KR900007818A - 소염제인 3.5-디-t.-부틸-4-히드록시페닐-1.3.4-티아디아졸 및 옥사디아졸과 3.5-디-t.-부틸-4-히드록시페닐-1.2.4-티아디아졸, 옥사디아졸 및 트리아졸 - Google Patents
소염제인 3.5-디-t.-부틸-4-히드록시페닐-1.3.4-티아디아졸 및 옥사디아졸과 3.5-디-t.-부틸-4-히드록시페닐-1.2.4-티아디아졸, 옥사디아졸 및 트리아졸 Download PDFInfo
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Abstract
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Claims (85)
- 하기 일반식(Ⅰ)의 화합물 및 그의 제약상 허용되는 산 부가염 또는 염기 부가염 또는 수화물.상기 식 중, n은 0 또는 1이고,W는또는이며,여기서, W는 N,NR1(여기서, R은 수소 또는 저급 알킬임) O, 또는 S이고,Z는 O,S,NR1또는 N(여기서, R1은 독립적으로 상기 정의한 바와 같음)이되, X및 Z가 동시에 N 또는 NR1일 경우, Z가 NR1일때 X 는 N이어야 하고, Z가 N일 때 X는 NR1이어야 하며, 또한 X가 S 또는 0인 경우 Z는 N이어야 하고, Z가 S 또는 0인 경우 X는 N이어야 하며,Y는 (1) C-SR1(여기서, R1은 독립적으로 상기 정의한 바와 같음),(2)(여기서, R2는 저급 알킬임),(3)(여기서, R1은 상기 정의한 바와 동일함),(4) C-NR1R3(여기서, R1은 독립적으로 상기 정의한 바와 동일하고, R3은 수소 또는 저급 알킬임),(5) COR1(여기서, R1은 독립적으로 상기 정의한 바와 동일함),(6) CR4(여기서, R4는 할로겐, CF3, CO2R1또는 페닐, 알킬, NH(CH2)mOH, CCL3, CONR1R3, CSNR1R3, CH2X10, CH2NR11R13, NHCSNHCO2R2, CH2SR2, CH2SO2R2또는 NHNH2이고, 이때 m은 1,2 또는 3이고, R11및 R13은 수소, 저급 알킬 또는 X과 함께 탄소 원자수 4내지 6의 포화 고리를 형성하고, X10은 할로겐 또는 NO2이고, R5는H, 저급 알킬 또는 OR1이고, R1,R2및R3는 독립적으로 상기 정의한 바와 같음)(7)이다.
- 제1항에 있어서, n이 0인 화합물.
- 제1항에 있어서, n이 1인 화합물.
- 제2항에 있어서, W가(여기서, X,Y 및 Z는 상기 정의한 바와 같음)인 화합물.
- 제4항에 있어서, Z가 N이고, X가 S이며, Y가 CR4(여기서, R4는 NHCSNHCO2R2임)인 화합물.
- 제2항에 있어서, X가 N,NR1(여기서, R1은 수소 또느 저급 알킬임) 또는 S이고, Z가 S,NR1또는 N이되,단 Z와 X가 동시에 NR1또는 N일때, Z가 NR1일 때 X는 N이어야 하고, Z가 N일 때 X는 NR1이어야 하며, X가 S일 때 Z는 N이어야 하고, Z가 S일 때 X는 반드시 N인 화합물.
- 제2항에 있어서, Y가 COR1, CSR1, C-NHCN,, C-NHCOCH3, CNHCOR5또는 C-NHSO2R2인 화합물.
- 제3항에 있어서, Y가 COR1, CSR1, CNR1R2, C-NHCN,, C-NHCOCH3, C-NHCOR5또는 C-NHSO2R2인 화합물.
- 제4항에 있어서, 화합물이 5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐〕-2,4-디히드로-3H-1,2,4-트리아졸 3티온인 화합물.
- 제4항에 있어서, 화합물이 5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐〕-1,3,4-티아디아졸-2(3H)-온인 화합물.
