KR900009992A - Ab-021 항생제 및 그의 제조방법 - Google Patents
Ab-021 항생제 및 그의 제조방법 Download PDFInfo
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- KR900009992A KR900009992A KR1019890017773A KR890017773A KR900009992A KR 900009992 A KR900009992 A KR 900009992A KR 1019890017773 A KR1019890017773 A KR 1019890017773A KR 890017773 A KR890017773 A KR 890017773A KR 900009992 A KR900009992 A KR 900009992A
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- methanol
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- antibiotics
- acetonitrile
- dihydrogen phosphate
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- 239000003242 anti bacterial agent Substances 0.000 title claims 11
- 229940088710 antibiotic agent Drugs 0.000 title claims 11
- 238000002360 preparation method Methods 0.000 title 1
- 230000003115 biocidal effect Effects 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 45
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 claims 6
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 claims 6
- 235000019837 monoammonium phosphate Nutrition 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 238000010521 absorption reaction Methods 0.000 claims 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 238000001228 spectrum Methods 0.000 claims 4
- 238000004809 thin layer chromatography Methods 0.000 claims 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 3
- 238000000855 fermentation Methods 0.000 claims 3
- 230000004151 fermentation Effects 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 235000015097 nutrients Nutrition 0.000 claims 3
- 238000004366 reverse phase liquid chromatography Methods 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 2
- 241000187747 Streptomyces Species 0.000 claims 2
- 241000187180 Streptomyces sp. Species 0.000 claims 2
- 238000010564 aerobic fermentation Methods 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 239000000417 fungicide Substances 0.000 claims 2
- 230000014759 maintenance of location Effects 0.000 claims 2
- 239000002609 medium Substances 0.000 claims 2
- 244000005700 microbiome Species 0.000 claims 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims 2
- 235000019796 monopotassium phosphate Nutrition 0.000 claims 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 claims 2
- 235000019799 monosodium phosphate Nutrition 0.000 claims 2
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 claims 2
- 238000004007 reversed phase HPLC Methods 0.000 claims 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 235000019270 ammonium chloride Nutrition 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 238000012258 culturing Methods 0.000 claims 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims 1
- 229910000388 diammonium phosphate Inorganic materials 0.000 claims 1
- 235000019838 diammonium phosphate Nutrition 0.000 claims 1
- 238000000921 elemental analysis Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 230000000855 fungicidal effect Effects 0.000 claims 1
- 239000001963 growth medium Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052500 inorganic mineral Chemical class 0.000 claims 1
- 229910017053 inorganic salt Inorganic materials 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000011707 mineral Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 239000011343 solid material Substances 0.000 claims 1
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
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- C12P1/06—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes by using actinomycetales
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- C12R2001/465—Streptomyces
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Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도는 AB-021a 항생제의 U.V. 흡수 스펙트럼을 나타낸다. 제2도는 AB-021a 항생제의 I.R. 흡수 스펙트럼을 나타낸다. 제3도는 AB-021a 항생제의1H N.M.R. 스펙트럼을 나타낸다.
