FI117865B - Läkemedelssalter - Google Patents

Läkemedelssalter Download PDF

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Publication number
FI117865B
FI117865B FI964918A FI964918A FI117865B FI 117865 B FI117865 B FI 117865B FI 964918 A FI964918 A FI 964918A FI 964918 A FI964918 A FI 964918A FI 117865 B FI117865 B FI 117865B
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FI
Finland
Prior art keywords
acid
salt
compound
compound according
sulfonic acid
Prior art date
Application number
FI964918A
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English (en)
Finnish (fi)
Other versions
FI964918A0 (sv
FI964918A (sv
Inventor
Hjarne Dyrsting
Torben Koch
Kim Voulund Petersen
Original Assignee
Dumex Alpharma As
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Priority claimed from GBGB9505021.7A external-priority patent/GB9505021D0/en
Application filed by Dumex Alpharma As filed Critical Dumex Alpharma As
Publication of FI964918A0 publication Critical patent/FI964918A0/sv
Publication of FI964918A publication Critical patent/FI964918A/sv
Application granted granted Critical
Publication of FI117865B publication Critical patent/FI117865B/sv

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/66—Phosphorus compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/14—Peptides containing saccharide radicals; Derivatives thereof, e.g. bleomycin, phleomycin, muramylpeptides or vancomycin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
    • C07C237/26—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton of a ring being part of a condensed ring system formed by at least four rings, e.g. tetracycline
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/117—Esters of phosphoric acids with cycloaliphatic alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
    • C07H11/04—Phosphates; Phosphites; Polyphosphates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
    • C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
    • C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
    • C07H15/228—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to adjacent ring-carbon atoms of the cyclohexane rings
    • C07H15/232—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to adjacent ring-carbon atoms of the cyclohexane rings with at least three saccharide radicals in the molecule, e.g. lividomycin, neomycin, paromomycin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
    • C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
    • C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
    • C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
    • C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
    • C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
    • C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
    • C07H15/236—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2 a saccharide radical being substituted by an alkylamino radical in position 3 and by two substituents different from hydrogen in position 4, e.g. gentamicin complex, sisomicin, verdamycin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
    • C07H15/238—Cyclohexane rings substituted by two guanidine radicals, e.g. streptomycins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/08—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to sulfur, selenium or tellurium
    • C07H5/10—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to sulfur, selenium or tellurium to sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
    • C08B37/0021—Dextran, i.e. (alpha-1,4)-D-glucan; Derivatives thereof, e.g. Sephadex, i.e. crosslinked dextran

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Confectionery (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Claims (24)

