KR860700254A - 메틸렌-비스포스폰산 유도체의 제조방법 - Google Patents
메틸렌-비스포스폰산 유도체의 제조방법Info
- Publication number
- KR860700254A KR860700254A KR1019860700180A KR860700180A KR860700254A KR 860700254 A KR860700254 A KR 860700254A KR 1019860700180 A KR1019860700180 A KR 1019860700180A KR 860700180 A KR860700180 A KR 860700180A KR 860700254 A KR860700254 A KR 860700254A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- alkyl
- carbon atoms
- ester
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 4
- MBKDYNNUVRNNRF-UHFFFAOYSA-N medronic acid Chemical class OP(O)(=O)CP(O)(O)=O MBKDYNNUVRNNRF-UHFFFAOYSA-N 0.000 title 1
- -1 phenoxy, mercapto Chemical group 0.000 claims 14
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000005846 1-(alkanoyloxy)ethyl group Chemical group 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims 1
- 125000005042 acyloxymethyl group Chemical group 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 1
- 125000005205 alkoxycarbonyloxyalkyl group Chemical group 0.000 claims 1
- 125000005206 alkoxycarbonyloxymethyl group Chemical group 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 150000003939 benzylamines Chemical class 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 1
- HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 claims 1
- 229960004919 procaine Drugs 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Biochemistry (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (5)
- 일반식(Ⅱ)의 디클로로메틸 에테르를 출발물질로 사용하고, 하기 반응순서를 따라서 일반식(Ⅰ)의 화합물 및 약제학적으로 허용되는 비독성 염과 신체에서 쉽게 가수분해되는 그의 에스테르를 제조하는 방법.[반응순서]상기 식에서,R1은 직쇄 또는 측쇄, 포화 또는 불포화 지방족 또는 지환식 C1-C10탄화수소기, 아릴 또는 아릴-C1-C4-알킬기이고, 경우에 따라 R1은 직쇄 또는 측쇄 C1-C4-알킬, 아미노, C1-C4-알킬아미노, 디-(C1-C4-알킬)-아미노, 카복시, C1-C4-알콕시카보닐, 하이드록시, C1-C4-알콕시, 페녹시, 머캅토, C1-C4-알킬티오, 페닐티오, 할로겐, 트리플루오로메틸로 치환 또는 비치환되며: R2는 수소, C1-C8-알킬, 아릴-C1-C4-알킬 또는 할로겐을 나타내고: X는 산소 또는 황이며, n은 0 내지 2의 정수이나: 단 n=0이고 R1이 메틸인 경우 R2가 수소 또는 메틸이 될 수 없으며, n=0이고 R1이 비치환된 n-부틸, n-펜틸 또는 n-헥실인 경우 R2가 수소가 될수는 없다.
- 제1항에 있어서, R1이 아미노, 하이드록시, 메틸 또는 할로겐으로 임의 치환된 직쇄 또는 측쇄 C3-C6알킬, 페닐 또는 벤질을 나타내고, R2가 수소, 직쇄 또는 측쇄 C1-C4-알킬, 벤질 또는 할로겐을 나타내며: 바람직하게는 R1이 프로필, 부틸, 아미노프로필, 아미노부틸, 2,2,2-트리플루오로에틸, 페닐 또는 톨릴이고, R2가 수소, 메틸 에틸 또는 염소인 방법.
- 제1항에 있어서, 알칼리 금속염, 알킬리성 토금속염, 암모니아와의 염, 저급 알킬아민, 저급 알카노일아민, 프로카인, 사이클로알킬아민, 벤질아민, 및 헤테로환식 아민으로 이루어진 그룹으로부터 선택한 염인, 일반식(Ⅰ)화합물의 1-, 2-, 3- 또는 4염기성 염인 방법.
- 제1항에 있어서, 생체내에서 쉽게 가수분해되는 에스테르로, 에스테르 형성 잔기는 탄소수 3 내지 6인 알카노일옥시메틸, 탄소수 4 내지 7인 1-(알카노일옥시)에틸, 탄소수 5 내지 8인 1-메틸-1-(알카노일옥시)에틸, 탄소수 3 내지 6인 알콕시카보닐옥시메틸, 탄소수 4 내지 7인 1-(알콕시보닐카옥시)에틸, 탄소수 5 내지 8인 1-메틸-1-(알콕시카보닐옥시)에틸, 3-프탈리딜, 4-크로토놀락토닐, γ-부티롤락톤-4-일, (2-옥소-1,3-디옥솔렌-4-일)메틸, (5-메틸-2-옥소-1,3-디옥솔렌-4-일)메틸, 및 (5-페닐-2-옥소-1,3-디옥솔렌-4-일)메틸, 뿐만 아니라 디알킬아미노알킬, 아세토닐, 및 메톡시메틸로 이루어진 그룹중에서 선택한, 일반식(Ⅰ)화합물의 모노-, 디-, 트리- 또는 테트라 에스테르인 방법.
