FI106027B - Förfarande för framställning av (S)(+)-2-etoxi-4-[N-[1-(2-piperidinofenyl)-3-metyl-1-butyl]aminokarbonylmetyl]-bensoesyra eller dess salt, samt N-acetyl-L-glutaminsaltar(s) (S)-1-2-piperidinofenyl)-3-metyl-1-butylamin och dess framställning - Google Patents
Förfarande för framställning av (S)(+)-2-etoxi-4-[N-[1-(2-piperidinofenyl)-3-metyl-1-butyl]aminokarbonylmetyl]-bensoesyra eller dess salt, samt N-acetyl-L-glutaminsaltar(s) (S)-1-2-piperidinofenyl)-3-metyl-1-butylamin och dess framställning Download PDFInfo
- Publication number
- FI106027B FI106027B FI935724A FI935724A FI106027B FI 106027 B FI106027 B FI 106027B FI 935724 A FI935724 A FI 935724A FI 935724 A FI935724 A FI 935724A FI 106027 B FI106027 B FI 106027B
- Authority
- FI
- Finland
- Prior art keywords
- group
- methyl
- compound
- phenyl
- general formula
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
-
- 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (15)
1. Förfarande för framställning av fysiologiskt verksam (S)(+)-2-etoxi-4-[N-[1 -(2-piperidino-fenyi)-3-metyl-1 -butyl]aminokarbonylmetyl]-bensoesyra och dess 5 salter med oorganiska eller organiska syror eller baser med formeln CH^ CH, CH ch2 _
10 NH - CO - CH2 —V y— COOH (A) . I / \ \ 0C2Hs kännetecknat därav, att 15 a) en (S)-amin med formeln (I) c V CH aCH2H ^NH2 (» O omsätts med en karboxylsyra med den allmänna formeln (II) 25 H00C-CH2_^~^— w (H) iL oc2hs där
30 W är en karboxigrupp eller en med en skyddsgrupp skyddad karboxigrupp, eller med dess eventuellt i reaktionsblandning framställda reaktiva derivat och vid behov avspjälks därefter den använda skyddsgruppen, eller 106027 47 b) en (S)-förening med den allmänna formeln (III) avspjälks CtL· CH, 3\ / 3 CH CH2H ,-v
5 NH - CO - CH2 —^ \—A (n|) ^•ry οολ där
10 A är ett genom hydrolys, termolys eller hydrogenolys tili en karboxigrupp över-förbart karboxylsyraderivat, eller c) en (S)-förening med den allmänna formeln(IV) CHs\ /CH»
15 CH CH2 μ . t NH - CO - CH2 —P \—W (|V> ti \ 0H 20. där W är en karboxigrupp eller alkoxikarbonylgrupp med tillsammans 2-5 kolato- « ·* mer, varvid alkoxigruppens alkyldel kan vara substituerad med en fenylgrupp, 25 omsätts med en förening med den allmänna formeln (V) Z-CH2-CH3 , (V) ✓ « där
30 Z är en nukleofilt utbytbar grupp eller ocksä tillsammans med bredvidliggande väteatom en diazogrupp, och vid behov hydrolyseras eller hydrogeneras den sä erhallna föreningen därefter, eller ·· • i. ^ 48 106027 d) en förening med den allmänna formeln (VI) reduceras enantioselektivt \—W (VI)
5 CXq _ 0C=H= där W är en karboxigrupp eller alkoxikarbonylgrupp med tillsammans 2-5 kolatomer, varvid alkoxigruppens alkyldel kan vara substituerad med en fenyl-10 grupp, och Y är en grupp med formeln nil CHjv «r^V" - L, 14 11 » |
15 -C-NH-, -C-NH- - C = N - och vid behov hydrolyseras den sa erhällna föreningen därefter eller e) en (S)-förening med den allmänna formeln (VII) ^ ch3 ch3 3\ / 3 CH ?^H /Γ~'\ NH - CO - CH2 —(f (V·1)
