RU2107686C1 - Производное 3-оксадиазолил-5,6,7,8-тетрагидро-1,6-нафтиридина и производное 5,6,7,8-тетрагидро-1,6-нафтиридина - Google Patents
Производное 3-оксадиазолил-5,6,7,8-тетрагидро-1,6-нафтиридина и производное 5,6,7,8-тетрагидро-1,6-нафтиридина Download PDFInfo
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- RU2107686C1 RU2107686C1 RU93050211A RU93050211A RU2107686C1 RU 2107686 C1 RU2107686 C1 RU 2107686C1 RU 93050211 A RU93050211 A RU 93050211A RU 93050211 A RU93050211 A RU 93050211A RU 2107686 C1 RU2107686 C1 RU 2107686C1
- Authority
- RU
- Russia
- Prior art keywords
- group
- tetrahydro
- benzyl
- compound
- naphthyridin
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 183
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- -1 5-methoxy-1,3,4-oxadiazol-2-yl Chemical group 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
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- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical group C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 3
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- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical group C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 2
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- MLOSGLZFFXVULD-UHFFFAOYSA-N 6-benzyl-3-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-1,5,7,8-tetrahydro-1,6-naphthyridin-2-one Chemical compound O=c1[nH]c2CCN(Cc3ccccc3)Cc2cc1-c1nnc(o1)C1CC1 MLOSGLZFFXVULD-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004429 atom Chemical group 0.000 claims 3
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- KPFCPYVACMZIEF-UHFFFAOYSA-N 2-oxo-1h-1,6-naphthyridine-3-carboxylic acid Chemical compound N1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 KPFCPYVACMZIEF-UHFFFAOYSA-N 0.000 claims 1
- FPEAARFNXIWCTP-UHFFFAOYSA-N 5,6,7,8-tetrahydro-1,6-naphthyridine Chemical compound C1=CC=C2CNCCC2=N1 FPEAARFNXIWCTP-UHFFFAOYSA-N 0.000 claims 1
- KLHWCRYJKXJVNT-UHFFFAOYSA-N 6-[(2-bromophenyl)methyl]-3-(5-methoxy-1,3,4-oxadiazol-2-yl)-1,5,7,8-tetrahydro-1,6-naphthyridin-2-one Chemical compound O1C(OC)=NN=C1C(C(N1)=O)=CC2=C1CCN(CC=1C(=CC=CC=1)Br)C2 KLHWCRYJKXJVNT-UHFFFAOYSA-N 0.000 claims 1
- ZJZRURJPCFAEDB-UHFFFAOYSA-N 6-[(2-chlorophenyl)methyl]-3-(5-methoxy-1,3,4-oxadiazol-2-yl)-1,5,7,8-tetrahydro-1,6-naphthyridin-2-one Chemical compound O1C(OC)=NN=C1C(C(N1)=O)=CC2=C1CCN(CC=1C(=CC=CC=1)Cl)C2 ZJZRURJPCFAEDB-UHFFFAOYSA-N 0.000 claims 1
- GIPOJACPFFVFMJ-UHFFFAOYSA-N 6-[(4-chlorophenyl)methyl]-3-(5-methoxy-1,3,4-oxadiazol-2-yl)-1,5,7,8-tetrahydro-1,6-naphthyridin-2-one Chemical compound O1C(OC)=NN=C1C(C(N1)=O)=CC2=C1CCN(CC=1C=CC(Cl)=CC=1)C2 GIPOJACPFFVFMJ-UHFFFAOYSA-N 0.000 claims 1
- JCXALDUUVYLQFY-UHFFFAOYSA-N 6-benzyl-3-(5-ethyl-1,3,4-oxadiazol-2-yl)-1,5,7,8-tetrahydro-1,6-naphthyridin-2-one Chemical compound O1C(CC)=NN=C1C(C(N1)=O)=CC2=C1CCN(CC=1C=CC=CC=1)C2 JCXALDUUVYLQFY-UHFFFAOYSA-N 0.000 claims 1
- WLDRDNFRXFCOSM-UHFFFAOYSA-N 6-benzyl-3-(5-propan-2-yl-1,3,4-oxadiazol-2-yl)-1,5,7,8-tetrahydro-1,6-naphthyridin-2-one Chemical compound CC(C)c1nnc(o1)-c1cc2CN(Cc3ccccc3)CCc2[nH]c1=O WLDRDNFRXFCOSM-UHFFFAOYSA-N 0.000 claims 1
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
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- 230000002829 reductive effect Effects 0.000 description 37
- 239000013078 crystal Substances 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
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- 238000001816 cooling Methods 0.000 description 30
