FI92192C - Menetelmä terapeuttisesti aktiivisten yhdisteiden valmistamiseksi sekä välituotteita - Google Patents

Menetelmä terapeuttisesti aktiivisten yhdisteiden valmistamiseksi sekä välituotteita Download PDF

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Publication number
FI92192C
FI92192C FI893936A FI893936A FI92192C FI 92192 C FI92192 C FI 92192C FI 893936 A FI893936 A FI 893936A FI 893936 A FI893936 A FI 893936A FI 92192 C FI92192 C FI 92192C
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amino
compound
formula
propyl
ethyl
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FI893936A
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English (en)
Swedish (sv)
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FI893936A0 (fi
FI893936A (fi
FI92192B (fi
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Knut Olle Seved Almgren
Bernt Goeran Duke Duker
Gert Christer Strandlund
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Haessle Ab
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/32—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/40—Y being a hydrogen or a carbon atom
    • C07C323/41—Y being a hydrogen or an acyclic carbon atom

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Cardiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cephalosporin Compounds (AREA)
  • Pyridine Compounds (AREA)

Claims (24)

  1. 92192 80
  2. 1. Menetelmå terapeuttisesti aktiivisen yhdisteen valmis-tamiseksi, jolla on kaava
  3. 5 O- (CH2) n-Y-CH2-A [O) 10 CN ja silloin kun se on soveliasta, raseemisen seoksen muodossa tai stereoisomeerisen komponentin muodossa, ja sen farma -15 seuttisesti hyvåksyttåvien suolojen valmistamiseksi, jossa kaavassa n on kokonaisluku 0, 1 tai 2, Y on [CH2] m, CHOH tai CHF, 20. on kokonaisluku 0 tai 1, ja A on ryhmå Ra (0)p Ra. (0)p
  4. 25 I || J || -N- [CH-,] s - S - Rc tai -®N- [CH2] s-S-Rc Ra- 30 jossa Ra on suoraketjuinen tai haaroittunut hydroksialkyyli- tai alkyyliryhmå, jossa on 1 - 5 hiiliatomia, Rc on tyydyttynyt tai tyydyttymåton, suoraketjuinen tai haaroittunut alkyyliryhmå, jossa on 1 - 4 hiiliatomia ja joka • 35 mahdollisesti on substituoitu yhdellå tai useammalla fluo-riatomilla, Ra. on sama kuin Ra ja riippumaton Ra.:sta, Ra- on sama kuin Ra ja riippumaton R,.:sta, 40. on kokonaisluku 0, 1 tai 2, s on kokonaisluku 2, 3, 4 tai 5, tunnettu si’tå, ettå 921 92 81 a) yhdiste, jolla on kaava Ia
  5. 5 O- (CH2)n-Y-CH2-N-H II Φ