25 OC!H5 där W” är en genom oxidering till en karboxigrupp överförbar grupp, oxideras eller 30 f) en blandning, som bestär av en godtycklig mängd av en (S)-enantiomer med den allmänna formeln (Vili) • *. 106027 49 CH3N ^ch, CH CH2 1^1 t V NH - CO - CH2—ft y—W' (VIII) f/ ^ OC2H5 och en godtycklig mängd av en (R)-enantiomer med den allmänna formeln (IX) CH,,. CH, 10 3\ / 3 1U CH a?HlH /-V NH - CO - CH2 —P W' <IX) /—\ N > 0=Λ 15 ^ i vilka W’ är en karboxigrupp eller alkoxikarbonylgrupp med tillsammans 2-5 kol-atomer, varvid alkoxigruppens alkyldel kan vara substituerad med en fenyl-grupp och vid behov med därefter följande hydrolys eller hydrogenolys, och 20 den sä erhällna föreningen vid behov omvandlas genom omkristallisering till en föreningen med högre enantiomerrenhet, varvid med etanol/vatten(2/1 )-kristallisering erhälls en högre smältande form, vars smältpunkt är 130 -131 °C, och med petroleter/toluen(5/3)-kristallisering erhälls en lägre smältande form 25 med en smältpunkt av 99 - 101°C, och den sä erhällna föreningen omvandlas till sitt salt, särskilt ett fysiologiskt acceptabelt salt med oorganiska eller organiska syror eller baser. 30 2. Förfarande enligt patentkravet 1, kännetecknat därav, att en förening, som är optiskt väsentligen ren, framställs. € • «· 106027 50
3. Förfarande enligt patentkravet 2, kännetecknat därav, att dess optiska renhet är ätminstone ee = 95 %.
4. Förfarande enligt patentkravet 2, kännetecknat därav, att dess optiska 5 renhet är ätminstone ee = 98 %.
5. N-acetyl-L-glutaminsalt av (S)-1-(2-piperidino-fenyl)-3-metyl-1-butylamin med den allmänna formeln (I) ch3N ^ch3
10 CH (I) 15 ^
6. Förfarande för framställning av N-acetyl-L-glutaminsalt av (S)-1-(2-piperidino-fenyl)-3-metyl-1-butylamin, kännetecknat därav, att racemisk 1-(2- 20 piperidino-fenyl)-3-metyl-1-butylamin och N-acetyl-L-glutaminsyra och det utfällda saltet av (S)-1-(2-piperidino-fenyl)-3-metyl-1-butylamin separeras med N-acetyl-L-glutaminsyra och vid behov kristalliseras. •. '
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP1991/001147 WO1993000337A1 (de) | 1991-06-21 | 1991-06-21 | (s)(+)-2-äthoxy-4-[n-[1-(2-piperidino-phenyl)-3-methyl-1-butyl]aminocarbonylmethyl]-benzoesäure |
| SG9602715 | 1991-06-21 | ||
| SG1996002715A SG43036A1 (en) | 1991-06-21 | 1991-06-21 | (S) (+) -2-ethoxy-4-[N-[1-(2-piperidino-phenyl)-3-methyl- 1-buthyl]aminocarbony methyl] - benzoic a cid |
| EP9101147 | 1991-06-21 | ||
| CA2111851 | 1991-06-21 | ||
| CA002111851A CA2111851C (en) | 1991-06-21 | 1991-06-21 | (s)(+)-2-ethoxy-4-[n-{1-(2-piperidino-phenyl)-3-methyl-1-butyl]aminocarbonylmethyl]benzoic acid |
| CN91104984A CN1048722C (zh) | 1991-06-21 | 1991-07-22 | (s)(+)-2-乙氧基-4-[n-[1-(2-哌啶子基-苯基)-3-甲基-1-丁基]氨基羰基甲基]苯甲酸,含该化合物的药物组合物及其制备方法 |
| CN91104984 | 1991-07-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI935724A0 FI935724A0 (fi) | 1993-12-20 |
| FI935724A FI935724A (fi) | 1993-12-20 |
| FI106027B true FI106027B (sv) | 2000-11-15 |
Family