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
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- 102000004300 GABA-A Receptors Human genes 0.000 description 6
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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- 206010053398 Clonic convulsion Diseases 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
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- 102000006240 membrane receptors Human genes 0.000 description 1
- 108020004084 membrane receptors Proteins 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
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- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
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- 239000010452 phosphate Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP260796/1992 | 1992-09-02 | ||
| JP26079692 | 1992-09-02 | ||
| JP124964/1992 | 1993-04-28 | ||
| JP12496493 | 1993-04-28 | ||
| JP124964/1993 | 1993-04-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU93050211A RU93050211A (ru) | 1996-12-10 |
| RU2107686C1 true RU2107686C1 (ru) | 1998-03-27 |
Family
ID=26461524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU93050211A RU2107686C1 (ru) | 1992-09-02 | 1993-09-01 | Производное 3-оксадиазолил-5,6,7,8-тетрагидро-1,6-нафтиридина и производное 5,6,7,8-тетрагидро-1,6-нафтиридина |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US5367078A (OSRAM) |
| EP (1) | EP0588500B1 (OSRAM) |
| KR (1) | KR0157068B1 (OSRAM) |
| CN (1) | CN1039010C (OSRAM) |
| AT (1) | ATE172974T1 (OSRAM) |
| AU (1) | AU664912B2 (OSRAM) |
| CA (1) | CA2104267A1 (OSRAM) |
| CZ (1) | CZ180793A3 (OSRAM) |
| DE (1) | DE69321915T2 (OSRAM) |
| DK (1) | DK0588500T3 (OSRAM) |
| ES (1) | ES2124771T3 (OSRAM) |
| FI (1) | FI102899B1 (OSRAM) |
| HU (1) | HUT65324A (OSRAM) |
| IL (1) | IL106728A (OSRAM) |
| MX (1) | MX9305300A (OSRAM) |
| NO (1) | NO301011B1 (OSRAM) |
| PH (1) | PH30251A (OSRAM) |
| PL (1) | PL174330B1 (OSRAM) |
| RU (1) | RU2107686C1 (OSRAM) |
| SG (1) | SG81849A1 (OSRAM) |
| TW (1) | TW227562B (OSRAM) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2240322C2 (ru) * | 1999-10-25 | 2004-11-20 | Яманоути Фармасьютикал Ко., Лтд. | Производные нафтиридина и содержащая их фармацевтическая композиция |
| RU2258506C2 (ru) * | 2000-06-21 | 2005-08-20 | Дайниппон Фармасьютикал Ко., Лтд. | Лекарственные средства для предупреждения и лечения нейродегенеративных заболеваний |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9711257D0 (en) | 1997-05-30 | 1997-07-30 | Smithkline Beecham Plc | Novel compounds |
| TW486479B (en) * | 1997-07-15 | 2002-05-11 | Dainippon Pharmaceutical Co | 5-substituted-3-oxadiazolyl-1,6-naphthyridin-2(1H)-one derivatives |
| JP4049297B2 (ja) | 2001-06-11 | 2008-02-20 | 株式会社ルネサステクノロジ | 半導体記憶装置 |
| AU2003249531A1 (en) * | 2002-08-13 | 2004-02-25 | Warner-Lambert Company Llc | Azaisoquinoline derivatives as matrix metalloproteinase inhibitors |
| US20250002488A1 (en) * | 2021-10-12 | 2025-01-02 | Brown University | Glioblastoma Multiforme Treatments |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3555034A (en) * | 1968-06-18 | 1971-01-12 | American Home Prod | Certain 5,6,7,8-tetrahydro-1,6-naphthyridin-2-ol esters |
| JPS579780A (en) * | 1980-06-21 | 1982-01-19 | Otsuka Pharmaceut Co Ltd | Carbostyril derivative |
| DE3535928A1 (de) * | 1985-10-04 | 1987-04-09 | Schering Ag | Tetrahydro-(beta)-carboline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| JPH08209780A (ja) * | 1995-02-06 | 1996-08-13 | Aisin Seiki Co Ltd | 便座装置 |
-
1993
- 1993-08-12 AU AU44587/93A patent/AU664912B2/en not_active Ceased
- 1993-08-17 CA CA002104267A patent/CA2104267A1/en not_active Abandoned
- 1993-08-18 AT AT93306510T patent/ATE172974T1/de not_active IP Right Cessation
- 1993-08-18 SG SG9600733A patent/SG81849A1/en unknown
- 1993-08-18 DK DK93306510T patent/DK0588500T3/da active
- 1993-08-18 EP EP93306510A patent/EP0588500B1/en not_active Expired - Lifetime
- 1993-08-18 DE DE69321915T patent/DE69321915T2/de not_active Expired - Fee Related
- 1993-08-18 ES ES93306510T patent/ES2124771T3/es not_active Expired - Lifetime
- 1993-08-18 IL IL10672893A patent/IL106728A/xx not_active IP Right Cessation
- 1993-08-19 PH PH46714A patent/PH30251A/en unknown
- 1993-08-24 TW TW082106850A patent/TW227562B/zh active
- 1993-08-27 US US08/112,660 patent/US5367078A/en not_active Expired - Fee Related
- 1993-08-31 MX MX9305300A patent/MX9305300A/es not_active IP Right Cessation
- 1993-09-01 RU RU93050211A patent/RU2107686C1/ru active
- 1993-09-01 NO NO933115A patent/NO301011B1/no not_active IP Right Cessation
- 1993-09-01 HU HU9302468A patent/HUT65324A/hu unknown
- 1993-09-01 FI FI933815A patent/FI102899B1/fi active
- 1993-09-01 CZ CZ931807A patent/CZ180793A3/cs unknown
- 1993-09-02 CN CN93116801A patent/CN1039010C/zh not_active Expired - Fee Related
- 1993-09-02 PL PL93300276A patent/PL174330B1/pl unknown
- 1993-09-02 KR KR1019930017471A patent/KR0157068B1/ko not_active Expired - Fee Related
-
1994
- 1994-06-16 US US08/260,800 patent/US5424433A/en not_active Expired - Fee Related
- 1994-06-16 US US08/260,835 patent/US5424434A/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| J of Medical Chem., 34, 2060, 1991. Рубцов М.В., Никитская Е.С. Успехи химии, 34, 1040, 1965. * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2240322C2 (ru) * | 1999-10-25 | 2004-11-20 | Яманоути Фармасьютикал Ко., Лтд. | Производные нафтиридина и содержащая их фармацевтическая композиция |
| RU2258506C2 (ru) * | 2000-06-21 | 2005-08-20 | Дайниппон Фармасьютикал Ко., Лтд. | Лекарственные средства для предупреждения и лечения нейродегенеративных заболеваний |
Also Published As
| Publication number | Publication date |
|---|---|
| IL106728A (en) | 1997-02-18 |
| PL174330B1 (pl) | 1998-07-31 |
| AU4458793A (en) | 1994-03-10 |
| CA2104267A1 (en) | 1994-03-03 |
| FI102899B (fi) | 1999-03-15 |
| ES2124771T3 (es) | 1999-02-16 |
| KR940007030A (ko) | 1994-04-26 |
| NO933115L (no) | 1994-03-03 |
| CN1086517A (zh) | 1994-05-11 |
| DE69321915T2 (de) | 1999-03-25 |
| ATE172974T1 (de) | 1998-11-15 |
| CN1039010C (zh) | 1998-07-08 |
| FI933815A0 (fi) | 1993-09-01 |
| DE69321915D1 (de) | 1998-12-10 |
| PH30251A (en) | 1997-02-05 |
| EP0588500A3 (en) | 1994-06-15 |
| SG81849A1 (en) | 2001-07-24 |
| US5424433A (en) | 1995-06-13 |
| FI102899B1 (fi) | 1999-03-15 |
| CZ180793A3 (en) | 1994-08-17 |
| PL300276A1 (en) | 1994-04-18 |
| HUT65324A (en) | 1994-05-02 |
| AU664912B2 (en) | 1995-12-07 |
| FI933815L (fi) | 1994-03-03 |
| US5424434A (en) | 1995-06-13 |
| EP0588500A2 (en) | 1994-03-23 |
| IL106728A0 (en) | 1993-12-08 |
| EP0588500B1 (en) | 1998-11-04 |
| KR0157068B1 (ko) | 1998-11-16 |
| TW227562B (OSRAM) | 1994-08-01 |
| DK0588500T3 (da) | 1999-07-19 |
| NO933115D0 (no) | 1993-09-01 |
| NO301011B1 (no) | 1997-09-01 |
| MX9305300A (es) | 1995-01-31 |
| US5367078A (en) | 1994-11-22 |
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