NO300771B1 - Nye hetaryloxy-<beta>-carboliner og deres anvendelse til fremstilling av legemidler - Google Patents
Nye hetaryloxy-<beta>-carboliner og deres anvendelse til fremstilling av legemidler Download PDFInfo
- Publication number
- NO300771B1 NO300771B1 NO930390A NO930390A NO300771B1 NO 300771 B1 NO300771 B1 NO 300771B1 NO 930390 A NO930390 A NO 930390A NO 930390 A NO930390 A NO 930390A NO 300771 B1 NO300771 B1 NO 300771B1
- Authority
- NO
- Norway
- Prior art keywords
- carboline
- methoxymethyl
- carboxylic acid
- isopropyl ester
- acid isopropyl
- Prior art date
Links
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BHNVVAZQKHLJAN-UHFFFAOYSA-N propan-2-yl 4-(methoxymethyl)-5-[5-(trifluoromethyl)pyridin-2-yl]oxy-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C=3C(COC)=C(C(=O)OC(C)C)N=CC=3NC2=CC=CC=1OC1=CC=C(C(F)(F)F)C=N1 BHNVVAZQKHLJAN-UHFFFAOYSA-N 0.000 description 1
- LAIBMPKOHCBASN-UHFFFAOYSA-N propan-2-yl 4-(methoxymethyl)-6-(1,3,5-triazin-2-yloxy)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C=3C(COC)=C(C(=O)OC(C)C)N=CC=3NC2=CC=C1OC1=NC=NC=N1 LAIBMPKOHCBASN-UHFFFAOYSA-N 0.000 description 1
- IJKCSWHRNLJTDX-UHFFFAOYSA-N propan-2-yl 4-(methoxymethyl)-6-(2-methylsulfonylpyrimidin-4-yl)oxy-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C=3C(COC)=C(C(=O)OC(C)C)N=CC=3NC2=CC=C1OC1=CC=NC(S(C)(=O)=O)=N1 IJKCSWHRNLJTDX-UHFFFAOYSA-N 0.000 description 1
- NPAVBCMELFYAIL-UHFFFAOYSA-N propan-2-yl 4-(methoxymethyl)-6-(5-methylpyrazin-2-yl)oxy-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C=3C(COC)=C(C(=O)OC(C)C)N=CC=3NC2=CC=C1OC1=CN=C(C)C=N1 NPAVBCMELFYAIL-UHFFFAOYSA-N 0.000 description 1
- GUOMAVLQUIXASK-UHFFFAOYSA-N propan-2-yl 4-(methoxymethyl)-6-(6-methoxypyridin-2-yl)oxy-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C=3C(COC)=C(C(=O)OC(C)C)N=CC=3NC2=CC=C1OC1=CC=CC(OC)=N1 GUOMAVLQUIXASK-UHFFFAOYSA-N 0.000 description 1
- IHGTYIMFKOKCSE-UHFFFAOYSA-N propan-2-yl 4-(methoxymethyl)-6-[5-(trifluoromethyl)pyridin-2-yl]oxy-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C=3C(COC)=C(C(=O)OC(C)C)N=CC=3NC2=CC=C1OC1=CC=C(C(F)(F)F)C=N1 IHGTYIMFKOKCSE-UHFFFAOYSA-N 0.000 description 1
- MYYPMKVDZCJAJU-UHFFFAOYSA-N propan-2-yl 4-(methoxymethyl)-6-[6-(4-methylphenyl)sulfonylpyridin-3-yl]oxy-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C=3C(COC)=C(C(=O)OC(C)C)N=CC=3NC2=CC=C1OC(C=N1)=CC=C1S(=O)(=O)C1=CC=C(C)C=C1 MYYPMKVDZCJAJU-UHFFFAOYSA-N 0.000 description 1
- UHEAVVAFLJCZSF-UHFFFAOYSA-N propan-2-yl 6-(2,6-dimethoxypyrimidin-4-yl)oxy-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C=3C(COC)=C(C(=O)OC(C)C)N=CC=3NC2=CC=C1OC1=CC(OC)=NC(OC)=N1 UHEAVVAFLJCZSF-UHFFFAOYSA-N 0.000 description 1
- COIMZCBCECDYBH-UHFFFAOYSA-N propan-2-yl 6-(4,6-dimethylpyrimidin-2-yl)oxy-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C=3C(COC)=C(C(=O)OC(C)C)N=CC=3NC2=CC=C1OC1=NC(C)=CC(C)=N1 COIMZCBCECDYBH-UHFFFAOYSA-N 0.000 description 1
- MXNQGKKDMKHWOL-UHFFFAOYSA-N propan-2-yl 6-(5-bromopyrazin-2-yl)oxy-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C=3C(COC)=C(C(=O)OC(C)C)N=CC=3NC2=CC=C1OC1=CN=C(Br)C=N1 MXNQGKKDMKHWOL-UHFFFAOYSA-N 0.000 description 1
- CLEBADWJPJRIDU-UHFFFAOYSA-N propan-2-yl 6-(5-bromopyrazin-2-yl)oxy-4-ethyl-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C=3C(CC)=C(C(=O)OC(C)C)N=CC=3NC2=CC=C1OC1=CN=C(Br)C=N1 CLEBADWJPJRIDU-UHFFFAOYSA-N 0.000 description 1
- TYLJJOIDTVRDAK-UHFFFAOYSA-N propan-2-yl 6-(5-bromopyrazin-2-yl)oxy-4-methyl-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C3=C(C)C(C(=O)OC(C)C)=NC=C3NC2=CC=C1OC1=CN=C(Br)C=N1 TYLJJOIDTVRDAK-UHFFFAOYSA-N 0.000 description 1
- QNCJWFMQHBMPCX-UHFFFAOYSA-N propan-2-yl 6-(5-bromopyrimidin-2-yl)oxy-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C=3C(COC)=C(C(=O)OC(C)C)N=CC=3NC2=CC=C1OC1=NC=C(Br)C=N1 QNCJWFMQHBMPCX-UHFFFAOYSA-N 0.000 description 1
- XOMFLFXVPSBVJZ-UHFFFAOYSA-N propan-2-yl 6-hydroxy-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound N1C2=CC=C(O)C=C2C2=C1C=NC(C(=O)OC(C)C)=C2 XOMFLFXVPSBVJZ-UHFFFAOYSA-N 0.000 description 1
- ALPOVKYFXHSNRA-UHFFFAOYSA-N propan-2-yl 6-isoquinolin-1-yloxy-4-(methoxymethyl)-9-(4-methylphenyl)sulfonylpyrido[3,4-b]indole-3-carboxylate Chemical compound C12=CC=C(OC=3C4=CC=CC=C4C=CN=3)C=C2C=2C(COC)=C(C(=O)OC(C)C)N=CC=2N1S(=O)(=O)C1=CC=C(C)C=C1 ALPOVKYFXHSNRA-UHFFFAOYSA-N 0.000 description 1
- BXKAAZLCJXWSQR-UHFFFAOYSA-N propan-2-yl 6-isoquinolin-1-yloxy-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=CC=C2C(OC3=CC=C4NC=5C=NC(=C(C=5C4=C3)COC)C(=O)OC(C)C)=NC=CC2=C1 BXKAAZLCJXWSQR-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- IPMPHGOTHAOAHA-UHFFFAOYSA-N tert-butyl 4-(methoxymethyl)-6-(5-methylpyrazin-2-yl)oxy-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C=3C(COC)=C(C(=O)OC(C)(C)C)N=CC=3NC2=CC=C1OC1=CN=C(C)C=N1 IPMPHGOTHAOAHA-UHFFFAOYSA-N 0.000 description 1
- LQINRSMNQLFGKS-UHFFFAOYSA-N tert-butyl 4-(methoxymethyl)-6-(6-methoxypyridin-2-yl)oxy-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C=3C(COC)=C(C(=O)OC(C)(C)C)N=CC=3NC2=CC=C1OC1=CC=CC(OC)=N1 LQINRSMNQLFGKS-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
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
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4118741A DE4118741A1 (de) | 1991-06-05 | 1991-06-05 | Neue hetaryloxy-(beta)-carboline, deren herstellung und verwendung in arzneimitteln |
