FR2680173A1 - 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 cardiovasculaires . Download PDFInfo
- Publication number
- FR2680173A1 FR2680173A1 FR9110039A FR9110039A FR2680173A1 FR 2680173 A1 FR2680173 A1 FR 2680173A1 FR 9110039 A FR9110039 A FR 9110039A FR 9110039 A FR9110039 A FR 9110039A FR 2680173 A1 FR2680173 A1 FR 2680173A1
- Authority
- FR
- France
- Prior art keywords
- dianhydro
- nitro
- deoxy
- amino
- glucitol
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 32
- 230000008569 process Effects 0.000 title claims abstract description 26
- 229940082615 organic nitrates used in cardiac disease Drugs 0.000 title claims abstract description 15
- 208000024172 Cardiovascular disease Diseases 0.000 title description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims abstract description 40
- 150000002823 nitrates Chemical class 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001413 amino acids Chemical class 0.000 claims abstract description 5
- 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
- 125000000539 amino acid group Chemical group 0.000 claims abstract description 4
- CDAISMWEOUEBRE-UHFFFAOYSA-N inositol Chemical group OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910002651 NO3 Inorganic materials 0.000 claims description 76
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 64
- -1 carbonyl- Chemical group 0.000 claims description 63
- 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 55
- 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 46
- 239000000047 product Substances 0.000 claims description 38
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- 239000004471 Glycine Substances 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 17
- 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 17
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- 125000004122 cyclic group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 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 8
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- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
- CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 claims description 7
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
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- 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 description 4
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims description 4
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- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 claims description 4
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 4
- 229930195722 L-methionine Natural products 0.000 claims description 4
- 229930182821 L-proline Natural products 0.000 claims description 4
- 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 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 229960004295 valine Drugs 0.000 claims description 4
- 125000006823 (C1-C6) acyl group Chemical group 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
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- 235000004279 alanine Nutrition 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 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
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-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
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- 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 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
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
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- 239000000006 Nitroglycerin Substances 0.000 description 1
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- RHMQNXNXUZLEIY-UHFFFAOYSA-N methanol;2-propan-2-yloxypropane Chemical compound OC.CC(C)OC(C)C RHMQNXNXUZLEIY-UHFFFAOYSA-N 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
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- YZZCJYJBCUJISI-UHFFFAOYSA-N propatylnitrate Chemical compound [O-][N+](=O)OCC(CC)(CO[N+]([O-])=O)CO[N+]([O-])=O YZZCJYJBCUJISI-UHFFFAOYSA-N 0.000 description 1
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
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- ICRHORQIUXBEPA-UHFFFAOYSA-N thionitrous acid Chemical group SN=O ICRHORQIUXBEPA-UHFFFAOYSA-N 0.000 description 1
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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)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9110039A FR2680173A1 (fr) | 1991-08-07 | 1991-08-07 | Nitrates organiques, leurs procedes de preparation et leur utilisation dans le traitement de maladies cardiovasculaires . |
| PCT/EP1992/001746 WO1993003037A1 (fr) | 1991-08-07 | 1992-08-01 | Nitrates organiques, leurs procedes de preparation et leur utilisation dans le traitement de maladies cardiovasculaires |
| HU9400327A HUT70546A (en) | 1991-08-07 | 1992-08-01 | Organic nitrates and process for producing them |
| EP92917213A EP0604459A1 (fr) | 1991-08-07 | 1992-08-01 | Nitrates organiques, leurs procedes de preparation et leur utilisation dans le traitement de maladies cardiovasculaires |
| JP5503265A JPH07500817A (ja) | 1991-08-07 | 1992-08-01 | 有機ニトラート、その製造方法及びこれを心臓血管疾患の治療に使用する方法 |
| CA002113922A CA2113922A1 (fr) | 1991-08-07 | 1992-08-01 | Nitrates organiques, leurs procedes de preparation et leur utilisation dans le traitement de maladies cardiovasculaires |
| US07/971,812 US5591758A (en) | 1991-08-07 | 1992-08-01 | Organic nitrates, processes for their preparation and their use in the treatment of cardiovascular diseases |
| EP92202500A EP0530887A1 (fr) | 1991-08-07 | 1992-08-01 | Nitrates organiques, leurs procédés de préparation et leur utilisation dans le traitement de maladies cardiovasculaires |
| ZA925892A ZA925892B (en) | 1991-08-07 | 1992-08-06 | Organic nitrates, processes for their preparation and their use in the treatment of cardiovascular diseases. |
| MX9204613A MX9204613A (es) | 1991-08-07 | 1992-08-07 | Nitratos organicos, procedimientos para su preparacion y su uso en el tratamiento de enfermedades cardiovasculares |
| TW081108315A TW213906B (enExample) | 1991-08-07 | 1992-10-17 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| FR2680173A1 true FR2680173A1 (fr) | 1993-02-12 |
| FR2680173B1 FR2680173B1 (enExample) | 1995-05-05 |
Family
ID=9415992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR9110039A Granted FR2680173A1 (fr) | 1991-08-07 | 1991-08-07 | 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) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0114270A1 (de) * | 1982-12-29 | 1984-08-01 | Heinrich Mack Nachf. | Acylderivate von 1,4:3,6-Dianhydro-hexiten, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| EP0290885A2 (en) * | 1987-05-08 | 1988-11-17 | CHIESI FARMACEUTICI S.p.A. | 1,4:3,6-Dianhydrosorbitol 2-mono-nitrate and 5-mononitrate esters, a process for the preparation thereof and pharmaceutical compositions therefrom |
| EP0362575A1 (de) * | 1988-09-15 | 1990-04-11 | Schwarz Pharma Ag | Neue organische Nitrate und Verfahren zu deren Herstellung |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0114270A1 (de) * | 1982-12-29 | 1984-08-01 | Heinrich Mack Nachf. | Acylderivate von 1,4:3,6-Dianhydro-hexiten, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| EP0290885A2 (en) * | 1987-05-08 | 1988-11-17 | CHIESI FARMACEUTICI S.p.A. | 1,4:3,6-Dianhydrosorbitol 2-mono-nitrate and 5-mononitrate esters, a process for the preparation thereof and pharmaceutical compositions therefrom |
| EP0362575A1 (de) * | 1988-09-15 | 1990-04-11 | Schwarz Pharma Ag | Neue organische Nitrate und Verfahren zu deren Herstellung |
Non-Patent Citations (1)
| Title |
|---|
| JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. vol. 80, no. 5, 12 Mars 1958, GASTON, PA US pages 1158 - 1164; J. C. SHEENAN ET AL.: 'A new synthesis of cysteinyl peptides' * |
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 |
| 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 |
| CA2113922A1 (fr) | 1993-02-18 |
| ZA925892B (en) | 1993-07-28 |
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