FI112220B - Förfarande för framställning av terapeutiskt användbara N-(1H-1,4-bensodiazepin-3-yl)ureaderivat - Google Patents

Förfarande för framställning av terapeutiskt användbara N-(1H-1,4-bensodiazepin-3-yl)ureaderivat Download PDF

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Publication number
FI112220B
FI112220B FI921576A FI921576A FI112220B FI 112220 B FI112220 B FI 112220B FI 921576 A FI921576 A FI 921576A FI 921576 A FI921576 A FI 921576A FI 112220 B FI112220 B FI 112220B
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Prior art keywords
phenyl
dihydro
benzodiazepin
urea
oxo
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FI921576A
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English (en)
Finnish (fi)
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FI921576A0 (fi
FI921576A (fi
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Mark G Bock
Roger M Freidinger
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Merck & Co Inc
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Priority claimed from US07/848,790 external-priority patent/US5220018A/en
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Publication of FI921576A publication Critical patent/FI921576A/fi
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/04—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 3
    • 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
    • C07D401/02—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 containing two hetero rings
    • C07D401/12—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 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
    • C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
    • C07D243/24—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
    • C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D419/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • 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
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • 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
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Addiction (AREA)
  • Ophthalmology & Optometry (AREA)
  • Anesthesiology (AREA)
  • Pain & Pain Management (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Joining Of Building Structures In Genera (AREA)
  • Materials For Medical Uses (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Prostheses (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Claims (10)

