KR970704716A - 사카린카르복실산 및 사카린카르복실산 에스테르의 제조(Preparation of Saccharincarboxylic Acids and Saccharincarboxylic Acid Esters) - Google Patents
사카린카르복실산 및 사카린카르복실산 에스테르의 제조(Preparation of Saccharincarboxylic Acids and Saccharincarboxylic Acid Esters) Download PDFInfo
- Publication number
- KR970704716A KR970704716A KR1019970700833A KR19970700833A KR970704716A KR 970704716 A KR970704716 A KR 970704716A KR 1019970700833 A KR1019970700833 A KR 1019970700833A KR 19970700833 A KR19970700833 A KR 19970700833A KR 970704716 A KR970704716 A KR 970704716A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- carboxylic acid
- hydrogen
- formula
- saccharin
- Prior art date
Links
- -1 Saccharin Carboxylic Acid Chemical class 0.000 title claims abstract 16
- 229940081974 saccharin Drugs 0.000 title claims abstract 10
- 235000019204 saccharin Nutrition 0.000 title claims abstract 10
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 title claims abstract 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 14
- 239000001257 hydrogen Substances 0.000 claims abstract 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract 4
- 239000003054 catalyst Substances 0.000 claims abstract 4
- 239000000460 chlorine Substances 0.000 claims abstract 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 4
- 229910052763 palladium Inorganic materials 0.000 claims abstract 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 2
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract 2
- 229910017052 cobalt Inorganic materials 0.000 claims abstract 2
- 239000010941 cobalt Substances 0.000 claims abstract 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 229910052759 nickel Inorganic materials 0.000 claims abstract 2
- 229910052703 rhodium Inorganic materials 0.000 claims abstract 2
- 239000010948 rhodium Substances 0.000 claims abstract 2
- 229910052723 transition metal Inorganic materials 0.000 claims abstract 2
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 4
- 239000002585 base Substances 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 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
- 230000021523 carboxylation Effects 0.000 claims 2
- 238000006473 carboxylation reaction Methods 0.000 claims 2
- 230000002363 herbicidal effect Effects 0.000 claims 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims 1
- CEJDLTNRMCYNBU-UHFFFAOYSA-N 4-chloro-1,1,3-trioxo-1,2-benzothiazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2S(=O)(=O)NC(=O)C2=C1Cl CEJDLTNRMCYNBU-UHFFFAOYSA-N 0.000 claims 1
- PCVAKZGUOLVXKS-UHFFFAOYSA-N 7-methyl-1,1,3-trioxo-1,2-benzothiazole-5-carboxylic acid Chemical compound CC1=CC(C(O)=O)=CC2=C1S(=O)(=O)NC2=O PCVAKZGUOLVXKS-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 238000005810 carbonylation reaction Methods 0.000 claims 1
- 229940125890 compound Ia Drugs 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229940054334 silver cation Drugs 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- 150000003754 zirconium Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 abstract 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical class C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B41/00—Formation or introduction of functional groups containing oxygen
- C07B41/08—Formation or introduction of functional groups containing oxygen of carboxyl groups or salts, halides or anhydrides thereof
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
하기 화학식(Ⅰ)의 사카린 카르복실산 및 사카린 카르복실산 에스테르는, 하기 화학식(Ⅱ)의 상응하는 브로모-또는 요오도-치환 사카린 유도체, 또는 ZH인 경우에는 하기 화학식(Ⅲ)의 화합물을 승압하에서 팔라듐, 니켈, 코발트 또는 로듐 전이금속 촉매 및 염기의 존재하에 일산화탄소 및 물 또는 C1-C6-알콜과 반응시킴으로써 제조된다.
