KR960034146A - 치환된 디플루오로메틸기를 하나 이상의 친전자 작용체를 함유하는 화합물상에 그라프팅하기 위한 시약 및 방법 - Google Patents
치환된 디플루오로메틸기를 하나 이상의 친전자 작용체를 함유하는 화합물상에 그라프팅하기 위한 시약 및 방법 Download PDFInfo
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- KR960034146A KR960034146A KR1019960008042A KR19960008042A KR960034146A KR 960034146 A KR960034146 A KR 960034146A KR 1019960008042 A KR1019960008042 A KR 1019960008042A KR 19960008042 A KR19960008042 A KR 19960008042A KR 960034146 A KR960034146 A KR 960034146A
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- 150000001875 compounds Chemical class 0.000 title claims abstract 22
- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract 20
- 238000000034 method Methods 0.000 title claims abstract 9
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 title claims abstract 3
- 239000002253 acid Substances 0.000 claims abstract 14
- 239000003880 polar aprotic solvent Substances 0.000 claims abstract 4
- 238000010438 heat treatment Methods 0.000 claims abstract 3
- 150000001767 cationic compounds Chemical class 0.000 claims abstract 2
- 239000012535 impurity Substances 0.000 claims abstract 2
- 229910001411 inorganic cation Inorganic materials 0.000 claims abstract 2
- -1 alkali metal salt Chemical class 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims 2
- 150000001299 aldehydes Chemical class 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- 150000002898 organic sulfur compounds Chemical class 0.000 claims 2
- 150000003461 sulfonyl halides Chemical class 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 150000003983 crown ethers Chemical class 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000006575 electron-withdrawing group Chemical group 0.000 claims 1
- 229910052730 francium Inorganic materials 0.000 claims 1
- KLMCZVJOEAUDNE-UHFFFAOYSA-N francium atom Chemical compound [Fr] KLMCZVJOEAUDNE-UHFFFAOYSA-N 0.000 claims 1
- 150000003951 lactams Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000002825 nitriles Chemical group 0.000 claims 1
- 239000012434 nucleophilic reagent Substances 0.000 claims 1
- 150000002892 organic cations Chemical class 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- 229910052701 rubidium Inorganic materials 0.000 claims 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010189 synthetic method Methods 0.000 abstract 1
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
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- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
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- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
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- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
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- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
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Abstract
본 발명은 하기 a)~b)로 구성되며, 불순물을 포함하여 다양한 성분들에 의해 운반되는 방출가능한 프로톤의 함량이 상기 플루오로카르복시산의 초기 몰농도의 절반 이하임을 특징으로 하는, 치환된 디플루오로메틸기를 하나 이상의 친전자 작용체를 함유하는 화합물 상에 그라프팅하는데 유용한 친핵 시약에 관한 것이다 : a) Ew가 유기 또는 무기 양이온으로써 적어도 부분적으로 염화된, 전자-끄는 원자 또는 기를 나타내는 식 Ew-CF2-COOH의 플루오로카르복시산, 및 b) 극성 비프로톤성 용매.
합성 방법은 치환된 디플루오로메틸기를 다양한 화합물 상에 가열에 의해 이 시약을 사용하여 그라프팅한다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (24)
- 하기 a)~b)로 구성되며, 불순물을 포함하여 다양한 성분들에 의해 운반되는 방출가능한 프로톤의 함량이 상기 플루오로카르복시산의 초기 몰농도의 절반 이하임을 특징으로 하는, 치환된 디플루오로메틸기를 하나 이상의 친전자 작용체를 함유하는 화합물 상에 그라프팅하는데 유용한 친핵성 시약 : a) Ew가 유기 또는 무기 양이온으로써 적어도 부분적으로 염화된, 전자-끄는 원자 또는 기를 나타내는 식 Ew-CF2-COOH의 플루오로카르복시산, 및 b) 극성 비프로톤성 용매.
- 제1항에 있어서, 상기 극성 비프로톤 용매가 하나 이상의 친전자 적용체를 함유함을 특징으로 하는 시약.
- 제1항에 있어서, 상기 프로톤 함량이 상기 플루오로카르복시산 염의 초기 몰농도의 10% 이하임을 특징으로 하는 시약.
- 제1항에 있어서, 물 함량이 상기 플루오로카르복시산 염의 몰농도의 10% 이하임을 특징으로 하는 시약.
- 제1항에 있어서, 안정한 2 이상의 원자가 상태를 갖는 전이 원소의 함량이 상기 플루오로카르복시산에 대하여 1000몰 ppm 이하임을 특징으로 하는 시약.
- 제1항에 있어서, 원소 주기율표의 Ⅷ족으로부터의 원소 함량이 상기 플루오로카르복시산 염에 대하여 100몰 ppm 이하임을 특징으로 하는 시약.
- 제1항에 있어서, 당량으로 표현된 이온성 불화물의 함량이 상기 플루오로카르복시산 염의 초기 몰농도 이하임을 특징으로 하는 시약.
- 제1항에 있어서, 상기 극성 비프로톤성 용매의 공여체수가 10~30임을 특징으로 하는 시약.
- 제1항에 있어서, 상기 용매의 수용체수가 20 이하임을 특징으로 하는 시약.
- 제1항에 있어서, 상기 용매의 제1산도에 사용하는 pKa가 20 이상임을 특징으로 하는 시약.
- 제1항에 있어서, 봉쇄 크라운 에테르를 함유함을 특징으로 하는 시약.
- 제1항에 있어서, 상기 전자-끄는 원자 또는 기가 하메트 상수 σp가 1이상인 전자-끄는 기로부터 선택됨을 특징으로 하는 시약.
- 제1항에 있어서, 상기 산이 식 (1) X-CF2COOH(식중, X는 할로겐 원자)의 화합물, 및 식 (2) R-G-CF2-COOH(식중, R-G는 니트릴기를 나타내거나 대안적으로 G는 〉C=0, 〉S=0 또는 -(CF2)n- (식중, n은 1 이상임)이고 R은 차별없이 유기 또는 무기 잔기를 나타냄)의 화합물로부터 선택됨을 특징으로 하는 시약.
- 제1항에 있어서, 상기 플루오로카르복시산 또는 산 염이 시약 매질내에 완전히 용해됨을 특징으로 하는 시약.
- 제1항에 있어서, 상기 산 염이 나트륨, 칼륨, 루비듐, 카에슘 및 프란슘으로부터 선택된 알카리 금속염 또는 4차 암모늄 염임을 특징으로 하는 시약.
- 제1항에 있어서, 용매는 사치환된 우레아를 및 일치환된 락탐을 포함하는 N-이치환 아미드, 고리형 또는 비고리형 에테르, 및 벤조니트릴로부터 선택됨을 특징으로 하는 시약.
- 하기의 단계들을 포함함을 특징으로 하는, 디플루오로메틸렌기를 함유하는 유기 유도체의 합성방법 : a) 제1~14항 중 한 항에 따른 시약을 하나 이상의 친전자 작용체를 함유하는 화합물과 함께 놓는 단계. 및 b) 100~200℃ 온도로 1/2시간 및 하루 미만의 기간 동안 상기 생성된 혼합물을 가열 하는 단계.
- 제2항에 따른 시약을 100~200℃로 1/2시간~하루 동안 가열시키는 단계를 포함함을 특징으로 하는 , 디플루오로메틸렌 기를 함유하는 유도체의 합성방법.
- 제17항에 있어서, 친전자 작용제를 함유하는 상기 화합물이 유기황 화합물의 할로 또는 유사할로 유도체; 디설파이드; 티오시안산염; 및 카르보닐화 화합물로부터 선택됨을 특징으로 하는 방법.
- 제17항에 있어서, 상기 화합물이, 강염기에 의해 제거될 수 있는 임의의 수소를 함유하지 않는 하나 이상의 친전자 작용체를 함유함을 특징으로 하는 방법.
- 제19항에 있어서, 친전자 작용제를 함유하는 상기 화합물이 설페닐 할라이드, 설피닐 할라이드, 설포닐 할라이드, 케톤, 알데히드, 산 할라이드, 활성화된 에스테르 및 무수물로부터 선택됨을 특징으로 하는 방법.
- 제18항에 있어서, 친전자 작용체를 함유하는 상기 화합물이 유기황 화합물의 할로 또는 유사할로 유도체; 디설파이드; 티오시안산염; 및 카르보닐화 화합물로부터 선택됨을 특징으로 하는 방법.
- 제22항에 있어서, 친권자 작용체를 함유하는 상기 화합물이 설페닐 할라이드, 설피닐 할라이드, 설포닐 할라이드, 케톤, 알데히드, 산 할라이드, 활성화된 에스테르 및 무수물로부터 선택됨을 특징으로 하는 방법.