1. Förfarande för framställning av nya tera-peutiskt användbara N- (1H-1,4-bensodiazepin-3-yl)ureaderi-5 vat med formeln I: R3 ifVi- ° Hl /—NH-C-R P 1 väri R är
15 O II nhpcoch3)2 - HN t N—N
2. PC. ApNH, * , - HN—^ /) OCH3 , -HN-<nJ>0 : : '—N . i 25 A Il 30 302N':i/V li -"““C-/ _hn-C3 * '- * ' J » Λ N-N i*.; 35 <N> so2nh2 H - HN—y f 112221 H iiS02NH2 5 - * I o J!~\ NH-SOzS4 10 '“ML/ o o 15 _ , O o
20 AA H /—\ N NR4 i _ N—r y H H > : 25 Aa3 ; —N ; h //Ά h /A H - N—\_ ) ’ - N— : 3o o •: A n n-ch3 '. i ‘ ^—N •»-O X . 35 S02N -S^j> H H. 112220 O 5 -¾¾. ' H H 10 o CN II --Ö . 15 o Λ 20 nh2 i eller - ™~\} ·, : 25 t R2 är H eller halogen; R3 är rakkedjad eller förgrenad C1-C6-alkyl eller 30 cyklopropylmetyl; R4 är rakkedjad eller förgrenad Ci-C6-alkyl, CF3, > cyklopropyl, 2,2-dimetylcyklopropyl, 2,2-difluorcyklo- propyl, cyklobutyl, cyklopentyl, cyklohexyl, fenyl eller mono- eller disubstituerad fenyl, väri substitution är F, \ 35 Cl, Br, CN, N02, CF3, 0CH3 eller NH2; 11 » R5 är H, metyl, etyl eller fenyl; och 11222 L Re är metyl, etyl eller fenyl; eller optiska isomerer, proläkemel eller farmaceutiskt godtagbara salter därav, kännetecknat därav, att 5 a) en förening med formeln: R - H väri R definieras som ovan, behandlas med trietylamin och 10 trifosgen, varefter en förening med formeln II R3 ί IT )-™2 ^V=-N II
15 I) väri R2 och R3 definieras som ovan, tillsatts i reaktions-20 blandningen, b) ett salt av en förening med formeln II, väri R2 och R3 definieras som ovan, behandlas med trietylamin och • 1 · omsätts därefter med ett isocyanat, väri NH2-gruppen av en j : ; förening med formeln R - H ersatts med gruppen -NCO och ·;· 1 25 väri R definieras som ovan, eller I c) ett salt av en förening med formeln R - H, vari • · . R definieras som ovan, behandlas först med trifosgen och * 1 · trietylamin, varefter det omsätts med en förening med for-;Vi mein II, väri R2 och R3 definieras som ovan, och 30 if all önskvärt, den sä erhällna föreningen med • · ·;1 formeln I omvandlas till ett salt därav. I 2. Förfarande enligt patentkrav 1, k ä n n e - t e c k n a t därav, att man framställer N-{1,3-dihydro-..\t l-etyl-2-oxo-5-fenyl-lH-1,4-bensodiazepin-3-yl}-N'-{[3 - 35 (lH-tetrazol-5-yl) fenyl] urea} eller ett farmaceutiskt god- » » · ’1 tagbart salt därav. 11222(
3. Förfarande enligt patentkrav 1, känne-t e c k n a t därav, att man framställer N-{1,3-dihydro-1- [2-propyl]-2-oxo-5-fenyl-1H-1,4-bensodiazepin-3-yl}-N'- { [3-(lH-tetrazol-5-yl)fenyl]urea} eller ett farmaceutiskt 5 godtagbart sait därav.
4. Förfarande enligt patentkrav 1, känne-t e c k n a t därav, att man framställer N-{1,3-dihydro-l-metyl-2-oxo-5-fenyl-lH-l,4-bensodiazepin-3-yl}-N'-{[5- (2-klor)pyridyl]urea} eller ett farmaceutiskt godtagbart 10 sait därav.
5. Förfarande enligt patentkrav 1, känne-t e c k n a t därav, att man framställer N- {l, 3-dihydro-l-metyl-2-oxo-5-fenyl-lH-l,4-bensodiazepin-3-yl}-N'-{[3-(lH-tetrazol-5-yl)fenyl]urea} eller ett farmaceutiskt god- 15 tagbart sait därav.
6. Förfarande enligt patentkrav 1, k ä n n e -t e c k n a t därav, att man framställer N- {1,3 -dihydro-1-[2-metyl]propyl-2-oxo-5-fenyl-1H-1,4-bensodiazepin-3- yl}-N'-{[3-(lH-tetrazol-5-yl)fenyl]urea} eller ett farma-20 ceutiskt godtagbart sait därav.
7. Förfarande enligt patentkrav 1, känne-t e c k n a t därav, att man framställer N- {1,3 -dihydro- | ’ . l-n-propyl-2-oxo-5-fenyl-lH-l,4-bensodiazepin-3-yl}-N'- ::: {[3-(lH-tetrazol-5-yl)fenyl]urea} eller ett farmaceutiskt ·; * 25 godtagbart sait därav.
.: 8. Förfarande enligt patentkrav 1, känne- , tecknat därav, att man framställer N-{1,3-dihydro- l-metyl-2-oxo-5-fenyl-lH-l,4-bensodiazepin-3-yl}-N'- { [3-(N-(t-butylsulfonyl)karboxamido)fenyl] urea} eller ett far-_ 3 0 maceutiskt godtagbart sait därav.
*"’ 9. Förfarande enligt patentkrav 1, känne- tecknat därav, att man framställer N-{1,3-dihydro-;' 1-metyl-2-oxo-5-fenyl-1H-1,4-bensodiazepin-3-yl}-N'-{[3 - (1,2,4-oxadiazol-5-on) fenyl]urea} eller ett farmaceutiskt ’ *} 3 5 godtagbart sait därav. » t I * 9 11222 C.
10. Förfarande enligt patentkrav 1, kanne-t e c k n a t därav, att man framställer N-{1,3-dihydro-1-cyklopropylmetyl-2-oxo-5 -fenyl-1H-1,4-bensodiazepin-3 -yl}-N'-{ [3-(1,2,4-oxadiazol-5-on)fenyl]urea} eller ett 5 farmaceutiskt godtagbart salt därav. s *
FI921576A 1991-04-10 1992-04-09 Förfarande för framställning av terapeutiskt användbara N-(1H-1,4-bensodiazepin-3-yl)ureaderivat FI112220B (sv)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US68300791A 1991-04-10 1991-04-10
US68300791 1991-04-10
US76427791A 1991-09-23 1991-09-23
US76427791 1991-09-23
US07/848,790 US5220018A (en) 1991-04-10 1992-03-10 Cholecystokinin antagonists
US84879092 1992-03-10

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FI921576A0 FI921576A0 (fi) 1992-04-09
FI921576A FI921576A (fi) 1992-10-11
FI112220B true FI112220B (sv) 2003-11-14

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FI921576A FI112220B (sv) 1991-04-10 1992-04-09 Förfarande för framställning av terapeutiskt användbara N-(1H-1,4-bensodiazepin-3-yl)ureaderivat

