GB2235626A - Medicaments for treating respiratory disorders - Google Patents

Medicaments for treating respiratory disorders Download PDF

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Publication number
GB2235626A
GB2235626A GB9019651A GB9019651A GB2235626A GB 2235626 A GB2235626 A GB 2235626A GB 9019651 A GB9019651 A GB 9019651A GB 9019651 A GB9019651 A GB 9019651A GB 2235626 A GB2235626 A GB 2235626A
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GB
United Kingdom
Prior art keywords
salmeterol
beclomethasone dipropionate
acceptable salt
physiologically acceptable
compositions
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
GB9019651A
Other versions
GB9019651D0 (en
GB2235626B (en
Inventor
James Barry Palmer
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.)
Glaxo Group Ltd
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Glaxo Group Ltd
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
Priority claimed from GB898920391A external-priority patent/GB8920391D0/en
Priority claimed from GB898923645A external-priority patent/GB8923645D0/en
Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd
Publication of GB9019651D0 publication Critical patent/GB9019651D0/en
Publication of GB2235626A publication Critical patent/GB2235626A/en
Application granted granted Critical
Publication of GB2235626B publication Critical patent/GB2235626B/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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Abstract

Pharmaceutical compositions comprise effective amounts of salmeterol (and/or physiologically acceptable salt thereof) and beclomethasone dipropionate, in a form suitable for simultaneous, sequential or separate administration by inhalation for the treatment of respiratory disorders.

Description

- 1 54-658-520 MEDICAMENTS -..- 1 This invention relates to improvements
in the treatment of asthma and other respiratory disorders. More particularly, it relates to the use of a bronchodilator drug in combination with a steroidal anti-inflammatory drug for the treatment of respiratory disorders such as asthma, and to pharmaceutical compositions containing the two active ingredients.
Asthma is a condition characterised by variable, reversible obstruction of the airways which is caused by a complex inflammatory process within the lungs. In most cases, this process is initiated and maintained by the inhalation of antigens by sensitive atopic individuals (extrinsic asthma). However, in some patients it is caused by other mechanisms which at present are poorly understood but do not involve an allergic process (intrinsic asthma). The disease has therefore two components, spasm of the bronchial (or breathing) tubes and inflammation or swelling of the breathing tubes.
Salbutamol, the first highly selective B2adrenoceptor stimulant has been used successfully and effectively by inhalation for the immediate relief of spasm in asthma. However, when given by inhalation, salbutamol has usually a four to six hour duration of action, which is too short either to control nocturnal asthma or for convenient maintenance of the disease in some patients.
Anti-inflammatory corticosteroids such as, for example, beclomethasone dipropionate have also been administered by inhalation in the treatment of asthma, although unlike salbutamol the therapeutic benefits may not be immediately apparent. Indeed, although the benefits of inhaled beclomethasone dipropionate and its safety and efficacy in asthma therapy are wellestablished in clinical practice, the true nature of asthma as an inflammatory disease and the consequent fundamental effects of inhaled beclomethasone dipropionate in its treatment have only recently been realised.
It has, however, been recognised that asthma may be treated by using both a bronchodilator for immediate relief and a prophylactic antiinflammatory corticosteroid to treat the underlying inflammation. Such combination therapy directed at the two main underlying events in the lung (i.e. relief of spasm in the breathing tubes and treatment of inflammation in the breathing tubes) using a combination of salbutamol and beclomethasone dipropionate has previously been proposed (Ventide, Glaxo Group trade mark), but suffers a number of disadvantages in view of the above-mentioned short duration of action exhibited by salbutamol. Thus the need for a 4-hourly dosing regimen may discourage effective patient compliance and also renders the product less than satisfactory in the treatment of nocturnal asthma since the bronchodilator may not remain effective for the duration of the night, leading to impaired sleep for asthmatics troubled by nocturnal cough, breathlessness and wheeze.
The present invention is based on the concept of a novel combination therapy which has greater efficiency and duration of bronchodilator action than previously known combinations and which permits the establishment of a twice daily (bis in diem - b.i.d) dosing regimen with consequent benefits in, for example, the treatment of asthma, particularly nocturnal asthma.
Thus we have found that if the 182 -adrenoreceptor stimulant bronchodilator salmeterol and/or a physioilogically acceptable salt thereof is combined with beclomethasone dipropionate in a form suitable for administration by inhalation, the resulting compositions 1 may be administered on a b.i.d. basis to provide effective treatment and/or prophylactic therapy for asthmatics. In particular such administration has been shown to lead to improvement in daytime lung function, requirement for additional symptomatic bronchodilator and almost complete abolition of nocturnal asthma while giving rise to minimal systemic side effects.
Salmeterol is one of a range of bronchodilators having extended duration of action which is described in British Patent Specification No. 2140800, and is systematically named 4-hydroxy-a1-[[[6(4phenylbutoxy)hexyl]amino]methyl]-1,3-benzenedimethanol.
According to one aspect of the invention there are provided pharmaceutical compositions comprising effective amounts of salmeterol (and/or a physiologically acceptable salt thereof) and beclomethasone dipropionate as a combined preparation for simultaneous, sequential or separate administration by inhalation in the treatment of respiratory disorders.
The invention additionally relates to the use of salmeterol (and/or a physiologically acceptable salt thereof) and beclomethasone dipropionate in the manufacture of pharmaceutical compositions as combined preparations for simultaneous, sequential or separate administration of salmeterol and beclomethasone dipropionate by inhalation in the treatment of respiratory disorders.
According to a further feature of the invention there is provided a method of treating respiratory disorders which comprises the simultaneous, sequential or separate administration by inhalation of effective amounts of salmeterol (and/or a physiologically acceptable salt thereof) and beclomethasone dipropionate.
Suitable physiologically acceptable salts of salmeterol include acid addition salts derived from inorganic and organic acids, such as the hydrochloride, hydrobromide, sulphate, phosphate, maleate, tartrate, citrate, benzoate, 4-methoxybenzoate, 2- or 4hydroxybenzoate, 4chlorobenzoate, p-toluenesulphonate, - 4 methanesulphonate, ascorbate, salicylate, acetate, fumarate, succinate, lactate, glutarate, gluconate, tricarballylate, hydroxynapthalenecarboxylate, e.g. 1hydroxy- or 3-hydroxy-2- naphthalenecarboxylate or oleate. Salmeterol is preferably used in the form of its 1-hydroyxy-2-napthalene carboxylate salt (hydroxynapthoate).
For administration by inhalation, the compositions according to the invention are conveniently delivered by conventional means i.e. in the form of a metered dose inhaler prepared in a conventional manner or in combination with a spacer device such as the Volumatic (Glaxo Group trade mark) device. In the case of a metered dose inhaler, a metering valve is provided to deliver a metered amount of the composition. Spray compositions may for example be formulated as aqueous solutions orsuspensions and may be administered by a nebuliser. Aerosol spray formulations for example in which the active ingredients are suspended, optionally together with one or more stabilisers, in a propellant, e.g. a halgenated hydrocarbon such as trichlorofluoromethane, dichlorodifluoromethane, 1,2dichlorotetrafluoroethane, trichlorotrifluoroethane, monochloropentafluoroethane, chloroform or methylene chloride may also be employed. The two drugs may be administered separately in similar ways.
Alternatively, for administration by inhalation or insufflation, the compositions according to the invention may take the form of a dry powder composition, for example a powder mix of the active ingredients and a suitable carrier such as lactose. The powder compositions may be presented in unit dosage form in, for example, capsules, cartrides or blister packs from which the powder may be administered with the aid of an inhaler such as the Rotahaler inhaler (Glaxo Group trade mark) or in the case of blister packs by means of the Diskhaler inhaler (Glaxo Group trade mark).
1 Z i The ratio of salmeterol to beclomethasone dipropionate in the compositions according to the invention is preferably within the range 2:1 to 1:40. The two drugs may be administered separately in the same ratio. Each metered dose or actuation of the inhaler will generally contain from 25 Mg to 100 Mg of salmeterol and from 50 gg to 1000 gg of beclomethasone dipropionate. As hereinbefore indicated, it is intended that the pharmaceutical compositions will be administered twice daily.
suitable daily dose of salmeterol for inhalation is in the range 20 gg to 200 gg.
suitable daily dose of beclomethasone dipropionate for inhalation is in the range of 100 gg to 2000 gg depending on the severity of the disease.
The precise dose employed will of course depend on the method of administration,the age, weight and condition of the patient and will be determined by the clinician depending on the severity and the type of asthma.
In order that the invention may be more fully understood, the following examples are given by way of illustration only.
EXAMPLE 1 - Metered Dose Inhaler Active Inqredient Tarqet per Per Inhaler Actuation % W/ Salmeterol 25.0 gg (as hydroxynapthoate) 0.0448 Beclomethasone dipropionate 50.0 gg BP 0.0647 Stabiliser 7.5 Mg 0.0110 Trichlorofluoromethane 23.67 mg Dichlorodifluoromethane 61.25 mg EXAMPLE 2 - Metered Dose Inhaler 27.8207 72.0588 Active Ingredient Tarqet per Per Inhaler Actuation % W/ Salmeterol 25.0 gg 0.0448 (as hydroxynapthoate) Beclomethasone dipropionate 100.0 gg BP 0.1294 Stabiliser 10.5 gg 0.0129 Trichlorofluoromethane 23.62 mg 27.7541 Dichlorodifluoromethane 61.25 mg 72.0588 p 1 7 - EXAMPLE 3 - Metered Dose Inhaler Active Inqredient Tarqet per Per Inhaler Actuation w/w Salmeterol 25.0 gg (as hydroxynapthoate) 0.0448 Beclomethasone dipropionate 250.0 gg BP 0.3235 Stabiliser 25.0 Mg 0.0324 Trichlorofluoromethane 23.45 mg 27.5405 Dichlorodifluoromethane 61.25 mg EXAMPLE 4 Metered Dose Inhaler 72.0588 Active Inqredient Tarqet per Per Inhaler Actuation % w/w Salmeterol 100.0 Ag (as hydroxynaphthoate) 0.1791 Beclomethasone dipropionate 125.0 gg BP 0.3235 Stabiliser 25.0 gg 0.0324 Trichlorofluoromethane 23.43 mg 27.4062 Dichlorodifluoromethane 61.25 mg 72.0588 In Examples 1 to 4 micronised beclomethasone dipropionate (as the trichlorofluoromethane solvate) and 8 - micronised salmeterol (as the hydroxynapthoate) are added in the proportions given above either dry or after predispersal in a small quantity of stabiliser (disodium dioctylsulphosuccinate, lecithin, oleic acid or sorbitan trioleate)/trichlorofluoromethane solution to a suspension vessel containing the main bulk of the trichlorofluoromethane solution. The resulting suspension is further dispersed by an appropriate mixing system using, for example, a high sheer blender, ultrasonics or a microfluidiser until an ultrafine dispersion is created. The suspension is then continuously recirculated to suitable filling equipment designed for cold fill or pre'ssure filling of dichlorodifluoromethane. Alternatively, the suspension may be prepared in a suitable chilled solution of stabiliser, in trichlorofluoromethane/ dichlorodifluromethane.
EXAMPLE 5 - Metered Dose Dry Powder Formulation Active Inqredient Salmeterol (as hydroxynaphthoate) Beclomethasone dipropionate BP (anhydrous or as monohydrate) Lactose Ph.Eur.
to to mq/cartridqe or bliste 36.3 50.00 12.5 mg or 2 5. Omg EXAMPLE 6 Metered Dose Dry Powder Formulation Active Ingredient Salmeterol (as hydroxynaphthoate) Beclomethasone dipropionate BP (anhydrous or as monohydrate) Lactose Ph.Eur.
to to U9/cartridqe or blister 36.25 100.00 12. 5 mg or 25.0 mg EXAMPLE 7 Metered Dose Drv Powder Formulation Active Inqredient Salmeterol (as hydroxynaphthoate) Beclomethasone dipropionate (anhydrous or as monohydrate) Lactose Ph.Cur.
to to ucr/cartridge or blister 72.5 100.00 12. 5 mg or 25. 0 mg EXAMPLE 8 - Metered Dose Dry Powder Formulation Active Ingredient Salmetreol (as hydroxynaphthoate) Beclomethasone dipropionate BP (anhydrous or as monohydrate) Lactose Ph.Eur.
t ucr/cartridqe or blister 72.5 200.00 to to 12. 5 mg or 25. 0 mg h 11 EXAMPLE 9 - Metered Dose Dry Powder Formulation Active Inqredient Salneterol (as hydroxynaphthoate) Beclomethasone dipropionate BP (anyhydrous or as monohydrate) Lactose Ph.Eur.
to to uq/cartridqe or blister 72.5 500.0 12. 5 mg or 25. 0 mg EXAMPLE 10 Metered Dose Dry Powder Formulation Active Ingredient Salmeterol (as hydroxynaphthoate) Beclomethasone dipropionate BP (anhydrous or as monohydrate) Lactose Ph. eur.
ucr/cartridqe or blister 72.5 1000.0 to to 12. 5 mg or 25.0 mg - 12 EXAMPLE 11 - Metered Dose Drv Powder Formulation Active Ingredient tLg/cartridqe or blister Salmeterol (as hydroxynaphthoate) 145.0 Beclomethasone dipropionate (anydrous or as monohydrate) 250.0 Lactose Ph. Eur.
to to 12. 5 mg or 25. 0 mg In Examples 5 to 11 the active ingredients are micronised and bulk blended with the lactose in the proportions given above. The blend is filled into hard gelatin capsules or cartridges or in specifically constructed double foil blister packs (Rotadisks blister packs, Glaxo Group trade mark) to be administered by an inhaler such as the Rotahaler inhaler (Glaxo Group trade mark) or in the case of the blister packs with the Diskhaler inhaler (Glaxo Group trade mark).
1 - 13