- 제4항에 있어서, 화합물이 N-〔5-〔3.5-비스(1,1-디메틸에틸)-4-히드록시페닐〕-1,3,4-티아디아졸-2-일〕우레아인 화합물.
- 제4항에 있어서, 화합물이 4-(5-아미노-1,3,4-옥사디아졸-2-일)-2,6-비스(1,1-디메틸에틸)-페놀인 화합물.
- 제4항에 있어서, 화합물이 2,6-비스-(1,1-디메틸에틸)-4-〔5-(메틸티오)-1,3,4-티아디아졸-2-일〕페놀인 화합물.
- 제4항에 있어서, 화합물이 〔〔5-〔3.5-비스(1,1-디메틸에틸)-4-히드록시페닐〕-1,3,4-티아디아졸-2-일〕티오]-아세트산인 화합물.
- 제4항에 있어서, 화합물이 2,6-비스(1,1-디메틸에틸)-4-〔5-(메틸술피닐)-1,3,4-티아디아졸-2-일]-페놀인 화합물.
- 제4항에 있어서, 화합물이 2,6-비스(1,1-디메틸에틸)-4-〔5-(메틸술피닐)-1,3,4-티아디아졸-2-일〕-페놀인 화합물.
- 제4항에 있어서, 화합물이 2,6-비스(1,1-디메틸에틸)-4-〔5-(메틸아미노)-1,3,4-티아디아졸-2-일]-페놀인 화합물.
- 제4항에 있어서, 화합물이 N-〔5-〔3.5-비스(1,1-디메틸에틸)-4-히드록시페닐〕-1,3,5-티아디아졸-2-일〕-구아니딘인 화합물.
- 제4항에 있어서, 화합물이 N-〔5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐〕-1,3,5-티아디아졸-2-일〕구아니딘, 일염산염인 화합물.
- 제4항에 있어서, 화합물이 에틸 5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐〕-1,3,4-티아디아졸-2-일〕-시안아미드인 화합물.
- 제4항에 있어서, 화합물이 콜린염인 화합물.
- 제4항에 있어서, 2,6-비스-(1,1-디메틸에틸)-4-〔5-〔(2-히드록시에틸)아미노〕-1,3,4-티아디아졸-2-일〕페놀인 화합물.
- 제4항에 있어서, 화합물이 5-〔3,5-비스-(1,1-디메틸에틸)-4-히드록시페닐)-2,4-디히드로 4-메틸-3H-1,2,4-트리아졸-3-티온인 화합물.
- 제4항에 있어서, 화합물이 2,6-비스(1,1-디메틸에틸)-4-〔5-메틸티오)-2H-1,2,4-트리아졸-3-일〕페놀인 화합물.
- 제4항에 있어서, 화합물이 2,6-비스(1,1-디메틸에틸)-4-〔5-(메틸술피닐)-2H-1,2,4-트리아졸-3-일〕페놀인 화합물.
- 제4항에 있어서, 화합물이 2,6-(비스(1,1-디메틸에틸)-4-〔3-(메틸술피닐)-1H-1,2,4-트리아졸-5-일〕페놀인 화합물.
- 제4항에 있어서, 화합물이 5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐)-1,3,4-티아디아졸-2-카르보니트릴인 화합물.
- 제1항에 있어서, 화합물이 2,6-비스(1,1-디메틸에틸)-4〔1,3,4-티아디아졸-2-일〕페놀인 화합물.
- 제4항에 있어서, 화합물이 2,6-비스(1,1-디메틸에틸)-4-(5-메틸-1,3,4-티아디아졸 2일〕페놀인 화합물.
- 제4항에 있어서, 화합물이 2,6-(비스(1,1-디메틸에틸)-4-(5-(트리플루오로메틸)-1,3,4-티아디아졸-2-일〕-페놀인 화합물.
- 제4항에 있어서, 화합물이 5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐)-1,3,4-티아디아졸-2-카르복실아미드인 화합물.