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EP (1) EP0508796B1 (sv)
JP (1) JP3012086B2 (sv)
KR (1) KR920019762A (sv)
AT (1) ATE168103T1 (sv)
AU (1) AU662322B2 (sv)
CA (1) CA2066083C (sv)
CY (1) CY2102B1 (sv)
DE (1) DE69226119T2 (sv)
DK (1) DK0508796T3 (sv)
ES (1) ES2117654T3 (sv)
FI (1) FI112220B (sv)
GR (1) GR3027672T3 (sv)
HK (1) HK1011016A1 (sv)
IE (1) IE921138A1 (sv)
IL (1) IL101514A (sv)
LV (1) LV12314B (sv)
NO (1) NO300971B1 (sv)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2682381B1 (fr) * 1991-10-10 1995-04-07 Rhone Poulenc Rorer Sa Derives de benzodiazepine, leur preparation et les medicaments les contenant.
WO1993008175A1 (en) * 1991-10-24 1993-04-29 Glaxo Group Limited Benzodiazepine derivatives as antagonists of gastrin and/or cholecystokinin
CA2130195A1 (en) * 1992-03-16 1993-09-30 Mark Gary Bock Benzodiazepine derivatives, compositions containing them and their use in therapy
JPH07505155A (ja) * 1992-03-24 1995-06-08 メルク　シヤープ　エンド　ドーム　リミテツド コレシストキニン及び／又はガストリン拮抗活性を有する３−ウレイド置換ベンゾジアゼピン−２−オン及び治療におけるその使用
US5378838A (en) * 1993-01-13 1995-01-03 Merck & Co., Inc. Benzodiazepine cholecystokinin antagonists
GB9308431D0 (en) * 1993-04-23 1993-06-09 Glaxo Spa Chemical compounds
GB9514031D0 (en) * 1995-07-10 1995-09-06 Zeneca Ltd Chemical process
US6107330A (en) * 1995-08-07 2000-08-22 Daiichi Pharmaceutical Co., Ltd. Inhibitor for narcotic analgesic dependence/resistance acquisition
US5952506A (en) * 1997-04-24 1999-09-14 American Home Products Corporation Process for the synthesis of 4- 6- (hexylcarbamoyloxy) hexylcarbamoyloxy!-piperidine-1-carboxylic acid 4-phenoxyphenyl ester
FR2782997A1 (fr) * 1998-09-08 2000-03-10 Hoechst Marion Roussel Inc Nouveaux derives de la benzodiazepinone, procede de preparation et intermediaires de ce procede, application a titre de medicaments et compositions pharmaceutiques les renfermant
WO2004101533A1 (en) * 2003-05-12 2004-11-25 Janssen Pharmaceutica, N.V. 1, 3, 4-benzotriazepin-2-one salts and their use as cck receptor ligands
CN101061116A (zh) * 2004-09-24 2007-10-24 詹森药业有限公司 磺酰胺化合物
US20130053392A1 (en) * 2010-02-12 2013-02-28 Peter Ebbesen Carbonic anhydrase inhibitors

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1332410C (en) * 1984-06-26 1994-10-11 Roger M. Freidinger Benzodiazepine analogs
US4820834A (en) * 1984-06-26 1989-04-11 Merck & Co., Inc. Benzodiazepine analogs
CA2032226A1 (en) * 1989-12-18 1991-06-19 Mark G. Bock Benzodiazepine analogs
IL96613A0 (en) * 1989-12-18 1991-09-16 Merck & Co Inc Pharmaceutical compositions containing benzodiazepine analogs

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IE921138A1 (en) 1992-10-21
LV12314B (en) 1999-11-20
DE69226119D1 (de) 1998-08-13
CA2066083C (en) 2002-10-08
FI921576A0 (fi) 1992-04-09
CY2102B1 (en) 2002-04-05
LV12314A (lv) 1999-07-20
EP0508796B1 (en) 1998-07-08
AU662322B2 (en) 1995-08-31
JP3012086B2 (ja) 2000-02-21
DE69226119T2 (de) 1999-02-11
JPH0687838A (ja) 1994-03-29
IL101514A (en) 1996-01-31
EP0508796A1 (en) 1992-10-14
FI921576A (fi) 1992-10-11
DK0508796T3 (da) 1998-10-26
NO921409L (no) 1992-10-12
GR3027672T3 (en) 1998-11-30
HK1011016A1 (en) 1999-07-02
ATE168103T1 (de) 1998-07-15
IL101514A0 (en) 1992-12-30
ES2117654T3 (es) 1998-08-16
KR920019762A (ko) 1992-11-19
NO300971B1 (no) 1997-08-25
NO921409D0 (no) 1992-04-09
CA2066083A1 (en) 1992-10-11
AU1479892A (en) 1992-11-19

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