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WO1991008737A3 - Pharmacologically active amide carboxylate derivatives - Google Patents

Pharmacologically active amide carboxylate derivatives Download PDF

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Publication number
WO1991008737A3
WO1991008737A3 PCT/GB1990/001941 GB9001941W WO9108737A3 WO 1991008737 A3 WO1991008737 A3 WO 1991008737A3 GB 9001941 W GB9001941 W GB 9001941W WO 9108737 A3 WO9108737 A3 WO 9108737A3
Authority
WO
WIPO (PCT)
Prior art keywords
aryl group
group
alkyl
optionally substituted
pharmacologically active
Prior art date
Application number
PCT/GB1990/001941
Other languages
French (fr)
Other versions
WO1991008737A2 (en
Inventor
Colin Bennion
Stephen Connolly
David Hulme Robinson
Original Assignee
Fisons Plc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from GB898928456A external-priority patent/GB8928456D0/en
Priority claimed from GB909023645A external-priority patent/GB9023645D0/en
Application filed by Fisons Plc filed Critical Fisons Plc
Priority to FI922720A priority Critical patent/FI922720A0/en
Publication of WO1991008737A2 publication Critical patent/WO1991008737A2/en
Publication of WO1991008737A3 publication Critical patent/WO1991008737A3/en
Priority to NO92922345A priority patent/NO922345L/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/49—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/51—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/12—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
    • 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
    • C07C323/50—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 carboxyl groups bound to the same carbon skeleton
    • C07C323/51—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 carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—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 carboxyl 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 further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—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 carboxyl 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 further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C07C323/59—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 carboxyl 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 further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino 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
    • C07C323/50—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 carboxyl groups bound to the same carbon skeleton
    • C07C323/51—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 carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—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 carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/38—One sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Epidemiology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Time-Division Multiplex Systems (AREA)
  • Use Of Switch Circuits For Exchanges And Methods Of Control Of Multiplex Exchanges (AREA)

Abstract

This invention relates to compounds having pharmacological activity, processes for their preparation, compositions containing them and methods of treatment involving their use. In its broadest aspect, the invention is concerned with compounds, having general formula (I) in which R1 represents an alkyl C¿1-18? group optionally substituted by an aryl group or hydroxy or a cycloalkyl C3-6 group, R?2¿ represents an alkyl C¿1-18? group optionally substituted by an aryl group, or R?2¿ represents a group -CH¿2¿-X-R4 wherein X represents O or S, and R4 represents hydrogen, an aryl group, or an alkyl or alkenyl C¿1-18? group optionally substituted by an aryl group, R?3¿ represents OH, alkoxy C¿1-6? or -NHR?31¿, wherein R31 represents hydrogen, alkyl C¿1-6?, OH or alkoxy C1-6 optionally substituted by an aryl group, R?5¿ represents hydrogen, an aryl group or an alkyl or alkenyl C¿1-18? group optionally substituted by an aryl group, n represents 0, 1, 2 or 3, p represents 0, 1 or 2, q represents 0 or 1, Y represents -CHR?6¿-, -CH=CH-, O or S, in which R6 represents hydrogen, an aryl group or an alkyl or alkenyl C¿1-18? group optionally substituted by an aryl group, and pharmaceutically acceptable derivates thereof.
PCT/GB1990/001941 1989-12-16 1990-12-12 Pharmacologically active amide carboxylate derivatives WO1991008737A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
FI922720A FI922720A0 (en) 1989-12-16 1990-12-12 PHARMACOLOGICALLY ACTIVE AMID CARBOXYLATERS.
NO92922345A NO922345L (en) 1989-12-16 1992-06-15 PHARMACOLOGICALLY ACTIVE AMIDE CARBOXYLATE DERIVATIVES

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB8928456.6 1989-12-16
GB898928456A GB8928456D0 (en) 1989-12-16 1989-12-16 Compounds
GB909023645A GB9023645D0 (en) 1990-10-31 1990-10-31 Compounds
GB9023645.6 1990-10-31

