YU46761B - Postupak za dobijanje piperazinil derivata purina i njihovih izostereomera - Google Patents
Postupak za dobijanje piperazinil derivata purina i njihovih izostereomeraInfo
- Publication number
- YU46761B YU46761B YU141088A YU141088A YU46761B YU 46761 B YU46761 B YU 46761B YU 141088 A YU141088 A YU 141088A YU 141088 A YU141088 A YU 141088A YU 46761 B YU46761 B YU 46761B
- Authority
- YU
- Yugoslavia
- Prior art keywords
- preparation
- isostereomers
- purine derivatives
- compounds
- piperazinyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- XHMOVCSOULHBDU-UHFFFAOYSA-N 2-piperazin-1-yl-7h-purine Chemical class C1CNCCN1C1=NC=C(NC=N2)C2=N1 XHMOVCSOULHBDU-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 abstract 2
- FFNVVVLETZYYJN-UHFFFAOYSA-N 6-piperazin-1-yl-7h-purine Chemical compound C1CNCCN1C1=NC=NC2=C1NC=N2 FFNVVVLETZYYJN-UHFFFAOYSA-N 0.000 abstract 1
- 206010022489 Insulin Resistance Diseases 0.000 abstract 1
- 208000008589 Obesity Diseases 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000008280 blood Substances 0.000 abstract 1
- 210000004369 blood Anatomy 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 230000002218 hypoglycaemic effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 235000020824 obesity Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/16—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/24—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one nitrogen and one sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Hematology (AREA)
- Veterinary Medicine (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cephalosporin Compounds (AREA)
Abstract
POSTUPAK ZA DOBIJANJE PIPERAZINIL DERIVATA PURINA I NJIHOVIH IZOSTEREOMERA, formule: u kojoj X i Y imaju sledeca znacenja: X Y N-(R3)m N-(R3)n CR3 N-R3 N S N O i R1 i R3 nezavisno su vodonik, C1-6alkil pravog ili racvastog niza, C3-6ciklonizialkil, C2-6nizialkenil, C1-6nizialkoksi C1-6nizialkil, C2-6nizialkinil, fenil C1-6nizialkil ili supstituisani C1-6nizialkil, gde 1 do 3 supstituenta je halogen fluor, hlor, brom ili jod, C1-6-nizialkiltio, C1-6nizialkilsulfinil, C1-6nizialkilsulfonil, C1-6nizialkilamino ili di C1-6nizialkilamino, ili supstituent je 5- ili 6-clani heteroaromaticni prstenasti sistem sa N,O ili S kao heteroatomom, narocito piridil, furil ili tienil, i m i n jesu 0 ili 1, tako da kad m je 0 n je 1, i kad m je 1 n je 0; R2 i R4 nezavisno su vodonik, C1-6nizialkil, C3-6ciklonizialkil, C1-6nizialkoksi, C1-6nizialkiltio, C1-6nizialkilsulfinil, C1-6nizialkilsul-fonil, C2-6-nizialkenil, C2-6nizialkeniloksi, C2-6nizialkinil, mono-di-ili trihaloC1-6nizialkil, gde halogen je fluor, hlor, brom ili jod, fenil ili supstituisani fenil gde supstituent je od 1 do 3 halo atoma ili C1-6nizialkil, fenilC1-6nizialkil, amino, C1-6nizialkilamino ili dialkilamino, gde alkil grupe mogu da budu linearne, racvaste ili spojene u 5-ili 6-clani prsten koji opciono sadrzi kiseonik ili azot kao heteroatom, i njihovih farmaceutski prihvatljivih soli, naznacen time, sto za dobijanje jedinjenja formule I reaguje sa R1 supstituisani ili zasticeni piperazin sa hlorheterociklicnim jedinjenjem formule gde X, Y, R1, R2 i R3 imaju napred navedena znacenja, na temperaturi od 100° do 150°C prvenstveno na 75° do 125°C u rastvaracu kao sto je N,N'-dimetilformamid, etanol, izoamilalkohol, u trajanju od 13 minuta do 16 casova. Prijava sadrzi jos jedan patentni zahtev.