KR850008677A - 글리세로포스포콜린 및 글리세로포스포-에탈올아민 유도체의 제조방법 - Google Patents
글리세로포스포콜린 및 글리세로포스포-에탈올아민 유도체의 제조방법 Download PDFInfo
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- KR850008677A KR850008677A KR1019850003277A KR850003277A KR850008677A KR 850008677 A KR850008677 A KR 850008677A KR 1019850003277 A KR1019850003277 A KR 1019850003277A KR 850003277 A KR850003277 A KR 850003277A KR 850008677 A KR850008677 A KR 850008677A
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- KR
- South Korea
- Prior art keywords
- triphenylmethyl
- glycero
- general formula
- substituted
- formula
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract 2
- SUHOQUVVVLNYQR-MRVPVSSYSA-N choline alfoscerate Chemical compound C[N+](C)(C)CCOP([O-])(=O)OC[C@H](O)CO SUHOQUVVVLNYQR-MRVPVSSYSA-N 0.000 title 1
- 150000002317 glycerophosphoethanolamines Chemical class 0.000 title 1
- 229960004956 glycerylphosphorylcholine Drugs 0.000 title 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract 7
- JZNWSCPGTDBMEW-YFKPBYRVSA-N sn-glycero-3-phosphoethanolamine Chemical compound NCCO[P@@](O)(=O)OC[C@@H](O)CO JZNWSCPGTDBMEW-YFKPBYRVSA-N 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 238000009835 boiling Methods 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- SUHOQUVVVLNYQR-MRVPVSSYSA-O glycerylphosphorylcholine Chemical compound C[N+](C)(C)CCO[P@](O)(=O)OC[C@H](O)CO SUHOQUVVVLNYQR-MRVPVSSYSA-O 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000003791 organic solvent mixture Substances 0.000 claims 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims 1
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- -1 di-substituted triphenylmethyl groups Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 238000005866 tritylation reaction Methods 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Epoxy Resins (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- 다음 일반식(II)의 sn-글리세로-3-포스포콜린 또는 sn -글리세포-3-포스포-(N-트리페닐메틸)-에탄올아민, 이들의 무기 또는 유기산 또는 염기와의 염 또는 이들의 금속과의 복합물을 불활성 유기용매 또는 용매혼합물 중에서, 실은 내지 용매의 비점 또는 용매혼합물중 저-비점 용매성분의 비점의 온도에서 다음 일반식(III)의 반응성 트리페닐메틸 유도체와 반응시켜 글리세롤의 1위치의 산소에서 트리틸화 시킴을 특징으로 하여 다음 일반식(I)의 sn-글리세로-3-포스포콜린 및 sn-글리세로-3-포스포에탄올 아민의 트리페닐메틸 유도체를 제조하는 방법.상기식에서, T는 비치환되거나 C1-C6-알킬, C1-C6-일콕시 또는 할로겐으로 일치환되거나 다치환된 트리페닐메틸 그룹이고, 라디칼 R1,R2및R3중 둘은 항상 수소이고 나머지 한 라디칼R1,R2및R3중 들은 항상 수소이고 나머지 한 라디칼은 비치환되거나 C1-C6-알킬 , C1-C6-알콕시 또는 할로겐으로 일치환 또는 다치환된 트리페닐메틸 그룹이고, X는 염소, 브롬 또는 요오드와 같은 반응성 이탈 그룹 다.
- 제1항에 있어서, 일반식(III)의 활성트리페닐메틸 유도체로서, 사용된 일반식 (II)화합물 몰당 1.5-때 내지 3-배 몰과량의 트리페닐 메틸클로아이드를 사용함을 특징으로 하는 방법.
- 제1항 또는 2항에 있어서, 반응을 과량의 양지수용체 존재하에서 수행함을 특징으로 하는 방법.
- 제1항 내지 3항중 어느 한 항에 있어서, 반응을 양자 수용체로서의 3급아민 또는 헤테로사이클릭 염기 존재하에서 수행함을 특징으로 하는 방법.
- 제1항 내지 4항중 어느 한항에 있어서, 반응을 20 내지 80℃의 온도에서 수행하는 방법.
- 다음 일반식 (I)화합물을 산수용체 존재하에서 일반식 R4COOH의 복카실산의 아실화 유도체로 아실화시켜 다음 일반식(V) 화합물을 수득한 다음, 생성된 일반식(V)화합물에 산(단, 라디칼 R1R2및 R3중 하나가 트리페닐메틸그룹인 일반식(V)화합물의 경우에는 루이스산을 사용한다)을 작용시킴으로서 1-0-트리페닐메틸그룹을 제거하여 다음 일반식(VI)의 2-아실-sn-글리세로-3-포스포콜린 또는 2-아실-sn-글리세로-3-포스포-(N-트리페닐메틸)에탄올아민을 형성시키고, 일반식(VI)화합물을 산수용체 존재하에서 일반식 R5COOH의 카복실산의 아실화 유도체와 반응시킴으로써 더아실화시켜 다음 일반식(IVa)의 1,2-디아실-sn-글리세로-3-포스포콜린 또는 1,2-디아실-sn-글리세로-3-포스포-(N-트리페닐메틸)-에탄올아민을 수득한 다음, 생성된 라디칼 R1R2및 R3중 하나가 트리페닐메틸 그룹이고 다른 둘은 수소인 일반식(Ⅳa)화합물을 비양자성 용매중에서 산과 작용시켜 라디칼 R1', R2' 및 R3'가 수소인 일반식(Ⅳ)화합물로 전화시킴을 특징으로 하여, 각기 상이한 치환제를 갖는 일반식(IV)의 1,2-디아실-sn-글리세로-3-포스포클린 및 1,2-디아실-sn-글리세로-3-포스포에탄올아민을 제조하는 방법.상기식에서, T는 비치환되거나 C1-C6-알킬, C1-C6-알콕시 또는 할로겐으로 일치환 또는 디치환된 트리페닐메틸 그룹으로, 라디칼 R1,R2및 R3는 동일하게 각기 메틸그룹이거나, 상이하게는 라디칼 R1,R2및 R3중 둘은 항상 수소이고 나머니 하나는 비치환되거나 C1-C6-알킬, C1-C6-알콕시 또는 할로겐으로 일치환 또는 디치환된 트리페닐메틸 그룹이고 R1′,R2′ 및 R3′는 동일하며 동일하며 각 경우에 있어서 모두 수소원자이거나 모두 메틸그룹이고 R4및 R5는 상이하며 서로 독립적으로 직쇄 또는 측쇄 C1-C24-알칼이거나, 할로겐 또는 알콕시로일치환 또는 디치환되거나 비치환된 직쇄 또는 측색의 모노불포화된 또는 풀리불포화된 C2-C24-알케닐 라디칼이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ATA1590/84 | 1984-05-15 | ||
| AT0159084A AT383130B (de) | 1984-05-15 | 1984-05-15 | Verfahren zur herstellung von an c1 und c2 verschieden substituierten phosphatidylcholinen und phosphatidylethanolaminen ueber die neuen verbindungen 1-0-tritylglycerophosphocholin beziehungsweise (1-0,n-ditrityl)-glycerophosphoethanolamin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850008677A true KR850008677A (ko) | 1985-12-21 |
| KR920009556B1 KR920009556B1 (ko) | 1992-10-19 |
Family
ID=3516711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019850003277A KR920009556B1 (ko) | 1984-05-15 | 1985-05-14 | 글리세로포스포콜린 및 글리세로포스포에탄올 아민유도체의 제조방법 |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US4622180A (ko) |
| EP (1) | EP0161519B1 (ko) |
| JP (1) | JPS60252490A (ko) |
| KR (1) | KR920009556B1 (ko) |
| CN (1) | CN1014791B (ko) |
| AT (2) | AT383130B (ko) |
| AU (1) | AU565316B2 (ko) |
| BR (1) | BR8502293A (ko) |
| CA (1) | CA1244462A (ko) |
| DD (2) | DD233130A1 (ko) |
| DE (1) | DE3563533D1 (ko) |
| DK (2) | DK167441C (ko) |
| ES (2) | ES8603900A1 (ko) |
| FI (1) | FI77663C (ko) |
| HU (2) | HU199486B (ko) |
| IE (1) | IE58511B1 (ko) |
| IL (1) | IL75133A (ko) |
| NO (1) | NO163100C (ko) |
| NZ (1) | NZ212067A (ko) |
| PH (2) | PH21831A (ko) |
| SU (2) | SU1400511A3 (ko) |
| TR (1) | TR22204A (ko) |
| YU (2) | YU45720B (ko) |
| ZA (1) | ZA853697B (ko) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT383130B (de) * | 1984-05-15 | 1987-05-25 | Chemie Linz Ag | Verfahren zur herstellung von an c1 und c2 verschieden substituierten phosphatidylcholinen und phosphatidylethanolaminen ueber die neuen verbindungen 1-0-tritylglycerophosphocholin beziehungsweise (1-0,n-ditrityl)-glycerophosphoethanolamin |