Claims (12)
- (a) 디메탈술폭시드 및 (1:1V/V) 에탄올/물 또는 (1;1 V/V) 메탄올/물 혼합물 [V/V=부피/부피]에 잘 용해되고, 물에는 잘 용해되지 않으며, 에탄올 및 메탄올에는 다소 잘 용해됨. (b) %값으로 나타낸 대략의 원소분석 : 탄소 : 64.3, 수소 : 9.15, 질소 : 1.04. (c) 분자량 : 약1139, (d) U.V. 광에서의 최대 흡수 피크(0.025mg/ml의 1:1(V/V)아세토니트릴/물) : 232.8nm에서 0.193:318.4nm에서 2.064, 332.6nm에서 2.44:349.6nm에서 2.113, (e) 적외선광에서의 최대흡수피크 (cm-1):3365:3015:2923:2851:1700:1634:1594:1541:1431:1380:1329:1262:1128:1095:1056:1004:968:919:878:843:804:754: (f)1H-N.M.R. 스펙트럼의 주요 피크 : δTMS(ppm) :7.18(d.1H) :6.69(dd.1H) :6.59(dd.1H) :6.52∼6.09(m.9H) :5.96∼5.70(m.3H) :5.70∼5.31(m.8H) :4.27∼4.02(m.4H) :4.02∼3.82(m.4H) :3.82∼3.58(m.4H) :3.30(t.1H) :2.82(t.2H) :2.73∼2.4(*)(m.3H) :2.41∼1.98(m.13H) :1.91(s.3H) :1.79∼1.12(m.24-25H) :1.00(d.3H) :0.95(d.3H) :0.89(d.3H) :0.85(d.3H) :범위내 (*)는 DMSOd6피크도 포함하는 것이다. (g)13C-N.M.R. 스펙트럼의 주요 피크:δTMS(ppm):212.1(s):169.9(s): 138.8(d):138.5(d):137.0(d):136.9(d):136.7(d):136.1(d):135.9(d):135.9(d):134.0(d):133.3(d):133.0(d):132.9(d):132.5(d):132.4(d):132.0(d):131.5(d):131.0(d):131.0(d):129.3(d):128.9(d):128.0(d):126.7(d):126.4(d):125.3(d):75.3(d):72.3(d):71.2(d):70.6(d):69.7(d):68.9(d):68.4(d):68.0(d):67.1(d):67.1(d):65.7(d):64.2(d):64.2(d):52.1(d):41.5(d):39.9(d):49.2(t):46.2(t):46.0(t):45.2(t):45.2(t):44.9(t):43.9(t):41.2(t):40.8(t):40.7(t):39.2(t):38.8(t):34.1(t):32.8(t):32.1(t):29.3(t):24.1(t)22.8(q):18.4(q):13.2(q):10.5(q):9.1(q). (h) 60F 254슬랩(Merck-Schuchardt)에서 박막크로마토그래피(TLC)에 의한 Rf값 ; 에탄올 : 디옥산 : 30% 암모니아 수용액 :물(8:1:1:1)에서 0.47∼0.57:메틸렌클로라이드:메탄올(17.3)에서 0.0:머크-스쿠챠르트 RP-18F 254 슬랩에서의 역상 크로마토그래피에 의한 Rf값 : 메탄올 : 아세토니트릴:물에용해시킨 25mM 인산일수소 나트륨 (4:4:2)에서 0.29:메탄올:아세토니트릴:물에 용해시킨 25mM 인산이수소칼륨+7mM 테트라메틸-암모늄클로라이드(4:4:2)에서 0.39;메탄올:물에 용해시키고, 인산을 사용하여 pH7.5로 조정한 10mM 인산일수소 암모늄용액(8:2)에서 0.21:메탄올:아세토니트릴:물에 용해시키고, 인산을 사용하여 pH7.5로 조정한 10mM 인산일수소암모늄 용액(4:4:2)에서 0.25, (ⅰ) 메탄올:아세토니트릴 :10mM 인산일수소암모늄 수용액 (1:1:1)을 사용하여 0.8ml/분의 유량으로 40℃에서 용출시키는 하이바 리-크로카르트 리-크로소르브(Hibar Li-ChrOCART Li-Chrosorb) RP-18 컬럼, 전컬럼 :가드팩(Guard Pak) RCSS C18 상에서의 역상 HPLC에 의한 머무름시간 (Rt) :8분를 특징으로하는 고체물질인 AB-021a 항생제.
