KR910007959A - 방사성 동위원소로 표지된 항응고성 펩티드 - Google Patents
방사성 동위원소로 표지된 항응고성 펩티드 Download PDFInfo
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- KR910007959A KR910007959A KR1019900015755A KR900015755A KR910007959A KR 910007959 A KR910007959 A KR 910007959A KR 1019900015755 A KR1019900015755 A KR 1019900015755A KR 900015755 A KR900015755 A KR 900015755A KR 910007959 A KR910007959 A KR 910007959A
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- Prior art keywords
- tyr
- peptide
- peptide derivative
- amino acid
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- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract 25
- 239000003146 anticoagulant agent Substances 0.000 title claims abstract 3
- 229940127219 anticoagulant drug Drugs 0.000 title claims abstract 3
- 102000004196 processed proteins & peptides Human genes 0.000 title 1
- 150000001413 amino acids Chemical class 0.000 claims 10
- 108010007267 Hirudins Proteins 0.000 claims 3
- 108090000190 Thrombin Proteins 0.000 claims 3
- 230000023555 blood coagulation Effects 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229960004072 thrombin Drugs 0.000 claims 3
- 102000007625 Hirudins Human genes 0.000 claims 2
- 125000000539 amino acid group Chemical group 0.000 claims 2
- 230000010100 anticoagulation Effects 0.000 claims 2
- 238000003556 assay Methods 0.000 claims 2
- 239000008280 blood Substances 0.000 claims 2
- 210000004369 blood Anatomy 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- WQPDUTSPKFMPDP-OUMQNGNKSA-N hirudin Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC(OS(O)(=O)=O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]1NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@H](C(NCC(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N2)=O)CSSC1)C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)[C@@H](C)O)CSSC1)C(C)C)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 WQPDUTSPKFMPDP-OUMQNGNKSA-N 0.000 claims 2
- 229940006607 hirudin Drugs 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims 1
- ROHFNLRQFUQHCH-RXMQYKEDSA-N D-leucine Chemical compound CC(C)C[C@@H](N)C(O)=O ROHFNLRQFUQHCH-RXMQYKEDSA-N 0.000 claims 1
- 108010016626 Dipeptides Proteins 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000729 N-terminal amino-acid group Chemical group 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000001514 detection method Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- 238000002372 labelling Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- -1 t-butyloxy carbonyl Chemical group 0.000 claims 1
- DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/86—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving blood coagulating time or factors, or their receptors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/81—Protease inhibitors
- C07K14/815—Protease inhibitors from leeches, e.g. hirudin, eglin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
- G01N2333/81—Protease inhibitors
- G01N2333/815—Protease inhibitors from leeches, e.g. hirudin, eglin
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Gastroenterology & Hepatology (AREA)
- Cell Biology (AREA)
- Pathology (AREA)
- General Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Tropical Medicine & Parasitology (AREA)
- Food Science & Technology (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (19)
- 방사성 동위원소로 표지된 다음 일반식의 펩티드 유도체.x-A1-A2-A3-A4-A5-A6-A7-A8-A9-A10-Y상기식에서, X는 수소, 탄소 원자수 1내지 10의 알킬기 1 또는 2개, 탄소 원자수 2내지 10의 아실기 1 또는 2개, 카르보벤질옥시 또는 t-부틸옥시 카르보닐로 구성되는 군으로부터 선택된 아미노 말단 잔기이고, A1은 하나의 결합이거나 또는, 히루딘 또는 그의 천연 변이체 또는 그의 일부의 서열이거나 또는 임의 아미노산 잔기 1내지 11개를 함유하는 펩티드이며, A2는 1-Tyr, [3H]-Tyr, [125I]-Tyr, [131I]-Tyr, 또는 A9가 방사송 동위 원소로 표지된 아미노산일 경우 L-방향족 아미노산의 0내지 5개의 잔기이고, A3는 Glu, Asp, Ala이며, A4는 임의 아미노산이고, A5는 Ile, Val, Leu, Nle, Ala, D-Leu 또는 Phe이며, A6는 Pro, Hyp, Azt, Pip, DhPro, 티아졸리딘-4-카르복실레이트, Sar, NMePgi 또는 D-Ala이고, A7은 임의 아미노산이며, A8은 임의 아미노산이며, A9는 Tyr, I-Tyr, [125I]-Tyr, [131I]-Tyr, [3H]-Tyr, Met, Trp, Phe, Leu, Nle, Ile, Val, Cha, His, Ala 및 Pro로 구성되는 군으로부터 선택된 친유성 아미노산이거나, 또는 이러한 아미노산 또는 임의 친유성 아미노산 중 적어도 1개를 함유하는 디펩티드이며, A10은 하나의 결합이거나, 또는 히루딘 또는 그의 천연 변이체 또는 그의 일부의 서열이거나, 또는 임의 아미노산 잔기를 1내지 1개 함유하는 펩티드이고, Y는 OH, (C1-C8)알콕시, 아미노, 또는 모노 또는 디(C1-C4)알킬 치환된 아미노산으로 구성되는 군으로부터 선택된 카르복시 말단 잔기기이거나 또는 알콜 말단 잔기이다.
- 제1항에 있어서, A2가 I-Tyt, [3H]-Tyr, [131I]-Tyr, [125I]-Tyr인 것을 특징으로 하는 펩티드 유도체.
- 제1항에 있어서, A3이 Glu인 것을 특징으로 하는 펩티드 유도체.
- 제1항에 있어서, A4이 Pro인 것을 특징으로 하는 펩티드 유도체.
- 제1항에 있어서, A5이 Ile인 것을 특징으로 하는 펩티드 유도체.
- 제1항에 있어서, A6이 Pro인 것을 특징으로 하는 펩티드 유도체.
- 제1항에 있어서, A7이 Glu인 것을 특징으로 하는 펩티드 유도체.
- 제1항에 있어서, A8이 Glu인 것을 특징으로 하는 펩티드 유도체.
- 제1항에 있어서, A9이 Ala-Cha인 것을 특징으로 하는 펩티드 유도체.
- 제1항에 있어서, A10이 D-Cha인 것을 특징으로 하는 펩티드 유도체.
- 제1항에 있어서, X가 H인 것을 특징으로 하는 펩티드 유도체.
- 제1항에 있어서, A9가 I-Tyt, [3H]-Tyr, [125I]-Tyr, [131I]-Tyr인 것을 특징으로 하는 펩티드 유도체.
- 제1항 내지 12항 중 어느 하나의 항의 펩티드 유도체 항응고 유효량 및 제약상 허용되는 담체를 투여하는 것을 특징으로 하는, 혈액 응고의 감소가 요구되는 환자에 있어서 혈액 응고를 감소시키는 방법.
- 제1항 내지 12항 중 어느 하나의 항의 펩티드 유도체 혈액 항응고 유효량을 매질과 접촉시키는 것을 특징으로 하는, 매질 중의 혈액 응고를 감소시키는 방법.
- 환장에 있어서, 제1항 내지 12항 중 어느 하나의 항의 표지된 하루딘 펩티드의 생분포 패턴을 진단학적으로 영상화 및 검출하여, 생체내트롬빈을 검출하는 방법.
- 제1항 내지 12항중 어느 하나의 항의 표지된 히루딘 펩티디를 사용하여 혈액, 조직 또는 스페슘(specium)시료 중에 이용 가능한 트롬빈의 농도를 측정하기 위해, 시험관내에서 트롬빈 검출을 위한 분석 또는 진단용 키트.
