HRP970146A2 - Epoxi-azetidines, preparation and use - Google Patents
Epoxi-azetidines, preparation and useInfo
- Publication number
- HRP970146A2 HRP970146A2 HR970146A HRP970146A HRP970146A2 HR P970146 A2 HRP970146 A2 HR P970146A2 HR 970146 A HR970146 A HR 970146A HR P970146 A HRP970146 A HR P970146A HR P970146 A2 HRP970146 A2 HR P970146A2
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- atoms
- isoxazol
- carbonylamino
- chlorophenyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 6
- -1 3-o-chlorophenyl-5-methyl-isoxazol-4-yl-carbonylamino, phthalimido Chemical group 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims description 4
- 238000006735 epoxidation reaction Methods 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 239000003781 beta lactamase inhibitor Substances 0.000 claims description 3
- 229940126813 beta-lactamase inhibitor Drugs 0.000 claims description 3
- 125000006262 isopropyl amino sulfonyl group Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 2
- FICBLGOBWCGQKR-SCSAIBSYSA-N (5R)-3-oxa-4-thia-1-azabicyclo[3.2.0]heptan-7-one Chemical class S1OCN2C(=O)C[C@H]21 FICBLGOBWCGQKR-SCSAIBSYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 7
- 239000011877 solvent mixture Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- SXTPCWDEYAMPTR-UHFFFAOYSA-N 4-oxoazetidine-2-sulfonic acid Chemical class OS(=O)(=O)C1CC(=O)N1 SXTPCWDEYAMPTR-UHFFFAOYSA-N 0.000 description 4
- 239000007832 Na2SO4 Substances 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002924 oxiranes Chemical class 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UBIRCWMYTXDXJX-RXMQYKEDSA-N (5r)-4-oxa-1-azabicyclo[3.2.0]heptan-7-one Chemical compound O1CCN2C(=O)C[C@H]21 UBIRCWMYTXDXJX-RXMQYKEDSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- QZIQJVCYUQZDIR-UHFFFAOYSA-N mechlorethamine hydrochloride Chemical compound Cl.ClCCN(C)CCCl QZIQJVCYUQZDIR-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- NWPMSXLAMMMLCC-UHFFFAOYSA-N [N].O=C1CCN1 Chemical compound [N].O=C1CCN1 NWPMSXLAMMMLCC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000001010 sulfinic acid amide group Chemical group 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- PWEFRKZZBVCRQB-ZCFIWIBFSA-N (6r)-5-oxa-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound O1CC=CN2C(=O)C[C@H]21 PWEFRKZZBVCRQB-ZCFIWIBFSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- FIEQMOCSOXENFX-UHFFFAOYSA-N 4-oxoazetidine-2-sulfinic acid Chemical class OS(=O)C1CC(=O)N1 FIEQMOCSOXENFX-UHFFFAOYSA-N 0.000 description 1
- 108020004256 Beta-lactamase Proteins 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 102000006635 beta-lactamase Human genes 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229940090805 clavulanate Drugs 0.000 description 1
- 229960003324 clavulanic acid Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- LQOLIRLGBULYKD-JKIFEVAISA-N cloxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl LQOLIRLGBULYKD-JKIFEVAISA-N 0.000 description 1
- 229960003326 cloxacillin Drugs 0.000 description 1
- SCLZRKVZRBKZCR-SLINCCQESA-M cloxacillin sodium Chemical compound [Na+].N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C([O-])=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl SCLZRKVZRBKZCR-SLINCCQESA-M 0.000 description 1
- 229960003026 cloxacillin sodium Drugs 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000001475 halogen functional group Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Epoxy Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HR970146A HRP970146A2 (en) | 1997-03-13 | 1997-03-13 | Epoxi-azetidines, preparation and use |
| BA980291A BA98291A (bs) | 1997-03-13 | 1998-03-04 | Epoksi-azetidinoni priprava i upotreba |
| SK304-98A SK30498A3 (en) | 1997-03-13 | 1998-03-06 | Epoxy - azetidinones, the preparation and use thereof |
| EP98104063A EP0864570A1 (en) | 1997-03-13 | 1998-03-06 | Epoxy-azetidinones, preparation and use thereof |
| CZ98721A CZ72198A3 (cs) | 1997-03-13 | 1998-03-10 | Epoxy-azetidinony, jejich příprava a použití |
| CA002229019A CA2229019A1 (en) | 1997-03-13 | 1998-03-10 | Epoxy-azetinidones preparation and use thereof |
