DK167808B1 - Methylen-bisphosphonsyrederivat, fremgangsmaade til fremstilling heraf samt farmaceutisk sammensaetning indeholdende disse derivater - Google Patents
Methylen-bisphosphonsyrederivat, fremgangsmaade til fremstilling heraf samt farmaceutisk sammensaetning indeholdende disse derivater Download PDFInfo
- Publication number
- DK167808B1 DK167808B1 DK147386A DK147386A DK167808B1 DK 167808 B1 DK167808 B1 DK 167808B1 DK 147386 A DK147386 A DK 147386A DK 147386 A DK147386 A DK 147386A DK 167808 B1 DK167808 B1 DK 167808B1
- Authority
- DK
- Denmark
- Prior art keywords
- methyl
- formula
- compound
- alkyl
- carbon atoms
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- MBKDYNNUVRNNRF-UHFFFAOYSA-N medronic acid Chemical class OP(O)(=O)CP(O)(O)=O MBKDYNNUVRNNRF-UHFFFAOYSA-N 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000008194 pharmaceutical composition Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 67
- -1 3 -phthalidyl Chemical group 0.000 claims description 56
- 239000000203 mixture Substances 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 238000007257 deesterification reaction Methods 0.000 claims description 6
- 239000012312 sodium hydride Substances 0.000 claims description 6
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 125000005848 1-(alkoxycarbonyloxy)ethyl group Chemical group 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
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- 241001460678 Napo <wasp> Species 0.000 claims description 3
- PJRBPPUAKJRQAP-UHFFFAOYSA-N [phenoxy(phosphono)methyl]phosphonic acid Chemical compound OP(O)(=O)C(P(O)(O)=O)OC1=CC=CC=C1 PJRBPPUAKJRQAP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims description 3
- 125000005042 acyloxymethyl group Chemical group 0.000 claims description 3
- 125000005206 alkoxycarbonyloxymethyl group Chemical group 0.000 claims description 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 3
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- 102000055006 Calcitonin Human genes 0.000 claims description 2
- 108060001064 Calcitonin Proteins 0.000 claims description 2
- FCBNUTOTWPYDNT-UHFFFAOYSA-N [(4-hydroxyphenoxy)-phosphonomethyl]phosphonic acid Chemical group OC1=CC=C(OC(P(O)(O)=O)P(O)(O)=O)C=C1 FCBNUTOTWPYDNT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
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- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
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- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 claims description 2
- 229960004015 calcitonin Drugs 0.000 claims description 2
- 239000000262 estrogen Substances 0.000 claims description 2
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- 150000002367 halogens Chemical group 0.000 claims description 2
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- CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 claims description 2
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229960003171 plicamycin Drugs 0.000 claims description 2
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 claims description 2
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- 239000011775 sodium fluoride Substances 0.000 claims description 2
- 235000013024 sodium fluoride Nutrition 0.000 claims description 2
- 229960000414 sodium fluoride Drugs 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000005847 1-methyl-1-(alkanoyloxy)-ethyl group Chemical group 0.000 claims 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
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Classifications
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- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3839—Polyphosphonic acids
- C07F9/386—Polyphosphonic acids containing hydroxy substituents in the hydrocarbon radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Nutrition Science (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8419489 | 1984-07-31 | ||
| GB848419489A GB8419489D0 (en) | 1984-07-31 | 1984-07-31 | Chemical compounds |
| DK8500071 | 1985-07-25 | ||
| PCT/DK1985/000071 WO1986000902A1 (en) | 1984-07-31 | 1985-07-25 | Derivatives of methylene-bisphosphonic acid, process for their preparation and a pharmaceutical composition |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK147386D0 DK147386D0 (da) | 1986-04-01 |
| DK147386A DK147386A (da) | 1986-04-01 |
| DK167808B1 true DK167808B1 (da) | 1993-12-20 |
Family
ID=10564711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK147386A DK167808B1 (da) | 1984-07-31 | 1986-04-01 | Methylen-bisphosphonsyrederivat, fremgangsmaade til fremstilling heraf samt farmaceutisk sammensaetning indeholdende disse derivater |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4732998A (xx) |
| EP (1) | EP0191044B1 (xx) |
| JP (1) | JPH068303B2 (xx) |
| KR (1) | KR860700254A (xx) |
| AU (1) | AU583848B2 (xx) |
| DE (1) | DE3575929D1 (xx) |
| DK (1) | DK167808B1 (xx) |
| ES (1) | ES8707964A1 (xx) |
| FI (1) | FI861357A0 (xx) |
| GB (1) | GB8419489D0 (xx) |
| GR (1) | GR851865B (xx) |
| IE (1) | IE58614B1 (xx) |
| PT (1) | PT80886B (xx) |
| WO (1) | WO1986000902A1 (xx) |
| ZA (1) | ZA855264B (xx) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3805663A1 (de) * | 1988-02-24 | 1989-09-07 | Henkel Kgaa | Oxaalkanpolyphosphonsaeuren, ihre verwendung als thresholder sowie diese verbindungen enthaltende, komplexierend wirkende zusammensetzungen |
| DE3822650A1 (de) * | 1988-07-05 | 1990-02-01 | Boehringer Mannheim Gmbh | Neue diphosphonsaeurederivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| US5266722A (en) * | 1988-11-09 | 1993-11-30 | W. R. Grace & Co.-Conn. | Polyether bis-phosphonic acid compounds |
| PH26923A (en) * | 1989-03-08 | 1992-12-03 | Ciba Geigy | N-substituted amino alkanediphosphonic acids |
| FI83421C (fi) * | 1989-06-21 | 1991-07-10 | Huhtamaeki Oy | Foerfarande foer framstaellning av farmakologiskt anvaendbara metylenbisfosfonsyraderivat. |
| US5227506A (en) * | 1989-09-06 | 1993-07-13 | Merck & Co., Inc. | Acyloxymethyl esters of bisphosphonic acids as bone resorption inhibitors |
| EP0416689B1 (en) * | 1989-09-06 | 1995-11-29 | Merck & Co. Inc. | Acyloxymethyl esters of bisphosphonic acids as bone resorption inhibitors |
| GB9024345D0 (en) * | 1990-11-08 | 1990-12-19 | Merck Sharp & Dohme | Therapeutic agents |
| JP3141053B2 (ja) * | 1991-12-26 | 2001-03-05 | アベンティス ファーマ株式会社 | ビスホスホン酸誘導体 |
| US5200554A (en) * | 1992-01-21 | 1993-04-06 | Nasman Jan Anders H | Bisphosphonic acid derivatives and their use |
| ES2155446T3 (es) * | 1992-07-10 | 2001-05-16 | Toray Industries | Derivado de metanodifosfonato, su produccion y su uso farmaceutico. |
| FR2703590B1 (fr) * | 1993-04-05 | 1995-06-30 | Sanofi Elf | Utilisation de derives d'acide bisphosphonique pour la preparation de medicaments destines a favoriser la reparation osseuse . |
| US20010007863A1 (en) * | 1998-06-18 | 2001-07-12 | Merck & Co., Inc. | Wet granulation formulation for bisphosphonic acids |
| US6315566B1 (en) | 1999-05-18 | 2001-11-13 | 3M Innovative Properties Company | Dental materials |
| US6143919A (en) * | 1999-05-18 | 2000-11-07 | 3M Innovative Properties Company | Polymerizable acidic compounds and methods of preparation |
| EP1435970A4 (en) * | 2001-10-18 | 2005-05-04 | Ilex Products Inc | METHOD OF TREATING SKIN WITH DIPHOSPHONATE DERIVATIVES |
| DE102004032781A1 (de) * | 2004-01-23 | 2005-08-11 | Mcs Micro Carrier Systems Gmbh | Bisphosphonsäurederivate |