상기 식 중, L 및 M은 수소, 알킬, 알콕시, 알킬티오, 염소, 시아노, 알킬술포닐, 니트로 또는 트리폴루오로메틸이고; Z는 수소, 알킬, 시클로알킬, 아릴 또는 아랄킬이고; R은 H 또는 C1-C6-알킬이다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (11)
- 하기 화학식(Ⅱ)의 상응하는 브로모-또는 요오도-치환 사카린 유도체, 또는 ZH인 경우에는 하기 화학식(Ⅲ)의 화합물을 승압하에서 팔라듐, 니켈, 코발트 또는 로듐 전이금속 촉매 및 염기의 존재하에 일산화탄소 및 물 또는 C1-C6-알콜과 반응시키는 것으로 이루어진 하기 화학식(Ⅰ)의 사카린 카르복실산과 사카린 카르복실산 에스테르의 제조 방법.상기 식 중, L 및 M은 수소, 알킬, 알콕시, 알킬티오, 염소, 시아노, 알킬술포닐, 니트로 또는 트리폴루오로메틸이고; Z는 수소, 알킬, 시클로알킬, 아릴 또는 아랄킬이고; R은 H 또는 C1-C6-알킬이다.
- 제1항에 있어서, 카르보닐화 반응에 통상 사용되는 팔라듐 촉매가 사용되는 방법.
- 제1항에 있어서, 카르복실화가 3차 포스핀들로부터의 포스핀 리간드를 함유하는 팔라듐 촉매의 존재하에서 수행되는 방법.
- 제1항에 있어서, 사용된 염기가 3차 아민 또는 테트라알킬-치환 우레아 유도체인 방법.
- 제1항에 있어서, 사용된 염기가 테트라메틸우레아인 방법.
- 제1항 또는 제5항에 있어서, 염기가 동시에 용매로서 사용되는 방법.
- 제1항에 있어서, 반응 성분인 물 또는 알콜이 동시에 용매로서 사용되는 방법.
- 제1항에 있어서, 카르복실화가 20 내지 200℃에서 수행되는 방법.
- 하기의 화학식(Ia)의 사카린 카르복실산 또는 사카린 카르복실산 에스테르.상기 식 중, L 및 M은 수소, C1-C4-알킬, C1-C4-알콕시, C1-C4-알킬티오, 염소, 시아노, 메틸술포닐, 니트로 또는 트리플루오로메틸이고; Z는 수소, C1-C4-알킬, C3-C8-시클로알킬, 벤질, 또는 비치환 또는 C1-C4-알킬로 치환된 페닐이고; R은 H 또는 C1-C6-알킬이며, 단, L 및 M이 수소일 때, Z는 메틸, 페닐, 수소 또는 알칼리금속 또는 은 양이온이 아니며, 5-카르복시-7-메틸사카린 및 5-카르복시-4-클로로사카린은 이 화합물에서 제외된다.
- 제9항에 따른 화합물 Ia 및 통상적인 불활성 담체를 함유하는 제초제 조성물.
- 제초제 활성량의 하기 화학식(Ia′)의 사카린 카르복실산 또는 사카린 카르복실산 에스테르 또는 화합물(Ia′)의 환경적으로 허용 가능한 염을 식물이나 그들의 서식지에 작용하게 하는 것으로 이루어진, 원하지 않은 식물 생장을 억제하는 방법.상기 식 중, L 및 M은 수소, C1-C4-알킬, C1-C4-알콕시, C1-C4-알킬티오, 염소, 시아노, 메틸술포닐, 니트로 또는 트리플루오로메틸이고; Z는 수소, C1-C4-알킬, C3-C8-시클로알킬, 벤질, 또는 비치환 또는 C1-C4-알킬로 치환된 페닐이고; R은 H 또는 C1-C6-알킬이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4427996.5 | 1994-08-08 | ||
| DE4427996A DE4427996A1 (de) | 1994-08-08 | 1994-08-08 | Verfahren zur Herstellung von Saccharincarbonsäuren und -carbonsäureestern |
| PCT/EP1995/003022 WO1996005184A1 (de) | 1994-08-08 | 1995-07-29 | Herbizide saccharincarbonsäure-derivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR970704716A true KR970704716A (ko) | 1997-09-06 |
Family
ID=6525160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019970700833A KR970704716A (ko) | 1994-08-08 | 1995-07-29 | 사카린카르복실산 및 사카린카르복실산 에스테르의 제조(Preparation of Saccharincarboxylic Acids and Saccharincarboxylic Acid Esters) |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5863864A (ko) |
| EP (1) | EP0775124B1 (ko) |
| JP (1) | JPH10503776A (ko) |
| KR (1) | KR970704716A (ko) |
| CN (1) | CN1059207C (ko) |
| AT (1) | ATE205840T1 (ko) |
| AU (1) | AU688562B2 (ko) |
| BR (1) | BR9508551A (ko) |
| CA (1) | CA2197120A1 (ko) |
| DE (2) | DE4427996A1 (ko) |
| ES (1) | ES2164775T3 (ko) |
| HU (1) | HU216290B (ko) |
| MX (1) | MX9700938A (ko) |
| RU (1) | RU2154640C2 (ko) |
| TW (1) | TW294664B (ko) |
| WO (1) | WO1996005184A1 (ko) |
| ZA (1) | ZA956576B (ko) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4427995A1 (de) * | 1994-08-08 | 1996-02-15 | Basf Ag | Saccharinderivate |
| JP2001514635A (ja) * | 1997-03-10 | 2001-09-11 | ビーエーエスエフ アクチェンゲゼルシャフト | サッカリン−５−カルボニルシクロヘキサン−１，３，５−トリオン誘導体 |
| US6605751B1 (en) * | 1997-11-14 | 2003-08-12 | Acrymed | Silver-containing compositions, devices and methods for making |
| EP0945449B1 (de) * | 1998-03-25 | 2001-05-23 | Basf Aktiengesellschaft | Verfahren zur Herstellung von Saccharincarbonsäurehalogeniden |
| WO2001049258A2 (en) * | 1999-12-30 | 2001-07-12 | Acrymed | Methods and compositions for improved delivery devices |
| US8486426B2 (en) | 2002-07-29 | 2013-07-16 | Kimberly-Clark Worldwide, Inc. | Methods and compositions for treatment of dermal conditions |
| CN102783499A (zh) | 2004-07-30 | 2012-11-21 | 金伯利-克拉克环球有限公司 | 抗微生物的装置和组合物 |
| US8361553B2 (en) | 2004-07-30 | 2013-01-29 | Kimberly-Clark Worldwide, Inc. | Methods and compositions for metal nanoparticle treated surfaces |
| AU2005280443B2 (en) * | 2004-07-30 | 2011-02-03 | Avent, Inc. | Antimicrobial silver compositions |
| US9289378B2 (en) * | 2004-09-20 | 2016-03-22 | Avent, Inc. | Antimicrobial amorphous compositions |
| EP2015722B1 (en) * | 2006-04-28 | 2016-11-16 | Avent, Inc. | Antimicrobial site dressings |
| CA2743774C (en) * | 2008-11-24 | 2017-11-28 | Kimberly-Clark Worldwide, Inc. | Antimicrobial laminate constructs |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE671788C (de) * | 1935-04-20 | 1939-02-15 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von Diazoaminoverbindungen |
| US3673200A (en) * | 1970-01-02 | 1972-06-27 | Monsanto Co | 3(2-sec-butyl-4,6-dimitrophenoxy)-1,2-benzisothiozole 1,1-dioxide |
| US4410353A (en) * | 1981-07-17 | 1983-10-18 | Rhone-Poulenc Agrochimie | Herbicidal N-sulfonyl 5-[substituted phenoxy]-2-substituted benzamides |
| FR2525593A1 (fr) * | 1982-04-23 | 1983-10-28 | Rhone Poulenc Agrochimie | Derives d'acides phenoxybenzoiques, leur preparation et leur utilisation pour le desherbage des cultures |
| DE3430805A1 (de) * | 1984-03-08 | 1985-09-19 | Bayer Ag, 5090 Leverkusen | Mikrobizide mittel |
| DE3607343A1 (de) * | 1985-03-19 | 1986-09-25 | Dr. Karl Thomae Gmbh, 88400 Biberach | Verfahren zur herstellung von 4-hydroxy-1,2-benzisothiazol-3(2h)-on-1,1-dioxid und seinen salzen |
| EP0308371A1 (de) * | 1987-09-18 | 1989-03-22 | Ciba-Geigy Ag | 4-Azasaccharine, 4-Aza-dihydro-oder-tetrahydrosaccharine und Verfahren zu deren Herstellung |
| EP0323869A1 (en) * | 1988-01-06 | 1989-07-12 | Shell Internationale Researchmaatschappij B.V. | Saccharin derivatives |
| WO1989010921A1 (en) * | 1988-05-12 | 1989-11-16 | E.I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US5034534A (en) * | 1988-07-15 | 1991-07-23 | E. I. Du Pont De Nemours And Company | Process for producing saccharin, saccharin analogues or their salts |