Publications (2)

Publication Number Publication Date
WO1991008737A2 WO1991008737A2 (en) 1991-06-27
WO1991008737A3 true WO1991008737A3 (en) 1992-04-16

Family

ID=26296380

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1990/001941 WO1991008737A2 (en) 1989-12-16 1990-12-12 Pharmacologically active amide carboxylate derivatives

Country Status (7)

Country Link
EP (1) EP0505467A1 (en)
JP (1) JPH05502233A (en)
CA (1) CA2072018A1 (en)
FI (1) FI922720A0 (en)
IE (1) IE904522A1 (en)
PT (1) PT96210A (en)
WO (1) WO1991008737A2 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5639746A (en) * 1994-12-29 1997-06-17 The Procter & Gamble Company Hydroxamic acid-containing inhibitors of matrix metalloproteases
US5672598A (en) * 1995-03-21 1997-09-30 The Procter & Gamble Company Lactam-containing hydroxamic acids
ES2247604T3 (en) * 1995-06-12 2006-03-01 G.D. SEARLE & CO. COMPOSITIONS THAT INCLUDE A CYCLLOXYGENASA-2 INHIBITOR AND A 5-LIPOXYGENASE INHIBITOR.
UA59384C2 (en) 1996-12-20 2003-09-15 Пфайзер, Інк. Preventing bone mass loss and recovery thereof by means of prostaglandin agonists
EP1309552A4 (en) 2000-07-24 2005-07-20 Univ Queensland COMPOUNDS AND INHIBITORS OF PHOSPHOLIPASES
US7323596B2 (en) * 2000-12-21 2008-01-29 De Novo Pharmaceuticals Ltd. Antimicrobial agents
GB0112324D0 (en) * 2001-05-21 2001-07-11 Croda Int Plc Compounds
ES2273560B1 (en) * 2005-02-25 2008-04-01 Consejo Superior Investig. Cientificas INHIBITOR COMPOUND OF THE CERAMIDASE ENZYME, SYNTHESIS PROCEDURE, PHARMACEUTICAL COMPOSITION CONTAINING IT AND ITS APPLICATIONS.
FR2968952A1 (en) * 2010-12-17 2012-06-22 Oreal N-ACYL AMINO ACID ESTER AS A SOOTHING AGENT

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7214520A (en) * 1971-10-28 1973-05-02
EP0226304A1 (en) * 1985-10-24 1987-06-24 Sankyo Company Limited Composition containing a penem or carbapenem antibiotic

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7214520A (en) * 1971-10-28 1973-05-02
EP0226304A1 (en) * 1985-10-24 1987-06-24 Sankyo Company Limited Composition containing a penem or carbapenem antibiotic

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Croatica Chemica Acta, volume 38, 1966 (Zagreb) B. Ladesic et al.: "Biochemical studies in tobacco plants. III. Synthesis and behaviour of potential metabolites of D-beta-methionine in nicotiana rustica", pages 155-160, see the whole document *
Journal of Medicinal Chemistry, volume 27, no. 6, June 1984, American Chemical Society, (Washington, US) R.P. Hanzlik et al.: "Vinylogous amino acid esters: a new class of inactivators for thiol proteases", pages 711-712, see the whole document, especially page 711, column 1 (cited in the application) *
Journal of Medicinal Chemistry, volume 29, no. 1, January 1986, American Chemical Society, (Washington, US) S.A. Thompson et al.: "Carboxyl-modified amino acids and peptides as protease inhibitors", pages 104-111, see the whole document, especially page 104, column 1 (cited in the application) *

Also Published As

Publication number Publication date
JPH05502233A (en) 1993-04-22
CA2072018A1 (en) 1991-06-17
WO1991008737A2 (en) 1991-06-27
FI922720A7 (en) 1992-06-12
FI922720A0 (en) 1992-06-12
EP0505467A1 (en) 1992-09-30
PT96210A (en) 1991-09-30
IE904522A1 (en) 1991-06-19

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