NL9202238A - Benzofuranylimidazoolderivaten, werkwijze voor de bereiding ervan en therapeutische preparaten die ze bevatten. - Google Patents
Benzofuranylimidazoolderivaten, werkwijze voor de bereiding ervan en therapeutische preparaten die ze bevatten. Download PDFInfo
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- NL9202238A NL9202238A NL9202238A NL9202238A NL9202238A NL 9202238 A NL9202238 A NL 9202238A NL 9202238 A NL9202238 A NL 9202238A NL 9202238 A NL9202238 A NL 9202238A NL 9202238 A NL9202238 A NL 9202238A
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- general formula
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- 238000000034 method Methods 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title claims description 19
- VBFQIUOSXHUWCT-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-1h-imidazole Chemical class C1=CNC(C=2OC3=CC=CC=C3C=2)=N1 VBFQIUOSXHUWCT-UHFFFAOYSA-N 0.000 title claims description 6
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 58
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000012380 dealkylating agent Substances 0.000 claims description 4
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical group C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 claims description 4
- LYIIBVSRGJSHAV-UHFFFAOYSA-N 2-aminoacetaldehyde Chemical compound NCC=O LYIIBVSRGJSHAV-UHFFFAOYSA-N 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- 239000011260 aqueous acid Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
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- 108010049134 Imidazoline Receptors Proteins 0.000 description 11
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- 229950001476 idazoxan Drugs 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 235000011167 hydrochloric acid Nutrition 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
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- RWPPGXMIQFYPRL-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-1h-imidazole;hydrochloride Chemical compound Cl.C1=CNC(C=2OC3=CC=CC=C3C=2)=N1 RWPPGXMIQFYPRL-UHFFFAOYSA-N 0.000 description 3
- CLACROOOBBIRQG-UHFFFAOYSA-N 2-(6-methoxy-1-benzofuran-2-yl)-1h-imidazole;hydrochloride Chemical compound Cl.O1C2=CC(OC)=CC=C2C=C1C1=NC=CN1 CLACROOOBBIRQG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
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- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- HPMRFMKYPGXPEP-UHFFFAOYSA-N idazoxan Chemical compound N1CCN=C1C1OC2=CC=CC=C2OC1 HPMRFMKYPGXPEP-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 239000002904 solvent Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 2
- 229930182837 (R)-adrenaline Natural products 0.000 description 2
- ZJDRDTZQVOCKPI-UHFFFAOYSA-N 1-benzofuran-2-carbonyl chloride Chemical compound C1=CC=C2OC(C(=O)Cl)=CC2=C1 ZJDRDTZQVOCKPI-UHFFFAOYSA-N 0.000 description 2
- QHKJIJXBJCOABP-UHFFFAOYSA-N 1-benzofuran-2-carboxamide Chemical compound C1=CC=C2OC(C(=O)N)=CC2=C1 QHKJIJXBJCOABP-UHFFFAOYSA-N 0.000 description 2
- OFFSPAZVIVZPHU-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 description 2
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 2
- AOTPFRLWMUNPFG-UHFFFAOYSA-N 2-(5-methoxy-1-benzofuran-2-yl)-1h-imidazole;hydrochloride Chemical compound Cl.C=1C2=CC(OC)=CC=C2OC=1C1=NC=CN1 AOTPFRLWMUNPFG-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
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- 241000699670 Mus sp. Species 0.000 description 2
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- 229920002472 Starch Polymers 0.000 description 2