| DE3638687A1 (de) * | 1986-11-13 | 1988-05-19 | Lentia Gmbh | Einstufiges verfahren zur herstellung von gemischt substituierten 1,2-di-acyl-sn-glycero-3-phosphocholinen |
| AT388165B (de) * | 1986-12-10 | 1989-05-10 | Chemie Linz Ag | Einstufiges verfahren zur herstellung von gemischt substituierten 1,2-di-acyl-sn-glycero-3- phosphocholinen |
| JP2657486B2 (ja) * | 1987-02-20 | 1997-09-24 | 花王株式会社 | 洗浄剤組成物 |
| US5144045A (en) * | 1990-11-13 | 1992-09-01 | American Cyanamid Company | Phosphocholine derivative inhibitors of phospholipase A2 |
| US5698537A (en) * | 1996-06-18 | 1997-12-16 | Clarion Pharmaceuticals Inc. | Method of lowering the viscosity of mucus |
| US6838452B2 (en) | 2000-11-24 | 2005-01-04 | Vascular Biogenics Ltd. | Methods employing and compositions containing defined oxidized phospholipids for prevention and treatment of atherosclerosis |
| WO2005018632A1 (en) * | 2003-08-18 | 2005-03-03 | Btg International Limited | Treatment of neurodegenerative conditions |
| US7807847B2 (en) | 2004-07-09 | 2010-10-05 | Vascular Biogenics Ltd. | Process for the preparation of oxidized phospholipids |
| GB0425932D0 (en) * | 2004-11-25 | 2004-12-29 | Btg Int Ltd | Structured phospholipids |
| GB0504362D0 (en) | 2005-03-02 | 2005-04-06 | Btg Int Ltd | Cytokine modulators |
| US8569529B2 (en) | 2007-01-09 | 2013-10-29 | Vascular Biogenics Ltd. | High-purity phospholipids |
| US9006217B2 (en) | 2007-01-09 | 2015-04-14 | Vascular Biogenics Ltd. | High-purity phospholipids |
| CN102271517B (zh) * | 2008-11-06 | 2015-04-08 | 脉管生物生长有限公司 | 氧化的脂质化合物和其用途 |
| CN104017019A (zh) * | 2014-06-12 | 2014-09-03 | 东南大学 | 一种氮芥-甘油磷脂酰胆碱化合物的合成方法 |
| ES2855299T3 (es) | 2014-11-26 | 2021-09-23 | Vascular Biogenics Ltd | Lípidos oxidados y tratamiento o prevención de la fibrosis |
| US9771385B2 (en) | 2014-11-26 | 2017-09-26 | Vascular Biogenics Ltd. | Oxidized lipids |
| CZ308596B6 (cs) * | 2017-04-03 | 2020-12-23 | Ústav molekulární genetiky AV ČR, v. v. i. | Deriváty fosfolipidů a jejich použití jako léčiva |
| PL232298B1 (pl) * | 2017-06-30 | 2019-06-28 | Univ Przyrodniczy We Wroclawiu | Sposób otrzymywania fosfatydylocholiny zawierającej ibuprofen w pozycji sn-1 |
| PL232663B1 (pl) * | 2017-06-30 | 2019-07-31 | Univ Przyrodniczy We Wroclawiu | Fosfatydylocholiny oraz sposób ich otrzymywania |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2820893C2 (de) * | 1978-05-12 | 1986-02-20 | A. Nattermann & Cie GmbH, 5000 Köln | Strukturanaloga von natürlichen Phospholipiden und Verfahren zur Herstellung dieser Verbindungen |
| IT1123187B (it) * | 1979-09-17 | 1986-04-30 | Lpb Ist Farm | Processo per la preparazione di l-alfa-glicerilfosforilcolina |
| DE3130867A1 (de) * | 1981-08-04 | 1983-02-24 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V., 3400 Göttingen | Zwischenprodukte zur herstellung von glycerinderivaten |
