KR890006215A - 킬레이트화제를 함유하는 광보호 조성물 - Google Patents
킬레이트화제를 함유하는 광보호 조성물 Download PDFInfo
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- KR890006215A KR890006215A KR1019880013864A KR880013864A KR890006215A KR 890006215 A KR890006215 A KR 890006215A KR 1019880013864 A KR1019880013864 A KR 1019880013864A KR 880013864 A KR880013864 A KR 880013864A KR 890006215 A KR890006215 A KR 890006215A
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Abstract
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Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (12)
- (a)시험관내 용액 라디칼 분석에서 철-촉매화된 하이드록실 라디칼 형성을 적어도 50% 억제시키는, 안전한 광 보호적 유효량의, 바람직하게는 1% 내지 10%의 킬레이트화제; 및 (b) 안전한 유효량의 국소용 담체를 함유함을 특징으로하는 국소 적용용 광보호 조성물.
- (a) 마우스 피부 주름형성 생체시험에서 피부 주름 등급을 적어도 20% 감소시키는, 안전한 광보호적 유효량의 바람직하게는 1% 내지 10%의 킬레이트화제; 및 (b) 안전한 유효량의 국소용 담체를 함유함을 특징으로 하는 국소 적용용 광보호 조성물.
- 제1항 또는 제2항에 있어서, 킬레이트화제가 (a) 2-2'-디피리딜아민;1,10-페난트롤린;디-2-피리딜켄톤;2,3비스(2-피리딜)피라진;2,3-비스(2-피리딜)5,6-디하이드로피라진;1,1'-카보닐디이미다졸;2,4-비스(5,6)디페닐01,2,4-트리아진-3-일)피리딘;2,4,6-트리(2-피리딜)-1,3,5-트리아진;4,4'-디메틸-2,2'-디피리딜;2,2'-비퀴놀린;디-2-피리딜 글리옥살;2-(2-피리딜)벤즈이미다졸;2,2'-비피라진;3-(2-피리딜)5,6-디메틸-1,2,4-트리아진;3-)4-페닐-2-피리딜)-5-페닐-1,2,4-트리아진;3-(4-페닐-2-피리딜)-5,6-디메틸-1,2,4-트리아진;2,3,5,6-테트라키스-(2'-피리딜)-피라진;2,6-피리딘디카복실산;2,4,5-트리하이드록시피리딘;페닐 2-피리딜 케톡심;3-아미노-5,6-디메틸-1,2,4-트리아진;6-하이드록시-2-페닐-3(2H)-피리다지논;2,4-테리딘디올;2,2-디피리딜;2,3-디하이드록시 피리딘;및 5,7-디클로로-8-하이드록시퀴놀린;및 이의 유사체, 동족체 및 이성체로부터 선택되는 방향족 아민 또는 하이드록시 방향족 아민;(b) 디-2-피리딜ㅋ톤;1,1'-카보닐디이미다졸;2,2'-피리딜;2-푸릴디옥심;페닐 2-피리딜케토심; 및 1,2-사이클로헥산디온 디옥심;및 이의 유사체, 동족체 및 이성체로부터 선택되는 카보닐 또는 옥시메이트; (c) 에틸렌디아민 -N,N-비스-(2-하이드록시페닐아세트산)디메틸 에스테르; 디에틸디티오카밤삼;1-피롤리딘카보디티오산; 및 3-아미노-5,6-디메틸-1,2,4-트리아진; 및 이의 유사체, 동족체 및 이성체로부터 선택되는 아민; (d) 2,3-디하이드록시벤조산; 3-하이드록시-5-(하이드록시메틸)-2-메틸-4-피리딘-카복실산; 에틸렌디아민-N,N-비스-(2-하이드록시페닐아세트산)딤틸에스테르; 2,6-피리딘디카복실산;N-벤조일-N-페닐-하이드록실아민;데스페리옥사민 B;1-하이드록시-4-메틸-6-(2,4,4-트리메틸펜틸)-2(1H)-피리돈;6-사이클로헥실-1-하이드록시-4-메틸-2(1H)-피리디논;및 이의 유사체, 동족체 및 이성체로부터 선택되는 카복실레이트, 하이드록시산, 하이드록사메이트 또는 방향족 하이드록시산; (e) 5-하이드록시-2-(하이드록시메틸)-4H-피란-4-온;3-하이드록시-5-(하이드록시메틸)--2-메틸-4--피리딘-카복.