| JP2006028024A (ja) * | 2004-07-12 | 2006-02-02 | Toray Ind Inc | リン含有有機化合物の製造方法。 |
| EP2289900A1 (en) * | 2009-08-26 | 2011-03-02 | Humboldt Universität zu Berlin | Bisphosphonates as inhibitors of acid sphingomyelinase |
| CA2878413A1 (en) * | 2012-07-05 | 2014-01-09 | University Of Iowa Research Foundation | Therapeutic bisphosphonates |
| CN109312171A (zh) * | 2016-02-22 | 2019-02-05 | 表面活性剂科技公司 | 包括溶解在氟化溶剂中的双膦酸根型化合物的组合物及其用于覆盖部件表面的用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA777769A (en) * | 1963-03-18 | 1968-02-06 | H. Roy Clarence | Substituted methylene diphosphonic acid compounds and detergent compositions |
| US3400131A (en) * | 1964-03-05 | 1968-09-03 | Hoffmann La Roche | 1, 3-di (4-pyridyl)-2-propanol derivatives |
| GB1115044A (en) * | 1964-08-06 | 1968-05-22 | Albright & Wilson Mfg Ltd | Derivatives of hydroxy diphosphonic acids |
| AT279051B (de) * | 1966-12-29 | 1970-02-25 | Procter & Gamble | Mundpflegemittel |
| US3400151A (en) * | 1967-12-28 | 1968-09-03 | Procter & Gamble | Bicyclic dimer of ethane-1-hydroxy-1, 1-diphosphonic acid and salts thereof |
| US4014959A (en) * | 1975-04-24 | 1977-03-29 | Monsanto Company | Phosphonoether carboxylates |
| SU772152A1 (ru) * | 1977-07-20 | 1983-02-15 | Центральный научно-исследовательский институт оловянной промышленности | 1-Алкоксиалкилиден-1,1-дифосфоновые кислоты или их калиевые,натриевые или аммониевые соли в качестве собирателей дл флотации касситерита и способ их получени |
| IT1201087B (it) * | 1982-04-15 | 1989-01-27 | Gentili Ist Spa | Bifosfonati farmacologicamente attivi,procedimento per la loro preparazione e relative composizioni farmaceutiche |
-
1984
- 1984-07-31 GB GB848419489A patent/GB8419489D0/en active Pending
-
1985
- 1985-07-08 IE IE171785A patent/IE58614B1/en not_active IP Right Cessation
- 1985-07-12 ZA ZA855264A patent/ZA855264B/xx unknown
- 1985-07-25 WO PCT/DK1985/000071 patent/WO1986000902A1/en active IP Right Grant
- 1985-07-25 AU AU46736/85A patent/AU583848B2/en not_active Ceased
- 1985-07-25 KR KR1019860700180A patent/KR860700254A/ko not_active Application Discontinuation
- 1985-07-25 DE DE8585903807T patent/DE3575929D1/de not_active Expired - Fee Related
- 1985-07-25 EP EP85903807A patent/EP0191044B1/en not_active Expired - Lifetime
- 1985-07-25 JP JP60503564A patent/JPH068303B2/ja not_active Expired - Lifetime
- 1985-07-25 US US06/852,248 patent/US4732998A/en not_active Expired - Fee Related
- 1985-07-29 GR GR851865A patent/GR851865B/el unknown
- 1985-07-30 PT PT80886A patent/PT80886B/pt not_active IP Right Cessation
- 1985-07-31 ES ES545783A patent/ES8707964A1/es not_active Expired
-
1986
- 1986-03-27 FI FI861357A patent/FI861357A0/fi not_active Application Discontinuation
- 1986-04-01 DK DK147386A patent/DK167808B1/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PT80886A (en) | 1985-08-01 |
| US4732998A (en) | 1988-03-22 |
| GB8419489D0 (en) | 1984-09-05 |
| PT80886B (pt) | 1987-11-30 |
| ZA855264B (en) | 1986-03-26 |
| AU4673685A (en) | 1986-02-25 |
| AU583848B2 (en) | 1989-05-11 |
| GR851865B (xx) | 1985-12-02 |
| DK147386D0 (da) | 1986-04-01 |
| IE851717L (en) | 1986-01-31 |
| JPH068303B2 (ja) | 1994-02-02 |
| EP0191044B1 (en) | 1990-02-07 |
| FI861357A (fi) | 1986-03-27 |
| DE3575929D1 (de) | 1990-03-15 |
| KR860700254A (ko) | 1986-08-01 |
| IE58614B1 (en) | 1993-10-20 |
| FI861357A0 (fi) | 1986-03-27 |
| WO1986000902A1 (en) | 1986-02-13 |
| JPS61503034A (ja) | 1986-12-25 |
| DK147386A (da) | 1986-04-01 |
| ES545783A0 (es) | 1987-09-01 |
| ES8707964A1 (es) | 1987-09-01 |
| EP0191044A1 (en) | 1986-08-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed | ||
| B1 | Patent granted (law 1993) | ||
| PBP | Patent lapsed |