- 제4항에 있어서, 화합물이 5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐)-1,3,4-티아디아졸-2-카르복스아미드인 화합물.
- 제4항에 있어서, 화합물이 5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐)-1,3,4-티아디아졸-2-카르보티오아미드인 화합물.
- 제4항에 있어서, 화합물이 5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐)-1H-1,2,4-트리아졸-3-아민인 화합물.
- 제4항에 있어서, 화합물이 5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐)-1H-1,2,4-트리아졸-3-아민인 일염산염인 화합물.
- 제4항에 있어서, 화합물이 3-〔3,5-비스(1,1,-디메틸에틸)-4-히드록시페닐)-1,2,4-옥사디아졸-5(4H)-온인 화합물.
- 제4항에 있어서, 화합물이 2,6-비스-(1,1-디메틸에틸)-4-(5-메틸-1,2,4-옥사디아졸-3-일〕페놀인 화합물.
- 제4항에 있어서, 화합물이 4-(5-아미노-1,2,4-옥사디아졸-3-일)-2,6-비스(1,1-디메틸에틸)페놀인 화합물.
- 제4항에 있어서, 화합물이 2,6-비스(1,1-디메틸에틸)-4-(3-트리클로로메틸-1,2,4-옥사디아졸-5-일)페놀인 화합물.
- 제2항에 있어서, W가(여기서, X, Y 및 Z는 상기 정의한 바와 같음)인 화합물.
- 제40항에 있어서, X가 N, NR1(여기서, R1은 수소 또는 저급 알킬임) 또는 S이고, Z가 S, NHR1또는 N이되, 단 Z와 X가 동시에 NR1또는 N일때, Z가 NR1일 때 X는 반드시 N이고, Z가 N일 때 X는 반드시 NR1이고, 또한 X가 S일 때 Z는 반드시 N이고, Z가 S일 때 X는 반드시 N인 화합물.
- 제40항에 있어서,Y가 COR1, CSR2, C-NHCN,, C-NHCOCH3, C-NHCOR5또는 C-NHSO2R2인 화합물.
- 제40항에 있어서, 화합물이 4-(3-브로모-1,2,4-옥사디아졸-5-일)-2,6-비스(1,1-디메틸에틸)페놀인 화합물.
- 제40항에 있어서, 화합물이 2,6-비스(1,1-디메틸에틸)-4-〔3-메틸-1,2,4-옥사디아졸-5-일〕페놀인 화합물.
- 제40항에 있어서, 화합물이 4-(3-(클로로메틸)-1,2,4-옥사디아졸-5-일)-2,6-비스(1,1-디메틸에틸)페놀인 화합물.
- 제40항에 있어서, 화합물이 2,6-비스(1,1-디메틸에틸)-4〔3-(1-피롤리디닐메틸)-1,2,4-옥사디아졸-5-일〕페놀인 화합물.
- 제40항에 있어서, 화합물이 4-〔3-〔(디메틸아미노)메틸〕-1,2,4-옥사디아졸-5-일)-2,6-비스(1,1-디메틸에틸)페놀인 화합물.
- 제40항에 있어서, 화합물이 2,6-비스(1,1-디메틸에틸)-4-〔3-〔(메틸아미노)메틸〕-1,2,4-옥사디아졸-5-일〕페놀인 화합물.
- 제40항에 있어서, 화합물이 2,6-비스(1,1-디메틸에틸)-4-〔3-(메틸티오)메틸〕-1,2,4-옥사디아졸-5-일〕페놀인 화합물.
- 제40항에 있어서, 화합물이 2,6-비스(1,1-디메틸에틸)-4-〔3-〔(메틸술포닐)메틸〕-1,2,4-옥사디아졸-5-일〕페놀인 화합물.
- 제40항에 있어서, 화합물이 4-(3-아미노-1,2,4-옥사디아졸-5-일)-2,6-비스-(1,1-디메틸에틸)페놀인 화합물.