실산;1,2-디메틸-3-하이드록시피리드-4-온;3-하이드록시-2-메틸-4-피론;1-하이드록시-4-메틸-6-(2,4,4-트리메틸펜틸)-2(1H)-피리돈;및 ;6-사이클로헥실-하이드록시-4-메틸-2(1H)-피리디논; 및 이의 유사체, 동족체 및 이성체로부터 선택되는 알콕사이드, 에놀레이트 또는 케토에놀레이트; (f) 1-하이드록시-4-메틸-6-(2,4,4-트리메틸펜틸)-2(1H)-피리돈;6-하이드록시-2-페닐-3(2H)-피리다지논;6-사이클로헥실-1-하이드록시-4-메틸-2(1H)-피리돈; 2,3-디하이드록시벤조산;4,5-디하이드록시-1,3-벤젠-디설폰산;엔틸렌디아민-N,N-비스-(2-하이드록시페닐아세트산)디메틸 에스테르; 피리독스산;2,3-디하이드록시피리딘;2,4,5-트리하이드록시피리미딘;2,3-디하이드록시나프탈렌;5-하이드록시-2-(하이드록시메틸)-4H-피란-4-온;2,3-디하이드록시피리딘;3-하이드록시-2-메틸-4-피론;4-(2-아미노-1-하이드록시에틸)-1,2-벤젠디올; 및 이의 유사체, 동족체 및 이서체로부터 선택되는 페녹사이드로 또는 카테콜레이트; 또는 (g) 디에틸디티오카밤산; 1-피롤리딘카보디티오산; 및 이의 유사체, 동족체 및 이성체로부터 선택되는 머캅티드로부터 선택됨을 특징으로하는 조성물.
- (a) 2-2'-디피리딜아민;1,10-페난트롤린;디-2-피리딜케논 ;2-푸릴디옥심 ; 2,3비스(2-피리딜)피라진;1-하이드록시-4-메틸-6-(2,4,4-트리메틸펜틸)-2(1H)-피리돈; 2,3-디하이드록시벤조산; 에틸렌디아민-N,N-비스-비스-2-하이드록시페닐아세트산), 디메틸 에스테르; 1,1'-카보닐디이미다졸;1,2-디메틸-3-하이드록시피리드-4-온;2,4,5-트리(20피리딜)-1,3,5-트리아진;1-피롤리딘카보디티오산;디에틸 디티오카밤산;6-사이클로헥실-1-하이드록시-4-메틸-2(1H)-피리돈;2,2'-디피리딜;1,2'-사이클로헥산디온 디옥심; 3-하이드록시-2-메틸-4-피톤 ;2,3-비스(2-피리딜)5,6-디하이트로피라진 ;3-(4-페닐-2-피리딜)-5-페닐-1,2,4-트리아 ; 5-하이드록시-2-(하이드록시메틸)-4-H-피란-4-온 ;2,3-디하이드록시피리딘 ; 2,2'-비퀴놀린 ;2,2'-비피라진;3-(2-피리딜-5,6-디페닐-1,2,4-트리아닌;4,4'-디메틸-2,2'-디피리딜을 4,5-디하이드록시-1,3-벤젠-디설폰산;페닐 2-피리딜 케톡심;데스페리옥사민B;3-하이드록시-5-(하이드록시메틸)-2-메틸-4-피리딘-카복실산;5,7-디클로로-8-하이드록시퀴놀린;2,3-디하이드록시나플탄렌;2,3,5,6-테트라키스-(2''-피리딜)-피라진;2,4-비스(5,6-디페닐-1,2,4-트리아진-3-일)피리딘;2,2'-피리딜;2-(2-피리딜)벤즈이미다졸;6-하이드록시-2-페닐-3(2H)피리다노지논;2,4-프테리딘디올;3-4-페닐-2-피리딜)5,6-디페닐-1,2,4트리아진;N-벤조일-N-페닐-하이드록시아민;3-(4-페닐-2-피리딜)-5,6-디페닐-1,2,4-트리아진;2,6-피리딘디카복실산; 및 2,4,5-트리하이드록시피리미디니 및 4-(2-아미노-1-하이드록시에틸)-1,2-벤젠디올로부터; 바람직하게는 2,2'-디피리딜아민; 1,10-페난트롤린; 디-2-피리딜케톤;및 2-푸릴디옥심; 및 2,3-비스(2-피리딜)피라진으로부터 선택되는 안전한 광보호적 유효량의 바람직하게는 1% 내지 10%의 킬레이트화ㅏ제; 및 (b) 안전한 유효량의 국소용 담체를 함유함을 특징으로하는 국소 적용용 광보호 조성물.