- 제4항에 있어서, 알카노일옥시알킬 또는 알콕시카보닐옥시 알킬 에스테르, 특히 피발로일옥시메틸 또는 에톡시카보닐옥시에틸 에스테르인 방법.※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8419489 | 1984-07-31 | ||
| GB848419489A GB8419489D0 (en) | 1984-07-31 | 1984-07-31 | Chemical compounds |
| 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 (1)
| Publication Number | Publication Date |
|---|---|
| KR860700254A true KR860700254A (ko) | 1986-08-01 |
Family
ID=10564711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019860700180A KR860700254A (ko) | 1984-07-31 | 1985-07-25 | 메틸렌-비스포스폰산 유도체의 제조방법 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4732998A (ko) |
| EP (1) | EP0191044B1 (ko) |
| JP (1) | JPH068303B2 (ko) |
| KR (1) | KR860700254A (ko) |
| AU (1) | AU583848B2 (ko) |
| DE (1) | DE3575929D1 (ko) |
| DK (1) | DK167808B1 (ko) |
| ES (1) | ES8707964A1 (ko) |
| FI (1) | FI861357A0 (ko) |
| GB (1) | GB8419489D0 (ko) |
| GR (1) | GR851865B (ko) |
| IE (1) | IE58614B1 (ko) |
| PT (1) | PT80886B (ko) |
| WO (1) | WO1986000902A1 (ko) |
| ZA (1) | ZA855264B (ko) |
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. |
| DE69023844T2 (de) * | 1989-09-06 | 1996-06-20 | Merck & Co Inc | Acyloxymethylester der Bisphonsäuren als Knochenresorptions-Inhibitoren. |
| US5227506A (en) * | 1989-09-06 | 1993-07-13 | 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 |
| KR100272907B1 (ko) * | 1992-07-10 | 2001-03-02 | 히라이 가쯔히꼬 | 메탄디포스폰산 유도체, 이의 제조방법 및 이의 의약 용도 |
| 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 |
| US6143919A (en) * | 1999-05-18 | 2000-11-07 | 3M Innovative Properties Company | Polymerizable acidic compounds and methods of preparation |
| US6315566B1 (en) | 1999-05-18 | 2001-11-13 | 3M Innovative Properties Company | Dental materials |
| AU2002337862A1 (en) * | 2001-10-18 | 2003-04-28 | Ilex Products, Inc. | Methods 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 |
| CN104822695B (zh) * | 2012-07-05 | 2018-01-09 | 衣阿华大学研究基金会 | 治疗性双膦酸盐 |
| US10557039B2 (en) * | 2016-02-22 | 2020-02-11 | Surfactis Technologies | Compositions comprising bisphosphonic compounds dissolved in a fluorinated solvent, and use thereof for covering the surface of a part |
Family Cites Families (8)
| 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 DE DE8585903807T patent/DE3575929D1/de not_active Expired - Fee Related
- 1985-07-25 WO PCT/DK1985/000071 patent/WO1986000902A1/en active IP Right Grant
- 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 AU AU46736/85A patent/AU583848B2/en not_active Ceased
- 1985-07-25 KR KR1019860700180A patent/KR860700254A/ko not_active Application Discontinuation
- 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 |
|---|---|
| IE851717L (en) | 1986-01-31 |
| ZA855264B (en) | 1986-03-26 |
| PT80886A (en) | 1985-08-01 |
| US4732998A (en) | 1988-03-22 |
| JPH068303B2 (ja) | 1994-02-02 |
| PT80886B (pt) | 1987-11-30 |
| GB8419489D0 (en) | 1984-09-05 |
| WO1986000902A1 (en) | 1986-02-13 |
| EP0191044B1 (en) | 1990-02-07 |
| IE58614B1 (en) | 1993-10-20 |
| GR851865B (ko) | 1985-12-02 |
| FI861357A (fi) | 1986-03-27 |
| JPS61503034A (ja) | 1986-12-25 |
| EP0191044A1 (en) | 1986-08-20 |
| ES545783A0 (es) | 1987-09-01 |
| DE3575929D1 (de) | 1990-03-15 |
| FI861357A0 (fi) | 1986-03-27 |
| AU583848B2 (en) | 1989-05-11 |
| DK147386D0 (da) | 1986-04-01 |
| AU4673685A (en) | 1986-02-25 |
| ES8707964A1 (es) | 1987-09-01 |
| DK167808B1 (da) | 1993-12-20 |
| DK147386A (da) | 1986-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |