SK29396A3 - A process for the preparation of 9-(2-hydroxy)-ethoxymethyl- -guanine - Google Patents
A process for the preparation of 9-(2-hydroxy)-ethoxymethyl- -guanine Download PDFInfo
- Publication number
- SK29396A3 SK29396A3 SK293-96A SK29396A SK29396A3 SK 29396 A3 SK29396 A3 SK 29396A3 SK 29396 A SK29396 A SK 29396A SK 29396 A3 SK29396 A3 SK 29396A3
- Authority
- SK
- Slovakia
- Prior art keywords
- acyclovir
- guanine
- ethoxymethyl
- solution
- hydroxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229960004150 aciclovir Drugs 0.000 claims abstract description 40
- 238000005804 alkylation reaction Methods 0.000 claims abstract description 3
- 230000029936 alkylation Effects 0.000 claims abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 14
- 229910001868 water Inorganic materials 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- QBDIHFHQWMGAGC-UHFFFAOYSA-N n-(6-oxo-3,7-dihydropurin-2-yl)formamide Chemical compound O=C1NC(NC=O)=NC2=C1NC=N2 QBDIHFHQWMGAGC-UHFFFAOYSA-N 0.000 claims description 9
- 238000000746 purification Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 239000003480 eluent Substances 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000003637 basic solution Substances 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 4
- 230000022244 formylation Effects 0.000 claims description 4
- 238000006170 formylation reaction Methods 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims description 2
- VGGRCVDNFAQIKO-UHFFFAOYSA-N formic anhydride Chemical compound O=COC=O VGGRCVDNFAQIKO-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- QWXRKGCSTOAWIV-UHFFFAOYSA-N 2-(ethoxymethylamino)-3,7-dihydropurin-6-one Chemical compound N1C(NCOCC)=NC(=O)C2=C1N=CN2 QWXRKGCSTOAWIV-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 abstract description 4
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- MEPVQQYWARDYNO-UHFFFAOYSA-N 2-amino-3,7-dihydropurin-6-one;oxaldehyde Chemical compound O=CC=O.N1C(N)=NC(=O)C2=C1N=CN2 MEPVQQYWARDYNO-UHFFFAOYSA-N 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- XEBPBJPZBUSUEO-UHFFFAOYSA-N n-(diaminomethylidene)formamide Chemical compound NC(=N)NC=O XEBPBJPZBUSUEO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- -1 2-benzoylethoxymethyl chloride Chemical compound 0.000 description 2
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 229940015043 glyoxal Drugs 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- 102100021935 C-C motif chemokine 26 Human genes 0.000 description 1
- MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 description 1
- NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 101000897493 Homo sapiens C-C motif chemokine 26 Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000872931 Myoporum sandwicense Species 0.000 description 1
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229940029575 guanosine Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- NALMPLUMOWIVJC-UHFFFAOYSA-N n,n,4-trimethylbenzeneamine oxide Chemical compound CC1=CC=C([N+](C)(C)[O-])C=C1 NALMPLUMOWIVJC-UHFFFAOYSA-N 0.000 description 1
- MXSMRDDXWJSGMC-UHFFFAOYSA-N n-(6-oxo-3,7-dihydropurin-2-yl)acetamide Chemical compound N1C(NC(=O)C)=NC(=O)C2=C1N=CN2 MXSMRDDXWJSGMC-UHFFFAOYSA-N 0.000 description 1