- 제1항 내지 제4항중 어느 한 항에 있어서, 2-에틸헥실 P-메톡시신남메이트, 부틸메녹시디벤조일메탄, 2-하이드록시-4-메톡시벤조페논, 옥틸디메틸 P-아미노벤조산, 2,4-디하이드록시벤조페논의 4-N,N-(20에틸헥실)-메틸 아미노벤조산 에스테르, 4-하이드록시디벤조일메탄의 N,N-디-(2-에틸헥실)-4-하이드록시디벤조일메탄의 N,N-디-(2-메틸헥실)-4-아미노조산 에스테르, 4-하이드록시디벤조일메탄의 4-N,N-(2-에틸헥실)메틸아미노 베노산 에스테르, 2-하이드록시-4-(2-하이드록시에톡시)벤조페논의 4-N,N-(2-에틸헥실)-메틸아미노벤조산 에스테르, 4-(2-하이드록시에톡시)디벤조일메탄의4-N,N-(2-에틸헥실)메틸아민 벤조산 에스테르 2-하이드록시-4-(2-하이드록시에톡시)벤조 페논의 메논의 N,N-디-(2-하이드록시에톡시)벤조 ㅍ논의 N,N-디-2-하이드록시에톡시)벤조펜노의 N,N-디-(2-에틸헥실)-4-아미노벤조산 에스테르, 4-(2-하이드록시에톡시)디벤조일메탄의 N,N-디-(2-에틸헥실)-4-아미노벤조산 및 이의 혼합물로부터 선택되는 안전한 광보호적 유효량, 바람직하게는 1% 내지 20%의 일광차단제를 추가로 함유함을 특징으로하는 조성물.
- 제1항 내지 제5항에 있어서, 하이드로코르티손, 이프로펜, 나프록센, 플루페남산, 메페남산, 메클로페남산, 피록시캄, 펠비낙, 4-(4'-펜틴-3'-온)-2,6디-t-부틸페놀, 4-(5'-헥시노일)-2,6-디-t-부틸페놀, 4-((S-)-(-)-3'-메틸-5'-헥시노일)-2,6-디-t-부틸페놀, 4-((R)-(+)-3'-메틸-5'-헥시노일)-2,6-디-t-부틸페놀, 4-(3',3'-디-메톡시프로피오닐)-2,6-디-t-부틸페놀, 만지스타, 구갈 및 이의 혼합물로부터 선택되는 안전한 광보호적 유효량 바람직하게는 0.1% 내지 10%의 소염제를 추가로 함유함을 특징으로하는 조성물.
- 제1항 내지 제6항중 어느 한 항에 있어서, 안전한 과오호적 유효량의 라디칼 제거 화합물을 추가로 함유함을 특징으로하는 조성물.
- 바람직하게는 0.001mg/cm2내지 1.0mg/cm2, 보다 바람직하게는 0.01mg/cm2내지; 0.1mg/cm2의 길레이트화제가 피부에 적용되도록 피부에 적용하여 피부의 자외선 노출에 의한 유해한 표과를 억제하는 국소용 조성물을 제조하기 위한, 시험관내 용액 라디칼 분석에서 철-촉매화된 하이드록실라디칼 형성을 적어도 50% 억제하는 킬레이트화제의 용도.
- 바람직하게는 0.001mg/cm2내지 1.0mg/cm2, 보다 바람직하게는 0.01mg/cm2내지 0.1mg/cm2의 길레이트화제가 피부에 적용되도록 피부에 적용하여, 피부의 자외선 노출에 의한 유해한 효과를 억제하는 국소용 조성물을 제조하기 위한, 마우스 피부 주름형성 생체내 시험에 피부 주름 등급을 적어도 20%감소시키는 킬레이트화제의 용도.