ID=36781542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI935724A FI106027B (sv) | 1991-06-21 | 1993-12-20 | Förfarande för framställning av (S)(+)-2-etoxi-4-[N-[1-(2-piperidinofenyl)-3-metyl-1-butyl]aminokarbonylmetyl]-bensoesyra eller dess salt, samt N-acetyl-L-glutaminsaltar(s) (S)-1-2-piperidinofenyl)-3-metyl-1-butylamin och dess framställning |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0589874B1 (sv) |
| JP (1) | JP2921982B2 (sv) |
| KR (1) | KR100496720B1 (sv) |
| CN (1) | CN1048722C (sv) |
| AU (1) | AU660930B2 (sv) |
| BG (1) | BG61690B1 (sv) |
| CA (1) | CA2111851C (sv) |
| DE (2) | DE10075006I2 (sv) |
| DK (2) | DK0965591T3 (sv) |
| FI (1) | FI106027B (sv) |
| GR (1) | GR3031654T3 (sv) |
| HK (1) | HK1011968A1 (sv) |
| NO (2) | NO303687B1 (sv) |
| PL (1) | PL170210B1 (sv) |
| RO (1) | RO113462B1 (sv) |
| SG (1) | SG43036A1 (sv) |
| SK (1) | SK281246B6 (sv) |
| UY (1) | UY25923A1 (sv) |
| WO (1) | WO1993000337A1 (sv) |
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| PT1011673E (pt) | 1997-06-13 | 2001-11-30 | Novo Nordisk As | Nova posologia para a dmni |
| IN192862B (sv) | 1999-11-16 | 2004-05-22 | Ranbaxy Lab Ltd | |
| AR033390A1 (es) | 2000-08-22 | 2003-12-17 | Novartis Ag | Una composicion farmaceutica que comprende un antagonista del receptor at1 y un potenciador de la secrecion de insulina, el uso de dicha composicion para la fabricacion de un medicamento y un kit de partes |
| CN1649614A (zh) | 2002-02-22 | 2005-08-03 | 新河药品股份有限公司 | 活性剂传递系统和保护及施用活性剂的方法 |
| WO2004018442A1 (en) * | 2002-08-23 | 2004-03-04 | Dr. Reddy's Laboratories Limited | Crystalline and amorphous forms of (s) -repaglinide and the processes for preparation thereof |
| US7915421B2 (en) * | 2003-05-14 | 2011-03-29 | Cilag Ltd. | Method for preparing phenyl acetic acid derivatives |
| AU2003237595A1 (en) * | 2003-05-26 | 2004-12-13 | Biocon Limited | Process for the preparation of s(+)-2-ethoxy-4-(n-{1-(2-piperidinophelyl)-3-methyl-1- butyl} aminocarbonylmethyl)benzoic acid derivatives |
| WO2005021524A1 (en) * | 2003-08-28 | 2005-03-10 | Ranbaxy Laboratories Limited | Process for the preparation of amorphous form of repaglinide |
| CN1305863C (zh) * | 2004-12-27 | 2007-03-21 | 浙江大学 | (s)－异丙基－(2－哌啶)苯基－甲基胺的合成方法 |
| GT200600381A (es) | 2005-08-25 | 2007-03-28 | Compuestos organicos | |
| FR2898894B1 (fr) * | 2006-03-24 | 2008-06-06 | Genfit Sa | Composes derives de n-(phenethyl)benzamide substitues, preparation et utilisations |
| US7763607B2 (en) * | 2006-04-27 | 2010-07-27 | Solvay Pharmaceuticals Gmbh | Pharmaceutical compositions comprising CBx cannabinoid receptor modulators and potassium channel modulators |
| CA2666846C (en) * | 2006-10-20 | 2018-04-10 | Cpd, Llc | Method of restoring the incretin effect |
| US8101769B2 (en) | 2007-02-15 | 2012-01-24 | Actavis Group Ptc Ehf | Process for preparing ethyl (S)-2-ethoxy-4-[N-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonyl methyl]benzoate and use thereof for the preparation of Repaglinide |
| CN101772491A (zh) * | 2007-06-06 | 2010-07-07 | 阿克塔维什集团Ptc公司 | 基本不含有二聚体杂质的瑞格列奈 |
| EP2019097A1 (en) | 2007-07-25 | 2009-01-28 | Aurobindo Pharma Limited | Process for preparing (alphaS)-alpha-(2-methylpropyl)-2-(1-piperidinyl)benzenemethanamine |