- 제40항에 있어서, 화합물이 4-〔3-(디메틸아미노)-1,2-4-옥사디아졸-5-일)-2,6-비스(1,1-디메틸에틸)페놀인 화합물.
- 제3항에 있어서, W가(여기서, X, Y 및 Z는 상기 정의와 같음)인 화합물.
- 제53항에 있어서, 화합물이 (E)-4-〔2-(5-아미노-1,3,5-옥사디아졸-2-일)에테닐〕-2,6-비스(1,1-디메틸에틸)페놀인 화합물.
- 제53항에 있어서, 화합물이 (E)-2,6-비스(1,1-디메틸에틸)-4-〔2-〔5-(메틸티오)-1,3,4-티아디아졸-2-일〕에테닐〕페놀인 화합물.
- 제53항에 있어서, (E)-2,6-비스(1,1-디메틸에틸)-4-〔2-〔5-(메틸술포닐)-1,3,4-티아디아졸-2-일〕에테닐〕페놀인 화합물.
- 제3항에 있어서, W가(상기 식에서 X, Y 및 Z는 상기 정의와 같음)인 화합물.
- 제4항에 있어서, 화합물이 5-〔3,5-비스-비스(1,1-디메틸에틸)-4-히드록시페닐〕-1,3,4-티아디아졸-2(3H)-티온인 화합물.
- 제58항에 있어서, 콜린, 나트륨, 칼슘, 마그네슘, 칼륨염.
- 제4항에 있어서, 화합물이 5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐〕-2,3,4-옥사디아졸-2(3H)-온인 화합물.
- 제4항에 있어서, 화합물이 5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐)-1,3,4-옥사디아졸-2(3H)-티온인 화합물.
- 제4항에 있어서, 화합물이 4-(5-아미노-1,3,4-티아디아졸-2-일)-2,6-비스(1,1-디메틸에틸)페놀인 화합물.
- 제53항에 있어서, 화합물이 5-〔2-〔3,5-비스-(1,1-디메틸에틸)-4-히드록시페닐〕에테닐〕-1,3,4-옥사디아졸-2(3H)-온인 화합물.
- 제53항에 있어서, 화합물이 (E)-2,4-디히드로-5-〔2-〔4-히드록시-3,5-비스(1,1-디메틸에틸)-페닐〕에테닐〕-3H-1,2,4-트리아졸-3-티온인 화합물.
- 제4항에 있어서, 화합물이 5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐)-2,4-디히드로-3H-1,2,4-트리아졸-3-온인 화합물.
- 제4항에 있어서, 화합물이 5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐)-2,4-디히드로-4-메닐-3H-1,2,4-트리아졸-3-온인 화합물.
- 제53항에 있어서, 화합물이 5-〔2-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐〕에테닐〕-2,4-디히드로-3H-1,2,4-트리아졸-3-온인 화합물.
- 제4항에 있어서, 화합물이 5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐)-3H-1,2,4-트리아졸-3-티온인 화합물.
- 제53항에 있어서, 화합물이 5-〔2-〔3,5-비스-(1,1-디메틸에틸)-4-히드록시페닐〕에테닐〕-1,3,4-옥사디아졸-2(3H)-티온인 화합물.
- 4-아미노-3-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐〕-2,4-디히드로-5H-1,2,4-트리아졸-5-티온인 화합물.
- 제4항에 있어서, 화합물이 2,6-비스(1,1-디메틸에틸)-4-〔5-메틸티오)-1,3,4-옥사디아졸-2-일〕페놀인 화합물.
- 제4항에 있어서, 화합물이 2,6-비스(1,1-디메틸에틸)-4-〔5-메틸술포닐)-1,3,4-옥사디아졸-2-일〕페놀인 화합물.
- 제4항에 있어서, 화합물이 N-〔5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐〕-1,3,4-옥사디아졸-2-일〕구아니딘, 일염산염인 화합물.
- 제4항에 있어서, 화합물이 에틸 〔5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐〕-1,3,4-옥사디아졸-2-일〕시안아미드인 화합물.