- (a) U.V 광에서의 최대흡수 피크(0.02mg/ml의 1:1 (V/V)아세토니트릴/물) :369.0nm에서 0.90:350.0nm에서 2.01:332.6nm에서 2.21:318.0nm에서 1.49: (b)적외선광에서의최대흡수피크(cm-1) 3902,3853,3747,3375,3013,2921,2853,2757,1895,1699,1669,1645,1576,1540,1430,1378,1324,1261,1160,1094,1059,1004,969,919,878,843,803,779,697: (c) 분자량 :약 1165; (d)1H-N.M.R. 스펙트럼의 주요 피크 : δTMS(ppm) :7.21(d.1H) :6.75(dd.1H) :6.63(dd.1H) :6.57∼6.07(m.11H) :5.93∼5.70(m.3H) :5.70∼5.33(m.8H) :4.25∼4.20(m.4H) :4.02∼3.83(m.4H) :3.83∼3.59(m.4H) :3.29(t.1H) :2.82(t.2H) :2.72∼2.44(*)(m.6-7H) :2.41∼2.00(m.14H) :1.92(s.3H) :1.80∼1.14(m.21H) :1.00(d.3H) :0.95(d.3H) :0.84(d.3H) :범위내 (*)는 DMSOd6피크도 포함하는 것이다. (e)13C-N.M.R. 스펙트럼의 주요 피크:δTMS(ppm):212.0(s):169.2(s): 139.1(d):138.1(d):137.1(d):136.7(d):136.2(d):135.8(d):135.8(d):135.1(d):133.8(d):133.1(d):132.8(d):132.8(d):132.6(d):132.3(d):132.2(d):132.1(d):131.8(d):131.2(d):130.9(d):130.8(d):129.2(d):128.7(d):127.9(d):126.4(d):126.2(d):125.2(d):75.4(d):72.6(d):71.0(d):70.6(d):69.6(d):68.9(d):68.4(d):68.0(d):67.3(d):67.2(d):65.6(d):64.4(d):64.4(d):51.9(d):41.3(t):39.6(t):49.2(t):45.8(t):45.7(t):45.0(t):44.9(t):44.7(t):43.6(t):41.1(t):40.7(t):40.5(t)39.0(t):38.7(t):33.9(t):32.5(t):31.9(t):29.0(t),23.9(t):18.1(q):12.8(q):10.4(q):8.7(q). (f) 60F 254슬랩(Merck-Schuchardt)에서 박막크로마토그래피(TLC)에 의한 Rf값 ; 에탄올 : 디옥산 :30% 암모니아 수용액 :물(8:1:1:1)에서 0.54:메틸렌클로라이드:메탄올(17.3)에서 0.00:머크-스쿠챠르트 RP-18F 254 슬랩에서의 역상 크로마토그래피에 의한 Rf값 : 메탄올 : 아세토니트릴:물에 용해시킨 25mM 인산일수소 나트륨 (4:4:2)에서 0.27:메탄올 : 아세토니트릴 :물에 용해시킨 25mM 인산이수소칼륨 + 물에 용해시킨 7mM 테트라메틸-암모늄클로라이드(4:4:2)에서 0.35:메탄올:물에 용해시킨, 인산을 사용하여 pH7.5로 조정한 10mM 인산일수소암모늄용액(8:2)에서 0.12:메탄올:아세토니트릴 : 인산을 사용하여 pH7.5로 조정한 10mM 인산일수소암모늄용액(4:4:2)에서 0.24, (g) 메탄올 : 아세토니트릴 : 10mM 인산일수소암모늄 수용액(1:1:1)을 사용하여 0.8ml/분의 유량으로 40℃에서 용출시키는 하이바 리-크로카르트 리-크로소르브 RP-18컬럼, 전컬럼;가드팩 RCSS C18 상에서의 역상 HPLC에 의한 머무름시간(Rt):11.8분:을 특징으로하는 고체물질인 AB-021a 항생제.
- 호기조건하, 탄소, 질소 및 무기염 원을 함유하는 수성 영양 배양 배지에서 스트렙토미세스 에스피.(Strept omyces sp.) NCIB 40068 또는 그의 해당 변이체를 조절 배양시켜 수득할 수 있고, 실질적으로 청구범위 제1 및 제2항에서 정의된 AB-021a 항생제 및 AB-021b 항생제로 구성된 AB-021 항생제.
- 조절호기성 발효 조건하, 동화될 수 있는 탄소, 질소 및 무기염 원을 함유하는 수성 영양 배지에서 스트렙토미세스 에스피. NCIB 40068 또는 그의 해당 변이체를 실질적인 항생제 활성이 얻어질때까지 배양한후, 본질적으로 공지된 방법으로 상기 항생제를 회수하고, 임의로 AB-021a 항생제 및 AB-021b 항생제로 명명된 주성분을 분리시킴을 특징으로하는 AB-021 항생제의 제조 방법.
