HU185523B - Method for producing a phenyl-alkyl-aminoethyl-salicylamide - Google Patents
Method for producing a phenyl-alkyl-aminoethyl-salicylamide Download PDFInfo
- Publication number
- HU185523B HU185523B HU79SCHE690A HUSC000690A HU185523B HU 185523 B HU185523 B HU 185523B HU 79SCHE690 A HU79SCHE690 A HU 79SCHE690A HU SC000690 A HUSC000690 A HU SC000690A HU 185523 B HU185523 B HU 185523B
- Authority
- HU
- Hungary
- Prior art keywords
- methyl
- phenylpropyl
- benzyl
- hydroxy
- salicylamide
- Prior art date
Links
- 229960000581 salicylamide Drugs 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 230000003287 optical effect Effects 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- -1 (R) - (1-methyl-3-phenylpropyl) -amino Chemical group 0.000 claims abstract description 26
- 239000002253 acid Substances 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012458 free base Substances 0.000 claims abstract description 10
- 125000006239 protecting group Chemical group 0.000 claims abstract description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 claims abstract 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 14
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- 238000004587 chromatography analysis Methods 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000000741 silica gel Substances 0.000 claims description 7
- 229910002027 silica gel Inorganic materials 0.000 claims description 7
- 239000012279 sodium borohydride Substances 0.000 claims description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 239000012448 Lithium borohydride Substances 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
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- 239000011591 potassium Substances 0.000 claims description 3
- 239000002516 radical scavenger Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 claims description 2
- UHDKXFCUGVGVDP-UHFFFAOYSA-N n-ethyl-2-hydroxybenzamide Chemical compound CCNC(=O)C1=CC=CC=C1O UHDKXFCUGVGVDP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 239000000969 carrier Substances 0.000 claims 2
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- LHJPQKAOZHDEFP-UHFFFAOYSA-N N-(2-aminoacetyl)-2-hydroxybenzamide Chemical compound C(C=1C(O)=CC=CC=1)(=O)NC(CN)=O LHJPQKAOZHDEFP-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 1
- 125000004344 phenylpropyl group Chemical group 0.000 claims 1
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- 229960002808 pholcodine Drugs 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- SGUAFYQXFOLMHL-UHFFFAOYSA-N 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide Chemical compound C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 SGUAFYQXFOLMHL-UHFFFAOYSA-N 0.000 abstract description 28
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- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
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- 239000006188 syrup Substances 0.000 description 1
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- 238000004809 thin layer chromatography Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
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- 229940078499 tricalcium phosphate Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
-
- 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
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Ophthalmology & Optometry (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94451678A | 1978-09-20 | 1978-09-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU185523B true HU185523B (en) | 1985-02-28 |
Family
ID=25481553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79SCHE690A HU185523B (en) | 1978-09-20 | 1979-09-19 | Method for producing a phenyl-alkyl-aminoethyl-salicylamide |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP0009702B1 (en, 2012) |
| JP (3) | JPS5555147A (en, 2012) |
| KR (2) | KR830000904A (en, 2012) |
| AT (1) | ATE351T1 (en, 2012) |
| AU (1) | AU528626B2 (en, 2012) |
| CA (1) | CA1151211A (en, 2012) |
| CY (1) | CY1175A (en, 2012) |
| DD (1) | DD150457A5 (en, 2012) |
| DE (1) | DE2961263D1 (en, 2012) |
| DK (1) | DK387579A (en, 2012) |
| FI (1) | FI792884A7 (en, 2012) |
| GR (1) | GR73179B (en, 2012) |
| HK (1) | HK13383A (en, 2012) |
| HU (1) | HU185523B (en, 2012) |
| IE (1) | IE49301B1 (en, 2012) |
| IL (1) | IL58258A (en, 2012) |
| KE (1) | KE3283A (en, 2012) |
| MY (1) | MY8500042A (en, 2012) |
| NO (1) | NO149660C (en, 2012) |
| NZ (1) | NZ191589A (en, 2012) |
| OA (1) | OA06339A (en, 2012) |
| PH (1) | PH16794A (en, 2012) |
| PL (1) | PL129114B1 (en, 2012) |
| PT (1) | PT70191A (en, 2012) |
| SG (1) | SG283G (en, 2012) |
| YU (1) | YU227379A (en, 2012) |