- 제 8 항 또는 제 9항에 있어서, 킬레이트화제가 (a) 2,2′-디피리딜아민 ; 1,10-페난트롤린 : 디-2-피리딜케톤 ; 2,3-비스(2-피리딘)피라진 ; 2,3-비스-(2-피리딜)-5,6-디하이드로피진 ; 1,1′-카보닐디이미다졸 : 2,4-비스(5,6-디페닐-1,24-트리아진-3-일)피리딘 ; 2,4,6-트리(2-피리딜)-1.3,5-트리아진 ; 4,4′디메닐-2,2′-디피리딜 ; 2, 2′-비퀴놀린 ; 디-2-피릴딜 글리옥살 ; 2-(2-피리딜)벤즈이미다졸 ;2,2'-비피라진 ; 3-(2-피리딜)5,6-디페닐-1,24-트리아닌 ; 3-(4-페닐-2-피리딜)-5-페닐-1,2,4-티리아진 ; 3-(4-페닐-2-피리딜)-5,6-디페닐-1,2,4-트리아진 ; 2,3,5,6-테르라키스-(2′-피리딜)-피라진 ; 2,6-피리딘디카복실산 ; 2,4,5-트리하이드록시피리미딘 ; 페닐 2-피리딜 케톡심 ; 3-아미노-5,6-디메틸-1,2,4-트리아진 ; 6-하이드록시-2-페닐-3(2H)-피리다지논 ; 2,4-프테리디올 ; 2,2′-디피리딜 ; 2,3-디하드록시피리딘 및 5,7-디클로로-8-하이드록시퀴놀린 ; 및 이으 유사체 동족체 및 이성체로부터 선택되는 방향족 아민 또는 하이드록시 방향족 아민 ; (b) 디-2-피리딜케톤 ; 1,1′-카보닐디이미자졸 ; 2,2′-피리딜 ; 2-푸릴디옥심 ; 페닐 2-피리딜케녹심 및 1,2-사이클로헥산디온 디옥실 ; 및 이의 유사체, 동족체 및 이성체로부터 선태되는 카보닐 또는 옥시메이트 ; (c) 에틸레디아민-N,N-비스-(2-하이드록시페닐아세트산)디메틸 에스테르 ; 디에틸디티오카밤산 ; 1-필로리딘카보디티오산 ; 및 3-아미노-5,6-디메닐-1,2,4-트리아진 ; 및 이의 유사체, 동족체 및 이성체로부터 선택되는 아민; (d) 2,3-디하이드로기벤조산 ; 3-하이드록시-5-(하이드록시메틸)-2-메틸-4-피리딘-카복실산 ; 에틸렌디아민-N,N-비스-(2-하이드롯시페닐아세트산)디메틸애스테르 ; 2,6-피리딘디카복실산 ; N-벤조일-N-페닐-하이드록실아민 ; 데스페리옥사민 B; 1-하이드록시-4-메틸-6-(2,4,4-트리메틸펜틸)-2(1H)-피리돈 : 6-사이클로헥실-1-하이드록시-4-메틸-2-(1H)-피리디논 ; 및 이의 유사체, 동족체 및 이성체로부터 선택되는 카복실레이트, 하이드록시산, 하이드록사메이트 또는 방향족 하이드록시 산 ; (e) 5-하이드록시-2-(하이드록시메틸)-4H-필란-4-온 ; 3-하이드록시-5-(하이드록시메틸)-2-메틸-4-피리딘-카복실산 ; 1,2-디메틸-3-하이드록시피리드-4-온 ; 3-하이드록시-2-메틸-4-피론 ; 1-하이드록시-4-메틸-6-(2,4,4-트리메틸펜틸)-2(1H)-피리돈 ; 및 6-사이클로헥실-1-하이드록시-4-메틸-2(H)-피리디논 ; 및 이의 유사체, 동족체 및 이성체로부터 선택되는 알콕사이드, 에놀레이트 또는 케토에놀레이트 ; (f) 1-하이드록시-4-메틸-6-(2,4,4-트리메틸펜틸)-2(1H)-피리돈 ; 6-하이드로시-2-페닐-3(2H)피리다지논 ; 6-사이클로헥실-1-하이드록시-4-메틸-2(1H)-피리딘 ; 2,3-디하이드록시벤조산 ; 4,5-디하이드록시-1,3-벤젠-디설폰사 ; 에틸렌디아민-N,N-비스-(2-하이드록시페닐아세트산)디메틸에스테르 ; 피리독스산 ; 2,3-디하이드록시피리딘 ; ,2,4,5-트리하이드록시피리미딘 ; 2,3-디하이드록시나프탈렌 ; 5-하이드록시-2-(하이드록시메틸)-4H-피란-4-온 ; 2,3-디하드록시피리딘 ; 3-하이드록시-2-메틸-4-피론 ; 4-(2-아미노-1-하이드록시에틸)-1,2-벤젠디올 ; 및 이의 유사체, 동족체 및 이성체로부터 선택되는 페녹사이드 ; 또는카콜레이트 ;또는 (g) 디에틸디티오카밤산 ; 1-피롤리디딘카보디티오산 ; 및 이의 유사체, 동족체 및 이성체로부터 선택되는 머캅티드로부터 선택됨을 특징으로 하는 용도.
