NO910191L - MACROCYCLIC TETRAAZA COMPOUNDS CONTAINING A SEXRING, PROCEDURE FOR PREPARING THEREOF, AND PHARMACEUTICAL AGENTS CONTAINING SUCH. - Google Patents
MACROCYCLIC TETRAAZA COMPOUNDS CONTAINING A SEXRING, PROCEDURE FOR PREPARING THEREOF, AND PHARMACEUTICAL AGENTS CONTAINING SUCH.Info
- Publication number
- NO910191L NO910191L NO91910191A NO910191A NO910191L NO 910191 L NO910191 L NO 910191L NO 91910191 A NO91910191 A NO 91910191A NO 910191 A NO910191 A NO 910191A NO 910191 L NO910191 L NO 910191L
- Authority
- NO
- Norway
- Prior art keywords
- denotes
- group
- hydrogen atom
- figures
- represent
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 239000008177 pharmaceutical agent Substances 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 7
- 150000001413 amino acids Chemical class 0.000 abstract 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 2
- 125000000524 functional group Chemical group 0.000 abstract 2
- 150000002678 macrocyclic compounds Chemical class 0.000 abstract 2
- 229920002521 macromolecule Polymers 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000000032 diagnostic agent Substances 0.000 abstract 1
- 229940039227 diagnostic agent Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- -1 hydroxymethylene Chemical group 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 229910021645 metal ion Inorganic materials 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
Classifications
-
- 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
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0474—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group
- A61K51/0482—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group chelates from cyclic ligands, e.g. DOTA
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2123/00—Preparations for testing in vivo
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Physics & Mathematics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Radiology & Medical Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
6-Membered-ring-containing macrocyclic tetraaza compounds of the general formula I <IMAGE> in which ... represents a single or double bond, Q represents a nitrogen atom or the radical NH, X<1> represents a hydrogen atom, -(CH2)n-R<1>- or <IMAGE> group where n denotes the figures 1 to 5, m denotes the figures 0 to 2 and R<1> denotes a hydrogen atom or a hydroxyl group, X<2> represents X<1> or a -(CH2)n-(O)l-(CH2)k-(C6H4)q-R<2> group where k denotes the figures 0 to 4, l and q denote the figures 0 or 1 and R<2> denotes a hydrogen atom, a C1-C4-alkoxy group, a functional group or, bonded by means of this functional group, a bio- or macromolecule, A<1>, A<2>, B<1>, B<2>, C<1>, C<2>, D<1>, D<2>, E<1>, E<2>, F<1> and F<2> independently of one another each represent X<2> G represents R<2> or a second macrocycle, bonded by means of K, of the general formula II <IMAGE> where K denotes a direct bond, a bis(carbonylamino) group (-NH-CO-CO-NH-) or a C1-C14-alkylene group which optionally at the ends carries carbonyl( &rdurule& CO) or carbonylamino (-NH-CO-) groups or oxygen atoms and optionally contains one or more oxygen atom(s), hydroxymethylene (-CH-OH-), CH(X<2>)COOZ, acyl or hydroxyacyl- substituted imino groups or one or two C-C double and/or C-C triple bonds, Z represents a hydrogen atom and/or a metal ion equivalent of an element of atomic number 21-29, 31, 32, 37-39, 42-44, 49 or 57-83, with the proviso that the 12 ring substituents A<1> to F<2> represent at least 8 hydrogen atoms, that X<1> and X<2> only simultaneously represent hydrogen atoms when at least one of the ring substituents A<1> to F<2> does not represent a hydrogen atom and that the macrocycle of the general formula I no longer contains a bio- or macromolecule and that, if desired, the radical of the CO2H groups is present as ester or amide, and their salts with inorganic and/or organic bases, amino acids or amino acid amides are useful diagnostic and therapeutic agents.