IL104060A - Bicyclopolyazamacyclophosphonic acids, their complexes and conjugates, for use as contrast agents, and processes for their preparation - Google Patents
Bicyclopolyazamacyclophosphonic acids, their complexes and conjugates, for use as contrast agents, and processes for their preparationInfo
- Publication number
- IL104060A IL104060A IL10406092A IL10406092A IL104060A IL 104060 A IL104060 A IL 104060A IL 10406092 A IL10406092 A IL 10406092A IL 10406092 A IL10406092 A IL 10406092A IL 104060 A IL104060 A IL 104060A
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- compound
- terms
- term
- equal
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 46
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- -1 isothiocyanato , semicarbazido, thiosemicarbazido , maleimido, bromoacetamido Chemical group 0.000 claims description 14
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- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical class C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 201000010989 colorectal carcinoma Diseases 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000001651 cyanato group Chemical group [*]OC#N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- 238000012631 diagnostic technique Methods 0.000 description 1
- NSSMTQDEWVTEKN-UHFFFAOYSA-N diethoxy(methyl)phosphane Chemical compound CCOP(C)OCC NSSMTQDEWVTEKN-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003722 extracellular fluid Anatomy 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- LGMLJQFQKXPRGA-VPVMAENOSA-K gadopentetate dimeglumine Chemical compound [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O LGMLJQFQKXPRGA-VPVMAENOSA-K 0.000 description 1
- RYHQMKVRYNEBNJ-BMWGJIJESA-K gadoterate meglumine Chemical compound [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 RYHQMKVRYNEBNJ-BMWGJIJESA-K 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 210000004408 hybridoma Anatomy 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- 230000000705 hypocalcaemia Effects 0.000 description 1
- 229940127121 immunoconjugate Drugs 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000005228 liver tissue Anatomy 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- BCDIWLCKOCHCIH-UHFFFAOYSA-N methylphosphinic acid Chemical class CP(O)=O BCDIWLCKOCHCIH-UHFFFAOYSA-N 0.000 description 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- WSNTXKRJEQZLES-UHFFFAOYSA-N o-[amino(aminooxy)phosphoryl]hydroxylamine Chemical compound NOP(N)(=O)ON WSNTXKRJEQZLES-UHFFFAOYSA-N 0.000 description 1
- 239000008375 oral care agent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- 229960003330 pentetic acid Drugs 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003007 phosphonic acid derivatives Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000000063 preceeding effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 210000005227 renal system Anatomy 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002455 scale inhibitor Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 210000001562 sternum Anatomy 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- QQWYQAQQADNEIC-RVDMUPIBSA-N tert-butyl [(z)-[cyano(phenyl)methylidene]amino] carbonate Chemical compound CC(C)(C)OC(=O)O\N=C(/C#N)C1=CC=CC=C1 QQWYQAQQADNEIC-RVDMUPIBSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000012800 visualization Methods 0.000 description 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
- 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
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- 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
- A61K51/0497—Organic compounds conjugates with a carrier being an organic 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
- 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
- C07F9/6524—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having four or more nitrogen atoms as the only ring hetero atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Optics & Photonics (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Radiology & Medical Imaging (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80555191A | 1991-12-10 | 1991-12-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL104060A0 IL104060A0 (en) | 1993-05-13 |
| IL104060A true IL104060A (en) | 1998-12-06 |
Family
ID=25191891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10406092A IL104060A (en) | 1991-12-10 | 1992-12-10 | Bicyclopolyazamacyclophosphonic acids, their complexes and conjugates, for use as contrast agents, and processes for their preparation |
Country Status (18)
| Country | Link |
|---|---|
| EP (2) | EP0570575B1 (fr) |
| JP (1) | JPH07502043A (fr) |
| CN (1) | CN1038328C (fr) |
| AT (1) | ATE160943T1 (fr) |
| AU (1) | AU3246893A (fr) |
| CA (1) | CA2103556C (fr) |
| DE (1) | DE69223504T2 (fr) |
| DK (1) | DK0570575T3 (fr) |
| ES (1) | ES2110593T3 (fr) |
| GR (1) | GR3026121T3 (fr) |
| HK (1) | HK1006654A1 (fr) |
| HU (1) | HUT66220A (fr) |
| IL (1) | IL104060A (fr) |
| MX (1) | MX9207166A (fr) |
| RU (1) | RU2114115C1 (fr) |
| SG (1) | SG46598A1 (fr) |
| WO (1) | WO1993011802A1 (fr) |
