SE440351B - 3-hydroxi-1,4-bensodiazepin-2-oner och forfarande for framstellning av dessa - Google Patents
3-hydroxi-1,4-bensodiazepin-2-oner och forfarande for framstellning av dessaInfo
- Publication number
- SE440351B SE440351B SE7910333A SE7910333A SE440351B SE 440351 B SE440351 B SE 440351B SE 7910333 A SE7910333 A SE 7910333A SE 7910333 A SE7910333 A SE 7910333A SE 440351 B SE440351 B SE 440351B
- Authority
- SE
- Sweden
- Prior art keywords
- hydroxy
- dihydro
- phenyl
- chloro
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 29
- -1 2-cyanethyl Chemical group 0.000 claims description 11
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- XTIGGAHUZJWQMD-UHFFFAOYSA-N 1-chloro-2-methoxyethane Chemical compound COCCCl XTIGGAHUZJWQMD-UHFFFAOYSA-N 0.000 claims description 3
- XAXMYHMKTCNRRZ-UHFFFAOYSA-N cinolazepam Chemical compound C12=CC(Cl)=CC=C2N(CCC#N)C(=O)C(O)N=C1C1=CC=CC=C1F XAXMYHMKTCNRRZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 claims description 2
- YSPYFFRTSUIPCB-UHFFFAOYSA-N 1h-1,4-benzodiazepine-2,3-dione Chemical class N1C(=O)C(=O)N=CC2=CC=CC=C21 YSPYFFRTSUIPCB-UHFFFAOYSA-N 0.000 claims description 2
- CQZIEDXCLQOOEH-UHFFFAOYSA-N 3-bromopropanenitrile Chemical compound BrCCC#N CQZIEDXCLQOOEH-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 229940049706 benzodiazepine Drugs 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 150000003983 crown ethers Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000002560 nitrile group Chemical group 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- OGGAKRAZPNNKQV-UHFFFAOYSA-N 3-(7-chloro-3-hydroxy-2-oxo-5-phenyl-3h-1,4-benzodiazepin-1-yl)propanenitrile Chemical compound C12=CC(Cl)=CC=C2N(CCC#N)C(=O)C(O)N=C1C1=CC=CC=C1 OGGAKRAZPNNKQV-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ADIMAYPTOBDMTL-UHFFFAOYSA-N oxazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 ADIMAYPTOBDMTL-UHFFFAOYSA-N 0.000 description 4
- 229960004535 oxazepam Drugs 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- DIWRORZWFLOCLC-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N([C@H](C(NC1=CC=C(Cl)C=C11)=O)O)=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-HNNXBMFYSA-N 0.000 description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- 241000700159 Rattus Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- SAADBVWGJQAEFS-UHFFFAOYSA-N flurazepam Chemical compound N=1CC(=O)N(CCN(CC)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F SAADBVWGJQAEFS-UHFFFAOYSA-N 0.000 description 3
- 229960003528 flurazepam Drugs 0.000 description 3
- 229960004391 lorazepam Drugs 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000003112 potassium compounds Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- GNHMRTZZNHZDDM-UHFFFAOYSA-N 3-chloropropionitrile Chemical compound ClCCC#N GNHMRTZZNHZDDM-UHFFFAOYSA-N 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000021824 exploration behavior Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 229960002456 hexobarbital Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity 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
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
-
- 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
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Anesthesiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT903178A AT361492B (de) | 1978-12-18 | 1978-12-18 | Verfahren zur herstellung von neuen 3-hydroxy- 1,4-benzodiazepin-2-onen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7910333L SE7910333L (sv) | 1980-06-19 |
| SE440351B true SE440351B (sv) | 1985-07-29 |
Family
ID=3610590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7910333A SE440351B (sv) | 1978-12-18 | 1979-12-14 | 3-hydroxi-1,4-bensodiazepin-2-oner och forfarande for framstellning av dessa |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4388313A (de) |
| JP (1) | JPS5583764A (de) |
| AT (1) | AT361492B (de) |
