CA1100040A - Sustained release pharmaceutical composition - Google Patents
Sustained release pharmaceutical compositionInfo
- Publication number
- CA1100040A CA1100040A CA286,153A CA286153A CA1100040A CA 1100040 A CA1100040 A CA 1100040A CA 286153 A CA286153 A CA 286153A CA 1100040 A CA1100040 A CA 1100040A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- composition
- spheroids
- propranolol
- film coat
- 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.)
- Expired
Links
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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
Abstract
ICI CASE PH. 29592 ABSTRACT OF THE DISCLOSURE
Sustained release pharmaceutical composition consisting of a hard gelatine capsule containing film coated spheroids, the spheroids comprising propranolol, or a pharmaceutically-acceptable salt thereof, in admixture with non - water-swellable microcrystalline cellulose, and the said spheroids having a film coat comprising ethylcellulose optionally together with hydroxypropyl methylcellulose and/or a plasticizer.
Sustained release pharmaceutical composition consisting of a hard gelatine capsule containing film coated spheroids, the spheroids comprising propranolol, or a pharmaceutically-acceptable salt thereof, in admixture with non - water-swellable microcrystalline cellulose, and the said spheroids having a film coat comprising ethylcellulose optionally together with hydroxypropyl methylcellulose and/or a plasticizer.
Description
llO~Q40 This invent,ion relates to a sustained release pharmaceutical c-mposition and more particularly it relatæs to a sust,ained release pharmaceutical composition containing propranolo~ or a pharmaceutically-acceptable acid-addition salt thereof.
Propranolol hydrochloride is an important med;c~amel~t hich is widely used throughout the world. It is a ~-adrenergic blocking agent which is mainly used for the treatmen~ of angina pectoris, cardiac arrhythmias and hypertension. The chemical name for propranolol is dl-l-isopropylamino-~-(l-naphthoxy)-2-propanol. This compound and its acid-additi~n salts, and processes of manufacture thereof, are claimed in our United Kingdom patent No. 994,918. Furthermore, pharmaceut-ical compositions comprising at least one of these substances in admixtllre with a pharmaceuti~ally-acceptable diluent or carrier are c~.aimed in our United Kingdom patent No. 995,8~0.
The present invent,ion relates t,o a new sustained release pharmaceuti~,al composi~ion which is not disclosed in, nor rendered obvious by, said patent No. 995,800 nor elsewhere in the art, ~ c~ording t,o the invention there is provided a sustained relea.se pharmaceutical composition consisting of a h~rd gelat,ine f~apsllle contairlinK film coated spheroids, the sa;d spheroids comprising, prior to ~oating, 40 to 65% by weight, of propran~lol cr a pharm~ceutica.lly-acceptable acid-addition salt t~hereof in a~mixture with non-water-swel].a~le microcrystallille 1100~4~
celluLose, and the said spheroids having a film coat comprising ethylcellulose optionally together with hydroxypropyl methyl-cellulose.
The term "spheroid" is weil known in the pharmaceutical art, and means a spherica] granule having a diameter of approx-imately 0.5 to 2mm. As a particularly suitable salt of propranolol there may be mentioned, for example, the hydrochloride.
A suitable microcrystalline cellulose is, for example, the mat-B erial sold as Avicel-PH-101 (available from FMC Corporati~n, American Viscose Division, Avicel Sales, Marcus Hook, Pa, U.S.A.).
According to one embodiment of the invention the uncoated spher-o;ds may, for example, contain 50 to 60% by weight of propr3nolol hydrochloride and 50 to 40% by weight of microcrystalline (ellulose, respectively.