| DK2200588T3 (da) | 2007-09-25 | 2019-07-01 | Solubest Ltd | Sammensætninger, som omfatter lipofile aktive forbindelser, og fremgangsmåde til fremstilling deraf |
| DE102008046995B4 (de) * | 2008-09-12 | 2010-08-26 | Stada Arzneimittel Ag | 2-Ethoxy-benzoesäurederivat |
| EP2177221A1 (en) | 2008-10-20 | 2010-04-21 | Krka Tovarna Zdravil, D.D., Novo Mesto | Process for the preparation of substantially optically pure Repaglinide and precursors thereof |
| BRPI1010600A2 (pt) | 2009-05-15 | 2016-03-15 | Novartis Ag | aril piridina como inibidores de aldosterona sintase |
| CN102459247B (zh) | 2009-05-15 | 2014-09-17 | 诺华股份有限公司 | 作为醛固酮合酶抑制剂的苯并噁唑酮衍生物 |
| SG176010A1 (en) | 2009-05-28 | 2011-12-29 | Novartis Ag | Substituted aminobutyric derivatives as neprilysin inhibitors |
| KR101442897B1 (ko) | 2009-05-28 | 2014-09-23 | 노파르티스 아게 | 네프릴리신 억제제로서의 치환된 아미노프로피온산 유도체 |
| US8519134B2 (en) | 2009-11-17 | 2013-08-27 | Novartis Ag | Aryl-pyridine derivatives as aldosterone synthase inhibitors |
| JO2967B1 (en) | 2009-11-20 | 2016-03-15 | نوفارتس ايه جي | Acetic acid derivatives of carbamoyl methyl amino are substituted as new NEP inhibitors |
| WO2011064376A1 (en) | 2009-11-30 | 2011-06-03 | Novartis Ag | Imidazole derivatives as aldosterone synthase inhibitors |
| EP2364977A1 (en) | 2010-01-26 | 2011-09-14 | Reuter Chemische Apparatebau KG | Process for the enantiomeric enrichment of 3-methyl-1-(2-piperidinophenyl)-1-butylamine |
| US8877815B2 (en) | 2010-11-16 | 2014-11-04 | Novartis Ag | Substituted carbamoylcycloalkyl acetic acid derivatives as NEP |
| US8673974B2 (en) | 2010-11-16 | 2014-03-18 | Novartis Ag | Substituted amino bisphenyl pentanoic acid derivatives as NEP inhibitors |
| CN102267959B (zh) * | 2011-07-06 | 2013-05-01 | 海南锦瑞制药股份有限公司 | 一种瑞格列奈晶体、其制备方法及含有该晶体的固体口服制剂 |
| CN103012319B (zh) * | 2011-09-20 | 2015-06-10 | 浙江九洲药业股份有限公司 | 瑞格列奈中间体的合成工艺改进 |
| CN102584743A (zh) * | 2011-12-28 | 2012-07-18 | 中国药科大学 | 对二甲氨基吡啶瑞格列奈共晶 |
| UY35144A (es) | 2012-11-20 | 2014-06-30 | Novartis Ag | Miméticos lineales sintéticos de apelina para el tratamiento de insuficiencia cardiaca |
| NZ710574A (en) | 2013-02-14 | 2017-11-24 | Novartis Ag | Substituted bisphenyl butanoic phosphonic acid derivatives as nep (neutral endopeptidase) inhibitors |
| US9340582B2 (en) | 2013-07-25 | 2016-05-17 | Novartis Ag | Bioconjugates of synthetic apelin polypeptides |
| WO2015013168A1 (en) | 2013-07-25 | 2015-01-29 | Novartis Ag | Cyclic polypeptides for the treatment of heart failure |
| WO2016073615A1 (en) | 2014-11-07 | 2016-05-12 | Regents Of The University Of Minnesota | Salts and compositions useful for treating disease |
| CA2972871A1 (en) | 2015-01-23 | 2016-07-28 | Novartis Ag | Synthetic apelin fatty acid conjugates with improved half-life |
| WO2018034627A1 (en) | 2016-08-18 | 2018-02-22 | İlko Ilaç Sanayi Ve Ticaret Anonim Şirketi | Pharmaceutical composition of antidiabetic tablet |