- (a) A10기로부터 C-말단이 보호된 아미노산이 적합하게 결합된 수지를 사용하는 단계, (b) 다른 α-아미노 보호된 아미노산 A9내지 A1를 순차적으로 커플링시켜 보호된 아미노산 서열을 얻는 단계, (c) 상기 보호기를 제거시킨 후 목적하는 펩티드를 정제하는 단계, (d) 이 펩티드를 방사성 할로겐으로 표지시키고, 표지된 펩티드를 정제하는 단계로 이루어지는, 제1 내지 12항중 어느 하나의 항에 기재된 펩티드 유도체 또는 그의 제약상 허용되는 염을 제조하는 방법.
- 제약상 활성물질로서 사용하기 위한 제1 내지 12항중 어느 하나의 항에 기재된 펩티드 유도체 또는 제약상 허용하는 이들의 염 또는 이들의 혼합물.
- 항응고제로서 사용하기 위한 제1 내지 12항중 어느 하나의 항에 기재된 펩티드 유도체 또는 제약상 허용되는 이들의 염 또는 이들의 혼합물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41633589A | 1989-10-03 | 1989-10-03 | |
| US416335 | 1989-10-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR910007959A true KR910007959A (ko) | 1991-05-30 |
| KR0168644B1 KR0168644B1 (ko) | 1999-01-15 |
Family
ID=23649537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019900015755A KR0168644B1 (ko) | 1989-10-03 | 1990-09-29 | 방사성 동위원소로 표지된 항응고성 펩티드 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5279812A (ko) |
| EP (1) | EP0421366B1 (ko) |
| JP (1) | JP2899390B2 (ko) |
| KR (1) | KR0168644B1 (ko) |
| CN (1) | CN1050721A (ko) |
| AT (1) | ATE125269T1 (ko) |
| AU (1) | AU631681B2 (ko) |
| CA (1) | CA2026377A1 (ko) |
| DE (1) | DE69021000T2 (ko) |
| ES (1) | ES2076999T3 (ko) |
| FI (1) | FI904851A0 (ko) |
| HU (1) | HU207525B (ko) |
| IE (1) | IE903531A1 (ko) |
| IL (1) | IL95864A0 (ko) |
| NO (1) | NO904291L (ko) |
| NZ (1) | NZ235499A (ko) |
| PT (1) | PT95485A (ko) |
| ZA (1) | ZA907743B (ko) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5395609A (en) * | 1989-06-19 | 1995-03-07 | Antisoma Limited | Synthetic peptides for use in tumor detection |
| GB8914020D0 (en) * | 1989-06-19 | 1989-08-09 | Antisoma Ltd | Synthetic peptides for use in thrombus detection |
| US5574012A (en) * | 1990-07-24 | 1996-11-12 | Merrell Pharmaceuticals Inc. | Analogs of hirudin having anti-platelet activity |
| DK0540574T3 (da) * | 1990-07-24 | 1996-09-30 | Merrell Pharma Inc | Antikoagulationspeptider |
| ZA915658B (en) * | 1990-07-24 | 1992-05-27 | Merrell Dow Pharma | Analogs of hirudin having antiplatelet activity |
| WO1993004082A1 (en) * | 1991-08-20 | 1993-03-04 | Baxter International Inc. | Analogs of hirudin |
| US5371184A (en) * | 1992-02-05 | 1994-12-06 | Mallinckrodt Medical, Inc. | Radiolabelled peptide compounds |
| EP1099693A1 (en) * | 1992-02-05 | 2001-05-16 | Mallinckrodt Inc. | Radiolabelled peptide compounds |
| US5879657A (en) * | 1993-03-30 | 1999-03-09 | The Dupont Merck Pharmaceutical Company | Radiolabeled platelet GPIIb/IIIa receptor antagonists as imaging agents for the diagnosis of thromboembolic disorders |
| US5750088A (en) | 1993-03-30 | 1998-05-12 | The Dupont Merck Pharmaceutical Company | Stable hydrazones linked to a peptide moiety as reagents for the preparation of radiopharmaceuticals |