A suitable form of ethylcellulose is that h~v;ng a visc~-sity in the range of 5 to 100 cps at 20C. (U.~S. National Formulary XIII) (content of ethoxy groups 44 to 51% by weight), and more p~rticularly a viscosity of 50 cps at 20C. (content of ethoxy groups 48 to 49% by weight). A suitable form of hydroxypropyl methylcellulose is th~t having a viscosity in the range 3 to 100 cps at 20C. (U.S. National Formulary XIII), and more particularly a viscosity of 6 cps at 20C. The film coat may, for example~ comprise ~0 to 100% by weighr of ethyl-cellulose and 20 to 0% by we~ight of hydroxypropyl methy~c~,lulose, and more particularly 90% by we;ght of ethylcellulo..e and 10% by wei~ht of hydroxypropyl methyl~ell1~lose. Tn additi~n, the film co~t may optionally contain up to 20% by weight of a rr~le~flr~
llOQO~O
plasticizer, for example a vegetable oil, for example castor oil, or glycerol, or a glyceryl ester of a fatty acid, for example glyceryl triacetate or glyceryl monoricinoleate. The film coat may comprise 5 to 15% by weight of the coated spheroids, and preferably 9 to 10% by weight thereof.
The sustained release composition of this invention may, for example, contain 100 to 200mg., and more ~articularly 160mg., of the medicament, for example propranolol hydr~chloride.
The sustained release compositions of this invention may be manufactured by well known pharmaceutical manufacturing methods. For example, the spheroids may be )nanufactured on a conventional spheroniser in which a horizontal, rough-surfaced plate rotates inside a stationary vertical cylinder, and then film coated in conventional manner in a perforated coatin~ drum, and finally the film coated spheroids filled into hard gelatine capsules using a conventional encapsulation machine.
The invent;on is illustrated hut not limited by the lollowing Example:-Example Propr~nolol hydrochloride (60kg.) and microcry.si;alline celllllose (Avicel-PH-101; 40k~.) were blended together in a 450 lilrt pl~netary mixer. Water (50kg.) was added, and the mixer was run for 10 mir.utes Imtil a homo~eneous, pla~lic m~ss was obtained. Ti,i mass was extruded under pressure through a perforaled cylinder to give ylindrical extrudates of nominally li~m. diameter.
110Q~40 The damp extrudates (in batches of 15 to 20 kg.) were placed in a spheroniser in which the rotating disc (diameter 68 cm.) rotated at 300 to 400 r.p.m. The rotation was continued for 10 minutes, and the resulting spheroids were then dried at 60 C. in a fluidised bed drier. The dried spheroids were passed over a 1.4 mm. screen, and those which passed through were subjected to a 0.7 mm. screen. The over-and under-sized spheroids were discarded.
Acceptable spheroids (100 kg.) were placed in a perfor-ated coating drum fitted with a 0.5 mm. screen and rotating at 17 r.p.m. A film formulation consisting of ethylcellulose (9 kg.) and hydroxypropyl methylcellulose (l kg.) dissolved in a mixture of dichloromethane (100 litre) and methanol (100 litre) was sprayed onto the rotating spheroids at a rate of 750 ml. per minute using a standard airless spray system. The resulting film coated spheroids were passed over a 1.4 mm. screen to remove any aggregates, and then filled into hard gelatine capsules using a conventional encapsulation machine, such that each capsule contained 160 mg. of propranolol hydrochloride. There was thus obtained a sustained release composition containing propranolol hydrochloride.
Propranolol hydrochloride is an important med;c~amel~t hich is widely used throughout the world. It is a ~-adrenergic blocking agent which is mainly used for the treatmen~ of angina pectoris, cardiac arrhythmias and hypertension. The chemical name for propranolol is dl-l-isopropylamino-~-(l-naphthoxy)-2-propanol. This compound and its acid-additi~n salts, and processes of manufacture thereof, are claimed in our United Kingdom patent No. 994,918. Furthermore, pharmaceut-ical compositions comprising at least one of these substances in admixtllre with a pharmaceuti~ally-acceptable diluent or carrier are c~.aimed in our United Kingdom patent No. 995,8~0.
The present invent,ion relates t,o a new sustained release pharmaceuti~,al composi~ion which is not disclosed in, nor rendered obvious by, said patent No. 995,800 nor elsewhere in the art, ~ c~ording t,o the invention there is provided a sustained relea.se pharmaceutical composition consisting of a h~rd gelat,ine f~apsllle contairlinK film coated spheroids, the sa;d spheroids comprising, prior to ~oating, 40 to 65% by weight, of propran~lol cr a pharm~ceutica.lly-acceptable acid-addition salt t~hereof in a~mixture with non-water-swel].a~le microcrystallille 1100~4~
celluLose, and the said spheroids having a film coat comprising ethylcellulose optionally together with hydroxypropyl methyl-cellulose.