- 제4항에 있어서, 발효를 20℃∼35℃의 온도 범위에서 수행하는 방법.
- 제4항에 있어서, 발효를 5∼9의 pH 범위에서 수행하는 방법.
- 제4항에 있어서, AB-021 항생제를 여과후 크로마토그래피 기술에 의해 발효 브로쓰로부터 단리하는 방법.
- 제4항에 있어서, AB-021a 항생제 및 AB-021b 항생제를 10mM/1의 인산일수소암모늄을 함유하는 물로 구성된 혼합물에서 메탄올 30%부터 70%까지의 직선구배로 용출시키는 실리카겔컬럼에서의 역상 크로마토그래피로 단리하는 방법.
- 스트렙토미세스 에스피. NCIB 40068 미생물.
- 동화될 수 있는 탄소, 질소 및 무역염원을 함유하는 수성 영양 배지에서의 조절 호기성 발효에 의해 AB-021 항생제를 단리할 수 있는 양으로 생산할 수 있는 스트렙토미세스 에스피. NCIB 40068 미생물 또는 그의 해당변이체의 생물학적 순수 배양액.
- 살진균제 및/또는 살균제로서 AB-021 항생제, AB-021a 항생제 및 AB-021b 항생제 중에서 선택된 화합물의 용도.
- 유효성분으로 AB-021 항생제, AB-021a 항생제 및 AB-021b 항생제 중에서 선택된 화합물을 불활성고체 또는 액체 담체 및 임의로 다른 부가제와 함께 함유하는 살진균 및/또는 살균 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22808A | 1988-12-01 | ||
| IT22808A/88 | 1988-12-01 | ||
| IT8822808A IT1227657B (it) | 1988-12-01 | 1988-12-01 | Antibiotici ab-021 e processo per la loro produzione |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR900009992A true KR900009992A (ko) | 1990-07-06 |
| KR0140218B1 KR0140218B1 (ko) | 1998-07-01 |
Family
ID=11200668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019890017773A KR0140218B1 (ko) | 1988-12-01 | 1989-12-01 | Ab-o21 항생제 및 그의 제조방법 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5126265A (ko) |
| EP (1) | EP0371509B1 (ko) |
| JP (1) | JPH02288889A (ko) |
| KR (1) | KR0140218B1 (ko) |
| AT (1) | ATE118011T1 (ko) |
| AU (1) | AU636317B2 (ko) |
| BR (1) | BR8906050A (ko) |
| CA (1) | CA2004197C (ko) |
| DE (1) | DE68920973T2 (ko) |
| ES (1) | ES2067520T3 (ko) |
| IL (1) | IL92452A (ko) |
| IT (1) | IT1227657B (ko) |
| ZA (1) | ZA899034B (ko) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK162990D0 (da) * | 1990-07-06 | 1990-07-06 | Novo Nordisk As | Mikroorganismer |
| IT1243795B (it) * | 1990-08-21 | 1994-06-28 | Mini Ricerca Scient Tecnolog | Antibiotici ab-023 e processo per la loro preparazione |
| IT1259423B (it) * | 1991-12-04 | 1996-03-18 | Giorgio Cassani | Antibiotico ab-041 dotato di attivita' erbicida, ottenuto dallo streptomyces sp., e processo per la sua produzione |
| US5885823A (en) * | 1995-06-05 | 1999-03-23 | Nobl Laboratories, Inc. | Lawsonia intracellularis cultivation, anti-Lawsonia intracellularis vaccines and diagnostic agents |
| US5714375A (en) * | 1995-06-05 | 1998-02-03 | Nobl Laboratories, Inc. | Ileal symbiont intracellularis propagation in suspended host cells |
| US6436395B1 (en) | 1996-09-18 | 2002-08-20 | Merck & Co., Inc. | Rosellinia subiculata ATCC 74386 and fungus ATCC 74387 for producing sordarin compounds for fungi control |
| JP3328250B2 (ja) * | 1998-12-09 | 2002-09-24 | 岸本産業株式会社 | レジスト残渣除去剤 |
| US8834891B2 (en) * | 2005-03-14 | 2014-09-16 | Boehringer Ingelheim Vetmedica, Inc. | Immunogenic compositions comprising Lawsonia intracellularis |
| US8398994B2 (en) * | 2005-07-15 | 2013-03-19 | Boehringer Ingelheim Vetmedica, Inc. | Lawsonia vaccine and methods of use thereof |
| US8470336B2 (en) * | 2006-05-25 | 2013-06-25 | Boehringer Ingelheim Vetmedica, Inc. | Vaccination of young animals against Lawsonia intracellularis infections |
| WO2009037262A2 (en) * | 2007-09-17 | 2009-03-26 | Boehringer Ingelheim Vetmedica, Inc. | Method of preventing early lawsonia intracellularis infections |
| DE102020129458B4 (de) | 2020-05-20 | 2024-04-04 | Andreas Plur | Verfahren und Vorrichtung zur Herstellung eines Überzugs |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2262510B1 (ko) * | 1974-03-01 | 1977-11-04 | Rhone Poulenc Ind | |
| US4076802A (en) * | 1977-03-30 | 1978-02-28 | Hoffmann-La Roche Inc. | Antibiotic X-4357B |
| US4133876A (en) * | 1977-05-31 | 1979-01-09 | Eli Lilly And Company | Antibiotic A-32887 and process for production thereof |
| US4132779A (en) * | 1977-06-20 | 1979-01-02 | American Cyanamid Company | Antibiotic BL580 Zeta and use thereof as anticoccidial agent |
| US4705688A (en) * | 1986-06-30 | 1987-11-10 | American Cyanamid Company | Antibiotic LL-E19020 α and β |
| IT1221982B (it) * | 1987-07-08 | 1990-08-31 | Mini Ricerca Scient Tecnolog | Antibiotici ab 006 e processo per la loro produzione |
-
1988
- 1988-12-01 IT IT8822808A patent/IT1227657B/it active
-
1989
- 1989-11-27 ZA ZA899034A patent/ZA899034B/xx unknown
- 1989-11-27 IL IL9245289A patent/IL92452A/en not_active IP Right Cessation
- 1989-11-27 US US07/441,652 patent/US5126265A/en not_active Expired - Fee Related
- 1989-11-29 AU AU45719/89A patent/AU636317B2/en not_active Ceased
- 1989-11-29 CA CA002004197A patent/CA2004197C/en not_active Expired - Fee Related
- 1989-11-30 DE DE68920973T patent/DE68920973T2/de not_active Expired - Fee Related
- 1989-11-30 ES ES89122134T patent/ES2067520T3/es not_active Expired - Lifetime
- 1989-11-30 AT AT89122134T patent/ATE118011T1/de not_active IP Right Cessation
- 1989-11-30 EP EP89122134A patent/EP0371509B1/en not_active Expired - Lifetime
- 1989-11-30 BR BR898906050A patent/BR8906050A/pt not_active Application Discontinuation
- 1989-12-01 KR KR1019890017773A patent/KR0140218B1/ko not_active IP Right Cessation
- 1989-12-01 JP JP1313098A patent/JPH02288889A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE68920973D1 (de) | 1995-03-16 |
| IL92452A0 (en) | 1990-08-31 |
| EP0371509A2 (en) | 1990-06-06 |
| JPH02288889A (ja) | 1990-11-28 |
| IL92452A (en) | 1994-06-24 |
| ZA899034B (en) | 1990-09-26 |
| AU4571989A (en) | 1990-06-14 |
| CA2004197A1 (en) | 1990-06-01 |
| DE68920973T2 (de) | 1995-09-28 |
| IT8822808A0 (it) | 1988-12-01 |
| BR8906050A (pt) | 1990-07-31 |
| EP0371509B1 (en) | 1995-02-01 |
| ES2067520T3 (es) | 1995-04-01 |
| US5126265A (en) | 1992-06-30 |
| EP0371509A3 (en) | 1991-03-13 |
| ATE118011T1 (de) | 1995-02-15 |
| AU636317B2 (en) | 1993-04-29 |
| IT1227657B (it) | 1991-04-23 |
| CA2004197C (en) | 1998-06-30 |
| KR0140218B1 (ko) | 1998-07-01 |
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