Claims (6)

CLAIMS:
1. Pharmaceutical compositions comprising effective amounts of salmeterol (and/or a physiologically acceptable salt thereof) and beclomethasone dipropionate as a combined preparation for simultaneous, sequential or separate administration by inhalation in the treatment-of respiratory disorders.
2. Compositions as claimed in claim 1 wherein salmeterol is present as its 1-hydroxy-2naphthalenecarboxylate salt.
3. Compositions as claimed in claim 1 or claim 2 presented in the form of a metered dose inhaler or a metered dry powder composition.
4. Compositions as claimed in any of claims 1 to 3 in dosage unit form containing 25-100pg of salmeterol (optionally in the form of a physiologically acceptable salt thereof) and 50-100Ogg of beclomethasone dipropionate per dosage unit.
5. The use of salmeterol (and/or a physiologically acceptable salt thereof) and beclomethasone dipropionate in the manufacture of pharmaceutical compositions as combined preparations for simultaneous, sequential or separate administration of salmeterol and beclomethasone dipropionate by inhalation in the treatment of respiratory disorders.
6. The use of salmeterol (and/or a physiologically acceptable salt thereof) and beclomethasone dipropionate according to claim 5 in the manufacture of pharmaceutical compositions for administration on a twice daily basis.
Published 1991 atThe Patent Office. State House. 66/71 HighHolborn, TondonWCIR4TP. Further copies may be obtained from Saks Branch, Unit 6. Nine Mile point. Cwmfelinfach. Cross Keys. NewporL NPI 714Z. Printed by Multiplex techniques ltd. St Mary Cray. Kent.
GB9019651A 1989-09-08 1990-09-07 Inhalation medicaments for treating respiratory disorders Expired - Fee Related GB2235626B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB898920391A GB8920391D0 (en) 1989-09-08 1989-09-08 Medicaments
GB898923645A GB8923645D0 (en) 1989-10-20 1989-10-20 Medicaments

Publications (3)

Publication Number Publication Date
GB9019651D0 GB9019651D0 (en) 1990-10-24
GB2235626A true GB2235626A (en) 1991-03-13
GB2235626B GB2235626B (en) 1994-02-09

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GB9019651A Expired - Fee Related GB2235626B (en) 1989-09-08 1990-09-07 Inhalation medicaments for treating respiratory disorders

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EP (1) EP0416950B1 (en)
JP (1) JP3042866B2 (en)
AT (1) ATE92762T1 (en)
AU (1) AU644094B2 (en)
CA (1) CA2024872C (en)
DE (1) DE69002718T2 (en)
DK (1) DK0416950T3 (en)
FR (1) FR2651678B1 (en)
GB (1) GB2235626B (en)
IT (1) IT1241997B (en)
NZ (1) NZ235222A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE40045E1 (en) 1989-09-08 2008-02-05 Glaxo Group Limited Medicaments