The term "spheroid" is weil known in the pharmaceutical art, and means a spherica] granule having a diameter of approx-imately 0.5 to 2mm. As a particularly suitable salt of propranolol there may be mentioned, for example, the hydrochloride.
A suitable microcrystalline cellulose is, for example, the mat-B erial sold as Avicel-PH-101 (available from FMC Corporati~n, American Viscose Division, Avicel Sales, Marcus Hook, Pa, U.S.A.).
According to one embodiment of the invention the uncoated spher-o;ds may, for example, contain 50 to 60% by weight of propr3nolol hydrochloride and 50 to 40% by weight of microcrystalline (ellulose, respectively.
A suitable form of ethylcellulose is that h~v;ng a visc~-sity in the range of 5 to 100 cps at 20C. (U.~S. National Formulary XIII) (content of ethoxy groups 44 to 51% by weight), and more p~rticularly a viscosity of 50 cps at 20C. (content of ethoxy groups 48 to 49% by weight). A suitable form of hydroxypropyl methylcellulose is th~t having a viscosity in the range 3 to 100 cps at 20C. (U.S. National Formulary XIII), and more particularly a viscosity of 6 cps at 20C. The film coat may, for example~ comprise ~0 to 100% by weighr of ethyl-cellulose and 20 to 0% by we~ight of hydroxypropyl methy~c~,lulose, and more particularly 90% by we;ght of ethylcellulo..e and 10% by wei~ht of hydroxypropyl methyl~ell1~lose. Tn additi~n, the film co~t may optionally contain up to 20% by weight of a rr~le~flr~
llOQO~O
plasticizer, for example a vegetable oil, for example castor oil, or glycerol, or a glyceryl ester of a fatty acid, for example glyceryl triacetate or glyceryl monoricinoleate. The film coat may comprise 5 to 15% by weight of the coated spheroids, and preferably 9 to 10% by weight thereof.
The sustained release composition of this invention may, for example, contain 100 to 200mg., and more ~articularly 160mg., of the medicament, for example propranolol hydr~chloride.
The sustained release compositions of this invention may be manufactured by well known pharmaceutical manufacturing methods. For example, the spheroids may be )nanufactured on a conventional spheroniser in which a horizontal, rough-surfaced plate rotates inside a stationary vertical cylinder, and then film coated in conventional manner in a perforated coatin~ drum, and finally the film coated spheroids filled into hard gelatine capsules using a conventional encapsulation machine.
The invent;on is illustrated hut not limited by the lollowing Example:-Example Propr~nolol hydrochloride (60kg.) and microcry.si;alline celllllose (Avicel-PH-101; 40k~.) were blended together in a 450 lilrt pl~netary mixer. Water (50kg.) was added, and the mixer was run for 10 mir.utes Imtil a homo~eneous, pla~lic m~ss was obtained. Ti,i mass was extruded under pressure through a perforaled cylinder to give ylindrical extrudates of nominally li~m. diameter.
110Q~40 The damp extrudates (in batches of 15 to 20 kg.) were placed in a spheroniser in which the rotating disc (diameter 68 cm.) rotated at 300 to 400 r.p.m. The rotation was continued for 10 minutes, and the resulting spheroids were then dried at 60 C. in a fluidised bed drier. The dried spheroids were passed over a 1.4 mm. screen, and those which passed through were subjected to a 0.7 mm. screen. The over-and under-sized spheroids were discarded.
Acceptable spheroids (100 kg.) were placed in a perfor-ated coating drum fitted with a 0.5 mm. screen and rotating at 17 r.p.m. A film formulation consisting of ethylcellulose (9 kg.) and hydroxypropyl methylcellulose (l kg.) dissolved in a mixture of dichloromethane (100 litre) and methanol (100 litre) was sprayed onto the rotating spheroids at a rate of 750 ml. per minute using a standard airless spray system. The resulting film coated spheroids were passed over a 1.4 mm. screen to remove any aggregates, and then filled into hard gelatine capsules using a conventional encapsulation machine, such that each capsule contained 160 mg. of propranolol hydrochloride. There was thus obtained a sustained release composition containing propranolol hydrochloride.