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4001655A DE4001655A1 (en) | 1990-01-18 | 1990-01-18 | 6-RING MACROCYCLIC TETRAAZA COMPOUNDS, METHOD FOR PRODUCING THE SAME AND PHARMACEUTICAL PRODUCTS CONTAINING THEM |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO910191D0 NO910191D0 (en) | 1991-01-17 |
| NO910191L true NO910191L (en) | 1991-07-19 |
Family
ID=6398485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO91910191A NO910191L (en) | 1990-01-18 | 1991-01-17 | MACROCYCLIC TETRAAZA COMPOUNDS CONTAINING A SEXRING, PROCEDURE FOR PREPARING THEREOF, AND PHARMACEUTICAL AGENTS CONTAINING SUCH. |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0438206B1 (en) |
| JP (1) | JPH05112567A (en) |
| KR (1) | KR910014377A (en) |
| AT (1) | ATE141602T1 (en) |
| AU (1) | AU6981291A (en) |
| CA (1) | CA2034242A1 (en) |
| DE (2) | DE4001655A1 (en) |
| DK (1) | DK0438206T3 (en) |
| ES (1) | ES2091865T3 (en) |
| FI (1) | FI94758C (en) |
| GR (1) | GR3020973T3 (en) |
| HU (1) | HUT56569A (en) |
| IE (1) | IE75898B1 (en) |
| IL (1) | IL96840A0 (en) |
| NO (1) | NO910191L (en) |
| NZ (1) | NZ236803A (en) |
| PT (1) | PT96505B (en) |
| TW (1) | TW233298B (en) |
| ZA (1) | ZA91389B (en) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2644785B1 (en) * | 1989-03-24 | 1991-07-05 | Guerbet Sa | NOVEL NITROGEN MACROCYCLIC LIGANDS, PROCESS FOR THEIR PREPARATION, METAL COMPLEXES FORMED BY SUCH LIGANDS AND DIAGNOSTIC COMPOSITION CONTAINING THEM |
| US5739294A (en) * | 1991-12-10 | 1998-04-14 | The Dow Chemical Company | Bicyclopol yazamacrocyclophosphonic acid complexes for use as contrast agents |
| CA2103553A1 (en) * | 1991-12-10 | 1993-06-11 | Garry E. Kiefer | Bicyclopolyazamacrocyclocarboxylic acid complexes their conjugates, processes for their preparation, and use as radiopharmaceuticals |
| AU3246893A (en) * | 1991-12-10 | 1993-07-19 | Dow Chemical Company, The | Bicycloazamacrocyclophosphonic acid, conjugates, contrast agents and preparation |
| WO1993011800A1 (en) * | 1991-12-10 | 1993-06-24 | The Dow Chemical Company | Bicycle-polyazamacrocyclocarboxylic acid complexes, conjugates, preparation and use as contrast agents |
| US5428139A (en) * | 1991-12-10 | 1995-06-27 | The Dow Chemical Company | Bicyclopolyazamacrocyclophosphonic acid complexes for use as radiopharmaceuticals |
| WO1994026313A1 (en) * | 1993-05-06 | 1994-11-24 | The Dow Chemical Company | Bicyclopolyazamacrocyclocarboxylic acid complexes, their conjugates, processes for their preparation, and use as contrast agents |
| US5480990A (en) * | 1991-12-10 | 1996-01-02 | The Dow Chemical Company | Bicyclopolyazamacrocyclocarboxylic acid complexes for use as contrast agents |
| WO1994026315A1 (en) * | 1993-05-06 | 1994-11-24 | The Dow Chemical Company | Bicyclopolyazamacrocyclocarboxylic acid complexes, their conjugates, processes for their preparation, and use as radiopharmaceuticals |
| US5358704A (en) * | 1993-09-30 | 1994-10-25 | Bristol-Myers Squibb | Hepatobiliary tetraazamacrocyclic magnetic resonance contrast agents |
| US5417959A (en) * | 1993-10-04 | 1995-05-23 | Mallinckrodt Medical, Inc. | Functionalized aza-crytand ligands for diagnostic imaging applications |
| EP0668274B1 (en) * | 1994-02-21 | 1998-08-26 | PLIVA, farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvo | Sulfonamidodioxepanes with hypoglycemic activity, methods of preparation, intermediates and salts thereof |