  6. 10 CN saatetaan reagoimaan yhdisteen kanssa, jolla on kaava (0)p
  7. 15 II L- [CH2]s-S-Rc jossa η, Y, Ra, s, p ja Rc ovat edellå esitetyt ja L on kor-vautuva ryhinå kuten Br, Cl, I, mesyylioksi tai tosyylioksi, 20 tai b) sellaisen kaavan I mukaisen yhdisteen valmistamiseksi, jossa p on 1 tai 2, kaavan I mukainen yhdiste, jossa p on 0, hapetetaan, tai 25 c) sellaisen kaavan I mukaisen yhdisteen valmistamiseksi, j ossa n = l, Y = CHOH, 30 p = 1 tai 2, ja Ra, Rc ja s ovat edellå esitetyt, saatetaan yhdiste, jolla on kaava o-ch2- Φ CN 40 reagoimaan yhdisteen kanssa, jolla on kaava 921 92 82 K (0),, I II ΗΝ- [CH:] , - S-R 5 jossa Ra, RcJ s ja p ovat edellå esitetyt, tai d) sellaisen kaavan I mukaisen yhdisteen valmistamiseksi, jossa n = 1,
  8. 10 Y = CHOH, p = 0, 1 tai 2, ja Ra, Rc ja s ovat edellå esitetyt, saatetaan yhdiste, jolla on kaava 15 0-CH2- Φ “ 20 1 CN reagoimaan yhdisteen kanssa, jolla on kaava 25 (0)p II H2N- [CH;] ,-s-r, 30 jossa Rc, s ja p ovat edellå esitetyt, kaavan IV mukaisen yhdisteen saamiseksi (0)p 35 ||
  9. 0-CH2-CH0H-CH2-NH- (CH2)s-S-Rc é)
  10. 40 I CN joka sitten alkyloidaan, tai 45 e) sellaisen kaavan I mukaisen yhdisteen valmistamiseksi, jossa 92192 83 Y = CHOH ja Ra, Rc, n, s ja p ovat edellå esitetyt, saatetaan yhdiste, jolla on kaava 5 0- (CH2)u-CH0H-CH2-0-S02M Φ
  11. 10 CN reagoimaan kaavan III mukaisen yhdisteen kanssa Ra (0)p is I II H-N- [CH2] s-S-Rc III jossa M on metyyli- tai 4-metyylifenyyliryhmå, Ra, Rc, s ja p ovat edellå esitetyt, minkå jålkeen, haluttaessa, jollakin 20 menetelmistå a) - e) saatu yhdiste muutetaan stereoisomee-rikseen tai farmaseuttisesti hyvåksytttåvåksi suolakseen.
  12. 2. Patenttivaatimuksen 1 mukainen menetelmå, tunnettu siitå, ettå valmistetaan sellainen kaavan I mukainen yhdis- 25 te, jossa n on 1, Y on CHOH, CHF tai (CH2)m, jossa m = 1, Ra (0),,
  13. 30. II A on -N- (CH2) S - R_., jossa Ra on CH3, C2H5, C3H7, CH2CH2OH tai CH2CHOHCH3, Rc on C2H5, C3H7 tai CH2CHFCH3> *35 s on 3 tai 4. 1 Patenttivaatimuksen 2 mukainen menetelmå, tunnettu siitå, ettå valmistetaan sellainen kaavan I mukainen yhdiste, jossa p on 1. 40 84 92192
  14. 4. Patenttivaatimuksen 3 mukainen menetelmå, tunnettu siitå, ettå valmistetaan sellainen kaavan I mukainen yhdis-te, jossa Y on CHOH tai (CH2)m, jossa m = 1, Ra on C2H5 tai CH2CH2OH, 5. on 3, Rc on C3H7.
  15. 5. Patenttivaatimuksen 4 mukainen menetelmå, tunnettu siitå, ettå valmistetaan sellainen kaavan I mukainen yhdis- 10 te, jossa Y on CHOH, ja R„ on C2H5.