Claims (16)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A sustained release pharmaceutical composition consisting of a hard gelatine capsule containing film coated spheroids, the said spheroids comprising, prior to coating, 40 to 65% by weight of propranolol or a pharmaceutically-acceptable acid-addition salt thereof in admixture with non-water-swellable microcrystalline cellulose, and the said spheroids having a film coat comprising either ethylcellulose or ethylcellulose together with hydroxypropyl methylcellulose.
2. A composition as claimed in claim 1 in which the acid-addition salt of propranolol is the hydrochloride.
3. A composition as claimed in claim 1 in which the uncoated spheroids contain 50 to 60% by weight of propranolol hydrochloride and 50 to 40% by weight of non-water-swellable microcrystalline cellulose, respectively.
4. A composition as claimed in any one of claims 1 to 3 in which the film coat comprises 5 to 15% by weight of the coated spheroids.
5. A composition as claimed in claim 1, 2, or 3 in which the film coat comprises 9 to 10% by weight of the coated spheroids.
6. A composition as claimed in any one of claims 1 to 3 in which the ethylcellulose has a viscosity in the range 5 to 100 cps at 20°C.
7. A composition as claimed in claim 1, 2, or 3 in which the ethyl-cellulose has a viscosity of 50 cps at 20°C.
8. A composition as claimed in any one of claims 1 to 3 in which the hydroxypropyl methylcellulose has a viscosity in the range 3 to 100 cps at 20°C. 6
9. A composition as claimed in claim 1, 2, or 3 in which the hydroxy-propyl methylcellulose has a viscosity of 6 cps at 20°C.
10. A composition as claimed in any one of claims 1 to 3 in which the film coat comprises 80 to 100% by weight of ethylcellulose and 20 to 0% by weight of hydroxypropyl methylcellulose.
11. A composition as claimed in claim 1, 2, or 3 in which the film coat comprises 90% by weight of ethylcellulose and 10% by weight of hydroxypropyl methylcellulose.
12. A composition as claimed in claim 1 in which the film coat contains up to 20% by weight of a plasticizer.
13. A composition as claimed in claim 12 in which the plasticizer is a vegetable oil, or glycerol, or a glyceryl ester of a fatty acid.
14. A composition as claimed in any one of claims 1 to 3 which contains 100 to 200 mg. of propranolol or a pharmaceutically-acceptable acid-addition salt thereof.
15. A composition as claimed in claim 1, 2, or 3 which contains 160 mg of propranolol hydrochloride.
16. A sustained release pharmaceutical composition as claimed in claim 1 consisting of a hard gelatine capsule containing film coated spheroids, the spheroids containing, prior to coating, 60% by weight of propranolol hydro-chloride in admixture with 40% by weight of non-water-swellable micro-crystalline cellulose, the said spheroids having a film coat consisting of 90% by weight of ethylcellulose having a viscosity of 50 cps at 20°C and 10%
by weight of hydroxypropyl methylcellulose having a viscosity of 6 cps at 20°C, the film coat comprising 9 to 10% by weight of the coated spheroids, and each capsule containing 160 mg. of propranolol hydrochloride.
by weight of hydroxypropyl methylcellulose having a viscosity of 6 cps at 20°C, the film coat comprising 9 to 10% by weight of the coated spheroids, and each capsule containing 160 mg. of propranolol hydrochloride.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB23114/77 | 1977-06-01 | ||
| GB23114/77A GB1561204A (en) | 1977-06-01 | 1977-06-01 | Sustained release pharmaceutical composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1100040A true CA1100040A (en) | 1981-04-28 |
Family
ID=10190344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA286,153A Expired CA1100040A (en) | 1977-06-01 | 1977-09-06 | Sustained release pharmaceutical composition |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4138475A (en) |
| JP (1) | JPS5459315A (en) |
| AU (1) | AU510215B2 (en) |
| BE (1) | BE859288A (en) |
| CA (1) | CA1100040A (en) |
| CH (1) | CH638399A5 (en) |
| DE (1) | DE2740286C2 (en) |
| DK (1) | DK153773C (en) |
| FR (1) | FR2392667A1 (en) |
| GB (1) | GB1561204A (en) |
| HK (1) | HK10381A (en) |
| IE (1) | IE45578B1 (en) |
| IL (1) | IL52914A (en) |
| IT (1) | IT1067667B (en) |
| KE (1) | KE3120A (en) |
| MY (1) | MY8100346A (en) |
| NL (1) | NL7805510A (en) |
| NO (1) | NO773293L (en) |
| NZ (1) | NZ185101A (en) |
| SE (1) | SE7806446L (en) |
| ZA (1) | ZA775370B (en) |
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| DE644759C (en) * | 1932-11-23 | 1937-05-12 | I G Farbenindustrie Akt Ges | Process for coating drug forms with coatings resistant to gastric acid and gastric enzymes |
| US2738303A (en) * | 1952-07-18 | 1956-03-13 | Smith Kline French Lab | Sympathomimetic preparation |
| GB742007A (en) * | 1953-04-01 | 1955-12-14 | Smith Kline & French Internat | Improvements in or relating to method of forming coated pharmaceutical pellets |
| US2853420A (en) * | 1956-01-25 | 1958-09-23 | Lowey Hans | Ethyl cellulose coatings for shaped medicinal preparations |
| US2921883A (en) * | 1957-05-03 | 1960-01-19 | Smith Kline French Lab | Novel coating material for medicaments |
| US2887440A (en) * | 1957-08-12 | 1959-05-19 | Dow Chemical Co | Enteric coating |
| US2928770A (en) * | 1958-11-28 | 1960-03-15 | Frank M Bardani | Sustained action pill |
| NL286829A (en) * | 1961-12-29 | |||
| US3146168A (en) * | 1962-04-10 | 1964-08-25 | Fmc Corp | Manufacture of pharmaceutical preparations containing cellulose crystallite aggregates |
| US3247066A (en) * | 1962-09-12 | 1966-04-19 | Parke Davis & Co | Controlled release dosage form containing water-swellable beadlet |
| US3400185A (en) * | 1965-04-08 | 1968-09-03 | Bristol Myers Co | Agglomeration of smaller pharmaceutical particles into larger microspherules and enteic-coating thereof |
| US3488418A (en) * | 1965-11-18 | 1970-01-06 | Sterling Drug Inc | Sustained relief analgesic composition |
| US3492397A (en) * | 1967-04-07 | 1970-01-27 | Warner Lambert Pharmaceutical | Sustained release dosage in the pellet form and process thereof |
| US3576759A (en) * | 1968-04-12 | 1971-04-27 | Ncr Co | Process for en masse production of spherules by desiccation |
| CA935093A (en) * | 1969-07-28 | 1973-10-09 | Eurand S.R.L. | Method of preparing granules with controlled release of the active substance contained therein |
| DE2010416B2 (en) * | 1970-03-05 | 1979-03-29 | Hoechst Ag, 6000 Frankfurt | Orally applicable dosage form with sustained release effect |
| BE795766A (en) * | 1972-02-22 | 1973-08-22 | Lilly Co Eli | PROPOXYPHENE DELAY NAPSYLATE PARTICLES AND PROCESS FOR MANUFACTURING SUCH PARTICLES |
| DE2223896A1 (en) * | 1972-05-17 | 1973-11-29 | Sanol Arznei Schwarz Gmbh | PROCESS FOR APPLYING FINE PARTICULAR MEDICINAL PRODUCTS |
| US3947592A (en) * | 1972-05-22 | 1976-03-30 | Indiana University Foundation | Treatment of opiate addiction |
| DE2301664C3 (en) * | 1973-01-13 | 1979-07-12 | Byk Gulden Lomberg Chemische Fabrik Gmbh, 7750 Konstanz | Oral medicine containing nitroglycerin |
| GB1468172A (en) * | 1973-03-28 | 1977-03-23 | Benzon As Alfred | Oral drug preparations |
| GB1425550A (en) * | 1973-04-25 | 1976-02-18 | Alza Corp | Device for releasing active agent and process for producing the same |
| ZA742728B (en) * | 1973-05-08 | 1975-04-30 | Simes | Pharmaceutical composition for the treatment of coronaric ailments |
| DE2336218C3 (en) * | 1973-07-17 | 1985-11-14 | Byk Gulden Lomberg Chemische Fabrik Gmbh, 7750 Konstanz | Oral dosage form |
| DE2343218C2 (en) * | 1973-08-28 | 1986-08-07 | Hoechst Ag, 6230 Frankfurt | Pellets containing furosemide |
| JPS50129727A (en) * | 1974-04-04 | 1975-10-14 |
-
1977
- 1977-06-01 GB GB23114/77A patent/GB1561204A/en not_active Expired
- 1977-09-02 IE IE1825/77A patent/IE45578B1/en not_active IP Right Cessation
- 1977-09-05 NZ NZ185101A patent/NZ185101A/en unknown
- 1977-09-06 ZA ZA00775370A patent/ZA775370B/en unknown
- 1977-09-06 CA CA286,153A patent/CA1100040A/en not_active Expired
- 1977-09-07 DE DE2740286A patent/DE2740286C2/en not_active Expired
- 1977-09-07 AU AU28614/77A patent/AU510215B2/en not_active Expired
- 1977-09-09 IL IL52914A patent/IL52914A/en unknown
- 1977-09-14 US US05/833,339 patent/US4138475A/en not_active Expired - Lifetime
- 1977-09-26 NO NO77773293A patent/NO773293L/en unknown
- 1977-09-30 BE BE181386A patent/BE859288A/en not_active IP Right Cessation
- 1977-11-04 FR FR7733239A patent/FR2392667A1/en active Granted
- 1977-12-09 IT IT26282/76A patent/IT1067667B/en active Protection Beyond IP Right Term
-
1978
- 1978-02-28 JP JP2273878A patent/JPS5459315A/en active Granted
- 1978-03-21 CH CH308478A patent/CH638399A5/en not_active IP Right Cessation
- 1978-05-22 NL NL7805510A patent/NL7805510A/en active Search and Examination
- 1978-06-01 SE SE7806446A patent/SE7806446L/en unknown
- 1978-06-01 DK DK244378A patent/DK153773C/en not_active IP Right Cessation
-
1981
- 1981-03-06 KE KE3120A patent/KE3120A/en unknown
- 1981-03-19 HK HK103/81A patent/HK10381A/en not_active IP Right Cessation
- 1981-12-30 MY MY346/81A patent/MY8100346A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KE3120A (en) | 1981-04-10 |
| IL52914A (en) | 1980-06-30 |
| GB1561204A (en) | 1980-02-13 |
| HK10381A (en) | 1981-03-27 |
| DE2740286C2 (en) | 1984-05-03 |
| NZ185101A (en) | 1979-03-28 |
| SE7806446L (en) | 1978-12-02 |
| IE45578B1 (en) | 1982-10-06 |
| JPS5740804B2 (en) | 1982-08-30 |
| BE859288A (en) | 1978-03-30 |
| DK244378A (en) | 1978-12-02 |
| MY8100346A (en) | 1981-12-31 |
| DE2740286A1 (en) | 1978-12-07 |
| FR2392667B1 (en) | 1981-07-31 |
| IE45578L (en) | 1978-12-01 |
| ZA775370B (en) | 1979-01-31 |
| CH638399A5 (en) | 1983-09-30 |
| AU510215B2 (en) | 1980-06-12 |
| NL7805510A (en) | 1978-12-05 |
| US4138475A (en) | 1979-02-06 |
| DK153773C (en) | 1989-01-16 |
| FR2392667A1 (en) | 1978-12-29 |
| JPS5459315A (en) | 1979-05-12 |
| AU2861477A (en) | 1979-03-15 |
| NO773293L (en) | 1978-12-04 |
| DK153773B (en) | 1988-09-05 |
| IT1067667B (en) | 1985-03-16 |
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