IT1252708B - STABLE SALTS OF (+) - (1R, 2S) -2 ((N- (2-HYDROXYLAMINE-2-OSSOETHL) -N-METHYLAMINE) CARBONYL) CYCLOHEXAN-1-CARBOXYL, ACE INHIBITIVE ACTIVITY, PROCEDURE FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM. - Google Patents

STABLE SALTS OF (+) - (1R, 2S) -2 ((N- (2-HYDROXYLAMINE-2-OSSOETHL) -N-METHYLAMINE) CARBONYL) CYCLOHEXAN-1-CARBOXYL, ACE INHIBITIVE ACTIVITY, PROCEDURE FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM.

Info

Publication number
IT1252708B
IT1252708B ITMI913448A ITMI913448A IT1252708B IT 1252708 B IT1252708 B IT 1252708B IT MI913448 A ITMI913448 A IT MI913448A IT MI913448 A ITMI913448 A IT MI913448A IT 1252708 B IT1252708 B IT 1252708B
Authority
IT
Italy
Prior art keywords
cyclohexan
ace
carbonyl
preparation
ossoethl
Prior art date
Application number
ITMI913448A
Other languages
Italian (it)
Inventor
Raffaello Giorgi
Alessandro Subissi
Luigi Turbanti
Original Assignee
Guidotti & C Spa Labor
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
Application filed by Guidotti & C Spa Labor filed Critical Guidotti & C Spa Labor
Publication of ITMI913448A0 publication Critical patent/ITMI913448A0/en
Priority to ITMI913448A priority Critical patent/IT1252708B/en
Priority to JP5511398A priority patent/JPH06506002A/en
Priority to RU9293052414A priority patent/RU2079489C1/en
Priority to CA002104372A priority patent/CA2104372A1/en
Priority to EP92924726A priority patent/EP0575572A1/en
Priority to HU9302389A priority patent/HUT69287A/en
Priority to AU30871/92A priority patent/AU657591B2/en
Priority to BR9205652A priority patent/BR9205652A/en
Priority to PCT/EP1992/002903 priority patent/WO1993013056A1/en
Priority to SK3796-92A priority patent/SK379692A3/en
Priority to NZ245547A priority patent/NZ245547A/en
Priority to CS923796A priority patent/CZ379692A3/en
Priority to SI9200409A priority patent/SI9200409A/en
Priority to HR921454A priority patent/HRP921454A2/en
Priority to MA23040A priority patent/MA22749A1/en
Priority to LVP-92-358A priority patent/LV10426B/en
Priority to MX9207543A priority patent/MX9207543A/en
Priority to YU110892A priority patent/YU110892A/en
Priority to PL92297118A priority patent/PL169086B1/en
Priority to ZA9210004A priority patent/ZA9210004B/en
Priority to PT101156A priority patent/PT101156A/en
Priority to CN92113839A priority patent/CN1079474A/en
Priority to TNTNSN92117A priority patent/TNSN92117A1/en
Publication of ITMI913448A1 publication Critical patent/ITMI913448A1/en
Priority to BG98050A priority patent/BG98050A/en
Priority to NO93932982A priority patent/NO932982L/en
Priority to FI933685A priority patent/FI933685A0/en
Priority to EE9400006A priority patent/EE9400006A/en
Application granted granted Critical
Publication of IT1252708B publication Critical patent/IT1252708B/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
    • 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
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/26—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one amino group bound to the carbon skeleton, e.g. lysine
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Peptides Or Proteins (AREA)