  16. 6. Patenttivaatimuksen 1 mukainen menetelmå, tunnettu siitå, ettå valmistetaan sellainen kaavan I mukainen yhdis- 15 te, jossa n on 1, Y on CHOH, CHF tai (CH2)m, jossa m = 1, Ra- (0)p J II 20. on -®N- [CH,] s-S-Rc, R.,.. jossa Ra· ja R.,~ ovat toisistaan riippumatta CH3, C2H5 tai C3H7,
  17. 25 Rc on C2H5, C3H7 tai CH2CHFCH3, s on 3 tai 4.
  18. 7. Patenttivaatimuksen 1 mukainen menetelmå 4-[3-[etyy-li[3-(propyylisulfinyyli)propyyli]amino]-2-hydroksipropok- 30 si]bentsonitriilin valmistamiseksi, tunnettu siitå, ettå 4-(oksiranyylimetoksi)bentsonitriili saatetaan reagoimaan etyyli-(3-propyylisulfinyyli)-propyyliamiinin kanssa sopi-• vassa liuottimessa, kuten asetonitriilisså, kuumentaen.
  19. 8. Patenttivaatimuksen 1 mukainen menetelmå, tunnettu sii tå, ettå valmistetaan 4 -[3 -[etyyli[3 -(propyylisulfinyyli)-propyyli]amino]- 2 -hydroksipropoksi]bentsonitriili. li 92192 85
  20. 9. Patenttivaatimuksen 1 mukainen menetelmå, tunnettu sii-tå, ettå valmistetaan 4-[3 -[etyyli[3 - (propyylisulfinyyli)-propyyli]amino]-2(R)-hydroksipropoksi]bentsonitriili.
  21. 10. Patenttivaatimuksen 1 mukainen menetelmå, tunnettu sii- tå, ettå valmistetaan 4-[3-[etyyli[3-(propyylisulfinyyli)-propyyli]amino]-2(S)-hydroksipropoksi]bentsonitriili.
  22. 11. Patenttivaatimuksen 1 mukainen menetelmå, tunnettu sii-10 tå, ettå valmistetaan 4-[3-[etyyli[4-(etyylisulfinyyli)bu- tyyli]amino]-2-hydroksipropoksi]bentsonitriili.
  23. 12. Patenttivaatimuksen 1 mukainen menetelmå, tunnettu sii-tå, ettå valmistetaan 4-[3-[etyyli[3-[(2-fluoripropyyli)sul- 15 finyyli]propyyli]amino]- 2-hydroksipropoksi]bentsonitriili.
  24. 13. Yhdiste, jolla on kaava (°)P 20 || 0- (CH,)„-Y-CH,-NH- (CH2)s-S-Rc „ Φ CN jossa n on kokonaisluku 0, 1 tai 2, 30. on [CH2] In, CHOH tai CHF, m on kokonaisluku 0 tax 1, Rc on tyydyttynyt tai tyydyttymåton, suoraketjuinen tai haa-roittunut alkyyliryhmå, jossa on 1 - 4 hiiliatomia ja joka : mahdollisesti on substituoitu yhdellå tai useammalla fluo- 35 riatomi11a, p on kokonaisluku 0, 1 tai 2, s on kokonaisluku 2, 3, 4 tai 5. 86 92192
FI893936A 1987-12-23 1989-08-22 Menetelmä terapeuttisesti aktiivisten yhdisteiden valmistamiseksi sekä välituotteita FI92192C (fi)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FI930337A FI930337A0 (fi) 1987-12-23 1993-01-27 N-alkyl-n-(alkyltioalkyl)aminderivat anvaendbara som mellanprodukter

