NL193066C - Methyl,isopropyl-4-(2,1,3-benzoxadiazool-4-yl)-2,6-dimethyl-1,4-dihydro pyridine-3,5-dicarboxylaat en farmaceutisch preparaat dat deze verbinding bevat. - Google Patents
Methyl,isopropyl-4-(2,1,3-benzoxadiazool-4-yl)-2,6-dimethyl-1,4-dihydro pyridine-3,5-dicarboxylaat en farmaceutisch preparaat dat deze verbinding bevat. Download PDFInfo
- Publication number
- NL193066C NL193066C NL7909024A NL7909024A NL193066C NL 193066 C NL193066 C NL 193066C NL 7909024 A NL7909024 A NL 7909024A NL 7909024 A NL7909024 A NL 7909024A NL 193066 C NL193066 C NL 193066C
- Authority
- NL
- Netherlands
- Prior art keywords
- compound
- formula
- benzoxadiazol
- isopropyl
- dimethyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- -1 2,1,3-benzoxadiazol-4-yl Chemical group 0.000 title description 4
- JNLUMMRKXUTNAA-UHFFFAOYSA-N 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-5-propan-2-yloxycarbonyl-1,4-dihydropyridine-3-carboxylic acid Chemical compound CC(C)OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC2=NON=C12 JNLUMMRKXUTNAA-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 8
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical group C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000017531 blood circulation Effects 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010052895 Coronary artery insufficiency Diseases 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 206010022562 Intermittent claudication Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000002213 calciumantagonistic effect Effects 0.000 description 2
- 208000026106 cerebrovascular disease Diseases 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 208000021156 intermittent vascular claudication Diseases 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- UKVYVZLTGQVOPX-IHWYPQMZSA-N (z)-3-aminobut-2-enoic acid Chemical compound C\C(N)=C\C(O)=O UKVYVZLTGQVOPX-IHWYPQMZSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical class C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical class C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- COLPLFZHPXIFCQ-UHFFFAOYSA-N 1,4-dihydropyridine-3,5-dicarboxylic acid Chemical class OC(=O)C1=CNC=C(C(O)=O)C1 COLPLFZHPXIFCQ-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- 206010058842 Cerebrovascular insufficiency Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000003727 cerebral blood flow Effects 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000002999 depolarising effect Effects 0.000 description 1
- 229940085304 dihydropyridine derivative selective calcium channel blockers with mainly vascular effects Drugs 0.000 description 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- DYYYPIJLRRHUPR-UHFFFAOYSA-N dimethyl 1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=CNC=C(C(=O)OC)C1 DYYYPIJLRRHUPR-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
- 229960001597 nifedipine Drugs 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1283578A CH639659A5 (de) | 1978-12-18 | 1978-12-18 | Neue 1,4-dihydropyridinderivate, deren herstellung und verwendung. |
| CH1283578 | 1978-12-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NL7909024A NL7909024A (nl) | 1980-06-20 |
| NL193066B NL193066B (nl) | 1998-05-06 |
| NL193066C true NL193066C (nl) | 1998-09-08 |
Family
ID=4386824
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL7909024A NL193066C (nl) | 1978-12-18 | 1979-12-14 | Methyl,isopropyl-4-(2,1,3-benzoxadiazool-4-yl)-2,6-dimethyl-1,4-dihydro pyridine-3,5-dicarboxylaat en farmaceutisch preparaat dat deze verbinding bevat. |
| NL990014C NL990014I1 (nl) | 1978-12-18 | 1999-05-11 | Methyl, isopropyl-4-(2,1,3-benzoxadiazool-4-yl)-2,6-dimethyl-1,4-dihydro pyridine-3,5-dicarboxylaat en farmaceutisch preparaat dat deze verbinding bevat. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL990014C NL990014I1 (nl) | 1978-12-18 | 1999-05-11 | Methyl, isopropyl-4-(2,1,3-benzoxadiazool-4-yl)-2,6-dimethyl-1,4-dihydro pyridine-3,5-dicarboxylaat en farmaceutisch preparaat dat deze verbinding bevat. |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5583783A (xx) |
| AU (1) | AU536055B2 (xx) |
| BE (1) | BE880591A (xx) |
| CH (1) | CH639659A5 (xx) |
| CY (1) | CY1321A (xx) |
| DE (1) | DE2949491A1 (xx) |
| FR (1) | FR2444681A1 (xx) |
| GB (2) | GB2037766B (xx) |
| HK (1) | HK16086A (xx) |
| IE (1) | IE49496B1 (xx) |
| IT (1) | IT1164097B (xx) |
| KE (1) | KE3593A (xx) |
| MY (1) | MY8500130A (xx) |
| NL (2) | NL193066C (xx) |
| NZ (1) | NZ192422A (xx) |
| SE (1) | SE445219B (xx) |
| SG (1) | SG97585G (xx) |
| ZA (1) | ZA796842B (xx) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3022030A1 (de) * | 1980-06-12 | 1981-12-17 | Bayer Ag, 5090 Leverkusen | 4-thiazol- bzw. 4-imidazol-substituierte, 1,4-dihydropyridine, verfahren zu deren herstellung sowie diese enthaltende arzneimittel |
| CH655658B (xx) * | 1980-09-18 | 1986-05-15 | ||
| DE3269219D1 (en) * | 1981-11-17 | 1986-03-27 | Fisons Plc | Dihydropyridines, methods for their production and their formulation and use as pharmaceuticals |
| ZA83959B (en) * | 1982-03-10 | 1984-09-26 | Sandoz Ltd | 1,4-dihydropyridine derivatives,their preparation and pharmaceutical compositions containing them |
| US4414213A (en) * | 1982-03-22 | 1983-11-08 | Mead Johnson & Company | Dihydropyridyl cyclic imidate esters and their pharmaceutical use |
| IL68975A (en) * | 1982-06-15 | 1987-01-30 | Sandoz Ag | 4-(2,1,3-benzoxadiazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylic acid ester derivatives in optically active form,their preparation and pharmaceutical compositions containing them |
| FR2528431B1 (fr) * | 1982-06-15 | 1986-01-10 | Sandoz Sa | Nouveaux derives de la 1,4-dihydropyridine, leur preparation et leur utilisation comme medicaments |
| JPS5978186A (ja) * | 1982-10-27 | 1984-05-04 | Yoshitomi Pharmaceut Ind Ltd | １，４−ジヒドロピリジン−３，５−ジカルボン酸エステル誘導体 |
| US4794111A (en) * | 1984-05-23 | 1988-12-27 | Bayer Aktiengesellschaft | Dihydropyridine preparations containing β-blockers |
| NL194389C (nl) * | 1984-06-14 | 2002-03-04 | Novartis Ag | Werkwijze voor het bereiden van een vaste dispersie van een farmaceutisch actief middel dat een lage oplosbaarheid in water heeft, in een vaste matrix van een in water oplosbaar polyalkyleenglycol als drager. |
| US5260321A (en) * | 1984-11-12 | 1993-11-09 | Sandoz Ltd. | Use of 1,4-dihydropyridine derivatives and combinations thereof with calcitonins |
| HU197201B (en) * | 1985-10-01 | 1989-03-28 | Sandoz Ag | Process for producing oral pharmaceutical compositions of controlled solubility of the active components |
| DE3542794A1 (de) * | 1985-12-04 | 1987-06-11 | Bayer Ag | Antihypertensives kombinationspraeparat |
| GB8626217D0 (en) * | 1986-11-03 | 1986-12-03 | Sandoz Ltd | Pharmaceutical compositions |
| US4816263A (en) * | 1987-10-02 | 1989-03-28 | Alza Corporation | Dosage form for treating cardiovascular diseases comprising isradipine |
| KR940003492B1 (ko) * | 1988-10-27 | 1994-04-23 | 주식회사 유한양행 | 1,4-디하이드로피리딘유도체 및 그의 제조방법 |
| DE4222770A1 (de) * | 1992-07-10 | 1994-01-13 | Bayer Ag | Lichtaktivierbare 1-(2-Nitrobenzyl)-substituierte 1,4-Dihydropyridine |
| AU2003217676B2 (en) | 2002-02-22 | 2009-06-11 | Takeda Pharmaceutical Company Limited | Active agent delivery systems and methods for protecting and administering active agents |
| WO2005023787A1 (en) * | 2003-09-10 | 2005-03-17 | Shasun Chemicals And Drugs Limited | Process for the manufacture of 2,1,3-benzoxadiazole-4-carboxaldehyde |
| CN103613584B (zh) * | 2013-11-27 | 2016-04-27 | 沈阳药科大学 | 一种伊拉地平合成产物后处理的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670824C3 (de) * | 1967-03-20 | 1978-08-03 | Bayer Ag, 5090 Leverkusen | 1,4-Dihydropyridin-33-dicarbonsäurealkylester |
| FR2320750A1 (fr) * | 1975-08-12 | 1977-03-11 | Hexachimie | Dihydro-1,4 pyridines et leur application therapeutique |
| DE2616991A1 (de) * | 1976-04-17 | 1977-10-27 | Bayer Ag | Heterocyclisch-substituierte schwefelhaltige dihydropyridine, mehrere verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| JPS5373327A (en) * | 1976-12-13 | 1978-06-29 | Matsushita Electric Ind Co Ltd | Power source system |
| FI64938C (fi) * | 1977-06-20 | 1984-02-10 | Sandoz Ag | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara bensoxa- och bensotiadiazolyl-1,4-dihydropyridinderivat |
-
1978
- 1978-12-18 CH CH1283578A patent/CH639659A5/de not_active IP Right Cessation
-
1979
- 1979-12-08 DE DE19792949491 patent/DE2949491A1/de active Granted
- 1979-12-11 SE SE7910188A patent/SE445219B/sv not_active IP Right Cessation
- 1979-12-13 BE BE1/9643A patent/BE880591A/fr not_active IP Right Cessation
- 1979-12-14 NL NL7909024A patent/NL193066C/nl not_active IP Right Cessation
- 1979-12-14 IT IT51095/79A patent/IT1164097B/it active Protection Beyond IP Right Term
- 1979-12-14 CY CY1321A patent/CY1321A/xx unknown
- 1979-12-14 GB GB7943113A patent/GB2037766B/en not_active Expired
- 1979-12-14 GB GB08215988A patent/GB2103203B/en not_active Expired
- 1979-12-17 JP JP16396579A patent/JPS5583783A/ja active Granted
- 1979-12-17 FR FR7930829A patent/FR2444681A1/fr active Granted
- 1979-12-17 AU AU53896/79A patent/AU536055B2/en not_active Expired
- 1979-12-17 NZ NZ192422A patent/NZ192422A/xx unknown
- 1979-12-17 IE IE2445/79A patent/IE49496B1/en not_active IP Right Cessation
- 1979-12-18 ZA ZA00796842A patent/ZA796842B/xx unknown
-
1985
- 1985-12-20 SG SG975/85A patent/SG97585G/en unknown
- 1985-12-30 MY MY130/85A patent/MY8500130A/xx unknown
-
1986
- 1986-01-08 KE KE3593A patent/KE3593A/xx unknown
- 1986-03-06 HK HK160/86A patent/HK16086A/xx not_active IP Right Cessation
-
1999
- 1999-05-11 NL NL990014C patent/NL990014I1/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SG97585G (en) | 1986-07-18 |
| GB2037766B (en) | 1983-02-16 |
| AU536055B2 (en) | 1984-04-19 |
| HK16086A (en) | 1986-03-14 |
| GB2103203A (en) | 1983-02-16 |
| CY1321A (en) | 1986-06-27 |
| BE880591A (fr) | 1980-06-13 |
| NZ192422A (en) | 1982-09-14 |
| NL7909024A (nl) | 1980-06-20 |
| MY8500130A (en) | 1985-12-31 |
| FR2444681B1 (xx) | 1982-10-29 |
| GB2037766A (en) | 1980-07-16 |
| AU5389679A (en) | 1980-06-26 |
| ZA796842B (en) | 1981-07-29 |
| SE7910188L (sv) | 1980-06-19 |
| IT1164097B (it) | 1987-04-08 |
| CH639659A5 (de) | 1983-11-30 |
| FR2444681A1 (fr) | 1980-07-18 |
| SE445219B (sv) | 1986-06-09 |
| JPS5583783A (en) | 1980-06-24 |
| GB2103203B (en) | 1983-06-08 |
| IT7951095A0 (it) | 1979-12-14 |
| NL990014I1 (nl) | 1999-07-01 |
| IE792445L (en) | 1980-06-18 |
| JPH0369910B2 (xx) | 1991-11-05 |
| DE2949491A1 (de) | 1980-06-26 |
| IE49496B1 (en) | 1985-10-16 |
| DE2949491C2 (xx) | 1988-10-27 |
| NL193066B (nl) | 1998-05-06 |
| KE3593A (en) | 1986-02-07 |
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