1. Terapeutisk förening, som är olöslig eller svärlöslig i vatten, kännetecknad av, att den 5 är ett mono- - oktasackaridsyrasalt av en biologiskt aktiv organisk förening, som är annan än ett sackaros-okta-O-sulfonsyrasalt av en aminoglykosid.
2. Förening enligt patentkrav 1, kännetecknad av, att den är olöslig eller svärlöslig i 10 dejoniserat vatten.
3. Förening enligt nägotdera av föregäende pa tentkrav, kännetecknad av, att nämnda syra är en poly-O-sulfonsyra.
4. Förening enligt nägot av föregäende patent- 15 krav, kännetecknad av, att nämnda syra är en disackaridpoly-O-sulfonsyra.
5. Förening enligt nägot av föregäende patentkrav, kännetecknad av, att nämnda syra är sackaros-okta-O-sulfonsyra. 20
6. Förening enligt nägot av föregäende patent krav, kännetecknad av, att den innehäller yt-terligare en fysiologiskt tolererbar motjon.
» · · *·*·* 7. Förening enligt nägot av föregäende patent- ’***: krav, kännetecknad av, att som nämnda motjon • · · V * 25 kommer i fräga alkalimetall-, jordalkalimetall-, ammonium- *:* och aluminiurnj oner.
···· -* : 8. Förening enligt patentkrav 7, k ä n n e - • · · ... ;*·*; t e c k n a d av, att nämnda motjon är en aluminiurnj on.
9. Förening enligt nägot av föregäende patent- , .·. 30 krav, kännetecknad av, att nämnda organiska • · · "I förening är en förening innehällande en basisk kväveatom. • · • ·
10. Förening enligt patentkrav 9, k ä n n e - t e c k n a d av, att nämnda organiska förening innehäl- ·:**: ler flera protonerbara kväveatomer. .··«. 35
11· Förening enligt nägot av föregäende patent- • * krav, kännetecknad av, att som nämnda or- • · · V * • * 57 1 1 7 8 6 5 ganiska förening kommer i fräga antibakteriella medel, an-tivirala medlen, antimykotiska medel, antiamöbiska medel, allergiläkemedel, kardioprotektiva medel, analgeter, an-xiolyter, sedativer, hypnotika, migrenläkemedel, ressjuke- | 5 läkemedel, antiemetica, adrenergica, antispasmodica, mus-kelrelaxanter, neuroleptica, depressionsläkemedel, antiko-linergica, antihistaminer, anorexiläkemedel och alka-loider.
12. Förening enligt nägot av föregäende patent-10 krav, kännetecknad av, att nämnda organiska förening är ett antibakteriellt medel.
13. Förening enligt patentkrav 12, kanne- : t e c k n a d av, att nämnda organiska förening är en aminoglykosid, en tetracyklin, en polypeptid, en glykopep- 15 tid eller en makrolid.
14. Förening enligt patentkrav 12, kanne-t e c k n a d av, att nämnda organiska förening är en tetracyklin.
15. Förening enligt patentkrav 11, k ä n n e - 20 tecknad av, att som nämnda organiska förening kom mer i fräga doxicyklin, diltiazem, cyklobensaprin, basit- ., racin, noskapin, erytromycin, polymyxin, vankomycin, nor- * 1 1 *·2 3] triptylin, kinidin, ergotamin, benstropin, verapamil, flu- 1 narizin och imipramin. 2 • · · *.1 1 25
16. Förening enligt patentkrav 1, k ä n n e - ,.!2 tecknad av, att som nämnda organiska förening kom- mer i fräga pindolol, diklofenak, desipramin, amitripty-Iin, klordiazepoxid, klorpromazin, difenylhydramin, tobramycin, cinnarizin, furosemid, cyproheptadien, karbamaze- « .1. 30 pin, indometacin och propranolol. ; 3 .·1·.
17. Förening enligt nägot av patentkraven 14 - 16, • kännetecknad av, att den är ett ett sacka- • 1 rosokta-O-sulfonsyrasalt av nämnda organiska förening.
18. Förening enligt nägot av patentkraven 1 - 16, • '1 · -· .2·. 35 kännetecknad av, att nämnda syra är en poly- • · · sulfon- eller polyfosfonsyra. • 1 > 117865
19. Förening enligt patentkrav 1, kanne- t e c k n a d av, att den är sackarosokta-O-sulfon- ; syrasaltet av doxicyklin.
20. Förening enligt nagot av patentkraven 1 - 19, § 5 kännetecknad av, att den är avsedd för an- vändning soin terapeutiskt medel.
21. Farmaceutisk komposition, som omfattar en biologiskt aktiv förening tillsammans med minst ett fysi-ologiskt godtagbart bärar- eller utdrygningsmedel, k ä n - 10 netecknad av, att nämnda förening, som är annan än ett sackarosokta-O-sulfonsyrasalt av en aminoglykosid, är närvarande i form av ett i vatten olösligt eller svär-lösligt sait bildat med en mono- - oktasackaridsyra.
22. Användning av en effektiv mängd av en biolo-15 giskt aktiv organisk förening för framställning av ett läkemedel med vilket man motverkar ett tillständ, som är responsivt för nämnda förening, kännetecknad av, att nämnda förening administreras som ett i vatten olösligt eller svärlösligt sait bildat med en mono- - ok-20 tasackaridsyra, förutsatt att nämnda sait är annat än ett sackarosokta-O-sulfonsyrasalt av en aminoglykosid.
,, 23. Användning enligt patentkrav 22, k ä n - • t ♦ **'·[ netecknad av, att nämnda sait administreras • · * · · ' * * peroralt. «·« \* : 25
24. Användning enligt patentkrav 22, k ä n - * netecknad av, att nämnda sait administreras Ιοί : : kait tili slemhinnan. • ♦ · ' • · ♦ • · · • · · ♦ t · · • · · • · · ·♦· • · ··· f ·····' • · • . n • * · · · • · «·« « · • · *·· Φ * · • « · • · « *
FI964918A 1994-06-10 1996-12-09 Läkemedelssalter FI117865B (sv)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
DK66794 1994-06-10
DK66794 1994-06-10
GB9505021 1995-03-13
GBGB9505021.7A GB9505021D0 (en) 1994-06-10 1995-03-13 Drag salts
PCT/EP1995/002254 WO1995034571A2 (en) 1994-06-10 1995-06-09 Drug salts
EP9502254 1995-06-09

Publications (3)

Publication Number Publication Date
FI964918A0 FI964918A0 (sv) 1996-12-09
FI964918A FI964918A (sv) 1997-02-07
FI117865B true FI117865B (sv) 2007-03-30

Family

ID=26064416

Family Applications (1)

Application Number Title Priority Date Filing Date
FI964918A FI117865B (sv) 1994-06-10 1996-12-09 Läkemedelssalter

Country Status (11)

Country Link
EP (1) EP0764169B1 (sv)
AT (1) ATE171456T1 (sv)
AU (1) AU702042B2 (sv)
CA (1) CA2192481C (sv)
DE (1) DE69504973T2 (sv)
DK (1) DK0764169T3 (sv)
ES (1) ES2121627T3 (sv)
FI (1) FI117865B (sv)
NO (1) NO307933B1 (sv)
NZ (1) NZ288612A (sv)
WO (1) WO1995034571A2 (sv)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69926770T2 (de) 1998-10-05 2006-06-29 Kabushiki Kaisha Yakult Honsha Antibakterielle mittel und ein herstellungsverfahren dafür
AU2007200916B2 (en) * 1998-10-05 2009-09-17 Kabushiki Kaisha Yakult Honsha Antibacterial agents and process for producing the same
IS6389A (is) * 2001-08-31 2003-03-03 Heraeus Kulzer Gmbh & Co. Kg Reynsla af sýklalyfjahúðun skrokka, sem í eru örholrými, og einnig af þannig húðuðum skrokkum og notkun þeirra
US20040043072A1 (en) * 2002-09-04 2004-03-04 Will Joanne Patricia Alleviation of upper gastrointestinal irritation
GB0400988D0 (en) * 2004-01-16 2004-02-18 Oxoid Ltd Therapeutically useful antibacterial compounds
CN103193835B (zh) * 2013-04-18 2015-06-24 安徽赛诺制药有限公司 一种蔗糖八磺酸酯钠合成及纯化的方法
DE102015214603B4 (de) * 2015-07-31 2019-01-24 Mathys Ag Bettlach Phosphorhaltige Aminoglycosid-Salze

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1227830A (sv) * 1968-07-18 1971-04-07
IT1201436B (it) * 1985-07-19 1989-02-02 Vincenzo Zappia Formulazioni topiche a lento rilascio
DK103493D0 (da) * 1993-09-14 1993-09-14 Dumex Ltd As Nye salte af aminoglykosider

Also Published As

Publication number Publication date
NO965258L (no) 1997-02-06
ES2121627T3 (es) 1998-12-01
AU2790795A (en) 1996-01-05
FI964918A0 (sv) 1996-12-09
NO965258D0 (no) 1996-12-09
DE69504973T2 (de) 1999-02-18
EP0764169A2 (en) 1997-03-26
ATE171456T1 (de) 1998-10-15
NO307933B1 (no) 2000-06-19
AU702042B2 (en) 1999-02-11
DK0764169T3 (da) 1999-06-14
CA2192481A1 (en) 1995-12-21
FI964918A (sv) 1997-02-07
WO1995034571A2 (en) 1995-12-21
NZ288612A (en) 1997-11-24
EP0764169B1 (en) 1998-09-23
DE69504973D1 (de) 1998-10-29
CA2192481C (en) 2003-01-07
WO1995034571A3 (en) 1996-05-02

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