- 제19항에 있어서, 상기 화합물이 강 염기에 의해 제거될 수 있는 임의의 수소를 함유하지 않는 하나 이상의 친전자 작용체를 함유하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR95-03512 | 1995-03-24 | ||
| FR9503512A FR2732010B1 (fr) | 1995-03-24 | 1995-03-24 | Reactif et procede utiles pour greffer un groupement difluoromethyle substitue sur un compose comportant au moins une fonction electrophile |
| FR9515763A FR2743065B1 (fr) | 1995-12-29 | 1995-12-29 | Reactif et procede utiles pour greffer un groupement difluoromethyle substitue sur un compose comportant au moins une fonction electrophile |
| FR95-15763 | 1995-12-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR960034146A true KR960034146A (ko) | 1996-10-22 |
| KR100436787B1 KR100436787B1 (ko) | 2004-09-18 |
Family
ID=26231834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019960008042A KR100436787B1 (ko) | 1995-03-24 | 1996-03-23 | 치환된디플루오로메틸기를하나이상의친전자성작용기를함유하는화합물상에그라프팅하기위한시약및방법 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5756849A (ko) |
| EP (1) | EP0733614B2 (ko) |
| JP (1) | JP4450875B2 (ko) |
| KR (1) | KR100436787B1 (ko) |
| CN (1) | CN1150148C (ko) |
| AT (1) | ATE201393T1 (ko) |
| AU (1) | AU4822896A (ko) |
| BR (1) | BR9601109A (ko) |
| CA (1) | CA2172450A1 (ko) |
| CZ (1) | CZ85596A3 (ko) |
| DE (1) | DE69612899T3 (ko) |
| DK (1) | DK0733614T3 (ko) |
| ES (1) | ES2157407T5 (ko) |
| HU (1) | HU217027B (ko) |
| IL (1) | IL117534A0 (ko) |
| PL (1) | PL313435A1 (ko) |
| PT (1) | PT733614E (ko) |
| RO (1) | RO117911B1 (ko) |
| RU (1) | RU2204545C2 (ko) |
| SK (1) | SK37096A3 (ko) |
| TR (1) | TR199600234A1 (ko) |
| UA (1) | UA45324C2 (ko) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19824488A1 (de) * | 1998-06-02 | 1999-12-09 | Bayer Ag | Verfahren zur Herstellung von Perfluoralkyl-aryl-sulfiden und neue Perfluoralkyl-aryl-sulfide |
| US7385063B2 (en) | 2001-01-26 | 2008-06-10 | Chugai Seiyaku Kabushiki Kaisha | Method for preparing imidazole derivatives |
| DE60215139T2 (de) | 2001-01-26 | 2007-08-16 | Chugai Seiyaku K.K. | Malonyl coa-decarboxylase inhibitoren als stoffwechselmodulatoren |
| CA2735267C (en) | 2001-01-26 | 2013-05-07 | Chugai Seiyaku Kabushiki Kaisha | Malonyl-coa decarboxylase inhibitors useful as metabolic modulators |
| US7709510B2 (en) | 2001-02-20 | 2010-05-04 | Chugai Seiyaku Kabushiki Kaisha | Azoles as malonyl-CoA decarboxylase inhibitors useful as metabolic modulators |
| KR100659427B1 (ko) | 2001-02-20 | 2006-12-18 | 추가이 세이야쿠 가부시키가이샤 | 대사조절인자로서 유용한 말로닐-코에이 데카르복실라제억제제로서의 아졸류 |
| FR2827285B1 (fr) * | 2001-07-10 | 2003-12-05 | Rhodia Chimie Sa | Reactif et procede pour la perfluoroalcoylation |
| US6803477B2 (en) | 2001-11-29 | 2004-10-12 | University Of Southern California | Magnesium mediated preparation of fluorinated alkyl silanes |
| CA2533763C (en) | 2003-08-01 | 2012-11-20 | Chugai Seiyaku Kabushiki Kaisha | Cyanoamide compounds useful as malonyl-coa decarboxylase inhibitors |
| ES2309563T3 (es) | 2003-08-01 | 2008-12-16 | Chugai Seiyaku Kabushiki Kaisha | Compuestos de piperidina utiles como inhibidores de malonil coenzima a descarboxilasa. |
| CA2533747C (en) | 2003-08-01 | 2012-11-13 | Chugai Seiyaku Kabushiki Kaisha | Heterocyclic compounds useful as malonyl-coa decarboxylase inhibitors |
| DE602004016530D1 (de) | 2003-08-01 | 2008-10-23 | Chugai Pharmaceutical Co Ltd | Azol-verbindungen auf cyanoguanidin-basis als malonyl-coa decarboxylase-hemmer |