| ARP980101077A AR011965A1 (es) | 1997-03-13 | 1998-03-11 | Compuestos epoxi-azetidinonas, un procedimiento para su preparacion y uso de dichos compuestos como intermedios para la preparacion de nuevos analogosde oxapenam |
| HU9800542A HUP9800542A3 (en) | 1997-03-13 | 1998-03-12 | Epoxy-azetidinones, preparation and use thereof |
| NO981089A NO981089L (no) | 1997-03-13 | 1998-03-12 | Epoksy-azetidinoner, fremstilling og anvendelse derav |
| CN98108076A CN1197071A (zh) | 1997-03-13 | 1998-03-12 | 环氧－氮杂环丁酮及其制备和用途 |
| JP10061199A JPH10306093A (ja) | 1997-03-13 | 1998-03-12 | エポキシ−アゼチジノン、その製造方法及びその使用 |
| BG102318A BG102318A (en) | 1997-03-13 | 1998-03-12 | Epoxy-azetidinons, their preparation and application |
| PL98325306A PL325306A1 (en) | 1997-03-13 | 1998-03-12 | Epoxyazetidiones, method of obtaining them and their application |
| RU98104948A RU2144537C1 (ru) | 1997-03-13 | 1998-03-12 | Эпоксиазетидиноны |
| KR1019980008418A KR19980080207A (ko) | 1997-03-13 | 1998-03-13 | 에폭시-아제티디논, 이의 제조법 및 이의 용도 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HR970146A HRP970146A2 (en) | 1997-03-13 | 1997-03-13 | Epoxi-azetidines, preparation and use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP970146A2 true HRP970146A2 (en) | 1998-10-31 |
Family
ID=10946554
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR970146A HRP970146A2 (en) | 1997-03-13 | 1997-03-13 | Epoxi-azetidines, preparation and use |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0864570A1 (sk) |
| JP (1) | JPH10306093A (sk) |
| KR (1) | KR19980080207A (sk) |
| CN (1) | CN1197071A (sk) |
| AR (1) | AR011965A1 (sk) |
| BA (1) | BA98291A (sk) |
| BG (1) | BG102318A (sk) |
| CA (1) | CA2229019A1 (sk) |
| CZ (1) | CZ72198A3 (sk) |
| HR (1) | HRP970146A2 (sk) |
| HU (1) | HUP9800542A3 (sk) |
| NO (1) | NO981089L (sk) |
| PL (1) | PL325306A1 (sk) |
| RU (1) | RU2144537C1 (sk) |
| SK (1) | SK30498A3 (sk) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1510794A (en) * | 1974-08-06 | 1978-05-17 | Univ Kingston | 1-oxacephems and intermediates therefor |
| GB1510795A (en) * | 1974-08-06 | 1978-05-17 | Univ Kingston | 2-(2'-chloro-3'-substituted-4-oxo)azetidinyl-3-methyl-3-butenoates |
| JPS609514B2 (ja) * | 1976-08-05 | 1985-03-11 | 塩野義製薬株式会社 | ７−アミノ−３′−ノルセファロスポラン酸類 |
| US4937331A (en) * | 1988-03-25 | 1990-06-26 | President And Fellows Of Harvard College | Chiral azetidinone epoxides |
| HU212573B (en) * | 1991-02-12 | 1996-08-29 | Pliva Pharm & Chem Works | Process for producing 4-oxo-azetidine-2-sulfonic acids and their salts |
| DE4230053A1 (de) * | 1992-09-08 | 1994-03-10 | Pliva Handels Gmbh | 4-Oxo-azetidin-2-sulfonsäureamide und ihre Salze, Verfahren zu deren Herstellung und ihre Verwendung |
-
1997
- 1997-03-13 HR HR970146A patent/HRP970146A2/hr not_active Application Discontinuation
-
1998
- 1998-03-04 BA BA980291A patent/BA98291A/bs unknown
- 1998-03-06 EP EP98104063A patent/EP0864570A1/en not_active Withdrawn
- 1998-03-06 SK SK304-98A patent/SK30498A3/sk unknown
- 1998-03-10 CZ CZ98721A patent/CZ72198A3/cs unknown
- 1998-03-10 CA CA002229019A patent/CA2229019A1/en not_active Abandoned
- 1998-03-11 AR ARP980101077A patent/AR011965A1/es unknown
- 1998-03-12 NO NO981089A patent/NO981089L/no not_active Application Discontinuation
- 1998-03-12 CN CN98108076A patent/CN1197071A/zh active Pending
- 1998-03-12 JP JP10061199A patent/JPH10306093A/ja active Pending
- 1998-03-12 RU RU98104948A patent/RU2144537C1/ru active
- 1998-03-12 PL PL98325306A patent/PL325306A1/xx unknown
- 1998-03-12 HU HU9800542A patent/HUP9800542A3/hu unknown
- 1998-03-12 BG BG102318A patent/BG102318A/xx unknown
- 1998-03-13 KR KR1019980008418A patent/KR19980080207A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0864570A1 (en) | 1998-09-16 |
| BG102318A (en) | 1999-08-31 |
| HUP9800542A2 (hu) | 1998-11-30 |
| CN1197071A (zh) | 1998-10-28 |
| RU2144537C1 (ru) | 2000-01-20 |
| HUP9800542A3 (en) | 1999-01-28 |
| CA2229019A1 (en) | 1998-09-13 |
| NO981089L (no) | 1998-09-14 |
| HU9800542D0 (en) | 1998-05-28 |
| JPH10306093A (ja) | 1998-11-17 |
| BA98291A (bs) | 2000-11-06 |
| AR011965A1 (es) | 2000-09-13 |
| CZ72198A3 (cs) | 1998-11-11 |
| PL325306A1 (en) | 1998-09-14 |
| NO981089D0 (no) | 1998-03-12 |
| SK30498A3 (en) | 1998-10-07 |
| KR19980080207A (ko) | 1998-11-25 |
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