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7536287A | 1987-07-20 | 1987-07-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| YU141088A YU141088A (en) | 1990-10-31 |
| YU46761B true YU46761B (sh) | 1994-05-10 |
Family
ID=22125206
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU141088A YU46761B (sh) | 1987-07-20 | 1988-07-20 | Postupak za dobijanje piperazinil derivata purina i njihovih izostereomera |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0300726B1 (sh) |
| JP (1) | JP2562181B2 (sh) |
| KR (1) | KR890002155A (sh) |
| AT (1) | ATE94877T1 (sh) |
| AU (1) | AU601862B2 (sh) |
| CA (1) | CA1341043C (sh) |
| DE (1) | DE3884304T2 (sh) |
| DK (1) | DK403188A (sh) |
| ES (1) | ES2058291T3 (sh) |
| FI (1) | FI883423A (sh) |
| HU (1) | HU199144B (sh) |
| IL (1) | IL87149A (sh) |
| NO (1) | NO167203C (sh) |
| NZ (1) | NZ225447A (sh) |
| PT (1) | PT88029B (sh) |
| YU (1) | YU46761B (sh) |
| ZA (1) | ZA885242B (sh) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL86007A0 (en) * | 1987-04-09 | 1988-09-30 | Wellcome Found | 6-substituted purine nucleosides,their preparation and pharmaceutical compositions containing them |
| GB8716313D0 (en) * | 1987-07-10 | 1987-08-19 | Janssen Pharmaceutica Nv | 2-(heterocyclylalkyl)imidazopyridines |
| GB8922076D0 (en) * | 1989-09-28 | 1989-11-15 | Beecham Group Plc | Novel process |
| DK150591D0 (da) * | 1991-08-26 | 1991-08-26 | Novo Nordisk As | Kemisk forbindelse |
| WO1993017021A1 (en) * | 1992-02-19 | 1993-09-02 | Pfizer, Inc. | Heterocyclic compounds for enhancing antitumor activity |
| US5864037A (en) * | 1996-06-06 | 1999-01-26 | Euro-Celtique, S.A. | Methods for the synthesis of chemical compounds having PDE-IV inhibitory activity |
| ATE496035T1 (de) | 1998-03-31 | 2011-02-15 | Kyowa Hakko Kirin Co Ltd | Stickstoffenthaltende heterocyclische verbindungen |
| US7544675B2 (en) | 2002-04-18 | 2009-06-09 | Ucb, S.A. | Chemical compounds with dual activity, processes for their preparation and pharmaceutical compositions |
| GB0215293D0 (en) | 2002-07-03 | 2002-08-14 | Rega Foundation | Viral inhibitors |
| EP1568699A4 (en) * | 2002-12-04 | 2007-08-15 | Eisai R&D Man Co Ltd | 1,3-DIHYDROIMIDAZOLE CONNECTION WITH CONDENSED RING |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| AU2004269923B2 (en) | 2003-09-05 | 2010-05-13 | Takeda Gmbh | Use of PDE4 inhibitors for the treatment of diabetes mellitus |
| US20050222198A1 (en) | 2003-12-22 | 2005-10-06 | K.U. Leuven Research & Development, Gerhard Puerstinger And Gilead Sciences, Inc. | Imidazo[4,5-c]pyridine compounds and methods of antiviral treatment |
| CN101006078A (zh) | 2004-06-17 | 2007-07-25 | 惠氏公司 | 促性腺素释放激素受体拮抗剂 |
| CN1968948A (zh) | 2004-06-17 | 2007-05-23 | 惠氏公司 | 用于制备促性腺激素释放激素受体拮抗剂的方法 |