- 바람직하게는 0.001mg/cm2내지 1.0mg/cm2, 더욱 바람직하게는 0.01mg/cm2내지 0.1mg/cm2의 킬레이트화제가 피부에 적용되도록 피부에 적용하여, 피부의 자외선 노출에 의한 유해한 표과를 억제하는 국소용 조성물을 제조하기 위한, 2,2′-디피리딜아민 ; 1,10-페난트롤린 ; 디-2-피리딜케톤 ; 2-푸릴디옥심 ;2,3-비스(2-피리딜)피라진 ; 1-하이드록시-4-메틸-6-(2,4,4-트리메틸펜틸)-2(1H)-피리돈 ; 2,3-디하이드록시벤조산 ; 에틸렌디아민-N,N-비스-(2-하이드로기페닐아세트산), 디메틸 에스테르 ; 1,1′-카보닐디이미다졸 ; 1,2-디메틸-3-하이드록시피리드-4-온 ; 2,4,5-트리(2-피리딜)-1,3,5-트리아진 ; 1-피롤리딘카보디티오산 ; 디에틸디티오카밤산 ; 6-사이클로헥실-1-하이드록시-4-메틸-2(1H)-피리돈 ; 2,2′-디피리딜 ; 1,2-사이클로헥산디온 디옥심 ; 3-하이드록시-2-메틸-4-피론 ; 2,3-비스(2-피리딜)-5,6-디하이드로피라진 ; 3-(4-페닐-2-피리딜)-5-페닐-1,2,4-트리아진 ; 5-하이드록시-2-(하이드록시메틸)-4H-피란-4-온 ; 2,3-디하이드록시피리딘 ; 2,2′-비퀴놀린 ; 2,2′-비피라진 ; 3-(2-피리딜)-5,6-디페닐-1,2,4-트리아진 ; 4,4′-디메틸-2,2′-디피리딜 ; 4,5-디하이드록시-1,3-벤젠-디설폰산 ; 페닐 2-피리딜 케톡심 ; 데스페리옥사민 B ; 3-하이드록시-5-(하이드록심메틸)-2-메틸-4-피리딘-카복실산 ; 5,7-디클로로-8-하이드록시 퀴놀린 ; 2,3-디하이드록시 나프탈렌 ; 2,3,,5,6-테트라키스-(2′-피리딜)-피라진 ; 2,4-비스(5,6-디페닐-1,2,4-트리아진-3-일)피리미딘 ; 2,2′-피리딜 ; 2-(2-피리딜)벤즈이미다졸 ; 6-하이드록시-2-페닐-3-(2H)-피리다조논 ; 2,4-프테리딘디올 ; 3-(4-페닐-2-피리딜)-5,6-디페닐-1,2,4-트리아진 ; N-벤조일-N-페닐-하이드록시아민 ; 3-아미노-5,6-디메틸-1,2,4-트리아진 ; 2,6-피리딘디카복실산 ; 2,4,5-트리하이드록시피리미딘 ; 및 4-(2-아미노-1-하이드록시에틸)-1,2-벤젠디올로부터 ; 바람직하게는 2,2′-디피리딜아민 ; 1,10-페난트롤린 ; 디-2-피리딜케톤 및 ; 2-푸릴디옥심 ; 및 2,3-비스(2-피리딜)피라진으로부터 선택되는 킬레이트화제의 용도.
- 제 8 항 내지 제11항중 어느 한 항에 있어서, 조성물이 2-에틸 헥실 P-메톡시신남메메이트, 부틸메톡시디벤조일메탄, 2-하이드록시-4-메톡시벤조페놀, 옥틸디메틸 P-아미노 벤조산, 2,4-디하이드록시벤조페놀의 4-N,N-(2-에틸헥실)-메틸아미노벤조산 에스테르, 4-하이드록시디벤조일메탄의 N,N-디-(2-에틸헥실)-4-아미노벤조산 에스테르 , 4-하이드록시의 벤조일메탄의 4-N,N-(2-에틸헥실)-메틸아미노벤조산 에스테르, 4-2-하이드록시-4-(2-하이드록시에톡시)벤조 페논의 4-N,N-디-(2-에틸헥실)-메틸아미노벤조산 에스테르, 4-(2-하이드록시에톡시)디벤조일메탄의 4-N,N-(2-에틸헥실)메틸아민 벤조산 에스테르, 2-하이드로시-4-(2-하이드록시에톡시)벤조페논의 N,N-디-(2-에틸헥실)-4-아미노벤조산 에스테르, 4-(2-하이드록시에톡시)디벤조일메탄의 N,N-디-(2-에틸헥실)-4-아미노벤조산 및 이의 혼합물로부터 선택되는, 안전한 광보호적 유효량, 바람직하게는 0.01mg/cm2내지 1.0mg/cm2, 더욱 바람직하게는 0.05mg/cm2내지 0.5mg.cm2의 일광차단제가 피부에 적용되도록 함유함을 특징으로 하는 용도.※ 참고사항 : 최초 출원 내용에 의하여 공개하는 것임.
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US11257687A | 1987-10-22 | 1987-10-22 | |
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US25191088A | 1988-10-04 | 1988-10-04 | |
US7/251,910 | 1988-10-04 | ||
US07/251,910 | 1988-10-05 |
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KR (1) | KR0166576B1 (ko) |
AT (2) | ATE176396T1 (ko) |
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-
1988
- 1988-10-18 AT AT92106052T patent/ATE176396T1/de active
- 1988-10-18 DE DE3856302T patent/DE3856302T2/de not_active Expired - Fee Related
- 1988-10-18 EP EP88309741A patent/EP0313305A3/en not_active Ceased
- 1988-10-18 AT AT92106051T patent/ATE177939T1/de not_active IP Right Cessation
- 1988-10-18 EP EP92106051A patent/EP0496433B1/en not_active Expired - Lifetime
- 1988-10-18 DE DE3856315T patent/DE3856315T2/de not_active Expired - Fee Related
- 1988-10-18 EP EP92106052A patent/EP0496434B1/en not_active Expired - Lifetime
- 1988-10-20 CA CA000580799A patent/CA1334008C/en not_active Expired - Fee Related
- 1988-10-21 NZ NZ226667A patent/NZ226667A/xx unknown
- 1988-10-21 AU AU24085/88A patent/AU629518B2/en not_active Ceased
- 1988-10-22 KR KR1019880013864A patent/KR0166576B1/ko not_active IP Right Cessation
- 1988-10-22 JP JP63267020A patent/JP2897832B2/ja not_active Expired - Fee Related
-
1993
- 1993-07-01 US US08/086,757 patent/US5487884A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
JP2897832B2 (ja) | 1999-05-31 |
DE3856315T2 (de) | 1999-10-14 |
EP0313305A2 (en) | 1989-04-26 |
EP0496434A2 (en) | 1992-07-29 |
DE3856302T2 (de) | 1999-09-09 |
CA1334008C (en) | 1995-01-17 |
DE3856315D1 (de) | 1999-04-29 |
NZ226667A (en) | 1993-11-25 |
AU2408588A (en) | 1989-04-27 |
EP0496433A3 (en) | 1994-05-18 |
AU629518B2 (en) | 1992-10-08 |
EP0313305A3 (en) | 1990-02-07 |
EP0496433A2 (en) | 1992-07-29 |
ATE176396T1 (de) | 1999-02-15 |
EP0496434A3 (en) | 1994-05-18 |
EP0496434B1 (en) | 1999-02-03 |
KR0166576B1 (ko) | 1999-01-15 |
DE3856302D1 (de) | 1999-03-18 |
JPH01265018A (ja) | 1989-10-23 |
ATE177939T1 (de) | 1999-04-15 |
EP0496433B1 (en) | 1999-03-24 |
US5487884A (en) | 1996-01-30 |
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