| US6207826B1 (en) | 1995-03-27 | 2001-03-27 | Isis Pharmaceuticals, Inc. | Macrocyclic compounds having nitrogen-containing linkages |
| US6107482A (en) | 1995-03-27 | 2000-08-22 | Isis Pharmaceuticals, Inc. | Nitrogenous macrocyclic compounds |
| EP0898574B1 (en) * | 1996-04-19 | 2003-11-12 | Dow Global Technologies Inc. | Fluorescent chelates as visual tissue specific imaging agents |
| IT1291624B1 (en) * | 1997-04-18 | 1999-01-11 | Bracco Spa | COMPLEX CHELATES OF PARAMAGNETIC METALS WITH LOW TOXICITY |
| EP0977598A1 (en) * | 1997-04-22 | 2000-02-09 | Nycomed Imaging As | Nmr image compounds |
| FR2794744B1 (en) * | 1999-06-09 | 2001-09-21 | Guerbet Sa | METAL COMPLEXES OF BICYCLIC POLYAMINOACIDS, THEIR PREPARATION PROCESS AND THEIR APPLICATION IN MEDICAL IMAGING |
| US8986650B2 (en) | 2005-10-07 | 2015-03-24 | Guerbet | Complex folate-NOTA-Ga68 |
| FR2891830B1 (en) | 2005-10-07 | 2011-06-24 | Guerbet Sa | SHORT AMINOALCOHOL COMPOUNDS AND METAL COMPLEXES FOR MEDICAL IMAGING |
| JP5368099B2 (en) | 2005-10-07 | 2013-12-18 | ゲルベ | A compound comprising a moiety for recognition of a biological target coupled to a signal moiety capable of complexing with gallium |
| US8198101B2 (en) | 2006-03-10 | 2012-06-12 | Nordion (Canada) Inc. | Bifunctional polyazamacrocyclic chelating agents |
| HRP20170874T4 (en) | 2013-04-26 | 2022-09-02 | Guerbet | Contrast medium formulation and related preparation method |
| JP7034160B2 (en) | 2016-11-28 | 2022-03-11 | バイエル・ファルマ・アクティエンゲゼルシャフト | High relaxation gadolinium chelate compound for use in magnetic resonance imaging |
| US11944690B2 (en) | 2018-11-23 | 2024-04-02 | Bayer Aktiengesellschaft | Formulation of contrast media and process of preparation thereof |
| FR3091872B1 (en) | 2019-01-17 | 2020-12-25 | Guerbet Sa | COMPLEX OF GADOLINIUM AND A LIGAND CHELATOR DERIVED FROM PCTA DIASTEREOISOMERICALLY ENRICHED AND PROCESS FOR SYNTHESIS |
| FR3091873B1 (en) | 2019-01-17 | 2020-12-25 | Guerbet Sa | COMPLEX OF GADOLINIUM AND A LIGAND CHELATOR DERIVED FROM PCTA DIASTEREOISOMERICALLY ENRICHED AND PROCESS FOR PREPARATION AND PURIFICATION |
| KR20230041007A (en) | 2020-07-17 | 2023-03-23 | 게르브 | Methods for preparing chelating ligands derived from PCTA |
| CN114105983B (en) * | 2021-11-09 | 2023-08-11 | 国科温州研究院(温州生物材料与工程研究所) | Preparation and application of chiral 1,4,7, 10-tetraaza-2, 6-pyridine cycloparaffin derivative and metal chelate thereof |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036945A (en) | 1976-05-03 | 1977-07-19 | The Massachusetts General Hospital | Composition and method for determining the size and location of myocardial infarcts |
| US4331647A (en) | 1980-03-03 | 1982-05-25 | Goldenberg Milton David | Tumor localization and therapy with labeled antibody fragments specific to tumor-associated markers |
| DE3129906C3 (en) * | 1981-07-24 | 1996-12-19 | Schering Ag | Paramagnetic complex salts, their preparation and agents for use in NMR diagnostics |
| DE3150917A1 (en) | 1981-12-18 | 1983-06-30 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | "2-AMINO-1- (1,3-DIOXOLAN-4-YL) -ETHANOL COMPOUNDS, THEIR PRODUCTION AND USE FOR PROCESSING" |
| NL194579C (en) * | 1983-01-21 | 2002-08-05 | Schering Ag | Diagnostic. |
| DE3324235A1 (en) * | 1983-07-01 | 1985-01-10 | Schering AG, 1000 Berlin und 4709 Bergkamen | NEW COMPLEX ILLUMINATORS, COMPLEX AND COMPLEX SALTS |
| DE3417413A1 (en) | 1984-05-11 | 1985-11-14 | Dr. Karl Thomae Gmbh, 7950 Biberach | Dicarboxylic acid monohydrazide derivatives, their preparation and their use as coupling components |
| SE8502573D0 (en) * | 1985-05-23 | 1985-05-23 | Jouko Kanakre | FLUORESCENT LANTHANIDE CHELATES USEFUL AS LABELS OF PHYSIOLOGICALLY ACTIVE MATERIALS |
