CA1174603A - Method of inhibiting the growth of protozoa - Google Patents
Method of inhibiting the growth of protozoaInfo
- Publication number
- CA1174603A CA1174603A CA000379588A CA379588A CA1174603A CA 1174603 A CA1174603 A CA 1174603A CA 000379588 A CA000379588 A CA 000379588A CA 379588 A CA379588 A CA 379588A CA 1174603 A CA1174603 A CA 1174603A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- group
- alpha
- amino acid
- compounds
- 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.)
- Expired
Links
- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 15
- 230000012010 growth Effects 0.000 title abstract description 21
- 238000000034 method Methods 0.000 title abstract description 18
- 241001465754 Metazoa Species 0.000 claims abstract description 30
- 150000001412 amines Chemical class 0.000 claims abstract description 22
- -1 procarbozine Chemical compound 0.000 claims description 73
- VLCYCQAOQCDTCN-UHFFFAOYSA-N eflornithine Chemical compound NCCCC(N)(C(F)F)C(O)=O VLCYCQAOQCDTCN-UHFFFAOYSA-N 0.000 claims description 45
- 238000011282 treatment Methods 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 150000001413 amino acids Chemical class 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 13
- 108010006654 Bleomycin Proteins 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229960001561 bleomycin Drugs 0.000 claims description 10
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 claims description 10
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 9
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 9
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 206010037075 Protozoal infections Diseases 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 230000003287 optical effect Effects 0.000 claims description 7
- 229940127089 cytotoxic agent Drugs 0.000 claims description 6
- KRUVSRGJKCHYMY-UHFFFAOYSA-N 1,3-bis(3-carbamimidoylphenyl)urea Chemical compound NC(=N)C1=CC=CC(NC(=O)NC=2C=C(C=CC=2)C(N)=N)=C1 KRUVSRGJKCHYMY-UHFFFAOYSA-N 0.000 claims description 5
- WZIPHSLUGLMTRU-UHFFFAOYSA-N 6-n-(2-amino-1,6-dimethylpyrimidin-1-ium-4-yl)-1,2-dimethylquinolin-1-ium-4,6-diamine;methyl sulfate Chemical compound COS(O)(=O)=O.COS([O-])(=O)=O.C=1C=C2N(C)C(C)=CC(=N)C2=CC=1NC1=CC(C)=[N+](C)C(N)=N1 WZIPHSLUGLMTRU-UHFFFAOYSA-N 0.000 claims description 5
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- 239000003904 antiprotozoal agent Substances 0.000 claims description 5
- 239000002254 cytotoxic agent Substances 0.000 claims description 5
- 231100000599 cytotoxic agent Toxicity 0.000 claims description 5
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 5
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- 238000011321 prophylaxis Methods 0.000 claims description 5
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- DYKFCLLONBREIL-KVUCHLLUSA-N minocycline Chemical compound C([C@H]1C2)C3=C(N(C)C)C=CC(O)=C3C(=O)C1=C(O)[C@@]1(O)[C@@H]2[C@H](N(C)C)C(O)=C(C(N)=O)C1=O DYKFCLLONBREIL-KVUCHLLUSA-N 0.000 claims description 4
- WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims description 4
- KMJWBVJQFGRCEB-UHFFFAOYSA-O 4-n-(4-imino-1,2-dimethylquinolin-6-yl)-1,6-dimethylpyrimidin-1-ium-2,4-diamine Chemical compound C=1C=C2N(C)C(C)=CC(=N)C2=CC=1NC1=CC(C)=[N+](C)C(N)=N1 KMJWBVJQFGRCEB-UHFFFAOYSA-O 0.000 claims description 3
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- MOOFYEJFXBSZGE-QJUDHZBZSA-N 1,2-bis[(z)-(4-chlorophenyl)methylideneamino]guanidine Chemical compound C=1C=C(Cl)C=CC=1\C=N/N=C(/N)N\N=C/C1=CC=C(Cl)C=C1 MOOFYEJFXBSZGE-QJUDHZBZSA-N 0.000 claims description 2
- NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 claims description 2
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- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 claims description 2
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- UKHWDRMMMYWSFL-UHFFFAOYSA-N Nicarbazin Chemical compound CC=1C=C(C)NC(=O)N=1.C1=CC([N+](=O)[O-])=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1 UKHWDRMMMYWSFL-UHFFFAOYSA-N 0.000 claims description 2
- FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 claims description 2
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- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims description 2
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CULOEOTWMUCRSJ-UHFFFAOYSA-M thallium(i) fluoride Chemical compound [Tl]F CULOEOTWMUCRSJ-UHFFFAOYSA-M 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- 210000003812 trophozoite Anatomy 0.000 description 1
- 208000037972 tropical disease Diseases 0.000 description 1
- 230000000654 trypanocidal effect Effects 0.000 description 1
- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019163 vitamin B12 Nutrition 0.000 description 1
- 239000011715 vitamin B12 Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/105—Aliphatic or alicyclic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/132—Heterocyclic compounds containing only one nitrogen as hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Polymers & Plastics (AREA)
- Epidemiology (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (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)
- Feed For Specific Animals (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15997380A | 1980-06-16 | 1980-06-16 | |
| US159,973 | 1980-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1174603A true CA1174603A (en) | 1984-09-18 |
Family
ID=22574910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000379588A Expired CA1174603A (en) | 1980-06-16 | 1981-06-11 | Method of inhibiting the growth of protozoa |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5731613A (de) |
| AT (1) | AT377180B (de) |
| AU (1) | AU544990B2 (de) |
| BE (1) | BE889230A (de) |
| CA (1) | CA1174603A (de) |
| CH (1) | CH651206A5 (de) |
| DE (2) | DE3123295A1 (de) |
| FR (1) | FR2484255A1 (de) |
| GB (1) | GB2078735B (de) |
| IE (1) | IE51300B1 (de) |
| IL (1) | IL63087A (de) |
| IT (1) | IT1171380B (de) |
| NL (1) | NL194153C (de) |
| NZ (1) | NZ197394A (de) |
| PH (1) | PH16634A (de) |
| SE (1) | SE460517B (de) |
| ZA (1) | ZA813953B (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58123555U (ja) * | 1982-02-17 | 1983-08-23 | 三菱電機株式会社 | インライン型電子銃の組立装置 |
| NL8400927A (nl) * | 1984-03-23 | 1985-10-16 | Philips Nv | Inrichting en werkwijze voor het monteren van een geintegreerd elektronenkanonsysteem. |
| DE3421384A1 (de) * | 1984-06-08 | 1985-12-12 | Standard Elektrik Lorenz Ag, 7000 Stuttgart | Vorrichtung zum zusammenbau von elektronenstrahlerzeugern |
| JPS62148462A (ja) * | 1985-12-19 | 1987-07-02 | メレルダウフア−マス−テイカルズ インコ−ポレ−テツド | 原生動物の生長を抑制する新規な方法 |
| EP0326766B1 (de) * | 1988-02-05 | 1992-06-17 | Merrell Dow Pharmaceuticals Inc. | 5-Substituierte Ornithin-Derivate |
| US5455234A (en) * | 1994-03-16 | 1995-10-03 | Ahluwalia; Gurpreet S. | Inhibition of hair growth |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR64495B (en) * | 1977-06-01 | 1980-03-31 | Merck & Co Inc | Novel fluorinated amino acids |
| US4139563A (en) * | 1977-07-01 | 1979-02-13 | Merrell Toraude Et Compagnie | α-ACETYLENIC DERIVATIVES OF AMINES |
| US4088667A (en) * | 1977-07-01 | 1978-05-09 | Merrell Toraude Et Compagnie | Lower alkyl 2-tri-(lower)alkylsilylacetylene-N-carbethoxyglycinates and process for using same |
| CA1121375A (en) * | 1977-07-01 | 1982-04-06 | Brian W. Metcalf | Derivatives of amines and amino acids |
| US4182891A (en) * | 1977-07-01 | 1980-01-08 | Merrell Toraude Et Compagnie | α-Acetylenic derivatives of α-amino acids |
| CA1091661A (en) | 1977-07-11 | 1980-12-16 | Philippe Bey | .alpha.-HALOMETHYL DERIVATIVES OF .alpha.-AMINO ACIDS |
| US4134918A (en) * | 1977-09-06 | 1979-01-16 | Merrell Toraude Et Compagnie | Alpha-halomethyl derivatives of amines |
-
1981
- 1981-06-11 CA CA000379588A patent/CA1174603A/en not_active Expired
- 1981-06-11 PH PH25759A patent/PH16634A/en unknown
- 1981-06-11 ZA ZA813953A patent/ZA813953B/xx unknown
- 1981-06-11 AU AU71654/81A patent/AU544990B2/en not_active Expired
- 1981-06-11 SE SE8103678A patent/SE460517B/sv not_active IP Right Cessation
- 1981-06-11 NZ NZ197394A patent/NZ197394A/en unknown
- 1981-06-12 DE DE19813123295 patent/DE3123295A1/de active Granted
- 1981-06-12 IE IE1308/81A patent/IE51300B1/en not_active IP Right Cessation
- 1981-06-12 IL IL63087A patent/IL63087A/xx not_active IP Right Cessation
- 1981-06-12 DE DE3153623A patent/DE3153623C2/de not_active Expired - Lifetime
- 1981-06-15 FR FR8111733A patent/FR2484255A1/fr active Granted
- 1981-06-15 NL NL8102863A patent/NL194153C/nl not_active IP Right Cessation
- 1981-06-15 JP JP9208181A patent/JPS5731613A/ja active Granted
- 1981-06-15 IT IT48684/81A patent/IT1171380B/it active
- 1981-06-15 GB GB8118326A patent/GB2078735B/en not_active Expired
- 1981-06-15 CH CH3939/81A patent/CH651206A5/de not_active IP Right Cessation
- 1981-06-15 BE BE0/205104A patent/BE889230A/fr not_active IP Right Cessation
- 1981-06-15 AT AT0266581A patent/AT377180B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT8148684A0 (it) | 1981-06-15 |
| IT1171380B (it) | 1987-06-10 |
| ATA266581A (de) | 1984-07-15 |
| NL194153C (nl) | 2001-08-03 |
| NL8102863A (nl) | 1982-01-18 |
| JPS5731613A (en) | 1982-02-20 |
| IE51300B1 (en) | 1986-11-26 |
| IL63087A (en) | 1984-10-31 |
| NZ197394A (en) | 1984-09-28 |
| SE8103678L (sv) | 1981-12-17 |
| DE3153623C2 (de) | 1991-06-27 |
| FR2484255B1 (de) | 1984-12-14 |
| AU544990B2 (en) | 1985-06-27 |
| PH16634A (en) | 1983-12-05 |
| DE3123295C2 (de) | 1990-07-12 |
| AU7165481A (en) | 1981-12-24 |
| CH651206A5 (de) | 1985-09-13 |
| IE811308L (en) | 1981-12-16 |
| ZA813953B (en) | 1982-06-30 |
| GB2078735B (en) | 1985-05-15 |
| DE3123295A1 (de) | 1982-04-29 |
| BE889230A (fr) | 1981-12-15 |
| AT377180B (de) | 1985-02-25 |
| GB2078735A (en) | 1982-01-13 |
| FR2484255A1 (fr) | 1981-12-18 |
| NL194153B (nl) | 2001-04-02 |
| SE460517B (sv) | 1989-10-23 |
| JPH0432052B2 (de) | 1992-05-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20010918 |