88 complex.
Amberlite IRP-88 is commercially available from Rohm & Haas in apharmaceutically acceptable grade. - 1 - AP'?·' 9 6 / 0 0 8 3 9 AJP . Ο Ο 6 1 1
The oral liquid pharmaceutical composition is prepared in conventionalmanner such as by mixing paroxetine and Amberlite IRP-88 together in an aqueousmedium. Suitably the ERP-88 and paroxetine are present in a ratio of 1:1 to 2:1. Itshould be appreciated that superior taste masking properties are obtained with a 2:1 5 ratio.
Other pharmaceutically acceptable excipients may also be added such asthickeners such as Keltrol and/or Avicel (in particular Avicel CL 611); dispersantssuch as propylene glycol; moisture retaining agents such as glycerol; sweetners suchas sorbitol and sodium saccharin buffering agents such as citric acid and sodium 10 citrate; preservatives such as sodium benzoate and mixtures of methyl and and propylparabens (parahydroxybenzoates), artificial colours such as F D and C Yellow No. 6Sunset Yellow; flavouring such as Givaudan Natural Orange and/or Lemon; andantifoaming agents such as silicone anti-foam.
Preferably the amounts of buffering agents are controlled to give a pH of 4'15 to 6. Most preferably a pH of 4.5 to 6.0.
The amount of paroxetine used is adjusted such that in a single unit dosethere is a therapeutically effective amount of paroxetine. Preferably the unit dosecontains from 10 to 100 mg paroxetine (as measured in terms of the free base). Morepreferable the amount of paroxetine in a unit dose is lOmg, 20mg, 30mg, 40mg or 20 50mg. The most preferred amount of paroxetine in a unit dose is 20rag of paroxetine.
Preferably the volume of liquid in a unit dose is in the range 5 to 20ml mostpreferably 10ml.
Preferably paroxetine used in the formulation is in the form of thehydrocholide hemi-hydrate which may be prepared according to the procedures 25 outlined in US Patent 4,721,723.
Suitable procedures for preparing paroxetine include those mentioned in US
Patents 4,009.196.4,902,801, 4,861,893 and 5,039,803 and PCT/GB 93/00721.
It has been mentioned that paroxetine has particular utility in the treatment of depression, paroxetine may also be used in the treatment of mixed anxiety and 30 depression, obsessive compulsive disorders, panic, pain, obesity, senile dementia,migraine, bulimia, anorexia, social phobia and the depression arising from pre-menstrual tension and adolescence.
The present invention therefore also provides a method of treating orpreventing any of the above disorders which comprises administering an effective or 35 prophylatic amount of an oral liquid pharmaceutical composition comprising aparoxetine-Amberlite IRP-88 complex to a sufferer in need thereof.
The present invention further provides the use of an oral liquidpharmaceutical composition comprising a paroxetine-Amberlite IRP-88 complex inthe manufacture of a medicament for treating or preventing the above disorders. -2- AP/P/ 9 6 / 0 0 8 3 9 AP . C0 6 1 1
The present invention yet further provides a pharmaceutical composition foruse in the treatment or prevention of the above disorders which comprises aparoxetine-Amberlite IRP-88 complex admixed with a pharmaceutically acceptablecarrier. 5 The following examples illustrate the present invention:
Example 1 (1:1) Ratio of Amberlite IRP-88 to paroxetine. mg/10 ml Paroxetine hydrochloride t 22.8 Amberlite IRP 88 (< 63 pm) 22.8 o Keltrol 40.0 Propylene Glycol 350.0 o Glycerol 350.0 Sorbitol (70%) 4000.0 Citric acid 15.0 Sodium Citrate 10.0 Sodium benzoate 10.0 Sodium Saccharin 5.0 Sunset Yellow 0.5 Givaudan Natural Orange 1.0 Givaudan Natural Lemon 2.0 Antifoam Silicone 20.0 Water to 10.0 ?/P/ 9 6 / 0 0 8 3 9 < 10 C Example 2 (2:1) Ratio of Amberlite IRP to paroxetine mg/lOml
Paroxetine hydrochloride (< 180 microns) 22.8 Amberlite IRP 88 (< 200 mesh) 40.0· Avicel CL 611 300.0 Propylene Glycol 500.0 Glycerol 500.0 Sorbitol (70%) 4000.0 Citric acid (anhydrous) 15.0 -3- AP. C Ο 6 1 1
Sodium Citrate (dihydrate) 10.0
Methyl parahydroxybenzoate 20.0
Propyl parahydroxybenzoate 6.0
Sodium Saccharin 5.0 FD&amp;C Yellow No. 6 0.9
Givaudan Natural Orange 74388-74 1.0 mcl
Givaudan Natural Lemon74940-74 2.0 mcl
Silicone Antifoam 1510 20.0
Water to 10.0 * on an Anhydrous basis
Example 35
As above but 40.0 mg was replaced with 300 mg of Avicel CL 611. c
Example 4 10 As above but 15 mg of Keltrol and 300 mg of Avicel CL 611 was used. AP/P/ 96 /00839 -4-

Claims (11)

  1. ί&amp; .00611 Claims 5 1. An oral liquid pharmaceutical composition comprising a paroxetine - AmberliteIRP-88 complex.
  2. 2. A process for preparing a pharmaceutical composition as defined in claim 1 whichprocess comprises mixing paroxetine and Amberlite IRP-88 together in aqueous medium. 10
  3. 3. A process according to claim 2 in which the molar ratio of IRP 88 to paroxetine is 1:1 to 2:1. r ' 15
  4. 4. A pharmaceutical composition according to claim 1 in which any one or more ofthe following is added; thickeners, dispersants, moisture retaining agents,sweeteners, buffering agents, preservatives, artificial colours, flavourings and r K. anti-foaming agents. 20
  5. 5. A pharmaceutical composition according to claim 4 in which the amount ofbuffering agents are controlled to give a pH of 4 to 6.
  6. 6. A pharmaceutical composition according to any one of claims 1,4 or 5 which isin the form of a unit dose. 25
  7. 7. A pharmaceutical composition according to claim 6 in which the amount ofparoxetine in the unit dose is lOmg, 20mg, 30mg, 40mg, or 50mg. c 30
  8. 8. A pharmaceutical composition according to claims 1 or 4 to 7 in which theparoxetine is in the form of the hydrochloride hemihydrate.
  9. 9. A method of treating or preventing mixed anxiety and depression, obsessivecompulsive disorders, panic, pain, obesity, senile dementia, migraine, bulimia, 35 anorexia, social phobia and depression arising from pre-menstrual tension andadolescence which comprises administering an effective or prophylatic amount ofan oral liquid pharmaceutical composition as defined in claim 1. According toany one of claims 1 and 4 to 8 to a sufferer in need thereof.
  10. 10. The use of an oral liquid pharmaceutical composition as defined in claim 1comprising a paroxetine-Amberlite IRP-88 complex in the manufacture ofmedicament for treating or preventing mixed anxiety and depression, obsessive -5- 6 £ 8 0 9 / 9 6 M/dV AP. Ο Ο 6 1 1 compulsive disorders, panic, pain, obesity, senile dementia, migraine, bulimia,anorexia, social phobia and depression arising from pre-menstrual tension andadolescence.
  11. 11. A pharmaceutical composition as defined in claim 1 for use in the treatment or5 prevention of anxiety and depression, obsessive compulsive disorders, panic, pain, obesity, senile dementia, migraine, bulimia, anorexia, social phobia anddepression arising from pre-menstrual tension and adolescence. CT> hO OO O o co £ £ < -6-
APAP/P/1996/000839A 1994-02-03 1995-01-30 Oral liquid compositions containing paroxetine resinate. AP611A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9402029A GB9402029D0 (en) 1994-02-03 1994-02-03 Novel formulation
PCT/EP1995/000319 WO1995020964A1 (en) 1994-02-03 1995-01-30 Oral liquid compositions containing paroxetine resinate

Publications (2)

Publication Number Publication Date
AP9600839A0 AP9600839A0 (en) 1996-07-31
AP611A true AP611A (en) 1997-09-03

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Family Applications (2)

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APAP/P/1996/000839A AP611A (en) 1994-02-03 1995-01-30 Oral liquid compositions containing paroxetine resinate.
APAP/P/1995/000715A AP536A (en) 1994-02-03 1995-02-01 Oral liquid compositions containing paroxetine resinate

Family Applications After (1)

Application Number Title Priority Date Filing Date
APAP/P/1995/000715A AP536A (en) 1994-02-03 1995-02-01 Oral liquid compositions containing paroxetine resinate

Country Status (34)

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US (1) US5811436A (en)
EP (1) EP0742715B1 (en)
JP (1) JP4445590B2 (en)
CN (1) CN1074922C (en)
AP (2) AP611A (en)
AT (1) ATE178489T1 (en)
AU (1) AU682091B2 (en)
BG (1) BG62843B1 (en)
BR (1) BR9507055A (en)
CA (1) CA2182593A1 (en)
CZ (1) CZ285128B6 (en)
DE (1) DE69508924T2 (en)
DK (1) DK0742715T3 (en)
DZ (1) DZ1850A1 (en)
ES (1) ES2129806T3 (en)
FI (1) FI118205B (en)
GB (1) GB9402029D0 (en)
GR (1) GR3030131T3 (en)
HK (1) HK1012288A1 (en)
HU (1) HUT75941A (en)
IL (1) IL112521A (en)
MA (1) MA23441A1 (en)
MX (1) MX9603203A (en)
MY (1) MY113036A (en)
NO (1) NO307954B1 (en)
NZ (1) NZ278891A (en)
OA (1) OA10446A (en)
PL (1) PL178331B1 (en)
RO (1) RO116342B1 (en)
RU (1) RU2136281C1 (en)
SK (1) SK281214B6 (en)
TW (1) TW436296B (en)
WO (1) WO1995020964A1 (en)
ZA (1) ZA95776B (en)

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GB0003232D0 (en) * 2000-02-11 2000-04-05 Smithkline Beecham Plc Novel composition
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GB0119467D0 (en) * 2001-08-09 2001-10-03 Smithkline Beecham Plc Novel compound
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US20040220153A1 (en) * 2002-09-24 2004-11-04 Jost-Price Edward Roydon Methods and reagents for the treatment of diseases and disorders associated with increased levels of proinflammatory cytokines
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US20050266082A1 (en) * 2004-05-26 2005-12-01 Patel Satishkumar A Preparation of stable paroxetine HC1 ER tablets using a melt granulation process
EP1778183B1 (en) * 2004-08-18 2018-06-27 Synthon B.V. Liquid paroxetine compositions
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KR100672184B1 (en) 2004-09-21 2007-01-19 주식회사종근당 Paroxetine cholate or cholic acid derivative salts
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CN102430122A (en) * 2005-12-13 2012-05-02 量子高科（北京）研究院有限公司 Fluoxertine hydrochloride orally disintegrating tablet and preparation method thereof
FR2912057B1 (en) * 2007-02-07 2009-04-17 Sanofi Aventis Sa PHARMACEUTICAL COMPOSITION COMPRISING SAREDUTANT AND A SELECTIVE SEROTONIN RECAPTURE INHIBITOR OR SEROTONIN / NOREPINEPHRINE RECAPTURE INHIBITOR
TW200817003A (en) * 2006-07-31 2008-04-16 Sanofi Aventis Pharmaceutical composition comprising, in combination, saredutant and a selective serotonin peuptake inhibitor or a serotonin/norepinephrine reuptake inhibitor
US20100273822A1 (en) * 2009-04-22 2010-10-28 William Wayne Howard Immediate release compositions and methods for delivering drug formulations using strong acid ion exchange resins
US8758779B2 (en) 2009-06-25 2014-06-24 Wockhardt Ltd. Pharmaceutical composition of duloxetine
US8187617B2 (en) * 2009-09-11 2012-05-29 William Wayne Howard Immediate release compositions and methods for delivering drug formulations using weak acid ion exchange resins in abnormally high pH environments
CN102905706A (en) 2010-05-19 2013-01-30 安斯泰来制药株式会社 Pharmaceutical composition containing solifenacin
CN104027306A (en) * 2014-06-25 2014-09-10 万特制药(海南)有限公司 Paroxetine oral suspension and preparation method thereof
GB201419261D0 (en) * 2014-10-29 2014-12-10 Therakind Ltd Formulations
CN104382870A (en) * 2014-10-30 2015-03-04 万全万特制药江苏有限公司 Compound containing polacrilin potassium-paroxetine
CN106309363A (en) * 2016-09-24 2017-01-11 万特制药(海南)有限公司 Paroxetine hydrochloride oral suspension and preparation method thereof
CN108926528A (en) * 2017-05-25 2018-12-04 北京万全德众医药生物技术有限公司 Liquid oral compositions containing Amisulpride resinate
WO2020160537A1 (en) 2019-02-01 2020-08-06 University Of South Carolina Bicyclic pyridine compositions and methods of using the same for cancer therapy
CN113209017B (en) * 2021-06-02 2023-06-20 上海美优制药有限公司 Paroxetine hydrochloride suspension and preparation method thereof
GB202212116D0 (en) 2022-08-19 2022-10-05 Beckley Psytech Ltd Pharmaceutically acceptable salts and Compositions thereof

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NZ278891A (en) 1998-01-26
NO963244L (en) 1996-08-02
MY113036A (en) 2001-11-30
PL178331B1 (en) 2000-04-28
DZ1850A1 (en) 2002-02-17
HK1012288A1 (en) 1999-07-30
CZ285128B6 (en) 1999-05-12
PL315679A1 (en) 1996-11-25
ATE178489T1 (en) 1999-04-15
NO307954B1 (en) 2000-06-26
DE69508924T2 (en) 1999-10-21
AP9600839A0 (en) 1996-07-31
NO963244D0 (en) 1996-08-02
RU2136281C1 (en) 1999-09-10
CN1074922C (en) 2001-11-21
JP4445590B2 (en) 2010-04-07
FI118205B (en) 2007-08-31
IL112521A0 (en) 1995-05-26
BR9507055A (en) 1997-09-02
AP536A (en) 1996-09-26
MX9603203A (en) 1997-03-29
TW436296B (en) 2001-05-28
CZ229396A3 (en) 1997-01-15
SK281214B6 (en) 2001-01-18
CA2182593A1 (en) 1995-08-10
ES2129806T3 (en) 1999-06-16
GR3030131T3 (en) 1999-07-30
OA10446A (en) 2002-03-26
RO116342B1 (en) 2001-01-30
FI963051A0 (en) 1996-08-01
BG62843B1 (en) 2000-09-29
EP0742715A1 (en) 1996-11-20
SK100496A3 (en) 1996-12-04
FI963051A (en) 1996-08-01
HU9602151D0 (en) 1996-09-30
GB9402029D0 (en) 1994-03-30
ZA95776B (en) 1996-08-01
AU682091B2 (en) 1997-09-18
DE69508924D1 (en) 1999-05-12
BG100763A (en) 1997-03-31
IL112521A (en) 1999-09-22
CN1140411A (en) 1997-01-15
HUT75941A (en) 1997-05-28
JPH09508402A (en) 1997-08-26
WO1995020964A1 (en) 1995-08-10
MA23441A1 (en) 1995-10-01
DK0742715T3 (en) 1999-10-18
AU1536895A (en) 1995-08-21
EP0742715B1 (en) 1999-04-07
AP9500715A0 (en) 1995-04-30
US5811436A (en) 1998-09-22

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