| ES2199963T3 (es) * | 1993-06-11 | 2004-03-01 | Merrell Pharmaceuticals Inc. | Peptidos trifuncionales antitrombina y antiplaquetarios. |
| US5457177A (en) * | 1993-06-16 | 1995-10-10 | Merck & Co., Inc. | Thrombin receptor radioligands |
| JP3349513B2 (ja) * | 1994-05-24 | 2002-11-25 | エーザイ株式会社 | ２，６−ジ−ヨードフェノール−４−イルを少なくとも２ケ含む化合物とヨードアレルギー診断薬 |
| US5808146A (en) * | 1995-11-09 | 1998-09-15 | Emory University | Amino acid analogs for tumor imaging |
| US6808698B1 (en) | 1999-03-26 | 2004-10-26 | Bristol-Myers Squibb Pharma Company | Method for localization of blood clots |
| US6254852B1 (en) | 1999-07-16 | 2001-07-03 | Dupont Pharmaceuticals Company | Porous inorganic targeted ultrasound contrast agents |
| US6685914B1 (en) * | 1999-09-13 | 2004-02-03 | Bristol-Myers Squibb Pharma Company | Macrocyclic chelants for metallopharmaceuticals |
| CN101041674A (zh) * | 2002-04-30 | 2007-09-26 | 埃默里大学 | 肿瘤成像化合物 |
| US7319149B2 (en) * | 2003-06-13 | 2008-01-15 | Bristol-Myers Squibb Pharma Company | Chelants and macrocyclic metal complex radiopharmaceuticals thereof |
| US7317104B2 (en) | 2003-06-13 | 2008-01-08 | Bristol-Myers Squibb Pharma Company | Chelants and macrocyclic metal complex radiopharmaceuticals thereof |
| CN100402092C (zh) * | 2005-06-07 | 2008-07-16 | 西安交通大学 | 血栓诊断和/或治疗用含气干粉活性剂及其制备工艺 |
| EP1893244A4 (en) | 2005-06-23 | 2009-06-24 | Univ Emory | AGENTS FOR IMAGING |
| JP5349960B2 (ja) * | 2005-06-23 | 2013-11-20 | エモリー ユニバーシティー | 腫瘍画像化のためのアミノ酸類似体の立体選択的合成 |
| US8246752B2 (en) | 2008-01-25 | 2012-08-21 | Clear Catheter Systems, Inc. | Methods and devices to clear obstructions from medical tubes |
| CN110437307B (zh) * | 2019-07-26 | 2020-11-13 | 暨南大学 | 一类具抗血栓和脑神经细胞保护作用的水蛭多肽及其应用 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5850213B2 (ja) * | 1977-06-20 | 1983-11-09 | 株式会社第一ラジオアイソト−プ研究所 | カルチトニンの定量法 |
| DE3040824A1 (de) * | 1980-10-30 | 1982-08-19 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neues dekapeptid, verfahren zu seiner herstellung und verwendung |
| US4455290A (en) * | 1981-04-02 | 1984-06-19 | Research Corporation | Inhibition of fibrin polymerization by a peptide isolated from fibrin Fragment D1 |
| US4585740A (en) * | 1983-05-03 | 1986-04-29 | The Whittier Institute For Diabetes And Endocrinology | Prolactin immunoassay using synthetic peptide |
| FR2550204B1 (fr) * | 1983-08-05 | 1987-11-13 | Toyo Jozo Kk | Derives peptidiques de (nle8,nle1b, tyr34)-h-pth |
| DE3445532A1 (de) * | 1984-12-13 | 1986-06-19 | Plantorgan Werk Heinrich G.E. Christensen, KG, 2903 Bad Zwischenahn | Hirudin-pa, desulfatohirudine-pa, verfahren zur herstellung und pharmazeutische mittel, die diese wirkstoffe enthalten |
| DE3689525D1 (de) * | 1985-07-17 | 1994-02-24 | Hoechst Ag | Neue Polypeptide mit blutgerinnungshemmender Wirkung, Verfahren zu deren Herstellung bzw. Gewinnung, deren Verwendung und diese enthaltende Mittel. |