| AU (1) | AU532331B2 (de) |
| BE (1) | BE880632A (de) |
| BG (1) | BG60474B2 (de) |
| CA (1) | CA1113464A (de) |
| CH (1) | CH643248A5 (de) |
| DE (1) | DE2950235A1 (de) |
| DK (1) | DK154973C (de) |
| ES (1) | ES486895A0 (de) |
| FI (1) | FI67375C (de) |
| FR (1) | FR2444672A1 (de) |
| GB (1) | GB2043630B (de) |
| GR (1) | GR73901B (de) |
| HK (1) | HK33385A (de) |
| IT (1) | IT1193345B (de) |
| LU (1) | LU81990A1 (de) |
| MY (1) | MY8600020A (de) |
| NL (1) | NL187068C (de) |
| NO (1) | NO151859C (de) |
| SE (1) | SE440351B (de) |
| SG (1) | SG13585G (de) |
| YU (1) | YU40586B (de) |
| ZA (1) | ZA796600B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3751673T2 (de) * | 1986-10-24 | 1996-08-01 | Abbott Lab | Test, Indikatoren, Immunogene und Antikörper für Benzodiazepine |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3311612A (en) * | 1967-03-28 | Process for preparing | ||
| US3371085A (en) * | 1959-12-10 | 1968-02-27 | Hoffmann La Roche | 5-aryl-3h-1,4-benzodiazepin-2(1h)-ones |
| BE621819A (de) * | 1961-08-29 | |||
| GB1050401A (de) * | 1963-02-19 | 1900-01-01 | ||
| NL298071A (de) * | 1963-06-04 | |||
| GB1051795A (de) * | 1964-02-11 | |||
| FR135F (de) * | 1964-08-13 | |||
| NO120269B (de) * | 1965-11-02 | 1970-09-28 | Hoffmann La Roche | |
| US3464978A (en) * | 1967-04-21 | 1969-09-02 | Hoffmann La Roche | 1-substituted urea alkyl 1,2-dihydro-1,4-benzodiazepines and benzodiazepin - 2-ones |
| CH574421A5 (en) * | 1969-02-14 | 1976-04-15 | Hoffmann La Roche | Benzodiazepines |
| AT309436B (de) * | 1970-06-23 | 1973-08-27 | Gerot Pharmazeutika | Verfahren zur Herstellung von 3-Hydroxy-1,4-benzodiazepin Derivaten oder deren Salzen |
| US4065451A (en) * | 1971-03-30 | 1977-12-27 | American Home Products | 1,3-Dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one, substituted diamino acetate esters and their acid salts |
| CH573416A5 (de) * | 1971-07-30 | 1976-03-15 | Sumitomo Chemical Co | |
| US3801568A (en) * | 1972-02-07 | 1974-04-02 | American Home Prod | Optically active 1,3-dihydro-3-substituted 5-phenyl-2h-1,4-benzodiazepin-2-ones and process for their separation |
| JPS494226A (de) * | 1972-04-27 | 1974-01-16 |
-
1978
- 1978-12-18 AT AT903178A patent/AT361492B/de not_active IP Right Cessation
-
1979
- 1979-11-26 NO NO793827A patent/NO151859C/no unknown
- 1979-11-30 DK DK510379A patent/DK154973C/da not_active IP Right Cessation
- 1979-12-05 ZA ZA00796600A patent/ZA796600B/xx unknown
- 1979-12-05 FR FR7929879A patent/FR2444672A1/fr active Granted
- 1979-12-11 AU AU53664/79A patent/AU532331B2/en not_active Expired
- 1979-12-11 NL NLAANVRAGE7908919,A patent/NL187068C/xx not_active IP Right Cessation
- 1979-12-13 LU LU81990A patent/LU81990A1/fr unknown
- 1979-12-13 DE DE19792950235 patent/DE2950235A1/de active Granted
- 1979-12-14 FI FI793924A patent/FI67375C/fi not_active IP Right Cessation
- 1979-12-14 ES ES486895A patent/ES486895A0/es active Granted
- 1979-12-14 SE SE7910333A patent/SE440351B/sv not_active IP Right Cessation
- 1979-12-14 GB GB7943107A patent/GB2043630B/en not_active Expired
- 1979-12-14 BE BE0/198574A patent/BE880632A/fr not_active IP Right Cessation
- 1979-12-17 GR GR60778A patent/GR73901B/el unknown
- 1979-12-17 CA CA342,046A patent/CA1113464A/en not_active Expired
- 1979-12-17 YU YU3087/79A patent/YU40586B/xx unknown
- 1979-12-18 JP JP16367879A patent/JPS5583764A/ja active Granted
- 1979-12-18 IT IT28149/79A patent/IT1193345B/it active
- 1979-12-18 CH CH1123179A patent/CH643248A5/de not_active IP Right Cessation
-
1981
- 1981-05-11 US US06/262,676 patent/US4388313A/en not_active Expired - Lifetime
-
1985
- 1985-02-19 SG SG135/85A patent/SG13585G/en unknown
- 1985-05-02 HK HK333/85A patent/HK33385A/xx not_active IP Right Cessation
-
1986
- 1986-12-30 MY MY20/86A patent/MY8600020A/xx unknown
-
1993
- 1993-07-21 BG BG097977A patent/BG60474B2/bg unknown
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