| PCT/DE1992/000465 WO1992021679A1 (de) | 1991-06-05 | 1992-06-04 | NEUE HETARYLOXY-β-CARBOLINE, DEREN HERSTELLUNG UND VERWENDUNG IN ARZNEIMITTELN |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO930390D0 NO930390D0 (no) | 1993-02-04 |
| NO930390L NO930390L (no) | 1993-02-04 |
| NO300771B1 true NO300771B1 (no) | 1997-07-21 |
Family
ID=6433410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO930390A NO300771B1 (no) | 1991-06-05 | 1993-02-04 | Nye hetaryloxy-<beta>-carboliner og deres anvendelse til fremstilling av legemidler |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US5348958A (zh) |
| EP (1) | EP0541757A1 (zh) |
| JP (1) | JPH06500341A (zh) |
| KR (1) | KR930701440A (zh) |
| CN (1) | CN1039906C (zh) |
| AU (1) | AU658631B2 (zh) |
| CA (1) | CA2087098A1 (zh) |
| CZ (1) | CZ281810B6 (zh) |
| DE (1) | DE4118741A1 (zh) |
| FI (1) | FI930293A0 (zh) |
| HU (1) | HUT63166A (zh) |
| IE (1) | IE921825A1 (zh) |
| IL (1) | IL102116A (zh) |
| MX (1) | MX9202616A (zh) |
| NO (1) | NO300771B1 (zh) |
| NZ (1) | NZ243014A (zh) |
| PL (1) | PL172481B1 (zh) |
| PT (1) | PT100565A (zh) |
| RU (1) | RU2105766C1 (zh) |
| WO (1) | WO1992021679A1 (zh) |
| ZA (1) | ZA924127B (zh) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4118741A1 (de) * | 1991-06-05 | 1992-12-10 | Schering Ag | Neue hetaryloxy-(beta)-carboline, deren herstellung und verwendung in arzneimitteln |
| DE4308788A1 (de) * | 1993-03-18 | 1994-09-22 | Bayer Ag | Hetero-tricyclisch-substituierte Phenyl-cyclohexan-carbonsäurederivate |
| DE4330175A1 (de) * | 1993-08-31 | 1995-03-02 | Schering Ag | Alkoxy-substituierte beta-Carboline |
| GB0108337D0 (en) * | 2001-04-03 | 2001-05-23 | Novartis Ag | Organic compounds |
| US8927551B2 (en) * | 2009-05-18 | 2015-01-06 | Infinity Pharmaceuticals, Inc. | Isoxazolines as inhibitors of fatty acid amide hydrolase |
| US9149465B2 (en) * | 2009-05-18 | 2015-10-06 | Infinity Pharmaceuticals, Inc. | Isoxazolines as inhibitors of fatty acid amide hydrolase |
| US8765735B2 (en) * | 2009-05-18 | 2014-07-01 | Infinity Pharmaceuticals, Inc. | Isoxazolines as inhibitors of fatty acid amide hydrolase |
| US20220411273A1 (en) * | 2019-11-27 | 2022-12-29 | Wacker Chemie Ag | Method for removing an impurity from a chlorosilane mixture |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3608089A1 (de) * | 1986-03-08 | 1987-09-10 | Schering Ag | Heteroaryl-oxy-ss-carbolinderivate, ihre herstellung und ihre verwendung als arzneimittel |
| IL87563A (en) * | 1987-08-28 | 1993-08-18 | Schering Ag | Isoxazole-b-carboline derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same |
| DE4118741A1 (de) * | 1991-06-05 | 1992-12-10 | Schering Ag | Neue hetaryloxy-(beta)-carboline, deren herstellung und verwendung in arzneimitteln |