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- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
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- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- ZOUIBNOTCCZKNC-UHFFFAOYSA-N 1-(1-benzofuran-2-yl)-4,5-dihydroimidazole Chemical class C1=NCCN1C1=CC2=CC=CC=C2O1 ZOUIBNOTCCZKNC-UHFFFAOYSA-N 0.000 description 1
- UDJHZXXDRXBGDX-UHFFFAOYSA-N 1-benzofuran-2-carbonitrile;methyl 1-benzofuran-2-carboximidate;hydrochloride Chemical compound Cl.C1=CC=C2OC(C#N)=CC2=C1.C1=CC=C2OC(C(=N)OC)=CC2=C1 UDJHZXXDRXBGDX-UHFFFAOYSA-N 0.000 description 1
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- GNYDFJVZQRHJEY-UHFFFAOYSA-N 2-(5-bromo-1-benzofuran-2-yl)-1h-imidazole;hydrochloride Chemical compound Cl.C=1C2=CC(Br)=CC=C2OC=1C1=NC=CN1 GNYDFJVZQRHJEY-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
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- IQELKSYGXWBQJA-UHFFFAOYSA-N 6-methoxy-1-benzofuran-2-carboxylic acid Chemical compound COC1=CC=C2C=C(C(O)=O)OC2=C1 IQELKSYGXWBQJA-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
-
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9127430 | 1991-12-27 | ||
| GB919127430A GB9127430D0 (en) | 1991-12-27 | 1991-12-27 | Benzofuranylimidazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL9202238A true NL9202238A (nl) | 1993-07-16 |
Family
ID=10706855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL9202238A NL9202238A (nl) | 1991-12-27 | 1992-12-23 | Benzofuranylimidazoolderivaten, werkwijze voor de bereiding ervan en therapeutische preparaten die ze bevatten. |
Country Status (34)
| Country | Link |
|---|---|
| US (2) | US5310930A (OSRAM) |
| JP (1) | JPH05271223A (OSRAM) |
| AT (1) | AT402071B (OSRAM) |
| AU (1) | AU652877B2 (OSRAM) |
| BE (1) | BE1006226A3 (OSRAM) |
| CA (1) | CA2086137C (OSRAM) |
| CH (1) | CH685344A5 (OSRAM) |
| DE (1) | DE4244342C2 (OSRAM) |
| DK (1) | DK155692A (OSRAM) |
| DZ (1) | DZ1655A1 (OSRAM) |
| ES (1) | ES2049186B1 (OSRAM) |
| FI (1) | FI111365B (OSRAM) |
| FR (2) | FR2685698B1 (OSRAM) |
| GB (2) | GB9127430D0 (OSRAM) |
| GR (1) | GR1001566B (OSRAM) |
| HK (1) | HK27096A (OSRAM) |
| HU (1) | HUT67269A (OSRAM) |
| IE (1) | IE73489B1 (OSRAM) |
| IN (1) | IN180496B (OSRAM) |
| IT (1) | IT1256238B (OSRAM) |
| LU (1) | LU88204A1 (OSRAM) |
| MA (1) | MA22752A1 (OSRAM) |
| MY (1) | MY109729A (OSRAM) |
| NL (1) | NL9202238A (OSRAM) |
| NO (1) | NO300841B1 (OSRAM) |
| NZ (1) | NZ245500A (OSRAM) |
| OA (1) | OA09903A (OSRAM) |
| PL (3) | PL170205B1 (OSRAM) |
| PT (1) | PT101158B (OSRAM) |
| RU (1) | RU2068416C1 (OSRAM) |
| SE (1) | SE503224C2 (OSRAM) |
| TN (1) | TNSN92118A1 (OSRAM) |
| TW (1) | TW226997B (OSRAM) |
| ZA (1) | ZA929736B (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9127050D0 (en) * | 1991-12-20 | 1992-02-19 | Orion Yhtymae Oy | Substituted imidazole derivatives and their preparation and use |
| EP1266897A3 (en) * | 1997-12-19 | 2003-12-03 | Eli Lilly And Company | Hypoglycemic imidazoline compounds |
| AU2201699A (en) * | 1997-12-19 | 1999-07-12 | Eli Lilly And Company | Hypoglycemic imidazoline compounds |
| GB2351082A (en) * | 1999-06-18 | 2000-12-20 | Lilly Forschung Gmbh | Synthesis of Cyclic Substituted Amidines |
| EP1602655A4 (en) * | 2003-03-07 | 2010-06-09 | Kowa Co | benzofuran |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH593967A5 (en) * | 1971-11-09 | 1977-12-30 | Ciba Geigy Ag | Optical brighteners for organic materials - consist of quaternised benzofuranyl or naphthofuranyl benzimidazole cpds. |
| US3927023A (en) * | 1974-05-24 | 1975-12-16 | Warner Lambert Co | Imidazolyl benzofurans |
| ZW13782A1 (en) * | 1981-07-28 | 1982-10-06 | Reckitt & Colmann Prod Ltd | Imidazoline derivatives |
| GB2122987B (en) * | 1982-06-01 | 1985-09-25 | Zyma Sa | (+)-cyanidan-3-ol derivatives and pharmaceutical preparations thereof |
| ES8503669A1 (es) * | 1982-07-05 | 1985-03-01 | Erba Farmitalia | Procedimiento para preparar derivados n-imidazolilicos de compuestos biciclicos. |
| GB2167408B (en) * | 1984-11-23 | 1988-05-25 | Farmos Oy | Substituted imidazole derivatives and their preparation and use |
| GB8720693D0 (en) * | 1987-09-03 | 1987-10-07 | Glaxo Group Ltd | Chemical compounds |
| GB8805628D0 (en) * | 1988-03-09 | 1988-04-07 | Erba Farmitalia | Hypolipidaemic imidazol-2-yl-derivatives of bicyclic compounds & process for their preparation |
-
1991
- 1991-12-27 GB GB919127430A patent/GB9127430D0/en active Pending
-
1992
- 1992-12-11 IN IN1187DE1992 patent/IN180496B/en unknown
- 1992-12-15 ZA ZA929736A patent/ZA929736B/xx unknown
- 1992-12-17 NZ NZ245500A patent/NZ245500A/xx unknown
- 1992-12-18 CH CH3891/92A patent/CH685344A5/fr not_active IP Right Cessation
- 1992-12-18 SE SE9203824A patent/SE503224C2/sv not_active IP Right Cessation
- 1992-12-18 MY MYPI92002345A patent/MY109729A/en unknown
- 1992-12-18 FI FI925755A patent/FI111365B/fi active
- 1992-12-18 GR GR920100564A patent/GR1001566B/el not_active IP Right Cessation
- 1992-12-21 AT AT0252892A patent/AT402071B/de not_active IP Right Cessation
- 1992-12-22 LU LU88204A patent/LU88204A1/fr unknown
- 1992-12-22 FR FR9215445A patent/FR2685698B1/fr not_active Expired - Fee Related
- 1992-12-22 FR FR9215446A patent/FR2685637B1/fr not_active Expired - Fee Related
- 1992-12-22 PL PL92297109A patent/PL170205B1/pl unknown
- 1992-12-22 BE BE9201126A patent/BE1006226A3/fr not_active IP Right Cessation
- 1992-12-22 PL PL92312900A patent/PL170404B1/pl unknown
- 1992-12-22 PL PL92312899A patent/PL170409B1/pl unknown
- 1992-12-23 PT PT101158A patent/PT101158B/pt not_active IP Right Cessation
- 1992-12-23 DK DK155692A patent/DK155692A/da not_active Application Discontinuation
- 1992-12-23 HU HU9204120A patent/HUT67269A/hu unknown
- 1992-12-23 IE IE922945A patent/IE73489B1/en not_active IP Right Cessation
- 1992-12-23 NO NO925007A patent/NO300841B1/no unknown
- 1992-12-23 IT ITMI922954A patent/IT1256238B/it active IP Right Grant
- 1992-12-23 NL NL9202238A patent/NL9202238A/nl not_active Application Discontinuation
- 1992-12-23 US US07/995,790 patent/US5310930A/en not_active Expired - Lifetime
- 1992-12-23 CA CA002086137A patent/CA2086137C/en not_active Expired - Fee Related
- 1992-12-24 OA OA60323A patent/OA09903A/fr unknown
- 1992-12-24 GB GB9226997A patent/GB2262739B/en not_active Expired - Fee Related
- 1992-12-24 ES ES09202615A patent/ES2049186B1/es not_active Expired - Fee Related
- 1992-12-24 AU AU30496/92A patent/AU652877B2/en not_active Ceased
- 1992-12-25 MA MA23044A patent/MA22752A1/fr unknown
- 1992-12-25 JP JP4347195A patent/JPH05271223A/ja active Pending
- 1992-12-25 RU RU9292016209A patent/RU2068416C1/ru active
- 1992-12-27 DZ DZ920169A patent/DZ1655A1/fr active
- 1992-12-27 TN TNTNSN92118A patent/TNSN92118A1/fr unknown
- 1992-12-28 DE DE4244342A patent/DE4244342C2/de not_active Expired - Fee Related
- 1992-12-29 TW TW081110441A patent/TW226997B/zh active
-
1993
- 1993-12-02 US US08/161,226 patent/US5354769A/en not_active Expired - Lifetime
-
1996
- 1996-02-15 HK HK27096A patent/HK27096A/xx not_active IP Right Cessation
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| BV | The patent application has lapsed |