| US7710197B2 (en) * | 2007-07-11 | 2010-05-04 | Axiom Microdevices, Inc. | Low offset envelope detector and method of use |
| US11028105B2 (en) | 2018-06-29 | 2021-06-08 | The Regents Of The University Of Michigan | Difluoromethyl and difluoromethylene transfer reagents |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4822904A (en) * | 1985-12-12 | 1989-04-18 | Ethyl Corporation | Perfluoroalkylation process |
| US4808748A (en) * | 1985-12-12 | 1989-02-28 | Ethyl Corporation | Trifluoromethylation process |
| US4990699A (en) * | 1988-10-17 | 1991-02-05 | Ethyl Corporation | Perfluoroalkylation process |
-
1996
- 1996-03-18 IL IL11753496A patent/IL117534A0/xx unknown
- 1996-03-20 SK SK370-96A patent/SK37096A3/sk unknown
- 1996-03-21 AU AU48228/96A patent/AU4822896A/en not_active Abandoned
- 1996-03-21 CZ CZ96855A patent/CZ85596A3/cs unknown
- 1996-03-22 AT AT96400625T patent/ATE201393T1/de not_active IP Right Cessation
- 1996-03-22 UA UA96031110A patent/UA45324C2/uk unknown
- 1996-03-22 DK DK96400625T patent/DK0733614T3/da active
- 1996-03-22 US US08/620,348 patent/US5756849A/en not_active Expired - Lifetime
- 1996-03-22 HU HU9600724A patent/HU217027B/hu not_active IP Right Cessation
- 1996-03-22 ES ES96400625T patent/ES2157407T5/es not_active Expired - Lifetime
- 1996-03-22 RO RO96-00640A patent/RO117911B1/ro unknown
- 1996-03-22 EP EP96400625A patent/EP0733614B2/fr not_active Expired - Lifetime
- 1996-03-22 CA CA002172450A patent/CA2172450A1/fr not_active Abandoned
- 1996-03-22 TR TR96/00234A patent/TR199600234A1/xx unknown
- 1996-03-22 DE DE69612899T patent/DE69612899T3/de not_active Expired - Lifetime
- 1996-03-22 BR BR9601109A patent/BR9601109A/pt not_active Application Discontinuation
- 1996-03-22 RU RU96105817/04A patent/RU2204545C2/ru not_active IP Right Cessation
- 1996-03-22 PT PT96400625T patent/PT733614E/pt unknown
- 1996-03-22 PL PL96313435A patent/PL313435A1/xx unknown
- 1996-03-22 CN CNB961057556A patent/CN1150148C/zh not_active Expired - Lifetime
- 1996-03-23 KR KR1019960008042A patent/KR100436787B1/ko not_active IP Right Cessation
- 1996-03-25 JP JP09296096A patent/JP4450875B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69612899D1 (de) | 2001-06-28 |
| HU217027B (hu) | 1999-11-29 |
| HUP9600724A1 (en) | 1997-04-28 |
| AU4822896A (en) | 1996-10-03 |
| RO117911B1 (ro) | 2002-09-30 |
| IL117534A0 (en) | 1996-07-23 |
| JPH08319251A (ja) | 1996-12-03 |
| CA2172450A1 (fr) | 1996-09-25 |
| SK37096A3 (en) | 1997-07-09 |
| HU9600724D0 (en) | 1996-05-28 |
| MX9601075A (es) | 1997-07-31 |
| PL313435A1 (en) | 1996-09-30 |
| EP0733614A1 (fr) | 1996-09-25 |
| EP0733614B2 (fr) | 2010-01-13 |
| PT733614E (pt) | 2001-08-30 |
| KR100436787B1 (ko) | 2004-09-18 |
| US5756849A (en) | 1998-05-26 |
| ES2157407T3 (es) | 2001-08-16 |
| DK0733614T3 (da) | 2001-09-10 |
| TR199600234A1 (tr) | 1997-03-21 |
| DE69612899T2 (de) | 2001-10-11 |
| ATE201393T1 (de) | 2001-06-15 |
| JP4450875B2 (ja) | 2010-04-14 |
| UA45324C2 (uk) | 2002-04-15 |
| CN1150148C (zh) | 2004-05-19 |
| EP0733614B1 (fr) | 2001-05-23 |
| CZ85596A3 (en) | 1996-10-16 |
| RU2204545C2 (ru) | 2003-05-20 |
| BR9601109A (pt) | 1998-01-06 |
| DE69612899T3 (de) | 2010-06-10 |
| ES2157407T5 (es) | 2010-04-20 |
| CN1137508A (zh) | 1996-12-11 |
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