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AU673660C (en) * 1991-12-18 2002-07-25 Astrazeneca Ab New combination of formoterol and budesonide
US6054487A (en) * 1997-03-18 2000-04-25 Basf Aktiengesellschaft Methods and compositions for modulating responsiveness to corticosteroids
PL336464A1 (en) * 1997-03-18 2000-06-19 Basf Ag Method of and compositions for modulating reactivity in respect to corticosteroids i
SE9703407D0 (en) 1997-09-19 1997-09-19 Astra Ab New use
SE9802073D0 (en) 1998-06-11 1998-06-11 Astra Ab New use
IT1303692B1 (en) * 1998-11-03 2001-02-23 Chiesi Farma Spa PROCEDURE FOR THE PREPARATION OF SUSPENSIONS OF PARTICLES OF DRUGS TO BE ADMINISTERED BY INHALATION.
DK1283036T3 (en) 1998-11-13 2008-03-25 Jagotec Ag Dry powder for inhalation
DE19921693A1 (en) * 1999-05-12 2000-11-16 Boehringer Ingelheim Pharma Pharmaceutical composition for treating respiratory disorders, e.g. asthma, comprises combination of anticholinergic and beta-mimetic agents having synergistic bronchospasmolytic activity and reduced side-effects
WO2001019373A2 (en) * 1999-09-17 2001-03-22 Basf Aktiengesellschaft Methods and compositions for modulating responsiveness to corticosteroids
GB0009617D0 (en) * 2000-04-18 2000-06-07 Glaxo Group Ltd Respiratory combinations
FI20002215A0 (en) 2000-10-06 2000-10-06 Orion Yhtymae Oyj Combination Particles
FI20002216A0 (en) 2000-10-06 2000-10-06 Orion Yhtymae Oyj Combination particles for asthma therapy
US7258118B2 (en) 2002-01-24 2007-08-21 Sofotec Gmbh & Co, Kg Pharmaceutical powder cartridge, and inhaler equipped with same
DE10202940A1 (en) 2002-01-24 2003-07-31 Sofotec Gmbh & Co Kg Cartridge for a powder inhaler
PT1572217E (en) 2002-12-12 2008-11-28 Nycomed Gmbh Combination medicament of r,r-formoterol and ciclesonide
SE527069C2 (en) 2003-06-19 2005-12-13 Mederio Ag Method and apparatus for administering drug powder
WO2005013963A1 (en) 2003-08-06 2005-02-17 Galephar M/F Advantageous combinations for inhalation of nacystelyn and bronchodilators
KR101214823B1 (en) 2004-07-16 2012-12-24 알미랄, 에스.에이. Inhaler for the administration of powdered pharmaceuticals, and a powder cartridge system for use with this inhaler
BRPI0720846A2 (en) 2006-12-22 2014-03-04 Almirall Lab INHALATION DEVICE FOR POWDERED DRUGS
US8815258B2 (en) 2009-05-29 2014-08-26 Pearl Therapeutics, Inc. Compositions, methods and systems for respiratory delivery of two or more active agents
CN107412212B (en) 2009-05-29 2021-01-22 珍珠治疗公司 Pulmonary delivery of long-acting muscarinic antagonists and long-acting beta2Compositions of adrenergic receptor agonists and related methods and systems
RU2696582C2 (en) 2013-03-15 2019-08-05 Перл Терапьютикс, Инк. Methods and systems for conditioning disperse crystalline materials

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Publication number Priority date Publication date Assignee Title
GB1571629A (en) * 1977-11-30 1980-07-16 Fisons Ltd Pharmaceutical compositions containing beclomethasone dipropionate
GB2107715A (en) * 1981-10-19 1983-05-05 Glaxo Group Ltd Micronised beclomethasone dipropionate monohydrate and powder inhalation compositions containing it
GB2140800A (en) * 1983-04-18 1984-12-05 Glaxo Group Ltd Phenethanolamine derivatives

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GB1571629A (en) * 1977-11-30 1980-07-16 Fisons Ltd Pharmaceutical compositions containing beclomethasone dipropionate
GB2107715A (en) * 1981-10-19 1983-05-05 Glaxo Group Ltd Micronised beclomethasone dipropionate monohydrate and powder inhalation compositions containing it
GB2140800A (en) * 1983-04-18 1984-12-05 Glaxo Group Ltd Phenethanolamine derivatives

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE40045E1 (en) 1989-09-08 2008-02-05 Glaxo Group Limited Medicaments

Also Published As

Publication number Publication date
FR2651678A1 (en) 1991-03-15
DK0416950T3 (en) 1993-10-11
AU6226090A (en) 1991-03-14
EP0416950B1 (en) 1993-08-11
JPH03167119A (en) 1991-07-19
ATE92762T1 (en) 1993-08-15
JP3042866B2 (en) 2000-05-22
CA2024872A1 (en) 1991-03-09
IT9048261A1 (en) 1992-03-07
CA2024872C (en) 2002-07-09
IT1241997B (en) 1994-02-02
AU644094B2 (en) 1993-12-02
IT9048261A0 (en) 1990-09-07
NZ235222A (en) 1992-11-25
DE69002718T2 (en) 1993-12-23
FR2651678B1 (en) 1992-04-30
GB9019651D0 (en) 1990-10-24
DE69002718D1 (en) 1993-09-16
EP0416950A1 (en) 1991-03-13
GB2235626B (en) 1994-02-09

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