| DE3772785D1 (en) | 1986-01-23 | 1991-10-17 | Squibb & Sons Inc | 1-SUBSTITUTED-4,7,10-TRISCARBOXYMETHYL-1,4,7,10-TETRAAZACYCLODODECAN AND ANALOG. |
| DE3625417C2 (en) * | 1986-07-28 | 1998-10-08 | Schering Ag | Tetraazacyclododecane derivatives |
| IT1224416B (en) | 1987-12-24 | 1990-10-04 | Bracco Ind Chimica Spa | MACROCYCLIC CHELANTS AND THEIR CHELATES |
| DE3713842A1 (en) | 1987-04-22 | 1988-11-17 | Schering Ag | SUBSTITUTED CYCLIC COMPLEX MAKERS, COMPLEX AND COMPLEX SALTS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL AGENTS CONTAINING THEM |
| DE3869251D1 (en) | 1987-07-16 | 1992-04-23 | Nycomed As | AMINOPOLYCARBONIC ACIDS AND THEIR DERIVATIVES. |
| DE3825040A1 (en) * | 1988-07-20 | 1990-01-25 | Schering Ag, 13353 Berlin | 5- OR 6-RING MACROCYCLIC POLYAZA COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL AGENTS CONTAINING THEM |
| FR2644785B1 (en) * | 1989-03-24 | 1991-07-05 | Guerbet Sa | NOVEL NITROGEN MACROCYCLIC LIGANDS, PROCESS FOR THEIR PREPARATION, METAL COMPLEXES FORMED BY SUCH LIGANDS AND DIAGNOSTIC COMPOSITION CONTAINING THEM |
| DE3938992A1 (en) * | 1989-11-21 | 1991-05-23 | Schering Ag | Cascade polymer-bound complex formers, their complexes and conjugates, process for their preparation and pharmaceutical compositions containing them |
-
1990
- 1990-01-18 DE DE4001655A patent/DE4001655A1/en not_active Withdrawn
- 1990-12-31 IL IL96840A patent/IL96840A0/en unknown
-
1991
- 1991-01-14 JP JP3002602A patent/JPH05112567A/en active Pending
- 1991-01-16 CA CA002034242A patent/CA2034242A1/en not_active Abandoned
- 1991-01-16 DK DK91250008.9T patent/DK0438206T3/da active
- 1991-01-16 ES ES91250008T patent/ES2091865T3/en not_active Expired - Lifetime
- 1991-01-16 AT AT91250008T patent/ATE141602T1/en not_active IP Right Cessation
- 1991-01-16 EP EP91250008A patent/EP0438206B1/en not_active Expired - Lifetime
- 1991-01-16 DE DE59108091T patent/DE59108091D1/en not_active Expired - Lifetime
- 1991-01-17 PT PT96505A patent/PT96505B/en not_active IP Right Cessation
- 1991-01-17 HU HU91156A patent/HUT56569A/en unknown
- 1991-01-17 NZ NZ236803A patent/NZ236803A/en unknown
- 1991-01-17 NO NO91910191A patent/NO910191L/en unknown
- 1991-01-18 ZA ZA91389A patent/ZA91389B/en unknown
- 1991-01-18 IE IE16291A patent/IE75898B1/en not_active IP Right Cessation
- 1991-01-18 KR KR1019910000816A patent/KR910014377A/en not_active Application Discontinuation
- 1991-01-18 FI FI910276A patent/FI94758C/en active
- 1991-01-18 AU AU69812/91A patent/AU6981291A/en not_active Abandoned
- 1991-08-06 TW TW080108935A patent/TW233298B/zh active
-
1996
- 1996-09-06 GR GR960402335T patent/GR3020973T3/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI910276A0 (en) | 1991-01-18 |
| KR910014377A (en) | 1991-08-31 |
| ZA91389B (en) | 1991-10-30 |
| FI94758B (en) | 1995-07-14 |
| PT96505A (en) | 1991-10-15 |
| IE75898B1 (en) | 1997-09-24 |
| JPH05112567A (en) | 1993-05-07 |
| DK0438206T3 (en) | 1997-01-20 |
| NO910191D0 (en) | 1991-01-17 |
| AU6981291A (en) | 1991-08-22 |
| ES2091865T3 (en) | 1996-11-16 |
| HU910156D0 (en) | 1991-08-28 |
| EP0438206B1 (en) | 1996-08-21 |
| NZ236803A (en) | 1993-08-26 |
| IE910162A1 (en) | 1991-07-31 |
| CA2034242A1 (en) | 1991-07-19 |
| IL96840A0 (en) | 1991-09-16 |
| FI94758C (en) | 1995-10-25 |
| TW233298B (en) | 1994-11-01 |
| DE59108091D1 (en) | 1996-09-26 |
| FI910276A (en) | 1991-07-19 |
| HUT56569A (en) | 1991-09-30 |
| EP0438206A1 (en) | 1991-07-24 |
| GR3020973T3 (en) | 1996-12-31 |
| DE4001655A1 (en) | 1991-07-25 |
| PT96505B (en) | 1998-07-31 |
| ATE141602T1 (en) | 1996-09-15 |
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