- GILZZWCROUGLIS-UHFFFAOYSA-N n-(9-acetyl-6-oxo-3h-purin-2-yl)acetamide Chemical group N1C(NC(=O)C)=NC(=O)C2=C1N(C(C)=O)C=N2 GILZZWCROUGLIS-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011697 sodium iodate Substances 0.000 description 1
- 235000015281 sodium iodate Nutrition 0.000 description 1
- 229940032753 sodium iodate Drugs 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT93RM000608A IT1266486B1 (it) | 1993-09-10 | 1993-09-10 | Procedimento per la preparazione della 9-(2-idrossi)etossimetil- guanina. |
| IT93MI002324A IT1266654B1 (it) | 1993-11-03 | 1993-11-03 | Procedimento per la purificazione della 9-(2-idrossi) etossimetilguanina |
| PCT/EP1994/000308 WO1995007281A1 (en) | 1993-09-10 | 1994-02-03 | A process for the preparation of 9-(2-hydroxy)-ethoxymethyl-guanine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK29396A3 true SK29396A3 (en) | 1996-10-02 |
Family
ID=26331057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK293-96A SK29396A3 (en) | 1993-09-10 | 1994-02-03 | A process for the preparation of 9-(2-hydroxy)-ethoxymethyl- -guanine |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5756737A (bg) |
| EP (1) | EP0717744B1 (bg) |
| JP (1) | JPH09502707A (bg) |
| CN (1) | CN1041632C (bg) |
| AT (1) | ATE152722T1 (bg) |
| AU (1) | AU685774B2 (bg) |
| BG (1) | BG61569B1 (bg) |
| BR (1) | BR9407426A (bg) |
| CA (1) | CA2171283A1 (bg) |
| DE (1) | DE69403087T2 (bg) |
| DK (1) | DK0717744T3 (bg) |
| ES (1) | ES2103575T3 (bg) |
| FI (1) | FI961054A0 (bg) |
| GR (1) | GR3024343T3 (bg) |
| HU (1) | HU214841B (bg) |
| NO (1) | NO960927L (bg) |
| NZ (1) | NZ261573A (bg) |
| PL (1) | PL174765B1 (bg) |
| RU (1) | RU2125570C1 (bg) |
| SK (1) | SK29396A3 (bg) |
| WO (1) | WO1995007281A1 (bg) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19536164A1 (de) * | 1995-09-28 | 1997-04-03 | Boehringer Ingelheim Kg | Verbessertes Verfahren zur Herstellung von 9-[(2-Hyroxyethoxy)methyl]guanin (Acyclovir) |
| IN179493B (bg) * | 1996-02-22 | 1997-10-11 | Lupin Laboraties Ltd | |
| EP0976751A1 (en) * | 1996-04-09 | 2000-02-02 | Lupin Laboratories Limited | A process for the isomerisation of an N-7 isomer into an N-9 isomer useful in the synthesis of acyclic nucleosides |
| US6440980B1 (en) * | 1996-09-17 | 2002-08-27 | Avanir Pharmaceuticals | Synergistic inhibition of viral replication by long-chain hydrocarbons and nucleoside analogs |
| EP1453833A2 (en) * | 2001-10-15 | 2004-09-08 | Ranbaxy Laboratories, Ltd. | A process for the preparation of ganciclovir intermediate n2-acetyl-9-(1,3-diacetoxy-2-propoxymethyl) guanine |
| YU31104A (sh) * | 2001-10-16 | 2006-08-17 | Avanir Pharmaceuticals | Inhibicija virusa n-dokozanolom |
| US7078524B2 (en) * | 2002-11-22 | 2006-07-18 | Ranbaxy Laboratories Limited | Process for the synthesis of ganciclovir |
| ES2289650T3 (es) * | 2004-03-03 | 2008-02-01 | Chemi S.P.A. | Sal monosodica del acido 3-piridil-1-hidroxietiliden-1,1-bifosfonico amorfa y procedimiento para la preparacion de la misma. |
| US7700694B2 (en) * | 2006-04-28 | 2010-04-20 | Tsrc Corporation | Catalyst composition and method for hydrogenating a polymer having a conjugated diene |
| CN117551100B (zh) * | 2024-01-12 | 2024-03-12 | 苏州诺维康生物科技有限公司 | (s)-9-[3-(4,4'-双甲氧基三苯甲基)-2-羟基丙基]-n2-乙酰基鸟嘌呤的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146715A (en) * | 1975-08-27 | 1979-03-27 | Burroughs Wellcome Co. | 2-amido-9-(2-acyloxyethoxymethyl)hypoxanthines |
| YU41079B (en) * | 1976-08-27 | 1986-12-31 | Wellcome Found | Process for the synthesis of substituted purine compounds |
| US4816447A (en) * | 1981-08-26 | 1989-03-28 | Merck & Co., Inc. | Anti-viral guanine compounds |
| JPS5980685A (ja) * | 1982-10-29 | 1984-05-10 | Fujisawa Pharmaceut Co Ltd | Ｎ−低級アルカノイルグアニン誘導体およびそれを用いる方法 |
| JP3225545B2 (ja) * | 1991-09-18 | 2001-11-05 | 味の素株式会社 | 非環状ヌクレオシド類の製造法 |
-
1994
- 1994-02-03 WO PCT/EP1994/000308 patent/WO1995007281A1/en not_active Application Discontinuation
- 1994-02-03 ES ES94906897T patent/ES2103575T3/es not_active Expired - Lifetime
- 1994-02-03 DE DE69403087T patent/DE69403087T2/de not_active Expired - Fee Related
- 1994-02-03 BR BR9407426A patent/BR9407426A/pt not_active Application Discontinuation
- 1994-02-03 AT AT94906897T patent/ATE152722T1/de not_active IP Right Cessation
- 1994-02-03 RU RU96107229A patent/RU2125570C1/ru active
- 1994-02-03 SK SK293-96A patent/SK29396A3/sk unknown
- 1994-02-03 AU AU60383/94A patent/AU685774B2/en not_active Ceased
- 1994-02-03 NZ NZ261573A patent/NZ261573A/en unknown
- 1994-02-03 US US08/602,789 patent/US5756737A/en not_active Expired - Fee Related
- 1994-02-03 HU HU9600556A patent/HU214841B/hu not_active IP Right Cessation
- 1994-02-03 EP EP94906897A patent/EP0717744B1/en not_active Expired - Lifetime
- 1994-02-03 CN CN94193288A patent/CN1041632C/zh not_active Expired - Fee Related
- 1994-02-03 DK DK94906897.7T patent/DK0717744T3/da active
- 1994-02-03 PL PL94313322A patent/PL174765B1/pl unknown
- 1994-02-03 CA CA002171283A patent/CA2171283A1/en not_active Abandoned
- 1994-02-03 JP JP7508403A patent/JPH09502707A/ja active Pending
-
1996
- 1996-03-04 BG BG100395A patent/BG61569B1/bg unknown
- 1996-03-07 FI FI961054A patent/FI961054A0/fi unknown
- 1996-03-07 NO NO960927A patent/NO960927L/no unknown
-
1997
- 1997-07-31 GR GR970401990T patent/GR3024343T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU9600556D0 (en) | 1996-05-28 |
| NO960927D0 (no) | 1996-03-07 |
| PL174765B1 (pl) | 1998-09-30 |
| JPH09502707A (ja) | 1997-03-18 |
| NZ261573A (en) | 1997-02-24 |
| EP0717744A1 (en) | 1996-06-26 |
| BR9407426A (pt) | 1996-04-09 |
| FI961054A (fi) | 1996-03-07 |
| ATE152722T1 (de) | 1997-05-15 |
| HU214841B (hu) | 1998-06-29 |
| EP0717744B1 (en) | 1997-05-07 |
| AU685774B2 (en) | 1998-01-29 |
| CN1130382A (zh) | 1996-09-04 |
| GR3024343T3 (en) | 1997-10-31 |
| DK0717744T3 (da) | 1997-12-08 |
| ES2103575T3 (es) | 1997-09-16 |
| CN1041632C (zh) | 1999-01-13 |
| AU6038394A (en) | 1995-03-27 |
| BG61569B1 (en) | 1997-12-30 |
| BG100395A (bg) | 1996-09-30 |
| NO960927L (no) | 1996-03-07 |
| DE69403087T2 (de) | 1997-08-14 |
| RU2125570C1 (ru) | 1999-01-27 |
| FI961054A0 (fi) | 1996-03-07 |
| HUT74295A (en) | 1996-11-28 |
| CA2171283A1 (en) | 1995-03-16 |
| DE69403087D1 (de) | 1997-06-12 |
| US5756737A (en) | 1998-05-26 |
| PL313322A1 (en) | 1996-06-24 |
| WO1995007281A1 (en) | 1995-03-16 |
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