| AT383130B (de) * | 1984-05-15 | 1987-05-25 | Chemie Linz Ag | Verfahren zur herstellung von an c1 und c2 verschieden substituierten phosphatidylcholinen und phosphatidylethanolaminen ueber die neuen verbindungen 1-0-tritylglycerophosphocholin beziehungsweise (1-0,n-ditrityl)-glycerophosphoethanolamin |
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1984
- 1984-05-15 AT AT0159084A patent/AT383130B/de not_active IP Right Cessation
-
1985
- 1985-04-19 EP EP85104662A patent/EP0161519B1/de not_active Expired
- 1985-04-19 AT AT85104662T patent/ATE35416T1/de not_active IP Right Cessation
- 1985-04-19 DE DE8585104662T patent/DE3563533D1/de not_active Expired
- 1985-05-07 FI FI851781A patent/FI77663C/fi not_active IP Right Cessation
- 1985-05-07 IE IE113685A patent/IE58511B1/en not_active IP Right Cessation
- 1985-05-08 IL IL75133A patent/IL75133A/xx unknown
- 1985-05-09 CA CA000481204A patent/CA1244462A/en not_active Expired
- 1985-05-13 US US06/733,619 patent/US4622180A/en not_active Expired - Lifetime
- 1985-05-13 PH PH32256A patent/PH21831A/en unknown
- 1985-05-14 HU HU851813A patent/HU199486B/hu not_active IP Right Cessation
- 1985-05-14 SU SU853896546A patent/SU1400511A3/ru active
- 1985-05-14 SU SU853898601A patent/SU1422999A3/ru active
- 1985-05-14 NZ NZ212067A patent/NZ212067A/xx unknown
- 1985-05-14 AU AU42448/85A patent/AU565316B2/en not_active Ceased
- 1985-05-14 HU HU895132A patent/HU203555B/hu not_active IP Right Cessation
- 1985-05-14 KR KR1019850003277A patent/KR920009556B1/ko not_active IP Right Cessation
- 1985-05-14 ES ES543147A patent/ES8603900A1/es not_active Expired
- 1985-05-14 DD DD85276324A patent/DD233130A1/de not_active IP Right Cessation
- 1985-05-14 DD DD85276325A patent/DD245668A1/de not_active IP Right Cessation
- 1985-05-14 NO NO851928A patent/NO163100C/no unknown
- 1985-05-14 ES ES543146A patent/ES8603899A1/es not_active Expired
- 1985-05-14 DK DK212185A patent/DK167441C/da not_active IP Right Cessation
- 1985-05-15 TR TR22204A patent/TR22204A/xx unknown
- 1985-05-15 YU YU81685A patent/YU45720B/sh unknown
- 1985-05-15 BR BR8502293A patent/BR8502293A/pt not_active IP Right Cessation
- 1985-05-15 ZA ZA853697A patent/ZA853697B/xx unknown
- 1985-05-15 JP JP60101644A patent/JPS60252490A/ja active Granted
- 1985-05-15 YU YU81585A patent/YU45719B/sh unknown
- 1985-06-11 CN CN85104463A patent/CN1014791B/zh not_active Expired
-
1986
- 1986-07-29 US US06/891,515 patent/US4717512A/en not_active Expired - Lifetime
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1987
- 1987-07-06 PH PH35499A patent/PH23978A/en unknown
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1992
- 1992-08-03 DK DK92981A patent/DK98192D0/da not_active Application Discontinuation
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