Abstract

I nuovi sali dell'acido (1) - (1R,2S) - 2-[[N-(2- idrossilammino-2- ossoetil)-N-metil- ammino]carbonil]cicloesan - 1 - carbossilico con metalli e con basi organiche, rappresentati dalla formula generale (1) Formula I in cui R ed R' se considerati insieme rappresentano un catione bivalente scelto tra calcio, etilendiammina ed altri cationi o basi organiche farmaceuticamente accettabili, oppure se R' = R rappresenta sodio, potassio, un gruppo imidazolico, lisina, colina, dietaloammina, arginina ed istidina, sono dotati di attività ACE*inibitrice e quindi sono utili quali ingredienti attivi di farmaci anti-ipertensivi. Il procedimento per la loro preparazione prevede di preferenza la reazione dell'acido di partenza prodotto con un gruppo benzilico con l'opportuno idrato, carbonato o base organica in condizioni di idrogenazione in presenza di un catalizzatore di idrogenzazione.The new salts of (1) - (1R, 2S) - 2 - [[N- (2- hydroxylamino-2- oxoethyl) -N-methyl- amino] carbonyl] cyclohexan - 1 - carboxylic with metals and bases organic, represented by the general formula (1) Formula I in which R and R 'if considered together represent a divalent cation chosen from calcium, ethylenediamine and other pharmaceutically acceptable cations or organic bases, or if R' = R represents sodium, potassium, a imidazole group, lysine, choline, dietaloamine, arginine and histidine, have ACE * inhibitory activity and are therefore useful as active ingredients of anti-hypertensive drugs. The process for their preparation preferably provides for the reaction of the starting acid produced with a benzyl group with the appropriate hydrate, carbonate or organic base under hydrogenation conditions in the presence of a hydrogenation catalyst.

ITMI913448A 1991-12-23 1991-12-23 STABLE SALTS OF (+) - (1R, 2S) -2 ((N- (2-HYDROXYLAMINE-2-OSSOETHL) -N-METHYLAMINE) CARBONYL) CYCLOHEXAN-1-CARBOXYL, ACE INHIBITIVE ACTIVITY, PROCEDURE FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM. IT1252708B (en)

Priority Applications (27)

Application Number Priority Date Filing Date Title
ITMI913448A IT1252708B (en) 1991-12-23 1991-12-23 STABLE SALTS OF (+) - (1R, 2S) -2 ((N- (2-HYDROXYLAMINE-2-OSSOETHL) -N-METHYLAMINE) CARBONYL) CYCLOHEXAN-1-CARBOXYL, ACE INHIBITIVE ACTIVITY, PROCEDURE FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM.
JP5511398A JPH06506002A (en) 1991-12-23 1992-12-12 Stable salt of (+)-(1S,2R)-2-[[N-(2-hydroxylamino-2-oxoethyl)-N-methyl-amino]carbonyl]cyclohexane-1-carboxylic acid
RU9293052414A RU2079489C1 (en) 1991-12-23 1992-12-12 (+)-(1s,2r)-2-[[n-(2-hydroxyamino-2-oxoethyl)-n-methylamino]- -carbonyl]-cyclohexane-1-carboxylic acid stable salts, method of their synthesis and pharmaceutical composition
CA002104372A CA2104372A1 (en) 1991-12-23 1992-12-12 Stable salts of (+)-(1s,2r)-2-¬¬n-(2-hydroxylamino-2-oxoethyl) -n-methyl-amino|carbonyl|cyclohexane-1-carboxylic acid, pro ess for their preparation and pharmaceutical compositions containing them
EP92924726A EP0575572A1 (en) 1991-12-23 1992-12-12 Stable salts of (+)-(1s,2r)-2- n-(2-hydroxylamino-2-oxoethyl)-n-methyl-amino]carbonyl]cyclohexane-1-carboxylic acid, process for their preparation and pharmaceutical compositions containing them
HU9302389A HUT69287A (en) 1991-12-23 1992-12-12 Process to prepare stable salts of(+)-(1s,2r)-2-{[n-(2-hydroxylamino-2-oxoethyl)-n-methyl-amino]carbonyl} cyclohexane-1-carboxylic acid and pharmaceutical compns. contg. them
AU30871/92A AU657591B2 (en) 1991-12-23 1992-12-12 Stable salts of (+)-(1S,2R)-2-((N-(2-hydroxylamino-2-oxoethyl)-N-methyl- amino)carbonyl)cyclohexane-1-carboxylic acid, process for their preparation and pharmaceutical compositions containing them
BR9205652A BR9205652A (en) 1991-12-23 1992-12-12 Stable salts of (+) - (15,2R) -N- (2-hydroxylamine-2-oxoethyl) N-methylamino carbonyl cyclohexane-carboxylic acid, process of its preparation, and pharmaceutical composition
PCT/EP1992/002903 WO1993013056A1 (en) 1991-12-23 1992-12-12 Stable salts of (+)-(1s,2r)-2-[[n-(2-hydroxylamino-2-oxoethyl)-n-methyl-amino]carbonyl]cyclohexane-1-carboxylic acid, process for their preparation and pharmaceutical compositions containing them
SK3796-92A SK379692A3 (en) 1991-12-23 1992-12-21 Stable salts of (+)-(1s,2r)-2-//n-(2-hydroxylamino-2- -oxoethyl)-n-methyl-amino/carbonyl/cyclohexan-1-carboxylic acid, method of their preparation and pharmaceutical agents containing these salts
NZ245547A NZ245547A (en) 1991-12-23 1992-12-21 Salts of (+)-(1s,2r)-2-[[n-(2-hydroxylamino-2- oxoethyl)-n-methylamino]carbonyl]cyclohexane-1- carboxylic acid with metals and organic bases; pharmaceutical compositions
CS923796A CZ379692A3 (en) 1991-12-23 1992-12-21 Stable salts of (+)-(1s,2r)-2-//n-(2-hydroxylamino-2-oxoethyl)-n-methyl-amino/carbonyl /cyclohexane-1-carboxylic acid, process of their preparation and pharmaceutical compositions in which said stable salts are contained
MA23040A MA22749A1 (en) 1991-12-23 1992-12-22 (+) - (15.2R) -2- (N-2 HYDROXYLAMINO -2-OXOETHYL) -N-METHYL-AMINO) CARBONYL) CYCLO HEXANE -1-CARBOXYLIC ACID SALTS; PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
HR921454A HRP921454A2 (en) 1991-12-23 1992-12-22 Stable salts of (1r,2s)-2-n-(2-hydroxylamino-2-oxoethyl)-n-methyl-amino onyl cyclohexane-1-carboxylic acid, process for their aration and pharmaceutical compositions containing them
SI9200409A SI9200409A (en) 1991-12-23 1992-12-22 (+)-(1s,1r)-2-((n-(2-hydroxylamino-2-oxoethyl)-n-methyl-amino) carbonyl)cyclohexan-1-carboxylic acids stable salts, process for the preparation thereof and pharmaceutical preparations comprising the same
CN92113839A CN1079474A (en) 1991-12-23 1992-12-23 New anti-hypertension compound and their preparation method and the pharmaceutical composition that contains them
TNTNSN92117A TNSN92117A1 (en) 1991-12-23 1992-12-23 STABLE ACID SALTS (+) (-1S, 2R) -2 [N-2-HYDROXYLAMINO-2- OXOETHYL] -N-METHYL-AMINO] CARBONYL] CYCLOHEXANE -1- CARBOXYLIC, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING
YU110892A YU110892A (en) 1991-12-23 1992-12-23 STABLE SALTS (+) - (1S, 2R) -2 - {[N- (2-HYDROXYAMINO-2-OXOETHYL) -N-METHYLAMINO] CARBONYL} -CYCLOHEXANE-1-CARBOHYLIC ACIDS, PROCEDURE FOR THEIR PRODUCTION AND PREPARATION CONTAIN
PL92297118A PL169086B1 (en) 1991-12-23 1992-12-23 Method of obtaining novel salts of (+)-(1s,2r)-2-{[n-(2-hydroxyamino-2-ketoethyl)-n-methylamine] carbonyl} cyclohehanocarboxylic-1 acid
ZA9210004A ZA9210004B (en) 1991-12-23 1992-12-23 Stable salts of (+)-(1S,2R)-2-((N-(-2-hydroxylamino-2-oxoethyl)-N-methyl-amino)carbonyl)cyclohexane-1-carboxylic acid, process for their preparation and pharmaceutical compositions containing them
PT101156A PT101156A (en) 1991-12-23 1992-12-23 (+) - (I, S, 2R) -2 - {{N- (2-HYDROXYLAMINO-2-OXOETHYL) N-METHYLAMINO} CARBONYL} CYCLOHEXANE-1-CARBOXYLIC ACID, ITS PREPARATION PROCESS, PHARMACEUTICAL COMPOSITIONS AND USE AS ANTI-HYPERTENSIVE
LVP-92-358A LV10426B (en) 1991-12-23 1992-12-23 STABLE SALTS OF (+)-(1S,2R)-2-{£N-(2-hydroxylamino-2-oxoethyl)-N-methylamino|carbonyl}-cyclohexane-1-carbocyclic acid, process for their preparation and pharmaceutical compositions containing them
MX9207543A MX9207543A (en) 1991-12-23 1992-12-23 STABLE SALTS OF ACID (+) - (1S, 2R) - [[B. (2-HYDROXYLAMINO-2-OXOETHYL) -N-METHYLAMINE] CARBONYL] CYCL OHEXAN-1-CARBOXYLIC, PROCEDURE FOR ITS PREPARATION, AND PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM
BG98050A BG98050A (en) 1991-12-23 1993-08-18 Salts resistant to (+)-(1s,2r)-2-[[n-(2-hydroxylamino-2-oxoethyl)-n-methyl-amino] carbonyl] cyclohexane-1-carbonic acid, method for their preparation and pharmaceutical compositions containing them
NO93932982A NO932982L (en) 1991-12-23 1993-08-20 STABLE SALTS OF (+) - (1S, 2R) -2 - ((N- (2-HYDROXYLAMINO-2-OXOETHYL) -N-METHYLAMINO) CARBONYL) CYCLOHEXAN-1-CARBOXYLIC ACID ACID AND PREPARING PROCESS FOR THE PREPARATION OF PREPARATION THEREOF
FI933685A FI933685A0 (en) 1991-12-23 1993-08-20 STABILA SALTER AV (+) - (1S, 2R) -2 - ((N- (2-HYDROXYLAMINO-2-OXOETHYL) -N-METHYLAMINO) CARBONYL) CYCLOHEXAN-1-CARBOXYL SYRIA,
EE9400006A EE9400006A (en) 1991-12-23 1994-05-23 Stable salts of (+) - (1R, 2S) -2 - [[N- (2-hydroxyamino-2-oxoethyl) -N-methylamino] carbonyl] cyclohexane-1-carboxylic acid, process for their preparation and pharmacological compounds containing them

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ITMI913448A IT1252708B (en) 1991-12-23 1991-12-23 STABLE SALTS OF (+) - (1R, 2S) -2 ((N- (2-HYDROXYLAMINE-2-OSSOETHL) -N-METHYLAMINE) CARBONYL) CYCLOHEXAN-1-CARBOXYL, ACE INHIBITIVE ACTIVITY, PROCEDURE FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM.

Publications (3)

Publication Number Publication Date
ITMI913448A0 ITMI913448A0 (en) 1991-12-23
ITMI913448A1 ITMI913448A1 (en) 1993-06-23
IT1252708B true IT1252708B (en) 1995-06-26

Family

ID=11361409

Family Applications (1)

Application Number Title Priority Date Filing Date
ITMI913448A IT1252708B (en) 1991-12-23 1991-12-23 STABLE SALTS OF (+) - (1R, 2S) -2 ((N- (2-HYDROXYLAMINE-2-OSSOETHL) -N-METHYLAMINE) CARBONYL) CYCLOHEXAN-1-CARBOXYL, ACE INHIBITIVE ACTIVITY, PROCEDURE FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM.

Country Status (26)

Country Link
EP (1) EP0575572A1 (en)
JP (1) JPH06506002A (en)
CN (1) CN1079474A (en)
AU (1) AU657591B2 (en)
BG (1) BG98050A (en)
BR (1) BR9205652A (en)
CA (1) CA2104372A1 (en)
CZ (1) CZ379692A3 (en)
EE (1) EE9400006A (en)
FI (1) FI933685A0 (en)
HR (1) HRP921454A2 (en)
HU (1) HUT69287A (en)
IT (1) IT1252708B (en)
LV (1) LV10426B (en)
MA (1) MA22749A1 (en)
MX (1) MX9207543A (en)
NZ (1) NZ245547A (en)
PL (1) PL169086B1 (en)
PT (1) PT101156A (en)
RU (1) RU2079489C1 (en)
SI (1) SI9200409A (en)
SK (1) SK379692A3 (en)
TN (1) TNSN92117A1 (en)
WO (1) WO1993013056A1 (en)
YU (1) YU110892A (en)
ZA (1) ZA9210004B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1264860B1 (en) * 1993-06-21 1996-10-17 Guidotti & C Spa Labor DERIVATIVES OF CIS- AND TRANS-2(((2-(HYDROXYAMINO)-2-OXOETHYL)- ALKYLAMINO)CARBONYL)CYCLOHEXINECARBOXYLIC ACIDS
US5639746A (en) * 1994-12-29 1997-06-17 The Procter & Gamble Company Hydroxamic acid-containing inhibitors of matrix metalloproteases
FR2817241B1 (en) 2000-11-30 2003-03-07 Cebal ALUMINUM TUBE WITH SPLITABLE END
US20100035991A1 (en) * 2006-09-28 2010-02-11 Mckeown Arlene Amide base salts of saha and polymorphis thereof
EP4030978A1 (en) * 2020-04-27 2022-07-27 Carter-Hoffmann, LLC Door movement system for cabinet

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1224627B (en) * 1988-04-12 1990-10-04 Guidotti & C Spa Labor ACID STARCHES CYCLOMETHYLEN_1,2_DICARBOSSILS THERAPEUTIC ADAPTIVITY, PROCEDURES FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.

Also Published As

Publication number Publication date
PT101156A (en) 1994-06-30
FI933685A (en) 1993-08-20
MA22749A1 (en) 1993-07-01
AU3087192A (en) 1993-07-28
SI9200409A (en) 1993-09-30
FI933685A0 (en) 1993-08-20
BG98050A (en) 1994-04-29
ZA9210004B (en) 1993-12-13
HU9302389D0 (en) 1993-11-29
JPH06506002A (en) 1994-07-07
SK379692A3 (en) 1995-04-12
YU110892A (en) 1996-01-08
EP0575572A1 (en) 1993-12-29
WO1993013056A1 (en) 1993-07-08
LV10426B (en) 1995-08-20
LV10426A (en) 1995-02-20
BR9205652A (en) 1994-05-03
PL297118A1 (en) 1993-09-06
AU657591B2 (en) 1995-03-16
TNSN92117A1 (en) 1993-06-08
PL169086B1 (en) 1996-05-31
ITMI913448A1 (en) 1993-06-23
HRP921454A2 (en) 1995-02-28
CN1079474A (en) 1993-12-15
MX9207543A (en) 1993-08-01
HUT69287A (en) 1995-09-28
RU2079489C1 (en) 1997-05-20
EE9400006A (en) 1995-12-15
NZ245547A (en) 1995-12-21
CA2104372A1 (en) 1993-06-24
CZ379692A3 (en) 1993-09-15
ITMI913448A0 (en) 1991-12-23

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