| UY38072A (es) | 2018-02-07 | 2019-10-01 | Novartis Ag | Compuestos derivados de éster butanoico sustituido con bisfenilo como inhibidores de nep, composiciones y combinaciones de los mismos |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3347565A1 (de) * | 1983-12-30 | 1985-07-11 | Thomae Gmbh Dr K | Neue phenylessigsaeurederivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
-
1991
- 1991-06-21 EP EP91911959A patent/EP0589874B1/de not_active Expired - Lifetime
- 1991-06-21 AU AU80781/91A patent/AU660930B2/en not_active Expired
- 1991-06-21 WO PCT/EP1991/001147 patent/WO1993000337A1/de active IP Right Grant
- 1991-06-21 SG SG1996002715A patent/SG43036A1/en unknown
- 1991-06-21 JP JP3511056A patent/JP2921982B2/ja not_active Expired - Lifetime
- 1991-06-21 DE DE2000175006 patent/DE10075006I2/de active Active
- 1991-06-21 PL PL91301997A patent/PL170210B1/pl unknown
- 1991-06-21 SK SK1280-93A patent/SK281246B6/sk not_active IP Right Cessation
- 1991-06-21 DE DE59109151T patent/DE59109151D1/de not_active Expired - Lifetime
- 1991-06-21 RO RO93-01692A patent/RO113462B1/ro unknown
- 1991-06-21 CA CA002111851A patent/CA2111851C/en not_active Expired - Lifetime
- 1991-06-21 DK DK99101810T patent/DK0965591T3/da active
- 1991-06-21 DK DK91911959T patent/DK0589874T3/da active
- 1991-06-21 KR KR1019930703974A patent/KR100496720B1/ko active
- 1991-07-22 CN CN91104984A patent/CN1048722C/zh not_active Expired - Lifetime
-
1993
- 1993-12-14 BG BG98300A patent/BG61690B1/bg unknown
- 1993-12-20 FI FI935724A patent/FI106027B/sv not_active IP Right Cessation
- 1993-12-20 NO NO934726A patent/NO303687B1/no not_active IP Right Cessation
-
1998
- 1998-12-08 HK HK98112967A patent/HK1011968A1/xx not_active IP Right Cessation
-
1999
- 1999-07-20 NO NO1999017C patent/NO1999017I1/no unknown
- 1999-10-27 GR GR990402743T patent/GR3031654T3/el unknown
-
2000
- 2000-01-17 UY UY25923A patent/UY25923A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2111851A1 (en) | 1993-01-07 |
| SK128093A3 (en) | 1994-11-09 |
| SK281246B6 (sk) | 2001-01-18 |
| NO934726L (no) | 1993-12-20 |
| AU660930B2 (en) | 1995-07-13 |
| GR3031654T3 (en) | 2000-02-29 |
| FI935724A0 (fi) | 1993-12-20 |
| NO1999017I1 (no) | 1999-07-20 |
| DK0589874T3 (da) | 2000-04-03 |
| JPH06508816A (ja) | 1994-10-06 |
| EP0589874B1 (de) | 1999-09-08 |
| AU8078191A (en) | 1993-01-25 |
| WO1993000337A1 (de) | 1993-01-07 |
| DE10075006I2 (de) | 2004-01-08 |
| JP2921982B2 (ja) | 1999-07-19 |
| BG98300A (bg) | 1994-09-30 |
| DE10075006I1 (de) | 2000-04-20 |
| CA2111851C (en) | 2002-02-26 |
| DE59109151D1 (de) | 1999-10-14 |
| NO303687B1 (no) | 1998-08-17 |
| CN1068820A (zh) | 1993-02-10 |
| PL170210B1 (pl) | 1996-11-29 |
| KR100496720B1 (ko) | 2006-01-27 |
| HK1011968A1 (en) | 1999-07-23 |
| FI935724A (fi) | 1993-12-20 |
| NO934726D0 (no) | 1993-12-20 |
| SG43036A1 (en) | 1997-10-17 |
| BG61690B1 (bg) | 1998-03-31 |
| DK0965591T3 (da) | 2002-11-18 |
| EP0589874A1 (de) | 1994-04-06 |
| RO113462B1 (ro) | 1998-07-30 |
| UY25923A1 (es) | 2001-08-27 |
| CN1048722C (zh) | 2000-01-26 |
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