- 제4항에 있어서, 화합물이 N-〔5-3,5-비스(1,1-디메틸에틸)-4-히드록시페닐〕-1,3,4-티아디아졸-2-일〕메탄술폰아미드인 화합물.
- 제4항에 있어서, 화합물이 N-〔5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐〕-1,3,4-티아디아졸-2-일〕-아세트아미드인 화합물.
- 제53항에 있어서, 화합물이 (E)-〔2-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐〕에테닐〕-1,3,4-티아디아졸-2(3H)-티온인 화합물.
- 제4항에 있어서, 화합물이 N-〔5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐〕-1,2,4-옥사디아졸-3-일〕메탄이미도에이트인 화합물.
- 제40항에 있어서, 화합물이 5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐)--1,2,4-티아디아졸-3-올인 화합물.
- 제4항에 있어서, 화합물이〔〔〔5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐〕-1,3,4-티아디아졸-2-일〕아미노〕티옥소메틸〕카르바메이트인 화합물.
- 제4항에 있어서, 화합물이 N-〔5-〔3,5-비스(1,1-디메틸에틸)-4-히드록시페닐〕-1,3,4-티아디아졸-2-일〕티오우레아인 화합물.
- 제1항의 화합물 소염량과 제약상 담체로 이루어진 소염제로서 유용한 제약 조성물.
- 제1항의 화합물을 단위 투여 형태로 투여하는 것을 특징으로 하는 포유동물에 있어서의 염증 치료 방법.
- 제82항에 있어서, 비스테로이드성 소염제, 말초 진통제, 시클로옥시게나제 억제제, 류코트리엔 길항제, 항히스타민제, 프로스타클란딘 길항제 또는 트롬복산 길항제인 제2의 유효 성분 유효량을 추가로 함유하는 것을 특징으로 하는 제약 조성물.
- 제82항 또는 84항의 조성물의 소염 유효량, 항알레르기 유효량, 항관절염 유효량, 항궤양, 유효량, 항천식 유효량, 항건선 유효량, 뇌혈관계 유효량을 치료를 요하는 포유동물에 단위 투여 형태로써, 투여하는 것을 특징으로 하는 염증, 관절염, 궤양, 알레르기, 천식, 건선 또는 심장 혈관계 질병 치료 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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US8580805B2 (en) * | 2010-08-31 | 2013-11-12 | Hubert Maehr | Pyrimidine carboxamide derivatives |
CN103102348B (zh) * | 2011-11-14 | 2016-06-08 | 上海交通大学 | 噁二唑类化合物及其制备方法、药物组合物及其用途 |
CL2012003253A1 (es) * | 2012-11-22 | 2013-01-11 | Univ Concepcion | Compuestos derivados de 1,3,4-tiadiazol alquilamidas y de chalconas, antagonistas del receptor trpv-1; uso de los compuestos para tratar el dolor cronico. |
GB201810581D0 (en) | 2018-06-28 | 2018-08-15 | Ctxt Pty Ltd | Compounds |
EP3986890B1 (en) | 2019-06-18 | 2023-11-15 | Pfizer Inc. | Benzisoxazole sulfonamide derivatives |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2215949B1 (ko) * | 1973-02-01 | 1976-07-02 | Delalande Sa | |
US4212970A (en) * | 1977-11-28 | 1980-07-15 | Fuji Photo Film Co., Ltd. | 2-Halomethyl-5-vinyl-1,3,4-oxadiazole compounds |
JPS58150576A (ja) * | 1982-03-03 | 1983-09-07 | Sumitomo Chem Co Ltd | 新規な1,2,4−オキサジアゾ−ル誘導体 |
DE3302120A1 (de) * | 1983-01-22 | 1984-07-26 | Bayer Ag, 5090 Leverkusen | (+)-antipode des (e)-1-cyclohexyl-4,4-dimethyl-3-hydroxy-2-(1,2,4-triazol-1-yl)-pent-1-ens |
IL79648A (en) * | 1985-08-09 | 1991-12-12 | Lilly Co Eli | Pharmaceutical anti-inflammatory and ischemia preventing compositions containing di-t-butylphenol derivatives,some such novel compounds and process for their preparation |