| ZA (1) | ZA929576B (fr) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5385893A (en) * | 1993-05-06 | 1995-01-31 | The Dow Chemical Company | Tricyclopolyazamacrocyclophosphonic acids, complexes and derivatives thereof, for use as contrast agents |
| EP0696290A1 (fr) * | 1993-05-06 | 1996-02-14 | The Dow Chemical Company | Acides bicyclopolyazamacrocyclophosphoniques, leurs complexes et conjugues, destines a etre utilises en tant qu'agents de contraste, et leurs procedes de preparation |
| US6207826B1 (en) | 1995-03-27 | 2001-03-27 | Isis Pharmaceuticals, Inc. | Macrocyclic compounds having nitrogen-containing linkages |
| EP0817787A4 (fr) * | 1995-03-27 | 2000-09-13 | Isis Pharmaceuticals Inc | Composes macrocycliques azotes |
| US5834456A (en) * | 1996-02-23 | 1998-11-10 | The Dow Chemical Company | Polyazamacrocyclofluoromonoalkylphosphonic acids, and their complexes, for use as contrast agents |
| CA2251924C (fr) * | 1996-04-19 | 2006-05-30 | The Dow Chemical Company | Chelates fluorescents utilises en tant qu'agents visuels destines a l'imagerie et specifiques de certains tissus |
| US5888476A (en) * | 1996-11-13 | 1999-03-30 | Mallinckrodt Medical, Inc. | Magnetic resonance blood pool agents |
| US6440389B1 (en) | 2000-07-19 | 2002-08-27 | The General Hospital Corporation | Fluorescent agents for real-time measurement of organ function |
| US8211401B2 (en) * | 2008-12-05 | 2012-07-03 | Molecular Insight Pharmaceuticals, Inc. | Technetium- and rhenium-bis(heteroaryl) complexes and methods of use thereof for inhibiting PSMA |
| NO331773B1 (no) * | 2009-12-18 | 2012-03-26 | Ge Healthcare As | Mangankelater, sammensetninger omfattende slike og anvendelse av disse som kontrastmidler for magnettomografi (MR) |
| GB201610738D0 (en) | 2016-06-20 | 2016-08-03 | Ge Healthcare As | Chelate compounds |
| ES2813077T3 (es) * | 2016-12-21 | 2021-03-22 | Ge Healthcare As | Compuestos quelatos de manganeso basados en macrociclo de tetraazabiciclo adecuados como agentes de imagen de IRM |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3825040A1 (de) * | 1988-07-20 | 1990-01-25 | Schering Ag, 13353 Berlin | 5- oder 6-ring- enthaltende makrocyclische polyaza-verbindungen, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| DE4001655A1 (de) * | 1990-01-18 | 1991-07-25 | Schering Ag | 6-ring enthaltende makrocyclische tetraaza-verbindungen, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| FR2644785B1 (fr) * | 1989-03-24 | 1991-07-05 | Guerbet Sa | Nouveaux ligands macrocycliques azotes, procede de preparation, complexes metalliques formes par ces ligands et composition de diagnostic les contenant |
| DE3938992A1 (de) * | 1989-11-21 | 1991-05-23 | Schering Ag | Kaskadenpolymer-gebundene komplexbildner, deren komplexe und konjugate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| EP0511275A1 (fr) * | 1990-01-19 | 1992-11-04 | Nycomed Imaging As | Composes de chelation |
| GB9001245D0 (en) * | 1990-01-19 | 1990-03-21 | Salutar Inc | Compounds |
-
1992
- 1992-12-10 SG SG1996006488A patent/SG46598A1/en unknown
- 1992-12-10 RU RU93053767A patent/RU2114115C1/ru active
- 1992-12-10 DE DE69223504T patent/DE69223504T2/de not_active Expired - Fee Related
- 1992-12-10 HU HU9302312A patent/HUT66220A/hu unknown
- 1992-12-10 WO PCT/US1992/010668 patent/WO1993011802A1/fr active IP Right Grant
- 1992-12-10 IL IL10406092A patent/IL104060A/en not_active IP Right Cessation
- 1992-12-10 AT AT93901000T patent/ATE160943T1/de not_active IP Right Cessation
- 1992-12-10 EP EP93901000A patent/EP0570575B1/fr not_active Expired - Lifetime
- 1992-12-10 ES ES93901000T patent/ES2110593T3/es not_active Expired - Lifetime
- 1992-12-10 DK DK93901000T patent/DK0570575T3/da active
- 1992-12-10 AU AU32468/93A patent/AU3246893A/en not_active Abandoned
- 1992-12-10 MX MX9207166A patent/MX9207166A/es not_active IP Right Cessation
- 1992-12-10 EP EP96107948A patent/EP0735040A3/fr not_active Withdrawn
- 1992-12-10 ZA ZA929576A patent/ZA929576B/xx unknown
- 1992-12-10 CN CN92115368A patent/CN1038328C/zh not_active Expired - Fee Related
- 1992-12-10 JP JP5511072A patent/JPH07502043A/ja active Pending
- 1992-12-10 CA CA002103556A patent/CA2103556C/fr not_active Expired - Fee Related
-
1998
- 1998-02-12 GR GR980400293T patent/GR3026121T3/el unknown
- 1998-06-23 HK HK98106042A patent/HK1006654A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU3246893A (en) | 1993-07-19 |
| HU9302312D0 (en) | 1993-12-28 |
| HUT66220A (en) | 1994-10-28 |
| SG46598A1 (en) | 1998-02-20 |
| DK0570575T3 (da) | 1998-08-24 |
| IL104060A0 (en) | 1993-05-13 |
| HK1006654A1 (en) | 1999-03-12 |
| ATE160943T1 (de) | 1997-12-15 |
| WO1993011802A1 (fr) | 1993-06-24 |
| CA2103556C (fr) | 2002-04-16 |
| MX9207166A (es) | 1993-07-01 |
| CN1074447A (zh) | 1993-07-21 |
| ZA929576B (en) | 1994-06-10 |
| RU2114115C1 (ru) | 1998-06-27 |
| DE69223504T2 (de) | 1998-04-02 |
| JPH07502043A (ja) | 1995-03-02 |
| EP0735040A2 (fr) | 1996-10-02 |
| EP0570575A1 (fr) | 1993-11-24 |
| ES2110593T3 (es) | 1998-02-16 |
| EP0570575B1 (fr) | 1997-12-10 |
| DE69223504D1 (de) | 1998-01-22 |
| EP0735040A3 (fr) | 1997-02-26 |
| GR3026121T3 (en) | 1998-05-29 |
| CN1038328C (zh) | 1998-05-13 |
| CA2103556A1 (fr) | 1993-06-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |