CA2113922A1 - Nitrates organiques, leurs procedes de preparation et leur utilisation dans le traitement de maladies cardiovasculaires - Google Patents
Nitrates organiques, leurs procedes de preparation et leur utilisation dans le traitement de maladies cardiovasculairesInfo
- Publication number
- CA2113922A1 CA2113922A1 CA002113922A CA2113922A CA2113922A1 CA 2113922 A1 CA2113922 A1 CA 2113922A1 CA 002113922 A CA002113922 A CA 002113922A CA 2113922 A CA2113922 A CA 2113922A CA 2113922 A1 CA2113922 A1 CA 2113922A1
- Authority
- CA
- Canada
- Prior art keywords
- dianhydro
- nitro
- amino
- deoxy
- carbonyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 27
- 230000008569 process Effects 0.000 title claims abstract description 21
- 229940082615 organic nitrates used in cardiac disease Drugs 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 208000024172 Cardiovascular disease Diseases 0.000 title description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims abstract description 42
- 150000002823 nitrates Chemical class 0.000 claims abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
- 150000001413 amino acids Chemical class 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 claims abstract description 3
- CDAISMWEOUEBRE-UHFFFAOYSA-N inositol Chemical group OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000011593 sulfur Substances 0.000 claims abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 93
- 229910002651 NO3 Inorganic materials 0.000 claims description 75
- 150000001875 compounds Chemical class 0.000 claims description 72
- 239000000047 product Substances 0.000 claims description 70
- -1 t-butoxy Chemical group 0.000 claims description 31
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 28
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- KLDXJTOLSGUMSJ-UHFFFAOYSA-N 2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical compound OC1COC2C(O)COC21 KLDXJTOLSGUMSJ-UHFFFAOYSA-N 0.000 claims description 20
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 20
- 150000001408 amides Chemical class 0.000 claims description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 229910004679 ONO2 Inorganic materials 0.000 claims description 12
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 12
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 239000004471 Glycine Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical compound [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 claims description 7
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 229960002429 proline Drugs 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000001893 nitrooxy group Chemical group [O-][N+](=O)O* 0.000 claims description 5
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 4
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 4
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 229940024606 amino acid Drugs 0.000 claims description 4
- 235000001014 amino acid Nutrition 0.000 claims description 4
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- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 3
- 229930182821 L-proline Natural products 0.000 claims description 3
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 3
- YWXYYJSYQOXTPL-JGWLITMVSA-N [(3r,3ar,6s,6as)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl] nitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-JGWLITMVSA-N 0.000 claims description 3
- 229960004452 methionine Drugs 0.000 claims description 3
- 229960005190 phenylalanine Drugs 0.000 claims description 3
- 239000004474 valine Substances 0.000 claims description 3
- 125000006823 (C1-C6) acyl group Chemical group 0.000 claims description 2
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 235000004279 alanine Nutrition 0.000 claims description 2
- 125000000539 amino acid group Chemical group 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 claims description 2
- 229960000367 inositol Drugs 0.000 claims description 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 2
- 235000008729 phenylalanine Nutrition 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 10
- PWKSKIMOESPYIA-UHFFFAOYSA-N 2-acetamido-3-sulfanylpropanoic acid Chemical compound CC(=O)NC(CS)C(O)=O PWKSKIMOESPYIA-UHFFFAOYSA-N 0.000 claims 9
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 9
- QDGAVODICPCDMU-UHFFFAOYSA-N 2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid Chemical compound OC(=O)C(N)CC1=CC=CC(N(CCCl)CCCl)=C1 QDGAVODICPCDMU-UHFFFAOYSA-N 0.000 claims 2
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims 2
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims 2
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 claims 2
- FBPFZTCFMRRESA-UNTFVMJOSA-N L-iditol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO FBPFZTCFMRRESA-UNTFVMJOSA-N 0.000 claims 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 2
- 229930195722 L-methionine Natural products 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 229940059574 pentaerithrityl Drugs 0.000 claims 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 22
- 206010002383 Angina Pectoris Diseases 0.000 abstract description 3
- 208000019553 vascular disease Diseases 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 193
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 112
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 106
- 239000000243 solution Substances 0.000 description 104
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 39
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- 238000001953 recrystallisation Methods 0.000 description 16
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/001—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR91/10039 | 1991-08-07 | ||
| FR9110039A FR2680173A1 (fr) | 1991-08-07 | 1991-08-07 | Nitrates organiques, leurs procedes de preparation et leur utilisation dans le traitement de maladies cardiovasculaires . |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2113922A1 true CA2113922A1 (fr) | 1993-02-18 |
Family
ID=9415992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002113922A Abandoned CA2113922A1 (fr) | 1991-08-07 | 1992-08-01 | Nitrates organiques, leurs procedes de preparation et leur utilisation dans le traitement de maladies cardiovasculaires |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5591758A (enExample) |
| EP (2) | EP0604459A1 (enExample) |
| JP (1) | JPH07500817A (enExample) |
| CA (1) | CA2113922A1 (enExample) |
| FR (1) | FR2680173A1 (enExample) |
| HU (1) | HUT70546A (enExample) |
| MX (1) | MX9204613A (enExample) |
| TW (1) | TW213906B (enExample) |
| WO (1) | WO1993003037A1 (enExample) |
| ZA (1) | ZA925892B (enExample) |
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| ES2142773B1 (es) * | 1998-10-07 | 2001-01-01 | Lacer Sa | Derivados de mononitrato de isosorbida y su empleo como agentes vasodilatadores con tolerancia desminuida. |
| US6284790B1 (en) * | 2000-06-15 | 2001-09-04 | Sachin Gupte | Methods of potentiating organic nitrates having vasodilating activity and formulations for the same |
| US20040019206A1 (en) * | 2001-09-27 | 2004-01-29 | Peter Ruminiski | Lactone integrin antagonists |
| US20040254238A1 (en) * | 2003-04-07 | 2004-12-16 | Osteoscreen | Bone growth stimulation with NO/statin and other NO modulating combinations |
| ES2258365B1 (es) * | 2003-10-03 | 2007-12-01 | Lacer, S.A. | Derivados de disulfuro, sulfuro, sulfoxido y sulfona de azucares ciclicos y sus usos. |
| EP2149576A1 (en) | 2008-07-22 | 2010-02-03 | Lacer, S.A. | Isosorbide Nitrates having vasodilating activity |
| US7807716B2 (en) * | 2008-09-24 | 2010-10-05 | Oral Delivery Technology Ltd. | Nitric oxide amino acid ester compound, compositions for increasing nitric oxide levels and method of use |
| WO2013060673A1 (en) | 2011-10-24 | 2013-05-02 | Nicox S.A. | Quinone based nitric oxide donating compounds |
| WO2014111465A1 (en) * | 2013-01-17 | 2014-07-24 | Sanofi | Isomannide derivatives as inhibitors of soluble epoxide hydrolase |
| WO2014169976A1 (en) | 2013-04-18 | 2014-10-23 | Nicox Science Ireland | Quinone based nitric oxide donating compounds |
| CN103897023A (zh) * | 2014-02-28 | 2014-07-02 | 苏州维泰生物技术有限公司 | 一种合成甘氨酸半胱氨酸伪二肽模块的新方法 |
| US10913748B2 (en) * | 2018-11-04 | 2021-02-09 | Coeurative, Inc. | Compounds useful for treating cardiovascular diseases |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3248548A1 (de) * | 1982-12-29 | 1984-07-05 | Heinrich Mack Nachf., 7918 Illertissen | Acylderivate von 1,4:3,6-dianhydro-hexiten, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| IT1204571B (it) * | 1987-05-08 | 1989-03-10 | Chiesi Farma Spa | Esteri di 1,4:3,6-dianidrosorbitolo-2-mononitrato e 5-mononitrato,loro procedimento di preparazione e loro composizioni farmaceutiche |
| JP2628756B2 (ja) * | 1988-09-15 | 1997-07-09 | シュバルツファルマ アクチェンゲゼルシャフト | 新規有機ニトレート及びそれらの製造方法 |
| NL9001955A (nl) * | 1990-09-05 | 1992-04-01 | Cedona Pharm Bv | Nieuwe thiazolidinederivaten. |
-
1991
- 1991-08-07 FR FR9110039A patent/FR2680173A1/fr active Granted
-
1992
- 1992-08-01 CA CA002113922A patent/CA2113922A1/fr not_active Abandoned
- 1992-08-01 JP JP5503265A patent/JPH07500817A/ja active Pending
- 1992-08-01 US US07/971,812 patent/US5591758A/en not_active Expired - Fee Related
- 1992-08-01 EP EP92917213A patent/EP0604459A1/fr not_active Withdrawn
- 1992-08-01 WO PCT/EP1992/001746 patent/WO1993003037A1/fr not_active Ceased
- 1992-08-01 HU HU9400327A patent/HUT70546A/hu unknown
- 1992-08-01 EP EP92202500A patent/EP0530887A1/fr active Pending
- 1992-08-06 ZA ZA925892A patent/ZA925892B/xx unknown
- 1992-08-07 MX MX9204613A patent/MX9204613A/es unknown
- 1992-10-17 TW TW081108315A patent/TW213906B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| HU9400327D0 (en) | 1994-05-30 |
| EP0604459A1 (fr) | 1994-07-06 |
| MX9204613A (es) | 1993-09-01 |
| WO1993003037A1 (fr) | 1993-02-18 |
| TW213906B (enExample) | 1993-10-01 |
| FR2680173A1 (fr) | 1993-02-12 |
| FR2680173B1 (enExample) | 1995-05-05 |
| EP0530887A1 (fr) | 1993-03-10 |
| US5591758A (en) | 1997-01-07 |
| JPH07500817A (ja) | 1995-01-26 |
| HUT70546A (en) | 1995-10-30 |
| ZA925892B (en) | 1993-07-28 |
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