US4743606A (en) * | 1986-03-25 | 1988-05-10 | Boehringer Ingelheim Pharmaceuticals, Inc. | 3-[2-(3',5'-di-t-butyl-4'-hydroxyphenyl)ethenyl]pyridine having anti-inflammatory and anti-arthritic properties |
US4758578A (en) * | 1987-01-29 | 1988-07-19 | Hoechst Roussel Pharmaceuticals, Inc. | Arylthiadiazolylsulfonamides, pharmaceutical compositions and use |
AU2948189A (en) * | 1987-12-31 | 1989-08-01 | Smithkline Beckman Corporation | 4-aralkyl-5-substituted-1,2,4-triazole-5-thiols |
-
1989
- 1989-11-27 NZ NZ231534A patent/NZ231534A/en unknown
- 1989-11-27 FI FI895669A patent/FI93954C/fi not_active IP Right Cessation
- 1989-11-28 AT AT89121896T patent/ATE127116T1/de not_active IP Right Cessation
- 1989-11-28 ES ES89121896T patent/ES2075845T3/es not_active Expired - Lifetime
- 1989-11-28 DK DK599789A patent/DK599789A/da not_active Application Discontinuation
- 1989-11-28 JP JP1306789A patent/JP2821208B2/ja not_active Expired - Fee Related
- 1989-11-28 PH PH39605A patent/PH27025A/en unknown
- 1989-11-28 DE DE68924044T patent/DE68924044T2/de not_active Expired - Fee Related
- 1989-11-28 IE IE378589A patent/IE68850B1/en not_active IP Right Cessation
- 1989-11-28 AU AU45625/89A patent/AU631385B2/en not_active Ceased
- 1989-11-28 NO NO894742A patent/NO178623C/no unknown
- 1989-11-28 KR KR1019890017310A patent/KR970004914B1/ko not_active IP Right Cessation
- 1989-11-28 EP EP89121896A patent/EP0371438B1/en not_active Expired - Lifetime
- 1989-11-29 CA CA002004154A patent/CA2004154C/en not_active Expired - Fee Related
- 1989-11-29 PT PT92451A patent/PT92451B/pt not_active IP Right Cessation
-
1995
- 1995-10-11 GR GR950402793T patent/GR3017688T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
NO178623C (no) | 1996-05-02 |
ES2075845T3 (es) | 1995-10-16 |
FI895669A0 (fi) | 1989-11-27 |
EP0371438A3 (en) | 1991-03-27 |
DK599789D0 (da) | 1989-11-28 |
JP2821208B2 (ja) | 1998-11-05 |
PH27025A (en) | 1993-02-01 |
IE68850B1 (en) | 1996-07-24 |
NO178623B (no) | 1996-01-22 |
ATE127116T1 (de) | 1995-09-15 |
NO894742D0 (no) | 1989-11-28 |
GR3017688T3 (en) | 1996-01-31 |
AU4562589A (en) | 1990-06-21 |
DK599789A (da) | 1990-05-30 |
CA2004154A1 (en) | 1990-05-29 |
DE68924044D1 (de) | 1995-10-05 |
PT92451A (pt) | 1990-05-31 |
NO894742L (no) | 1990-05-30 |
FI93954C (fi) | 1995-06-26 |
EP0371438B1 (en) | 1995-08-30 |
FI93954B (fi) | 1995-03-15 |
IE893785L (en) | 1990-05-29 |
PT92451B (pt) | 1995-07-18 |
AU631385B2 (en) | 1992-11-26 |
KR970004914B1 (ko) | 1997-04-08 |
JPH02270865A (ja) | 1990-11-05 |
EP0371438A2 (en) | 1990-06-06 |
DE68924044T2 (de) | 1996-02-15 |
NZ231534A (en) | 1992-02-25 |
CA2004154C (en) | 1997-10-07 |
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