-
1991
- 1991-06-05 DE DE4118741A patent/DE4118741A1/de not_active Withdrawn
-
1992
- 1992-06-02 MX MX9202616A patent/MX9202616A/es not_active IP Right Cessation
- 1992-06-04 KR KR1019930700323A patent/KR930701440A/ko not_active Application Discontinuation
- 1992-06-04 RU RU93005125A patent/RU2105766C1/ru active
- 1992-06-04 WO PCT/DE1992/000465 patent/WO1992021679A1/de not_active Application Discontinuation
- 1992-06-04 CZ CS923968A patent/CZ281810B6/cs unknown
- 1992-06-04 NZ NZ243014A patent/NZ243014A/en unknown
- 1992-06-04 CA CA002087098A patent/CA2087098A1/en not_active Abandoned
- 1992-06-04 PT PT100565A patent/PT100565A/pt not_active Application Discontinuation
- 1992-06-04 CN CN92105684A patent/CN1039906C/zh not_active Expired - Fee Related
- 1992-06-04 HU HU9300595A patent/HUT63166A/hu unknown
- 1992-06-04 EP EP92911058A patent/EP0541757A1/de not_active Withdrawn
- 1992-06-04 PL PL92297839A patent/PL172481B1/pl unknown
- 1992-06-04 JP JP4509774A patent/JPH06500341A/ja active Pending
- 1992-06-05 IL IL10211692A patent/IL102116A/xx not_active IP Right Cessation
- 1992-06-05 ZA ZA924127A patent/ZA924127B/xx unknown
- 1992-06-05 US US07/892,819 patent/US5348958A/en not_active Expired - Fee Related
- 1992-06-05 AU AU18074/92A patent/AU658631B2/en not_active Ceased
- 1992-07-01 IE IE182592A patent/IE921825A1/en not_active Application Discontinuation
-
1993
- 1993-01-25 FI FI930293A patent/FI930293A0/fi not_active Application Discontinuation
- 1993-02-04 NO NO930390A patent/NO300771B1/no unknown
-
1994
- 1994-07-11 US US08/272,464 patent/US5698555A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| PL172481B1 (pl) | 1997-09-30 |
| CA2087098A1 (en) | 1992-12-06 |
| WO1992021679A1 (de) | 1992-12-10 |
| FI930293A (fi) | 1993-01-25 |
| FI930293A0 (fi) | 1993-01-25 |
| KR930701440A (ko) | 1993-06-11 |
| AU1807492A (en) | 1992-12-10 |
| PL297839A1 (en) | 1993-11-02 |
| ZA924127B (en) | 1993-02-24 |
| US5348958A (en) | 1994-09-20 |
| IL102116A (en) | 1997-02-18 |
| EP0541757A1 (de) | 1993-05-19 |
| AU658631B2 (en) | 1995-04-27 |
| CN1039906C (zh) | 1998-09-23 |
| US5698555A (en) | 1997-12-16 |
| HUT63166A (en) | 1993-07-28 |
| IL102116A0 (en) | 1993-01-14 |
| IE921825A1 (en) | 1992-12-16 |
| NO930390D0 (no) | 1993-02-04 |
| MX9202616A (es) | 1993-09-01 |
| NZ243014A (en) | 1995-04-27 |
| RU2105766C1 (ru) | 1998-02-27 |
| JPH06500341A (ja) | 1994-01-13 |
| DE4118741A1 (de) | 1992-12-10 |
| CZ396892A3 (en) | 1993-10-13 |
| PT100565A (pt) | 1993-08-31 |
| CN1069270A (zh) | 1993-02-24 |
| HU9300595D0 (en) | 1993-05-28 |
| NO930390L (no) | 1993-02-04 |
| CZ281810B6 (cs) | 1997-02-12 |
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