KR960704876A - 혈소판 응집 저해 작용을 갖는 신규 화합물 (Novel Compound Having Platelet Aggregation Inhibitor Effect) - Google Patents
혈소판 응집 저해 작용을 갖는 신규 화합물 (Novel Compound Having Platelet Aggregation Inhibitor Effect)Info
- Publication number
- KR960704876A KR960704876A KR1019960701317A KR19960701317A KR960704876A KR 960704876 A KR960704876 A KR 960704876A KR 1019960701317 A KR1019960701317 A KR 1019960701317A KR 19960701317 A KR19960701317 A KR 19960701317A KR 960704876 A KR960704876 A KR 960704876A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- lower alkyl
- piperidin
- acetyl
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract 14
- 229940127218 antiplatelet drug Drugs 0.000 title claims 3
- 239000000106 platelet aggregation inhibitor Substances 0.000 title claims 3
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 title claims 2
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 10
- 150000003839 salts Chemical class 0.000 claims abstract 3
- 230000004962 physiological condition Effects 0.000 claims abstract 2
- 239000012453 solvate Substances 0.000 claims abstract 2
- -1 2-oxodioxol-4-yl group Chemical class 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 208000007536 Thrombosis Diseases 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 4
- 206010002383 Angina Pectoris Diseases 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 206010008118 cerebral infarction Diseases 0.000 claims 3
- 208000026106 cerebrovascular disease Diseases 0.000 claims 3
- 208000010125 myocardial infarction Diseases 0.000 claims 3
- 230000002093 peripheral effect Effects 0.000 claims 3
- 238000011282 treatment Methods 0.000 claims 3
- 208000031104 Arterial Occlusive disease Diseases 0.000 claims 2
- 208000021328 arterial occlusion Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- AICXVQJAEGSARR-UHFFFAOYSA-N 2-[4-[2-(2,5-dioxo-4-piperidin-4-ylpiperazin-1-yl)acetyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1C(=O)CN1C(=O)CN(C2CCNCC2)C(=O)C1 AICXVQJAEGSARR-UHFFFAOYSA-N 0.000 claims 1
- 206010061216 Infarction Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000007574 infarction Effects 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 206010043554 thrombocytopenia Diseases 0.000 claims 1
- 150000002148 esters Chemical group 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
혈소판 응집 저해 작용을 갖는 아래 일반식(I)의 화합물 및 그 약리학상 허용되는 염 및 용매화물이 개시되고 있다.
상기 식에서, A, B 및 C는 CH2또는 C=O이고, X 및 Y는 서로 다르게 CH 또는 N이며, D는 기 -(CH2)k- 또는 -(CH2)m-CO-(여기서 k는 1 내지 4의 정수이고, m은 0내지 3의 정수임)이고 C는 아래의 기(II) 또는 기(III)
(여기서, n은 1내지 3의 정수이고, Z은 -W-(CH2)p-COOR3이며, 여기서 W는 -O- 또는 결합을 나타내고, p는 1 내지 4의 정수이며, R3은 수소 원자, 저급 알킬 또는 생리적 조건하에서 제거될 수 있는 에스테르 잔기임)을 표시하며, R1은 수소원자 또는 저급 알킬이고, R2는 수소원자 및 저급 알킬기이다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (16)
- 다음 일반식(I)으로 표시되는 화합물 및 약리학적으로 허용되는 이들의 염 및 용매화물.상기 식에서, A, B 및 C는 CH2또는 C=O이고, X 및 Y는 서로 다르게 CH 또는 N이며, D는 기 -(CH2)k- 또는 -(CH2)m-CO-(여기서, k는 1 내지 4의 정수이고, m은 0 내지 3의 정수임)이고 E는 아래의 기(II) 또는 기(III)(여기서 n은 1 내지 3의 정수이고, Z은 -W-(CH2)p-COOR3이며, 여기서, W는 -O- 또는 결합을 나타내고, p는 1 내지 4의 정수미여, R3은 수소원자, 저급 알킬 또는 생리적 조건하에서 제거될 수 있는 에스테르 잔기임)을 표시하며, R1은 수소원자 또는 저급 알킬기(이 저급 알킬기의 1이상의 수소원자는 수산기, 할로겐 원자, 아미노기, 저급 알킬아미노기 또는 이미노기, 또는 저급 알킬기 치환-2-옥소디옥솔-4-일기로 치환되어도 좋음)이고, R2는 수소원자, 저급 알킬기(이 저급 알킬기의 1이상의 수소원자는 수산기, 할로겐 원자, 아미노기, 카르복실기, 저급 알콕시기, 저급 알킬아미노기 또는 저급 알콕시카르보닐기로 치환되어도 좋음).페닐기(이 페닐기의 1이상의 수소원자는 수산기, 할로겐 원자, 아미노기, 카르복실기, 저급 알콕시기, 저급 알킬 아미노기, 저급 알콕시카르보닐기 또는 할로 저급 알킬기로 치환되어도 좋음), 또는 페닐 저급 알킬기(이 페닐기의 1이상의 수소원자는 수산기, 할로겐 원자, 아미노기, 카르복실기, 저급 알콕시기, 저급 알킬아미노기, 저급 알콕시카르보닐기 또는 할로 저급 알킬기로 치환되어도 좋음)이다.
- 제 1항에 있어서, X가 CH이고, Y가 N인 화합물.
- 제 1항에 있어서, A가 C=O이고, B 및 C가 CH2이거나, 또는 A, B 및 C중 어느 2개가 C=O이며, 남은 1개 CH2인 화합물.
- 제 1항에 있어서, D가 -(CH2)m-CO-인 화합물.
- 제 1항에 있어서, m이 0 내지 3의 정수인 화합물.
- 제 1항에 있어서, Z가 기 -W(CH2)p-COOR3(여기서, W은 -O-임)인 화합물.
- 제 1항에 있어서, [[4-[[4-(피페리딘-4-일)-2-옥소피페라진-1-일]아세틸]-O-페닐렌]디옥시]디아세트산, [[4-[[4-(피페리딘-4-일)피페라진-1-일]아세틸]-O-페닐렌]디옥시]디아세트산, [[4-[[4-(피페리딘-4-일)-2-옥소피페라진-1-일]아세틸]페녹시아세트산, 디에틸[[4-[[4-(피페리딘-4-일)-2-옥소피페라진-1-일]아세틸]-O-페닐렌]디옥시]디아세테이트, n-부틸 4-[[4-(피페리딘-4-일)-2,6-디옥소피페라진-1-일]아세틸]페녹시아세트, 4-[[4-(피페리딘-4-일)-2,3-디옥소피페라진-1-일]페녹시아세트산, n-부틸 4-[[4-(피페리딘-4-일)-2,5-디옥소피페라진-1-일]아세틸]페녹시아세트, 4-[[4-(피페리딘-4-일)-2,5-디옥소피페라진-1-일]아세틸]페녹시아세트산, n-부틸 4-[[4-(피페리딘-4-일)-2-옥소피페라진-1-일]아세틸]페녹시아세트.2염산염, 및 에틸 4-[[4-(피페리딘-4-일)-2-옥소피페라진-1-일]아세틸]페녹시아세테이트로 이루어진 군으로부터 선택되는 화합물.,
- 제 1항에 기재된 화합물 또는 그 약리학상 허용되는 염 또는 용매 화합물의 유효량을 약리학상 허용되는 담체와 함께 포함하여 이루어지는 의약 조성물.
- 제 8항에 있어서, 혈소판 응집 저해제로서 사용되는 의약 조성물.
- 제 9항에 있어서, 혈전성 질환의 치료 또는 예방에 사용되는 의약 조성물.
- 제 10항에 있어서, 혈전성 질환이 뇌경색증, 심근 경색증, 협심증 및 말초성동맥 폐색증인 의약 조성물.
- 제 1항에 기재된 화합물 유효량을 포유류에 투여하는 것으로 이루어진는 혈저성 절환의 치료 또는 예방법.
- 제 12항에 있어서, 혈전성 질환이 뇌색경증, 심근 경색증, 협심증 및 말초성 동맥 페색증인 치료 또는 예방법.
- 혈소판 응집 저해제의 제조를 위한 제 1항에 기재된 화합물의 용도.
- 혈전성 질환의 치료 또는 예방에 사용되는 의약 조성물의 제조를 위한 제 1항에 기재된 화합물의 용도.
- 제 15항에 있어서, 혈전성 질환이 뇌경색증, 심근 경색증, 협심증, 말초성 동맥 폐색증인 치료 또는 예방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP94-163506 | 1994-07-15 | ||
| JP16350694 | 1994-07-15 | ||
| JP13551495 | 1995-06-02 | ||
| JP95-135514 | 1995-06-02 | ||
| PCT/JP1995/001419 WO1996002503A1 (fr) | 1994-07-15 | 1995-07-17 | Nouveaux composes ayant un effet inhibant l'agregation plaquettaire |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR960704876A true KR960704876A (ko) | 1996-10-09 |
| KR100254666B1 KR100254666B1 (ko) | 2000-05-01 |
Family
ID=26469352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019960701317A KR100254666B1 (ko) | 1994-07-15 | 1995-07-17 | 혈소판 응집 저해 작용을 갖는 신규 화합물 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5814636A (ko) |
| EP (1) | EP0721941A4 (ko) |
| KR (1) | KR100254666B1 (ko) |
| CN (1) | CN1134695A (ko) |
| AU (1) | AU709070B2 (ko) |
| CA (1) | CA2171850A1 (ko) |
| NO (1) | NO305951B1 (ko) |
| NZ (1) | NZ289498A (ko) |
| RU (1) | RU2156763C2 (ko) |
| TW (1) | TW397831B (ko) |
| WO (1) | WO1996002503A1 (ko) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU691361B2 (en) * | 1994-12-01 | 1998-05-14 | Toyama Chemical Co. Ltd. | Novel 2,3-diketopiperazine derivative or salt thereof |
| US6069143A (en) * | 1994-12-20 | 2000-05-30 | Smithkline Beecham Corporation | Fibrinogen receptor antagonists |
| WO1996019223A1 (en) * | 1994-12-22 | 1996-06-27 | Smithkline Beecham Corporation | Fibrinogen receptor antagonists |
| AU4432496A (en) * | 1994-12-23 | 1996-07-19 | Dr. Karl Thomae Gmbh | Piperazine derivatives, medicaments containing the same, their use and process for preparing the same |
| US5889006A (en) * | 1995-02-23 | 1999-03-30 | Schering Corporation | Muscarinic antagonists |
| NZ321575A (en) * | 1995-10-30 | 1999-05-28 | Janssen Pharmaceutica Nv | 1-(1,2-disubstituted piperidinyl)-4- substituted piperazine derivatives |
| TW429256B (en) * | 1995-12-27 | 2001-04-11 | Janssen Pharmaceutica Nv | 1-(1,2-disubstituted piperidinyl)-4-(benzimidazolyl- and imidazopyridinyl)-piperidine derivatives |
| TW531537B (en) | 1995-12-27 | 2003-05-11 | Janssen Pharmaceutica Nv | 1-(1,2-disubstituted piperidinyl)-4-substituted piperidine derivatives |
| TW382017B (en) | 1995-12-27 | 2000-02-11 | Janssen Pharmaceutica Nv | 1-(1,2-disubstituted piperidinyl)-4-(fused imidazole)-piperidine derivatives |
| WO1997036887A1 (fr) * | 1996-03-29 | 1997-10-09 | Meiji Seika Kaisha, Ltd. | Nouveaux composes heterocycliques ayant un effet d'inhibition de l'agregation des plaquettes |
| US5990107A (en) * | 1996-06-28 | 1999-11-23 | Merck & Co., Inc. | Fibrinogen receptor antagonist prodrugs |
| UA62985C2 (en) * | 1997-11-10 | 2004-01-15 | Lunnbeck As H | A method for the preparation of citalopram |
| AU7675798A (en) | 1998-04-09 | 1999-11-01 | Meiji Seika Kaisha Ltd. | Nitrogen-containing heterocyclic compounds having antiplatelet aggregation effect and medicinal use thereof |
| GB0025354D0 (en) | 2000-10-17 | 2000-11-29 | Glaxo Group Ltd | Chemical compounds |
| US7482365B2 (en) | 2002-02-08 | 2009-01-27 | Glaxo Group Limited | Piperidylcarboxamide derivatives and their use in the treatment of tachykinin-mediated diseases |
| GB0203020D0 (en) * | 2002-02-08 | 2002-03-27 | Glaxo Group Ltd | Chemical compounds |
| GB0203022D0 (en) | 2002-02-08 | 2002-03-27 | Glaxo Group Ltd | Chemical compounds |
| JP5078869B2 (ja) * | 2005-03-08 | 2012-11-21 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ニューロキニン（ｎｋ１）拮抗物質としてのジアザ−スピロ−［４．４］−ノナン誘導体 |
| EP2670722B1 (en) | 2011-01-31 | 2016-10-12 | Council of Scientific & Industrial Research | Chiral 1-(4-methylphenylmethyl)-5-oxo-{n-[(3-t-butoxycarbonyl-aminomethyl)]-piperidin-1-yl}-pyrrolidine-2-carboxamides as inhibitors of collagen induced platelet activation and adhesion |
| CN114920722B (zh) * | 2021-06-02 | 2024-03-08 | 何黎琴 | 一种7-羟基-3-乙酰基香豆素肟类化合物、其制备方法及医药用途 |
| WO2023122481A2 (en) * | 2021-12-20 | 2023-06-29 | Sigma-Aldrich Co. Llc | Chemical linkers |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB1278166A (en) * | 1970-04-14 | 1972-06-14 | Yoshitomo Pharmaceutical Ind L | Novel pyrrolidine and piperidine derivarives and pharmaceutical compositions containing them |
| US5225402A (en) * | 1989-02-10 | 1993-07-06 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives |
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| US5442004A (en) * | 1989-10-05 | 1995-08-15 | Raychem Limited | Gels |
| US5273982A (en) * | 1990-03-09 | 1993-12-28 | Hoffmann-La Roche Inc. | Acetic acid derivatives |
| DE4107857A1 (de) * | 1991-03-12 | 1992-09-17 | Thomae Gmbh Dr K | Cyclische harnstoffderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE4127404A1 (de) * | 1991-08-19 | 1993-02-25 | Thomae Gmbh Dr K | Cyclische iminoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| AU2915892A (en) * | 1991-11-14 | 1993-06-15 | Glaxo Group Limited | Piperidine acetic acid derivatives as inhibitors of fibrinogen-dependent blood platelet aggregation |
| DE4241632A1 (de) * | 1992-12-10 | 1994-06-16 | Thomae Gmbh Dr K | Carbonsäurederivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| DE4326344A1 (de) * | 1993-08-05 | 1995-02-09 | Thomae Gmbh Dr K | Carbonamide, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| US5700801A (en) * | 1994-12-23 | 1997-12-23 | Karl Thomae, Gmbh | Piperazine derivatives, pharmaceutical compositions containing these compounds, their use and processes for preparing them |
-
1995
- 1995-07-17 EP EP95925137A patent/EP0721941A4/en not_active Ceased
- 1995-07-17 WO PCT/JP1995/001419 patent/WO1996002503A1/ja not_active Application Discontinuation
- 1995-07-17 KR KR1019960701317A patent/KR100254666B1/ko not_active IP Right Cessation
- 1995-07-17 CA CA002171850A patent/CA2171850A1/en not_active Abandoned
- 1995-07-17 CN CN95190807A patent/CN1134695A/zh active Pending
- 1995-07-17 RU RU96109467/04A patent/RU2156763C2/ru active
- 1995-07-17 TW TW084107435A patent/TW397831B/zh not_active IP Right Cessation
- 1995-07-17 US US08/615,227 patent/US5814636A/en not_active Expired - Fee Related
- 1995-07-17 AU AU29367/95A patent/AU709070B2/en not_active Ceased
- 1995-07-17 NZ NZ289498A patent/NZ289498A/en unknown
-
1996
- 1996-03-07 NO NO960919A patent/NO305951B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2936795A (en) | 1996-02-16 |
| WO1996002503A1 (fr) | 1996-02-01 |
| KR100254666B1 (ko) | 2000-05-01 |
| CN1134695A (zh) | 1996-10-30 |
| NO960919D0 (no) | 1996-03-07 |
| NO960919L (no) | 1996-05-10 |
| EP0721941A1 (en) | 1996-07-17 |
| US5814636A (en) | 1998-09-29 |
| TW397831B (en) | 2000-07-11 |
| RU2156763C2 (ru) | 2000-09-27 |
| EP0721941A4 (en) | 1996-09-25 |
| CA2171850A1 (en) | 1996-02-01 |
| NZ289498A (en) | 1998-02-26 |
| AU709070B2 (en) | 1999-08-19 |
| NO305951B1 (no) | 1999-08-23 |
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