| CA1341032C (en) * | 1987-01-23 | 2000-06-20 | John L. Krstenansky | Anticoagulant peptides |
| ZA883444B (ko) * | 1987-05-21 | 1988-11-16 | ||
| ZA883443B (en) * | 1987-05-21 | 1988-11-16 | Merrell Dow Pharmaceuticals Inc. | Cyclic anticoagulant peptides |
| AU3098289A (en) * | 1988-03-04 | 1989-09-07 | Biogen, Inc. | Hirudin peptides |
| ES2052062T3 (es) * | 1988-06-11 | 1994-07-01 | Ciba Geigy Ag | Nuevos polipeptidos con actividad anticoagulante. |
| US5192747A (en) * | 1989-10-03 | 1993-03-09 | Merrell Dow Pharmaceuticals Inc. | Anticoagulant peptides |
-
1990
- 1990-09-27 ZA ZA907743A patent/ZA907743B/xx unknown
- 1990-09-27 CA CA002026377A patent/CA2026377A1/en not_active Abandoned
- 1990-09-28 NZ NZ235499A patent/NZ235499A/xx unknown
- 1990-09-28 HU HU906271A patent/HU207525B/hu not_active IP Right Cessation
- 1990-09-29 KR KR1019900015755A patent/KR0168644B1/ko not_active IP Right Cessation
- 1990-09-30 CN CN90108051A patent/CN1050721A/zh active Pending
- 1990-10-01 IL IL95864A patent/IL95864A0/xx unknown
- 1990-10-01 AU AU63689/90A patent/AU631681B2/en not_active Ceased
- 1990-10-02 FI FI904851A patent/FI904851A0/fi not_active IP Right Cessation
- 1990-10-02 IE IE353190A patent/IE903531A1/en unknown
- 1990-10-02 JP JP2263233A patent/JP2899390B2/ja not_active Expired - Lifetime
- 1990-10-02 NO NO90904291A patent/NO904291L/no unknown
- 1990-10-02 PT PT95485A patent/PT95485A/pt not_active Application Discontinuation
- 1990-10-03 AT AT90118902T patent/ATE125269T1/de not_active IP Right Cessation
- 1990-10-03 DE DE69021000T patent/DE69021000T2/de not_active Expired - Fee Related
- 1990-10-03 EP EP90118902A patent/EP0421366B1/en not_active Expired - Lifetime
- 1990-10-03 ES ES90118902T patent/ES2076999T3/es not_active Expired - Lifetime
-
1991
- 1991-03-28 US US07/676,592 patent/US5279812A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US5279812A (en) | 1994-01-18 |
| AU6368990A (en) | 1991-04-11 |
| KR0168644B1 (ko) | 1999-01-15 |
| JP2899390B2 (ja) | 1999-06-02 |
| ATE125269T1 (de) | 1995-08-15 |
| JPH03120296A (ja) | 1991-05-22 |
| EP0421366B1 (en) | 1995-07-19 |
| NO904291L (no) | 1991-04-04 |
| DE69021000T2 (de) | 1996-04-04 |
| ZA907743B (en) | 1991-07-31 |
| AU631681B2 (en) | 1992-12-03 |
| HU906271D0 (en) | 1991-03-28 |
| ES2076999T3 (es) | 1995-11-16 |
| NO904291D0 (no) | 1990-10-02 |
| IL95864A0 (en) | 1991-07-18 |
| CA2026377A1 (en) | 1991-04-04 |
| HUT55801A (en) | 1991-06-28 |
| FI904851A0 (fi) | 1990-10-02 |
| HU207525B (en) | 1993-04-28 |
| IE903531A1 (en) | 1991-04-10 |
| NZ235499A (en) | 1993-04-28 |
| DE69021000D1 (de) | 1995-08-24 |
| EP0421366A1 (en) | 1991-04-10 |
| PT95485A (pt) | 1991-06-25 |
| CN1050721A (zh) | 1991-04-17 |
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