| DE602005013580D1 (de) | 2004-12-21 | 2009-05-07 | Leuven K U Res & Dev | Imidazoä4,5-cüpyridinverbindung und verfahren zur antiviralen behandlung |
| US7538113B2 (en) * | 2005-02-18 | 2009-05-26 | Wyeth | 4-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
| US7534796B2 (en) | 2005-02-18 | 2009-05-19 | Wyeth | Imidazo[4,5-b]pyridine antagonists of gonadotropin releasing hormone receptor |
| US7582634B2 (en) | 2005-02-18 | 2009-09-01 | Wyeth | 7-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
| US8017633B2 (en) | 2005-03-08 | 2011-09-13 | Nycomed Gmbh | Roflumilast for the treatment of diabetes mellitus |
| US7531542B2 (en) | 2005-05-18 | 2009-05-12 | Wyeth | Benzooxazole and benzothiazole antagonists of gonadotropin releasing hormone receptor |
| US7582636B2 (en) | 2005-05-26 | 2009-09-01 | Wyeth | Piperazinylimidazopyridine and piperazinyltriazolopyridine antagonists of Gonadotropin Releasing Hormone receptor |
| AU2007269614B2 (en) | 2006-07-07 | 2011-09-08 | Gilead Sciences, Inc. | Novel pyridazine compound and use thereof |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| US20100120694A1 (en) | 2008-06-04 | 2010-05-13 | Synergy Pharmaceuticals, Inc. | Agonists of Guanylate Cyclase Useful for the Treatment of Gastrointestinal Disorders, Inflammation, Cancer and Other Disorders |
| US7879802B2 (en) | 2007-06-04 | 2011-02-01 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| UA99466C2 (en) | 2007-07-06 | 2012-08-27 | Гилиад Сайенсиз, Инк. | Crystalline pyridazine compound |
| US8513221B2 (en) * | 2008-07-07 | 2013-08-20 | Xcovery Holding, LLC | PI3K isoform selective inhibitors |
| ES2624828T3 (es) | 2008-07-16 | 2017-07-17 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros |
| UA104010C2 (en) | 2008-12-18 | 2013-12-25 | Эли Лилли Энд Компани | Purine compounds |
| ES2665277T3 (es) * | 2009-03-13 | 2018-04-25 | Katholieke Universiteit Leuven K.U. Leuven R&D | Análogos de purina y su uso como agentes inmunosupresores |
| AR080711A1 (es) | 2010-03-31 | 2012-05-02 | Lilly Co Eli | Compuesto de piperazin-purina composicion farmaceutica que lo comprende y su uso para preparar un medicamento util para el tratamiento o prevencion del dolor |
| MX2012011164A (es) | 2010-03-31 | 2012-11-12 | Lilly Co Eli | Compuesto de purina usados como agonistas de cb2. |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| MX357121B (es) | 2011-03-01 | 2018-06-27 | Synergy Pharmaceuticals Inc Star | Proceso de preparacion de agonistas c de guanilato ciclasa. |
| US9545446B2 (en) | 2013-02-25 | 2017-01-17 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase and their uses |
| CA2905438A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| AU2014235209B2 (en) | 2013-03-15 | 2018-06-14 | Bausch Health Ireland Limited | Guanylate cyclase receptor agonists combined with other drugs |
| JP6513636B2 (ja) * | 2013-05-02 | 2019-05-15 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | Ｃｂ２受容体アゴニストとしてのプリン誘導体 |
| EP3004138B1 (en) | 2013-06-05 | 2024-03-13 | Bausch Health Ireland Limited | Ultra-pure agonists of guanylate cyclase c, method of making and using same |