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
SE8705150A SE8705150D0 (sv) 1987-12-23 1987-12-23 Novel antiarrhythmic agents
SE8705150 1987-12-23
PCT/SE1988/000691 WO1989005794A1 (en) 1987-12-23 1988-12-20 Novel antiarrhythmic agents i
SE8800691 1988-12-20

Publications (4)

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FI893936A0 FI893936A0 (fi) 1989-08-22
FI893936A FI893936A (fi) 1989-08-22
FI92192B FI92192B (fi) 1994-06-30
FI92192C true FI92192C (fi) 1994-10-10

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FI893936A FI92192C (fi) 1987-12-23 1989-08-22 Menetelmä terapeuttisesti aktiivisten yhdisteiden valmistamiseksi sekä välituotteita
FI893937A FI893937A (fi) 1987-12-23 1989-08-22 Nya antiarytmiska aemnen ii.

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FI893937A FI893937A (fi) 1987-12-23 1989-08-22 Nya antiarytmiska aemnen ii.

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EP (2) EP0322390B1 (fi)
JP (2) JPH0637458B2 (fi)
KR (2) KR900700441A (fi)
CN (3) CN1033804A (fi)
AR (1) AR247729A1 (fi)
AT (2) ATE82257T1 (fi)
AU (4) AU625774B2 (fi)
DD (2) DD277274A5 (fi)
DE (2) DE3875934T2 (fi)
DK (2) DK404889A (fi)
EG (1) EG18681A (fi)
ES (2) ES2043891T3 (fi)
FI (2) FI92192C (fi)
GR (2) GR3006241T3 (fi)
HU (3) HUT54346A (fi)
IE (2) IE883859L (fi)
IL (2) IL103741A (fi)
IS (1) IS1558B (fi)
LT (4) LTIP1687A (fi)
LV (1) LV10250A (fi)
MX (1) MX174084B (fi)
MY (1) MY103945A (fi)
NO (2) NO171724C (fi)
NZ (1) NZ227381A (fi)
PH (2) PH25526A (fi)
PL (2) PL157747B1 (fi)
PT (2) PT89311B (fi)
RU (3) RU1836342C (fi)
SE (1) SE8705150D0 (fi)
WO (3) WO1989005795A1 (fi)
YU (2) YU47580B (fi)
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Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE8705150D0 (sv) * 1987-12-23 1987-12-23 Haessle Ab Novel antiarrhythmic agents
SE8902235D0 (sv) * 1989-06-20 1989-06-20 Haessle Ab Novel cyclodextrin inclusion complexes
SE9003902D0 (sv) * 1990-12-07 1990-12-07 Astra Ab Solid dosage forms of a drug
SE8902236D0 (sv) * 1989-06-20 1989-06-20 Haessle Ab Novel polystyrenesulfonate
SE8902237D0 (sv) * 1989-06-20 1989-06-20 Haessle Ab Novel stereoisomers
US5084463A (en) * 1989-12-11 1992-01-28 American Home Products Corporation N-quinolinyl alkyl-substituted 1-aryloxy-2-propanolamine and propylamine derivatives possessing class III antiarrhythmic activity
US5619274A (en) * 1990-09-10 1997-04-08 Starsight Telecast, Inc. Television schedule information transmission and utilization system and process
UA26190C2 (uk) * 1992-07-28 1999-07-19 Сейфтек Ай Лімітед Шприц
US5679706A (en) * 1994-09-30 1997-10-21 Bristol-Myers Squibb Company Combination of a potassium channel activator and an antiarrhythmic agent
US6143569A (en) * 1998-08-31 2000-11-07 The United States Of America As Represented By The Secretary Of The Navy Chelators exhibiting triple fluorescence
GB0123961D0 (en) * 2001-10-05 2001-11-28 Astrazeneca Ab Process and intermediates
WO2004113305A2 (en) 2003-06-16 2004-12-29 Vertex Pharmaceuticals Incorporated Diamino substituted quinazoline derivatives as promoters of smn2
US7356365B2 (en) * 2003-07-09 2008-04-08 Glucolight Corporation Method and apparatus for tissue oximetry
RU2631231C1 (ru) * 2016-12-01 2017-09-19 Научно-производственная ассоциация "Технопарк Авиационных Технологий" Способ получения заготовки лопатки газотурбинного двигателя для линейной сварки трением
CN115417973B (zh) * 2022-11-03 2023-03-24 广东粤港澳大湾区黄埔材料研究院 抗菌聚氨酯材料及其制备方法和应用

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SE404793B (sv) * 1973-05-25 1978-10-30 Boehringer Sohn Ingelheim Forfarande for framstellning av vissa angivna nitrilsubstituerade 1-fenoxi-2-hydroxi-3-lagalkylaminopropaner
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US4614746A (en) * 1985-03-21 1986-09-30 American Cyanamid Company 5-fluorobenzonitrile derivatives for increasing the lean meat to fat ratio and/or enhancing the growth rate of warm-blooded animals
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SE8705150D0 (sv) * 1987-12-23 1987-12-23 Haessle Ab Novel antiarrhythmic agents
SE8902237D0 (sv) * 1989-06-20 1989-06-20 Haessle Ab Novel stereoisomers
SE8902236D0 (sv) * 1989-06-20 1989-06-20 Haessle Ab Novel polystyrenesulfonate

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ZA894441B (en) 1990-02-28
US5034411A (en) 1991-07-23
JPH02502726A (ja) 1990-08-30
YU19690A (en) 1992-05-28
FI893936A0 (fi) 1989-08-22
ATE82257T1 (de) 1992-11-15
ATE81848T1 (de) 1992-11-15
MX14310A (es) 1993-10-01
AU2910389A (en) 1989-07-19
WO1989005806A1 (en) 1989-06-29
AU625872B2 (en) 1992-07-16
GR3006241T3 (fi) 1993-06-21
LTIP1720A (en) 1995-07-25
EP0322390A2 (en) 1989-06-28
FI893936A (fi) 1989-08-22
AR247729A1 (es) 1995-03-31
RU2024503C1 (ru) 1994-12-15
NO171724C (no) 1993-04-28
HUT54345A (en) 1991-02-28
PH26828A (en) 1992-11-05
JPH0637458B2 (ja) 1994-05-18
FI92192B (fi) 1994-06-30
DD295353A5 (de) 1991-10-31
NO171784C (no) 1993-05-05
YU234088A (en) 1990-06-30
EP0322389A2 (en) 1989-06-28
MX174084B (es) 1994-04-20
RU1836343C (ru) 1993-08-23
SE8705150D0 (sv) 1987-12-23
DE3875600T2 (de) 1993-03-11
EP0322389B1 (en) 1992-10-28
DE3875934D1 (de) 1992-12-17
HU913679D0 (en) 1992-02-28
RU1836342C (ru) 1993-08-23
HUT54346A (en) 1991-02-28
PT89311B (pt) 1993-08-31
PL159551B1 (pl) 1992-12-31
LTIP1687A (en) 1995-07-25
AU2824189A (en) 1989-07-19
YU47580B (sh) 1995-10-24
LTIP1752A (en) 1995-07-25
IE883860L (en) 1989-06-23
NZ227381A (en) 1992-07-28
ZA889424B (en) 1989-08-30
ES2043891T3 (es) 1994-01-01
GR3006912T3 (fi) 1993-06-30
NO171724B (no) 1993-01-18
NO893375L (no) 1989-08-22
IE883859L (en) 1989-06-23
NO893375D0 (no) 1989-08-22
DE3875934T2 (de) 1993-03-25
IL103741A (en) 1994-04-12
NO171784B (no) 1993-01-25
ES2045189T3 (es) 1994-01-16
CN1097736A (zh) 1995-01-25
DK404789A (da) 1989-10-19
DK404789D0 (da) 1989-08-17
FI893937A0 (fi) 1989-08-22
FI893937A (fi) 1989-08-22
IS1558B (is) 1994-10-05
DK404889A (da) 1989-10-19
PL157747B1 (pl) 1992-06-30
JPH02502725A (ja) 1990-08-30
DD277274A5 (de) 1990-03-28
KR900700442A (ko) 1990-08-13
KR900700441A (ko) 1990-08-13
IS3425A7 (is) 1989-06-24
AU625774B2 (en) 1992-07-16
DE3875600D1 (de) 1992-12-03
EP0322390B1 (en) 1992-11-11
AU2824489A (en) 1989-07-19
CN1048214A (zh) 1991-01-02
LTIP1688A (en) 1995-07-25
PH25526A (en) 1991-07-24
MY103945A (en) 1993-10-30
HU205895B (en) 1992-07-28
WO1989005794A1 (en) 1989-06-29
PT89312B (pt) 1993-08-31
NO893376L (no) 1989-08-22
PL276698A1 (en) 1989-08-07
DK404889D0 (da) 1989-08-17
US5155133A (en) 1992-10-13
WO1989005795A1 (en) 1989-06-29
LV10250A (lv) 1994-10-20
EP0322390A3 (en) 1989-09-06
PT89311A (pt) 1989-12-29
EP0322389A3 (en) 1989-09-06
PT89312A (pt) 1989-12-29
CN1033804A (zh) 1989-07-12
NO893376D0 (no) 1989-08-22
EG18681A (en) 1993-10-30
IL88749A (en) 1994-04-12

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