LU86958A1 - Sels d'acide thiamorpholinone carboxylique et de derives de diamino-2,4 pyrimidine,leur utilisation en cosmetique et pharmacie - Google Patents
Sels d'acide thiamorpholinone carboxylique et de derives de diamino-2,4 pyrimidine,leur utilisation en cosmetique et pharmacie Download PDFInfo
- Publication number
- LU86958A1 LU86958A1 LU86958A LU86958A LU86958A1 LU 86958 A1 LU86958 A1 LU 86958A1 LU 86958 A LU86958 A LU 86958A LU 86958 A LU86958 A LU 86958A LU 86958 A1 LU86958 A1 LU 86958A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- thiamorpholinone
- diamino
- piperidino
- carboxylate
- pyrimidine
- Prior art date
Links
- 239000002537 cosmetic Substances 0.000 title claims description 9
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical class NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 title description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 24
- 210000004761 scalp Anatomy 0.000 claims description 8
- 201000004384 Alopecia Diseases 0.000 claims description 7
- 230000000699 topical effect Effects 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 230000003676 hair loss Effects 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000006210 lotion Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 206010039792 Seborrhoea Diseases 0.000 claims description 3
- 231100000360 alopecia Toxicity 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 208000024963 hair loss Diseases 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- HWYHDWGGACRVEH-UHFFFAOYSA-N n-methyl-n-(4-pyrrolidin-1-ylbut-2-ynyl)acetamide Chemical compound CC(=O)N(C)CC#CCN1CCCC1 HWYHDWGGACRVEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 208000008742 seborrheic dermatitis Diseases 0.000 claims description 3
- PNCWHIAZZSDHPU-UHFFFAOYSA-N 2-benzylsulfanylethanamine Chemical compound NCCSCC1=CC=CC=C1 PNCWHIAZZSDHPU-UHFFFAOYSA-N 0.000 claims description 2
- 201000004624 Dermatitis Diseases 0.000 claims description 2
- 239000000443 aerosol Substances 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 239000000499 gel Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- -1 alkyl radical Chemical class 0.000 claims 2
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical group [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 claims 1
- 230000003779 hair growth Effects 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 230000004936 stimulating effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 150000003839 salts Chemical class 0.000 description 24
- 239000002253 acid Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001734 carboxylic acid salts Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229960003632 minoxidil Drugs 0.000 description 4
- 239000013543 active substance Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- IPFIEHIRBSTAKA-UHFFFAOYSA-N 6-piperidin-1-ylpyrimidine-2,4-diamine Chemical compound NC1=NC(N)=CC(N2CCCCC2)=N1 IPFIEHIRBSTAKA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 208000004631 alopecia areata Diseases 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- SAALQYKUFCIMHR-UHFFFAOYSA-N propan-2-ol;2-propan-2-yloxypropane Chemical compound CC(C)O.CC(C)OC(C)C SAALQYKUFCIMHR-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
- NBAJYWQRWMFKCA-UHFFFAOYSA-N 5-piperidin-1-ylpyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1N1CCCCC1 NBAJYWQRWMFKCA-UHFFFAOYSA-N 0.000 description 1
- 241000928106 Alain Species 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 125000002066 L-histidyl group Chemical group [H]N1C([H])=NC(C([H])([H])[C@](C(=O)[*])([H])N([H])[H])=C1[H] 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 230000003659 hair regrowth Effects 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000029305 taxis Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- SLYPOVJCSQHITR-UHFFFAOYSA-N tioxolone Chemical compound OC1=CC=C2SC(=O)OC2=C1 SLYPOVJCSQHITR-UHFFFAOYSA-N 0.000 description 1
- 229960003070 tioxolone Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU86958A LU86958A1 (fr) | 1987-07-31 | 1987-07-31 | Sels d'acide thiamorpholinone carboxylique et de derives de diamino-2,4 pyrimidine,leur utilisation en cosmetique et pharmacie |
| EP88112024A EP0304649B1 (de) | 1987-07-31 | 1988-07-26 | Salze von 6-Piperidino-2,4-diaminopyrimidin-3-oxyd und von Derivaten der Thiamorpholin-3-on-5-carbonsäure und deren Verwendung in kosmetischen Stoffen und als Heilmittel |
| DE8888112024T DE3862083D1 (de) | 1987-07-31 | 1988-07-26 | Salze von 6-piperidino-2,4-diaminopyrimidin-3-oxyd und von derivaten der thiamorpholin-3-on-5-carbonsaeure und deren verwendung in kosmetischen stoffen und als heilmittel. |
| AT88112024T ATE61801T1 (de) | 1987-07-31 | 1988-07-26 | Salze von 6-piperidino-2,4-diaminopyrimidin-3oxyd und von derivaten der thiamorpholin-3-on-5- carbonsaeure und deren verwendung in kosmetischen stoffen und als heilmittel. |
| CA000573492A CA1314884C (fr) | 1987-07-31 | 1988-07-29 | Sels d'acide thiamorpholinone carboxylique et de derives de diamino-2,4 pyrimidine, leur utilisation en cosmetique et pharmacie |
| US07/225,818 US4970063A (en) | 1987-07-31 | 1988-07-29 | Salts of thiamorpholinone carboxylic acid with 2,4-diaminopyrimidine derivatives and their use in cosmetics and pharmaceuticals |
| JP63188534A JPS6450867A (en) | 1987-07-31 | 1988-07-29 | Salts of thiamorpholinonecarboxylic acid and 2,4-diaminopyrimidine derivative and use for cosmetic and pharmaceutical composition |
| GR91400638T GR3001965T3 (en) | 1987-07-31 | 1991-05-20 | Salts of 6-piperidino-2,4-diaminopyrimidin-3-oxide and of derivatives of thiamorpholin-3-on-5-carboxylic acid, their cosmetical and medicinal use |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU86958A LU86958A1 (fr) | 1987-07-31 | 1987-07-31 | Sels d'acide thiamorpholinone carboxylique et de derives de diamino-2,4 pyrimidine,leur utilisation en cosmetique et pharmacie |
| LU86958 | 1987-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU86958A1 true LU86958A1 (fr) | 1989-03-08 |
Family
ID=19730954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU86958A LU86958A1 (fr) | 1987-07-31 | 1987-07-31 | Sels d'acide thiamorpholinone carboxylique et de derives de diamino-2,4 pyrimidine,leur utilisation en cosmetique et pharmacie |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4970063A (de) |
| EP (1) | EP0304649B1 (de) |
| JP (1) | JPS6450867A (de) |
| AT (1) | ATE61801T1 (de) |
| CA (1) | CA1314884C (de) |
| DE (1) | DE3862083D1 (de) |
| GR (1) | GR3001965T3 (de) |
| LU (1) | LU86958A1 (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU87304A1 (fr) * | 1988-07-29 | 1990-02-07 | Oreal | Nouveaux derives d'ureylene triamino-2,4,6 pyrimidine oxyde-3,leur preparation et leur utilisation en cosmetique et dermopharmacie |
| JP2869168B2 (ja) * | 1990-08-10 | 1999-03-10 | 鐘紡株式会社 | 育毛剤及びそれを含有する養毛化粧料 |
| AU690069B2 (en) * | 1993-02-09 | 1998-04-23 | Tulsa Forte Pharmacy Enterprises, Inc. | A method for stimulating hair growth with cationic derivatives of minoxidil using therapeutic iontophoresis |
| CN112811614A (zh) * | 2020-12-03 | 2021-05-18 | 嘉兴沃特泰科环保科技股份有限公司 | 一种循环水无磷阻垢剂及其制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3382248A (en) * | 1965-11-01 | 1968-05-07 | Upjohn Co | 6-amino-4, 5-di(substituted amino)-1, 2-dihydro-1-hydroxy-2-iminopyrimidines |
| US4139619A (en) * | 1976-05-24 | 1979-02-13 | The Upjohn Company | 6-Amino-4-(substituted amino)-1,2-dihydro-1-hydroxy-2-iminopyrimidine, topical compositions and process for hair growth |
| HU177601B (en) * | 1978-10-27 | 1981-11-28 | Egyt Gyogyszervegyeszeti Gyar | New process for preparing 6-piperidino-2,4-diamino-pyrimidine-3-oxide |
| FR2525220A1 (fr) * | 1982-04-15 | 1983-10-21 | Oreal | Nouveaux derives substitues de la thiamorpholinone et leurs procedes de preparation |
| FR2525106B1 (fr) * | 1982-04-15 | 1985-06-07 | Oreal | Composition cosmetique contenant en tant qu'agent actif sur l'elasticite et la souplesse de la peau, de la thiamorpholinone ou l'un de ses derives |
| IT1201436B (it) * | 1985-07-19 | 1989-02-02 | Vincenzo Zappia | Formulazioni topiche a lento rilascio |
-
1987
- 1987-07-31 LU LU86958A patent/LU86958A1/fr unknown
-
1988
- 1988-07-26 AT AT88112024T patent/ATE61801T1/de not_active IP Right Cessation
- 1988-07-26 DE DE8888112024T patent/DE3862083D1/de not_active Expired - Lifetime
- 1988-07-26 EP EP88112024A patent/EP0304649B1/de not_active Expired - Lifetime
- 1988-07-29 JP JP63188534A patent/JPS6450867A/ja active Pending
- 1988-07-29 CA CA000573492A patent/CA1314884C/fr not_active Expired - Fee Related
- 1988-07-29 US US07/225,818 patent/US4970063A/en not_active Expired - Fee Related
-
1991
- 1991-05-20 GR GR91400638T patent/GR3001965T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1314884C (fr) | 1993-03-23 |
| EP0304649B1 (de) | 1991-03-20 |
| EP0304649A1 (de) | 1989-03-01 |
| GR3001965T3 (en) | 1992-11-23 |
| ATE61801T1 (de) | 1991-04-15 |
| US4970063A (en) | 1990-11-13 |
| DE3862083D1 (de) | 1991-04-25 |
| JPS6450867A (en) | 1989-02-27 |
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