| JP6694385B2 (ja) | 2013-08-09 | 2020-05-13 | アーデリクス，インコーポレーテッド | リン酸塩輸送阻害のための化合物及び方法 |
| CN104497085B (zh) * | 2015-01-16 | 2017-05-24 | 华东理工大学 | 腺苷衍生物及其用途 |
| US20200368223A1 (en) | 2019-05-21 | 2020-11-26 | Ardelyx, Inc. | Methods for inhibiting phosphate transport |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1115260B (de) * | 1957-02-27 | 1961-10-19 | Thomae Gmbh Dr K | Verfahren zur Herstellung von Purinderivaten |
| GB1186504A (en) * | 1966-10-15 | 1970-04-02 | Fisons Pest Control Ltd | Substituted Heterocyclic Compounds |
| JPS60260579A (ja) * | 1984-01-13 | 1985-12-23 | Yoshitomi Pharmaceut Ind Ltd | プリン誘導体 |
| JPS6210085A (ja) * | 1985-07-05 | 1987-01-19 | Yoshitomi Pharmaceut Ind Ltd | トリフルオロメチルプリン誘導体 |
-
1988
- 1988-07-18 NZ NZ225447A patent/NZ225447A/en unknown
- 1988-07-18 IL IL8714988A patent/IL87149A/xx unknown
- 1988-07-19 AU AU19230/88A patent/AU601862B2/en not_active Ceased
- 1988-07-19 FI FI883423A patent/FI883423A/fi not_active Application Discontinuation
- 1988-07-19 PT PT88029A patent/PT88029B/pt not_active IP Right Cessation
- 1988-07-19 DK DK403188A patent/DK403188A/da not_active Application Discontinuation
- 1988-07-19 CA CA000572450A patent/CA1341043C/en not_active Expired - Fee Related
- 1988-07-19 EP EP88306584A patent/EP0300726B1/en not_active Expired - Lifetime
- 1988-07-19 DE DE88306584T patent/DE3884304T2/de not_active Expired - Fee Related
- 1988-07-19 HU HU883774A patent/HU199144B/hu not_active IP Right Cessation
- 1988-07-19 ES ES88306584T patent/ES2058291T3/es not_active Expired - Lifetime
- 1988-07-19 AT AT88306584T patent/ATE94877T1/de not_active IP Right Cessation
- 1988-07-19 NO NO883204A patent/NO167203C/no unknown
- 1988-07-20 KR KR1019880009044A patent/KR890002155A/ko not_active Application Discontinuation
- 1988-07-20 JP JP63179325A patent/JP2562181B2/ja not_active Expired - Fee Related
- 1988-07-20 YU YU141088A patent/YU46761B/sh unknown
- 1988-07-20 ZA ZA885242A patent/ZA885242B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR890002155A (ko) | 1989-04-08 |
| PT88029B (pt) | 1995-03-01 |
| FI883423A (fi) | 1989-01-21 |
| NO167203B (no) | 1991-07-08 |
| ES2058291T3 (es) | 1994-11-01 |
| YU141088A (en) | 1990-10-31 |
| EP0300726A1 (en) | 1989-01-25 |
| IL87149A0 (en) | 1988-12-30 |
| DK403188A (da) | 1989-03-30 |
| DE3884304T2 (de) | 1994-03-24 |
| CA1341043C (en) | 2000-07-04 |
| EP0300726B1 (en) | 1993-09-22 |
| NO883204D0 (no) | 1988-07-19 |
| HU199144B (en) | 1990-01-29 |
| HUT47575A (en) | 1989-03-28 |
| NO883204L (no) | 1989-01-23 |
| NZ225447A (en) | 1991-12-23 |
| ATE94877T1 (de) | 1993-10-15 |
| JPH01104074A (ja) | 1989-04-21 |
| IL87149A (en) | 1994-05-30 |
| AU601862B2 (en) | 1990-09-20 |
| ZA885242B (en) | 1989-03-29 |
| PT88029A (pt) | 1989-06-30 |
| NO167203C (no) | 1991-10-16 |
| FI883423A0 (fi) | 1988-07-19 |
| AU1923088A (en) | 1989-01-27 |
| DE3884304D1 (de) | 1993-10-28 |
| JP2562181B2 (ja) | 1996-12-11 |
| DK403188D0 (da) | 1988-07-19 |
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