| DK0471756T3 (da) * | 1989-05-04 | 1998-05-18 | Sanofi Sa | Saccharinderivater, der er egnede som proteolytiske enzyminhibitorer, og fremstilling deraf |
| US5236917A (en) * | 1989-05-04 | 1993-08-17 | Sterling Winthrop Inc. | Saccharin derivatives useful as proteolytic enzyme inhibitors and compositions and method of use thereof |
| AU642537B2 (en) * | 1990-11-01 | 1993-10-21 | Sanofi | 2-saccharinylmethyl aryl carboxylates useful as proteolytic enzyme inhibitors and compositions and method of use thereof |
-
1994
- 1994-08-08 DE DE4427996A patent/DE4427996A1/de not_active Withdrawn
-
1995
- 1995-07-29 CN CN95195020A patent/CN1059207C/zh not_active Expired - Fee Related
- 1995-07-29 DE DE59509621T patent/DE59509621D1/de not_active Expired - Lifetime
- 1995-07-29 CA CA002197120A patent/CA2197120A1/en not_active Abandoned
- 1995-07-29 ES ES95928489T patent/ES2164775T3/es not_active Expired - Lifetime
- 1995-07-29 WO PCT/EP1995/003022 patent/WO1996005184A1/de active IP Right Grant
- 1995-07-29 RU RU97103532/04A patent/RU2154640C2/ru not_active IP Right Cessation
- 1995-07-29 EP EP95928489A patent/EP0775124B1/de not_active Expired - Lifetime
- 1995-07-29 HU HU9700383A patent/HU216290B/hu not_active IP Right Cessation
- 1995-07-29 KR KR1019970700833A patent/KR970704716A/ko active IP Right Grant
- 1995-07-29 US US08/776,567 patent/US5863864A/en not_active Expired - Fee Related
- 1995-07-29 BR BR9508551A patent/BR9508551A/pt not_active IP Right Cessation
- 1995-07-29 AU AU32231/95A patent/AU688562B2/en not_active Ceased
- 1995-07-29 AT AT95928489T patent/ATE205840T1/de not_active IP Right Cessation
- 1995-07-29 MX MX9700938A patent/MX9700938A/es not_active IP Right Cessation
- 1995-07-29 JP JP8506963A patent/JPH10503776A/ja active Pending
- 1995-08-07 ZA ZA9506576A patent/ZA956576B/xx unknown
- 1995-08-07 TW TW084108198A patent/TW294664B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| HUT77182A (hu) | 1998-03-02 |
| CA2197120A1 (en) | 1996-02-22 |
| EP0775124B1 (de) | 2001-09-19 |
| AU688562B2 (en) | 1998-03-12 |
| WO1996005184A1 (de) | 1996-02-22 |
| BR9508551A (pt) | 1997-10-28 |
| DE59509621D1 (de) | 2001-10-25 |
| ZA956576B (en) | 1997-02-07 |
| CN1159189A (zh) | 1997-09-10 |
| RU2154640C2 (ru) | 2000-08-20 |
| AU3223195A (en) | 1996-03-07 |
| US5863864A (en) | 1999-01-26 |
| ES2164775T3 (es) | 2002-03-01 |
| MX9700938A (es) | 1997-04-30 |
| HU216290B (hu) | 1999-06-28 |
| ATE205840T1 (de) | 2001-10-15 |
| TW294664B (ko) | 1997-01-01 |
| CN1059207C (zh) | 2000-12-06 |
| JPH10503776A (ja) | 1998-04-07 |
| EP0775124A1 (de) | 1997-05-28 |
| DE4427996A1 (de) | 1996-02-15 |
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