| ZA (1) | ZA794872B (en, 2012) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4658060A (en) * | 1982-04-26 | 1987-04-14 | Schering Corporation | Preparation of (-)-5-(beta)-1-hydroxy-2-((beta)-1-methyl-3-phenylpropyl)aminoethyl) salicylamide |
| IT1194406B (it) * | 1983-09-27 | 1988-09-22 | Scharper S P A | Procedimento per la preparazione di 2-idrossi-5-01-idrossi-2-((4-fenil-2-butil)ammino) etil benzammide |
| HU190867B (en) * | 1984-01-20 | 1986-11-28 | Egyt Gyogyszervegyeszeti Gyar,Hu | Process for preparing 2-hydroxy-5-/1-hydroxy-2-/1-methyl-3-phenyl-propyl/-amino/ethyl/-benzamide and pharmaceutically acceptable salts thereof |
| US4788183A (en) * | 1987-11-30 | 1988-11-29 | Schering Corporation | Method for treatment of dyslipidemia in humans |
| US4879233A (en) * | 1989-02-10 | 1989-11-07 | Schering Corporation | Novel Aspergillus niveus microorganism used for the chiral reduction of carbonyl groups |
| US5858684A (en) * | 1991-08-23 | 1999-01-12 | The Brigham And Women's Hospital, Inc. | Method of screening calcium receptor-active molecules |
| US6031003A (en) * | 1991-08-23 | 2000-02-29 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6001884A (en) * | 1991-08-23 | 1999-12-14 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6313146B1 (en) | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6011068A (en) * | 1991-08-23 | 2000-01-04 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US5688938A (en) * | 1991-08-23 | 1997-11-18 | The Brigham & Women's Hospital, Inc. | Calcium receptor-active molecules |
| US5763569A (en) * | 1991-08-23 | 1998-06-09 | The Brigham And Women's Hospital, Inc | Calcium receptor-active molecules |
| ATE312347T1 (de) * | 1991-08-23 | 2005-12-15 | Nps Pharma Inc | Screening-verfahren für kalzium-rezeptor aktive verbindungen |
| US5962314A (en) * | 1993-02-23 | 1999-10-05 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| PL183499B1 (pl) | 1994-10-21 | 2002-06-28 | Nps Pharma Inc | Związki do modulowania receptorów wapniowych i kompozycje farmaceutyczne |
| DE69722934T2 (de) | 1996-05-01 | 2004-05-27 | NPS Pharmaceuticals, Inc., Salt Lake City | Verbindungen , die auf anorganische ionen-rezeptoren wirken |
| IT1313583B1 (it) | 1999-07-30 | 2002-09-09 | Chiesi Farma Spa | Derivati 2-amminotetralinici per la terapia del glaucoma. |
| DE602007003312D1 (de) * | 2007-02-22 | 2009-12-31 | Indena Spa | Verfahren zur Herstellung von (2r,3s)-3-Phenylisoserin-Methylester-Acetatsalz |
| CN103347517B (zh) | 2010-08-11 | 2018-10-02 | 德雷克塞尔大学 | 治疗帕金森病中运动障碍的d3多巴胺受体激动剂 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1266058A (en, 2012) * | 1969-07-08 | 1972-03-08 | ||
| US4012444A (en) * | 1969-07-08 | 1977-03-15 | Allen & Hanburys Limited | 5-[1-Hydroxy-2-(1-methyl-3-phenylpropyl)aminoethyl] salicylamide and physiologically acceptable acid addition salts thereof |
| LU74760A1 (en, 2012) * | 1975-04-17 | 1977-02-04 |
-
1979
- 1979-09-13 ZA ZA00794872A patent/ZA794872B/xx unknown
- 1979-09-17 NO NO792993A patent/NO149660C/no unknown
- 1979-09-17 FI FI792884A patent/FI792884A7/fi not_active Application Discontinuation
- 1979-09-17 AT AT79103473T patent/ATE351T1/de not_active IP Right Cessation
- 1979-09-17 NZ NZ191589A patent/NZ191589A/en unknown
- 1979-09-17 PH PH23042A patent/PH16794A/en unknown
- 1979-09-17 CY CY1175A patent/CY1175A/xx unknown
- 1979-09-17 AU AU50881/79A patent/AU528626B2/en not_active Ceased
- 1979-09-17 DE DE7979103473T patent/DE2961263D1/de not_active Expired
- 1979-09-17 DK DK387579A patent/DK387579A/da not_active Application Discontinuation
- 1979-09-17 EP EP79103473A patent/EP0009702B1/en not_active Expired
- 1979-09-18 IL IL58258A patent/IL58258A/xx unknown
- 1979-09-18 CA CA000335885A patent/CA1151211A/en not_active Expired
- 1979-09-18 OA OA56898A patent/OA06339A/xx unknown
- 1979-09-18 IE IE1770/79A patent/IE49301B1/en unknown
- 1979-09-18 PT PT70191A patent/PT70191A/pt unknown
- 1979-09-18 JP JP11996879A patent/JPS5555147A/ja active Granted
- 1979-09-18 YU YU02273/79A patent/YU227379A/xx unknown
- 1979-09-18 KR KR1019790003218A patent/KR830000904A/ko not_active Ceased
- 1979-09-18 GR GR60059A patent/GR73179B/el unknown
- 1979-09-19 HU HU79SCHE690A patent/HU185523B/hu unknown
- 1979-09-19 DD DD79215640A patent/DD150457A5/de unknown
- 1979-09-19 PL PL1979218408A patent/PL129114B1/pl unknown
-
1983
- 1983-01-04 SG SG2/83A patent/SG283G/en unknown
- 1983-04-21 HK HK133/83A patent/HK13383A/xx unknown
- 1983-04-25 KE KE3283A patent/KE3283A/xx unknown
- 1983-11-17 JP JP58217073A patent/JPS59108749A/ja active Pending
-
1984
- 1984-04-09 KR KR1019840001867A patent/KR890001998B1/ko not_active Expired
-
1985
- 1985-12-30 MY MY42/85A patent/MY8500042A/xx unknown
-
1989
- 1989-11-13 JP JP1292552A patent/JPH02167253A/ja active Pending
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